HRP20030346A2 - Propionic acid derivatives - Google Patents
Propionic acid derivatives Download PDFInfo
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- HRP20030346A2 HRP20030346A2 HR20030346A HRP20030346A HRP20030346A2 HR P20030346 A2 HRP20030346 A2 HR P20030346A2 HR 20030346 A HR20030346 A HR 20030346A HR P20030346 A HRP20030346 A HR P20030346A HR P20030346 A2 HRP20030346 A2 HR P20030346A2
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- Croatia
- Prior art keywords
- methyl
- amino
- compounds
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- phenyl
- Prior art date
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- 229940111131 antiinflammatory and antirheumatic product propionic acid derivative Drugs 0.000 title 1
- 150000005599 propionic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 157
- -1 furanylmethyl Chemical group 0.000 claims description 125
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 93
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 74
- 239000001257 hydrogen Substances 0.000 claims description 70
- 229910052739 hydrogen Inorganic materials 0.000 claims description 70
- 238000000034 method Methods 0.000 claims description 62
- 239000002904 solvent Substances 0.000 claims description 47
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 38
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 34
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 33
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 31
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 27
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 21
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 19
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 14
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 14
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 13
- 239000011737 fluorine Substances 0.000 claims description 13
- 150000002431 hydrogen Chemical group 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 12
- 238000011282 treatment Methods 0.000 claims description 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 11
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- 150000001735 carboxylic acids Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 9
- 150000004677 hydrates Chemical class 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 9
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 239000000460 chlorine Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000012453 solvate Substances 0.000 claims description 8
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 238000003786 synthesis reaction Methods 0.000 claims description 7
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 6
- 150000001408 amides Chemical class 0.000 claims description 6
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 239000007790 solid phase Substances 0.000 claims description 5
- 125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 claims description 5
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 5
- WTGULPIOCRAFHN-UHFFFAOYSA-N COClOC(F)(F)F Chemical compound COClOC(F)(F)F WTGULPIOCRAFHN-UHFFFAOYSA-N 0.000 claims description 4
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 4
- 238000011321 prophylaxis Methods 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 3
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 3
- 230000004913 activation Effects 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 238000005804 alkylation reaction Methods 0.000 claims description 3
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 3
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 239000002270 dispersing agent Substances 0.000 claims description 3
- 239000003995 emulsifying agent Substances 0.000 claims description 3
- 125000001072 heteroaryl group Chemical group 0.000 claims description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 231100000252 nontoxic Toxicity 0.000 claims description 3
- 230000003000 nontoxic effect Effects 0.000 claims description 3
- 230000009467 reduction Effects 0.000 claims description 3
- 238000010532 solid phase synthesis reaction Methods 0.000 claims description 3
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims description 2
