SU1169536A3 - Способ получени производных фурилоксазолилуксусной кислоты или их фармацевтически приемлемых солей - Google Patents
Способ получени производных фурилоксазолилуксусной кислоты или их фармацевтически приемлемых солей Download PDFInfo
- Publication number
- SU1169536A3 SU1169536A3 SU833555401A SU3555401A SU1169536A3 SU 1169536 A3 SU1169536 A3 SU 1169536A3 SU 833555401 A SU833555401 A SU 833555401A SU 3555401 A SU3555401 A SU 3555401A SU 1169536 A3 SU1169536 A3 SU 1169536A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- furyl
- acetic acid
- oxazolyl
- max
- furylcarbonyl
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims abstract description 9
- 238000000034 method Methods 0.000 title claims description 5
- 150000003839 salts Chemical class 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 15
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 6
- 125000000217 alkyl group Chemical group 0.000 claims abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 239000012024 dehydrating agents Substances 0.000 claims 1
- 230000018044 dehydration Effects 0.000 claims 1
- 238000006297 dehydration reaction Methods 0.000 claims 1
- 125000005843 halogen group Chemical group 0.000 claims 1
- 238000007363 ring formation reaction Methods 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 239000003524 antilipemic agent Substances 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 46
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 40
- -1 ethyl 3- (4-methoxy-benzoylamino) -3- (2-furylcarbonyl) propionic acid Chemical compound 0.000 description 39
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 26
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 22
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 16
- 235000017557 sodium bicarbonate Nutrition 0.000 description 16
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 13
- 239000012312 sodium hydride Substances 0.000 description 13
- 229910000104 sodium hydride Inorganic materials 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical compound CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 9
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 125000004494 ethyl ester group Chemical group 0.000 description 8
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 8
- 210000004185 liver Anatomy 0.000 description 7
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 238000000354 decomposition reaction Methods 0.000 description 5
- 241000700159 Rattus Species 0.000 description 4
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- RKEARERKYHKVQD-UHFFFAOYSA-N 2-amino-1-(furan-2-yl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C1=CC=CO1 RKEARERKYHKVQD-UHFFFAOYSA-N 0.000 description 3
- CHOQKBKQDVRWOT-UHFFFAOYSA-N 2-amino-1-(furan-3-yl)ethanone;hydrochloride Chemical compound Cl.NCC(=O)C=1C=COC=1 CHOQKBKQDVRWOT-UHFFFAOYSA-N 0.000 description 3
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 210000001772 blood platelet Anatomy 0.000 description 3
- 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 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 3
