WO1996032003A3 - Tetrahydroimidazopyridoindolediones and their use as medicaments - Google Patents
Tetrahydroimidazopyridoindolediones and their use as medicaments Download PDFInfo
- Publication number
- WO1996032003A3 WO1996032003A3 PCT/EP1996/003023 EP9603023W WO9632003A3 WO 1996032003 A3 WO1996032003 A3 WO 1996032003A3 EP 9603023 W EP9603023 W EP 9603023W WO 9632003 A3 WO9632003 A3 WO 9632003A3
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- alkyl
- halogen
- optionally substituted
- phenyl
- membered heterocyclic
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains three hetero rings
- C07D471/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/02—Nasal agents, e.g. decongestants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic 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
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Abstract
Priority Applications (9)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
BR9609503-2A BR9609503A (en) | 1995-07-14 | 1996-07-11 | Compound, use of a compound, process of treatment of conditions where the inhibition of pg specific pgmp is of therapeutic benefit, in human or non-human animal body, pharmaceutical composition, and processes to prepare it and a compound |
MX9800415A MX9800415A (en) | 1995-07-14 | 1996-07-11 | Chemical compounds. |
US08/981,966 US6001847A (en) | 1995-07-14 | 1996-07-11 | Chemical compounds |
AT96925709T ATE211139T1 (en) | 1995-07-14 | 1996-07-11 | TETRAHYDROIMIDAZOPYRIDOINDOLDIONE AS CGMP SPECIFIC PDE INHIBITORS |
JP53072796A JP4012246B2 (en) | 1995-07-14 | 1996-07-11 | Chemical substance |
DE69618231T DE69618231T2 (en) | 1995-07-14 | 1996-07-11 | TETRAHYDROIMIDAZOPYRIDOINDOLDIONE AS cGMP SPECIFIC PDE INHIBITORS |
EP96925709A EP0859778B1 (en) | 1995-07-14 | 1996-07-11 | TETRAHYDROIMIDAZOPYRIDOINDOLEDIONES AS INHIBITORS OF cGMP SPECIFIC PDE |
AU66138/96A AU702548B2 (en) | 1995-07-14 | 1996-07-11 | Chemical compounds |
US09/154,619 US6143757A (en) | 1995-07-14 | 1998-09-16 | Chemical compounds |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB9514473.9 | 1995-07-14 | ||
GBGB9514473.9A GB9514473D0 (en) | 1995-07-14 | 1995-07-14 | Chemical compounds |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US09/154,619 Continuation-In-Part US6143757A (en) | 1995-07-14 | 1998-09-16 | Chemical compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
WO1996032003A2 WO1996032003A2 (en) | 1996-10-17 |
WO1996032003A3 true WO1996032003A3 (en) | 1997-01-03 |
Family
ID=10777704
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP1996/003023 WO1996032003A2 (en) | 1995-07-14 | 1996-07-11 | Tetrahydroimidazopyridoindolediones and their use as medicaments |
Country Status (13)
Country | Link |
---|---|
US (3) | US6001847A (en) |
EP (1) | EP0859778B1 (en) |
JP (1) | JP4012246B2 (en) |
CN (1) | CN1095841C (en) |
AT (1) | ATE211139T1 (en) |
AU (1) | AU702548B2 (en) |
BR (1) | BR9609503A (en) |
CA (1) | CA2226759A1 (en) |
DE (1) | DE69618231T2 (en) |
ES (1) | ES2170252T3 (en) |
GB (1) | GB9514473D0 (en) |
MX (1) | MX9800415A (en) |
WO (1) | WO1996032003A2 (en) |
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DE69833254T2 (en) | 1997-06-23 | 2006-11-02 | Cellegy Pharmaceuticals, Inc., Brisbane | MICRODOSIS THERAPY OF VASCULAR EXPOSURE BY NO-DONORS |
