SK16412000A3 - Deriváty kyseliny oxyiminoalkánovej - Google Patents
Deriváty kyseliny oxyiminoalkánovej Download PDFInfo
- Publication number
- SK16412000A3 SK16412000A3 SK1641-2000A SK16412000A SK16412000A3 SK 16412000 A3 SK16412000 A3 SK 16412000A3 SK 16412000 A SK16412000 A SK 16412000A SK 16412000 A3 SK16412000 A3 SK 16412000A3
- Authority
- SK
- Slovakia
- Prior art keywords
- optionally substituted
- group
- ethyl acetate
- hydrogen atom
- hydrocarbon group
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 25
- 230000002218 hypoglycaemic effect Effects 0.000 title description 7
- 230000000055 hyoplipidemic effect Effects 0.000 title description 5
- 150000001875 compounds Chemical class 0.000 claims abstract description 162
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 93
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 84
- 150000002430 hydrocarbons Chemical group 0.000 claims abstract description 70
- 125000001424 substituent group Chemical group 0.000 claims abstract description 54
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 53
- 125000001183 hydrocarbyl group Chemical group 0.000 claims abstract description 49
- 125000002252 acyl group Chemical group 0.000 claims abstract description 42
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 39
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 32
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 32
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 32
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 24
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 18
- 125000004430 oxygen atom Chemical group O* 0.000 claims abstract description 17
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 16
- 238000004519 manufacturing process Methods 0.000 claims abstract description 13
- 230000002265 prevention Effects 0.000 claims abstract description 13
- 239000000203 mixture Substances 0.000 claims description 242
- -1 C 1 -C 3 alkyl Chemical group 0.000 claims description 211
- 239000003795 chemical substances by application Substances 0.000 claims description 47
- 102000005962 receptors Human genes 0.000 claims description 31
- 108020003175 receptors Proteins 0.000 claims description 31
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 19
- 206010022489 Insulin Resistance Diseases 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 16
- 125000001544 thienyl group Chemical group 0.000 claims description 16
- 206010012601 diabetes mellitus Diseases 0.000 claims description 14
- 125000002541 furyl group Chemical group 0.000 claims description 14
- 150000004492 retinoid derivatives Chemical class 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 12
- 108010038912 Retinoid X Receptors Proteins 0.000 claims description 11
- 102000034527 Retinoid X Receptors Human genes 0.000 claims description 11
- 239000003446 ligand Substances 0.000 claims description 10
- 210000002824 peroxisome Anatomy 0.000 claims description 9
- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 9
- 208000002705 Glucose Intolerance Diseases 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 201000009104 prediabetes syndrome Diseases 0.000 claims description 8
- 201000005577 familial hyperlipidemia Diseases 0.000 claims description 7
- 208000011775 arteriosclerosis disease Diseases 0.000 claims description 6
- 208000027866 inflammatory disease Diseases 0.000 claims description 6
- 206010003210 Arteriosclerosis Diseases 0.000 claims description 5
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 208000011580 syndromic disease Diseases 0.000 abstract description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 837
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 224
- 239000000243 solution Substances 0.000 description 206
