JP2007502808A5 - - Google Patents
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- JP2007502808A5 JP2007502808A5 JP2006523697A JP2006523697A JP2007502808A5 JP 2007502808 A5 JP2007502808 A5 JP 2007502808A5 JP 2006523697 A JP2006523697 A JP 2006523697A JP 2006523697 A JP2006523697 A JP 2006523697A JP 2007502808 A5 JP2007502808 A5 JP 2007502808A5
- Authority
- JP
- Japan
- Prior art keywords
- chlorophenyl
- phenyl
- aza
- hydroxy
- bicyclo
- 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.)
- Pending
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- -1 2-hydroxy-1,2,3,4-tetrahydro-naphthalen-2-ylmethyl Chemical group 0.000 claims 28
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 15
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 14
- KBPHGUKTJKPERJ-UHFFFAOYSA-N 2-methoxyethanesulfonic acid Chemical compound COCCS(O)(=O)=O KBPHGUKTJKPERJ-UHFFFAOYSA-N 0.000 claims 13
- 150000001408 amides Chemical class 0.000 claims 13
- 239000008194 pharmaceutical composition Substances 0.000 claims 12
- 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 claims 9
- 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 claims 9
- 206010012335 Dependence Diseases 0.000 claims 8
- 150000001875 compounds Chemical class 0.000 claims 8
- 150000004677 hydrates Chemical class 0.000 claims 8
- 239000012453 solvate Substances 0.000 claims 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 6
- NOVIRJZSSSHOFF-UHFFFAOYSA-N 3-[1-(2,3-dihydro-1h-inden-2-ylmethyl)-3,4-dimethylpiperidin-4-yl]benzamide Chemical compound CC1CN(CC2CC3=CC=CC=C3C2)CCC1(C)C1=CC=CC(C(N)=O)=C1 NOVIRJZSSSHOFF-UHFFFAOYSA-N 0.000 claims 3
- CMXNJCYHOYIGPE-UHFFFAOYSA-N 3-[1-[(1-hydroxy-3-phenylcyclobutyl)methyl]-3,4-dimethylpiperidin-4-yl]benzamide Chemical compound C1CC(C=2C=C(C=CC=2)C(N)=O)(C)C(C)CN1CC(C1)(O)CC1C1=CC=CC=C1 CMXNJCYHOYIGPE-UHFFFAOYSA-N 0.000 claims 3
- VLJHXPKDNBNFPN-UHFFFAOYSA-N 3-[1-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-3,4-dimethylpiperidin-4-yl]benzamide Chemical compound CC1CN(CC2(O)CC3=CC=CC=C3C2)CCC1(C)C1=CC=CC(C(N)=O)=C1 VLJHXPKDNBNFPN-UHFFFAOYSA-N 0.000 claims 3
- LTENPJFSBSGWFV-UHFFFAOYSA-N 3-[1-[3-(1-hydroxycyclohexyl)propyl]-3,4-dimethylpiperidin-4-yl]benzamide Chemical compound C1CC(C=2C=C(C=CC=2)C(N)=O)(C)C(C)CN1CCCC1(O)CCCCC1 LTENPJFSBSGWFV-UHFFFAOYSA-N 0.000 claims 3
- YZMRJTFTIRSULG-UHFFFAOYSA-N 3-[2-[(1-hydroxy-3-phenylcyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2(O)CC(C2)C=2C=CC=CC=2)CC3)=C1 YZMRJTFTIRSULG-UHFFFAOYSA-N 0.000 claims 3
- ZCDWSEYWBPLIPE-UHFFFAOYSA-N 3-[2-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4CC2)CC3)=C1 ZCDWSEYWBPLIPE-UHFFFAOYSA-N 0.000 claims 3
- KDAMUYVTYZYYMY-UHFFFAOYSA-N 3-[2-[3-(1-hydroxycyclohexyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCCC2)CC3)=C1 KDAMUYVTYZYYMY-UHFFFAOYSA-N 0.000 claims 3
- NQDNSVFGDWTZRD-UHFFFAOYSA-N 3-[3-(2,3-dihydro-1h-inden-2-ylmethyl)-6-ethyl-3-azabicyclo[3.1.0]hexan-6-yl]benzamide Chemical compound C12CN(CC3CC4=CC=CC=C4C3)CC2C1(CC)C1=CC=CC(C(N)=O)=C1 NQDNSVFGDWTZRD-UHFFFAOYSA-N 0.000 claims 3
- CQMGDWUBLFGSDQ-UHFFFAOYSA-N 3-[3-[(1-hydroxy-3-phenylcyclobutyl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CC(C1)(O)CC1C1=CC=CC=C1 CQMGDWUBLFGSDQ-UHFFFAOYSA-N 0.000 claims 3
