JP5269795B2 - 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 - Google Patents
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 Download PDFInfo
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- JP5269795B2 JP5269795B2 JP2009530273A JP2009530273A JP5269795B2 JP 5269795 B2 JP5269795 B2 JP 5269795B2 JP 2009530273 A JP2009530273 A JP 2009530273A JP 2009530273 A JP2009530273 A JP 2009530273A JP 5269795 B2 JP5269795 B2 JP 5269795B2
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- Prior art keywords
- chlorophenyl
- dichlorophenyl
- pyrazol
- methyl
- oxadiazole
- 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.)
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- 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 title 1
- -1 pyrididinyl Chemical group 0.000 claims description 159
- 150000001875 compounds Chemical class 0.000 claims description 118
- 125000000217 alkyl group Chemical group 0.000 claims description 45
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 125000001072 heteroaryl group Chemical group 0.000 claims description 37
- 229910052736 halogen Chemical group 0.000 claims description 36
- 125000003545 alkoxy group Chemical group 0.000 claims description 35
- 150000002367 halogens Chemical group 0.000 claims description 35
- 125000000623 heterocyclic group Chemical group 0.000 claims description 34
- 239000002904 solvent Substances 0.000 claims description 31
- 208000008589 Obesity Diseases 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
- 235000020824 obesity Nutrition 0.000 claims description 24
- 150000003839 salts Chemical class 0.000 claims description 22
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 18
- 238000004519 manufacturing process Methods 0.000 claims description 15
- 239000007822 coupling agent Substances 0.000 claims description 13
- 229920006395 saturated elastomer Polymers 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 12
- 239000001257 hydrogen Substances 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 229930003827 cannabinoid Natural products 0.000 claims description 11
- 239000003557 cannabinoid Substances 0.000 claims description 11
- 125000001153 fluoro group Chemical group F* 0.000 claims description 11
- 125000004104 aryloxy group Chemical group 0.000 claims description 9
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical group C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 8
- 208000030159 metabolic disease Diseases 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000003107 substituted aryl group Chemical group 0.000 claims description 8
- 150000003536 tetrazoles Chemical group 0.000 claims description 8
- 239000012024 dehydrating agents Substances 0.000 claims description 7
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims description 7
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000004423 acyloxy group Chemical group 0.000 claims description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Chemical group C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 5
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 5
- 150000003852 triazoles Chemical group 0.000 claims description 5
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
- OCHGJFRPNCHNPG-UHFFFAOYSA-N 2-tert-butyl-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(tetrazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C1CN1N=NN=C1 OCHGJFRPNCHNPG-UHFFFAOYSA-N 0.000 claims description 4
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical group C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000005842 heteroatom Chemical group 0.000 claims description 4
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
- 230000002401 inhibitory effect Effects 0.000 claims description 4
- RWIQXQQIIXYVSV-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclobutyl]-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2(CCC2)C=2C=CC(Cl)=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 RWIQXQQIIXYVSV-UHFFFAOYSA-N 0.000 claims description 3
- WGXALGODPQPDFI-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopentyl]-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2(CCCC2)C=2C=CC(Cl)=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 WGXALGODPQPDFI-UHFFFAOYSA-N 0.000 claims description 3
