RU2324694C2 - Производные 2-пирролидин-2-ил-[1,3,4]оксадиазола и их применение в качестве антидепрессантов - Google Patents
Производные 2-пирролидин-2-ил-[1,3,4]оксадиазола и их применение в качестве антидепрессантов Download PDFInfo
- Publication number
- RU2324694C2 RU2324694C2 RU2005109164/04A RU2005109164A RU2324694C2 RU 2324694 C2 RU2324694 C2 RU 2324694C2 RU 2005109164/04 A RU2005109164/04 A RU 2005109164/04A RU 2005109164 A RU2005109164 A RU 2005109164A RU 2324694 C2 RU2324694 C2 RU 2324694C2
- Authority
- RU
- Russia
- Prior art keywords
- pyrrolidin
- oxadiazol
- phenyl
- alkyl
- methanone
- Prior art date
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- HYSNXVPAKDTRDH-UHFFFAOYSA-N 2-pyrrolidin-2-yl-1,3,4-oxadiazole Chemical class C1CCNC1C1=NN=CO1 HYSNXVPAKDTRDH-UHFFFAOYSA-N 0.000 title claims abstract description 18
- 239000000935 antidepressant agent Substances 0.000 title claims description 8
- -1 hept-3-yl Chemical group 0.000 claims abstract description 129
- 150000001875 compounds Chemical class 0.000 claims abstract description 50
- 125000003118 aryl group Chemical group 0.000 claims abstract description 39
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 27
- 239000003814 drug Substances 0.000 claims abstract description 22
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 17
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 11
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 10
- 238000000034 method Methods 0.000 claims abstract description 10
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000007942 carboxylates Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- 125000001544 thienyl group Chemical group 0.000 claims abstract description 6
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims abstract description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims abstract description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 4
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002541 furyl group Chemical group 0.000 claims abstract description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 4
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 4
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims abstract description 4
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001847 2-phenylcyclopropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 3
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000003852 triazoles Chemical class 0.000 claims abstract description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 31
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 27
- 125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 25
- 125000001424 substituent group Chemical group 0.000 claims description 20
- 208000002193 Pain Diseases 0.000 claims description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 17
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 230000036407 pain Effects 0.000 claims description 15
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 9
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 8
- 230000001430 anti-depressive effect Effects 0.000 claims description 7
- 229940005513 antidepressants Drugs 0.000 claims description 7
- 238000011282 treatment Methods 0.000 claims description 7
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 230000000202 analgesic effect Effects 0.000 claims description 5
