CA2612723A1 - Tetrahydrocarbazole derivatives useful as androgen receptor modulators - Google Patents
Tetrahydrocarbazole derivatives useful as androgen receptor modulators Download PDFInfo
- Publication number
- CA2612723A1 CA2612723A1 CA002612723A CA2612723A CA2612723A1 CA 2612723 A1 CA2612723 A1 CA 2612723A1 CA 002612723 A CA002612723 A CA 002612723A CA 2612723 A CA2612723 A CA 2612723A CA 2612723 A1 CA2612723 A1 CA 2612723A1
- Authority
- CA
- Canada
- Prior art keywords
- halo
- alkyl
- group
- alkoxy
- methyl
- 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.)
- Abandoned
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- XKLNOVWDVMWTOB-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazole Chemical class N1C2=CC=CC=C2C2=C1CCCC2 XKLNOVWDVMWTOB-UHFFFAOYSA-N 0.000 title 1
- 239000000849 selective androgen receptor modulator Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 43
- 150000003839 salts Chemical class 0.000 claims abstract 10
- 206010057671 Female sexual dysfunction Diseases 0.000 claims abstract 4
- 208000036119 Frailty Diseases 0.000 claims abstract 4
- 206010057672 Male sexual dysfunction Diseases 0.000 claims abstract 4
- 208000029725 Metabolic bone disease Diseases 0.000 claims abstract 4
- 206010049088 Osteopenia Diseases 0.000 claims abstract 4
- 208000001132 Osteoporosis Diseases 0.000 claims abstract 4
- 206010003549 asthenia Diseases 0.000 claims abstract 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 3
- 208000035475 disorder Diseases 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims abstract 3
- 239000003085 diluting agent Substances 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims abstract 2
- 125000005843 halogen group Chemical group 0.000 claims 53
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 46
- -1 amino, hydroxy Chemical group 0.000 claims 40
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 37
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 32
- 125000004093 cyano group Chemical group *C#N 0.000 claims 25
- 125000001424 substituent group Chemical group 0.000 claims 25
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims 20
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 15
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 13
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 12
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims 11
- 229910052739 hydrogen Inorganic materials 0.000 claims 11
- 239000001257 hydrogen Substances 0.000 claims 11
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical group F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims 10
- 108010081348 HRT1 protein Hairy Chemical group 0.000 claims 10
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 claims 10
- 150000003973 alkyl amines Chemical class 0.000 claims 10
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- 125000001153 fluoro group Chemical group F* 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 9
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000000335 thiazolyl group Chemical group 0.000 claims 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 7
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 6
- 125000001544 thienyl group Chemical group 0.000 claims 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 5
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims 4
- 125000003373 pyrazinyl group Chemical group 0.000 claims 4
- 125000000714 pyrimidinyl group Chemical group 0.000 claims 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims 4
