KR920014804A - 아릴 (또는 헤테로아릴) 피페라지닐알킬아졸 유도체 및 그의 제조방법 및 그의 의약품으로의 이용 - Google Patents
아릴 (또는 헤테로아릴) 피페라지닐알킬아졸 유도체 및 그의 제조방법 및 그의 의약품으로의 이용 Download PDFInfo
- Publication number
- KR920014804A KR920014804A KR1019920001213A KR920001213A KR920014804A KR 920014804 A KR920014804 A KR 920014804A KR 1019920001213 A KR1019920001213 A KR 1019920001213A KR 920001213 A KR920001213 A KR 920001213A KR 920014804 A KR920014804 A KR 920014804A
- Authority
- KR
- South Korea
- Prior art keywords
- butyl
- piperazinyl
- pyrimidinyl
- formula
- compound
- Prior art date
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- 238000000034 method Methods 0.000 title claims 7
- 125000003118 aryl group Chemical group 0.000 title claims 6
- 239000003814 drug Substances 0.000 title claims 3
- 125000001072 heteroaryl group Chemical group 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 18
- -1 alkyl radical Chemical class 0.000 claims 6
- 229910052757 nitrogen Inorganic materials 0.000 claims 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 5
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 2
- 125000000477 aza group Chemical group 0.000 claims 2
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000001424 substituent group Chemical group 0.000 claims 2
- SMPRUJMRROLHLK-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperazine Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCN(C=2C(=CC=CC=2)Cl)CC1 SMPRUJMRROLHLK-UHFFFAOYSA-N 0.000 claims 1
- IJHYWNSXROVFEB-UHFFFAOYSA-N 1-(2-chlorophenyl)-4-[4-(4-chloropyrazol-1-yl)butyl]piperazine Chemical compound C1=C(Cl)C=NN1CCCCN1CCN(C=2C(=CC=CC=2)Cl)CC1 IJHYWNSXROVFEB-UHFFFAOYSA-N 0.000 claims 1
- ASZFAUXWSFVZAB-UHFFFAOYSA-N 1-(2-methoxyphenyl)-4-(4-pyrrol-1-ylbutyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCCN2C=CC=C2)CC1 ASZFAUXWSFVZAB-UHFFFAOYSA-N 0.000 claims 1
- KABUQOGOEPRZLF-UHFFFAOYSA-N 1-(3-chlorophenyl)-4-[4-(4-chloropyrazol-1-yl)butyl]piperazine Chemical compound C1=C(Cl)C=NN1CCCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 KABUQOGOEPRZLF-UHFFFAOYSA-N 0.000 claims 1
- SJHNVFCZXGWJTB-UHFFFAOYSA-N 1-(4-methoxyphenyl)-4-(4-pyrrol-1-ylbutyl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(CCCCN2C=CC=C2)CC1 SJHNVFCZXGWJTB-UHFFFAOYSA-N 0.000 claims 1
- BGMONSPMFSWTDE-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCCN2C(=C(Cl)N=C2C)Cl)CC1 BGMONSPMFSWTDE-UHFFFAOYSA-N 0.000 claims 1
- CNNRSXJDTGAFFI-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-(4-methoxyphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(CCCCN2C(=C(Cl)N=C2C)Cl)CC1 CNNRSXJDTGAFFI-UHFFFAOYSA-N 0.000 claims 1
- HECQSSYFOSYMDF-UHFFFAOYSA-N 1-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]-4-phenylpiperazine Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCN(C=2C=CC=CC=2)CC1 HECQSSYFOSYMDF-UHFFFAOYSA-N 0.000 claims 1
- LKXRSRWCCCBMKO-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-(2-methoxyphenyl)piperazine Chemical compound COC1=CC=CC=C1N1CCN(CCCCN2N=CC(Cl)=C2)CC1 LKXRSRWCCCBMKO-UHFFFAOYSA-N 0.000 claims 1
- WBDLDVVKTVPZFO-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-(4-methoxyphenyl)piperazine Chemical compound C1=CC(OC)=CC=C1N1CCN(CCCCN2N=CC(Cl)=C2)CC1 WBDLDVVKTVPZFO-UHFFFAOYSA-N 0.000 claims 1
- URUJIBBTPVGPFD-UHFFFAOYSA-N 1-[4-(4-chloropyrazol-1-yl)butyl]-4-phenylpiperazine Chemical compound C1=C(Cl)C=NN1CCCCN1CCN(C=2C=CC=CC=2)CC1 URUJIBBTPVGPFD-UHFFFAOYSA-N 0.000 claims 1
