JP2005500986A5 - - Google Patents
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- Publication number
- JP2005500986A5 JP2005500986A5 JP2002573767A JP2002573767A JP2005500986A5 JP 2005500986 A5 JP2005500986 A5 JP 2005500986A5 JP 2002573767 A JP2002573767 A JP 2002573767A JP 2002573767 A JP2002573767 A JP 2002573767A JP 2005500986 A5 JP2005500986 A5 JP 2005500986A5
- Authority
- JP
- Japan
- Prior art keywords
- ethyl
- benzofuran
- methyl
- pyrrolidinyl
- group
- 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.)
- Granted
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- -1 (2R) -2-methyl-1-pyrrolidinyl Chemical group 0.000 claims 91
- 125000000217 alkyl group Chemical group 0.000 claims 69
- 150000001875 compounds Chemical class 0.000 claims 40
- 125000004093 cyano group Chemical group *C#N 0.000 claims 37
- 229910052739 hydrogen Inorganic materials 0.000 claims 37
- 239000001257 hydrogen Substances 0.000 claims 37
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 34
- 150000002431 hydrogen Chemical class 0.000 claims 31
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 29
- 125000003545 alkoxy group Chemical group 0.000 claims 27
- 229910052736 halogen Inorganic materials 0.000 claims 27
- 150000002367 halogens Chemical class 0.000 claims 27
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 25
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 25
- 125000001188 haloalkyl group Chemical group 0.000 claims 25
- 125000000623 heterocyclic group Chemical group 0.000 claims 25
- 125000004438 haloalkoxy group Chemical group 0.000 claims 23
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims 22
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 21
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims 21
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 21
- 125000004414 alkyl thio group Chemical group 0.000 claims 21
- 125000004181 carboxyalkyl group Chemical group 0.000 claims 21
- 125000004966 cyanoalkyl group Chemical group 0.000 claims 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 21
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 21
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- 125000000168 pyrrolyl group Chemical group 0.000 claims 14
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 13
- 125000002757 morpholinyl group Chemical group 0.000 claims 12
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 11
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims 11
- 125000002393 azetidinyl group Chemical group 0.000 claims 10
- 125000004193 piperazinyl group Chemical group 0.000 claims 10
- 125000003386 piperidinyl group Chemical group 0.000 claims 10
- 125000004076 pyridyl group Chemical group 0.000 claims 10
- 125000004568 thiomorpholinyl group Chemical group 0.000 claims 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 9
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 8
- 125000003725 azepanyl group Chemical group 0.000 claims 8
- 125000002883 imidazolyl group Chemical group 0.000 claims 8
- 150000001408 amides Chemical class 0.000 claims 7
- 125000003118 aryl group Chemical group 0.000 claims 7
