HRP20040185A2 - 1h-imidazole derivatives having cb<sub>1</sub> agonistic, cb<sub>1</sub> partial agonistic or cb<sub>1</sub> antagonistic activity - Google Patents
1h-imidazole derivatives having cb<sub>1</sub> agonistic, cb<sub>1</sub> partial agonistic or cb<sub>1</sub> antagonistic activity Download PDFInfo
- Publication number
- HRP20040185A2 HRP20040185A2 HR20040185A HRP20040185A HRP20040185A2 HR P20040185 A2 HRP20040185 A2 HR P20040185A2 HR 20040185 A HR20040185 A HR 20040185A HR P20040185 A HRP20040185 A HR P20040185A HR P20040185 A2 HRP20040185 A2 HR P20040185A2
- Authority
- HR
- Croatia
- Prior art keywords
- group
- whose
- groups
- substituted
- imidazole
- Prior art date
Links
- 230000003042 antagnostic effect Effects 0.000 title description 2
- 230000001270 agonistic effect Effects 0.000 title 2
- RAXXELZNTBOGNW-MQIHXRCWSA-N 1h-imidazole Chemical class C1=C[15NH]C=[15N]1 RAXXELZNTBOGNW-MQIHXRCWSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 58
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 25
- -1 2-pyridinyl Chemical group 0.000 claims description 21
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 17
- 229930003827 cannabinoid Natural products 0.000 claims description 16
- 239000003557 cannabinoid Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 16
- 125000005842 heteroatom Chemical group 0.000 claims description 16
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 15
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 125000000623 heterocyclic group Chemical group 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 125000005843 halogen group Chemical group 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 7
- 125000004076 pyridyl group Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 208000006011 Stroke Diseases 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052794 bromium Inorganic materials 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 201000010099 disease Diseases 0.000 claims description 5
- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 5
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- 125000004306 triazinyl group Chemical group 0.000 claims description 5
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- 125000000081 (C5-C8) cycloalkenyl group Chemical group 0.000 claims description 4
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000003277 amino group Chemical group 0.000 claims description 4
- 125000004429 atom Chemical group 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 230000005062 synaptic transmission Effects 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 208000012902 Nervous system disease Diseases 0.000 claims description 3
- 208000025966 Neurological disease Diseases 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 208000020016 psychiatric disease Diseases 0.000 claims description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 208000019901 Anxiety disease Diseases 0.000 claims description 2
- 201000006474 Brain Ischemia Diseases 0.000 claims description 2
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 2
- 206010008190 Cerebrovascular accident Diseases 0.000 claims description 2
- 206010012289 Dementia Diseases 0.000 claims description 2
- 208000016192 Demyelinating disease Diseases 0.000 claims description 2
- 206010012305 Demyelination Diseases 0.000 claims description 2
- 206010012335 Dependence Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
- 208000014094 Dystonic disease Diseases 0.000 claims description 2
- 208000030814 Eating disease Diseases 0.000 claims description 2
- 206010014612 Encephalitis viral Diseases 0.000 claims description 2
- 208000019454 Feeding and Eating disease Diseases 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 206010019196 Head injury Diseases 0.000 claims description 2
- 208000023105 Huntington disease Diseases 0.000 claims description 2
- 208000026139 Memory disease Diseases 0.000 claims description 2
- 208000007101 Muscle Cramp Diseases 0.000 claims description 2
- 206010028813 Nausea Diseases 0.000 claims description 2
- 206010028980 Neoplasm Diseases 0.000 claims description 2
- 208000036110 Neuroinflammatory disease Diseases 0.000 claims description 2
- 208000008589 Obesity Diseases 0.000 claims description 2
- 208000018737 Parkinson disease Diseases 0.000 claims description 2
- 208000028017 Psychotic disease Diseases 0.000 claims description 2
- 208000034189 Sclerosis Diseases 0.000 claims description 2
- 208000027520 Somatoform disease Diseases 0.000 claims description 2
- 208000005392 Spasm Diseases 0.000 claims description 2
- 208000007107 Stomach Ulcer Diseases 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims description 2
- 208000016620 Tourette disease Diseases 0.000 claims description 2
- 208000030886 Traumatic Brain injury Diseases 0.000 claims description 2
- 206010044565 Tremor Diseases 0.000 claims description 2
- 206010047700 Vomiting Diseases 0.000 claims description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 230000036506 anxiety Effects 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 150000001602 bicycloalkyls Chemical group 0.000 claims description 2
- 201000011510 cancer Diseases 0.000 claims description 2
- 230000002490 cerebral effect Effects 0.000 claims description 2
- 206010008118 cerebral infarction Diseases 0.000 claims description 2
- 208000010877 cognitive disease Diseases 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 206010012601 diabetes mellitus Diseases 0.000 claims description 2
- 235000014632 disordered eating Nutrition 0.000 claims description 2
- 206010013663 drug dependence Diseases 0.000 claims description 2
- 208000010118 dystonia Diseases 0.000 claims description 2
- 125000002950 monocyclic group Chemical group 0.000 claims description 2
- 201000006417 multiple sclerosis Diseases 0.000 claims description 2
- 230000008693 nausea Effects 0.000 claims description 2
- 208000004296 neuralgia Diseases 0.000 claims description 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 2
- 208000021722 neuropathic pain Diseases 0.000 claims description 2
- 230000000269 nucleophilic effect Effects 0.000 claims description 2
- 235000020824 obesity Nutrition 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 208000027753 pain disease Diseases 0.000 claims description 2
- 208000023504 respiratory system disease Diseases 0.000 claims description 2
- 208000020431 spinal cord injury Diseases 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 230000009529 traumatic brain injury Effects 0.000 claims description 2
- 201000002498 viral encephalitis Diseases 0.000 claims description 2
- 230000008673 vomiting Effects 0.000 claims description 2
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims 1
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 1
- 206010040070 Septic Shock Diseases 0.000 claims 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 239000000651 prodrug Substances 0.000 claims 1
- 229940002612 prodrug Drugs 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000036303 septic shock Effects 0.000 claims 1
- 208000011117 substance-related disease Diseases 0.000 claims 1
- 238000002844 melting Methods 0.000 description 94
- 230000008018 melting Effects 0.000 description 94
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 46
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
- 239000000203 mixture Substances 0.000 description 29
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 22
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 18
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 15
- 239000000741 silica gel Substances 0.000 description 15
- 229910002027 silica gel Inorganic materials 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 102000009132 CB1 Cannabinoid Receptor Human genes 0.000 description 12
- 108010073366 CB1 Cannabinoid Receptor Proteins 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 238000004440 column chromatography Methods 0.000 description 9
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 8
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000007832 Na2SO4 Substances 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229910052938 sodium sulfate Inorganic materials 0.000 description 7
