CZ305195A3 - Carbazole derivatives, process of their preparation, their use and pharmaceutical compositions containing thereof - Google Patents
Carbazole derivatives, process of their preparation, their use and pharmaceutical compositions containing thereof Download PDFInfo
- Publication number
- CZ305195A3 CZ305195A3 CZ953051A CZ305195A CZ305195A3 CZ 305195 A3 CZ305195 A3 CZ 305195A3 CZ 953051 A CZ953051 A CZ 953051A CZ 305195 A CZ305195 A CZ 305195A CZ 305195 A3 CZ305195 A3 CZ 305195A3
- Authority
- CZ
- Czechia
- Prior art keywords
- formula
- compound
- carbazole
- ylmethyl
- fluoro
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 16
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 150
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000012453 solvate Substances 0.000 claims abstract description 23
- 239000003098 androgen Substances 0.000 claims abstract description 14
- 239000003814 drug Substances 0.000 claims abstract description 12
- 239000000262 estrogen Substances 0.000 claims abstract description 12
- 125000006575 electron-withdrawing group Chemical group 0.000 claims abstract description 8
- 125000005843 halogen group Chemical group 0.000 claims abstract description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 55
- 238000006243 chemical reaction Methods 0.000 claims description 27
- 239000004480 active ingredient Substances 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 238000011282 treatment Methods 0.000 claims description 12
- 229940011871 estrogen Drugs 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 229940124597 therapeutic agent Drugs 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
- LFCQNAOJQWIHSR-UHFFFAOYSA-N 2-fluoro-7-(pyridin-3-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CC1=CC=CN=C1 LFCQNAOJQWIHSR-UHFFFAOYSA-N 0.000 claims description 5
- 229940030486 androgens Drugs 0.000 claims description 5
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 4
- 239000002552 dosage form Substances 0.000 claims description 4
- SSPREYNSXYGGTR-UHFFFAOYSA-N 1,4,7-trifluoro-2-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=C(F)C=3)C=1NC2=C(F)C=3CN1C=NC=N1 SSPREYNSXYGGTR-UHFFFAOYSA-N 0.000 claims description 3
- GJYDAAIUCZMZGI-UHFFFAOYSA-N 1,7-difluoro-2-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=C(F)C=3CN1C=NC=N1 GJYDAAIUCZMZGI-UHFFFAOYSA-N 0.000 claims description 3
- UUNNIGZLLLUITE-UHFFFAOYSA-N 2,4-difluoro-7-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC(F)=C(C2=CC=3)C=1NC2=CC=3CN1C=NC=N1 UUNNIGZLLLUITE-UHFFFAOYSA-N 0.000 claims description 3
- CDFBRMQNNCVRSY-UHFFFAOYSA-N 2-fluoro-7-(1,2,4-triazol-1-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CN1C=NC=N1 CDFBRMQNNCVRSY-UHFFFAOYSA-N 0.000 claims description 3
- CJKAHOZICMOBTA-UHFFFAOYSA-N 2-fluoro-7-(pyridin-4-ylmethyl)-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CC1=CC=NC=C1 CJKAHOZICMOBTA-UHFFFAOYSA-N 0.000 claims description 3
- AXUGYCMGYYRNSE-UHFFFAOYSA-N 2-fluoro-7-[(3-fluoropyridin-4-yl)methyl]-9h-carbazole Chemical compound C=1C(F)=CC=C(C2=CC=3)C=1NC2=CC=3CC1=CC=NC=C1F AXUGYCMGYYRNSE-UHFFFAOYSA-N 0.000 claims description 3
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- JJSUEFIAVOMCKU-UHFFFAOYSA-N tert-butyl 2-fluoro-7-formylcarbazole-9-carboxylate Chemical compound C1=C(C=O)C=C2N(C(=O)OC(C)(C)C)C3=CC(F)=CC=C3C2=C1 JJSUEFIAVOMCKU-UHFFFAOYSA-N 0.000 description 1
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- USFPINLPPFWTJW-UHFFFAOYSA-N tetraphenylphosphonium Chemical compound C1=CC=CC=C1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 USFPINLPPFWTJW-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939310635A GB9310635D0 (en) | 1993-05-21 | 1993-05-21 | Chemical compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CZ305195A3 true CZ305195A3 (en) | 1996-06-12 |