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 2
- 208000035150 Hypercholesterolemia Diseases 0.000 claims description 2
- 239000000556 agonist Substances 0.000 claims description 2
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 210000002824 peroxisome Anatomy 0.000 claims 1
- NRNFVPWVQAOXTC-UHFFFAOYSA-N trifluoro(dimethoxy)-lambda5-chlorane Chemical compound COCl(OC)(F)(F)F NRNFVPWVQAOXTC-UHFFFAOYSA-N 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 285
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 210
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 172
- 238000005160 1H NMR spectroscopy Methods 0.000 description 145
- 239000000203 mixture Substances 0.000 description 114
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 106
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 105
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 103
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 98
- 239000000243 solution Substances 0.000 description 95
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 85
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 69
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 65
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 61
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 58
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 58
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 50
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 48
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 46
- 230000002829 reductive effect Effects 0.000 description 39
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 38
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 36
- 238000004587 chromatography analysis Methods 0.000 description 35
- 239000012074 organic phase Substances 0.000 description 35
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 31
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 29
- 235000019341 magnesium sulphate Nutrition 0.000 description 29
- 239000011347 resin Substances 0.000 description 29
- 229920005989 resin Polymers 0.000 description 29
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 25
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 22
- 239000011780 sodium chloride Substances 0.000 description 21
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 20
- 229910052796 boron Inorganic materials 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 18
- CZZZABOKJQXEBO-UHFFFAOYSA-N 2,4-dimethylaniline Chemical compound CC1=CC=C(N)C(C)=C1 CZZZABOKJQXEBO-UHFFFAOYSA-N 0.000 description 16
- 239000000126 substance Substances 0.000 description 16
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 16
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 229910052938 sodium sulfate Inorganic materials 0.000 description 15
- 235000011152 sodium sulphate Nutrition 0.000 description 15
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 14
- 239000002585 base Substances 0.000 description 14
- 229960004132 diethyl ether Drugs 0.000 description 14
- 239000000047 product Substances 0.000 description 14
- ASOKPJOREAFHNY-UHFFFAOYSA-N 1-Hydroxybenzotriazole Chemical compound C1=CC=C2N(O)N=NC2=C1 ASOKPJOREAFHNY-UHFFFAOYSA-N 0.000 description 13
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 13
- 150000003254 radicals Chemical class 0.000 description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 12
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 235000017557 sodium bicarbonate Nutrition 0.000 description 12
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
- 238000012360 testing method Methods 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
- 229960000583 acetic acid Drugs 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000012321 sodium triacetoxyborohydride Substances 0.000 description 11
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 10
- 230000007062 hydrolysis Effects 0.000 description 10
- 238000006460 hydrolysis reaction Methods 0.000 description 10
- 239000003921 oil Substances 0.000 description 10
