JP2009542661A5 - - Google Patents
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- Publication number
- JP2009542661A5 JP2009542661A5 JP2009518233A JP2009518233A JP2009542661A5 JP 2009542661 A5 JP2009542661 A5 JP 2009542661A5 JP 2009518233 A JP2009518233 A JP 2009518233A JP 2009518233 A JP2009518233 A JP 2009518233A JP 2009542661 A5 JP2009542661 A5 JP 2009542661A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- phenyl
- acetic acid
- alkyl
- piperazin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 125000000217 alkyl group Chemical group 0.000 claims 59
- 150000001875 compounds Chemical class 0.000 claims 46
- -1 di-substituted amino Chemical group 0.000 claims 41
- 229910052739 hydrogen Inorganic materials 0.000 claims 41
- 239000001257 hydrogen Substances 0.000 claims 41
- 125000003545 alkoxy group Chemical group 0.000 claims 32
- 125000001188 haloalkyl group Chemical group 0.000 claims 28
- 125000004438 haloalkoxy group Chemical group 0.000 claims 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 26
- 125000000753 cycloalkyl group Chemical group 0.000 claims 24
- 125000005843 halogen group Chemical group 0.000 claims 23
- 150000002431 hydrogen Chemical class 0.000 claims 22
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 22
- 125000003118 aryl group Chemical group 0.000 claims 20
- 125000001072 heteroaryl group Chemical group 0.000 claims 20
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims 15
- 125000004453 alkoxycarbonyl group Chemical class 0.000 claims 14
- 125000004414 alkyl thio group Chemical group 0.000 claims 14
- 125000000623 heterocyclic group Chemical group 0.000 claims 13
- 125000004442 acylamino group Chemical group 0.000 claims 12
- 125000004183 alkoxy alkyl group Chemical class 0.000 claims 12
- 125000005083 alkoxyalkoxy group Chemical class 0.000 claims 12
- 125000002431 aminoalkoxy group Chemical class 0.000 claims 12
- 125000004397 aminosulfonyl group Chemical class NS(=O)(=O)* 0.000 claims 12
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 claims 12
- 125000005113 hydroxyalkoxy group Chemical class 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 12
- 125000002252 acyl group Chemical class 0.000 claims 11
- 125000002947 alkylene group Chemical group 0.000 claims 11
- 125000004103 aminoalkyl group Chemical class 0.000 claims 11
- 125000002768 hydroxyalkyl group Chemical class 0.000 claims 11
- 229910052799 carbon Inorganic materials 0.000 claims 10
- 125000001153 fluoro group Chemical group F* 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 125000003917 carbamoyl group Chemical class [H]N([H])C(*)=O 0.000 claims 9
- 125000003709 fluoroalkyl group Chemical group 0.000 claims 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 8
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
- 125000004193 piperazinyl group Chemical group 0.000 claims 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 5
- 150000001721 carbon Chemical group 0.000 claims 5
- 125000004432 carbon atom Chemical group C* 0.000 claims 5
