NZ524633A - 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity - Google Patents
4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activityInfo
- Publication number
- NZ524633A NZ524633A NZ524633A NZ52463302A NZ524633A NZ 524633 A NZ524633 A NZ 524633A NZ 524633 A NZ524633 A NZ 524633A NZ 52463302 A NZ52463302 A NZ 52463302A NZ 524633 A NZ524633 A NZ 524633A
- Authority
- NZ
- New Zealand
- Prior art keywords
- chlorophenyl
- phenyl
- dihydro
- pyrazole
- carboxamidine
- Prior art date
Links
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 title claims abstract description 5
- 230000000694 effects Effects 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 53
- 229930003827 cannabinoid Natural products 0.000 claims abstract description 14
- 239000003557 cannabinoid Substances 0.000 claims abstract description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 8
- 238000002360 preparation method Methods 0.000 claims abstract description 8
- 230000005062 synaptic transmission Effects 0.000 claims abstract description 5
- 208000020016 psychiatric disease Diseases 0.000 claims abstract description 4
- 208000024172 Cardiovascular disease Diseases 0.000 claims abstract description 3
- 208000018522 Gastrointestinal disease Diseases 0.000 claims abstract description 3
- 230000008018 melting Effects 0.000 claims description 31
- 238000002844 melting Methods 0.000 claims description 31
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- AXJQVVLKUYCICH-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AXJQVVLKUYCICH-UHFFFAOYSA-N 0.000 claims description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 208000027559 Appetite disease Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 2
- 208000016620 Tourette disease Diseases 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 239000012876 carrier material Substances 0.000 claims description 2
- 208000015114 central nervous system disease Diseases 0.000 claims description 2
- 230000006735 deficit Effects 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 206010015037 epilepsy Diseases 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 229940002612 prodrug Drugs 0.000 claims description 2
- 239000000651 prodrug Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 9
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 claims 6
- 230000005526 G1 to G0 transition Effects 0.000 claims 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims 3
- 238000013375 chromatographic separation Methods 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- GBSRSSIBIGRSBE-JOCHJYFZSA-N (4S)-5-(4-chlorophenyl)-N,N-dimethyl-N'-(2-methylphenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound CN(C(=NS(=O)(=O)C1=C(C=CC=C1)C)N1N=C([C@H](C1)C1=CC=CC=C1)C1=CC=C(C=C1)Cl)C GBSRSSIBIGRSBE-JOCHJYFZSA-N 0.000 claims 1
- RKVDQNXSXIWCQP-JOCHJYFZSA-N (4s)-5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-n-(dimethylamino)-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(/NN(C)C)=N\S(=O)(=O)C1=CC=C(Cl)C=C1 RKVDQNXSXIWCQP-JOCHJYFZSA-N 0.000 claims 1
- NMOHILMYXVQGHO-OAQYLSRUSA-N (4s)-5-(4-chlorophenyl)-n'-methyl-4-phenyl-n-[4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(NC)=NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 NMOHILMYXVQGHO-OAQYLSRUSA-N 0.000 claims 1
- WNHXVUIPVMASEZ-LJQANCHMSA-N (4s)-5-(4-chlorophenyl)-n-(2,4-difluorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(F)C=C1F WNHXVUIPVMASEZ-LJQANCHMSA-N 0.000 claims 1
- AYYMXSJOWFVFIO-JOCHJYFZSA-N (4s)-5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-ethyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(=NCC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AYYMXSJOWFVFIO-JOCHJYFZSA-N 0.000 claims 1
- AXJQVVLKUYCICH-OAQYLSRUSA-N (4s)-5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1C([C@H](C1)C=2C=CC=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AXJQVVLKUYCICH-OAQYLSRUSA-N 0.000 claims 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 1
