CA2094773A1 - 2,4-dioxoimidazolidine derivatives - Google Patents
2,4-dioxoimidazolidine derivativesInfo
- Publication number
- CA2094773A1 CA2094773A1 CA002094773A CA2094773A CA2094773A1 CA 2094773 A1 CA2094773 A1 CA 2094773A1 CA 002094773 A CA002094773 A CA 002094773A CA 2094773 A CA2094773 A CA 2094773A CA 2094773 A1 CA2094773 A1 CA 2094773A1
- Authority
- CA
- Canada
- Prior art keywords
- dioxoimidazolidine
- derivatives
- alkyl
- hydrogen
- integer
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/10—Tetrapeptides
- C07K5/1024—Tetrapeptides with the first amino acid being heterocyclic
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/72—Two oxygen atoms, e.g. hydantoin
- C07D233/76—Two oxygen atoms, e.g. hydantoin with substituted hydrocarbon radicals attached to the third ring carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/96—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
Abstract
The present invention relates to 2,4-dioxoimidazolidine derivatives of the general formula I
(see figure I) wherein R1 is, fox example,-(CH2)n-NH-X, where n is an integer from 1 to 6 and X is, for example, hydrogen or (C1-C6)-alkyl, R2 is hydrogen or (C1-C6)-alkyl, R3 is hydrogen or phenyl, R4 is, for example, COOR5, where R5 is (C1-C28)-alkyl and Y is, for example, -(CH2)m-CO- radical where m represents an integer from 1 to 4. The compounds of the invention are useful as inhibitors of platelet aggregation, metastasis of carcinoma cells and osteoclast binding to the bone surfaces.
(see figure I) wherein R1 is, fox example,-(CH2)n-NH-X, where n is an integer from 1 to 6 and X is, for example, hydrogen or (C1-C6)-alkyl, R2 is hydrogen or (C1-C6)-alkyl, R3 is hydrogen or phenyl, R4 is, for example, COOR5, where R5 is (C1-C28)-alkyl and Y is, for example, -(CH2)m-CO- radical where m represents an integer from 1 to 4. The compounds of the invention are useful as inhibitors of platelet aggregation, metastasis of carcinoma cells and osteoclast binding to the bone surfaces.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DEP4213634.2 | 1992-04-24 | ||
DE4213634A DE4213634A1 (en) | 1992-04-24 | 1992-04-24 | 2,4-dioxo-imidazolidin-derivatives |
Publications (2)
Publication Number | Publication Date |
---|---|
CA2094773A1 true CA2094773A1 (en) | 1993-10-25 |
CA2094773C CA2094773C (en) | 2003-11-04 |
Family
ID=6457462
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA002094773A Expired - Lifetime CA2094773C (en) | 1992-04-24 | 1993-04-23 | 2,4-dioxoimidazolidine derivatives |
Country Status (11)
Country | Link |
---|---|
US (1) | US5397796A (en) |
EP (1) | EP0566919B1 (en) |
JP (1) | JP3793242B2 (en) |
AT (1) | ATE236886T1 (en) |
AU (1) | AU665068B2 (en) |
CA (1) | CA2094773C (en) |
CZ (1) | CZ287885B6 (en) |
DE (2) | DE4213634A1 (en) |
ES (1) | ES2194842T3 (en) |
IL (1) | IL105511A (en) |
SK (1) | SK39293A3 (en) |
Cited By (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5494922A (en) * | 1993-06-28 | 1996-02-27 | Zeneca Limited | Allophanic acid derivatives |
US5556977A (en) * | 1993-03-29 | 1996-09-17 | Zeneca Limited | Heterocyclic derivatives |
US5563158A (en) * | 1993-12-28 | 1996-10-08 | The Dupont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