- 125000004428 fluoroalkoxy group Chemical group 0.000 claims 5
- MDLQJNCGZVDZFV-LJQANCHMSA-N 2-[4-[(r)-phenyl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1[C@@H](C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 MDLQJNCGZVDZFV-LJQANCHMSA-N 0.000 claims 4
- 125000002723 alicyclic group Chemical group 0.000 claims 4
- 125000004429 atom Chemical group 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 4
- 125000003003 spiro group Chemical group 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 3
- VGNWGNMSURARCW-DYESRHJHSA-N 2-[(2r)-2-methyl-4-[(r)-(3-methylphenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(C)C=CC=1)C1=CC=CC=C1 VGNWGNMSURARCW-DYESRHJHSA-N 0.000 claims 2
- BHYTUTVYZHKTTJ-MTATWXBHSA-N 2-[(2r)-4-[cyclopropyl-[3-(trifluoromethyl)phenyl]methyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(C=CC=1)C(F)(F)F)C1CC1 BHYTUTVYZHKTTJ-MTATWXBHSA-N 0.000 claims 2
- PLDUPXSUYLZYBN-UHFFFAOYSA-N Fluphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2SC2=CC=CC=C21 PLDUPXSUYLZYBN-UHFFFAOYSA-N 0.000 claims 2
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 2
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 2
- 102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 claims 2
- 101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 claims 2
- HWHLPVGTWGOCJO-UHFFFAOYSA-N Trihexyphenidyl Chemical compound C1CCCCC1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 HWHLPVGTWGOCJO-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 2
- 229960002690 fluphenazine Drugs 0.000 claims 2
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 2
- 230000005764 inhibitory process Effects 0.000 claims 2
- 229960004502 levodopa Drugs 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 229960005017 olanzapine Drugs 0.000 claims 2
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 229960004431 quetiapine Drugs 0.000 claims 2
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 229960001032 trihexyphenidyl Drugs 0.000 claims 2
- IFDAFHYQCHIWOU-HUUCEWRRSA-N (2r)-2-[(2r)-4-[bis(4-chlorophenyl)methyl]-2-methylpiperazin-1-yl]propanoic acid Chemical compound C1[C@@H](C)N([C@H](C)C(O)=O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 IFDAFHYQCHIWOU-HUUCEWRRSA-N 0.000 claims 1
- FTCZTBBFXDTQRT-CABCVRRESA-N (2s)-2-[(3r)-4-[bis(4-chlorophenyl)methyl]-3-methylpiperazin-1-yl]propanoic acid Chemical compound C[C@@H]1CN([C@@H](C)C(O)=O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 FTCZTBBFXDTQRT-CABCVRRESA-N 0.000 claims 1
- MKJIEFSOBYUXJB-HOCLYGCPSA-N (3S,11bS)-9,10-dimethoxy-3-isobutyl-1,3,4,6,7,11b-hexahydro-2H-pyrido[2,1-a]isoquinolin-2-one Chemical compound C1CN2C[C@H](CC(C)C)C(=O)C[C@H]2C2=C1C=C(OC)C(OC)=C2 MKJIEFSOBYUXJB-HOCLYGCPSA-N 0.000 claims 1
- BGRJTUBHPOOWDU-NSHDSACASA-N (S)-(-)-sulpiride Chemical compound CCN1CCC[C@H]1CNC(=O)C1=CC(S(N)(=O)=O)=CC=C1OC BGRJTUBHPOOWDU-NSHDSACASA-N 0.000 claims 1
- WSPOMRSOLSGNFJ-AUWJEWJLSA-N (Z)-chlorprothixene Chemical compound C1=C(Cl)C=C2C(=C/CCN(C)C)\C3=CC=CC=C3SC2=C1 WSPOMRSOLSGNFJ-AUWJEWJLSA-N 0.000 claims 1
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims 1
