MX2010010241A - Derivados de piperidina novedosos como inhibidores de estearoil-coa desaturasa. - Google Patents
Derivados de piperidina novedosos como inhibidores de estearoil-coa desaturasa.Info
- Publication number
- MX2010010241A MX2010010241A MX2010010241A MX2010010241A MX2010010241A MX 2010010241 A MX2010010241 A MX 2010010241A MX 2010010241 A MX2010010241 A MX 2010010241A MX 2010010241 A MX2010010241 A MX 2010010241A MX 2010010241 A MX2010010241 A MX 2010010241A
- Authority
- MX
- Mexico
- Prior art keywords
- phenyl
- piperidin
- ethyl
- mol
- oxo
- Prior art date
Links
- 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 11
- 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract description 11
- 239000003112 inhibitor Substances 0.000 title claims abstract description 9
- 150000003053 piperidines Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 185
- 238000000034 method Methods 0.000 claims abstract description 47
- 238000011282 treatment Methods 0.000 claims abstract description 20
- -1 cyano, nitro, amino Chemical group 0.000 claims description 479
- 150000003839 salts Chemical class 0.000 claims description 96
- 125000003118 aryl group Chemical group 0.000 claims description 78
- 125000000217 alkyl group Chemical group 0.000 claims description 75
- 125000001072 heteroaryl group Chemical group 0.000 claims description 66
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 58
- 239000012453 solvate Substances 0.000 claims description 37
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 16
- 208000008589 Obesity Diseases 0.000 claims description 13
- 235000020824 obesity Nutrition 0.000 claims description 13
- 125000001769 aryl amino group Chemical group 0.000 claims description 12
- 125000002252 acyl group Chemical group 0.000 claims description 11
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000003368 amide group Chemical group 0.000 claims description 11
- DBYLAWFMMVZTRR-UHFFFAOYSA-N 1-phenylimidazole-4-carboxylic acid Chemical compound C1=NC(C(=O)O)=CN1C1=CC=CC=C1 DBYLAWFMMVZTRR-UHFFFAOYSA-N 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 150000004677 hydrates Chemical class 0.000 claims description 8
- GFQYKYPGSBTSII-HHHXNRCGSA-N 4-[[(2r)-2-methyl-6-nitro-3h-imidazo[2,1-b][1,3]oxazol-2-yl]methoxy]-n-[2-oxo-2-[4-[4-(trifluoromethoxy)phenoxy]piperidin-1-yl]ethyl]benzamide Chemical compound C([C@]1(C)OC2=NC(=CN2C1)[N+]([O-])=O)OC(C=C1)=CC=C1C(=O)NCC(=O)N(CC1)CCC1OC1=CC=C(OC(F)(F)F)C=C1 GFQYKYPGSBTSII-HHHXNRCGSA-N 0.000 claims description 6
- VZTKTOKASVGDFZ-UHFFFAOYSA-N 4-amino-n-[2-[4-[[4-amino-5-(2,6-difluorobenzoyl)-1,3-thiazol-2-yl]amino]piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound S1C(C(=O)C=2C(=CC=CC=2F)F)=C(N)N=C1NC(CC1)CCN1C(=O)CNC(=O)C1=CC=C(N)C=C1 VZTKTOKASVGDFZ-UHFFFAOYSA-N 0.000 claims description 6
- 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 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- KERBTFURRLPANO-UHFFFAOYSA-N n-[2-[4-[[4-amino-5-(2,6-difluorobenzoyl)-1,3-thiazol-2-yl]amino]piperidin-1-yl]-2-oxoethyl]-3-methylbenzamide Chemical compound CC1=CC=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2SC(=C(N)N=2)C(=O)C=2C(=CC=CC=2F)F)=C1 KERBTFURRLPANO-UHFFFAOYSA-N 0.000 claims description 6
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- PWOBDMNCYMQTCE-UHFFFAOYSA-N 2-chlorobenzenethiol Chemical compound SC1=CC=CC=C1Cl PWOBDMNCYMQTCE-UHFFFAOYSA-N 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- RNISSEZJCVBQCP-UHFFFAOYSA-N 2-amino-1-[4-(2,5-difluorophenoxy)piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1OC1=CC(F)=CC=C1F RNISSEZJCVBQCP-UHFFFAOYSA-N 0.000 claims description 2
- SFYYEFCAGKWVGZ-UHFFFAOYSA-N C=1C=CC=C(C(F)(F)F)C=1N(C)C1CCN(C(=O)CN)CC1 Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C1CCN(C(=O)CN)CC1 SFYYEFCAGKWVGZ-UHFFFAOYSA-N 0.000 claims description 2
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical group C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 2
- 150000003852 triazoles Chemical group 0.000 claims description 2
- 229940123980 Desaturase inhibitor Drugs 0.000 claims 2
- FUQVEOXNFSKAFB-UHFFFAOYSA-N 2-[1-[2-[(3-phenyl-1h-pyrazole-5-carbonyl)amino]acetyl]piperidin-4-yl]oxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 FUQVEOXNFSKAFB-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 270
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 616
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 311
- 239000000243 solution Substances 0.000 description 299
- 235000019439 ethyl acetate Nutrition 0.000 description 206
- 229910001868 water Inorganic materials 0.000 description 202
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 192
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 183
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 176
- 239000011541 reaction mixture Substances 0.000 description 163
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 158
- 230000015572 biosynthetic process Effects 0.000 description 155
- 238000003786 synthesis reaction Methods 0.000 description 152
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 143
- 230000002829 reductive effect Effects 0.000 description 132
- 238000005481 NMR spectroscopy Methods 0.000 description 109
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 93
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 90
- 239000000047 product Substances 0.000 description 90
- 229910052938 sodium sulfate Inorganic materials 0.000 description 90
- 235000011152 sodium sulphate Nutrition 0.000 description 90
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 82
- 239000012267 brine Substances 0.000 description 81
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 73
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 70
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- 238000001914 filtration Methods 0.000 description 67
- 239000002244 precipitate Substances 0.000 description 67
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 64
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 60
- 238000004440 column chromatography Methods 0.000 description 60
- 239000010410 layer Substances 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- 239000012044 organic layer Substances 0.000 description 46
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 42
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 41
- 239000002253 acid Substances 0.000 description 40
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 39
- 239000000741 silica gel Substances 0.000 description 38
- 229910002027 silica gel Inorganic materials 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 37
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 36
- 238000003756 stirring Methods 0.000 description 35
- 101000797623 Homo sapiens Protein AMBP Proteins 0.000 description 31
- 102100032859 Protein AMBP Human genes 0.000 description 31
- 201000010099 disease Diseases 0.000 description 31
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 30
- 238000000746 purification Methods 0.000 description 29
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 26
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 25
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 24
- XHZJCANBGSMDCL-UHFFFAOYSA-N 2-[(3-phenyl-1h-pyrazole-5-carbonyl)amino]acetic acid Chemical compound N1N=C(C(=O)NCC(=O)O)C=C1C1=CC=CC=C1 XHZJCANBGSMDCL-UHFFFAOYSA-N 0.000 description 21
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 21
- 125000004432 carbon atom Chemical group C* 0.000 description 21
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 19
- 239000003039 volatile agent Substances 0.000 description 19
- 241000700605 Viruses Species 0.000 description 18
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 18
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 17
- 101150041968 CDC13 gene Proteins 0.000 description 17
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 17
- 229910052799 carbon Inorganic materials 0.000 description 16
- 125000003282 alkyl amino group Chemical group 0.000 description 15
- 229910052786 argon Inorganic materials 0.000 description 15
- 150000001721 carbon Chemical group 0.000 description 15
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 15
- 125000004494 ethyl ester group Chemical group 0.000 description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 14
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 description 14
- 150000002431 hydrogen Chemical group 0.000 description 14
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 230000008878 coupling Effects 0.000 description 13
- 238000010168 coupling process Methods 0.000 description 13
- 238000005859 coupling reaction Methods 0.000 description 13
- NRKBZJMRGOIHDU-UHFFFAOYSA-N n-(2-chlorophenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.ClC1=CC=CC=C1NC1CCNCC1 NRKBZJMRGOIHDU-UHFFFAOYSA-N 0.000 description 13
- 230000007935 neutral effect Effects 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 229910000024 caesium carbonate Inorganic materials 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 230000001404 mediated effect Effects 0.000 description 12
- 239000012299 nitrogen atmosphere Substances 0.000 description 12
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- QBPUOAJBMXXBNU-UHFFFAOYSA-N 3-phenyl-1H-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=CC=CC=2)=N1 QBPUOAJBMXXBNU-UHFFFAOYSA-N 0.000 description 11
- 241001465754 Metazoa Species 0.000 description 11
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Chemical class OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 125000003435 aroyl group Chemical group 0.000 description 11
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 11
- 239000000543 intermediate Substances 0.000 description 11
- MYJXSDFBYVYUCD-UHFFFAOYSA-N 2-[(4-phenylbenzoyl)amino]acetic acid Chemical compound C1=CC(C(=O)NCC(=O)O)=CC=C1C1=CC=CC=C1 MYJXSDFBYVYUCD-UHFFFAOYSA-N 0.000 description 10
- LEWJPYZUHQHNOJ-UHFFFAOYSA-N 3-oxo-3-[(6-phenylpyridin-3-yl)amino]propanoic acid Chemical compound N1=CC(NC(=O)CC(=O)O)=CC=C1C1=CC=CC=C1 LEWJPYZUHQHNOJ-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 10
- 125000003342 alkenyl group Chemical group 0.000 description 10
- 238000010976 amide bond formation reaction Methods 0.000 description 10
- 125000003710 aryl alkyl group Chemical group 0.000 description 10
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 10
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 10
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 10
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 10
- 125000004104 aryloxy group Chemical group 0.000 description 10
- 125000000000 cycloalkoxy group Chemical group 0.000 description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 10
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 description 10
- 125000004986 diarylamino group Chemical group 0.000 description 10
- 208000035475 disorder Diseases 0.000 description 10
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 10
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 10
- 125000005553 heteroaryloxy group Chemical group 0.000 description 10
- 125000005226 heteroaryloxycarbonyl group Chemical group 0.000 description 10
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 description 10
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- OWOPJLHKPATCOS-UHFFFAOYSA-N 4-(2-chlorophenoxy)piperidin-1-ium;chloride Chemical compound Cl.ClC1=CC=CC=C1OC1CCNCC1 OWOPJLHKPATCOS-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 9
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 9
- 230000007062 hydrolysis Effects 0.000 description 9
- 238000006460 hydrolysis reaction Methods 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- 239000000651 prodrug Substances 0.000 description 9
- 229940002612 prodrug Drugs 0.000 description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- 125000005110 aryl thio group Chemical group 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 8
- 239000005457 ice water Substances 0.000 description 8
