DK172190B1 - Anvendelse af alfa-heterocyclisk substituerede tolunitriler og salte deraf til fremstilling af farmaceutiske præparater, nye forbindelser af denne klasse samt farmaceutisk præparat - Google Patents
Anvendelse af alfa-heterocyclisk substituerede tolunitriler og salte deraf til fremstilling af farmaceutiske præparater, nye forbindelser af denne klasse samt farmaceutisk præparat Download PDFInfo
- Publication number
- DK172190B1 DK172190B1 DK117687A DK117687A DK172190B1 DK 172190 B1 DK172190 B1 DK 172190B1 DK 117687 A DK117687 A DK 117687A DK 117687 A DK117687 A DK 117687A DK 172190 B1 DK172190 B1 DK 172190B1
- Authority
- DK
- Denmark
- Prior art keywords
- lower alkyl
- alkyl
- pyridyl
- aryl
- hydrogen
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 46
- 150000001875 compounds Chemical class 0.000 title claims description 127
- 238000002360 preparation method Methods 0.000 title claims description 11
- 239000000825 pharmaceutical preparation Substances 0.000 title description 3
- -1 1-imidazolyl Chemical group 0.000 claims abstract description 104
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 94
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 41
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 38
- 150000002367 halogens Chemical class 0.000 claims abstract description 35
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 31
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 29
- 125000001118 alkylidene group Chemical group 0.000 claims abstract description 22
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 20
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 17
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 16
- 125000004423 acyloxy group Chemical group 0.000 claims abstract description 15
- 125000003435 aroyl group Chemical group 0.000 claims abstract description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 13
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract description 12
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000001589 carboacyl group Chemical group 0.000 claims abstract description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
- 125000005333 aroyloxy group Chemical group 0.000 claims abstract description 8
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 6
- CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical group C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 claims abstract description 5
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 81
- 229910052739 hydrogen Inorganic materials 0.000 claims description 45
- 239000001257 hydrogen Substances 0.000 claims description 45
- 239000000203 mixture Substances 0.000 claims description 37
- 150000002431 hydrogen Chemical class 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 20
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 claims description 14
- 239000000262 estrogen Substances 0.000 claims description 13
- 229940011871 estrogen Drugs 0.000 claims description 13
- 125000002541 furyl group Chemical group 0.000 claims description 12
- 125000001041 indolyl group Chemical group 0.000 claims description 12
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 11
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 8
- 102000014654 Aromatase Human genes 0.000 claims description 7
- 108010078554 Aromatase Proteins 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 230000002401 inhibitory effect Effects 0.000 claims description 7
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000005153 alkyl sulfamoyl group Chemical group 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 5
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 5
