JP2010509402A5 - - Google Patents
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- Publication number
- JP2010509402A5 JP2010509402A5 JP2009537305A JP2009537305A JP2010509402A5 JP 2010509402 A5 JP2010509402 A5 JP 2010509402A5 JP 2009537305 A JP2009537305 A JP 2009537305A JP 2009537305 A JP2009537305 A JP 2009537305A JP 2010509402 A5 JP2010509402 A5 JP 2010509402A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- methyl
- amino
- methanone
- thiophen
- 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.)
- Withdrawn
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- 150000001875 compounds Chemical class 0.000 claims description 28
- FHMKBGPASICGMG-UHFFFAOYSA-N [2-amino-4-[[4-(3-fluorophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=C(F)C=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 FHMKBGPASICGMG-UHFFFAOYSA-N 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 32
- 239000001257 hydrogen Substances 0.000 claims 32
- 150000002431 hydrogen Chemical class 0.000 claims 26
- 150000003839 salts Chemical class 0.000 claims 23
- 125000003118 aryl group Chemical group 0.000 claims 14
- 125000003107 substituted aryl group Chemical group 0.000 claims 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims 13
- 229910052736 halogen Inorganic materials 0.000 claims 13
- 150000002367 halogens Chemical class 0.000 claims 13
- 125000000217 alkyl group Chemical group 0.000 claims 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims 9
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 9
- 125000004432 carbon atom Chemical group C* 0.000 claims 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 6
- 125000002252 acyl group Chemical group 0.000 claims 6
- 125000004475 heteroaralkyl group Chemical group 0.000 claims 6
- 125000001072 heteroaryl group Chemical group 0.000 claims 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 5
- 229910052760 oxygen Inorganic materials 0.000 claims 5
- 239000001301 oxygen Substances 0.000 claims 5
- 239000008194 pharmaceutical composition Substances 0.000 claims 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 4
- 150000001721 carbon Chemical group 0.000 claims 4
- 208000019622 heart disease Diseases 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 3
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 3
- 101150007969 ADORA1 gene Proteins 0.000 claims 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- MLBNYNHTFZBWOO-UHFFFAOYSA-N [2-amino-4-[(4-cyclopentylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1CCCC1 MLBNYNHTFZBWOO-UHFFFAOYSA-N 0.000 claims 2
- WBVSHKCZLDSJBP-UHFFFAOYSA-N [2-amino-4-[(4-phenylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=C1 WBVSHKCZLDSJBP-UHFFFAOYSA-N 0.000 claims 2
- WTJJQPAIMDOFHJ-UHFFFAOYSA-N [2-amino-4-[[4-(4-chlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(Cl)C=C1 WTJJQPAIMDOFHJ-UHFFFAOYSA-N 0.000 claims 2