- BZRFUJDWZRSMPO-UHFFFAOYSA-N n-(2-bromophenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.BrC1=CC=CC=C1NC1CCNCC1 BZRFUJDWZRSMPO-UHFFFAOYSA-N 0.000 description 8
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 8
- 229940080818 propionamide Drugs 0.000 description 8
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 8
- PJBOIQUPTSKSFR-UHFFFAOYSA-N 2-[(4-anilinobenzoyl)amino]acetic acid Chemical compound C1=CC(C(=O)NCC(=O)O)=CC=C1NC1=CC=CC=C1 PJBOIQUPTSKSFR-UHFFFAOYSA-N 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
- 239000012458 free base Substances 0.000 description 7
- 239000007788 liquid Substances 0.000 description 7
- 239000004533 oil dispersion Substances 0.000 description 7
- 125000004076 pyridyl group Chemical group 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 125000003107 substituted aryl group Chemical group 0.000 description 7
- KYLZZJIUYCARJX-UHFFFAOYSA-N 2-[(5-phenyl-1,2-oxazole-3-carbonyl)amino]acetic acid Chemical compound O1N=C(C(=O)NCC(=O)O)C=C1C1=CC=CC=C1 KYLZZJIUYCARJX-UHFFFAOYSA-N 0.000 description 6
- JVVRCYWZTJLJSG-UHFFFAOYSA-N 4-dimethylaminophenol Chemical compound CN(C)C1=CC=C(O)C=C1 JVVRCYWZTJLJSG-UHFFFAOYSA-N 0.000 description 6
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 6
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-dimethylaminopyridine Substances CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- FOWOXWLATUAFNQ-UHFFFAOYSA-N 4-oxopiperidine-1-carboxylic acid Chemical compound OC(=O)N1CCC(=O)CC1 FOWOXWLATUAFNQ-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- 208000001145 Metabolic Syndrome Diseases 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 description 6
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 6
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 6
- 239000003480 eluent Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 238000001704 evaporation Methods 0.000 description 6
- 230000008020 evaporation Effects 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- 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 6
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 6
- 108090000623 proteins and genes Proteins 0.000 description 6
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 6
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 5
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 5
- FLIQYTXJLWGVBG-UHFFFAOYSA-N 6-phenylpyridin-3-amine Chemical compound N1=CC(N)=CC=C1C1=CC=CC=C1 FLIQYTXJLWGVBG-UHFFFAOYSA-N 0.000 description 5
- 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 5
- AEDMQUAPBVOJNN-UHFFFAOYSA-N [3-[2-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]-1,3-thiazol-5-yl]-1,2,4-oxadiazol-5-yl]methanol Chemical compound O1C(CO)=NC(C=2SC(=NC=2)N2CCC(CC2)OC=2C(=CC=CC=2)C(F)(F)F)=N1 AEDMQUAPBVOJNN-UHFFFAOYSA-N 0.000 description 5
- 239000004480 active ingredient Substances 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 5
- 229910052794 bromium Inorganic materials 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 229910052801 chlorine Inorganic materials 0.000 description 5
- 206010012601 diabetes mellitus Diseases 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 208000006575 hypertriglyceridemia Diseases 0.000 description 5
- JEWGYTYWPNLTOE-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.FC(F)(F)C1=CC=CC=C1NC1CCNCC1 JEWGYTYWPNLTOE-UHFFFAOYSA-N 0.000 description 5
- LHGSAIOZULAFFG-UHFFFAOYSA-N n-methyl-n-[2-(trifluoromethyl)phenyl]piperidin-4-amine;hydrochloride Chemical compound Cl.C=1C=CC=C(C(F)(F)F)C=1N(C)C1CCNCC1 LHGSAIOZULAFFG-UHFFFAOYSA-N 0.000 description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 125000006413 ring segment Chemical group 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
- 235000017550 sodium carbonate Nutrition 0.000 description 5
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 5
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 4
- SSVLBWJQUGGAPW-UHFFFAOYSA-N 1-[(4-phenylphenyl)carbamoyl]cyclopropane-1-carboxylic acid Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(=O)C1(C(=O)O)CC1 SSVLBWJQUGGAPW-UHFFFAOYSA-N 0.000 description 4
- FVBSPRNOVNLJTM-UHFFFAOYSA-N 2-[(5-anilinopyridine-2-carbonyl)amino]acetic acid Chemical compound C1=NC(C(=O)NCC(=O)O)=CC=C1NC1=CC=CC=C1 FVBSPRNOVNLJTM-UHFFFAOYSA-N 0.000 description 4
- CNFJJZMYHCLKLO-UHFFFAOYSA-N 2-[(5-phenylpyridine-2-carbonyl)amino]acetic acid Chemical compound C1=NC(C(=O)NCC(=O)O)=CC=C1C1=CC=CC=C1 CNFJJZMYHCLKLO-UHFFFAOYSA-N 0.000 description 4
- KYRFAIYLVSCGMW-UHFFFAOYSA-N 2-[(6-anilinopyridine-3-carbonyl)amino]acetic acid Chemical compound N1=CC(C(=O)NCC(=O)O)=CC=C1NC1=CC=CC=C1 KYRFAIYLVSCGMW-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 4
- DSXYSIWOUJDQJB-UHFFFAOYSA-N 3-oxo-3-[(5-phenyl-1,3-thiazol-2-yl)amino]propanoic acid Chemical compound S1C(NC(=O)CC(=O)O)=NC=C1C1=CC=CC=C1 DSXYSIWOUJDQJB-UHFFFAOYSA-N 0.000 description 4
- KGZWUTBUWZZBDR-UHFFFAOYSA-N 4-(2,5-difluorophenoxy)piperidine;hydrochloride Chemical compound Cl.FC1=CC=C(F)C(OC2CCNCC2)=C1 KGZWUTBUWZZBDR-UHFFFAOYSA-N 0.000 description 4
- OZZKKBDEMFLNAX-UHFFFAOYSA-N 4-(2-bromophenoxy)piperidine;2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.BrC1=CC=CC=C1OC1CCNCC1 OZZKKBDEMFLNAX-UHFFFAOYSA-N 0.000 description 4
- BQKZGPWCYWHOSM-UHFFFAOYSA-N 5-(2-hydroxyphenyl)-1-methylpyrazole-3-carboxylic acid Chemical compound CN1N=C(C(O)=O)C=C1C1=CC=CC=C1O BQKZGPWCYWHOSM-UHFFFAOYSA-N 0.000 description 4
- 241000283690 Bos taurus Species 0.000 description 4
- 241000711573 Coronaviridae Species 0.000 description 4
- 102000004190 Enzymes Human genes 0.000 description 4
- 108090000790 Enzymes Proteins 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 206010019708 Hepatic steatosis Diseases 0.000 description 4
- 206010022489 Insulin Resistance Diseases 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical class CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- 206010028980 Neoplasm Diseases 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 239000000443 aerosol Substances 0.000 description 4
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 235000008504 concentrate Nutrition 0.000 description 4
- 125000004093 cyano group Chemical group *C#N 0.000 description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 4
- 230000007812 deficiency Effects 0.000 description 4
- 235000014113 dietary fatty acids Nutrition 0.000 description 4
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 229930195729 fatty acid Natural products 0.000 description 4
- 150000004665 fatty acids Chemical class 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 230000006870 function Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 238000004128 high performance liquid chromatography Methods 0.000 description 4
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- WLTMPXAIVSBZEQ-UHFFFAOYSA-N n-(2-methylphenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC=C1NC1CCNCC1 WLTMPXAIVSBZEQ-UHFFFAOYSA-N 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 238000002953 preparative HPLC Methods 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 229930195734 saturated hydrocarbon Natural products 0.000 description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 208000011580 syndromic disease Diseases 0.000 description 4
- 239000003826 tablet Substances 0.000 description 4
- WOEQSXAIPTXOPY-UHFFFAOYSA-N tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(OS(C)(=O)=O)CC1 WOEQSXAIPTXOPY-UHFFFAOYSA-N 0.000 description 4
- ROUYFJUVMYHXFJ-UHFFFAOYSA-N tert-butyl 4-oxopiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(=O)CC1 ROUYFJUVMYHXFJ-UHFFFAOYSA-N 0.000 description 4
- RXRYMZDQIVBQLZ-UHFFFAOYSA-N 1-[4-(2-chlorophenoxy)piperidine-1-carbonyl]-n-(4-phenylphenyl)cyclopropane-1-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)C2(CC2)C(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 RXRYMZDQIVBQLZ-UHFFFAOYSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- IPOVOSHRRIJKBR-UHFFFAOYSA-N 2-ethylpropanedioyl dichloride Chemical compound CCC(C(Cl)=O)C(Cl)=O IPOVOSHRRIJKBR-UHFFFAOYSA-N 0.000 description 3
- RNTFBCPBIIECHG-UHFFFAOYSA-N 3-[4-(2,5-dimethylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC=C(C)C(NC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 RNTFBCPBIIECHG-UHFFFAOYSA-N 0.000 description 3
- UUIGUCKWXJLEEO-UHFFFAOYSA-N 3-[4-(2-bromophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound BrC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 UUIGUCKWXJLEEO-UHFFFAOYSA-N 0.000 description 3
- GFIFKGLZEGKMTK-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 GFIFKGLZEGKMTK-UHFFFAOYSA-N 0.000 description 3
- WCAVUEHNHOEMSX-UHFFFAOYSA-N 3-[4-(2-chloroanilino)piperidin-1-yl]-3-oxo-n-(5-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)CC1 WCAVUEHNHOEMSX-UHFFFAOYSA-N 0.000 description 3
- BKKAQJXEIVTPGM-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxo-n-(3-phenyl-1,2,4-thiadiazol-5-yl)propanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2SN=C(N=2)C=2C=CC=CC=2)CC1 BKKAQJXEIVTPGM-UHFFFAOYSA-N 0.000 description 3
- DUIQSVQAWKATIR-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxo-n-(5-phenyl-1,3-thiazol-2-yl)propanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2SC(=CN=2)C=2C=CC=CC=2)CC1 DUIQSVQAWKATIR-UHFFFAOYSA-N 0.000 description 3
- BBFBPVOSCMRHAO-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 BBFBPVOSCMRHAO-UHFFFAOYSA-N 0.000 description 3
- DAWLJPOZGTYCCA-UHFFFAOYSA-N 3-[4-(2-nitrophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound [O-][N+](=O)C1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 DAWLJPOZGTYCCA-UHFFFAOYSA-N 0.000 description 3
- ANILIVZLWJKPRD-UHFFFAOYSA-N 3-[4-(2-tert-butylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC(C)(C)C1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 ANILIVZLWJKPRD-UHFFFAOYSA-N 0.000 description 3
- FIBIXFDKDBAPET-UHFFFAOYSA-N 3-oxo-3-(4-phenylanilino)propanoic acid Chemical compound C1=CC(NC(=O)CC(=O)O)=CC=C1C1=CC=CC=C1 FIBIXFDKDBAPET-UHFFFAOYSA-N 0.000 description 3
- GYELPMCREZETQR-UHFFFAOYSA-N 3-oxo-n-(6-phenylpyridin-3-yl)-3-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 GYELPMCREZETQR-UHFFFAOYSA-N 0.000 description 3
- VZCDZCUPZRFWAW-UHFFFAOYSA-N 3-pyridin-3-yl-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=NC=CC=2)=N1 VZCDZCUPZRFWAW-UHFFFAOYSA-N 0.000 description 3
- KGUZRMOXECFUGA-UHFFFAOYSA-N 4-(1,2,4-oxadiazol-3-yl)aniline Chemical compound C1=CC(N)=CC=C1C1=NOC=N1 KGUZRMOXECFUGA-UHFFFAOYSA-N 0.000 description 3
- ABOWEJNMSYULQQ-UHFFFAOYSA-N 4-(2-chloro-5-fluorophenoxy)piperidine;hydrochloride Chemical compound Cl.FC1=CC=C(Cl)C(OC2CCNCC2)=C1 ABOWEJNMSYULQQ-UHFFFAOYSA-N 0.000 description 3
- JGIKYGXQGXORFY-UHFFFAOYSA-N 4-(2-nitrophenoxy)piperidine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC=C1OC1CCNCC1 JGIKYGXQGXORFY-UHFFFAOYSA-N 0.000 description 3
- IFSNPHMPXKRXHP-UHFFFAOYSA-N 4-anilino-2-[2-[4-(2-bromophenoxy)piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound BrC1=C(OC2CCN(CC2)C(CC2=C(C(=O)N)C=CC(=C2)NC2=CC=CC=C2)=O)C=CC=C1 IFSNPHMPXKRXHP-UHFFFAOYSA-N 0.000 description 3
- DPAMLADQPZFXMD-UHFFFAOYSA-N 4-anilinobenzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC1=CC=CC=C1 DPAMLADQPZFXMD-UHFFFAOYSA-N 0.000 description 3
- 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 3
- CNCJXSKAKGXNKJ-UHFFFAOYSA-N 5-phenylpyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1C1=CC=CC=C1 CNCJXSKAKGXNKJ-UHFFFAOYSA-N 0.000 description 3
- OMGPNSFUSJHLFT-UHFFFAOYSA-N 6-anilinopyridine-3-carboxylic acid Chemical compound N1=CC(C(=O)O)=CC=C1NC1=CC=CC=C1 OMGPNSFUSJHLFT-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- 208000024172 Cardiovascular disease Diseases 0.000 description 3
- 208000032928 Dyslipidaemia Diseases 0.000 description 3
- 108010010234 HDL Lipoproteins Proteins 0.000 description 3
- 241000282412 Homo Species 0.000 description 3
- 241000725303 Human immunodeficiency virus Species 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical class OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
- MUALRAIOVNYAIW-UHFFFAOYSA-N binap Chemical compound C1=CC=CC=C1P(C=1C(=C2C=CC=CC2=CC=1)C=1C2=CC=CC=C2C=CC=1P(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 MUALRAIOVNYAIW-UHFFFAOYSA-N 0.000 description 3
