AU2005316313B2 - Novel MCH receptor antagonists - Google Patents
Novel MCH receptor antagonists Download PDFInfo
- Publication number
- AU2005316313B2 AU2005316313B2 AU2005316313A AU2005316313A AU2005316313B2 AU 2005316313 B2 AU2005316313 B2 AU 2005316313B2 AU 2005316313 A AU2005316313 A AU 2005316313A AU 2005316313 A AU2005316313 A AU 2005316313A AU 2005316313 B2 AU2005316313 B2 AU 2005316313B2
- Authority
- AU
- Australia
- Prior art keywords
- methyl
- amino
- carboxylic acid
- amide
- biphenyl
- 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.)
- Ceased
Links
- 108010047068 Melanin-concentrating hormone receptor Proteins 0.000 title description 4
- 102000006953 melanin-concentrating hormone receptor activity proteins Human genes 0.000 title description 4
- 229940044551 receptor antagonist Drugs 0.000 title description 2
- 239000002464 receptor antagonist Substances 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 267
- 208000008589 Obesity Diseases 0.000 claims abstract description 29
- 235000020824 obesity Nutrition 0.000 claims abstract description 29
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 25
- 238000011282 treatment Methods 0.000 claims abstract description 24
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 18
- 239000012453 solvate Substances 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 148
- -1 CI-C 4 alkyl Chemical group 0.000 claims description 90
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 78
- LXWNTLBMNCXRQN-UHFFFAOYSA-N 4'-fluoro-1,1'-biphenyl-4-carboxylic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1 LXWNTLBMNCXRQN-UHFFFAOYSA-N 0.000 claims description 60
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 229910052739 hydrogen Inorganic materials 0.000 claims description 39
- 239000001257 hydrogen Substances 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 38
- 125000000623 heterocyclic group Chemical group 0.000 claims description 36
- 229910052757 nitrogen Inorganic materials 0.000 claims description 35
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000005843 halogen group Chemical group 0.000 claims description 26
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
- 150000002431 hydrogen Chemical group 0.000 claims description 22
- KXDAEFPNCMNJSK-UHFFFAOYSA-N benzene carboxamide Natural products NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 18
- 125000001424 substituent group Chemical group 0.000 claims description 18
- OZFFPJBMCGKDGO-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1Cl OZFFPJBMCGKDGO-UHFFFAOYSA-N 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- NNJMFJSKMRYHSR-UHFFFAOYSA-N 4-phenylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1 NNJMFJSKMRYHSR-UHFFFAOYSA-N 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000001188 haloalkyl group Chemical group 0.000 claims description 10
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 9
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 9
- 125000004076 pyridyl group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000003386 piperidinyl group Chemical group 0.000 claims description 8
- LRGLZMCAACXDKG-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)benzoic acid Chemical compound CC1=CC(Cl)=CC=C1C1=CC=C(C(O)=O)C=C1 LRGLZMCAACXDKG-UHFFFAOYSA-N 0.000 claims description 7
- 208000035475 disorder Diseases 0.000 claims description 7
- UDUYQYBNZRZQIZ-UHFFFAOYSA-N 5-(4-fluorophenyl)pyrazine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN=C1C1=CC=C(F)C=C1 UDUYQYBNZRZQIZ-UHFFFAOYSA-N 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000004043 oxo group Chemical group O=* 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 5
- DGHGRAZWNAQANC-UHFFFAOYSA-N 4-(2,4-difluorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1F DGHGRAZWNAQANC-UHFFFAOYSA-N 0.000 claims description 5
- HSVPCRUODVLCAE-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)benzoic acid Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(O)=O)C=C1 HSVPCRUODVLCAE-UHFFFAOYSA-N 0.000 claims description 5
- PZJQKDATDRPIFT-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)benzoic acid Chemical compound ClC1=CC(C)=CC=C1C1=CC=C(C(O)=O)C=C1 PZJQKDATDRPIFT-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 5
- KTEKPJWBYQYJLW-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1Cl KTEKPJWBYQYJLW-UHFFFAOYSA-N 0.000 claims description 4
- DENUYBFZOWWZMD-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(pyrrolidin-3-ylmethyl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CC1CCNC1 DENUYBFZOWWZMD-UHFFFAOYSA-N 0.000 claims description 4
- PFEVGHCXMYFBMG-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 PFEVGHCXMYFBMG-UHFFFAOYSA-N 0.000 claims description 4
- 201000001320 Atherosclerosis Diseases 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 125000005750 substituted cyclic group Chemical group 0.000 claims description 4
- VPVLGKHWGDSWOS-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)C2CN(C)CC2)C=C1 VPVLGKHWGDSWOS-UHFFFAOYSA-N 0.000 claims description 3
- AOTYKBXXCYCXRZ-UHFFFAOYSA-N 4-(2-chlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1Cl AOTYKBXXCYCXRZ-UHFFFAOYSA-N 0.000 claims description 3
- YOUDKBGMWRQAIS-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethyl)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(F)(F)F)C=C1Cl YOUDKBGMWRQAIS-UHFFFAOYSA-N 0.000 claims description 3
- PHEPUGXCVVHZGS-UHFFFAOYSA-N 5-(3-chlorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1 PHEPUGXCVVHZGS-UHFFFAOYSA-N 0.000 claims description 3
- 206010012689 Diabetic retinopathy Diseases 0.000 claims description 3
- 208000031226 Hyperlipidaemia Diseases 0.000 claims description 3
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 3
- 125000005213 alkyl heteroaryl group Chemical group 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000005518 carboxamido group Chemical group 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 201000001421 hyperglycemia Diseases 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001624 naphthyl group Chemical group 0.000 claims description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 229910052717 sulfur Inorganic materials 0.000 claims description 3
- STLGUJTWUAPIIL-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC(Cl)=C1Cl STLGUJTWUAPIIL-UHFFFAOYSA-N 0.000 claims description 2
- OFOKUKWYWDEYOG-UHFFFAOYSA-N 4-(4-fluoro-2-methylphenyl)benzoic acid Chemical compound CC1=CC(F)=CC=C1C1=CC=C(C(O)=O)C=C1 OFOKUKWYWDEYOG-UHFFFAOYSA-N 0.000 claims description 2
- IZDIJERBVRWNHB-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)CC1 IZDIJERBVRWNHB-UHFFFAOYSA-N 0.000 claims description 2
- MYCAHXOIIAWKMI-UHFFFAOYSA-N 5-(3,4-difluorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(F)C(F)=C1 MYCAHXOIIAWKMI-UHFFFAOYSA-N 0.000 claims description 2
- YOFXYDVYMHOXSY-UHFFFAOYSA-N 5-(4-fluorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(F)C=C1 YOFXYDVYMHOXSY-UHFFFAOYSA-N 0.000 claims description 2
- CGCBAGCSAKDINT-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3SC(Cl)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 CGCBAGCSAKDINT-UHFFFAOYSA-N 0.000 claims description 2
- QGMFBCDNJUZQBZ-UHFFFAOYSA-N 5-phenylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC=C1 QGMFBCDNJUZQBZ-UHFFFAOYSA-N 0.000 claims description 2
- 206010004446 Benign prostatic hyperplasia Diseases 0.000 claims description 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 2
- 206010011224 Cough Diseases 0.000 claims description 2
- 208000011231 Crohn disease Diseases 0.000 claims description 2
- 206010012735 Diarrhoea Diseases 0.000 claims description 2
- 208000008279 Dumping Syndrome Diseases 0.000 claims description 2
- 208000007882 Gastritis Diseases 0.000 claims description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 claims description 2
- 208000010412 Glaucoma Diseases 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 2
- 206010022714 Intestinal ulcer Diseases 0.000 claims description 2
- 208000007920 Neurogenic Inflammation Diseases 0.000 claims description 2
- 208000000693 Neurogenic Urinary Bladder Diseases 0.000 claims description 2
- 206010029279 Neurogenic bladder Diseases 0.000 claims description 2
- 206010030216 Oesophagitis Diseases 0.000 claims description 2
- 208000008469 Peptic Ulcer Diseases 0.000 claims description 2
- 208000032395 Post gastric surgery syndrome Diseases 0.000 claims description 2
- 206010036774 Proctitis Diseases 0.000 claims description 2
- 208000025865 Ulcer Diseases 0.000 claims description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 2
- DFPAKSUCGFBDDF-ZQBYOMGUSA-N [14c]-nicotinamide Chemical compound N[14C](=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-ZQBYOMGUSA-N 0.000 claims description 2
- 210000001367 artery Anatomy 0.000 claims description 2
- 208000006673 asthma Diseases 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 230000003247 decreasing effect Effects 0.000 claims description 2
- 230000004064 dysfunction Effects 0.000 claims description 2
- 230000004406 elevated intraocular pressure Effects 0.000 claims description 2
- 208000006881 esophagitis Diseases 0.000 claims description 2
- 230000002496 gastric effect Effects 0.000 claims description 2
- 230000010243 gut motility Effects 0.000 claims description 2
- 208000006575 hypertriglyceridemia Diseases 0.000 claims description 2
- 208000002551 irritable bowel syndrome Diseases 0.000 claims description 2
- 125000006431 methyl cyclopropyl group Chemical group 0.000 claims description 2
- MJCKIPNEXQMFHC-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 MJCKIPNEXQMFHC-UHFFFAOYSA-N 0.000 claims description 2
- PPALLMCFTWSXNB-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-5-(4-fluorophenyl)pyrazine-2-carboxamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(N=C1)=CN=C1C1=CC=C(F)C=C1 PPALLMCFTWSXNB-UHFFFAOYSA-N 0.000 claims description 2
- NJHKQNLAMYYREO-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-5-thiophen-3-ylthiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C3=CSC=C3)=CC=C2OC=1N(C)C1CCN(C)CC1 NJHKQNLAMYYREO-UHFFFAOYSA-N 0.000 claims description 2
- 208000011906 peptic ulcer disease Diseases 0.000 claims description 2
- 230000002093 peripheral effect Effects 0.000 claims description 2
- 229910052698 phosphorus Inorganic materials 0.000 claims description 2
- 208000017497 prostate disease Diseases 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000036269 ulceration Effects 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 5
- 125000002632 imidazolidinyl group Chemical group 0.000 claims 4
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- GWRSATNRNFYMDI-UHFFFAOYSA-N 4-[(9-cyclopentyl-7,7-difluoro-5-methyl-6-oxo-8h-pyrimido[4,5-b][1,4]diazepin-2-yl)amino]-2-fluoro-5-methoxy-n-(1-methylpiperidin-4-yl)benzamide Chemical compound FC=1C=C(NC=2N=C3N(C4CCCC4)CC(F)(F)C(=O)N(C)C3=CN=2)C(OC)=CC=1C(=O)NC1CCN(C)CC1 GWRSATNRNFYMDI-UHFFFAOYSA-N 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 2
- 125000002755 pyrazolinyl group Chemical group 0.000 claims 2
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- TURNUHGAWRVUEN-UHFFFAOYSA-N 1-chloro-4-(2-chlorophenyl)-N-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]cyclohexa-2,4-diene-1-carboxamide Chemical compound CN(CCN(C=1SC2=C(N1)C=CC(=C2)NC(=O)C2(CC=C(C=C2)C2=C(C=CC=C2)Cl)Cl)C)C TURNUHGAWRVUEN-UHFFFAOYSA-N 0.000 claims 1
- ALLIZEAXNXSFGD-UHFFFAOYSA-N 1-methyl-2-phenylbenzene Chemical group CC1=CC=CC=C1C1=CC=CC=C1 ALLIZEAXNXSFGD-UHFFFAOYSA-N 0.000 claims 1
- LZYQNYCOIAILLB-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1C LZYQNYCOIAILLB-UHFFFAOYSA-N 0.000 claims 1
- YXKFVWASWPAUPW-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethoxy)phenyl]-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1Cl YXKFVWASWPAUPW-UHFFFAOYSA-N 0.000 claims 1
- PLIKAWJENQZMHA-UHFFFAOYSA-N 4-aminophenol Chemical compound NC1=CC=C(O)C=C1 PLIKAWJENQZMHA-UHFFFAOYSA-N 0.000 claims 1
- SVFIPJLEPHBEDN-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=C4OCOC4=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 SVFIPJLEPHBEDN-UHFFFAOYSA-N 0.000 claims 1
- ZZVWDOFDAVXTIS-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC(Cl)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZZVWDOFDAVXTIS-UHFFFAOYSA-N 0.000 claims 1
- BRTSOBBUFALQCT-UHFFFAOYSA-N 5-(4-methoxyphenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3N=C(OC3=CC=2)N(C)C2CCN(C)CC2)S1 BRTSOBBUFALQCT-UHFFFAOYSA-N 0.000 claims 1
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 claims 1
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- VDTOLZSLLBILOP-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-4-(4-fluorophenyl)benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 VDTOLZSLLBILOP-UHFFFAOYSA-N 0.000 claims 1
- GSXMLQGRFQUXJQ-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-5-(4-methylphenyl)thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC(C)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 GSXMLQGRFQUXJQ-UHFFFAOYSA-N 0.000 claims 1
- 125000001422 pyrrolinyl group Chemical group 0.000 claims 1
- 101800002739 Melanin-concentrating hormone Proteins 0.000 abstract description 31
- ORRDHOMWDPJSNL-UHFFFAOYSA-N melanin concentrating hormone Chemical compound N1C(=O)C(C(C)C)NC(=O)C(CCCNC(N)=N)NC(=O)CNC(=O)C(C(C)C)NC(=O)C(CCSC)NC(=O)C(NC(=O)C(CCCNC(N)=N)NC(=O)C(NC(=O)C(NC(=O)C(N)CC(O)=O)C(C)O)CCSC)CSSCC(C(=O)NC(CC=2C3=CC=CC=C3NC=2)C(=O)NC(CCC(O)=O)C(=O)NC(C(C)C)C(O)=O)NC(=O)C2CCCN2C(=O)C(CCCNC(N)=N)NC(=O)C1CC1=CC=C(O)C=C1 ORRDHOMWDPJSNL-UHFFFAOYSA-N 0.000 abstract description 31
- 230000002265 prevention Effects 0.000 abstract description 8
- 208000024891 symptom Diseases 0.000 abstract description 5
- 239000003667 hormone antagonist Substances 0.000 abstract 1
- 102000047659 melanin-concentrating hormone Human genes 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 280
- 238000001819 mass spectrum Methods 0.000 description 146
- 238000000034 method Methods 0.000 description 137
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 103
- 239000012141 concentrate Substances 0.000 description 101
- 235000008504 concentrate Nutrition 0.000 description 92
- 239000000460 chlorine Substances 0.000 description 85
- 239000000047 product Substances 0.000 description 85
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 81
- 238000003756 stirring Methods 0.000 description 75
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 72
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 72
- 238000005481 NMR spectroscopy Methods 0.000 description 71
- 230000014759 maintenance of location Effects 0.000 description 70
- 239000007921 spray Substances 0.000 description 67
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 60
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 58
- 238000006243 chemical reaction Methods 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 49