- 206010060862 Prostate cancer Diseases 0.000 claims 3
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 3
- 125000001246 bromo group Chemical group Br* 0.000 claims 3
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 3
- 125000002541 furyl group Chemical group 0.000 claims 2
- 125000001072 heteroaryl group Chemical group 0.000 claims 2
- 125000002883 imidazolyl group Chemical group 0.000 claims 2
- 125000001786 isothiazolyl group Chemical group 0.000 claims 2
- HQCNDGFHYHHGGO-GOSISDBHSA-N n-[(3r)-6-(methoxyiminomethyl)-9-(pyridin-2-ylmethyl)-1,2,3,4-tetrahydrocarbazol-3-yl]cyclopropanecarboxamide Chemical compound C([C@@H](CCC=12)NC(=O)C3CC3)C=1C1=CC(C=NOC)=CC=C1N2CC1=CC=CC=N1 HQCNDGFHYHHGGO-GOSISDBHSA-N 0.000 claims 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims 2
- 125000002971 oxazolyl group Chemical group 0.000 claims 2
- 125000003226 pyrazolyl group Chemical group 0.000 claims 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000003831 tetrazolyl group Chemical group 0.000 claims 2
- 125000004306 triazinyl group Chemical group 0.000 claims 2
- 125000001425 triazolyl group Chemical group 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 208000010392 Bone Fractures Diseases 0.000 claims 1
- 208000010228 Erectile Dysfunction Diseases 0.000 claims 1
- 206010058359 Hypogonadism Diseases 0.000 claims 1
- 206010024264 Lethargy Diseases 0.000 claims 1
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000009167 androgen deprivation therapy Methods 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 230000003930 cognitive ability Effects 0.000 claims 1
- 230000003247 decreasing effect Effects 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000008717 functional decline Effects 0.000 claims 1
- 201000001881 impotence Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000003205 muscle Anatomy 0.000 claims 1
- FTPCLTKRSBYWCA-IBGZPJMESA-N n-[(3s)-6-cyano-9-[(3-fluorophenyl)methyl]-1,2,3,4-tetrahydrocarbazol-3-yl]-2-methylpropanamide Chemical compound C([C@@H](C1)NC(=O)C(C)C)CC2=C1C1=CC(C#N)=CC=C1N2CC1=CC=CC(F)=C1 FTPCLTKRSBYWCA-IBGZPJMESA-N 0.000 claims 1
- WIUNAUKEVPPYJI-UHFFFAOYSA-N n-[6-cyano-9-[(6-fluoropyridin-2-yl)methyl]-1,2,3,4-tetrahydrocarbazol-3-yl]cyclopropanecarboxamide Chemical compound FC1=CC=CC(CN2C3=CC=C(C=C3C=3CC(CCC=32)NC(=O)C2CC2)C#N)=N1 WIUNAUKEVPPYJI-UHFFFAOYSA-N 0.000 claims 1
- 208000001076 sarcopenia Diseases 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 claims 1
Classifications
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- 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
- C07D401/14—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 three or more hetero rings
-
- 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
- A61P15/10—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
- A61P19/00—Drugs for skeletal disorders
-
- 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
- A61P19/08—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- 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
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
-
- 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
- C07D401/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Physical Education & Sports Medicine (AREA)
- Reproductive Health (AREA)
- Neurology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Psychiatry (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Pregnancy & Childbirth (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US69360405P | 2005-06-24 | 2005-06-24 | |