- YLDDKRPMUDJBEJ-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-9h-carbazole Chemical compound C=1C=CC=2C3=CC=CC=C3NC=2C=1CCCCN(CC1)CCN1C1=NC=CC=N1 YLDDKRPMUDJBEJ-UHFFFAOYSA-N 0.000 claims 1
- RKZCHNZWRHNEJL-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzimidazole Chemical compound C1=NC2=CC=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 RKZCHNZWRHNEJL-UHFFFAOYSA-N 0.000 claims 1
- KJCNIHPJAPIEQO-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzotriazole Chemical compound N1=NC2=CC=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 KJCNIHPJAPIEQO-UHFFFAOYSA-N 0.000 claims 1
- CPRKRLWYJRLBCG-UHFFFAOYSA-N 1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]indole Chemical compound C1=CC2=CC=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 CPRKRLWYJRLBCG-UHFFFAOYSA-N 0.000 claims 1
- NFCIKJHTSWMUOJ-UHFFFAOYSA-N 1-phenyl-4-(4-pyrrol-1-ylbutyl)piperazine Chemical compound C1CN(C=2C=CC=CC=2)CCN1CCCCN1C=CC=C1 NFCIKJHTSWMUOJ-UHFFFAOYSA-N 0.000 claims 1
- XKXOJCMGWOFARI-UHFFFAOYSA-N 2,3-diphenyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]indole Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN(C1=CC=CC=C11)C(C=2C=CC=CC=2)=C1C1=CC=CC=C1 XKXOJCMGWOFARI-UHFFFAOYSA-N 0.000 claims 1
- GFISDBXSWQMOND-UHFFFAOYSA-N 2,5-dimethoxyoxolane Chemical compound COC1CCC(OC)O1 GFISDBXSWQMOND-UHFFFAOYSA-N 0.000 claims 1
- LJAUERDRVNMYTC-UHFFFAOYSA-N 2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzotriazole Chemical compound N1=C2C=CC=CC2=NN1CCCCN(CC1)CCN1C1=NC=CC=N1 LJAUERDRVNMYTC-UHFFFAOYSA-N 0.000 claims 1
- DPVBORWRJDDYOO-UHFFFAOYSA-N 2-[4-[4-(1,2,4-triazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN1C=NC=N1 DPVBORWRJDDYOO-UHFFFAOYSA-N 0.000 claims 1
- WRENIUFLMSOSQY-UHFFFAOYSA-N 2-[4-[4-(2,4,5-triphenylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN1C(C=2C=CC=CC=2)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 WRENIUFLMSOSQY-UHFFFAOYSA-N 0.000 claims 1
- JXILGMCIFQBYHY-UHFFFAOYSA-N 2-[4-[4-(2-methyl-4,5-diphenylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN1C(C)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 JXILGMCIFQBYHY-UHFFFAOYSA-N 0.000 claims 1
- ZBSUKJJLDMRCRH-UHFFFAOYSA-N 2-[4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound CC1=NC(Cl)=C(Cl)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 ZBSUKJJLDMRCRH-UHFFFAOYSA-N 0.000 claims 1
- NTKJAOXUEPWSCE-UHFFFAOYSA-N 2-[4-[4-(4,5-dichloro-2-methylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine;2-hydroxypropane-1,2,3-tricarboxylic acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O.CC1=NC(Cl)=C(Cl)N1CCCCN1CCN(C=2N=CC=CN=2)CC1 NTKJAOXUEPWSCE-UHFFFAOYSA-N 0.000 claims 1
- AFSMOCWESFBRCB-UHFFFAOYSA-N 2-[4-[4-(4-phenylimidazol-1-yl)butyl]piperazin-1-yl]pyrimidine Chemical compound C1CN(C=2N=CC=CN=2)CCN1CCCCN(C=1)C=NC=1C1=CC=CC=C1 AFSMOCWESFBRCB-UHFFFAOYSA-N 0.000 claims 1
- PRNCKYBEKYQAOL-UHFFFAOYSA-N 2-chloro-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzimidazole Chemical compound ClC1=NC2=CC=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 PRNCKYBEKYQAOL-UHFFFAOYSA-N 0.000 claims 1
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims 1
- IADBTPHJJXGQSG-UHFFFAOYSA-N 2-methyl-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzimidazole Chemical compound CC1=NC2=CC=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 IADBTPHJJXGQSG-UHFFFAOYSA-N 0.000 claims 1
- JVPBFKATUYFDED-UHFFFAOYSA-N 5-chloro-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzimidazole Chemical compound C1=NC2=CC(Cl)=CC=C2N1CCCCN(CC1)CCN1C1=NC=CC=N1 JVPBFKATUYFDED-UHFFFAOYSA-N 0.000 claims 1