- 150000002148 esters Chemical class 0.000 claims 7
- 229940002612 prodrug Drugs 0.000 claims 7
- 239000000651 prodrug Substances 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000005129 aryl carbonyl group Chemical group 0.000 claims 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 229910052717 sulfur Inorganic materials 0.000 claims 4
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- 125000002947 alkylene group Chemical group 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- OAGQKGSJQMWGBI-LJQANCHMSA-N (3-fluorophenyl)-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(=O)C=3C=C(F)C=CC=3)=CC=C2O1 OAGQKGSJQMWGBI-LJQANCHMSA-N 0.000 claims 2
- KPNUCNMZTCZSCQ-CYBMUJFWSA-N 3,5-dimethyl-4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C3=C(ON=C3C)C)=CC=C2O1 KPNUCNMZTCZSCQ-CYBMUJFWSA-N 0.000 claims 2
- WWEXCCZITRBBJR-INIZCTEOSA-N 3-[2-[2-[(2s)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2O1 WWEXCCZITRBBJR-INIZCTEOSA-N 0.000 claims 2
- NSWXSLGPNBDJSG-MRXNPFEDSA-N 3-ethyl-1-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pentan-1-one Chemical compound C=1C2=CC(C(=O)CC(CC)CC)=CC=C2OC=1CCN1CCC[C@H]1C NSWXSLGPNBDJSG-MRXNPFEDSA-N 0.000 claims 2
- INMKIUUCZWOKBP-OAQYLSRUSA-N 4-[2-[2-[(2r)-2-ethylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound CC[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 INMKIUUCZWOKBP-OAQYLSRUSA-N 0.000 claims 2
- MLKLMMHXAFOMLR-UJONTBEJSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-2,3-dihydro-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1OC2=CC=C(C=3C=CC(=CC=3)C#N)C=C2C1 MLKLMMHXAFOMLR-UJONTBEJSA-N 0.000 claims 2
- SUXVYLBRHCOYGN-IRXDYDNUSA-N 4-[2-[2-[(2s,5s)-2,5-dimethylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@H]1CC[C@H](C)N1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 SUXVYLBRHCOYGN-IRXDYDNUSA-N 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- KFHYZKCRXNRKRC-MRXNPFEDSA-N abt-239 Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 KFHYZKCRXNRKRC-MRXNPFEDSA-N 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 229920006391 phthalonitrile polymer Polymers 0.000 claims 2
- WRJKIXYAASDVFO-OAHLLOKOSA-N (2-fluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C(=CC=CC=3)F)=CC=C2O1 WRJKIXYAASDVFO-OAHLLOKOSA-N 0.000 claims 1
- BCDZCOWNIXKIFN-MRXNPFEDSA-N (2-methoxyphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound COC1=CC=CC=C1C(=O)C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 BCDZCOWNIXKIFN-MRXNPFEDSA-N 0.000 claims 1
- OYUBXZVOQPBECQ-QGZVFWFLSA-N (2r)-1-[2-(5-benzyl-1-benzofuran-2-yl)ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(CC=3C=CC=CC=3)=CC=C2O1 OYUBXZVOQPBECQ-QGZVFWFLSA-N 0.000 claims 1
- RKQFJBLBZHLARI-OAHLLOKOSA-N (2r)-1-[2-[4-(3,6-dihydro-2h-pyran-5-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C=3COCCC=3)C=CC=C2O1 RKQFJBLBZHLARI-OAHLLOKOSA-N 0.000 claims 1
- WUMZKGKEDCMAKO-QGZVFWFLSA-N (2r)-1-[2-[4-(cyclohepten-1-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C=3CCCCCC=3)C=CC=C2O1 WUMZKGKEDCMAKO-QGZVFWFLSA-N 0.000 claims 1
- URPSLNWDHBYYIR-JOCHJYFZSA-N (2r)-1-[2-[4-[2-(6h-benzo[c][1]benzothiepin-11-ylidene)ethyl]-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC(OC1=CC=C2)=CC1=C2CC=C1C2=CC=CC=C2SCC2=CC=CC=C21 URPSLNWDHBYYIR-JOCHJYFZSA-N 0.000 claims 1