- 229960001214 clofibrate Drugs 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 235000019260 propionic acid Nutrition 0.000 description 3
- 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 3
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 3
- 125000000242 4-chlorobenzoyl group Chemical group ClC1=CC=C(C(=O)*)C=C1 0.000 description 2
- DXKAWTDZKYJZRD-UHFFFAOYSA-N 5-(furan-3-yl)-1,3-oxazole-4-carboxylic acid Chemical compound N1=COC(C2=COC=C2)=C1C(=O)O DXKAWTDZKYJZRD-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- MCPPAMUZFODBCY-UHFFFAOYSA-N C(C)C(C(=O)O)C(C(=O)C1=COC=C1)NC(C1=CC=C(C=C1)Cl)=O Chemical compound C(C)C(C(=O)O)C(C(=O)C1=COC=C1)NC(C1=CC=C(C=C1)Cl)=O MCPPAMUZFODBCY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- CTSCEDUOAMLTQE-UHFFFAOYSA-N furan-2-yl hydrogen carbonate Chemical compound OC(=O)OC1=CC=CO1 CTSCEDUOAMLTQE-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- ZUMGFYQZTDTOIZ-UHFFFAOYSA-N n-[2-(furan-2-yl)-2-oxoethyl]acetamide Chemical compound CC(=O)NCC(=O)C1=CC=CO1 ZUMGFYQZTDTOIZ-UHFFFAOYSA-N 0.000 description 2
- BBADSCPFRUEVCB-UHFFFAOYSA-N n-methylfuran-2-carboxamide;hydrochloride Chemical compound Cl.CNC(=O)C1=CC=CO1 BBADSCPFRUEVCB-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 210000002966 serum Anatomy 0.000 description 2
- 239000010414 supernatant solution Substances 0.000 description 2
- XUVVPUSARWFTRS-UHFFFAOYSA-N 2-(1,3-oxazol-2-yl)acetic acid Chemical compound OC(=O)CC1=NC=CO1 XUVVPUSARWFTRS-UHFFFAOYSA-N 0.000 description 1
- ZIAZNINVEBDUKC-UHFFFAOYSA-N 2-[2-cyclohexyl-5-(furan-2-yl)-1,3-oxazol-4-yl]acetic acid Chemical compound OC(=O)CC=1N=C(C2CCCCC2)OC=1C1=CC=CO1 ZIAZNINVEBDUKC-UHFFFAOYSA-N 0.000 description 1
- ABFPKTQEQNICFT-UHFFFAOYSA-M 2-chloro-1-methylpyridin-1-ium;iodide Chemical compound [I-].C[N+]1=CC=CC=C1Cl ABFPKTQEQNICFT-UHFFFAOYSA-M 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- LEPLGTJRKGCSTN-UHFFFAOYSA-N 4-chloro-n-[2-(furan-3-yl)-2-oxoethyl]benzamide Chemical compound C1=CC(Cl)=CC=C1C(=O)NCC(=O)C1=COC=C1 LEPLGTJRKGCSTN-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-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
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- PAOUBRCVOVUHDU-UHFFFAOYSA-N C(C)C(C(=O)O)C(C(=O)C1=COC=C1)NC(C1=CC=CC=C1)=O Chemical compound C(C)C(C(=O)O)C(C(=O)C1=COC=C1)NC(C1=CC=CC=C1)=O PAOUBRCVOVUHDU-UHFFFAOYSA-N 0.000 description 1
- SHXHYDJFJFXSJH-UHFFFAOYSA-N C(C)C(C(=O)O)C=1N=C(OC1C=1OC=CC1)C1CCCCC1 Chemical compound C(C)C(C(=O)O)C=1N=C(OC1C=1OC=CC1)C1CCCCC1 SHXHYDJFJFXSJH-UHFFFAOYSA-N 0.000 description 1
- UYBHIVDCZRTLDM-UHFFFAOYSA-N C(C)OC(C(C(C(=O)C=1OC=CC1)NC(C1=CC=C(C=C1)Cl)=O)CC)=O Chemical compound C(C)OC(C(C(C(=O)C=1OC=CC1)NC(C1=CC=C(C=C1)Cl)=O)CC)=O UYBHIVDCZRTLDM-UHFFFAOYSA-N 0.000 description 1
- 101100129500 Caenorhabditis elegans max-2 gene Proteins 0.000 description 1
- 102000008186 Collagen Human genes 0.000 description 1
- 108010035532 Collagen Proteins 0.000 description 1
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
- OGEMUNOAKYMNPW-UHFFFAOYSA-N FC1=CC=CC=C1.Cl Chemical compound FC1=CC=CC=C1.Cl OGEMUNOAKYMNPW-UHFFFAOYSA-N 0.000 description 1
- 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 1