- PIGHLLPGQFTIDD-UHFFFAOYSA-N [2-amino-4-[[4-[4-(trifluoromethyl)phenyl]piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(C(F)(F)F)C=C1 PIGHLLPGQFTIDD-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- WGSAKPFHJLTQFG-UHFFFAOYSA-N 1-[4-[[5-amino-4-(4-chlorobenzoyl)thiophen-3-yl]methyl]piperazin-1-yl]-2-(4-chlorophenyl)ethanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C(=O)CC1=CC=C(Cl)C=C1 WGSAKPFHJLTQFG-UHFFFAOYSA-N 0.000 claims 1
- BTURCFCECILJTE-UHFFFAOYSA-N 2-[4-[[5-amino-4-(4-chlorobenzoyl)thiophen-3-yl]methyl]piperazin-1-yl]-1-(4-chlorophenyl)ethanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CC(=O)C1=CC=C(Cl)C=C1 BTURCFCECILJTE-UHFFFAOYSA-N 0.000 claims 1
- 125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
- ITIPXEQVFANBBI-UHFFFAOYSA-N 4-[4-[[5-amino-4-(4-chlorobenzoyl)-2-methylthiophen-3-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound C1CN(C=2C=CC(=CC=2)C#N)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 ITIPXEQVFANBBI-UHFFFAOYSA-N 0.000 claims 1
- GBEKMUYDTMZKOO-UHFFFAOYSA-N 4-[4-[[5-amino-4-(4-chlorobenzoyl)thiophen-3-yl]methyl]piperazin-1-yl]benzonitrile Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(C#N)C=C1 GBEKMUYDTMZKOO-UHFFFAOYSA-N 0.000 claims 1
- 206010002383 Angina Pectoris Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000025966 Neurological disease Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000027418 Wounds and injury Diseases 0.000 claims 1
- LGTDDJCWKVBENO-UHFFFAOYSA-N [2-amino-4-(spiro[1,3-benzodioxole-2,4'-piperidine]-1'-ylmethyl)thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound NC=1SC=C(CN2CCC3(CC2)OC2=CC=CC=C2O3)C=1C(=O)C1=CC=C(Cl)C=C1 LGTDDJCWKVBENO-UHFFFAOYSA-N 0.000 claims 1
- HYXHXEHHOZDASV-UHFFFAOYSA-N [2-amino-4-[(4-benzylpiperazin-1-yl)methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(CC=2C=CC=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 HYXHXEHHOZDASV-UHFFFAOYSA-N 0.000 claims 1
- VLUIIUMESZDQJJ-UHFFFAOYSA-N [2-amino-4-[(4-benzylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1CC1=CC=CC=C1 VLUIIUMESZDQJJ-UHFFFAOYSA-N 0.000 claims 1
- PNTFMBLZDHRWEH-UHFFFAOYSA-N [2-amino-4-[(4-cyclohexylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1CCCCC1 PNTFMBLZDHRWEH-UHFFFAOYSA-N 0.000 claims 1
- GZDAZWLRSGSJFO-UHFFFAOYSA-N [2-amino-4-[(4-cyclooctylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1CCCCCCC1 GZDAZWLRSGSJFO-UHFFFAOYSA-N 0.000 claims 1
- UUYUBKMEGGSUJJ-UHFFFAOYSA-N [2-amino-4-[(4-fluorospiro[1,3-benzodioxole-2,4'-piperidine]-1'-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound NC=1SC=C(CN2CCC3(CC2)OC2=C(F)C=CC=C2O3)C=1C(=O)C1=CC=C(Cl)C=C1 UUYUBKMEGGSUJJ-UHFFFAOYSA-N 0.000 claims 1
- FBLJFWZLJFATLC-UHFFFAOYSA-N [2-amino-4-[(4-methylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C)CCN1CC1=CSC(N)=C1C(=O)C1=CC=C(Cl)C=C1 FBLJFWZLJFATLC-UHFFFAOYSA-N 0.000 claims 1
- FVCNDFNVEXZHJO-UHFFFAOYSA-N [2-amino-4-[(4-methylspiro[1,3-benzodioxole-2,4'-piperidine]-1'-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound O1C=2C(C)=CC=CC=2OC1(CC1)CCN1CC1=CSC(N)=C1C(=O)C1=CC=C(Cl)C=C1 FVCNDFNVEXZHJO-UHFFFAOYSA-N 0.000 claims 1