- LDTHNPZYPMICEJ-OAHLLOKOSA-N (2r)-1-[2-[5-(2-chlorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C(=CC=CC=3)Cl)=CC=C2O1 LDTHNPZYPMICEJ-OAHLLOKOSA-N 0.000 claims 1
- LPQCQSGBEKRXHW-MRXNPFEDSA-N (2r)-1-[2-[5-(2-methoxyphenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound COC1=CC=CC=C1C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 LPQCQSGBEKRXHW-MRXNPFEDSA-N 0.000 claims 1
- KNMDVDZWMCZHKS-CQSZACIVSA-N (2r)-1-[2-[5-(3,4-dichlorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(Cl)C(Cl)=CC=3)=CC=C2O1 KNMDVDZWMCZHKS-CQSZACIVSA-N 0.000 claims 1
- AFWVNISWIRNOQW-GOSISDBHSA-N (2r)-1-[2-[5-(3,4-dimethylphenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C)C(C)=CC=3)=CC=C2O1 AFWVNISWIRNOQW-GOSISDBHSA-N 0.000 claims 1
- UJMOZVIDJBIDOA-CQSZACIVSA-N (2r)-1-[2-[5-(3,5-dichlorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(Cl)C=C(Cl)C=3)=CC=C2O1 UJMOZVIDJBIDOA-CQSZACIVSA-N 0.000 claims 1
- FNDBIFGTMPJYFO-GOSISDBHSA-N (2r)-1-[2-[5-(3,5-dimethylphenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C)C=C(C)C=3)=CC=C2O1 FNDBIFGTMPJYFO-GOSISDBHSA-N 0.000 claims 1
- RAOKWCNQFSXBHU-OAHLLOKOSA-N (2r)-1-[2-[5-(3,6-dihydro-2h-pyran-5-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3COCCC=3)=CC=C2O1 RAOKWCNQFSXBHU-OAHLLOKOSA-N 0.000 claims 1
- RRORGXIKKDQOND-OAHLLOKOSA-N (2r)-1-[2-[5-(3-chlorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(Cl)C=CC=3)=CC=C2O1 RRORGXIKKDQOND-OAHLLOKOSA-N 0.000 claims 1
- BAFBEWGRSDVGJO-OAHLLOKOSA-N (2r)-1-[2-[5-(3-fluorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(F)C=CC=3)=CC=C2O1 BAFBEWGRSDVGJO-OAHLLOKOSA-N 0.000 claims 1
- VYWRLQUSTFQPKZ-OAHLLOKOSA-N (2r)-1-[2-[5-(3-fluorophenyl)sulfanyl-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(SC=3C=C(F)C=CC=3)=CC=C2O1 VYWRLQUSTFQPKZ-OAHLLOKOSA-N 0.000 claims 1
- XNDYCOPRKJMNGV-MRXNPFEDSA-N (2r)-1-[2-[5-(3-methoxyphenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound COC1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 XNDYCOPRKJMNGV-MRXNPFEDSA-N 0.000 claims 1
- LCWMVSMZFNKPMC-OAHLLOKOSA-N (2r)-1-[2-[5-(4-fluorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(F)=CC=3)=CC=C2O1 LCWMVSMZFNKPMC-OAHLLOKOSA-N 0.000 claims 1
- UANSUUBAEVNXGD-MRXNPFEDSA-N (2r)-1-[2-[5-(4-methoxyphenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C1=CC(OC)=CC=C1C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 UANSUUBAEVNXGD-MRXNPFEDSA-N 0.000 claims 1
- BWLHRHCJSILDQR-QGZVFWFLSA-N (2r)-1-[2-[5-[2-(4-fluorophenyl)ethenyl]-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=CC=3C=CC(F)=CC=3)=CC=C2O1 BWLHRHCJSILDQR-QGZVFWFLSA-N 0.000 claims 1
- UIUPEGIYJQJGQS-JOCHJYFZSA-N (2r)-1-[2-[5-[2-(6h-benzo[c][1]benzothiepin-11-ylidene)ethyl]-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(CC=C3C4=CC=CC=C4SCC4=CC=CC=C43)=CC=C2O1 UIUPEGIYJQJGQS-JOCHJYFZSA-N 0.000 claims 1
- DZQSOGYVMGOTPN-OAHLLOKOSA-N (2r)-1-[2-[6-(3,6-dihydro-2h-pyran-5-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3COCCC=3)C=C2O1 DZQSOGYVMGOTPN-OAHLLOKOSA-N 0.000 claims 1
