AU2004283055A1 - Combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity and lipase inhibitors - Google Patents
Combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity and lipase inhibitors Download PDFInfo
- Publication number
- AU2004283055A1 AU2004283055A1 AU2004283055A AU2004283055A AU2004283055A1 AU 2004283055 A1 AU2004283055 A1 AU 2004283055A1 AU 2004283055 A AU2004283055 A AU 2004283055A AU 2004283055 A AU2004283055 A AU 2004283055A AU 2004283055 A1 AU2004283055 A1 AU 2004283055A1
- Authority
- AU
- Australia
- Prior art keywords
- compound
- obesity
- antagonistic
- treatment
- prophylaxis
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 208000008589 Obesity Diseases 0.000 title claims description 98
- 235000020824 obesity Nutrition 0.000 title claims description 98
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 title claims description 15
- 229940127470 Lipase Inhibitors Drugs 0.000 title description 19
- 230000000694 effects Effects 0.000 title description 15
- 238000011284 combination treatment Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 162
- 108090001060 Lipase Proteins 0.000 claims description 92
- 239000004367 Lipase Substances 0.000 claims description 92
- 102000004882 Lipase Human genes 0.000 claims description 92
- 235000019421 lipase Nutrition 0.000 claims description 92
- 230000002401 inhibitory effect Effects 0.000 claims description 79
- 238000011282 treatment Methods 0.000 claims description 78
- 230000003042 antagnostic effect Effects 0.000 claims description 65
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 239000003814 drug Substances 0.000 claims description 47
- 238000011321 prophylaxis Methods 0.000 claims description 47
- 150000003839 salts Chemical class 0.000 claims description 40
- 230000000366 juvenile effect Effects 0.000 claims description 38
- 229940079593 drug Drugs 0.000 claims description 35
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 claims description 32
- 239000000651 prodrug Substances 0.000 claims description 32
- 229940002612 prodrug Drugs 0.000 claims description 32
- 229960001243 orlistat Drugs 0.000 claims description 31
- -1 trifluoromethoxy, nitro, amino Chemical group 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 27
- MVCQKIKWYUURMU-UHFFFAOYSA-N cetilistat Chemical compound C1=C(C)C=C2C(=O)OC(OCCCCCCCCCCCCCCCC)=NC2=C1 MVCQKIKWYUURMU-UHFFFAOYSA-N 0.000 claims description 24
- 229950002397 cetilistat Drugs 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229920000642 polymer Polymers 0.000 claims description 23
- 239000005557 antagonist Substances 0.000 claims description 20
- 229910052736 halogen Inorganic materials 0.000 claims description 20
- 150000002367 halogens Chemical class 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
- SIKWOTFNWURSAY-UHFFFAOYSA-N Lipstatin Natural products CCCCCCC1C(CC(CC=CCC=CCCCCC)C(=O)OC(CC(C)C)NC=O)OC1=O SIKWOTFNWURSAY-UHFFFAOYSA-N 0.000 claims description 14
- 230000003389 potentiating effect Effects 0.000 claims description 14
- 241000218236 Cannabis Species 0.000 claims description 13
- OQMAKWGYQLJJIA-CUOOPAIESA-N lipstatin Chemical compound CCCCCC[C@H]1[C@H](C[C@H](C\C=C/C\C=C/CCCCC)OC(=O)[C@H](CC(C)C)NC=O)OC1=O OQMAKWGYQLJJIA-CUOOPAIESA-N 0.000 claims description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000004076 pyridyl group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000001624 naphthyl group Chemical group 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 5
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 229940127557 pharmaceutical product Drugs 0.000 claims description 3
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 3
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 claims description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 229940040461 lipase Drugs 0.000 description 62
- 125000003118 aryl group Chemical group 0.000 description 22
- 125000001072 heteroaryl group Chemical group 0.000 description 17
- 229940086609 Lipase inhibitor Drugs 0.000 description 15
- 241000700159 Rattus Species 0.000 description 14
- 208000021017 Weight Gain Diseases 0.000 description 13
- 235000019786 weight gain Nutrition 0.000 description 13
- AHLBNYSZXLDEJQ-UHFFFAOYSA-N N-formyl-L-leucylester Natural products CCCCCCCCCCCC(OC(=O)C(CC(C)C)NC=O)CC1OC(=O)C1CCCCCC AHLBNYSZXLDEJQ-UHFFFAOYSA-N 0.000 description 12
- 230000002829 reductive effect Effects 0.000 description 12
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 12
- 108050006759 Pancreatic lipases Proteins 0.000 description 11
- 208000007683 Pediatric Obesity Diseases 0.000 description 11