US6403597B1 (en) | 1997-10-28 | 2002-06-11 | Vivus, Inc. | Administration of phosphodiesterase inhibitors for the treatment of premature ejaculation |
US6548490B1 (en) * | 1997-10-28 | 2003-04-15 | Vivus, Inc. | Transmucosal administration of phosphodiesterase inhibitors for the treatment of erectile dysfunction |
CA2339630C (en) * | 1998-09-16 | 2006-05-23 | Icos Corporation | Carboline derivatives as cgmp phosphodiesterase inhibitors |
US6451807B1 (en) | 1999-04-30 | 2002-09-17 | Lilly Icos, Llc. | Methods of treating sexual dysfunction in an individual suffering from a retinal disease, class 1 congestive heart failure, or myocardial infarction using a PDE5 inhibitor |
HUP0001632A3 (en) | 1999-04-30 | 2001-12-28 | Lilly Icos Llc Wilmington | Pharmaceutical compositions comprising selective phosphodiestherase inhibitors |
US20010036959A1 (en) * | 2000-04-03 | 2001-11-01 | Gabel Rolf Dieter | Carvedilol-hydrophilic solutions |
JP2004500425A (en) | 2000-04-19 | 2004-01-08 | リリー アイコス リミテッド ライアビリティ カンパニー | Use of cyclic GMP-specific phosphodiesterase inhibitors for the treatment of Parkinson's disease |
JP2004501920A (en) * | 2000-06-23 | 2004-01-22 | リリー アイコス リミテッド ライアビリティ カンパニー | Cyclic GMP-specific phosphodiesterase inhibitor |
ES2248399T3 (en) | 2000-10-02 | 2006-03-16 | Lilly Icos Llc | CONDENSED PYRIDOINDOL DERIVATIVES. |
AU2002213421A1 (en) * | 2000-10-03 | 2002-04-15 | Lilly Icos Llc | Condensed pyridoindole derivatives |
JP4179784B2 (en) * | 2001-02-15 | 2008-11-12 | 田辺三菱製薬株式会社 | Orally disintegrating tablets |
DE10118306A1 (en) | 2001-04-12 | 2002-10-17 | Bayer Ag | Composition for intranasal administration of imidazo-triazinone derivative cGMP PDE inhibitor for treatment of erectile dysfunction, also containing local anesthetic to prevent nasal blockage and improve absorption |
JP4216606B2 (en) * | 2001-04-25 | 2009-01-28 | リリー アイコス リミテッド ライアビリティ カンパニー | Chemical compound |
JP2004536816A (en) * | 2001-06-05 | 2004-12-09 | リリー アイコス リミテッド ライアビリティ カンパニー | Carboline derivatives as PDE5 inhibitors |
US7335680B2 (en) * | 2001-12-20 | 2008-02-26 | Laboratoires Serono Sa | Pyrrolidine derivatives as prostaglandin modulators |
MY140561A (en) * | 2002-02-20 | 2009-12-31 | Nycomed Gmbh | Dosage form containing pde 4 inhibitor as active ingredient |
US7208516B2 (en) * | 2002-03-20 | 2007-04-24 | Celgene Corporation | Methods of the treatment of psoriatic arthritis using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
US6962940B2 (en) | 2002-03-20 | 2005-11-08 | Celgene Corporation | (+)-2-[1-(3-Ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione: methods of using and compositions thereof |
US7276529B2 (en) * | 2002-03-20 | 2007-10-02 | Celgene Corporation | Methods of the treatment or prevention of exercise-induced asthma using (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione |
US7893101B2 (en) * | 2002-03-20 | 2011-02-22 | Celgene Corporation | Solid forms comprising (+)-2-[1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethyl]-4-acetylaminoisoindoline-1,3-dione, compositions thereof, and uses thereof |