- 235000011152 sodium sulphate Nutrition 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
- 229940065144 cannabinoids Drugs 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 239000004031 partial agonist Substances 0.000 description 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 4
- 108050007331 Cannabinoid receptor Proteins 0.000 description 4
- 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
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000005557 antagonist Substances 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- UZYBCYPTBNXRLH-UHFFFAOYSA-N ethyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxylate Chemical compound N=1C(C(=O)OCC)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl UZYBCYPTBNXRLH-UHFFFAOYSA-N 0.000 description 4
- 229940044551 receptor antagonist Drugs 0.000 description 4
- 239000002464 receptor antagonist Substances 0.000 description 4
- DYWNLSQWJMTVGJ-DKXTVVGFSA-N (1s,2s)-2-amino-1-phenylpropan-1-ol;hydron;chloride Chemical compound Cl.C[C@H](N)[C@@H](O)C1=CC=CC=C1 DYWNLSQWJMTVGJ-DKXTVVGFSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
- 239000000556 agonist Substances 0.000 description 3
- 244000309464 bull Species 0.000 description 3
- 238000010168 coupling process Methods 0.000 description 3
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
- 239000003446 ligand Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 239000003208 petroleum Substances 0.000 description 3
- LWMPFIOTEAXAGV-UHFFFAOYSA-N piperidin-1-amine Chemical compound NN1CCCCC1 LWMPFIOTEAXAGV-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000018 receptor agonist Substances 0.000 description 3
- 229940044601 receptor agonist Drugs 0.000 description 3
- 238000001953 recrystallisation Methods 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- KUGXDNUGDPKZBW-UHFFFAOYSA-N tert-butyl 1-(4-chlorophenyl)-5-cyano-2-(2,4-dichlorophenyl)imidazole-4-carboxylate Chemical compound C=1C=C(Cl)C=CC=1N1C(C#N)=C(C(=O)OC(C)(C)C)N=C1C1=CC=C(Cl)C=C1Cl KUGXDNUGDPKZBW-UHFFFAOYSA-N 0.000 description 3
- OCQYXZPKOQZUNQ-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxylic acid Chemical compound N=1C(C(=O)O)=CN(C=2C=CC(Br)=CC=2)C=1C1=CC=C(Cl)C=C1Cl OCQYXZPKOQZUNQ-UHFFFAOYSA-N 0.000 description 2
- FQVFACGJHHJQNN-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxylic acid Chemical compound N=1C(C(=O)O)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl FQVFACGJHHJQNN-UHFFFAOYSA-N 0.000 description 2
- TXTLOBKZXYXVBX-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-cyano-2-(2,4-dichlorophenyl)imidazole-4-carboxylic acid Chemical compound C=1C=C(Cl)C=CC=1N1C(C#N)=C(C(=O)O)N=C1C1=CC=C(Cl)C=C1Cl TXTLOBKZXYXVBX-UHFFFAOYSA-N 0.000 description 2
- QQIRTFPHUHBRRB-UHFFFAOYSA-N 2,4-dichloro-n'-(4-chlorophenyl)benzenecarboximidamide Chemical compound C1=CC(Cl)=CC=C1NC(=N)C1=CC=C(Cl)C=C1Cl QQIRTFPHUHBRRB-UHFFFAOYSA-N 0.000 description 2
- GACNIJHLDRRTOL-UHFFFAOYSA-N 2,4-dichloro-n'-[4-(trifluoromethyl)phenyl]benzenecarboximidamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=N)C1=CC=C(Cl)C=C1Cl GACNIJHLDRRTOL-UHFFFAOYSA-N 0.000 description 2
- CKHKFNQLWIROHE-UHFFFAOYSA-N 2,4-dichloro-n-[4-(trifluoromethyl)phenyl]benzamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C1=CC=C(Cl)C=C1Cl CKHKFNQLWIROHE-UHFFFAOYSA-N 0.000 description 2
- KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 2
- SNXHEKLUMHMSNN-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methylimidazole-4-carboxylic acid Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(O)=O)=C1C SNXHEKLUMHMSNN-UHFFFAOYSA-N 0.000 description 2
- QHQZFBXRRMRFSQ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methylimidazole-4-carbonyl chloride Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(C)=C(C(Cl)=O)N=C1C1=CC=C(Cl)C=C1 QHQZFBXRRMRFSQ-UHFFFAOYSA-N 0.000 description 2
- GJNGXPDXRVXSEH-UHFFFAOYSA-N 4-chlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C=C1 GJNGXPDXRVXSEH-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 101710187010 Cannabinoid receptor 1 Proteins 0.000 description 2
- 102100033868 Cannabinoid receptor 1 Human genes 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
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 230000003375 cannabimimetic effect Effects 0.000 description 2
- 239000003795 chemical substances by application Substances 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
- 150000003983 crown ethers Chemical class 0.000 description 2
- 239000002739 cryptand Substances 0.000 description 2
- PAFZNILMFXTMIY-UHFFFAOYSA-N cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- WNNIGAWMMGEJKM-UHFFFAOYSA-N ethyl 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxylate Chemical compound N=1C(C(=O)OCC)=CN(C=2C=CC(Br)=CC=2)C=1C1=CC=C(Cl)C=C1Cl WNNIGAWMMGEJKM-UHFFFAOYSA-N 0.000 description 2
- ZRUUNAARBYPXJU-UHFFFAOYSA-N ethyl 1-(4-bromophenyl)-5-chloro-2-(2,4-dichlorophenyl)imidazole-4-carboxylate Chemical compound C=1C=C(Br)C=CC=1N1C(Cl)=C(C(=O)OCC)N=C1C1=CC=C(Cl)C=C1Cl ZRUUNAARBYPXJU-UHFFFAOYSA-N 0.000 description 2
- HZQIKMFUCARKQP-UHFFFAOYSA-N ethyl 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methylimidazole-4-carboxylate Chemical compound C=1C=C(OC)C=CC=1N1C(C)=C(C(=O)OCC)N=C1C1=CC=C(Cl)C=C1Cl HZQIKMFUCARKQP-UHFFFAOYSA-N 0.000 description 2
- CXGJBCMYPMUFSU-UHFFFAOYSA-N ethyl 2-(2,4-dichlorophenyl)-5-methyl-1-[4-(trifluoromethyl)phenyl]imidazole-4-carboxylate Chemical compound C=1C=C(C(F)(F)F)C=CC=1N1C(C)=C(C(=O)OCC)N=C1C1=CC=C(Cl)C=C1Cl CXGJBCMYPMUFSU-UHFFFAOYSA-N 0.000 description 2
- JMQXRRBDPSPHKV-UHFFFAOYSA-N ethyl 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxylate Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(C)=C(C(=O)OCC)N=C1C1=CC=C(Cl)C=C1 JMQXRRBDPSPHKV-UHFFFAOYSA-N 0.000 description 2
- SIOIQIWIQSMQAG-UHFFFAOYSA-N ethyl 3-bromo-2-oxobutanoate Chemical compound CCOC(=O)C(=O)C(C)Br SIOIQIWIQSMQAG-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- KQLIBRYGIIAMAM-UHFFFAOYSA-N tert-butyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxylate Chemical compound N=1C(C(=O)OC(C)(C)C)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl KQLIBRYGIIAMAM-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- JONIMGVUGJVFQD-UHFFFAOYSA-N (4-methylphenyl)sulfonylformonitrile Chemical compound CC1=CC=C(S(=O)(=O)C#N)C=C1 JONIMGVUGJVFQD-UHFFFAOYSA-N 0.000 description 1
- NLMDJJTUQPXZFG-UHFFFAOYSA-N 1,4,10,13-tetraoxa-7,16-diazacyclooctadecane Chemical compound C1COCCOCCNCCOCCOCCN1 NLMDJJTUQPXZFG-UHFFFAOYSA-N 0.000 description 1
- TZEUEXZROXFIIO-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NOC(C)(C)C)N=C1C1=CC=C(Cl)C=C1Cl TZEUEXZROXFIIO-UHFFFAOYSA-N 0.000 description 1
- VNSIAYZGNJDGOE-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1Cl VNSIAYZGNJDGOE-UHFFFAOYSA-N 0.000 description 1
- AFBXAMDVJUKHMK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl AFBXAMDVJUKHMK-UHFFFAOYSA-N 0.000 description 1
- XTZUEDAKHUNVEK-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(C)=C(C(=O)NOC(C)(C)C)N=C1C1=CC=C(Cl)C=C1Cl XTZUEDAKHUNVEK-UHFFFAOYSA-N 0.000 description 1
- PLTSATGWXQRBDE-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl PLTSATGWXQRBDE-UHFFFAOYSA-N 0.000 description 1
- YCZSEPKOSIJWCU-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound N=1C(C(=O)NOC(C)(C)C)=CN(C=2C=CC(Br)=CC=2)C=1C1=CC=C(Cl)C=C1Cl YCZSEPKOSIJWCU-UHFFFAOYSA-N 0.000 description 1
- GCQWDIQUVRTULL-UHFFFAOYSA-N 1-(4-bromophenyl)-2-(2,4-dichlorophenyl)-n-pyrrolidin-1-ylimidazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCC2)=CN1C1=CC=C(Br)C=C1 GCQWDIQUVRTULL-UHFFFAOYSA-N 0.000 description 1
- SHLMKTXWDGEQRU-UHFFFAOYSA-N 1-(4-bromophenyl)-5-chloro-2-(2,4-dichlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(Cl)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl SHLMKTXWDGEQRU-UHFFFAOYSA-N 0.000 description 1
- XWUCVTHIHTTWIK-UHFFFAOYSA-N 1-(4-bromophenyl)-n-cyclohexyl-2-(2,4-dichlorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C=C(Br)C=CC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl XWUCVTHIHTTWIK-UHFFFAOYSA-N 0.000 description 1