- RAGQJBPOJXGIDH-QGZVFWFLSA-N (2r)-1-[2-[6-(cyclohepten-1-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3CCCCCC=3)C=C2O1 RAGQJBPOJXGIDH-QGZVFWFLSA-N 0.000 claims 1
- VLSBUMPPEHJKRF-JOCHJYFZSA-N (2r)-1-[2-[6-[2-(6h-benzo[c][1]benzothiepin-11-ylidene)ethyl]-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC(OC1=C2)=CC1=CC=C2CC=C1C2=CC=CC=C2SCC2=CC=CC=C21 VLSBUMPPEHJKRF-JOCHJYFZSA-N 0.000 claims 1
- XOZUSOVMOYQVNG-OAHLLOKOSA-N (2r)-1-[2-[7-(3,6-dihydro-2h-pyran-5-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3COCCC=3)=C2O1 XOZUSOVMOYQVNG-OAHLLOKOSA-N 0.000 claims 1
- AOQCCHDOIXWRSV-QGZVFWFLSA-N (2r)-1-[2-[7-(cyclohepten-1-yl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3CCCCCC=3)=C2O1 AOQCCHDOIXWRSV-QGZVFWFLSA-N 0.000 claims 1
- AJVVZFJUXPSHPI-JOCHJYFZSA-N (2r)-1-[2-[7-[2-(6h-benzo[c][1]benzothiepin-11-ylidene)ethyl]-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(CC=C3C4=CC=CC=C4SCC4=CC=CC=C43)=C2O1 AJVVZFJUXPSHPI-JOCHJYFZSA-N 0.000 claims 1
- WNGGFYSKLHPGQM-MRXNPFEDSA-N (2r)-2-methyl-1-[2-(5-phenoxy-1-benzofuran-2-yl)ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(OC=3C=CC=CC=3)=CC=C2O1 WNGGFYSKLHPGQM-MRXNPFEDSA-N 0.000 claims 1
- QQVDGSPBKSWRPI-QGZVFWFLSA-N (2r)-2-methyl-1-[2-[5-(2-methylphenyl)-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C(=CC=CC=3)C)=CC=C2O1 QQVDGSPBKSWRPI-QGZVFWFLSA-N 0.000 claims 1
- CLXZDMPQYPJIJY-QGZVFWFLSA-N (2r)-2-methyl-1-[2-[5-(3-methylphenyl)-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C)C=CC=3)=CC=C2O1 CLXZDMPQYPJIJY-QGZVFWFLSA-N 0.000 claims 1
- YFUNNJDKYIPKBS-QGZVFWFLSA-N (2r)-2-methyl-1-[2-[5-(4-methylphenyl)-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(C)=CC=3)=CC=C2O1 YFUNNJDKYIPKBS-QGZVFWFLSA-N 0.000 claims 1
- TVSZABXTLKHYJQ-OAHLLOKOSA-N (2r)-2-methyl-1-[2-[5-[3-(trifluoromethyl)phenyl]-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(F)(F)F)=CC=C2O1 TVSZABXTLKHYJQ-OAHLLOKOSA-N 0.000 claims 1
- QLBAREAFIHKHJX-OAHLLOKOSA-N (2r)-2-methyl-1-[2-[5-[4-(trifluoromethoxy)phenyl]-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(OC(F)(F)F)=CC=3)=CC=C2O1 QLBAREAFIHKHJX-OAHLLOKOSA-N 0.000 claims 1
- SYHRFRKBBMDSID-OAHLLOKOSA-N (2r)-2-methyl-1-[2-[5-[4-(trifluoromethyl)phenyl]-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(F)(F)F)=CC=C2O1 SYHRFRKBBMDSID-OAHLLOKOSA-N 0.000 claims 1
- JSFFTMNTWAMSKS-CQSZACIVSA-N (3,5-difluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(F)C=C(F)C=3)=CC=C2O1 JSFFTMNTWAMSKS-CQSZACIVSA-N 0.000 claims 1
- ARRAWZMFGXGZJA-OAHLLOKOSA-N (3-chlorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(Cl)C=CC=3)=CC=C2O1 ARRAWZMFGXGZJA-OAHLLOKOSA-N 0.000 claims 1
- OKOPCYYMBGBJLQ-OAHLLOKOSA-N (3-fluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(F)C=CC=3)=CC=C2O1 OKOPCYYMBGBJLQ-OAHLLOKOSA-N 0.000 claims 1
- ZCQGCYSLQDBETN-MRXNPFEDSA-N (3-methoxyphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound COC1=CC=CC(C(=O)C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 ZCQGCYSLQDBETN-MRXNPFEDSA-N 0.000 claims 1
- PWRBPHUOIIYBHI-MRXNPFEDSA-N (4-chloro-3-methylphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(C)C(Cl)=CC=3)=CC=C2O1 PWRBPHUOIIYBHI-MRXNPFEDSA-N 0.000 claims 1
