JP2005500986A5 - - Google Patents
Download PDFInfo
- 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
Links
- -1 (2R) -2-methyl-1-pyrrolidinyl Chemical group 0.000 claims 89
- 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 group [H]S* 0.000 claims 21
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 19
- 229910052757 nitrogen Inorganic materials 0.000 claims 19
- JFDZBHWFFUWGJE-UHFFFAOYSA-N Benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims 14
- 125000000168 pyrrolyl group Chemical group 0.000 claims 14
- 150000002829 nitrogen Chemical group 0.000 claims 13
- 125000002757 morpholinyl group Chemical group 0.000 claims 12
- 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
- 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
- 239000000651 prodrug Substances 0.000 claims 7
- 229940002612 prodrugs Drugs 0.000 claims 7
- 150000003839 salts Chemical class 0.000 claims 7
- 239000011780 sodium chloride Substances 0.000 claims 7
- 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
- UFHFLCQGNIYNRP-UHFFFAOYSA-N hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000000304 alkynyl group Chemical group 0.000 claims 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 4
- 229940113083 morpholine Drugs 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
- 201000010099 disease Diseases 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
- 206010057668 Cognitive disease Diseases 0.000 claims 2
- 241000124008 Mammalia Species 0.000 claims 2
- 125000004450 alkenylene group Chemical group 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 230000000051 modifying Effects 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
- KCQLVGXLAGACJI-OAHLLOKOSA-N (2R)-2-methyl-1-[2-[5-[3-(trifluoromethoxy)phenyl]-1-benzofuran-2-yl]ethyl]pyrrolidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(OC(F)(F)F)C=CC=3)=CC=C2O1 KCQLVGXLAGACJI-OAHLLOKOSA-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
- NISULOSDVFYWIH-GVKDRIAJSA-N (2R,3S)-2,3-dihydroxybutanedioic acid;4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O.C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 NISULOSDVFYWIH-GVKDRIAJSA-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
- NCMDQOIHFGGPGZ-OAHLLOKOSA-N (4-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=CC(Cl)=CC=3)=CC=C2O1 NCMDQOIHFGGPGZ-OAHLLOKOSA-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
- YANFQSPNBDHUOP-QGZVFWFLSA-N (4-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=CC(C)=CC=3)=CC=C2O1 YANFQSPNBDHUOP-QGZVFWFLSA-N 0.000 claims 1
- PNKWFQCOTNIHSE-UHFFFAOYSA-N 1,4$l^{2}-thiazinane Chemical group C1CSCC[N]1 PNKWFQCOTNIHSE-UHFFFAOYSA-N 0.000 claims 1
- XMFGAKCDWKKTRX-OAHLLOKOSA-N 1-[1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrrol-3-yl]ethanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C=C(C=C3)C(C)=O)=CC=C2O1 XMFGAKCDWKKTRX-OAHLLOKOSA-N 0.000 claims 1
- SYKZBFMOAVGFQH-CYBMUJFWSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-3,4-bis(trifluoromethyl)pyrrole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C=C(C(=C3)C(F)(F)F)C(F)(F)F)=CC=C2O1 SYKZBFMOAVGFQH-CYBMUJFWSA-N 0.000 claims 1
- PLRBHSSVBVBIBD-MRXNPFEDSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzimidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C4=CC=CC=C4N=C3)=CC=C2O1 PLRBHSSVBVBIBD-MRXNPFEDSA-N 0.000 claims 1
- GEGFJMYOFOIEEZ-CQSZACIVSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C=NC=C3)=CC=C2O1 GEGFJMYOFOIEEZ-CQSZACIVSA-N 0.000 claims 1
- XKRZACAXNDQINU-CQSZACIVSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazole-4,5-dicarbonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C(=C(C#N)N=C3)C#N)=CC=C2O1 XKRZACAXNDQINU-CQSZACIVSA-N 0.000 claims 1
- JICYBUUSLSEHKI-CQSZACIVSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3N=CC=C3)=CC=C2O1 JICYBUUSLSEHKI-CQSZACIVSA-N 0.000 claims 1
- PCNMJNWQYWANGI-CQSZACIVSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrazole-4-carbonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3N=CC(=C3)C#N)=CC=C2O1 PCNMJNWQYWANGI-CQSZACIVSA-N 0.000 claims 1
- QEYMYMCVILKGFP-OAHLLOKOSA-N 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrrole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C=CC=C3)=CC=C2O1 QEYMYMCVILKGFP-OAHLLOKOSA-N 0.000 claims 1
- SXAHXCFHDVGDRN-UHFFFAOYSA-N 1-[2-[5-(4-chlorophenyl)-1-benzofuran-2-yl]ethyl]-2-methylpyrrolidine Chemical compound CC1CCCN1CCC1=CC2=CC(C=3C=CC(Cl)=CC=3)=CC=C2O1 SXAHXCFHDVGDRN-UHFFFAOYSA-N 0.000 claims 1
- DMJYWUDBYVJYJG-TZHYSIJRSA-N 1-[3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]ethanol Chemical compound CC(O)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 DMJYWUDBYVJYJG-TZHYSIJRSA-N 0.000 claims 1
- AZWATKGVDUSMSO-MRXNPFEDSA-N 1-[3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]ethanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)=O)=CC=C2O1 AZWATKGVDUSMSO-MRXNPFEDSA-N 0.000 claims 1
- CELAAZUTSNRGKM-QGZVFWFLSA-N 1-[3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]propan-1-one Chemical compound CCC(=O)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 CELAAZUTSNRGKM-QGZVFWFLSA-N 0.000 claims 1
- YMVHIGHEQPRIGD-CQSZACIVSA-N 1-methyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-4-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C=3N=CN(C)C=3)C=CC=C2O1 YMVHIGHEQPRIGD-CQSZACIVSA-N 0.000 claims 1
- XNLHHXUVLAESTO-CQSZACIVSA-N 1-methyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=CN(C)C=3)=CC=C2O1 XNLHHXUVLAESTO-CQSZACIVSA-N 0.000 claims 1
- AALLFCXWHBVCPG-CQSZACIVSA-N 1-methyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3N=CN(C)C=3)C=C2O1 AALLFCXWHBVCPG-CQSZACIVSA-N 0.000 claims 1
- HNGPWXZIXJADNH-CQSZACIVSA-N 1-methyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3N=CN(C)C=3)=C2O1 HNGPWXZIXJADNH-CQSZACIVSA-N 0.000 claims 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- DTOQWRCYIBXBAZ-OAHLLOKOSA-N 2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-N-(oxan-4-yl)-1-benzofuran-5-amine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(NC3CCOCC3)=CC=C2O1 DTOQWRCYIBXBAZ-OAHLLOKOSA-N 0.000 claims 1
