CA2369591A1 - Disodium salts, monohydrate, and ethanol solvates - Google Patents

Disodium salts, monohydrate, and ethanol solvates Download PDF

Info

Publication number
CA2369591A1
CA2369591A1 CA002369591A CA2369591A CA2369591A1 CA 2369591 A1 CA2369591 A1 CA 2369591A1 CA 002369591 A CA002369591 A CA 002369591A CA 2369591 A CA2369591 A CA 2369591A CA 2369591 A1 CA2369591 A1 CA 2369591A1
Authority
CA
Canada
Prior art keywords
delivery agent
disodium salt
composition
unsubstituted
substituted
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
CA002369591A
Other languages
French (fr)
Other versions
CA2369591C (en
Inventor
William E. Bay
Rajesh K. Agarwal
Kiran Chaudhary
Shingai Majuru
Michael M. Goldberg
Joanne P. Russo
Moise Azria
Joseph Murray Ault
Simon David Bateman
Subash Patel
Joseph Sikora
Rebecca Fai-Ying Yang
Joseph L. Zielinski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Emisphere Technologies Inc
Original Assignee
Individual
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Priority to CA002487952A priority Critical patent/CA2487952A1/en
Publication of CA2369591A1 publication Critical patent/CA2369591A1/en
Application granted granted Critical
Publication of CA2369591C publication Critical patent/CA2369591C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K47/00—Medicinal preparations characterised by the non-active ingredients used, e.g. carriers or inert additives; Targeting or modifying agents chemically bound to the active ingredient
    • A61K47/06—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite
    • A61K47/16—Organic compounds, e.g. natural or synthetic hydrocarbons, polyolefins, mineral oil, petrolatum or ozokerite containing nitrogen, e.g. nitro-, nitroso-, azo-compounds, nitriles, cyanates
    • A61K47/18—Amines; Amides; Ureas; Quaternary ammonium compounds; Amino acids; Oligopeptides having up to five amino acids
    • A61K47/183—Amino acids, e.g. glycine, EDTA or aspartame
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/12—Drugs for disorders of the metabolism for electrolyte homeostasis
    • A61P3/14—Drugs for disorders of the metabolism for electrolyte homeostasis for calcium homeostasis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P7/00—Drugs for disorders of the blood or the extracellular fluid
    • A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
    • C07C235/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C235/44—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/58—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C235/60—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings and singly-bound oxygen atoms bound to the same carbon skeleton with carbon atoms of carboxamide groups and singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring with carbon atoms of carboxamide groups and singly-bound oxygen atoms, bound in ortho-position to carbon atoms of the same non-condensed six-membered aromatic ring having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
    • C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
    • C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D265/24—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in positions 2 and 4
    • C07D265/26—Two oxygen atoms, e.g. isatoic anhydride
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K9/00—Medicinal preparations characterised by special physical form
    • A61K9/20—Pills, tablets, discs, rods
    • A61K9/2004—Excipients; Inactive ingredients
    • A61K9/2013—Organic compounds, e.g. phospholipids, fats

Abstract

The inventors have discovered that the disodium salt of certain delivery agents has surprisingly greater efficacy for delivering active agents than t he corresponding monosodium salt. Furthermore, the inventors have discovered th at the disodium salts of these delivery agents form solvates with ethanol and hydrates with water. The delivery agents have formula (I) wherein R1, R2, R3 , and R4 are indepedently hydrogen, halogen, C1-C4 alkyl, or C1-C4 alkoxy; and R5 is a substituted or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene). The hydrates and solvates of present invention also have surprisingly greater efficacy for delivering active agents, such as heparin and calcitonin, than their corresponding monosodium salts and free acids. The present invention provides an alcohol solvate, such as ethanol solvate, of a disodium salt of a delivery agent of formula (I) above. Preferred delivery agents include, but are not limited to, N-(5-chlorosalicyloyl)-8-aminocaprylic acid (5-CNAC),N-( 10- [2-hydroxybenzoyl]amino)decanoic acid (SNAD), and sodium N-(8-[2- hydroxybenzoyl]amino)caprylate (SNAC). The invention also provides methods o f preparing the disodium salt, ethanol solvate, and hydrate and compositions containing the disodium salt, ethanol solvate, and/or hydrate.

Claims (28)