- 208000002193 Pain Diseases 0.000 claims 1
- 239000000908 ammonium hydroxide Substances 0.000 claims 1
- 239000007864 aqueous solution Substances 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- -1 makes the 25 CB Proteins 0.000 description 6
- 229940044551 receptor antagonist Drugs 0.000 description 6
- 239000002464 receptor antagonist Substances 0.000 description 6
- 102000005962 receptors Human genes 0.000 description 6
- 108020003175 receptors Proteins 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 4
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- UCQFSGCWHRTMGG-UHFFFAOYSA-N pyrazole-1-carboximidamide Chemical compound NC(=N)N1C=CC=N1 UCQFSGCWHRTMGG-UHFFFAOYSA-N 0.000 description 4
- 239000012258 stirred mixture Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- SKLKZKAMWPQZLM-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-phenyl-4,5-dihydro-1h-pyrazole Chemical compound C1=CC(Cl)=CC=C1C1=NNCC1C1=CC=CC=C1 SKLKZKAMWPQZLM-UHFFFAOYSA-N 0.000 description 3
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 3
- 108050007331 Cannabinoid receptor Proteins 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000005557 antagonist Substances 0.000 description 3
- 229940093499 ethyl acetate Drugs 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- ASEXGSBVONTDSP-UHFFFAOYSA-N n-[bis(methylsulfanyl)methylidene]-4-chlorobenzenesulfonamide Chemical compound CSC(SC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 ASEXGSBVONTDSP-UHFFFAOYSA-N 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
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- 230000003389 potentiating effect Effects 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- CFRTVWXEOOFFPO-UHFFFAOYSA-N 4-phenylpyrazole-1-carboximidamide Chemical compound C1=NN(C(=N)N)C=C1C1=CC=CC=C1 CFRTVWXEOOFFPO-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- SUZLHDUTVMZSEV-UHFFFAOYSA-N Deoxycoleonol Natural products C12C(=O)CC(C)(C=C)OC2(C)C(OC(=O)C)C(O)C2C1(C)C(O)CCC2(C)C SUZLHDUTVMZSEV-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 239000000556 agonist Substances 0.000 description 2
- 230000003042 antagnostic effect Effects 0.000 description 2
- OHCQJHSOBUTRHG-UHFFFAOYSA-N colforsin Natural products OC12C(=O)CC(C)(C=C)OC1(C)C(OC(=O)C)C(O)C1C2(C)C(O)CCC1(C)C OHCQJHSOBUTRHG-UHFFFAOYSA-N 0.000 description 2
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- 240000004308 marijuana Species 0.000 description 2
- CJHMNJCPDWKHIJ-UHFFFAOYSA-N methyl 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidothioate Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(SC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 CJHMNJCPDWKHIJ-UHFFFAOYSA-N 0.000 description 2
- FCMYFMSWNFVHAC-UHFFFAOYSA-N methyl n-(4-chlorophenyl)sulfonylcarbamate Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(Cl)C=C1 FCMYFMSWNFVHAC-UHFFFAOYSA-N 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- KEQTWHPMSVAFDA-UHFFFAOYSA-N 2,3-dihydro-1h-pyrazole Chemical group C1NNC=C1 KEQTWHPMSVAFDA-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- FGCBXTLVUQGHQP-UHFFFAOYSA-N 3,4-dihydropyrazole-2-carboxamide Chemical class NC(=O)N1CCC=N1 FGCBXTLVUQGHQP-UHFFFAOYSA-N 0.000 description 1
- BMKMVBXDEAVUTE-UHFFFAOYSA-N 3,4-dihydropyrazole-2-carboximidamide Chemical class NC(=N)N1CCC=N1 BMKMVBXDEAVUTE-UHFFFAOYSA-N 0.000 description 1
- NRGOZJYSRXOCFH-UHFFFAOYSA-N 4,5-bis(4-methoxyphenyl)-n'-(4-methoxyphenyl)sulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(OC)=CC=C1C1C(C=2C=CC(OC)=CC=2)=NN(C(=N)NS(=O)(=O)C=2C=CC(OC)=CC=2)C1 NRGOZJYSRXOCFH-UHFFFAOYSA-N 0.000 description 1
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
- XPJPCDIVXGVHLY-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound N=1N(C(=N)N)CC(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 XPJPCDIVXGVHLY-UHFFFAOYSA-N 0.000 description 1