- IJKZKLQZILWOJX-CYBMUJFWSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,3-thiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3SC=CN=3)=CC=C2O1 IJKZKLQZILWOJX-CYBMUJFWSA-N 0.000 claims 1
- OWSCGPCEBHQRJR-CYBMUJFWSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1H-imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3NC=CN=3)=CC=C2O1 OWSCGPCEBHQRJR-CYBMUJFWSA-N 0.000 claims 1
- HCAQEFBWQFNUAJ-CQSZACIVSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=CC=NC=3)=CC=C2O1 HCAQEFBWQFNUAJ-CQSZACIVSA-N 0.000 claims 1
- OGCKIHBPWCSRQN-CYBMUJFWSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1,3-thiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3SC=CN=3)C=C2O1 OGCKIHBPWCSRQN-CYBMUJFWSA-N 0.000 claims 1
- CBMDYUTVCMIJID-CYBMUJFWSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1H-imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3NC=CN=3)C=C2O1 CBMDYUTVCMIJID-CYBMUJFWSA-N 0.000 claims 1
- DCTKXPNQQIRMHJ-CQSZACIVSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]pyrazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3N=CC=NC=3)C=C2O1 DCTKXPNQQIRMHJ-CQSZACIVSA-N 0.000 claims 1
- DXPUVMZIIFCQOC-CYBMUJFWSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1,3-thiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3SC=CN=3)=C2O1 DXPUVMZIIFCQOC-CYBMUJFWSA-N 0.000 claims 1
- MRSSNVXGQNSMBT-CYBMUJFWSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1H-imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3NC=CN=3)=C2O1 MRSSNVXGQNSMBT-CYBMUJFWSA-N 0.000 claims 1
- BZFZOSVSQFLYNR-CQSZACIVSA-N 2-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]pyrazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3N=CC=NC=3)=C2O1 BZFZOSVSQFLYNR-CQSZACIVSA-N 0.000 claims 1
- CIPPJHOVCBGSOP-QGZVFWFLSA-N 2-[3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]propan-2-ol Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)(C)O)=CC=C2O1 CIPPJHOVCBGSOP-QGZVFWFLSA-N 0.000 claims 1
- WPPQUNPJCSHTHG-OAHLLOKOSA-N 2-fluoro-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(F)C(C#N)=CC=3)=CC=C2O1 WPPQUNPJCSHTHG-OAHLLOKOSA-N 0.000 claims 1
- IWKJHKKUCUSQIS-QGZVFWFLSA-N 2-methyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C)C(C#N)=CC=3)=CC=C2O1 IWKJHKKUCUSQIS-QGZVFWFLSA-N 0.000 claims 1
- QKUQBIOGJCVQIC-CYBMUJFWSA-N 3,5-dimethyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1,2-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C3=C(ON=C3C)C)C=C2O1 QKUQBIOGJCVQIC-CYBMUJFWSA-N 0.000 claims 1
- HWRLMINPOKWFCR-CYBMUJFWSA-N 3,5-dimethyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1,2-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C3=C(ON=C3C)C)=C2O1 HWRLMINPOKWFCR-CYBMUJFWSA-N 0.000 claims 1
- NAMSNEYZOTVZHH-OAHLLOKOSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-ium-1-yl]ethyl]-1-benzofuran-5-yl]benzoate Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(O)=O)=CC=C2O1 NAMSNEYZOTVZHH-OAHLLOKOSA-N 0.000 claims 1
- PUYLRAJUSRKGNY-OAHLLOKOSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-5-(thiophen-2-ylmethyl)-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(CC=4SC=CC=4)ON=3)=CC=C2O1 PUYLRAJUSRKGNY-OAHLLOKOSA-N 0.000 claims 1
- SHNOSBODSBRATB-MRXNPFEDSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-5-phenyl-1,2,4-oxadiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(ON=3)C=3C=CC=CC=3)=CC=C2O1 SHNOSBODSBRATB-MRXNPFEDSA-N 0.000 claims 1
- MHOQYRLYWGQIPR-CQSZACIVSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-5-propyl-1,2,4-oxadiazole Chemical compound O1C(CCC)=NC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=N1 MHOQYRLYWGQIPR-CQSZACIVSA-N 0.000 claims 1
- GZQDEENZRDJPIY-MRXNPFEDSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzaldehyde Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=O)C=CC=3)=CC=C2O1 GZQDEENZRDJPIY-MRXNPFEDSA-N 0.000 claims 1
- WWEXCCZITRBBJR-MRXNPFEDSA-N 3-[2-[2-[(2R)-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-MRXNPFEDSA-N 0.000 claims 1
- ZXBZIFLDLUDVNG-OAHLLOKOSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazo[4,5-c]pyridine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C4=CN=CC=C4N=C3)=CC=C2O1 ZXBZIFLDLUDVNG-OAHLLOKOSA-N 0.000 claims 1
- GLRCFSKHGSEDQU-OAHLLOKOSA-N 3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=NC=CC=3)=CC=C2O1 GLRCFSKHGSEDQU-OAHLLOKOSA-N 0.000 claims 1
- POCPMVTZVLIWHY-QGZVFWFLSA-N 3-[2-[3-[(2R)-2-methylpyrrolidin-1-yl]propyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCCC1=CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2O1 POCPMVTZVLIWHY-QGZVFWFLSA-N 0.000 claims 1
- IIGYMOYWZOWDDU-GOSISDBHSA-N 3-[2-[4-[(2R)-2-methylpyrrolidin-1-yl]butyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCCCC1=CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2O1 IIGYMOYWZOWDDU-GOSISDBHSA-N 0.000 claims 1
- SYXSTKXZFAIHJX-OAHLLOKOSA-N 3-[2-[[(2R)-2-methylpyrrolidin-1-yl]methyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CC1=CC2=CC(C=3C=C(C=CC=3)C#N)=CC=C2O1 SYXSTKXZFAIHJX-OAHLLOKOSA-N 0.000 claims 1
- JJUWVXWBUYSZSD-QGZVFWFLSA-N 3-[[3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazol-5-yl]methyl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=C(CC=4C=C(C=CC=4)C#N)ON=3)=CC=C2O1 JJUWVXWBUYSZSD-QGZVFWFLSA-N 0.000 claims 1
- YGRMUPQBFBMRIZ-MRXNPFEDSA-N 3-methyl-1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrrole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C=C(C)C=C3)=CC=C2O1 YGRMUPQBFBMRIZ-MRXNPFEDSA-N 0.000 claims 1
- MRGQYFQFEWCMPP-LJQANCHMSA-N 3-methyl-1-[3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]butan-1-one Chemical compound CC(C)CC(=O)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 MRGQYFQFEWCMPP-LJQANCHMSA-N 0.000 claims 1
- PJIVVAJXWKUQRT-QGZVFWFLSA-N 3-methyl-4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C(=CC(=CC=3)C#N)C)=CC=C2O1 PJIVVAJXWKUQRT-QGZVFWFLSA-N 0.000 claims 1