- 235000010290 biphenyl Nutrition 0.000 description 3
- 239000004305 biphenyl Substances 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- YAYDMJNTBGROTD-UHFFFAOYSA-N chembl1528711 Chemical compound N1N=C(C(=O)O)C=C1C1=CC=C(O)C=C1 YAYDMJNTBGROTD-UHFFFAOYSA-N 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000002552 dosage form Substances 0.000 description 3
- 239000006196 drop Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 208000006454 hepatitis Diseases 0.000 description 3
- 231100000283 hepatitis Toxicity 0.000 description 3
- 208000015181 infectious disease Diseases 0.000 description 3
- 125000000842 isoxazolyl group Chemical group 0.000 description 3
- 150000002632 lipids Chemical class 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- 125000002950 monocyclic group Chemical group 0.000 description 3
- YPADSCOAFMYSQK-UHFFFAOYSA-N n-(2,4-dimethylphenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.CC1=CC(C)=CC=C1NC1CCNCC1 YPADSCOAFMYSQK-UHFFFAOYSA-N 0.000 description 3
- YANYODVHQHCXLA-UHFFFAOYSA-N n-(2,5-dimethylphenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=C(C)C(NC2CCNCC2)=C1 YANYODVHQHCXLA-UHFFFAOYSA-N 0.000 description 3
- VUBUUVPULBVPLO-UHFFFAOYSA-N n-(2-chlorophenyl)-n-methylpiperidin-4-amine;hydrochloride Chemical compound Cl.C=1C=CC=C(Cl)C=1N(C)C1CCNCC1 VUBUUVPULBVPLO-UHFFFAOYSA-N 0.000 description 3
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- SIARJEKBADXQJG-LFZQUHGESA-N stearoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 SIARJEKBADXQJG-LFZQUHGESA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- VNWVBOIKZGLVQW-UHFFFAOYSA-N tert-butyl 4-(2-chloroanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC=C1Cl VNWVBOIKZGLVQW-UHFFFAOYSA-N 0.000 description 3
- 230000001225 therapeutic effect Effects 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Chemical class OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 description 2
- ZJABPUSDYOXUKS-UHFFFAOYSA-N 1-(2-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 ZJABPUSDYOXUKS-UHFFFAOYSA-N 0.000 description 2
- FGQMEAWGAUALJQ-UHFFFAOYSA-N 1-(3-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 FGQMEAWGAUALJQ-UHFFFAOYSA-N 0.000 description 2
- MKYMYZJJFMPDOA-UHFFFAOYSA-N 1-(4-phenylmethoxyphenyl)ethanone Chemical compound C1=CC(C(=O)C)=CC=C1OCC1=CC=CC=C1 MKYMYZJJFMPDOA-UHFFFAOYSA-N 0.000 description 2
- DNUTZBZXLPWRJG-UHFFFAOYSA-N 1-Piperidine carboxylic acid Chemical compound OC(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-N 0.000 description 2
- KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical compound OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 2
- YHMJTZDBYNNSLO-UHFFFAOYSA-N 2,2,2-trifluoroacetic acid;4-[2-(trifluoromethyl)phenoxy]piperidine Chemical compound OC(=O)C(F)(F)F.FC(F)(F)C1=CC=CC=C1OC1CCNCC1 YHMJTZDBYNNSLO-UHFFFAOYSA-N 0.000 description 2
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 2
- VOWZNBNDMFLQGM-UHFFFAOYSA-N 2,5-dimethylaniline Chemical compound CC1=CC=C(C)C(N)=C1 VOWZNBNDMFLQGM-UHFFFAOYSA-N 0.000 description 2
- XVGQHRKNXSUPEF-UHFFFAOYSA-N 2-(trifluoromethyl)benzenethiol Chemical compound FC(F)(F)C1=CC=CC=C1S XVGQHRKNXSUPEF-UHFFFAOYSA-N 0.000 description 2
- VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 2
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 2
- JECYUBVRTQDVAT-UHFFFAOYSA-N 2-acetylphenol Chemical compound CC(=O)C1=CC=CC=C1O JECYUBVRTQDVAT-UHFFFAOYSA-N 0.000 description 2
- PLDBMKVHTSHIMR-UHFFFAOYSA-N 2-amino-1-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1OC1=CC(F)=CC=C1Cl PLDBMKVHTSHIMR-UHFFFAOYSA-N 0.000 description 2
- MZQHROOIVZSLHQ-UHFFFAOYSA-N 2-amino-1-[4-(2-chloroanilino)piperidin-1-yl]ethanone;hydrochloride Chemical compound Cl.C1CN(C(=O)CN)CCC1NC1=CC=CC=C1Cl MZQHROOIVZSLHQ-UHFFFAOYSA-N 0.000 description 2
- YUQUNWNSQDULTI-UHFFFAOYSA-N 2-bromobenzenethiol Chemical compound SC1=CC=CC=C1Br YUQUNWNSQDULTI-UHFFFAOYSA-N 0.000 description 2
- AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 2
- KWOHXJCKLMGBFD-UHFFFAOYSA-N 3-(4-nitrophenyl)-1,2,4-oxadiazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=NOC=N1 KWOHXJCKLMGBFD-UHFFFAOYSA-N 0.000 description 2
- HOFZUBUICNNTOE-UHFFFAOYSA-N 3-[4-(2,3-dimethylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC=CC(NC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1C HOFZUBUICNNTOE-UHFFFAOYSA-N 0.000 description 2
- XPXXYCCHDJLLLG-UHFFFAOYSA-N 3-[4-(2,4-dimethylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC(C)=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 XPXXYCCHDJLLLG-UHFFFAOYSA-N 0.000 description 2
- BDOBLCDYWFTAGA-UHFFFAOYSA-N 3-[4-(2,5-difluorophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound FC1=CC=C(F)C(OC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 BDOBLCDYWFTAGA-UHFFFAOYSA-N 0.000 description 2
- PVMAVVKCBJVOIS-UHFFFAOYSA-N 3-[4-(2-aminophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound NC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 PVMAVVKCBJVOIS-UHFFFAOYSA-N 0.000 description 2
- LMTFETKUEHTGOQ-UHFFFAOYSA-N 3-[4-(2-bromoanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound BrC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 LMTFETKUEHTGOQ-UHFFFAOYSA-N 0.000 description 2
- XFCKOIMBVJSVGH-UHFFFAOYSA-N 3-[4-(2-bromophenyl)sulfanylpiperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound BrC1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 XFCKOIMBVJSVGH-UHFFFAOYSA-N 0.000 description 2
- BDNUNADUZOTDKX-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxo-n-(5-phenylpyridin-2-yl)propanamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CC(=O)NC=2N=CC(=CC=2)C=2C=CC=CC=2)=C1 BDNUNADUZOTDKX-UHFFFAOYSA-N 0.000 description 2
- XYMHUTNQALHNMM-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)=C1 XYMHUTNQALHNMM-UHFFFAOYSA-N 0.000 description 2
- LYZYOMIFKVOTRA-UHFFFAOYSA-N 3-[4-(2-chloroanilino)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 LYZYOMIFKVOTRA-UHFFFAOYSA-N 0.000 description 2
- TWDRZQIOZPBBOQ-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxopropanoic acid Chemical compound C1CN(C(=O)CC(=O)O)CCC1OC1=CC=CC=C1Cl TWDRZQIOZPBBOQ-UHFFFAOYSA-N 0.000 description 2
- HEDUOWWFDPUAQS-UHFFFAOYSA-N 3-[4-(2-chlorophenoxy)piperidin-1-yl]-n-[4-(1,2,4-oxadiazol-3-yl)phenyl]-3-oxopropanamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C2=NOC=N2)CC1 HEDUOWWFDPUAQS-UHFFFAOYSA-N 0.000 description 2
- ALWOANMIKBRIPL-UHFFFAOYSA-N 3-[4-(2-chlorophenyl)sulfanylpiperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound ClC1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 ALWOANMIKBRIPL-UHFFFAOYSA-N 0.000 description 2
- CTKAWQIIQDLYMX-UHFFFAOYSA-N 3-[4-(2-methylanilino)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound CC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 CTKAWQIIQDLYMX-UHFFFAOYSA-N 0.000 description 2
- LUJMEECXHPYQOF-UHFFFAOYSA-N 3-hydroxyacetophenone Chemical compound CC(=O)C1=CC=CC(O)=C1 LUJMEECXHPYQOF-UHFFFAOYSA-N 0.000 description 2
- NXRWUHBEAUHMOQ-UHFFFAOYSA-N 3-oxo-n-(6-phenylpyridin-3-yl)-3-[4-[2-(trifluoromethyl)anilino]piperidin-1-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 NXRWUHBEAUHMOQ-UHFFFAOYSA-N 0.000 description 2
- TXFPEBPIARQUIG-UHFFFAOYSA-N 4'-hydroxyacetophenone Chemical compound CC(=O)C1=CC=C(O)C=C1 TXFPEBPIARQUIG-UHFFFAOYSA-N 0.000 description 2
- PTYSBGOBFBVYLO-UHFFFAOYSA-N 4-[2-(trifluoromethyl)phenyl]sulfanylpiperidine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC=C1SC1CCNCC1 PTYSBGOBFBVYLO-UHFFFAOYSA-N 0.000 description 2
- 125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- BANGXRDZWHJOEP-UHFFFAOYSA-N 5-(2-phenylmethoxyphenyl)-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1=CC=CC=C1OCC1=CC=CC=C1 BANGXRDZWHJOEP-UHFFFAOYSA-N 0.000 description 2
- OAPVIBHQRYFYSE-UHFFFAOYSA-N 5-Phenyl-2-pyridinamine Chemical compound C1=NC(N)=CC=C1C1=CC=CC=C1 OAPVIBHQRYFYSE-UHFFFAOYSA-N 0.000 description 2
- FMAXVPXZZVRKAC-UHFFFAOYSA-N 5-anilinopyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1NC1=CC=CC=C1 FMAXVPXZZVRKAC-UHFFFAOYSA-N 0.000 description 2
- SJXVYJBKNRMBKF-UHFFFAOYSA-N 5-anilinopyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC=C1NC1=CC=CC=C1 SJXVYJBKNRMBKF-UHFFFAOYSA-N 0.000 description 2
- WTHODOKFSYPTKA-UHFFFAOYSA-N 5-chloropyridine-2-carbonitrile Chemical compound ClC1=CC=C(C#N)N=C1 WTHODOKFSYPTKA-UHFFFAOYSA-N 0.000 description 2
- WJOAJTWVYTULDB-UHFFFAOYSA-N 5-nitro-2-phenylpyridine Chemical compound N1=CC([N+](=O)[O-])=CC=C1C1=CC=CC=C1 WJOAJTWVYTULDB-UHFFFAOYSA-N 0.000 description 2
- FOMAKWRPGGQFNG-UHFFFAOYSA-N 5-phenylpyridine-2-carbonitrile Chemical compound C1=NC(C#N)=CC=C1C1=CC=CC=C1 FOMAKWRPGGQFNG-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- 241000271566 Aves Species 0.000 description 2
- ZYFRBEJYRHBUSJ-UHFFFAOYSA-N C1CN(C(=O)CN)CCC1OC1=CC=CC=C1Cl Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=CC=C1Cl ZYFRBEJYRHBUSJ-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 2
- 208000004930 Fatty Liver Diseases 0.000 description 2
- 241000710781 Flaviviridae Species 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 239000004471 Glycine Substances 0.000 description 2
- 241000711549 Hepacivirus C Species 0.000 description 2
- 206010019728 Hepatitis alcoholic Diseases 0.000 description 2
- 101000639987 Homo sapiens Stearoyl-CoA desaturase 5 Proteins 0.000 description 2
- 206010020772 Hypertension Diseases 0.000 description 2
- 201000001431 Hyperuricemia Diseases 0.000 description 2
- 108010007622 LDL Lipoproteins Proteins 0.000 description 2
- 102000007330 LDL Lipoproteins Human genes 0.000 description 2
- 102000016267 Leptin Human genes 0.000 description 2
- 108010092277 Leptin Proteins 0.000 description 2
- 208000017170 Lipid metabolism disease Diseases 0.000 description 2
- HGINADPHJQTSKN-UHFFFAOYSA-N Monoethyl malonic acid Chemical compound CCOC(=O)CC(O)=O HGINADPHJQTSKN-UHFFFAOYSA-N 0.000 description 2
- 208000021642 Muscular disease Diseases 0.000 description 2
- 201000009623 Myopathy Diseases 0.000 description 2
- 101100109871 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) aro-8 gene Proteins 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical class OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 102000001708 Protein Isoforms Human genes 0.000 description 2
- 108010029485 Protein Isoforms Proteins 0.000 description 2
- 241000315672 SARS coronavirus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000282898 Sus scrofa Species 0.000 description 2
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 2
- 208000032109 Transient ischaemic attack Diseases 0.000 description 2
- 241000710772 Yellow fever virus Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 208000002353 alcoholic hepatitis Diseases 0.000 description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
- 125000005741 alkyl alkenyl group Chemical group 0.000 description 2
- VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- 125000004799 bromophenyl group Chemical group 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000004296 chiral HPLC Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 125000000068 chlorophenyl group Chemical group 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 208000019425 cirrhosis of liver Diseases 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000010511 deprotection reaction Methods 0.000 description 2
- 238000009795 derivation Methods 0.000 description 2
- 125000004212 difluorophenyl group Chemical group 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 241001493065 dsRNA viruses Species 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 206010014599 encephalitis Diseases 0.000 description 2
- OBRWDBDUWYHFLV-UHFFFAOYSA-N ethyl 1-methyl-5-(2-phenylmethoxyphenyl)pyrazole-3-carboxylate Chemical compound CN1N=C(C(=O)OCC)C=C1C1=CC=CC=C1OCC1=CC=CC=C1 OBRWDBDUWYHFLV-UHFFFAOYSA-N 0.000 description 2
- XTQGEHBWLFMCQN-UHFFFAOYSA-N ethyl 2,4-dioxo-4-(2-phenylmethoxyphenyl)butanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 XTQGEHBWLFMCQN-UHFFFAOYSA-N 0.000 description 2