- 235000019198 oils Nutrition 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- VZSRBBMJRBPUNF-UHFFFAOYSA-N 2-(2,3-dihydro-1H-inden-2-ylamino)-N-[3-oxo-3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propyl]pyrimidine-5-carboxamide Chemical compound C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C(=O)NCCC(N1CC2=C(CC1)NN=N2)=O VZSRBBMJRBPUNF-UHFFFAOYSA-N 0.000 description 9
- 239000012230 colorless oil Substances 0.000 description 9
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 description 9
- 235000017550 sodium carbonate Nutrition 0.000 description 9
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 9
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
- 238000011097 chromatography purification Methods 0.000 description 8
- 235000019253 formic acid Nutrition 0.000 description 8
- BEIXLIAQDVVISA-UHFFFAOYSA-N tert-butyl 2-(4-formylphenyl)sulfanyl-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)SC1=CC=C(C=O)C=C1 BEIXLIAQDVVISA-UHFFFAOYSA-N 0.000 description 8
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 8
- ZCKVENPXPQNFSH-UHFFFAOYSA-N 4-methoxy-2,5-dimethylaniline Chemical compound COC1=CC(C)=C(N)C=C1C ZCKVENPXPQNFSH-UHFFFAOYSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
- 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 7
- 230000000694 effects Effects 0.000 description 7
- NPZTUJOABDZTLV-UHFFFAOYSA-N hydroxybenzotriazole Substances O=C1C=CC=C2NNN=C12 NPZTUJOABDZTLV-UHFFFAOYSA-N 0.000 description 7
- 238000002844 melting Methods 0.000 description 7
- 230000008018 melting Effects 0.000 description 7
- ADAMEOZKZQRNKP-UHFFFAOYSA-N n'-propylmethanediimine Chemical compound CCCN=C=N ADAMEOZKZQRNKP-UHFFFAOYSA-N 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 7
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 6
- JMTMSDXUXJISAY-UHFFFAOYSA-N 2H-benzotriazol-4-ol Chemical compound OC1=CC=CC2=C1N=NN2 JMTMSDXUXJISAY-UHFFFAOYSA-N 0.000 description 6
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 description 6
- 239000007821 HATU Substances 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 239000008346 aqueous phase Substances 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 6
- XBMFHBLYZLGJNH-UHFFFAOYSA-N tert-butyl 2-[4-[(2-methoxyethylamino)methyl]phenoxy]-2-methylpropanoate Chemical compound COCCNCC1=CC=C(OC(C)(C)C(=O)OC(C)(C)C)C=C1 XBMFHBLYZLGJNH-UHFFFAOYSA-N 0.000 description 6
- 238000004809 thin layer chromatography Methods 0.000 description 6
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 5
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 5
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 5
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 5
- 210000004027 cell Anatomy 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 239000001632 sodium acetate Substances 0.000 description 5
- 235000017281 sodium acetate Nutrition 0.000 description 5
- CRJMKQQIXUFDBM-UHFFFAOYSA-N tert-butyl 2-(4-formylphenoxy)-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)OC1=CC=C(C=O)C=C1 CRJMKQQIXUFDBM-UHFFFAOYSA-N 0.000 description 5
- PHMVAJCBKCCHHG-UHFFFAOYSA-N tert-butyl 2-[4-[(furan-2-ylmethylamino)methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C1=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CO1 PHMVAJCBKCCHHG-UHFFFAOYSA-N 0.000 description 5
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- AXFWSWUXEROATH-UHFFFAOYSA-N tert-butyl 2-[4-(1,3-dioxoisoindol-2-yl)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1N1C(=O)C2=CC=CC=C2C1=O AXFWSWUXEROATH-UHFFFAOYSA-N 0.000 description 1
- RBWSVDKKZKPEHT-UHFFFAOYSA-N tert-butyl 2-[4-(2-aminoethyl)phenyl]sulfanyl-2-methylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)SC1=CC=C(CCN)C=C1 RBWSVDKKZKPEHT-UHFFFAOYSA-N 0.000 description 1
- KVMPTLLCCVLFJI-UHFFFAOYSA-N tert-butyl 2-[4-(furan-2-ylmethylamino)phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1NCC1=CC=CO1 KVMPTLLCCVLFJI-UHFFFAOYSA-N 0.000 description 1
- IJKNBZZGHWILJE-UHFFFAOYSA-N tert-butyl 2-[4-[(furan-2-ylmethylamino)methyl]phenoxy]-2-methylpropanoate Chemical compound C1=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CO1 IJKNBZZGHWILJE-UHFFFAOYSA-N 0.000 description 1
- MLZUUQKOKXAMJZ-UHFFFAOYSA-N tert-butyl 2-[4-[2-[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]ethyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1OC=CC=1)CCC1=CC=C(SC(C)(C)C(=O)OC(C)(C)C)C=C1 MLZUUQKOKXAMJZ-UHFFFAOYSA-N 0.000 description 1