- RITYNZBWVKWGFS-UHFFFAOYSA-N [2-amino-4-[(4-naphthalen-1-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound NC=1SC=C(CN2CCN(CC2)C=2C3=CC=CC=C3C=CC=2)C=1C(=O)C1=CC=C(Cl)C=C1 RITYNZBWVKWGFS-UHFFFAOYSA-N 0.000 claims 1
- ZTWZRYZHIXOGES-UHFFFAOYSA-N [2-amino-4-[(4-propan-2-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C(C)C)CCN1CC1=CSC(N)=C1C(=O)C1=CC=C(Cl)C=C1 ZTWZRYZHIXOGES-UHFFFAOYSA-N 0.000 claims 1
- LRNXGDCNTQAXDV-UHFFFAOYSA-N [2-amino-4-[(4-pyridin-2-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=N1 LRNXGDCNTQAXDV-UHFFFAOYSA-N 0.000 claims 1
- JKXQLDDFLKSYTM-UHFFFAOYSA-N [2-amino-4-[(4-pyridin-3-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CN=C1 JKXQLDDFLKSYTM-UHFFFAOYSA-N 0.000 claims 1
- PTDILEGANSBTSE-UHFFFAOYSA-N [2-amino-4-[(4-pyridin-4-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=NC=C1 PTDILEGANSBTSE-UHFFFAOYSA-N 0.000 claims 1
- FJHGONQMXVSBES-UHFFFAOYSA-N [2-amino-4-[(4-pyrimidin-2-ylpiperazin-1-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=NC=CC=N1 FJHGONQMXVSBES-UHFFFAOYSA-N 0.000 claims 1
- VGTGXMREKQFXNQ-UHFFFAOYSA-N [2-amino-4-[(5-methylspiro[1,3-benzodioxole-2,4'-piperidine]-1'-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound O1C2=CC(C)=CC=C2OC1(CC1)CCN1CC1=CSC(N)=C1C(=O)C1=CC=C(Cl)C=C1 VGTGXMREKQFXNQ-UHFFFAOYSA-N 0.000 claims 1
- LXZNFZIWNXAXPF-UHFFFAOYSA-N [2-amino-4-[(5-tert-butylspiro[1,3-benzodioxole-2,4'-piperidine]-1'-yl)methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound O1C2=CC(C(C)(C)C)=CC=C2OC1(CC1)CCN1CC1=CSC(N)=C1C(=O)C1=CC=C(Cl)C=C1 LXZNFZIWNXAXPF-UHFFFAOYSA-N 0.000 claims 1
- BKVQQVAZXXNRAL-UHFFFAOYSA-N [2-amino-4-[[2-(4-chlorophenyl)-2,5-diazabicyclo[2.2.1]heptan-5-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN1CC2CC1CN2C1=CC=C(Cl)C=C1 BKVQQVAZXXNRAL-UHFFFAOYSA-N 0.000 claims 1
- XEJIHQOMTYJWCT-UHFFFAOYSA-N [2-amino-4-[[2-(4-chlorophenyl)-2,7-diazaspiro[4.4]nonan-7-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(C1)CCC1(C1)CCN1C1=CC=C(Cl)C=C1 XEJIHQOMTYJWCT-UHFFFAOYSA-N 0.000 claims 1
- VETJLOKKGTWBFO-UHFFFAOYSA-N [2-amino-4-[[4-(1,3-benzodioxol-5-yl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound NC=1SC=C(CN2CCN(CC2)C=2C=C3OCOC3=CC=2)C=1C(=O)C1=CC=C(Cl)C=C1 VETJLOKKGTWBFO-UHFFFAOYSA-N 0.000 claims 1
- BRWGCTMCYZVICL-UHFFFAOYSA-N [2-amino-4-[[4-(2,3-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(Cl)=C1Cl BRWGCTMCYZVICL-UHFFFAOYSA-N 0.000 claims 1
- SKVYUUPKEQJOOR-UHFFFAOYSA-N [2-amino-4-[[4-(2,3-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(F)=C1F SKVYUUPKEQJOOR-UHFFFAOYSA-N 0.000 claims 1
- QLXKABIMWDIRKB-UHFFFAOYSA-N [2-amino-4-[[4-(2,4,6-trifluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(F)C=C(F)C=C1F QLXKABIMWDIRKB-UHFFFAOYSA-N 0.000 claims 1
- RLQCJMVZVOGKBW-UHFFFAOYSA-N [2-amino-4-[[4-(2,4-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(Cl)C=C1Cl RLQCJMVZVOGKBW-UHFFFAOYSA-N 0.000 claims 1
- VUSWZWCZLQPKBC-UHFFFAOYSA-N [2-amino-4-[[4-(2,4-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(F)C=C1F VUSWZWCZLQPKBC-UHFFFAOYSA-N 0.000 claims 1
