CA2724629C - Tetrahydrocyclopenta[b]indole androgen receptor modulators - Google Patents
Tetrahydrocyclopenta[b]indole androgen receptor modulators Download PDFInfo
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- CA2724629C CA2724629C CA2724629A CA2724629A CA2724629C CA 2724629 C CA2724629 C CA 2724629C CA 2724629 A CA2724629 A CA 2724629A CA 2724629 A CA2724629 A CA 2724629A CA 2724629 C CA2724629 C CA 2724629C
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- IAZKTAKWBHQCGF-UHFFFAOYSA-N 1,2,3,3a-tetrahydrocyclopenta[b]indole Chemical compound N1=C2C=CC=CC2=C2C1CCC2 IAZKTAKWBHQCGF-UHFFFAOYSA-N 0.000 title description 10
- 239000000849 selective androgen receptor modulator Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 168
- 150000003839 salts Chemical class 0.000 claims abstract description 58
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- 238000004519 manufacturing process Methods 0.000 claims description 8
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- FBCDRHDULQYRTB-UHFFFAOYSA-N 2-[2-ethoxy-5-(4-ethylpiperazin-1-yl)sulfonylphenyl]-5-methyl-7-propyl-1h-imidazo[5,1-f][1,2,4]triazin-4-one;trihydrate;hydrochloride Chemical compound O.O.O.Cl.CCCC1=NC(C)=C(C(N=2)=O)N1NC=2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(CC)CC1 FBCDRHDULQYRTB-UHFFFAOYSA-N 0.000 claims description 4
- DEIYFTQMQPDXOT-UHFFFAOYSA-N sildenafil citrate Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CCCC1=NN(C)C(C(N2)=O)=C1N=C2C(C(=CC=1)OCC)=CC=1S(=O)(=O)N1CCN(C)CC1 DEIYFTQMQPDXOT-UHFFFAOYSA-N 0.000 claims description 4
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- HNKVROGLZCBJBV-KRWDZBQOSA-N propan-2-yl n-[(2s)-7-cyano-4-[(2-hydroxyphenyl)methyl]-2,3-dihydro-1h-cyclopenta[b]indol-2-yl]carbamate Chemical compound C([C@H](C1)NC(=O)OC(C)C)C2=C1C1=CC(C#N)=CC=C1N2CC1=CC=CC=C1O HNKVROGLZCBJBV-KRWDZBQOSA-N 0.000 claims 1
- RUXJDAYOICLRHH-INIZCTEOSA-N propan-2-yl n-[(2s)-7-cyano-4-[(3-fluoro-2-hydroxyphenyl)methyl]-2,3-dihydro-1h-cyclopenta[b]indol-2-yl]carbamate Chemical compound C([C@H](C1)NC(=O)OC(C)C)C2=C1C1=CC(C#N)=CC=C1N2CC1=CC=CC(F)=C1O RUXJDAYOICLRHH-INIZCTEOSA-N 0.000 claims 1
- RIZZCKXDHXXMQI-KRWDZBQOSA-N propan-2-yl n-[(2s)-7-cyano-4-[(5-fluoro-2-hydroxyphenyl)methyl]-2,3-dihydro-1h-cyclopenta[b]indol-2-yl]carbamate Chemical compound C([C@H](C1)NC(=O)OC(C)C)C2=C1C1=CC(C#N)=CC=C1N2CC1=CC(F)=CC=C1O RIZZCKXDHXXMQI-KRWDZBQOSA-N 0.000 claims 1
- GAVLUGRJEJKCRF-RVHYNSKXSA-N propan-2-yl n-[(2s)-7-cyano-4-[[(2r,3s)-3-hydroxy-1-methylpyrrolidin-2-yl]methyl]-2,3-dihydro-1h-cyclopenta[b]indol-2-yl]carbamate Chemical compound C([C@H](C1)NC(=O)OC(C)C)C2=C1C1=CC(C#N)=CC=C1N2C[C@@H]1[C@@H](O)CCN1C GAVLUGRJEJKCRF-RVHYNSKXSA-N 0.000 claims 1
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- 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/06—Anabolic agents
-
- 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
-
- 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
- A61P5/24—Drugs for disorders of the endocrine system of the sex hormones
- A61P5/26—Androgens
-
- 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
- C07D401/06—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 carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Physical Education & Sports Medicine (AREA)
- Endocrinology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5372208P | 2008-05-16 | 2008-05-16 | |
| US61/053,722 | 2008-05-16 | ||
| PCT/US2009/043875 WO2009140448A1 (en) | 2008-05-16 | 2009-05-14 | Tetrahydrocyclopenta[b]indole androgen receptor modulators |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2724629A1 CA2724629A1 (en) | 2009-11-19 |
| CA2724629C true CA2724629C (en) | 2014-08-19 |
Family