- LJYKHPSJOACCMJ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(1,5-dimethylpyrrol-2-yl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound CN1C(C)=CC=C1C1=NC(C(=O)NN2CCCCC2)=C(C)N1C1=CC=C(Cl)C=C1 LJYKHPSJOACCMJ-UHFFFAOYSA-N 0.000 description 1
- UXXRGXFIRDLVIT-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CC)=C(C(=O)NOC(C)(C)C)N=C1C1=CC=C(Cl)C=C1Cl UXXRGXFIRDLVIT-UHFFFAOYSA-N 0.000 description 1
- RQFDHAZJXWQQBK-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl RQFDHAZJXWQQBK-UHFFFAOYSA-N 0.000 description 1
- MCLDRTREOJASMB-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-iodo-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1I MCLDRTREOJASMB-UHFFFAOYSA-N 0.000 description 1
- LECJJHPDXALPIK-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-(oxan-2-yloxy)imidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NOC2OCCCC2)N=C1C1=CC=C(Cl)C=C1Cl LECJJHPDXALPIK-UHFFFAOYSA-N 0.000 description 1
- PNYCYGVLNOKFSQ-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NOC(C)(C)C)N=C1C1=CC=C(Cl)C=C1Cl PNYCYGVLNOKFSQ-UHFFFAOYSA-N 0.000 description 1
- GJJWPAHIGGXADY-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-morpholin-4-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCOCC2)N=C1C1=CC=C(Cl)C=C1Cl GJJWPAHIGGXADY-UHFFFAOYSA-N 0.000 description 1
- GGRYXYYKYMJWIV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1Cl GGRYXYYKYMJWIV-UHFFFAOYSA-N 0.000 description 1
- QPHDCJUYVKUJRA-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-phenylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NC=2C=CC=CC=2)N=C1C1=CC=C(Cl)C=C1Cl QPHDCJUYVKUJRA-UHFFFAOYSA-N 0.000 description 1
- KKEBVIMUGTZZBL-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl KKEBVIMUGTZZBL-UHFFFAOYSA-N 0.000 description 1
- OGHUHFAJQSONNN-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methyl-n-pyrrolidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCCC2)N=C1C1=CC=C(Cl)C=C1Cl OGHUHFAJQSONNN-UHFFFAOYSA-N 0.000 description 1
- XBQPLQNMIBRBCV-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n,n-diethylimidazole-4-carboxamide Chemical compound N=1C(C(=O)N(CC)CC)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl XBQPLQNMIBRBCV-UHFFFAOYSA-N 0.000 description 1
- HTRCGPITLYPGLB-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-(2-fluoroethyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCCF)N=C1C1=CC=C(Cl)C=C1Cl HTRCGPITLYPGLB-UHFFFAOYSA-N 0.000 description 1
- RHWRJKGGXVYGPD-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound N=1C(C(=O)NOC(C)(C)C)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl RHWRJKGGXVYGPD-UHFFFAOYSA-N 0.000 description 1
- RGDWYZVJKQZPCR-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-[(4-fluorophenyl)methyl]-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCC=2C=CC(F)=CC=2)N=C1C1=CC=C(Cl)C=C1Cl RGDWYZVJKQZPCR-UHFFFAOYSA-N 0.000 description 1
- DKSATWBFRZWIOX-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-[(4-fluorophenyl)methyl]imidazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CN(C=2C=CC(Cl)=CC=2)C(C=2C(=CC(Cl)=CC=2)Cl)=N1 DKSATWBFRZWIOX-UHFFFAOYSA-N 0.000 description 1
- MYSGZZOTCIEIBN-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-phenylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC=2C=CC=CC=2)=C1 MYSGZZOTCIEIBN-UHFFFAOYSA-N 0.000 description 1
- CPZFFCWPBSKKAF-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1 CPZFFCWPBSKKAF-UHFFFAOYSA-N 0.000 description 1
- MAUBLDPPCZITOG-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-pyrrolidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCC2)=C1 MAUBLDPPCZITOG-UHFFFAOYSA-N 0.000 description 1
- HIEMKJSSXPDXSO-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carbonyl chloride Chemical compound N=1C(C(=O)Cl)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1Cl HIEMKJSSXPDXSO-UHFFFAOYSA-N 0.000 description 1
- LOYBJSXDJRFXGA-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1C(F)(F)F LOYBJSXDJRFXGA-UHFFFAOYSA-N 0.000 description 1
- KBSISTGQJOICMP-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1C(F)(F)F KBSISTGQJOICMP-UHFFFAOYSA-N 0.000 description 1
- BSOQXJWSLLCWAT-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]-n-(2,2,2-trifluoroethyl)imidazole-4-carboxamide Chemical compound N=1C(C(=O)NCC(F)(F)F)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1C(F)(F)F BSOQXJWSLLCWAT-UHFFFAOYSA-N 0.000 description 1
- YQAPRDAMNGCMED-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]-n-cyclohexyl-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1C(F)(F)F YQAPRDAMNGCMED-UHFFFAOYSA-N 0.000 description 1
- WWFMEJFZCAXZPY-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]-n-cyclohexylimidazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1C1=NC(C(=O)NC2CCCCC2)=CN1C1=CC=C(Cl)C=C1 WWFMEJFZCAXZPY-UHFFFAOYSA-N 0.000 description 1
- CQDOGEXMJOZWAE-UHFFFAOYSA-N 1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=CN1C1=CC=C(Cl)C=C1 CQDOGEXMJOZWAE-UHFFFAOYSA-N 0.000 description 1
- XIRHISFCEKCBJD-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-cyano-2-(2,4-dichlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C#N)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl XIRHISFCEKCBJD-UHFFFAOYSA-N 0.000 description 1
- OKDOSEGZYWGKMW-UHFFFAOYSA-N 1-(4-chlorophenyl)-5-cyano-n-cyclohexyl-2-(2,4-dichlorophenyl)imidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C#N)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl OKDOSEGZYWGKMW-UHFFFAOYSA-N 0.000 description 1
- UYDJPLQCNWEWBD-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-2-(1,5-dimethylpyrrol-2-yl)-5-methylimidazole-4-carboxamide Chemical compound CN1C(C)=CC=C1C1=NC(C(=O)NC2CCCCC2)=C(C)N1C1=CC=C(Cl)C=C1 UYDJPLQCNWEWBD-UHFFFAOYSA-N 0.000 description 1
- DOCHZHSBYZUORF-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-2-(2,4-dichlorophenyl)-5-iodoimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1I DOCHZHSBYZUORF-UHFFFAOYSA-N 0.000 description 1
- YCVHHBIJYZETRR-UHFFFAOYSA-N 1-(4-chlorophenyl)-n-cyclohexyl-2-(2,4-dichlorophenyl)imidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1 YCVHHBIJYZETRR-UHFFFAOYSA-N 0.000 description 1
- UDNOQKDUBDNUIZ-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethyl-n-[(4-fluorophenyl)methyl]imidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NCC=2C=CC(F)=CC=2)N=C1C1=CC=C(Cl)C=C1Cl UDNOQKDUBDNUIZ-UHFFFAOYSA-N 0.000 description 1
- ZDTZDVGEOOVXTH-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethyl-n-morpholin-4-ylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NN2CCOCC2)N=C1C1=CC=C(Cl)C=C1Cl ZDTZDVGEOOVXTH-UHFFFAOYSA-N 0.000 description 1
- FRVBQUOHEOBURA-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1Cl FRVBQUOHEOBURA-UHFFFAOYSA-N 0.000 description 1
- VXNVNNMYAHHVCN-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl VXNVNNMYAHHVCN-UHFFFAOYSA-N 0.000 description 1
- DUJBTKLEZZOSNY-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-methyl-n-morpholin-4-ylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NN2CCOCC2)N=C1C1=CC=C(Cl)C=C1Cl DUJBTKLEZZOSNY-UHFFFAOYSA-N 0.000 description 1
- NHPFFTWZTVFBMZ-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-methyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1Cl NHPFFTWZTVFBMZ-UHFFFAOYSA-N 0.000 description 1
- QGQXUYUPKOKDNE-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl QGQXUYUPKOKDNE-UHFFFAOYSA-N 0.000 description 1
- ZCSRAGFSWYIFHI-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-n-[(4-fluorophenyl)methyl]-5-methylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NCC=2C=CC(F)=CC=2)N=C1C1=CC=C(Cl)C=C1Cl ZCSRAGFSWYIFHI-UHFFFAOYSA-N 0.000 description 1
- FETBGDMTRFHVPE-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-n-cyclohexyl-2-(2,4-dichlorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl FETBGDMTRFHVPE-UHFFFAOYSA-N 0.000 description 1
- UBMWLNKLJXXNBQ-UHFFFAOYSA-N 1-(4-chloropyridin-2-yl)-n-cyclohexyl-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl UBMWLNKLJXXNBQ-UHFFFAOYSA-N 0.000 description 1
- NOUDGPISLXECAJ-UHFFFAOYSA-N 1h-imidazole-5-carbonyl chloride Chemical compound ClC(=O)C1=CNC=N1 NOUDGPISLXECAJ-UHFFFAOYSA-N 0.000 description 1
