MXPA05002298A - Derivados de 2-pirrolidin-2-il-[1,3,4]-oxadiazol y su uso como antidepresivos. - Google Patents
Derivados de 2-pirrolidin-2-il-[1,3,4]-oxadiazol y su uso como antidepresivos.Info
- Publication number
- MXPA05002298A MXPA05002298A MXPA05002298A MXPA05002298A MXPA05002298A MX PA05002298 A MXPA05002298 A MX PA05002298A MX PA05002298 A MXPA05002298 A MX PA05002298A MX PA05002298 A MXPA05002298 A MX PA05002298A MX PA05002298 A MXPA05002298 A MX PA05002298A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- pyrrolidin
- oxadiazol
- methanone
- pyridin
- Prior art date
Links
- 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 14
- 239000000935 antidepressant agent Substances 0.000 title description 10
- 229940005513 antidepressants Drugs 0.000 title description 10
- 239000003814 drug Substances 0.000 claims abstract description 36
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 239000000126 substance Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- 238000000034 method Methods 0.000 claims abstract description 11
- -1 (Ci_s-alkyl) -aryl Chemical group 0.000 claims description 221
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 28
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 19
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 17
- 229940079593 drug Drugs 0.000 claims description 15
- 230000002265 prevention Effects 0.000 claims description 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 13
- 208000002193 Pain Diseases 0.000 claims description 12
- 125000000623 heterocyclic group Chemical group 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 230000036407 pain Effects 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000005842 heteroatom Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 150000004866 oxadiazoles Chemical class 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 claims description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 6
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- QKIUAMUSENSFQQ-UHFFFAOYSA-N dimethylazanide Chemical compound C[N-]C QKIUAMUSENSFQQ-UHFFFAOYSA-N 0.000 claims description 5
- 125000004494 ethyl ester group Chemical group 0.000 claims description 5
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
- 125000001544 thienyl group Chemical group 0.000 claims description 5
- 206010012735 Diarrhoea Diseases 0.000 claims description 4
- 208000003251 Pruritus Diseases 0.000 claims description 4
- 206010046543 Urinary incontinence Diseases 0.000 claims description 4
- 206010047700 Vomiting Diseases 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 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
- 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
- NONVYBGSSQYHHW-UHFFFAOYSA-N 1-[2-[5-(3-chlorophenyl)-1,3,4-oxadiazol-2-yl]pyrrolidin-1-yl]-3-cyclopentylpropan-1-one Chemical compound ClC1=CC=CC(C=2OC(=NN=2)C2N(CCC2)C(=O)CCC2CCCC2)=C1 NONVYBGSSQYHHW-UHFFFAOYSA-N 0.000 claims description 3
- PRBFBDOMXJCOMM-UHFFFAOYSA-N 2-[5-(3-methoxyphenyl)-1,3,4-oxadiazol-2-yl]pyrrolidine-1-carbaldehyde Chemical compound COC=1C=C(C=CC=1)C1=NN=C(O1)C1N(CCC1)C=O PRBFBDOMXJCOMM-UHFFFAOYSA-N 0.000 claims description 3
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
- 125000004863 4-trifluoromethoxyphenyl group Chemical group [H]C1=C([H])C(OC(F)(F)F)=C([H])C([H])=C1* 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
- 230000015572 biosynthetic process Effects 0.000 claims description 3
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 3
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 230000000144 pharmacologic effect Effects 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 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
- SLLFVLKNXABYGI-UHFFFAOYSA-N 1,2,3-benzoxadiazole Chemical compound C1=CC=C2ON=NC2=C1 SLLFVLKNXABYGI-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
- 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 2
- 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 2
- 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 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
- 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
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 2
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- DSSYKIVIOFKYAU-UHFFFAOYSA-N camphor Chemical compound C1CC2(C)C(=O)CC1C2(C)C DSSYKIVIOFKYAU-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 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 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 2
- 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 1
- 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 1
- 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 1
- 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 1
- UTYDSRLFMRPPHP-UHFFFAOYSA-N 2-pyridin-4-yl-1,3,4-oxadiazole Chemical compound O1C=NN=C1C1=CC=NC=C1 UTYDSRLFMRPPHP-UHFFFAOYSA-N 0.000 claims 1
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- 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 1
- 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 1
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- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- ZQRLJFPNFOPYSM-UHFFFAOYSA-N furan-2-yl-[2-(5-thiophen-2-yl-1,3,4-oxadiazol-2-yl)pyrrolidin-1-yl]methanone Chemical compound C=1C=COC=1C(=O)N1CCCC1C(O1)=NN=C1C1=CC=CS1 ZQRLJFPNFOPYSM-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 125000006038 hexenyl group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
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- 239000012948 isocyanate Substances 0.000 description 1
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- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
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- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
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- 229960002748 norepinephrine Drugs 0.000 description 1
- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- BHAAPTBBJKJZER-UHFFFAOYSA-N p-anisidine Chemical compound COC1=CC=C(N)C=C1 BHAAPTBBJKJZER-UHFFFAOYSA-N 0.000 description 1
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- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
- 125000005981 pentynyl group Chemical group 0.000 description 1
- 208000033808 peripheral neuropathy Diseases 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009103 reabsorption Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229940076279 serotonin Drugs 0.000 description 1
- 230000000697 serotonin reuptake Effects 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000010532 solid phase synthesis reaction Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
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- 230000002194 synthesizing effect Effects 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 230000008733 trauma Effects 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- C07D413/02—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/04—Antipruritics
-
- 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
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
-
- 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
- A61P25/30—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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/32—Alcohol-abuse
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Addiction (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Obesity (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10240818A DE10240818A1 (de) | 2002-08-30 | 2002-08-30 | Substituierte 2-Pyrrolidin-2-yl-[1,3,4]-oxadiazol-Derivate |
| PCT/EP2003/009390 WO2004024725A1 (de) | 2002-08-30 | 2003-08-25 | 2-pyrrolidin-2-yl-[1,3,4]-oxadiazol-derivate und ihre verwendung als antidepressiva |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MXPA05002298A true MXPA05002298A (es) | 2005-06-08 |
Family
ID=31983895
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MXPA05002298A MXPA05002298A (es) | 2002-08-30 | 2003-08-25 | Derivados de 2-pirrolidin-2-il-[1,3,4]-oxadiazol y su uso como antidepresivos. |
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) |
Families Citing this family (10)
| 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 |
| 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 |
| 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 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2215949B1 (enExample) * | 1973-02-01 | 1976-07-02 | Delalande Sa | |
| US4784998A (en) * | 1987-04-06 | 1988-11-15 | Bristol-Myers Company | 1,3,4-oxadiazole pyschotropic compounds |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| US5965537A (en) * | 1997-03-10 | 1999-10-12 | Basf Aktiengesellschaft | Dolastatin 15 derivatives with carbonyl and heterocyclic functionalities at the C-terminus |
| CN1382140A (zh) * | 1999-07-09 | 2002-11-27 | 奥索-麦克尼尔药品公司 | 具有神经营养活性的吡咯烷和哌啶、以及含有它们的相关组合物 |
| 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 |
| US6589978B2 (en) * | 2000-06-30 | 2003-07-08 | Hoffman-La Roche Inc. | 1-sulfonyl pyrrolidine derivatives |
-
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
Also Published As
| Publication number | Publication date |
|---|---|
| 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 |
| RU2324694C2 (ru) | 2008-05-20 |
| 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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