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 176
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 165
- 239000013078 crystal Substances 0.000 description 136
- 239000010410 layer Substances 0.000 description 127
- 125000004432 carbon atom Chemical group C* 0.000 description 120
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 118
- 229920006395 saturated elastomer Polymers 0.000 description 115
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 113
- 239000011541 reaction mixture Substances 0.000 description 112
- 239000011780 sodium chloride Substances 0.000 description 110
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 104
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 88
- 235000019341 magnesium sulphate Nutrition 0.000 description 88
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 79
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 76
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 66
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 64
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 63
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 52
- 238000003756 stirring Methods 0.000 description 51
- 239000000741 silica gel Substances 0.000 description 49
- 229910002027 silica gel Inorganic materials 0.000 description 49
- 238000000034 method Methods 0.000 description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000003921 oil Substances 0.000 description 44
- 235000019198 oils Nutrition 0.000 description 44
- 125000000217 alkyl group Chemical group 0.000 description 37
- 238000006243 chemical reaction Methods 0.000 description 37
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
- 238000010992 reflux Methods 0.000 description 33
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 32
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 30
- 239000000725 suspension Substances 0.000 description 28
- 239000002585 base Substances 0.000 description 27
- 238000001953 recrystallisation Methods 0.000 description 27
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 23
- 239000013612 plasmid Substances 0.000 description 23
- 239000012312 sodium hydride Substances 0.000 description 23
- 229910000104 sodium hydride Inorganic materials 0.000 description 23
- 239000002904 solvent Substances 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 125000003118 aryl group Chemical group 0.000 description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 19
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 19
- 230000000694 effects Effects 0.000 description 19
- 239000012634 fragment Substances 0.000 description 19
- 239000007788 liquid Substances 0.000 description 19
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 18
- 239000012299 nitrogen atmosphere Substances 0.000 description 18
- 239000001632 sodium acetate Substances 0.000 description 18
- 235000017281 sodium acetate Nutrition 0.000 description 18
- 239000012230 colorless oil Substances 0.000 description 17
- 238000004440 column chromatography Methods 0.000 description 17
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- 125000001931 aliphatic group Chemical group 0.000 description 15
- 238000010898 silica gel chromatography Methods 0.000 description 15
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 14
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- 210000004027 cell Anatomy 0.000 description 14
- 239000000460 chlorine Substances 0.000 description 14
- 229910052801 chlorine Inorganic materials 0.000 description 14
- 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 14
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 13
- 125000002723 alicyclic group Chemical group 0.000 description 13