- RRXKFDQOOZHJTF-UHFFFAOYSA-N [2-amino-4-[[4-(2,5-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(Cl)=CC=C1Cl RRXKFDQOOZHJTF-UHFFFAOYSA-N 0.000 claims 1
- DXGZCDTWBDRRKI-UHFFFAOYSA-N [2-amino-4-[[4-(2,5-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(F)=CC=C1F DXGZCDTWBDRRKI-UHFFFAOYSA-N 0.000 claims 1
- BHNZEYVIYRIQCZ-UHFFFAOYSA-N [2-amino-4-[[4-(2,6-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(Cl)C=CC=C1Cl BHNZEYVIYRIQCZ-UHFFFAOYSA-N 0.000 claims 1
- DHAUTGJWCQUFII-UHFFFAOYSA-N [2-amino-4-[[4-(2,6-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(F)C=CC=C1F DHAUTGJWCQUFII-UHFFFAOYSA-N 0.000 claims 1
- HDQFEKGOVIJERJ-UHFFFAOYSA-N [2-amino-4-[[4-(2,6-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-[3-(trifluoromethyl)phenyl]methanone Chemical compound C=1C=CC(C(F)(F)F)=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=C(F)C=CC=C1F HDQFEKGOVIJERJ-UHFFFAOYSA-N 0.000 claims 1
- FJERGVLETHXCBK-UHFFFAOYSA-N [2-amino-4-[[4-(2-chloro-4-fluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(F)C=C1Cl FJERGVLETHXCBK-UHFFFAOYSA-N 0.000 claims 1
- ZGNUUPGCNLNRGC-UHFFFAOYSA-N [2-amino-4-[[4-(2-chlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=C1Cl ZGNUUPGCNLNRGC-UHFFFAOYSA-N 0.000 claims 1
- KFWAXNAVBQKIAZ-UHFFFAOYSA-N [2-amino-4-[[4-(2-fluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC=C1F KFWAXNAVBQKIAZ-UHFFFAOYSA-N 0.000 claims 1
- NQOCPHPCHPECPX-UHFFFAOYSA-N [2-amino-4-[[4-(3,4-dichlorophenyl)piperazin-1-yl]methyl]-5-methylthiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C1CN(C=2C=C(Cl)C(Cl)=CC=2)CCN1CC1=C(C)SC(N)=C1C(=O)C1=CC=C(Cl)C=C1 NQOCPHPCHPECPX-UHFFFAOYSA-N 0.000 claims 1
- HZIBFSCCTZORDE-UHFFFAOYSA-N [2-amino-4-[[4-(3,4-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(Cl)C(Cl)=C1 HZIBFSCCTZORDE-UHFFFAOYSA-N 0.000 claims 1
- RQMCCXLNHOFIBT-UHFFFAOYSA-N [2-amino-4-[[4-(3,4-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(F)C(F)=C1 RQMCCXLNHOFIBT-UHFFFAOYSA-N 0.000 claims 1
- ACGNVIYHWCNNLW-UHFFFAOYSA-N [2-amino-4-[[4-(3,5-dichlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(Cl)=CC(Cl)=C1 ACGNVIYHWCNNLW-UHFFFAOYSA-N 0.000 claims 1
- UFSBQTGZKIHMDQ-UHFFFAOYSA-N [2-amino-4-[[4-(3,5-difluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC(F)=CC(F)=C1 UFSBQTGZKIHMDQ-UHFFFAOYSA-N 0.000 claims 1
- KFWLBGALSCQPIL-UHFFFAOYSA-N [2-amino-4-[[4-(3-chloro-4-fluorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=C(F)C(Cl)=C1 KFWLBGALSCQPIL-UHFFFAOYSA-N 0.000 claims 1
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- NDWVFXKAKMRXDA-UHFFFAOYSA-N [2-amino-4-[[4-(3-chlorophenyl)piperazin-1-yl]methyl]thiophen-3-yl]-(4-chlorophenyl)methanone Chemical compound C=1C=C(Cl)C=CC=1C(=O)C1=C(N)SC=C1CN(CC1)CCN1C1=CC=CC(Cl)=C1 NDWVFXKAKMRXDA-UHFFFAOYSA-N 0.000 claims 1
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|---|---|---|---|
| US85850506P | 2006-11-13 | 2006-11-13 | |
| US11/938,465 US7855209B2 (en) | 2006-11-13 | 2007-11-12 | Allosteric modulators of the A1 adenosine receptor |
| US11/938,514 US7897596B2 (en) | 2006-11-13 | 2007-11-12 | Allosteric modulators of the A1 adenosine receptor |