- YCKSFFKKEWTLIZ-UHFFFAOYSA-N 2-(4-benzhydrylpiperazin-1-ium-1-yl)acetate Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YCKSFFKKEWTLIZ-UHFFFAOYSA-N 0.000 claims 1
- ATVRCQYLGRVROG-UJONTBEJSA-N 2-[(2r)-2-methyl-4-[(3-methylsulfanylphenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound CSC1=CC=CC(C(N2C[C@@H](C)N(CC(O)=O)CC2)C=2C=CC=CC=2)=C1 ATVRCQYLGRVROG-UJONTBEJSA-N 0.000 claims 1
- ATVRCQYLGRVROG-IIBYNOLFSA-N 2-[(2r)-2-methyl-4-[(r)-(3-methylsulfanylphenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound CSC1=CC=CC([C@H](N2C[C@@H](C)N(CC(O)=O)CC2)C=2C=CC=CC=2)=C1 ATVRCQYLGRVROG-IIBYNOLFSA-N 0.000 claims 1
- ZBNXGLCWANFABX-IIBYNOLFSA-N 2-[(2r)-2-methyl-4-[(r)-(4-methylsulfanylphenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1=CC(SC)=CC=C1[C@@H](C=1C=CC=CC=1)N1C[C@@H](C)N(CC(O)=O)CC1 ZBNXGLCWANFABX-IIBYNOLFSA-N 0.000 claims 1
- QDNCLRODUIGLOQ-WZONZLPQSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-(3-propan-2-ylphenyl)methyl]piperazin-1-yl]acetic acid Chemical compound CC(C)C1=CC=CC([C@H](N2C[C@@H](C)N(CC(O)=O)CC2)C=2C=CC=CC=2)=C1 QDNCLRODUIGLOQ-WZONZLPQSA-N 0.000 claims 1
- LAKPWFQFXOTPTB-HOYKHHGWSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-(3-thiophen-2-ylphenyl)methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(C=CC=1)C=1SC=CC=1)C1=CC=CC=C1 LAKPWFQFXOTPTB-HOYKHHGWSA-N 0.000 claims 1
- YXOALCHAZKUKKM-JIPXPUAJSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-[3-(2-pyridin-3-ylethynyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(C=CC=1)C#CC=1C=NC=CC=1)C1=CC=CC=C1 YXOALCHAZKUKKM-JIPXPUAJSA-N 0.000 claims 1
- VLWVOPPEPGWJMV-JIPXPUAJSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-[3-(2-pyridin-4-ylethynyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(C=CC=1)C#CC=1C=CN=CC=1)C1=CC=CC=C1 VLWVOPPEPGWJMV-JIPXPUAJSA-N 0.000 claims 1
- XKQWYNSQJZYUDX-FOIQADDNSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-[3-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(OC(F)(F)F)C=CC=1)C1=CC=CC=C1 XKQWYNSQJZYUDX-FOIQADDNSA-N 0.000 claims 1
- QNCGXRCZIJEMGS-FOIQADDNSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 QNCGXRCZIJEMGS-FOIQADDNSA-N 0.000 claims 1
- IUPFIUUFWNDGBI-SKCUWOTOSA-N 2-[(2r)-2-methyl-4-[(r)-phenyl-[4-(2-phenylethynyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=CC(=CC=1)C#CC=1C=CC=CC=1)C1=CC=CC=C1 IUPFIUUFWNDGBI-SKCUWOTOSA-N 0.000 claims 1
- YYQMYLPZPJXTOC-FZKQIMNGSA-N 2-[(2r)-2-methyl-4-[(r)-thiophen-2-yl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CS1 YYQMYLPZPJXTOC-FZKQIMNGSA-N 0.000 claims 1
- ATVRCQYLGRVROG-IERDGZPVSA-N 2-[(2r)-2-methyl-4-[(s)-(3-methylsulfanylphenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound CSC1=CC=CC([C@@H](N2C[C@@H](C)N(CC(O)=O)CC2)C=2C=CC=CC=2)=C1 ATVRCQYLGRVROG-IERDGZPVSA-N 0.000 claims 1
- XKQWYNSQJZYUDX-QRWLVFNGSA-N 2-[(2r)-2-methyl-4-[(s)-phenyl-[3-(trifluoromethoxy)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C=C(OC(F)(F)F)C=CC=1)C1=CC=CC=C1 XKQWYNSQJZYUDX-QRWLVFNGSA-N 0.000 claims 1