Family
ID=10736007
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CZ953051A CZ305195A3 (en) | 1993-05-21 | 1994-05-19 | Carbazole derivatives, process of their preparation, their use and pharmaceutical compositions containing thereof |
Country Status (19)
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|---|---|
| EP (1) | EP0699196A1 (cg-RX-API-DMAC10.html) |
| JP (1) | JPH08510455A (cg-RX-API-DMAC10.html) |
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| BG (1) | BG100154A (cg-RX-API-DMAC10.html) |
| CA (1) | CA2162921A1 (cg-RX-API-DMAC10.html) |
| CZ (1) | CZ305195A3 (cg-RX-API-DMAC10.html) |
| FI (1) | FI955587A0 (cg-RX-API-DMAC10.html) |
| GB (1) | GB9310635D0 (cg-RX-API-DMAC10.html) |
| HU (1) | HUT73790A (cg-RX-API-DMAC10.html) |
| IL (1) | IL109703A0 (cg-RX-API-DMAC10.html) |
| NO (1) | NO954681L (cg-RX-API-DMAC10.html) |
| OA (1) | OA10195A (cg-RX-API-DMAC10.html) |
| PE (1) | PE31195A1 (cg-RX-API-DMAC10.html) |
| PL (1) | PL311702A1 (cg-RX-API-DMAC10.html) |
| SK (1) | SK142495A3 (cg-RX-API-DMAC10.html) |
| TW (1) | TW279866B (cg-RX-API-DMAC10.html) |
| WO (1) | WO1994027989A1 (cg-RX-API-DMAC10.html) |
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Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ273681A (en) * | 1993-09-30 | 1996-09-25 | Yamanouchi Pharma Co Ltd | Fluoroenylmethylazole derivatives (including tricyclic ring systems where the middle ring is heterosubstituted) |
| WO1996014090A1 (en) * | 1994-11-07 | 1996-05-17 | Janssen Pharmaceutica N.V. | Compositions comprising carbazoles and cyclodextrins |
| EP0820989A4 (en) * | 1995-03-01 | 1998-05-06 | Yamanouchi Pharma Co Ltd | IMIDAZOLE DERIVATIVES AND MEDICINAL COMPOSITION BASED ON SAID DERIVATIVES |
| US6420375B1 (en) * | 1997-02-21 | 2002-07-16 | Takeda Chemical Industries, Ltd. | Fused ring compounds, process for producing the same and use thereof |
| AR034854A1 (es) | 2000-11-17 | 2004-03-24 | Takeda Chemical Industries Ltd | Compuesto de imidazol condensado, prodroga del mismo, composición farmaceutica y agente para reducir androgenos que lo contienen ,metodo para producirlo, sal diastereomerica de dicho compuesto y metodo para producir un compuesto opticamente activo del compuesto |
| CA2429437A1 (en) | 2000-11-20 | 2002-05-23 | Takeda Chemical Industries, Ltd. | Imidazole derivatives, process for their preparation and their use |
| EP1348706B1 (en) | 2000-12-08 | 2009-08-19 | Takeda Pharmaceutical Company Limited | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| DE602006012322D1 (de) * | 2005-06-24 | 2010-04-01 | Lilly Co Eli | Als androgen-rezeptor-modulatoren verwendbare tetrahydrocarbazol-derivate |
| GB0525323D0 (en) | 2005-12-13 | 2006-01-18 | Sterix Ltd | Compound |
| US8093279B2 (en) | 2005-12-13 | 2012-01-10 | Gillian Reed, legal representative | Compound |
| CN100586932C (zh) * | 2007-01-26 | 2010-02-03 | 中国医学科学院医药生物技术研究所 | 抗肿瘤化合物及其制备方法 |
| NZ596488A (en) | 2009-06-26 | 2012-11-30 | Novartis Ag | 1, 3-disubstituted imidazolidin-2-one derivatives as inhibitors of cyp 17 |
| WO2011097496A1 (en) * | 2010-02-04 | 2011-08-11 | Radius Health, Inc. | Selective androgen receptor modulators |
| MX342898B (es) | 2010-05-12 | 2016-10-18 | Radius Health Inc * | Regimen terapéutico de la sal de diclorhidrato del (r) -6-(2-(etil (4-2(etilamino) etil) bencil) amino)-4-metoxifenil)-5, 6,7,8-tetrahidronaftaleno-2-ol. |
| EP2600855A2 (en) | 2010-08-04 | 2013-06-12 | Pellficure Pharmaceuticals, Inc. | Combination therapy for the treatment of prostate carcinoma |