| PCT/US2007/084490 WO2008063984A2 (en) | 2006-11-13 | 2007-11-13 | Allosteric modulators of the a1 adenosine receptor |
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| JP2010509402A JP2010509402A (ja) | 2010-03-25 |
| JP2010509402A5 true JP2010509402A5 (enExample) | 2011-01-06 |
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| JP (1) | JP2010509402A (enExample) |
| KR (1) | KR20090112627A (enExample) |
| AU (1) | AU2007323888A1 (enExample) |
| BR (1) | BRPI0718520A2 (enExample) |
| CA (1) | CA2669447A1 (enExample) |
| IL (1) | IL198402A0 (enExample) |
| MX (1) | MX2009004763A (enExample) |
| WO (1) | WO2008063984A2 (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103739588B (zh) * | 2014-01-04 | 2015-07-01 | 新发药业有限公司 | 一种2-氨基噻吩衍生物的简便合成方法 |
| US10434099B2 (en) | 2016-09-22 | 2019-10-08 | The National Institute for Biotechnology in the Negev Ltd. | Methods for treating central nervous system disorders using VDAC inhibitors |
| ES2815539T3 (es) * | 2015-09-14 | 2021-03-30 | Nat Inst Biotechnology Negev Ltd | Nuevos derivados de piperazina y piperidina, síntesis y uso de los mismos en la inhibición de la oligomerización de VDAC, la apoptosis y la disfunción mitocondrial |
| US10787423B2 (en) | 2015-09-14 | 2020-09-29 | The National Institute For Biotechnolgy In The Negev Ltd. | Piperazine and piperidine derivatives, their synthesis and use thereof in inhibiting VDAC oligomerization, apoptosis and mitochondria dysfunction |
| US11220505B2 (en) * | 2017-03-21 | 2022-01-11 | Temple University-Of The Commonwealth System Of Higher Education | 5-hydroxytryptamine receptor 7 modulators and their use as therapeutic agents |
| JP7365237B2 (ja) * | 2017-03-21 | 2023-10-19 | テンプル・ユニバーシティ－オブ・ザ・コモンウェルス・システム・オブ・ハイアー・エデュケイション | シグマ－２受容体の新規調節物質およびその使用方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| US5332732A (en) * | 1992-09-11 | 1994-07-26 | Mcneilab, Inc. | Thiophene and pyridine antipsychotic agents |
| EP0595150B1 (de) * | 1992-10-29 | 1996-07-31 | Hoechst Aktiengesellschaft | Verfahren zur Herstellung von aromatischen Brommethyl-Verbindungen |
| US5939432A (en) * | 1997-10-29 | 1999-08-17 | Medco Research, Inc. | Thiophenes useful for modulating the adenosine receptor |
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2007
- 2007-11-13 EP EP07864306A patent/EP2081575A4/en not_active Withdrawn
- 2007-11-13 KR KR1020097009765A patent/KR20090112627A/ko not_active Withdrawn
- 2007-11-13 CA CA002669447A patent/CA2669447A1/en not_active Abandoned
- 2007-11-13 MX MX2009004763A patent/MX2009004763A/es not_active Application Discontinuation
- 2007-11-13 AU AU2007323888A patent/AU2007323888A1/en not_active Abandoned
- 2007-11-13 BR BRPI0718520-0A patent/BRPI0718520A2/pt not_active IP Right Cessation
- 2007-11-13 WO PCT/US2007/084490 patent/WO2008063984A2/en not_active Ceased
- 2007-11-13 JP JP2009537305A patent/JP2010509402A/ja not_active Withdrawn
-
2009
- 2009-04-26 IL IL198402A patent/IL198402A0/en unknown
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