- NOADONVIZUCJNO-UHFFFAOYSA-N ethyl 2,4-dioxo-4-(3-phenylmethoxyphenyl)butanoate Chemical compound CCOC(=O)C(=O)CC(=O)C1=CC=CC(OCC=2C=CC=CC=2)=C1 NOADONVIZUCJNO-UHFFFAOYSA-N 0.000 description 2
- CZJRJPULNAADOX-UHFFFAOYSA-N ethyl 2-[(4-anilinobenzoyl)amino]acetate Chemical compound C1=CC(C(=O)NCC(=O)OCC)=CC=C1NC1=CC=CC=C1 CZJRJPULNAADOX-UHFFFAOYSA-N 0.000 description 2
- STMZPXPSTZEIGX-UHFFFAOYSA-N ethyl 3-(2-phenylmethoxyphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OCC)C=C1C1=CC=CC=C1OCC1=CC=CC=C1 STMZPXPSTZEIGX-UHFFFAOYSA-N 0.000 description 2
- ZYPPRMRWHYHYSH-UHFFFAOYSA-N ethyl 3-(4-phenylmethoxyphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OCC)C=C1C(C=C1)=CC=C1OCC1=CC=CC=C1 ZYPPRMRWHYHYSH-UHFFFAOYSA-N 0.000 description 2
- BQTVHGGFKNHDSB-UHFFFAOYSA-N ethyl 3-oxo-3-[(3-phenyl-1,2,4-thiadiazol-5-yl)amino]propanoate Chemical compound S1C(NC(=O)CC(=O)OCC)=NC(C=2C=CC=CC=2)=N1 BQTVHGGFKNHDSB-UHFFFAOYSA-N 0.000 description 2
- QXRBMVDPLUUGIL-UHFFFAOYSA-N ethyl 3-oxo-3-[(6-phenylpyridin-3-yl)amino]propanoate Chemical compound N1=CC(NC(=O)CC(=O)OCC)=CC=C1C1=CC=CC=C1 QXRBMVDPLUUGIL-UHFFFAOYSA-N 0.000 description 2
- AZZHJDRWBMQEKD-UHFFFAOYSA-N ethyl 3-phenyl-1h-pyrazole-5-carboxylate Chemical compound N1C(C(=O)OCC)=CC(C=2C=CC=CC=2)=N1 AZZHJDRWBMQEKD-UHFFFAOYSA-N 0.000 description 2
- MTOLFTWMGRZCNF-UHFFFAOYSA-N ethyl 5-(2-hydroxyphenyl)-1-methylpyrazole-3-carboxylate Chemical compound CN1N=C(C(=O)OCC)C=C1C1=CC=CC=C1O MTOLFTWMGRZCNF-UHFFFAOYSA-N 0.000 description 2
- HJYKHSARQWFWEN-UHFFFAOYSA-N ethyl 5-(2-phenylmethoxyphenyl)-1,2-oxazole-3-carboxylate Chemical compound O1N=C(C(=O)OCC)C=C1C1=CC=CC=C1OCC1=CC=CC=C1 HJYKHSARQWFWEN-UHFFFAOYSA-N 0.000 description 2
- PKIKWIRBQHJXJM-UHFFFAOYSA-N ethyl 6-anilinopyridine-3-carboxylate Chemical compound N1=CC(C(=O)OCC)=CC=C1NC1=CC=CC=C1 PKIKWIRBQHJXJM-UHFFFAOYSA-N 0.000 description 2
- 208000010706 fatty liver disease Diseases 0.000 description 2
- 229960002449 glycine Drugs 0.000 description 2
- 150000002332 glycine derivatives Chemical class 0.000 description 2
- 229960001269 glycine hydrochloride Drugs 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 description 2
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 2
- 102000050986 human SCD5 Human genes 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 2
- 125000002883 imidazolyl group Chemical group 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 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 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- NRYBAZVQPHGZNS-ZSOCWYAHSA-N leptin Chemical compound O=C([C@H](CO)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CO)NC(=O)CNC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](N)CC(C)C)CCSC)N1CCC[C@H]1C(=O)NCC(=O)N[C@@H](CS)C(O)=O NRYBAZVQPHGZNS-ZSOCWYAHSA-N 0.000 description 2
- 229940039781 leptin Drugs 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical class OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000012528 membrane Substances 0.000 description 2
- 210000004379 membrane Anatomy 0.000 description 2
- 230000002503 metabolic effect Effects 0.000 description 2
- FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- XMPLCJOQBDGMKT-UHFFFAOYSA-N methyl 5-phenyl-1,2-oxazole-3-carboxylate Chemical compound O1N=C(C(=O)OC)C=C1C1=CC=CC=C1 XMPLCJOQBDGMKT-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- 235000021281 monounsaturated fatty acids Nutrition 0.000 description 2
- 210000003205 muscle Anatomy 0.000 description 2
- BMJKBMKUPRKBQR-UHFFFAOYSA-N n-(2,3-dimethylphenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.CC1=CC=CC(NC2CCNCC2)=C1C BMJKBMKUPRKBQR-UHFFFAOYSA-N 0.000 description 2
- HSPUCPKFVRPATB-UHFFFAOYSA-N n-(2-bromophenyl)-n-methylpiperidin-4-amine Chemical compound C=1C=CC=C(Br)C=1N(C)C1CCNCC1 HSPUCPKFVRPATB-UHFFFAOYSA-N 0.000 description 2
- HJKLYHRGLFHTSO-UHFFFAOYSA-N n-(2-bromophenyl)-n-methylpiperidin-4-amine;hydrochloride Chemical compound Cl.C=1C=CC=C(Br)C=1N(C)C1CCNCC1 HJKLYHRGLFHTSO-UHFFFAOYSA-N 0.000 description 2
- AFKLAENYADRSGT-UHFFFAOYSA-N n-(2-tert-butylphenyl)piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.CC(C)(C)C1=CC=CC=C1NC1CCNCC1 AFKLAENYADRSGT-UHFFFAOYSA-N 0.000 description 2
- KFQKKPOQRLXIFO-UHFFFAOYSA-N n-[2-[4-(2-bromo-n-methylanilino)piperidin-1-yl]-2-oxoethyl]-5-phenyl-1,2-oxazole-3-carboxamide Chemical compound C=1C=CC=C(Br)C=1N(C)C(CC1)CCN1C(=O)CNC(=O)C(=NO1)C=C1C1=CC=CC=C1 KFQKKPOQRLXIFO-UHFFFAOYSA-N 0.000 description 2
- NORABPMBUQMZLT-UHFFFAOYSA-N n-hydroxy-4-nitrobenzamide Chemical compound ONC(=O)C1=CC=C([N+]([O-])=O)C=C1 NORABPMBUQMZLT-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
- DFPAKSUCGFBDDF-UHFFFAOYSA-N nicotinic acid amide Natural products NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 2
- 125000006501 nitrophenyl group Chemical group 0.000 description 2
- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 description 2
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 description 2
- RNVCVTLRINQCPJ-UHFFFAOYSA-N o-toluidine Chemical compound CC1=CC=CC=C1N RNVCVTLRINQCPJ-UHFFFAOYSA-N 0.000 description 2
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 125000002971 oxazolyl group Chemical group 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 239000012026 peptide coupling reagents Substances 0.000 description 2
- 235000020777 polyunsaturated fatty acids Nutrition 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 235000011181 potassium carbonates Nutrition 0.000 description 2
- 238000012746 preparative thin layer chromatography Methods 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 231100000240 steatosis hepatitis Toxicity 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 235000002906 tartaric acid Nutrition 0.000 description 2
- 239000011975 tartaric acid Substances 0.000 description 2
- HBDPIRYLUOFUFP-UHFFFAOYSA-N tert-butyl 4-(2,3-dimethylanilino)piperidine-1-carboxylate Chemical compound CC1=CC=CC(NC2CCN(CC2)C(=O)OC(C)(C)C)=C1C HBDPIRYLUOFUFP-UHFFFAOYSA-N 0.000 description 2
- RGQRYFMEGSEPQV-UHFFFAOYSA-N tert-butyl 4-(2-bromo-n-methylanilino)piperidine-1-carboxylate Chemical compound C=1C=CC=C(Br)C=1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 RGQRYFMEGSEPQV-UHFFFAOYSA-N 0.000 description 2
- VULMUWBVTRHXFN-UHFFFAOYSA-N tert-butyl 4-(2-bromoanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC=C1Br VULMUWBVTRHXFN-UHFFFAOYSA-N 0.000 description 2
- HZMFHOJDYUQWFD-UHFFFAOYSA-N tert-butyl 4-(2-bromophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1Br HZMFHOJDYUQWFD-UHFFFAOYSA-N 0.000 description 2
- QQKRXIBPRNXHHS-UHFFFAOYSA-N tert-butyl 4-(2-nitrophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1[N+]([O-])=O QQKRXIBPRNXHHS-UHFFFAOYSA-N 0.000 description 2
- CUHAMCCERFSWRB-UHFFFAOYSA-N tert-butyl 4-[2-(trifluoromethyl)anilino]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC=C1C(F)(F)F CUHAMCCERFSWRB-UHFFFAOYSA-N 0.000 description 2
- YUDXRZNXUGFMGP-UHFFFAOYSA-N tert-butyl 4-[2-(trifluoromethyl)phenyl]sulfanylpiperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1SC1=CC=CC=C1C(F)(F)F YUDXRZNXUGFMGP-UHFFFAOYSA-N 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 description 2
- 125000000335 thiazolyl group Chemical group 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 201000005665 thrombophilia Diseases 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- 238000011200 topical administration Methods 0.000 description 2
- 201000010875 transient cerebral ischemia Diseases 0.000 description 2
- 150000003626 triacylglycerols Chemical class 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- 229940051021 yellow-fever virus Drugs 0.000 description 2
- QBYIENPQHBMVBV-HFEGYEGKSA-N (2R)-2-hydroxy-2-phenylacetic acid Chemical compound O[C@@H](C(O)=O)c1ccccc1.O[C@@H](C(O)=O)c1ccccc1 QBYIENPQHBMVBV-HFEGYEGKSA-N 0.000 description 1
- DNISEZBAYYIQFB-PHDIDXHHSA-N (2r,3r)-2,3-diacetyloxybutanedioic acid Chemical compound CC(=O)O[C@@H](C(O)=O)[C@H](C(O)=O)OC(C)=O DNISEZBAYYIQFB-PHDIDXHHSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical class C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- PQQRHWFRZHFGFM-UHFFFAOYSA-N 1,3-thiazole-4-carboxamide Chemical compound NC(=O)C1=CSC=N1 PQQRHWFRZHFGFM-UHFFFAOYSA-N 0.000 description 1
- KPQFZAJJGWLXIK-UHFFFAOYSA-N 1-(2-nitrophenoxy)piperidine;hydrochloride Chemical compound Cl.[O-][N+](=O)C1=CC=CC=C1ON1CCCCC1 KPQFZAJJGWLXIK-UHFFFAOYSA-N 0.000 description 1
- SLGDDWABRNAGHM-UHFFFAOYSA-N 1-(3-methylphenyl)triazole-4-carboxylic acid Chemical compound CC1=CC=CC(N2N=NC(=C2)C(O)=O)=C1 SLGDDWABRNAGHM-UHFFFAOYSA-N 0.000 description 1
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 1
- FQYWDWKZXRCZIZ-UHFFFAOYSA-N 1-[4-(2-chlorophenoxy)piperidin-1-yl]-2-[(4-phenylphenyl)methylamino]ethanone Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNCC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 FQYWDWKZXRCZIZ-UHFFFAOYSA-N 0.000 description 1
- HBRVWQZNYJKJEF-UHFFFAOYSA-N 1-cyclopropyltriazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1C1CC1 HBRVWQZNYJKJEF-UHFFFAOYSA-N 0.000 description 1
- 125000006218 1-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006219 1-ethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- IZYOHLOUZVEIOS-UHFFFAOYSA-N 1-methoxycarbonylcyclopropane-1-carboxylic acid Chemical compound COC(=O)C1(C(O)=O)CC1 IZYOHLOUZVEIOS-UHFFFAOYSA-N 0.000 description 1
- 125000001088 1-naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 description 1
- IVDBIFHDJPMBFG-UHFFFAOYSA-N 1-phenyltriazole-4-carboxylic acid Chemical compound N1=NC(C(=O)O)=CN1C1=CC=CC=C1 IVDBIFHDJPMBFG-UHFFFAOYSA-N 0.000 description 1
- BNYCHCAYYYRJSH-UHFFFAOYSA-N 1h-pyrazole-5-carboxamide Chemical compound NC(=O)C1=CC=NN1 BNYCHCAYYYRJSH-UHFFFAOYSA-N 0.000 description 1
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 description 1
- INXKVYFOWNAVMU-UHFFFAOYSA-N 2,5-difluorophenol Chemical compound OC1=CC(F)=CC=C1F INXKVYFOWNAVMU-UHFFFAOYSA-N 0.000 description 1
- MSFWCLUJEBQNPL-UHFFFAOYSA-N 2-(2-fluorophenyl)-1-phenylethanone Chemical compound FC1=CC=CC=C1CC(=O)C1=CC=CC=C1 MSFWCLUJEBQNPL-UHFFFAOYSA-N 0.000 description 1
- JDWWQTXSCOQPGB-UHFFFAOYSA-N 2-(3H-oxadiazol-2-yl)benzamide Chemical compound O1N(NC=C1)C1=C(C(=O)N)C=CC=C1 JDWWQTXSCOQPGB-UHFFFAOYSA-N 0.000 description 1
- VBLXCTYLWZJBKA-UHFFFAOYSA-N 2-(trifluoromethyl)aniline Chemical compound NC1=CC=CC=C1C(F)(F)F VBLXCTYLWZJBKA-UHFFFAOYSA-N 0.000 description 1
- ZOQOPXVJANRGJZ-UHFFFAOYSA-N 2-(trifluoromethyl)phenol Chemical compound OC1=CC=CC=C1C(F)(F)F ZOQOPXVJANRGJZ-UHFFFAOYSA-N 0.000 description 1
- RBRDCYCLEIWWIU-UHFFFAOYSA-N 2-amino-1-[4-(2-chloroanilino)piperidin-1-yl]ethanone;dihydrochloride Chemical compound Cl.Cl.C1CN(C(=O)CN)CCC1NC1=CC=CC=C1Cl RBRDCYCLEIWWIU-UHFFFAOYSA-N 0.000 description 1
- GIBABBJFACCPRR-UHFFFAOYSA-N 2-amino-1-[4-(5-bromo-2-methoxyanilino)piperidin-1-yl]ethanone;hydrochloride Chemical compound Cl.COC1=CC=C(Br)C=C1NC1CCN(C(=O)CN)CC1 GIBABBJFACCPRR-UHFFFAOYSA-N 0.000 description 1
- NRRWGZXBTDGOCW-UHFFFAOYSA-N 2-amino-1-[4-[2-(trifluoromethyl)phenoxy]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=CC=C1C(F)(F)F NRRWGZXBTDGOCW-UHFFFAOYSA-N 0.000 description 1
- UJWBFVKKNZXICC-UHFFFAOYSA-N 2-amino-1-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethanone Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=CC(C(F)(F)F)=C1 UJWBFVKKNZXICC-UHFFFAOYSA-N 0.000 description 1
- QKPAGFYVAZILTG-UHFFFAOYSA-N 2-amino-1-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethanone;hydrochloride Chemical compound Cl.C1CN(C(=O)CN)CCC1OC1=CC=CC(C(F)(F)F)=C1 QKPAGFYVAZILTG-UHFFFAOYSA-N 0.000 description 1
- AOPBDRUWRLBSDB-UHFFFAOYSA-N 2-bromoaniline Chemical compound NC1=CC=CC=C1Br AOPBDRUWRLBSDB-UHFFFAOYSA-N 0.000 description 1
- CMQOZIKIOASEIN-UHFFFAOYSA-N 2-chloro-5-fluorophenol Chemical compound OC1=CC(F)=CC=C1Cl CMQOZIKIOASEIN-UHFFFAOYSA-N 0.000 description 1
- ISPYQTSUDJAMAB-UHFFFAOYSA-N 2-chlorophenol Chemical compound OC1=CC=CC=C1Cl ISPYQTSUDJAMAB-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- 125000006176 2-ethylbutyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 1