- 239000000741 silica gel Substances 0.000 description 49
- 229910002027 silica gel Inorganic materials 0.000 description 49
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 48
- 239000011541 reaction mixture Substances 0.000 description 46
- 239000000243 solution Substances 0.000 description 38
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 37
- 238000003818 flash chromatography Methods 0.000 description 37
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
- 239000007787 solid Substances 0.000 description 31
- 102400001132 Melanin-concentrating hormone Human genes 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 29
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 27
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 26
- 239000007821 HATU Substances 0.000 description 26
- 239000000543 intermediate Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 24
- 238000007429 general method Methods 0.000 description 24
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 24
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 23
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 22
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 21
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 150000001412 amines Chemical class 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- 239000011734 sodium Substances 0.000 description 18
- DMPWOCLZSODJHJ-UHFFFAOYSA-N 2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-amine Chemical compound C1C(N(C)C)CCN1C1=NC2=CC=C(N)C=C2S1 DMPWOCLZSODJHJ-UHFFFAOYSA-N 0.000 description 17
- 235000019439 ethyl acetate Nutrition 0.000 description 17
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 16
- 239000012044 organic layer Substances 0.000 description 14
- 239000002244 precipitate Substances 0.000 description 14
- FBXBOUVPPFDYKE-UHFFFAOYSA-N 2-n-[2-(dimethylamino)ethyl]-2-n-methyl-1,3-benzothiazole-2,6-diamine Chemical compound C1=C(N)C=C2SC(N(C)CCN(C)C)=NC2=C1 FBXBOUVPPFDYKE-UHFFFAOYSA-N 0.000 description 13
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 150000001408 amides Chemical class 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 12
- 239000003153 chemical reaction reagent Substances 0.000 description 12
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- 238000010898 silica gel chromatography Methods 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- KUCSJGBXJBQHNI-UHFFFAOYSA-N 2-chloro-6-nitro-1,3-benzothiazole Chemical group [O-][N+](=O)C1=CC=C2N=C(Cl)SC2=C1 KUCSJGBXJBQHNI-UHFFFAOYSA-N 0.000 description 10
- 101000581402 Homo sapiens Melanin-concentrating hormone receptor 1 Proteins 0.000 description 10
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 10
- 229960000583 acetic acid Drugs 0.000 description 10
- 210000004027 cell Anatomy 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 102100027375 Melanin-concentrating hormone receptor 1 Human genes 0.000 description 9
- 241001465754 Metazoa Species 0.000 description 9
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
- 239000005557 antagonist Substances 0.000 description 9
- 229940043279 diisopropylamine Drugs 0.000 description 9
- 238000011068 loading method Methods 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000012074 organic phase Substances 0.000 description 9
- 125000006239 protecting group Chemical group 0.000 description 9
- VVJXRBOQZCFBSR-UHFFFAOYSA-N 2-n-[2-(dimethylamino)ethyl]-2-n-methyl-1,3-benzoxazole-2,5-diamine Chemical compound NC1=CC=C2OC(N(C)CCN(C)C)=NC2=C1 VVJXRBOQZCFBSR-UHFFFAOYSA-N 0.000 description 8
- 239000004793 Polystyrene Substances 0.000 description 8
- 239000012267 brine Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- 229920002223 polystyrene Polymers 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 230000009467 reduction Effects 0.000 description 8
- 230000004044 response Effects 0.000 description 8
- VGKDLMBJGBXTGI-SJCJKPOMSA-N sertraline Chemical compound C1([C@@H]2CC[C@@H](C3=CC=CC=C32)NC)=CC=C(Cl)C(Cl)=C1 VGKDLMBJGBXTGI-SJCJKPOMSA-N 0.000 description 8
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
- IAWQUHCVFXQBMC-UHFFFAOYSA-N 1,3-benzoxazol-5-amine Chemical class NC1=CC=C2OC=NC2=C1 IAWQUHCVFXQBMC-UHFFFAOYSA-N 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 7
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 7
- GIBVENMRXKZTPM-UHFFFAOYSA-N 2-n-methyl-2-n-(1-methylpiperidin-4-yl)-1,3-benzoxazole-2,5-diamine Chemical compound N=1C2=CC(N)=CC=C2OC=1N(C)C1CCN(C)CC1 GIBVENMRXKZTPM-UHFFFAOYSA-N 0.000 description 7
- UZNXBVMOUKUHHZ-UHFFFAOYSA-N 2-n-methyl-2-n-[(1-methylpyrrolidin-3-yl)methyl]-1,3-benzoxazole-2,5-diamine Chemical compound N=1C2=CC(N)=CC=C2OC=1N(C)CC1CCN(C)C1 UZNXBVMOUKUHHZ-UHFFFAOYSA-N 0.000 description 7
- 238000005917 acylation reaction Methods 0.000 description 7
- 230000027455 binding Effects 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
- 239000012043 crude product Substances 0.000 description 7
- 239000000706 filtrate Substances 0.000 description 7
- MYTXLYWRSPXGAD-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-iodobenzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C1=CC=C(I)C=C1 MYTXLYWRSPXGAD-UHFFFAOYSA-N 0.000 description 7
- 229920005990 polystyrene resin Polymers 0.000 description 7
- 238000010992 reflux Methods 0.000 description 7
- 229920005989 resin Polymers 0.000 description 7
- 239000011347 resin Substances 0.000 description 7
- 238000012546 transfer Methods 0.000 description 7
- 238000005160 1H NMR spectroscopy Methods 0.000 description 6
- OEDLGBGVVRSXGG-UHFFFAOYSA-N 2-bromo-6-nitro-1,3-benzothiazole Chemical compound [O-][N+](=O)C1=CC=C2N=C(Br)SC2=C1 OEDLGBGVVRSXGG-UHFFFAOYSA-N 0.000 description 6
- FXJOTWLLDJYKAG-UHFFFAOYSA-N 5-chloropyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=C(Cl)C=N1 FXJOTWLLDJYKAG-UHFFFAOYSA-N 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 239000007995 HEPES buffer Substances 0.000 description 6
- QPJVMBTYPHYUOC-UHFFFAOYSA-N Methyl benzoate Natural products COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- FAYAYUOZWYJNBD-UHFFFAOYSA-N 1,3-benzothiazol-6-amine Chemical class NC1=CC=C2N=CSC2=C1 FAYAYUOZWYJNBD-UHFFFAOYSA-N 0.000 description 5
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000000556 agonist Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 229910052736 halogen Inorganic materials 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 5
- 244000144972 livestock Species 0.000 description 5
- 239000012528 membrane Substances 0.000 description 5
- 239000002480 mineral oil Substances 0.000 description 5
- 235000010446 mineral oil Nutrition 0.000 description 5
- JMSNXQWUGURTSO-UHFFFAOYSA-N n-methyl-6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(NC)=NC2=C1 JMSNXQWUGURTSO-UHFFFAOYSA-N 0.000 description 5
- 238000003752 polymerase chain reaction Methods 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 125000006850 spacer group Chemical group 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- QYYZXEPEVBXNNA-QGZVFWFLSA-N (1R)-2-acetyl-N-[4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)phenyl]-5-methylsulfonyl-1,3-dihydroisoindole-1-carboxamide Chemical compound C(C)(=O)N1[C@H](C2=CC=C(C=C2C1)S(=O)(=O)C)C(=O)NC1=CC=C(C=C1)C(C(F)(F)F)(C(F)(F)F)O QYYZXEPEVBXNNA-QGZVFWFLSA-N 0.000 description 4
- HGSZQBRMZNHXJZ-UHFFFAOYSA-N 1,3-benzothiazole-2,5-diamine Chemical compound NC1=CC=C2SC(N)=NC2=C1 HGSZQBRMZNHXJZ-UHFFFAOYSA-N 0.000 description 4
- HYBCFWFWKXJYFT-UHFFFAOYSA-N 1,3-benzothiazole-2,6-diamine Chemical compound C1=C(N)C=C2SC(N)=NC2=C1 HYBCFWFWKXJYFT-UHFFFAOYSA-N 0.000 description 4
- KFWNENMCZMPWSZ-UHFFFAOYSA-N 2-[2-(dimethylamino)ethyl]-2-N-methyl-3H-1,3-benzoxazole-2,5-diamine Chemical compound CN(CCC1(OC2=C(N1)C=C(C=C2)N)NC)C KFWNENMCZMPWSZ-UHFFFAOYSA-N 0.000 description 4
- BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 4
- HRELECNTXGCNGC-UHFFFAOYSA-N 2-methylsulfanyl-5-nitro-1,3-benzoxazole Chemical compound [O-][N+](=O)C1=CC=C2OC(SC)=NC2=C1 HRELECNTXGCNGC-UHFFFAOYSA-N 0.000 description 4
- HXUGEMWSWGXJMI-UHFFFAOYSA-N 2-n-methyl-2-n-propan-2-yl-1,3-benzothiazole-2,6-diamine Chemical compound C1=C(N)C=C2SC(N(C)C(C)C)=NC2=C1 HXUGEMWSWGXJMI-UHFFFAOYSA-N 0.000 description 4
- VFQOFJQVKVEXIY-UHFFFAOYSA-N 3-(phenylmethoxycarbonylamino)-3-piperidin-3-ylpropanoic acid Chemical compound C1CCNCC1C(CC(=O)O)NC(=O)OCC1=CC=CC=C1 VFQOFJQVKVEXIY-UHFFFAOYSA-N 0.000 description 4
- ROPCOJIWLNCMDP-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethoxy)phenyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(OC(F)(F)F)C=C1Cl ROPCOJIWLNCMDP-UHFFFAOYSA-N 0.000 description 4
- QCIWHVKGVVQHIY-UHFFFAOYSA-N 4-cyclohexylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1CCCCC1 QCIWHVKGVVQHIY-UHFFFAOYSA-N 0.000 description 4
- LBUNNMJLXWQQBY-UHFFFAOYSA-N 4-fluorophenylboronic acid Chemical compound OB(O)C1=CC=C(F)C=C1 LBUNNMJLXWQQBY-UHFFFAOYSA-N 0.000 description 4
- HCZZAVGTGZXIDY-UHFFFAOYSA-N 5-chloro-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]pyrazine-2-carboxamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C1=CN=C(Cl)C=N1 HCZZAVGTGZXIDY-UHFFFAOYSA-N 0.000 description 4
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 4
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 4
- XUMBMVFBXHLACL-UHFFFAOYSA-N Melanin Chemical compound O=C1C(=O)C(C2=CNC3=C(C(C(=O)C4=C32)=O)C)=C2C4=CNC2=C1C XUMBMVFBXHLACL-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 101100030361 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) pph-3 gene Proteins 0.000 description 4
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 4
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 4
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 4
- 239000000883 anti-obesity agent Substances 0.000 description 4
- 239000002830 appetite depressant Substances 0.000 description 4
- 238000003556 assay Methods 0.000 description 4
- 239000011324 bead Substances 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- 239000002299 complementary DNA Substances 0.000 description 4
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 4
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 4
- 235000013305 food Nutrition 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Natural products O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 150000002430 hydrocarbons Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- DAZXVJBJRMWXJP-UHFFFAOYSA-N n,n-dimethylethylamine Chemical compound CCN(C)C DAZXVJBJRMWXJP-UHFFFAOYSA-N 0.000 description 4
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 4
- 229910000027 potassium carbonate Inorganic materials 0.000 description 4
- 238000002821 scintillation proximity assay Methods 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 238000006467 substitution reaction Methods 0.000 description 4
- 230000009466 transformation Effects 0.000 description 4
- 238000000844 transformation Methods 0.000 description 4
- 239000003981 vehicle Substances 0.000 description 4
- 238000005406 washing Methods 0.000 description 4
- 208000016261 weight loss Diseases 0.000 description 4
- QNEGDGPAXKYZHZ-UHFFFAOYSA-N (2,4-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=C(Cl)C=C1Cl QNEGDGPAXKYZHZ-UHFFFAOYSA-N 0.000 description 3
- AVAWMINJNRAQFS-ZCFIWIBFSA-N (3r)-n,n-dimethylpyrrolidin-3-amine Chemical compound CN(C)[C@@H]1CCNC1 AVAWMINJNRAQFS-ZCFIWIBFSA-N 0.000 description 3
- ANRMAUMHJREENI-ZZXKWVIFSA-N (E)-4-(trifluoromethyl)cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(C(F)(F)F)C=C1 ANRMAUMHJREENI-ZZXKWVIFSA-N 0.000 description 3
- MOBRPMALMYCCOQ-UHFFFAOYSA-N 2-N-methyl-2-N-(1-methylpyrrolidin-3-yl)-1,3-benzothiazole-2,6-diamine Chemical compound N=1C2=CC=C(N)C=C2SC=1N(C)C1CCN(C)C1 MOBRPMALMYCCOQ-UHFFFAOYSA-N 0.000 description 3
- SPRWTZHUKWETFN-UHFFFAOYSA-N 2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzoxazol-5-amine Chemical compound C1C(N(C)C)CCN1C1=NC2=CC(N)=CC=C2O1 SPRWTZHUKWETFN-UHFFFAOYSA-N 0.000 description 3
- FRUONTASXOVPNT-UHFFFAOYSA-N 2-ethylsulfanyl-5-nitro-1,3-benzoxazole Chemical compound [O-][N+](=O)C1=CC=C2OC(SCC)=NC2=C1 FRUONTASXOVPNT-UHFFFAOYSA-N 0.000 description 3
- YOQXZKKBAFEEQH-UHFFFAOYSA-N 2-methyl-2-N-(1-methylpiperidin-4-yl)-3H-1,3-benzoxazole-2,5-diamine Chemical compound CC1(OC2=C(N1)C=C(C=C2)N)NC2CCN(CC2)C YOQXZKKBAFEEQH-UHFFFAOYSA-N 0.000 description 3
- ITLWSYAJGXPQSO-UHFFFAOYSA-N 3-methyl-4-phenylbenzoic acid Chemical compound CC1=CC(C(O)=O)=CC=C1C1=CC=CC=C1 ITLWSYAJGXPQSO-UHFFFAOYSA-N 0.000 description 3
- NXTDJHZGHOFSQG-UHFFFAOYSA-N 3-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 NXTDJHZGHOFSQG-UHFFFAOYSA-N 0.000 description 3
- JVNPYEWTCDJEFW-UHFFFAOYSA-N 4-(4-fluorophenyl)benzoyl chloride Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(Cl)=O)C=C1 JVNPYEWTCDJEFW-UHFFFAOYSA-N 0.000 description 3
- VVAQLOMOWIACOF-UHFFFAOYSA-N 4-(cyclohexylmethoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OCC1CCCCC1 VVAQLOMOWIACOF-UHFFFAOYSA-N 0.000 description 3
- GHICCUXQJBDNRN-UHFFFAOYSA-N 4-iodobenzoic acid Chemical compound OC(=O)C1=CC=C(I)C=C1 GHICCUXQJBDNRN-UHFFFAOYSA-N 0.000 description 3
- FQOGSTGLRLMQOV-UHFFFAOYSA-N 5-nitro-3h-1,3-benzoxazole-2-thione Chemical compound [O-][N+](=O)C1=CC=C2OC(=S)NC2=C1 FQOGSTGLRLMQOV-UHFFFAOYSA-N 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
- 102000004877 Insulin Human genes 0.000 description 3
- 108090001061 Insulin Proteins 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- PVNIIMVLHYAWGP-UHFFFAOYSA-N Niacin Chemical compound OC(=O)C1=CC=CN=C1 PVNIIMVLHYAWGP-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- 239000012317 TBTU Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 230000010933 acylation Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 230000003042 antagnostic effect Effects 0.000 description 3
- 230000008485 antagonism Effects 0.000 description 3
- 150000001491 aromatic compounds Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 229940098773 bovine serum albumin Drugs 0.000 description 3
- 210000004556 brain Anatomy 0.000 description 3
- 239000000872 buffer Substances 0.000 description 3
- 239000012230 colorless oil Substances 0.000 description 3
- 230000001143 conditioned effect Effects 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- 238000010511 deprotection reaction Methods 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000012065 filter cake Substances 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- 239000012442 inert solvent Substances 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 229940125396 insulin Drugs 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- TXDXBAGPLUULRS-UHFFFAOYSA-N n-methyl-5-nitro-1,3-benzoxazol-2-amine Chemical compound [O-][N+](=O)C1=CC=C2OC(NC)=NC2=C1 TXDXBAGPLUULRS-UHFFFAOYSA-N 0.000 description 3
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 3
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 3
