JP2009542661A5 - - Google Patents
Download PDFInfo
- 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
Links
- 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
- MIDDUNWOCFPOEG-QRWLVFNGSA-N 2-[(2r)-4-[(s)-(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-QRWLVFNGSA-N 0.000 claims 1
- 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
- YVTLMYCLJISGFQ-CQSZACIVSA-N 2-[(2r)-4-[bis(3-chlorophenyl)methyl]-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(Cl)=C1 YVTLMYCLJISGFQ-CQSZACIVSA-N 0.000 claims 1
- SAZISGPTZMZEHS-CQSZACIVSA-N 2-[(2r)-4-[bis(3-fluorophenyl)methyl]-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(F)=C1 SAZISGPTZMZEHS-CQSZACIVSA-N 0.000 claims 1
- MYCXKSYMFPEZNF-FQEVSTJZSA-N 2-[(2r)-4-[bis(4-chlorophenyl)methyl]-2-propan-2-ylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C(C)C)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 MYCXKSYMFPEZNF-FQEVSTJZSA-N 0.000 claims 1
- PORWTURWAOHGHM-CQSZACIVSA-N 2-[(2r)-4-[bis(4-fluorophenyl)methyl]-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 PORWTURWAOHGHM-CQSZACIVSA-N 0.000 claims 1
- OWKBCWMUJDSKIA-CQSZACIVSA-N 2-[(2r)-4-[bis[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)C1=CC=CC(C(F)(F)F)=C1 OWKBCWMUJDSKIA-CQSZACIVSA-N 0.000 claims 1
- OTAHYZCSVKSJHZ-AJTIQKQFSA-N 2-[(2r)-4-[cyclopropyl-[3-(trifluoromethyl)phenyl]methyl]-2-methylpiperazin-1-yl]acetic acid;dihydrochloride Chemical compound Cl.Cl.C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=C(C=CC=1)C(F)(F)F)C1CC1 OTAHYZCSVKSJHZ-AJTIQKQFSA-N 0.000 claims 1
- YZLHCJXFENMEAB-MRXNPFEDSA-N 2-[(2r)-4-benzhydryl-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YZLHCJXFENMEAB-MRXNPFEDSA-N 0.000 claims 1
- GRLGGVFIOIYHEB-GGMCWBHBSA-N 2-[(2r)-4-benzhydryl-2-methylpiperazin-1-yl]acetic acid;dihydrochloride Chemical compound Cl.Cl.C1CN(CC(O)=O)[C@H](C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 GRLGGVFIOIYHEB-GGMCWBHBSA-N 0.000 claims 1
- QNCGXRCZIJEMGS-OOJLDXBWSA-N 2-[(2s)-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-OOJLDXBWSA-N 0.000 claims 1
- YZLHCJXFENMEAB-INIZCTEOSA-N 2-[(2s)-4-benzhydryl-2-methylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)[C@@H](C)CN1C(C=1C=CC=CC=1)C1=CC=CC=C1 YZLHCJXFENMEAB-INIZCTEOSA-N 0.000 claims 1
- OVALBRNFTICKFG-GASCZTMLSA-N 2-[(2s,6r)-4-[bis(4-chlorophenyl)methyl]-2,6-dimethylpiperazin-1-yl]acetic acid Chemical compound C1[C@@H](C)N(CC(O)=O)[C@@H](C)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 OVALBRNFTICKFG-GASCZTMLSA-N 0.000 claims 1
- ARIHZEQODHIPOR-CQSZACIVSA-N 2-[(3r)-4-[bis(4-fluorophenyl)methyl]-3-methylpiperazin-1-yl]acetic acid Chemical compound C[C@@H]1CN(CC(O)=O)CCN1C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 ARIHZEQODHIPOR-CQSZACIVSA-N 0.000 claims 1
- UFEQVRJHUYMMJL-MRXNPFEDSA-N 2-[(3r)-4-benzhydryl-3-methylpiperazin-1-yl]acetic acid Chemical compound C[C@@H]1CN(CC(O)=O)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UFEQVRJHUYMMJL-MRXNPFEDSA-N 0.000 claims 1