- HZUGXKOBWNOCKU-UHFFFAOYSA-N 2,4-dichloro-n'-(4-methoxyphenyl)benzenecarboximidamide Chemical compound C1=CC(OC)=CC=C1NC(=N)C1=CC=C(Cl)C=C1Cl HZUGXKOBWNOCKU-UHFFFAOYSA-N 0.000 description 1
- GRUHREVRSOOQJG-UHFFFAOYSA-N 2,4-dichlorobenzonitrile Chemical compound ClC1=CC=C(C#N)C(Cl)=C1 GRUHREVRSOOQJG-UHFFFAOYSA-N 0.000 description 1
- CEOCVKWBUWKBKA-UHFFFAOYSA-N 2,4-dichlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1Cl CEOCVKWBUWKBKA-UHFFFAOYSA-N 0.000 description 1
- PIQKCFMGYGBVIK-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl PIQKCFMGYGBVIK-UHFFFAOYSA-N 0.000 description 1
- HZDHNBOYRXSVQJ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1 HZDHNBOYRXSVQJ-UHFFFAOYSA-N 0.000 description 1
- VZVKCHVLMNXLHW-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1C VZVKCHVLMNXLHW-UHFFFAOYSA-N 0.000 description 1
- MIHNLYOTRRTNFJ-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1 MIHNLYOTRRTNFJ-UHFFFAOYSA-N 0.000 description 1
- XJQDCMMEDVRVBS-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-5-methyl-1-[4-(trifluoromethyl)phenyl]imidazole-4-carboxylic acid Chemical compound C=1C=C(C(F)(F)F)C=CC=1N1C(C)=C(C(O)=O)N=C1C1=CC=C(Cl)C=C1Cl XJQDCMMEDVRVBS-UHFFFAOYSA-N 0.000 description 1
- LXHJQKRDYPVDAL-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-5-methyl-n-piperidin-1-yl-1-[4-(trifluoromethyl)phenyl]imidazole-4-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl LXHJQKRDYPVDAL-UHFFFAOYSA-N 0.000 description 1
- KHBUUJAPLBLUGB-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-pentyl-1-pyridin-3-ylimidazole-4-carboxamide Chemical compound N=1C(C(=O)NCCCCC)=CN(C=2C=NC=CC=2)C=1C1=CC=C(Cl)C=C1Cl KHBUUJAPLBLUGB-UHFFFAOYSA-N 0.000 description 1
- ZZPDODRCDPPYKC-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-piperidin-1-yl-1-[4-(trifluoromethyl)phenyl]imidazole-4-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CCCCC2)=C1 ZZPDODRCDPPYKC-UHFFFAOYSA-N 0.000 description 1
- WNJDNWXZMKFRJK-UHFFFAOYSA-N 2-(2,4-dichlorophenyl)-n-piperidin-1-yl-1-pyridin-3-ylimidazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=CN1C1=CC=CN=C1 WNJDNWXZMKFRJK-UHFFFAOYSA-N 0.000 description 1
- RJMNZCAGYIQAGQ-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-5-ethyl-1-phenyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(CC)=C(C(=O)NN2CCCCC2)N=C1C1=CC(Cl)=CC=C1Cl RJMNZCAGYIQAGQ-UHFFFAOYSA-N 0.000 description 1
- WUJTXJXXRUZZPV-UHFFFAOYSA-N 2-(2,5-dichlorophenyl)-5-methyl-1-phenyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC(Cl)=CC=C1Cl WUJTXJXXRUZZPV-UHFFFAOYSA-N 0.000 description 1
- AJBLNNZIKFJBGJ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(3-fluorophenyl)-5-methyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1N1C(C)=C(C(=O)NCCCCC)N=C1C1=CC=CC=C1Cl AJBLNNZIKFJBGJ-UHFFFAOYSA-N 0.000 description 1
- AOCHSHKWGVRFEO-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(3-fluorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=CC=C1Cl AOCHSHKWGVRFEO-UHFFFAOYSA-N 0.000 description 1
- ZLEZEXVOMLFEJQ-UHFFFAOYSA-N 2-(2-chlorophenyl)-1-(3-fluorophenyl)-n-[2-(4-fluorophenyl)ethyl]-5-methylimidazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1N1C(C)=C(C(=O)NCCC=2C=CC(F)=CC=2)N=C1C1=CC=CC=C1Cl ZLEZEXVOMLFEJQ-UHFFFAOYSA-N 0.000 description 1
- SPDFXOWMDJEXAR-UHFFFAOYSA-N 2-(2-chlorophenyl)-n-cyclohexyl-1-(3-fluorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=CC(F)=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=CC=C1Cl SPDFXOWMDJEXAR-UHFFFAOYSA-N 0.000 description 1
- DCMOKKLQDPGGHS-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1-(4-chlorophenyl)-5-methyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1F DCMOKKLQDPGGHS-UHFFFAOYSA-N 0.000 description 1
- DUXPSBPTHURSBA-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1-(4-chlorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCCCC2)N=C1C1=CC=C(Cl)C=C1F DUXPSBPTHURSBA-UHFFFAOYSA-N 0.000 description 1
- HAZKVWRKKUQVSH-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1-(4-chlorophenyl)-n-cyclohexyl-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1F HAZKVWRKKUQVSH-UHFFFAOYSA-N 0.000 description 1
- JDEOVZDYIHGPOO-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1-(4-chlorophenyl)-n-cyclohexylimidazole-4-carboxamide Chemical compound FC1=CC(Cl)=CC=C1C1=NC(C(=O)NC2CCCCC2)=CN1C1=CC=C(Cl)C=C1 JDEOVZDYIHGPOO-UHFFFAOYSA-N 0.000 description 1
- JFSXLPIMYXNSMQ-UHFFFAOYSA-N 2-(4-chloro-2-fluorophenyl)-1-(4-chlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound FC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=CN1C1=CC=C(Cl)C=C1 JFSXLPIMYXNSMQ-UHFFFAOYSA-N 0.000 description 1
- XWKPZKFXLHZNQX-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-1-(4-chlorophenyl)-5-methyl-n-pentylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NCCCCC)N=C1C1=CC=C(Cl)C=C1OC XWKPZKFXLHZNQX-UHFFFAOYSA-N 0.000 description 1
- LVCXSRWNHMLVCP-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-1-(4-chlorophenyl)-5-methyl-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=C(C)N1C1=CC=C(Cl)C=C1 LVCXSRWNHMLVCP-UHFFFAOYSA-N 0.000 description 1
- WBNNOAZNGYXUBK-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-1-(4-chlorophenyl)-n-cyclohexyl-5-methylimidazole-4-carboxamide Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C(=O)NC2CCCCC2)=C(C)N1C1=CC=C(Cl)C=C1 WBNNOAZNGYXUBK-UHFFFAOYSA-N 0.000 description 1
- VZWSQUIVWPZHIX-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-1-(4-chlorophenyl)-n-cyclohexylimidazole-4-carboxamide Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C(=O)NC2CCCCC2)=CN1C1=CC=C(Cl)C=C1 VZWSQUIVWPZHIX-UHFFFAOYSA-N 0.000 description 1
- YVZPKZRRXGGHGN-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-1-(4-chlorophenyl)-n-pentylimidazole-4-carboxamide Chemical compound N=1C(C(=O)NCCCCC)=CN(C=2C=CC(Cl)=CC=2)C=1C1=CC=C(Cl)C=C1OC YVZPKZRRXGGHGN-UHFFFAOYSA-N 0.000 description 1
- NQZVEBSGPMWCFR-UHFFFAOYSA-N 2-(4-chloro-2-methoxyphenyl)-1-(4-chlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound COC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=CN1C1=CC=C(Cl)C=C1 NQZVEBSGPMWCFR-UHFFFAOYSA-N 0.000 description 1
- NNCYNUUMISWPFX-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methyl-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(C)=C(C(=O)NOC(C)(C)C)N=C1C1=CC=C(Cl)C=C1 NNCYNUUMISWPFX-UHFFFAOYSA-N 0.000 description 1
- DMTUNYPKQZNKIZ-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxylic acid Chemical compound C=1C=C(Cl)C=C(Cl)C=1N1C(C)=C(C(O)=O)N=C1C1=CC=C(Cl)C=C1 DMTUNYPKQZNKIZ-UHFFFAOYSA-N 0.000 description 1
- XZUKDNRETJUNGW-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n-[(2-methylpropan-2-yl)oxy]imidazole-4-carboxamide Chemical compound N=1C(C(=O)NOC(C)(C)C)=CN(C=2C(=CC(Cl)=CC=2)Cl)C=1C1=CC=C(Cl)C=C1 XZUKDNRETJUNGW-UHFFFAOYSA-N 0.000 description 1
- BSROPESOPXQHJD-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-n-piperidin-1-ylimidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCC2)=CN1C1=CC=C(Cl)C=C1Cl BSROPESOPXQHJD-UHFFFAOYSA-N 0.000 description 1
- QSNSCYSYFYORTR-UHFFFAOYSA-N 4-chloroaniline Chemical compound NC1=CC=C(Cl)C=C1 QSNSCYSYFYORTR-UHFFFAOYSA-N 0.000 description 1
- ODGIMMLDVSWADK-UHFFFAOYSA-N 4-trifluoromethylaniline Chemical compound NC1=CC=C(C(F)(F)F)C=C1 ODGIMMLDVSWADK-UHFFFAOYSA-N 0.000 description 1
- CYJRNFFLTBEQSQ-UHFFFAOYSA-N 8-(3-methyl-1-benzothiophen-5-yl)-N-(4-methylsulfonylpyridin-3-yl)quinoxalin-6-amine Chemical compound CS(=O)(=O)C1=C(C=NC=C1)NC=1C=C2N=CC=NC2=C(C=1)C=1C=CC2=C(C(=CS2)C)C=1 CYJRNFFLTBEQSQ-UHFFFAOYSA-N 0.000 description 1
- 241000722948 Apocynum cannabinum Species 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- 229940124802 CB1 antagonist Drugs 0.000 description 1
- 229940123158 Cannabinoid CB1 receptor antagonist Drugs 0.000 description 1
- 229940122820 Cannabinoid receptor antagonist Drugs 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000008697 Cannabis sativa Nutrition 0.000 description 1
- 241000699802 Cricetulus griseus Species 0.000 description 1
- IVOMOUWHDPKRLL-KQYNXXCUSA-N Cyclic adenosine monophosphate Chemical compound C([C@H]1O2)OP(O)(=O)O[C@H]1[C@@H](O)[C@@H]2N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-KQYNXXCUSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 235000015928 Hibiscus cannabinus Nutrition 0.000 description 1