- PNUIAAYEYHRGJI-UHFFFAOYSA-N 3-[3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C1N(CC2(O)CC3=CC=CC=C3C2)CC2CCC1C2(OC)C1=CC=CC(C(N)=O)=C1 PNUIAAYEYHRGJI-UHFFFAOYSA-N 0.000 claims 3
- PCUUSYJXGVLVTO-UHFFFAOYSA-N 3-[3-[3-(1-hydroxycyclohexyl)propyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]benzamide Chemical compound C=1C=CC(C(N)=O)=CC=1C1(OC)C(C2)CCC1CN2CCCC1(O)CCCCC1 PCUUSYJXGVLVTO-UHFFFAOYSA-N 0.000 claims 3
- KJJLEOOLZLWLSS-UHFFFAOYSA-N 3-[6-ethyl-3-[(1-hydroxy-3-phenylcyclobutyl)methyl]-3-azabicyclo[3.1.0]hexan-6-yl]benzamide Chemical compound C1C2C(CC)(C=3C=C(C=CC=3)C(N)=O)C2CN1CC(C1)(O)CC1C1=CC=CC=C1 KJJLEOOLZLWLSS-UHFFFAOYSA-N 0.000 claims 3
- SCNSHBHEDUUZDM-UHFFFAOYSA-N 3-[6-ethyl-3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-3-azabicyclo[3.1.0]hexan-6-yl]benzamide Chemical compound C12CN(CC3(O)CC4=CC=CC=C4C3)CC2C1(CC)C1=CC=CC(C(N)=O)=C1 SCNSHBHEDUUZDM-UHFFFAOYSA-N 0.000 claims 3
- ZFMTXYPTAWEVCX-UHFFFAOYSA-N 3-[6-ethyl-3-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-3-azabicyclo[3.1.0]hexan-6-yl]benzamide Chemical compound C12CN(CC3(O)CC4=CC=CC=C4CC3)CC2C1(CC)C1=CC=CC(C(N)=O)=C1 ZFMTXYPTAWEVCX-UHFFFAOYSA-N 0.000 claims 3
- IIMDLDQJDZKMRU-UHFFFAOYSA-N 3-[6-ethyl-3-[3-(1-hydroxycyclohexyl)propyl]-3-azabicyclo[3.1.0]hexan-6-yl]benzamide Chemical compound C1C2C(CC)(C=3C=C(C=CC=3)C(N)=O)C2CN1CCCC1(O)CCCCC1 IIMDLDQJDZKMRU-UHFFFAOYSA-N 0.000 claims 3
- 229940123257 Opioid receptor antagonist Drugs 0.000 claims 3
- DQASZCKCSVFDCH-UHFFFAOYSA-N n-[3-[2-[(1-hydroxy-3-phenylcyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC(C2)C=2C=CC=CC=2)CC3)=C1 DQASZCKCSVFDCH-UHFFFAOYSA-N 0.000 claims 3
- RQZJNXFHIROAPH-UHFFFAOYSA-N n-[3-[2-[(1-hydroxy-3-phenylcyclobutyl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC(C2)C=2C=CC=CC=2)CC3)=C1 RQZJNXFHIROAPH-UHFFFAOYSA-N 0.000 claims 3
- PARWEPAVIFDMQQ-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4C2)CC3)=C1 PARWEPAVIFDMQQ-UHFFFAOYSA-N 0.000 claims 3
- MWQBBRUNZRMVLU-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4C2)CC3)=C1 MWQBBRUNZRMVLU-UHFFFAOYSA-N 0.000 claims 3
- HFTKEKZOAHFQKB-UHFFFAOYSA-N n-[3-[2-[(2-hydroxy-3,4-dihydro-1h-naphthalen-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4CC2)CC3)=C1 HFTKEKZOAHFQKB-UHFFFAOYSA-N 0.000 claims 3
- VWCPRVNVISOSDS-UHFFFAOYSA-N n-[3-[2-[3-(1-hydroxycyclohexyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]methanesulfonamide Chemical compound CS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCCC2)CC3)=C1 VWCPRVNVISOSDS-UHFFFAOYSA-N 0.000 claims 3
- UWTVBOIAYXZBRE-UHFFFAOYSA-N n-[3-[3-(2,3-dihydro-1h-inden-2-ylmethyl)-6-ethyl-3-azabicyclo[3.1.0]hexan-6-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound C12CN(CC3CC4=CC=CC=C4C3)CC2C1(CC)C1=CC=CC(NS(=O)(=O)CCOC)=C1 UWTVBOIAYXZBRE-UHFFFAOYSA-N 0.000 claims 3
- YXMNCEWFXWZDRL-UHFFFAOYSA-N n-[3-[3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-8-methoxy-3-azabicyclo[3.2.1]octan-8-yl]phenyl]methanesulfonamide Chemical compound C1N(CC2(O)CC3=CC=CC=C3C2)CC2CCC1C2(OC)C1=CC=CC(NS(C)(=O)=O)=C1 YXMNCEWFXWZDRL-UHFFFAOYSA-N 0.000 claims 3
- ZBVPUFSKFGYNLC-UHFFFAOYSA-N n-[3-[6-ethyl-3-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-3-azabicyclo[3.1.0]hexan-6-yl]phenyl]methanesulfonamide Chemical compound C12CN(CC3(O)CC4=CC=CC=C4C3)CC2C1(CC)C1=CC=CC(NS(C)(=O)=O)=C1 ZBVPUFSKFGYNLC-UHFFFAOYSA-N 0.000 claims 3