- 230000002265 prevention Effects 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- XSUCTMWHNPDEHX-UHFFFAOYSA-N 1-[2-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]pentan-1-one Chemical compound CCCCC(=O)N1CCCC1C1=NN=C(C=2C=C(Cl)C=CC=2)O1 XSUCTMWHNPDEHX-UHFFFAOYSA-N 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 0.000 claims description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 4
- OQPLZCXCCFRYET-UHFFFAOYSA-N (1-phenyl-5-propylpyrazol-4-yl)-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound CCCC1=C(C(=O)N2C(CCC2)C=2OC(=NN=2)C=2C=NC=CC=2)C=NN1C1=CC=CC=C1 OQPLZCXCCFRYET-UHFFFAOYSA-N 0.000 claims description 3
- YSPDOKCTLOLLFG-UHFFFAOYSA-N (2,3-difluorophenyl)-[2-[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC=CC(C=2OC(=NN=2)C2N(CCC2)C(=O)C=2C(=C(F)C=CC=2)F)=C1 YSPDOKCTLOLLFG-UHFFFAOYSA-N 0.000 claims description 3
- FXHHDMQUIQFVQZ-UHFFFAOYSA-N (2,4-dimethoxyphenyl)-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound COC1=CC(OC)=CC=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CN=CC=2)CCC1 FXHHDMQUIQFVQZ-UHFFFAOYSA-N 0.000 claims description 3
- SLRWDRBKHCMLHT-UHFFFAOYSA-N (2-chloropyridin-3-yl)-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound ClC1=NC=CC=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CN=CC=2)CCC1 SLRWDRBKHCMLHT-UHFFFAOYSA-N 0.000 claims description 3
- GCLXDUJQFVNPLW-UHFFFAOYSA-N (2-chloropyridin-4-yl)-[2-[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC=CC(C=2OC(=NN=2)C2N(CCC2)C(=O)C=2C=C(Cl)N=CC=2)=C1 GCLXDUJQFVNPLW-UHFFFAOYSA-N 0.000 claims description 3
- MMKCDFOWYBKUSH-UHFFFAOYSA-N (4-bromophenyl)-[2-[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound COC1=CC=CC(C=2OC(=NN=2)C2N(CCC2)C(=O)C=2C=CC(Br)=CC=2)=C1 MMKCDFOWYBKUSH-UHFFFAOYSA-N 0.000 claims description 3
- AODUNNOUXUDRET-UHFFFAOYSA-N (4-ethoxyphenyl)-[2-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound C1=CC(OCC)=CC=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CC=CC=2)CCC1 AODUNNOUXUDRET-UHFFFAOYSA-N 0.000 claims description 3
- PUOKPUFCNARKLS-UHFFFAOYSA-N (5-methyl-2-phenyltriazol-4-yl)-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound CC1=NN(C=2C=CC=CC=2)N=C1C(=O)N1CCCC1C(O1)=NN=C1C1=CC=NC=C1 PUOKPUFCNARKLS-UHFFFAOYSA-N 0.000 claims description 3
- NFNBCRRNVXKEHI-UHFFFAOYSA-N 1-(4-methylphenyl)-n-[1-oxo-3-phenyl-1-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]propan-2-yl]methanesulfonamide Chemical compound C1=CC(C)=CC=C1CS(=O)(=O)NC(C(=O)N1C(CCC1)C=1OC(=NN=1)C=1C=CN=CC=1)CC1=CC=CC=C1 NFNBCRRNVXKEHI-UHFFFAOYSA-N 0.000 claims description 3
- LWHXFOOMFJNDNX-UHFFFAOYSA-N 2,2,2-trifluoro-1-[7-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]sulfonyl-3,4-dihydro-1h-isoquinolin-2-yl]ethanone Chemical compound C1=C2CN(C(=O)C(F)(F)F)CCC2=CC=C1S(=O)(=O)N1CCCC1C(O1)=NN=C1C1=CC=NC=C1 LWHXFOOMFJNDNX-UHFFFAOYSA-N 0.000 claims description 3
- AIHSPTIYEYXVOJ-UHFFFAOYSA-N 2-(2-fluorophenyl)-5-[1-[(2,4,6-trimethylphenyl)methylsulfonyl]pyrrolidin-2-yl]-1,3,4-oxadiazole Chemical compound CC1=CC(C)=CC(C)=C1CS(=O)(=O)N1C(C=2OC(=NN=2)C=2C(=CC=CC=2)F)CCC1 AIHSPTIYEYXVOJ-UHFFFAOYSA-N 0.000 claims description 3
- IUUIQDHPEYVZSO-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]ethanone Chemical compound C1=C(OC)C(OC)=CC=C1CC(=O)N1C(C=2OC(=NN=2)C=2C=CN=CC=2)CCC1 IUUIQDHPEYVZSO-UHFFFAOYSA-N 0.000 claims description 3
- OOVHSRTZJYLOER-UHFFFAOYSA-N 2-(4-chlorophenoxy)-1-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]ethanone Chemical compound C1=CC(Cl)=CC=C1OCC(=O)N1C(C=2OC(=NN=2)C=2C=CN=CC=2)CCC1 OOVHSRTZJYLOER-UHFFFAOYSA-N 0.000 claims description 3
- ULPOXKYPMMUGNH-UHFFFAOYSA-N 7,7-dimethyl-4-[[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]sulfonylmethyl]bicyclo[2.2.1]heptan-3-one Chemical compound CC1(C)C(CC2=O)CCC12CS(=O)(=O)N1CCCC1C(O1)=NN=C1C1=CC=NC=C1 ULPOXKYPMMUGNH-UHFFFAOYSA-N 0.000 claims description 3
