JP2010510231A5 - - Google Patents
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- Publication number
- JP2010510231A5 JP2010510231A5 JP2009537272A JP2009537272A JP2010510231A5 JP 2010510231 A5 JP2010510231 A5 JP 2010510231A5 JP 2009537272 A JP2009537272 A JP 2009537272A JP 2009537272 A JP2009537272 A JP 2009537272A JP 2010510231 A5 JP2010510231 A5 JP 2010510231A5
- Authority
- JP
- Japan
- Prior art keywords
- thiazol
- pyridin
- cyano
- amino
- pyrazin
- 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
- -1 methoxy, ethoxy, propoxy, isopropoxy, isobutoxy, tert-butoxy, cyclopropyl Chemical group 0.000 claims 19
- 150000001875 compounds Chemical class 0.000 claims 5
- 230000003247 decreasing effect Effects 0.000 claims 5
- 150000003839 salts Chemical class 0.000 claims 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- IHIWYQYVBNODSV-KRWDZBQOSA-N propan-2-yl n-[(2s)-7-cyano-4-(pyridin-2-ylmethyl)-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=N1 IHIWYQYVBNODSV-KRWDZBQOSA-N 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 206010012205 Delayed puberty Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 206010024264 Lethargy Diseases 0.000 claims 1
- 208000029725 Metabolic bone disease Diseases 0.000 claims 1
- 206010049088 Osteopenia Diseases 0.000 claims 1
- 208000001132 Osteoporosis Diseases 0.000 claims 1
- 230000032683 aging Effects 0.000 claims 1
- 208000007502 anemia Diseases 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000004064 dysfunction Effects 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 230000006870 function Effects 0.000 claims 1
- 125000001072 heteroaryl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 125000002249 indol-2-yl group Chemical group [H]C1=C([H])C([H])=C2N([H])C([*])=C([H])C2=C1[H] 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000001793 isothiazol-3-yl group Chemical group [H]C1=C([H])C(*)=NS1 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- QIODLAKLXOMDJQ-INIZCTEOSA-N propan-2-yl n-[(2s)-4-[(2-aminopyridin-3-yl)methyl]-7-cyano-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=CN=C1N QIODLAKLXOMDJQ-INIZCTEOSA-N 0.000 claims 1
- QOGITFZSMDQJMF-ZDUSSCGKSA-N propan-2-yl n-[(2s)-4-[(4-amino-1,3-thiazol-5-yl)methyl]-7-cyano-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=C1N2CC=1SC=NC=1N QOGITFZSMDQJMF-ZDUSSCGKSA-N 0.000 claims 1
- CFZPNDIMNLMLED-AWEZNQCLSA-N propan-2-yl n-[(2s)-7-cyano-4-(1,3-thiazol-5-ylmethyl)-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=CN=CS1 CFZPNDIMNLMLED-AWEZNQCLSA-N 0.000 claims 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims 1
- 125000003373 pyrazinyl group Chemical group 0.000 claims 1
- 125000002206 pyridazin-3-yl group Chemical group [H]C1=C([H])C([H])=C(*)N=N1 0.000 claims 1
- 125000002098 pyridazinyl group Chemical group 0.000 claims 1
- 125000004076 pyridyl group Chemical group 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 1
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 1
- 208000001076 sarcopenia Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 230000036299 sexual function Effects 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 claims 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 claims 1
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims 1
- 125000000335 thiazolyl group Chemical group 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US86648406P | 2006-11-20 | 2006-11-20 | |
| US60/866,484 | 2006-11-20 | ||
| PCT/US2007/083745 WO2008063867A2 (en) | 2006-11-20 | 2007-11-06 | Tetrahydrocyclopenta[b] indole compounds as androgen receptor modulators |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010510231A JP2010510231A (ja) | 2010-04-02 |
| JP2010510231A5 true JP2010510231A5 (OSRAM) | 2010-12-16 |
| JP5399259B2 JP5399259B2 (ja) | 2014-01-29 |
Family
ID=39415431