ES2211295B1 (en) * | 2002-07-19 | 2005-12-01 | Consejo Sup. De Investig. Cientificas | TETRAHYDRO-BETA-PHENOLIC CARBOLINS AS ANTIOXIDANTS. |
ES2318175T3 (en) * | 2002-07-31 | 2009-05-01 | Lilly Icos Llc | PICTET-SPLENGER MODIFIED REACTION AND PRODUCTS PREPARED FROM THE SAME. |
US20050048573A1 (en) * | 2003-02-03 | 2005-03-03 | Plexxikon, Inc. | PDE5A crystal structure and uses |
DE602004023921D1 (en) | 2003-03-10 | 2009-12-17 | Nycomed Gmbh | NEW PROCESS FOR THE PRODUCTION OF ROLUMUMILAST |
DK1644021T3 (en) * | 2003-06-13 | 2012-10-29 | Ironwood Pharmaceuticals Inc | METHODS AND COMPOSITIONS FOR THE TREATMENT OF GASTROINTESTINAL DISEASES |
DE10348022A1 (en) * | 2003-10-15 | 2005-05-25 | Imtm Gmbh | New dipeptidyl peptidase IV inhibitors for the functional influence of different cells and for the treatment of immunological, inflammatory, neuronal and other diseases |
US8076353B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Inhibition of VEGF translation |
JP2007529533A (en) | 2004-03-15 | 2007-10-25 | ピーティーシー セラピューティクス,インコーポレーテッド | Tetracyclic carboline derivatives useful for inhibiting angiogenesis |
AU2005222632B2 (en) | 2004-03-15 | 2012-02-09 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the inhibition of angiogenesis |
US8076352B2 (en) | 2004-03-15 | 2011-12-13 | Ptc Therapeutics, Inc. | Administration of carboline derivatives useful in the treatment of cancer and other diseases |
US7767689B2 (en) | 2004-03-15 | 2010-08-03 | Ptc Therapeutics, Inc. | Carboline derivatives useful in the treatment of cancer |
CA2576619A1 (en) | 2004-08-18 | 2006-02-23 | Altana Pharma Ag | Benzothienopyridines for use as inhibitors of eg5 kinesin |
US8663694B2 (en) * | 2005-03-16 | 2014-03-04 | Takeda Gmbh | Taste masked dosage form containing roflumilast |
US20070155791A1 (en) * | 2005-12-29 | 2007-07-05 | Zeldis Jerome B | Methods for treating cutaneous lupus using aminoisoindoline compounds |
UA96592C2 (en) | 2006-02-22 | 2011-11-25 | 4Сц Аг | Indolopyridines as eg5 kinesin modulators |
WO2007113243A2 (en) * | 2006-03-31 | 2007-10-11 | Investigación Y Clínica Andrológicas S.L. | Use of pde 5 inhibitors for the treatment of overactive bladder |
FR2912405A1 (en) * | 2007-02-08 | 2008-08-15 | Fourtillan Snc | DERIVATIVES OF IMIDAZO [1 ', 5': 1,6] PYRIDO [3,4-B] INDOLES AND THEIR USE IN THERAPEUTICS |
US20110027226A1 (en) * | 2007-08-22 | 2011-02-03 | 4Sc Ag | Indolopyridines as inhibitors of the kinesin spindle protein (eg5) |
EP2098524A1 (en) * | 2008-03-05 | 2009-09-09 | 4Sc Ag | Process for preparing enantiomerically pure indolopyrinidines |
MX2010010334A (en) * | 2008-03-24 | 2010-10-08 | Celgene Corp | Treatment of psoriasis or psoriatic arthritis using cyclopropyl-n-{2-{(1s)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsu lfonyl)ethyl]-3-oxoisoindoline-4-yl}carboxamide. |
CN105793253B (en) | 2013-11-22 | 2019-08-23 | 法玛克亚公司 | Autotaxin inhibitors compound |
BR112016010221A2 (en) * | 2013-11-22 | 2018-05-02 | Pharmakea Inc | tetracyclic autotaxin inhibitors. |
US20160317542A1 (en) | 2013-12-09 | 2016-11-03 | Respira Therapeutics, Inc. | Pde5 inhibitor powder formulations and methods relating thereto |
EP3157520B1 (en) | 2014-06-23 | 2019-09-04 | Celgene Corporation | Apremilast for the treatment of a liver disease or a liver function abnormality |