- QNCGXRCZIJEMGS-QRWLVFNGSA-N 2-[(2r)-2-methyl-4-[(s)-phenyl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 QNCGXRCZIJEMGS-QRWLVFNGSA-N 0.000 claims 1
- YYQMYLPZPJXTOC-ACJLOTCBSA-N 2-[(2r)-2-methyl-4-[(s)-thiophen-2-yl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CS1 YYQMYLPZPJXTOC-ACJLOTCBSA-N 0.000 claims 1
- QNCGXRCZIJEMGS-IWPPFLRJSA-N 2-[(2r)-2-methyl-4-[phenyl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 QNCGXRCZIJEMGS-IWPPFLRJSA-N 0.000 claims 1
- YYQMYLPZPJXTOC-YJJYDOSJSA-N 2-[(2r)-2-methyl-4-[thiophen-2-yl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CS1 YYQMYLPZPJXTOC-YJJYDOSJSA-N 0.000 claims 1
- UGIBFMLFMVOLKX-QMRFKDRMSA-N 2-[(2r)-4-[(3-bromophenyl)-(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(Br)C=CC=1)C1=CC=C(F)C=C1 UGIBFMLFMVOLKX-QMRFKDRMSA-N 0.000 claims 1
- OIVVLOMKKYRLKQ-IWPPFLRJSA-N 2-[(2r)-4-[(3-bromophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(Br)C=CC=1)C1=CC=CC=C1 OIVVLOMKKYRLKQ-IWPPFLRJSA-N 0.000 claims 1
- CPEYULHHFFTAOZ-IWPPFLRJSA-N 2-[(2r)-4-[(3-chlorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(Cl)C=CC=1)C1=CC=CC=C1 CPEYULHHFFTAOZ-IWPPFLRJSA-N 0.000 claims 1
- MIDDUNWOCFPOEG-IWPPFLRJSA-N 2-[(2r)-4-[(3-fluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(F)C=CC=1)C1=CC=CC=C1 MIDDUNWOCFPOEG-IWPPFLRJSA-N 0.000 claims 1
- CRCVETNPVOPKBV-IWPPFLRJSA-N 2-[(2r)-4-[(4-bromophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 CRCVETNPVOPKBV-IWPPFLRJSA-N 0.000 claims 1
- LQRBCWKOHCKPNU-IWPPFLRJSA-N 2-[(2r)-4-[(4-chlorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 LQRBCWKOHCKPNU-IWPPFLRJSA-N 0.000 claims 1
- SQEYLVSNTHBOBX-UJONTBEJSA-N 2-[(2r)-4-[(4-cyanophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC(=CC=1)C#N)C1=CC=CC=C1 SQEYLVSNTHBOBX-UJONTBEJSA-N 0.000 claims 1
- QLVYCQMDCDWCMY-IWPPFLRJSA-N 2-[(2r)-4-[(4-fluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC(F)=CC=1)C1=CC=CC=C1 QLVYCQMDCDWCMY-IWPPFLRJSA-N 0.000 claims 1
- HMWZKVCJOXBADA-JLTOFOAXSA-N 2-[(2r)-4-[(r)-(2,4-difluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C(=CC(F)=CC=1)F)C1=CC=CC=C1 HMWZKVCJOXBADA-JLTOFOAXSA-N 0.000 claims 1
- QRMSKDYJTOHJPI-FOIQADDNSA-N 2-[(2r)-4-[(r)-(2-bromophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C(=CC=CC=1)Br)C1=CC=CC=C1 QRMSKDYJTOHJPI-FOIQADDNSA-N 0.000 claims 1
- OIVVLOMKKYRLKQ-FOIQADDNSA-N 2-[(2r)-4-[(r)-(3-bromophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(Br)C=CC=1)C1=CC=CC=C1 OIVVLOMKKYRLKQ-FOIQADDNSA-N 0.000 claims 1
- MIDDUNWOCFPOEG-FOIQADDNSA-N 2-[(2r)-4-[(r)-(3-fluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(F)C=CC=1)C1=CC=CC=C1 MIDDUNWOCFPOEG-FOIQADDNSA-N 0.000 claims 1
- KVKFQXAUFPDEBM-FOIQADDNSA-N 2-[(2r)-4-[(r)-(3-iodophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=C(I)C=CC=1)C1=CC=CC=C1 KVKFQXAUFPDEBM-FOIQADDNSA-N 0.000 claims 1
- QLVYCQMDCDWCMY-FOIQADDNSA-N 2-[(2r)-4-[(r)-(4-fluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@@H](C=1C=CC(F)=CC=1)C1=CC=CC=C1 QLVYCQMDCDWCMY-FOIQADDNSA-N 0.000 claims 1
- HMWZKVCJOXBADA-VLIAUNLRSA-N 2-[(2r)-4-[(s)-(2,4-difluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C(=CC(F)=CC=1)F)C1=CC=CC=C1 HMWZKVCJOXBADA-VLIAUNLRSA-N 0.000 claims 1