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000001376 1,2,4-triazolyl group Chemical group N1N=C(N=C1)* 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims description 2
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 abstract description 2
- OAWQIDWSFKXRCS-UHFFFAOYSA-N 4-(1H-imidazol-2-yl)naphthalene-1-carbonitrile Chemical class C(#N)C1=CC=C(C2=CC=CC=C12)C=1NC=CN=1 OAWQIDWSFKXRCS-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 229910006074 SO2NH2 Inorganic materials 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000565 sulfonamide group Chemical group 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 78
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- 238000006243 chemical reaction Methods 0.000 description 49
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 26
- 239000002904 solvent Substances 0.000 description 20
- 239000011541 reaction mixture Substances 0.000 description 19
- 239000007858 starting material Substances 0.000 description 19
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 18
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- 229910000041 hydrogen chloride Inorganic materials 0.000 description 17
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 13
- 239000000284 extract Substances 0.000 description 13
- 229960004592 isopropanol Drugs 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
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- ICGOVDHTTBNXJI-UHFFFAOYSA-N 4-(1h-imidazol-2-ylmethyl)benzonitrile Chemical compound C1=CC(C#N)=CC=C1CC1=NC=CN1 ICGOVDHTTBNXJI-UHFFFAOYSA-N 0.000 description 9
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- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 description 9
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- 238000000354 decomposition reaction Methods 0.000 description 8
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 8
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- 230000015572 biosynthetic process Effects 0.000 description 7
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- 229910052794 bromium Inorganic materials 0.000 description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 7
- 239000000460 chlorine Substances 0.000 description 7
- 238000010828 elution Methods 0.000 description 7
- 238000001704 evaporation Methods 0.000 description 7
- 230000008020 evaporation Effects 0.000 description 7
- 230000005764 inhibitory process Effects 0.000 description 7
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 239000000741 silica gel Substances 0.000 description 7
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- AEKVBBNGWBBYLL-UHFFFAOYSA-N 4-fluorobenzonitrile Chemical group FC1=CC=C(C#N)C=C1 AEKVBBNGWBBYLL-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
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- 241000124008 Mammalia Species 0.000 description 6
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- 230000001419 dependent effect Effects 0.000 description 3
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- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/02—Drugs for disorders of the urinary system of urine or of the urinary tract, e.g. urine acidifiers
-
- 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
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/57—Nitriles
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Endocrinology (AREA)
- Urology & Nephrology (AREA)
- Reproductive Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Fats And Perfumes (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Polymers With Sulfur, Phosphorus Or Metals In The Main Chain (AREA)
- Saccharide Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Indole Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Hydrogenated Pyridines (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US83748986 | 1986-03-07 | ||