- MYZPSDPMRKDBAI-UHFFFAOYSA-N tert-butyl 2-[4-[2-[furan-2-ylmethyl-[2-(4-methoxy-2,5-dimethylanilino)-2-oxoethyl]amino]ethyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C1=C(C)C(OC)=CC(C)=C1NC(=O)CN(CC=1OC=CC=1)CCC1=CC=C(SC(C)(C)C(=O)OC(C)(C)C)C=C1 MYZPSDPMRKDBAI-UHFFFAOYSA-N 0.000 description 1
- BQAJUYSCESOWDT-UHFFFAOYSA-N tert-butyl 2-[4-[[(2-ethoxy-2-oxoethyl)-(furan-2-ylmethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CC(=O)OCC)CC1=CC=CO1 BQAJUYSCESOWDT-UHFFFAOYSA-N 0.000 description 1
- CYXDEVFCDZCCCZ-UHFFFAOYSA-N tert-butyl 2-[4-[[2-methoxyethyl-[2-oxo-2-[4-propan-2-yl-2-(trifluoromethyl)anilino]ethyl]amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC1=CC=C(C(C)C)C=C1C(F)(F)F CYXDEVFCDZCCCZ-UHFFFAOYSA-N 0.000 description 1
- SQXGFIGDSMWRQE-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1C=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 SQXGFIGDSMWRQE-UHFFFAOYSA-N 0.000 description 1
- ZNWKQQDVBIQYGZ-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1C=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 ZNWKQQDVBIQYGZ-UHFFFAOYSA-N 0.000 description 1
- NGZQIAZXJVNMFF-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-(4-cyclohexyl-2-methylanilino)-2-oxoethyl]-(2-methoxyethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound C=1C=C(OC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC(C(=C1)C)=CC=C1C1CCCCC1 NGZQIAZXJVNMFF-UHFFFAOYSA-N 0.000 description 1
- GYXMUYCKIDXMOB-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-[(2,4-dimethylphenyl)methylamino]-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenoxy]-2-methylpropanoate Chemical compound CC1=CC(C)=CC=C1CNC(=O)CN(CC=1C=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 GYXMUYCKIDXMOB-UHFFFAOYSA-N 0.000 description 1
- WDCNSAUUSRGRFJ-UHFFFAOYSA-N tert-butyl 2-[4-[[[2-[5-chloro-2-methyl-4-(trifluoromethoxy)anilino]-2-oxoethyl]-(2-methoxyethyl)amino]methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C=1C=C(SC(C)(C)C(=O)OC(C)(C)C)C=CC=1CN(CCOC)CC(=O)NC1=CC(Cl)=C(OC(F)(F)F)C=C1C WDCNSAUUSRGRFJ-UHFFFAOYSA-N 0.000 description 1
- GFZNRFKHTYFIGQ-UHFFFAOYSA-N tert-butyl 2-[4-[[furan-2-ylmethyl-[2-(4-methoxy-2,5-dimethylanilino)-2-oxoethyl]amino]methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound C1=C(C)C(OC)=CC(C)=C1NC(=O)CN(CC=1C=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 GFZNRFKHTYFIGQ-UHFFFAOYSA-N 0.000 description 1
- NTZUJKHVKMXTCI-UHFFFAOYSA-N tert-butyl 2-[4-[[furan-2-ylmethyl-[2-(4-methoxy-2-methylanilino)-2-oxoethyl]amino]methyl]phenyl]sulfanyl-2-methylpropanoate Chemical compound CC1=CC(OC)=CC=C1NC(=O)CN(CC=1C=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 NTZUJKHVKMXTCI-UHFFFAOYSA-N 0.000 description 1
- VTXIFRSXTZOIRC-UHFFFAOYSA-N tert-butyl 2-bromo-2-ethylbutanoate Chemical compound CCC(Br)(CC)C(=O)OC(C)(C)C VTXIFRSXTZOIRC-UHFFFAOYSA-N 0.000 description 1
- BNWCETAHAJSBFG-UHFFFAOYSA-N tert-butyl 2-bromoacetate Chemical compound CC(C)(C)OC(=O)CBr BNWCETAHAJSBFG-UHFFFAOYSA-N 0.000 description 1
- ZGDDPWSMFGALOO-UHFFFAOYSA-N tert-butyl 2-ethyl-2-[4-[(furan-2-ylmethylamino)methyl]phenyl]sulfanylbutanoate Chemical compound C1=CC(SC(CC)(CC)C(=O)OC(C)(C)C)=CC=C1CNCC1=CC=CO1 ZGDDPWSMFGALOO-UHFFFAOYSA-N 0.000 description 1
- WZKVLWLEVMIHRA-UHFFFAOYSA-N tert-butyl 2-methyl-2-[4-[[(4-methyl-1,3-oxazol-5-yl)methylamino]methyl]phenoxy]propanoate Chemical compound N1=COC(CNCC=2C=CC(OC(C)(C)C(=O)OC(C)(C)C)=CC=2)=C1C WZKVLWLEVMIHRA-UHFFFAOYSA-N 0.000 description 1
- SLTSZNQIHLLJQI-UHFFFAOYSA-N tert-butyl 2-methyl-2-[4-[[(4-methyl-1,3-oxazol-5-yl)methylamino]methyl]phenyl]sulfanylpropanoate Chemical compound N1=COC(CNCC=2C=CC(SC(C)(C)C(=O)OC(C)(C)C)=CC=2)=C1C SLTSZNQIHLLJQI-UHFFFAOYSA-N 0.000 description 1
- UNKNQVLOGUDYEO-UHFFFAOYSA-N tert-butyl 3-[4-[[[1-amino-2-(2,4-dimethylphenyl)-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenyl]-2,2-dimethylpropanoate Chemical compound CC1=CC(C)=CC=C1C(=O)C(N)N(CC=1C=CC(CC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 UNKNQVLOGUDYEO-UHFFFAOYSA-N 0.000 description 1