- 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 description 3
- 229960001243 orlistat Drugs 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 230000001575 pathological effect Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 3
- 150000003141 primary amines Chemical class 0.000 description 3
- 238000000159 protein binding assay Methods 0.000 description 3
- DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 description 3
- 238000010791 quenching Methods 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 102000005962 receptors Human genes 0.000 description 3
- 108020003175 receptors Proteins 0.000 description 3
- 230000002829 reductive effect Effects 0.000 description 3
- 229960004425 sibutramine Drugs 0.000 description 3
- UNAANXDKBXWMLN-UHFFFAOYSA-N sibutramine Chemical compound C=1C=C(Cl)C=CC=1C1(C(N(C)C)CC(C)C)CCC1 UNAANXDKBXWMLN-UHFFFAOYSA-N 0.000 description 3
- 239000011550 stock solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- 235000019786 weight gain Nutrition 0.000 description 3
- LOCGPWGCRVKCFN-UHFFFAOYSA-N (2-chloro-4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C(Cl)=C1 LOCGPWGCRVKCFN-UHFFFAOYSA-N 0.000 description 2
- ZGGHKIMDNBDHJB-NRFPMOEYSA-M (3R,5S)-fluvastatin sodium Chemical compound [Na+].C12=CC=CC=C2N(C(C)C)C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)=C1C1=CC=C(F)C=C1 ZGGHKIMDNBDHJB-NRFPMOEYSA-M 0.000 description 2
- AFDXODALSZRGIH-QPJJXVBHSA-N (E)-3-(4-methoxyphenyl)prop-2-enoic acid Chemical compound COC1=CC=C(\C=C\C(O)=O)C=C1 AFDXODALSZRGIH-QPJJXVBHSA-N 0.000 description 2
- GVJHHUAWPYXKBD-UHFFFAOYSA-N (±)-α-Tocopherol Chemical compound OC1=C(C)C(C)=C2OC(CCCC(C)CCCC(C)CCCC(C)C)(C)CCC2=C1C GVJHHUAWPYXKBD-UHFFFAOYSA-N 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 2
- BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 2
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 2
- VLZVIIYRNMWPSN-UHFFFAOYSA-N 2-Amino-4-nitrophenol Chemical compound NC1=CC([N+]([O-])=O)=CC=C1O VLZVIIYRNMWPSN-UHFFFAOYSA-N 0.000 description 2
- YPTWPDOGEAHMOR-UHFFFAOYSA-N 2-chloro-1,3-benzothiazol-6-amine Chemical compound NC1=CC=C2N=C(Cl)SC2=C1 YPTWPDOGEAHMOR-UHFFFAOYSA-N 0.000 description 2
- PPQVAHVZIBDHDB-UHFFFAOYSA-N 2-phenyl-1,3-oxazole-5-carboxylic acid Chemical compound O1C(C(=O)O)=CN=C1C1=CC=CC=C1 PPQVAHVZIBDHDB-UHFFFAOYSA-N 0.000 description 2
- SRVXSISGYBMIHR-UHFFFAOYSA-N 3-[3-[3-(2-amino-2-oxoethyl)phenyl]-5-chlorophenyl]-3-(5-methyl-1,3-thiazol-2-yl)propanoic acid Chemical compound S1C(C)=CN=C1C(CC(O)=O)C1=CC(Cl)=CC(C=2C=C(CC(N)=O)C=CC=2)=C1 SRVXSISGYBMIHR-UHFFFAOYSA-N 0.000 description 2
- ANRMAUMHJREENI-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=C(C(F)(F)F)C=C1 ANRMAUMHJREENI-UHFFFAOYSA-N 0.000 description 2
- SUFQYLDLNPIWFA-UHFFFAOYSA-N 4-(2,4-difluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(F)=CC=3)F)=CC=C2OC=1N(C)C1CCN(C)CC1 SUFQYLDLNPIWFA-UHFFFAOYSA-N 0.000 description 2
- KUQZEMQWDYZMGV-UHFFFAOYSA-N 4-(2-chloro-4-ethoxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OCC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 KUQZEMQWDYZMGV-UHFFFAOYSA-N 0.000 description 2
- ZDHPDAAQJNYBSN-UHFFFAOYSA-N 4-(2-chloro-4-ethoxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide;hydrochloride Chemical compound Cl.ClC1=CC(OCC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 ZDHPDAAQJNYBSN-UHFFFAOYSA-N 0.000 description 2
- BUXUVDHTHUVLOI-UHFFFAOYSA-N 4-(4-fluorophenyl)-N-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide hydrochloride Chemical compound Cl.N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 BUXUVDHTHUVLOI-UHFFFAOYSA-N 0.000 description 2
- ZKZAICOOMBXCAD-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZKZAICOOMBXCAD-UHFFFAOYSA-N 0.000 description 2
- MAFONNJRIJQKRN-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[3-[methyl(quinolin-2-yl)amino]propyl]amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C=1C=C2C=CC=CC2=NC=1N(C)CCCN(C)C(SC1=C2)=NC1=CC=C2NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 MAFONNJRIJQKRN-UHFFFAOYSA-N 0.000 description 2
- BWCBPFAOWPSQBS-UHFFFAOYSA-N 4-(cyclopenten-1-yl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CCCC1 BWCBPFAOWPSQBS-UHFFFAOYSA-N 0.000 description 2
- PMCNQGKUEOMDHQ-UHFFFAOYSA-N 4-[2-chloro-4-(trifluoromethoxy)phenyl]-N-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide hydrochloride Chemical compound Cl.C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(OC(F)(F)F)C=C1Cl PMCNQGKUEOMDHQ-UHFFFAOYSA-N 0.000 description 2
- IOZTWPVHQPXZIB-UHFFFAOYSA-N 4-butyl-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C1=CC(CCCC)=CC=C1C(=O)NC1=CC=C(OC(=N2)N(C)C3CCN(C)CC3)C2=C1 IOZTWPVHQPXZIB-UHFFFAOYSA-N 0.000 description 2
- MKBJAZHGVVOAJV-UHFFFAOYSA-N 4-cyclohex-2-en-1-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1C=CCCC1 MKBJAZHGVVOAJV-UHFFFAOYSA-N 0.000 description 2
- OTPHEAKUEAICPM-UHFFFAOYSA-N 4-cyclohexyloxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1CCCCC1 OTPHEAKUEAICPM-UHFFFAOYSA-N 0.000 description 2
- PRMIERMZDSQDSC-UHFFFAOYSA-N 4-cyclopentyl-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1CCCC1 PRMIERMZDSQDSC-UHFFFAOYSA-N 0.000 description 2
- RYAQFHLUEMJOMF-UHFFFAOYSA-N 4-phenoxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=CC=C1 RYAQFHLUEMJOMF-UHFFFAOYSA-N 0.000 description 2
- BZMIRENONUYABD-UHFFFAOYSA-N 5-(2,4-difluorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(F)C=C1F BZMIRENONUYABD-UHFFFAOYSA-N 0.000 description 2
- GWLCYLPZQKOCTB-UHFFFAOYSA-N 5-(4-chlorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(Cl)C=C1 GWLCYLPZQKOCTB-UHFFFAOYSA-N 0.000 description 2
- JETRXAHRPACNMA-UHFFFAOYSA-N 5-chloro-1-benzofuran-2-carboxylic acid Chemical compound ClC1=CC=C2OC(C(=O)O)=CC2=C1 JETRXAHRPACNMA-UHFFFAOYSA-N 0.000 description 2
- XJYOBHXWBRKOQO-UHFFFAOYSA-N 5-phenyl-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1=CC=CC=C1 XJYOBHXWBRKOQO-UHFFFAOYSA-N 0.000 description 2
- LJIXMNTVEKBCRG-UHFFFAOYSA-N 6-(4-fluorophenyl)pyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1C1=CC=C(F)C=C1 LJIXMNTVEKBCRG-UHFFFAOYSA-N 0.000 description 2
- GPNAVOJCQIEKQF-UHFFFAOYSA-N 6-nitro-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N)=NC2=C1 GPNAVOJCQIEKQF-UHFFFAOYSA-N 0.000 description 2
- ZNIGKQDVUDYWSZ-UHFFFAOYSA-N 7-methyl-6-nitro-1,3-benzothiazol-2-amine Chemical compound CC1=C([N+]([O-])=O)C=CC2=C1SC(N)=N2 ZNIGKQDVUDYWSZ-UHFFFAOYSA-N 0.000 description 2
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
- 208000007848 Alcoholism Diseases 0.000 description 2
- 241000272517 Anseriformes Species 0.000 description 2
- 208000019901 Anxiety disease Diseases 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- XUKUURHRXDUEBC-KAYWLYCHSA-N Atorvastatin Chemical compound C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CC[C@@H](O)C[C@@H](O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-KAYWLYCHSA-N 0.000 description 2
- XUKUURHRXDUEBC-UHFFFAOYSA-N Atorvastatin Natural products C=1C=CC=CC=1C1=C(C=2C=CC(F)=CC=2)N(CCC(O)CC(O)CC(O)=O)C(C(C)C)=C1C(=O)NC1=CC=CC=C1 XUKUURHRXDUEBC-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910021592 Copper(II) chloride Inorganic materials 0.000 description 2
- 239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 2
- 101100441092 Danio rerio crlf3 gene Proteins 0.000 description 2
- 206010012335 Dependence Diseases 0.000 description 2
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 2
- 208000001613 Gambling Diseases 0.000 description 2
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 description 2
- 239000012981 Hank's balanced salt solution Substances 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- PCZOHLXUXFIOCF-UHFFFAOYSA-N Monacolin X Natural products C12C(OC(=O)C(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 PCZOHLXUXFIOCF-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- AYCPARAPKDAOEN-LJQANCHMSA-N N-[(1S)-2-(dimethylamino)-1-phenylethyl]-6,6-dimethyl-3-[(2-methyl-4-thieno[3,2-d]pyrimidinyl)amino]-1,4-dihydropyrrolo[3,4-c]pyrazole-5-carboxamide Chemical compound C1([C@H](NC(=O)N2C(C=3NN=C(NC=4C=5SC=CC=5N=C(C)N=4)C=3C2)(C)C)CN(C)C)=CC=CC=C1 AYCPARAPKDAOEN-LJQANCHMSA-N 0.000 description 2
- CDRSUAAJUPFYDC-UHFFFAOYSA-N N-[2-[methyl-(1-methylpiperidin-3-yl)amino]-1,3-benzoxazol-5-yl]-4-phenylbenzamide hydrochloride Chemical compound Cl.N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC=CC=3)=CC=C2OC=1N(C)C1CCCN(C)C1 CDRSUAAJUPFYDC-UHFFFAOYSA-N 0.000 description 2
- 102000003797 Neuropeptides Human genes 0.000 description 2
- 108090000189 Neuropeptides Proteins 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
- TUZYXOIXSAXUGO-UHFFFAOYSA-N Pravastatin Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(O)C=C21 TUZYXOIXSAXUGO-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- RYMZZMVNJRMUDD-UHFFFAOYSA-N SJ000286063 Natural products C12C(OC(=O)C(C)(C)CC)CC(C)C=C2C=CC(C)C1CCC1CC(O)CC(=O)O1 RYMZZMVNJRMUDD-UHFFFAOYSA-N 0.000 description 2
- 238000000297 Sandmeyer reaction Methods 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 208000006011 Stroke Diseases 0.000 description 2
- 241000271567 Struthioniformes Species 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- 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 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000004809 Teflon Substances 0.000 description 2
- 229920006362 Teflon® Polymers 0.000 description 2
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
- 241001061127 Thione Species 0.000 description 2
- OKJPEAGHQZHRQV-UHFFFAOYSA-N Triiodomethane Natural products IC(I)I OKJPEAGHQZHRQV-UHFFFAOYSA-N 0.000 description 2
- 108010046516 Wheat Germ Agglutinins Proteins 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000001266 acyl halides Chemical class 0.000 description 2
- 210000000577 adipose tissue Anatomy 0.000 description 2
- 206010001584 alcohol abuse Diseases 0.000 description 2
- 208000025746 alcohol use disease Diseases 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 2
- 125000006242 amine protecting group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 230000000578 anorexic effect Effects 0.000 description 2
- 230000003579 anti-obesity Effects 0.000 description 2
- 239000003529 anticholesteremic agent Substances 0.000 description 2
- 229940127226 anticholesterol agent Drugs 0.000 description 2
- 229940125710 antiobesity agent Drugs 0.000 description 2
- 230000036506 anxiety Effects 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 229960005370 atorvastatin Drugs 0.000 description 2
- 108010014210 axokine Proteins 0.000 description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 125000002619 bicyclic group Chemical group 0.000 description 2
- 125000004744 butyloxycarbonyl group Chemical group 0.000 description 2
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 2
- 150000003857 carboxamides Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 238000002648 combination therapy Methods 0.000 description 2
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 2
- 230000001186 cumulative effect Effects 0.000 description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 description 2
- LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 description 2
- 206010061428 decreased appetite Diseases 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 2
- 229940042399 direct acting antivirals protease inhibitors Drugs 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 238000003821 enantio-separation Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011049 filling Methods 0.000 description 2
- 229960003765 fluvastatin Drugs 0.000 description 2
- 238000002825 functional assay Methods 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 229940088597 hormone Drugs 0.000 description 2
- 239000005556 hormone Substances 0.000 description 2
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 229910052742 iron Inorganic materials 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000012160 loading buffer Substances 0.000 description 2
- 229960004844 lovastatin Drugs 0.000 description 2
- PCZOHLXUXFIOCF-BXMDZJJMSA-N lovastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)[C@@H](C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 PCZOHLXUXFIOCF-BXMDZJJMSA-N 0.000 description 2
- QLJODMDSTUBWDW-UHFFFAOYSA-N lovastatin hydroxy acid Natural products C1=CC(C)C(CCC(O)CC(O)CC(O)=O)C2C(OC(=O)C(C)CC)CC(C)C=C21 QLJODMDSTUBWDW-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- QXKIBABMVWKPEO-UHFFFAOYSA-N methyl 4-(2,4-difluorophenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(F)C=C1F QXKIBABMVWKPEO-UHFFFAOYSA-N 0.000 description 2
- WTDLGUCVGZQNIQ-UHFFFAOYSA-N methyl 4-(2-chloro-4-ethoxyphenyl)benzoate Chemical compound ClC1=CC(OCC)=CC=C1C1=CC=C(C(=O)OC)C=C1 WTDLGUCVGZQNIQ-UHFFFAOYSA-N 0.000 description 2
- OQKJWBSHXXOKNF-UHFFFAOYSA-N methyl 4-(2-chloro-4-methoxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC)C=C1Cl OQKJWBSHXXOKNF-UHFFFAOYSA-N 0.000 description 2
- QYWCUTPMTMDOIX-UHFFFAOYSA-N methyl 4-(2-chloro-4-propan-2-yloxyphenyl)benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC(C)C)C=C1Cl QYWCUTPMTMDOIX-UHFFFAOYSA-N 0.000 description 2
- SSSHTHOAZKVZAZ-UHFFFAOYSA-N methyl 4-[2-chloro-4-(trifluoromethoxy)phenyl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=CC=C(OC(F)(F)F)C=C1Cl SSSHTHOAZKVZAZ-UHFFFAOYSA-N 0.000 description 2
- CVVMLRFXZPKILB-UHFFFAOYSA-N methyl 5-chloropyrazine-2-carboxylate Chemical compound COC(=O)C1=CN=C(Cl)C=N1 CVVMLRFXZPKILB-UHFFFAOYSA-N 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- HVOYZOQVDYHUPF-UHFFFAOYSA-N n,n',n'-trimethylethane-1,2-diamine Chemical compound CNCCN(C)C HVOYZOQVDYHUPF-UHFFFAOYSA-N 0.000 description 2
- KYPOHILNJHCBPJ-UHFFFAOYSA-N n,n,n'-trimethyl-n'-(6-nitro-1,3-benzothiazol-2-yl)ethane-1,2-diamine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N(C)CCN(C)C)=NC2=C1 KYPOHILNJHCBPJ-UHFFFAOYSA-N 0.000 description 2
- BSDHLTVXPGOMCF-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(2-methylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC=C1C BSDHLTVXPGOMCF-UHFFFAOYSA-N 0.000 description 2
- VDKMGNHGKUOTAG-UHFFFAOYSA-N n-methyl-5-nitro-n-(2-pyrrolidin-1-ylethyl)-1,3-benzoxazol-2-amine Chemical compound N=1C2=CC([N+]([O-])=O)=CC=C2OC=1N(C)CCN1CCCC1 VDKMGNHGKUOTAG-UHFFFAOYSA-N 0.000 description 2
- QYWYMAVGVWCQTD-UHFFFAOYSA-N n-methyl-6-nitro-n-propan-2-yl-1,3-benzothiazol-2-amine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N(C)C(C)C)=NC2=C1 QYWYMAVGVWCQTD-UHFFFAOYSA-N 0.000 description 2
- DBNRTYUDAUTHAZ-UHFFFAOYSA-N n-methyl-n-(1-methylpiperidin-3-yl)-5-nitro-1,3-benzoxazol-2-amine Chemical compound N=1C2=CC([N+]([O-])=O)=CC=C2OC=1N(C)C1CCCN(C)C1 DBNRTYUDAUTHAZ-UHFFFAOYSA-N 0.000 description 2
- RJQCXCHZRBFLME-UHFFFAOYSA-N n-methyl-n-(1-methylpiperidin-4-yl)-5-nitro-1,3-benzoxazol-2-amine Chemical compound N=1C2=CC([N+]([O-])=O)=CC=C2OC=1N(C)C1CCN(C)CC1 RJQCXCHZRBFLME-UHFFFAOYSA-N 0.000 description 2