- 101000710899 Homo sapiens Cannabinoid receptor 1 Proteins 0.000 description 1
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 1
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- 229910006024 SO2Cl2 Inorganic materials 0.000 description 1
- 229910006124 SOCl2 Inorganic materials 0.000 description 1
- CYQFCXCEBYINGO-UHFFFAOYSA-N THC Natural products C1=C(C)CCC2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3C21 CYQFCXCEBYINGO-UHFFFAOYSA-N 0.000 description 1
- IVOMOUWHDPKRLL-UHFFFAOYSA-N UNPD107823 Natural products O1C2COP(O)(=O)OC2C(O)C1N1C(N=CN=C2N)=C2N=C1 IVOMOUWHDPKRLL-UHFFFAOYSA-N 0.000 description 1
- RUAYKRGXLHCWBI-UHFFFAOYSA-N [1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazol-4-yl]-(1,2,3,4-tetrahydroisoquinolin-1-yl)methanone Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)C2C3=CC=CC=C3CCN2)N=C1C1=CC=C(Cl)C=C1Cl RUAYKRGXLHCWBI-UHFFFAOYSA-N 0.000 description 1
- JHZQLCVGUFCRSM-UHFFFAOYSA-N [1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazol-4-yl]-(4-hydroxypiperidin-1-yl)methanone Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)N2CCC(O)CC2)N=C1C1=CC=C(Cl)C=C1Cl JHZQLCVGUFCRSM-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 238000007112 amidation reaction Methods 0.000 description 1
- LGEQQWMQCRIYKG-DOFZRALJSA-N anandamide Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO LGEQQWMQCRIYKG-DOFZRALJSA-N 0.000 description 1
- LGEQQWMQCRIYKG-UHFFFAOYSA-N arachidonic acid ethanolamide Natural products CCCCCC=CCC=CCC=CCC=CCCCC(=O)NCCO LGEQQWMQCRIYKG-UHFFFAOYSA-N 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 230000001593 cAMP accumulation Effects 0.000 description 1
- 239000003554 cannabinoid 1 receptor agonist Substances 0.000 description 1
- 239000003555 cannabinoid 1 receptor antagonist Substances 0.000 description 1
- 239000003536 cannabinoid receptor antagonist Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- QODRGVWMWOLMTE-SAABIXHNSA-N chembl176198 Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)N[C@@H]2CC[C@@H](O)CC2)N=C1C1=CC=C(Cl)C=C1Cl QODRGVWMWOLMTE-SAABIXHNSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000001907 coumarones Chemical class 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- CYQFCXCEBYINGO-IAGOWNOFSA-N delta1-THC Chemical compound C1=C(C)CC[C@H]2C(C)(C)OC3=CC(CCCCC)=CC(O)=C3[C@@H]21 CYQFCXCEBYINGO-IAGOWNOFSA-N 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 229940043279 diisopropylamine Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 150000002066 eicosanoids Chemical class 0.000 description 1
- 238000010931 ester hydrolysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- VICYTAYPKBLQFB-UHFFFAOYSA-N ethyl 3-bromo-2-oxopropanoate Chemical compound CCOC(=O)C(=O)CBr VICYTAYPKBLQFB-UHFFFAOYSA-N 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 230000002140 halogenating effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- DLEDOFVPSDKWEF-UHFFFAOYSA-N lithium butane Chemical compound [Li+].CCC[CH2-] DLEDOFVPSDKWEF-UHFFFAOYSA-N 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- BGJXNYVUVCFFFF-UHFFFAOYSA-N n'-(4-bromophenyl)-2,4-dichlorobenzenecarboximidamide Chemical compound ClC1=CC(Cl)=CC=C1C(=N)NC1=CC=C(Br)C=C1 BGJXNYVUVCFFFF-UHFFFAOYSA-N 0.000 description 1
- DBNQIOANXZVWIP-UHFFFAOYSA-N n,n-dimethyl-1,1-bis[(2-methylpropan-2-yl)oxy]methanamine Chemical compound CC(C)(C)OC(N(C)C)OC(C)(C)C DBNQIOANXZVWIP-UHFFFAOYSA-N 0.000 description 1
- IVMOOXFELCCOMP-UHFFFAOYSA-N n-(1-adamantyl)-1-(4-chlorophenyl)-2-[4-chloro-2-(trifluoromethyl)phenyl]imidazole-4-carboxamide Chemical compound FC(F)(F)C1=CC(Cl)=CC=C1C1=NC(C(=O)NC23CC4CC(CC(C4)C2)C3)=CN1C1=CC=C(Cl)C=C1 IVMOOXFELCCOMP-UHFFFAOYSA-N 0.000 description 1
- SVSQPQKRRBNFOC-UHFFFAOYSA-N n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CC3CCCC3C2)N=C1C1=CC=C(Cl)C=C1Cl SVSQPQKRRBNFOC-UHFFFAOYSA-N 0.000 description 1
- GEUFMHWPIXFMJY-UHFFFAOYSA-N n-(3,3a,4,5,6,6a-hexahydro-1h-cyclopenta[c]pyrrol-2-yl)-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxamide Chemical compound C1=CC(Cl)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NN2CC3CCCC3C2)=C1 GEUFMHWPIXFMJY-UHFFFAOYSA-N 0.000 description 1
- HXLFSLVUWNBRDT-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-bromophenyl)-2-(2,4-dichlorophenyl)imidazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(C(=O)NN2CCCCCC2)=CN1C1=CC=C(Br)C=C1 HXLFSLVUWNBRDT-UHFFFAOYSA-N 0.000 description 1
- SMEFNROEYLLVDY-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)NN2CCCCCC2)N=C1C1=CC=C(Cl)C=C1Cl SMEFNROEYLLVDY-UHFFFAOYSA-N 0.000 description 1
- UNINKSRMOUERSC-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(CC)=C(C(=O)NN2CCCCCC2)N=C1C1=CC=C(Cl)C=C1Cl UNINKSRMOUERSC-UHFFFAOYSA-N 0.000 description 1
- GUNCGMZWTDRAJL-UHFFFAOYSA-N n-(azepan-1-yl)-1-(4-chloropyridin-2-yl)-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C(Cl)=CC=NC=1N1C(C)=C(C(=O)NN2CCCCCC2)N=C1C1=CC=C(Cl)C=C1Cl GUNCGMZWTDRAJL-UHFFFAOYSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- RYQNMPVOTHTFIF-UHFFFAOYSA-N n-benzyl-1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-n-methylimidazole-4-carboxamide Chemical compound C=1N(C=2C=CC(Cl)=CC=2)C(C=2C(=CC(Cl)=CC=2)Cl)=NC=1C(=O)N(C)CC1=CC=CC=C1 RYQNMPVOTHTFIF-UHFFFAOYSA-N 0.000 description 1
- NMJMVGDVVZUPOP-UHFFFAOYSA-N n-cyclohexyl-2-(1,5-dimethylpyrrol-2-yl)-5-ethyl-1-phenylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(C)N1C NMJMVGDVVZUPOP-UHFFFAOYSA-N 0.000 description 1
- VSXOYDKSPXUUIJ-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(2,5-difluorophenyl)-5-ethylimidazole-4-carboxamide Chemical compound C=1C(F)=CC=C(F)C=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl VSXOYDKSPXUUIJ-UHFFFAOYSA-N 0.000 description 1
- WUDKZQUCAOXVAT-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(2,5-difluorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C(F)=CC=C(F)C=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl WUDKZQUCAOXVAT-UHFFFAOYSA-N 0.000 description 1
- USKQSLWBDDIJSQ-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-fluorophenyl)-5-methylimidazole-4-carboxamide Chemical compound C=1C=C(F)C=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl USKQSLWBDDIJSQ-UHFFFAOYSA-N 0.000 description 1
- ZMRMCCQCBIVGDN-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-fluorophenyl)imidazole-4-carboxamide Chemical compound C1=CC(F)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1 ZMRMCCQCBIVGDN-UHFFFAOYSA-N 0.000 description 1
- XJWCYWLSWSGANR-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)-5-methylimidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1C XJWCYWLSWSGANR-UHFFFAOYSA-N 0.000 description 1
- TWRSTCDKXCLFEK-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-(4-methoxyphenyl)imidazole-4-carboxamide Chemical compound C1=CC(OC)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1 TWRSTCDKXCLFEK-UHFFFAOYSA-N 0.000 description 1
- ZJVOQGJSTHDEJL-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-[4-(trifluoromethyl)phenyl]imidazole-4-carboxamide Chemical compound C1=CC(C(F)(F)F)=CC=C1N1C(C=2C(=CC(Cl)=CC=2)Cl)=NC(C(=O)NC2CCCCC2)=C1 ZJVOQGJSTHDEJL-UHFFFAOYSA-N 0.000 description 1
- SBNWHIPARXVTSU-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-1-pyridin-3-ylimidazole-4-carboxamide Chemical compound ClC1=CC(Cl)=CC=C1C1=NC(C(=O)NC2CCCCC2)=CN1C1=CC=CN=C1 SBNWHIPARXVTSU-UHFFFAOYSA-N 0.000 description 1
- HTHSZSOQRAXEAS-UHFFFAOYSA-N n-cyclohexyl-2-(2,4-dichlorophenyl)-5-methyl-1-[4-(trifluoromethyl)phenyl]imidazole-4-carboxamide Chemical compound C=1C=C(C(F)(F)F)C=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC=C(Cl)C=C1Cl HTHSZSOQRAXEAS-UHFFFAOYSA-N 0.000 description 1
- VPVSRBWIFNSDMF-UHFFFAOYSA-N n-cyclohexyl-2-(2,5-dichlorophenyl)-5-ethyl-1-phenylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(CC)=C(C(=O)NC2CCCCC2)N=C1C1=CC(Cl)=CC=C1Cl VPVSRBWIFNSDMF-UHFFFAOYSA-N 0.000 description 1