- AGNGUYAQBIAHBH-OAHLLOKOSA-N 3-methyl-6-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-4-yl]pyridazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C=3N=NC(C)=CC=3)C=CC=C2O1 AGNGUYAQBIAHBH-OAHLLOKOSA-N 0.000 claims 1
- CDOCQFAWLLNKHB-OAHLLOKOSA-N 3-methyl-6-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=NC(C)=CC=3)=CC=C2O1 CDOCQFAWLLNKHB-OAHLLOKOSA-N 0.000 claims 1
- URWUAIMOYIFADV-OAHLLOKOSA-N 3-methyl-6-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]pyridazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3N=NC(C)=CC=3)C=C2O1 URWUAIMOYIFADV-OAHLLOKOSA-N 0.000 claims 1
- MHSLRVBRCNMYPN-OAHLLOKOSA-N 3-methyl-6-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]pyridazine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3N=NC(C)=CC=3)=C2O1 MHSLRVBRCNMYPN-OAHLLOKOSA-N 0.000 claims 1
- PCAPWQNCQZOXPX-GFCCVEGCSA-N 4,5-dichloro-1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C(=C(Cl)N=C3)Cl)=CC=C2O1 PCAPWQNCQZOXPX-GFCCVEGCSA-N 0.000 claims 1
- ROXWBFUEWXMEKJ-UHFFFAOYSA-N 4-[2-(2-aminoethyl)-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN)=CC2=CC=1C1=CC=C(C#N)C=C1 ROXWBFUEWXMEKJ-UHFFFAOYSA-N 0.000 claims 1
- LVZJESUDRWGMGZ-UHFFFAOYSA-N 4-[2-(2-imidazol-1-ylethyl)-1-benzofuran-5-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=C(OC(CCN2C=NC=C2)=C2)C2=C1 LVZJESUDRWGMGZ-UHFFFAOYSA-N 0.000 claims 1
- CKFMMVLRYYANSV-UHFFFAOYSA-N 4-[2-(2-piperidin-1-ylethyl)-1-benzofuran-5-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=C(OC(CCN2CCCCC2)=C2)C2=C1 CKFMMVLRYYANSV-UHFFFAOYSA-N 0.000 claims 1
- NAQIDFISILZVAV-UHFFFAOYSA-N 4-[2-(2-pyrrolidin-1-ylethyl)-1-benzofuran-5-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=C(OC(CCN2CCCC2)=C2)C2=C1 NAQIDFISILZVAV-UHFFFAOYSA-N 0.000 claims 1
- INMKIUUCZWOKBP-UHFFFAOYSA-N 4-[2-[2-(2-ethylpyrrolidin-1-yl)ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound CCC1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 INMKIUUCZWOKBP-UHFFFAOYSA-N 0.000 claims 1
- IHTBDEYRRPLDAI-UHFFFAOYSA-N 4-[2-[2-(2-methylpiperidin-1-yl)ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound CC1CCCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 IHTBDEYRRPLDAI-UHFFFAOYSA-N 0.000 claims 1
- ZLCKROBKBCZLCK-UHFFFAOYSA-N 4-[2-[2-(3,6-dihydro-2H-pyridin-1-yl)ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=C(OC(CCN2CC=CCC2)=C2)C2=C1 ZLCKROBKBCZLCK-UHFFFAOYSA-N 0.000 claims 1
- HRPKXNNRDDPCBN-UHFFFAOYSA-N 4-[2-[2-(4-methylpiperidin-1-yl)ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C1CC(C)CCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 HRPKXNNRDDPCBN-UHFFFAOYSA-N 0.000 claims 1
- CEVDQDHDUGZWIN-UHFFFAOYSA-N 4-[2-[2-(azepan-1-yl)ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C1=CC(C#N)=CC=C1C1=CC=C(OC(CCN2CCCCCC2)=C2)C2=C1 CEVDQDHDUGZWIN-UHFFFAOYSA-N 0.000 claims 1
- DRLVHRPQTXISJB-UHFFFAOYSA-N 4-[2-[2-(diethylamino)ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN(CC)CC)=CC2=CC=1C1=CC=C(C#N)C=C1 DRLVHRPQTXISJB-UHFFFAOYSA-N 0.000 claims 1
- JFCPJZQAWZEYPU-HXUWFJFHSA-N 4-[2-[2-[(2R)-2-(hydroxymethyl)pyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound OC[C@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 JFCPJZQAWZEYPU-HXUWFJFHSA-N 0.000 claims 1
- RYSCTIJOMWWPSQ-OAHLLOKOSA-N 4-[2-[2-[(2R)-2-methyl-5-oxopyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCC(=O)N1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 RYSCTIJOMWWPSQ-OAHLLOKOSA-N 0.000 claims 1
- LTKBEKWYXONRLE-MRXNPFEDSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-4-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C=3C=CC(=CC=3)C#N)C=CC=C2O1 LTKBEKWYXONRLE-MRXNPFEDSA-N 0.000 claims 1
- 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
- VIVRQTMYTCNEBD-GOSISDBHSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1-phenylpyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C3=CN(N=C3)C=3C=CC=CC=3)=CC=C2O1 VIVRQTMYTCNEBD-GOSISDBHSA-N 0.000 claims 1
- 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
- DATDVQKGDSNVRT-CYBMUJFWSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1H-pyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C3=CNN=C3)=CC=C2O1 DATDVQKGDSNVRT-CYBMUJFWSA-N 0.000 claims 1
- YXCKFAAPQNFHIP-CYBMUJFWSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1,3-thiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3N=CSC=3)C=C2O1 YXCKFAAPQNFHIP-CYBMUJFWSA-N 0.000 claims 1
- FSJOECWBSLNAHO-GOSISDBHSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1-phenylpyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C3=CN(N=C3)C=3C=CC=CC=3)C=C2O1 FSJOECWBSLNAHO-GOSISDBHSA-N 0.000 claims 1
- DKWQJMYZTVOTNX-OAHLLOKOSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1H-benzimidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=4N=CNC=4C=CC=3)C=C2O1 DKWQJMYZTVOTNX-OAHLLOKOSA-N 0.000 claims 1
- GBUXLEJFFMWWOL-MRXNPFEDSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1H-indole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=4C=CNC=4C=CC=3)C=C2O1 GBUXLEJFFMWWOL-MRXNPFEDSA-N 0.000 claims 1
- NZJGTDMHQUZREC-CYBMUJFWSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-1H-pyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C3=CNN=C3)C=C2O1 NZJGTDMHQUZREC-CYBMUJFWSA-N 0.000 claims 1
- HLMKABGIWSQBNO-MRXNPFEDSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]benzene-1,2-dicarbonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=C(C(C#N)=CC=3)C#N)C=C2O1 HLMKABGIWSQBNO-MRXNPFEDSA-N 0.000 claims 1
- KOJILSQOYUKYDK-MRXNPFEDSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=CC(=CC=3)C#N)C=C2O1 KOJILSQOYUKYDK-MRXNPFEDSA-N 0.000 claims 1
- FUDDLYFJGTYJSZ-OAHLLOKOSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]pyridine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=CN=CC=3)C=C2O1 FUDDLYFJGTYJSZ-OAHLLOKOSA-N 0.000 claims 1