- 239000011737 fluorine Substances 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 13
- 238000009472 formulation Methods 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 12
- 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 12
- 101001093899 Homo sapiens Retinoic acid receptor RXR-alpha Proteins 0.000 description 12
- 125000003545 alkoxy group Chemical group 0.000 description 12
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 12
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 12
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 12
- 229910052794 bromium Inorganic materials 0.000 description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 description 12
- 108020004414 DNA Proteins 0.000 description 11
- 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 11
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 11
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 11
- 239000003623 enhancer Substances 0.000 description 11
- 239000011734 sodium Substances 0.000 description 11
- 229910052708 sodium Inorganic materials 0.000 description 11
- QJEWQQYHYXDLRZ-UHFFFAOYSA-N 4-[[4-(chloromethyl)phenoxy]methyl]-5-methyl-2-phenyl-1,3-oxazole Chemical compound CC=1OC(C=2C=CC=CC=2)=NC=1COC1=CC=C(CCl)C=C1 QJEWQQYHYXDLRZ-UHFFFAOYSA-N 0.000 description 10
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 10
- 206010006895 Cachexia Diseases 0.000 description 10
- 230000002411 adverse Effects 0.000 description 10
- 239000001768 carboxy methyl cellulose Substances 0.000 description 10
- 125000005843 halogen group Chemical group 0.000 description 10
- 238000000926 separation method Methods 0.000 description 10
- 239000012279 sodium borohydride Substances 0.000 description 10
- 229910000033 sodium borohydride Inorganic materials 0.000 description 10
- 241000282414 Homo sapiens Species 0.000 description 9
- 108010016731 PPAR gamma Proteins 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 9
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 8
- 102000003728 Peroxisome Proliferator-Activated Receptors Human genes 0.000 description 8
- 108090000029 Peroxisome Proliferator-Activated Receptors Proteins 0.000 description 8
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 8
- 125000003342 alkenyl group Chemical group 0.000 description 8
- 239000000872 buffer Substances 0.000 description 8
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 8
- 239000008112 carboxymethyl-cellulose Substances 0.000 description 8
- 229940105329 carboxymethylcellulose Drugs 0.000 description 8
- 239000011248 coating agent Substances 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine hydrate Chemical compound O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 125000001624 naphthyl group Chemical group 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 230000002829 reductive effect Effects 0.000 description 8
- 235000000346 sugar Nutrition 0.000 description 8
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
- 102000004877 Insulin Human genes 0.000 description 7
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- 229920002472 Starch Polymers 0.000 description 7
- 125000004104 aryloxy group Chemical group 0.000 description 7
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
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- 229940125396 insulin Drugs 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- 239000008107 starch Substances 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
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- 239000003054 catalyst Substances 0.000 description 6
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- 239000002299 complementary DNA Substances 0.000 description 6
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 6
- 201000010099 disease Diseases 0.000 description 6