ID=40847864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2724629A Expired - Fee Related CA2724629C (en) | 2008-05-16 | 2009-05-14 | Tetrahydrocyclopenta[b]indole androgen receptor modulators |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8486943B2 (https=) |
| EP (1) | EP2297100B1 (https=) |
| JP (1) | JP5603327B2 (https=) |
| KR (1) | KR101278788B1 (https=) |
| CN (1) | CN102026974B (https=) |
| AU (1) | AU2009246348B2 (https=) |
| BR (1) | BRPI0912394A2 (https=) |
| CA (1) | CA2724629C (https=) |
| CY (1) | CY1113341T1 (https=) |
| DK (1) | DK2297100T3 (https=) |
| EA (1) | EA019713B1 (https=) |
| ES (1) | ES2396612T3 (https=) |
| HR (1) | HRP20120917T1 (https=) |
| MX (1) | MX2010012436A (https=) |
| PL (1) | PL2297100T3 (https=) |
| PT (1) | PT2297100E (https=) |
| SI (1) | SI2297100T1 (https=) |
| WO (1) | WO2009140448A1 (https=) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA98777C2 (en) | 2006-11-20 | 2012-06-25 | Эли Лилли Энд Компани | Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| CA2716320C (en) | 2008-02-22 | 2014-01-28 | Radius Health, Inc. | Selective androgen receptor modulators |
| AU2011212813B2 (en) | 2010-02-04 | 2014-10-23 | Radius Health, Inc. | Selective androgen receptor modulators |
| HUE030072T2 (en) | 2010-05-12 | 2017-04-28 | Radius Health Inc | Therapeutic prescriptions |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9133182B2 (en) | 2010-09-28 | 2015-09-15 | Radius Health, Inc. | Selective androgen receptor modulators |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| ES3055185T3 (en) | 2014-03-28 | 2026-02-10 | Univ Duke | Treatment of an estrogen receptor positive breast cancer using a selective estrogen receptor modulator |
| JOP20180072A1 (ar) * | 2014-09-11 | 2019-01-30 | Lilly Co Eli | علاج الأعراض المرتبطة بالعلاج بالحرمان من الأندروجين |
| MX389702B (es) | 2016-06-22 | 2025-03-20 | Ellipses Pharma Ltd | Compuestos para usarse en el tratamiento de cancer de mama que expresa el receptor de androgenos (ar+). |
| US20180185347A1 (en) * | 2016-11-16 | 2018-07-05 | Transition Therapeutics (Ireland 2) Limited | Tetrahydrocyclopenta[b]indole compounds and phosphodiesterase inhibitors for the treatment of the signs and symptoms of bhp |
| JP7481115B2 (ja) | 2017-01-05 | 2024-05-10 | ラジウス ファーマシューティカルズ，インコーポレイテッド | Ｒａｄ１９０１－２ｈｃｌの多形性形態 |
| MX2020013713A (es) | 2018-07-04 | 2021-03-02 | Radius Pharmaceuticals Inc | Formas polimorficas de rad1901-2hcl. |
| EP3924328A1 (en) | 2019-02-12 | 2021-12-22 | Radius Pharmaceuticals, Inc. | Processes and compounds |
| CN115023225A (zh) * | 2020-01-27 | 2022-09-06 | 伊尔根制药有限公司 | 用于治疗肾病的四氢环戊[b]吲哚化合物 |
| CN116761598A (zh) * | 2020-07-06 | 2023-09-15 | 新月生物科学 | Fabp4调节化合物的抗病毒用途 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US4988820A (en) * | 1986-02-21 | 1991-01-29 | Bayer Aktiengesellschaft | Cycloalkano(1,2-B) indole-sulponamides |
| GB8924392D0 (en) * | 1989-10-30 | 1989-12-20 | Bayer Ag | Substituted cycloalkano/b/dihydroindole-and-indolesulphonamides |
| GB9008108D0 (en) * | 1990-04-10 | 1990-06-06 | Bayer Ag | Cycloalkano(b)dihydroindoles and-indolesulphonamides substituted by heterocycles |
| DE4027278A1 (de) * | 1990-08-29 | 1992-03-05 | Bayer Ag | Heterocyclisch substituierte indolsulfonamide |
| DE4131346A1 (de) * | 1991-09-20 | 1993-03-25 | Bayer Ag | Indolsulfonamid substituierte dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| US7160909B2 (en) | 2001-08-09 | 2007-01-09 | Eli Lilly And Company | Cyclopenta[b]indole derivatives as sPLA2 inhibitors |
| DE10164564B4 (de) * | 2001-12-14 | 2007-05-16 | Zentaris Gmbh | Tetrahydrocarbazolderivate als Liganden für G-Protein gekoppelte Rezeptoren (GPCR) |
| AU2003231509A1 (en) * | 2002-05-16 | 2003-12-02 | Shionogi And Co., Ltd. | Compound exhibiting pgd 2 receptor antagonism |
