RU2319692C2 - Derivatives of tetrahydrocarbazole, method for preparing tetrahydrocarbazole (variants), their using (variants) and pharmaceutical composition possessing activity of antagonist of gonadotropin-releasing hormone (variants) - Google Patents
Derivatives of tetrahydrocarbazole, method for preparing tetrahydrocarbazole (variants), their using (variants) and pharmaceutical composition possessing activity of antagonist of gonadotropin-releasing hormone (variants) Download PDFInfo
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- RU2319692C2 RU2319692C2 RU2004121776/04A RU2004121776A RU2319692C2 RU 2319692 C2 RU2319692 C2 RU 2319692C2 RU 2004121776/04 A RU2004121776/04 A RU 2004121776/04A RU 2004121776 A RU2004121776 A RU 2004121776A RU 2319692 C2 RU2319692 C2 RU 2319692C2
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- Prior art keywords
- amino
- carbonyl
- tetrahydro
- methylbutyl
- carbazol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- C07K5/0202—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link containing the structure -NH-X-X-C(=0)-, X being an optionally substituted carbon atom or a heteroatom, e.g. beta-amino acids
-
- 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
- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
-
- 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
- A61P15/16—Masculine 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
- A61P15/18—Feminine contraceptives
-
- 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
- A61P5/00—Drugs for disorders of the endocrine system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 carbon atoms of the ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Biophysics (AREA)
- Pregnancy & Childbirth (AREA)
- Crystallography & Structural Chemistry (AREA)
- Biochemistry (AREA)
- Diabetes (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
FIELD: organic chemistry, medicine, pharmacy.
SUBSTANCE: invention relates to novel derivatives of tetrahydrocarbazole of the general formula (I): wherein R1 means hydrogen atom (H), (C1-C6)-alkyl and can be optionally substituted with groups aryl, heteroaryl or -COOR11 wherein aryl or heteroaryl can be substituted with up to three substitutes that are chosen independently from group comprising -NO2, -CH3, -CF3, -OCH3, -OCF3 and halogen atoms; R11 means H, (C1-C12)-alkyl, (C1-C12)-aralkyl, aryl, heteroaryl, -COCH3 and can be optionally substituted with one substitute chosen from group comprising -CONH2, -COCH3, -COOCH3, -SO2CH3 and aryl; each R2, R3, R4 and R5 means independently H, halogen atom, -COOH, - CONH2, -CF3, -OCF3, -NO2, (C1-C6)-alkyl, (C1-C6)-alkoxy group, (C1-C12)-aralkyl, aryl, heteroaryl; R6 means -CONR8R9, -COOR8, -CH2NR8R9, -CH2R8, -CH2OR8; each R8 and R9 means independently H, (C1-C12)-alkyl, (C1-C12)-aralkyl, (C1-C12)-heteroaryl, aryl or heteroaryl wherein each of them can be with one or more substitutes chosen from group comprising -OH, -NH2, -CONHR10, -COOR10, -NH-C(=NH)-NH2 and halogen atom and wherein R10 means H, (C1-C12)-alkyl, (C1-C12)-aralkyl, aryl or heteroaryl and it is substituted optionally with group -CON(R11)2, or wherein radicals R8 and R9 in common with nitrogen atom to which they are bound form heterocyclic structure; R7 means H, (C1-C12)-alkyl, (C1-C12)-aralkyl, aryl or heteroaryl, -NR12R13, -NHCOR14, -NHCONHR14, -NHCOOR14, -NHSO2R14 and can be substituted optionally with one or more substitutes chosen from group comprising -OH, -NH2, -CONH2, -COOH and halogen atom; each among R12 and R13 means independently H, (C1-C12)-alkyl and can be substituted optionally with one or more substitutes chosen from aryl, heteroaryl that in turn can comprise up to three substitutes chosen independently from -NO2, -CH3, -CF3, -OCH3, -OCF3 and halogen atom; R14 means H, (C1-C12)-alkyl, (C1-C12)-aralkyl, aryl or heteroaryl that can be substituted optionally with one or more substitutes chosen from group comprising -NO2, -CH3, -OR11, -CF3, -OCF3, -OH, -N(R11)2, -OCOR11, -COOH, -CONH2, -NHCONHR11, -NHCOOR11 and halogen atom; each radical among Ra, Rb, Rc, Rd, Re and Rf means independently H, halogen atom, -COOH, -CONH2, -CF3, -OCF3, -NO2, (C1-C6)-alkyl, (C1-C6)-alkoxy group, aryl or heteroaryl wherein heteroaryl and heterocyclic group if it presents means pyridinyl, pyrrolidinyl, indolyl and under condition that compound of the general formula (I) is not chosen from group comprising 3-amino-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid, 3-amino-6-methoxy-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid, 3-amino-6-benzyloxy-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid, 3-acetamido-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid, 3-acetamido-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid methyl ester, 3-acetamido-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid (-)-menthyl ester, 3-tert.-butoxycarbonylamino-1,2,3,4-tetrahydrocarbazole 3-carboxylic acid, 9-methyl-1,2,3,4-tetrahydrocarbazole 4-carboxylic acid, 6-methoxy-9-methyl-1,2,3,4-tetrahydrocarbazole 4-carboxylic acid, 9-methyl-1,2,3,4-tetrahydrocarbazole 4-carboxamide, 6-methoxy-9-methyl-1,2,3,4-tetrahydrocarbazole 4-carboxamide. Compounds possess activity of antagonist of gonadotropin-releasing hormone that allows their using in pharmaceutical compositions. Also, invention describes methods for synthesis of these compounds.