- 102000005962 receptors Human genes 0.000 description 11
- 108020003175 receptors Proteins 0.000 description 11
- 102000019280 Pancreatic lipases Human genes 0.000 description 10
- 230000004584 weight gain Effects 0.000 description 10
- 229940124802 CB1 antagonist Drugs 0.000 description 9
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 229930003827 cannabinoid Natural products 0.000 description 9
- 239000003557 cannabinoid Substances 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- 239000003925 fat Substances 0.000 description 9
- 229940116369 pancreatic lipase Drugs 0.000 description 9
- 239000000902 placebo Substances 0.000 description 9
- 229940068196 placebo Drugs 0.000 description 9
- 239000003981 vehicle Substances 0.000 description 9
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 8
- 230000007062 hydrolysis Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 8
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 125000004093 cyano group Chemical group *C#N 0.000 description 6
- 125000005842 heteroatom Chemical group 0.000 description 6
- 230000005764 inhibitory process Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 230000000144 pharmacologic effect Effects 0.000 description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 5
- UNBMQQNYLCPCHS-UHFFFAOYSA-N Ebelactone B Natural products CCC(C)C(O)C(C)C(=O)C(C)C=C(C)CC(C)C1OC(=O)C1CC UNBMQQNYLCPCHS-UHFFFAOYSA-N 0.000 description 5
- 206010020772 Hypertension Diseases 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 239000003693 atypical antipsychotic agent Substances 0.000 description 5
- 229940127236 atypical antipsychotics Drugs 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 230000037396 body weight Effects 0.000 description 5
- 125000000392 cycloalkenyl group Chemical group 0.000 description 5
- 201000010099 disease Diseases 0.000 description 5
- UNBMQQNYLCPCHS-VYNDPHDASA-N ebelactone b Chemical compound CC[C@@H](C)[C@@H](O)[C@H](C)C(=O)[C@H](C)\C=C(/C)C[C@H](C)[C@@H]1OC(=O)[C@H]1CC UNBMQQNYLCPCHS-VYNDPHDASA-N 0.000 description 5
- 125000004430 oxygen atom Chemical group O* 0.000 description 5
- 239000000546 pharmaceutical excipient Substances 0.000 description 5
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 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
- 241001465754 Metazoa Species 0.000 description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 4
- 230000009286 beneficial effect Effects 0.000 description 4
- 230000003197 catalytic effect Effects 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 230000007246 mechanism Effects 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 241000282414 Homo sapiens Species 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 125000000304 alkynyl group Chemical group 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- 235000013305 food Nutrition 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 230000001965 increasing effect Effects 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 230000002503 metabolic effect Effects 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- 239000000178 monomer Substances 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 208000020016 psychiatric disease Diseases 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 208000024891 symptom Diseases 0.000 description 3
- 230000004580 weight loss Effects 0.000 description 3
- YYPXNAAEYOJYES-UHFFFAOYSA-N 2-amino-3,1-benzoxazin-4-one Chemical class C1=CC=C2C(=O)OC(N)=NC2=C1 YYPXNAAEYOJYES-UHFFFAOYSA-N 0.000 description 2
- YFYFOQXEXGLUOM-UHFFFAOYSA-N 3-phenylpyrazole-1-carboximidamide Chemical compound C1(=CC=CC=C1)C1=NN(C=C1)C(=N)N YFYFOQXEXGLUOM-UHFFFAOYSA-N 0.000 description 2
- QEICTDUJEAPNJN-UHFFFAOYSA-N 4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound NC(=N)N1CC(C=N1)c1ccccc1 QEICTDUJEAPNJN-UHFFFAOYSA-N 0.000 description 2
- 244000141218 Alpinia officinarum Species 0.000 description 2
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 2
- 102000018208 Cannabinoid Receptor Human genes 0.000 description 2
- 108050007331 Cannabinoid receptor Proteins 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
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 2
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 208000012902 Nervous system disease Diseases 0.000 description 2
- 208000025966 Neurological disease Diseases 0.000 description 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 description 2
- BAECOWNUKCLBPZ-HIUWNOOHSA-N Triolein Natural products O([C@H](OCC(=O)CCCCCCC/C=C\CCCCCCCC)COC(=O)CCCCCCC/C=C\CCCCCCCC)C(=O)CCCCCCC/C=C\CCCCCCCC BAECOWNUKCLBPZ-HIUWNOOHSA-N 0.000 description 2