| US8946260B2 (en) | 2010-09-16 | 2015-02-03 | Novartis Ag | 17α-hydroxylase/C17,20-lyase inhibitors |
| ES2550319T3 (es) | 2010-09-28 | 2015-11-06 | Radius Health, Inc | Moduladores selectivos del receptor de andrógenos |
| EP2702052B1 (en) | 2011-04-28 | 2017-10-18 | Novartis AG | 17alpha-hydroxylase/c17,20-lyase inhibitors |
| US9492460B2 (en) * | 2013-02-27 | 2016-11-15 | Bristol-Myers Squibb Company | Carbazole compounds useful as bromodomain inhibitors |
| WO2014158875A1 (en) | 2013-03-14 | 2014-10-02 | Pellficure Pharmaceuticals Inc. | Novel therapy for prostate carcinoma |
| SI3122426T1 (sl) | 2014-03-28 | 2023-04-28 | Duke University | Zdravljenje raka dojk z uporabo selektivnih modulatorjev estrogenskih receptorjev |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| WO2016040896A1 (en) | 2014-09-12 | 2016-03-17 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| CA3027563C (en) | 2016-06-22 | 2024-07-02 | Ellipses Pharma Ltd | AR+ METHODS FOR BREAST CANCER TREATMENT |
| AU2017350690A1 (en) | 2016-10-24 | 2019-06-13 | Pellficure Pharmaceuticals Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione |
| ES2981967T3 (es) | 2017-01-05 | 2024-10-14 | Radius Pharmaceuticals Inc | Formas polimórficas de RAD1901-2HCl |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS229934B2 (en) * | 1981-07-07 | 1984-07-16 | Pfizer | Production method subst.indolylacryte acid derivative |
| GB8518743D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
-
1993
- 1993-05-21 GB GB939310635A patent/GB9310635D0/en active Pending
-
1994
- 1994-05-02 ZA ZA943494A patent/ZA943494B/xx unknown
- 1994-05-17 TW TW083104441A patent/TW279866B/zh active
- 1994-05-19 CZ CZ953051A patent/CZ305195A3/cs unknown
- 1994-05-19 AU AU69287/94A patent/AU6928794A/en not_active Abandoned
- 1994-05-19 WO PCT/EP1994/001613 patent/WO1994027989A1/en not_active Ceased
- 1994-05-19 CA CA002162921A patent/CA2162921A1/en not_active Abandoned
- 1994-05-19 PL PL94311702A patent/PL311702A1/xx unknown
- 1994-05-19 EP EP94917647A patent/EP0699196A1/en not_active Withdrawn
- 1994-05-19 JP JP7500181A patent/JPH08510455A/ja active Pending
- 1994-05-19 SK SK1424-95A patent/SK142495A3/sk unknown
- 1994-05-19 CN CN94192683A patent/CN1126473A/zh active Pending
- 1994-05-19 HU HU9503321A patent/HUT73790A/hu unknown
- 1994-05-20 IL IL10970394A patent/IL109703A0/xx unknown
- 1994-11-18 PE PE1994255110A patent/PE31195A1/es not_active Application Discontinuation
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1995
- 1995-11-17 OA OA60742A patent/OA10195A/en unknown
- 1995-11-20 NO NO954681A patent/NO954681L/no unknown
- 1995-11-20 FI FI955587A patent/FI955587A0/fi not_active Application Discontinuation
- 1995-11-21 BG BG100154A patent/BG100154A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| NO954681D0 (no) | 1995-11-20 |
| GB9310635D0 (en) | 1993-07-07 |
| HU9503321D0 (en) | 1996-01-29 |
| IL109703A0 (en) | 1994-08-26 |
| CA2162921A1 (en) | 1994-12-08 |
| PL311702A1 (en) | 1996-03-04 |
| NO954681L (no) | 1995-11-20 |
| BG100154A (en) | 1996-07-31 |
| EP0699196A1 (en) | 1996-03-06 |
| CN1126473A (zh) | 1996-07-10 |
| SK142495A3 (en) | 1996-06-05 |
| TW279866B (cg-RX-API-DMAC10.html) | 1996-07-01 |
| JPH08510455A (ja) | 1996-11-05 |
| FI955587A7 (fi) | 1995-11-20 |
| WO1994027989A1 (en) | 1994-12-08 |
| FI955587A0 (fi) | 1995-11-20 |
| HUT73790A (en) | 1996-09-30 |
| OA10195A (en) | 1996-12-18 |
| PE31195A1 (es) | 1995-10-18 |
| AU6928794A (en) | 1994-12-20 |
| ZA943494B (en) | 1995-01-23 |
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