HU188123B - Process for preparing new substituted imidazole derivatives and acid addition salts thereof - Google Patents
Process for preparing new substituted imidazole derivatives and acid addition salts thereof Download PDFInfo
- Publication number
- HU188123B HU188123B HU80410A HU41080A HU188123B HU 188123 B HU188123 B HU 188123B HU 80410 A HU80410 A HU 80410A HU 41080 A HU41080 A HU 41080A HU 188123 B HU188123 B HU 188123B
- Authority
- HU
- Hungary
- Prior art keywords
- bicyclo
- imidazole
- heteroatoms
- preparation
- formula
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title claims abstract description 21
- 239000002253 acid Chemical class 0.000 title claims abstract description 20
- 150000002460 imidazoles Chemical class 0.000 title claims abstract description 7
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 2
- -1 adamantanyl group Chemical group 0.000 claims abstract description 58
- 238000000034 method Methods 0.000 claims abstract description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002837 carbocyclic group Chemical group 0.000 claims abstract description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 77
- 150000001875 compounds Chemical class 0.000 claims description 44
- 238000002360 preparation method Methods 0.000 claims description 41
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 125000001118 alkylidene group Chemical group 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- 239000005977 Ethylene Substances 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 125000006833 (C1-C5) alkylene group Chemical group 0.000 claims description 2
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims 2
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 239000000969 carrier Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract description 46
- 125000005842 heteroatom Chemical group 0.000 abstract description 16
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract description 12
- 229910052757 nitrogen Chemical group 0.000 abstract description 6
- 229920006395 saturated elastomer Polymers 0.000 abstract description 6
- 229910052799 carbon Inorganic materials 0.000 abstract description 5
- 239000000126 substance Substances 0.000 abstract description 4
- 230000009424 thromboembolic effect Effects 0.000 abstract description 4
- 238000011282 treatment Methods 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- 125000004122 cyclic group Chemical group 0.000 abstract description 3
- 150000001721 carbon Chemical group 0.000 abstract description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 4
- 239000005864 Sulphur Chemical group 0.000 abstract 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 4
- 229910052760 oxygen Inorganic materials 0.000 abstract 4
- 239000001301 oxygen Substances 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000004043 oxo group Chemical group O=* 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 150000003568 thioethers Chemical class 0.000 abstract 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 52
- 239000000243 solution Substances 0.000 description 47
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 44
- 239000011541 reaction mixture Substances 0.000 description 34
- 239000003921 oil Substances 0.000 description 31
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
- 239000000203 mixture Substances 0.000 description 29
- 230000002829 reductive effect Effects 0.000 description 28
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
- 239000000706 filtrate Substances 0.000 description 20
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 16
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
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- 239000007787 solid Substances 0.000 description 15
- 238000009835 boiling Methods 0.000 description 14
- 239000012230 colorless oil Substances 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 238000001816 cooling Methods 0.000 description 11
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 10
- 238000010992 reflux Methods 0.000 description 10