- VHTBLLLPQLGVEX-UHFFFAOYSA-N tert-butyl 3-[4-[[[2-(2,4-dimethylanilino)-2-oxoethyl]-(furan-2-ylmethyl)amino]methyl]phenyl]-2,2-dimethylpropanoate Chemical compound CC1=CC(C)=CC=C1NC(=O)CN(CC=1C=CC(CC(C)(C)C(=O)OC(C)(C)C)=CC=1)CC1=CC=CO1 VHTBLLLPQLGVEX-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
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- FKKJJPMGAWGYPN-UHFFFAOYSA-N thiophen-2-ylmethanamine Chemical compound NCC1=CC=CS1 FKKJJPMGAWGYPN-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 0.000 description 1
- 230000009261 transgenic effect Effects 0.000 description 1
- 238000011830 transgenic mouse model Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011269 treatment regimen Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 description 1
- 238000011144 upstream manufacturing Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000011995 wilkinson's catalyst Substances 0.000 description 1
- UTODFRQBVUVYOB-UHFFFAOYSA-P wilkinson's catalyst Chemical compound [Cl-].C1=CC=CC=C1P(C=1C=CC=CC=1)(C=1C=CC=CC=1)[Rh+](P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C=1C=CC=CC=1)P(C=1C=CC=CC=1)(C=1C=CC=CC=1)C1=CC=CC=C1 UTODFRQBVUVYOB-UHFFFAOYSA-P 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/16—Drugs for disorders of the alimentary tract or the digestive system for liver or gallbladder disorders, e.g. hepatoprotective agents, cholagogues, litholytics
-
- 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
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/18—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/34—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton
- C07C237/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atoms of the carboxamide groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/26—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C317/28—Sulfones; Sulfoxides having sulfone or sulfoxide groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton with sulfone or sulfoxide groups bound to acyclic carbon atoms of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
- C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
- C07C323/52—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton the carbon skeleton being acyclic and saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/52—Radicals substituted by nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Cardiology (AREA)
- Obesity (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Vascular Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Urology & Nephrology (AREA)
- Endocrinology (AREA)
- Gastroenterology & Hepatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Furan Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10049208 | 2000-10-05 | ||
DE10124905A DE10124905A1 (de) | 2000-10-05 | 2001-05-22 | Propionsäurederivate |
PCT/EP2001/011005 WO2002028821A2 (de) | 2000-10-05 | 2001-09-24 | Propionsäurederivate mit ppar-alpha aktivierenden eigenschaften. |
Publications (1)
Publication Number | Publication Date |
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HRP20030346A2 true HRP20030346A2 (en) | 2005-04-30 |
Family
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20030346A HRP20030346A2 (en) | 2000-10-05 | 2003-05-02 | Propionic acid derivatives |
Country Status (22)
Country | Link |
---|---|
EP (1) | EP1328508A2 (de) |
JP (1) | JP2004510757A (de) |
CN (1) | CN1479716A (de) |
AU (1) | AU2001293838A1 (de) |
BG (1) | BG107684A (de) |
BR (1) | BR0114437A (de) |
CA (1) | CA2424540A1 (de) |
CZ (1) | CZ2003964A3 (de) |
EE (1) | EE200300140A (de) |
HN (1) | HN2001000223A (de) |
HR (1) | HRP20030346A2 (de) |
HU (1) | HUP0302306A3 (de) |
IL (1) | IL155125A0 (de) |
MA (1) | MA25917A1 (de) |
MX (1) | MXPA03002901A (de) |
NO (1) | NO20031517L (de) |
NZ (1) | NZ525119A (de) |
PL (1) | PL361162A1 (de) |
RU (1) | RU2003112968A (de) |
SK (1) | SK4132003A3 (de) |
UY (1) | UY26951A1 (de) |
WO (1) | WO2002028821A2 (de) |
Families Citing this family (16)
Publication number | Priority date | Publication date | Assignee | Title |
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DE10151390A1 (de) * | 2001-10-18 | 2003-05-08 | Bayer Ag | Essigsäurederivate |
GB0214254D0 (en) | 2002-06-20 | 2002-07-31 | Glaxo Group Ltd | Chemical compounds |
BR0315596A (pt) * | 2002-10-21 | 2005-09-06 | Janssen Pharmaceutica Nv | Tetralinas e indanos substituìdos |
