CA2495589A1 - Composes azabicycliques comme agents actifs du systeme nerveux central - Google Patents
Composes azabicycliques comme agents actifs du systeme nerveux central Download PDFInfo
- Publication number
- CA2495589A1 CA2495589A1 CA002495589A CA2495589A CA2495589A1 CA 2495589 A1 CA2495589 A1 CA 2495589A1 CA 002495589 A CA002495589 A CA 002495589A CA 2495589 A CA2495589 A CA 2495589A CA 2495589 A1 CA2495589 A1 CA 2495589A1
- Authority
- CA
- Canada
- Prior art keywords
- pyridinyl
- cis
- heterocycle
- thieno
- compound according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 355
- 239000013543 active substance Substances 0.000 title abstract description 3
- 210000003169 central nervous system Anatomy 0.000 title description 18
- 208000002193 Pain Diseases 0.000 claims abstract description 25
- 230000036407 pain Effects 0.000 claims abstract description 25
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 22
- 208000035475 disorder Diseases 0.000 claims abstract description 12
- -1 furo[3,2-b]pyridinyl Chemical group 0.000 claims description 1056
- 125000000623 heterocyclic group Chemical group 0.000 claims description 428
- 229910052739 hydrogen Inorganic materials 0.000 claims description 239
- 239000001257 hydrogen Substances 0.000 claims description 239
- 125000000217 alkyl group Chemical group 0.000 claims description 233
- 125000004076 pyridyl group Chemical group 0.000 claims description 213
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 150
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 141
- 125000003545 alkoxy group Chemical group 0.000 claims description 135
- 241000350052 Daniellia ogea Species 0.000 claims description 134
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 130
- 229910052736 halogen Inorganic materials 0.000 claims description 130
- 150000002367 halogens Chemical group 0.000 claims description 130
- 125000000304 alkynyl group Chemical group 0.000 claims description 129
- 125000003342 alkenyl group Chemical group 0.000 claims description 127
- 125000001424 substituent group Chemical group 0.000 claims description 127
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 90
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 84
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 84
- 125000000335 thiazolyl group Chemical group 0.000 claims description 84
- 125000001544 thienyl group Chemical group 0.000 claims description 84
- 125000002883 imidazolyl group Chemical group 0.000 claims description 83
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 83
- 125000003831 tetrazolyl group Chemical group 0.000 claims description 82
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 80
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 71
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 68
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 65
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 54
- 125000003118 aryl group Chemical group 0.000 claims description 52
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 50
- 125000005243 carbonyl alkyl group Chemical group 0.000 claims description 50
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 50
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 50
- 150000002431 hydrogen Chemical group 0.000 claims description 50
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 49
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 48
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 48