- UFEQVRJHUYMMJL-INIZCTEOSA-N 2-[(3s)-4-benzhydryl-3-methylpiperazin-1-yl]acetic acid Chemical compound C[C@H]1CN(CC(O)=O)CCN1C(C=1C=CC=CC=1)C1=CC=CC=C1 UFEQVRJHUYMMJL-INIZCTEOSA-N 0.000 claims 1
- ADHSFKIVEHYSFA-UHFFFAOYSA-N 2-[4-[(2-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C(=CC=CC=1)Br)C1=CC=CC=C1 ADHSFKIVEHYSFA-UHFFFAOYSA-N 0.000 claims 1
- LTIDOYNTBFBRMP-UHFFFAOYSA-N 2-[4-[(3,5-dichlorophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=C(Cl)C=C(Cl)C=1)C1=CC=CC=C1 LTIDOYNTBFBRMP-UHFFFAOYSA-N 0.000 claims 1
- PBOWWHHRBMJHES-UHFFFAOYSA-N 2-[4-[(3-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=C(Br)C=CC=1)C1=CC=CC=C1 PBOWWHHRBMJHES-UHFFFAOYSA-N 0.000 claims 1
- MITIBVNRPIVOGS-UHFFFAOYSA-N 2-[4-[(4-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=CC(Br)=CC=1)C1=CC=CC=C1 MITIBVNRPIVOGS-UHFFFAOYSA-N 0.000 claims 1
- NBQBQRKLQXVPIS-UHFFFAOYSA-N 2-[4-[(4-chlorophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=CC=C1 NBQBQRKLQXVPIS-UHFFFAOYSA-N 0.000 claims 1
- PBOWWHHRBMJHES-LJQANCHMSA-N 2-[4-[(r)-(3-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1[C@@H](C=1C=C(Br)C=CC=1)C1=CC=CC=C1 PBOWWHHRBMJHES-LJQANCHMSA-N 0.000 claims 1
- MITIBVNRPIVOGS-LJQANCHMSA-N 2-[4-[(r)-(4-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1[C@@H](C=1C=CC(Br)=CC=1)C1=CC=CC=C1 MITIBVNRPIVOGS-LJQANCHMSA-N 0.000 claims 1
- PBOWWHHRBMJHES-IBGZPJMESA-N 2-[4-[(s)-(3-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1[C@H](C=1C=C(Br)C=CC=1)C1=CC=CC=C1 PBOWWHHRBMJHES-IBGZPJMESA-N 0.000 claims 1
- MITIBVNRPIVOGS-IBGZPJMESA-N 2-[4-[(s)-(4-bromophenyl)-phenylmethyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1[C@H](C=1C=CC(Br)=CC=1)C1=CC=CC=C1 MITIBVNRPIVOGS-IBGZPJMESA-N 0.000 claims 1
- MDLQJNCGZVDZFV-IBGZPJMESA-N 2-[4-[(s)-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-IBGZPJMESA-N 0.000 claims 1
- ZFCGIKQYYZCVDR-UHFFFAOYSA-N 2-[4-[[3-(trifluoromethyl)phenyl]-[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=C(C(F)(F)F)C=C1 ZFCGIKQYYZCVDR-UHFFFAOYSA-N 0.000 claims 1
- GDURPIMZHVOHJJ-UHFFFAOYSA-N 2-[4-[bis(4-chlorophenyl)methyl]-2,2-dimethylpiperazin-1-yl]acetic acid Chemical compound C1CN(CC(O)=O)C(C)(C)CN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 GDURPIMZHVOHJJ-UHFFFAOYSA-N 0.000 claims 1
- DAUGSLOOURQCPC-UHFFFAOYSA-N 2-[4-[bis(4-chlorophenyl)methyl]-2-oxopiperazin-1-yl]acetic acid Chemical compound C1C(=O)N(CC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 DAUGSLOOURQCPC-UHFFFAOYSA-N 0.000 claims 1
- AACCKCZNUBWIJU-UHFFFAOYSA-N 2-[4-[bis(4-chlorophenyl)methyl]-3-oxopiperazin-1-yl]acetic acid Chemical compound O=C1CN(CC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 AACCKCZNUBWIJU-UHFFFAOYSA-N 0.000 claims 1
- JXBXMYFRUKHWCQ-UHFFFAOYSA-N 2-[4-[bis(4-chlorophenyl)methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JXBXMYFRUKHWCQ-UHFFFAOYSA-N 0.000 claims 1
- JYYGQGRFWADHGO-UHFFFAOYSA-N 2-[4-[bis(4-chlorophenyl)methyl]piperazin-1-yl]propanoic acid Chemical compound C1CN(C(C)C(O)=O)CCN1C(C=1C=CC(Cl)=CC=1)C1=CC=C(Cl)C=C1 JYYGQGRFWADHGO-UHFFFAOYSA-N 0.000 claims 1