CN100354259C (zh) | 2002-10-21 | 2007-12-12 | 詹森药业有限公司 | 取代的四氢化萘和茚满及其用途 |
MXPA05004296A (es) * | 2002-10-21 | 2005-11-23 | Johnson & Johnson | Tratamiento del sindrome x con tetralinas e indanos sustituidos. |
EP1583754A1 (de) | 2003-01-06 | 2005-10-12 | Eli Lilly And Company | Thiophenderivate ppar modulatoren |
JP4947406B2 (ja) | 2003-08-29 | 2012-06-06 | 小野薬品工業株式会社 | S1p受容体結合能を有する化合物およびその医薬用途 |
AR048931A1 (es) | 2004-04-21 | 2006-06-14 | Janssen Pharmaceutica Nv | Proceso para la preparacion de derivados de tetralina sustituida e indano sustituido y preparacion de intermediarios de sintesis |
CN100344618C (zh) * | 2004-05-24 | 2007-10-24 | 北京摩力克科技有限公司 | 作为hPPARα和hPPARγ激动剂的N-芳丙烯酰基取代的酪氨酸衍生物 |
KR100699928B1 (ko) | 2004-10-05 | 2007-03-26 | 재단법인서울대학교산학협력재단 | 퍼록시솜 증식자 활성화 수용체 알파 리간드를 제조하기위한 중간체의 제조방법 |
AU2005314938B2 (en) | 2004-12-13 | 2011-06-09 | Ono Pharmaceutical Co., Ltd. | Aminocarboxylic acid derivative and medicinal use thereof |
CN101054372B (zh) * | 2006-04-11 | 2010-10-13 | 中国科学院上海药物研究所 | 嘧啶取代苯丙酸衍生化合物、其制法和在治疗多囊肾疾病中的用途 |
TW201022221A (en) | 2008-12-01 | 2010-06-16 | Mitsubishi Tanabe Pharma Corp | Carboxylic acid derivatives containing thiazole ring and pharmaceutical use thereof |
JP5436941B2 (ja) * | 2009-06-03 | 2014-03-05 | あすか製薬株式会社 | ラクタム化合物又はその塩及びppar活性化剤 |
UY34200A (es) | 2011-07-21 | 2013-02-28 | Bayer Ip Gmbh | 3-(fluorovinil)pirazoles y su uso |
EP3230304B1 (de) * | 2014-12-11 | 2020-01-01 | Centrient Pharmaceuticals Netherlands B.V. | Verfahren zur acylierung eines cyclischen peptids |
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DE2320387A1 (de) * | 1973-04-21 | 1974-10-31 | Boehringer Mannheim Gmbh | Phenoxyalkylcarbonsaeurederivate und verfahren zur herstellung derselben |
GB9822473D0 (en) * | 1998-10-16 | 1998-12-09 | Glaxo Group Ltd | Chemical compounds |
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2001
- 2001-09-24 NZ NZ525119A patent/NZ525119A/en unknown
- 2001-09-24 EE EEP200300140A patent/EE200300140A/xx unknown
- 2001-09-24 CZ CZ2003964A patent/CZ2003964A3/cs unknown
- 2001-09-24 PL PL01361162A patent/PL361162A1/xx not_active Application Discontinuation
- 2001-09-24 IL IL15512501A patent/IL155125A0/xx unknown
- 2001-09-24 RU RU2003112968/04A patent/RU2003112968A/ru not_active Application Discontinuation
- 2001-09-24 MX MXPA03002901A patent/MXPA03002901A/es unknown
- 2001-09-24 JP JP2002532408A patent/JP2004510757A/ja active Pending
- 2001-09-24 BR BR0114437-5A patent/BR0114437A/pt not_active IP Right Cessation
- 2001-09-24 CA CA002424540A patent/CA2424540A1/en not_active Abandoned
- 2001-09-24 HU HU0302306A patent/HUP0302306A3/hu unknown
- 2001-09-24 EP EP01974287A patent/EP1328508A2/de not_active Withdrawn
- 2001-09-24 WO PCT/EP2001/011005 patent/WO2002028821A2/de active IP Right Grant
- 2001-09-24 SK SK413-2003A patent/SK4132003A3/sk not_active Application Discontinuation
- 2001-09-24 AU AU2001293838A patent/AU2001293838A1/en not_active Abandoned
- 2001-09-24 CN CNA018200885A patent/CN1479716A/zh active Pending
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- 2003-04-03 NO NO20031517A patent/NO20031517L/no not_active Application Discontinuation
- 2003-04-04 MA MA27091A patent/MA25917A1/fr unknown
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Also Published As
Publication number | Publication date |
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NZ525119A (en) | 2005-04-29 |
HUP0302306A2 (hu) | 2003-10-28 |
IL155125A0 (en) | 2003-10-31 |
WO2002028821A2 (de) | 2002-04-11 |
BG107684A (bg) | 2003-10-31 |
WO2002028821A3 (de) | 2002-08-15 |
NO20031517D0 (no) | 2003-04-03 |
AU2001293838A1 (en) | 2002-04-15 |
MA25917A1 (fr) | 2003-10-01 |
CZ2003964A3 (cs) | 2003-08-13 |
UY26951A1 (es) | 2002-06-20 |
HUP0302306A3 (en) | 2005-02-28 |
SK4132003A3 (en) | 2004-02-03 |
NO20031517L (no) | 2003-05-28 |
CA2424540A1 (en) | 2003-04-02 |
CN1479716A (zh) | 2004-03-03 |
BR0114437A (pt) | 2003-07-01 |
RU2003112968A (ru) | 2004-09-20 |
MXPA03002901A (es) | 2003-10-15 |
HN2001000223A (es) | 2001-10-25 |
EE200300140A (et) | 2003-08-15 |
JP2004510757A (ja) | 2004-04-08 |
EP1328508A2 (de) | 2003-07-23 |
PL361162A1 (en) | 2004-09-20 |
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