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 47
- 125000004181 carboxyalkyl group Chemical group 0.000 claims description 47
- 125000004967 formylalkyl group Chemical group 0.000 claims description 47
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 47
- 125000001188 haloalkyl group Chemical group 0.000 claims description 47
- 125000005358 mercaptoalkyl group Chemical group 0.000 claims description 47
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 46
- 125000004414 alkyl thio group Chemical group 0.000 claims description 46
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 45
- 125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 45
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 45
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 45
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 43
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 42
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 42
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 42
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 42
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 42
- 125000001041 indolyl group Chemical group 0.000 claims description 42
- 125000005990 isobenzothienyl group Chemical group 0.000 claims description 42
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 42
- 125000001786 isothiazolyl group Chemical group 0.000 claims description 42
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 42
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 42
- 125000002971 oxazolyl group Chemical group 0.000 claims description 42
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 42
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 42
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 42
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 42
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 42
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 42
- 125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 claims description 42
- 125000004306 triazinyl group Chemical group 0.000 claims description 42
- 125000001425 triazolyl group Chemical group 0.000 claims description 42
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 41
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 41
- 125000000259 cinnolinyl group Chemical group N1=NC(=CC2=CC=CC=C12)* 0.000 claims description 41
- 125000001977 isobenzofuranyl group Chemical group C=1(OC=C2C=CC=CC12)* 0.000 claims description 41
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 41
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 41
- MKYRMMMSZSVIGD-UHFFFAOYSA-N thieno[3,2-c]pyridine Chemical compound N1=CC=C2SC=CC2=C1 MKYRMMMSZSVIGD-UHFFFAOYSA-N 0.000 claims description 41
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 40
- GDQBPBMIAFIRIU-UHFFFAOYSA-N thieno[2,3-c]pyridine Chemical compound C1=NC=C2SC=CC2=C1 GDQBPBMIAFIRIU-UHFFFAOYSA-N 0.000 claims description 40
- 125000002541 furyl group Chemical group 0.000 claims description 37
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 36
- 150000001408 amides Chemical class 0.000 claims description 34
- 150000002148 esters Chemical class 0.000 claims description 34
- 150000003839 salts Chemical class 0.000 claims description 34
- 239000000651 prodrug Substances 0.000 claims description 33
- 229940002612 prodrug Drugs 0.000 claims description 33
- 241000124008 Mammalia Species 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 17