AU2016268250B2 (en) | 2015-05-27 | 2020-08-27 | Sabre Therapeutics Llc | Autotaxin inhibitors and uses thereof |
WO2017168174A1 (en) | 2016-04-02 | 2017-10-05 | N4 Pharma Uk Limited | New pharmaceutical forms of sildenafil |
Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995019978A1 (en) * | 1994-01-21 | 1995-07-27 | Laboratoires Glaxo Wellcome S.A. | Tetracyclic derivatives, process of preparation and use |
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US3644384A (en) * | 1969-06-09 | 1972-02-22 | Sterling Drug Inc | Certain 2-(alpha-haloacetyl) - 1 2 3 4-tetrahydro - 9h - pyrido(3 4-b)indole-3-carboxylates and derivatives |
US3717638A (en) * | 1971-03-11 | 1973-02-20 | Sterling Drug Inc | 1,2,3,4,6,7,12,12A-OCTAHYDRO-2-PHENYLPYRAZINO[2',1':6,1]PYRIDO[3,4-b]INDOLES AND INTERMEDIATES THEREFOR |
US3917599A (en) * | 1973-03-30 | 1975-11-04 | Council Scient Ind Res | 2-Substituted-1,2,3,4,6,7,12,12A-octahydropyrazino(2{40 ,1{40 :6,1)pyrido(3,4-B)indoles |
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IT1217190B (en) * | 1988-04-22 | 1990-03-14 | Recordati Chem Pharm | USEFUL COMPOUNDS FOR THE TREATMENT AND DIAGNOSIS OF HURRY DYSFUNCTIONS |
EP0357122A3 (en) * | 1988-08-29 | 1991-10-23 | Duphar International Research B.V | Use of beta-carbolines, their bio-isosteric benzofuran and benzothiophene analogues for the manufacture of a medicament having cytostatic properties |
DE3830096A1 (en) * | 1988-09-03 | 1990-03-15 | Hoechst Ag | PIPERAZINDIONE WITH PSYCHOTROPER EFFECT |
FR2649613B1 (en) * | 1989-07-11 | 1991-09-27 | Virag Ronald | VASO-ACTIVE MEDICINE |
JPH0344324A (en) * | 1989-07-13 | 1991-02-26 | Kazuoki Tsuchiya | Sexual function invigorator |
US5270323A (en) * | 1990-05-31 | 1993-12-14 | Pfizer Inc. | Method of treating impotence |
DK0459666T3 (en) * | 1990-05-31 | 1994-12-05 | Pfizer | Medicines for impotence |
GB9013750D0 (en) * | 1990-06-20 | 1990-08-08 | Pfizer Ltd | Therapeutic agents |
GB9114760D0 (en) * | 1991-07-09 | 1991-08-28 | Pfizer Ltd | Therapeutic agents |
GB9218322D0 (en) * | 1992-08-28 | 1992-10-14 | Pfizer Ltd | Therapeutic agents |
GB9301192D0 (en) * | 1993-06-09 | 1993-06-09 | Trott Francis W | Flower shaped mechanised table |
GB9514465D0 (en) * | 1995-07-14 | 1995-09-13 | Glaxo Lab Sa | Chemical compounds |
DE10199068I2 (en) * | 1994-04-22 | 2004-05-06 | Pentech Pharmaceuticals Inc | Sublingual dosage forms containing apomorphine for use in the treatment of erectile dysfunction. |
US5874437A (en) * | 1996-11-01 | 1999-02-23 | Nitromed, Inc. | Nitrosated and nitrosylated phosphodiesterase inhibitor compounds, compositions and their uses |
-
1995
- 1995-07-14 GB GBGB9514473.9A patent/GB9514473D0/en active Pending
-
1996
- 1996-07-11 BR BR9609503-2A patent/BR9609503A/en not_active IP Right Cessation
- 1996-07-11 MX MX9800415A patent/MX9800415A/en unknown
- 1996-07-11 AT AT96925709T patent/ATE211139T1/en not_active IP Right Cessation
- 1996-07-11 ES ES96925709T patent/ES2170252T3/en not_active Expired - Lifetime
- 1996-07-11 US US08/981,966 patent/US6001847A/en not_active Expired - Lifetime
- 1996-07-11 JP JP53072796A patent/JP4012246B2/en not_active Expired - Fee Related