- RVZFLXOAUXUWPA-UHFFFAOYSA-N 2-[4-[bis[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC(C(F)(F)F)=C1 RVZFLXOAUXUWPA-UHFFFAOYSA-N 0.000 claims 1
- VHIBWFFUHGHDEM-UHFFFAOYSA-N 2-[4-[phenyl-[3-(trifluoromethyl)phenyl]methyl]-1,4-diazepan-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCCN1C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 VHIBWFFUHGHDEM-UHFFFAOYSA-N 0.000 claims 1
- MDLQJNCGZVDZFV-UHFFFAOYSA-N 2-[4-[phenyl-[3-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=C(C=CC=1)C(F)(F)F)C1=CC=CC=C1 MDLQJNCGZVDZFV-UHFFFAOYSA-N 0.000 claims 1
- VNFPTUUVWAKYMQ-UHFFFAOYSA-N 2-[4-[phenyl-[4-(trifluoromethyl)phenyl]methyl]piperazin-1-yl]acetic acid Chemical compound C1CN(CC(=O)O)CCN1C(C=1C=CC(=CC=1)C(F)(F)F)C1=CC=CC=C1 VNFPTUUVWAKYMQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 1
- TWUJBHBRYYTEDL-UHFFFAOYSA-N Alentemol Chemical compound OC1=CC(CC(N(CCC)CCC)C2)=C3C2=CC=CC3=C1 TWUJBHBRYYTEDL-UHFFFAOYSA-N 0.000 claims 1
- CEUORZQYGODEFX-UHFFFAOYSA-N Aripirazole Chemical compound ClC1=CC=CC(N2CCN(CCCCOC=3C=C4NC(=O)CCC4=CC=3)CC2)=C1Cl CEUORZQYGODEFX-UHFFFAOYSA-N 0.000 claims 1
- RGCVKNLCSQQDEP-UHFFFAOYSA-N Perphenazine Chemical compound C1CN(CCO)CCN1CCCN1C2=CC(Cl)=CC=C2SC2=CC=CC=C21 RGCVKNLCSQQDEP-UHFFFAOYSA-N 0.000 claims 1
- BKRGVLQUQGGVSM-KBXCAEBGSA-N Revanil Chemical compound C1=CC(C=2[C@H](N(C)C[C@H](C=2)NC(=O)N(CC)CC)C2)=C3C2=CNC3=C1 BKRGVLQUQGGVSM-KBXCAEBGSA-N 0.000 claims 1
- KLBQZWRITKRQQV-UHFFFAOYSA-N Thioridazine Chemical compound C12=CC(SC)=CC=C2SC2=CC=CC=C2N1CCC1CCCCN1C KLBQZWRITKRQQV-UHFFFAOYSA-N 0.000 claims 1
- GFBKORZTTCHDGY-UWVJOHFNSA-N Thiothixene Chemical compound C12=CC(S(=O)(=O)N(C)C)=CC=C2SC2=CC=CC=C2\C1=C\CCN1CCN(C)CC1 GFBKORZTTCHDGY-UWVJOHFNSA-N 0.000 claims 1
- IHTYTYHXCRAMAV-UHFFFAOYSA-N acetic acid;dihydrochloride Chemical compound Cl.Cl.CC(O)=O IHTYTYHXCRAMAV-UHFFFAOYSA-N 0.000 claims 1
- 229960000276 acetophenazine Drugs 0.000 claims 1
- WNTYBHLDCKXEOT-UHFFFAOYSA-N acetophenazine Chemical compound C12=CC(C(=O)C)=CC=C2SC2=CC=CC=C2N1CCCN1CCN(CCO)CC1 WNTYBHLDCKXEOT-UHFFFAOYSA-N 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 229950007263 alentemol Drugs 0.000 claims 1
- 229960003036 amisulpride Drugs 0.000 claims 1
- NTJOBXMMWNYJFB-UHFFFAOYSA-N amisulpride Chemical compound CCN1CCCC1CNC(=O)C1=CC(S(=O)(=O)CC)=C(N)C=C1OC NTJOBXMMWNYJFB-UHFFFAOYSA-N 0.000 claims 1
- 230000000561 anti-psychotic effect Effects 0.000 claims 1
- 239000000164 antipsychotic agent Substances 0.000 claims 1
- 229960004372 aripiprazole Drugs 0.000 claims 1
- BNQDCRGUHNALGH-UHFFFAOYSA-N benserazide Chemical compound OCC(N)C(=O)NNCC1=CC=C(O)C(O)=C1O BNQDCRGUHNALGH-UHFFFAOYSA-N 0.000 claims 1
- 229960000911 benserazide Drugs 0.000 claims 1
- YSXKPIUOCJLQIE-UHFFFAOYSA-N biperiden Chemical compound C1C(C=C2)CC2C1C(C=1C=CC=CC=1)(O)CCN1CCCCC1 YSXKPIUOCJLQIE-UHFFFAOYSA-N 0.000 claims 1
- 239000004305 biphenyl Substances 0.000 claims 1
- 125000006268 biphenyl-3-yl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C1=C([H])C(*)=C([H])C([H])=C1[H] 0.000 claims 1
- 229960002802 bromocriptine Drugs 0.000 claims 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims 1