- 239000011630 iodine Substances 0.000 description 6
- 229910052740 iodine Inorganic materials 0.000 description 6
- 235000010355 mannitol Nutrition 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 125000004076 pyridyl group Chemical group 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 5
- 229940126033 PPAR agonist Drugs 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 125000004423 acyloxy group Chemical group 0.000 description 5
- 125000003302 alkenyloxy group Chemical group 0.000 description 5
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003153 chemical reaction reagent Substances 0.000 description 5
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 5
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- 239000012452 mother liquor Substances 0.000 description 5
- 125000002971 oxazolyl group Chemical group 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 239000002307 peroxisome proliferator activated receptor agonist Substances 0.000 description 5
- 239000002953 phosphate buffered saline Substances 0.000 description 5
- 239000000049 pigment Substances 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 108090000623 proteins and genes Proteins 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 238000000638 solvent extraction Methods 0.000 description 5
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
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Applications Claiming Priority (3)
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| JP12792298 | 1998-05-11 | ||
| JP12792198 | 1998-05-11 | ||
| PCT/JP1999/002407 WO1999058510A1 (en) | 1998-05-11 | 1999-05-10 | Oxyiminoalkanoic acid derivatives with hypoglycemic and hypolipidemic activity |
Publications (1)
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| SK16412000A3 true SK16412000A3 (sk) | 2001-08-06 |
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| SK1641-2000A SK16412000A3 (sk) | 1998-05-11 | 1999-05-10 | Deriváty kyseliny oxyiminoalkánovej |
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| CA2382966A1 (en) | 1999-08-27 | 2001-03-08 | Eli Lilly And Company | Biaryl-oxa(thia)zole derivatives and their use as ppars modulators |
| DE19948126A1 (de) * | 1999-10-06 | 2001-04-12 | Max Delbrueck Centrum | Pharmazeutisches Mittel zur Behandlung von Kachexie und/oder kardiogenem Schock |
| TW558554B (en) * | 1999-10-29 | 2003-10-21 | Takeda Chemical Industries Ltd | Crystals of oxyiminoalkanoic acid derivative |
| EP1227081A4 (en) * | 1999-10-29 | 2004-08-11 | Takeda Chemical Industries Ltd | PROCESS FOR THE PREPARATION OF OXYMINOALKANOIC ACID DERIVATIVES |
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| CA2390928A1 (en) * | 1999-11-10 | 2001-05-17 | Takeda Chemical Industries, Ltd. | Alkoxyiminoalkanoic acid derivatives |
| JP3723071B2 (ja) | 1999-11-10 | 2005-12-07 | 武田薬品工業株式会社 | 含窒素5員複素環化合物 |
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| ATE542805T1 (de) * | 2000-08-11 | 2012-02-15 | Nippon Chemiphar Co | Ppar-delta aktivatoren |
| US20060089389A1 (en) * | 2000-08-22 | 2006-04-27 | Malcolm Allison | Combination |
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| DE60139025D1 (de) | 2000-12-28 | 2009-07-30 | Takeda Pharmaceutical | Alkansäurederivate, verfahren zu deren herstellung und deren verwendung |
| US7241785B2 (en) | 2001-03-23 | 2007-07-10 | Takeda Pharmaceutical Company Limited | Five-membered heterocyclic alkanoic acid derivative |
| ATE480236T1 (de) * | 2001-04-25 | 2010-09-15 | Takeda Pharmaceutical | Verwendung des abc-expressionspromotors pioglitazon zur behandlung von arteriosklerose obliterans |
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| US8168233B2 (en) * | 2002-10-18 | 2012-05-01 | Amylin Pharmaceuticals, Inc. | Treatment of pancreatitis with amylin |