- RBDSMVUZBCAAEN-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-n'-(2,4,6-trimethylphenyl)sulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC(=N)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 RBDSMVUZBCAAEN-UHFFFAOYSA-N 0.000 description 1
- ABGOLZSZPVOQPE-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(3-methoxyphenyl)sulfonyl-n,n-dimethyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound COC1=CC=CC(S(=O)(=O)N=C(N(C)C)N2N=C(C(C2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABGOLZSZPVOQPE-UHFFFAOYSA-N 0.000 description 1
- SLWAJDMCAIQFOY-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-n-ethyl-n-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(N(C)CC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 SLWAJDMCAIQFOY-UHFFFAOYSA-N 0.000 description 1
- PMFKSNJVULPDBR-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-fluorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=N)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 PMFKSNJVULPDBR-UHFFFAOYSA-N 0.000 description 1
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- NVJVDZMNNYMORJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-pyridin-3-yl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=NC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 NVJVDZMNNYMORJ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D231/08—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with oxygen or sulfur atoms directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP01201062 | 2001-03-22 | ||
| PCT/EP2002/003079 WO2002076949A1 (en) | 2001-03-22 | 2002-03-18 | 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NZ524633A true NZ524633A (en) | 2005-02-25 |
Family
ID=8180044
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NZ524633A NZ524633A (en) | 2001-03-22 | 2002-03-18 | 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity |
Country Status (25)
| Country | Link |
|---|---|
| EP (1) | EP1373216B1 (enExample) |
| JP (1) | JP4373675B2 (enExample) |
| KR (1) | KR100846614B1 (enExample) |
| CN (1) | CN100366614C (enExample) |
| AR (1) | AR033046A1 (enExample) |
| AT (1) | ATE284872T1 (enExample) |
| AU (1) | AU2002256690B2 (enExample) |
| BR (1) | BR0205602A (enExample) |
| CA (1) | CA2422708C (enExample) |
| CZ (1) | CZ2003698A3 (enExample) |
| DE (1) | DE60202270T2 (enExample) |
| ES (1) | ES2229132T3 (enExample) |
| HU (1) | HUP0303148A3 (enExample) |
| IL (1) | IL153508A (enExample) |
| MX (1) | MXPA03003534A (enExample) |
| NO (1) | NO324953B1 (enExample) |
| NZ (1) | NZ524633A (enExample) |
| PL (1) | PL363751A1 (enExample) |
| PT (1) | PT1373216E (enExample) |
| RU (1) | RU2281941C2 (enExample) |
| SI (1) | SI1373216T1 (enExample) |
| SK (1) | SK287592B6 (enExample) |
| UA (1) | UA74066C2 (enExample) |
| WO (1) | WO2002076949A1 (enExample) |
| ZA (1) | ZA200307322B (enExample) |
Families Citing this family (125)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI231757B (en) | 2001-09-21 | 2005-05-01 | Solvay Pharm Bv | 1H-Imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
| JP3813152B2 (ja) | 2002-03-12 | 2006-08-23 | メルク エンド カムパニー インコーポレーテッド | 置換アミド類 |
| US7105526B2 (en) | 2002-06-28 | 2006-09-12 | Banyu Pharmaceuticals Co., Ltd. | Benzimidazole derivatives |
| 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 |
| US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
| 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 |
| US7268133B2 (en) | 2003-04-23 | 2007-09-11 | Pfizer, Inc. Patent Department | Cannabinoid receptor ligands and uses thereof |
| US7141669B2 (en) | 2003-04-23 | 2006-11-28 | Pfizer Inc. | Cannabiniod receptor ligands and uses thereof |
| US7145012B2 (en) | 2003-04-23 | 2006-12-05 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
| US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
| AR045533A1 (es) * | 2003-09-02 | 2005-11-02 | Solvay Pharm Gmbh | Uso de un compuesto antagonista de receptor de cb1, composicion farmaceutica y metodo de tratamiento y/o profilaxis de enfermedades relacionadas con dicho receptor de cb1 |