- 1996-07-11 CA CA002226759A patent/CA2226759A1/en not_active Abandoned
- 1996-07-11 AU AU66138/96A patent/AU702548B2/en not_active Ceased
- 1996-07-11 CN CN96196779A patent/CN1095841C/en not_active Expired - Fee Related
- 1996-07-11 EP EP96925709A patent/EP0859778B1/en not_active Expired - Lifetime
- 1996-07-11 WO PCT/EP1996/003023 patent/WO1996032003A2/en active IP Right Grant
- 1996-07-11 DE DE69618231T patent/DE69618231T2/en not_active Expired - Fee Related
-
1998
- 1998-09-16 US US09/154,619 patent/US6143757A/en not_active Expired - Fee Related
-
1999
- 1999-08-24 US US09/382,240 patent/US6218400B1/en not_active Expired - Fee Related
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1995019978A1 (en) * | 1994-01-21 | 1995-07-27 | Laboratoires Glaxo Wellcome S.A. | Tetracyclic derivatives, process of preparation and use |
Non-Patent Citations (7)
Title |
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J. SANDRIN ET AL.: "13-C-NMR of 1,3-Disubstituted-1,2,3,4-tetrahydro-beta-carbolines", HETEROCYCLES, vol. 4, no. 7, 1976, pages 1249 - 55, XP000196527 * |
M.F. BRAÑA ET AL.: "One-Pot Synthesis of a 2-Dialkylaminoalkyl-Substituted Tetrahydro-beta-carboline-hydantoin System", LIEBIGS ANNALEN DER CHEMIE, no. 8, 1992, pages 867 - 9, XP000608323 * |
M.F. BRAÑA ET AL.: "Synthesis and reactivity of beta-carboline-hydantoin systems", SYNTHETIC COMMUNICATIONS, vol. 20, no. 12, 1990, pages 1793 - 810, XP000196528 * |
M.F. BRAÑA ET AL.: "Synthesis of New Derivatives of beta-Carboline-hydantoin", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 27, no. 3, 1990, pages 703 - 6, XP000608321 * |
M.L. LOPEZ-RODRIGUEZ ET AL.: "alpha-1-Adrenoceptor Reagents. Synthesis of Some 5,6,11,11a-Tetrahydro-1H-imidazo- [1',5':1,6]pyrido and 5,6,11,11b-Tetra- hydro-1H-imidazo[1',5':1,2]pyrido[3,4-b]- indole-1,3(2H)-diones", CHEMICAL AND PHARMACEUTICAL BULLETIN, vol. 43, no. 6, June 1995 (1995-06-01), pages 941 - 6, XP000608287 * |
M.L. LÓPEZ-RODRÍGUEZ ET AL.: "Stereospecificity in the Reaction of Tetrahydro-beta-carboline-3-carboxylic Acids with Isocyanates and Isothiocyanates. Kinetic vs Thermodynamic Control", JOURNAL OF ORGANIC CHEMISTRY, vol. 59, no. 6, 1994, pages 1583 - 5, XP000196493 * |
P. DE MIGUEL ET AL.: "Synthesis of Tetrahydroimidazo[1,5-b]-beta-carboline Derivatives with Complex Basic Substituents", JOURNAL OF HETEROCYCLIC CHEMISTRY, vol. 31, no. 5, 1994, pages 1235 - 9, XP000608322 * |
Also Published As
Publication number | Publication date |
---|---|
JP4012246B2 (en) | 2007-11-21 |
US6143757A (en) | 2000-11-07 |
DE69618231D1 (en) | 2002-01-31 |
AU6613896A (en) | 1996-10-30 |
MX9800415A (en) | 1998-04-30 |
CN1095841C (en) | 2002-12-11 |
CA2226759A1 (en) | 1996-10-17 |
EP0859778A2 (en) | 1998-08-26 |
WO1996032003A2 (en) | 1996-10-17 |
JPH11509517A (en) | 1999-08-24 |
ES2170252T3 (en) | 2002-08-01 |
US6001847A (en) | 1999-12-14 |
ATE211139T1 (en) | 2002-01-15 |
AU702548B2 (en) | 1999-02-25 |
EP0859778B1 (en) | 2001-12-19 |
GB9514473D0 (en) | 1995-09-13 |
US6218400B1 (en) | 2001-04-17 |
BR9609503A (en) | 2000-03-08 |
CN1195350A (en) | 1998-10-07 |
DE69618231T2 (en) | 2002-08-22 |
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