- UFZNAQYYJCEXFE-UHFFFAOYSA-N 6-chloro-1-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]benzimidazole Chemical compound C12=CC(Cl)=CC=C2N=CN1CCCCN(CC1)CCN1C1=NC=CC=N1 UFZNAQYYJCEXFE-UHFFFAOYSA-N 0.000 claims 1
- 208000019901 Anxiety disease Diseases 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 206010020772 Hypertension Diseases 0.000 claims 1
- 206010040007 Sense of oppression Diseases 0.000 claims 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims 1
- 206010048010 Withdrawal syndrome Diseases 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 125000005599 alkyl carboxylate group Chemical group 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 230000036506 anxiety Effects 0.000 claims 1
- 239000002249 anxiolytic agent Substances 0.000 claims 1
- 230000000949 anxiolytic effect Effects 0.000 claims 1
- 150000001556 benzimidazoles Chemical class 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- TUJKJAMUKRIRHC-UHFFFAOYSA-N hydroxyl Chemical compound [OH] TUJKJAMUKRIRHC-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 150000002460 imidazoles Chemical class 0.000 claims 1
- 125000004857 imidazopyridinyl group Chemical class N1C(=NC2=C1C=CC=N2)* 0.000 claims 1
- 125000005905 mesyloxy group Chemical group 0.000 claims 1
- 125000006574 non-aromatic ring group Chemical group 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 238000006722 reduction reaction Methods 0.000 claims 1
- 239000003381 stabilizer Substances 0.000 claims 1
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two 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 with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- 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
-
- 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
- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/16—Halogen atoms or nitro radicals
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- 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
- C07D231/14—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
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- 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
- 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
- C07D233/66—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/68—Halogen atoms
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- 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
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Pain & Pain Management (AREA)
- Anesthesiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
Abstract
내용 없음
Description
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Claims (11)
- 히기의 일반식(Ⅰ)을 가지는 것을 특징으로 하는 복소환식 화합물.상기의 일반식에서, Ar은 질소를 포함하거나 포함하지 않으며, 다른 치환체를 가진 아릴류, 2-피리미딘, 2-N-메틸이미다졸 및 3-(1,2-벤즈이소트리아졸)로부어 선택되어지는 방향족 리디킬을 나타내며, n은 1 내지 6의 값, Z1은 질소원자 또는 C-R1기, Z2는 질소원자 또는 C-R2기, Z4는 질소원자 또는 C-R4기, Z5는 질소원자 또는 탄소원자, Z6는 아자기 또는 치환되거나 치환되지 않은 메틸렌기를 나타내는데 Z5가 질소원자일 경우에는 Z6는 메틸렌기, Z5가 탄소원자일 경우에는 Z6는 치환되거나 치환되지 않은 아자기를 나타낸다. R1, R2, R3, R4는 동일하거나 다를 수 있으며, 또다른 방향족 또는 비방향족 고리르 형성할 수도 있다. R1, R2, R3, R4는 수소원자, 할로겐, 저급 알킬 라디칼, 히드록실 라디칼, 카르복실 라디칼, 카르복스아미도 라디칼, 알킬카르복실레이트라디칼 또는 아릴 또는 치환된 아릴 라디칼을 나타내는데, Ar이 2-피리미딘이고, Z6가 치환되거나 치환되지 않은 메틸렌기일 때 Z1내지 Z6은 모두 3치환된 이미다졸, 치환되거나 치환되지 않은 벤즈이미다졸 및 치환되거나 치환되지 않은 이미다조피리딘으로 구성된 그룹으로부터 선택되는 복소환식 방향족 라디칼 및 그들의 제약학적으로 수용가능한 산부가염을 나타낸다. 다만, 여기서 Ar이 치환되거나, 치환되지 않는 페닐기이고, Z2및 Z5가 모두 질소원자, Z1이 C-R1기, Z4는 C-R4기, R3-R4가 또다른 방향족 고리를 형성하는 화합물은 제외된다.