1. A disodium salt of a delivery agent having the formula wherein R1, R2, R3, and R4 are independently hydrogen, -OH, -NR6R7, halogen, C1-C4 alkyl, or C1-C4 alkoxy;
R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene); and R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.
2. The disodium salt of claim 1, wherein the delivery agent is N-(5-chlorosalicyloyl)-8-aminocaprylic acid.
3. The disodium salt of claim 1, wherein the delivery agent is N-(10-[2-hydroxybenzoyl]amino)decanoic acid.
4. The disodium salt of claim 1, wherein the delivery agent is sodium N-(8-[2-hydroxybenzoyl]amino)caprylic acid.
5. An ethanol solvate of the disodium salt of claim 1.
6. The ethanol solvate of claim 5, wherein the delivery agent is N-(5-chlorosalicyloyl)-8-aminocaprylic acid.
7. The ethanol solvate of claim 5, wherein the delivery agent is N-(10-[2-hydroxybenzoyl]amino)decanoic acid.
8. The ethanol solvate of claim 5, wherein the delivery agent is sodium N-(8-[2-hydroxybenzoyl]amino)caprylic acid.
9. A monohydrate of the disodium salt of claim 1.
10. The monohydrate of claim 9, wherein the delivery agent is N-(5-chlorosalicyloyl)-8-aminocaprylic acid.
11. The monohydrate of claim 9, wherein the delivery agent is N-(10-[2-hydroxybenzoyl]amino)decanoic acid.
12. The monohydrate of claim 9, wherein the delivery agent is sodium N-(8-[2-hydroxybenzoyl]amino)caprylic acid.
13. A composition comprising at least about 50% by weight of the disodium salt of claim 1, based upon 100% total weight of delivery agent and salts thereof in the composition.
14. The composition of claim 13, wherein the composition comprises at least about 90% by weight of the disodium salt, based upon 100% total weight of delivery agent and salts thereof in the composition.
15. A composition comprising:
(a) the disodium salt of claim 1, ethanol solvate thereof, or monohydrate thereof; and (b) at least one active agent.
16. The composition of claim 15, wherein the composition comprises at least about 50% by weight of the disodium salt, based upon 100% total weight of delivery agent and salts thereof in the composition.
17. The composition of claim 16, wherein the composition comprises at least about 90% by weight of the disodium salt, based upon 100% total weight of delivery agent and salts thereof in the composition.
18. The composition of claim 15, wherein the composition comprises at least about 90% by weight of the monohydrate, based upon 100% total weight of hydrate of the disodium salt of the delivery agent in the composition.
19. The composition of claim 15, wherein the active agent is selected from the group consisting of growth hormones; human growth hormones; recombinant human growth hormones; bovine growth hormones; porcine growth hormones; growth hormone-releasing hormones; interferons; .alpha.-interferon; .beta.-interferon;
.gamma.-interferon; interleukin-1;
interleukin-2; insulin; porcine insulin; bovine insulin; human insulin; human recombinant insulin; insulin-like growth factor; IGF-1; heparin; unfractionated heparin;
heparinoids;
dermatans; chondroitins; low molecular weight heparin; very low molecular weight heparin;
ultra low molecular weight heparin; calcitonin; salmon calcitonin; eel calcitonin; human calcitonin; porcine calcitonin; erythropoietin; atrial naturetic factor;
antigens; monoclonal antibodies; somatostatin; protease inhibitors; adrenocorticotropin;
gonadotropin releasing hormone; oxytocin; leutinizing-hormone-releasing-hormone; follicle stimulating hormone;
glucocerebrosidase; thrombopoietin; filgrastim; prostaglandins; cyclosporin;
vasopressin;
cromolyn sodium; sodium chromoglycate; disodium chromoglycate; vancomycin;
desferrioxamine; parathyroid hormone; fragments of parathyroid hormone;
antimicrobials;
anti-fungal agents; vitamins; analogs, fragments, mimetics and polyethylene glycol-modified derivatives of these compounds; and any combination thereof.
20. The composition of claim 15, wherein the active agent is selected from the group consisting of heparin and calcitonin.
21. A dosage unit form comprising:

(a) the composition of claim 15; and (b) (i) an excipient, (ii) a diluent, (iii) a disintegrant, (iv) a lubricant, (v) a plasticizer, (vi) a colorant, (vii) a dosing vehicle, or (viii) any combination thereof.
22. A solid dosage unit form comprising a lyophilized mixture comprising (a) the disodium salt of claim 1; and (b) at least one active agent.
23. A method for administering heparin to an animal in need thereof, the method comprising administering orally to the animal the composition of claim 15.
24. A method for preparing a composition comprising mixing:
(a) at least one member selected from the group consisting of the disodium salt of claim 1, ethanol solvates thereof, and monohydrates thereof;
(b) at least one active agent; and (c) optionally, a dosing vehicle.
25. A method for preparing an anhydrous disodium salt of a delivery agent comprising drying the ethanol solvate of the disodium salt of the delivery agent, wherein the delivery agent has the formula wherein R1, R2, R3, and R4 are independently hydrogen, -OH, -NR6R', halogen, C1-C4 alkyl, or C1-C4 alkoxy;
R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene); and R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.
26. A method of preparing an ethanol solvate of the disodium salt of a delivery agent comprising:
(a) dissolving the delivery agent in ethanol to form a delivery agent/ethanol solution; and (b) reacting the delivery agent/ethanol solution with a molar excess of a sodium containing salt to form the ethanol solvate, wherein the delivery agent has the formula wherein R1, R2, R3, and R4 are independently hydrogen, -OH, -NR6R7, halogen, C1-C4 alkyl, or C1-C4 alkoxy;

R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene); and R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.
27. The method of claim 26, further comprising the step of:
(c) recovering the ethanol solvate from the solution containing the ethanol solvate formed in step (b).
28. A method of preparing a monohydrate of a disodium salt of a delivery agent, the method comprising (a) obtaining an ethanol solvate of the disodium salt of the delivery agent;
(b) drying the solvate to form an anhydrous disodium salt; and (c) hydrating the anhydrous disodium salt to form the hydrate, wherein the delivery agent has the formula wherein R1, R2, R3, and R4 are independently hydrogen, -OH, -NR6R7, halogen, C1-C4 alkyl, or C1-C4 alkoxy;
R5 is a substitued or unsubstituted C2-C16 alkylene, substituted or unsubstituted C2-C16 alkenylene, substituted or unsubstituted C1-C12 alkyl(arylene), or substituted or unsubstituted aryl(C1-C12 alkylene); and R6 and R7 are independently hydrogen, oxygen, or C1-C4 alkyl.
CA2369591A 1999-04-05 2000-04-05 Disodium salts, monohydrate, and ethanol solvates Expired - Lifetime CA2369591C (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CA002487952A CA2487952A1 (en) 1999-04-05 2000-04-05 Disodium salts, monohydrates, and ethanol solvates for delivering active agents

Applications Claiming Priority (9)

