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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- KCIDZIIHRGYJAE-YGFYJFDDSA-L dipotassium;[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] phosphate Chemical compound [K+].[K+].OC[C@H]1O[C@H](OP([O-])([O-])=O)[C@H](O)[C@@H](O)[C@H]1O KCIDZIIHRGYJAE-YGFYJFDDSA-L 0.000 description 1
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- MKXKFYHWDHIYRV-UHFFFAOYSA-N flutamide Chemical compound CC(C)C(=O)NC1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 MKXKFYHWDHIYRV-UHFFFAOYSA-N 0.000 description 1
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
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- 230000014759 maintenance of location Effects 0.000 description 1
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- 239000000594 mannitol Substances 0.000 description 1
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- 238000004949 mass spectrometry Methods 0.000 description 1
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- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- GSYSFVSGPABNNL-UHFFFAOYSA-N methyl 2-dimethoxyphosphoryl-2-(phenylmethoxycarbonylamino)acetate Chemical group COC(=O)C(P(=O)(OC)OC)NC(=O)OCC1=CC=CC=C1 GSYSFVSGPABNNL-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- LOTBYPQQWICYBB-UHFFFAOYSA-N methyl n-hexyl-n-[2-(hexylamino)ethyl]carbamate Chemical compound CCCCCCNCCN(C(=O)OC)CCCCCC LOTBYPQQWICYBB-UHFFFAOYSA-N 0.000 description 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 229960002216 methylparaben Drugs 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910000402 monopotassium phosphate Inorganic materials 0.000 description 1
- 235000019796 monopotassium phosphate Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000006199 nebulizer Substances 0.000 description 1
- XWXYUMMDTVBTOU-UHFFFAOYSA-N nilutamide Chemical compound O=C1C(C)(C)NC(=O)N1C1=CC=C([N+]([O-])=O)C(C(F)(F)F)=C1 XWXYUMMDTVBTOU-UHFFFAOYSA-N 0.000 description 1
- 229960002653 nilutamide Drugs 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 239000012454 non-polar solvent Substances 0.000 description 1
- 239000002687 nonaqueous vehicle Substances 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 210000000496 pancreas Anatomy 0.000 description 1
- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
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- 229920000098 polyolefin Polymers 0.000 description 1
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- GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
- 229960003415 propylparaben Drugs 0.000 description 1
- 201000004240 prostatic hypertrophy Diseases 0.000 description 1
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- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
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- 238000011552 rat model Methods 0.000 description 1
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- 125000006413 ring segment Chemical group 0.000 description 1
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- 238000000926 separation method Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
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- 159000000000 sodium salts Chemical class 0.000 description 1
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- 239000011877 solvent mixture Substances 0.000 description 1
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- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
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- 239000002511 suppository base Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- 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
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 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
- 230000001225 therapeutic effect Effects 0.000 description 1
- 231100001274 therapeutic index Toxicity 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229940100640 transdermal system Drugs 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
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)
| Country | Link |
|---|---|
| EP (1) | EP0699196A1 (Direct) |
| JP (1) | JPH08510455A (Direct) |
| CN (1) | CN1126473A (Direct) |
| AU (1) | AU6928794A (Direct) |
| BG (1) | BG100154A (Direct) |
| CA (1) | CA2162921A1 (Direct) |
| CZ (1) | CZ305195A3 (Direct) |
| FI (1) | FI955587A7 (Direct) |
| GB (1) | GB9310635D0 (Direct) |
| HU (1) | HUT73790A (Direct) |
| IL (1) | IL109703A0 (Direct) |
| NO (1) | NO954681L (Direct) |
| OA (1) | OA10195A (Direct) |
| PE (1) | PE31195A1 (Direct) |
| PL (1) | PL311702A1 (Direct) |
| SK (1) | SK142495A3 (Direct) |
| TW (1) | TW279866B (Direct) |
| WO (1) | WO1994027989A1 (Direct) |