- 제1항에 있어서, 상기 일반식(Ⅰ)이 하기의 군으로부터 선택되는 것을 특징으로 하는 복소환식 화합물 1) 1-{4-[4-(2-피리미디닐)-1-페페라지닐]-부틸}-피롤 2) 1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-카아바졸 3)1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-인돌 4) 2,3-디페닐-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-인돌 5) 2,4,5-트리페닐-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-이미다졸 6) 4,5-디페닐-2메틸-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-이미다졸 7) 4,5-디클로로-2-메틸-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-이미다졸 8) 4-페닐-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-이미다졸 9) 1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤즈이미다졸 10)1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-3H-이미다조[5,4-b]피리미딘 11) 1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-이미다조[4,5-b]피리미딘 12) 1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤조트리 아졸 13) 2-클로로 -1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤즈이미다졸 14) 5-클로로-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤즈이미다졸 15) 6-클로로-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤즈 이미다졸 16) 1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-1,2,4-트리아졸 17) 2-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-2H-벤조트리아졸 18) 2-메틸-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤즈이미다졸 19) 5,6-디메틸-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-벤즈 이미다졸 20) 4-클로로-1-{4-[4-(4-메톡시페닐)-1-피페라지닐]-부틸}-1H-피라졸 21) 4,5-디클로로-2-메틸-1-{4-[4-(4-메톡시페닐)-1-피페라지닐]-부틸}-1H-이미다졸 22) 4-클로로-1-{4-[4-(2-메톡시페닐)-1-피페라지닐]-부틸}-1H-피라졸 23) 4,5-디클로로-2-메틸-1-{4-[4-(2-메톡시페닐)-1-피페라지닐]-부틸}-1H-이미다졸 24) 4-클로로-1-{4-[4-(2-메톡시페닐)-1-피페라지닐]-부틸}-1H-피라졸 25) 1-{4-[4-(4-메톡시페닐)-1-피페라지닐]-부틸}-피롤 26) 1-{4-[4-(2-메톡시페닐)-1-피페라지닐]-부틸}-피롤 27) 1-{4-[4-페닐-1-피페라지닐]-부틸}-피롤 28) 4-클로로-1-{4-[4-페닐-1-피페라지닐]-부틸}-1H-피라졸 29) 4,5-디클로로-2-메틸-1-{4-[4-페닐-1-피페라지닐]-부틸}-1H-이미다졸 30) 4-클로로-1-{4-[4-(2-클로로페닐)-1-피페라지닐]-부틸}-1H-피라졸 31) 4,5-디클로로-2-메틸-1-{4-[4-(2-클로로페닐)-1-피페라지닐]-부틸}-1H-이미다졸 32) 4-클로로-1-{4-[4-(3-클로로페닐)-1-피페라지닐]-부틸}-1H-피라졸 33) 1-{4-[4-(2-N-메틸이미다졸일)-1-피페라지닐]-부틸}-1H-피라졸 34) 4-클로로-1-{2-[4-(2-메톡시페닐)-1-피페라지닐]-부틸}-1H-피라졸 35) 4,5-디클로로-2-메틸-1-{4-[4-(2-피리미디닐)-1-피페라지닐]-부틸}-1H-이미다졸 시트르산염 36) 4-클로로-1-{4-[4-(3-(1,2-벤즈이소트리아졸일)-1-피페라지닐]-부틸}-1H-피라졸 37) 4,5-디클로로-2메틸-1-{4-[4-(3-(1,2-벤즈이소트리아졸일)-1-피페라지닐]-부틸}-1H-이미다졸 38) 1,3{-디메틸-5-3-[4-(2-(메톡시페닐)-1-피페라지닐]-프로필아미노}-1H-피라졸.
- 하기 일반식(Ⅱ)의 화합물과 하기 일반식(Ⅲ)의 화합물의 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의 제조방법.상기 식에서 Ar및 n은 제1항에서와 같이 의미를 가지며, X는 할로겐 원자 또는 토실옥시나 메실옥시로부터 선택되는 이탈기를 나타낸다.상기 식에서 Z1, Z2, Z4및 R3는 제1항에서의 의미와 같다.
- 하기 일반식(Ⅳ)의 화합물과 하기 일반식(Ⅴ)의 화합물의 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의 제조방법.상기 식에서 Z1, Z2, Z4, Z5, Z6, Z3, n 및 X는 제1항에서의 의미와 같다.상기 식에서 Ar은 제1항에서의 의미와 같다.