Application Number Priority Date Filing Date Title
US12775499P 1999-04-05 1999-04-05
US60/127,754 1999-04-05
US18614300P 2000-03-01 2000-03-01
US18614200P 2000-03-01 2000-03-01
US60/186,142 2000-03-01
US60/186,143 2000-03-01
US19128600P 2000-03-21 2000-03-21
US60/191,286 2000-03-21
PCT/US2000/009390 WO2000059863A1 (en) 1999-04-05 2000-04-05 Disodium salts, monohydrates, and ethanol solvates

Related Child Applications (1)

Application Number Title Priority Date Filing Date
CA002487952A Division CA2487952A1 (en) 1999-04-05 2000-04-05 Disodium salts, monohydrates, and ethanol solvates for delivering active agents

Publications (2)

Publication Number Publication Date
CA2369591A1 true CA2369591A1 (en) 2000-10-12
CA2369591C CA2369591C (en) 2011-06-14

Family

ID=27494697

Family Applications (1)

Application Number Title Priority Date Filing Date
CA2369591A Expired - Lifetime CA2369591C (en) 1999-04-05 2000-04-05 Disodium salts, monohydrate, and ethanol solvates

Country Status (12)

Country Link
US (6) US20020065255A1 (en)
EP (1) EP1175390B1 (en)
JP (2) JP4588221B2 (en)
AT (1) ATE288415T1 (en)
AU (1) AU4216700A (en)
CA (1) CA2369591C (en)
DE (1) DE60017888T2 (en)
ES (1) ES2235854T3 (en)
HK (1) HK1045680A1 (en)
IL (4) IL145546A0 (en)
NZ (1) NZ534409A (en)
WO (1) WO2000059863A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8513300B2 (en) 2001-11-29 2013-08-20 Emisphere Technologies, Inc. Formulations for oral administration of cromolyn sodium