- LWWRWOHYBARKAQ-UHFFFAOYSA-N n-[3-[6-ethyl-3-[3-(1-hydroxycyclohexyl)propyl]-3-azabicyclo[3.1.0]hexan-6-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound C1C2C(CC)(C=3C=C(NS(=O)(=O)CCOC)C=CC=3)C2CN1CCCC1(O)CCCCC1 LWWRWOHYBARKAQ-UHFFFAOYSA-N 0.000 claims 3
- 239000003401 opiate antagonist Substances 0.000 claims 3
- CZLBJIOKKYHVOG-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)-3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]-3-(ethylamino)azetidine-3-carboxamide Chemical compound C1C(NCC)(C(N)=O)CN1C1=CC=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 CZLBJIOKKYHVOG-UHFFFAOYSA-N 0.000 claims 2
- ZNNPDKATJWCFJB-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)-3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]-4-(ethylamino)piperidine-4-carboxamide Chemical compound C1CC(NCC)(C(N)=O)CCN1C1=CC=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 ZNNPDKATJWCFJB-UHFFFAOYSA-N 0.000 claims 2
- INMZIBQWBSNYED-UHFFFAOYSA-N 1-[2-(2-chlorophenyl)-3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]-4-(propan-2-ylamino)piperidine-4-carboxamide Chemical compound C1CC(NC(C)C)(C(N)=O)CCN1C1=CC=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 INMZIBQWBSNYED-UHFFFAOYSA-N 0.000 claims 2
- XJFUIILGVMOOHV-UHFFFAOYSA-N 1-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-(ethylamino)azetidine-3-carboxamide Chemical compound C1C(NCC)(C(N)=O)CN1C1=NC(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 XJFUIILGVMOOHV-UHFFFAOYSA-N 0.000 claims 2
- HYBPYDGGQPVUBJ-UHFFFAOYSA-N 1-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-3-(propan-2-ylamino)azetidine-3-carboxamide Chemical compound C1C(NC(C)C)(C(N)=O)CN1C1=NC(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 HYBPYDGGQPVUBJ-UHFFFAOYSA-N 0.000 claims 2
- MKULERGVQWMOJY-UHFFFAOYSA-N 1-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-4-(ethylamino)piperidine-4-carboxamide Chemical compound C1CC(NCC)(C(N)=O)CCN1C1=NC(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 MKULERGVQWMOJY-UHFFFAOYSA-N 0.000 claims 2
- DDLXFJXATMJVFP-UHFFFAOYSA-N 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-3-(ethylamino)azetidine-3-carboxamide Chemical compound C1C(NCC)(C(N)=O)CN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 DDLXFJXATMJVFP-UHFFFAOYSA-N 0.000 claims 2
- SQSZXZKMVHUPRD-UHFFFAOYSA-N 1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-4-(propan-2-ylamino)piperidine-4-carboxamide Chemical compound C1CC(NC(C)C)(C(N)=O)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 SQSZXZKMVHUPRD-UHFFFAOYSA-N 0.000 claims 2
- BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims 2
- XWJBBHRGYQANKK-UHFFFAOYSA-N 3-[2-[(2-hydroxy-1,3-dihydroinden-2-yl)methyl]-2-azabicyclo[3.3.1]nonan-5-yl]benzamide Chemical compound NC(=O)C1=CC=CC(C23CC(CCC2)N(CC2(O)CC4=CC=CC=C4C2)CC3)=C1 XWJBBHRGYQANKK-UHFFFAOYSA-N 0.000 claims 2
- YBQGLTGAHBCMME-UHFFFAOYSA-N 4-amino-1-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]piperidine-4-carboxamide Chemical compound C1CC(C(=O)N)(N)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 YBQGLTGAHBCMME-UHFFFAOYSA-N 0.000 claims 2