| US06/837,489 US4749713A (en) | 1986-03-07 | 1986-03-07 | Alpha-heterocycle substituted tolunitriles |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK117687D0 DK117687D0 (da) | 1987-03-06 |
| DK117687A DK117687A (da) | 1987-09-08 |
| DK172190B1 true DK172190B1 (da) | 1997-12-22 |
Family
ID=25274596
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK117687A DK172190B1 (da) | 1986-03-07 | 1987-03-06 | Anvendelse af alfa-heterocyclisk substituerede tolunitriler og salte deraf til fremstilling af farmaceutiske præparater, nye forbindelser af denne klasse samt farmaceutisk præparat |
Country Status (36)
| Country | Link |
|---|---|
| US (1) | US4749713A (cs) |
| EP (1) | EP0236940B3 (cs) |
| JP (1) | JPH0755930B2 (cs) |
| KR (1) | KR910000482B1 (cs) |
| AT (1) | ATE94873T1 (cs) |
| BG (4) | BG45700A3 (cs) |
| CA (1) | CA1316928C (cs) |
| CY (1) | CY1905A (cs) |
| CZ (3) | CZ279026B6 (cs) |
| DD (1) | DD264432A5 (cs) |
| DE (2) | DE19775016I2 (cs) |
| DK (1) | DK172190B1 (cs) |
| DZ (1) | DZ1055A1 (cs) |
| ES (1) | ES2059317T3 (cs) |
| FI (1) | FI91857C (cs) |
| HK (1) | HK50296A (cs) |
| HU (1) | HU202843B (cs) |
| IE (1) | IE61101B1 (cs) |
| IL (1) | IL81746A (cs) |
| LU (1) | LU90128I2 (cs) |
| LV (1) | LV5769B4 (cs) |
| MA (1) | MA20888A1 (cs) |
| MC (1) | MC1805A1 (cs) |
| MT (1) | MTP998B (cs) |
| MX (1) | MX5496A (cs) |
| MY (1) | MY102428A (cs) |
| NL (1) | NL970011I2 (cs) |
| NO (2) | NO170277C (cs) |
| PH (1) | PH24159A (cs) |
| PL (2) | PL151490B1 (cs) |
| PT (1) | PT84410B (cs) |
| RO (2) | RO101533B1 (cs) |
| SK (3) | SK279103B6 (cs) |
| SU (3) | SU1470184A3 (cs) |
| TN (1) | TNSN87033A1 (cs) |
| ZA (1) | ZA871637B (cs) |
Families Citing this family (49)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5112845A (en) * | 1986-03-07 | 1992-05-12 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| US5352795A (en) * | 1986-03-07 | 1994-10-04 | Ciba-Geigy Corporation | Alpha-heterocycle substituted tolunitriles |
| GB8714013D0 (en) * | 1987-06-16 | 1987-07-22 | Ici Plc | (substituted-aralkyl)heterocyclic compounds |
| DE3811574A1 (de) * | 1988-03-31 | 1989-10-19 | Schering Ag | N-substituierte imidazole, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| DE59010171D1 (de) * | 1989-07-14 | 1996-04-11 | Ciba Geigy Ag | Substituierte Benzonitrile |
| DE3926365A1 (de) * | 1989-08-04 | 1991-02-07 | Schering Ag | Cycloalkylenazole, verfahren zu deren herstellung, pharmazeutische praeparate, die diese enthalten sowie ihre verwendung zur herstellung von arzneimitteln |
| JP2602456B2 (ja) * | 1990-04-12 | 1997-04-23 | 雪印乳業株式会社 | 子宮内膜症治療剤 |
| EP0457716A1 (de) * | 1990-04-20 | 1991-11-21 | Ciba-Geigy Ag | Naphthalinderivate |
| DE4039559A1 (de) * | 1990-12-07 | 1992-06-11 | Schering Ag | Funktionalisierte vinylazole, verfahren zu deren herstellung, pharmazeutische praeparate die diese vinylazole enthalten sowie deren verwendung zur herstellung von arzneimitteln |
| TW210334B (cs) * | 1990-12-12 | 1993-08-01 | Ciba Geigy Ag | |
| CH683151A5 (de) * | 1991-04-24 | 1994-01-31 | Ciba Geigy Ag | Antikonzeption bei weiblichen Primaten ohne Beeinflussung des menstruellen Zyklus. |
| DE4120107A1 (de) * | 1991-06-14 | 1992-12-17 | Schering Ag | Bicyclisch substituierte vinylimidazole, -triazole und -tetrazole |
| WO1993005027A1 (fr) | 1991-09-02 | 1993-03-18 | Yamanouchi Pharmaceutical Co., Ltd. | Amine tertiaire triazolylee ou un sel de celle-ci |
| US5223539A (en) * | 1991-11-22 | 1993-06-29 | G. D. Searle & Co. | N,n-di-alkyl(phenoxy)benzamide derivatives |
| AU5285593A (en) * | 1992-10-21 | 1994-05-09 | Sankyo Company Limited | Azole compound |
| GB2273704B (en) * | 1992-12-16 | 1997-01-22 | Orion Yhtymae Oy | Triazolyl diaryl selective aromatase inhibiting compounds |
