KR101121471B1 - 안드로겐 수용체 조정제로서의 테트라히드로시클로펜타［ｂ］인돌 화합물 - Google Patents
안드로겐 수용체 조정제로서의 테트라히드로시클로펜타［ｂ］인돌 화합물 Download PDFInfo
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- KR101121471B1 KR101121471B1 KR1020097010232A KR20097010232A KR101121471B1 KR 101121471 B1 KR101121471 B1 KR 101121471B1 KR 1020097010232 A KR1020097010232 A KR 1020097010232A KR 20097010232 A KR20097010232 A KR 20097010232A KR 101121471 B1 KR101121471 B1 KR 101121471B1
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- South Korea
- Prior art keywords
- tetrahydrocyclopenta
- delete delete
- cyano
- pyridin
- thiazol
- 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.)
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- IAZKTAKWBHQCGF-UHFFFAOYSA-N 1,2,3,3a-tetrahydrocyclopenta[b]indole Chemical class N1=C2C=CC=CC2=C2C1CCC2 IAZKTAKWBHQCGF-UHFFFAOYSA-N 0.000 title abstract description 11
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 125000004496 thiazol-5-yl group Chemical group S1C=NC=C1* 0.000 claims description 12
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
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- LFKDJXLFVYVEFG-UHFFFAOYSA-N tert-butyl carbamate Chemical compound CC(C)(C)OC(N)=O LFKDJXLFVYVEFG-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- WQCGDEQLNYULRY-UHFFFAOYSA-N tert-butyl n-(7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl)carbamate Chemical compound N1C2=CC=C(C#N)C=C2C2=C1CC(NC(=O)OC(C)(C)C)C2 WQCGDEQLNYULRY-UHFFFAOYSA-N 0.000 description 1
- WQCGDEQLNYULRY-LLVKDONJSA-N tert-butyl n-[(2r)-7-cyano-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl]carbamate Chemical compound N1C2=CC=C(C#N)C=C2C2=C1C[C@H](NC(=O)OC(C)(C)C)C2 WQCGDEQLNYULRY-LLVKDONJSA-N 0.000 description 1
- FHHKQFJHKLKWFQ-LLVKDONJSA-N tert-butyl n-[(2r)-7-formyl-1,2,3,4-tetrahydrocyclopenta[b]indol-2-yl]carbamate Chemical compound N1C2=CC=C(C=O)C=C2C2=C1C[C@H](NC(=O)OC(C)(C)C)C2 FHHKQFJHKLKWFQ-LLVKDONJSA-N 0.000 description 1
- UHDCOVNPQFZHIG-KRWDZBQOSA-N tert-butyl 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)C)C2=C1C1=CC(C#N)=CC=C1N2CC1=CC=CC=N1 UHDCOVNPQFZHIG-KRWDZBQOSA-N 0.000 description 1
- UHDCOVNPQFZHIG-UHFFFAOYSA-N tert-butyl n-[7-cyano-4-(pyridin-2-ylmethyl)-2,3-dihydro-1h-cyclopenta[b]indol-2-yl]carbamate Chemical compound C1C(NC(=O)OC(C)(C)C)CC2=C1C1=CC(C#N)=CC=C1N2CC1=CC=CC=N1 UHDCOVNPQFZHIG-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 210000002303 tibia Anatomy 0.000 description 1
- 238000013518 transcription Methods 0.000 description 1
- 230000035897 transcription Effects 0.000 description 1
- 239000012096 transfection reagent Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
Classifications
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- 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
- C07D209/58—[b]- or [c]-condensed
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- 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
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- 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
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- 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
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- 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
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- 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
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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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
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- 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
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- 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
- A61P7/06—Antianaemics
-
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
-
- 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
- C07D209/58—[b]- or [c]-condensed
- C07D209/70—[b]- or [c]-condensed containing carbocyclic rings other than six-membered