- 하기 일반식(Ⅵ)의 화합물과 하기 일반식(Ⅶ)의 화합물의 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의 제조방법.상기 식에서 Z1, Z2, Z4, Z5, Z6, R3및 n은 제1항에서의 의미와 같다.Ar-X(Ⅶ)상기 식에서 Ar 및 X는 제1항에서의 의미와 같다.
- 하기 일반식(Ⅷ)의 화합물과 2,5-디메톡시테트라하이드로 퓨란과의 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의제조방법.상기 식에서 Ar 및 n은 제1항에서의 의미와 같다.
- Ar, n, Z1, Z2, Z4, Z5, Z6및 R3가 알킬카르복실레이트기를 나타낼 때 상기 일반식(Ⅰ)의 화합물의 가수분해 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의 제조방법.
- Ar, n, Z1, Z2, Z4, Z5, Z6및 R3가 제1항에서의 의미와 같으며, 치환체 R1, R2, R3및 R4가 카르복실 라디칼을 나타내는 상기 일반식(Ⅰ)의 화합물과 아민과의 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의 제조방법.
- 하기 일반식(Ⅸ)의 화합물의 환원 반응을 포함하는 조작을 사용하는 것을 특징으로 하는 제1항 또는 제2항에 따른 화합물의 제조방법.상기 식에서 Ar, Z1, Z2, Z4, Z5, Z6, R3및 n은 제1항에 있어서의 의미와 같다.
- 불안증의 치료를 위한 의약품의 제조, 특히 정신안정제 및/또는 불안해소제의 제조 및, 억압, 금단증후군, 인식 장해 및 고혈압의 치료를 위한 의약품의 제조를 위한, 제1항 내지 제5항중 어느 한 항에 따른 일반식(Ⅰ)의 유도체 및 그들의 생리학적으로 수용가능한 염의 이용.
- 제약학적으로 수용가능한 부형제에 부가하여 제1항 내지 제4항중 어느 한 항에 따른 일반식(Ⅰ)의 적어도 하나의 유도체 또는 그의 생리학적으로 수용가능한 염의 적어도 하나를 포함하는 것을 특징으로 하는 제약학적 조성.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
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FR9100923A FR2672052B1 (fr) | 1991-01-28 | 1991-01-28 | Derives d'aryl (ou heteroaryl)-piperazinyl-alkyl-azoles, leur preparation et leur application en tant que medicaments. |
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Families Citing this family (41)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
FR2665160A1 (fr) * | 1990-07-26 | 1992-01-31 | Esteve Labor Dr | Nouveaux derives de 1-diphenylmethylpiperazine, leur preparation et leur application en tant que medicaments. |
FR2665161B1 (fr) * | 1990-07-26 | 1992-11-27 | Esteve Labor Dr | Nouveaux derives de benzimidazole, leur preparation et leur application en tant que medicaments. |
US5646281A (en) * | 1990-12-28 | 1997-07-08 | Neurogen Corporation | Certain 4-piperidino- and piperazinomethyl-2-phenyl imidazole derivatives; dopamine receptor subtype specific ligands |
US5681956A (en) * | 1990-12-28 | 1997-10-28 | Neurogen Corporation | 4-aryl substituted piperazinylmethyl phenylimidazole derivatives; a new class of dopamine receptor subtype specific ligands |
FR2673628B1 (fr) * | 1991-03-07 | 1993-07-09 | Esteve Labor Dr | Procede de preparation de derives d'aryl (ou heteroaryl)-piperazinyl-butyl-azoles. |
FR2701260B1 (fr) * | 1993-02-05 | 1995-05-05 | Esteve Labor Dr | Dérivés de 2-[4-(4-azolylbutyl)-1-pipérazinyl]-5-hydroxypyrimidine, leur préparation et leur application en tant que médicaments. |
FR2705098B1 (fr) * | 1993-05-10 | 1995-08-04 | Esteve Labor Dr | Procédé de préparation de 2-{4-[4-(chloro-1-pyrazolyl)butyl]1-pipérazinyl}pyrimidine (Lesopitron) . |
WO1995003298A1 (en) * | 1993-07-19 | 1995-02-02 | Fujisawa Pharmaceutical Co., Ltd. | BENZIMIDAZOLE DERIVATIVES USEFUL AS DOPAMINE RECEPTOR ANTAGONIST, 5-HT RECEPTOR AGONIST OR α1 RECEPTOR ANTAGONIST |
FR2712808B1 (fr) * | 1993-11-25 | 1996-02-16 | Esteve Labor Dr | Utilisation des dérivés de 1-{4-[4-aryl(ou hétéroaryl)-1-pipérazinyl]-butyl}-1-H-azole pour la préparation de médicaments destinés au traitement des troubles de la sécrétion gastrique . |