- FBFGYIWCXJGEAG-UHFFFAOYSA-N n-cyclohexyl-2-(2,5-dichlorophenyl)-5-methyl-1-phenylimidazole-4-carboxamide Chemical compound C=1C=CC=CC=1N1C(C)=C(C(=O)NC2CCCCC2)N=C1C1=CC(Cl)=CC=C1Cl FBFGYIWCXJGEAG-UHFFFAOYSA-N 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 238000010647 peptide synthesis reaction Methods 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- IVSBKGWMJJCQHO-UHFFFAOYSA-N tert-butyl 1-(4-chlorophenyl)-2-(2,4-dichlorophenyl)-5-methylimidazole-4-carboxylate Chemical compound C=1C=C(Cl)C=CC=1N1C(C)=C(C(=O)OC(C)(C)C)N=C1C1=CC=C(Cl)C=C1Cl IVSBKGWMJJCQHO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/28—Nitrogen atoms
- C07D295/30—Nitrogen atoms non-acylated
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/08—Drugs for disorders of the alimentary tract or the digestive system for nausea, cinetosis or vertigo; Antiemetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/12—Antidiarrhoeals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/08—Antiepileptics; Anticonvulsants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/22—Anxiolytics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C257/00—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines
- C07C257/10—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines
- C07C257/18—Compounds containing carboxyl groups, the doubly-bound oxygen atom of a carboxyl group being replaced by a doubly-bound nitrogen atom, this nitrogen atom not being further bound to an oxygen atom, e.g. imino-ethers, amidines with replacement of the other oxygen atom of the carboxyl group by nitrogen atoms, e.g. amidines having carbon atoms of amidino groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- C07D401/02—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 two hetero rings
- C07D401/04—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 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
- C07D403/02—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
- 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
- C07D405/02—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 two hetero rings
- C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Diabetes (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Pulmonology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Cardiology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Child & Adolescent Psychology (AREA)
- Oncology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Addiction (AREA)
- Rheumatology (AREA)
- Communicable Diseases (AREA)
- Vascular Medicine (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01203851 | 2001-09-21 | ||
PCT/EP2002/010434 WO2003027076A2 (fr) | 2001-09-21 | 2002-09-17 | Derives de 1h-imidazole ayant une activite antagoniste de cb1 |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20040185A2 true HRP20040185A2 (en) | 2004-08-31 |
Family
ID=8181044
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20040185A HRP20040185A2 (en) | 2001-09-21 | 2004-02-25 | 1h-imidazole derivatives having cb<sub>1</sub> agonistic, cb<sub>1</sub> partial agonistic or cb<sub>1</sub> antagonistic activity |
Country Status (26)
Country | Link |
---|---|
US (2) | US20040235854A1 (fr) |
EP (1) | EP1438296B1 (fr) |
JP (1) | JP4393869B2 (fr) |
KR (1) | KR100950431B1 (fr) |
CN (2) | CN101538244A (fr) |
AR (1) | AR036597A1 (fr) |
AT (1) | ATE415391T1 (fr) |
AU (1) | AU2002337106B2 (fr) |
BR (1) | BR0212481A (fr) |
CA (1) | CA2457444C (fr) |
DE (1) | DE60230054D1 (fr) |
DK (1) | DK1438296T3 (fr) |
ES (1) | ES2318045T3 (fr) |
HR (1) | HRP20040185A2 (fr) |
HU (1) | HUP0402150A3 (fr) |
IL (2) | IL160522A0 (fr) |
MX (1) | MXPA04002669A (fr) |
NO (1) | NO20041171L (fr) |
PL (1) | PL367998A1 (fr) |
PT (1) | PT1438296E (fr) |
RU (1) | RU2299200C2 (fr) |
SI (1) | SI1438296T1 (fr) |
TW (1) | TWI231757B (fr) |
UA (1) | UA77440C2 (fr) |
WO (1) | WO2003027076A2 (fr) |
ZA (1) | ZA200402188B (fr) |
Families Citing this family (113)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AU2002319627A1 (en) | 2001-07-20 | 2003-03-03 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
US7109216B2 (en) | 2001-09-21 | 2006-09-19 | Solvay Pharmaceuticals B.V. | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
US20060100196A1 (en) * | 2001-09-24 | 2006-05-11 | Andrea Gailunas | Substituted amines for the treatment of alzheimer's disease |
AR036608A1 (es) | 2001-09-24 | 2004-09-22 | Bayer Corp | Derivados de imidazol, composiciones farmaceuticas y el uso de dichos derivados para la fabricacion de un medicamento para el tratamiento de la obesidad |
CA2478183C (fr) | 2002-03-12 | 2010-02-16 | Merck & Co. Inc. | Amides substitues |
US7405221B2 (en) | 2002-09-27 | 2008-07-29 | Merck & Co., Inc. | Substituted pyrimidines |
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 |
MXPA05007114A (es) * | 2003-01-02 | 2005-08-26 | Hoffmann La Roche | Nuevos agonistas inversos del receptor cb1. |
EP1586068B1 (fr) * | 2003-01-23 | 2008-07-30 | U.S. Genomics, Inc. | Methodes d'analyse de populations de polymeres |
US7772188B2 (en) | 2003-01-28 | 2010-08-10 | Ironwood Pharmaceuticals, Inc. | Methods and compositions for the treatment of gastrointestinal disorders |
KR20050096956A (ko) | 2003-02-07 | 2005-10-06 | 다이이찌 세이야꾸 가부시기가이샤 | 피라졸 유도체 |
US7176210B2 (en) | 2003-02-10 | 2007-02-13 | Pfizer Inc. | Cannabinoid receptor ligands and uses thereof |
EP1621537A4 (fr) * | 2003-04-21 | 2008-12-31 | Daiichi Seiyaku Co | Derive heterocyclique a cinq chainons |
US7145012B2 (en) | 2003-04-23 | 2006-12-05 | 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 |
US20040224962A1 (en) * | 2003-05-09 | 2004-11-11 | Pfizer Inc | Pharmaceutical composition for the treatment of obesity or to facilitate or promote weight loss |
US20040224963A1 (en) * | 2003-05-09 | 2004-11-11 | Pfizer Inc | Pharmaceutical composition for the prevention and treatment of nicotine addiction in a mammal |
SE0301446D0 (sv) | 2003-05-16 | 2003-05-16 | Astrazeneca Ab | New Compounds |
US7232823B2 (en) | 2003-06-09 | 2007-06-19 | Pfizer, Inc. | Cannabinoid receptor ligands and uses thereof |
SE0301699D0 (sv) * | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
SE0301698D0 (sv) * | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
SE0301701D0 (sv) | 2003-06-10 | 2003-06-10 | Astrazeneca Ab | Benzimidazole derivatives, compositions containing them, preparation thereof and uses thereof |
US20040259887A1 (en) * | 2003-06-18 | 2004-12-23 | Pfizer Inc | Cannabinoid receptor ligands and uses thereof |
US7276608B2 (en) | 2003-07-11 | 2007-10-02 | Bristol-Myers Squibb Company | Tetrahydroquinoline derivatives as cannabinoid receptor modulators |
US20050026983A1 (en) * | 2003-07-30 | 2005-02-03 | Pfizer Inc | Imidazole compounds and uses thereof |
US7326706B2 (en) | 2003-08-15 | 2008-02-05 | Bristol-Myers Squibb Company | Pyrazine modulators of cannabinoid receptors |
US20050239859A2 (en) * | 2003-09-03 | 2005-10-27 | Solvay Pharmaceuticals Gmbh | Novel medical uses of 4,5-dihydro-1h-pyrazole derivatives having cb1- antagonistic activity |
AR046182A1 (es) * | 2003-10-20 | 2005-11-30 | Solvay Pharm Bv | Derivados de 1h- imidazol como moduladores del receptor canabinoide. composiciones farmaceuticas que los contienen. |
BRPI0414511A (pt) * | 2003-10-20 | 2006-11-07 | Solvay Pharm Bv | composto, composições farmacêuticas, e, uso de um composto |
CA2543338A1 (fr) * | 2003-10-24 | 2005-05-06 | Solvay Pharmaceuticals Gmbh | Nouvelles utilisations medicales de composes a activite antagoniste de cb1 et traitement combine impliquant ces composes |
US20050143441A1 (en) * | 2003-10-27 | 2005-06-30 | Jochen Antel | Novel medical combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity |
US20050124660A1 (en) * | 2003-10-27 | 2005-06-09 | Jochen Antel | Novel medical uses of compounds showing CB1-antagonistic activity and combination treatment involving said compounds |
JP2007509996A (ja) | 2003-11-05 | 2007-04-19 | エフ.ホフマン−ラ ロシュ アーゲー | Ppar活性化剤としてのヘテロアリール誘導体 |
TW200522944A (en) | 2003-12-23 | 2005-07-16 | Lilly Co Eli | CB1 modulator compounds |
FR2866340B1 (fr) | 2004-02-13 | 2006-11-24 | Sanofi Synthelabo | Derives d'oxazole, leur preparation et leur utilisation en therapeutique. |
US7173044B2 (en) | 2004-02-19 | 2007-02-06 | Solvay Pharmaceuticals B.V. | Imidazoline derivatives having CB1-antagonistic activity |
AR047613A1 (es) * | 2004-02-19 | 2006-01-25 | Solvay Pharm Bv | Derivados de imidazolina que tienen actividad antagonista cb1 |