| US60/693,604 | 2005-06-24 | ||
| PCT/US2006/024122 WO2007002181A2 (en) | 2005-06-24 | 2006-06-21 | Tetrahydrocarbazole derivatives useful as androgen receptor modulators (sarm) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2612723A1 true CA2612723A1 (en) | 2007-01-04 |
Family
ID=37315277
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002612723A Abandoned CA2612723A1 (en) | 2005-06-24 | 2006-06-21 | Tetrahydrocarbazole derivatives useful as androgen receptor modulators |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US7935722B2 (enExample) |
| EP (1) | EP1902026B1 (enExample) |
| JP (1) | JP5204650B2 (enExample) |
| CN (1) | CN101203491A (enExample) |
| AT (1) | ATE457979T1 (enExample) |
| AU (1) | AU2006262283B2 (enExample) |
| BR (1) | BRPI0611705A2 (enExample) |
| CA (1) | CA2612723A1 (enExample) |
| CY (1) | CY1110014T1 (enExample) |
| DE (1) | DE602006012322D1 (enExample) |
| DK (1) | DK1902026T3 (enExample) |
| ES (1) | ES2339480T3 (enExample) |
| MX (1) | MX2007015905A (enExample) |
| PL (1) | PL1902026T3 (enExample) |
| PT (1) | PT1902026E (enExample) |
| SI (1) | SI1902026T1 (enExample) |
| WO (1) | WO2007002181A2 (enExample) |
Families Citing this family (36)
| 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 |
| US8563542B2 (en) | 2007-09-28 | 2013-10-22 | Cyclacel Limited | Pyrimidine derivatives as protein kinase inhibitors |
| MX2010009162A (es) | 2008-02-22 | 2010-12-21 | Radius Health Inc | Moduladores selectivos del receptor de androgeno. |
| US8268872B2 (en) | 2008-02-22 | 2012-09-18 | Radius Health, Inc. | Selective androgen receptor modulators |
| BRPI0912394A2 (pt) * | 2008-05-16 | 2016-07-26 | Lilly Co Eli | moduladores do receptor de androgênio à base de tetra-hidrociclopenta[b]indol |
| CN101648933B (zh) * | 2009-09-21 | 2011-07-20 | 四川大学 | 3,4-二氢-4-氧-2h-1-苯并吡喃曼尼希碱类化合物、其制备方法和用途 |
| 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 |
| KR101779630B1 (ko) | 2009-12-21 | 2017-09-18 | 어레이 바이오파마 인크. | ｃＦＭＳ 억제제로서 치환된 Ｎ-（１Ｈ-인다졸-４-일）이미다조［１,２-ａ］피리딘-３-카복사미드 화합물 |
| CA2788907A1 (en) * | 2010-02-04 | 2011-08-11 | 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 |
| ES2550319T3 (es) | 2010-09-28 | 2015-11-06 | Radius Health, Inc | Moduladores selectivos del receptor de andrógenos |
| BR112013028895A2 (pt) | 2011-05-10 | 2016-08-09 | Bayer Ip Gmbh | (tio)carbonilamidinas bicíclicas |
| US9624214B2 (en) | 2012-11-05 | 2017-04-18 | Bayer Pharma Aktiengesellschaft | Amino-substituted imidazo[1,2-a]pyridinecarboxamides and their use |
| US8778964B2 (en) | 2012-11-05 | 2014-07-15 | Bayer Pharma Aktiengesellschaft | Hydroxy-substituted imidazo[1,2-a]-pyridinecarboxamides and their use |
| CN105339368B (zh) | 2013-06-04 | 2017-08-15 | 拜耳制药股份公司 | 3‑芳基‑取代的咪唑并[1,2‑a]吡啶及其用途 |
| CN103694142A (zh) * | 2013-11-28 | 2014-04-02 | 浙江科技学院 | 4-N-Boc-氨基环己酮的制备方法 |
| WO2015124544A1 (de) | 2014-02-19 | 2015-08-27 | Bayer Pharma Aktiengesellschaft | 3-(pyrimidin-2-yl)imidazo[1,2-a]pyridine |
| JP2017508810A (ja) | 2014-03-21 | 2017-03-30 | バイエル・ファルマ・アクティエンゲゼルシャフト | シアノ置換イミダゾ［１，２−ａ］ピリジンカルボキサミドおよびその使用 |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| RS67458B1 (sr) | 2014-03-28 | 2025-12-31 | Univ Duke | Lečenje kancera dojke pozitivnog na receptor estrogena upotrebom selektivnih modulatora receptora estrogena |
| JP2017536396A (ja) | 2014-12-02 | 2017-12-07 | バイエル・ファルマ・アクティエンゲゼルシャフト | ヘテロアリール置換イミダゾ［１，２−ａ］ピリジンおよびその使用 |
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| KR102881465B1 (ko) | 2017-01-05 | 2025-11-04 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