- 125000004493 2-methylbut-1-yl group Chemical group CC(C*)CC 0.000 description 1
- 125000005916 2-methylpentyl group Chemical group 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- HLTDBMHJSBSAOM-UHFFFAOYSA-N 2-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CC=N1 HLTDBMHJSBSAOM-UHFFFAOYSA-N 0.000 description 1
- AEIOZWYBDBVCGW-UHFFFAOYSA-N 2-tert-butylaniline Chemical compound CC(C)(C)C1=CC=CC=C1N AEIOZWYBDBVCGW-UHFFFAOYSA-N 0.000 description 1
- GTODOEDLCNTSLG-UHFFFAOYSA-N 2h-triazole-4-carboxylic acid Chemical compound OC(=O)C1=CNN=N1 GTODOEDLCNTSLG-UHFFFAOYSA-N 0.000 description 1
- KOWRVFWZCLHEIU-UHFFFAOYSA-N 3-(3-hydroxyphenyl)-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=C(O)C=CC=2)=N1 KOWRVFWZCLHEIU-UHFFFAOYSA-N 0.000 description 1
- VRGJLAQKUUOLIR-UHFFFAOYSA-N 3-(3-phenylmethoxyphenyl)-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 VRGJLAQKUUOLIR-UHFFFAOYSA-N 0.000 description 1
- JFCYETQEMDKJAU-UHFFFAOYSA-N 3-(4-phenylmethoxyphenyl)-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2C=CC(OCC=3C=CC=CC=3)=CC=2)=N1 JFCYETQEMDKJAU-UHFFFAOYSA-N 0.000 description 1
- VAEWAVHUBWTGSH-UHFFFAOYSA-N 3-[4-(2-bromoanilino)piperidin-1-yl]-3-oxo-n-(6-phenylpyridin-3-yl)propanamide Chemical compound BrC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 VAEWAVHUBWTGSH-UHFFFAOYSA-N 0.000 description 1
- QGWBZLVWAMPTAZ-UHFFFAOYSA-N 3-[4-(2-bromophenyl)sulfanylpiperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound BrC1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 QGWBZLVWAMPTAZ-UHFFFAOYSA-N 0.000 description 1
- YVHSWXNIQYWREU-UHFFFAOYSA-N 3-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-3-oxopropanoic acid Chemical compound C1CN(C(=O)CC(=O)O)CCC1OC1=CC(F)=CC=C1Cl YVHSWXNIQYWREU-UHFFFAOYSA-N 0.000 description 1
- ODSKZIKVMYRKMD-UHFFFAOYSA-N 3-[4-(2-methylanilino)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound CC1=CC=CC=C1NC1CCN(C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 ODSKZIKVMYRKMD-UHFFFAOYSA-N 0.000 description 1
- OXFGKEMWMUFPOP-UHFFFAOYSA-N 3-[4-(3-cyanophenoxy)piperidin-1-yl]-3-oxo-n-(4-phenylphenyl)propanamide Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(=O)CC(=O)N(CC1)CCC1OC1=CC=CC(C#N)=C1 OXFGKEMWMUFPOP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical class OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-UHFFFAOYSA-N 0.000 description 1
- HGINADPHJQTSKN-UHFFFAOYSA-M 3-ethoxy-3-oxopropanoate Chemical compound CCOC(=O)CC([O-])=O HGINADPHJQTSKN-UHFFFAOYSA-M 0.000 description 1
- 125000005917 3-methylpentyl group Chemical group 0.000 description 1
- PZGXZOUKCOBABU-UHFFFAOYSA-N 3-oxo-3-[(3-phenyl-1,2,4-thiadiazol-5-yl)amino]propanoic acid Chemical compound S1C(NC(=O)CC(=O)O)=NC(C=2C=CC=CC=2)=N1 PZGXZOUKCOBABU-UHFFFAOYSA-N 0.000 description 1
- MJQWEOVOAFYGBS-UHFFFAOYSA-N 3-oxo-n-(4-phenylphenyl)-3-[4-(3,4,5-trifluorophenoxy)piperidin-1-yl]propanamide Chemical compound FC1=C(F)C(F)=CC(OC2CCN(CC2)C(=O)CC(=O)NC=2C=CC(=CC=2)C=2C=CC=CC=2)=C1 MJQWEOVOAFYGBS-UHFFFAOYSA-N 0.000 description 1
- OVJSTHBDUBWNDW-UHFFFAOYSA-N 3-oxo-n-(6-phenylpyridin-3-yl)-3-[4-[2-(trifluoromethyl)phenyl]sulfanylpiperidin-1-yl]propanamide Chemical compound FC(F)(F)C1=CC=CC=C1SC1CCN(C(=O)CC(=O)NC=2C=NC(=CC=2)C=2C=CC=CC=2)CC1 OVJSTHBDUBWNDW-UHFFFAOYSA-N 0.000 description 1
- XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical class OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
- SJBWHTBPIJXUFP-UHFFFAOYSA-N 3-pyridin-2-yl-1h-pyrazole-5-carboxylic acid Chemical compound N1C(C(=O)O)=CC(C=2N=CC=CC=2)=N1 SJBWHTBPIJXUFP-UHFFFAOYSA-N 0.000 description 1
- UIMMTLBEKPSEGH-UHFFFAOYSA-N 4-(2-bromophenoxy)piperidine Chemical compound BrC1=CC=CC=C1OC1CCNCC1 UIMMTLBEKPSEGH-UHFFFAOYSA-N 0.000 description 1
- IYGLJQDJMSCRPK-UHFFFAOYSA-N 4-(2-bromophenyl)sulfanylpiperidine;hydrochloride Chemical compound Cl.BrC1=CC=CC=C1SC1CCNCC1 IYGLJQDJMSCRPK-UHFFFAOYSA-N 0.000 description 1
- MDEROWMZTRTVTC-UHFFFAOYSA-N 4-(2-chlorophenyl)sulfanylpiperidine;hydrochloride Chemical compound Cl.ClC1=CC=CC=C1SC1CCNCC1 MDEROWMZTRTVTC-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- KQJNEJZQJRLPPB-UHFFFAOYSA-N 4-anilino-n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]benzamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(NC=3C=CC=CC=3)=CC=2)CC1 KQJNEJZQJRLPPB-UHFFFAOYSA-N 0.000 description 1
- JRTQQQRGUVTUJK-UHFFFAOYSA-N 4-anilinopyridine-2-carboxylic acid Chemical compound C1=NC(C(=O)O)=CC(NC=2C=CC=CC=2)=C1 JRTQQQRGUVTUJK-UHFFFAOYSA-N 0.000 description 1
- TUXYZHVUPGXXQG-UHFFFAOYSA-N 4-bromobenzoic acid Chemical compound OC(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-N 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- OHZUEFKOZYWUFF-UHFFFAOYSA-N 4-hydroxypiperidine-1-carboxylic acid Chemical compound OC1CCN(C(O)=O)CC1 OHZUEFKOZYWUFF-UHFFFAOYSA-N 0.000 description 1
- NKJIFDNZPGLLSH-UHFFFAOYSA-N 4-nitrobenzonitrile Chemical compound [O-][N+](=O)C1=CC=C(C#N)C=C1 NKJIFDNZPGLLSH-UHFFFAOYSA-N 0.000 description 1
- PZNGOFHHOGORBU-UHFFFAOYSA-N 5-(2-fluorophenyl)-1h-pyrazole Chemical compound FC1=CC=CC=C1C1=CC=NN1 PZNGOFHHOGORBU-UHFFFAOYSA-N 0.000 description 1
- UZFWPGDNEOHFBK-UHFFFAOYSA-N 5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxylic acid Chemical compound O1N=C(C(=O)O)C=C1C1=CC=CC=C1O UZFWPGDNEOHFBK-UHFFFAOYSA-N 0.000 description 1
- IVILGUFRMDBUEQ-UHFFFAOYSA-N 5-iodopyridin-2-amine Chemical compound NC1=CC=C(I)C=N1 IVILGUFRMDBUEQ-UHFFFAOYSA-N 0.000 description 1
- OEDUIFSDODUDRK-UHFFFAOYSA-N 5-phenyl-1h-pyrazole Chemical compound N1N=CC=C1C1=CC=CC=C1 OEDUIFSDODUDRK-UHFFFAOYSA-N 0.000 description 1
- 102000014156 AMP-Activated Protein Kinases Human genes 0.000 description 1
- 108010011376 AMP-Activated Protein Kinases Proteins 0.000 description 1
- 208000002874 Acne Vulgaris Diseases 0.000 description 1
- 101710159293 Acyl-CoA desaturase 1 Proteins 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- 241000710929 Alphavirus Species 0.000 description 1
- 108010071619 Apolipoproteins Proteins 0.000 description 1
- 102000007592 Apolipoproteins Human genes 0.000 description 1
- 102000013918 Apolipoproteins E Human genes 0.000 description 1
- 108010025628 Apolipoproteins E Proteins 0.000 description 1
- 241001533362 Astroviridae Species 0.000 description 1
- 201000001320 Atherosclerosis Diseases 0.000 description 1
- 241000711515 Berne virus Species 0.000 description 1
- 241000711443 Bovine coronavirus Species 0.000 description 1
- 241000203231 Breda virus Species 0.000 description 1
- 241001533357 Bymovirus Species 0.000 description 1
- SBKWBARKBFNGAG-UHFFFAOYSA-N C1CN(C(=O)CN)CCC1OC1=CC(F)=CC(C(F)(F)F)=C1 Chemical compound C1CN(C(=O)CN)CCC1OC1=CC(F)=CC(C(F)(F)F)=C1 SBKWBARKBFNGAG-UHFFFAOYSA-N 0.000 description 1
- AHCWPIQMAYFEHQ-UHFFFAOYSA-N C1CN(C(=O)CN)CCC1OC1=CC=C(F)C(C(F)(F)F)=C1 Chemical compound C1CN(C(=O)CN)CCC1OC1=CC=C(F)C(C(F)(F)F)=C1 AHCWPIQMAYFEHQ-UHFFFAOYSA-N 0.000 description 1
- IYPSTCMUBLJALL-UHFFFAOYSA-N C1N(C(=O)CN)CC1OC1=CC(F)=CC(C(F)(F)F)=C1 Chemical compound C1N(C(=O)CN)CC1OC1=CC(F)=CC(C(F)(F)F)=C1 IYPSTCMUBLJALL-UHFFFAOYSA-N 0.000 description 1
- QDQMTEJVJYNPPB-UHFFFAOYSA-N C1N(C(=O)CN)CC1OC1=CC=CC(C(F)(F)F)=C1 Chemical compound C1N(C(=O)CN)CC1OC1=CC=CC(C(F)(F)F)=C1 QDQMTEJVJYNPPB-UHFFFAOYSA-N 0.000 description 1
- STGMPRKJNLMSOM-UHFFFAOYSA-N C1N(C(=O)CN)CC1OC1=CC=CC=C1Cl Chemical compound C1N(C(=O)CN)CC1OC1=CC=CC=C1Cl STGMPRKJNLMSOM-UHFFFAOYSA-N 0.000 description 1
- SEMRXIPDBPUHJQ-UHFFFAOYSA-N C1N(C(=O)CN)CCC1OC1=CC(F)=CC=C1F Chemical compound C1N(C(=O)CN)CCC1OC1=CC(F)=CC=C1F SEMRXIPDBPUHJQ-UHFFFAOYSA-N 0.000 description 1
- NLHAJXBPDZSNDR-UHFFFAOYSA-N C=1C=CC=C(Br)C=1N(C)C1CCN(C(=O)CN)CC1 Chemical compound C=1C=CC=C(Br)C=1N(C)C1CCN(C(=O)CN)CC1 NLHAJXBPDZSNDR-UHFFFAOYSA-N 0.000 description 1
- IXHFROZZKRCQQP-UHFFFAOYSA-N CC(C)(C)C1=CC=CC=C1NC1CCN(C(=O)CN)CC1 Chemical compound CC(C)(C)C1=CC=CC=C1NC1CCN(C(=O)CN)CC1 IXHFROZZKRCQQP-UHFFFAOYSA-N 0.000 description 1
- XKDSOLKNLGHVRZ-UHFFFAOYSA-N CC1=CC=C(C#N)C=C1NC1CCN(C(=O)CN)CC1 Chemical compound CC1=CC=C(C#N)C=C1NC1CCN(C(=O)CN)CC1 XKDSOLKNLGHVRZ-UHFFFAOYSA-N 0.000 description 1
- UWKQESXIAZDLGF-UHFFFAOYSA-N CC1=CC=C(C#N)C=C1OC1CCN(C(=O)CN)CC1 Chemical compound CC1=CC=C(C#N)C=C1OC1CCN(C(=O)CN)CC1 UWKQESXIAZDLGF-UHFFFAOYSA-N 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 241000714198 Caliciviridae Species 0.000 description 1
- 241000711506 Canine coronavirus Species 0.000 description 1
- 241000282465 Canis Species 0.000 description 1
- 241000282472 Canis lupus familiaris Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 208000005623 Carcinogenesis Diseases 0.000 description 1
- 102000002666 Carnitine O-palmitoyltransferase Human genes 0.000 description 1
- 108010018424 Carnitine O-palmitoyltransferase Proteins 0.000 description 1
- 102100027943 Carnitine O-palmitoyltransferase 1, liver isoform Human genes 0.000 description 1
- 101710120614 Carnitine O-palmitoyltransferase 1, liver isoform Proteins 0.000 description 1
- 101710108984 Carnitine O-palmitoyltransferase 1, muscle isoform Proteins 0.000 description 1
- 201000002929 Carnitine palmitoyltransferase II deficiency Diseases 0.000 description 1
- 206010050215 Carnitine palmitoyltransferase deficiency Diseases 0.000 description 1
- 208000008964 Chemical and Drug Induced Liver Injury Diseases 0.000 description 1
- 241001502567 Chikungunya virus Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 206010008631 Cholera Diseases 0.000 description 1
- 239000004381 Choline salt Substances 0.000 description 1
- 208000031288 Combined hyperlipidaemia Diseases 0.000 description 1
- 241000709687 Coxsackievirus Species 0.000 description 1
- 201000003883 Cystic fibrosis Diseases 0.000 description 1
- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
- 208000001490 Dengue Diseases 0.000 description 1
- 206010012310 Dengue fever Diseases 0.000 description 1
- 201000004624 Dermatitis Diseases 0.000 description 1
- 208000002249 Diabetes Complications Diseases 0.000 description 1
- 206010012655 Diabetic complications Diseases 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 206010072268 Drug-induced liver injury Diseases 0.000 description 1
- 241000710945 Eastern equine encephalitis virus Species 0.000 description 1
- 241000710188 Encephalomyocarditis virus Species 0.000 description 1
- 241000709661 Enterovirus Species 0.000 description 1
- 241000991587 Enterovirus C Species 0.000 description 1
- 206010066919 Epidemic polyarthritis Diseases 0.000 description 1
- 241000283073 Equus caballus Species 0.000 description 1
- 208000010201 Exanthema Diseases 0.000 description 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 description 1
- 241000711475 Feline infectious peritonitis virus Species 0.000 description 1
- 241000282324 Felis Species 0.000 description 1
- 241000282326 Felis catus Species 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000531123 GB virus C Species 0.000 description 1
- 241000287828 Gallus gallus Species 0.000 description 1
- 208000005577 Gastroenteritis Diseases 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
- 208000002705 Glucose Intolerance Diseases 0.000 description 1
- 206010018429 Glucose tolerance impaired Diseases 0.000 description 1
- 108010023302 HDL Cholesterol Proteins 0.000 description 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 description 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 description 1
- 208000036066 Hemophagocytic Lymphohistiocytosis Diseases 0.000 description 1
- 241000700721 Hepatitis B virus Species 0.000 description 1
- 241000709721 Hepatovirus A Species 0.000 description 1
- 208000033981 Hereditary haemochromatosis Diseases 0.000 description 1
- 101100041816 Homo sapiens SCD gene Proteins 0.000 description 1
- 101100309604 Homo sapiens SCD5 gene Proteins 0.000 description 1
- 244000309467 Human Coronavirus Species 0.000 description 1
- 241001479210 Human astrovirus Species 0.000 description 1
- 241001428935 Human coronavirus OC43 Species 0.000 description 1
- 208000035150 Hypercholesterolemia Diseases 0.000 description 1
- 208000001021 Hyperlipoproteinemia Type I Diseases 0.000 description 1