- MWEANMBJIUETSG-UHFFFAOYSA-N n-methyl-n-[(1-methylpyrrolidin-3-yl)methyl]-5-nitro-1,3-benzoxazol-2-amine Chemical compound N=1C2=CC([N+]([O-])=O)=CC=C2OC=1N(C)CC1CCN(C)C1 MWEANMBJIUETSG-UHFFFAOYSA-N 0.000 description 2
- 235000005152 nicotinamide Nutrition 0.000 description 2
- 239000011570 nicotinamide Substances 0.000 description 2
- 229960003966 nicotinamide Drugs 0.000 description 2
- 229960003512 nicotinic acid Drugs 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- 150000002828 nitro derivatives Chemical class 0.000 description 2
- AFDXODALSZRGIH-UHFFFAOYSA-N p-coumaric acid methyl ether Natural products COC1=CC=C(C=CC(O)=O)C=C1 AFDXODALSZRGIH-UHFFFAOYSA-N 0.000 description 2
- 229910052763 palladium Inorganic materials 0.000 description 2
- 239000008188 pellet Substances 0.000 description 2
- 239000000137 peptide hydrolase inhibitor Substances 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- DHHVAGZRUROJKS-UHFFFAOYSA-N phentermine Chemical compound CC(C)(N)CC1=CC=CC=C1 DHHVAGZRUROJKS-UHFFFAOYSA-N 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 239000002953 phosphate buffered saline Substances 0.000 description 2
- HYAFETHFCAUJAY-UHFFFAOYSA-N pioglitazone Chemical compound N1=CC(CC)=CC=C1CCOC(C=C1)=CC=C1CC1C(=O)NC(=O)S1 HYAFETHFCAUJAY-UHFFFAOYSA-N 0.000 description 2
- 239000013612 plasmid Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 208000028173 post-traumatic stress disease Diseases 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 229960002965 pravastatin Drugs 0.000 description 2
- TUZYXOIXSAXUGO-PZAWKZKUSA-N pravastatin Chemical compound C1=C[C@H](C)[C@H](CC[C@@H](O)C[C@@H](O)CC(O)=O)[C@H]2[C@@H](OC(=O)[C@@H](C)CC)C[C@H](O)C=C21 TUZYXOIXSAXUGO-PZAWKZKUSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000004237 preparative chromatography Methods 0.000 description 2
- 108090000765 processed proteins & peptides Proteins 0.000 description 2
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 2
- 230000001850 reproductive effect Effects 0.000 description 2
- 239000000523 sample Substances 0.000 description 2
- 150000003334 secondary amides Chemical class 0.000 description 2
- 229960002855 simvastatin Drugs 0.000 description 2
- RYMZZMVNJRMUDD-HGQWONQESA-N simvastatin Chemical compound C([C@H]1[C@@H](C)C=CC2=C[C@H](C)C[C@@H]([C@H]12)OC(=O)C(C)(C)CC)C[C@@H]1C[C@@H](O)CC(=O)O1 RYMZZMVNJRMUDD-HGQWONQESA-N 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- DAEPDZWVDSPTHF-UHFFFAOYSA-M sodium pyruvate Chemical compound [Na+].CC(=O)C([O-])=O DAEPDZWVDSPTHF-UHFFFAOYSA-M 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 201000009032 substance abuse Diseases 0.000 description 2
- 231100000736 substance abuse Toxicity 0.000 description 2
- 208000011117 substance-related disease Diseases 0.000 description 2
- 239000005720 sucrose Substances 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 2
- 239000012414 tert-butyl nitrite Substances 0.000 description 2
- 125000003831 tetrazolyl group Chemical group 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- 229930192474 thiophene Natural products 0.000 description 2
- 125000001425 triazolyl group Chemical group 0.000 description 2
- 230000004584 weight gain Effects 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- 239000013585 weight reducing agent Substances 0.000 description 2
- DBGIVFWFUFKIQN-VIFPVBQESA-N (+)-Fenfluramine Chemical compound CCN[C@@H](C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-VIFPVBQESA-N 0.000 description 1
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 1
- VCGRFBXVSFAGGA-UHFFFAOYSA-N (1,1-dioxo-1,4-thiazinan-4-yl)-[6-[[3-(4-fluorophenyl)-5-methyl-1,2-oxazol-4-yl]methoxy]pyridin-3-yl]methanone Chemical compound CC=1ON=C(C=2C=CC(F)=CC=2)C=1COC(N=C1)=CC=C1C(=O)N1CCS(=O)(=O)CC1 VCGRFBXVSFAGGA-UHFFFAOYSA-N 0.000 description 1
- TYIKXPOMOYDGCS-UHFFFAOYSA-N (2,3-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC(Cl)=C1Cl TYIKXPOMOYDGCS-UHFFFAOYSA-N 0.000 description 1
- TYONHSPZXLFWKI-UHFFFAOYSA-N (2,4-dimethylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C(C)=C1 TYONHSPZXLFWKI-UHFFFAOYSA-N 0.000 description 1
- NNTFPBXQPOQRBT-UHFFFAOYSA-N (2,5-dichlorophenyl)boronic acid Chemical compound OB(O)C1=CC(Cl)=CC=C1Cl NNTFPBXQPOQRBT-UHFFFAOYSA-N 0.000 description 1
- UKYCKUPXBPLXBA-UHFFFAOYSA-N (2-chloro-4-methylphenyl)boronic acid Chemical compound CC1=CC=C(B(O)O)C(Cl)=C1 UKYCKUPXBPLXBA-UHFFFAOYSA-N 0.000 description 1
- RRCMGJCFMJBHQC-UHFFFAOYSA-N (2-chlorophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1Cl RRCMGJCFMJBHQC-UHFFFAOYSA-N 0.000 description 1
- NPLZNDDFVCGRAG-UHFFFAOYSA-N (2-cyanophenyl)boronic acid Chemical compound OB(O)C1=CC=CC=C1C#N NPLZNDDFVCGRAG-UHFFFAOYSA-N 0.000 description 1
- ROEQGIFOWRQYHD-UHFFFAOYSA-N (2-methoxyphenyl)boronic acid Chemical compound COC1=CC=CC=C1B(O)O ROEQGIFOWRQYHD-UHFFFAOYSA-N 0.000 description 1
- NSJVYHOPHZMZPN-UHFFFAOYSA-N (2-methylphenyl)boronic acid Chemical compound CC1=CC=CC=C1B(O)O NSJVYHOPHZMZPN-UHFFFAOYSA-N 0.000 description 1
- XUFXOAAUWZOOIT-SXARVLRPSA-N (2R,3R,4R,5S,6R)-5-[[(2R,3R,4R,5S,6R)-5-[[(2R,3R,4S,5S,6R)-3,4-dihydroxy-6-methyl-5-[[(1S,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)-1-cyclohex-2-enyl]amino]-2-oxanyl]oxy]-3,4-dihydroxy-6-(hydroxymethyl)-2-oxanyl]oxy]-6-(hydroxymethyl)oxane-2,3,4-triol Chemical compound O([C@H]1O[C@H](CO)[C@H]([C@@H]([C@H]1O)O)O[C@H]1O[C@@H]([C@H]([C@H](O)[C@H]1O)N[C@@H]1[C@@H]([C@@H](O)[C@H](O)C(CO)=C1)O)C)[C@@H]1[C@@H](CO)O[C@@H](O)[C@H](O)[C@H]1O XUFXOAAUWZOOIT-SXARVLRPSA-N 0.000 description 1
- BJQCPCFFYBKRLM-UHFFFAOYSA-N (3-methylphenyl)boronic acid Chemical compound CC1=CC=CC(B(O)O)=C1 BJQCPCFFYBKRLM-UHFFFAOYSA-N 0.000 description 1
- MAYZWDRUFKUGGP-VIFPVBQESA-N (3s)-1-[5-tert-butyl-3-[(1-methyltetrazol-5-yl)methyl]triazolo[4,5-d]pyrimidin-7-yl]pyrrolidin-3-ol Chemical compound CN1N=NN=C1CN1C2=NC(C(C)(C)C)=NC(N3C[C@@H](O)CC3)=C2N=N1 MAYZWDRUFKUGGP-VIFPVBQESA-N 0.000 description 1
- MBEQXBKSJCOKJF-UHFFFAOYSA-N (4-ethoxy-2-methylphenyl)boronic acid Chemical compound CCOC1=CC=C(B(O)O)C(C)=C1 MBEQXBKSJCOKJF-UHFFFAOYSA-N 0.000 description 1
- IQMLIVUHMSIOQP-UHFFFAOYSA-N (4-fluoro-2-methylphenyl)boronic acid Chemical compound CC1=CC(F)=CC=C1B(O)O IQMLIVUHMSIOQP-UHFFFAOYSA-N 0.000 description 1
- PQCXFUXRTRESBD-UHFFFAOYSA-N (4-methoxycarbonylphenyl)boronic acid Chemical compound COC(=O)C1=CC=C(B(O)O)C=C1 PQCXFUXRTRESBD-UHFFFAOYSA-N 0.000 description 1
- VOAAEKKFGLPLLU-UHFFFAOYSA-N (4-methoxyphenyl)boronic acid Chemical compound COC1=CC=C(B(O)O)C=C1 VOAAEKKFGLPLLU-UHFFFAOYSA-N 0.000 description 1
- RWIUTHWKQHRQNP-ZDVGBALWSA-N (9e,12e)-n-(1-phenylethyl)octadeca-9,12-dienamide Chemical compound CCCCC\C=C\C\C=C\CCCCCCCC(=O)NC(C)C1=CC=CC=C1 RWIUTHWKQHRQNP-ZDVGBALWSA-N 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- UCTWMZQNUQWSLP-VIFPVBQESA-N (R)-adrenaline Chemical compound CNC[C@H](O)C1=CC=C(O)C(O)=C1 UCTWMZQNUQWSLP-VIFPVBQESA-N 0.000 description 1
- 229930182837 (R)-adrenaline Natural products 0.000 description 1
- RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 description 1
- XNCRUNXWPDJHGV-BQYQJAHWSA-N (e)-2-methyl-3-phenylprop-2-enoic acid Chemical compound OC(=O)C(/C)=C/C1=CC=CC=C1 XNCRUNXWPDJHGV-BQYQJAHWSA-N 0.000 description 1
- RRLUFPHCTSFKNR-DUXPYHPUSA-N (e)-3-(3,4-dichlorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(Cl)C(Cl)=C1 RRLUFPHCTSFKNR-DUXPYHPUSA-N 0.000 description 1
- HXBOHZQZTWAEHJ-DUXPYHPUSA-N (e)-3-(3,4-difluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(F)C(F)=C1 HXBOHZQZTWAEHJ-DUXPYHPUSA-N 0.000 description 1
- OYFKFZBXVYKVCD-DUXPYHPUSA-N (e)-3-(3-chloro-4-fluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=C(F)C(Cl)=C1 OYFKFZBXVYKVCD-DUXPYHPUSA-N 0.000 description 1
- RTSIUKMGSDOSTI-SNAWJCMRSA-N (e)-3-(3-fluorophenyl)prop-2-enoic acid Chemical compound OC(=O)\C=C\C1=CC=CC(F)=C1 RTSIUKMGSDOSTI-SNAWJCMRSA-N 0.000 description 1
- KWGPBDBAAXYWOJ-SOFGYWHQSA-N (e)-3-naphthalen-2-ylprop-2-enoic acid Chemical compound C1=CC=CC2=CC(/C=C/C(=O)O)=CC=C21 KWGPBDBAAXYWOJ-SOFGYWHQSA-N 0.000 description 1
- MOWXJLUYGFNTAL-DEOSSOPVSA-N (s)-[2-chloro-4-fluoro-5-(7-morpholin-4-ylquinazolin-4-yl)phenyl]-(6-methoxypyridazin-3-yl)methanol Chemical compound N1=NC(OC)=CC=C1[C@@H](O)C1=CC(C=2C3=CC=C(C=C3N=CN=2)N2CCOCC2)=C(F)C=C1Cl MOWXJLUYGFNTAL-DEOSSOPVSA-N 0.000 description 1
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 1
- JQIZHNLEFQMDCQ-UHFFFAOYSA-N 1,2,3,4-tetrahydropyridazine Chemical compound C1CC=CNN1 JQIZHNLEFQMDCQ-UHFFFAOYSA-N 0.000 description 1
- OTPDWCMLUKMQNO-UHFFFAOYSA-N 1,2,3,4-tetrahydropyrimidine Chemical compound C1NCC=CN1 OTPDWCMLUKMQNO-UHFFFAOYSA-N 0.000 description 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
- CIISBYKBBMFLEZ-UHFFFAOYSA-N 1,2-oxazolidine Chemical compound C1CNOC1 CIISBYKBBMFLEZ-UHFFFAOYSA-N 0.000 description 1
- CZSRXHJVZUBEGW-UHFFFAOYSA-N 1,2-thiazolidine Chemical compound C1CNSC1 CZSRXHJVZUBEGW-UHFFFAOYSA-N 0.000 description 1
- FKASFBLJDCHBNZ-UHFFFAOYSA-N 1,3,4-oxadiazole Chemical compound C1=NN=CO1 FKASFBLJDCHBNZ-UHFFFAOYSA-N 0.000 description 1
- MBIZXFATKUQOOA-UHFFFAOYSA-N 1,3,4-thiadiazole Chemical compound C1=NN=CS1 MBIZXFATKUQOOA-UHFFFAOYSA-N 0.000 description 1
- KGVVXUNDDIZWEL-UHFFFAOYSA-N 1,3-benzoxazole-2,5-diamine Chemical compound NC1=CC=C2OC(N)=NC2=C1 KGVVXUNDDIZWEL-UHFFFAOYSA-N 0.000 description 1
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 description 1
- APWRZPQBPCAXFP-UHFFFAOYSA-N 1-(1-oxo-2H-isoquinolin-5-yl)-5-(trifluoromethyl)-N-[2-(trifluoromethyl)pyridin-4-yl]pyrazole-4-carboxamide Chemical compound O=C1NC=CC2=C(C=CC=C12)N1N=CC(=C1C(F)(F)F)C(=O)NC1=CC(=NC=C1)C(F)(F)F APWRZPQBPCAXFP-UHFFFAOYSA-N 0.000 description 1
- VFLQQZCRHPIGJU-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine;hydron;chloride Chemical compound Cl.ClCCN1CCCCC1 VFLQQZCRHPIGJU-UHFFFAOYSA-N 0.000 description 1
- NDMFETHQFUOIQX-UHFFFAOYSA-N 1-(3-chloropropyl)imidazolidin-2-one Chemical compound ClCCCN1CCNC1=O NDMFETHQFUOIQX-UHFFFAOYSA-N 0.000 description 1
- ABDDQTDRAHXHOC-QMMMGPOBSA-N 1-[(7s)-5,7-dihydro-4h-thieno[2,3-c]pyran-7-yl]-n-methylmethanamine Chemical compound CNC[C@@H]1OCCC2=C1SC=C2 ABDDQTDRAHXHOC-QMMMGPOBSA-N 0.000 description 1
- BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
- DYSJMQABFPKAQM-UHFFFAOYSA-N 1-benzothiophene-2-carboxylic acid Chemical compound C1=CC=C2SC(C(=O)O)=CC2=C1 DYSJMQABFPKAQM-UHFFFAOYSA-N 0.000 description 1
- RRRFVMOJVRRZMM-UHFFFAOYSA-N 1-bromo-2-chloro-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(Br)C(Cl)=C1 RRRFVMOJVRRZMM-UHFFFAOYSA-N 0.000 description 1
- QOVFYQVZTTUBMW-UHFFFAOYSA-N 1-bromo-2-chloro-4-ethoxybenzene Chemical compound CCOC1=CC=C(Br)C(Cl)=C1 QOVFYQVZTTUBMW-UHFFFAOYSA-N 0.000 description 1
- SUFFQYRWSRMBQC-UHFFFAOYSA-N 1-bromo-2-chloro-4-methoxybenzene Chemical compound COC1=CC=C(Br)C(Cl)=C1 SUFFQYRWSRMBQC-UHFFFAOYSA-N 0.000 description 1
- AMQWLZQIHOTRTG-UHFFFAOYSA-N 1-bromo-2-chloro-4-propan-2-yloxybenzene Chemical compound CC(C)OC1=CC=C(Br)C(Cl)=C1 AMQWLZQIHOTRTG-UHFFFAOYSA-N 0.000 description 1
- UKANCZCEGQDKGF-UHFFFAOYSA-N 1-methylpiperidin-3-ol Chemical compound CN1CCCC(O)C1 UKANCZCEGQDKGF-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- YKLDMAPEGQYZRT-UHFFFAOYSA-N 2,4-difluoro-1-iodobenzene Chemical compound FC1=CC=C(I)C(F)=C1 YKLDMAPEGQYZRT-UHFFFAOYSA-N 0.000 description 1
- ZHPGAWQGOLXMRK-UHFFFAOYSA-N 2-(2-chloro-4-fluorophenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane Chemical compound O1C(C)(C)C(C)(C)OB1C1=CC=C(F)C=C1Cl ZHPGAWQGOLXMRK-UHFFFAOYSA-N 0.000 description 1
- AVNABWMTQCQPIY-UHFFFAOYSA-N 2-(3,4-dichlorophenoxy)-n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]acetamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)COC1=CC=C(Cl)C(Cl)=C1 AVNABWMTQCQPIY-UHFFFAOYSA-N 0.000 description 1
- AYUDXVQMLKGODN-UHFFFAOYSA-N 2-(4-chlorophenyl)-1,3,4-oxadiazole Chemical compound C1=CC(Cl)=CC=C1C1=NN=CO1 AYUDXVQMLKGODN-UHFFFAOYSA-N 0.000 description 1
- BOLUTFLCJITYBW-UHFFFAOYSA-N 2-(4-chlorophenyl)-4-methyl-1,3-thiazole Chemical compound CC1=CSC(C=2C=CC(Cl)=CC=2)=N1 BOLUTFLCJITYBW-UHFFFAOYSA-N 0.000 description 1
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- GLHGZSNEDTZWBG-UHFFFAOYSA-N 2-[3-(diethylamino)propyl]-2-N-methyl-3H-1,3-benzoxazole-2,5-diamine Chemical compound C(C)N(CCCC1(OC2=C(N1)C=C(C=C2)N)NC)CC GLHGZSNEDTZWBG-UHFFFAOYSA-N 0.000 description 1
- ZDMPQJBHNNWMPL-UHFFFAOYSA-N 2-chloro-7-methyl-6-nitro-1,3-benzothiazole Chemical compound CC1=C([N+]([O-])=O)C=CC2=C1SC(Cl)=N2 ZDMPQJBHNNWMPL-UHFFFAOYSA-N 0.000 description 1
- KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 description 1
- JVLRXDDVYGLFHJ-UHFFFAOYSA-N 2-methyl-2-N-(1-methylpiperidin-3-yl)-3H-1,3-benzothiazole-2,6-diamine Chemical compound CC1(SC2=C(N1)C=CC(=C2)N)NC1CN(CCC1)C JVLRXDDVYGLFHJ-UHFFFAOYSA-N 0.000 description 1
- KDEFDLUVGXNAII-UHFFFAOYSA-N 2-methyl-2-N-(1-methylpiperidin-3-yl)-3H-1,3-benzoxazole-2,5-diamine Chemical compound CC1(OC2=C(N1)C=C(C=C2)N)NC1CN(CCC1)C KDEFDLUVGXNAII-UHFFFAOYSA-N 0.000 description 1
- OJWQVTDUHYJLAQ-UHFFFAOYSA-N 2-methyl-2-N-(2-piperidin-1-ylethyl)-3H-1,3-benzothiazole-2,6-diamine Chemical compound CC1(SC2=C(N1)C=CC(=C2)N)NCCN1CCCCC1 OJWQVTDUHYJLAQ-UHFFFAOYSA-N 0.000 description 1
- VWSLLSXLURJCDF-UHFFFAOYSA-N 2-methyl-4,5-dihydro-1h-imidazole Chemical compound CC1=NCCN1 VWSLLSXLURJCDF-UHFFFAOYSA-N 0.000 description 1
- YNNZFLLVBUMSDY-UHFFFAOYSA-N 2-n-methyl-2-n-(1-methylpiperidin-3-yl)-1,3-benzoxazole-2,5-diamine Chemical compound N=1C2=CC(N)=CC=C2OC=1N(C)C1CCCN(C)C1 YNNZFLLVBUMSDY-UHFFFAOYSA-N 0.000 description 1
- ZAHRGHLXBGLZIM-UHFFFAOYSA-N 2-n-methyl-2-n-(2-pyrrolidin-1-ylethyl)-1,3-benzoxazole-2,5-diamine Chemical compound N=1C2=CC(N)=CC=C2OC=1N(C)CCN1CCCC1 ZAHRGHLXBGLZIM-UHFFFAOYSA-N 0.000 description 1
- PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
- VSWICNJIUPRZIK-UHFFFAOYSA-N 2-piperideine Chemical compound C1CNC=CC1 VSWICNJIUPRZIK-UHFFFAOYSA-N 0.000 description 1
- RSEBUVRVKCANEP-UHFFFAOYSA-N 2-pyrroline Chemical compound C1CC=CN1 RSEBUVRVKCANEP-UHFFFAOYSA-N 0.000 description 1
- SNYRXHULAWEECU-UHFFFAOYSA-N 3,4-dichlorophenoxyacetic acid Chemical compound OC(=O)COC1=CC=C(Cl)C(Cl)=C1 SNYRXHULAWEECU-UHFFFAOYSA-N 0.000 description 1
- HCDMJFOHIXMBOV-UHFFFAOYSA-N 3-(2,6-difluoro-3,5-dimethoxyphenyl)-1-ethyl-8-(morpholin-4-ylmethyl)-4,7-dihydropyrrolo[4,5]pyrido[1,2-d]pyrimidin-2-one Chemical compound C=1C2=C3N(CC)C(=O)N(C=4C(=C(OC)C=C(OC)C=4F)F)CC3=CN=C2NC=1CN1CCOCC1 HCDMJFOHIXMBOV-UHFFFAOYSA-N 0.000 description 1
- XUWQPAJIBUAHKI-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)-n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]prop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C=CC1=CC=C(Cl)C(Cl)=C1 XUWQPAJIBUAHKI-UHFFFAOYSA-N 0.000 description 1