- PHYFQTYBJUILEZ-UHFFFAOYSA-N Trioleoylglycerol Natural products CCCCCCCCC=CCCCCCCCC(=O)OCC(OC(=O)CCCCCCCC=CCCCCCCCC)COC(=O)CCCCCCCC=CCCCCCCCC PHYFQTYBJUILEZ-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000002723 alicyclic group Chemical group 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000000164 antipsychotic agent Substances 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 2
- 229960004170 clozapine Drugs 0.000 description 2
- QZUDBNBUXVUHMW-UHFFFAOYSA-N clozapine Chemical compound C1CN(C)CCN1C1=NC2=CC(Cl)=CC=C2NC2=CC=CC=C12 QZUDBNBUXVUHMW-UHFFFAOYSA-N 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
- 229920001577 copolymer Polymers 0.000 description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 238000013461 design Methods 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000011835 investigation Methods 0.000 description 2
- 239000003446 ligand Substances 0.000 description 2
- 238000011866 long-term treatment Methods 0.000 description 2
- 238000002483 medication Methods 0.000 description 2
- 208000030159 metabolic disease Diseases 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 229960005017 olanzapine Drugs 0.000 description 2
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 2
- ZVTQYRVARPYRRE-UHFFFAOYSA-N oxadiazol-4-one Chemical class O=C1CON=N1 ZVTQYRVARPYRRE-UHFFFAOYSA-N 0.000 description 2
- 210000000496 pancreas Anatomy 0.000 description 2
- 229940124531 pharmaceutical excipient Drugs 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 230000005180 public health Effects 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 239000003001 serine protease inhibitor Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 2
- PHYFQTYBJUILEZ-IUPFWZBJSA-N triolein Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CCCCCCCC)COC(=O)CCCCCCC\C=C/CCCCCCCC PHYFQTYBJUILEZ-IUPFWZBJSA-N 0.000 description 2
- 229940117972 triolein Drugs 0.000 description 2
- GLGNXYJARSMNGJ-VKTIVEEGSA-N (1s,2s,3r,4r)-3-[[5-chloro-2-[(1-ethyl-6-methoxy-2-oxo-4,5-dihydro-3h-1-benzazepin-7-yl)amino]pyrimidin-4-yl]amino]bicyclo[2.2.1]hept-5-ene-2-carboxamide Chemical compound CCN1C(=O)CCCC2=C(OC)C(NC=3N=C(C(=CN=3)Cl)N[C@H]3[C@H]([C@@]4([H])C[C@@]3(C=C4)[H])C(N)=O)=CC=C21 GLGNXYJARSMNGJ-VKTIVEEGSA-N 0.000 description 1
- MTCFGRXMJLQNBG-REOHCLBHSA-N (2S)-2-Amino-3-hydroxypropansäure Chemical compound OC[C@H](N)C(O)=O MTCFGRXMJLQNBG-REOHCLBHSA-N 0.000 description 1
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 description 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 1
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 description 1
- HTWMTDKMOSSPMU-UHFFFAOYSA-N 1,2-benzoxazin-4-one Chemical class C1=CC=C2C(=O)C=NOC2=C1 HTWMTDKMOSSPMU-UHFFFAOYSA-N 0.000 description 1
- XQBHAZDVLGNSOJ-UHFFFAOYSA-N 1-(4-ethenylphenyl)-n,n-dimethylmethanamine Chemical compound CN(C)CC1=CC=C(C=C)C=C1 XQBHAZDVLGNSOJ-UHFFFAOYSA-N 0.000 description 1
- QDNFIYLWAMNCGV-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazol-2-yl]-3-(4-chlorophenyl)sulfonylbutan-1-one Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)C(C)CC(=O)N(N=1)CC(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 QDNFIYLWAMNCGV-UHFFFAOYSA-N 0.000 description 1
- HRWGXPSWTHOGEW-UHFFFAOYSA-N 1-[5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazol-2-yl]-3-(4-chlorophenyl)sulfonylpropan-1-one Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(=O)CCS(=O)(=O)C=2C=CC(Cl)=CC=2)CC1C1=CC=CC=C1 HRWGXPSWTHOGEW-UHFFFAOYSA-N 0.000 description 1
- XIRPMPKSZHNMST-UHFFFAOYSA-N 1-ethenyl-2-phenylbenzene Chemical group C=CC1=CC=CC=C1C1=CC=CC=C1 XIRPMPKSZHNMST-UHFFFAOYSA-N 0.000 description 1
- IGGDKDTUCAWDAN-UHFFFAOYSA-N 1-vinylnaphthalene Chemical compound C1=CC=C2C(C=C)=CC=CC2=C1 IGGDKDTUCAWDAN-UHFFFAOYSA-N 0.000 description 1
- YBMMBGKWEDRYNB-UHFFFAOYSA-N 2-(2-benzylsulfonylethyl)-5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazole Chemical compound C1=CC(Cl)=CC=C1C(C(C1)C=2C=CC=CC=2)=NN1CCS(=O)(=O)CC1=CC=CC=C1 YBMMBGKWEDRYNB-UHFFFAOYSA-N 0.000 description 1
- UABZBFJRDPRXJR-UHFFFAOYSA-N 2-methylidenebutanoate;trimethylazanium Chemical compound C[NH+](C)C.CCC(=C)C([O-])=O UABZBFJRDPRXJR-UHFFFAOYSA-N 0.000 description 1
- UWRZIZXBOLBCON-UHFFFAOYSA-N 2-phenylethenamine Chemical compound NC=CC1=CC=CC=C1 UWRZIZXBOLBCON-UHFFFAOYSA-N 0.000 description 1
- WSTGSFBSMRBHTJ-UHFFFAOYSA-N 3-(4-chlorophenyl)-2-(4-chlorophenyl)sulfonyl-4-phenylpyrazolidine-1-carboximidamide Chemical compound NC(=N)N1CC(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)N1S(=O)(=O)C1=CC=C(Cl)C=C1 WSTGSFBSMRBHTJ-UHFFFAOYSA-N 0.000 description 1