- 208000024827 Alzheimer disease Diseases 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 239000003937 drug carrier Substances 0.000 claims description 9
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical group [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 9
- 125000004615 furo[2,3-b]pyridinyl group Chemical group O1C(=CC=2C1=NC=CC2)* 0.000 claims description 8
- UZHVXJZEHGSWQV-UHFFFAOYSA-N 1,2,3,3a,4,5,6,6a-octahydrocyclopenta[c]pyrrole Chemical compound C1NCC2CCCC21 UZHVXJZEHGSWQV-UHFFFAOYSA-N 0.000 claims description 7
- OARHBHCOPBHQDY-UHFFFAOYSA-N 1,2,3,5,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C1NCC2=CCCC21 OARHBHCOPBHQDY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 5
- YAQNASWWTSADND-MNOVXSKESA-N (3as,6ar)-5-(6-chloropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C1=NC(Cl)=CC=C1C(C1)=C[C@H]2[C@@H]1CNC2 YAQNASWWTSADND-MNOVXSKESA-N 0.000 claims description 4
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 4
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000018737 Parkinson disease Diseases 0.000 claims description 4
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 4
- 208000016620 Tourette disease Diseases 0.000 claims description 4
- 239000001961 anticonvulsive agent Substances 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims description 4
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 4
- 201000000980 schizophrenia Diseases 0.000 claims description 4
- 229940123445 Tricyclic antidepressant Drugs 0.000 claims description 3
- 230000001773 anti-convulsant effect Effects 0.000 claims description 3
- 229960003965 antiepileptics Drugs 0.000 claims description 3
- 125000006678 phenoxycarbonyl group Chemical group 0.000 claims description 3
- 239000003029 tricyclic antidepressant agent Substances 0.000 claims description 3
- UTBFDRZURAFKKX-CMPLNLGQSA-N (1r,5r)-6-(6-methylpyridin-3-yl)-3-azabicyclo[3.2.0]hept-6-ene Chemical compound C1=NC(C)=CC=C1C1=C[C@@H]2[C@H]1CNC2 UTBFDRZURAFKKX-CMPLNLGQSA-N 0.000 claims description 2
- LWRFZZWFCQQXNI-GZMMTYOYSA-N (3ar,6ar)-4-(6-chloropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical group C1=NC(Cl)=CC=C1C1=CC[C@@H]2[C@H]1CNC2 LWRFZZWFCQQXNI-GZMMTYOYSA-N 0.000 claims description 2
- CIVMSIMWOAAUSS-NEPJUHHUSA-N (3as,6ar)-5-(2-methylpyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound CC1=NC=CC=C1C(C1)=C[C@H]2[C@@H]1CNC2 CIVMSIMWOAAUSS-NEPJUHHUSA-N 0.000 claims description 2
- KITBQYINDRYHAR-ZJUUUORDSA-N (3as,6ar)-5-(5-bromopyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound BrC1=CN=CC(C=2C[C@H]3CNC[C@H]3C=2)=C1 KITBQYINDRYHAR-ZJUUUORDSA-N 0.000 claims description 2
- HAGCSLRQJQKFEQ-KGLIPLIRSA-N (3as,6ar)-5-(5-ethenylpyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C=CC1=CN=CC(C=2C[C@H]3CNC[C@H]3C=2)=C1 HAGCSLRQJQKFEQ-KGLIPLIRSA-N 0.000 claims description 2
- OXLZLZNNUDEYMM-BDAKNGLRSA-N (3as,6ar)-5-(6-chloro-5-fluoropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound N1=C(Cl)C(F)=CC(C=2C[C@H]3CNC[C@H]3C=2)=C1 OXLZLZNNUDEYMM-BDAKNGLRSA-N 0.000 claims description 2
- KQEJMSIHYNXRKN-NEPJUHHUSA-N (3as,6ar)-5-(6-methylpyridin-2-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound CC1=CC=CC(C=2C[C@H]3CNC[C@H]3C=2)=N1 KQEJMSIHYNXRKN-NEPJUHHUSA-N 0.000 claims description 2
- SPCUUEGNKNAVFJ-NEPJUHHUSA-N (3as,6ar)-5-pyridin-3-yl-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C1=CC=CN=C1 SPCUUEGNKNAVFJ-NEPJUHHUSA-N 0.000 claims description 2