| US5426196A (en) * | 1993-12-22 | 1995-06-20 | Glaxo Inc. | Synthesis of diaryl methanes |
| AU703203B2 (en) * | 1996-01-30 | 1999-03-18 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| WO1997027853A1 (en) * | 1996-01-30 | 1997-08-07 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| EP0891360A4 (en) * | 1996-04-03 | 2002-05-15 | Merck & Co Inc | INHIBITORS OF FARNESYL PROTEIN TRANSFERASE |
| US6080870A (en) * | 1996-04-03 | 2000-06-27 | Merck & Co., Inc. | Biaryl substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| WO1997036876A1 (en) * | 1996-04-03 | 1997-10-09 | Merck & Co., Inc. | Inhibitors of farnesyl-protein transferase |
| US6063930A (en) * | 1996-04-03 | 2000-05-16 | Merck & Co., Inc. | Substituted imidazole compounds useful as farnesyl-protein transferase inhibitors |
| US6833373B1 (en) | 1998-12-23 | 2004-12-21 | G.D. Searle & Co. | Method of using an integrin antagonist and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| US6858598B1 (en) | 1998-12-23 | 2005-02-22 | G. D. Searle & Co. | Method of using a matrix metalloproteinase inhibitor and one or more antineoplastic agents as a combination therapy in the treatment of neoplasia |
| AU2002342335B2 (en) | 2001-05-16 | 2006-02-02 | Novartis Ag | Combination comprising N-{5-[4-(4-methyl-piperazino-methyl)-benzoylamido]-2-methylphenyl}-4-(3-pyridyl)-2pyrimidine-amine and a chemotherapeutic agent |
| US20050113432A1 (en) * | 2001-12-11 | 2005-05-26 | Tekmal Rajeshwar R. | Bis(cyanophenyl)methyl-triazole for use in prevention of breast cancer |
| CN100593401C (zh) * | 2002-07-30 | 2010-03-10 | 诺瓦提斯公司 | 芳香酶抑制剂和双膦酸酯的组合 |
| GB0217636D0 (en) * | 2002-07-30 | 2002-09-11 | Novartis Ag | Organic compounds |
| JP2004196795A (ja) * | 2002-12-16 | 2004-07-15 | Wyeth | 外部寄生虫駆除剤としてのｎ−フェニル−３−シクロプロピルピラゾール−４−カルボニトリル |
| AU2003282380A1 (en) * | 2003-11-14 | 2004-06-06 | ADIBHATLA, KALI,SATYA, Bhujanga,rao | A method for the separation of the letrozole precursor 4-1-(1,2,4-triazolyl) methyl benzonitrile from its 1,3,4-triazolyl isomer |
| EP1694650A1 (en) * | 2003-12-15 | 2006-08-30 | Laboratoire Theramex | 1-n-phenyl-amino-1h-imidazole derivatives and pharmaceutical compositions containing them |
| JP2008516005A (ja) * | 2005-07-06 | 2008-05-15 | シコール インコーポレイティド | レトロゾールの改良された調製方法 |
| GT200600381A (es) | 2005-08-25 | 2007-03-28 | Compuestos organicos | |
| US20090082413A1 (en) * | 2007-09-26 | 2009-03-26 | Protia, Llc | Deuterium-enriched letrozole |
| RU2425038C2 (ru) * | 2009-11-27 | 2011-07-27 | Федеральное государственное унитарное предприятие "Государственный научный центр "Научно-исследовательский институт органических полупродуктов и красителей" (ФГУП "ГНЦ "НИОПИК") | Способ получения 1-[ди(4-цианфенил)метил]-1,2,4-триазола |
| WO2011128434A2 (en) | 2010-04-16 | 2011-10-20 | Novartis Ag | Treatment of endocrine resistant breast cancer |
| CA2809086A1 (en) * | 2010-08-27 | 2012-03-01 | Generics (Uk) Limited | Pure intermediate |
| JP6280501B2 (ja) * | 2011-09-08 | 2018-02-14 | メレオ バイオファーマ ２ リミテッド | 性腺機能低下症および関連疾患の処置ためのアロマターゼ阻害剤の使用 |
| KR101915942B1 (ko) | 2012-06-08 | 2018-11-06 | 에프. 호프만-라 로슈 아게 | 암의 치료를 위한 포스포이노시타이드 3 키나제 억제제 화합물 및 화학치료제의 돌연변이체 선택성 및 조합물 |
| BR112016002465B1 (pt) | 2013-08-14 | 2022-09-20 | Novartis Ag | Combinação farmacêutica e seu uso |
| AR104068A1 (es) | 2015-03-26 | 2017-06-21 | Hoffmann La Roche | Combinaciones de un compuesto inhibidor de fosfoinosítido 3-cinasa y un compuesto inhibidor de cdk4/6 para el tratamiento del cáncer |
| GB201614179D0 (en) | 2016-08-19 | 2016-10-05 | Mereo Biopharma 2 Ltd | Dosage regimen for the treatment of endometriosis |