- 229960004205 carbidopa Drugs 0.000 claims 1
- TZFNLOMSOLWIDK-JTQLQIEISA-N carbidopa (anhydrous) Chemical compound NN[C@@](C(O)=O)(C)CC1=CC=C(O)C(O)=C1 TZFNLOMSOLWIDK-JTQLQIEISA-N 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 229960001076 chlorpromazine Drugs 0.000 claims 1
- ZPEIMTDSQAKGNT-UHFFFAOYSA-N chlorpromazine Chemical compound C1=C(Cl)C=C2N(CCCN(C)C)C3=CC=CC=C3SC2=C1 ZPEIMTDSQAKGNT-UHFFFAOYSA-N 0.000 claims 1
- 229960001552 chlorprothixene Drugs 0.000 claims 1
- 229960004170 clozapine Drugs 0.000 claims 1
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 0.000 claims 1
- 208000010877 cognitive disease Diseases 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 229960003529 diazepam Drugs 0.000 claims 1
- AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 229960002724 fenoldopam Drugs 0.000 claims 1
- TVURRHSHRRELCG-UHFFFAOYSA-N fenoldopam Chemical compound C1=CC(O)=CC=C1C1C2=CC(O)=C(O)C(Cl)=C2CCNC1 TVURRHSHRRELCG-UHFFFAOYSA-N 0.000 claims 1
- 229960003878 haloperidol Drugs 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 230000003301 hydrolyzing effect Effects 0.000 claims 1
- 229960003587 lisuride Drugs 0.000 claims 1
- 229960000423 loxapine Drugs 0.000 claims 1
- XJGVXQDUIWGIRW-UHFFFAOYSA-N loxapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2OC2=CC=C(Cl)C=C12 XJGVXQDUIWGIRW-UHFFFAOYSA-N 0.000 claims 1
- 229960000300 mesoridazine Drugs 0.000 claims 1
- SLVMESMUVMCQIY-UHFFFAOYSA-N mesoridazine Chemical compound CN1CCCCC1CCN1C2=CC(S(C)=O)=CC=C2SC2=CC=CC=C21 SLVMESMUVMCQIY-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 229950005651 naxagolide Drugs 0.000 claims 1
- JCSREICEMHWFAY-HUUCEWRRSA-N naxagolide Chemical compound C1=C(O)C=C2[C@H]3OCCN(CCC)[C@@H]3CCC2=C1 JCSREICEMHWFAY-HUUCEWRRSA-N 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 229960000762 perphenazine Drugs 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- YVUQSNJEYSNKRX-UHFFFAOYSA-N pimozide Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)CCCN1CCC(N2C(NC3=CC=CC=C32)=O)CC1 YVUQSNJEYSNKRX-UHFFFAOYSA-N 0.000 claims 1
- 229960003634 pimozide Drugs 0.000 claims 1
- FASDKYOPVNHBLU-ZETCQYMHSA-N pramipexole Chemical compound C1[C@@H](NCCC)CCC2=C1SC(N)=N2 FASDKYOPVNHBLU-ZETCQYMHSA-N 0.000 claims 1
- 229960003089 pramipexole Drugs 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- 229960001534 risperidone Drugs 0.000 claims 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 claims 1
- 229960004940 sulpiride Drugs 0.000 claims 1
- 229960005333 tetrabenazine Drugs 0.000 claims 1
- 229960002784 thioridazine Drugs 0.000 claims 1
- 229960005013 tiotixene Drugs 0.000 claims 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims 1
- 0 CC(*)N(C)C(*)(*)C(O)=O Chemical compound CC(*)N(C)C(*)(*)C(O)=O 0.000 description 8
- JAPMJSVZDUYFKL-UHFFFAOYSA-N C1C2C1CCC2 Chemical compound C1C2C1CCC2 JAPMJSVZDUYFKL-UHFFFAOYSA-N 0.000 description 1