- FMQLEHWCAMNBAG-UHFFFAOYSA-N 8-[7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-yl]-1-propan-2-yl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound CC(C)N1CNC(=O)C11CCN(C=2N3N=C(C(=C3N=C(C)N=2)C=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 FMQLEHWCAMNBAG-UHFFFAOYSA-N 0.000 claims 2
- MGXWXNOHTWTTFC-UHFFFAOYSA-N 8-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-1-propan-2-yl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound CC(C)N1CNC(=O)C11CCN(C=2C=3N=C(N(C=3N=CN=2)C=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 MGXWXNOHTWTTFC-UHFFFAOYSA-N 0.000 claims 2
- 208000007848 Alcoholism Diseases 0.000 claims 2
- 208000022497 Cocaine-Related disease Diseases 0.000 claims 2
- 206010013654 Drug abuse Diseases 0.000 claims 2
- 241000208125 Nicotiana Species 0.000 claims 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims 2
- 208000029650 alcohol withdrawal Diseases 0.000 claims 2
- 230000003542 behavioural effect Effects 0.000 claims 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 2
- 201000006145 cocaine dependence Diseases 0.000 claims 2
- 206010013663 drug dependence Diseases 0.000 claims 2
- VWHWAPBGKJVPNM-UHFFFAOYSA-N n-[3-[2-[3-(1-hydroxycyclohexyl)propyl]-2-azabicyclo[3.3.1]nonan-5-yl]phenyl]-2-methoxyethanesulfonamide Chemical compound COCCS(=O)(=O)NC1=CC=CC(C23CC(CCC2)N(CCCC2(O)CCCCC2)CC3)=C1 VWHWAPBGKJVPNM-UHFFFAOYSA-N 0.000 claims 2
- UNAZAADNBYXMIV-UHFFFAOYSA-N otenabant Chemical compound C1CC(NCC)(C(N)=O)CCN1C1=NC=NC2=C1N=C(C=1C(=CC=CC=1)Cl)N2C1=CC=C(Cl)C=C1 UNAZAADNBYXMIV-UHFFFAOYSA-N 0.000 claims 2
- 208000011117 substance-related disease Diseases 0.000 claims 2
- 208000024891 symptom Diseases 0.000 claims 2
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 claims 1
- NBBLBZXXTIHYGR-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-3-[1-(2,2-dimethyloxan-4-yl)imidazol-4-yl]-4-methylpyrazole Chemical compound CC=1C(C=2N=CN(C=2)C2CC(C)(C)OCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 NBBLBZXXTIHYGR-UHFFFAOYSA-N 0.000 claims 1
- RSHRLSNTSNPHBI-UHFFFAOYSA-N 1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methyl-3-[1-(1-phenylethyl)imidazol-4-yl]pyrazole Chemical compound C1=NC(C=2C(=C(N(N=2)C=2C(=CC=CC=2)Cl)C=2C=CC(Cl)=CC=2)C)=CN1C(C)C1=CC=CC=C1 RSHRLSNTSNPHBI-UHFFFAOYSA-N 0.000 claims 1
- CTSFSQZYEGEKNJ-UHFFFAOYSA-N 1-(oxazepan-4-yl)ethanone Chemical compound O1NCC(CCC1)C(C)=O CTSFSQZYEGEKNJ-UHFFFAOYSA-N 0.000 claims 1
- KGJHVABFBBJFIG-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-(3,3-dimethylpiperidin-1-yl)ethanol Chemical compound CC=1C(C(O)CN2CC(C)(C)CCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 KGJHVABFBBJFIG-UHFFFAOYSA-N 0.000 claims 1
- FLLKDUQZOAVVFU-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-(3,5-dimethylpiperidin-1-yl)ethanol Chemical compound C1C(C)CC(C)CN1CC(O)C1=NN(C=2C(=CC=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C1C FLLKDUQZOAVVFU-UHFFFAOYSA-N 0.000 claims 1
- CSIFSTSKGZGCOA-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-[4-(1-methylcyclopropanecarbonyl)piperazin-1-yl]ethanone Chemical compound CC=1C(C(=O)CN2CCN(CC2)C(=O)C2(C)CC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 CSIFSTSKGZGCOA-UHFFFAOYSA-N 0.000 claims 1
- MJKOCBMDVCJJOQ-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-[4-(1-methylpyrrole-2-carbonyl)piperazin-1-yl]ethanone Chemical compound CC=1C(C(=O)CN2CCN(CC2)C(=O)C=2N(C=CC=2)C)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 MJKOCBMDVCJJOQ-UHFFFAOYSA-N 0.000 claims 1