| CN109730996B (zh) * | 2017-03-01 | 2021-08-24 | 浙江大学 | 喹啉结构类型雄激素受体拮抗剂及其应用 |
| WO2019170543A1 (en) | 2018-03-07 | 2019-09-12 | Bayer Aktiengesellschaft | Identification and use of erk5 inhibitors |
| SG11202011135WA (en) | 2018-05-14 | 2020-12-30 | Nuvation Bio Inc | Anti-cancer nuclear hormone receptor-targeting compounds |
| CN112423844B (zh) | 2018-07-04 | 2024-08-13 | 雷迪厄斯制药公司 | Rad1901-2hcl的多晶型形式 |
| JOP20210218A1 (ar) | 2019-02-12 | 2023-01-30 | Radius Pharmaceuticals Inc | عمليات ومركبات |
| US11826430B2 (en) | 2019-05-14 | 2023-11-28 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
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| KR20230160299A (ko) | 2021-03-23 | 2023-11-23 | 누베이션 바이오 인크. | 항암 핵 호르몬 수용체 표적화 화합물 |
| US12006314B2 (en) | 2021-05-03 | 2024-06-11 | Nuvation Bio Inc. | Anti-cancer nuclear hormone receptor-targeting compounds |
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| CN118993985A (zh) * | 2023-05-17 | 2024-11-22 | 中国医学科学院药物研究所 | 一种具有抗肿瘤活性的化合物，其制备方法及制药用途 |
| CN119874601B (zh) * | 2025-01-06 | 2025-10-31 | 山东大学 | 一种3,3-二甲基-1,2,3,4-四氢-9h-咔唑类衍生物及其制备方法与应用 |
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| US3959309A (en) * | 1968-01-24 | 1976-05-25 | Sterling Drug Inc. | 3-Amido-1,2,3,4-tetrahydrocarbazoles |
| 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 |
| GB9310635D0 (en) * | 1993-05-21 | 1993-07-07 | Glaxo Group Ltd | Chemical compounds |
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| WO2003051837A2 (de) * | 2001-12-14 | 2003-06-26 | Zentaris Gmbh | Tetrahydrocarbazolderivate als liganden für g-protein gekoppelte rezeptoren (gpcr) |
| WO2003097598A1 (en) | 2002-05-16 | 2003-11-27 | Shionogi & Co., Ltd. | Compound exhibiting pgd 2 receptor antagonism |
| UA79504C2 (en) * | 2002-11-07 | 2007-06-25 | Organon Nv | Indols for treating diseases associated with androgen receptors |
| EP1648466A1 (en) * | 2003-07-07 | 2006-04-26 | Boehringer Ingelheim International GmbH | Use of cgrp antagonists in treatment and prevention of hot flushes in prostate cancer patients |
| US7019022B2 (en) | 2003-12-15 | 2006-03-28 | Merck Frosst Canada & Co. | Substituted tetrahydrocarbazole and cyclopentanoindole derivatives |
| JP2008520741A (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 | 翻訳制御によるｖｅｇｆ生成を阻害するための活性因子としてのテトラヒドロカルバゾール |
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- 2006-06-21 CN CNA200680022629XA patent/CN101203491A/zh active Pending
- 2006-06-21 CA CA002612723A patent/CA2612723A1/en not_active Abandoned
- 2006-06-21 WO PCT/US2006/024122 patent/WO2007002181A2/en not_active Ceased
- 2006-06-21 BR BRPI0611705A patent/BRPI0611705A2/pt not_active IP Right Cessation
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| MX2007015905A (es) | 2008-03-06 |
| SI1902026T1 (sl) | 2010-07-30 |
| BRPI0611705A2 (pt) | 2016-11-16 |
| AU2006262283B2 (en) | 2011-10-13 |
| JP5204650B2 (ja) | 2013-06-05 |
| WO2007002181A2 (en) | 2007-01-04 |
| CN101203491A (zh) | 2008-06-18 |
| US7935722B2 (en) | 2011-05-03 |
| EP1902026B1 (en) | 2010-02-17 |
| CY1110014T1 (el) | 2015-01-14 |
| WO2007002181A3 (en) | 2007-03-01 |
| US20100022550A1 (en) | 2010-01-28 |
| JP2008546791A (ja) | 2008-12-25 |
| EP1902026A2 (en) | 2008-03-26 |
| ATE457979T1 (de) | 2010-03-15 |
| AU2006262283A1 (en) | 2007-01-04 |
| PT1902026E (pt) | 2010-03-17 |
| DE602006012322D1 (de) | 2010-04-01 |
| ES2339480T3 (es) | 2010-05-20 |
| DK1902026T3 (da) | 2010-04-26 |
| PL1902026T3 (pl) | 2010-07-30 |
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