- HZBKICSBEFOPSG-IKJXHCRLSA-N C[C@H](C1)NCCN1C(c1ccccc1)c1cc(C(F)(F)F)ccc1 Chemical compound C[C@H](C1)NCCN1C(c1ccccc1)c1cc(C(F)(F)F)ccc1 HZBKICSBEFOPSG-IKJXHCRLSA-N 0.000 description 1
- VOQCGPJENVDOCK-UHFFFAOYSA-N FC(c1cccc(C(c2ccccc2)N2CCNCC2)c1)(F)F Chemical compound FC(c1cccc(C(c2ccccc2)N2CCNCC2)c1)(F)F VOQCGPJENVDOCK-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81693606P | 2006-06-28 | 2006-06-28 | |
| US60/816,936 | 2006-06-28 | ||
| US85002706P | 2006-10-06 | 2006-10-06 | |
| US60/850,027 | 2006-10-06 | ||
| PCT/US2007/014842 WO2008002583A1 (en) | 2006-06-28 | 2007-06-26 | Glycine transporter-1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2009542661A JP2009542661A (ja) | 2009-12-03 |
| JP2009542661A5 true JP2009542661A5 (https=) | 2011-02-17 |
| JP5179486B2 JP5179486B2 (ja) | 2013-04-10 |
Family
ID=38565553
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009518233A Expired - Fee Related JP5179486B2 (ja) | 2006-06-28 | 2007-06-26 | グリシン輸送体−１阻害剤 |
Country Status (28)
| Country | Link |
|---|---|
| US (4) | US7538114B2 (https=) |
| EP (3) | EP2565183A1 (https=) |
| JP (1) | JP5179486B2 (https=) |
| KR (2) | KR101288781B1 (https=) |
| AR (1) | AR077156A1 (https=) |
| AU (1) | AU2007265467C1 (https=) |
| BR (1) | BRPI0713381A2 (https=) |
| CA (1) | CA2655159C (https=) |
| CR (1) | CR10570A (https=) |
| CY (1) | CY1115119T1 (https=) |
| DK (1) | DK2041088T3 (https=) |
| EA (1) | EA014959B3 (https=) |
| ES (1) | ES2452822T3 (https=) |
| HR (1) | HRP20140336T1 (https=) |
| IL (1) | IL195473A (https=) |
| MX (1) | MX2008015448A (https=) |
| MY (1) | MY153714A (https=) |
| NO (1) | NO20090402L (https=) |
| NZ (1) | NZ573129A (https=) |
| PE (2) | PE20080271A1 (https=) |
| PL (1) | PL2041088T3 (https=) |
| PT (1) | PT2041088E (https=) |
| RS (1) | RS53277B (https=) |
| SG (1) | SG172685A1 (https=) |
| SI (1) | SI2041088T1 (https=) |
| TW (1) | TWI429631B (https=) |
| WO (1) | WO2008002583A1 (https=) |
| ZA (1) | ZA201004216B (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ573129A (en) * | 2006-06-28 | 2011-06-30 | Amgen Inc | Piperazine acetic acid glycine transporter-1 inhibitors |
| EP2231601B1 (en) * | 2007-12-12 | 2014-06-18 | Amgen Inc. | Glycine transporter-1 inhibitors |
| AU2011261375B2 (en) * | 2010-06-04 | 2016-09-22 | Albany Molecular Research, Inc. | Glycine transporter-1 inhibitors, methods of making them, 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 |
| MA39888A (fr) | 2014-04-24 | 2017-03-01 | Dart Neuroscience Cayman Ltd | Composés de 2,4,5,6-tétrahydropyrrolo[3,4-c] pyrazole et 4,5,6,7-tétrahydro-2 h-pyrazolo [4,3-c] pyridine utilisés comme inhibiteurs de glyt1 |
| JP7055017B2 (ja) | 2014-09-29 | 2022-04-15 | 武田薬品工業株式会社 | 結晶形の１－（１－メチル－１ｈ－ピラゾール－４－イル）－ｎ－（（１ｒ，５ｓ，７ｓ）－９－メチル－３－オキサ－９－アザビシクロ［３．３．１］ノナン－７－イル）－１ｈ－インドール－３－カルボキサミド |
| TWI601712B (zh) | 2014-11-05 | 2017-10-11 | 達特神經科學（開曼）有限責任公司 | 作為ｇｌｙｔ１抑制劑之經取代之氮雜環丁基化合物 |
| 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 (https=) | 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 |
| DK154078C (da) | 1981-02-06 | 1989-05-22 | Ucb Sa | Analogifremgangsmaade til fremstilling af 2-(2-(4-(diphenyl-methyl)-1-piperazinyl)ethoxy)-acetamider eller syreadditionssalte heraf |