- ZIKXMOOJNIZFNL-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-morpholin-4-ylethanol Chemical compound CC=1C(C(O)CN2CCOCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 ZIKXMOOJNIZFNL-UHFFFAOYSA-N 0.000 claims 1
- JBCFDMJWDPFMLH-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-morpholin-4-ylethanone Chemical compound CC=1C(C(=O)CN2CCOCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 JBCFDMJWDPFMLH-UHFFFAOYSA-N 0.000 claims 1
- WFUGOPUQRHLVDJ-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-piperidin-1-ylethanol Chemical compound CC=1C(C(O)CN2CCCCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 WFUGOPUQRHLVDJ-UHFFFAOYSA-N 0.000 claims 1
- KEKFWCUOYHQBHF-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-piperidin-1-ylethanone Chemical compound CC=1C(C(=O)CN2CCCCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 KEKFWCUOYHQBHF-UHFFFAOYSA-N 0.000 claims 1
- LMVIYCSQQODEFW-UHFFFAOYSA-N 1-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-pyrrolidin-1-ylethanone Chemical compound CC=1C(C(=O)CN2CCCC2)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 LMVIYCSQQODEFW-UHFFFAOYSA-N 0.000 claims 1
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- KPQBABKRCICYCP-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-(2-cyclohexyl-1H-imidazol-5-yl)-1-(2,4-dichlorophenyl)-4-methylpyrazole Chemical compound CC=1C(C=2NC(=NC=2)C2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 KPQBABKRCICYCP-UHFFFAOYSA-N 0.000 claims 1
- MAOZBIOYMACLOW-UHFFFAOYSA-N 5-(4-chlorophenyl)-3-(5-cyclohexyl-1H-imidazol-2-yl)-1-(2,4-dichlorophenyl)-4-methylpyrazole Chemical compound CC=1C(C=2NC(=CN=2)C2CCCCC2)=NN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 MAOZBIOYMACLOW-UHFFFAOYSA-N 0.000 claims 1
- MBJUYTICAOCFKW-UHFFFAOYSA-N 5-[2-(2,4-dichlorophenyl)-4-methyl-5-[1-(2-phenylpropan-2-yl)imidazol-4-yl]pyrazol-3-yl]-2-methoxypyridine Chemical compound C1=NC(OC)=CC=C1C1=C(C)C(C=2N=CN(C=2)C(C)(C)C=2C=CC=CC=2)=NN1C1=CC=C(Cl)C=C1Cl MBJUYTICAOCFKW-UHFFFAOYSA-N 0.000 claims 1
- MZRPLPNMEBKVMW-UHFFFAOYSA-N 6-(1-benzylpyrrolidin-3-yl)oxy-9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(OC3CN(CC=4C=CC=CC=4)CC3)=C2N=C1C1=CC=C(Cl)C=C1Cl MZRPLPNMEBKVMW-UHFFFAOYSA-N 0.000 claims 1
- CYZRHEQQZJGZRH-UHFFFAOYSA-N 7-(1-benzylpyrrolidin-3-yl)oxy-2-(2-chlorophenyl)-3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidine Chemical compound C1=CC(Cl)=CC=C1C1=C2N=CC=C(OC3CN(CC=4C=CC=CC=4)CC3)N2N=C1C1=CC=CC=C1Cl CYZRHEQQZJGZRH-UHFFFAOYSA-N 0.000 claims 1
- MPCZFCKCHMXKSZ-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-4-(4-propan-2-ylsulfonylpiperazin-1-yl)pyrazolo[1,5-a][1,3,5]triazine Chemical compound C1CN(S(=O)(=O)C(C)C)CCN1C1=NC(C)=NC2=C(C=3C=CC(Cl)=CC=3)C(C=3C(=CC=CC=3)Cl)=NN12 MPCZFCKCHMXKSZ-UHFFFAOYSA-N 0.000 claims 1
- VUTLQAOPBPMEKF-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-4-(4-pyrimidin-2-ylpiperazin-1-yl)pyrazolo[1,5-a][1,3,5]triazine Chemical compound N12N=C(C=3C(=CC=CC=3)Cl)C(C=3C=CC(Cl)=CC=3)=C2N=C(C)N=C1N(CC1)CCN1C1=NC=CC=N1 VUTLQAOPBPMEKF-UHFFFAOYSA-N 0.000 claims 1