- HWKQQDAOVCROKN-SFYZADRCSA-N 2-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-1,3,4-thiadiazole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C1=NN=CS1 HWKQQDAOVCROKN-SFYZADRCSA-N 0.000 claims description 2
- BKVOSWFCWCIVOR-BDAKNGLRSA-N 2-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-1,3-thiazole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C1=NC=CS1 BKVOSWFCWCIVOR-BDAKNGLRSA-N 0.000 claims description 2
- YPCQGVRMWNJBRL-MNOVXSKESA-N 2-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]thieno[3,2-b]pyridine Chemical compound C1=CC=C2SC(C3=C[C@@H]4CNC[C@@H]4C3)=CC2=N1 YPCQGVRMWNJBRL-MNOVXSKESA-N 0.000 claims description 2
- GQFLKJQLECEKGI-NEPJUHHUSA-N 5-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]thieno[2,3-b]pyridine Chemical compound N1=C2SC=CC2=CC(C2=C[C@@H]3CNC[C@@H]3C2)=C1 GQFLKJQLECEKGI-NEPJUHHUSA-N 0.000 claims description 2
- TYTYGNYDODGHMD-BDAKNGLRSA-N 5-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]thiophene-2-sulfonamide Chemical compound S1C(S(=O)(=O)N)=CC=C1C(C1)=C[C@H]2[C@@H]1CNC2 TYTYGNYDODGHMD-BDAKNGLRSA-N 0.000 claims description 2
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims description 2
- 206010048010 Withdrawal syndrome Diseases 0.000 claims description 2
- ZYXBIOIYWUIXSM-UHFFFAOYSA-N furo[2,3-c]pyridine Chemical compound C1=NC=C2OC=CC2=C1 ZYXBIOIYWUIXSM-UHFFFAOYSA-N 0.000 claims 7
- WJDMEHCIRPKRRQ-UHFFFAOYSA-N furo[3,2-c]pyridine Chemical compound N1=CC=C2OC=CC2=C1 WJDMEHCIRPKRRQ-UHFFFAOYSA-N 0.000 claims 7
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 claims 2
- OMTUWDNEHIWIAD-SKDRFNHKSA-N (3aR,6aS)-5-pyridin-3-yl-1,2,3,3a,6,6a-hexahydrocyclopenta[b]pyrrole Chemical group C([C@H]1CCN[C@H]1C1)=C1C1=CC=CN=C1 OMTUWDNEHIWIAD-SKDRFNHKSA-N 0.000 claims 1
- YAQNASWWTSADND-WDEREUQCSA-N (3ar,6as)-5-(6-chloropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C1=NC(Cl)=CC=C1C(C1)=C[C@@H]2[C@H]1CNC2 YAQNASWWTSADND-WDEREUQCSA-N 0.000 claims 1
- VTSPVGKLJVWSSM-USUYBEQLSA-N (3ar,6as)-5-(6-chloropyridin-3-yl)-2,3,3a,4,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-5-ol Chemical compound C([C@H]1CNC[C@H]1C1)C1(O)C1=CC=C(Cl)N=C1 VTSPVGKLJVWSSM-USUYBEQLSA-N 0.000 claims 1
- VAHDXXMXJJNPJF-CVEARBPZSA-N (3as,6ar)-2-methyl-5-(6-phenylpyridazin-3-yl)-3,3a,6,6a-tetrahydro-1h-cyclopenta[c]pyrrole Chemical compound C([C@H]1CN(C[C@H]1C=1)C)C=1C(N=N1)=CC=C1C1=CC=CC=C1 VAHDXXMXJJNPJF-CVEARBPZSA-N 0.000 claims 1
- ZDFXASSATQIVHP-RPWUZVMVSA-N (3as,6ar)-5-(1-tritylimidazol-4-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C(N=C1)=CN1C(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 ZDFXASSATQIVHP-RPWUZVMVSA-N 0.000 claims 1
- CDDRCSRASTZWPL-SFYZADRCSA-N (3as,6ar)-5-(2-methyltetrazol-5-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound CN1N=NC(C=2C[C@H]3CNC[C@H]3C=2)=N1 CDDRCSRASTZWPL-SFYZADRCSA-N 0.000 claims 1
- LLNCAWVTLZLEMS-BDAKNGLRSA-N (3as,6ar)-5-(5,6-dichloropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound N1=C(Cl)C(Cl)=CC(C=2C[C@H]3CNC[C@H]3C=2)=C1 LLNCAWVTLZLEMS-BDAKNGLRSA-N 0.000 claims 1
- WSVOKZXOLZYPOI-ZJUUUORDSA-N (3as,6ar)-5-(5-chloropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound ClC1=CN=CC(C=2C[C@H]3CNC[C@H]3C=2)=C1 WSVOKZXOLZYPOI-ZJUUUORDSA-N 0.000 claims 1
- YASHSULMNPGWAU-MNOVXSKESA-N (3as,6ar)-5-(6-fluoropyridin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C1=NC(F)=CC=C1C(C1)=C[C@H]2[C@@H]1CNC2 YASHSULMNPGWAU-MNOVXSKESA-N 0.000 claims 1
- IURRVWTVDWZLPB-CABCVRRESA-N (3as,6ar)-5-(6-phenylpyridazin-3-yl)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C(N=N1)=CC=C1C1=CC=CC=C1 IURRVWTVDWZLPB-CABCVRRESA-N 0.000 claims 1