- QRMSKDYJTOHJPI-QRWLVFNGSA-N 2-[(2r)-4-[(s)-(2-bromophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C(=CC=CC=1)Br)C1=CC=CC=C1 QRMSKDYJTOHJPI-QRWLVFNGSA-N 0.000 claims 1
- JFIVZNHZQZTSMN-QRWLVFNGSA-N 2-[(2r)-4-[(s)-(2-fluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C(=CC=CC=1)F)C1=CC=CC=C1 JFIVZNHZQZTSMN-QRWLVFNGSA-N 0.000 claims 1
- OIVVLOMKKYRLKQ-QRWLVFNGSA-N 2-[(2r)-4-[(s)-(3-bromophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C=C(Br)C=CC=1)C1=CC=CC=C1 OIVVLOMKKYRLKQ-QRWLVFNGSA-N 0.000 claims 1
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- QLVYCQMDCDWCMY-QRWLVFNGSA-N 2-[(2r)-4-[(s)-(4-fluorophenyl)-phenylmethyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1[C@H](C=1C=CC(F)=CC=1)C1=CC=CC=C1 QLVYCQMDCDWCMY-QRWLVFNGSA-N 0.000 claims 1
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| PE (2) | PE20120223A1 (enExample) |
| PL (1) | PL2041088T3 (enExample) |
| PT (1) | PT2041088E (enExample) |
| RS (1) | RS53277B (enExample) |
| SG (1) | SG172685A1 (enExample) |
| SI (1) | SI2041088T1 (enExample) |
| TW (1) | TWI429631B (enExample) |
| WO (1) | WO2008002583A1 (enExample) |
| ZA (1) | ZA201004216B (enExample) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK2041088T3 (da) | 2006-06-28 | 2014-04-07 | Amgen Inc | Glycintransporter-1 inhibitorer |
| US8258306B2 (en) * | 2007-12-12 | 2012-09-04 | Amgen Inc. | Glycine transporter-1 inhibitors |
| EP2575815A4 (en) * | 2010-06-04 | 2013-12-25 | Albany Molecular Res Inc | GLYCIN TRANSPORTER 1 INHIBITORS, METHODS OF MAKING THE SAME, AND USES THEREOF |
| US9012489B2 (en) | 2011-08-03 | 2015-04-21 | Boehringer Ingelheim International Gmbh | Phenyl-3-aza-bicyclo[3.1.0]hex-3-yl-methanones and the use thereof as medicament |
| JOP20130213B1 (ar) | 2012-07-17 | 2021-08-17 | Takeda Pharmaceuticals Co | معارضات لمستقبلht3-5 |
| EP3134406A1 (en) | 2014-04-24 | 2017-03-01 | Dart Neuroscience (Cayman) Ltd | Substituted 2,4,5,6-tetrahydropyrrolo[3,4-c]pyrazole and 4,5,6,7-tetrahydro-2h-pyrazolo [4,3-c]pyridine compounds as glyt1 inhibitors |
| ES2883295T3 (es) | 2014-09-29 | 2021-12-07 | Takeda Pharmaceuticals Co | Forma cristalina de 1-(1-metil-1h-pirazol-4-il)-n-((1r,5s,7s)-9-metil-3-oxa-9-azabiciclo[3.3.1]nonan-7-il)-1h-indol-3-carboxamida |
| EP3215500A1 (en) | 2014-11-05 | 2017-09-13 | Dart NeuroScience (Cayman) Ltd. | Substituted azetidinyl compounds as glyt1 inhibitors |
| KR101753617B1 (ko) | 2016-05-10 | 2017-07-11 | 주식회사 뉴로벤티 | 피페라진-1-카복사미딘 또는 이의 약학적으로 허용가능한 염을 유효성분으로 포함하는 자폐 범주성 장애 예방 및 치료용 약학적 조성물 |
Family Cites Families (71)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3032556A (en) * | 1962-05-01 | Process for the preparation of new | ||
| GB817231A (en) * | 1956-01-27 | 1959-07-29 | Henri Morren | New derivatives of n-mono-benzhydryl-piperazine and process for the preparation thereof |
| US3928356A (en) * | 1967-10-06 | 1975-12-23 | Fujisawa Pharmaceutical Co | 10-{8 4-({107 -Hydroxy alkyl)-1-piperazimyl{9 -dibenzo (h,f) oxofins and thiepins and acetyl esters thereof |