- OCQLVFVXVCTHHD-ROUUACIJSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-4-[(1s,4s)-2-methylsulfonyl-2,5-diazabicyclo[2.2.1]heptan-5-yl]pyrazolo[1,5-a][1,3,5]triazine Chemical compound C([C@]1(N(C[C@@]2(C1)[H])S(C)(=O)=O)[H])N2C(N1N=2)=NC(C)=NC1=C(C=1C=CC(Cl)=CC=1)C=2C1=CC=CC=C1Cl OCQLVFVXVCTHHD-ROUUACIJSA-N 0.000 claims 1
- GPSKJJNUXWWNBR-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-4-piperidin-1-ylpyrazolo[1,5-a][1,3,5]triazine Chemical compound N12N=C(C=3C(=CC=CC=3)Cl)C(C=3C=CC(Cl)=CC=3)=C2N=C(C)N=C1N1CCCCC1 GPSKJJNUXWWNBR-UHFFFAOYSA-N 0.000 claims 1
- WKMDUNKYIDESRF-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-4-propan-2-yloxypyrazolo[1,5-a][1,3,5]triazine Chemical compound N=1N2C(OC(C)C)=NC(C)=NC2=C(C=2C=CC(Cl)=CC=2)C=1C1=CC=CC=C1Cl WKMDUNKYIDESRF-UHFFFAOYSA-N 0.000 claims 1
- BSEUFVUYWQGTQO-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methyl-n-(2-morpholin-4-ylethyl)pyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound N12N=C(C=3C(=CC=CC=3)Cl)C(C=3C=CC(Cl)=CC=3)=C2N=C(C)N=C1NCCN1CCOCC1 BSEUFVUYWQGTQO-UHFFFAOYSA-N 0.000 claims 1
- BACFLWLVLGFHMI-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-4-(1-cyclohexylazetidin-3-yl)oxy-2-methylpyrazolo[1,5-a][1,3,5]triazine Chemical compound N12N=C(C=3C(=CC=CC=3)Cl)C(C=3C=CC(Cl)=CC=3)=C2N=C(C)N=C1OC(C1)CN1C1CCCCC1 BACFLWLVLGFHMI-UHFFFAOYSA-N 0.000 claims 1
- QDDSPBSONLNBDS-UHFFFAOYSA-N 7-(2-chlorophenyl)-8-(4-chlorophenyl)-n-[2-(4-fluorophenyl)ethyl]-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound N12N=C(C=3C(=CC=CC=3)Cl)C(C=3C=CC(Cl)=CC=3)=C2N=C(C)N=C1NCCC1=CC=C(F)C=C1 QDDSPBSONLNBDS-UHFFFAOYSA-N 0.000 claims 1
- QVYSNUZRPPOOSX-UHFFFAOYSA-N 8-[2-(2-chlorophenyl)-3-(4-chlorophenyl)pyrazolo[1,5-a]pyrimidin-7-yl]-1-propan-2-yl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound CC(C)N1CNC(=O)C11CCN(C=2N3N=C(C(=C3N=CC=2)C=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 QVYSNUZRPPOOSX-UHFFFAOYSA-N 0.000 claims 1
- UTVMMSUELWAQIR-UHFFFAOYSA-N 8-[9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)purin-6-yl]-1-propan-2-yl-1,3,8-triazaspiro[4.5]decan-4-one Chemical compound CC(C)N1CNC(=O)C11CCN(C=2C=3N=C(N(C=3N=CN=2)C=2C=CC(Cl)=CC=2)C=2C(=CC(Cl)=CC=2)Cl)CC1 UTVMMSUELWAQIR-UHFFFAOYSA-N 0.000 claims 1
- NVEWRUMMUBKWLP-UHFFFAOYSA-N 9-(4-chlorophenyl)-6-(1-cyclohexylazetidin-3-yl)oxy-8-(2,4-dichlorophenyl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(OC3CN(C3)C3CCCCC3)=C2N=C1C1=CC=C(Cl)C=C1Cl NVEWRUMMUBKWLP-UHFFFAOYSA-N 0.000 claims 1
- HDPLEFUIDWOLLX-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyridin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CC=3)=C2N=C1C1=CC=C(Cl)C=C1Cl HDPLEFUIDWOLLX-UHFFFAOYSA-N 0.000 claims 1
- VNOGOEOTNFURPS-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-(4-pyrimidin-2-ylpiperazin-1-yl)purine Chemical compound C1=CC(Cl)=CC=C1N1C2=NC=NC(N3CCN(CC3)C=3N=CC=CN=3)=C2N=C1C1=CC=C(Cl)C=C1Cl VNOGOEOTNFURPS-UHFFFAOYSA-N 0.000 claims 1
- PPNKCVSOPVJBPB-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-[(2-methylpropan-2-yl)oxy]purine Chemical compound N=1C=2C(OC(C)(C)C)=NC=NC=2N(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl PPNKCVSOPVJBPB-UHFFFAOYSA-N 0.000 claims 1
- MOMMTIGOEFZQSC-UHFFFAOYSA-N 9-(4-chlorophenyl)-8-(2,4-dichlorophenyl)-6-propan-2-yloxypurine Chemical compound N=1C=2C(OC(C)C)=NC=NC=2N(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl MOMMTIGOEFZQSC-UHFFFAOYSA-N 0.000 claims 1