US5563141A (en) * | 1993-03-29 | 1996-10-08 | Zeneca Limited | Heterocyclic compounds |
US5576334A (en) * | 1993-06-28 | 1996-11-19 | Zeneca Limited | Acylurea derivatives |
US5612373A (en) * | 1993-06-28 | 1997-03-18 | Zeneca Limited | Certain diacyl hydrazine derivatives |
US5652242A (en) * | 1993-03-29 | 1997-07-29 | Zeneca Limited | Heterocyclic derivatives |
US5750754A (en) * | 1993-03-29 | 1998-05-12 | Zeneca Limited | Heterocyclic compounds |
US5753659A (en) * | 1993-03-29 | 1998-05-19 | Zeneca Limited | Heterocyclic compouds |
US5811441A (en) * | 1995-05-24 | 1998-09-22 | The Dupont Merck Pharmaceutical Company | Isoxazoline fibrinogen receptor antagonists |
US5849736A (en) * | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE4224414A1 (en) * | 1992-07-24 | 1994-01-27 | Cassella Ag | Phenylimidazolidine derivatives, their preparation and their use |
DE4228717A1 (en) * | 1992-08-28 | 1994-03-03 | Cassella Ag | Imidazolidine derivatives |
DE4308034A1 (en) * | 1993-03-13 | 1994-09-15 | Cassella Ag | New heterocycles, their preparation and their use |
DE4427979A1 (en) * | 1993-11-15 | 1996-02-15 | Cassella Ag | Substituted 5-ring heterocycles, their preparation and their use |
PT796855E (en) | 1996-03-20 | 2002-07-31 | Hoechst Ag | INHIBITION OF REABSORCAO IN BONES AND ANTAGONISTS OF VITRONECTIN |
DE19622489A1 (en) | 1996-06-05 | 1997-12-11 | Hoechst Ag | Salts of 3- (2- (4- (4- (aminoimino-methyl) -phenyl) -4-methyl-2,5-dioxo-imidazolidin-1-yl) -acetylamino) -3-phenyl-propionic acid- ethyl esters |
DE19629816A1 (en) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | New cycloalkyl derivatives as inhibitors of bone resorption and vitronectin receptor antagonists |
DE19629817A1 (en) * | 1996-07-24 | 1998-01-29 | Hoechst Ag | New imino derivatives as inhibitors of bone resorption and vitronectin receptor antagonists |
DE19647380A1 (en) * | 1996-11-15 | 1998-05-20 | Hoechst Ag | 5-ring heterocycles as inhibitors of leukocyte adhesion and VLA-4 antagonists |
DE19741235A1 (en) * | 1997-09-18 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | Novel imidazolidine derivatives, their preparation, their use and pharmaceutical compositions containing them |
DE19741873A1 (en) * | 1997-09-23 | 1999-03-25 | Hoechst Marion Roussel De Gmbh | New 5-ring heterocycles, their preparation, their use and pharmaceutical preparations containing them |
DE19751251A1 (en) * | 1997-11-19 | 1999-05-20 | Hoechst Marion Roussel De Gmbh | Substituted imidazolidine derivatives, their manufacture, their use and pharmaceutical preparations containing them |
DE19821483A1 (en) | 1998-05-14 | 1999-11-18 | Hoechst Marion Roussel De Gmbh | New imidazolidine derivatives useful as leukocyte adhesion and migration inhibitors and/or VLA-4 receptor antagonists for treating E.G. inflammatory and allergic disorders |
DE19922462A1 (en) | 1999-05-17 | 2000-11-23 | Aventis Pharma Gmbh | New phenylureidobenzyl-substituted spiro-imidazolidinedione derivatives, are inhibitors of leukocyte adhesion or migration or VLA-4 receptors, useful e.g. for treating inflammatory or allergic disease |
DE10111877A1 (en) | 2001-03-10 | 2002-09-12 | Aventis Pharma Gmbh | Novel imidazolidine derivatives, their preparation, their use and pharmaceutical compositions containing them |