- LSJFPFPCUYVELQ-MRXNPFEDSA-N (4-fluoro-3-methylphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=C(C)C(F)=CC=3)=CC=C2O1 LSJFPFPCUYVELQ-MRXNPFEDSA-N 0.000 claims 1
- VGSYEFOBFMUWGO-OAHLLOKOSA-N (4-fluorophenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=CC(F)=CC=3)=CC=C2O1 VGSYEFOBFMUWGO-OAHLLOKOSA-N 0.000 claims 1
- ZGSUVVWUSJSBAJ-MRXNPFEDSA-N (4-methoxyphenyl)-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 ZGSUVVWUSJSBAJ-MRXNPFEDSA-N 0.000 claims 1
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- RCKVIIQYEWLWRQ-CYBMUJFWSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,3-thiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=CSC=3)=CC=C2O1 RCKVIIQYEWLWRQ-CYBMUJFWSA-N 0.000 claims 1
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- HIIOCRFTDQIWTM-OAHLLOKOSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1h-benzimidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=4N=CNC=4C=CC=3)=CC=C2O1 HIIOCRFTDQIWTM-OAHLLOKOSA-N 0.000 claims 1
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- RYCZSWCHJYEBNO-MRXNPFEDSA-N 4-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzothiophen-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2S1 RYCZSWCHJYEBNO-MRXNPFEDSA-N 0.000 claims 1
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- FGFIZYSOAVFQGI-UHFFFAOYSA-N 4-[2-[2-[ethyl(propan-2-yl)amino]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN(CC)C(C)C)=CC2=CC=1C1=CC=C(C#N)C=C1 FGFIZYSOAVFQGI-UHFFFAOYSA-N 0.000 claims 1
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- NCOMQTHNEIBOFC-UHFFFAOYSA-N 4-[2-[2-[methyl(propan-2-yl)amino]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN(C)C(C)C)=CC2=CC=1C1=CC=C(C#N)C=C1 NCOMQTHNEIBOFC-UHFFFAOYSA-N 0.000 claims 1
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- MPEHTRLBLLNSLX-GOSISDBHSA-N 4-[3-(2-formylthiophen-3-yl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C2=C(SC=C2)C=O)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 MPEHTRLBLLNSLX-GOSISDBHSA-N 0.000 claims 1
- KUNUOGUHYDNMMV-GOSISDBHSA-N 4-[3-(furan-2-yl)-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C=2OC=CC=2)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 KUNUOGUHYDNMMV-GOSISDBHSA-N 0.000 claims 1
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- YSEGCOZIKAWISO-MRXNPFEDSA-N 4-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazol-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(ON=3)C=3C=CC(=CC=3)C#N)=CC=C2O1 YSEGCOZIKAWISO-MRXNPFEDSA-N 0.000 claims 1
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- QVKBRVOCZODGHW-MRXNPFEDSA-N 4-[3-bromo-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-2-methylbenzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(Br)C2=CC(C=3C=C(C)C(C#N)=CC=3)=CC=C2O1 QVKBRVOCZODGHW-MRXNPFEDSA-N 0.000 claims 1
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- ICYZSKRHQGWZSQ-OAHLLOKOSA-N 5-(2-chlorophenyl)-3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(ON=3)C=3C(=CC=CC=3)Cl)=CC=C2O1 ICYZSKRHQGWZSQ-OAHLLOKOSA-N 0.000 claims 1
- KKVBCLFGDFBRGV-CQSZACIVSA-N 5-(3-chloro-4-fluorophenyl)-3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(ON=3)C=3C=C(Cl)C(F)=CC=3)=CC=C2O1 KKVBCLFGDFBRGV-CQSZACIVSA-N 0.000 claims 1