- MORJVKIITZSFQB-CYBMUJFWSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1,3-thiazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3N=CSC=3)=C2O1 MORJVKIITZSFQB-CYBMUJFWSA-N 0.000 claims 1
- AMWJXPOYKMPOQQ-GOSISDBHSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1-phenylpyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C3=CN(N=C3)C=3C=CC=CC=3)=C2O1 AMWJXPOYKMPOQQ-GOSISDBHSA-N 0.000 claims 1
- MQQRHDOVERRLJK-OAHLLOKOSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1H-benzimidazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=4N=CNC=4C=CC=3)=C2O1 MQQRHDOVERRLJK-OAHLLOKOSA-N 0.000 claims 1
- OHDLNLPMUITORL-MRXNPFEDSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1H-indole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=4C=CNC=4C=CC=3)=C2O1 OHDLNLPMUITORL-MRXNPFEDSA-N 0.000 claims 1
- PYPDRKOYCTVCIV-CYBMUJFWSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-1H-pyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C3=CNN=C3)=C2O1 PYPDRKOYCTVCIV-CYBMUJFWSA-N 0.000 claims 1
- UYLGIZJONQCZPH-MRXNPFEDSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]benzene-1,2-dicarbonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=C(C(C#N)=CC=3)C#N)=C2O1 UYLGIZJONQCZPH-MRXNPFEDSA-N 0.000 claims 1
- QTTNVCWKEBQNOK-OAHLLOKOSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]pyridine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=CN=CC=3)=C2O1 QTTNVCWKEBQNOK-OAHLLOKOSA-N 0.000 claims 1
- 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
- OSFVYVDBXSUKGK-LJQANCHMSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-3-pyridin-3-yl-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C=2C=NC=CC=2)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 OSFVYVDBXSUKGK-LJQANCHMSA-N 0.000 claims 1
- JNJKWLXXDYXBIF-GOSISDBHSA-N 4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-3-thiophen-3-yl-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C2=CSC=C2)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 JNJKWLXXDYXBIF-GOSISDBHSA-N 0.000 claims 1
- SUXVYLBRHCOYGN-IAGOWNOFSA-N 4-[2-[2-[(2R,5R)-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-IAGOWNOFSA-N 0.000 claims 1
- DCIRDTIBHJXEGG-HDICACEKSA-N 4-[2-[2-[(2R,6S)-2,6-dimethylpiperidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@H]1CCC[C@@H](C)N1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 DCIRDTIBHJXEGG-HDICACEKSA-N 0.000 claims 1
- RYMGYDNLRZISML-FQEVSTJZSA-N 4-[2-[2-[(2S)-2-(fluoromethyl)pyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound FC[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 RYMGYDNLRZISML-FQEVSTJZSA-N 0.000 claims 1
- JFCPJZQAWZEYPU-FQEVSTJZSA-N 4-[2-[2-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound OC[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 JFCPJZQAWZEYPU-FQEVSTJZSA-N 0.000 claims 1
- INMKIUUCZWOKBP-NRFANRHFSA-N 4-[2-[2-[(2S)-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-NRFANRHFSA-N 0.000 claims 1
- LTKBEKWYXONRLE-INIZCTEOSA-N 4-[2-[2-[(2S)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-4-yl]benzonitrile Chemical compound C[C@H]1CCCN1CCC1=CC2=C(C=3C=CC(=CC=3)C#N)C=CC=C2O1 LTKBEKWYXONRLE-INIZCTEOSA-N 0.000 claims 1
- KOJILSQOYUKYDK-INIZCTEOSA-N 4-[2-[2-[(2S)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]benzonitrile Chemical compound C[C@H]1CCCN1CCC1=CC2=CC=C(C=3C=CC(=CC=3)C#N)C=C2O1 KOJILSQOYUKYDK-INIZCTEOSA-N 0.000 claims 1
- GXIARDOKAMVMMN-LJQANCHMSA-N 4-[2-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C1[C@H](O)CCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 GXIARDOKAMVMMN-LJQANCHMSA-N 0.000 claims 1
- ARDRZCADVURIHZ-NRFANRHFSA-N 4-[2-[2-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C1[C@@H](N(C)C)CCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 ARDRZCADVURIHZ-NRFANRHFSA-N 0.000 claims 1
- 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
- NEPGMLPWQPTHQU-UHFFFAOYSA-N 4-[2-[2-[ethyl(propyl)amino]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN(CC)CCC)=CC2=CC=1C1=CC=C(C#N)C=C1 NEPGMLPWQPTHQU-UHFFFAOYSA-N 0.000 claims 1
- YLQCEFIAJCBORL-UHFFFAOYSA-N 4-[2-[2-[methyl(2-methylpropyl)amino]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN(C)CC(C)C)=CC2=CC=1C1=CC=C(C#N)C=C1 YLQCEFIAJCBORL-UHFFFAOYSA-N 0.000 claims 1
- 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
- LLWAOCRNMSZQOZ-UHFFFAOYSA-N 4-[2-[2-[tert-butyl(methyl)amino]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C=1C=C2OC(CCN(C)C(C)(C)C)=CC2=CC=1C1=CC=C(C#N)C=C1 LLWAOCRNMSZQOZ-UHFFFAOYSA-N 0.000 claims 1
- WEYXJYZKLIWNLU-CQSZACIVSA-N 4-[3,6-dichloro-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(Cl)C2=CC(C=3C=CC(=CC=3)C#N)=C(Cl)C=C2O1 WEYXJYZKLIWNLU-CQSZACIVSA-N 0.000 claims 1
- 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
- NODVSZXJRDDEHY-UHFFFAOYSA-N 4-[3-[2-(diethylamino)ethyl]-4-methyl-2-oxochromen-7-yl]benzonitrile Chemical compound C1=C2OC(=O)C(CCN(CC)CC)=C(C)C2=CC=C1C1=CC=C(C#N)C=C1 NODVSZXJRDDEHY-UHFFFAOYSA-N 0.000 claims 1
- 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
- GWMPELZQCAJOJN-MRXNPFEDSA-N 4-[3-acetyl-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(C(C)=O)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 GWMPELZQCAJOJN-MRXNPFEDSA-N 0.000 claims 1
- 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
- GQHZXYMFMVSJMK-OAHLLOKOSA-N 4-[3-bromo-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(Br)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 GQHZXYMFMVSJMK-OAHLLOKOSA-N 0.000 claims 1
- FFVNCGPPEXUMRZ-OAHLLOKOSA-N 4-[3-chloro-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(Cl)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 FFVNCGPPEXUMRZ-OAHLLOKOSA-N 0.000 claims 1
- YTVBWCGJJJJGGC-OAHLLOKOSA-N 4-[3-iodo-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=C(I)C2=CC(C=3C=CC(=CC=3)C#N)=CC=C2O1 YTVBWCGJJJJGGC-OAHLLOKOSA-N 0.000 claims 1
- KUKYHFQMNOCTSC-MRXNPFEDSA-N 4-[4-methyl-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=C(C)C(C=3C=CC(=CC=3)C#N)=CC=C2O1 KUKYHFQMNOCTSC-MRXNPFEDSA-N 0.000 claims 1