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009537272A Active JP5399259B2 (ja) | 2006-11-20 | 2007-11-06 | アンドロゲン受容体モジュレータとしてのテトラヒドロペンタ［ｂ］インドール化合物 |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US7968587B2 (OSRAM) |
| EP (1) | EP2094658B1 (OSRAM) |
| JP (1) | JP5399259B2 (OSRAM) |
| KR (1) | KR101121471B1 (OSRAM) |
| CN (1) | CN101541749B (OSRAM) |
| AR (1) | AR063559A1 (OSRAM) |
| AT (1) | ATE538091T1 (OSRAM) |
| AU (1) | AU2007324046B2 (OSRAM) |
| BR (1) | BRPI0719092B8 (OSRAM) |
| CA (1) | CA2670340C (OSRAM) |
| CL (1) | CL2007003182A1 (OSRAM) |
| CO (1) | CO6190513A2 (OSRAM) |
| CR (1) | CR10802A (OSRAM) |
| CY (1) | CY1112284T1 (OSRAM) |
| DK (1) | DK2094658T3 (OSRAM) |
| EA (1) | EA015627B1 (OSRAM) |
| EC (1) | ECSP099350A (OSRAM) |
| ES (1) | ES2376048T3 (OSRAM) |
| HR (1) | HRP20120032T1 (OSRAM) |
| IL (1) | IL198410A (OSRAM) |
| JO (1) | JO2800B1 (OSRAM) |
| MA (1) | MA31072B1 (OSRAM) |
| MX (1) | MX2009005251A (OSRAM) |
| MY (1) | MY154547A (OSRAM) |
| NO (1) | NO342531B1 (OSRAM) |
| NZ (1) | NZ576296A (OSRAM) |
| PE (1) | PE20081161A1 (OSRAM) |
| PL (1) | PL2094658T3 (OSRAM) |
| PT (1) | PT2094658E (OSRAM) |
| RS (1) | RS52191B (OSRAM) |
| SI (1) | SI2094658T1 (OSRAM) |
| TN (1) | TN2009000189A1 (OSRAM) |
| TW (1) | TWI398438B (OSRAM) |
| UA (1) | UA98777C2 (OSRAM) |
| WO (1) | WO2008063867A2 (OSRAM) |
| ZA (1) | ZA200903096B (OSRAM) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BRPI0907844B8 (pt) | 2008-02-22 | 2021-05-25 | Radius Health Inc | compostos e método para modular um receptor de andrógeno, processos de preparação e composição farmacêutica dos mesmos e seus usos |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| EP2297100B1 (en) * | 2008-05-16 | 2012-10-31 | Eli Lilly & Company | Tetrahydrocyclopenta[b]indole androgen receptor modulators |
| AR078862A1 (es) | 2009-11-13 | 2011-12-07 | Lilly Co Eli | Ester isopropilico del acido ((s)-7-ciano-4-((2r,3s)-3-hidroxitetrahidrofuran-2-ilmetil)-1,2,3,4-tetrahidro-ciclopenta(b)indol-2-il)carbamico, composiciones farmaceuticas que lo comprenden y su uso en terapia |
| US8987319B2 (en) | 2010-02-04 | 2015-03-24 | Radius Health, Inc. | Selective androgen receptor modulators |
| PT2568806T (pt) | 2010-05-12 | 2016-08-05 | Radius Health Inc | Regimes terapêuticos |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| WO2012047617A1 (en) | 2010-09-28 | 2012-04-12 | Radius Health, Inc. | Selective androgen receptor modulators |
| US20140113824A1 (en) | 2011-05-10 | 2014-04-24 | Bayer Intellectual Property Gmbh | Bicyclic (thio)carbonylamidines |
| CN103265479B (zh) * | 2013-06-14 | 2017-12-08 | 南开大学 | 一种6‑氯甲基烟酸叔丁酯的合成方法 |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| PL3122426T3 (pl) | 2014-03-28 | 2023-05-15 | Duke University | Leczenie raka sutka z zastosowaniem selektywnych modulatorów receptora estrogenowego |
| TWI744723B (zh) | 2014-06-20 | 2021-11-01 | 美商基利科學股份有限公司 | 多環型胺甲醯基吡啶酮化合物之合成 |
| JOP20180072A1 (ar) | 2014-09-11 | 2019-01-30 | Lilly Co Eli | علاج الأعراض المرتبطة بالعلاج بالحرمان من الأندروجين |
| SMT202200199T1 (it) | 2016-06-22 | 2022-07-21 | Ellipses Pharma Ltd | Metodi di trattamento del cancro del seno 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 |
| EP4374925A3 (en) | 2017-01-05 | 2025-01-15 | Radius Pharmaceuticals, Inc. | Polymorphic forms of rad1901-2hcl |
| CN112423844B (zh) | 2018-07-04 | 2024-08-13 | 雷迪厄斯制药公司 | Rad1901-2hcl的多晶型形式 |
| CN119390714A (zh) | 2019-02-12 | 2025-02-07 | 雷迪厄斯制药公司 | 方法和化合物 |
| EP4096660A1 (en) * | 2020-01-27 | 2022-12-07 | EirGen Pharma Ltd. | Tetrahydrocyclopenta[b]indole compounds for the treatment of renal disease |
| US11986461B1 (en) * | 2023-08-24 | 2024-05-21 | King Faisal University | 3-(1-(3-(dimethylamino)propyl)-4,5-diphenyl-1H-imidazol-2-yl)pyridin-2-ol as an antitumor and antimicrobial compound |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| WO2001027086A1 (en) * | 1999-10-14 | 2001-04-19 | Kaken Pharmaceutical Co., Ltd. | Tetrahydroquinoline derivatives |
