CN1057085C - 杂环取代的苯基－环己烷羧酸衍生物 - Google Patents
杂环取代的苯基－环己烷羧酸衍生物 Download PDFInfo
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- CN1057085C CN1057085C CN94101553A CN94101553A CN1057085C CN 1057085 C CN1057085 C CN 1057085C CN 94101553 A CN94101553 A CN 94101553A CN 94101553 A CN94101553 A CN 94101553A CN 1057085 C CN1057085 C CN 1057085C
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- phenyl
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- QXXHHHWXFHPNOS-UHFFFAOYSA-N 1-phenylcyclohexane-1-carboxylic acid Chemical class C=1C=CC=CC=1C1(C(=O)O)CCCCC1 QXXHHHWXFHPNOS-UHFFFAOYSA-N 0.000 title claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 72
- -1 cyclohexanebenzyl halides Chemical class 0.000 claims abstract description 20
- 239000003814 drug Substances 0.000 claims abstract description 7
- 201000001320 Atherosclerosis Diseases 0.000 claims abstract description 4
- 208000037849 arterial hypertension Diseases 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 70
- 125000000217 alkyl group Chemical group 0.000 claims description 62
- 229910052739 hydrogen Inorganic materials 0.000 claims description 54
- 239000001257 hydrogen Substances 0.000 claims description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
- 238000000034 method Methods 0.000 claims description 28
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000460 chlorine Chemical group 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 20
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 18
- 229910052794 bromium Inorganic materials 0.000 claims description 18
- 229910052731 fluorine Inorganic materials 0.000 claims description 18
- 239000011737 fluorine Substances 0.000 claims description 18
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 18
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 17
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
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- 125000003831 tetrazolyl group Chemical group 0.000 claims description 13
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- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical group OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 12
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 12
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 11
- 230000007062 hydrolysis Effects 0.000 claims description 11
- 238000006460 hydrolysis reaction Methods 0.000 claims description 11
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 10
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 10
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 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 claims description 10
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical group 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
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- 125000004076 pyridyl group Chemical group 0.000 claims description 8
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- 238000007112 amidation reaction Methods 0.000 claims description 6
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000001153 fluoro group Chemical group F* 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
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- UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 3
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- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
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- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
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- 125000001424 substituent group Chemical group 0.000 claims description 2
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- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims 1
- 239000012752 auxiliary agent Substances 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 69
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 56
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
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- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
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- 239000003085 diluting agent Substances 0.000 description 1
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- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
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- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- QWMUDOFWQWBHFI-UHFFFAOYSA-N hydroxy-imino-diphenoxy-$l^{5}-phosphane Chemical compound C=1C=CC=CC=1OP(=O)(N)OC1=CC=CC=C1 QWMUDOFWQWBHFI-UHFFFAOYSA-N 0.000 description 1