US5418236A (en) * | 1993-12-23 | 1995-05-23 | Ortho Pharmaceutical Corporation | Anxiolytic aroyl piperidinyl and piperazinylacyl pyrroles |
DE4425144A1 (de) * | 1994-07-15 | 1996-01-18 | Basf Ag | Triazolverbindungen und deren Verwendung |
FR2723091B1 (fr) * | 1994-07-29 | 1996-11-08 | Esteve Labor Dr | Tetrahydropyridine-(6,4-hydroxypiperidine) alkylazoles |
ES2117934B1 (es) * | 1994-07-29 | 1999-04-01 | Esteve Labor Dr | Tetrahidropiridinas (0 4-hidroxipiperidinas) alquilazoles. |
US6355659B1 (en) | 1994-07-29 | 2002-03-12 | Laboratorios Del Dr. Esteve, S.A. | 4-(4-Chlorophenyl)-1236-tetrahydro-1(1H-124-triazol-1-yl)butty)pyrideine and salts thereof; pharmaceutical compositions and method of treating psychoses utilizing same |
US5618816A (en) * | 1995-03-02 | 1997-04-08 | Bristol-Myers Squibb Company | Antimigraine 1,2,5-thiadiazole derivatives of indolylalkyl-pyridnyl and pyrimidinylpiperazines |
ES2099031B1 (es) * | 1995-05-31 | 1997-12-01 | Esteve Labor Dr | Nuevos polimorfos de diclorhidrato de lesopitron y sus formas hidratadas, procedimientos de preparacion y composiciones que los contienen. |
AU6517196A (en) * | 1995-07-13 | 1997-02-10 | Knoll Aktiengesellschaft | Piperazine derivatives as therapeutic agents |
FR2742052B1 (fr) * | 1995-12-12 | 1998-04-10 | Esteve Labor Dr | Utilisation des derives 1-(4-(4-aryl (ou heteroaryl)-1-piper azinyl)-buty)-1h-azole pour le traitement de la depression, des troubles obsessifs compulsifs, l'apnee du sommeil, les dysfonctions sexuelles, l'emese et le mal des transports |
FR2763950B1 (fr) * | 1997-06-02 | 2002-09-20 | Esteve Labor Dr | 2- {4- [4-(4,5-dichloro-2-methylimidazol-1-yl)butyl] -1- piperazinyl }-5-fluoropyrimidine, sa preparation et son utilisation therapeutique |
DE19728996A1 (de) | 1997-07-07 | 1999-01-14 | Basf Ag | Triazolverbindungen und deren Verwendung |
ES2125206B1 (es) * | 1997-07-21 | 1999-11-16 | Esteve Labor Dr | Derivados de acil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos. |
US6166205A (en) * | 1998-09-02 | 2000-12-26 | Neurogen Corporation | 2-Aryl-4-(1-[4-heteroaryl]piperazin-1-yl)methylimidazoles: dopamine . D.sub4 receptor subtype ligands |
TW526202B (en) | 1998-11-27 | 2003-04-01 | Shionogi & Amp Co | Broad spectrum cephem having benzo[4,5-b]pyridium methyl group of antibiotic activity |
US6046331A (en) * | 1998-12-17 | 2000-04-04 | Synaptic Pharmaceutical Corporation | Imidazolones and their use in treating benign prostatic hyperplasia and other disorders |
ES2167276B1 (es) | 2000-10-20 | 2003-04-01 | Esteve Labor Dr | Nuevos derivados de cianoaril (o cianoheteroaril)-carbonil-piperazinil-pirimidinas, su preparacion y su aplicacion como medicamentos. |
US20050256130A1 (en) * | 2002-06-12 | 2005-11-17 | Chemocentryx, Inc. | Substituted piperazines |
CN1867336B (zh) | 2002-06-12 | 2010-05-12 | 凯莫森特里克斯股份有限公司 | 1-芳基-4-取代的哌嗪衍生物及其制药用途 |
US7842693B2 (en) * | 2002-06-12 | 2010-11-30 | Chemocentryx, Inc. | Substituted piperazines |
US7589199B2 (en) * | 2002-06-12 | 2009-09-15 | Chemocentryx, Inc. | Substituted piperazines |