| BR112021001233A2 (pt) | 2018-07-23 | 2021-04-20 | F. Hoffmann-La Roche Ag | método para tratar câncer em um paciente, uso de uma quantidade terapeuticamente eficaz de gdc-0077 e quantidade terapeuticamente eficaz de gdc-0077 |
| CN112839642A (zh) | 2018-10-08 | 2021-05-25 | 豪夫迈·罗氏有限公司 | 用PI3Kα抑制剂和二甲双胍治疗癌症的方法 |
| CN114786666A (zh) | 2019-12-03 | 2022-07-22 | 基因泰克公司 | 治疗乳腺癌的组合疗法 |
| IL303502A (en) | 2020-12-11 | 2023-08-01 | Genentech Inc | Combination therapies for treatment of her2 cancer |
| CN116925001B (zh) * | 2023-07-26 | 2025-09-30 | 陕西师范大学 | 一种抗乳腺癌药物来曲唑类似物的合成方法 |
| WO2025122745A1 (en) | 2023-12-05 | 2025-06-12 | Genentech, Inc. | Combination therapies for treatment of her2 cancer |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3290281A (en) * | 1963-07-18 | 1966-12-06 | Weinstein Julius | Photochromic nitrobenzylpyridines |
| US3397273A (en) * | 1966-02-18 | 1968-08-13 | Lilly Co Eli | Controlling phytopathogenic fungi on plants with 3-pyridyl methane derivatives |
| GB1170188A (en) * | 1967-09-15 | 1969-11-12 | Bayer Ag | N-trityl-imidazoles and salts and uses thereof |
| DE1670976B2 (de) * | 1968-01-29 | 1976-07-22 | N-trityl-imidazole | |
| DE1908991B2 (de) * | 1969-02-22 | 1977-05-26 | Bayer Ag, 5090 Leverkusen | Alpha, alpha-disubstituierte n- benzylimidazole und deren salze |
| BR6915465D0 (pt) * | 1969-03-07 | 1973-01-04 | Bayer Ag | Processo para preparar n-benzimidazois substituidos na posicao alfa por heterociclos penta-membrados com atividade antimicotica |
| DE2007794A1 (de) * | 1970-02-20 | 1971-09-02 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Fungizide Mittel |
| DE2009020C3 (de) * | 1970-02-26 | 1979-09-13 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von N-(l,l,l-trisubstituierten)-Methylazolen |
| US3764690A (en) * | 1972-03-03 | 1973-10-09 | Bayer Ag | Substituted n-benzylimidazoles as antimycotic agents |
| US3927017A (en) * | 1974-06-27 | 1975-12-16 | Janssen Pharmaceutica Nv | 1-({62 -Aryl-{62 -R-ethyl)imidazoles |
| DE2628152C2 (de) * | 1976-06-23 | 1985-03-28 | Bayer Ag, 5090 Leverkusen | Fungizide und nematizide Mittel |
| DE2732531A1 (de) * | 1977-07-19 | 1979-02-01 | Hoechst Ag | Imidazolcarbonsaeuren und deren derivate |
| DE2735314A1 (de) * | 1977-08-05 | 1979-02-22 | Basf Ag | Alpha-azolylsulfide und deren derivate |
| US4431815A (en) * | 1977-08-26 | 1984-02-14 | Burroughs Wellcome Co. | 1-[3-(2,4-Dichlorophenyl)propyl]imidazole and salts thereof |
| DE2862340D1 (en) * | 1978-02-01 | 1983-11-24 | Wellcome Found | Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations thereof |
| DE2808086A1 (de) * | 1978-02-24 | 1979-08-30 | Bayer Ag | Substituierte diphenyl-imidazolyl- methane, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| DE2821829A1 (de) * | 1978-05-19 | 1979-11-22 | Basf Ag | Mittel zur regulierung des pflanzenwachstums |
| JPS55313A (en) * | 1978-06-13 | 1980-01-05 | Kissei Pharmaceut Co Ltd | Imidazole derivative |
| DE2847441A1 (de) * | 1978-11-02 | 1980-05-22 | Basf Ag | Imidazol-kupferkomplexverbindungen |
| DK157860C (da) * | 1979-06-07 | 1990-07-30 | Shionogi & Co | Analogifremgangsmaade til fremstilling af benzylimidazolderivater samt farmaceutisk acceptable syreadditionssalte deraf |
| US4281141A (en) * | 1980-05-30 | 1981-07-28 | Eli Lilly And Company | 3-(Imidazol-4-yl)-2-phenylpropanenitriles |
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| US4562199A (en) * | 1983-08-11 | 1985-12-31 | Thorogood Peter B | Imidazole derivatives, compositions and use |
| EP0149976A3 (de) * | 1983-12-30 | 1986-12-10 | Ciba-Geigy Ag | Substituierte Imidazole |
| US4602025A (en) * | 1984-06-18 | 1986-07-22 | Eli Lilly And Company | Aromatase inhibitors |
| US4801594A (en) * | 1984-06-18 | 1989-01-31 | Eli Lilly And Company | Aromatase inhibitors |
| US4755526A (en) * | 1984-06-18 | 1988-07-05 | Eli Lilly And Company | Method of inhibiting aromatase |