Families Citing this family (100)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6461643B2 (en) 1993-04-22 2002-10-08 Emisphere Technologies, Inc. Oral drug delivery compositions and methods
SI9720025A (en) 1996-03-29 1999-08-31 Emishphere Technologies, Inc. Compounds and compositions for delivering active agents
US6440929B1 (en) 1998-07-27 2002-08-27 Emisphere Technologies, Inc. Pulmonary delivery of active agents
WO2000006184A1 (en) 1998-07-27 2000-02-10 Emisphere Technologies, Inc. Pulmonary delivery of active agents
CA2369591C (en) * 1999-04-05 2011-06-14 Emisphere Technologies, Inc. Disodium salts, monohydrate, and ethanol solvates
US7151191B2 (en) * 2000-01-13 2006-12-19 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US7049283B2 (en) * 2000-12-06 2006-05-23 Novartis Ag Pharmaceutical compositions for the oral delivery of pharmacologically active agents
NZ529439A (en) 2001-06-01 2005-11-25 Novartis Ag Method for orally administering parathyroid hormone (PTH)
PT1420827E (en) * 2001-08-17 2009-12-15 Novartis Ag 5-cnac as oral delivery agent for parathyroid hormone fragments
CA2471144C (en) 2002-01-09 2011-06-07 Emisphere Technologies, Inc. Polymorphs of sodium 4-[(4-chloro-2-hydroxybenzoyl)amino]butanoate
RU2332229C2 (en) 2002-02-20 2008-08-27 Эмисфире Текнолоджис Инк. Method of glp-1 molecules introduction
US20050054557A1 (en) * 2002-05-09 2005-03-10 Goldberg Michael M. Compositions for delivering parathyroid hormone and calcitonin
TW200403052A (en) * 2002-07-17 2004-03-01 Novartis Ag Use of organic compounds
AR040737A1 (en) * 2002-08-01 2005-04-20 Novartis Ag ORAL CALCITONINE ADMINISTRATION
MXPA06000446A (en) 2003-07-11 2006-04-07 Novartis Ag Orally dosed pharmaceutical compositions comprising a delivery agent in micronized form.
NZ544645A (en) 2003-07-23 2009-04-30 Novartis Ag Use of calcitonin in osteoarthritis
US7318925B2 (en) * 2003-08-08 2008-01-15 Amgen Fremont, Inc. Methods of use for antibodies against parathyroid hormone
CN100398536C (en) 2003-08-20 2008-07-02 爱密斯菲尔科技公司 Compounds, methods and formulations for the oral delivery of a glucagon like peptide (glp)-1 compound or an melanocortin 4 receptor (mc4) agonist peptide
ES2278346T3 (en) 2003-08-20 2007-08-01 Eli Lilly And Company COMPOUNDS, PROCEDURES AND FORMULATIONS FOR ORAL SUPPLY OF A PEPTIDE COMPOUND (LPG) -1 OF THE TYPE OF GLUCAGON OR AN AGONISTIC PEPTIDE (LPG) -4 OF THE RECEIVER 4 OF MELACORTINE (MC4).
US20060286129A1 (en) 2003-12-19 2006-12-21 Emisphere Technologies, Inc. Oral GLP-1 formulations
WO2005115406A2 (en) 2004-04-16 2005-12-08 Emisphere Technologies, Inc. 8-(2-hydroxyphenoxy)octyldiethanolamine and salts thereof for delivery of active agents
KR20070008720A (en) 2004-05-06 2007-01-17 에미스페어 테크놀로지스, 인코포레이티드 Solid dosage form of wetted heparin
EP1773351B1 (en) 2004-05-06 2019-04-24 Emisphere Technologies, Inc. Crystalline polymorphic forms of monosodium n-[8-(2-hydroxybenzoyl)amino]caprylate
KR101193228B1 (en) * 2004-05-06 2012-10-22 에미스페어 테크놀로지스, 인코포레이티드 Crystalline polymorphine forms of monosodium n-[8-2-hydroxybenzoylamino]caprylate
CN1953753B (en) * 2004-05-06 2011-02-09 爱密斯菲尔科技公司 Crystalline polymorphic forms of monosodium N-[8-(2-hydroxybenzoyl)amino]caprylate
ES2586423T3 (en) 2004-05-14 2016-10-14 Emisphere Technologies, Inc. Aryl ketone compounds and compositions for administering active ingredients
RU2403237C2 (en) * 2004-05-14 2010-11-10 Эмисфире Текнолоджис, Инк. Compositions and mixtures for delivery of active agents
CA2565188C (en) 2004-05-14 2014-03-04 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US20080132527A1 (en) 2004-05-19 2008-06-05 Emisphere Technologies, Inc. Compositions For Delivering Acyclovir
CN1968704B (en) * 2004-05-19 2010-12-08 爱密斯菲尔科技公司 Topical cromolyn formulations
US9399054B2 (en) * 2004-07-12 2016-07-26 Emisphere Technologies, Inc. Compositions for delivering peptide YY and PYY agonists
EP2248531A1 (en) 2004-08-03 2010-11-10 Emisphere Technologies, Inc. Antidiabetic oral insulin-biguanide combination
GB0422644D0 (en) * 2004-10-12 2004-11-10 Novartis Ag Organic compounds
GB0427600D0 (en) * 2004-12-16 2005-01-19 Novartis Ag Organic compounds
GB0427603D0 (en) 2004-12-16 2005-01-19 Novartis Ag Organic compounds
WO2006072070A2 (en) 2004-12-29 2006-07-06 Emisphere Technologies, Inc. Pharmaceutical formulations of gallium salts
US8110547B2 (en) 2005-01-12 2012-02-07 Emisphere Technologies, Inc. Compositions for buccal delivery of parathyroid hormone
WO2007005995A2 (en) * 2005-07-05 2007-01-11 Emisphere Technologies, Inc. Compositions for buccal delivery of human growth hormone
US20070049557A1 (en) 2005-08-24 2007-03-01 Hashim Ahmed Solid pharmaceutical dosage forms comprising bisphosphonates and modified amino acid carriers
BRPI0616558B1 (en) * 2005-09-19 2021-09-08 Emisphere Technologies, Inc FORM I N-(5-CHLOROSSALICYLOYL)-5-AMINOCAPROIC ACID DISODIUM SALT, N-(5-SALICYLOYL)-8-AMINOCAPRYLIC ACID DISODIUM MONHYDRATE N-(5- CHLOROSSALICYLOIL)-5-AMINOCAPROIC, N-(5-SALICIOLOIL)-8-AMINOCAPROIC ACID DISODIUM ETHANOL Solvate, N-(5-CHLOROSALICYLOIL)-5-AMINOCAPROIC ACID DISODIUM SALT FORM III N-(5-SALICILOYL)-8-AMINOCAPRYLIC ACID DISODIUM, N-(5-SALICILOYL)-8-AMINOCAPRYLIC ACID DISODIUM CRYSTALLINE MONHYDRATE (5-SALICILOIL)-8-AMINOCAPRIL, PROCESS FOR PREPARING A MONOETHANOL SOLVATE FROM N-(5-SALICILOIL)-8-(...)
GB0522566D0 (en) 2005-11-04 2005-12-14 Novartis Ag Organic compounds
KR101432313B1 (en) 2005-11-17 2014-08-20 노파르티스 아게 Pharmaceutical composition
US20070232537A1 (en) * 2005-12-19 2007-10-04 Nastech Pharmaceutical Company Inc. Intranasal pyy formulations with improved transmucosal pharmacokinetics
WO2007121318A2 (en) 2006-04-12 2007-10-25 Emisphere Technologies, Inc. Formulations for delivering insulin
WO2007133944A2 (en) 2006-05-09 2007-11-22 Emisphere Technologies, Inc. Topical administration of acyclovir
WO2008003050A2 (en) * 2006-06-28 2008-01-03 Emisphere Technologies, Inc. Gallium nitrate formulations
EP2049137A4 (en) 2006-08-08 2013-05-01 Univ California Salicylanilides enhance oral delivery of therapeutic peptides
CA2662853C (en) 2006-08-31 2016-07-26 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
ES2426485T3 (en) 2006-08-31 2013-10-23 Novartis Ag Pharmaceutical compositions comprising hGH for oral administration