EP1720545B1 (en) | 2004-03-03 | 2014-10-29 | ChemoCentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
US7435831B2 (en) * | 2004-03-03 | 2008-10-14 | Chemocentryx, Inc. | Bicyclic and bridged nitrogen heterocycles |
US7781478B2 (en) | 2004-07-14 | 2010-08-24 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7772271B2 (en) | 2004-07-14 | 2010-08-10 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
US7868037B2 (en) | 2004-07-14 | 2011-01-11 | Ptc Therapeutics, Inc. | Methods for treating hepatitis C |
NZ553329A (en) | 2004-07-22 | 2010-09-30 | Ptc Therapeutics Inc | Thienopyridines for treating hepatitis C |
FR2877005A1 (fr) * | 2004-10-22 | 2006-04-28 | Bioprojet Soc Civ Ile | Nouveaux derives d'arylpiperazine |
KR100654328B1 (ko) | 2005-08-26 | 2006-12-08 | 한국과학기술연구원 | 피페라지닐알킬피라졸계 t-타입 칼슘 채널 억제 화합물 및이의 제조방법 |
GB2435827A (en) * | 2006-03-09 | 2007-09-12 | Del Dr Esteve S A Spain Lab | Use of substituted piperazine compounds for the treatment of food related disorders |
KR100882925B1 (ko) * | 2007-06-14 | 2009-02-10 | 한국과학기술연구원 | 세로토닌 5-ht₃a 길항적 효과를 갖는 피라졸 유도체함유 약제 조성물 |
EP2924032B1 (en) * | 2012-11-26 | 2019-03-06 | Shenyang Haiwang Biotechnology Co., Ltd | Benzo five-membered nitrogen heterocyclic piperidine or piperazine derivatives and preparation methods and pharmaceutical compositions thereof |
EP2924033B1 (en) * | 2012-11-26 | 2019-02-27 | Shenyang Haiwang Biotechnology Co., Ltd | Use of benzo five-membered nitrogen heterocyclic piperazine or piperidine derivatives |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3362956A (en) * | 1965-08-19 | 1968-01-09 | Sterling Drug Inc | 1-[(heterocyclyl)-lower-alkyl]-4-substituted-piperazines |
GB1117068A (en) * | 1965-12-15 | 1968-06-12 | Acraf | S-triazole-[4,3-a]-pyridine derivatives and processes for their preparation |
US3468882A (en) * | 1966-10-07 | 1969-09-23 | Sterling Drug Inc | Phenylhydrazone derivatives as intermediates for preparing indoles |
GB1189064A (en) * | 1967-05-01 | 1970-04-22 | Sterling Drug Inc | Indole Derivatives |
US3491098A (en) * | 1967-05-29 | 1970-01-20 | Sterling Drug Inc | 1-((imidazolyl)-lower-alkyl)-4-substituted-piperazines |
US3472855A (en) * | 1967-05-29 | 1969-10-14 | Sterling Drug Inc | 1-((benz(g)-indolyl)-lower-alkyl)-4-substituted-piperazines |
US3511841A (en) * | 1967-05-29 | 1970-05-12 | Sterling Drug Inc | 1-((4-,5-,6-,and 7-azaindolyl)-lower-alkyl)- 4-substituted-piperazines |
DE2143730A1 (de) * | 1971-09-01 | 1973-03-08 | Byk Gulden Lomberg Chem Fab | Substituierte pyridine, verfahren zu deren herstellung und sie enthaltende arzneimittel |
DE3101502A1 (de) * | 1981-01-19 | 1982-08-26 | Basf Ag, 6700 Ludwigshafen | Phenylpiperazinderivate von hetarylphenolen und hetarylanilinen, ihre hersttellung und diese enthaltendetherapeutische mittel |
US4605655A (en) * | 1984-03-06 | 1986-08-12 | Bristol-Myers Company | Antipsychotic 1-fluorophenylbutyl-4-(2-pyrimidinyl)piperazine derivatives |
US4547499A (en) * | 1984-05-10 | 1985-10-15 | The Upjohn Company | 2,4-Dihydro-2(omega-aminoalkyl)-1H-[1,2,4]triazolo[3,4-c]benzoxazin-1-one anti-allergy drug compounds, compositions and use |