- RZPBOBILFDCNDZ-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopentyl]-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2(CCCC2)C=2C=CC(Cl)=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 RZPBOBILFDCNDZ-UHFFFAOYSA-N 0.000 claims description 3
- IOFYFYDHJRCFEN-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2(CC2)C=2C=CC(Cl)=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 IOFYFYDHJRCFEN-UHFFFAOYSA-N 0.000 claims description 3
- MVKGXECUXFMXAW-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)cyclopropyl]-5-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2(CC2)C=2C=CC(Cl)=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 MVKGXECUXFMXAW-UHFFFAOYSA-N 0.000 claims description 3
- YNIPAVLUZDOMRZ-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(4-chlorophenyl)cyclopropyl]-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C1(C=2OC(=NN=2)C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Br)=CC=2)CN2N=CN=C2)CC1 YNIPAVLUZDOMRZ-UHFFFAOYSA-N 0.000 claims description 3
- XKTGAOKUZKGROW-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(4-chlorophenyl)cyclopropyl]-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C1(C=2SC(=NN=2)C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Br)=CC=2)CN2N=CN=C2)CC1 XKTGAOKUZKGROW-UHFFFAOYSA-N 0.000 claims description 3
- SMMDQQCYEUMSNY-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Br)=CC=2)CN2N=CN=C2)OC=1C1(C(F)(F)F)CC1 SMMDQQCYEUMSNY-UHFFFAOYSA-N 0.000 claims description 3
- UQFXYRPRLVAAOP-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-thiadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Br)=CC=2)CN2N=CN=C2)SC=1C1(C(F)(F)F)CC1 UQFXYRPRLVAAOP-UHFFFAOYSA-N 0.000 claims description 3
- DGTIQUVYTKPRJK-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-tert-butyl-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C1CN1N=CN=C1 DGTIQUVYTKPRJK-UHFFFAOYSA-N 0.000 claims description 3
- KBDZMHUBIGWJPD-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-tert-butyl-1,3,4-thiadiazole Chemical compound S1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C1CN1N=CN=C1 KBDZMHUBIGWJPD-UHFFFAOYSA-N 0.000 claims description 3
- DYSLBYWNVXHZIH-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(tetrazol-1-ylmethyl)pyrazol-3-yl]-5-tert-butyl-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C1CN1N=NN=C1 DYSLBYWNVXHZIH-UHFFFAOYSA-N 0.000 claims description 3
- HSDFLFRHUYEMKW-UHFFFAOYSA-N 2-[5-(4-bromophenyl)-1-(2,4-dichlorophenyl)-4-(tetrazol-2-ylmethyl)pyrazol-3-yl]-5-tert-butyl-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC(Cl)=CC=2)Cl)C(C=2C=CC(Br)=CC=2)=C1CN1N=NC=N1 HSDFLFRHUYEMKW-UHFFFAOYSA-N 0.000 claims description 3
- PWQFFQRBKLPONF-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-(1-methylcyclopropyl)-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)OC=1C1(C)CC1 PWQFFQRBKLPONF-UHFFFAOYSA-N 0.000 claims description 3
- ZSSRUEITPKPQOW-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-(1-methylcyclopropyl)-1,3,4-thiadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)SC=1C1(C)CC1 ZSSRUEITPKPQOW-UHFFFAOYSA-N 0.000 claims description 3
- XDQFLQKVRZKXHU-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-(1-phenylcyclopentyl)-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2(CCCC2)C=2C=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 XDQFLQKVRZKXHU-UHFFFAOYSA-N 0.000 claims description 3
- KWQKWVARAVTLQA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-(1-phenylcyclopentyl)-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2(CCCC2)C=2C=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 KWQKWVARAVTLQA-UHFFFAOYSA-N 0.000 claims description 3
- ACIDUOVQXWIJER-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-(1-phenylcyclopropyl)-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2(CC2)C=2C=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 ACIDUOVQXWIJER-UHFFFAOYSA-N 0.000 claims description 3
- IYLHAOFOPKLWMF-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-(1-phenylcyclopropyl)-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2(CC2)C=2C=CC=CC=2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 IYLHAOFOPKLWMF-UHFFFAOYSA-N 0.000 claims description 3