- PTKMGIYABHEVJU-UHFFFAOYSA-N 3-(4-chlorophenyl)-4-phenyl-1,5-dihydropyrazol-4-ol Chemical compound C=1C=CC=CC=1C1(O)CNN=C1C1=CC=C(Cl)C=C1 PTKMGIYABHEVJU-UHFFFAOYSA-N 0.000 description 1
- CFRTVWXEOOFFPO-UHFFFAOYSA-N 4-phenylpyrazole-1-carboximidamide Chemical compound C1=NN(C(=N)N)C=C1C1=CC=CC=C1 CFRTVWXEOOFFPO-UHFFFAOYSA-N 0.000 description 1
- OYRYLTWYQHMSAP-UHFFFAOYSA-N 5-(4-chlorophenyl)-4-phenyl-2-[2-[3-(trifluoromethyl)phenyl]sulfonylethyl]-3,4-dihydropyrazole Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)CCN2N=C(C(C2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 OYRYLTWYQHMSAP-UHFFFAOYSA-N 0.000 description 1
- VHRQDVXOLLGRSP-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-4-phenyl-n-pyridin-2-yl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(\NC=2N=CC=CC=2)=N\S(=O)(=O)C=2C=CC(Cl)=CC=2)CC1C1=CC=CC=C1 VHRQDVXOLLGRSP-UHFFFAOYSA-N 0.000 description 1
- CCXWULHEPDRGMF-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-4-phenyl-n-pyridin-4-yl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(\NC=2C=CN=CC=2)=N\S(=O)(=O)C=2C=CC(Cl)=CC=2)CC1C1=CC=CC=C1 CCXWULHEPDRGMF-UHFFFAOYSA-N 0.000 description 1
- OVBPZWWNLXSVAC-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-n,4-diphenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(Cl)=CC=C1C1=NN(C(\NC=2C=CC=CC=2)=N\S(=O)(=O)C=2C=CC(Cl)=CC=2)CC1C1=CC=CC=C1 OVBPZWWNLXSVAC-UHFFFAOYSA-N 0.000 description 1
- ATGPYUSOVVWMQP-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-fluorophenyl)sulfonyl-4-hydroxy-4-phenyl-3h-pyrazole-2-carboximidamide Chemical compound C=1C=CC=CC=1C1(O)CN(C(=N)NS(=O)(=O)C=2C=CC(F)=CC=2)N=C1C1=CC=C(Cl)C=C1 ATGPYUSOVVWMQP-UHFFFAOYSA-N 0.000 description 1
- PMFKSNJVULPDBR-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-(4-fluorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(F)=CC=C1S(=O)(=O)NC(=N)N1N=C(C=2C=CC(Cl)=CC=2)C(C=2C=CC=CC=2)C1 PMFKSNJVULPDBR-UHFFFAOYSA-N 0.000 description 1
- NMOHILMYXVQGHO-UHFFFAOYSA-N 5-(4-chlorophenyl)-n'-methyl-4-phenyl-n-[4-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)C1=CC=C(C(F)(F)F)C=C1 NMOHILMYXVQGHO-UHFFFAOYSA-N 0.000 description 1
- WNHXVUIPVMASEZ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(2,4-difluorophenyl)sulfonyl-n'-methyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(F)C=C1F WNHXVUIPVMASEZ-UHFFFAOYSA-N 0.000 description 1
- AYYMXSJOWFVFIO-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-ethyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(=NCC)NS(=O)(=O)C1=CC=C(Cl)C=C1 AYYMXSJOWFVFIO-UHFFFAOYSA-N 0.000 description 1
- NVJVDZMNNYMORJ-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-pyridin-3-yl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=NC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(NC)=NS(=O)(=O)C1=CC=C(Cl)C=C1 NVJVDZMNNYMORJ-UHFFFAOYSA-N 0.000 description 1
- CXNXHKUCYNGGIR-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n'-methyl-4-pyridin-4-yl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CN=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(=NC)NS(=O)(=O)C1=CC=C(Cl)C=C1 CXNXHKUCYNGGIR-UHFFFAOYSA-N 0.000 description 1
- MXVJHHZCQUGIBP-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-chlorophenyl)sulfonyl-n-ethyl-4-hydroxy-4-phenyl-3h-pyrazole-2-carboximidamide Chemical compound C=1C=C(Cl)C=CC=1S(=O)(=O)N(CC)C(=N)N(N=1)CC(O)(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 MXVJHHZCQUGIBP-UHFFFAOYSA-N 0.000 description 1
- XXYLQSSZLZNJAF-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-(4-fluorophenyl)sulfonyl-4-phenyl-n'-propyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(=NCCC)NS(=O)(=O)C1=CC=C(F)C=C1 XXYLQSSZLZNJAF-UHFFFAOYSA-N 0.000 description 1
- DAQCUXYFZBBWOG-UHFFFAOYSA-N 5-dodecoxy-3-[4-(trifluoromethoxy)phenyl]-1,3,4-oxadiazol-2-one Chemical compound O=C1OC(OCCCCCCCCCCCC)=NN1C1=CC=C(OC(F)(F)F)C=C1 DAQCUXYFZBBWOG-UHFFFAOYSA-N 0.000 description 1
- 206010067484 Adverse reaction Diseases 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 102000004400 Aminopeptidases Human genes 0.000 description 1
- 108090000915 Aminopeptidases Proteins 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- 241000722948 Apocynum cannabinum Species 0.000 description 1
- 208000027559 Appetite disease Diseases 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 108010006654 Bleomycin Proteins 0.000 description 1
- 201000006474 Brain Ischemia Diseases 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
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- 206010010144 Completed suicide Diseases 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