- DLYPHYKGBGECJS-UHFFFAOYSA-N [2,5-bis(trifluoromethyl)phenyl]-[2-(5-thiophen-2-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C(=O)N2C(CCC2)C=2OC(=NN=2)C=2SC=CC=2)=C1 DLYPHYKGBGECJS-UHFFFAOYSA-N 0.000 claims description 3
- QEGYQKMVRCMLSM-UHFFFAOYSA-N [2,5-bis(trifluoromethyl)phenyl]-[2-[5-(4-chlorophenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C(=O)N2C(CCC2)C=2OC(=NN=2)C=2C=CC(Cl)=CC=2)=C1 QEGYQKMVRCMLSM-UHFFFAOYSA-N 0.000 claims description 3
- DTAOFRRNVHZAAU-UHFFFAOYSA-N [2-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]-[4-(trifluoromethylsulfanyl)phenyl]methanone Chemical compound C1=CC(SC(F)(F)F)=CC=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CC=CC=2)CCC1 DTAOFRRNVHZAAU-UHFFFAOYSA-N 0.000 claims description 3
- NYQPMOZWMICUNQ-UHFFFAOYSA-N [2-methyl-6-(trifluoromethyl)pyridin-3-yl]-[2-(5-phenyl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound CC1=NC(C(F)(F)F)=CC=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CC=CC=2)CCC1 NYQPMOZWMICUNQ-UHFFFAOYSA-N 0.000 claims description 3
- BZGOHXPVKPNPHQ-UHFFFAOYSA-N [3-(dimethylamino)phenyl]-[2-(5-pyridin-3-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound CN(C)C1=CC=CC(C(=O)N2C(CCC2)C=2OC(=NN=2)C=2C=NC=CC=2)=C1 BZGOHXPVKPNPHQ-UHFFFAOYSA-N 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- BIEJPIYZVCSMKC-UHFFFAOYSA-N ethyl 4-oxo-4-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]butanoate Chemical compound CCOC(=O)CCC(=O)N1CCCC1C1=NN=C(C=2C=CN=CC=2)O1 BIEJPIYZVCSMKC-UHFFFAOYSA-N 0.000 claims description 3
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 3
- ZXRCHYMCQVKDMW-UHFFFAOYSA-N (2,6-difluorophenyl)-[2-(5-pyridin-4-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound FC1=CC=CC(F)=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CN=CC=2)CCC1 ZXRCHYMCQVKDMW-UHFFFAOYSA-N 0.000 claims description 2
- RTGZEAOBKVKXLM-UHFFFAOYSA-N (4-chlorophenyl)-[2-[5-(4-phenylphenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]methanone Chemical compound C1=CC(Cl)=CC=C1C(=O)N1C(C=2OC(=NN=2)C=2C=CC(=CC=2)C=2C=CC=CC=2)CCC1 RTGZEAOBKVKXLM-UHFFFAOYSA-N 0.000 claims description 2
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 2
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000006239 protecting group Chemical group 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 2
- UGCLWPUCRTYGJJ-UHFFFAOYSA-N 1-(1h-isoquinolin-2-yl)ethanone Chemical compound C1=CC=C2C=CN(C(=O)C)CC2=C1 UGCLWPUCRTYGJJ-UHFFFAOYSA-N 0.000 claims 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 abstract 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 abstract 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 13
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 8
- WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 6
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- RLQZIECDMISZHS-UHFFFAOYSA-N 2-phenylcyclohexa-2,5-diene-1,4-dione Chemical compound O=C1C=CC(=O)C(C=2C=CC=CC=2)=C1 RLQZIECDMISZHS-UHFFFAOYSA-N 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- 230000005764 inhibitory process Effects 0.000 description 5
- 229910052760 oxygen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
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Classifications
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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- Health & Medical Sciences (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10240818.1 | 2002-08-30 | ||