SI1725536T1 (sl) * | 2004-02-19 | 2009-04-30 | Solvay Pharm Bv | Derivati imidazolina s cb1-antagonistiäśno aktivnostjo |
GB0404105D0 (en) * | 2004-02-24 | 2004-03-31 | Glaxo Group Ltd | Novel compounds |
CN1938023A (zh) * | 2004-03-08 | 2007-03-28 | 惠氏公司 | 离子通道调节剂 |
EP2305352A1 (fr) | 2004-04-02 | 2011-04-06 | Merck Sharp & Dohme Corp. | Inhibiteurs de la 5-alpha-reductase pour le traitement d'hommes aux troubles métaboliques et anthropométriques |
BRPI0509515A (pt) * | 2004-04-03 | 2007-09-11 | Astrazeneca Ab | composto, formulação farmacêutica, uso de um composto método para tratamento de doenças, e, processo para a preparação de um composto |
ES2324720T3 (es) | 2004-05-10 | 2009-08-13 | F. Hoffmann-La Roche Ag | Pirrol o imidazol amidas para tratar la obesidad. |
US7524867B2 (en) | 2004-05-28 | 2009-04-28 | Solvay Pharmaceuticals, B.V. | Tetrasubstituted imidazole derivatives as cannabinoid CB1 receptor modulators with a high CB1/CB2 receptor subtype selectivity |
CA2565326A1 (fr) * | 2004-05-28 | 2005-12-15 | Solvay Pharmaceuticals B.V. | Derives d'imidazole tetrasubstitues utilises comme modulateurs du recepteur des cannabinoides cb<sb>1</sb> a activite de selectivite de sous-types du recepteur cb<sb>1</sb>/cb<sb>2</sb> elevee |
TW200608968A (en) * | 2004-05-28 | 2006-03-16 | Solvay Pharm Bv | Tetrasubstituted imidazole derivatives as cannabinoid cb1 receptor modulators with a high cb1/cb2 receptor subtype selectivity |
TW200602314A (en) | 2004-05-28 | 2006-01-16 | Tanabe Seiyaku Co | A novel pyrrolidine compound and a process for preparing the same |
NZ580387A (en) | 2004-07-12 | 2011-06-30 | Cadila Healthcare Ltd | Tricyclic pyrazole derivatives as cannabinoid receptor modulators |
US20060025448A1 (en) | 2004-07-22 | 2006-02-02 | Cadila Healthcare Limited | Hair growth stimulators |
FR2874012B1 (fr) * | 2004-08-09 | 2008-08-22 | Sanofi Synthelabo | Derives de pyrrole, leur preparation et leur utlisation en therapeutique |
BRPI0517434A (pt) * | 2004-10-25 | 2008-10-07 | Solvay Pharm Gmbh | composições farmacêuticas compreendendo antagonistas do receptor canabinóide cb1 e abridores de canal de potássio para o tratamento de diabetes mellitus do tipo i, obesidade e estados relacionados |
WO2006060202A2 (fr) * | 2004-11-30 | 2006-06-08 | Bayer Pharmaceuticals Corporation | Derives d'imidazole utilises dans le traitement de troubles psychiatriques |
WO2006060190A2 (fr) * | 2004-11-30 | 2006-06-08 | Bayer Pharmaceuticals Corporation | Derives d'imidazole |
WO2006060203A2 (fr) * | 2004-11-30 | 2006-06-08 | Bayer Pharmaceuticals Corporation | Derives d'imidazole utilises dans le traitement de la demence et des troubles associes |
CA2589483C (fr) | 2004-12-03 | 2013-10-29 | Schering Corporation | Piperazines substituees en tant qu'antagonistes de cb1 |
WO2006067428A2 (fr) * | 2004-12-23 | 2006-06-29 | Astrazeneca Ab | Agents therapeutiques |
EP1845972A4 (fr) | 2005-01-10 | 2010-12-22 | Univ Connecticut | Nouveaux analogues d'heteropyrroles agissant sur les recepteurs cannabinoides |
AU2006205220B2 (en) * | 2005-01-10 | 2012-09-13 | Exelixis, Inc. | Heterocyclic carboxamide compounds as steroid nuclear receptors ligands |
US8937184B2 (en) | 2005-02-16 | 2015-01-20 | Abbvie B.V. | 1H-imidazole derivatives as cannabinoid CB2 receptor modulators |
CA2613678A1 (fr) | 2005-06-02 | 2006-12-07 | Glenmark Pharmaceuticals S.A. | Nouveaux ligands des recepteurs des cannabinoides, compositions pharmaceutiques contenant ces ligands, et procede servant a leur preparation |
US7923465B2 (en) | 2005-06-02 | 2011-04-12 | Glenmark Pharmaceuticals S.A. | Cannabinoid receptor ligands, pharmaceutical compositions containing them, and process for their preparation |
US20100063081A1 (en) | 2005-06-30 | 2010-03-11 | Stuart Edward Bradly | CPCR Agonists |
WO2007024744A2 (fr) * | 2005-08-21 | 2007-03-01 | Exelixis, Inc. | Composes de carboxamide heterocycliques en tant qu'agents pharmaceutiques |
GB0518819D0 (en) * | 2005-09-15 | 2005-10-26 | Astrazeneca Ab | Therapeutic agents |
GB0518817D0 (en) * | 2005-09-15 | 2005-10-26 | Astrazeneca Ab | Therapeutic agents |
KR100694181B1 (ko) * | 2005-11-25 | 2007-03-12 | 연세대학교 산학협력단 | 근원세포 또는 근섬유로부터 신경세포 분화를 유도하는화합물, 이를 포함하는 약학적 조성물, 신경세포 분화를유도하는 방법 및 신경세포 분화를 유도하는 화합물을검색하는 스크리닝 방법 |
TW200736227A (en) | 2005-12-23 | 2007-10-01 | Astrazeneca Ab | New compounds III |
BRPI0706623A2 (pt) * | 2006-01-18 | 2011-04-12 | Schering Corp | moduladores de receptor canabinóide |
TWI433839B (zh) | 2006-08-11 | 2014-04-11 | Neomed Inst | 新穎的苯并咪唑衍生物290 |
PE20081849A1 (es) | 2007-01-04 | 2009-01-26 | Prosidion Ltd | Derivados de piperidin-4-il-propoxi-benzamida como agonistas de gpcr |
EP2114936A1 (fr) | 2007-01-04 | 2009-11-11 | Prosidion Limited | Agonistes de gpcr pipéridiniques |
JP2010514828A (ja) | 2007-01-04 | 2010-05-06 | プロシディオン・リミテッド | ピペリジンgpcrアゴニスト |
GB0700122D0 (en) | 2007-01-04 | 2007-02-14 | Prosidion Ltd | GPCR agonists |
PE20081659A1 (es) | 2007-01-04 | 2008-10-24 | Prosidion Ltd | Agonistas de gpcr |
WO2008130616A2 (fr) * | 2007-04-19 | 2008-10-30 | Schering Corporation | Diaryl morpholines comme modulateurs des récepteurs cb1 |
AU2008261102B2 (en) | 2007-06-04 | 2013-11-28 | Bausch Health Ireland Limited | Agonists of guanylate cyclase useful for the treatment of gastrointestinal disorders, inflammation, cancer and other disorders |
US8969514B2 (en) | 2007-06-04 | 2015-03-03 | Synergy Pharmaceuticals, Inc. | Agonists of guanylate cyclase useful for the treatment of hypercholesterolemia, atherosclerosis, coronary heart disease, gallstone, obesity and other cardiovascular diseases |
CN101790521A (zh) * | 2007-06-28 | 2010-07-28 | 英特维特国际股份有限公司 | 作为cb1拮抗剂的取代哌嗪 |
MX2010000334A (es) * | 2007-06-28 | 2010-04-22 | Intervet Int Bv | Piperazinas sustituidas como antagonistas de cannabinoides 1. |
GB0720390D0 (en) | 2007-10-18 | 2007-11-28 | Prosidion Ltd | G-Protein coupled receptor agonists |
GB0720389D0 (en) | 2007-10-18 | 2008-11-12 | Prosidion Ltd | G-Protein Coupled Receptor Agonists |
ES2716407T3 (es) | 2007-11-30 | 2019-06-12 | Zynerba Pharmaceuticals Inc | Profármacos de tetrahidrocannabinol, composiciones que comprenden profármacos de tetrahidrocannabinol y métodos para uso de los mismos |
CA2930674A1 (fr) | 2008-06-04 | 2009-12-10 | Synergy Pharmaceuticals Inc. | Agonistes de guanylate cyclase utile dans le traitement de troubles gastro-intestinaux, d'une inflammation, d'un cancer et d'autres troubles |
US9447049B2 (en) | 2010-03-01 | 2016-09-20 | University Of Tennessee Research Foundation | Compounds for treatment of cancer |
MX2010014066A (es) * | 2008-06-16 | 2011-06-01 | Univ Tennessee Res Foundation | Compuestos para el tratamiento del cancer. |
US9029408B2 (en) | 2008-06-16 | 2015-05-12 | Gtx, Inc. | Compounds for treatment of cancer |
US8822513B2 (en) | 2010-03-01 | 2014-09-02 | Gtx, Inc. | Compounds for treatment of cancer |
JP2011528375A (ja) | 2008-07-16 | 2011-11-17 | シナジー ファーマシューティカルズ インコーポレイテッド | 胃腸障害、炎症、癌、およびその他の障害の治療のために有用なグアニル酸シクラーゼのアゴニスト |
CN102264228A (zh) | 2008-10-22 | 2011-11-30 | 默沙东公司 | 用于抗糖尿病药的新的环状苯并咪唑衍生物 |
AU2009309037A1 (en) | 2008-10-31 | 2010-05-06 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
WO2010079241A1 (fr) | 2009-01-12 | 2010-07-15 | Fundacion Hospital Nacional De Paraplejicos Para La Investigacion Y La Integracion | Utilisation d'antagonistes et/ou d'agonistes inverses des récepteurs cb1 pour la préparation de médicaments qui augmentent l'excitabilité des motoneurones |
AU2011218830B2 (en) | 2010-02-25 | 2014-07-24 | Merck Sharp & Dohme Corp. | Novel cyclic benzimidazole derivatives useful anti-diabetic agents |
WO2011109059A1 (fr) | 2010-03-01 | 2011-09-09 | Gtx, Inc. | Composés destinés au traitement du cancer |
US9616097B2 (en) | 2010-09-15 | 2017-04-11 | Synergy Pharmaceuticals, Inc. | Formulations of guanylate cyclase C agonists and methods of use |
ES2652662T3 (es) | 2011-02-25 | 2018-02-05 | Merck Sharp & Dohme Corp. | Novedosos derivados de azabencimidazol cíclicos útiles como agentes antidiabéticos |
AU2013296470B2 (en) | 2012-08-02 | 2016-03-17 | Merck Sharp & Dohme Corp. | Antidiabetic tricyclic compounds |