| US7960369B2 (en) | 2002-11-08 | 2011-06-14 | Takeda Pharmaceutical Company Limited | Receptor function regulator |
| EP1583836A4 (en) * | 2002-12-11 | 2006-12-27 | Univ Massachusetts | METHOD OF INTRODUCING siRNA IN ADIPOCYTES |
| US7790681B2 (en) * | 2002-12-17 | 2010-09-07 | Amylin Pharmaceuticals, Inc. | Treatment of cardiac arrhythmias with GLP-1 receptor ligands |
| US20040209803A1 (en) * | 2002-12-19 | 2004-10-21 | Alain Baron | Compositions for the treatment and prevention of nephropathy |
| AU2003292775A1 (en) * | 2002-12-27 | 2004-07-29 | Takeda Pharmaceutical Company Limited | Body weight gain inhibitor |
| JP5140881B2 (ja) * | 2003-09-17 | 2013-02-13 | 要 川杉 | 医薬組成物 |
| AU2005217641B2 (en) * | 2004-02-24 | 2008-02-14 | Irm Llc | Immunosuppressant compounds and compositions |
| CN1972715A (zh) * | 2004-03-29 | 2007-05-30 | 三共株式会社 | 含有胰岛素抵抗改善剂的糖尿病治疗剂 |
| EP1731505B1 (en) | 2004-03-30 | 2015-01-14 | Takeda Pharmaceutical Company Limited | Alkoxyphenylpropanoic acid derivatives |
| ATE493973T1 (de) | 2004-06-04 | 2011-01-15 | Teva Pharma | Irbesartan enthaltende pharmazeutische zusammensetzung |
| CA2579490A1 (en) * | 2004-09-13 | 2006-03-23 | Santen Pharmaceutical Co., Ltd. | Therapeutic agent for keratoconjunctiva disorder |
| US7556933B2 (en) * | 2004-10-01 | 2009-07-07 | Luminultra Technologies Ltd. | Reagent system and process for adenosine triphosphate monitoring |
| WO2006112549A1 (ja) | 2005-04-20 | 2006-10-26 | Takeda Pharmaceutical Company Limited | 縮合複素環化合物 |
| EP1876179B1 (en) | 2005-04-28 | 2015-03-25 | Takeda Pharmaceutical Company Limited | Thienopyrimidone compounds |
| WO2006126514A1 (ja) | 2005-05-27 | 2006-11-30 | Shionogi & Co., Ltd. | イソキサゾール骨格を有するアリール酢酸誘導体 |
| MY152185A (en) | 2005-06-10 | 2014-08-29 | Novartis Ag | Modified release 1-[(3-hydroxy-adamant-1-ylamino)-acetyl]-pyrrolidine-2(s)-carbonitrile formulation |
| US7491414B2 (en) * | 2005-10-12 | 2009-02-17 | Gaia Herbs, Inc. | Anti-inflammatory substances extracted from Echinacea |
| JPWO2008136428A1 (ja) | 2007-04-27 | 2010-07-29 | 武田薬品工業株式会社 | 含窒素5員複素環化合物 |
| EP2266983B1 (en) | 2008-04-16 | 2013-06-05 | Takeda Pharmaceutical Company Limited | Nitrogenated 5-membered heterocyclic compound |
| WO2010011302A1 (en) * | 2008-07-22 | 2010-01-28 | Chdi, Inc. | Certain kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| JPWO2010016552A1 (ja) | 2008-08-07 | 2012-01-26 | 武田薬品工業株式会社 | 過敏性腸症候群治療薬 |
| WO2010064147A2 (en) | 2008-12-04 | 2010-06-10 | Ikfe Gmbh | Biomarkers for atherosclerosis |
| EP2376926A1 (en) | 2008-12-11 | 2011-10-19 | IKFE GmbH | Biomarkers for insulin sensitizer drug response |
| EP2382467A1 (en) | 2008-12-30 | 2011-11-02 | IKFE GmbH | Biomarkers for adipose tissue activity |
| EP2382475A2 (en) | 2009-01-07 | 2011-11-02 | IKFE GmbH | Biomarkers for appetite regulation |
| CN102875548A (zh) * | 2011-07-14 | 2013-01-16 | 中国科学院大连化学物理研究所 | 一类基于肟的通过[2+2+2]环加成合成吡啶衍生物的方法 |
| WO2013033085A1 (en) | 2011-08-30 | 2013-03-07 | Stephen Martin Courtney | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| US9428464B2 (en) | 2011-08-30 | 2016-08-30 | Chdi Foundation, Inc. | Kynurenine-3-monooxygenase inhibitors, pharmaceutical compositions, and methods of use thereof |
| WO2013082106A1 (en) | 2011-12-02 | 2013-06-06 | The General Hospital Corporation | Differentiation into brown adipocytes |
| JP6299591B2 (ja) | 2012-07-03 | 2018-03-28 | 小野薬品工業株式会社 | ソマトスタチン受容体作動活性を有する化合物およびその医薬用途 |
| BR112016007078A2 (pt) | 2013-09-30 | 2017-12-12 | Ono Pharmaceutical Co | composto tendo atividade agonística do receptor de somatostatina e uso farmacêutico do mesmo |
| US20160083380A1 (en) * | 2013-12-16 | 2016-03-24 | Cadila Healthcare Limited | Oximino derivatives for the treatment of dyslipidemia |