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- 239000004310 lactic acid Substances 0.000 description 1
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- 210000004072 lung Anatomy 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Chemical class 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000028161 membrane depolarization Effects 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
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- 238000002156 mixing Methods 0.000 description 1
- 229960005181 morphine Drugs 0.000 description 1
- 230000022082 negative regulation of vasoconstriction Effects 0.000 description 1
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
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- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 230000003836 peripheral circulation Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- ZZYXNRREDYWPLN-UHFFFAOYSA-N pyridine-2,3-diamine Chemical compound NC1=CC=CN=C1N ZZYXNRREDYWPLN-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
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- 230000010076 replication Effects 0.000 description 1
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- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 235000002639 sodium chloride Nutrition 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 238000001356 surgical procedure Methods 0.000 description 1
- 210000002820 sympathetic nervous system Anatomy 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- VLKJJJUJOJNSKE-JKSUJKDBSA-N tert-butyl (1r,2r)-2-(4-methylphenyl)cyclohexane-1-carboxylate Chemical class C1=CC(C)=CC=C1[C@H]1[C@H](C(=O)OC(C)(C)C)CCCC1 VLKJJJUJOJNSKE-JKSUJKDBSA-N 0.000 description 1
- CPKLXNJCDGSLKB-JKSUJKDBSA-N tert-butyl (1r,2r)-2-[4-(bromomethyl)phenyl]cyclohexane-1-carboxylate Chemical class CC(C)(C)OC(=O)[C@@H]1CCCC[C@H]1C1=CC=C(CBr)C=C1 CPKLXNJCDGSLKB-JKSUJKDBSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4304455.7 | 1993-02-15 | ||
| DE4304455A DE4304455A1 (de) | 1993-02-15 | 1993-02-15 | Heterocyclisch substituierte Phenyl-cyclohexan-carbonsäurederivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1108257A CN1108257A (zh) | 1995-09-13 |
| CN1057085C true CN1057085C (zh) | 2000-10-04 |
Family
ID=6480447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN94101553A Expired - Fee Related CN1057085C (zh) | 1993-02-15 | 1994-02-15 | 杂环取代的苯基－环己烷羧酸衍生物 |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US5395840A (OSRAM) |
| EP (1) | EP0611767B1 (OSRAM) |
| JP (1) | JPH06293741A (OSRAM) |
| KR (1) | KR940019708A (OSRAM) |
| CN (1) | CN1057085C (OSRAM) |
| AT (1) | ATE196141T1 (OSRAM) |
| AU (1) | AU672262B2 (OSRAM) |
| CA (1) | CA2115536C (OSRAM) |
| CZ (1) | CZ289096B6 (OSRAM) |
| DE (2) | DE4304455A1 (OSRAM) |
| DK (1) | DK0611767T3 (OSRAM) |
| ES (1) | ES2151908T3 (OSRAM) |
| FI (1) | FI106716B (OSRAM) |
| GR (1) | GR3034957T3 (OSRAM) |
| IL (1) | IL108625A (OSRAM) |
| MY (1) | MY131595A (OSRAM) |
| NO (1) | NO300810B1 (OSRAM) |
| NZ (1) | NZ250864A (OSRAM) |
| PH (1) | PH30172A (OSRAM) |
| PL (1) | PL177834B1 (OSRAM) |
| PT (1) | PT611767E (OSRAM) |
| RU (1) | RU2119480C1 (OSRAM) |
| SK (1) | SK15294A3 (OSRAM) |
| UA (1) | UA35574C2 (OSRAM) |
| ZA (1) | ZA94984B (OSRAM) |
Families Citing this family (25)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW300219B (OSRAM) * | 1991-09-14 | 1997-03-11 | Hoechst Ag | |
| DE19503160A1 (de) * | 1995-02-01 | 1996-08-08 | Bayer Ag | Verwendung von Phenylcyclohexylcarbonsäureamiden |
| HRP960015B1 (en) * | 1995-02-01 | 2000-12-31 | Bayer Ag | Substituted indole derivatives |
| DE19525028A1 (de) * | 1995-07-10 | 1997-01-16 | Bayer Ag | Amide und Sulfonamide von heterocyclisch substituierten Benzylaminen |
| EP0994877A1 (en) | 1997-07-03 | 2000-04-26 | Du Pont Pharmaceuticals Company | Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders |
| US6124463A (en) * | 1998-07-02 | 2000-09-26 | Dupont Pharmaceuticals | Benzimidazoles as corticotropin release factor antagonists |
| US6365589B1 (en) | 1998-07-02 | 2002-04-02 | Bristol-Myers Squibb Pharma Company | Imidazo-pyridines, -pyridazines, and -triazines as corticotropin releasing factor antagonists |
| HRP20010451A2 (en) * | 1998-11-17 | 2003-04-30 | Basf Ag | 2-phenylbenzimidazoles and 2-phenylindoles, and production and use thereof |
| DE19924819A1 (de) * | 1999-05-29 | 2000-11-30 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäurebenzylamid (Adenosinaufnahmeinhibitoren) |