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- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 9
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- 239000003208 petroleum Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 239000000741 silica gel Substances 0.000 description 8
- 229910002027 silica gel Inorganic materials 0.000 description 8
- BSQIDYZRDPHJNG-UHFFFAOYSA-N 1-[2-(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)ethyl]imidazole Chemical compound CC1(C)C(CC2)CC1C2CCN1C=CN=C1 BSQIDYZRDPHJNG-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- 210000000601 blood cell Anatomy 0.000 description 6
- 238000004821 distillation Methods 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- JYLUIKJKJDPRAY-UHFFFAOYSA-N 1-[2-(1-adamantyl)ethyl]imidazole Chemical class C1C(C2)CC(C3)CC2CC13CCN1C=CN=C1 JYLUIKJKJDPRAY-UHFFFAOYSA-N 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000003367 polycyclic group Chemical group 0.000 description 5
- 239000007818 Grignard reagent Substances 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 239000012670 alkaline solution Substances 0.000 description 4
- 239000002026 chloroform extract Substances 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000004795 grignard reagents Chemical class 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- 238000002054 transplantation Methods 0.000 description 4
- OVKAIZXCUJMFLN-UHFFFAOYSA-N 1-(2-bromoethyl)adamantane Chemical compound C1C(C2)CC3CC2CC1(CCBr)C3 OVKAIZXCUJMFLN-UHFFFAOYSA-N 0.000 description 3
- DSFWVXXIMCQWRI-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanylmethyl)imidazole Chemical compound C1C(C2)CCC2C1CN1C=CN=C1 DSFWVXXIMCQWRI-UHFFFAOYSA-N 0.000 description 3
- VZUOFLCVOCPUCM-UHFFFAOYSA-N 1-(chloromethyl)adamantane Chemical compound C1C(C2)CC3CC2CC1(CCl)C3 VZUOFLCVOCPUCM-UHFFFAOYSA-N 0.000 description 3
- VUULVGVPEOWYET-UHFFFAOYSA-N 1-[(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methyl]imidazole Chemical compound CC1(C)C(CC=2)CC1C=2CN1C=CN=C1 VUULVGVPEOWYET-UHFFFAOYSA-N 0.000 description 3
- SAYAOEYRSNXJCV-UHFFFAOYSA-N 1-[2-(6,6-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)ethyl]imidazole Chemical compound CC1(C)C(CC=2)CC1C=2CCN1C=CN=C1 SAYAOEYRSNXJCV-UHFFFAOYSA-N 0.000 description 3
- ASRLPYUFROGXNU-UHFFFAOYSA-N 3-(1-adamantyl)propan-1-ol Chemical compound C1C(C2)CC3CC2CC1(CCCO)C3 ASRLPYUFROGXNU-UHFFFAOYSA-N 0.000 description 3
- UVFFMASFIIKUOD-UHFFFAOYSA-N 5-(chloromethyl)bicyclo[2.2.1]hept-2-ene Chemical compound C1C2C(CCl)CC1C=C2 UVFFMASFIIKUOD-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000124008 Mammalia Species 0.000 description 3
- 229930040373 Paraformaldehyde Natural products 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000002744 anti-aggregatory effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- 230000037396 body weight Effects 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000002178 crystalline material Substances 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 235000006408 oxalic acid Nutrition 0.000 description 3
- 229920002866 paraformaldehyde Polymers 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- YIBNHAJFJUQSRA-YNNPMVKQSA-N prostaglandin H2 Chemical compound C1[C@@H]2OO[C@H]1[C@H](/C=C/[C@@H](O)CCCCC)[C@H]2C\C=C/CCCC(O)=O YIBNHAJFJUQSRA-YNNPMVKQSA-N 0.000 description 3
- 150000003180 prostaglandins Chemical class 0.000 description 3
- RXBQNMWIQKOSCS-UHFFFAOYSA-N (7,7-dimethyl-4-bicyclo[3.1.1]hept-3-enyl)methanol Chemical compound C1C2C(C)(C)C1CC=C2CO RXBQNMWIQKOSCS-UHFFFAOYSA-N 0.000 description 2
- ONUXQVADXWYYEX-UHFFFAOYSA-N 1-(1-adamantylmethyl)imidazole Chemical compound C1C(C2)CC(C3)CC2CC13CN1C=CN=C1 ONUXQVADXWYYEX-UHFFFAOYSA-N 0.000 description 2
- FUFMGIODEOGUGN-UHFFFAOYSA-N 1-(3-bicyclo[2.2.1]heptanyl)imidazole Chemical compound C1CC2CC1CC2N1C=CN=C1 FUFMGIODEOGUGN-UHFFFAOYSA-N 0.000 description 2
- SMVDINZSSSQDRF-UHFFFAOYSA-N 1-(5-bicyclo[2.2.1]hept-2-enylmethyl)imidazole Chemical compound C1C(C=C2)CC2C1CN1C=CN=C1 SMVDINZSSSQDRF-UHFFFAOYSA-N 0.000 description 2