- UOGAWYNXQXKNEC-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(2,4-dichlorophenyl)cyclopropyl]-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2(CC2)C=2C(=CC(Cl)=CC=2)Cl)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 UOGAWYNXQXKNEC-UHFFFAOYSA-N 0.000 claims description 3
- OJKWSCXXBHORPR-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(4-methoxyphenyl)cyclopropyl]-1,3,4-oxadiazole Chemical compound C1=CC(OC)=CC=C1C1(C=2OC(=NN=2)C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)CC1 OJKWSCXXBHORPR-UHFFFAOYSA-N 0.000 claims description 3
- XKTDQRWCVPQRJA-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(4-methoxyphenyl)cyclopropyl]-1,3,4-thiadiazole Chemical compound C1=CC(OC)=CC=C1C1(C=2SC(=NN=2)C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)CC1 XKTDQRWCVPQRJA-UHFFFAOYSA-N 0.000 claims description 3
- LDJRQIYPZSOSRH-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(4-methylphenyl)cyclopropyl]-1,3,4-oxadiazole Chemical compound C1=CC(C)=CC=C1C1(C=2OC(=NN=2)C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)CC1 LDJRQIYPZSOSRH-UHFFFAOYSA-N 0.000 claims description 3
- LLFJPGDWIRCNTP-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(4-methylphenyl)cyclopropyl]-1,3,4-thiadiazole Chemical compound C1=CC(C)=CC=C1C1(C=2SC(=NN=2)C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)CC1 LLFJPGDWIRCNTP-UHFFFAOYSA-N 0.000 claims description 3
- MXDYVLWGDAKEMQ-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(trifluoromethyl)cyclobutyl]-1,3,4-oxadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)OC=1C1(C(F)(F)F)CCC1 MXDYVLWGDAKEMQ-UHFFFAOYSA-N 0.000 claims description 3
- VWGSYATZAOMKDD-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(trifluoromethyl)cyclobutyl]-1,3,4-thiadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)SC=1C1(C(F)(F)F)CCC1 VWGSYATZAOMKDD-UHFFFAOYSA-N 0.000 claims description 3
- OMTNSTLCWWWNGB-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-[1-(trifluoromethyl)cyclopropyl]-1,3,4-thiadiazole Chemical compound N=1N=C(C=2C(=C(N(N=2)C=2C(=CC(Cl)=CC=2)Cl)C=2C=CC(Cl)=CC=2)CN2N=CN=C2)SC=1C1(C(F)(F)F)CC1 OMTNSTLCWWWNGB-UHFFFAOYSA-N 0.000 claims description 3
- ZMDJKTGYEYFYOB-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-cyclobutyl-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2CCC2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 ZMDJKTGYEYFYOB-UHFFFAOYSA-N 0.000 claims description 3
- JDRPPEGCDUNMCT-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-cyclobutyl-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2CCC2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 JDRPPEGCDUNMCT-UHFFFAOYSA-N 0.000 claims description 3
- XFGTYRPQZDHPFQ-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-cyclohexyl-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2OC(=NN=2)C2CCCCC2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 XFGTYRPQZDHPFQ-UHFFFAOYSA-N 0.000 claims description 3
- MEVLZSORHWCFKQ-UHFFFAOYSA-N 2-[5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-5-cyclohexyl-1,3,4-thiadiazole Chemical compound C1=CC(Cl)=CC=C1C(N(N=C1C=2SC(=NN=2)C2CCCCC2)C=2C(=CC(Cl)=CC=2)Cl)=C1CN1N=CN=C1 MEVLZSORHWCFKQ-UHFFFAOYSA-N 0.000 claims description 3
- MZESHBNUIYUEHZ-UHFFFAOYSA-N 2-tert-butyl-5-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-oxadiazole Chemical compound O1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C1CN1N=CN=C1 MZESHBNUIYUEHZ-UHFFFAOYSA-N 0.000 claims description 3
- AYVOANBRQFDRFL-UHFFFAOYSA-N 2-tert-butyl-5-[1-(2-chlorophenyl)-5-(4-chlorophenyl)-4-(1,2,4-triazol-1-ylmethyl)pyrazol-3-yl]-1,3,4-thiadiazole Chemical compound S1C(C(C)(C)C)=NN=C1C1=NN(C=2C(=CC=CC=2)Cl)C(C=2C=CC(Cl)=CC=2)=C1CN1N=CN=C1 AYVOANBRQFDRFL-UHFFFAOYSA-N 0.000 claims description 3
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
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- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
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- Animal Behavior & Ethology (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US11/541,269 | 2006-09-29 | ||
US11/541,269 US20080081815A1 (en) | 2006-09-29 | 2006-09-29 | Heteroaryl-pyrazole derivatives as cannabinoid CB1 receptor antagonists |
KR10-2006-0132606 | 2006-12-22 | ||
KR20060132606 | 2006-12-22 | ||
PCT/KR2007/004754 WO2008039023A1 (fr) | 2006-09-29 | 2007-09-28 | Dérivés d'hétéroaryl-pyrazole utilisés en tant qu'antagonistes du récepteur cb1 des cannabinoïdes |