| DE10240818A DE10240818A1 (de) | 2002-08-30 | 2002-08-30 | Substituierte 2-Pyrrolidin-2-yl-[1,3,4]-oxadiazol-Derivate |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005109164A RU2005109164A (ru) | 2006-01-20 |
| RU2324694C2 true RU2324694C2 (ru) | 2008-05-20 |
Family
ID=31983895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005109164/04A RU2324694C2 (ru) | 2002-08-30 | 2003-08-25 | Производные 2-пирролидин-2-ил-[1,3,4]оксадиазола и их применение в качестве антидепрессантов |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US7105538B2 (enExample) |
| EP (1) | EP1532141B1 (enExample) |
| JP (1) | JP2006506348A (enExample) |
| CN (1) | CN100390168C (enExample) |
| AR (1) | AR041093A1 (enExample) |
| AT (1) | ATE484503T1 (enExample) |
| CA (1) | CA2497078A1 (enExample) |
| CY (1) | CY1110913T1 (enExample) |
| DE (2) | DE10240818A1 (enExample) |
| DK (1) | DK1532141T3 (enExample) |
| ES (1) | ES2351119T3 (enExample) |
| MX (1) | MXPA05002298A (enExample) |
| PE (1) | PE20040983A1 (enExample) |
| PL (1) | PL375627A1 (enExample) |
| PT (1) | PT1532141E (enExample) |
| RU (1) | RU2324694C2 (enExample) |
| SI (1) | SI1532141T1 (enExample) |
| WO (1) | WO2004024725A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2417995C1 (ru) * | 2009-09-21 | 2011-05-10 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический университет" (ГОУ ВПО "КубГТУ") | Способ получения 3-(2-замещенных-1,3-оксазол-4-ил)пиридин-2(1н)-онов |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PT2291080E (pt) | 2008-05-14 | 2015-10-30 | Scripps Research Inst | Novos modelamodeladores dos recetores da esfingosina fosfato |
| CN103420998A (zh) * | 2012-05-16 | 2013-12-04 | 苏州爱斯鹏药物研发有限责任公司 | 一种新型噁二唑衍生物的合成方法 |
| DK2855453T3 (en) | 2012-06-04 | 2017-02-06 | Actelion Pharmaceuticals Ltd | Benzimidazol-proline derivatives |
| US10092574B2 (en) | 2012-09-26 | 2018-10-09 | Valorisation-Recherche, Limited Partnership | Inhibitors of polynucleotide repeat-associated RNA foci and uses thereof |
| BR112015007516A2 (pt) * | 2012-10-10 | 2017-07-04 | Actelion Pharmaceuticals Ltd | antagonistas do receptor de orexina que são derivados de [orto bi-(hetero-)aril]-[2-(meta bi-(hetero-)aril)- pirrolidin-1-il]-metanona |
| CN105051040A (zh) * | 2013-03-12 | 2015-11-11 | 埃科特莱茵药品有限公司 | 作为食欲素受体拮抗剂的氮杂环丁烷酰胺衍生物 |
| CN103333165B (zh) * | 2013-07-01 | 2016-02-24 | 河南理工大学 | 2-苯基-5-(3,4-二甲基)吡咯基-1,3,4-噁二唑及制备方法 |
| SI3077391T1 (sl) | 2013-12-04 | 2018-11-30 | Idorsia Pharmaceuticals Ltd | Uporaba benzimidazol-prolinskih derivatov |
| CN111978311B (zh) * | 2019-05-21 | 2024-05-31 | 中国科学院上海有机化学研究所 | 一类细胞程序性坏死抑制剂及其制备方法和用途 |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912747A (en) * | 1973-02-01 | 1975-10-14 | Delalande Sa | Derivatives of 2-hydroxymethyl-1,3,4-oxadiazole |
| US4784998A (en) * | 1987-04-06 | 1988-11-15 | Bristol-Myers Company | 1,3,4-oxadiazole pyschotropic compounds |
| WO2001004116A2 (en) * | 1999-07-09 | 2001-01-18 | Ortho-Mcneil Pharmaceutical, Inc. | Neurotrophic pyrrolidines and piperidines, and related compositions containing them |
| JP2001247569A (ja) * | 1999-08-12 | 2001-09-11 | Japan Tobacco Inc | ピロリジン誘導体又はピペリジン誘導体及びその医薬用途 |
| WO2002002554A1 (en) * | 2000-06-30 | 2002-01-10 | F. Hoffmann-La Roche Ag | Sulfonyl-pyrrolidine derivatives useful for the treatment of neurological disorders |
| RU2182905C2 (ru) * | 1996-10-18 | 2002-05-27 | Берингер Ингельхайм Фарма Кг | Производные оксадиазола |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5965537A (en) * | 1997-03-10 | 1999-10-12 | Basf Aktiengesellschaft | Dolastatin 15 derivatives with carbonyl and heterocyclic functionalities at the C-terminus |