| US4766140A (en) * | 1984-06-18 | 1988-08-23 | Eli Lilly And Company | Method of inhibiting aromatase |
| US4605661A (en) * | 1984-06-18 | 1986-08-12 | Eli Lilly And Company | Aromastase inhibiting α,α-diarylimidazole-4(5)-propionitriles, α,α-diarylimidazole-4(5)-propionamides, and 4(5)-(2,2-diarylethyl)imidazoles |
-
1986
- 1986-03-07 US US06/837,489 patent/US4749713A/en not_active Expired - Lifetime
-
1987
- 1987-03-02 FI FI870903A patent/FI91857C/fi not_active IP Right Cessation
- 1987-03-03 DD DD87300415A patent/DD264432A5/de not_active IP Right Cessation
- 1987-03-03 IL IL81746A patent/IL81746A/xx not_active IP Right Cessation
- 1987-03-04 DZ DZ870031A patent/DZ1055A1/fr active
- 1987-03-05 BG BG081514A patent/BG45700A3/xx unknown
- 1987-03-05 HU HU87952A patent/HU202843B/hu unknown
- 1987-03-05 BG BG081515A patent/BG45701A3/xx unknown
- 1987-03-05 RO RO1987134372A patent/RO101533B1/ro unknown
- 1987-03-05 MC MC871874A patent/MC1805A1/fr unknown
- 1987-03-05 MA MA21124A patent/MA20888A1/fr unknown
- 1987-03-05 PL PL1987264460A patent/PL151490B1/pl unknown
- 1987-03-05 ES ES87103099T patent/ES2059317T3/es not_active Expired - Lifetime
- 1987-03-05 PL PL1987280247A patent/PL152025B1/pl unknown
- 1987-03-05 CA CA000531185A patent/CA1316928C/en not_active Expired - Lifetime
- 1987-03-05 AT AT87103099T patent/ATE94873T1/de active
- 1987-03-05 DE DE1997175016 patent/DE19775016I2/de active Active
- 1987-03-05 RO RO1987134373A patent/RO101532B1/ro unknown
- 1987-03-05 CY CY190587A patent/CY1905A/xx unknown
- 1987-03-05 PT PT84410A patent/PT84410B/pt unknown
- 1987-03-05 EP EP87103099A patent/EP0236940B3/en not_active Expired - Lifetime
- 1987-03-05 DE DE87103099T patent/DE3787480T2/de not_active Expired - Lifetime
- 1987-03-05 BG BG078756A patent/BG46598A3/xx unknown
- 1987-03-06 PH PH34986A patent/PH24159A/en unknown
- 1987-03-06 TN TNTNSN87033A patent/TNSN87033A1/fr unknown
- 1987-03-06 SK SK7368-87A patent/SK279103B6/sk unknown
- 1987-03-06 JP JP62050446A patent/JPH0755930B2/ja not_active Expired - Lifetime
- 1987-03-06 DK DK117687A patent/DK172190B1/da not_active IP Right Cessation
- 1987-03-06 MY MYPI87000247A patent/MY102428A/en unknown
- 1987-03-06 CZ CS871512A patent/CZ279026B6/cs not_active IP Right Cessation
- 1987-03-06 CZ CS877367A patent/CZ279027B6/cs not_active IP Right Cessation
- 1987-03-06 IE IE57587A patent/IE61101B1/en not_active IP Right Cessation
- 1987-03-06 SU SU874202145A patent/SU1470184A3/ru active
- 1987-03-06 MT MT998A patent/MTP998B/xx unknown
- 1987-03-06 CZ CS877368A patent/CZ279028B6/cs not_active IP Right Cessation
- 1987-03-06 MX MX549687A patent/MX5496A/es unknown
- 1987-03-06 KR KR1019870002004A patent/KR910000482B1/ko not_active Expired
- 1987-03-06 SK SK1512-87A patent/SK151287A3/sk unknown
- 1987-03-06 ZA ZA871637A patent/ZA871637B/xx unknown
- 1987-03-06 SK SK7367-87A patent/SK736787A3/sk unknown
- 1987-03-06 NO NO870937A patent/NO170277C/no not_active IP Right Cessation
-
1988
- 1988-01-18 SU SU884203999A patent/SU1577695A3/ru active
- 1988-01-18 SU SU884203990A patent/SU1549478A3/ru active
-
1993
- 1993-11-11 BG BG098212A patent/BG61204B2/bg unknown
-
1996
- 1996-03-21 HK HK50296A patent/HK50296A/en not_active IP Right Cessation
- 1996-07-18 LV LV960274A patent/LV5769B4/xx unknown
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1997
- 1997-03-03 NL NL970011C patent/NL970011I2/nl unknown
- 1997-08-20 LU LU90128C patent/LU90128I2/fr unknown
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1998
- 1998-03-04 NO NO1998010C patent/NO1998010I1/no unknown
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| Date | Code | Title | Description |
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| PUP | Patent expired |