| 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) |
| US7534897B2 (en) | 2002-05-16 | 2009-05-19 | Shionogi & Co., Ltd. | Indole arylsulfonaimide compounds exhibiting PGD 2 receptor antagonism |
| US20060074124A1 (en) | 2003-09-12 | 2006-04-06 | Andrew Napper | Methods of treating a disorder |
| US20050245540A1 (en) * | 2003-12-09 | 2005-11-03 | Fujisawa Pharmaceutical Co., Ltd. | New methods |
| US7019022B2 (en) | 2003-12-15 | 2006-03-28 | Merck Frosst Canada & Co. | Substituted tetrahydrocarbazole and cyclopentanoindole derivatives |
| EP1723105B1 (en) * | 2004-03-03 | 2013-05-15 | Eli Lilly And Company | Bicyclic substituted indole-derivative steroid hormone nuclear receptor modulators |
| US20090170923A1 (en) * | 2004-11-22 | 2009-07-02 | Kristjan Gudmundsson | Hcv inhibitors |
| JP2008520742A (ja) | 2004-11-23 | 2008-06-19 | ピーティーシー セラピューティクス， インコーポレイテッド | Ｖｅｇｆ産生の阻害に有用なカルバゾール誘導体、カルボリン誘導体およびインドール誘導体 |
| EP1856126A2 (en) | 2005-02-17 | 2007-11-21 | Wyeth a Corporation of the State of Delaware | Cycloalkylfused indole, benzothiophene, benzofuran and indene derivatives |
| JP5204650B2 (ja) | 2005-06-24 | 2013-06-05 | イーライ リリー アンド カンパニー | アンドロゲン受容体調節物質として有用なテトラヒドロカルバゾール誘導体 |
| 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 |
| EP2297100B1 (en) | 2008-05-16 | 2012-10-31 | Eli Lilly & Company | Tetrahydrocyclopenta[b]indole androgen receptor modulators |
-
2007
- 2007-06-11 UA UAA200904819A patent/UA98777C2/ru unknown
- 2007-11-02 TW TW096141527A patent/TWI398438B/zh not_active IP Right Cessation
- 2007-11-05 AR ARP070104913A patent/AR063559A1/es active IP Right Grant
- 2007-11-05 CL CL200703182A patent/CL2007003182A1/es unknown
- 2007-11-06 WO PCT/US2007/083745 patent/WO2008063867A2/en not_active Ceased
- 2007-11-06 ES ES07844898T patent/ES2376048T3/es active Active
- 2007-11-06 PL PL07844898T patent/PL2094658T3/pl unknown
- 2007-11-06 NZ NZ576296A patent/NZ576296A/en not_active IP Right Cessation
- 2007-11-06 DK DK07844898.2T patent/DK2094658T3/da active
- 2007-11-06 HR HR20120032T patent/HRP20120032T1/hr unknown
- 2007-11-06 MY MYPI20092021A patent/MY154547A/en unknown
- 2007-11-06 AT AT07844898T patent/ATE538091T1/de active
- 2007-11-06 BR BRPI0719092A patent/BRPI0719092B8/pt active IP Right Grant
- 2007-11-06 SI SI200730864T patent/SI2094658T1/sl unknown
- 2007-11-06 RS RS20120056A patent/RS52191B/sr unknown
- 2007-11-06 EA EA200970500A patent/EA015627B1/ru unknown
- 2007-11-06 JP JP2009537272A patent/JP5399259B2/ja active Active
- 2007-11-06 KR KR1020097010232A patent/KR101121471B1/ko active Active
- 2007-11-06 MX MX2009005251A patent/MX2009005251A/es active IP Right Grant
- 2007-11-06 US US12/447,693 patent/US7968587B2/en active Active
- 2007-11-06 AU AU2007324046A patent/AU2007324046B2/en active Active
- 2007-11-06 PT PT07844898T patent/PT2094658E/pt unknown
- 2007-11-06 EP EP07844898A patent/EP2094658B1/en active Active
- 2007-11-06 CA CA2670340A patent/CA2670340C/en active Active
- 2007-11-06 CN CN2007800430385A patent/CN101541749B/zh active Active
- 2007-11-08 PE PE2007001544A patent/PE20081161A1/es active IP Right Grant
- 2007-11-11 JO JO2007470A patent/JO2800B1/en active
-
2009
- 2009-04-27 IL IL198410A patent/IL198410A/en active IP Right Grant
- 2009-05-05 ZA ZA200903096A patent/ZA200903096B/xx unknown
- 2009-05-15 TN TNP2009000189A patent/TN2009000189A1/fr unknown
- 2009-05-18 CO CO09050693A patent/CO6190513A2/es active IP Right Grant
- 2009-05-19 CR CR10802A patent/CR10802A/es unknown
- 2009-05-20 EC EC2009009350A patent/ECSP099350A/es unknown
- 2009-05-28 NO NO20092103A patent/NO342531B1/no unknown
- 2009-06-17 MA MA32013A patent/MA31072B1/fr unknown
-
2012
- 2012-02-14 CY CY20121100148T patent/CY1112284T1/el unknown
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