- WTSUXNYJXLMBIO-UHFFFAOYSA-N 4-[4-methyl-2-oxo-3-(2-piperidin-1-ylethyl)chromen-7-yl]benzonitrile Chemical compound O=C1OC=2C=C(C=3C=CC(=CC=3)C#N)C=CC=2C(C)=C1CCN1CCCCC1 WTSUXNYJXLMBIO-UHFFFAOYSA-N 0.000 claims 1
- BDGZSZLSIHDPAV-UHFFFAOYSA-N 4-[4-methyl-2-oxo-3-(2-pyrrolidin-1-ylethyl)chromen-7-yl]benzonitrile Chemical compound O=C1OC=2C=C(C=3C=CC(=CC=3)C#N)C=CC=2C(C)=C1CCN1CCCC1 BDGZSZLSIHDPAV-UHFFFAOYSA-N 0.000 claims 1
- FXGAPEOCLPYRLZ-QGZVFWFLSA-N 4-[6-methyl-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=C(C)C=C2O1 FXGAPEOCLPYRLZ-QGZVFWFLSA-N 0.000 claims 1
- BYXKUYQJFGQCAP-OAHLLOKOSA-N 4-[7-fluoro-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC(F)=C2O1 BYXKUYQJFGQCAP-OAHLLOKOSA-N 0.000 claims 1
- UCACSHIPFQVVQO-QGZVFWFLSA-N 4-[7-methyl-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]benzonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C#N)=CC(C)=C2O1 UCACSHIPFQVVQO-QGZVFWFLSA-N 0.000 claims 1
- INSZNKUHAMEKSG-CYBMUJFWSA-N 4-chloro-1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3N=CC(Cl)=C3)=CC=C2O1 INSZNKUHAMEKSG-CYBMUJFWSA-N 0.000 claims 1
- YIPHOJHIPFCSCR-OAHLLOKOSA-N 4-methyl-1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3N=CC(C)=C3)=CC=C2O1 YIPHOJHIPFCSCR-OAHLLOKOSA-N 0.000 claims 1
- 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
- MFNYOZPLNSIUJC-GFCCVEGCSA-N 5-(chloromethyl)-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(CCl)ON=3)=CC=C2O1 MFNYOZPLNSIUJC-GFCCVEGCSA-N 0.000 claims 1
- NANUHNWKEYBEHX-MRXNPFEDSA-N 5-[(4-fluorophenyl)methyl]-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(CC=4C=CC(F)=CC=4)ON=3)=CC=C2O1 NANUHNWKEYBEHX-MRXNPFEDSA-N 0.000 claims 1
- YQDIQRGRAIXEQQ-QGZVFWFLSA-N 5-[(4-methoxyphenyl)methyl]-3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1CC1=NC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=NO1 YQDIQRGRAIXEQQ-QGZVFWFLSA-N 0.000 claims 1
- IOMVCVJIHYWSAZ-QGZVFWFLSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-2-phenyl-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3OC(=NC=3)C=3C=CC=CC=3)=CC=C2O1 IOMVCVJIHYWSAZ-QGZVFWFLSA-N 0.000 claims 1
- YEWLWFUNBISKSB-MRXNPFEDSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-2,3-dihydroinden-1-one Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=C4CCC(=O)C4=CC=3)C=C2O1 YEWLWFUNBISKSB-MRXNPFEDSA-N 0.000 claims 1
- QRGMOUYYLXHLMQ-QGZVFWFLSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]-2-phenyl-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3OC(=NC=3)C=3C=CC=CC=3)C=C2O1 QRGMOUYYLXHLMQ-QGZVFWFLSA-N 0.000 claims 1
- XFXXBRHYBCGVRI-CYBMUJFWSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]pyridazin-4-amine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C(=CN=NC=3)N)C=C2O1 XFXXBRHYBCGVRI-CYBMUJFWSA-N 0.000 claims 1
- NYFXYIXRYDZBHB-OAHLLOKOSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]pyridine-3-carbonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=C(C=NC=3)C#N)C=C2O1 NYFXYIXRYDZBHB-OAHLLOKOSA-N 0.000 claims 1
- DTODENPLUGFFKT-CQSZACIVSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-6-yl]pyrimidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=C(C=3C=NC=NC=3)C=C2O1 DTODENPLUGFFKT-CQSZACIVSA-N 0.000 claims 1
- RVMRTIPZWWTFGX-MRXNPFEDSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-2,3-dihydroinden-1-one Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=C4CCC(=O)C4=CC=3)=C2O1 RVMRTIPZWWTFGX-MRXNPFEDSA-N 0.000 claims 1
- GUQPBLQGZQRBNO-QGZVFWFLSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]-2-phenyl-1,3-oxazole Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3OC(=NC=3)C=3C=CC=CC=3)=C2O1 GUQPBLQGZQRBNO-QGZVFWFLSA-N 0.000 claims 1
- BZTGDBGFDDPDAB-CYBMUJFWSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]pyridazin-4-amine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C(=CN=NC=3)N)=C2O1 BZTGDBGFDDPDAB-CYBMUJFWSA-N 0.000 claims 1
- DWODDFBMWREQFA-OAHLLOKOSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]pyridine-3-carbonitrile Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=C(C=NC=3)C#N)=C2O1 DWODDFBMWREQFA-OAHLLOKOSA-N 0.000 claims 1
- FXGTUMDBWLCHJS-CQSZACIVSA-N 5-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-7-yl]pyrimidine Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC=CC(C=3C=NC=NC=3)=C2O1 FXGTUMDBWLCHJS-CQSZACIVSA-N 0.000 claims 1
- MRCBIQKULVRXDD-CYBMUJFWSA-N 5-ethyl-3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-1,2,4-oxadiazole Chemical compound O1C(CC)=NC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=N1 MRCBIQKULVRXDD-CYBMUJFWSA-N 0.000 claims 1
- JWXAEIFUNBARCI-GFCCVEGCSA-N 5-methyl-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(C)ON=3)=CC=C2O1 JWXAEIFUNBARCI-GFCCVEGCSA-N 0.000 claims 1
- 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 1
- 206010000891 Acute myocardial infarction Diseases 0.000 claims 1
- 206010001897 Alzheimer's disease Diseases 0.000 claims 1
- 208000006673 Asthma Diseases 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 206010003736 Attention deficit/hyperactivity disease Diseases 0.000 claims 1
- 206010004938 Bipolar disease Diseases 0.000 claims 1
- AGQLUSLUHUOAGQ-GOSISDBHSA-N CCON=C(C)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 Chemical compound CCON=C(C)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 AGQLUSLUHUOAGQ-GOSISDBHSA-N 0.000 claims 1
- CIXCYLNQQWNUBV-QGZVFWFLSA-N CON=C(C)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 Chemical compound CON=C(C)C1=CC=CC(C=2C=C3C=C(CCN4[C@@H](CCC4)C)OC3=CC=2)=C1 CIXCYLNQQWNUBV-QGZVFWFLSA-N 0.000 claims 1
- NDFTXWCJAJOUSX-LJQANCHMSA-N C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)=NOC(C)(C)C)=CC=C2O1 Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(C=CC=3)C(C)=NOC(C)(C)C)=CC=C2O1 NDFTXWCJAJOUSX-LJQANCHMSA-N 0.000 claims 1
- 206010009191 Circadian rhythm sleep disease Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 208000002173 Dizziness Diseases 0.000 claims 1
- 206010013654 Drug abuse Diseases 0.000 claims 1