- 206010012289 Dementia Diseases 0.000 description 1
- 208000032928 Dyslipidaemia Diseases 0.000 description 1
- WOISDAHQBUYEAF-UHFFFAOYSA-N Ebelactone A Natural products CCC(C)C(O)C(C)C(=O)C(C)C=C(C)CC(C)C1OC(=O)C1C WOISDAHQBUYEAF-UHFFFAOYSA-N 0.000 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 208000007530 Essential hypertension Diseases 0.000 description 1
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 206010056465 Food craving Diseases 0.000 description 1
- LYISDADPVOHJBJ-UHFFFAOYSA-N Galangin 3-methyl ether Natural products O1C2=CC(O)=CC(O)=C2C(=O)C(OC)=C1C1=CC=CC=C1 LYISDADPVOHJBJ-UHFFFAOYSA-N 0.000 description 1
- 208000018522 Gastrointestinal disease Diseases 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 235000015928 Hibiscus cannabinus Nutrition 0.000 description 1
- 241000282412 Homo Species 0.000 description 1
- 208000023105 Huntington disease Diseases 0.000 description 1
- 208000031226 Hyperlipidaemia Diseases 0.000 description 1
- 208000001953 Hypotension Diseases 0.000 description 1
- 206010061216 Infarction Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 208000031773 Insulin resistance syndrome Diseases 0.000 description 1
- 241000958270 Kitasatospora aburaviensis Species 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- 108010028554 LDL Cholesterol Proteins 0.000 description 1
- 238000008214 LDL Cholesterol Methods 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 208000007177 Left Ventricular Hypertrophy Diseases 0.000 description 1
- 208000017170 Lipid metabolism disease Diseases 0.000 description 1
- 208000026139 Memory disease Diseases 0.000 description 1
- 206010028980 Neoplasm Diseases 0.000 description 1
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 108010067035 Pancrelipase Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 229920002845 Poly(methacrylic acid) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 101001064310 Rattus norvegicus Gastric triacylglycerol lipase Proteins 0.000 description 1
- 102000012479 Serine Proteases Human genes 0.000 description 1
- 108010022999 Serine Proteases Proteins 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 208000027520 Somatoform disease Diseases 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000946767 Streptomyces toxytricini Species 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 230000024932 T cell mediated immunity Effects 0.000 description 1
- 208000000323 Tourette Syndrome Diseases 0.000 description 1
- 208000016620 Tourette disease Diseases 0.000 description 1
- 229940123445 Tricyclic antidepressant Drugs 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
- 235000021068 Western diet Nutrition 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 230000001800 adrenalinergic effect Effects 0.000 description 1
- 230000006838 adverse reaction Effects 0.000 description 1
- 239000000556 agonist Substances 0.000 description 1
- 125000003295 alanine group Chemical group N[C@@H](C)C(=O)* 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 229940024606 amino acid Drugs 0.000 description 1
- 125000000539 amino acid group Chemical group 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000001539 anorectic effect Effects 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
- 230000000561 anti-psychotic effect Effects 0.000 description 1
- 230000000259 anti-tumor effect Effects 0.000 description 1
- 239000003472 antidiabetic agent Substances 0.000 description 1
- 229940005529 antipsychotics Drugs 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
- 229940009098 aspartate Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- OYVAGSVQBOHSSS-UAPAGMARSA-O bleomycin A2 Chemical class N([C@H](C(=O)N[C@H](C)[C@@H](O)[C@H](C)C(=O)N[C@@H]([C@H](O)C)C(=O)NCCC=1SC=C(N=1)C=1SC=C(N=1)C(=O)NCCC[S+](C)C)[C@@H](O[C@H]1[C@H]([C@@H](O)[C@H](O)[C@H](CO)O1)O[C@@H]1[C@H]([C@@H](OC(N)=O)[C@H](O)[C@@H](CO)O1)O)C=1N=CNC=1)C(=O)C1=NC([C@H](CC(N)=O)NC[C@H](N)C(N)=O)=NC(N)=C1C OYVAGSVQBOHSSS-UAPAGMARSA-O 0.000 description 1
- 230000036772 blood pressure Effects 0.000 description 1
- 210000004556 brain Anatomy 0.000 description 1
- MPMBRWOOISTHJV-UHFFFAOYSA-N but-1-enylbenzene Chemical compound CCC=CC1=CC=CC=C1 MPMBRWOOISTHJV-UHFFFAOYSA-N 0.000 description 1
- 239000003536 cannabinoid receptor antagonist Substances 0.000 description 1
- 229940065144 cannabinoids Drugs 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 235000014633 carbohydrates Nutrition 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 210000000170 cell membrane Anatomy 0.000 description 1