Publications (2)
Publication Number | Publication Date |
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JP2010504961A JP2010504961A (ja) | 2010-02-18 |
JP5269795B2 true JP5269795B2 (ja) | 2013-08-21 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2009530273A Expired - Fee Related JP5269795B2 (ja) | 2006-09-29 | 2007-09-28 | 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 |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP2097410A4 (fr) |
JP (1) | JP5269795B2 (fr) |
KR (1) | KR101100028B1 (fr) |
CN (1) | CN101528740B (fr) |
WO (1) | WO2008039023A1 (fr) |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
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EP2025674A1 (fr) | 2007-08-15 | 2009-02-18 | sanofi-aventis | Tetrahydronaphthaline substituée, son procédé de fabrication et son utilisation en tant que médicament |
ES2390560T3 (es) * | 2008-04-22 | 2012-11-14 | Eli Lilly And Company | Compuestos de 1,5-difenil-pirrolidin-2-ona como ligandos CB-1 |
AU2009238444B2 (en) * | 2008-04-22 | 2013-08-29 | Eli Lilly And Company | 1,5-diphenyl-pyrrolidin-2-one compounds as CB-1 ligands |
ES2639940T3 (es) | 2011-04-27 | 2017-10-30 | Shionogi & Co., Ltd. | Derivado heterocíclico aromático de 5 miembros anillo que tiene actividad antagonista del receptor Y5 de NPY |
WO2013005168A2 (fr) * | 2011-07-05 | 2013-01-10 | Lupin Limited | Modulateurs des récepteurs de cannabinoïdes |
TWI673429B (zh) | 2013-03-14 | 2019-10-01 | 美商漢特道格拉斯股份有限公司 | 用以控制建築開口遮蓋物總成之方法及裝置 |
WO2015162452A1 (fr) * | 2014-04-23 | 2015-10-29 | Piramal Enterprises Limited | Composés pyrazole substitués comme antagonistes du récepteur cb1 et leurs utilisations |
CN108586436A (zh) * | 2018-07-06 | 2018-09-28 | 南京大学 | 一类含吲哚骨架的双酰肼类衍生物及其制备方法和应用 |
Family Cites Families (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4146721A (en) * | 1969-09-12 | 1979-03-27 | Byk Gulden Lomberg Chemische Fabrik Gmbh | Pyrazol-4-acetic acid compounds |
DE2906252A1 (de) * | 1979-02-19 | 1980-08-28 | Merck Patent Gmbh | Pyrazolderivate, diese enthaltende pharmazeutische zubereitungen und verfahren zu ihrer herstellung |
PH27357A (en) * | 1989-09-22 | 1993-06-21 | Fujisawa Pharmaceutical Co | Pyrazole derivatives and pharmaceutical compositions comprising the same |
FR2714057B1 (fr) | 1993-12-17 | 1996-03-08 | Sanofi Elf | Nouveaux dérivés du 3-pyrazolecarboxamide, procédé pour leur préparation et compositions pharmaceutiques les contenant. |
EP1300159B1 (fr) * | 2000-06-29 | 2007-10-10 | Anthera Pharmaceuticals, Inc. | Remedes contre le cancer |
CN1638776A (zh) * | 2001-06-08 | 2005-07-13 | 西托维亚公司 | 取代的3-芳基-5-芳基-[1,2,4]-噁二唑和类似物 |
BR0314872A (pt) * | 2002-10-18 | 2005-08-02 | Pfizer Prod Inc | Ligandos do receptor canabinóide e usos dos mesmos |
JP2006514693A (ja) | 2002-12-18 | 2006-05-11 | スミスクライン・ビーチャム・コーポレイション | ペプチドデホルミラーゼ阻害剤 |
US20050043327A1 (en) * | 2003-08-21 | 2005-02-24 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of addiction in a mammal |
EP1697333A4 (fr) | 2003-12-17 | 2009-07-08 | Merck & Co Inc | Carboxylates propanoiques 3,4-disusbstitues utilises en tant qu'agonistes du recepteur s1p (edg) |
JP2007530690A (ja) * | 2004-03-29 | 2007-11-01 | メルク エンド カムパニー インコーポレーテッド | 11−β−ヒドロキシステロイドデヒドロゲナーゼ−1の阻害剤としてのジアリールトリアゾール |
FR2882365B1 (fr) * | 2005-02-21 | 2007-09-07 | Sanofi Aventis Sa | Derives de 2-(1,5-diphenyl-1h-pyrazol-3-yl)-1,3,4-oxadiazole leur preparation et leur application en therapeutique |
-
2007
- 2007-09-28 EP EP07833072A patent/EP2097410A4/fr not_active Withdrawn
- 2007-09-28 KR KR1020097008743A patent/KR101100028B1/ko active IP Right Grant
- 2007-09-28 JP JP2009530273A patent/JP5269795B2/ja not_active Expired - Fee Related
- 2007-09-28 CN CN2007800363304A patent/CN101528740B/zh not_active Expired - Fee Related
- 2007-09-28 WO PCT/KR2007/004754 patent/WO2008039023A1/fr active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP2097410A1 (fr) | 2009-09-09 |
WO2008039023A1 (fr) | 2008-04-03 |
CN101528740A (zh) | 2009-09-09 |
JP2010504961A (ja) | 2010-02-18 |
CN101528740B (zh) | 2012-09-19 |
KR20090061076A (ko) | 2009-06-15 |
EP2097410A4 (fr) | 2009-11-25 |
KR101100028B1 (ko) | 2011-12-29 |
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