- 241000711450 Infectious bronchitis virus Species 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- LNQCUTNLHUQZLR-VNPYQEQNSA-N Iridin Natural products O(C)c1c(O)c2C(=O)C(c3cc(OC)c(OC)c(O)c3)=COc2cc1O[C@H]1[C@@H](O)[C@@H](O)[C@H](O)[C@H](CO)O1 LNQCUTNLHUQZLR-VNPYQEQNSA-N 0.000 description 1
- 206010065973 Iron Overload Diseases 0.000 description 1
- 241000710842 Japanese encephalitis virus Species 0.000 description 1
- 206010023330 Keloid scar Diseases 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 241000710770 Langat virus Species 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229930195725 Mannitol Natural products 0.000 description 1
- 241000608292 Mayaro virus Species 0.000 description 1
- 241000710185 Mengo virus Species 0.000 description 1
- 206010027476 Metastases Diseases 0.000 description 1
- 241000711466 Murine hepatitis virus Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- RWKMMQRQJJXJNX-UHFFFAOYSA-N N-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)NC=2C(=CC=CC=2)Cl)=NO1 RWKMMQRQJJXJNX-UHFFFAOYSA-N 0.000 description 1
- KDYWKUHLQPGVBV-UHFFFAOYSA-N N-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-3-(2-hydroxyphenyl)-1H-pyrazole-5-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=NN1 KDYWKUHLQPGVBV-UHFFFAOYSA-N 0.000 description 1
- BVXVSCNTHVGDRU-UHFFFAOYSA-N N-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-5-(2-hydroxyphenyl)-1,2-oxazole-3-carboxamide Chemical compound OC1=CC=CC=C1C1=CC(C(=O)NCC(=O)N2CCC(CC2)OC=2C(=CC=CC=2)Cl)=NO1 BVXVSCNTHVGDRU-UHFFFAOYSA-N 0.000 description 1
- 125000000815 N-oxide group Chemical group 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- 208000012902 Nervous system disease Diseases 0.000 description 1
- 208000025966 Neurological disease Diseases 0.000 description 1
- 241000714209 Norwalk virus Species 0.000 description 1
- 241000725177 Omsk hemorrhagic fever virus Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 206010033307 Overweight Diseases 0.000 description 1
- 206010033645 Pancreatitis Diseases 0.000 description 1
- 208000002606 Paramyxoviridae Infections Diseases 0.000 description 1
- 241001494479 Pecora Species 0.000 description 1
- 208000018262 Peripheral vascular disease Diseases 0.000 description 1
- 241000710778 Pestivirus Species 0.000 description 1
- 241000286209 Phasianidae Species 0.000 description 1
- 241000709664 Picornaviridae Species 0.000 description 1
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical class C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 1
- 241001135549 Porcine epidemic diarrhea virus Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001533393 Potyviridae Species 0.000 description 1
- 241000710078 Potyvirus Species 0.000 description 1
- 241000710884 Powassan virus Species 0.000 description 1
- 206010036618 Premenstrual syndrome Diseases 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-N R-2-phenyl-2-hydroxyacetic acid Natural products OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
- 241000903330 Rabbit coronavirus Species 0.000 description 1
- 241001428933 Rat coronavirus Species 0.000 description 1
- 208000017442 Retinal disease Diseases 0.000 description 1
- 206010038923 Retinopathy Diseases 0.000 description 1
- 241000710942 Ross River virus Species 0.000 description 1
- 241000710799 Rubella virus Species 0.000 description 1
- 241001533356 Rymovirus Species 0.000 description 1
- 101150048395 SCD gene Proteins 0.000 description 1
- 101100101423 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) UBI4 gene Proteins 0.000 description 1
- 101150042597 Scd2 gene Proteins 0.000 description 1
- 241000710961 Semliki Forest virus Species 0.000 description 1
- 241000710960 Sindbis virus Species 0.000 description 1
- 241000710888 St. Louis encephalitis virus Species 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 102100033930 Stearoyl-CoA desaturase 5 Human genes 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Chemical class OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 241000282887 Suidae Species 0.000 description 1
- 208000004006 Tick-borne encephalitis Diseases 0.000 description 1
- 241000710771 Tick-borne encephalitis virus Species 0.000 description 1
- 241000710924 Togaviridae Species 0.000 description 1
- 241000711508 Turkey coronavirus Species 0.000 description 1
- 206010067584 Type 1 diabetes mellitus Diseases 0.000 description 1
- 229910052770 Uranium Inorganic materials 0.000 description 1
- 108010062497 VLDL Lipoproteins Proteins 0.000 description 1
- 241000710959 Venezuelan equine encephalitis virus Species 0.000 description 1
- 206010051511 Viral diarrhoea Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- 208000010094 Visna Diseases 0.000 description 1
- 239000004164 Wax ester Substances 0.000 description 1
- 241000710886 West Nile virus Species 0.000 description 1
- 241000710951 Western equine encephalitis virus Species 0.000 description 1
- 230000003187 abdominal effect Effects 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 206010000496 acne Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 238000010171 animal model Methods 0.000 description 1
- 208000022531 anorexia Diseases 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-L aspartate group Chemical class N[C@@H](CC(=O)[O-])C(=O)[O-] CKLJMWTZIZZHCS-REOHCLBHSA-L 0.000 description 1
- 208000006673 asthma Diseases 0.000 description 1
- 244000309743 astrovirus Species 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 150000001558 benzoic acid derivatives Chemical class 0.000 description 1
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- DMVOXQPQNTYEKQ-UHFFFAOYSA-N biphenyl-4-amine Chemical compound C1=CC(N)=CC=C1C1=CC=CC=C1 DMVOXQPQNTYEKQ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M bisulphate group Chemical group S([O-])(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical class O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000004648 butanoic acid derivatives Chemical class 0.000 description 1
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 201000011510 cancer Diseases 0.000 description 1
- 230000036952 cancer formation Effects 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 1
- 231100000504 carcinogenesis Toxicity 0.000 description 1
- 230000001364 causal effect Effects 0.000 description 1
- 208000026106 cerebrovascular disease Diseases 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000013330 chicken meat Nutrition 0.000 description 1
- 150000001840 cholesterol esters Chemical class 0.000 description 1
- 235000019417 choline salt Nutrition 0.000 description 1
- 150000001860 citric acid derivatives Chemical class 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000002648 combination therapy Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 208000029078 coronary artery disease Diseases 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 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
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 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
- FDKLLWKMYAMLIF-UHFFFAOYSA-N cyclopropane-1,1-dicarboxylic acid Chemical compound OC(=O)C1(C(O)=O)CC1 FDKLLWKMYAMLIF-UHFFFAOYSA-N 0.000 description 1
- 206010061428 decreased appetite Diseases 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 208000025729 dengue disease Diseases 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000001975 deuterium Chemical class 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000005911 diet Nutrition 0.000 description 1
- 230000037213 diet Effects 0.000 description 1
- KYYUCZOHNYSLFV-UHFFFAOYSA-N diethyl cyclopropane-1,1-dicarboxylate Chemical compound CCOC(=O)C1(C(=O)OCC)CC1 KYYUCZOHNYSLFV-UHFFFAOYSA-N 0.000 description 1
- 125000005043 dihydropyranyl group Chemical group O1C(CCC=C1)* 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 239000007884 disintegrant Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical class CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 238000009509 drug development Methods 0.000 description 1
- 238000007876 drug discovery Methods 0.000 description 1
- 201000008865 drug-induced hepatitis Diseases 0.000 description 1
- 210000005069 ears Anatomy 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000003821 enantio-separation Methods 0.000 description 1
- 201000002491 encephalomyelitis Diseases 0.000 description 1
- 230000019439 energy homeostasis Effects 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 201000008220 erythropoietic protoporphyria Diseases 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- BTUJZIGPAGODTR-UHFFFAOYSA-N ethyl 2,4-dioxo-4-(4-phenylmethoxyphenyl)butanoate Chemical compound C1=CC(C(=O)CC(=O)C(=O)OCC)=CC=C1OCC1=CC=CC=C1 BTUJZIGPAGODTR-UHFFFAOYSA-N 0.000 description 1
- QTCLCIIEFPASIP-UHFFFAOYSA-N ethyl 2-(4,6-dioxocyclohex-2-en-1-yl)butanoate Chemical compound C(C)OC(C(CC)C1C(CC(C=C1)=O)=O)=O QTCLCIIEFPASIP-UHFFFAOYSA-N 0.000 description 1
- DPCNNYQSXXLCNW-UHFFFAOYSA-N ethyl 2-[(5-phenyl-1,2-oxazole-3-carbonyl)amino]acetate Chemical compound O1N=C(C(=O)NCC(=O)OCC)C=C1C1=CC=CC=C1 DPCNNYQSXXLCNW-UHFFFAOYSA-N 0.000 description 1
- QXBCPGQHNLZBNL-UHFFFAOYSA-N ethyl 2-[(5-phenylpyridine-2-carbonyl)amino]acetate Chemical compound C1=NC(C(=O)NCC(=O)OCC)=CC=C1C1=CC=CC=C1 QXBCPGQHNLZBNL-UHFFFAOYSA-N 0.000 description 1
- QJYCIKQLKFPZMB-UHFFFAOYSA-N ethyl 2-[(6-anilinopyridine-3-carbonyl)amino]acetate Chemical compound N1=CC(C(=O)NCC(=O)OCC)=CC=C1NC1=CC=CC=C1 QJYCIKQLKFPZMB-UHFFFAOYSA-N 0.000 description 1
- NTNZTEQNFHNYBC-UHFFFAOYSA-N ethyl 2-aminoacetate Chemical compound CCOC(=O)CN NTNZTEQNFHNYBC-UHFFFAOYSA-N 0.000 description 1
- XUSPYXHOXCPIAP-UHFFFAOYSA-N ethyl 3-(3-phenylmethoxyphenyl)-1h-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OCC)C=C1C1=CC=CC(OCC=2C=CC=CC=2)=C1 XUSPYXHOXCPIAP-UHFFFAOYSA-N 0.000 description 1
- XGOMKBCULHQOGC-UHFFFAOYSA-N ethyl 3-(4-hydroxyphenyl)-1H-pyrazole-5-carboxylate Chemical compound N1N=C(C(=O)OCC)C=C1C1=CC=C(O)C=C1 XGOMKBCULHQOGC-UHFFFAOYSA-N 0.000 description 1
- DSCUGMAJSWDJBR-UHFFFAOYSA-N ethyl 3-[4-(2-chlorophenoxy)piperidin-1-yl]-3-oxopropanoate Chemical compound C1CN(C(=O)CC(=O)OCC)CCC1OC1=CC=CC=C1Cl DSCUGMAJSWDJBR-UHFFFAOYSA-N 0.000 description 1
- VEPCCHPCDSGOGF-UHFFFAOYSA-N ethyl 3-oxo-3-(4-phenylanilino)propanoate Chemical compound C1=CC(NC(=O)CC(=O)OCC)=CC=C1C1=CC=CC=C1 VEPCCHPCDSGOGF-UHFFFAOYSA-N 0.000 description 1
- ILDJJTQWIZLGPO-UHFFFAOYSA-N ethyl 6-chloropyridine-3-carboxylate Chemical compound CCOC(=O)C1=CC=C(Cl)N=C1 ILDJJTQWIZLGPO-UHFFFAOYSA-N 0.000 description 1
- LJJVZJSGXHJIPP-UHFFFAOYSA-N ethylpentyl Chemical group [CH2+]CCC[CH]C[CH2-] LJJVZJSGXHJIPP-UHFFFAOYSA-N 0.000 description 1
- 125000006125 ethylsulfonyl group Chemical group 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 201000005884 exanthem Diseases 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 208000029944 familial hemophagocytic lymphohistiocytosis type 1 Diseases 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229960002598 fumaric acid Drugs 0.000 description 1
- 235000011087 fumaric acid Nutrition 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 239000008103 glucose Substances 0.000 description 1
- 150000002315 glycerophosphates Chemical class 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000001492 haemagglutinating effect Effects 0.000 description 1
- 230000005802 health problem Effects 0.000 description 1
- 208000019622 heart disease Diseases 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 201000010284 hepatitis E Diseases 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical class CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical class CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- SXWRTZOXMUOJER-UHFFFAOYSA-N hydron;piperidin-4-one;chloride;hydrate Chemical compound O.Cl.O=C1CCNCC1 SXWRTZOXMUOJER-UHFFFAOYSA-N 0.000 description 1
- 208000020346 hyperlipoproteinemia Diseases 0.000 description 1