- 206010015037 Epilepsy Diseases 0.000 claims 1
- 208000008665 Gastrointestinal Disease Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 1
- 206010025650 Malignant melanoma Diseases 0.000 claims 1
- 206010027175 Memory impairment Diseases 0.000 claims 1
- 206010027183 Meniere's disease Diseases 0.000 claims 1
- 206010027599 Migraine Diseases 0.000 claims 1
- 208000008085 Migraine Disorders Diseases 0.000 claims 1
- ZZXNMHSGRITGIL-QGZVFWFLSA-N N-(4-methoxyphenyl)-N-methyl-2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-amine Chemical compound C1=CC(OC)=CC=C1N(C)C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 ZZXNMHSGRITGIL-QGZVFWFLSA-N 0.000 claims 1
- 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
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims 1
- 208000008589 Obesity Diseases 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 206010061536 Parkinson's disease Diseases 0.000 claims 1
- 206010037175 Psychiatric disease Diseases 0.000 claims 1
- 206010039085 Rhinitis allergic Diseases 0.000 claims 1
- 206010040070 Septic shock Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000000323 Tourette Syndrome Diseases 0.000 claims 1
- 206010044126 Tourette's disease Diseases 0.000 claims 1
- BUUBCROLVQFZAY-MRXNPFEDSA-N [2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-(4-methylsulfanylphenyl)methanone Chemical compound C1=CC(SC)=CC=C1C(=O)C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 BUUBCROLVQFZAY-MRXNPFEDSA-N 0.000 claims 1
- PDVKXZUSXVGYMI-MRXNPFEDSA-N [2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]-phenylmethanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C=3C=CC=CC=3)=CC=C2O1 PDVKXZUSXVGYMI-MRXNPFEDSA-N 0.000 claims 1
- UDITUAWGQZPNSI-MRXNPFEDSA-N [3-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]methanol Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=C(CO)C=CC=3)=CC=C2O1 UDITUAWGQZPNSI-MRXNPFEDSA-N 0.000 claims 1
- ZQCABOOXQFMEIL-QGZVFWFLSA-N [4-(dimethylamino)phenyl]-[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)N(C)C)=CC=C2O1 ZQCABOOXQFMEIL-QGZVFWFLSA-N 0.000 claims 1
- BPKCXWNXUDTFIV-UHFFFAOYSA-N [4-[2-[2-(1H-azepin-2-yl)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(C=2C=C3C=C(CCC=4NC=CC=CC=4)OC3=CC=2)C=CC=1C(=O)N1CCOCC1 BPKCXWNXUDTFIV-UHFFFAOYSA-N 0.000 claims 1
- AWAROEZGWJEDHM-UHFFFAOYSA-N [4-[2-[2-(2-methylpiperidin-1-yl)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1CCCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 AWAROEZGWJEDHM-UHFFFAOYSA-N 0.000 claims 1
- NBGOTRKECBBASK-UHFFFAOYSA-N [4-[2-[2-(2-methylpyrrolidin-1-yl)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound CC1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 NBGOTRKECBBASK-UHFFFAOYSA-N 0.000 claims 1
- LPLQDVMVHQTAGL-UHFFFAOYSA-N [4-[2-[2-(3,6-dihydro-2H-pyridin-1-yl)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CC=CCC4)OC3=CC=2)C=CC=1C(=O)N1CCOCC1 LPLQDVMVHQTAGL-UHFFFAOYSA-N 0.000 claims 1
- PWTQSKSCUUEZIK-UHFFFAOYSA-N [4-[2-[2-(4-methylpiperidin-1-yl)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1CC(C)CCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 PWTQSKSCUUEZIK-UHFFFAOYSA-N 0.000 claims 1
- URZQWXKZZXBEAA-UHFFFAOYSA-N [4-[2-[2-(diethylamino)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(CC)CC)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 URZQWXKZZXBEAA-UHFFFAOYSA-N 0.000 claims 1
- RZTFZPKLYCKYCQ-UHFFFAOYSA-N [4-[2-[2-(dimethylamino)ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)C)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 RZTFZPKLYCKYCQ-UHFFFAOYSA-N 0.000 claims 1
- ZXYGRUFRRCHPAK-MRXNPFEDSA-N [4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]methanol Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(CO)=CC=3)=CC=C2O1 ZXYGRUFRRCHPAK-MRXNPFEDSA-N 0.000 claims 1
- BQAYROGJKLQKEO-WOJBJXKFSA-N [4-[2-[2-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C[C@@H]1CC[C@@H](C)N1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 BQAYROGJKLQKEO-WOJBJXKFSA-N 0.000 claims 1
- QOZSXRMOBARPHS-OYRHEFFESA-N [4-[2-[2-[(2S,6R)-2,6-dimethylpiperidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C[C@H]1CCC[C@@H](C)N1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 QOZSXRMOBARPHS-OYRHEFFESA-N 0.000 claims 1
- SCEIICQFBQDVDO-JOCHJYFZSA-N [4-[2-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C1[C@H](O)CCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 SCEIICQFBQDVDO-JOCHJYFZSA-N 0.000 claims 1
- KHVLJWYZILAGFW-UHFFFAOYSA-N [4-[2-[2-[ethyl(propan-2-yl)amino]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(CC)C(C)C)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 KHVLJWYZILAGFW-UHFFFAOYSA-N 0.000 claims 1
- UENGAGWCNSADCX-UHFFFAOYSA-N [4-[2-[2-[ethyl(propyl)amino]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(CC)CCC)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 UENGAGWCNSADCX-UHFFFAOYSA-N 0.000 claims 1
- VRPNNYHINXCZBS-UHFFFAOYSA-N [4-[2-[2-[methyl(2-methylpropyl)amino]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)CC(C)C)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 VRPNNYHINXCZBS-UHFFFAOYSA-N 0.000 claims 1
- ISURZDWFHMMOKT-UHFFFAOYSA-N [4-[2-[2-[methyl(propan-2-yl)amino]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)C(C)C)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 ISURZDWFHMMOKT-UHFFFAOYSA-N 0.000 claims 1
- SMFSOGWNQLKATH-UHFFFAOYSA-N [4-[2-[2-[tert-butyl(methyl)amino]ethyl]-1-benzofuran-5-yl]phenyl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)C(C)(C)C)=CC2=CC=1C(C=C1)=CC=C1C(=O)N1CCOCC1 SMFSOGWNQLKATH-UHFFFAOYSA-N 0.000 claims 1
- SHLLTDPYLXWHDN-CQSZACIVSA-N [5-(hydroxymethyl)-1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]imidazol-4-yl]methanol Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(N3C(=C(CO)N=C3)CO)=CC=C2O1 SHLLTDPYLXWHDN-CQSZACIVSA-N 0.000 claims 1