CA2662080C (en) * 2006-09-07 2012-07-17 F. Hoffmann-La Roche Ag A process for the manufacture of snac (salcaprozate sodium)
DE602008006700D1 (en) * 2007-03-02 2011-06-16 Novartis Ag
CA2681158C (en) 2007-03-13 2018-09-18 Nutrition 21, Inc. Methods and compositions for the sustained release of chromium
WO2009002867A2 (en) 2007-06-26 2008-12-31 Nutrition 21, Inc. Multiple unit dosage form having a therapeutic agents in combination with a nutritional supplement
EP2185136A2 (en) 2007-08-09 2010-05-19 Novartis Ag Oral calcitonin compositions and applications thereof
ES2443817T3 (en) * 2007-11-02 2014-02-20 Emisphere Technologies, Inc. Method to treat vitamin B12 deficiency
EP2331522B1 (en) * 2008-08-01 2013-09-18 Purdue Pharma LP Tetrahydropyridinyl and dihydropyrrolyl compounds and the use thereof
ES2626327T3 (en) 2009-02-06 2017-07-24 The Regents Of The University Of California Calcium binding agents that induce hair growth and / or nail growth
BRPI1009392A2 (en) 2009-03-12 2016-03-08 Nordic Bioscience As "pharmaceutical formulation, and use of a pharmaceutically effective amount of a pharmaceutical formulation."
EP2461803B1 (en) * 2009-08-03 2018-10-17 Emisphere Technologies, Inc. Fast-acting naproxen composition with reduced gastrointestinal effects
EP3028709B1 (en) * 2010-02-24 2019-08-28 Emisphere Technologies, Inc Oral b12 therapy
KR101811376B1 (en) * 2010-06-09 2017-12-22 에미스페어 테크놀로지스, 인코포레이티드 Oral iron deficiency therapy
JP6250394B2 (en) 2010-08-19 2017-12-20 バック・インスティテュート・フォー・リサーチ・オン・エイジング Method for treating mild cognitive impairment (MCI) and related disorders
ES2678145T3 (en) 2010-08-24 2018-08-09 Abbott Laboratories Specific antibodies against HIV core protein and their uses
TW201309346A (en) * 2011-01-05 2013-03-01 Hospira Inc Spray drying vancomycin
CA2828572C (en) 2011-03-01 2021-02-23 Jds Therapeutics, Llc Compositions of insulin and chromium for the treatment and prevention of diabetes, hypoglycemia and related disorders
DK2773365T3 (en) 2011-11-02 2016-08-29 Keybioscience Ag Peptide FOR THE TREATMENT OF DISEASES AND DISORDERS
RU2616511C2 (en) 2011-11-02 2017-04-17 Кибайосайнс Аг Peptide analogs for treatment of diseases and disorders
US9533022B2 (en) * 2011-11-02 2017-01-03 KeyBioscience A/S Peptide analogs for treating diseases and disorders
JP2015527351A (en) 2012-08-16 2015-09-17 オハイオ・ステイト・イノベーション・ファウンデーション STAT3 inhibitor and its anticancer use
CA2922849A1 (en) 2012-08-31 2014-03-06 Ixchel Pharma, Llc Agents useful for treating obesity, diabetes and related disorders
DK2897620T3 (en) 2012-09-21 2020-08-17 Intensity Therapeutics Inc CANCER TREATMENT PROCEDURE
EP4335505A2 (en) 2012-11-30 2024-03-13 The Regents of The University of California Anticonvulsant activity of steroids
CN104043104B (en) 2013-03-15 2018-07-10 浙江创新生物有限公司 The spray dried powder and its industrialized process for preparing of hydrochloric vancomycin
EP3536699A1 (en) 2013-07-12 2019-09-11 F. Hoffmann-La Roche AG Elucidation of ion exchange chromatography input optimization
AU2014350328B2 (en) 2013-11-14 2018-04-05 Keybioscience Ag Calcitonin mimetics for treating diseases and disorders
EP3006045B3 (en) 2014-10-07 2021-03-17 Cyprumed GmbH Pharmaceutical formulations for the oral delivery of peptide or protein drugs
WO2016061144A1 (en) 2014-10-14 2016-04-21 The Regents Of The University Of California Use of cdk9 and brd4 inhibitors to inhibit inflammation
GB201500263D0 (en) 2015-01-08 2015-02-25 Keybioscience Ag Calcitonin analogues for treating diseases and disorders
CA2975710C (en) 2015-02-09 2023-08-08 Entera Bio Ltd. Treatment of osteoporosis
CA2997343A1 (en) 2015-10-07 2017-04-13 Cyprumed Gmbh Pharmaceutical formulations for the oral delivery of peptide drugs
MX2018009748A (en) 2016-02-11 2019-02-07 Nutrition 21 Llc Chromium containing compositions for improving health and fitness.
KR102393596B1 (en) 2016-04-22 2022-05-04 리셉터 홀딩스, 인크. Fast-acting plant-based medicinal compounds and nutritional supplements
WO2018065634A1 (en) 2016-10-07 2018-04-12 Cyprumed Gmbh Pharmaceutical compositions for the nasal delivery of peptide or protein drugs
EA201892396A1 (en) 2016-12-02 2019-04-30 Ресептор Лайф Сайенсиз, Инк. QUICKLY PRODUCTIVE PLANT MEDICINES AND BIOLOGICALLY ACTIVE ADDITIVES
MX2019008056A (en) 2017-01-05 2019-11-21 Univ California Pac1 receptor agonists (maxcaps) and uses thereof.
GB201704429D0 (en) 2017-03-21 2017-05-03 Keybioscience Ag Calcitonin mimetics for treating diseases and disorders
GB201707955D0 (en) 2017-05-18 2017-07-05 Keybioscience Ag Dual amylin and calcitonin receptor agonists for treating diseases and disorders
EA202090890A1 (en) * 2017-10-05 2020-09-03 Ресептор Холдингз, Инк. COMPOSITION OF PLANT AND SYNTHETIC CANNABINOID OF RAPID-ON-START AND LONGER ACTION
AU2018345812A1 (en) * 2017-10-05 2020-05-14 Spoke Sciences, Inc. Herbal compositions with improved bioavailability
WO2019083904A1 (en) 2017-10-23 2019-05-02 Chan Zuckerberg Biohub, Inc. Measurement of afucosylated igg fc glycans and related treatment methods
US20210087250A1 (en) 2018-04-06 2021-03-25 Cyprumed Gmbh Pharmaceutical compositions for the transmucosal delivery of therapeutic peptides and proteins
GB201813678D0 (en) 2018-08-22 2018-10-03 Keybioscience Ag Acylated calcitonin mimetics
GB201813677D0 (en) 2018-08-22 2018-10-03 Keybioscience Ag Calcitonin mimetics for treating diseases and disorders
CN111057165A (en) * 2020-01-13 2020-04-24 苏州健飞肠衣有限公司 Preparation method of high-purity heparin sodium
CN116419750A (en) 2020-09-07 2023-07-11 西普鲁梅有限公司 Improved pharmaceutical formulations of GLP-1 receptor agonists
US11667614B2 (en) 2021-04-16 2023-06-06 Navinta III Inc. Process for the preparation of highly pure Salcaprozic Acid and pharmaceutically acceptable salts thereof
EP4323330A1 (en) 2021-04-16 2024-02-21 Navinta III Inc Process for the preparation of highly pure salcaprozic acid and pharmaceutically acceptable salts thereof
CR20230471A (en) 2021-04-22 2023-11-01 Civi Biopharma Inc Oral delivery of oligonucleotides
CA3223247A1 (en) 2021-07-16 2023-01-19 Thomas Kvistgaard Vilhelmsen Sodium n-(8-(2- hydroxybenzoyl)amino)caprylate polymorphic form a
WO2023166179A1 (en) 2022-03-03 2023-09-07 Cyprumed Gmbh Improved oral pharmaceutical formulations of therapeutic peptides and proteins