- 210000000987 immune system Anatomy 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 201000006747 infectious mononucleosis Diseases 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 206010022000 influenza Diseases 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 108010047623 iridine Proteins 0.000 description 1
- 230000000302 ischemic effect Effects 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 230000000155 isotopic effect Effects 0.000 description 1
- 125000003971 isoxazolinyl group Chemical group 0.000 description 1
- 150000003903 lactic acid esters Chemical class 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 239000000865 liniment Substances 0.000 description 1
- 230000037356 lipid metabolism Effects 0.000 description 1
- 230000004132 lipogenesis Effects 0.000 description 1
- 230000008604 lipoprotein metabolism Effects 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011976 maleic acid Chemical class 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 230000036210 malignancy Effects 0.000 description 1
- 230000003211 malignant effect Effects 0.000 description 1
- CGJMROBVSBIBKP-UHFFFAOYSA-N malonamic acid Chemical compound NC(=O)CC(O)=O CGJMROBVSBIBKP-UHFFFAOYSA-N 0.000 description 1
- 229960002510 mandelic acid Drugs 0.000 description 1
- 239000000594 mannitol Substances 0.000 description 1
- 235000010355 mannitol Nutrition 0.000 description 1
- 235000013372 meat Nutrition 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 208000030159 metabolic disease Diseases 0.000 description 1
- 230000037353 metabolic pathway Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- KTPWETRNSUKEME-UHFFFAOYSA-N methoxymethane;trifluoroborane Chemical compound COC.FB(F)F KTPWETRNSUKEME-UHFFFAOYSA-N 0.000 description 1
- AVPKQULHGRGLBO-UHFFFAOYSA-N methyl 1-[(4-phenylphenyl)carbamoyl]cyclopropane-1-carboxylate Chemical compound C=1C=C(C=2C=CC=CC=2)C=CC=1NC(=O)C1(C(=O)OC)CC1 AVPKQULHGRGLBO-UHFFFAOYSA-N 0.000 description 1
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002757 morpholinyl group Chemical group 0.000 description 1
- 210000004400 mucous membrane Anatomy 0.000 description 1
- 201000006417 multiple sclerosis Diseases 0.000 description 1
- 230000035772 mutation Effects 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- DDUJGDYZGFWDFN-UHFFFAOYSA-N n-(2,3-dimethylphenyl)piperidin-4-amine Chemical compound CC1=CC=CC(NC2CCNCC2)=C1C DDUJGDYZGFWDFN-UHFFFAOYSA-N 0.000 description 1
- BZXFRLHYZOEMTG-UHFFFAOYSA-N n-(2-bromophenyl)sulfanylpiperidin-4-amine;hydrochloride Chemical compound Cl.BrC1=CC=CC=C1SNC1CCNCC1 BZXFRLHYZOEMTG-UHFFFAOYSA-N 0.000 description 1
- HVRZFWSRCMXDGO-UHFFFAOYSA-N n-(2-chlorophenoxy)piperidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC=C1ONC1CCNCC1 HVRZFWSRCMXDGO-UHFFFAOYSA-N 0.000 description 1
- QGZRNDFESGXJLO-UHFFFAOYSA-N n-(2-chlorophenyl)sulfanylpiperidin-4-amine;hydrochloride Chemical compound Cl.ClC1=CC=CC=C1SNC1CCNCC1 QGZRNDFESGXJLO-UHFFFAOYSA-N 0.000 description 1
- DGXULSZBGQRRHG-UHFFFAOYSA-N n-(2-tert-butylphenyl)piperidin-4-amine Chemical compound CC(C)(C)C1=CC=CC=C1NC1CCNCC1 DGXULSZBGQRRHG-UHFFFAOYSA-N 0.000 description 1
- REKCWASNQGVOED-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenoxy]piperidin-4-amine;hydrochloride Chemical compound Cl.FC(F)(F)C1=CC=CC=C1ONC1CCNCC1 REKCWASNQGVOED-UHFFFAOYSA-N 0.000 description 1
- JCJUDXXSMQFAEQ-UHFFFAOYSA-N n-[2-(trifluoromethyl)phenyl]piperidin-4-amine Chemical compound FC(F)(F)C1=CC=CC=C1NC1CCNCC1 JCJUDXXSMQFAEQ-UHFFFAOYSA-N 0.000 description 1
- XPLOYTMHUQOYEC-UHFFFAOYSA-N n-[2-[4-(2,4-dimethylanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC(C)=CC=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 XPLOYTMHUQOYEC-UHFFFAOYSA-N 0.000 description 1
- QIIFXXGOKSHPRE-UHFFFAOYSA-N n-[2-[4-(2-bromoanilino)piperidin-1-yl]-2-oxoethyl]-4-phenylbenzamide Chemical compound BrC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 QIIFXXGOKSHPRE-UHFFFAOYSA-N 0.000 description 1
- ZRNIUDKBANEGCD-UHFFFAOYSA-N n-[2-[4-(2-bromophenoxy)piperidin-1-yl]-2-oxoethyl]-4-phenylbenzamide Chemical compound BrC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 ZRNIUDKBANEGCD-UHFFFAOYSA-N 0.000 description 1
- LTCKSRPBZATNQS-UHFFFAOYSA-N n-[2-[4-(2-chloro-5-fluorophenoxy)piperidin-1-yl]-2-oxoethyl]-5-phenylpyridine-2-carboxamide Chemical compound FC1=CC=C(Cl)C(OC2CCN(CC2)C(=O)CNC(=O)C=2N=CC(=CC=2)C=2C=CC=CC=2)=C1 LTCKSRPBZATNQS-UHFFFAOYSA-N 0.000 description 1
- XOEFGDDDWBYUIB-UHFFFAOYSA-N n-[2-[4-(2-chloro-n-methylanilino)piperidin-1-yl]-2-oxoethyl]-4-phenylbenzamide Chemical compound C=1C=CC=C(Cl)C=1N(C)C(CC1)CCN1C(=O)CNC(=O)C(C=C1)=CC=C1C1=CC=CC=C1 XOEFGDDDWBYUIB-UHFFFAOYSA-N 0.000 description 1
- YXWTVUAGHOZUIC-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 YXWTVUAGHOZUIC-UHFFFAOYSA-N 0.000 description 1
- UEMGNPVRLDFYRX-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-4-phenylbenzamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 UEMGNPVRLDFYRX-UHFFFAOYSA-N 0.000 description 1
- BWFZXKALYDFNKM-UHFFFAOYSA-N n-[2-[4-(2-chloroanilino)piperidin-1-yl]-2-oxoethyl]-5-phenyl-1,2-oxazole-3-carboxamide Chemical compound ClC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C2=NOC(=C2)C=2C=CC=CC=2)CC1 BWFZXKALYDFNKM-UHFFFAOYSA-N 0.000 description 1
- QWOXZZIDYAZGKM-UHFFFAOYSA-N n-[2-[4-(2-chlorophenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound ClC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 QWOXZZIDYAZGKM-UHFFFAOYSA-N 0.000 description 1
- PQLJHGORBYLEKR-UHFFFAOYSA-N n-[2-[4-(2-cyanophenoxy)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound C1CC(OC=2C(=CC=CC=2)C#N)CCN1C(=O)CNC(=O)C(=NN1)C=C1C1=CC=CC=C1 PQLJHGORBYLEKR-UHFFFAOYSA-N 0.000 description 1
- JBVNMGBOMGFTEA-UHFFFAOYSA-N n-[2-[4-(2-methylanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CC1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 JBVNMGBOMGFTEA-UHFFFAOYSA-N 0.000 description 1
- FOOPBMPCPXTHPU-UHFFFAOYSA-N n-[2-[4-(5-bromo-2-methoxyanilino)piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound COC1=CC=C(Br)C=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 FOOPBMPCPXTHPU-UHFFFAOYSA-N 0.000 description 1
- ODVMMVWKYBXLCA-UHFFFAOYSA-N n-[2-[4-[2-(hydroxyiminomethyl)phenoxy]piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound ON=CC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 ODVMMVWKYBXLCA-UHFFFAOYSA-N 0.000 description 1
- WVNYGZREPZQXRL-UHFFFAOYSA-N n-[2-[4-[2-(methoxyiminomethyl)phenoxy]piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound CON=CC1=CC=CC=C1OC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 WVNYGZREPZQXRL-UHFFFAOYSA-N 0.000 description 1
- XXZFYGVUMOUZCB-UHFFFAOYSA-N n-[2-[4-[4-fluoro-2-(trifluoromethyl)anilino]piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound FC(F)(F)C1=CC(F)=CC=C1NC1CCN(C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)CC1 XXZFYGVUMOUZCB-UHFFFAOYSA-N 0.000 description 1
- FCMPOSVCDYMBBY-UHFFFAOYSA-N n-[2-[4-[5-fluoro-2-(trifluoromethyl)anilino]piperidin-1-yl]-2-oxoethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound FC1=CC=C(C(F)(F)F)C(NC2CCN(CC2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 FCMPOSVCDYMBBY-UHFFFAOYSA-N 0.000 description 1
- NXLHLAPPWKQPGM-UHFFFAOYSA-N n-[2-[4-[n-methyl-2-(trifluoromethyl)anilino]piperidin-1-yl]-2-oxoethyl]-5-phenyl-1,2-oxazole-3-carboxamide Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C(CC1)CCN1C(=O)CNC(=O)C(=NO1)C=C1C1=CC=CC=C1 NXLHLAPPWKQPGM-UHFFFAOYSA-N 0.000 description 1
- XJJQRNRRAFNMCA-UHFFFAOYSA-N n-[2-oxo-2-[4-[2-(trifluoromethyl)anilino]piperidin-1-yl]ethyl]-4-phenylbenzamide Chemical compound FC(F)(F)C1=CC=CC=C1NC1CCN(C(=O)CNC(=O)C=2C=CC(=CC=2)C=2C=CC=CC=2)CC1 XJJQRNRRAFNMCA-UHFFFAOYSA-N 0.000 description 1
- DSLPYHOJHSHWOO-UHFFFAOYSA-N n-[2-oxo-2-[4-[3-(trifluoromethyl)phenoxy]piperidin-1-yl]ethyl]-3-phenyl-1h-pyrazole-5-carboxamide Chemical compound FC(F)(F)C1=CC=CC(OC2CCN(CC2)C(=O)CNC(=O)C2=NNC(=C2)C=2C=CC=CC=2)=C1 DSLPYHOJHSHWOO-UHFFFAOYSA-N 0.000 description 1
- TVCROBWSLSJLBF-UHFFFAOYSA-N n-[5-fluoro-2-(trifluoromethyl)phenyl]piperidin-4-amine;dihydrochloride Chemical compound Cl.Cl.FC1=CC=C(C(F)(F)F)C(NC2CCNCC2)=C1 TVCROBWSLSJLBF-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical class C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- 125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000002814 niacins Chemical class 0.000 description 1
- 235000001968 nicotinic acid Nutrition 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- XDUHQPOXLUAVEE-BPMMELMSSA-N oleoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCC\C=C/CCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 XDUHQPOXLUAVEE-BPMMELMSSA-N 0.000 description 1
- 239000006186 oral dosage form Substances 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 125000001715 oxadiazolyl group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 125000004287 oxazol-2-yl group Chemical group [H]C1=C([H])N=C(*)O1 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- MNBKLUUYKPBKDU-BBECNAHFSA-N palmitoyl-CoA Chemical compound O[C@@H]1[C@H](OP(O)(O)=O)[C@@H](COP(O)(=O)OP(O)(=O)OCC(C)(C)[C@@H](O)C(=O)NCCC(=O)NCCSC(=O)CCCCCCCCCCCCCCC)O[C@H]1N1C2=NC=NC(N)=C2N=C1 MNBKLUUYKPBKDU-BBECNAHFSA-N 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 230000008506 pathogenesis Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- JRKICGRDRMAZLK-UHFFFAOYSA-L persulfate group Chemical group S(=O)(=O)([O-])OOS(=O)(=O)[O-] JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940124531 pharmaceutical excipient Drugs 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 150000003904 phospholipids Chemical class 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical class OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 125000004193 piperazinyl group Chemical group 0.000 description 1
- BCIIMDOZSUCSEN-UHFFFAOYSA-N piperidin-4-amine Chemical compound NC1CCNCC1 BCIIMDOZSUCSEN-UHFFFAOYSA-N 0.000 description 1
- FKUNXXGNWCRVNU-UHFFFAOYSA-N piperidin-4-ol;hydrate;hydrochloride Chemical compound O.Cl.OC1CCNCC1 FKUNXXGNWCRVNU-UHFFFAOYSA-N 0.000 description 1
- IRWXYFWBGITFAG-UHFFFAOYSA-N piperidin-4-yl methanesulfonate Chemical compound CS(=O)(=O)OC1CCNCC1 IRWXYFWBGITFAG-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 125000005547 pivalate group Chemical group 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 230000035935 pregnancy Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 208000020016 psychiatric disease Diseases 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 206010037844 rash Diseases 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 238000006268 reductive amination reaction Methods 0.000 description 1
- 230000003362 replicative effect Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004141 reverse cholesterol transport Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 206010039073 rheumatoid arthritis Diseases 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000009097 single-agent therapy Methods 0.000 description 1
- 201000009890 sinusitis Diseases 0.000 description 1
- 210000002027 skeletal muscle Anatomy 0.000 description 1
- 208000017520 skin disease Diseases 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- UKLNMMHNWFDKNT-UHFFFAOYSA-M sodium chlorite Chemical compound [Na+].[O-]Cl=O UKLNMMHNWFDKNT-UHFFFAOYSA-M 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- LZCVVMQABORALM-UHFFFAOYSA-N spiro[2.5]octyl Chemical group [CH]1CC11CCCCC1 LZCVVMQABORALM-UHFFFAOYSA-N 0.000 description 1
- GAJDDVONBAWAGB-UHFFFAOYSA-N spiro[2.6]nonyl Chemical group [CH]1CC11CCCCCC1 GAJDDVONBAWAGB-UHFFFAOYSA-N 0.000 description 1
- LMUMMJCCZMWLEN-UHFFFAOYSA-N spiro[3.3]heptyl Chemical group [CH]1CCC11CCC1 LMUMMJCCZMWLEN-UHFFFAOYSA-N 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 125000005017 substituted alkenyl group Chemical group 0.000 description 1
- 125000004426 substituted alkynyl group Chemical group 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- QJEXFQIDEHSWNM-UHFFFAOYSA-N sulfonylmethane hydrochloride Chemical compound Cl.C=S(=O)=O QJEXFQIDEHSWNM-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 150000003899 tartaric acid esters Chemical class 0.000 description 1