- CYIZTTVBRFBRAY-UHFFFAOYSA-N [6-[2-[2-(3-hydroxypropylamino)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCNCCCO)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 CYIZTTVBRFBRAY-UHFFFAOYSA-N 0.000 claims 1
- WICYEJWLHJNDAV-UHFFFAOYSA-N [6-[2-[2-(4-methylpiperidin-1-yl)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C1CC(C)CCN1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 WICYEJWLHJNDAV-UHFFFAOYSA-N 0.000 claims 1
- RPBNYUHYVUUVSR-UHFFFAOYSA-N [6-[2-[2-(azepan-1-yl)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CCCCCC4)OC3=CC=2)N=CC=1C(=O)N1CCOCC1 RPBNYUHYVUUVSR-UHFFFAOYSA-N 0.000 claims 1
- JQKTWMIOZFCFLY-UHFFFAOYSA-N [6-[2-[2-(dimethylamino)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)C)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 JQKTWMIOZFCFLY-UHFFFAOYSA-N 0.000 claims 1
- STRFUFNUDIMYMO-GOSISDBHSA-N [6-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 STRFUFNUDIMYMO-GOSISDBHSA-N 0.000 claims 1
- IAKBYDDHAFZACO-RTBURBONSA-N [6-[2-[2-[(2R,5R)-2,5-dimethylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C[C@@H]1CC[C@@H](C)N1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 IAKBYDDHAFZACO-RTBURBONSA-N 0.000 claims 1
- AVRVEOIQFGIKNN-QHCPKHFHSA-N [6-[2-[2-[(2S)-2-hydroxypyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound O[C@H]1CCCN1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 AVRVEOIQFGIKNN-QHCPKHFHSA-N 0.000 claims 1
- STRFUFNUDIMYMO-SFHVURJKSA-N [6-[2-[2-[(2S)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C[C@H]1CCCN1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 STRFUFNUDIMYMO-SFHVURJKSA-N 0.000 claims 1
- RGTJDTJZMPHCGP-BGYRXZFFSA-N [6-[2-[2-[(2S,6R)-2,6-dimethylpiperidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C[C@H]1CCC[C@@H](C)N1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 RGTJDTJZMPHCGP-BGYRXZFFSA-N 0.000 claims 1
- OPORWMPRRDKQPR-HXUWFJFHSA-N [6-[2-[2-[(3R)-3-hydroxypyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C1[C@H](O)CCN1CCC1=CC2=CC(C=3N=CC(=CC=3)C(=O)N3CCOCC3)=CC=C2O1 OPORWMPRRDKQPR-HXUWFJFHSA-N 0.000 claims 1
- FZCQHAIQSBJAMI-UHFFFAOYSA-N [6-[2-[2-[ethyl(propan-2-yl)amino]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(CC)C(C)C)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 FZCQHAIQSBJAMI-UHFFFAOYSA-N 0.000 claims 1
- ZSMNJIVXBWEGNQ-UHFFFAOYSA-N [6-[2-[2-[ethyl(propyl)amino]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(CC)CCC)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 ZSMNJIVXBWEGNQ-UHFFFAOYSA-N 0.000 claims 1
- JYOBHRHELSIQRG-UHFFFAOYSA-N [6-[2-[2-[methyl(2-methylpropyl)amino]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)CC(C)C)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 JYOBHRHELSIQRG-UHFFFAOYSA-N 0.000 claims 1
- AIIZUZNYRFOOEZ-UHFFFAOYSA-N [6-[2-[2-[methyl(propan-2-yl)amino]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)C(C)C)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 AIIZUZNYRFOOEZ-UHFFFAOYSA-N 0.000 claims 1
- JPMLKJHXENVRNP-UHFFFAOYSA-N [6-[2-[2-[tert-butyl(methyl)amino]ethyl]-1-benzofuran-5-yl]pyridin-3-yl]-morpholin-4-ylmethanone Chemical compound C=1C=C2OC(CCN(C)C(C)(C)C)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 JPMLKJHXENVRNP-UHFFFAOYSA-N 0.000 claims 1
- 201000010105 allergic rhinitis Diseases 0.000 claims 1
- 230000037007 arousal Effects 0.000 claims 1
- 125000003710 aryl alkyl group Chemical group 0.000 claims 1
- 201000006287 attention deficit hyperactivity disease Diseases 0.000 claims 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 201000009030 carcinoma Diseases 0.000 claims 1
- 230000037410 cognitive enhancement Effects 0.000 claims 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 1
- BGHFRTUKSRZCQR-CYBMUJFWSA-N cyclopropyl-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C(=O)C3CC3)=CC=C2O1 BGHFRTUKSRZCQR-CYBMUJFWSA-N 0.000 claims 1
- BQTMIBGMCRVQPU-QGZVFWFLSA-N cyclopropyl-[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)C3CC3)=CC=C2O1 BQTMIBGMCRVQPU-QGZVFWFLSA-N 0.000 claims 1
- POAWKGPFNHDXRG-QGZVFWFLSA-N cyclopropyl-[4-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]phenyl]methanone Chemical compound C[C@@H]1CCCN1CCC1=CC2=CC(C=3C=CC(=CC=3)C(=O)C3CC3)=CC=C2O1 POAWKGPFNHDXRG-QGZVFWFLSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- CAMHJTUNMMWJCB-OAHLLOKOSA-N ethyl 1-[2-[2-[(2R)-2-methylpyrrolidin-1-yl]ethyl]-1-benzofuran-5-yl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OCC)C=NN1C1=CC=C(OC(CCN2[C@@H](CCC2)C)=C2)C2=C1 CAMHJTUNMMWJCB-OAHLLOKOSA-N 0.000 claims 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Substances C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- 125000003588 lysine group Chemical group [H]N([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
- 208000009018 medullary Thyroid cancer Diseases 0.000 claims 1
- 201000001441 melanoma Diseases 0.000 claims 1
- LPGWMTZIZATUKM-UHFFFAOYSA-N methyl 4-[2-[2-(2-methylpyrrolidin-1-yl)ethyl]-1-benzofuran-5-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC(CCN2C(CCC2)C)=C2)C2=C1 LPGWMTZIZATUKM-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 230000036651 mood Effects 0.000 claims 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims 1
- XTRCLTAVBBHIAR-UHFFFAOYSA-N morpholin-4-yl-[4-[2-(2-piperidin-1-ylethyl)-1-benzofuran-5-yl]phenyl]methanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CCCCC4)OC3=CC=2)C=CC=1C(=O)N1CCOCC1 XTRCLTAVBBHIAR-UHFFFAOYSA-N 0.000 claims 1
- YKVQQYCLIBHWNP-UHFFFAOYSA-N morpholin-4-yl-[6-[2-(2-morpholin-4-ylethyl)-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CCOCC4)OC3=CC=2)N=CC=1C(=O)N1CCOCC1 YKVQQYCLIBHWNP-UHFFFAOYSA-N 0.000 claims 1
- XNUIRGHKJISNSI-UHFFFAOYSA-N morpholin-4-yl-[6-[2-(2-piperidin-1-ylethyl)-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CCCCC4)OC3=CC=2)N=CC=1C(=O)N1CCOCC1 XNUIRGHKJISNSI-UHFFFAOYSA-N 0.000 claims 1
- RRLCACGGDHPKNQ-UHFFFAOYSA-N morpholin-4-yl-[6-[2-(2-pyrrolidin-1-ylethyl)-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C(C=2C=C3C=C(CCN4CCCC4)OC3=CC=2)N=CC=1C(=O)N1CCOCC1 RRLCACGGDHPKNQ-UHFFFAOYSA-N 0.000 claims 1