Family Cites Families (84)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES369853A1 (en) * 1969-07-24 1971-07-16 Bama S A Lab Procedure for the obtaining of derivatives of the epsilon-amino-caproico acid. (Machine-translation by Google Translate, not legally binding)
US3795739A (en) 1972-02-14 1974-03-05 Hoffmann La Roche Treatment of parkinson disease
US3939253A (en) 1973-11-02 1976-02-17 Interx Research Corporation Novel, transient pro-drug forms of l-dopa useful in the treatment of parkinson's disease
US4061466A (en) 1974-10-16 1977-12-06 Ingvar Gosta Holger Sjoholm Biologically active composition and the use thereof
DE2500157C2 (en) 1975-01-03 1983-09-15 Hoechst Ag, 6230 Frankfurt N-acyl-4- (2-aminoethyl) benzoic acids, their salts and esters, process for their preparation and their use
US4035507A (en) 1975-04-17 1977-07-12 Interx Research Corporation Novel, transient pro-drug forms of L-DOPA to treat Parkinson's disease
DE2517229A1 (en) 1975-04-18 1976-10-28 Boehringer Mannheim Gmbh PHENYLALKYLCARBONIC ACID DERIVATIVES AND PROCESS FOR THEIR PRODUCTION
DE2532420A1 (en) 1975-07-19 1977-02-03 Boehringer Mannheim Gmbh PHENYL ACID DERIVATIVES AND THE PROCESS FOR THEIR PRODUCTION
CA1077842A (en) 1975-10-09 1980-05-20 Minnesota Mining And Manufacturing Company Albumin medicament carrier system
FR2374910A1 (en) 1976-10-23 1978-07-21 Choay Sa PREPARATION BASED ON HEPARIN, INCLUDING LIPOSOMES, PROCESS FOR OBTAINING IT AND MEDICINAL PRODUCTS CONTAINING SUCH PREPARATIONS
NZ196349A (en) 1980-03-07 1984-08-24 Interx Research Corp Enhancement of absorption rate of orally administered polar bioactive agents
US4442090A (en) 1980-11-09 1984-04-10 Kyoto Yakuhin Kogyo Kabushiki Kaisha Absorption-promoting compounds, compositions thereof with pharmaceuticals and/or bases for rectal administration and method of use
US4900730A (en) 1981-01-14 1990-02-13 Toyo Jozo Co., Ltd. Preparation which promotes the absorption of peptides
GB2092136B (en) 1981-01-17 1985-06-05 Mitsui Toatsu Chemicals Production of n-substituted amide compounds
JPS58140026A (en) 1982-01-14 1983-08-19 Toyo Jozo Co Ltd Pharmaceutical having improved absorbability
FR2509175B1 (en) 1981-03-06 1987-01-16 Toyo Jozo Kk THERAPEUTIC PREPARATION HAVING EXCELLENT ABSORPTION PROPERTIES
US4499299A (en) 1981-12-30 1985-02-12 Ici Americas Inc. Pharmaceutically active phenylcarboxylic acid derivatives
US4654327A (en) 1982-04-21 1987-03-31 Research Corp. Quaternary ammonium complexes of heparin
US4393192A (en) 1982-12-21 1983-07-12 The Standard Oil Company Crystalline copolymers prepared from N,N'-terephthaloyldi-beta-alanine and a glycol
DE3331009A1 (en) 1983-08-27 1985-03-14 Basf Ag, 6700 Ludwigshafen METHOD FOR INCREASING THE ENTERAL RESORBABILITY OF HEPARIN OR. HEPARINOIDS AND THE SO AVAILABLE HEPARIN OR HEPARINOID PREPARATION
US4692433A (en) 1983-10-12 1987-09-08 The Regents Of The University Of California Method and composition for regulating serum calcium levels of mammals
US4898729A (en) * 1983-12-09 1990-02-06 Euroceltique, S.A. Treatment of hypertension, compounds and compositions for antihypertension and diuresis
US4757066A (en) 1984-10-15 1988-07-12 Sankyo Company Limited Composition containing a penem or carbapenem antibiotic and the use of the same
CA1234561A (en) 1985-06-26 1988-03-29 Kenneth M. White Profiled body roller-reamer stabilizer
IL77186A0 (en) 1985-11-29 1986-04-29 Touitou Elka Pharmaceutical insulin composition
US4689182A (en) 1985-12-20 1987-08-25 Warner-Lambert Company Benzoic acid and benzoic acid ester derivatives having anti-inflammatory and analgesic activity
LU86258A1 (en) 1986-01-21 1987-09-03 Rech Dermatologiques C I R D S BENZAMIDO AROMATIC COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USE IN HUMAN OR VETERINARY MEDICINE AND IN COSMETICS
USRE35862E (en) 1986-08-18 1998-07-28 Emisphere Technologies, Inc. Delivery systems for pharmacological agents encapsulated with proteinoids
GB8705477D0 (en) 1987-03-09 1987-04-15 Carlton Med Prod Drug delivery systems
JPH0725725B2 (en) 1987-07-23 1995-03-22 保土谷化学工業株式会社 Benzamide derivative
FR2636238B1 (en) 1988-09-14 1994-01-21 Morelle Jean NEW ANTISUDORAL COMPOSITIONS
GB8823731D0 (en) 1988-10-10 1988-11-16 Smith Kline French Lab Biologically active compounds
FR2639395B1 (en) 1988-11-18 1991-02-15 Rockwell Cim COUPLING DEVICE BETWEEN A WINDOW AND AN OSCILLATING ARM WINDOW MECHANISM IN A MOTOR VEHICLE
JPH02239980A (en) 1989-03-15 1990-09-21 Fuji Photo Film Co Ltd Thermal recording material
GB9007052D0 (en) 1990-03-29 1990-05-30 Skua Investments Ltd Pharmaceutical formulations
US6099856A (en) 1992-06-15 2000-08-08 Emisphere Technologies, Inc. Active agent transport systems
US5629020A (en) * 1994-04-22 1997-05-13 Emisphere Technologies, Inc. Modified amino acids for drug delivery
US5447728A (en) 1992-06-15 1995-09-05 Emisphere Technologies, Inc. Desferrioxamine oral delivery system
US5451410A (en) 1993-04-22 1995-09-19 Emisphere Technologies, Inc. Modified amino acids for encapsulating active agents
US5714167A (en) 1992-06-15 1998-02-03 Emisphere Technologies, Inc. Active agent transport systems
US6221367B1 (en) 1992-06-15 2001-04-24 Emisphere Technologies, Inc. Active agent transport systems