- 208000015114 central nervous system disease Diseases 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 210000004978 chinese hamster ovary cell Anatomy 0.000 description 1
- 235000012000 cholesterol Nutrition 0.000 description 1
- 238000010367 cloning Methods 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- 229940125758 compound 15 Drugs 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000011340 continuous therapy Methods 0.000 description 1
- 235000019788 craving Nutrition 0.000 description 1
- 229940095074 cyclic amp Drugs 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 235000021316 daily nutritional intake Nutrition 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 235000013367 dietary fats Nutrition 0.000 description 1
- 210000002249 digestive system Anatomy 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000019620 fat digestibility Nutrition 0.000 description 1
- 210000003608 fece Anatomy 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 108010091264 gastric triacylglycerol lipase Proteins 0.000 description 1
- 239000003365 glass fiber Substances 0.000 description 1
- 125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000008821 health effect Effects 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 229920001600 hydrophobic polymer Polymers 0.000 description 1
- 201000010066 hyperandrogenism Diseases 0.000 description 1
- 208000021822 hypotensive Diseases 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 230000001900 immune effect Effects 0.000 description 1
- 206010021654 increased appetite Diseases 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- 230000007574 infarction Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002596 lactones Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000021633 leukocyte mediated immunity Effects 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 238000005567 liquid scintillation counting Methods 0.000 description 1
- 230000004807 localization Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000682 maximum tolerated dose Toxicity 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- XZWYZXLIPXDOLR-UHFFFAOYSA-N metformin Chemical compound CN(C)C(=N)NC(N)=N XZWYZXLIPXDOLR-UHFFFAOYSA-N 0.000 description 1
- 229960003105 metformin Drugs 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000004050 mood stabilizer Substances 0.000 description 1
- 229940127237 mood stabilizer Drugs 0.000 description 1
- YNTNKIJUFXILJN-UHFFFAOYSA-N n'-(4-fluorophenyl)sulfonyl-4,5-bis(4-methoxyphenyl)-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1=CC(OC)=CC=C1C1C(C=2C=CC(OC)=CC=2)=NN(C(=N)NS(=O)(=O)C=2C=CC(F)=CC=2)C1 YNTNKIJUFXILJN-UHFFFAOYSA-N 0.000 description 1
- HLKNXPDTYQPHFF-UHFFFAOYSA-N n-[2-[5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazol-2-yl]ethyl]-3-(trifluoromethyl)benzenesulfonamide Chemical compound FC(F)(F)C1=CC=CC(S(=O)(=O)NCCN2N=C(C(C2)C=2C=CC=CC=2)C=2C=CC(Cl)=CC=2)=C1 HLKNXPDTYQPHFF-UHFFFAOYSA-N 0.000 description 1
- SCJVBJZQVUMHTE-UHFFFAOYSA-N n-[amino-[5-(4-chlorophenyl)-4-phenyl-3,4-dihydropyrazol-2-yl]methylidene]naphthalene-1-carboxamide Chemical compound C=1C=CC2=CC=CC=C2C=1C(=O)N=C(N)N(N=1)CC(C=2C=CC=CC=2)C=1C1=CC=C(Cl)C=C1 SCJVBJZQVUMHTE-UHFFFAOYSA-N 0.000 description 1
- SCGPTIIGSPSBRD-UHFFFAOYSA-N n-acetamido-5-(4-chlorophenyl)-n'-(4-chlorophenyl)sulfonyl-4-phenyl-3,4-dihydropyrazole-2-carboximidamide Chemical compound C1C(C=2C=CC=CC=2)C(C=2C=CC(Cl)=CC=2)=NN1C(/NNC(=O)C)=N/S(=O)(=O)C1=CC=C(Cl)C=C1 SCGPTIIGSPSBRD-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000002547 new drug Substances 0.000 description 1
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 1
- 231100000956 nontoxicity Toxicity 0.000 description 1
- SFBTTWXNCQVIEC-UHFFFAOYSA-N o-Vinylanisole Chemical compound COC1=CC=CC=C1C=C SFBTTWXNCQVIEC-UHFFFAOYSA-N 0.000 description 1
- 208000001797 obstructive sleep apnea Diseases 0.000 description 1
- 239000003538 oral antidiabetic agent Substances 0.000 description 1
- 229940127209 oral hypoglycaemic agent Drugs 0.000 description 1
- 230000000399 orthopedic effect Effects 0.000 description 1
- 210000001672 ovary Anatomy 0.000 description 1
- 208000027753 pain disease Diseases 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000083 poly(allylamine) Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 201000010065 polycystic ovary syndrome Diseases 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 125000001325 propanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 229960004431 quetiapine Drugs 0.000 description 1