- 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
- WFRCRYDOGIICLA-UHFFFAOYSA-N morpholin-4-yl-[6-[2-[2-(prop-2-enylamino)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C2OC(CCNCC=C)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 WFRCRYDOGIICLA-UHFFFAOYSA-N 0.000 claims 1
- QSGSWTUMLIKXLT-UHFFFAOYSA-N morpholin-4-yl-[6-[2-[2-(propylamino)ethyl]-1-benzofuran-5-yl]pyridin-3-yl]methanone Chemical compound C=1C=C2OC(CCNCCC)=CC2=CC=1C(N=C1)=CC=C1C(=O)N1CCOCC1 QSGSWTUMLIKXLT-UHFFFAOYSA-N 0.000 claims 1
- 201000003152 motion sickness Diseases 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- 201000008430 obsessive-compulsive disease Diseases 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 201000005204 thyroid medullary carcinoma Diseases 0.000 claims 1
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005500986A JP2005500986A (ja) | 2005-01-13 |
| JP2005500986A5 true JP2005500986A5 (US06653308-20031125-C00057.png) | 2005-12-22 |
| JP4612990B2 JP4612990B2 (ja) | 2011-01-12 |
Family
ID=27366495
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2002573767A Expired - Fee Related JP4612990B2 (ja) | 2001-03-16 | 2002-03-11 | ヒスタミン−３受容体リガンドとしての新規アミンおよびそれらの治療的適用 |
Country Status (7)
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| PL376751A1 (pl) * | 2002-11-12 | 2006-01-09 | Abbott Laboratories | Bicykliczne podstawione aminy jako ligandy receptora histaminowego-3 |
| US7244852B2 (en) | 2003-02-27 | 2007-07-17 | Abbott Laboratories | Process for preparing 2-methylpyrrolidine and specific enantiomers thereof |
| CN101928284A (zh) | 2003-03-14 | 2010-12-29 | 小野药品工业株式会社 | 含氮杂环衍生物以及包含所述化合物作为活性成分的药物 |
| CA2521000A1 (en) * | 2003-04-03 | 2004-10-21 | Kyowa Hakko Kogyo Co., Ltd. | Preventive and/or therapeutic agent for neuropathic pain |
| US7094790B2 (en) | 2003-05-07 | 2006-08-22 | Abbott Laboratories | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| US20040224952A1 (en) * | 2003-05-07 | 2004-11-11 | Cowart Marlon D. | Fused bicyclic-substituted amines as histamine-3 receptor ligands |
| CA2524787A1 (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 |
| SE0303480D0 (sv) * | 2003-12-19 | 2003-12-19 | Biovitrum Ab | Benzofuranes |
| AU2005219791B2 (en) * | 2004-03-05 | 2011-06-09 | Msd K.K. | Diaryl-substituted five-membered heterocycle derivative |
| WO2005097127A2 (en) | 2004-04-02 | 2005-10-20 | Merck & Co., Inc. | Method of treating men with metabolic and anthropometric disorders |
| US7098222B2 (en) | 2004-05-12 | 2006-08-29 | Abbott Laboratories | 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 |
| 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 |
| 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 |
| CA2610655A1 (en) | 2005-06-03 | 2006-12-14 | Abbott Laboratories | Cyclobutyl amine derivatives |
| US8003642B2 (en) | 2006-03-10 | 2011-08-23 | Ono Pharmaceutical Co., Ltd. | Nitrogenated heterocyclic derivative, and pharmaceutical agent comprising the derivative as active ingredient |
| WO2007149395A2 (en) * | 2006-06-20 | 2007-12-27 | Amphora Discovery Corporation | 2,5-substituted oxazole derivatives as protein kinase inhibitors for the treatment of cancer |
| US9108948B2 (en) | 2006-06-23 | 2015-08-18 | Abbvie Inc. | Cyclopropyl amine derivatives |
| CN103382174A (zh) | 2006-06-23 | 2013-11-06 | 雅培制药有限公司 | 作为组胺h3受体调节物的环丙胺衍生物 |
| EP2221298B1 (en) | 2007-11-13 | 2013-11-06 | Taisho Pharmaceutical Co., Ltd | Phenylpyrazole derivatives |
| US8383657B2 (en) | 2007-12-21 | 2013-02-26 | Abbott Laboratories | Thiazolylidine urea and amide derivatives and methods of use thereof |
| EP2344484B1 (en) * | 2008-10-17 | 2016-06-08 | Akaal Pharma Pty Ltd | S1p receptors modulators and use thereof |
| EP2344446A4 (en) | 2008-10-17 | 2012-04-04 | Akaal Pharma Pty Ltd | S1P RECEPTOR 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 |
| EP3309150B1 (en) * | 2013-01-09 | 2021-06-02 | Arena Pharmaceuticals, Inc. | (r)-3-(4'-(2-(2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)propanoic acid as histamine h3 receptor modulators for the treatment of cognitive disorders |
| EP3236964A4 (en) * | 2014-12-22 | 2018-09-19 | Teva Pharmaceuticals International GmbH | L-tartrate salt of pridopidine |
| 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 |
| EP4251148A1 (en) | 2020-11-27 | 2023-10-04 | 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 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| US6130187A (en) * | 1996-02-09 | 2000-10-10 | Kumiai Chemical Industry Co., Ltd. | Benzofuran-7-yl uracil derivatives and herbicides |
| US6077812A (en) * | 1997-02-26 | 2000-06-20 | Fmc Corporation | Cycloimido-substituted benzofused heterocyclic herbicides |
| WO1998052946A1 (en) * | 1997-12-02 | 1998-11-26 | Dr. Reddy's Research Foundation | Azolidinediones useful for the treatment of diabetes, dyslipidemia and hypertension |
| EP0982300A3 (en) * | 1998-07-29 | 2000-03-08 | Societe Civile Bioprojet | Non-imidazole alkylamines as histamine H3 - receptor ligands and their therapeutic applications |
| 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 |
| WO2002010156A1 (en) * | 2000-07-29 | 2002-02-07 | Arpida Ag | Benzofuran derivatives and their use as antibacterial agents |
-
2002
- 2002-03-11 BR BR0205829-4A patent/BR0205829A/pt not_active IP Right Cessation
- 2002-03-11 JP JP2002573767A patent/JP4612990B2/ja not_active Expired - Fee Related
- 2002-03-11 EP EP02715079A patent/EP1370546A2/en not_active Withdrawn
- 2002-03-11 WO PCT/US2002/007107 patent/WO2002074758A2/en active Application Filing
- 2002-03-11 MX MXPA03008319A patent/MXPA03008319A/es active IP Right Grant
- 2002-03-11 EP EP10180385A patent/EP2258694A1/en not_active Withdrawn
- 2002-03-11 CA CA2440238A patent/CA2440238C/en not_active Expired - Fee Related
- 2002-03-15 AR ARP020100947A patent/AR035783A1/es unknown