- IYLOHCJIQJNDGN-MNOVXSKESA-N (3as,6ar)-5-pyridin-2-yl-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C1=CC=CC=N1 IYLOHCJIQJNDGN-MNOVXSKESA-N 0.000 claims 1
- POEAVFSTQDHXDD-NEPJUHHUSA-N (3as,6ar)-5-pyridin-4-yl-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C1=CC=NC=C1 POEAVFSTQDHXDD-NEPJUHHUSA-N 0.000 claims 1
- XNQHHSMFZZIQIV-OLZOCXBDSA-N 2-[(3as,6ar)-5-(6-chloropyridin-3-yl)-3,3a,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-2-yl]acetonitrile Chemical compound C1=NC(Cl)=CC=C1C(C1)=C[C@H]2[C@@H]1CN(CC#N)C2 XNQHHSMFZZIQIV-OLZOCXBDSA-N 0.000 claims 1
- WCKLVAAMXJBUPF-NEPJUHHUSA-N 3-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]imidazo[1,2-a]pyridine Chemical compound C1=CC=CN2C(C3=C[C@@H]4CNC[C@@H]4C3)=CN=C21 WCKLVAAMXJBUPF-NEPJUHHUSA-N 0.000 claims 1
- YQTZOKBFHXXHPM-BDAKNGLRSA-N 5-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-1,3-thiazole Chemical compound C([C@@H]1CNC[C@@H]1C1)=C1C1=CN=CS1 YQTZOKBFHXXHPM-BDAKNGLRSA-N 0.000 claims 1
- IWSAVLITNBDMEU-RQJHMYQMSA-N 5-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-3-bromo-1,2,4-thiadiazole Chemical compound BrC1=NSC(C=2C[C@H]3CNC[C@H]3C=2)=N1 IWSAVLITNBDMEU-RQJHMYQMSA-N 0.000 claims 1
- MFAMXRYQCDYWRY-ZJUUUORDSA-N 5-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]-3-methyl-1,2-oxazole Chemical compound O1N=C(C)C=C1C(C1)=C[C@H]2[C@@H]1CNC2 MFAMXRYQCDYWRY-ZJUUUORDSA-N 0.000 claims 1
- STHYMKBVPVSCEQ-BDAKNGLRSA-N 5-[(3as,6ar)-1,2,3,3a,6,6a-hexahydrocyclopenta[c]pyrrol-5-yl]thiophene-2-carboximidamide Chemical compound S1C(C(=N)N)=CC=C1C(C1)=C[C@H]2[C@@H]1CNC2 STHYMKBVPVSCEQ-BDAKNGLRSA-N 0.000 claims 1
- QWSJKODWNZCABE-MNOVXSKESA-N 5-[(3as,6ar)-2-methyl-3,3a,6,6a-tetrahydro-1h-cyclopenta[c]pyrrol-5-yl]-3-methyl-1,2-oxazole Chemical compound C([C@H]1CN(C[C@H]1C=1)C)C=1C1=CC(C)=NO1 QWSJKODWNZCABE-MNOVXSKESA-N 0.000 claims 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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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
- A61P25/28—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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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- 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
- C07D403/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
-
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Addiction (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
L'invention concerne des composés représentés par la formule (I), qui constituent de nouveaux agents actifs du SNC et sont utiles dans le traitement de la douleur et d'autres troubles associés au système cholinergique.
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10/219,223 | 2002-08-14 | ||
| US10/219,223 US20040044029A1 (en) | 2002-08-14 | 2002-08-14 | Azabicyclic compounds are central nervous system active agents |
| US10/638,381 | 2003-08-12 | ||
| US10/638,381 US7135484B2 (en) | 2002-08-14 | 2003-08-12 | Azabicyclic compounds are central nervous system active agents |
| PCT/US2003/025471 WO2004016604A2 (fr) | 2002-08-14 | 2003-08-13 | Composes azabicycliques comme agents actifs du systeme nerveux central |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2495589A1 true CA2495589A1 (fr) | 2004-02-26 |
Family
ID=32044938
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002495589A Abandoned CA2495589A1 (fr) | 2002-08-14 | 2003-08-13 | Composes azabicycliques comme agents actifs du systeme nerveux central |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JP4629576B2 (fr) |