- URKOMYMAXPYINW-UHFFFAOYSA-N quetiapine Chemical compound C1CN(CCOCCO)CCN1C1=NC2=CC=CC=C2SC2=CC=CC=C12 URKOMYMAXPYINW-UHFFFAOYSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000018 receptor agonist Substances 0.000 description 1
- 229940044601 receptor agonist Drugs 0.000 description 1
- 229940044551 receptor antagonist Drugs 0.000 description 1
- 239000002464 receptor antagonist Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 229960001534 risperidone Drugs 0.000 description 1
- RAPZEAPATHNIPO-UHFFFAOYSA-N risperidone Chemical compound FC1=CC=C2C(C3CCN(CC3)CCC=3C(=O)N4CCCCC4=NC=3C)=NOC2=C1 RAPZEAPATHNIPO-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000002295 serotoninergic effect Effects 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 210000000813 small intestine Anatomy 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000000087 stabilizing effect Effects 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 230000005062 synaptic transmission Effects 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 description 1
- 229960000607 ziprasidone Drugs 0.000 description 1
- MVWVFYHBGMAFLY-UHFFFAOYSA-N ziprasidone Chemical compound C1=CC=C2C(N3CCN(CC3)CCC3=CC=4CC(=O)NC=4C=C3Cl)=NSC2=C1 MVWVFYHBGMAFLY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/365—Lactones
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/415—1,2-Diazoles
- A61K31/4155—1,2-Diazoles non condensed and containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/74—Synthetic polymeric materials
- A61K31/785—Polymers containing nitrogen
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Child & Adolescent Psychology (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03103961.3 | 2003-10-24 | ||
| EP03103961 | 2003-10-24 | ||
| PCT/EP2004/052618 WO2005039566A1 (en) | 2003-10-24 | 2004-10-22 | Combination treatment of obesity involving 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity and lipase inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004283055A1 true AU2004283055A1 (en) | 2005-05-06 |
Family
ID=34486362
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004283055A Abandoned AU2004283055A1 (en) | 2003-10-24 | 2004-10-22 | Combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity and lipase inhibitors |
Country Status (13)
| Country | Link |
|---|---|
| EP (1) | EP1680106B1 (https=) |
| JP (1) | JP2007509110A (https=) |
| CN (2) | CN1921849A (https=) |
| AR (1) | AR046132A1 (https=) |
| AT (1) | ATE438394T1 (https=) |
| AU (1) | AU2004283055A1 (https=) |
| BR (1) | BRPI0415463A (https=) |
| CA (1) | CA2543342A1 (https=) |
| DE (1) | DE602004022445D1 (https=) |
| MX (1) | MXPA06004390A (https=) |
| RU (1) | RU2006117639A (https=) |
| TW (1) | TW200528102A (https=) |
| WO (1) | WO2005039566A1 (https=) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20080039996A (ko) * | 2005-08-17 | 2008-05-07 | 솔베이 파머슈티컬스 게엠베하 | 칼륨 채널 억제 화합물의 사용 방법 |
| CN102731418B (zh) * | 2012-07-15 | 2015-03-11 | 浙江大学 | 1-取代-1h-1,2,4-三氮唑-甲酰胺衍生物及其制备和用途 |
| CN113166068B (zh) * | 2018-11-20 | 2024-08-16 | 上海科技大学 | MmpL3抑制剂、组合物及其用途 |
| CN117551046B (zh) * | 2023-11-17 | 2025-10-28 | 广东药科大学附属第一医院 | 二氨基脲类hsl抑制剂、制备方法及其用途 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DZ3335A1 (fr) * | 2000-03-23 | 2001-09-27 | Solvay Pharm Bv | Derives de 4,5-dihydro-1h-pyrazole ayant une activite antagoniste de cb1 |
| PL363751A1 (en) * | 2001-03-22 | 2004-11-29 | Solvay Pharmaceuticals B.V. | 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity |
| KR100903760B1 (ko) * | 2001-09-21 | 2009-06-19 | 솔베이 파마슈티칼스 비. 브이 | Ｃｂ1-길항 작용을 가지는 신규한4,5-디하이드로-1ｈ-피라졸 유도체 |
| IL157704A0 (en) * | 2001-09-21 | 2004-03-28 | Solvay Pharm Bv | 4,5-dihydro-1h-pyrazole derivatives having potent cbi-antagonistic activity |
| SE0104330D0 (sv) * | 2001-12-19 | 2001-12-19 | Astrazeneca Ab | Therapeutic agents |
| GB0202015D0 (en) * | 2002-01-29 | 2002-03-13 | Hoffmann La Roche | Piperazine Derivatives |
| AU2003209388A1 (en) * | 2002-01-29 | 2003-09-02 | Merck And Co., Inc. | Substituted imidazoles as cannabinoid receptor modulators |
| TW200412942A (en) * | 2002-08-06 | 2004-08-01 | Abbott Lab | Appetite control method |
| US20040122033A1 (en) * | 2002-12-10 | 2004-06-24 | Nargund Ravi P. | Combination therapy for the treatment of obesity |
| RU2344132C2 (ru) * | 2003-06-20 | 2009-01-20 | Ф.Хоффманн-Ля Рош Аг | 2-аминобензотиазолы в качестве обратных агонистов рецепторов cb1 |
| MXPA06002064A (es) * | 2003-10-20 | 2006-05-19 | Solvay Pharm Bv | Derivados e 1h imidazol como moduladores del receptor cannabinoide. |