| ZA (1) | ZA943494B (Direct) |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1131944A (zh) * | 1993-09-30 | 1996-09-25 | 山之内制药株式会社 | 唑类衍生物和它的药物组合物 |
| WO1996014090A1 (en) * | 1994-11-07 | 1996-05-17 | Janssen Pharmaceutica N.V. | Compositions comprising carbazoles and cyclodextrins |
| PL322028A1 (en) * | 1995-03-01 | 1998-01-05 | Yamanouchi Pharma Co Ltd | Derivatives of imidazoles and pharmaceutic composition containing them |
| EP0974584B1 (en) * | 1997-02-21 | 2003-01-15 | Takeda Chemical Industries, Ltd. | Fused ring compounds, process for producing the same and use thereof |
| EP1334106B1 (en) | 2000-11-17 | 2006-05-24 | Takeda Pharmaceutical Company Limited | Imidazole derivatives, production method thereof and use thereof |
| ATE502030T1 (de) | 2000-11-20 | 2011-04-15 | Takeda Pharmaceutical | Imidazolderivate, verfahren zu deren herstellung und deren verwendung |
| WO2002046186A1 (en) | 2000-12-08 | 2002-06-13 | Takeda Chemical Industries, Ltd. | Substituted thiazole derivatives bearing 3-pyridyl groups, process for preparing the same and use thereof |
| MX2007015905A (es) * | 2005-06-24 | 2008-03-06 | Lilly Co Eli | Derivados de tetrahidrocarbazol utiles como moduladores de receptor de androgeno (sarm). |
| 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 |
| MA33451B1 (fr) | 2009-06-26 | 2012-07-03 | Novartis Ag | Dérivés d'imidazolidin-2-one 1,3-disubstitués en tant qu'inhibiteurs de cyp 17 |
| 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 |
| US9132105B2 (en) | 2010-08-04 | 2015-09-15 | Pellficure Pharmaceuticals, Inc. | Treatment of prostate carcinoma |
| JP2013537210A (ja) | 2010-09-16 | 2013-09-30 | ノバルティス アーゲー | １７α−ヒドロキシラーゼ／Ｃ１７，２０−リアーゼ阻害剤 |
| ES2550319T3 (es) | 2010-09-28 | 2015-11-06 | Radius Health, Inc | Moduladores selectivos del receptor de andrógenos |
| EA023064B1 (ru) | 2011-04-28 | 2016-04-29 | Новартис Аг | ИНГИБИТОРЫ 17α-ГИДРОКСИЛАЗЫ/C-ЛИАЗЫ |
| US9492460B2 (en) * | 2013-02-27 | 2016-11-15 | Bristol-Myers Squibb Company | Carbazole compounds useful as bromodomain inhibitors |
| AU2014241816B9 (en) | 2013-03-14 | 2019-02-14 | Pellficure Pharmaceuticals Inc. | Novel therapy for prostate carcinoma |
| RS67458B1 (sr) | 2014-03-28 | 2025-12-31 | Univ Duke | Lečenje kancera dojke pozitivnog na receptor estrogena upotrebom selektivnih modulatora receptora estrogena |
| US9421264B2 (en) | 2014-03-28 | 2016-08-23 | Duke University | Method of treating cancer using selective estrogen receptor modulators |
| CA2960750A1 (en) | 2014-09-12 | 2016-03-17 | Pellficure Pharmaceuticals, Inc. | Compositions and methods for treatment of prostate carcinoma |
| RS63311B1 (sr) | 2016-06-22 | 2022-07-29 | Ellipses Pharma Ltd | Ar+ metode lečenja raka dojke |
| WO2018080933A1 (en) | 2016-10-24 | 2018-05-03 | Pellficure Pharmaceuticals Inc. | Pharmaceutical compositions of 5-hydroxy-2-methylnaphthalene-1, 4-dione |
| KR102881465B1 (ko) | 2017-01-05 | 2025-11-04 | 래디어스 파마슈티컬스, 인코포레이티드 | Rad1901-2hcl의 다형 형태 |
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 PL PL94311702A patent/PL311702A1/xx unknown
- 1994-05-19 SK SK1424-95A patent/SK142495A3/sk unknown
- 1994-05-19 EP EP94917647A patent/EP0699196A1/en not_active Withdrawn
- 1994-05-19 CA CA002162921A patent/CA2162921A1/en not_active Abandoned
- 1994-05-19 JP JP7500181A patent/JPH08510455A/ja active Pending
- 1994-05-19 HU HU9503321A patent/HUT73790A/hu unknown
- 1994-05-19 CN CN94192683A patent/CN1126473A/zh active Pending
- 1994-05-19 WO PCT/EP1994/001613 patent/WO1994027989A1/en not_active Ceased
- 1994-05-19 AU AU69287/94A patent/AU6928794A/en not_active Abandoned
- 1994-05-19 CZ CZ953051A patent/CZ305195A3/cs unknown
- 1994-05-20 IL IL10970394A patent/IL109703A0/xx unknown
- 1994-11-18 PE PE1994255110A patent/PE31195A1/es not_active Application Discontinuation
-
1995
- 1995-11-17 OA OA60742A patent/OA10195A/en unknown
- 1995-11-20 FI FI955587A patent/FI955587A7/fi not_active Application Discontinuation
- 1995-11-20 NO NO954681A patent/NO954681L/no unknown
- 1995-11-21 BG BG100154A patent/BG100154A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP0699196A1 (en) | 1996-03-06 |
| OA10195A (en) | 1996-12-18 |
| JPH08510455A (ja) | 1996-11-05 |
| NO954681D0 (no) | 1995-11-20 |
| IL109703A0 (en) | 1994-08-26 |
| PE31195A1 (es) | 1995-10-18 |
| CA2162921A1 (en) | 1994-12-08 |
| SK142495A3 (en) | 1996-06-05 |
| CN1126473A (zh) | 1996-07-10 |
| FI955587A0 (fi) | 1995-11-20 |
| PL311702A1 (en) | 1996-03-04 |
| WO1994027989A1 (en) | 1994-12-08 |
| FI955587A7 (fi) | 1995-11-20 |
| HU9503321D0 (en) | 1996-01-29 |
| BG100154A (en) | 1996-07-31 |
| GB9310635D0 (en) | 1993-07-07 |
| TW279866B (Direct) | 1996-07-01 |
| HUT73790A (en) | 1996-09-30 |
| ZA943494B (en) | 1995-01-23 |
| AU6928794A (en) | 1994-12-20 |
| NO954681L (no) | 1995-11-20 |
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