| CA (1) | CA2495589A1 (fr) |
| MX (1) | MXPA05001726A (fr) |
| WO (1) | WO2004016604A2 (fr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2004282201A1 (en) | 2003-10-15 | 2005-04-28 | Targacept, Inc. | Azabicycyclic compounds for relieving pain and treating central nervous system disorders |
| TW200845977A (en) | 2007-03-30 | 2008-12-01 | Targacept Inc | Sub-type selective azabicycloalkane derivatives |
| CN103242216A (zh) * | 2013-05-07 | 2013-08-14 | 兰州梦唐精细化工有限公司 | N- Boc -六氢-5-氧代环戊[C]并吡咯的合成方法 |
| CN112010859B (zh) * | 2019-05-30 | 2022-07-19 | 中国科学院上海药物研究所 | 一种并环化合物、其制备方法和用途 |
| WO2024125395A1 (fr) * | 2022-12-12 | 2024-06-20 | 江苏恩华药业股份有限公司 | Dérivé de tétrahydrocyclopentyl[c]pyrrole substitué, procédé de préparation, intermédiaire et utilisation associés |
| CN118356426A (zh) * | 2023-01-18 | 2024-07-19 | 苏州旺山旺水生物医药股份有限公司 | 一种包含并环化合物的药物组合物及其制备方法和应用 |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2592879B1 (fr) * | 1986-01-13 | 1988-04-29 | Roussel Uclaf | Nouveaux derives de la decahydroquinoleine, leur procede de preparation, les intermediaires de preparation, leur application a titre de medicaments et les compositions les renfermant |
| DE4332168A1 (de) * | 1993-02-22 | 1995-03-23 | Thomae Gmbh Dr K | Cyclische Derivate, diese Verbindungen enthaltende Arzneimittel und Verfahren zu ihrer Herstellung |
| US5508424A (en) * | 1993-03-26 | 1996-04-16 | Ortho Pharmaceutical Corporation | 4-arylisoindole analgesics |
| DE4341402A1 (de) * | 1993-12-04 | 1995-06-08 | Basf Ag | N-substituierte Azabicycloheptan-Derivate, ihre Herstellung und Verwendung |
| DE4341403A1 (de) * | 1993-12-04 | 1995-06-08 | Basf Ag | N-substituierte 3-Azabicycloalkan-Derivate, ihre Herstellung und Verwendung |
| US5543530A (en) * | 1993-12-23 | 1996-08-06 | Ortho Pharmaceutical Corporation | 4-arylisoindole analgesics |
| US5541217A (en) * | 1995-05-17 | 1996-07-30 | Ortho Pharmaceutical Corporation | 4-arylcyclopenta[c]pyrrole analgesics |
| US5929087A (en) * | 1997-04-08 | 1999-07-27 | Regents Of The University Of Minnesota | Decahydroquinoline-based anti-cholinergic agents |
| JPH11106375A (ja) * | 1997-08-18 | 1999-04-20 | Pfizer Pharmaceut Inc | ブラジキニンアンタゴニストとしての光学的に活性な1,4−ジヒドロピリジン化合物 |
| JP5000068B2 (ja) * | 2000-08-11 | 2012-08-15 | ベーリンガー インゲルハイム ファーマシューティカルズ インコーポレイテッド | チロシンキナーゼのインヒビターとして有用な複素環化合物 |
| US20020094989A1 (en) * | 2000-10-11 | 2002-07-18 | Hale Jeffrey J. | Pyrrolidine modulators of CCR5 chemokine receptor activity |
| JP2002193964A (ja) * | 2000-12-22 | 2002-07-10 | Sumitomo Pharmaceut Co Ltd | ピラゾール誘導体およびその医薬用途 |
| JPWO2002085890A1 (ja) * | 2001-04-20 | 2004-08-12 | 萬有製薬株式会社 | ベンズイミダゾロン誘導体 |
| MXPA04000012A (es) * | 2001-07-06 | 2004-05-21 | Neurosearch As | Compuestos novedosos, su preparacion y uso. |
-
2003
- 2003-08-13 MX MXPA05001726A patent/MXPA05001726A/es active IP Right Grant
- 2003-08-13 CA CA002495589A patent/CA2495589A1/fr not_active Abandoned
- 2003-08-13 JP JP2005502054A patent/JP4629576B2/ja not_active Expired - Fee Related
- 2003-08-13 WO PCT/US2003/025471 patent/WO2004016604A2/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP2006513256A (ja) | 2006-04-20 |
| WO2004016604A3 (fr) | 2004-04-08 |
| WO2004016604A2 (fr) | 2004-02-26 |
| MXPA05001726A (es) | 2005-05-27 |
| JP4629576B2 (ja) | 2011-02-09 |
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| FZDE | Dead |