- CMHLWPWBXGCPGW-UHFFFAOYSA-N tert-butyl 4-(2,4-dimethylanilino)piperidine-1-carboxylate Chemical compound CC1=CC(C)=CC=C1NC1CCN(C(=O)OC(C)(C)C)CC1 CMHLWPWBXGCPGW-UHFFFAOYSA-N 0.000 description 1
- BSKBAIKXWXHBKK-UHFFFAOYSA-N tert-butyl 4-(2,5-difluorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(F)=CC=C1F BSKBAIKXWXHBKK-UHFFFAOYSA-N 0.000 description 1
- KYIXHOSOZYFWMS-UHFFFAOYSA-N tert-butyl 4-(2,5-dimethylanilino)piperidine-1-carboxylate Chemical compound CC1=CC=C(C)C(NC2CCN(CC2)C(=O)OC(C)(C)C)=C1 KYIXHOSOZYFWMS-UHFFFAOYSA-N 0.000 description 1
- KMBSMBPVRYKLIA-UHFFFAOYSA-N tert-butyl 4-(2-chloro-5-fluorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC(F)=CC=C1Cl KMBSMBPVRYKLIA-UHFFFAOYSA-N 0.000 description 1
- YBZRUUFGFIXTCZ-UHFFFAOYSA-N tert-butyl 4-(2-chloro-n-methylanilino)piperidine-1-carboxylate Chemical compound C=1C=CC=C(Cl)C=1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 YBZRUUFGFIXTCZ-UHFFFAOYSA-N 0.000 description 1
- QMADZUIDYBWTFY-UHFFFAOYSA-N tert-butyl 4-(2-chlorophenoxy)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1Cl QMADZUIDYBWTFY-UHFFFAOYSA-N 0.000 description 1
- BOGXZBVKQDEROE-UHFFFAOYSA-N tert-butyl 4-(2-tert-butylanilino)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1NC1=CC=CC=C1C(C)(C)C BOGXZBVKQDEROE-UHFFFAOYSA-N 0.000 description 1
- NMYLUTZGNZLFET-UHFFFAOYSA-N tert-butyl 4-[2-(trifluoromethyl)phenoxy]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1OC1=CC=CC=C1C(F)(F)F NMYLUTZGNZLFET-UHFFFAOYSA-N 0.000 description 1
- PBEAHUOAXQPWRU-UHFFFAOYSA-N tert-butyl 4-[n-methyl-2-(trifluoromethyl)anilino]piperidine-1-carboxylate Chemical compound C=1C=CC=C(C(F)(F)F)C=1N(C)C1CCN(C(=O)OC(C)(C)C)CC1 PBEAHUOAXQPWRU-UHFFFAOYSA-N 0.000 description 1
- PWQLFIKTGRINFF-UHFFFAOYSA-N tert-butyl 4-hydroxypiperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(O)CC1 PWQLFIKTGRINFF-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000005958 tetrahydrothienyl group Chemical group 0.000 description 1
- PVGHNTXQMCYYGF-UHFFFAOYSA-N thiadiazol-5-amine Chemical compound NC1=CN=NS1 PVGHNTXQMCYYGF-UHFFFAOYSA-N 0.000 description 1
- 125000005302 thiazolylmethyl group Chemical group [H]C1=C([H])N=C(S1)C([H])([H])* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 1
- 150000003567 thiocyanates Chemical class 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical compound SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
- 125000005490 tosylate group Chemical group 0.000 description 1
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical class CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 235000019386 wax ester Nutrition 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
- 230000004580 weight loss Effects 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- 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
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Child & Adolescent Psychology (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (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 |
|---|---|---|---|
| IN575KO2008 | 2008-03-20 | ||
| US4948008P | 2008-05-01 | 2008-05-01 | |
| PCT/US2009/037835 WO2009117676A2 (en) | 2008-03-20 | 2009-03-20 | Novel piperidine derivatives as inhibitors of stearoyl-coa desaturase |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| MX2010010241A true MX2010010241A (es) | 2010-12-06 |
Family
ID=41089526
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MX2010010241A MX2010010241A (es) | 2008-03-20 | 2009-03-20 | Derivados de piperidina novedosos como inhibidores de estearoil-coa desaturasa. |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8129376B2 (OSRAM) |
| EP (1) | EP2268143A4 (OSRAM) |
| JP (1) | JP2011518774A (OSRAM) |
| KR (1) | KR20100134680A (OSRAM) |
| CN (1) | CN102036558A (OSRAM) |
| AU (1) | AU2009225441B2 (OSRAM) |
| BR (1) | BRPI0909183A2 (OSRAM) |
| CA (1) | CA2719000A1 (OSRAM) |
| IL (1) | IL208232A0 (OSRAM) |
| MX (1) | MX2010010241A (OSRAM) |
| NZ (1) | NZ588633A (OSRAM) |
| RU (1) | RU2010142937A (OSRAM) |
| WO (1) | WO2009117676A2 (OSRAM) |
| ZA (1) | ZA201007252B (OSRAM) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2009051244A1 (ja) | 2007-10-18 | 2009-04-23 | Takeda Pharmaceutical Company Limited | 複素環化合物 |
| US8642583B2 (en) | 2008-10-30 | 2014-02-04 | Janssen Pharmaceutica Nv | Serotonin receptor modulators |
| SG182662A1 (en) | 2010-01-28 | 2012-08-30 | Harvard College | Compositions and methods for enhancing proteasome activity |
| JP5996532B2 (ja) | 2010-07-15 | 2016-09-21 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングBayer Intellectual Property GmbH | 有害生物防除剤としての新規複素環式化合物 |
| WO2012154967A1 (en) | 2011-05-12 | 2012-11-15 | Proteostasis Therapeutics, Inc. | Proteostasis regulators |
| NO2686520T3 (OSRAM) | 2011-06-06 | 2018-03-17 | ||
| FR3000491B1 (fr) * | 2012-09-27 | 2015-08-28 | Univ Lille Ii Droit & Sante | Composes utilisables dans le traitement des infections mycobacteriennes |
| CN103772267A (zh) * | 2012-10-24 | 2014-05-07 | 常州化学研究所 | 一种二苯胺制备咔唑的方法 |
| US9849135B2 (en) | 2013-01-25 | 2017-12-26 | President And Fellows Of Harvard College | USP14 inhibitors for treating or preventing viral infections |
| WO2015073528A1 (en) | 2013-11-12 | 2015-05-21 | Proteostasis Therapeutics, Inc. | Proteasome activity enhancing compounds |
| UA118034C2 (uk) * | 2013-11-14 | 2018-11-12 | Елі Ліллі Енд Компані | Заміщений піперидилетилпіримідин як інгібітор грелін-o-ацилтрансферази |
| SG11201607920RA (en) | 2014-04-04 | 2016-10-28 | X Rx Inc | Substituted spirocyclic inhibitors of autotaxin |
| BR112016024473A2 (pt) * | 2014-04-23 | 2018-01-23 | X Rx Inc | composto, composição farmacêutica, e, método para tratamento de uma doença e/ou condição |
| US20160047307A1 (en) * | 2014-08-15 | 2016-02-18 | General Electric Company | Power train architectures with low-loss lubricant bearings and low-density materials |
| WO2016054560A1 (en) | 2014-10-02 | 2016-04-07 | Flatley Discovery Lab | Isoxazole compounds and methods for the treatment of cystic fibrosis |
| CN106432232A (zh) * | 2016-09-18 | 2017-02-22 | 苏州汉德创宏生化科技有限公司 | 1‑哌啶‑4‑基‑1,3‑二氢‑咪唑[4,5‑b]吡啶‑2‑酮的合成方法 |
| US11384081B2 (en) | 2016-09-20 | 2022-07-12 | Centre Leon Berard | Benzoimidazole derivatives as anticancer agents |
| US11970486B2 (en) | 2016-10-24 | 2024-04-30 | Janssen Pharmaceutica Nv | Compounds and uses thereof |
| TW201822637A (zh) | 2016-11-07 | 2018-07-01 | 德商拜耳廠股份有限公司 | 用於控制動物害蟲的經取代磺醯胺類 |
| JP2020514293A (ja) | 2017-01-06 | 2020-05-21 | ユマニティ セラピューティクス,インコーポレーテッド | 神経障害を治療する方法 |
| CA3083000A1 (en) | 2017-10-24 | 2019-05-02 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| CN107663184A (zh) * | 2017-11-15 | 2018-02-06 | 上海皓伯化工科技有限公司 | 一种N‑Boc‑4‑羟基哌啶的合成方法 |
| EP3768269B1 (en) | 2018-03-23 | 2025-08-20 | Janssen Pharmaceutica NV | Compounds and uses thereof |
| US10919885B2 (en) | 2018-04-25 | 2021-02-16 | Yumanity Therapeutics, Inc. | Compounds and uses thereof |
| MX2020011845A (es) | 2018-05-09 | 2021-01-15 | Akebia Therapeutics Inc | Proceso para preparar acido 2-[[5-(3-clorofenil)-3-hidroxipiridina -2-carbonil]amino]acetico. |
| TWI767148B (zh) | 2018-10-10 | 2022-06-11 | 美商弗瑪治療公司 | 抑制脂肪酸合成酶(fasn) |
| MX2021008903A (es) * | 2019-01-24 | 2021-11-04 | Yumanity Therapeutics Inc | Compuestos y usos de los mismos. |
| CA3148310A1 (en) * | 2019-09-13 | 2021-03-18 | Jun Qi | Kdm inhibitors and uses thereof |
| CN110845396B (zh) * | 2019-11-07 | 2023-01-20 | 宿迁联盛科技股份有限公司 | 一种2,2,6,6-四甲基-4-哌啶胺类化合物的制备方法 |
| EA202192047A1 (ru) | 2019-11-13 | 2021-12-08 | Юманити Терапьютикс, Инк. | Соединения и их применение |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU6659090A (en) | 1989-11-16 | 1991-06-13 | Warner-Lambert Company | Acat inhibitors |
| US5459151A (en) | 1993-04-30 | 1995-10-17 | American Home Products Corporation | N-acyl substituted phenyl piperidines as bronchodilators and antiinflammatory agents |
| US6334997B1 (en) | 1994-03-25 | 2002-01-01 | Isotechnika, Inc. | Method of using deuterated calcium channel blockers |
| CA2186371A1 (en) | 1994-03-25 | 1995-10-05 | Robert T. Foster | Enhancement of the efficacy of dihydropyridines by deuteration |
| CA2398940C (en) | 2000-02-24 | 2012-02-21 | Xenon Genetics, Inc. | Methods and compositions using stearoyl-coa desaturase to identify triglyceride reducing therapeutic agents |
| DE60134995D1 (de) | 2000-09-26 | 2008-09-04 | Xenon Pharmaceuticals Inc | Verfahren und zusammensetzungen, die eine stearoyl-coa desuturase-hscd5 verwenden |
| EP1597256A1 (en) * | 2003-02-21 | 2005-11-23 | Pfizer Inc. | N-heterocyclyl-substituted amino-thiazole derivatives as protein kinase inhibitors |
| KR20050045927A (ko) | 2003-11-12 | 2005-05-17 | 주식회사 엘지생명과학 | 멜라노코틴 수용체의 항진제 |
| JP4787529B2 (ja) * | 2004-04-09 | 2011-10-05 | 大塚製薬株式会社 | 医薬組成物 |
| MX2007003319A (es) * | 2004-09-20 | 2007-06-05 | Xenon Pharmaceuticals Inc | Derivados heterociclicos y su uso como agentes terapeuticos. |
| CN101084212A (zh) * | 2004-09-20 | 2007-12-05 | 泽农医药公司 | 杂环衍生物及其作为硬脂酰CoA去饱和酶介导剂的用途 |
| CN101090724A (zh) * | 2004-09-20 | 2007-12-19 | 泽农医药公司 | 用于抑制人硬脂酰CoA去饱和酶的吡啶衍生物 |
| WO2008157844A1 (en) * | 2007-06-21 | 2008-12-24 | Forest Laboratories Holdings Limited | Novel piperazine derivatives as inhibitors of stearoyl-coa desaturase |
| JPWO2009119537A1 (ja) * | 2008-03-26 | 2011-07-21 | 第一三共株式会社 | ヒドロキシキノキサリンカルボキサミド誘導体 |
-
2009
- 2009-03-20 RU RU2010142937/04A patent/RU2010142937A/ru unknown
- 2009-03-20 US US12/408,486 patent/US8129376B2/en not_active Expired - Fee Related
- 2009-03-20 EP EP09721822A patent/EP2268143A4/en not_active Withdrawn
- 2009-03-20 WO PCT/US2009/037835 patent/WO2009117676A2/en not_active Ceased
- 2009-03-20 NZ NZ588633A patent/NZ588633A/en not_active IP Right Cessation
- 2009-03-20 CN CN2009801176982A patent/CN102036558A/zh active Pending
- 2009-03-20 KR KR1020107023415A patent/KR20100134680A/ko not_active Ceased
- 2009-03-20 AU AU2009225441A patent/AU2009225441B2/en not_active Expired - Fee Related
- 2009-03-20 BR BRPI0909183-1A patent/BRPI0909183A2/pt not_active IP Right Cessation
- 2009-03-20 MX MX2010010241A patent/MX2010010241A/es active IP Right Grant
- 2009-03-20 JP JP2011500989A patent/JP2011518774A/ja active Pending
- 2009-03-20 CA CA2719000A patent/CA2719000A1/en not_active Abandoned
-
2010
- 2010-09-19 IL IL208232A patent/IL208232A0/en unknown
- 2010-10-11 ZA ZA2010/07252A patent/ZA201007252B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA201007252B (en) | 2011-12-28 |
| US20090239810A1 (en) | 2009-09-24 |
| KR20100134680A (ko) | 2010-12-23 |
| EP2268143A4 (en) | 2012-06-27 |
| AU2009225441A1 (en) | 2009-09-24 |
| RU2010142937A (ru) | 2012-04-27 |
| NZ588633A (en) | 2012-03-30 |
| AU2009225441B2 (en) | 2012-12-13 |
| BRPI0909183A2 (pt) | 2015-08-25 |
| IL208232A0 (en) | 2010-12-30 |
| EP2268143A2 (en) | 2011-01-05 |
| US8129376B2 (en) | 2012-03-06 |
| CN102036558A (zh) | 2011-04-27 |
| WO2009117676A3 (en) | 2010-01-07 |
| WO2009117676A2 (en) | 2009-09-24 |
| JP2011518774A (ja) | 2011-06-30 |
| CA2719000A1 (en) | 2009-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| MX2010010241A (es) | Derivados de piperidina novedosos como inhibidores de estearoil-coa desaturasa. | |
| US20100160323A1 (en) | NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE | |
| US7304077B2 (en) | Chemical compounds | |
| JP5094398B2 (ja) | 複素環式誘導体およびステアロイル−CoAデサチュラーゼのメディエータとしてのそれらの使用 | |
| JP4853965B2 (ja) | アダマンタン誘導体およびアザビシクロオクタン誘導体およびアザビシクロノナン誘導体、ならびにこれらの調製方法およびdpp−iv阻害剤としてのこれらの使用 | |
| US8039463B2 (en) | Piperazine derivatives as inhibitors of stearoyl-CoA desaturase | |
| WO2001092227A1 (en) | Chemical compounds | |
| JP2008513505A5 (OSRAM) | ||
| CN101198604A (zh) | Npy拮抗剂、及其制备和应用 | |
| US20050014788A1 (en) | Piperidine derivatives and their use as modulators of chemokine receptor activity (especially ccr5) | |
| WO2002079156A1 (en) | Novel piperidine derivatives as modulators of chemokine receptor | |
| JP5073758B2 (ja) | Nk3アンタゴニストとしてのスピロピペリジン誘導体 | |
| AU2002349840A1 (en) | Piperidine derivatives and their use as modulators of chemokine receptor activity (especially CCR5) |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG | Grant or registration |