| 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 |
| CA2113449A1 (en) | 1991-07-19 | 1993-02-04 | Kazuhiro Kumagai | Piperazine derivatives and pharmaceuticals containing the same |
| 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 |
| AU3186395A (en) * | 1994-08-10 | 1996-03-07 | British Biotech Pharmaceuticals Limited | Imidazopyridine derivatives as dual histamine (h1) and platelet activating factor (paf) antagonists |
| 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 |
| AU4432496A (en) | 1994-12-23 | 1996-07-19 | Dr. Karl Thomae Gmbh | Piperazine derivatives, medicaments containing the same, their use and process for preparing the same |
| 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 |
| EP0918767A4 (en) * | 1996-05-31 | 2000-04-26 | Allelix Neuroscience Inc | PHARMACEUTICAL PRODUCT FOR THE TREATMENT OF NEUROLOGICAL AND NEUROPSYCHIATRIC DISORDERS |
| NZ332780A (en) | 1996-05-31 | 2000-07-28 | Allelix Neuroscience Inc | Substituted amines for the treatment of neurological and neuropsychiatric disorders |
| US6001854A (en) * | 1996-05-31 | 1999-12-14 | Allelix Neuroscience Inc. | Pharmaceutical for treating of neurological and neuropsychiatric disorders |
| 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 |
| CA2267500A1 (en) | 1996-10-04 | 1998-04-16 | Novo Nordisk A/S | 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 |
| WO1998055459A1 (en) * | 1997-06-04 | 1998-12-10 | Azwell Inc. | Process for producing piperazinesulfonamide derivatives and salts thereof |
| WO1999000376A1 (en) | 1997-06-25 | 1999-01-07 | 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 |
| ATE455108T1 (de) | 2001-02-16 | 2010-01-15 | Aventis Pharma Inc | Heterocyclische substituierte carbonyl derivate und ihre verwendung als dopamin d3 rezeptor liganden |
| EP1427418B1 (en) | 2001-08-24 | 2009-11-11 | Yale University | Piperazinone compounds as anti-tumor and anti-cancer agents |
| AR036492A1 (es) * | 2001-09-06 | 2004-09-15 | Schering Corp | Inhibidores de la 17beta-hidroxiesteroide deshidrogenasa tipo 3, composiciones farmaceuticas y el uso de dichos inhibidores para la elaboracion de un medicamento para el tratamiento de enfermedades androgeno dependientes |
| WO2003029199A1 (en) * | 2001-09-28 | 2003-04-10 | Takeda Chemical Industries, Ltd. | Benzene derivatives, process for preparing the same and use thereof |
| DE10149370A1 (de) * | 2001-10-06 | 2003-04-10 | Merck Patent Gmbh | Pyrazolderivate |
| AU2002347906A2 (en) * | 2001-10-16 | 2003-04-28 | Hypnion, Inc. | Treatment of CNS disorders using CNS target modulators |
| US7355042B2 (en) | 2001-10-16 | 2008-04-08 | 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 |
| US7378411B2 (en) | 2001-12-06 | 2008-05-27 | Merck & Co., Inc. | Substituted thienopyrimidinones as a mitotic kinesin inhibitor |
| AU2002364128B2 (en) | 2001-12-06 | 2008-03-06 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| AU2002363960B2 (en) | 2001-12-06 | 2008-07-10 | Merck Sharp & Dohme Corp. | Mitotic kinesin inhibitors |