US5541155A (en) 1994-04-22 1996-07-30 Emisphere Technologies, Inc. Acids and acid salts and their use in delivery systems
CA2070061C (en) 1991-06-07 2004-02-10 Shigeyuki Takama Physiologically active polypeptide-containing pharmaceutical composition
US5352461A (en) 1992-03-11 1994-10-04 Pharmaceutical Discovery Corporation Self assembling diketopiperazine drug delivery system
US5811127A (en) 1992-06-15 1998-09-22 Emisphere Technologies, Inc. Desferrioxamine oral delivery system
US5792451A (en) 1994-03-02 1998-08-11 Emisphere Technologies, Inc. Oral drug delivery compositions and methods
HU211995B (en) 1992-06-30 1996-01-29 Gyogyszerkutato Intezet Process to prepare novel benzoyl amino acid derivs. and pharmaceutical compns. contg.them
US5958457A (en) 1993-04-22 1999-09-28 Emisphere Technologies, Inc. Compositions for the delivery of antigens
US5643957A (en) 1993-04-22 1997-07-01 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
EP1025840B1 (en) 1993-04-22 2005-06-29 Emisphere Technologies, Inc. Oral drug compositions
US5709861A (en) 1993-04-22 1998-01-20 Emisphere Technologies, Inc. Compositions for the delivery of antigens
BR9604880A (en) 1995-03-31 1998-05-19 Emisphere Tech Inc Compound composition dosage unit form methods for administering a biologically active agent for preparing a composition for administering an active agent and for preparing a compound and pharmacological composition
US5866536A (en) * 1995-03-31 1999-02-02 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5989539A (en) 1995-03-31 1999-11-23 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5650386A (en) * 1995-03-31 1997-07-22 Emisphere Technologies, Inc. Compositions for oral delivery of active agents
US6090958A (en) 1995-03-31 2000-07-18 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US6001347A (en) 1995-03-31 1999-12-14 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5965121A (en) 1995-03-31 1999-10-12 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5750147A (en) 1995-06-07 1998-05-12 Emisphere Technologies, Inc. Method of solubilizing and encapsulating itraconazole
US6051258A (en) 1995-06-07 2000-04-18 Emisphere Technologies, Inc. Proteinoid emulsions and methods for preparation and use thereof
SI9720025A (en) 1996-03-29 1999-08-31 Emishphere Technologies, Inc. Compounds and compositions for delivering active agents
GB2314189B (en) 1996-06-14 2000-08-09 Mars Inc Coin handling apparatus
US5990166A (en) 1997-02-07 1999-11-23 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5776888A (en) 1997-02-07 1998-07-07 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5804688A (en) 1997-02-07 1998-09-08 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5879681A (en) 1997-02-07 1999-03-09 Emisphere Technolgies Inc. Compounds and compositions for delivering active agents
US5876710A (en) 1997-02-07 1999-03-02 Emisphere Technologies Inc. Compounds and compositions for delivering active agents
US6051561A (en) 1997-02-07 2000-04-18 Emisphere Technologies Inc. Compounds and compositions for delivering active agents
US6313088B1 (en) 1997-02-07 2001-11-06 Emisphere Technologies, Inc. 8-[(2-hydroxy-4-methoxy benzoyl) amino]-octanoic acid compositions for delivering active agents
US5773647A (en) * 1997-02-07 1998-06-30 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5939381A (en) 1997-02-07 1999-08-17 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
CA2319672C (en) * 1997-02-07 2011-01-04 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US6060513A (en) 1997-02-07 2000-05-09 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
US5863944A (en) * 1997-04-30 1999-01-26 Emisphere Technologies, Inc. Compounds and compositions for delivering active agents
AR017426A1 (en) * 1997-12-08 2001-09-05 Smithkline Beecham Corp ACID MONOARGININYL SALT (E) -3- [1-N-BUTIL-5- [2- (2-CARBOXIFENIL) METOXI-4-CHLOROPHENYL] -1H-PIRAZOL-4-IL] -2 - [(5- METOXI-2,3-DIHIDROBENZOFURAN-6-IL) METHYL] -PROP-2-ENOICO, PHARMACEUTICAL COMPOSITION CONTAINING IT, ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT AND PROCEDURE FOR PREPARATION
WO2000006184A1 (en) 1998-07-27 2000-02-10 Emisphere Technologies, Inc. Pulmonary delivery of active agents
JP4430235B2 (en) 1998-08-07 2010-03-10 エミスフェアー・テクノロジーズ・インク Compounds and compositions for delivery of active agents
US6066015A (en) 1998-08-17 2000-05-23 Brown; James D. Method and system for anchoring a buoy via a screw-type anchor
WO2000048589A1 (en) 1999-02-22 2000-08-24 Emisphere Holdings, Inc. Solid oral dosage form containing heparin or a heparinoid in combination with a carrier
CA2369591C (en) 1999-04-05 2011-06-14 Emisphere Technologies, Inc. Disodium salts, monohydrate, and ethanol solvates
US7049283B2 (en) * 2000-12-06 2006-05-23 Novartis Ag Pharmaceutical compositions for the oral delivery of pharmacologically active agents
US20070048725A1 (en) 2005-08-25 2007-03-01 Arrington Ben O'mar Machine perfusion of tissue grafts for transplantation
CA2620616C (en) 2005-08-25 2016-06-14 Arizona Board Of Regents On Behalf Of The University Of Arizona Stem cell fusion model of carcinogenesis
WO2011048589A2 (en) 2009-10-23 2011-04-28 Ben Gurion University Of The Negev Research And Development Authority Ion exchangers and methods of use thereof