| MXPA06004434A (es) * | 2003-10-24 | 2006-06-20 | Solvay Pharm Gmbh | Usos medicos novedosos de compuestos que muestran actividad antagonista cb1 y tratamiento de combinacion que involucra tales compuestos. |
-
2004
- 2004-10-20 TW TW093131751A patent/TW200528102A/zh unknown
- 2004-10-20 AR ARP040103804A patent/AR046132A1/es unknown
- 2004-10-22 AT AT04791282T patent/ATE438394T1/de not_active IP Right Cessation
- 2004-10-22 CA CA002543342A patent/CA2543342A1/en not_active Abandoned
- 2004-10-22 RU RU2006117639/15A patent/RU2006117639A/ru unknown
- 2004-10-22 WO PCT/EP2004/052618 patent/WO2005039566A1/en not_active Ceased
- 2004-10-22 AU AU2004283055A patent/AU2004283055A1/en not_active Abandoned
- 2004-10-22 CN CNA2004800300871A patent/CN1921849A/zh active Pending
- 2004-10-22 EP EP04791282A patent/EP1680106B1/en not_active Expired - Lifetime
- 2004-10-22 DE DE602004022445T patent/DE602004022445D1/de not_active Expired - Fee Related
- 2004-10-22 JP JP2006536092A patent/JP2007509110A/ja not_active Withdrawn
- 2004-10-22 MX MXPA06004390A patent/MXPA06004390A/es not_active Application Discontinuation
- 2004-10-22 CN CNA2004800301164A patent/CN1997364A/zh active Pending
- 2004-10-22 BR BRPI0415463-0A patent/BRPI0415463A/pt not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2007509110A (ja) | 2007-04-12 |
| CA2543342A1 (en) | 2005-05-06 |
| EP1680106B1 (en) | 2009-08-05 |
| DE602004022445D1 (de) | 2009-09-17 |
| BRPI0415463A (pt) | 2006-12-19 |
| RU2006117639A (ru) | 2007-12-10 |
| TW200528102A (en) | 2005-09-01 |
| EP1680106A1 (en) | 2006-07-19 |
| CN1997364A (zh) | 2007-07-11 |
| WO2005039566A1 (en) | 2005-05-06 |
| ATE438394T1 (de) | 2009-08-15 |
| AR046132A1 (es) | 2005-11-23 |
| MXPA06004390A (es) | 2006-06-14 |
| CN1921849A (zh) | 2007-02-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US20050124660A1 (en) | Novel medical uses of compounds showing CB1-antagonistic activity and combination treatment involving said compounds | |
| US20070060638A1 (en) | Methods and therapies for potentiating therapeutic activities of a cannabinoid receptor agonist via administration of a cannabinoid receptor antagonist | |
| AU2005298692A1 (en) | Pharmaceutical compositions comprising CB1 cannabinoid receptor antagonists and potassium channel openers for the treatment of diabetes mellitus type I, obesity and related conditions | |
| WO2007072083A1 (en) | Treatment of type 2 diabetes with a combination of dpiv inhibitor and metformin or thiazolidinedione | |
| CA2601509A1 (en) | Alpha7 neuronal nicotinic receptor ligand and antipsychotic compositions | |
| EP2089031B1 (en) | Reduction of overweight or obesity | |
| AU2004283056A1 (en) | Novel medical uses of compounds showing CB1-antagonistic activity and combination treatment involving said compounds | |
| KR20060100443A (ko) | 이상지혈증의 예방과 치료, 및 이상지혈증 및(또는) 비만과관련된 질환의 예방과 치료를 위한 약제의 제조에있어서의 피라졸 유도체의 용도 | |
| JP2006524699A (ja) | 腎機能障害を持つ個体における利尿改善法 | |
| AU2004283055A1 (en) | Combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity and lipase inhibitors | |
| US20050143441A1 (en) | Novel medical combination treatment of obesity involving 4,5-dihydro-1H-pyrazole derivatives having CB1-antagonistic activity | |
| US20050239859A2 (en) | Novel medical uses of 4,5-dihydro-1h-pyrazole derivatives having cb1- antagonistic activity | |
| CA2543197A1 (en) | Combination treatment of obesity involving selective cb1-antagonists and lipase inhibitors | |
| US20100056460A1 (en) | Combination of organic compounds | |
| JP2007504201A (ja) | 真性糖尿病の治療のためのｐｄｅ４阻害剤の使用 | |
| EP1663205A1 (en) | Use of 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity | |
| US20080188508A1 (en) | Methods and Therapies for Potentiating a Therapeutic Action of an Opioid Receptor Agonist and Inhibiting and/or Reversing Tolerance to Opioid Receptor Agonists | |
| HK1101029A (en) | Combination treatment of obesity involving 4,5-dihydro-1h-pyrazole derivatives having cb1-antagonistic activity and lipase inhibitors | |
| US20090170900A1 (en) | Dosing regimen for weight loss | |
| JPWO2007037296A1 (ja) | インスリン抵抗性改善剤を含有する薬剤 | |
| WO2007016771A1 (en) | Dosing regimen for weight loss | |
| HK1096292A (en) | Combination treatment of obesity involving selective cb1-antagonists and lipase inhibitors | |
| JP2018035086A (ja) | 低活動膀胱の予防及び／又は治療薬 | |
| HK1101275A (en) | Novel medical uses of compounds showing cb1-antagonistic activity and combination treatment involving said compounds | |
| JP2007031348A (ja) | 蛋白修飾物生成抑制配合剤 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK4 | Application lapsed section 142(2)(d) - no continuation fee paid for the application |