CA1279645C (en) * | 1986-02-27 | 1991-01-29 | Ineke Van Wijngaarden | Aryl-substituted (n-piperidinyl)methyl- and (n-piperazinyl)methylazoles having antipsychotic properties |
IT1230703B (it) * | 1989-01-26 | 1991-10-29 | Luso Farmaco Inst | Derivati imidazolonici ad attivita' antiipertensiva, loro metodi di preparazione e composizioni farmaceutiche che li contengono. |
FR2642759B1 (fr) * | 1989-02-09 | 1991-05-17 | Laboratorios Esteve Sa | Derives de pyrimidyl-piperazinyl-alkyl azoles avec activite anxiolytique et/ou tranquillisante |
DE3923045A1 (de) * | 1989-07-13 | 1991-01-17 | Merck Patent Gmbh | Indolderivate |
-
1991
- 1991-01-28 FR FR9100923A patent/FR2672052B1/fr not_active Expired - Fee Related
-
1992
- 1992-01-22 DE DE69209679T patent/DE69209679T2/de not_active Expired - Fee Related
- 1992-01-22 AT AT92400164T patent/ATE136547T1/de not_active IP Right Cessation
- 1992-01-22 EP EP92400164A patent/EP0497659B1/fr not_active Expired - Lifetime
- 1992-01-22 DK DK92400164.7T patent/DK0497659T3/da active
- 1992-01-27 CA CA002060090A patent/CA2060090A1/fr not_active Abandoned
- 1992-01-27 US US07/825,929 patent/US5292739A/en not_active Expired - Fee Related
- 1992-01-27 YU YU8292A patent/YU48180B/sh unknown
- 1992-01-27 ZA ZA92534A patent/ZA92534B/xx unknown
- 1992-01-27 ES ES09200159A patent/ES2042385B1/es not_active Expired - Fee Related
- 1992-01-27 RU SU925010640A patent/RU2088582C1/ru active
- 1992-01-27 NO NO920348A patent/NO180539C/no not_active IP Right Cessation
- 1992-01-28 JP JP4013318A patent/JPH0745496B2/ja not_active Expired - Lifetime
- 1992-01-28 AU AU10479/92A patent/AU658389B2/en not_active Ceased
- 1992-01-28 HU HU9200262A patent/HU219909B/hu not_active IP Right Cessation
- 1992-01-28 KR KR1019920001213A patent/KR0135969B1/ko not_active IP Right Cessation
-
1993
- 1993-12-06 US US08/163,329 patent/US5382586A/en not_active Expired - Fee Related
-
1996
- 1996-07-02 GR GR960401810T patent/GR3020437T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
DE69209679D1 (de) | 1996-05-15 |
YU8292A (sh) | 1995-03-27 |
GR3020437T3 (en) | 1996-10-31 |
RU2088582C1 (ru) | 1997-08-27 |
NO180539B (no) | 1997-01-27 |
JPH0745496B2 (ja) | 1995-05-17 |
CA2060090A1 (fr) | 1992-07-29 |
AU658389B2 (en) | 1995-04-13 |
AU1047992A (en) | 1992-07-30 |
NO180539C (no) | 1997-05-07 |
ZA92534B (en) | 1992-10-28 |
US5292739A (en) | 1994-03-08 |
HUT60265A (en) | 1992-08-28 |
YU48180B (sh) | 1997-07-31 |
HU219909B (hu) | 2001-09-28 |
ATE136547T1 (de) | 1996-04-15 |
FR2672052B1 (fr) | 1995-05-24 |
JPH04312584A (ja) | 1992-11-04 |
EP0497659A1 (fr) | 1992-08-05 |
FR2672052A1 (fr) | 1992-07-31 |
ES2042385A1 (es) | 1993-12-01 |
HU9200262D0 (en) | 1992-04-28 |
DE69209679T2 (de) | 1996-10-10 |
KR0135969B1 (ko) | 1998-04-25 |
US5382586A (en) | 1995-01-17 |
ES2042385B1 (es) | 1994-08-01 |
EP0497659B1 (fr) | 1996-04-10 |
DK0497659T3 (da) | 1996-07-15 |
NO920348D0 (no) | 1992-01-27 |
NO920348L (no) | 1992-07-29 |
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