| US20050107404A1 (en) | 2001-12-06 | 2005-05-19 | Fraley Mark E. | Mitotic kinesin inhibitors |
| US7262187B2 (en) | 2001-12-06 | 2007-08-28 | Merck & Co., Inc. | Substituted oxazolo- and thizaolopyrimidinones as a mitotic kinesin inhibitor |
| WO2003053942A1 (en) * | 2001-12-20 | 2003-07-03 | H. Lundbeck A/S | Aryloxyphenyl and arylsulfanylphenyl derivatives |
| KR100995557B1 (ko) | 2002-03-27 | 2010-11-22 | 썬 파마 어드밴스트 리서치 컴패니 리미티드 | 4-(디아릴메틸)-1-피페라지닐 유도체 |
| 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 |
| AU2003249881A1 (en) | 2002-07-02 | 2004-01-23 | Ucb Farchim S.A. | Diarylmethylpiperazines as prophylactic or therapeutic agents for viral myocarditis |
| SE0203303D0 (sv) | 2002-11-07 | 2002-11-07 | Astrazeneca Ab | Novel Compounds |
| RS53252B (sr) | 2003-08-11 | 2014-08-29 | F.Hoffmann-La Roche Ag. | Piperazin sa or-supstituisanom fenil grupom i njihova upotreba kao inhibitora glyt1 |
| 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 |
| US20100029681A1 (en) * | 2006-05-26 | 2010-02-04 | Hassan Pajouhesh | Heterocyclic compounds as calcium channel blockers |
| NZ573129A (en) * | 2006-06-28 | 2011-06-30 | Amgen Inc | Piperazine acetic acid glycine transporter-1 inhibitors |
| 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 |
-
2007
- 2007-06-26 NZ NZ573129A patent/NZ573129A/en not_active IP Right Cessation
- 2007-06-26 US US11/823,027 patent/US7538114B2/en not_active Expired - Fee Related
- 2007-06-26 EP EP12178740A patent/EP2565183A1/en not_active Withdrawn
- 2007-06-26 AU AU2007265467A patent/AU2007265467C1/en not_active Ceased
- 2007-06-26 DK DK07796466.6T patent/DK2041088T3/da active
- 2007-06-26 BR BRPI0713381-2A patent/BRPI0713381A2/pt not_active IP Right Cessation
- 2007-06-26 EA EA200900065A patent/EA014959B3/ru not_active IP Right Cessation
- 2007-06-26 MY MYPI20085047A patent/MY153714A/en unknown
- 2007-06-26 JP JP2009518233A patent/JP5179486B2/ja not_active Expired - Fee Related
- 2007-06-26 ES ES07796466.6T patent/ES2452822T3/es active Active
- 2007-06-26 PT PT77964666T patent/PT2041088E/pt unknown
- 2007-06-26 WO PCT/US2007/014842 patent/WO2008002583A1/en not_active Ceased
- 2007-06-26 PL PL07796466T patent/PL2041088T3/pl unknown
- 2007-06-26 KR KR1020117020250A patent/KR101288781B1/ko not_active Expired - Fee Related
- 2007-06-26 SI SI200731427T patent/SI2041088T1/sl unknown
- 2007-06-26 KR KR1020087032067A patent/KR101086589B1/ko not_active Expired - Fee Related
- 2007-06-26 EP EP07796466.6A patent/EP2041088B1/en active Active
- 2007-06-26 MX MX2008015448A patent/MX2008015448A/es active IP Right Grant
- 2007-06-26 EP EP15154777.5A patent/EP2947067A1/en not_active Withdrawn
- 2007-06-26 HR HRP20140336TT patent/HRP20140336T1/hr unknown
- 2007-06-26 SG SG2011041423A patent/SG172685A1/en unknown
- 2007-06-26 RS RS20140163A patent/RS53277B/sr unknown
- 2007-06-26 CA CA2655159A patent/CA2655159C/en not_active Expired - Fee Related
- 2007-06-27 TW TW096123386A patent/TWI429631B/zh not_active IP Right Cessation