-
2002
- 2002-08-30 DE DE10240818A patent/DE10240818A1/de not_active Withdrawn
-
2003
- 2003-08-25 RU RU2005109164/04A patent/RU2324694C2/ru not_active IP Right Cessation
- 2003-08-25 EP EP03794933A patent/EP1532141B1/de not_active Expired - Lifetime
- 2003-08-25 DK DK03794933.6T patent/DK1532141T3/da active
- 2003-08-25 WO PCT/EP2003/009390 patent/WO2004024725A1/de not_active Ceased
- 2003-08-25 CN CNB038201976A patent/CN100390168C/zh not_active Expired - Fee Related
- 2003-08-25 PT PT03794933T patent/PT1532141E/pt unknown
- 2003-08-25 CA CA002497078A patent/CA2497078A1/en not_active Abandoned
- 2003-08-25 ES ES03794933T patent/ES2351119T3/es not_active Expired - Lifetime
- 2003-08-25 PL PL03375627A patent/PL375627A1/xx not_active Application Discontinuation
- 2003-08-25 JP JP2004535155A patent/JP2006506348A/ja active Pending
- 2003-08-25 DE DE50313185T patent/DE50313185D1/de not_active Expired - Lifetime
- 2003-08-25 MX MXPA05002298A patent/MXPA05002298A/es active IP Right Grant
- 2003-08-25 AT AT03794933T patent/ATE484503T1/de active
- 2003-08-25 SI SI200331896T patent/SI1532141T1/sl unknown
- 2003-08-28 PE PE2003000883A patent/PE20040983A1/es not_active Application Discontinuation
- 2003-08-29 AR ARP030103137A patent/AR041093A1/es unknown
-
2005
- 2005-02-28 US US11/066,981 patent/US7105538B2/en not_active Expired - Fee Related
-
2010
- 2010-11-17 CY CY20101101028T patent/CY1110913T1/el unknown
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3912747A (en) * | 1973-02-01 | 1975-10-14 | Delalande Sa | Derivatives of 2-hydroxymethyl-1,3,4-oxadiazole |
| US4784998A (en) * | 1987-04-06 | 1988-11-15 | Bristol-Myers Company | 1,3,4-oxadiazole pyschotropic compounds |
| RU2182905C2 (ru) * | 1996-10-18 | 2002-05-27 | Берингер Ингельхайм Фарма Кг | Производные оксадиазола |
| WO2001004116A2 (en) * | 1999-07-09 | 2001-01-18 | Ortho-Mcneil Pharmaceutical, Inc. | Neurotrophic pyrrolidines and piperidines, and related compositions containing them |
| JP2001247569A (ja) * | 1999-08-12 | 2001-09-11 | Japan Tobacco Inc | ピロリジン誘導体又はピペリジン誘導体及びその医薬用途 |
| WO2002002554A1 (en) * | 2000-06-30 | 2002-01-10 | F. Hoffmann-La Roche Ag | Sulfonyl-pyrrolidine derivatives useful for the treatment of neurological disorders |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2417995C1 (ru) * | 2009-09-21 | 2011-05-10 | Государственное образовательное учреждение высшего профессионального образования "Кубанский государственный технологический университет" (ГОУ ВПО "КубГТУ") | Способ получения 3-(2-замещенных-1,3-оксазол-4-ил)пиридин-2(1н)-онов |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA05002298A (es) | 2005-06-08 |
| JP2006506348A (ja) | 2006-02-23 |
| PT1532141E (pt) | 2010-11-02 |
| EP1532141B1 (de) | 2010-10-13 |
| SI1532141T1 (sl) | 2010-12-31 |
| DK1532141T3 (da) | 2010-11-22 |
| CN1678609A (zh) | 2005-10-05 |
| ES2351119T3 (es) | 2011-01-31 |
| US20050187260A1 (en) | 2005-08-25 |
| CA2497078A1 (en) | 2004-03-25 |
| US7105538B2 (en) | 2006-09-12 |
| PE20040983A1 (es) | 2005-01-12 |
| AR041093A1 (es) | 2005-05-04 |
| AU2003264097A1 (en) | 2004-04-30 |
| EP1532141A1 (de) | 2005-05-25 |
| PL375627A1 (en) | 2005-12-12 |
| RU2005109164A (ru) | 2006-01-20 |
| DE50313185D1 (de) | 2010-11-25 |
| DE10240818A1 (de) | 2004-05-13 |
| CY1110913T1 (el) | 2015-06-10 |
| CN100390168C (zh) | 2008-05-28 |
| ATE484503T1 (de) | 2010-10-15 |
| WO2004024725A1 (de) | 2004-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20110826 |