| DE19924818A1 (de) * | 1999-05-29 | 2000-11-30 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäureamide |
| DE10044792A1 (de) | 2000-09-11 | 2002-04-04 | Bayer Ag | Substituierte Phenylcyclohexancarbonsäureamide und ihre Verwendung |
| EP2017252B1 (en) | 2006-05-09 | 2012-12-19 | Mitsubishi Gas Chemical Company, Inc. | Preparation of 4-(4-alkylcyclohexyl)benzaldehyde |
| AU2010262905B2 (en) | 2009-06-17 | 2015-04-16 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| KR20140014110A (ko) | 2010-12-16 | 2014-02-05 | 버텍스 파마슈티칼스 인코포레이티드 | 인플루엔자 바이러스 복제의 억제제 |
| EP2723717A2 (en) | 2011-06-24 | 2014-04-30 | Amgen Inc. | Trpm8 antagonists and their use in treatments |
| MX2013015058A (es) | 2011-06-24 | 2014-01-20 | Amgen Inc | Antagonistas de melastatina 8 de potencial receptor transitorio y su uso en tratamientos. |
| UA118010C2 (uk) | 2011-08-01 | 2018-11-12 | Вертекс Фармасьютікалз Інкорпорейтед | Інгібітори реплікації вірусів грипу |
| EP3255049A1 (en) | 2012-06-29 | 2017-12-13 | Pfizer Inc | Novel 4-(substituted-amino)-7h-pyrrolo[2,3-d]pyrimidines as lrrk2 inhibitors |
| US8952009B2 (en) | 2012-08-06 | 2015-02-10 | Amgen Inc. | Chroman derivatives as TRPM8 inhibitors |
| EP3068782B1 (en) | 2013-11-13 | 2018-05-23 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| ES2741444T3 (es) | 2013-11-13 | 2020-02-11 | Vertex Pharma | Inhibidores de la replicación de virus de la gripe |
| EP3083618B1 (en) | 2013-12-17 | 2018-02-21 | Pfizer Inc | Novel 3,4-disubstituted-1h-pyrrolo[2,3-b]pyridines and 4,5-disubstituted-7h-pyrrolo[2,3-c]pyridazines as lrrk2 inhibitors |
| WO2016183120A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Inhibitors of influenza viruses replication |
| WO2016183116A1 (en) | 2015-05-13 | 2016-11-17 | Vertex Pharmaceuticals Incorporated | Methods of preparing inhibitors of influenza viruses replication |
| EP3350178B1 (en) | 2015-09-14 | 2021-10-20 | Pfizer Inc. | Novel imidazo [4,5-c]quinoline and imidazo [4,5-c][1,5]naphthyridine derivatives as lrrk2 inhibitors |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1066065A (zh) * | 1991-04-26 | 1992-11-11 | 拜尔公司 | 杂环取代的苯乙酸衍生物及其制法和药物用途 |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5138069A (en) * | 1986-07-11 | 1992-08-11 | E. I. Du Pont De Nemours And Company | Angiotensin II receptor blocking imidazoles |
| GB8911854D0 (en) * | 1989-05-23 | 1989-07-12 | Ici Plc | Heterocyclic compounds |
| IE64514B1 (en) * | 1989-05-23 | 1995-08-09 | Zeneca Ltd | Azaindenes |
| US5164407A (en) * | 1989-07-03 | 1992-11-17 | Merck & Co., Inc. | Substituted imidazo-fused 5-membered ring heterocycles and their use as angiotensin ii antagonsists |
| AU7820091A (en) * | 1990-06-08 | 1991-12-12 | Roussel-Uclaf | New benzimidazole derivatives, their preparation process, the new intermediates obtained, their use as medicaments and the pharmaceutical compositions containing them |
| RU1836357C (ru) * | 1990-07-23 | 1993-08-23 | Др.Карл Томэ ГмбХ | Производные бензимидазола, их изомеры, смеси изомеров, гидраты или их физиологически переносимые соли, обладающие антагонистическими в отношении ангиотензина свойствами |
| EP0470543A1 (de) * | 1990-08-10 | 1992-02-12 | Dr. Karl Thomae GmbH | Heterocyclische Imidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zur ihrer Herstellung |
| DE4031635A1 (de) * | 1990-10-05 | 1992-04-09 | Thomae Gmbh Dr K | Substituierte 1-benzyl-benzimidazole, diese verbindungen enthaltende arzneimittel und verfahren zu ihrer herstellung |
| DE4224133A1 (de) * | 1992-07-22 | 1994-01-27 | Thomae Gmbh Dr K | Benzimidazole, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
-
1993
- 1993-02-15 DE DE4304455A patent/DE4304455A1/de not_active Withdrawn
-
1994
- 1994-01-31 AU AU54807/94A patent/AU672262B2/en not_active Ceased
- 1994-02-02 DK DK94101543T patent/DK0611767T3/da active
- 1994-02-02 DE DE59409509T patent/DE59409509D1/de not_active Expired - Fee Related
- 1994-02-02 AT AT94101543T patent/ATE196141T1/de not_active IP Right Cessation
- 1994-02-02 ES ES94101543T patent/ES2151908T3/es not_active Expired - Lifetime
- 1994-02-02 PT PT94101543T patent/PT611767E/pt unknown
- 1994-02-02 EP EP94101543A patent/EP0611767B1/de not_active Expired - Lifetime
- 1994-02-08 US US08/193,835 patent/US5395840A/en not_active Expired - Fee Related
- 1994-02-09 SK SK152-94A patent/SK15294A3/sk unknown
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1066065A (zh) * | 1991-04-26 | 1992-11-11 | 拜尔公司 | 杂环取代的苯乙酸衍生物及其制法和药物用途 |
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