| FR2081579B1 (enExample) | 1970-03-18 | 1973-04-06 | Delalande Sa | |
| US4107288A (en) | 1974-09-18 | 1978-08-15 | Pharmaceutical Society Of Victoria | Injectable compositions, nanoparticles useful therein, and process of manufacturing same |
| GB1574822A (en) | 1976-03-23 | 1980-09-10 | Lafon Labor | Acetohydroxamic acid derivatives and pharmaceutical compositions thereof |
| US4082755A (en) * | 1977-02-14 | 1978-04-04 | Janssen Pharmaceutica N.V. | 1-[(Diarylmethyl)aminoalkyl]piperidimes |
| FI75816C (fi) | 1981-02-06 | 1988-08-08 | Ucb Sa | Foerfarande foer framstaellning av terapeutiskt aktiv 2-/4-(difenylmetyl)-1-piperazinyl/-aettiksyror eller dess amid. |
| US4929618A (en) | 1988-03-25 | 1990-05-29 | Ube Industries, Ltd. | Piperdine and piperazine derivatives, and antihistaminic pharmaceutical compositions containing the same |
| CA2015949A1 (en) | 1989-05-22 | 1990-11-22 | Yasuo Ito | Piperidine derivative, method for preparation thereof, and a pharmaceutical composition comprising the same |
| JPH03184963A (ja) | 1989-12-13 | 1991-08-12 | Hokuriku Seiyaku Co Ltd | ジベンズオキサゼピン誘導体 |
| JPH03246287A (ja) | 1990-02-22 | 1991-11-01 | Hokuriku Seiyaku Co Ltd | ピペラジン誘導体 |
| US5145684A (en) | 1991-01-25 | 1992-09-08 | Sterling Drug Inc. | Surface modified drug nanoparticles |
| EP0598123A4 (en) | 1991-07-19 | 1995-02-15 | Zeria Pharm Co Ltd | PIPERAZINE DERIVATIVES AND MEDICINAL PRODUCTS CONTAINING THEM. |
| JPH05148234A (ja) | 1991-10-02 | 1993-06-15 | Hokuriku Seiyaku Co Ltd | アルカン酸誘導体 |
| GB9202238D0 (en) | 1992-02-03 | 1992-03-18 | Wellcome Found | Compounds |
| US5807858A (en) | 1996-06-05 | 1998-09-15 | Delta Pharmaceutical, Inc. | Compositions and methods for reducing respiratory depression |
| US5538973A (en) | 1992-03-27 | 1996-07-23 | Kyoto Pharmaceutical Industries, Ltd. | Imidazole derivative, pharmaceutical use thereof, and intermediate therefor |
| JP3352184B2 (ja) | 1993-11-12 | 2002-12-03 | 株式会社アズウェル | ピペラジン不飽和脂肪酸誘導体 |
| HU213107B (en) | 1994-02-23 | 1997-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing acetic acid derivatives and pharmaceutical compositions containing them |
| US5753671A (en) * | 1994-08-10 | 1998-05-19 | British Biotech Pharmaceuticals Limited | Imidazopyridine derivatives as dual histamine (H1) and platelet activating factor (PAF) antagonists |
| PL321003A1 (en) | 1994-12-23 | 1997-11-24 | Thomae Gmbh Dr K | Derivatives of piperasine, drugs containing them, their application and methods of obtaining them |
| US5700801A (en) * | 1994-12-23 | 1997-12-23 | Karl Thomae, Gmbh | Piperazine derivatives, pharmaceutical compositions containing these compounds, their use and processes for preparing them |
| IL117798A (en) | 1995-04-07 | 2001-11-25 | Schering Plough Corp | Tricyclic compounds useful for inhibiting the function of protein - G and for the treatment of malignant diseases, and pharmaceutical preparations containing them |
| UA54385C2 (uk) | 1995-04-07 | 2003-03-17 | Ново Нордіск А/С | N-заміщені азагетероциклічні карбонові кислоти та їх ефіри, спосіб їх одержання, фармацевтична композиція та спосіб лікування |