DE10137595A1 (en) * | 2001-08-01 | 2003-02-13 | Aventis Pharma Gmbh | New 3-alkylaminoalkyl-imdazolidin-4-one derivatives, are VLA-4 receptor and leukocyte adhesion and/or migration inhibitors, useful e.g. for treating inflammatory, allergic, autoimmune or cardiovascular disease |
JP2007500213A (en) * | 2003-05-07 | 2007-01-11 | サイトキネティクス・インコーポレーテッド | Compounds, compositions and methods |
US20060039949A1 (en) * | 2004-08-20 | 2006-02-23 | Nycz Jeffrey H | Acetabular cup with controlled release of an osteoinductive formulation |
US20060045902A1 (en) * | 2004-09-01 | 2006-03-02 | Serbousek Jon C | Polymeric wrap for in vivo delivery of osteoinductive formulations |
US20060057184A1 (en) * | 2004-09-16 | 2006-03-16 | Nycz Jeffrey H | Process to treat avascular necrosis (AVN) with osteoinductive materials |
US8414907B2 (en) | 2005-04-28 | 2013-04-09 | Warsaw Orthopedic, Inc. | Coatings on medical implants to guide soft tissue healing |
US9119901B2 (en) * | 2005-04-28 | 2015-09-01 | Warsaw Orthopedic, Inc. | Surface treatments for promoting selective tissue attachment to medical impants |
US20070077267A1 (en) * | 2005-10-03 | 2007-04-05 | Sdgi Holdings, Inc. | Bioactive composite implants |
US20070179615A1 (en) * | 2006-01-31 | 2007-08-02 | Sdgi Holdings, Inc. | Intervertebral prosthetic disc |
US20070179618A1 (en) * | 2006-01-31 | 2007-08-02 | Sdgi Holdings, Inc. | Intervertebral prosthetic disc |
US20070280986A1 (en) * | 2006-06-01 | 2007-12-06 | Carlos Gil | Intra-operative coating of implants |
US8133553B2 (en) | 2007-06-18 | 2012-03-13 | Zimmer, Inc. | Process for forming a ceramic layer |
US8309521B2 (en) | 2007-06-19 | 2012-11-13 | Zimmer, Inc. | Spacer with a coating thereon for use with an implant device |
US20110230973A1 (en) * | 2007-10-10 | 2011-09-22 | Zimmer, Inc. | Method for bonding a tantalum structure to a cobalt-alloy substrate |
US8608049B2 (en) * | 2007-10-10 | 2013-12-17 | Zimmer, Inc. | Method for bonding a tantalum structure to a cobalt-alloy substrate |
US20090187256A1 (en) * | 2008-01-21 | 2009-07-23 | Zimmer, Inc. | Method for forming an integral porous region in a cast implant |
WO2009096945A1 (en) * | 2008-01-29 | 2009-08-06 | Zimmer, Inc. | Implant device for use in an implant system |
US20090198286A1 (en) * | 2008-02-05 | 2009-08-06 | Zimmer, Inc. | Bone fracture fixation system |
US11020160B2 (en) | 2016-03-21 | 2021-06-01 | Warsaw Orthopedic, Inc. | Surgical injection system and method |
US10709814B2 (en) | 2016-04-22 | 2020-07-14 | Warsaw Orthopedic, Inc. | Osteoimplant comprising an insoluble fibrous polymer |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3300510A (en) * | 1964-03-06 | 1967-01-24 | American Home Prod | Hydantoins |
DE2714655A1 (en) * | 1977-04-01 | 1978-10-05 | Bayer Ag | METHOD OF MANUFACTURING HYDANTOIN |
IL57504A0 (en) * | 1978-06-15 | 1979-10-31 | Beecham Group Ltd | Prostagandin analogues,their preparation and pharmaceutical compositions containing |
DE4009506A1 (en) * | 1990-03-24 | 1991-09-26 | Hoechst Ag | hydantoin |
US5100907A (en) * | 1990-05-02 | 1992-03-31 | Lonza, Inc. | Hydantoin esters |
DE4126277A1 (en) * | 1991-08-08 | 1993-02-11 | Cassella Ag | HYDANTO DERIVATIVES |
-
1992
- 1992-04-24 DE DE4213634A patent/DE4213634A1/en not_active Withdrawn