EFFECT: improved method of synthesis, valuable medicinal properties of compounds and pharmaceutical composition.
22 cl, 1 tbl, 32 ex
Description
Claims (24)
Applications Claiming Priority (6)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10164564 | 2001-12-14 | ||
DE10164564A DE10164564B4 (en) | 2001-12-14 | 2001-12-14 | Tetrahydrocarbazole derivatives as ligands for G-protein coupled receptors (GPCR) |
US34187801P | 2001-12-21 | 2001-12-21 | |
US60/341,878 | 2001-12-21 | ||
PCT/EP2002/014344 WO2003051837A2 (en) | 2001-12-14 | 2002-12-16 | Tetrahydrocarbozole derivatives as ligands for g-protein coupled receptors (gpcr) |
EPPCT/EP02/14344 | 2002-12-16 |
Publications (2)
Publication Number | Publication Date |
---|---|
RU2004121776A RU2004121776A (en) | 2005-05-10 |
RU2319692C2 true RU2319692C2 (en) | 2008-03-20 |
Family
ID=26010882
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RU2004121776/04A RU2319692C2 (en) | 2001-12-14 | 2002-12-16 | Derivatives of tetrahydrocarbazole, method for preparing tetrahydrocarbazole (variants), their using (variants) and pharmaceutical composition possessing activity of antagonist of gonadotropin-releasing hormone (variants) |
Country Status (17)
Country | Link |
---|---|
EP (1) | EP1453803A2 (en) |
JP (1) | JP2005518375A (en) |
CN (1) | CN100500654C (en) |
AR (1) | AR037863A1 (en) |
AU (1) | AU2002361430B2 (en) |
BR (1) | BR0214958A (en) |
CA (1) | CA2468880A1 (en) |
HR (1) | HRP20040609A2 (en) |
HU (1) | HUP0500014A3 (en) |
IL (2) | IL161626A0 (en) |
MX (1) | MXPA04005768A (en) |
NO (1) | NO326692B1 (en) |
NZ (1) | NZ533430A (en) |
PL (1) | PL373400A1 (en) |
RU (1) | RU2319692C2 (en) |
TW (1) | TWI246423B (en) |
WO (1) | WO2003051837A2 (en) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ATE537825T1 (en) * | 2003-05-19 | 2012-01-15 | Irm Llc | IMMUNOSUPPRESSIVE COMPOUNDS AND COMPOSITIONS |
RU2318810C2 (en) * | 2003-06-10 | 2008-03-10 | Смитклайн Бичем Корпорейшн | Derivatives of tetrahydrocarbazole and their pharmaceutical using |
US20060074124A1 (en) | 2003-09-12 | 2006-04-06 | Andrew Napper | Methods of treating a disorder |
ES2530972T3 (en) * | 2003-09-12 | 2015-03-09 | Elixir Pharmaceuticals Inc | Methods of treatment of disorders |
DE102004033902A1 (en) | 2004-07-14 | 2006-02-16 | Zentaris Gmbh | New tetrahydrocarbazole compounds are neurokinin-1 receptor antagonists useful to treat or prevent e.g. pubertas praecox, hirsutism, polycystic ovary syndrome, hormone dependent neoplastic diseases and Alzheimer's disease |
RU2404163C2 (en) * | 2004-12-27 | 2010-11-20 | Актелион Фармасьютиклз Лтд | 2,3,4,9-tetrahydro-1h-carbazole derivatives as crth2 receptor antagonists |
BRPI0611705A2 (en) * | 2005-06-24 | 2016-11-16 | Lilly Co Eli | compound or a pharmaceutically acceptable salt thereof, pharmaceutical composition, and use of compound |
KR101411820B1 (en) * | 2006-08-07 | 2014-06-24 | 액테리온 파마슈티칼 리미티드 | (3-amino-1,2,3,4-tetrahydro-9h-carbazol-9-yl)-acetic acid derivatives |
EP1967202A1 (en) * | 2007-03-05 | 2008-09-10 | AEterna Zentaris GmbH | Use of LHRH Antagonists for the Treatment of Lower Urinary Tract Symptoms, in particular Overactive Bladder and/or Detrusor Overactivity |
EP1988098A1 (en) * | 2007-04-27 | 2008-11-05 | AEterna Zentaris GmbH | Novel Tetrahydrocarbazole Derivatives as Ligands of G-protein Coupled Receptors |
EP2095818A1 (en) * | 2008-02-29 | 2009-09-02 | AEterna Zentaris GmbH | Use of LHRH antagonists at non-castrating doses |
MY183111A (en) | 2010-03-22 | 2021-02-15 | Idorsia Pharmaceuticals Ltd | 3-(heteroaryl-amino)-1,2,3,4-tetrahydro-9h-carbazole derivatives and their use as prostaglandin d2 receptor modulators |