| JP3246287B2 (ja) | 1995-09-08 | 2002-01-15 | 株式会社大林組 | 既存建物のジャッキアップ工法 |
| US6469009B1 (en) | 1996-04-08 | 2002-10-22 | Ucb, S.A. | Pharmaceutical compositions for the treatment of rhinitis |
| AT403803B (de) * | 1996-04-19 | 1998-05-25 | Sanochemia Ltd | Neue benzazepinderivate, diese enthaltende arzneimittel und verwendung derselben zum herstellen von arzneimitteln |
| US6001854A (en) * | 1996-05-31 | 1999-12-14 | Allelix Neuroscience Inc. | Pharmaceutical for treating of neurological and neuropsychiatric disorders |
| WO1997045423A1 (en) | 1996-05-31 | 1997-12-04 | Trophix Neuroscience Inc. | Pharmaceutical for treating of neurological and neuropsychiatric disorders |
| SI1014966T1 (sl) | 1996-05-31 | 2006-10-31 | Allelix Neuroscience Inc | Zdravilo za zdravljenje nevroloskih in nevripsihiatricnih bolezni |
| TW416953B (en) * | 1996-09-25 | 2001-01-01 | Takeda Chemical Industries Ltd | Tricyclic compounds for eliciting a prostaglandin I2 receptor agonistic effect, their production and use |
| IL129122A0 (en) * | 1996-10-04 | 2000-02-17 | Novo Nordisk As | N-substituted azaheterocyclic compounds |
| TW486475B (en) | 1996-12-26 | 2002-05-11 | Ube Industries | Acid addition salt of optically active piperidine compound and process for preparing the same |
| GB9709972D0 (en) | 1997-05-19 | 1997-07-09 | Pfizer Ltd | Tetrazoles |
| AU7455798A (en) * | 1997-06-04 | 1998-12-21 | Nippon Shoji Kaisha, Ltd. | Process for producing piperazinesulfonamide derivatives and salts thereof |
| AU7907298A (en) | 1997-06-25 | 1999-01-19 | Novo Nordisk A/S | Novel heterocyclic compounds |
| GB9804734D0 (en) | 1998-03-05 | 1998-04-29 | Pfizer Ltd | Compounds |
| CA2233763C (en) * | 1998-03-31 | 2005-01-11 | Teknion Furniture Systems Limited | Electrical station |
| US6894059B1 (en) | 1999-03-26 | 2005-05-17 | Ucb S.A. | Compounds and methods for treatment of asthma, allergy and inflammatory disorders |
| US6693099B2 (en) | 2000-10-17 | 2004-02-17 | The Procter & Gamble Company | Substituted piperazine compounds optionally containing a quinolyl moiety for treating multidrug resistance |
| ES2317116T3 (es) | 2001-02-16 | 2009-04-16 | Aventis Pharmaceuticals Inc. | Derivados de carbonilos sustituidos heterociclicos y su uso como ligandos del receptor de dopamina d3. |
| CA2458009C (en) | 2001-08-24 | 2011-08-16 | Yale University | Piperazinone compounds as anti-tumor and anti-cancer agents and methods of treatment |
| TWI329108B (en) * | 2001-09-06 | 2010-08-21 | Schering Corp | 17-hydroxysteroid dehydrogenase type 3 inhibitors for the treatment of androgen dependent diseases |
| US20040259912A1 (en) * | 2001-09-28 | 2004-12-23 | Takahiro Matsumoto | Benzine derivatives, process for preparing the same and use thereof |
| DE10149370A1 (de) * | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| AU2002347906A2 (en) | 2001-10-16 | 2003-04-28 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| CN100500679C (zh) | 2001-11-01 | 2009-06-17 | 中国人民解放军军事医学科学院毒物药物研究所 | 具有调节血管内皮细胞功能活性的化合物及其制备方法和用途 |