-
1993
- 1993-04-03 DE DE59310337T patent/DE59310337D1/en not_active Expired - Lifetime
- 1993-04-03 EP EP93105575A patent/EP0566919B1/en not_active Expired - Lifetime
- 1993-04-03 AT AT93105575T patent/ATE236886T1/en not_active IP Right Cessation
- 1993-04-03 ES ES93105575T patent/ES2194842T3/en not_active Expired - Lifetime
- 1993-04-05 CZ CZ1993586A patent/CZ287885B6/en not_active IP Right Cessation
- 1993-04-12 US US08/045,994 patent/US5397796A/en not_active Expired - Lifetime
- 1993-04-23 SK SK392-93A patent/SK39293A3/en unknown
- 1993-04-23 JP JP09809893A patent/JP3793242B2/en not_active Expired - Fee Related
- 1993-04-23 CA CA002094773A patent/CA2094773C/en not_active Expired - Lifetime
- 1993-04-23 IL IL10551193A patent/IL105511A/en not_active IP Right Cessation
- 1993-04-28 AU AU38203/93A patent/AU665068B2/en not_active Ceased
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5652242A (en) * | 1993-03-29 | 1997-07-29 | Zeneca Limited | Heterocyclic derivatives |
US5753659A (en) * | 1993-03-29 | 1998-05-19 | Zeneca Limited | Heterocyclic compouds |
US5750754A (en) * | 1993-03-29 | 1998-05-12 | Zeneca Limited | Heterocyclic compounds |
US5563141A (en) * | 1993-03-29 | 1996-10-08 | Zeneca Limited | Heterocyclic compounds |
US5728701A (en) * | 1993-03-29 | 1998-03-17 | Zeneca Limited | Heterocyclic derivatives |
US5556977A (en) * | 1993-03-29 | 1996-09-17 | Zeneca Limited | Heterocyclic derivatives |
US5612373A (en) * | 1993-06-28 | 1997-03-18 | Zeneca Limited | Certain diacyl hydrazine derivatives |
US5576334A (en) * | 1993-06-28 | 1996-11-19 | Zeneca Limited | Acylurea derivatives |
US5494922A (en) * | 1993-06-28 | 1996-02-27 | Zeneca Limited | Allophanic acid derivatives |
US5760057A (en) * | 1993-06-28 | 1998-06-02 | Zeneca Limited | Certain (piperidin-4-yl-alkanoyl)carbazoyl!-carboxy-phenoxy derivatives |
US5981531A (en) * | 1993-06-28 | 1999-11-09 | Zeneca Limited | Acid derivatives |
US5849736A (en) * | 1993-11-24 | 1998-12-15 | The Dupont Merck Pharmaceutical Company | Isoxazoline and isoxazole fibrinogen receptor antagonists |
US5563158A (en) * | 1993-12-28 | 1996-10-08 | The Dupont Merck Pharmaceutical Company | Aromatic compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
US5691329A (en) * | 1993-12-28 | 1997-11-25 | The Dupont Merck Pharmaceutical Company | Compounds containing basic and acidic termini useful as fibrinogen receptor antagonists |
US5811441A (en) * | 1995-05-24 | 1998-09-22 | The Dupont Merck Pharmaceutical Company | Isoxazoline fibrinogen receptor antagonists |
Also Published As
Publication number | Publication date |
---|---|
SK39293A3 (en) | 1994-02-02 |
JP3793242B2 (en) | 2006-07-05 |
CZ287885B6 (en) | 2001-03-14 |
CZ58693A3 (en) | 1994-02-16 |
DE59310337D1 (en) | 2003-05-15 |
EP0566919A1 (en) | 1993-10-27 |
AU3820393A (en) | 1993-10-28 |
CA2094773C (en) | 2003-11-04 |
IL105511A0 (en) | 1993-08-18 |
DE4213634A1 (en) | 1993-10-28 |
ES2194842T3 (en) | 2003-12-01 |
US5397796A (en) | 1995-03-14 |
JPH06116245A (en) | 1994-04-26 |
EP0566919B1 (en) | 2003-04-09 |
ATE236886T1 (en) | 2003-04-15 |
AU665068B2 (en) | 1995-12-14 |
IL105511A (en) | 1997-02-18 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
EEER | Examination request |