EP2697223B1 (en) | 2011-04-14 | 2016-07-13 | Actelion Pharmaceuticals Ltd. | 7-(heteroaryl-amino)-6,7,8,9-tetrahydropyrido[1,2-a]indol acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
WO2015140684A1 (en) | 2014-03-17 | 2015-09-24 | Actelion Pharmaceuticals Ltd | Azaindole acetic acid derivatives and their use as prostaglandin d2 receptor modulators |
CN106103437A (en) | 2014-03-18 | 2016-11-09 | 埃科特莱茵药品有限公司 | Azaindole acetogenin and the purposes as prostaglandin D 2 receptor regulator thereof |
ES2867757T3 (en) | 2015-09-15 | 2021-10-20 | Idorsia Pharmaceuticals Ltd | Crystalline forms |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1418703A (en) * | 1973-06-02 | 1975-12-24 | Pfizer Ltd | 3-alkyl-9-substituted-1,2,3,4-tetrahydrocarbazoles |
ATE90076T1 (en) * | 1986-03-27 | 1993-06-15 | Merck Frosst Canada Inc | TETRAHYDROCARBAZOLE ESTER. |
US5607939A (en) * | 1994-04-28 | 1997-03-04 | Takeda Chemical Industries, Ltd. | Condensed heterocyclic compounds, their production and use |
AU728988B2 (en) * | 1997-06-05 | 2001-01-25 | Merck & Co., Inc. | Antagonists of gonadotropin releasing hormone |
-
2002
- 2002-12-16 JP JP2003552724A patent/JP2005518375A/en active Pending
- 2002-12-16 WO PCT/EP2002/014344 patent/WO2003051837A2/en active Application Filing
- 2002-12-16 PL PL02373400A patent/PL373400A1/en not_active Application Discontinuation
- 2002-12-16 HU HU0500014A patent/HUP0500014A3/en unknown
- 2002-12-16 MX MXPA04005768A patent/MXPA04005768A/en active IP Right Grant
- 2002-12-16 NZ NZ533430A patent/NZ533430A/en unknown
- 2002-12-16 CN CNB028241487A patent/CN100500654C/en not_active Expired - Fee Related
- 2002-12-16 EP EP02796648A patent/EP1453803A2/en not_active Withdrawn
- 2002-12-16 AU AU2002361430A patent/AU2002361430B2/en not_active Ceased
- 2002-12-16 RU RU2004121776/04A patent/RU2319692C2/en not_active IP Right Cessation
- 2002-12-16 IL IL16162602A patent/IL161626A0/en unknown
- 2002-12-16 TW TW091136440A patent/TWI246423B/en not_active IP Right Cessation
- 2002-12-16 CA CA002468880A patent/CA2468880A1/en not_active Abandoned
- 2002-12-16 BR BR0214958-3A patent/BR0214958A/en not_active IP Right Cessation
- 2002-12-17 AR ARP020104893A patent/AR037863A1/en unknown
-
2004
- 2004-05-26 NO NO20042198A patent/NO326692B1/en not_active IP Right Cessation
- 2004-07-05 HR HR20040609A patent/HRP20040609A2/en not_active Application Discontinuation
-
2008
- 2008-07-23 IL IL192991A patent/IL192991A0/en unknown
Non-Patent Citations (1)
Title |
---|
J. Med. Chem. 1998, 41, р.451-467. * |
Also Published As
Publication number | Publication date |
---|---|
AU2002361430A1 (en) | 2003-06-30 |
IL161626A0 (en) | 2004-09-27 |
HUP0500014A3 (en) | 2010-06-28 |
NZ533430A (en) | 2005-12-23 |
CA2468880A1 (en) | 2003-06-26 |
JP2005518375A (en) | 2005-06-23 |
CN1599720A (en) | 2005-03-23 |
NO326692B1 (en) | 2009-02-02 |
AR037863A1 (en) | 2004-12-09 |
AU2002361430B2 (en) | 2007-09-13 |
MXPA04005768A (en) | 2004-09-10 |
BR0214958A (en) | 2004-12-28 |
RU2004121776A (en) | 2005-05-10 |
HRP20040609A2 (en) | 2005-06-30 |
PL373400A1 (en) | 2005-08-22 |
HUP0500014A2 (en) | 2005-04-28 |
WO2003051837A2 (en) | 2003-06-26 |
EP1453803A2 (en) | 2004-09-08 |
WO2003051837A8 (en) | 2004-05-06 |
NO20042198L (en) | 2004-07-09 |
TW200305405A (en) | 2003-11-01 |
CN100500654C (en) | 2009-06-17 |
TWI246423B (en) | 2006-01-01 |
IL192991A0 (en) | 2011-08-01 |
WO2003051837A3 (en) | 2004-02-26 |
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MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20091217 |