- QDWNRFRNRJYFSG-UHFFFAOYSA-N 3-(3-chlorophenyl)-n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]prop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C=CC1=CC=CC(Cl)=C1 QDWNRFRNRJYFSG-UHFFFAOYSA-N 0.000 description 1
- FFKGOJWPSXRALK-UHFFFAOYSA-N 3-(3-chlorophenyl)prop-2-enoic acid Chemical compound OC(=O)C=CC1=CC=CC(Cl)=C1 FFKGOJWPSXRALK-UHFFFAOYSA-N 0.000 description 1
- BYHQTRFJOGIQAO-GOSISDBHSA-N 3-(4-bromophenyl)-8-[(2R)-2-hydroxypropyl]-1-[(3-methoxyphenyl)methyl]-1,3,8-triazaspiro[4.5]decan-2-one Chemical compound C[C@H](CN1CCC2(CC1)CN(C(=O)N2CC3=CC(=CC=C3)OC)C4=CC=C(C=C4)Br)O BYHQTRFJOGIQAO-GOSISDBHSA-N 0.000 description 1
- BUDSGDGFXQMCAY-UHFFFAOYSA-N 3-(4-chlorophenyl)-n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]prop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C=CC1=CC=C(Cl)C=C1 BUDSGDGFXQMCAY-UHFFFAOYSA-N 0.000 description 1
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 1
- RIYDEYWRFIHXBD-UHFFFAOYSA-N 3-[4-(trifluoromethyl)phenyl]prop-2-enoyl chloride Chemical compound FC(F)(F)C1=CC=C(C=CC(Cl)=O)C=C1 RIYDEYWRFIHXBD-UHFFFAOYSA-N 0.000 description 1
- XPAYEWBTLKOEDA-UHFFFAOYSA-N 3-methyl-4-nitroaniline Chemical compound CC1=CC(N)=CC=C1[N+]([O-])=O XPAYEWBTLKOEDA-UHFFFAOYSA-N 0.000 description 1
- TTZXIWBOKOZOPL-UHFFFAOYSA-N 3-phenoxybenzoyl chloride Chemical compound ClC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1 TTZXIWBOKOZOPL-UHFFFAOYSA-N 0.000 description 1
- YGTFDJRCCBKLDM-UHFFFAOYSA-N 3-phenyl-1,2-oxazole-5-carboxylic acid Chemical compound O1C(C(=O)O)=CC(C=2C=CC=CC=2)=N1 YGTFDJRCCBKLDM-UHFFFAOYSA-N 0.000 description 1
- MVQVNTPHUGQQHK-UHFFFAOYSA-N 3-pyridinemethanol Chemical compound OCC1=CC=CN=C1 MVQVNTPHUGQQHK-UHFFFAOYSA-N 0.000 description 1
- YEVSVQXTBWMTFO-UHFFFAOYSA-N 4-(2,3-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC(Cl)=C1Cl YEVSVQXTBWMTFO-UHFFFAOYSA-N 0.000 description 1
- ONBXLEVZJQBTIT-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1Cl ONBXLEVZJQBTIT-UHFFFAOYSA-N 0.000 description 1
- VHPFTQKHIJACDN-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide;hydrochloride Chemical compound Cl.C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1Cl VHPFTQKHIJACDN-UHFFFAOYSA-N 0.000 description 1
- TZRCFKJUNKUMMV-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide;hydrochloride Chemical compound Cl.N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=CC=C2OC=1N(C)C1CCN(C)CC1 TZRCFKJUNKUMMV-UHFFFAOYSA-N 0.000 description 1
- STUCRICXTMRQCU-UHFFFAOYSA-N 4-(2,4-dichlorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(Cl)=CC=3)Cl)=CC=C2OC=1N(C)CC1CCN(C)C1 STUCRICXTMRQCU-UHFFFAOYSA-N 0.000 description 1
- XAKPMSIGBXHCRV-UHFFFAOYSA-N 4-(2,5-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC(Cl)=CC=C1Cl XAKPMSIGBXHCRV-UHFFFAOYSA-N 0.000 description 1
- BPFJHGMEQCPSSE-UHFFFAOYSA-N 4-(2-chloro-4-cyclopentyloxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C(=C1)Cl)=CC=C1OC1CCCC1 BPFJHGMEQCPSSE-UHFFFAOYSA-N 0.000 description 1
- ZXKIKZSRFDVTSY-UHFFFAOYSA-N 4-(2-chloro-4-ethoxyphenyl)benzoic acid Chemical compound ClC1=CC(OCC)=CC=C1C1=CC=C(C(O)=O)C=C1 ZXKIKZSRFDVTSY-UHFFFAOYSA-N 0.000 description 1
- HBRUMVZFJJFINL-UHFFFAOYSA-N 4-(2-chloro-4-fluorophenyl)-N-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide hydrochloride Chemical compound Cl.CN(C=1OC2=C(N1)C=C(C=C2)NC(=O)C2=CC=C(C=C2)C2=C(C=C(C=C2)F)Cl)C2CCN(CC2)C HBRUMVZFJJFINL-UHFFFAOYSA-N 0.000 description 1
- GEYIMGZCBBHLLS-UHFFFAOYSA-N 4-(2-chloro-4-methoxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 GEYIMGZCBBHLLS-UHFFFAOYSA-N 0.000 description 1
- JUGMJUMMUIXDDH-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1Cl JUGMJUMMUIXDDH-UHFFFAOYSA-N 0.000 description 1
- PPGKLLXDIAASEU-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide;hydrochloride Chemical compound Cl.C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1Cl PPGKLLXDIAASEU-UHFFFAOYSA-N 0.000 description 1
- SABVGGGSSMUCHU-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1Cl SABVGGGSSMUCHU-UHFFFAOYSA-N 0.000 description 1
- IMJSHZCHEKCMMO-UHFFFAOYSA-N 4-(2-chloro-4-methylphenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C(=CC(C)=CC=3)Cl)=CC=C2OC=1N(C)C1CCN(C)CC1 IMJSHZCHEKCMMO-UHFFFAOYSA-N 0.000 description 1
- TYOQFWFBDQVNKR-UHFFFAOYSA-N 4-(2-chloro-4-propan-2-yloxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound ClC1=CC(OC(C)C)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 TYOQFWFBDQVNKR-UHFFFAOYSA-N 0.000 description 1
- IEUCYUMKUIONTK-UHFFFAOYSA-N 4-(2-chloro-4-propan-2-yloxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide;hydrochloride Chemical compound Cl.ClC1=CC(OC(C)C)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 IEUCYUMKUIONTK-UHFFFAOYSA-N 0.000 description 1
- ZJZBTQNBVRGRKW-UHFFFAOYSA-N 4-(2-chloro-4-propan-2-yloxyphenyl)benzoic acid Chemical compound ClC1=CC(OC(C)C)=CC=C1C1=CC=C(C(O)=O)C=C1 ZJZBTQNBVRGRKW-UHFFFAOYSA-N 0.000 description 1
- NBJHDLKSWUDGJG-UHFFFAOYSA-N 4-(2-chloroethyl)morpholin-4-ium;chloride Chemical compound Cl.ClCCN1CCOCC1 NBJHDLKSWUDGJG-UHFFFAOYSA-N 0.000 description 1
- MZIFVOLYXURHDM-UHFFFAOYSA-N 4-(2-cyanophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CC=C1C#N MZIFVOLYXURHDM-UHFFFAOYSA-N 0.000 description 1
- NYJHTTLXERQUIV-UHFFFAOYSA-N 4-(2-methyl-4-thiazolyl)benzoic acid Chemical compound S1C(C)=NC(C=2C=CC(=CC=2)C(O)=O)=C1 NYJHTTLXERQUIV-UHFFFAOYSA-N 0.000 description 1
- NDNIPPKLIDCYGD-UHFFFAOYSA-N 4-(2-methylphenyl)benzoic acid Chemical compound CC1=CC=CC=C1C1=CC=C(C(O)=O)C=C1 NDNIPPKLIDCYGD-UHFFFAOYSA-N 0.000 description 1
- WTIHDAFXKHTFEG-UHFFFAOYSA-N 4-(2-methylpropoxy)benzoic acid Chemical compound CC(C)COC1=CC=C(C(O)=O)C=C1 WTIHDAFXKHTFEG-UHFFFAOYSA-N 0.000 description 1
- NVYOOVLWXDVFAA-UHFFFAOYSA-N 4-(3,4-dichlorophenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(Cl)C(Cl)=C1 NVYOOVLWXDVFAA-UHFFFAOYSA-N 0.000 description 1
- CLTCTEGBNKFLOW-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide;hydrochloride Chemical compound Cl.C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1C CLTCTEGBNKFLOW-UHFFFAOYSA-N 0.000 description 1
- ZNIIXHHZSKDKNX-UHFFFAOYSA-N 4-(4-chloro-2-methylphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1C ZNIIXHHZSKDKNX-UHFFFAOYSA-N 0.000 description 1
- PDJSQOOSDBPCLX-UHFFFAOYSA-N 4-(4-ethoxy-2-methylphenyl)benzoic acid Chemical compound CC1=CC(OCC)=CC=C1C1=CC=C(C(O)=O)C=C1 PDJSQOOSDBPCLX-UHFFFAOYSA-N 0.000 description 1
- BMLVSCQHWVAPEW-UHFFFAOYSA-N 4-(4-fluorophenyl)-N-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide hydrochloride Chemical compound Cl.N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 BMLVSCQHWVAPEW-UHFFFAOYSA-N 0.000 description 1
- UMLUBRVQADDSOX-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(2-morpholin-4-ylethyl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CCN1CCOCC1 UMLUBRVQADDSOX-UHFFFAOYSA-N 0.000 description 1
- DTUTWRXCWDQXLW-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(2-pyrrolidin-1-ylethyl)amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CCN1CCCC1 DTUTWRXCWDQXLW-UHFFFAOYSA-N 0.000 description 1
- AJBWHDAYUKKLMC-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl(propan-2-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)C(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 AJBWHDAYUKKLMC-UHFFFAOYSA-N 0.000 description 1
- HZXNSRKYOLVDLC-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 HZXNSRKYOLVDLC-UHFFFAOYSA-N 0.000 description 1
- YCMLBMBFGGTDJG-UHFFFAOYSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[(4-methylmorpholin-2-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CN(C)CCO1 YCMLBMBFGGTDJG-UHFFFAOYSA-N 0.000 description 1
- XVYHQBXGHZYEHB-GNAFDRTKSA-N 4-(4-fluorophenyl)-n-[2-[methyl-[[(2r)-4-methylmorpholin-2-yl]methyl]amino]-1,3-benzoxazol-5-yl]benzamide;hydrochloride Chemical compound Cl.N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C[C@H]1CN(C)CCO1 XVYHQBXGHZYEHB-GNAFDRTKSA-N 0.000 description 1
- JBUCVFXBYNQNIR-UHFFFAOYSA-N 4-(cyclohexylmethoxy)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1OCC1CCCCC1 JBUCVFXBYNQNIR-UHFFFAOYSA-N 0.000 description 1
- PVZKHGCZCWBUFT-UHFFFAOYSA-N 4-(cyclohexylmethoxy)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(OCC4CCCCC4)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 PVZKHGCZCWBUFT-UHFFFAOYSA-N 0.000 description 1
- FPUIRKKWAUSKJL-UHFFFAOYSA-N 4-(cyclohexylmethoxy)-n-[2-[methyl-(1-methylpyrrolidin-3-yl)amino]-1,3-benzothiazol-6-yl]benzamide;hydrochloride Chemical compound Cl.N=1C2=CC=C(NC(=O)C=3C=CC(OCC4CCCCC4)=CC=3)C=C2SC=1N(C)C1CCN(C)C1 FPUIRKKWAUSKJL-UHFFFAOYSA-N 0.000 description 1
- RURHILYUWQEGOS-VOTSOKGWSA-N 4-Methylcinnamic acid Chemical compound CC1=CC=C(\C=C\C(O)=O)C=C1 RURHILYUWQEGOS-VOTSOKGWSA-N 0.000 description 1
- MGGVALXERJRIRO-UHFFFAOYSA-N 4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]-2-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-1H-pyrazol-5-one Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C=1C(=NN(C=1)CC(=O)N1CC2=C(CC1)NN=N2)O MGGVALXERJRIRO-UHFFFAOYSA-N 0.000 description 1
- KVCQTKNUUQOELD-UHFFFAOYSA-N 4-amino-n-[1-(3-chloro-2-fluoroanilino)-6-methylisoquinolin-5-yl]thieno[3,2-d]pyrimidine-7-carboxamide Chemical compound N=1C=CC2=C(NC(=O)C=3C4=NC=NC(N)=C4SC=3)C(C)=CC=C2C=1NC1=CC=CC(Cl)=C1F KVCQTKNUUQOELD-UHFFFAOYSA-N 0.000 description 1
- BPHGMWVJJCWDPB-UHFFFAOYSA-N 4-aminobutylazanium;chloride Chemical compound Cl.NCCCCN BPHGMWVJJCWDPB-UHFFFAOYSA-N 0.000 description 1
- JFKUBRAOUZEZSL-UHFFFAOYSA-N 4-butylbenzoic acid Chemical compound CCCCC1=CC=C(C(O)=O)C=C1 JFKUBRAOUZEZSL-UHFFFAOYSA-N 0.000 description 1
- OUOWCSJYDCPVDM-UHFFFAOYSA-N 4-butylbenzoyl chloride Chemical compound CCCCC1=CC=C(C(Cl)=O)C=C1 OUOWCSJYDCPVDM-UHFFFAOYSA-N 0.000 description 1
- GXLIFJYFGMHYDY-ZZXKWVIFSA-N 4-chlorocinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(Cl)C=C1 GXLIFJYFGMHYDY-ZZXKWVIFSA-N 0.000 description 1
- MGCLDXAOQBXHKC-UHFFFAOYSA-N 4-cyclohex-2-en-1-yl-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1CCCC=C1 MGCLDXAOQBXHKC-UHFFFAOYSA-N 0.000 description 1
- RBUXIZRDHUTKLX-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1CCCCC1 RBUXIZRDHUTKLX-UHFFFAOYSA-N 0.000 description 1
- MHLZYUDQMAURHU-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[3-(dimethylamino)propyl-methylamino]-1,3-benzoxazol-5-yl]benzamide Chemical compound C=1C=C2OC(N(C)CCCN(C)C)=NC2=CC=1NC(=O)C(C=C1)=CC=C1C1CCCCC1 MHLZYUDQMAURHU-UHFFFAOYSA-N 0.000 description 1
- FQSXZROVGPLTIC-UHFFFAOYSA-N 4-cyclohexyl-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]benzamide Chemical compound N=1C2=CC(NC(=O)C=3C=CC(=CC=3)C3CCCCC3)=CC=C2OC=1N(C)CC1CCN(C)C1 FQSXZROVGPLTIC-UHFFFAOYSA-N 0.000 description 1
- MWLQEWDQXQHQED-UHFFFAOYSA-N 4-cyclohexylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1CCCCC1 MWLQEWDQXQHQED-UHFFFAOYSA-N 0.000 description 1
- HQVFLHIVNFRORQ-UHFFFAOYSA-N 4-cyclohexyloxy-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1OC1CCCCC1 HQVFLHIVNFRORQ-UHFFFAOYSA-N 0.000 description 1
- URANGAMHASGWGX-UHFFFAOYSA-N 4-cyclopentylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1CCCC1 URANGAMHASGWGX-UHFFFAOYSA-N 0.000 description 1
- NSTJDFGPPOXIAT-UHFFFAOYSA-N 4-cyclopentyloxybenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1CCCC1 NSTJDFGPPOXIAT-UHFFFAOYSA-N 0.000 description 1
- JPVUWCPKMYXOKW-UHFFFAOYSA-N 4-phenylbenzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=CC=C1 JPVUWCPKMYXOKW-UHFFFAOYSA-N 0.000 description 1
- CVDUBQJEQNRCIZ-UHFFFAOYSA-N 4-thiophen-2-ylbenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=CS1 CVDUBQJEQNRCIZ-UHFFFAOYSA-N 0.000 description 1
- FLDSMVTWEZKONL-AWEZNQCLSA-N 5,5-dimethyl-N-[(3S)-5-methyl-4-oxo-2,3-dihydro-1,5-benzoxazepin-3-yl]-1,4,7,8-tetrahydrooxepino[4,5-c]pyrazole-3-carboxamide Chemical compound CC1(CC2=C(NN=C2C(=O)N[C@@H]2C(N(C3=C(OC2)C=CC=C3)C)=O)CCO1)C FLDSMVTWEZKONL-AWEZNQCLSA-N 0.000 description 1
- QQUOQIUCFSVSAR-UHFFFAOYSA-N 5-(1,3-benzodioxol-5-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(OCO2)C2=C1 QQUOQIUCFSVSAR-UHFFFAOYSA-N 0.000 description 1
- ALAZOWJFLQPDBR-UHFFFAOYSA-N 5-(2,4-dichlorophenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]pyrazine-2-carboxamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(N=C1)=CN=C1C1=CC=C(Cl)C=C1Cl ALAZOWJFLQPDBR-UHFFFAOYSA-N 0.000 description 1
- HQFSPWWAPVGNMA-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)-n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]pyrazine-2-carboxamide Chemical compound ClC1=CC(OC)=CC=C1C1=CN=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=N1 HQFSPWWAPVGNMA-UHFFFAOYSA-N 0.000 description 1
- ZYGVEKCFDQOYFF-UHFFFAOYSA-N 5-(2-chloro-4-methoxyphenyl)pyrazine-2-carboxylic acid Chemical compound ClC1=CC(OC)=CC=C1C1=CN=C(C(O)=O)C=N1 ZYGVEKCFDQOYFF-UHFFFAOYSA-N 0.000 description 1
- WLBXMBPSORBEAK-UHFFFAOYSA-N 5-(3-fluorophenyl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CC(F)=C1 WLBXMBPSORBEAK-UHFFFAOYSA-N 0.000 description 1
- SKMSNYWMPSAJFB-UHFFFAOYSA-N 5-(4-chlorophenyl)-n-[2-[methyl(propan-2-yl)amino]-1,3-benzothiazol-6-yl]-1,2-oxazole-3-carboxamide Chemical compound C1=C2SC(N(C)C(C)C)=NC2=CC=C1NC(=O)C(=NO1)C=C1C1=CC=C(Cl)C=C1 SKMSNYWMPSAJFB-UHFFFAOYSA-N 0.000 description 1
- ZMNNARNHHOQVNW-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]pyrazine-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3N=CC(=NC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 ZMNNARNHHOQVNW-UHFFFAOYSA-N 0.000 description 1
- KDNFSIYGFOKCPG-UHFFFAOYSA-N 5-(4-fluorophenyl)-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]thiophene-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3SC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 KDNFSIYGFOKCPG-UHFFFAOYSA-N 0.000 description 1
- XLTXZWKQUHETLK-UHFFFAOYSA-N 5-(4-methoxyphenyl)thiophene-2-carboxylic acid Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(O)=O)S1 XLTXZWKQUHETLK-UHFFFAOYSA-N 0.000 description 1
- HAJCITVNZKDTPX-UHFFFAOYSA-N 5-(4-methylphenyl)thiophene-2-carboxylic acid Chemical compound C1=CC(C)=CC=C1C1=CC=C(C(O)=O)S1 HAJCITVNZKDTPX-UHFFFAOYSA-N 0.000 description 1
- OHEOLKHLDJYUCZ-UHFFFAOYSA-N 5-(5-chlorothiophen-2-yl)thiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=C(Cl)S1 OHEOLKHLDJYUCZ-UHFFFAOYSA-N 0.000 description 1
- IRPVABHDSJVBNZ-RTHVDDQRSA-N 5-[1-(cyclopropylmethyl)-5-[(1R,5S)-3-(oxetan-3-yl)-3-azabicyclo[3.1.0]hexan-6-yl]pyrazol-3-yl]-3-(trifluoromethyl)pyridin-2-amine Chemical compound C1=C(C(F)(F)F)C(N)=NC=C1C1=NN(CC2CC2)C(C2[C@@H]3CN(C[C@@H]32)C2COC2)=C1 IRPVABHDSJVBNZ-RTHVDDQRSA-N 0.000 description 1
- MVDXXGIBARMXSA-PYUWXLGESA-N 5-[[(2r)-2-benzyl-3,4-dihydro-2h-chromen-6-yl]methyl]-1,3-thiazolidine-2,4-dione Chemical compound S1C(=O)NC(=O)C1CC1=CC=C(O[C@@H](CC=2C=CC=CC=2)CC2)C2=C1 MVDXXGIBARMXSA-PYUWXLGESA-N 0.000 description 1
- COWZPSUDTMGBAT-UHFFFAOYSA-N 5-bromothiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=C(Br)S1 COWZPSUDTMGBAT-UHFFFAOYSA-N 0.000 description 1