- HZTKCUBRPQETLS-OAHLLOKOSA-N 5-(4-chlorophenyl)-3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(ON=3)C=3C=CC(Cl)=CC=3)=CC=C2O1 HZTKCUBRPQETLS-OAHLLOKOSA-N 0.000 claims 1
- AYBKWLIHGFBJJT-OAHLLOKOSA-N 5-(4-fluorophenyl)-3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(ON=3)C=3C=CC(F)=CC=3)=CC=C2O1 AYBKWLIHGFBJJT-OAHLLOKOSA-N 0.000 claims 1
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- MNUQMQWKCPNQIW-UHFFFAOYSA-N morpholin-4-yl-[6-[2-[2-(2-oxa-5-azabicyclo[2.2.1]heptan-5-yl)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4C5CC(OC5)C4)OC3=CC=2)N=CC=1C(=O)N1CCOCC1 MNUQMQWKCPNQIW-UHFFFAOYSA-N 0.000 claims 1
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- NVBRBYHGZWOTEG-MRXNPFEDSA-N n-[1-[3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]ethylidene]hydroxylamine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)=NO)=CC=C2O1 NVBRBYHGZWOTEG-MRXNPFEDSA-N 0.000 claims 1
- LBWLQQTUPHFQQE-QGZVFWFLSA-N n-cyclohexyl-n-methyl-2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-amine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N(C)C3CCCCC3)=CC=C2O1 LBWLQQTUPHFQQE-QGZVFWFLSA-N 0.000 claims 1
- OWBLQGYUIKRMSC-QGZVFWFLSA-N n-methoxy-n-methyl-3-[2-[2-[(2r)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzamide Chemical compound CON(C)C(=O)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 OWBLQGYUIKRMSC-QGZVFWFLSA-N 0.000 claims 1
- OWOFFZJYWRZHME-UHFFFAOYSA-N n-methyl-n-[2-[2-(2-methylpyrrolidin-1-yl)ethyl]-1-benzofuran-5-yl]-1,3-benzodioxol-5-amine Chemical compound CC1CCCN1CCC1=CC2=CC(N(C)C=3C=C4OCOC4=CC=3)=CC=C2O1 OWOFFZJYWRZHME-UHFFFAOYSA-N 0.000 claims 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
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| US09/810,648 US20020177589A1 (en) | 2001-03-16 | 2001-03-16 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| US10/044,495 US20020183309A1 (en) | 2001-03-16 | 2002-01-11 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
| US10/081,207 US6969730B2 (en) | 2001-03-16 | 2002-02-25 | Amines as histamine-3 receptor ligands and their therapeutic applications |
| PCT/US2002/007107 WO2002074758A2 (en) | 2001-03-16 | 2002-03-11 | Novel amines as histamine-3 receptor ligands and their therapeutic applications |
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| JP2005500986A JP2005500986A (ja) | 2005-01-13 |
| JP2005500986A5 true JP2005500986A5 (https=) | 2005-12-22 |
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| JP (1) | JP4612990B2 (https=) |
| AR (1) | AR035783A1 (https=) |
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| CA (1) | CA2440238C (https=) |
| MX (1) | MXPA03008319A (https=) |
| WO (1) | WO2002074758A2 (https=) |
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| US7314937B2 (en) | 2002-03-21 | 2008-01-01 | Eli Lilly And Company | Non-imidazole aryl alkylamines compounds as histamine H3 receptor antagonists, preparation and therapeutic uses |
| US6822101B2 (en) | 2002-09-16 | 2004-11-23 | Abbott Laboratories | Process for preparing amine-substituted benzofurans |
| US7153889B2 (en) | 2002-11-12 | 2006-12-26 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