- PNSQECQNDFACOV-UHFFFAOYSA-N 1-[2-(3,3-dimethyl-2-bicyclo[2.2.1]heptanylidene)ethyl]imidazole Chemical compound CC1(C)C(C2)CCC2C1=CCN1C=CN=C1 PNSQECQNDFACOV-UHFFFAOYSA-N 0.000 description 2
- XBNUFUMDFVXKDV-UHFFFAOYSA-N 1-[3-(1-adamantyl)propyl]imidazole Chemical compound C1C(C2)CC(C3)CC2CC13CCCN1C=CN=C1 XBNUFUMDFVXKDV-UHFFFAOYSA-N 0.000 description 2
- BESCHJUENMYCOJ-UHFFFAOYSA-N 1-chloro-2-methylheptane Chemical compound CCCCCC(C)CCl BESCHJUENMYCOJ-UHFFFAOYSA-N 0.000 description 2
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- PGUHVWPZZXEHFH-UHFFFAOYSA-N 4-(2-bromoethyl)-6,6-dimethylbicyclo[3.1.1]heptane Chemical compound C1C2C(C)(C)C1CCC2CCBr PGUHVWPZZXEHFH-UHFFFAOYSA-N 0.000 description 2
- HJMBBNXCSKYLPS-UHFFFAOYSA-N 4-(chloromethyl)-6,6-dimethylbicyclo[3.1.1]hept-3-ene Chemical compound C1C2C(C)(C)C1CC=C2CCl HJMBBNXCSKYLPS-UHFFFAOYSA-N 0.000 description 2
- JKTORXLUQLQJCM-UHFFFAOYSA-N 4-phosphonobutylphosphonic acid Chemical compound OP(O)(=O)CCCCP(O)(O)=O JKTORXLUQLQJCM-UHFFFAOYSA-N 0.000 description 2
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- FMNQRUKVXAQEAZ-JNRFBPFXSA-N (5z,8s,9r,10e,12s)-9,12-dihydroxy-8-[(1s)-1-hydroxy-3-oxopropyl]heptadeca-5,10-dienoic acid Chemical compound CCCCC[C@H](O)\C=C\[C@@H](O)[C@H]([C@@H](O)CC=O)C\C=C/CCCC(O)=O FMNQRUKVXAQEAZ-JNRFBPFXSA-N 0.000 description 1
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- FCYVSPJGKAWDOH-UHFFFAOYSA-N 1-(2-chloroethyl)adamantane Chemical compound C1C(C2)CC3CC2CC1(CCCl)C3 FCYVSPJGKAWDOH-UHFFFAOYSA-N 0.000 description 1
- AJGRMWDNGMWBHY-WLHGVMLRSA-N 1-[2-(1-adamantyl)ethyl]imidazole;(e)-but-2-enedioic acid Chemical compound OC(=O)\C=C\C(O)=O.C1C(C2)CC(C3)CC2CC13CCN1C=CN=C1 AJGRMWDNGMWBHY-WLHGVMLRSA-N 0.000 description 1
- BAMDLWWZUXMNSN-UHFFFAOYSA-N 1-[2-(6,6-dimethyl-4-bicyclo[3.1.1]heptanyl)ethyl]imidazole;oxalic acid Chemical compound OC(=O)C(O)=O.CC1(C)C(CC2)CC1C2CCN1C=CN=C1 BAMDLWWZUXMNSN-UHFFFAOYSA-N 0.000 description 1
- MDVGOOIANLZFCP-UHFFFAOYSA-N 1-adamantylmethanol Chemical compound C1C(C2)CC3CC2CC1(CO)C3 MDVGOOIANLZFCP-UHFFFAOYSA-N 0.000 description 1
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- 238000003776 cleavage reaction Methods 0.000 description 1
- IQFVPQOLBLOTPF-HKXUKFGYSA-L congo red Chemical compound [Na+].[Na+].C1=CC=CC2=C(N)C(/N=N/C3=CC=C(C=C3)C3=CC=C(C=C3)/N=N/C3=C(C4=CC=CC=C4C(=C3)S([O-])(=O)=O)N)=CC(S([O-])(=O)=O)=C21 IQFVPQOLBLOTPF-HKXUKFGYSA-L 0.000 description 1
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- 238000000746 purification Methods 0.000 description 1
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- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
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- 239000012439 solid excipient Substances 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-M succinate(1-) Chemical compound OC(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-M 0.000 description 1
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- 239000011975 tartaric acid Substances 0.000 description 1
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- 238000004809 thin layer chromatography Methods 0.000 description 1
- RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 1
- FIQMHBFVRAXMOP-UHFFFAOYSA-N triphenylphosphane oxide Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=O)C1=CC=CC=C1 FIQMHBFVRAXMOP-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/72—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 spiro-condensed with carbocyclic rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
-
- 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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
-
- 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
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/58—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin
- A61K31/585—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids containing heterocyclic rings, e.g. danazol, stanozolol, pancuronium or digitogenin containing lactone rings, e.g. oxandrolone, bufalin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/36—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal
- C07C29/38—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones
- C07C29/40—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring increasing the number of carbon atoms by reactions with formation of hydroxy groups, which may occur via intermediates being derivatives of hydroxy, e.g. O-metal by reaction with aldehydes or ketones with compounds containing carbon-to-metal bonds
-
- 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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D453/00—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids
- C07D453/02—Heterocyclic compounds containing quinuclidine or iso-quinuclidine ring systems, e.g. quinine alkaloids containing not further condensed quinuclidine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/36—Systems containing two condensed rings the rings having more than two atoms in common
- C07C2602/42—Systems containing two condensed rings the rings having more than two atoms in common the bicyclo ring system containing seven carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB7906243 | 1979-02-22 |
Publications (1)
Publication Number | Publication Date |
---|---|
HU188123B true HU188123B (en) | 1986-03-28 |
Family
ID=10503360
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HU80410A HU188123B (en) | 1979-02-22 | 1980-02-21 | Process for preparing new substituted imidazole derivatives and acid addition salts thereof |
Country Status (20)
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
HU188123B (en) * | 1979-02-22 | 1986-03-28 | The Wellcome Foundation Ltd,Gb | Process for preparing new substituted imidazole derivatives and acid addition salts thereof |
DE2944662A1 (de) * | 1979-11-06 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Cycloheptatrienylimidazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
DE2944663A1 (de) * | 1979-11-06 | 1981-05-14 | Bayer Ag, 5090 Leverkusen | Imidazolderivate, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
JPS6036427B2 (ja) * | 1980-12-05 | 1985-08-20 | 塩野義製薬株式会社 | 1−ベンジルイミダゾ−ル誘導体 |
DE3465993D1 (en) * | 1983-08-11 | 1987-10-15 | Synthelabo | Indole derivatives, their preparation and their therapeutical application |
DE3508905A1 (de) * | 1985-03-13 | 1986-09-18 | Hoechst Ag, 6230 Frankfurt | Neue imidazolylverbindungen und verfahren zu ihrer herstellung |
US4783474A (en) * | 1985-07-20 | 1988-11-08 | Bayer Aktiengesellschaft | Halogenoalkyl-, alkenyl- and alkinyl-azoles |
DE3700916A1 (de) * | 1987-01-14 | 1988-07-28 | Bayer Ag | Halogenalkyl-, alkenyl- und alkinyl-azole |
US5272167A (en) * | 1986-12-10 | 1993-12-21 | Schering Corporation | Pharmaceutically active compounds |
DE3827117A1 (de) * | 1988-08-10 | 1990-02-15 | Ruetgerswerke Ag | Verfahren zur herstellung von chinuclidin-3-methanol |
IT1251431B (it) * | 1991-10-25 | 1995-05-09 | Costante Fontana | Composto ad elevate caratteristiche stabilizzanti particolarmente per perossidi inorganici utilizzati in applicazioni industriali |
DE69637097T2 (de) * | 1995-10-13 | 2007-09-20 | Neurosearch A/S | 8-Azabicyclo(3.2.1)Oct-2-en-Derivate, deren Herstellung und Anwendung |
WO2006105217A2 (en) * | 2005-03-31 | 2006-10-05 | Schering Corporation | Spirocyclic thrombin receptor antagonists |
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US2836598A (en) * | 1958-05-27 | Tertiary-amino - substituted i | ||
US29935A (en) * | 1860-09-04 | Joseph f | ||
US3259637A (en) * | 1963-05-27 | 1966-07-05 | Frosst & Co Charles E | 3, 3-dimethyl-8-bromomethyl-2, 7-dioxaspiro (4.4)nonane |
GB1164564A (en) | 1967-08-21 | 1969-09-17 | Shell Int Research | Novel Cyclobexylpentadienone Acid Derivatives, the preparation thereof and Compositions containing the same |
USRE29935E (en) * | 1968-11-29 | 1979-03-13 | Bayer Aktiengesellschaft | N-Substituted imidazoles and their salts |
DE2007794A1 (de) * | 1970-02-20 | 1971-09-02 | Farbenfabriken Bayer Aktiengesell schaft, 5090 Leverkusen | Fungizide Mittel |