- YLUIDVIWVCPUHM-UHFFFAOYSA-N 5-chloro-n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]pyrazine-2-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3N=CC(Cl)=NC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 YLUIDVIWVCPUHM-UHFFFAOYSA-N 0.000 description 1
- WTXBRZCVLDTWLP-UHFFFAOYSA-N 5-fluoro-1H-indole-2-carboxylic acid Chemical compound FC1=CC=C2NC(C(=O)O)=CC2=C1 WTXBRZCVLDTWLP-UHFFFAOYSA-N 0.000 description 1
- HCTMDIVCEAEJOQ-UHFFFAOYSA-N 5-phenyl-1,3,4-oxadiazole-2-carboxylic acid Chemical compound O1C(C(=O)O)=NN=C1C1=CC=CC=C1 HCTMDIVCEAEJOQ-UHFFFAOYSA-N 0.000 description 1
- YULGUYOVJXOPLU-UHFFFAOYSA-N 5-phenyl-1,3-oxazole-2-carboxylic acid Chemical compound O1C(C(=O)O)=NC=C1C1=CC=CC=C1 YULGUYOVJXOPLU-UHFFFAOYSA-N 0.000 description 1
- HENDYXUZFUWIMG-UHFFFAOYSA-N 5-pyridin-3-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CN=C1 HENDYXUZFUWIMG-UHFFFAOYSA-N 0.000 description 1
- OJOWGMLSJKRJNV-UHFFFAOYSA-N 5-pyridin-4-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=NC=C1 OJOWGMLSJKRJNV-UHFFFAOYSA-N 0.000 description 1
- PTNWHEHDBNNKEO-UHFFFAOYSA-N 5-thiophen-2-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CC=CS1 PTNWHEHDBNNKEO-UHFFFAOYSA-N 0.000 description 1
- NUZWQKDXTFZYAX-UHFFFAOYSA-N 5-thiophen-3-ylthiophene-2-carboxylic acid Chemical compound S1C(C(=O)O)=CC=C1C1=CSC=C1 NUZWQKDXTFZYAX-UHFFFAOYSA-N 0.000 description 1
- KCBWAFJCKVKYHO-UHFFFAOYSA-N 6-(4-cyclopropyl-6-methoxypyrimidin-5-yl)-1-[[4-[1-propan-2-yl-4-(trifluoromethyl)imidazol-2-yl]phenyl]methyl]pyrazolo[3,4-d]pyrimidine Chemical compound C1(CC1)C1=NC=NC(=C1C1=NC=C2C(=N1)N(N=C2)CC1=CC=C(C=C1)C=1N(C=C(N=1)C(F)(F)F)C(C)C)OC KCBWAFJCKVKYHO-UHFFFAOYSA-N 0.000 description 1
- ZALQSURZVFZOEZ-UHFFFAOYSA-N 6-(4-fluorophenyl)-n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]pyridine-3-carboxamide Chemical compound N=1C2=CC(NC(=O)C=3C=NC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 ZALQSURZVFZOEZ-UHFFFAOYSA-N 0.000 description 1
- CGQFCIHUUCMACC-UHFFFAOYSA-N 6-oxo-1h-pyrazine-3-carboxylic acid Chemical compound OC(=O)C1=CNC(=O)C=N1 CGQFCIHUUCMACC-UHFFFAOYSA-N 0.000 description 1
- 125000003341 7 membered heterocyclic group Chemical group 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
- 241001474033 Acar Species 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 229940077274 Alpha glucosidase inhibitor Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 208000000103 Anorexia Nervosa Diseases 0.000 description 1
- 241000271566 Aves Species 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 229940123208 Biguanide Drugs 0.000 description 1
- 241000283726 Bison Species 0.000 description 1
- 208000031648 Body Weight Changes Diseases 0.000 description 1
- 208000010392 Bone Fractures Diseases 0.000 description 1
- 241000282817 Bovidae Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 241000030939 Bubalus bubalis Species 0.000 description 1
- 229940124802 CB1 antagonist Drugs 0.000 description 1
- GXSPHHWVQAJUIM-UHFFFAOYSA-N CN(CCN(C=1SC2=C(N1)C=CC(=C2)NC(=O)C2=CC(=C(C=C2)C2=CC=C(C=C2)OC2CCCC2)Cl)C)C Chemical compound CN(CCN(C=1SC2=C(N1)C=CC(=C2)NC(=O)C2=CC(=C(C=C2)C2=CC=C(C=C2)OC2CCCC2)Cl)C)C GXSPHHWVQAJUIM-UHFFFAOYSA-N 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 206010007559 Cardiac failure congestive Diseases 0.000 description 1
- 206010008111 Cerebral haemorrhage Diseases 0.000 description 1
- 229920001268 Cholestyramine Polymers 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 229920002911 Colestipol Polymers 0.000 description 1
- 206010010904 Convulsion Diseases 0.000 description 1
- 229910021590 Copper(II) bromide Inorganic materials 0.000 description 1
- 241000270722 Crocodylidae Species 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 102000016928 DNA-directed DNA polymerase Human genes 0.000 description 1
- 108010014303 DNA-directed DNA polymerase Proteins 0.000 description 1
- 102000007260 Deoxyribonuclease I Human genes 0.000 description 1
- 108010008532 Deoxyribonuclease I Proteins 0.000 description 1
- 229920002307 Dextran Polymers 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- 241000271571 Dromaius novaehollandiae Species 0.000 description 1
- 208000030814 Eating disease Diseases 0.000 description 1
- 208000019454 Feeding and Eating disease Diseases 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- OZLGRUXZXMRXGP-UHFFFAOYSA-N Fluo-3 Chemical compound CC1=CC=C(N(CC(O)=O)CC(O)=O)C(OCCOC=2C(=CC=C(C=2)C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)N(CC(O)=O)CC(O)=O)=C1 OZLGRUXZXMRXGP-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
- 108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- HEMJJKBWTPKOJG-UHFFFAOYSA-N Gemfibrozil Chemical compound CC1=CC=C(C)C(OCCCC(C)(C)C(O)=O)=C1 HEMJJKBWTPKOJG-UHFFFAOYSA-N 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 101000581408 Homo sapiens Melanin-concentrating hormone receptor 2 Proteins 0.000 description 1
- 206010022489 Insulin Resistance Diseases 0.000 description 1
- 229940122355 Insulin sensitizer Drugs 0.000 description 1
- ZDXPYRJPNDTMRX-VKHMYHEASA-N L-glutamine Chemical compound OC(=O)[C@@H](N)CCC(N)=O ZDXPYRJPNDTMRX-VKHMYHEASA-N 0.000 description 1
- 229930182816 L-glutamine Natural products 0.000 description 1
- 229910008293 Li—C Inorganic materials 0.000 description 1
- 102100027373 Melanin-concentrating hormone receptor 2 Human genes 0.000 description 1
- 108010008364 Melanocortins Proteins 0.000 description 1
- 239000000637 Melanocyte-Stimulating Hormone Substances 0.000 description 1
- 101710151321 Melanostatin Proteins 0.000 description 1
- 241000699660 Mus musculus Species 0.000 description 1
- WRQHWCLSHDFVLA-UHFFFAOYSA-N N-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(2,4-dimethylphenyl)benzamide hydrochloride Chemical compound Cl.C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1C WRQHWCLSHDFVLA-UHFFFAOYSA-N 0.000 description 1
- VCUFZILGIRCDQQ-KRWDZBQOSA-N N-[[(5S)-2-oxo-3-(2-oxo-3H-1,3-benzoxazol-6-yl)-1,3-oxazolidin-5-yl]methyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C1O[C@H](CN1C1=CC2=C(NC(O2)=O)C=C1)CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F VCUFZILGIRCDQQ-KRWDZBQOSA-N 0.000 description 1
- 108010025020 Nerve Growth Factor Proteins 0.000 description 1
- 102000015336 Nerve Growth Factor Human genes 0.000 description 1
- 102400000064 Neuropeptide Y Human genes 0.000 description 1
- IDRGFNPZDVBSSE-UHFFFAOYSA-N OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F Chemical compound OCCN1CCN(CC1)c1ccc(Nc2ncc3cccc(-c4cccc(NC(=O)C=C)c4)c3n2)c(F)c1F IDRGFNPZDVBSSE-UHFFFAOYSA-N 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- 238000012408 PCR amplification Methods 0.000 description 1
- 101150014691 PPARA gene Proteins 0.000 description 1
- 208000002193 Pain Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 229920001774 Perfluoroether Polymers 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 102000001708 Protein Isoforms Human genes 0.000 description 1
- 108010029485 Protein Isoforms Proteins 0.000 description 1
- YASAKCUCGLMORW-UHFFFAOYSA-N Rosiglitazone Chemical compound C=1C=CC=NC=1N(C)CCOC(C=C1)=CC=C1CC1SC(=O)NC1=O YASAKCUCGLMORW-UHFFFAOYSA-N 0.000 description 1
- 241000282849 Ruminantia Species 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 102000001494 Sterol O-Acyltransferase Human genes 0.000 description 1
- 108010054082 Sterol O-acyltransferase Proteins 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 229940100389 Sulfonylurea Drugs 0.000 description 1
- JLRGJRBPOGGCBT-UHFFFAOYSA-N Tolbutamide Chemical compound CCCCNC(=O)NS(=O)(=O)C1=CC=C(C)C=C1 JLRGJRBPOGGCBT-UHFFFAOYSA-N 0.000 description 1
- 229930003427 Vitamin E Natural products 0.000 description 1
- 108010084455 Zeocin Proteins 0.000 description 1
- LXRZVMYMQHNYJB-UNXOBOICSA-N [(1R,2S,4R)-4-[[5-[4-[(1R)-7-chloro-1,2,3,4-tetrahydroisoquinolin-1-yl]-5-methylthiophene-2-carbonyl]pyrimidin-4-yl]amino]-2-hydroxycyclopentyl]methyl sulfamate Chemical compound CC1=C(C=C(S1)C(=O)C1=C(N[C@H]2C[C@H](O)[C@@H](COS(N)(=O)=O)C2)N=CN=C1)[C@@H]1NCCC2=C1C=C(Cl)C=C2 LXRZVMYMQHNYJB-UNXOBOICSA-N 0.000 description 1
- JKSUCAFAUNSPLO-UHFFFAOYSA-N [2-chloro-4-(trifluoromethyl)phenyl]boronic acid Chemical compound OB(O)C1=CC=C(C(F)(F)F)C=C1Cl JKSUCAFAUNSPLO-UHFFFAOYSA-N 0.000 description 1
- 229960002632 acarbose Drugs 0.000 description 1
- XUFXOAAUWZOOIT-UHFFFAOYSA-N acarviostatin I01 Natural products OC1C(O)C(NC2C(C(O)C(O)C(CO)=C2)O)C(C)OC1OC(C(C1O)O)C(CO)OC1OC1C(CO)OC(O)C(O)C1O XUFXOAAUWZOOIT-UHFFFAOYSA-N 0.000 description 1
- 230000021736 acetylation Effects 0.000 description 1
- 238000006640 acetylation reaction Methods 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 238000000246 agarose gel electrophoresis Methods 0.000 description 1
- 230000002776 aggregation Effects 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000004422 alkyl sulphonamide group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 239000003888 alpha glucosidase inhibitor Substances 0.000 description 1
- 238000010640 amide synthesis reaction Methods 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000003321 amplification Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 230000000692 anti-sense effect Effects 0.000 description 1
- 239000000164 antipsychotic agent Substances 0.000 description 1
- 238000009360 aquaculture Methods 0.000 description 1
- 244000144974 aquaculture Species 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RFRXIWQYSOIBDI-UHFFFAOYSA-N benzarone Chemical compound CCC=1OC2=CC=CC=C2C=1C(=O)C1=CC=C(O)C=C1 RFRXIWQYSOIBDI-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 150000004283 biguanides Chemical class 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000004579 body weight change Effects 0.000 description 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 244000309464 bull Species 0.000 description 1
- 239000004197 calcium inosinate Substances 0.000 description 1
- 229930003827 cannabinoid Natural products 0.000 description 1
- 239000003557 cannabinoid Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
- 125000002837 carbocyclic group Chemical group 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 description 1
- 230000001906 cholesterol absorption Effects 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 1
- GMRWGQCZJGVHKL-UHFFFAOYSA-N colestipol Chemical compound ClCC1CO1.NCCNCCNCCNCCN GMRWGQCZJGVHKL-UHFFFAOYSA-N 0.000 description 1
- 229960002604 colestipol Drugs 0.000 description 1
- 238000011284 combination treatment Methods 0.000 description 1
- 238000012875 competitive assay Methods 0.000 description 1
- 230000002860 competitive effect Effects 0.000 description 1
- 238000010668 complexation reaction Methods 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- NKNDPYCGAZPOFS-UHFFFAOYSA-M copper(i) bromide Chemical compound Br[Cu] NKNDPYCGAZPOFS-UHFFFAOYSA-M 0.000 description 1
- IDLFZVILOHSSID-OVLDLUHVSA-N corticotropin Chemical compound C([C@@H](C(=O)N[C@@H](CO)C(=O)N[C@@H](CCSC)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1NC=NC=1)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)NCC(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CCCCN)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(N)=O)C(=O)NCC(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CO)C(=O)N[C@@H](C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(O)=O)NC(=O)[C@@H](N)CO)C1=CC=C(O)C=C1 IDLFZVILOHSSID-OVLDLUHVSA-N 0.000 description 1
- 229960000258 corticotropin Drugs 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000001047 cyclobutenyl group Chemical group C1(=CCC1)* 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001162 cycloheptenyl group Chemical group C1(=CCCCCC1)* 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- 125000000522 cyclooctenyl group Chemical group C1(=CCCCCCC1)* 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
- 125000000298 cyclopropenyl group Chemical group [H]C1=C([H])C1([H])* 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 235000021316 daily nutritional intake Nutrition 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- 238000004925 denaturation Methods 0.000 description 1
- 230000036425 denaturation Effects 0.000 description 1
- 238000009795 derivation Methods 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 229960004597 dexfenfluramine Drugs 0.000 description 1
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000006193 diazotization reaction Methods 0.000 description 1
- 125000003963 dichloro group Chemical group Cl* 0.000 description 1
- SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
- BSHICDXRSZQYBP-UHFFFAOYSA-N dichloromethane;palladium(2+) Chemical compound [Pd+2].ClCCl BSHICDXRSZQYBP-UHFFFAOYSA-N 0.000 description 1
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 1
- 235000014632 disordered eating Nutrition 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 235000006694 eating habits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 229950002375 englitazone Drugs 0.000 description 1
- 238000006911 enzymatic reaction Methods 0.000 description 1
- 206010015037 epilepsy Diseases 0.000 description 1
- 208000028329 epileptic seizure Diseases 0.000 description 1
- 229960005139 epinephrine Drugs 0.000 description 1
- XBRDBODLCHKXHI-UHFFFAOYSA-N epolamine Chemical compound OCCN1CCCC1 XBRDBODLCHKXHI-UHFFFAOYSA-N 0.000 description 1
- 125000006437 ethyl cyclopropyl group Chemical group 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000004634 feeding behavior Effects 0.000 description 1
- 229960001582 fenfluramine Drugs 0.000 description 1
- 229960002297 fenofibrate Drugs 0.000 description 1
- YMTINGFKWWXKFG-UHFFFAOYSA-N fenofibrate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)C)=CC=C1C(=O)C1=CC=C(Cl)C=C1 YMTINGFKWWXKFG-UHFFFAOYSA-N 0.000 description 1
- MQOBSOSZFYZQOK-UHFFFAOYSA-N fenofibric acid Chemical class C1=CC(OC(C)(C)C(O)=O)=CC=C1C(=O)C1=CC=C(Cl)C=C1 MQOBSOSZFYZQOK-UHFFFAOYSA-N 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 125000001207 fluorophenyl group Chemical group 0.000 description 1
- 229960002464 fluoxetine Drugs 0.000 description 1
- 238000011010 flushing procedure Methods 0.000 description 1
- 150000003948 formamides Chemical class 0.000 description 1
- 239000012634 fragment Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- WIGCFUFOHFEKBI-UHFFFAOYSA-N gamma-tocopherol Natural products CC(C)CCCC(C)CCCC(C)CCCC1CCC2C(C)C(O)C(C)C(C)C2O1 WIGCFUFOHFEKBI-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 229960003627 gemfibrozil Drugs 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- ZJJXGWJIGJFDTL-UHFFFAOYSA-N glipizide Chemical compound C1=NC(C)=CN=C1C(=O)NCCC1=CC=C(S(=O)(=O)NC(=O)NC2CCCCC2)C=C1 ZJJXGWJIGJFDTL-UHFFFAOYSA-N 0.000 description 1
- 229960001381 glipizide Drugs 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 244000309465 heifer Species 0.000 description 1