| AU2003291329A1 (en) * | 2002-11-12 | 2004-06-03 | Abbott Laboratories | Bicyclic-substituted amines as histamine-3 receptor ligands |
| US7244852B2 (en) | 2003-02-27 | 2007-07-17 | Abbott Laboratories | Process for preparing 2-methylpyrrolidine and specific enantiomers thereof |
| RU2366655C2 (ru) | 2003-03-14 | 2009-09-10 | Оно Фармасьютикал Ко., Лтд. | Азотсодержащие гетероциклические производные и лекарственные средства, содержащие их в качестве активного ингредиента |
| EP1611902A4 (en) * | 2003-04-03 | 2006-04-12 | Kyowa Hakko Kogyo Kk | MEANS FOR THE PREVENTION AND / OR TREATMENT OF NEUROPATHIC PAIN |
| US20040224952A1 (en) * | 2003-05-07 | 2004-11-11 | Cowart Marlon D. | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| US7094790B2 (en) | 2003-05-07 | 2006-08-22 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| WO2004101559A1 (en) * | 2003-05-07 | 2004-11-25 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| CA2542220A1 (en) * | 2003-10-22 | 2005-05-06 | Eli Lilly And Company | Novel mch receptor antagonists |
| US7435837B2 (en) | 2003-10-24 | 2008-10-14 | Wyeth | Dihydrobenzofuranyl alkanamine derivatives and methods for using same |
| SE0303480D0 (sv) * | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| CN1934094A (zh) * | 2004-03-05 | 2007-03-21 | 万有制药株式会社 | 二芳基取代杂环5元环衍生物 |
| EP1734963A4 (en) | 2004-04-02 | 2008-06-18 | Merck & Co Inc | METHOD FOR TREATING PEOPLE WITH METABOLIC AND ANTHROPOMETRIC DISORDER |
| US7145005B2 (en) | 2004-05-12 | 2006-12-05 | Abbott Laboratories | 2-(6-{2-[(2R)-2-Methyl-1-pyrrolidin-1-yl]-ethyl}-2-naphthalen-2-yl)-2H-pyridazin-3-one salts and their preparation |
| US20050256118A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| US7205316B2 (en) | 2004-05-12 | 2007-04-17 | Abbott Laboratories | Tri- and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US20050256309A1 (en) * | 2004-05-12 | 2005-11-17 | Altenbach Robert J | Tri-and bi-cyclic heteroaryl histamine-3 receptor ligands |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | Bicyclic-substituted amines having cyclic-substituted monocyclic substituents |
| DE102004030099A1 (de) * | 2004-06-22 | 2006-01-12 | Grünenthal GmbH | Gesättigte und ungesättigte 3-Pyridyl-benzocycloalkylmethyl-amine als Serotonin- und/oder Noradrenalin-Reuptake-Hemmer und/oder µ-Opioidrezeptor-Modulatoren |
| US8143404B2 (en) | 2004-09-13 | 2012-03-27 | Ono Pharmaceutical Co., Ltd | Nitrogenous heterocylic derivative and medicine containing the same as an active ingredient |
| US7553964B2 (en) | 2005-06-03 | 2009-06-30 | Abbott Laboratories | Cyclobutyl amine derivatives |
| CA2644368A1 (en) | 2006-03-10 | 2007-09-20 | Ono Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient |
| US20080015193A1 (en) * | 2006-06-20 | 2008-01-17 | Mendoza Jose S | Certain azoles exhibiting ATP-utilizing enzyme inhibitory activity, compositions, and uses thereof |
| BRPI0712823A2 (pt) | 2006-06-23 | 2012-07-24 | Abbott Lab | derivados de ciclopropil amina como moduladores de receptor de histamina h3 |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| CN101855211B (zh) | 2007-11-13 | 2013-06-12 | 大正制药株式会社 | 苯基吡唑衍生物 |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| WO2010043000A1 (en) * | 2008-10-17 | 2010-04-22 | Akaal Pharma Pty Ltd | S1p receptors modulators and their use thereof |