- QMTNIILDNUELGY-UHFFFAOYSA-N 9-[8-(2-chlorophenyl)-9-(4-chlorophenyl)purin-6-yl]-1-methyl-4-oxa-1,9-diazaspiro[5.5]undecan-2-one Chemical compound CN1C(=O)COCC11CCN(C=2C=3N=C(N(C=3N=CN=2)C=2C=CC(Cl)=CC=2)C=2C(=CC=CC=2)Cl)CC1 QMTNIILDNUELGY-UHFFFAOYSA-N 0.000 claims 1
- 208000001613 Gambling Diseases 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- MKJDUHZPLQYUCB-UHFFFAOYSA-N decan-4-one Chemical compound CCCCCCC(=O)CCC MKJDUHZPLQYUCB-UHFFFAOYSA-N 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000037406 food intake Effects 0.000 claims 1
- 125000006178 methyl benzyl group Chemical group 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- UANAQVHSLHQZFG-UHFFFAOYSA-N n-[1-[2-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-methylpyrazol-3-yl]-2-oxoethyl]piperidin-4-yl]-2,2,2-trifluoroacetamide Chemical compound CC=1C(C(=O)CN2CCC(CC2)NC(=O)C(F)(F)F)=NN(C=2C(=CC=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 UANAQVHSLHQZFG-UHFFFAOYSA-N 0.000 claims 1
- MRKIECYDPOPRBO-UHFFFAOYSA-N n-butyl-7-(2-chlorophenyl)-8-(4-chlorophenyl)-2-methylpyrazolo[1,5-a][1,3,5]triazin-4-amine Chemical compound N=1N2C(NCCCC)=NC(C)=NC2=C(C=2C=CC(Cl)=CC=2)C=1C1=CC=CC=C1Cl MRKIECYDPOPRBO-UHFFFAOYSA-N 0.000 claims 1
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| US49680303P | 2003-08-21 | 2003-08-21 | |
| PCT/IB2004/002596 WO2005018645A1 (en) | 2003-08-21 | 2004-08-09 | A pharmaceutical composition for the prevention and treatment of addiction in a mammal |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2007502808A JP2007502808A (ja) | 2007-02-15 |
| JP2007502808A5 true JP2007502808A5 (https=) | 2007-08-16 |
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| JP2006523697A Pending JP2007502808A (ja) | 2003-08-21 | 2004-08-09 | 哺乳類における依存症の予防と治療のための薬剤組成物 |
Country Status (7)
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| US (1) | US20050043327A1 (https=) |
| EP (1) | EP1658082A1 (https=) |
| JP (1) | JP2007502808A (https=) |
| BR (1) | BRPI0413693A (https=) |
| CA (1) | CA2536280A1 (https=) |
| MX (1) | MXPA06002035A (https=) |
| WO (1) | WO2005018645A1 (https=) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1440059B1 (en) * | 2001-10-22 | 2008-04-16 | Pfizer Products Inc. | 3-azabicyclo(3.1.0)hexane derivatives as opioid receptor antagonists |
| CA2499994C (en) * | 2002-09-23 | 2012-07-10 | Verion, Inc. | Abuse-resistant pharmaceutical compositions |
| US7129239B2 (en) * | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| MXPA05007485A (es) | 2003-01-14 | 2006-01-30 | Arena Pharm Inc | Derivados de arilo y heteroarilo 1,2,3-trisubstituidos como moduladores del metabolismo y la profilaxis y tratamiento de trastornos relacionados con ello tales como diabetes e hiperglicemia. |
| US7132426B2 (en) * | 2003-07-14 | 2006-11-07 | Arena Pharmaceuticals, Inc. | Fused-aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| AU2006305104B2 (en) * | 2005-10-21 | 2009-10-22 | Mitsubishi Tanabe Pharma Corporation | Pyrazolo[1,5-a]pyrimidine compounds as cannabinoid receptor antagonists |
| AR061793A1 (es) | 2006-07-05 | 2008-09-24 | Mitsubishi Tanabe Pharma Corp | Compuesto de pirazolo[1,5-a] pirimidina y composicion farmaceutica |