- 125000003707 hexyloxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 102000047277 human MCHR1 Human genes 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 230000003166 hypermetabolic effect Effects 0.000 description 1
- 230000002806 hypometabolic effect Effects 0.000 description 1
- 230000001639 hypophagic effect Effects 0.000 description 1
- 230000004179 hypothalamic–pituitary–adrenal axis Effects 0.000 description 1
- 238000003384 imaging method Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000007918 intramuscular administration Methods 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- FMKOJHQHASLBPH-UHFFFAOYSA-N isopropyl iodide Chemical compound CC(C)I FMKOJHQHASLBPH-UHFFFAOYSA-N 0.000 description 1
- IXFLTVWYYQIVRB-UHFFFAOYSA-N isoquinoline-3-carboxylic acid;hydrate Chemical compound O.C1=CC=C2C=NC(C(=O)O)=CC2=C1 IXFLTVWYYQIVRB-UHFFFAOYSA-N 0.000 description 1
- 125000001786 isothiazolyl group Chemical group 0.000 description 1
- 210000000629 knee joint Anatomy 0.000 description 1
- 238000011813 knockout mouse model Methods 0.000 description 1
- 210000003796 lateral hypothalamic area Anatomy 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000013289 male long evans rat Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000002483 medication Methods 0.000 description 1
- 239000002865 melanocortin Substances 0.000 description 1
- 229950008446 melinamide Drugs 0.000 description 1
- 108020004999 messenger RNA Proteins 0.000 description 1
- 230000002503 metabolic effect Effects 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
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- AZRDKIMMTUWBOS-UHFFFAOYSA-N methyl 3-methyl-4-phenylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1C1=CC=CC=C1 AZRDKIMMTUWBOS-UHFFFAOYSA-N 0.000 description 1
- GTZTYNPAPQKIIR-UHFFFAOYSA-N methyl 4-bromo-3-methylbenzoate Chemical compound COC(=O)C1=CC=C(Br)C(C)=C1 GTZTYNPAPQKIIR-UHFFFAOYSA-N 0.000 description 1
- FEKSIFWGIQSXKQ-UHFFFAOYSA-N methyl 5-phenyl-1,3,4-oxadiazole-2-carboxylate Chemical compound O1C(C(=O)OC)=NN=C1C1=CC=CC=C1 FEKSIFWGIQSXKQ-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 239000003068 molecular probe Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- XRYGCVVVDCEPRL-UHFFFAOYSA-N n,1-dimethylpiperidin-4-amine Chemical compound CNC1CCN(C)CC1 XRYGCVVVDCEPRL-UHFFFAOYSA-N 0.000 description 1
- YZHDYCIEOHSXQC-UHFFFAOYSA-N n,n'-dimethyl-n'-(6-nitro-1,3-benzothiazol-2-yl)ethane-1,2-diamine Chemical compound C1=C([N+]([O-])=O)C=C2SC(N(C)CCNC)=NC2=C1 YZHDYCIEOHSXQC-UHFFFAOYSA-N 0.000 description 1
- BFWPUEIQCXQGOY-UHFFFAOYSA-N n,n'-dimethyl-n'-quinolin-2-ylpropane-1,3-diamine Chemical compound C1=CC=CC2=NC(N(C)CCCNC)=CC=C21 BFWPUEIQCXQGOY-UHFFFAOYSA-N 0.000 description 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 description 1
- BBQGZCOECNMDHN-UHFFFAOYSA-N n,n,n'-trimethyl-n'-(5-nitro-1,3-benzoxazol-2-yl)ethane-1,2-diamine Chemical compound [O-][N+](=O)C1=CC=C2OC(N(C)CCN(C)C)=NC2=C1 BBQGZCOECNMDHN-UHFFFAOYSA-N 0.000 description 1
- DTKKDUXAKODAIE-UHFFFAOYSA-N n,n-dimethylpyrrolidin-1-amine Chemical compound CN(C)N1CCCC1 DTKKDUXAKODAIE-UHFFFAOYSA-N 0.000 description 1
- DFFFKTMARDIDRZ-UHFFFAOYSA-N n-(2-chloro-1,3-benzothiazol-6-yl)-4-(4-chlorophenyl)benzamide Chemical compound C1=C2SC(Cl)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(Cl)C=C1 DFFFKTMARDIDRZ-UHFFFAOYSA-N 0.000 description 1
- RUYFRSCWBAKOLV-UHFFFAOYSA-N n-(2-chloro-1,3-benzothiazol-6-yl)-4-(4-fluorophenyl)benzamide Chemical compound C1=CC(F)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(Cl)=NC3=CC=2)C=C1 RUYFRSCWBAKOLV-UHFFFAOYSA-N 0.000 description 1
- TZAMPEVMXMOTSL-UHFFFAOYSA-N n-[2-[(1-acetylpyrrolidin-3-yl)methyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound N=1C2=CC=C(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)C=C2SC=1N(C)CC1CCN(C(C)=O)C1 TZAMPEVMXMOTSL-UHFFFAOYSA-N 0.000 description 1
- IKUCMRISMDTNMJ-UHFFFAOYSA-N n-[2-[(1-ethylpyrrolidin-3-yl)methyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1N(CC)CCC1CN(C)C(SC1=C2)=NC1=CC=C2NC(=O)C1=CC=C(C=2C=CC(F)=CC=2)C=C1 IKUCMRISMDTNMJ-UHFFFAOYSA-N 0.000 description 1
- UNPRHKRDEALJPS-UHFFFAOYSA-N n-[2-[(6-amino-1,3-benzothiazol-2-yl)-methylamino]ethyl]-n-methylacetamide Chemical compound C1=C(N)C=C2SC(N(C)CCN(C)C(C)=O)=NC2=C1 UNPRHKRDEALJPS-UHFFFAOYSA-N 0.000 description 1
- HHVIRNBZQDAASK-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C=CC1=CC=C(C(F)(F)F)C=C1 HHVIRNBZQDAASK-UHFFFAOYSA-N 0.000 description 1
- NORNJUVLUKPBIK-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-3-methyl-4-phenylbenzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1C)=CC=C1C1=CC=CC=C1 NORNJUVLUKPBIK-UHFFFAOYSA-N 0.000 description 1
- FKVFZSUYEOVNQG-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-3-phenoxybenzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 FKVFZSUYEOVNQG-UHFFFAOYSA-N 0.000 description 1
- IUVLNRPQZDDSDE-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(2,4-dimethylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(C)C=C1C IUVLNRPQZDDSDE-UHFFFAOYSA-N 0.000 description 1
- JJALPJONYNBPPJ-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(2-methoxyphenyl)benzamide Chemical compound COC1=CC=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 JJALPJONYNBPPJ-UHFFFAOYSA-N 0.000 description 1
- CRSAIDAXJBYEFQ-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(3-methylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CC(C)=C1 CRSAIDAXJBYEFQ-UHFFFAOYSA-N 0.000 description 1
- DXNJCJRPPBOPQU-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluoro-2-methylphenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1C DXNJCJRPPBOPQU-UHFFFAOYSA-N 0.000 description 1
- SKTNBTHKDFUSLI-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-methoxyphenyl)benzamide Chemical compound C1=CC(OC)=CC=C1C1=CC=C(C(=O)NC=2C=C3SC(=NC3=CC=2)N(C)CCN(C)C)C=C1 SKTNBTHKDFUSLI-UHFFFAOYSA-N 0.000 description 1
- RSVROADAIGMSLF-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-thiophen-2-ylbenzamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=CS1 RSVROADAIGMSLF-UHFFFAOYSA-N 0.000 description 1
- YZODGMDYKXBTNH-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-5-(4-fluorophenyl)thiophene-2-carboxamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(S1)=CC=C1C1=CC=C(F)C=C1 YZODGMDYKXBTNH-UHFFFAOYSA-N 0.000 description 1
- HOFBJWXQWBMOMV-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-5-phenylthiophene-2-carboxamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(S1)=CC=C1C1=CC=CC=C1 HOFBJWXQWBMOMV-UHFFFAOYSA-N 0.000 description 1
- XEAOXVUGACRDSN-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzothiazol-6-yl]-6-phenylpyridine-3-carboxamide Chemical compound C1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=N1)=CC=C1C1=CC=CC=C1 XEAOXVUGACRDSN-UHFFFAOYSA-N 0.000 description 1
- KFWKWURGAWHHAU-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-4-(2-methylpropoxy)benzamide Chemical compound C1=CC(OCC(C)C)=CC=C1C(=O)NC1=CC=C(OC(=N2)N(C)CCN(C)C)C2=C1 KFWKWURGAWHHAU-UHFFFAOYSA-N 0.000 description 1
- SMMBKVUQNTZIHC-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-1,3-benzoxazol-5-yl]-5-(4-fluorophenyl)pyridine-2-carboxamide;hydrochloride Chemical compound Cl.C=1C=C2OC(N(C)CCN(C)C)=NC2=CC=1NC(=O)C(N=C1)=CC=C1C1=CC=C(F)C=C1 SMMBKVUQNTZIHC-UHFFFAOYSA-N 0.000 description 1
- IHJIMOCVNKSVJX-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethyl-methylamino]-7-methyl-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound CC1=C2SC(N(C)CCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 IHJIMOCVNKSVJX-UHFFFAOYSA-N 0.000 description 1
- KFWWFAQUOLEZGX-UHFFFAOYSA-N n-[2-[2-(dimethylamino)ethylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(NCCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 KFWWFAQUOLEZGX-UHFFFAOYSA-N 0.000 description 1
- FJXFUZDXHJOZRQ-UHFFFAOYSA-N n-[2-[2-[acetyl(methyl)amino]ethyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(N(C)CCN(C)C(C)=O)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 FJXFUZDXHJOZRQ-UHFFFAOYSA-N 0.000 description 1
- PDEZEBRAVBUFRU-UHFFFAOYSA-N n-[2-[3-(diethylamino)propyl-methylamino]-1,3-benzoxazol-5-yl]-3-phenoxybenzamide;hydrochloride Chemical compound Cl.C=1C=C2OC(N(C)CCCN(CC)CC)=NC2=CC=1NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 PDEZEBRAVBUFRU-UHFFFAOYSA-N 0.000 description 1
- NMXCLBSETQNABX-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propyl-methylamino]-1,3-benzothiazol-6-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1=C2SC(N(C)CCCN(C)C)=NC2=CC=C1NC(=O)C(C=C1)=CC=C1C1=CC=C(F)C=C1 NMXCLBSETQNABX-UHFFFAOYSA-N 0.000 description 1
- IJTNZPZVMRDFJW-UHFFFAOYSA-N n-[2-[3-(dimethylamino)propyl-methylamino]-1,3-benzoxazol-5-yl]-3-phenoxybenzamide;hydrochloride Chemical compound Cl.C=1C=C2OC(N(C)CCCN(C)C)=NC2=CC=1NC(=O)C(C=1)=CC=CC=1OC1=CC=CC=C1 IJTNZPZVMRDFJW-UHFFFAOYSA-N 0.000 description 1
- YHOCUAYHBJSJPM-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]-2-methyl-3-phenylprop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C(C)=CC1=CC=CC=C1 YHOCUAYHBJSJPM-UHFFFAOYSA-N 0.000 description 1
- MSFXJMASKCXEDZ-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]-3-(4-methylphenyl)prop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C=CC1=CC=C(C)C=C1 MSFXJMASKCXEDZ-UHFFFAOYSA-N 0.000 description 1
- JXFGLDAQVSAWJN-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]-3-naphthalen-2-ylprop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C=CC1=CC=C(C=CC=C2)C2=C1 JXFGLDAQVSAWJN-UHFFFAOYSA-N 0.000 description 1
- FRNDSDRBNGAGDA-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]-3-phenylprop-2-enamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C=CC1=CC=CC=C1 FRNDSDRBNGAGDA-UHFFFAOYSA-N 0.000 description 1
- JUYJPXCGCPFKAL-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]-5-fluoro-1h-indole-2-carboxamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C1=CC2=CC(F)=CC=C2N1 JUYJPXCGCPFKAL-UHFFFAOYSA-N 0.000 description 1
- DSBOKLJXBHDCIP-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzothiazol-6-yl]-5-phenyl-1,2-oxazole-3-carboxamide Chemical compound C1C(N(C)C)CCN1C(SC1=C2)=NC1=CC=C2NC(=O)C1=NOC(C=2C=CC=CC=2)=C1 DSBOKLJXBHDCIP-UHFFFAOYSA-N 0.000 description 1
- QCOLEOBZBJYJEC-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzoxazol-5-yl]-3-(4-fluorophenyl)prop-2-enamide Chemical compound C1C(N(C)C)CCN1C1=NC2=CC(NC(=O)C=CC=3C=CC(F)=CC=3)=CC=C2O1 QCOLEOBZBJYJEC-UHFFFAOYSA-N 0.000 description 1
- XYJLSCGMVOSJEH-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzoxazol-5-yl]-3-(4-methoxyphenyl)prop-2-enamide Chemical compound C1=CC(OC)=CC=C1C=CC(=O)NC1=CC=C(OC(=N2)N3CC(CC3)N(C)C)C2=C1 XYJLSCGMVOSJEH-UHFFFAOYSA-N 0.000 description 1
- HPFJXRDEMDXIGU-UHFFFAOYSA-N n-[2-[3-(dimethylamino)pyrrolidin-1-yl]-1,3-benzoxazol-5-yl]-4-(4-fluorophenyl)benzamide Chemical compound C1C(N(C)C)CCN1C1=NC2=CC(NC(=O)C=3C=CC(=CC=3)C=3C=CC(F)=CC=3)=CC=C2O1 HPFJXRDEMDXIGU-UHFFFAOYSA-N 0.000 description 1
- QFIRAEXHTWHQST-UHFFFAOYSA-N n-[2-[methyl(propan-2-yl)amino]-1,3-benzothiazol-6-yl]-3-[4-(trifluoromethyl)phenyl]prop-2-enamide Chemical compound C1=C2SC(N(C)C(C)C)=NC2=CC=C1NC(=O)C=CC1=CC=C(C(F)(F)F)C=C1 QFIRAEXHTWHQST-UHFFFAOYSA-N 0.000 description 1
- TWNYZFKMAOXGSF-UHFFFAOYSA-N n-[2-[methyl-(1-methylpiperidin-4-yl)amino]-1,3-benzoxazol-5-yl]-3-phenoxybenzamide Chemical compound N=1C2=CC(NC(=O)C=3C=C(OC=4C=CC=CC=4)C=CC=3)=CC=C2OC=1N(C)C1CCN(C)CC1 TWNYZFKMAOXGSF-UHFFFAOYSA-N 0.000 description 1
- ZHSLKJJMXIZNJO-UHFFFAOYSA-N n-[2-[methyl-[(1-methylpyrrolidin-3-yl)methyl]amino]-1,3-benzoxazol-5-yl]-3-phenoxybenzamide Chemical compound N=1C2=CC(NC(=O)C=3C=C(OC=4C=CC=CC=4)C=CC=3)=CC=C2OC=1N(C)CC1CCN(C)C1 ZHSLKJJMXIZNJO-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- ZLDWGNZSKNMPRQ-UHFFFAOYSA-N n-methyl-1-(1-methylpyrrolidin-3-yl)methanamine Chemical compound CNCC1CCN(C)C1 ZLDWGNZSKNMPRQ-UHFFFAOYSA-N 0.000 description 1
- HGJBHLXETHCNQT-UHFFFAOYSA-N n-methyl-6-nitro-n-(2-piperidin-1-ylethyl)-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=C([N+]([O-])=O)C=C2SC=1N(C)CCN1CCCCC1 HGJBHLXETHCNQT-UHFFFAOYSA-N 0.000 description 1
- OUKJJKVEUCIMEE-UHFFFAOYSA-N n-methyl-6-nitro-n-(2-pyrrolidin-1-ylethyl)-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=C([N+]([O-])=O)C=C2SC=1N(C)CCN1CCCC1 OUKJJKVEUCIMEE-UHFFFAOYSA-N 0.000 description 1
- UALOUFHSURJRSA-UHFFFAOYSA-N n-methyl-n-(1-methylpiperidin-3-yl)-6-nitro-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=C([N+]([O-])=O)C=C2SC=1N(C)C1CCCN(C)C1 UALOUFHSURJRSA-UHFFFAOYSA-N 0.000 description 1
- ATTIAKRRPKDZHN-UHFFFAOYSA-N n-methyl-n-(2-morpholin-4-ylethyl)-6-nitro-1,3-benzothiazol-2-amine Chemical compound N=1C2=CC=C([N+]([O-])=O)C=C2SC=1N(C)CCN1CCOCC1 ATTIAKRRPKDZHN-UHFFFAOYSA-N 0.000 description 1
- OORKVEQNDSMHLI-UHFFFAOYSA-N n-methyl-n-[2-[methyl-(6-nitro-1,3-benzothiazol-2-yl)amino]ethyl]acetamide Chemical compound C1=C([N+]([O-])=O)C=C2SC(N(C)CCN(C)C(C)=O)=NC2=C1 OORKVEQNDSMHLI-UHFFFAOYSA-N 0.000 description 1
- XHFGWHUWQXTGAT-UHFFFAOYSA-N n-methylpropan-2-amine Chemical compound CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
- 229960004927 neomycin Drugs 0.000 description 1
- 229940053128 nerve growth factor Drugs 0.000 description 1
- PKWDZWYVIHVNKS-UHFFFAOYSA-N netoglitazone Chemical compound FC1=CC=CC=C1COC1=CC=C(C=C(CC2C(NC(=O)S2)=O)C=C2)C2=C1 PKWDZWYVIHVNKS-UHFFFAOYSA-N 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 229960004738 nicotinyl alcohol Drugs 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 230000009871 nonspecific binding Effects 0.000 description 1
- 238000003199 nucleic acid amplification method Methods 0.000 description 1
- URPYMXQQVHTUDU-OFGSCBOVSA-N nucleopeptide y Chemical compound C([C@@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(N)=O)NC(=O)[C@H](CC=1NC=NC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CC=1C=CC(O)=CC=1)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](C)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)CNC(=O)[C@H]1N(CCC1)C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H]1N(CCC1)C(=O)[C@H](CCCCN)NC(=O)[C@H](CO)NC(=O)[C@H]1N(CCC1)C(=O)[C@@H](N)CC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 URPYMXQQVHTUDU-OFGSCBOVSA-N 0.000 description 1
- KVWDHTXUZHCGIO-UHFFFAOYSA-N olanzapine Chemical compound C1CN(C)CCN1C1=NC2=CC=CC=C2NC2=C1C=C(C)S2 KVWDHTXUZHCGIO-UHFFFAOYSA-N 0.000 description 1
- 229960005017 olanzapine Drugs 0.000 description 1
- 238000003305 oral gavage Methods 0.000 description 1
- 230000001956 orexigenic effect Effects 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- COWNFYYYZFRNOY-UHFFFAOYSA-N oxazolidinedione Chemical compound O=C1COC(=O)N1 COWNFYYYZFRNOY-UHFFFAOYSA-N 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 230000036407 pain Effects 0.000 description 1
- SVHOVVJFOWGYJO-UHFFFAOYSA-N pentabromophenol Chemical compound OC1=C(Br)C(Br)=C(Br)C(Br)=C1Br SVHOVVJFOWGYJO-UHFFFAOYSA-N 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- ICFJFFQQTFMIBG-UHFFFAOYSA-N phenformin Chemical compound NC(=N)NC(=N)NCCC1=CC=CC=C1 ICFJFFQQTFMIBG-UHFFFAOYSA-N 0.000 description 1