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8513300B2 (en) 2001-11-29 2013-08-20 Emisphere Technologies, Inc. Formulations for oral administration of cromolyn sodium

Also Published As

Publication number Publication date
JP4642435B2 (en) 2011-03-02
AU4216700A (en) 2000-10-23
ES2235854T3 (en) 2005-07-16
US20020065255A1 (en) 2002-05-30
JP2005068161A (en) 2005-03-17
US20110251125A1 (en) 2011-10-13
US7384982B2 (en) 2008-06-10
US20080269134A1 (en) 2008-10-30
IL145546A0 (en) 2002-06-30
WO2000059863A1 (en) 2000-10-12
US20040106825A1 (en) 2004-06-03
IL166158A (en) 2010-12-30
EP1175390A4 (en) 2002-09-04
US20120264834A1 (en) 2012-10-18
DE60017888D1 (en) 2005-03-10
EP1175390A1 (en) 2002-01-30
US8658695B2 (en) 2014-02-25
US8003697B2 (en) 2011-08-23
IL180118A0 (en) 2007-06-03
US7659311B2 (en) 2010-02-09
IL166158A0 (en) 2006-01-15
CA2369591C (en) 2011-06-14
NZ534409A (en) 2006-03-31
IL180118A (en) 2010-12-30
IL145546A (en) 2007-10-31
US8207227B2 (en) 2012-06-26
EP1175390B1 (en) 2005-02-02
DE60017888T2 (en) 2006-01-19
US20100099621A1 (en) 2010-04-22
JP4588221B2 (en) 2010-11-24
HK1045680A1 (en) 2002-12-06
JP2002541132A (en) 2002-12-03
ATE288415T1 (en) 2005-02-15

Similar Documents

Publication Publication Date Title
CA2369591A1 (en) Disodium salts, monohydrate, and ethanol solvates
US6646162B2 (en) Compounds and compositions for delivering active agents
AU2006200678B2 (en) Compounds and compositions for delivering active agents
CA2421575A1 (en) Cyanophenoxy carboxylic acid compounds and compositions for delivering active agents
JP2002541132A5 (en)
ES2267283T3 (en) COMPOUNDS AND COMPOSITIONS FOR THE ADMINISTRATION OF ACTIVE AGENTS.
US7049283B2 (en) Pharmaceutical compositions for the oral delivery of pharmacologically active agents
CA2388240A1 (en) Phenoxy carboxylic acid compounds and compositions for delivering active agents
CA2360220C (en) Oxadiazole compounds and compositions for delivering active agents
CA2465641A1 (en) Phenoxy amine compounds and compositions for delivering active agents
CA2338419A1 (en) Pulmonary delivery of active agents
RU2003102615A (en) COMPOSITIONS AND COMPOUNDS FOR THE DELIVERY OF ACTIVE AGENTS
AU2001273153A1 (en) Compounds and compositions for delivering active agents
AU2002234547A1 (en) Pharmaceutical compositions for the oral delivery of pharmacologically active agents
EP1322595A4 (en) (5-(2-hydroxy-4-chlorobenzoyl) aminovaleric acid and salts thereof and compositions containing the same for delivering active agents
US7417061B2 (en) Oxadiazole compounds and compositions for delivering active agents
AU2004201178A1 (en) Compounds and compositions for delivering active agents
EP1535625A1 (en) Composition containing n-(5-chlorosalicyloyl)-8-aminocaprylic acid and salmon calcitonin
AU2005202705B2 (en) Pharmaceutical compositions for the oral delivery of pharmacologically active agents
RU2002114698A (en) COMPOUNDS OF PHENOXICARBOXYLIC ACID AND COMPOSITIONS FOR DELIVERY OF ACTIVE SUBSTANCES

Legal Events

Date Code Title Description
EEER Examination request
MKEX Expiry

Effective date: 20200405