| JP5269795B2 (ja) * | 2006-09-29 | 2013-08-21 | グリーン・クロス・コーポレイション | カンナビノイドｃｂ１受容体アンタゴニストとしてのヘテロアリール−ピラゾール誘導体 |
| WO2008044111A1 (en) * | 2006-10-13 | 2008-04-17 | Pfizer Products Inc. | Pharmaceutical formulation tablet |
| JP3145620U (ja) | 2008-07-30 | 2008-10-16 | 公二 平井 | 擬似嗜好物品 |
| US8252791B2 (en) * | 2008-08-13 | 2012-08-28 | Jenrin Discovery, Inc. | Purine compounds as cannabinoid receptor blockers |
| UA104010C2 (en) * | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| GB0908394D0 (en) | 2009-05-15 | 2009-06-24 | Univ Leuven Kath | Novel viral replication inhibitors |
| GB0913636D0 (en) | 2009-08-05 | 2009-09-16 | Univ Leuven Kath | Novel viral replication inhibitors |
| PH12013500547A1 (en) | 2010-09-22 | 2013-06-10 | Arena Pharm Inc | Modulators of the gpr119 receptor and the treatment of disorders related thereto |
| JP2013542243A (ja) | 2010-11-15 | 2013-11-21 | カトリーケ ウニヴェルシテイト ルーヴェン | 新規な抗ウイルス性化合物 |
| US9663463B2 (en) | 2013-11-20 | 2017-05-30 | Sanwa Kagaku Kenkyusho Co., Ltd. | 3-azabicyclo[3.1.0]hexane derivative and use thereof for medical purpose |
| MX386419B (es) | 2015-01-06 | 2025-03-18 | Arena Pharm Inc | Metodos de condiciones de tratamiento relacionadas con el receptor s1p1. |
| KR20180004734A (ko) | 2015-05-20 | 2018-01-12 | 가부시키가이샤산와카가쿠켄큐쇼 | 신규 3-아자비시클로［3.1.0］헥산 유도체의 염의 결정 및 그의 의약 용도 |
| CA3036382A1 (en) * | 2016-12-21 | 2018-06-28 | Research Triangle Institute | Diaryl purine derivatives with improved bioavailability |
| CN110352055A (zh) * | 2017-03-02 | 2019-10-18 | 株式会社三和化学研究所 | 酒精使用障碍的治疗药物 |
| SG11202007422QA (en) * | 2018-02-05 | 2020-09-29 | Alkermes Inc | Compounds for the treatment of pain |
| WO2023064228A1 (en) * | 2021-10-11 | 2023-04-20 | Anebulo Pharmaceuticals, Inc. | Method of treating addiction |
| AU2022362107A1 (en) | 2021-10-11 | 2024-05-02 | Anebulo Pharmaceuticals, Inc. | Crystalline forms of a cannabinoid receptor type 1 (cb1) modulator and methods of use and preparation thereof |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1440059B1 (en) * | 2001-10-22 | 2008-04-16 | Pfizer Products Inc. | 3-azabicyclo(3.1.0)hexane derivatives as opioid receptor antagonists |
| AU2003267728A1 (en) * | 2002-10-18 | 2004-05-04 | Pfizer Products Inc. | Cannabinoid receptor ligands and uses thereof |
| US7129239B2 (en) * | 2002-10-28 | 2006-10-31 | Pfizer Inc. | Purine compounds and uses thereof |
| US7247628B2 (en) * | 2002-12-12 | 2007-07-24 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| US7329658B2 (en) * | 2003-02-06 | 2008-02-12 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
| US7176210B2 (en) * | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
-
2004
- 2004-06-17 US US10/870,209 patent/US20050043327A1/en not_active Abandoned
- 2004-08-09 JP JP2006523697A patent/JP2007502808A/ja active Pending
- 2004-08-09 CA CA002536280A patent/CA2536280A1/en not_active Abandoned
- 2004-08-09 BR BRPI0413693-4A patent/BRPI0413693A/pt not_active IP Right Cessation
- 2004-08-09 WO PCT/IB2004/002596 patent/WO2005018645A1/en not_active Ceased
- 2004-08-09 MX MXPA06002035A patent/MXPA06002035A/es not_active Application Discontinuation
- 2004-08-09 EP EP04744231A patent/EP1658082A1/en not_active Withdrawn
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