| US10258621B2 (en) | 2014-07-17 | 2019-04-16 | Chdi Foundation, Inc. | Methods and compositions for treating HIV-related disorders |
| FR3042903B1 (fr) * | 2015-10-21 | 2017-12-08 | Commissariat Energie Atomique | Utilisation d'acides hydroxyiminoalcanoiques comme agents anti-nitreux dans des operations de desextraction reductrice du plutonium |
| WO2018002673A1 (en) | 2016-07-01 | 2018-01-04 | N4 Pharma Uk Limited | Novel formulations of angiotensin ii receptor antagonists |
| MX2019009419A (es) | 2017-02-08 | 2019-10-02 | Ono Pharmaceutical Co | Compuesto que tiene actividad agonista del receptor de somatostatina y uso farmaceutico del mismo. |
| AU2020224628B2 (en) | 2019-02-21 | 2025-04-24 | Steelcase Inc. | Body support assembly and methods for the use and assembly thereof |
| US11357329B2 (en) | 2019-12-13 | 2022-06-14 | Steelcase Inc. | Body support assembly and methods for the use and assembly thereof |
Family Cites Families (34)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU177578B (en) | 1976-08-27 | 1981-11-28 | Chinoin Gyogyszer Es Vegyeszet | Process for preparing new 0-/3-amino-2-hydroxy-propyl/-amidoxime derivatives |
| JPS5849382A (ja) | 1981-09-18 | 1983-03-23 | Kyowa Hakko Kogyo Co Ltd | β−ラクタム化合物 |
| JPS59167576A (ja) | 1983-03-15 | 1984-09-21 | Kyowa Hakko Kogyo Co Ltd | β−ラクタム化合物 |
| JPS6277391A (ja) | 1984-12-21 | 1987-04-09 | Mochida Pharmaceut Co Ltd | セフアロスポリン誘導体、その製法およびそれらを有効成分とする抗菌剤 |
| JPS62158290A (ja) * | 1985-12-28 | 1987-07-14 | Banyu Pharmaceut Co Ltd | 新規セフアロスポリン誘導体 |
| US4698338A (en) | 1986-02-19 | 1987-10-06 | Eli Lilly And Company | 7[2-(2-aminothiazol-4-yl)-2-benzyloximino]acetamido-3[4-alkyl-5-oxo-6-hydroxy-3,4-dihydro-1,2,4-triazin-3-yl]thiomethyl cephalosporins |
| US5750532A (en) * | 1986-12-10 | 1998-05-12 | Schering Corporation | Pharmaceutically active compounds |
| JPH0277391A (ja) | 1988-09-14 | 1990-03-16 | Suzuki Motor Co Ltd | 水ジェット推進船のビルジ水排水装置 |
| ATE169616T1 (de) | 1988-11-21 | 1998-08-15 | Zeneca Ltd | Zwischenverbindungen zur herstellung von fungiziden |
| EP0400805A1 (en) | 1989-04-25 | 1990-12-05 | Toshiyasu Ishimaru | Cephalosporin compounds and their use |
| JPH03115272A (ja) * | 1989-10-19 | 1991-05-16 | Banyu Pharmaceut Co Ltd | マンデル酸誘導体およびその製法 |
| IE912046A1 (en) * | 1990-06-18 | 1991-12-18 | Fujisawa Pharmaceutical Co | New polypeptide compound and a process for preparation¹thereof |
| EP0463488B2 (de) * | 1990-06-27 | 2004-04-21 | BASF Aktiengesellschaft | O-Benzyl-Oximether und diese Verbindungen enthaltende Pflanzenschutzmittel |
| JPH04112890A (ja) * | 1990-09-04 | 1992-04-14 | Ajinomoto Co Inc | 新規チアゾール誘導体及び該誘導体を含有する抗菌剤 |
| EP0486011A3 (en) * | 1990-11-16 | 1992-07-15 | Fujisawa Pharmaceutical Co., Ltd. | Pharmaceutical composition against pneumocystis carinii |
| DE4105551A1 (de) * | 1991-02-22 | 1992-08-27 | Bayer Ag | 2-substituierte chinoline, verfahren zu ihrer herstellung sowie ihre verwendung in arzneimitteln |
| RU2032677C1 (ru) * | 1992-05-05 | 1995-04-10 | Бристоль-Мейерз Сквибб Компани | Производные оксазола |
| KR100191137B1 (ko) * | 1992-07-21 | 1999-06-15 | 사노 가즈오 | 옥심 유도체 |
| US5512581A (en) * | 1994-07-18 | 1996-04-30 | Abbott Laboratories | Iminoxycarboxylates and derivatives as inhibitors of leukotriene biosynthesis |
| CA2159938A1 (en) | 1994-10-07 | 1996-04-08 | Hiroaki Yanagisawa | Oxime derivatives, their preparation and their therapeutic use |
| CH689228A5 (de) | 1994-10-07 | 1998-12-31 | Novartis Ag | Oximether, sowie diese enthaltende Pflanzenschutzmittel. |
| US5902726A (en) | 1994-12-23 | 1999-05-11 | Glaxo Wellcome Inc. | Activators of the nuclear orphan receptor peroxisome proliferator-activated receptor gamma |