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Physical Education & Sports Medicine (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Endocrinology (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Epidemiology (AREA)
- Reproductive Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Biomedical Technology (AREA)
- Anesthesiology (AREA)
- Gynecology & Obstetrics (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Immunology (AREA)
- Pulmonology (AREA)
- Psychiatry (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
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 (2)
| Publication Number | Publication Date |
|---|---|
| KR20090082229A KR20090082229A (ko) | 2009-07-29 |
| KR101121471B1 true KR101121471B1 (ko) | 2012-02-28 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
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| KR1020097010232A Active KR101121471B1 (ko) | 2006-11-20 | 2007-11-06 | 안드로겐 수용체 조정제로서의 테트라히드로시클로펜타［ｂ］인돌 화합물 |
Country Status (36)
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| MX2010009162A (es) | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| HRP20120917T1 (hr) * | 2008-05-16 | 2012-12-31 | Eli Lilly & Company | TETRAHIDROCIKLOPENTA[b]INDOLSKI MODULATORI ANDROGENOG RECEPTORA |
| 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 |
| MX338831B (es) | 2010-02-04 | 2016-05-03 | Radius Health Inc | Moduladores selectivos de receptores de androgenos. |
| ME02474B (me) | 2010-05-12 | 2017-02-20 | Radius Health Inc | Terapijski režimi |
| US8642632B2 (en) | 2010-07-02 | 2014-02-04 | Radius Health, Inc. | Selective androgen receptor modulators |
| EP2621901B1 (en) | 2010-09-28 | 2015-07-29 | 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 |
| SMT202300072T1 (it) | 2014-03-28 | 2023-05-12 | Univ Duke | Cancro della mammella mediante l'utilizzo di modulatori selettivi del recetiore degli estrogeni |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| 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 |
| RU2022108295A (ru) | 2016-06-22 | 2022-04-06 | Эллипсес Фарма Лтд | Способы лечения ar+ рака молочной железы |
| 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 |
| CN117417263A (zh) | 2017-01-05 | 2024-01-19 | 雷迪厄斯制药公司 | Rad1901-2hcl的多晶型形式 |
| CN112423844B (zh) | 2018-07-04 | 2024-08-13 | 雷迪厄斯制药公司 | Rad1901-2hcl的多晶型形式 |
| MA54946A (fr) | 2019-02-12 | 2021-12-22 | Radius Pharmaceuticals Inc | Procédés et composés |
| 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 |
| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005092854A1 (en) | 2004-03-03 | 2005-10-06 | Eli Lilly And Company | Bicyclic substituted indole-derivative steroid hormone nuclear receptor modulators |
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| 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 |
| ATE350036T1 (de) * | 1999-10-14 | 2007-01-15 | Kaken Pharma Co Ltd | Tetrahydroquinolin-derivate |
| EP1423366A1 (en) | 2001-08-09 | 2004-06-02 | 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 |
| 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 |
| US20090170923A1 (en) * | 2004-11-22 | 2009-07-02 | Kristjan Gudmundsson | Hcv inhibitors |
| EP1824821A2 (en) | 2004-11-23 | 2007-08-29 | PTC Therapeutics, Inc. | Carbazole, carboline and indole derivatives useful in the inhibition of vegf production |
| TW200640931A (en) | 2005-02-17 | 2006-12-01 | Wyeth Corp | 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 |
| WO2007047604A2 (en) | 2005-10-18 | 2007-04-26 | Elixir Pharmaceuticals, Inc. | 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 |
| HRP20120917T1 (hr) | 2008-05-16 | 2012-12-31 | Eli Lilly & Company | TETRAHIDROCIKLOPENTA[b]INDOLSKI MODULATORI ANDROGENOG RECEPTORA |
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Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005092854A1 (en) | 2004-03-03 | 2005-10-06 | Eli Lilly And Company | Bicyclic substituted indole-derivative steroid hormone nuclear receptor modulators |
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| Arch. Pharm. Pharm. Med. Chem. 333, 305-311. (2000) |
| Current Topics in Medicinal Chemistry 6, 245-270. (2006) |
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