MX2015010935A (es) | 2013-02-22 | 2015-10-29 | Merck Sharp & Dohme | Compuestos biciclicos antidiabeticos. |
WO2014139388A1 (fr) | 2013-03-14 | 2014-09-18 | Merck Sharp & Dohme Corp. | Nouveaux dérivés d'indole utiles en tant qu'agents antidiabétiques |
CA2905438A1 (fr) | 2013-03-15 | 2014-09-25 | Synergy Pharmaceuticals Inc. | Agonistes de la guanylate cyclase et leurs utilisations |
JP2016514670A (ja) | 2013-03-15 | 2016-05-23 | シナジー ファーマシューティカルズ インコーポレイテッド | 他の薬物と組み合わせたグアニル酸シクラーゼ受容体アゴニスト |
JP6606491B2 (ja) | 2013-06-05 | 2019-11-13 | シナジー ファーマシューティカルズ インコーポレイテッド | グアニル酸シクラーゼcの超高純度アゴニスト、その作成および使用方法 |
WO2015051496A1 (fr) | 2013-10-08 | 2015-04-16 | Merck Sharp & Dohme Corp. | Composés tricycliques antidiabétiques |
CA2949559C (fr) | 2014-06-06 | 2023-08-29 | Research Triangle Institute | Agonistes du recepteur de l'apeline (apj) et leurs utilisations |
CN108602806B (zh) | 2015-12-09 | 2022-07-12 | 研究三角协会 | 改进的爱帕琳肽受体(apj)激动剂及其用途 |
KR102541080B1 (ko) * | 2016-10-12 | 2023-06-08 | 리서치 트라이앵글 인스티튜트 | 복소환식 아펠린 수용체(apj) 작용제 및 이의 용도 |
WO2018106518A1 (fr) | 2016-12-06 | 2018-06-14 | Merck Sharp & Dohme Corp. | Composés hétérocycliques antidiabétiques |
WO2019042267A1 (fr) * | 2017-08-28 | 2019-03-07 | 中国医学科学院药物研究所 | Composé pyrrole-2-formamide, son procédé de préparation et ses applications |
CN113166068A (zh) * | 2018-11-20 | 2021-07-23 | 上海科技大学 | MmpL3抑制剂、组合物及其用途 |
CN112558265B (zh) * | 2019-09-26 | 2022-04-19 | 张家港梓阳电子科技有限公司 | 一种用于气体准分子激光器镜头的锁定装置 |
CA3125847A1 (fr) | 2020-07-27 | 2022-01-27 | Makscientific, Llc | Procede de fabrication de composes biologiquement actifs et d'intermediaires connexes |
WO2024009283A1 (fr) * | 2022-07-07 | 2024-01-11 | University Of Southern California | Antagonistes at2 pour soulager la douleur non addictive |
Family Cites Families (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DD140966A1 (de) * | 1978-12-28 | 1980-04-09 | Doerthe Creuzburg | Mittel zur regulierung des pflanzenwachstums |
US4813998A (en) * | 1986-02-27 | 1989-03-21 | Janssen Pharmaceutica N.V. | Herbicidal 1H-imidazole-5-carboxylic acid derivatives |
FR2692575B1 (fr) | 1992-06-23 | 1995-06-30 | Sanofi Elf | Nouveaux derives du pyrazole, procede pour leur preparation et compositions pharmaceutiques les contenant. |
US5616601A (en) * | 1994-07-28 | 1997-04-01 | Gd Searle & Co | 1,2-aryl and heteroaryl substituted imidazolyl compounds for the treatment of inflammation |
FR2789079B3 (fr) * | 1999-02-01 | 2001-03-02 | Sanofi Synthelabo | Derive d'acide pyrazolecarboxylique, sa preparation, les compositions pharmaceutiques en contenant |
CO5170501A1 (es) * | 1999-04-14 | 2002-06-27 | Novartis Ag | AZOLES SUSTITUIDOS UTILES PARA EL TRATAMIENTO DE ENFERMEDADES MEDIADAS POR TNFa eIL-1 Y ENFERMEDADES DEL METABOLISMO OSEO |
US6492516B1 (en) * | 1999-05-14 | 2002-12-10 | Merck & Co., Inc. | Compounds having cytokine inhibitory activity |
DE60124685T2 (de) | 2000-03-23 | 2007-03-29 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-1h-pyrazolderivate mit cb1-antagonistischer aktivität |
DE60202270T2 (de) | 2001-03-22 | 2005-05-19 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-1h-pyrazolderivate mit cb1-antagonistischer wirkung |
US7109216B2 (en) * | 2001-09-21 | 2006-09-19 | Solvay Pharmaceuticals B.V. | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity |
AR036608A1 (es) * | 2001-09-24 | 2004-09-22 | Bayer Corp | Derivados de imidazol, composiciones farmaceuticas y el uso de dichos derivados para la fabricacion de un medicamento para el tratamiento de la obesidad |
US20040248956A1 (en) * | 2002-01-29 | 2004-12-09 | Hagmann William K | Substituted imidazoles as cannabinoid receptor modulators |
US7524867B2 (en) * | 2004-05-28 | 2009-04-28 | Solvay Pharmaceuticals, B.V. | Tetrasubstituted imidazole derivatives as cannabinoid CB1 receptor modulators with a high CB1/CB2 receptor subtype selectivity |
-
2002
- 2002-08-30 TW TW091119798A patent/TWI231757B/zh not_active IP Right Cessation
- 2002-09-17 US US10/490,019 patent/US20040235854A1/en not_active Abandoned
- 2002-09-17 UA UA20040402980A patent/UA77440C2/uk unknown
- 2002-09-17 PT PT02772314T patent/PT1438296E/pt unknown
- 2002-09-17 HU HU0402150A patent/HUP0402150A3/hu unknown
- 2002-09-17 CA CA2457444A patent/CA2457444C/fr not_active Expired - Fee Related
- 2002-09-17 CN CNA2008101896834A patent/CN101538244A/zh active Pending
- 2002-09-17 AT AT02772314T patent/ATE415391T1/de active
- 2002-09-17 DK DK02772314T patent/DK1438296T3/da active
- 2002-09-17 CN CNA028183460A patent/CN1556703A/zh active Pending
- 2002-09-17 JP JP2003530667A patent/JP4393869B2/ja not_active Expired - Fee Related
- 2002-09-17 RU RU2004111979/04A patent/RU2299200C2/ru not_active IP Right Cessation
- 2002-09-17 EP EP02772314A patent/EP1438296B1/fr not_active Expired - Lifetime
- 2002-09-17 IL IL16052202A patent/IL160522A0/xx unknown
- 2002-09-17 KR KR1020047004084A patent/KR100950431B1/ko not_active IP Right Cessation
- 2002-09-17 WO PCT/EP2002/010434 patent/WO2003027076A2/fr active IP Right Grant
- 2002-09-17 MX MXPA04002669A patent/MXPA04002669A/es active IP Right Grant
- 2002-09-17 ES ES02772314T patent/ES2318045T3/es not_active Expired - Lifetime
- 2002-09-17 DE DE60230054T patent/DE60230054D1/de not_active Expired - Lifetime
- 2002-09-17 SI SI200230794T patent/SI1438296T1/sl unknown
- 2002-09-17 PL PL02367998A patent/PL367998A1/xx unknown
- 2002-09-17 AU AU2002337106A patent/AU2002337106B2/en not_active Ceased
- 2002-09-17 BR BR0212481-5A patent/BR0212481A/pt not_active IP Right Cessation
- 2002-09-18 AR ARP020103507A patent/AR036597A1/es unknown
-
2004
- 2004-02-23 IL IL160522A patent/IL160522A/en not_active IP Right Cessation
- 2004-02-25 HR HR20040185A patent/HRP20040185A2/hr not_active Application Discontinuation
- 2004-03-18 ZA ZA200402188A patent/ZA200402188B/en unknown
- 2004-03-19 NO NO20041171A patent/NO20041171L/no not_active Application Discontinuation
-
2008
- 2008-09-02 US US12/203,113 patent/US8729101B2/en not_active Expired - Fee Related
Also Published As
Similar Documents
Publication | Publication Date | Title |
---|---|---|
HRP20040185A2 (en) | 1h-imidazole derivatives having cb<sub>1</sub> agonistic, cb<sub>1</sub> partial agonistic or cb<sub>1</sub> antagonistic activity | |
US7109216B2 (en) | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1-antagonistic activity | |
AU2002337106A1 (en) | 1H-imidazole derivatives having CB1 agonistic, CB1 partial agonistic or CB1- antagonistic activity | |
CA2753061C (fr) | Nouveaux analogues heteropyrroles agissant sur les recepteurs cannabinoides | |
HRP20040085A2 (en) | Novel 4,5-dihydro-1h-pyrazole derivatives having cb-1 agonistic activity | |
JP2004500401A (ja) | Cb1−拮抗活性を有する4,5−ジヒドロ−1h−ピラゾール誘導体 | |
CZ20031795A3 (cs) | Fenylethenylové nebo fenylethynylové deriváty jako antagonisté glutamátového receptoru | |
AU2006328483A1 (en) | 4,5-dihydro- (1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators | |
TW200934497A (en) | Heterocyclic derivatives | |
KR20130143141A (ko) | 피라졸리딘-3-온 유도체 | |
EP1675833B1 (fr) | Derives de 1h-imidazole comme modulateurs du recepteur de cannabinoides | |
KR20100072037A (ko) | 칸나비노이드 cb₁수용체 효능제로서의 5-아릴-4,5-디하이드로-(1h)-피라졸 | |
US8410135B2 (en) | 4,5 dihydro-(1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators | |
Lange et al. | 4, 5 Dihydro-(1H)-Pyrazole Derivatives as Cannabinoid CB1 Receptor Modulators | |
AU2008263915A1 (en) | 4,5-dihydro-(1H)-pyrazole derivatives as cannabinoid CB1 receptor modulators | |
TW200916442A (en) | 4, 5-dihydro-(1H)-pyrazole derivatives as cannabinoid CB1receptor modulators | |
TW200524908A (en) | 1H-imidazole derivatives as cannabinoid receptor modulators | |
TW200305411A (en) | Thiazole derivatives having CB-antagonistic, agonistic or partial agonistic activity |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
A1OB | Publication of a patent application | ||
ARAI | Request for the grant of a patent on the basis of the submitted results of a substantive examination of a patent application | ||
ODRP | Renewal fee for the maintenance of a patent |
Payment date: 20100906 Year of fee payment: 9 |
|
OBST | Application withdrawn |