| CA2551037A1 (en) | 2003-09-22 | 2005-03-31 | Banyu Pharmaceutical Co., Ltd. | Novel piperidine derivative |
| TW200528102A (en) * | 2003-10-24 | 2005-09-01 | Solvay Pharm Gmbh | Novel medical combination treatment of obesity involving 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| CA2543338A1 (en) * | 2003-10-24 | 2005-05-06 | Solvay Pharmaceuticals Gmbh | Novel medical uses of compounds showing cb1-antagonistic activity and combination treatment involving said compounds |
| WO2005049615A1 (en) * | 2003-11-21 | 2005-06-02 | Pfizer Products Inc. | Pyrazolo`1,5-a!`1,3,5! triazin -4-one derivatives as cb1 receptor antagonists |
| BRPI0507120A (pt) | 2004-01-28 | 2007-06-19 | Hoffmann La Roche | compostos, processo para a manufatura dos mesmos, composições farmacêuticas que os compreendem, método para o tratamento e/ou profilaxia de enfermidades que estão associadas com a modulação de receptores de cb1 e sua utilização |
| PL1713475T3 (pl) * | 2004-01-30 | 2009-03-31 | Solvay Pharm Bv | 1,3,5-tripodstawione pochodne 4,5-dihydro-1-H-pirazolu wykazujące antagonistyczną aktywność w stosunku do CB1 |
| US7649002B2 (en) | 2004-02-04 | 2010-01-19 | Pfizer Inc | (3,5-dimethylpiperidin-1yl)(4-phenylpyrrolidin-3-yl)methanone derivatives as MCR4 agonists |
| CA2560314A1 (en) | 2004-03-29 | 2005-10-20 | Merck & Co., Inc. | Diaryltriazoles as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
| EP2305352A1 (en) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | 5-alpha-reductase inhibitors for use in the treatment of men with metabolic and anthropometric disorders |
| US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
| CA2575736A1 (en) | 2004-08-06 | 2006-02-16 | Merck & Co., Inc. | Sulfonyl compounds as inhibitors of 11-beta-hydroxysteroid dehydrogenase-1 |
| US7572783B2 (en) | 2004-08-13 | 2009-08-11 | Amgen Inc. | Substituted benzofused heterocycles |
| RU2007119315A (ru) * | 2004-10-25 | 2008-11-27 | Зольвай Фармасьютиклз Гмбх (De) | Фармацевтические композиции, содержащие антагонисты каннабиноидного рецептора св1 и открыватели калиевых каналов, предназначенные для лечения сахарного диабета типа i, ожирения и связанных с ними состояний |
| US8394765B2 (en) | 2004-11-01 | 2013-03-12 | Amylin Pharmaceuticals Llc | Methods of treating obesity with two different anti-obesity agents |
| BRPI0518241A (pt) | 2004-11-01 | 2008-04-22 | Amylin Pharmaceuticals Inc | métodos para tratar obesidade e doenças e distúrbios relacionados à obesidade |
| JP4675969B2 (ja) | 2004-11-09 | 2011-04-27 | エフ．ホフマン−ラ ロシュ アーゲー | ジベンゾスベロン誘導体 |
| WO2006060186A2 (en) * | 2004-11-30 | 2006-06-08 | Bayer Pharmaceuticals Corporation | Pyrazole derivatives for the treatment of dementia and related disorders |
| WO2006060201A2 (en) * | 2004-11-30 | 2006-06-08 | Bayer Pharmaceuticals Corporation | Pyrazole derivatives for the treatment of psychiatric disorders |
| PA8660701A1 (es) | 2005-02-04 | 2006-09-22 | Pfizer Prod Inc | Agonistas de pyy y sus usos |
| US7737155B2 (en) | 2005-05-17 | 2010-06-15 | Schering Corporation | Nitrogen-containing heterocyclic compounds and methods of use thereof |
| EP1892241B1 (en) | 2005-05-30 | 2016-03-30 | Msd K.K. | Novel piperidine derivative |
| US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| EP1902034B1 (en) | 2005-06-02 | 2011-03-30 | Glenmark Pharmaceuticals S.A. | Novel cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
| EP1757587A1 (en) * | 2005-07-15 | 2007-02-28 | Laboratorios Del Dr. Esteve, S.A. | Substituted pyrazoline compounds, their preparation and use as medicaments |
| JPWO2007018248A1 (ja) | 2005-08-10 | 2009-02-19 | 萬有製薬株式会社 | ピリドン化合物 |
| EP2330125A3 (en) | 2005-08-11 | 2012-12-12 | Amylin Pharmaceuticals, Inc. | Hybrid polypeptides with selectable properties |
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