US3666755A (en) * | 1970-03-26 | 1972-05-30 | Merck & Co Inc | 2-imidazolylbicyclo{8 2.2.2{9 octanes |
DE2016839C3 (de) * | 1970-04-09 | 1979-03-22 | Bayer Ag, 5090 Leverkusen | PhenyM4-phenoxyphenyi)-imidazol-1-yl-methane, Verfahren zu ihrer Herstellung sowie diese Verbindungen enthaltende Arzneimittel |
US3682951A (en) * | 1970-11-02 | 1972-08-08 | Searle & Co | 1-{8 {62 -(1-adamantyloxy)halophenethyl{9 {0 imidazoles and congeners |
FR2129838A1 (en) * | 1971-03-16 | 1972-11-03 | Boehringer Mannheim Gmbh | Diuretic/saluretic dibenzo cycloheptene - derivs |
US4107206A (en) * | 1974-04-08 | 1978-08-15 | Akzona Incorporated | Benzo-bicyclononene- derivatives |
SE7600674L (sv) * | 1975-02-05 | 1976-08-06 | Rohm & Haas | Fungicider |
US4057549A (en) * | 1975-04-16 | 1977-11-08 | G. D. Searle & Co. | Triarylpropyl-azabicyclooctanes |
US4156694A (en) * | 1975-04-29 | 1979-05-29 | Akzona Incorporated | Benzobicyclononene derivatives |
US4036975A (en) * | 1975-07-28 | 1977-07-19 | Xyntex (U.S.A) Inc. | 1-[2-(1-Adamantyl)-2-(R-thio)ethyl]imidazoles and 1-[2-(1-adamantyl)-2-(R-oxy)ethyl]imidazoles |
US4031224A (en) * | 1976-04-29 | 1977-06-21 | American Hoechst Corporation | 1,3-Dihydro-heteroarylspiro (isobenzofuran)s |
US4396771A (en) * | 1977-10-19 | 1983-08-02 | Burroughs Wellcome Co. | Imidazole derivatives and salts thereof |
EP0003732B1 (en) * | 1978-02-01 | 1983-10-19 | The Wellcome Foundation Limited | Imidazole derivatives and salts thereof, their synthesis, and pharmaceutical formulations thereof |
HU188123B (en) * | 1979-02-22 | 1986-03-28 | The Wellcome Foundation Ltd,Gb | Process for preparing new substituted imidazole derivatives and acid addition salts thereof |
-
1980
- 1980-02-21 HU HU80410A patent/HU188123B/hu unknown
- 1980-02-21 FI FI800519A patent/FI800519A7/fi not_active Application Discontinuation
- 1980-02-21 GB GB800588A patent/GB2044259B/en not_active Expired
- 1980-02-21 IL IL59444A patent/IL59444A0/xx unknown
- 1980-02-21 JP JP2106080A patent/JPS55115872A/ja active Pending
- 1980-02-21 AU AU55765/80A patent/AU531899B2/en not_active Ceased
- 1980-02-21 IE IE341/80A patent/IE49744B1/en unknown
- 1980-02-21 NZ NZ192941A patent/NZ192941A/xx unknown
- 1980-02-21 AT AT0097580A patent/AT373881B/de not_active IP Right Cessation
- 1980-02-21 DE DE8080100869T patent/DE3067505D1/de not_active Expired
- 1980-02-21 DK DK75680A patent/DK75680A/da not_active Application Discontinuation
- 1980-02-21 US US06/123,712 patent/US4328234A/en not_active Expired - Lifetime
- 1980-02-21 IT IT47968/80A patent/IT1128095B/it active
- 1980-02-21 ES ES488803A patent/ES8103055A1/es not_active Expired
- 1980-02-21 MC MC801433A patent/MC1315A1/xx unknown
- 1980-02-21 GR GR61259A patent/GR70277B/el unknown
- 1980-02-21 KR KR1019800000712A patent/KR850000380B1/ko not_active Expired
- 1980-02-21 PT PT70856A patent/PT70856B/pt unknown
- 1980-02-21 ZA ZA00800996A patent/ZA80996B/xx unknown
- 1980-02-21 EP EP80100869A patent/EP0015002B1/en not_active Expired
-
1982
- 1982-09-29 US US06/427,856 patent/US4525475A/en not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
AT373881B (de) | 1984-02-27 |
US4525475A (en) | 1985-06-25 |
DK75680A (da) | 1980-08-23 |
IT8047968A0 (it) | 1980-02-21 |
KR850000380B1 (ko) | 1985-03-23 |
ATA97580A (de) | 1983-07-15 |
IT1128095B (it) | 1986-05-28 |
IE800341L (en) | 1980-08-22 |
ZA80996B (en) | 1981-04-29 |
EP0015002A1 (en) | 1980-09-03 |
FI800519A7 (fi) | 1981-01-01 |
IE49744B1 (en) | 1985-12-11 |
KR830001904A (ko) | 1983-05-19 |
GR70277B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-09-03 |
GB2044259A (en) | 1980-10-15 |
ES488803A0 (es) | 1981-02-16 |
ES8103055A1 (es) | 1981-02-16 |
EP0015002B1 (en) | 1984-04-18 |
PT70856A (en) | 1980-03-01 |
MC1315A1 (fr) | 1981-03-10 |
NZ192941A (en) | 1984-10-19 |
AU531899B2 (en) | 1983-09-08 |
PT70856B (en) | 1981-06-11 |
AU5576580A (en) | 1980-08-28 |
US4328234A (en) | 1982-05-04 |
GB2044259B (en) | 1983-08-03 |
JPS55115872A (en) | 1980-09-06 |
IL59444A0 (en) | 1980-05-30 |
DE3067505D1 (en) | 1984-05-24 |
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