| CN100486982C (zh) | 2001-11-02 | 2009-05-13 | 中国人民解放军军事医学科学院毒物药物研究所 | 具有预防和治疗血栓性疾病功能的化合物,含它们的药物组合物和它们的医药用途 |
| CN100486981C (zh) | 2001-11-02 | 2009-05-13 | 中国人民解放军军事医学科学院毒物药物研究所 | 具有预防和治疗动脉粥样硬化功能的化合物及其在生物医药学中的应用 |
| WO2003039255A1 (en) | 2001-11-05 | 2003-05-15 | Basf Aktiengesellschaft | Use of substituted dibenzothiepine derivatives as insecticidal, acaricidal and nematicidal agents |
| TW200300757A (en) * | 2001-11-16 | 2003-06-16 | Schering Corp | Azetidinyl diamines useful as ligands of the nociceptin receptor orl-1 |
| JP4391825B2 (ja) | 2001-12-06 | 2009-12-24 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂キネシン阻害剤 |
| JP4467979B2 (ja) | 2001-12-06 | 2010-05-26 | メルク・シャープ・エンド・ドーム・コーポレイション | 有糸分裂キネシン阻害剤 |
| WO2003049527A2 (en) | 2001-12-06 | 2003-06-19 | Merck & Co., Inc. | Mitotic kinesin inhibitors |
| JP2005515208A (ja) | 2001-12-06 | 2005-05-26 | メルク エンド カムパニー インコーポレーテッド | 有糸分裂性キネシン阻害剤 |
| ATE372341T1 (de) | 2001-12-06 | 2007-09-15 | Merck & Co Inc | Inhibitoren von mitotischem kinesin |
| MXPA04005989A (es) * | 2001-12-20 | 2004-09-27 | Lundbeck & Co As H | Derivados de ariloxifenilo y arilsulfanilfenilo. |
| DK1487810T3 (da) | 2002-03-27 | 2010-05-17 | Sun Pharma Advanced Res Co Ltd | 4-(Diarylmethyl)-1-piperazinylderivater |
| US8476280B2 (en) | 2002-05-09 | 2013-07-02 | Versi Group, Llc | Compositions and methods for combating lower urinary tract dysfunctions with delta opioid receptor agonists |
| ATE386526T1 (de) | 2002-07-02 | 2008-03-15 | Ucb Farchim Sa | Diarylmethylpiperazines als prophylaktische oder therapeutische mittel gegen virale myocarditis |
| SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| AU2004263306B2 (en) | 2003-08-11 | 2010-04-22 | F. Hoffmann-La Roche Ag | Piperazine with or-substituted phenyl group and their use as GLYT1 inhibitors |
| SE0400027D0 (sv) | 2004-01-09 | 2004-01-09 | Astrazeneca Ab | Diarylmethyl piperazine derivatives, preparations thereof and uses thereof |
| WO2005077373A2 (en) | 2004-02-03 | 2005-08-25 | Astrazeneca Ab | Treatment of gastro-esophageal reflux disease (gerd) |
| WO2006043691A1 (ja) | 2004-10-18 | 2006-04-27 | Reverse Proteomics Research Institute Co., Ltd. | 創薬標的タンパク質及び標的遺伝子、並びにスクリーニング方法 |
| CN1709870B (zh) * | 2005-07-19 | 2011-07-06 | 中国科学院成都生物研究所 | 光学纯n′,n′-二取代脯氨酰肼化合物及其制备方法和应用 |
| CA2653497A1 (en) * | 2006-05-26 | 2007-12-06 | Neuromed Pharmaceuticals Ltd. | Heterocyclic compounds as calcium channel blockers |
| DK2041088T3 (da) * | 2006-06-28 | 2014-04-07 | Amgen Inc | Glycintransporter-1 inhibitorer |
| CN100506809C (zh) * | 2006-11-28 | 2009-07-01 | 广西大学 | 手性二苯甲基哌嗪衍生物及其制备方法 |
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- 2007-06-26 PT PT77964666T patent/PT2041088E/pt unknown
- 2007-06-26 PL PL07796466T patent/PL2041088T3/pl unknown
- 2007-06-26 AU AU2007265467A patent/AU2007265467C1/en not_active Ceased
- 2007-06-26 SG SG2011041423A patent/SG172685A1/en unknown
- 2007-06-26 EP EP12178740A patent/EP2565183A1/en not_active Withdrawn
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