- 2007-06-28 AR ARP070102897A patent/AR077156A1/es not_active Application Discontinuation
- 2007-07-02 PE PE2007000843A patent/PE20080271A1/es not_active Application Discontinuation
- 2007-07-02 PE PE2011002078A patent/PE20120223A1/es not_active Application Discontinuation
-
2008
- 2008-11-24 IL IL195473A patent/IL195473A/en not_active IP Right Cessation
-
2009
- 2009-01-16 CR CR10570A patent/CR10570A/es unknown
- 2009-01-27 NO NO20090402A patent/NO20090402L/no not_active Application Discontinuation
- 2009-05-12 US US12/464,697 patent/US8183244B2/en not_active Expired - Fee Related
-
2010
- 2010-06-14 ZA ZA2010/04216A patent/ZA201004216B/en unknown
-
2012
- 2012-03-21 US US13/426,539 patent/US8735383B2/en not_active Expired - Fee Related
-
2014
- 2014-03-31 CY CY20141100243T patent/CY1115119T1/el unknown
- 2014-04-29 US US14/264,731 patent/US9663476B2/en not_active Expired - Fee Related
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| JP2009542661A5 (https=) | ||
| RU2006105717A (ru) | Производные пиперазина и их применение в качестве терапевтических агентов | |
| JP2008513515A5 (https=) | ||
| RU2205827C2 (ru) | Производное ацилпиперазинилпиримидина, способы его получения, фармацевтическая композиция | |
| NZ598294A (en) | Heterocyclic compounds for the inhibition of pask | |
| NZ601126A (en) | Voltage-gated sodium channel blockers | |
| CA2584666A1 (en) | Pyrimidine derivative condensed with a non-aromatic ring | |
| JPH11193281A (ja) | アデノシンａ３受容体拮抗剤およびチアゾール化合物 | |
| JP2009539762A (ja) | Ｈ３受容体のテトラリン拮抗薬 | |
| RU2009117705A (ru) | Производные 2-аминокарбонилпиридина | |
| JP2017526734A5 (https=) | ||
| NZ703941A (en) | Apoptosis-inducing agents for the treatment of cancer and immune and autoimmune diseases | |
| PE20080360A1 (es) | Derivados 4-bencilftalazinona 2-sustituidos como antagonistas de histaminas h1 y h3 | |
| JP2014523897A5 (https=) | ||
| AR048306A1 (es) | Derivados de acidos carboxilicos aromaticos con capacidad moduladora de los niveles de insulina, composiciones farmaceuticas que los contienen y su uso en el tratamiento de trastornos metabolicos que responden a la regulacion de gpr40 | |
| TW200745070A (en) | Novel 1,4-benzothiazepine 1,1-dioxide derivative with improved properties, process for its preparation, medicaments comprising this compound and their use | |
| MX2007008279A (es) | Compuestos de arilamina sustituidos y su uso como moduladores de la 5-ht6. | |
| WO2000069432A1 (en) | Remedies or preventives for diseases in association with chemokines | |
| AU2013309124B2 (en) | Reduced central corneal thickening by use of hydrophilic ester prodrugs of beta-chlorocyclopentanes | |
| JP2012505234A5 (https=) | ||
| US9663476B2 (en) | Glycine transporter-1 inhibitors | |
| EA200971086A1 (ru) | Фармацевтические композиции и способ лечения шизофрении | |
| RU2011102396A (ru) | Аминосоединения и их медицинское применение | |
| JP2015524483A5 (https=) | ||
| RU2016120610A (ru) | Производное сульфонамида и его применение в медицине |