| AU2009304596A1 (en) | 2008-10-17 | 2010-04-22 | Akaal Pharma Pty Ltd | S1P receptors modulators |
| US9186353B2 (en) | 2009-04-27 | 2015-11-17 | Abbvie Inc. | Treatment of osteoarthritis pain |
| JP2012082186A (ja) * | 2010-09-15 | 2012-04-26 | Bayer Cropscience Ag | 殺虫性アリールピロリジン類 |
| GB201113538D0 (en) * | 2011-08-04 | 2011-09-21 | Karobio Ab | Novel estrogen receptor ligands |
| US9365511B2 (en) * | 2013-01-09 | 2016-06-14 | Arena Pharmaceuticals, Inc. | Biphenyl-ethyl-pyrrolidine derivatives as histamine H3 receptor modulators for the treatment of cognitive disorders |
| MX2017008136A (es) * | 2014-12-22 | 2018-03-06 | Teva Pharmaceuticals Int Gmbh | Sal de l-tartrato de pridopidina. |
| CN109456292B (zh) * | 2018-10-23 | 2022-06-10 | 中山大学 | 一种海洋真菌来源的香豆素类化合物及其制备方法与应用 |
| WO2022113008A1 (en) | 2020-11-27 | 2022-06-02 | Richter Gedeon Nyrt. | Histamine h3 receptor antagonists/inverse agonists for the treatment of autism spectrum disorder |
| CN114805261B (zh) * | 2021-01-18 | 2023-03-21 | 沈阳药科大学 | 苯并呋喃类lsd1抑制剂及其制备方法 |
| CN115385885A (zh) * | 2022-05-05 | 2022-11-25 | 深圳海创生物科技有限公司 | 一种蓝莓多酚、组合物及其在制备具有降血脂和/或减肥作用的药物或食品中的应用 |
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| US4237144A (en) * | 1979-06-21 | 1980-12-02 | Merck & Co., Inc. | 2,3-Dihydro-2,6,7-trisubstituted-5-acylbenzofurans |
| IL101785A0 (en) * | 1991-05-10 | 1992-12-30 | Fujisawa Pharmaceutical Co | Urea derivatives,processes for the preparation thereof and pharmaceutical compositions containing the same |
| US5436246A (en) * | 1992-09-17 | 1995-07-25 | Merrell Dow Pharmaceuticals Inc. | Serotonin receptor agents |
| JP2759257B2 (ja) * | 1993-09-28 | 1998-05-28 | 大塚製薬株式会社 | 糖尿病治療剤 |
| JPH07173158A (ja) * | 1993-12-17 | 1995-07-11 | Taiho Yakuhin Kogyo Kk | チアゾリジンジオン誘導体又はその塩 |
| US5585492A (en) * | 1994-10-11 | 1996-12-17 | G. D. Searle & Co. | LTA4 Hydrolase inhibitors |
| WO1997029105A1 (en) * | 1996-02-09 | 1997-08-14 | Kumiai Chemical Industry Co., Ltd. | Benzofuran-7-yluracil derivatives and herbicides |
| US6077812A (en) * | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
| EP0977753A1 (en) * | 1997-12-02 | 2000-02-09 | Dr. Reddy's Research Foundation | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension |
| EP0978512A1 (en) * | 1998-07-29 | 2000-02-09 | Societe Civile Bioprojet | Non-imidazole aryloxy (or arylthio) alkylamines as histamine H3-receptor antagonists and their therapeutic applications |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
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- 2002-03-11 EP EP02715079A patent/EP1370546A2/en not_active Withdrawn
- 2002-03-11 JP JP2002573767A patent/JP4612990B2/ja not_active Expired - Fee Related
- 2002-03-11 BR BR0205829-4A patent/BR0205829A/pt not_active IP Right Cessation
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- 2002-03-11 EP EP10180385A patent/EP2258694A1/en not_active Withdrawn
- 2002-03-11 MX MXPA03008319A patent/MXPA03008319A/es active IP Right Grant
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