| US6022897A (en) | 1995-04-25 | 2000-02-08 | The Salk Institute For Biological Studies | Selective modulators of peroxisome proliferator activated receptor-gamma, and methods for the use thereof |
| AU5701896A (en) * | 1995-06-02 | 1996-12-18 | Sankyo Company Limited | Aromatic oxyimino derivatives |
| US5939442A (en) | 1995-06-07 | 1999-08-17 | The Salk Institute For Biological Studies | Modulations of peroxisome proliferator activated receptor-γ, and methods for the use thereof |
| FR2737893B1 (fr) * | 1995-08-16 | 1997-09-12 | Roussel Uclaf | Nouvelles cephalosporines comportant en position 7, un radical benzyloxyimino substitue, leur procede et intermediaires de preparation, leur application comme medicaments |
| GB9600464D0 (en) | 1996-01-09 | 1996-03-13 | Smithkline Beecham Plc | Novel method |
| GB9604242D0 (en) * | 1996-02-28 | 1996-05-01 | Glaxo Wellcome Inc | Chemical compounds |
| JPH09323929A (ja) | 1996-04-02 | 1997-12-16 | Sankyo Co Ltd | オキシム誘導体を含有する医薬 |
| RU2169141C2 (ru) | 1996-04-04 | 2001-06-20 | Санкио Компани Лимитед | Производные фенилалкилкарбоновой кислоты и фармацевтическая композиция на их основе |
| AU4050797A (en) | 1996-08-02 | 1998-02-25 | Ligand Pharmaceuticals Incorporated | Prevention or treatment of type 2 diabetes or cardiovascular disease with ppar modulators |
| EP1023907B1 (en) | 1997-07-24 | 2009-01-21 | Astellas Pharma Inc. | Medicinal compositions with cholesterol-lowering effect |
| JPH11193272A (ja) | 1997-10-01 | 1999-07-21 | Sankyo Co Ltd | フェニルアルキルカルボン酸誘導体を含有する医薬 |
| BR9910371A (pt) * | 1998-05-11 | 2001-01-09 | Takera Chemical Ind Ltd | Composto, composição farmacêutica, agente para controlar os receptores relacionados com a retinóide, processos de prevenção e terapia da diabetes mellitus, de prevenção e terapia da hiperlipemia, para acentuar uma sensibilidade à insulina, para melhorar uma resistência à insulina, de prevenção e terapia da tolerância à glicose prejudicada, de prevenção e terapia de uma doença inflamatória, de prevenção de uma esclerose arterial, e, uso do composto |
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- 1999-05-10 IL IL13947099A patent/IL139470A0/xx unknown
- 1999-05-10 ES ES99918355T patent/ES2226377T3/es not_active Expired - Lifetime
- 1999-05-10 EP EP04075569A patent/EP1428531A1/en not_active Withdrawn
- 1999-05-10 DE DE69919156T patent/DE69919156T2/de not_active Expired - Lifetime
- 1999-05-10 PT PT99918355T patent/PT1077957E/pt unknown
- 1999-05-10 KR KR10-2000-7000081A patent/KR100388120B1/ko not_active Expired - Fee Related
- 1999-05-10 MY MYPI99001832A patent/MY123337A/en unknown
- 1999-05-10 SK SK1641-2000A patent/SK16412000A3/sk unknown
- 1999-05-10 RU RU2000131183/04A patent/RU2213738C2/ru not_active IP Right Cessation
- 1999-05-10 ID IDW20002324A patent/ID28699A/id unknown
- 1999-05-10 WO PCT/JP1999/002407 patent/WO1999058510A1/en not_active Ceased
- 1999-05-10 CA CA002331879A patent/CA2331879A1/en not_active Abandoned
- 1999-05-10 AT AT99918355T patent/ATE272625T1/de not_active IP Right Cessation
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- 1999-05-10 PL PL99344002A patent/PL344002A1/xx not_active Application Discontinuation
- 1999-05-10 US US09/423,854 patent/US6251926B1/en not_active Expired - Fee Related
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- 1999-05-10 CN CNB998060070A patent/CN1148361C/zh not_active Expired - Fee Related
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- 1999-05-11 CO CO99029123A patent/CO5040066A1/es unknown
- 1999-12-28 JP JP11373202A patent/JP2000198772A/ja active Pending
-
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- 2000-11-02 NO NO20005531A patent/NO317426B1/no unknown
- 2000-11-16 US US09/714,699 patent/US6495581B1/en not_active Expired - Fee Related
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