- 229960003243 phenformin Drugs 0.000 description 1
- 229960003562 phentermine Drugs 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- CWCMIVBLVUHDHK-ZSNHEYEWSA-N phleomycin D1 Chemical compound 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@@H](N=1)C=1SC=C(N=1)C(=O)NCCCCNC(N)=N)[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 CWCMIVBLVUHDHK-ZSNHEYEWSA-N 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229960005095 pioglitazone Drugs 0.000 description 1
- 229940096701 plain lipid modifying drug hmg coa reductase inhibitors Drugs 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920002717 polyvinylpyridine Polymers 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 244000144977 poultry Species 0.000 description 1
- 235000013594 poultry meat Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- FYPMFJGVHOHGLL-UHFFFAOYSA-N probucol Chemical compound C=1C(C(C)(C)C)=C(O)C(C(C)(C)C)=CC=1SC(C)(C)SC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 FYPMFJGVHOHGLL-UHFFFAOYSA-N 0.000 description 1
- 229960003912 probucol Drugs 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000651 prodrug Substances 0.000 description 1
- 229940002612 prodrug Drugs 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000010926 purge Methods 0.000 description 1
- USPWKWBDZOARPV-UHFFFAOYSA-N pyrazolidine Chemical compound C1CNNC1 USPWKWBDZOARPV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- 239000001397 quillaja saponaria molina bark Substances 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000003488 releasing hormone Substances 0.000 description 1
- 230000000452 restraining effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 238000007790 scraping Methods 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 239000003352 sequestering agent Substances 0.000 description 1
- 239000004001 serotonin 1D antagonist Substances 0.000 description 1
- 239000003772 serotonin uptake inhibitor Substances 0.000 description 1
- 229960002073 sertraline Drugs 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 235000015170 shellfish Nutrition 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229950005143 sitosterol Drugs 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229940054269 sodium pyruvate Drugs 0.000 description 1
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 230000009870 specific binding Effects 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000012058 sterile packaged powder Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- TZGODTCAKVHMFG-UHFFFAOYSA-N sulfanylmethoxymethanethiol Chemical compound SCOCS TZGODTCAKVHMFG-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- GGQGISCAEVDYDY-UHFFFAOYSA-N tert-butyl 3-[[(6-amino-1,3-benzothiazol-2-yl)-methylamino]methyl]pyrrolidine-1-carboxylate Chemical compound N=1C2=CC=C(N)C=C2SC=1N(C)CC1CCN(C(=O)OC(C)(C)C)C1 GGQGISCAEVDYDY-UHFFFAOYSA-N 0.000 description 1
- CNOSLJILEHXLJY-UHFFFAOYSA-N tert-butyl 3-[[(6-nitro-1,3-benzothiazol-2-yl)amino]methyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1CNC1=NC2=CC=C([N+]([O-])=O)C=C2S1 CNOSLJILEHXLJY-UHFFFAOYSA-N 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- FQFILJKFZCVHNH-UHFFFAOYSA-N tert-butyl n-[3-[(5-bromo-2-chloropyrimidin-4-yl)amino]propyl]carbamate Chemical compound CC(C)(C)OC(=O)NCCCNC1=NC(Cl)=NC=C1Br FQFILJKFZCVHNH-UHFFFAOYSA-N 0.000 description 1
- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical compound OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000000929 thyromimetic effect Effects 0.000 description 1
- 229960005371 tolbutamide Drugs 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-N trans-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-N 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- GXPHKUHSUJUWKP-UHFFFAOYSA-N troglitazone Chemical compound C1CC=2C(C)=C(O)C(C)=C(C)C=2OC1(C)COC(C=C1)=CC=C1CC1SC(=O)NC1=O GXPHKUHSUJUWKP-UHFFFAOYSA-N 0.000 description 1
- 229960001641 troglitazone Drugs 0.000 description 1
- GXPHKUHSUJUWKP-NTKDMRAZSA-N troglitazone Natural products C([C@@]1(OC=2C(C)=C(C(=C(C)C=2CC1)O)C)C)OC(C=C1)=CC=C1C[C@H]1SC(=O)NC1=O GXPHKUHSUJUWKP-NTKDMRAZSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/58—Benzoxazoles; Hydrogenated benzoxazoles 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 in position 2
-
- 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
- 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
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/08—Drugs for disorders of the urinary system of the prostate
-
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
-
- 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
- A61P3/00—Drugs for disorders of the metabolism
-
- 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
- A61P3/06—Antihyperlipidemics
-
- 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
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/82—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Pulmonology (AREA)
- Ophthalmology & Optometry (AREA)
- Urology & Nephrology (AREA)
- Emergency Medicine (AREA)
- Neurosurgery (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Cardiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US63711604P | 2004-12-17 | 2004-12-17 | |
| US60/637,116 | 2004-12-17 | ||
| PCT/US2005/045864 WO2006066173A2 (en) | 2004-12-17 | 2005-12-16 | Novel mch receptor antagonists |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| AU2005316313A1 AU2005316313A1 (en) | 2006-06-22 |
| AU2005316313B2 true AU2005316313B2 (en) | 2011-09-29 |
Family
ID=36481254
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2005316313A Ceased AU2005316313B2 (en) | 2004-12-17 | 2005-12-16 | Novel MCH receptor antagonists |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7838543B2 (enExample) |
| EP (1) | EP1828177B1 (enExample) |
| JP (1) | JP4988591B2 (enExample) |
| CN (1) | CN101072775A (enExample) |
| AT (1) | ATE404555T1 (enExample) |
| AU (1) | AU2005316313B2 (enExample) |
| BR (1) | BRPI0517425A (enExample) |
| CA (1) | CA2589678A1 (enExample) |
| DE (1) | DE602005009021D1 (enExample) |
| DK (1) | DK1828177T3 (enExample) |
| ES (1) | ES2312048T3 (enExample) |
| MX (1) | MX2007007226A (enExample) |
| PL (1) | PL1828177T3 (enExample) |
| PT (1) | PT1828177E (enExample) |
| SI (1) | SI1828177T1 (enExample) |
| WO (1) | WO2006066173A2 (enExample) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2005290436A1 (en) | 2004-10-01 | 2006-04-13 | Banyu Pharmaceutical Co.,Ltd | 2-arylcarboxamide-nitrogeneous heterocycle compound |
| CA2589695A1 (en) * | 2004-12-17 | 2006-06-22 | Eli Lilly And Company | Thiazolopyridinone derivates as mch receptor antagonists |
| AU2006208045B2 (en) | 2005-01-25 | 2012-08-30 | Synta Pharmaceuticals Corp. | Compounds for inflammation and immune-related uses |
| US8153813B2 (en) * | 2007-12-20 | 2012-04-10 | Abbott Laboratories | Benzothiazole and benzooxazole derivatives and methods of use |
| CA2725481A1 (en) | 2008-06-18 | 2009-12-23 | Pfizer Limited | Nicotinamide derivatives |
| WO2010010435A2 (en) * | 2008-07-22 | 2010-01-28 | Glenmark Pharmaceutical S.A. | Fused oxazole and thiazole derivatives as trpms modulators |
| SA110310332B1 (ar) | 2009-05-01 | 2013-12-10 | Astrazeneca Ab | مركبات ميثانون (3 استبدال -ازيتيدين -1-يل )(5- فينيل -1، 3، 4- أوكساديازول -2-يل ) |
| AU2011275547B2 (en) | 2010-07-06 | 2015-10-29 | Astrazeneca Ab | Therapeutic agents 976 |
| ES2603032T3 (es) * | 2010-07-15 | 2017-02-23 | Bayer Intellectual Property Gmbh | Compuestos de 3-piridil-heteroarilcarboxamida como pesticidas |
| WO2012081563A1 (ja) * | 2010-12-14 | 2012-06-21 | 塩野義製薬株式会社 | 血管内皮リパーゼ阻害活性を有するベンゾチアゾールおよびアザベンゾチアゾール誘導体 |
| UY34194A (es) | 2011-07-15 | 2013-02-28 | Astrazeneca Ab | ?(3-(4-(espiroheterocíclico)metil)fenoxi)azetidin-1-il)(5-(fenil)-1,3,4-oxadiazol-2-il)metanona en el tratamiento de la obesidad? |
| JO3225B1 (ar) * | 2012-11-27 | 2018-03-08 | Lilly Co Eli | 6-((s)-1-{1-[5-(2-هيدروكسي-إيثوكسي)-بيريدين-2-يل]-1h-بيرازول-3-يل}إيثيل)-3h-1 ، 3-بنزو ثيازول-2- أون باعتباره مضاد مستقبل ampa يعتمد على tarp- جاما 8 |
| US9732095B2 (en) | 2014-01-13 | 2017-08-15 | Aurigene Discovery Technologies Limited | Bicyclic heterocyclyl derivatives as IRAK4 inhibitors |
| JP6802194B2 (ja) | 2015-06-22 | 2020-12-16 | アクテリオン ファーマシューティカルズ リミテッドＡｃｔｅｌｉｏｎ Ｐｈａｒｍａｃｅｕｔｉｃａｌｓ Ｌｔｄ | Ｎａｄｐｈオキシダーゼ４阻害剤 |
| AU2016293446A1 (en) * | 2015-07-15 | 2018-02-15 | Aurigene Discovery Technologies Limited | Substituted aza compounds as IRAK-4 inhibitors |
| CN110691589A (zh) | 2017-03-31 | 2020-01-14 | 奥列基因发现技术有限公司 | 用于治疗血液病的化合物和组合物 |
| FI3704108T3 (fi) | 2017-10-31 | 2024-05-23 | Curis Inc | Irak4-estäjä yhdistelmässä bcl-2-estäjän kanssa käytettäväksi syövän hoitoon |
| CN109485620A (zh) * | 2018-12-26 | 2019-03-19 | 安徽工大化工科技有限公司 | 一种2-甲氧基-6-甲氧基苯并噻唑的制备方法 |
| CN114008025A (zh) * | 2019-05-14 | 2022-02-01 | 美特波米德有限公司 | Acss2抑制剂和其使用方法 |
| IL307465A (en) | 2021-04-08 | 2023-12-01 | Curis Inc | Combined therapies for cancer treatment |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2565595A (en) | 1994-05-28 | 1995-12-21 | Smithkline Beecham Plc | Amide derivatives having 5ht1d-antagonist activity |
| PT971878E (pt) | 1997-02-27 | 2008-07-08 | Takeda Pharmaceutical | Compostos de amina, sua produção e utilização como inibidores da produção de amilóide beta |
| US7115750B1 (en) | 1999-09-20 | 2006-10-03 | Takeda Pharmaceutical Company Limited | Melanin concentrating hormone antagonist |
| US7091227B2 (en) * | 2000-02-07 | 2006-08-15 | Abbott Gmbh & Co. Kg | Benzothiazole derivatives |
| US6930185B2 (en) * | 2000-04-28 | 2005-08-16 | Takeda Chemical Industries, Ltd. | Melanin-concentrating hormone antagonist |
| US7229986B2 (en) * | 2000-05-16 | 2007-06-12 | Takeda Pharmaceutical Company Ltd. | Melanin-concentrating hormone antagonist |
| US6642252B2 (en) * | 2000-11-07 | 2003-11-04 | Bristol-Myers Squibb Company | Acid derivatives useful as serine protease inhibitors |
| DE10139126A1 (de) * | 2001-08-09 | 2003-02-20 | Ciba Sc Pfersee Gmbh | Zusammensetzungen aus Polysiloxanen, Fluorpolymeren und Extendern |
| DE10139416A1 (de) * | 2001-08-17 | 2003-03-06 | Aventis Pharma Gmbh | Aminoalkyl substituierte aromatische Bicyclen, Verfahren zu ihrer Herstellung und ihre Verwendung als Arzneimittel |
| EP1463714A4 (en) * | 2001-12-10 | 2005-10-19 | Amgen Inc | VANILLOID RECEPTOR LIGANDS AND THEIR USE IN TREATMENTS |
| DE60329513D1 (de) * | 2002-07-30 | 2009-11-12 | Banyu Pharma Co Ltd | Antagonist des melanin-concentrating-hormone-rezeptors, enthaltend ein benzimidazolderivat als wirkstoff |
| EP1585726A1 (en) * | 2003-01-06 | 2005-10-19 | Eli Lilly And Company | Fused heterocyclic derivatives as ppar modulators |
| BRPI0608245A2 (pt) * | 2005-03-09 | 2009-12-01 | Hoffmann La Roche | compostos; processo para a sua fabricação; composições farmacêuticas; método para o tratamento e/ou prevenção de doenças que estejam associadas à modulação de receptores de sst subtipo 5 e uso dos compostos |
-
2005
- 2005-12-16 CA CA002589678A patent/CA2589678A1/en not_active Abandoned
- 2005-12-16 PT PT05854552T patent/PT1828177E/pt unknown
- 2005-12-16 DE DE602005009021T patent/DE602005009021D1/de active Active
- 2005-12-16 DK DK05854552T patent/DK1828177T3/da active
- 2005-12-16 AU AU2005316313A patent/AU2005316313B2/en not_active Ceased
- 2005-12-16 SI SI200530456T patent/SI1828177T1/sl unknown
- 2005-12-16 PL PL05854552T patent/PL1828177T3/pl unknown
- 2005-12-16 US US11/719,576 patent/US7838543B2/en not_active Expired - Fee Related
- 2005-12-16 BR BRPI0517425-2A patent/BRPI0517425A/pt not_active IP Right Cessation
- 2005-12-16 CN CNA2005800418488A patent/CN101072775A/zh active Pending
- 2005-12-16 MX MX2007007226A patent/MX2007007226A/es active IP Right Grant
- 2005-12-16 EP EP05854552A patent/EP1828177B1/en not_active Expired - Lifetime
- 2005-12-16 ES ES05854552T patent/ES2312048T3/es not_active Expired - Lifetime
- 2005-12-16 AT AT05854552T patent/ATE404555T1/de active
- 2005-12-16 WO PCT/US2005/045864 patent/WO2006066173A2/en not_active Ceased
- 2005-12-16 JP JP2007546990A patent/JP4988591B2/ja not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| US20090170913A1 (en) | 2009-07-02 |
| DE602005009021D1 (de) | 2008-09-25 |
| PT1828177E (pt) | 2008-10-28 |
| CA2589678A1 (en) | 2006-06-22 |
| WO2006066173A2 (en) | 2006-06-22 |
| PL1828177T3 (pl) | 2009-01-30 |
| US7838543B2 (en) | 2010-11-23 |
| EP1828177B1 (en) | 2008-08-13 |
| EP1828177A2 (en) | 2007-09-05 |
| DK1828177T3 (da) | 2008-11-17 |
| ES2312048T3 (es) | 2009-02-16 |
| WO2006066173A3 (en) | 2006-07-27 |
| JP4988591B2 (ja) | 2012-08-01 |
| ATE404555T1 (de) | 2008-08-15 |
| CN101072775A (zh) | 2007-11-14 |
| BRPI0517425A (pt) | 2008-10-07 |
| JP2008524249A (ja) | 2008-07-10 |
| AU2005316313A1 (en) | 2006-06-22 |
| SI1828177T1 (sl) | 2009-02-28 |
| MX2007007226A (es) | 2007-08-21 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2005316313B2 (en) | Novel MCH receptor antagonists | |
| JP6560436B2 (ja) | ヒストン脱アセチル化酵素６阻害剤としての１，３，４−オキサジアゾールスルホンアミド誘導体化合物及びこれを含有する薬剤学的組成物 | |
| US9622991B2 (en) | Hematopoietic growth factor mimetic small molecule compounds and their uses | |
| AU2007316248B2 (en) | Indazole derivatives useful as L-CPT1 inhibitors | |
| JP5140577B2 (ja) | ヒドロキシステロイドデヒドロゲナーゼ阻害剤 | |
| US20080153810A1 (en) | Indazole derivatives useful as melanin concentrating receptor ligands | |
| US20140243324A1 (en) | Use of hematopoietic growth factor mimetics | |
| NZ566862A (en) | Diarylamine-containing compounds and compositions, and their use as modulators of C-kit receptors | |
| CA2484233A1 (en) | Multicyclic compounds for use as melanin concentrating hormone antagonists in the treatment of obesity and diabetes | |
| TW200843770A (en) | RHO kinase inhibitors | |
| US20120135964A1 (en) | Certain chemical entities, compositions, and methods | |
| JP2003532730A (ja) | 細胞増殖抑制剤として有用な１，１−ジオキソイソチアゾリジンを持つインダゾール | |
| EP2630144B1 (en) | Rho kinase inhibitors | |
| US20100222396A1 (en) | 4-aryl-butane-1,3-diamides | |
| EP1622884A1 (en) | New heterocyclic amides exhibiting an inhibitory activity at the vanilloid receptor 1 (vr1). | |
| JP2007510629A (ja) | 新規ｍｃｈ受容体アンタゴニスト | |
| CN101823987B (zh) | 一类新的dpp-ⅳ抑制剂及其制备方法和用途 | |
| US20120015957A1 (en) | Piperazinyl derivatives useful as modulators of the neuropeptide y2 receptor | |
| IL302247A (en) | Cftr modulator compounds, compositions, and uses thereof | |
| US20240391901A1 (en) | Substituted heterocyclic compound containing alpha-ketone framework, and use thereof | |
| CN1759095A (zh) | N,n'－取代的－1,3－二氨基－2－羟基丙烷衍生物 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FGA | Letters patent sealed or granted (standard patent) | ||
| MK14 | Patent ceased section 143(a) (annual fees not paid) or expired |