| US20060074124A1 (en) * | 2003-09-12 | 2006-04-06 | Andrew Napper | Methods of treating a disorder |
| US7019022B2 (en) | 2003-12-15 | 2006-03-28 | Merck Frosst Canada & Co. | Substituted tetrahydrocarbazole and cyclopentanoindole derivatives |
| BRPI0507657A (pt) | 2004-03-03 | 2007-07-10 | Lilly Co Eli | composto ou um sal farmaceuticamente aceitável do mesmo, composição farmacêutica, método para tratar um distúrbio, e, uso de um composto ou um sal farmaceuticamente aceitável do mesmo |
| WO2006058088A2 (en) | 2004-11-23 | 2006-06-01 | Ptc Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| JP2008530229A (ja) | 2005-02-17 | 2008-08-07 | ワイス | シクロアルキル縮合インドール、ベンゾチオフェン、ベンゾフランおよびインデン誘導体 |
| CA2612723A1 (en) * | 2005-06-24 | 2007-01-04 | Eli Lilly And Company | Tetrahydrocarbazole derivatives useful as androgen receptor modulators |
| US20090022694A1 (en) | 2005-10-18 | 2009-01-22 | Distefano Peter | Sirt1 inhibition |
| WO2008019825A1 (en) | 2006-08-14 | 2008-02-21 | Santhera Pharmaceuticals (Schweiz) Ag | Use of tricyclic indole derivatives for the treatment of muscular diseases |
| UA98777C2 (en) * | 2006-11-20 | 2012-06-25 | Эли Лилли Энд Компани | Tetrahydrocyclopenta[b]indole compounds as androgen receptor modulators |
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2009
- 2009-05-14 EA EA201071317A patent/EA019713B1/ru not_active IP Right Cessation
- 2009-05-14 KR KR1020107025588A patent/KR101278788B1/ko not_active Expired - Fee Related
- 2009-05-14 PL PL09747531T patent/PL2297100T3/pl unknown
- 2009-05-14 BR BRPI0912394A patent/BRPI0912394A2/pt not_active IP Right Cessation
- 2009-05-14 CA CA2724629A patent/CA2724629C/en not_active Expired - Fee Related
- 2009-05-14 EP EP09747531A patent/EP2297100B1/en active Active
- 2009-05-14 US US12/989,959 patent/US8486943B2/en active Active
- 2009-05-14 AU AU2009246348A patent/AU2009246348B2/en not_active Ceased
- 2009-05-14 WO PCT/US2009/043875 patent/WO2009140448A1/en not_active Ceased
- 2009-05-14 HR HRP20120917AT patent/HRP20120917T1/hr unknown
- 2009-05-14 MX MX2010012436A patent/MX2010012436A/es active IP Right Grant
- 2009-05-14 ES ES09747531T patent/ES2396612T3/es active Active
- 2009-05-14 JP JP2011509679A patent/JP5603327B2/ja active Active
- 2009-05-14 CN CN200980117076XA patent/CN102026974B/zh active Active
- 2009-05-14 PT PT97475313T patent/PT2297100E/pt unknown
- 2009-05-14 SI SI200930447T patent/SI2297100T1/sl unknown
- 2009-05-14 DK DK09747531.3T patent/DK2297100T3/da active
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2012
- 2012-11-14 CY CY20121101095T patent/CY1113341T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US8486943B2 (en) | 2013-07-16 |
| EA019713B1 (ru) | 2014-05-30 |
| EP2297100B1 (en) | 2012-10-31 |
| JP2011520903A (ja) | 2011-07-21 |
| SI2297100T1 (sl) | 2013-02-28 |
| AU2009246348A8 (en) | 2010-12-16 |
| EP2297100A1 (en) | 2011-03-23 |
| AU2009246348B2 (en) | 2012-04-12 |
| MX2010012436A (es) | 2010-12-06 |
| JP5603327B2 (ja) | 2014-10-08 |
| CY1113341T1 (el) | 2016-06-22 |
| US20110039855A1 (en) | 2011-02-17 |
| PT2297100E (pt) | 2013-01-24 |
| AU2009246348A1 (en) | 2009-11-19 |
| HRP20120917T1 (hr) | 2012-12-31 |
| ES2396612T3 (es) | 2013-02-22 |
| CA2724629A1 (en) | 2009-11-19 |
| KR101278788B1 (ko) | 2013-06-25 |
| BRPI0912394A2 (pt) | 2016-07-26 |
| EA201071317A1 (ru) | 2011-06-30 |
| CN102026974A (zh) | 2011-04-20 |
| CN102026974B (zh) | 2013-08-28 |
| KR20100132551A (ko) | 2010-12-17 |
| WO2009140448A8 (en) | 2010-01-07 |
| DK2297100T3 (da) | 2012-12-17 |
| WO2009140448A1 (en) | 2009-11-19 |
| PL2297100T3 (pl) | 2013-03-29 |
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| MKLA | Lapsed |
Effective date: 20180514 |