- PZFCULWHBNSEBH-UHFFFAOYSA-N N-methylfuran-3-carboxamide hydrochloride Chemical compound Cl.CNC(=O)C=1C=COC=1 PZFCULWHBNSEBH-UHFFFAOYSA-N 0.000 description 1
- 206010050661 Platelet aggregation inhibition Diseases 0.000 description 1
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
- VZWGRQBCURJOMT-UHFFFAOYSA-N acetic acid n-dodecyl ester Natural products CCCCCCCCCCCCOC(C)=O VZWGRQBCURJOMT-UHFFFAOYSA-N 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 1
- 210000000702 aorta abdominal Anatomy 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229920001436 collagen Polymers 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- VCNTYBUVWLCMLB-UHFFFAOYSA-N ethyl 3-[(4-chlorobenzoyl)amino]-4-(furan-2-yl)-4-oxobutanoate Chemical compound C=1C=COC=1C(=O)C(CC(=O)OCC)NC(=O)C1=CC=C(Cl)C=C1 VCNTYBUVWLCMLB-UHFFFAOYSA-N 0.000 description 1
- MLVZZYXRCNHOMD-UHFFFAOYSA-N ethyl 3-[(4-fluorobenzoyl)amino]-4-(furan-3-yl)-4-oxobutanoate Chemical compound C1=COC=C1C(=O)C(CC(=O)OCC)NC(=O)C1=CC=C(F)C=C1 MLVZZYXRCNHOMD-UHFFFAOYSA-N 0.000 description 1
- MCWZRZXTGVMVFF-UHFFFAOYSA-N ethyl 3-benzamido-4-(furan-2-yl)-4-oxobutanoate Chemical compound C=1C=COC=1C(=O)C(CC(=O)OCC)NC(=O)C1=CC=CC=C1 MCWZRZXTGVMVFF-UHFFFAOYSA-N 0.000 description 1
- DOWJUSPHGWWKMY-UHFFFAOYSA-N ethyl 4-(furan-2-yl)-3-(2-methylpropanoylamino)-4-oxobutanoate Chemical compound CCOC(=O)CC(NC(=O)C(C)C)C(=O)C1=CC=CO1 DOWJUSPHGWWKMY-UHFFFAOYSA-N 0.000 description 1
- ZRRYYWIJRJYWNW-UHFFFAOYSA-N ethyl 4-(furan-2-yl)-3-[(4-methylbenzoyl)amino]-4-oxobutanoate Chemical compound C=1C=COC=1C(=O)C(CC(=O)OCC)NC(=O)C1=CC=C(C)C=C1 ZRRYYWIJRJYWNW-UHFFFAOYSA-N 0.000 description 1
- BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- YWGHUJQYGPDNKT-UHFFFAOYSA-N hexanoyl chloride Chemical compound CCCCCC(Cl)=O YWGHUJQYGPDNKT-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- QTBFPMKWQKYFLR-UHFFFAOYSA-N isobutyl chloride Chemical compound CC(C)CCl QTBFPMKWQKYFLR-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- PBIULHQYEUKHPR-UHFFFAOYSA-N methyl 5-(furan-3-yl)-1,3-oxazole-4-carboxylate Chemical compound N1=COC(C2=COC=C2)=C1C(=O)OC PBIULHQYEUKHPR-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- NQMRYBIKMRVZLB-UHFFFAOYSA-N methylamine hydrochloride Chemical compound [Cl-].[NH3+]C NQMRYBIKMRVZLB-UHFFFAOYSA-N 0.000 description 1
- GEAUWUZGLTXKCJ-UHFFFAOYSA-N n-[2-(furan-2-yl)-2-oxoethyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCC(=O)C1=CC=CO1 GEAUWUZGLTXKCJ-UHFFFAOYSA-N 0.000 description 1
- UENJRTOGKKSMSB-UHFFFAOYSA-N n-[2-(furan-2-yl)-2-oxoethyl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NCC(=O)C1=CC=CO1 UENJRTOGKKSMSB-UHFFFAOYSA-N 0.000 description 1
- FHCIKSCEFONQSB-UHFFFAOYSA-N n-[2-(furan-2-yl)-2-oxoethyl]-4-methylbenzamide Chemical compound C1=CC(C)=CC=C1C(=O)NCC(=O)C1=CC=CO1 FHCIKSCEFONQSB-UHFFFAOYSA-N 0.000 description 1
- NLFMGFZCSIOZPU-UHFFFAOYSA-N n-[2-(furan-3-yl)-2-oxoethyl]benzamide Chemical compound C1=COC=C1C(=O)CNC(=O)C1=CC=CC=C1 NLFMGFZCSIOZPU-UHFFFAOYSA-N 0.000 description 1
- MXGRCIBAPXPYMA-UHFFFAOYSA-N n-methylfuran-2-carboxamide Chemical compound CNC(=O)C1=CC=CO1 MXGRCIBAPXPYMA-UHFFFAOYSA-N 0.000 description 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 229940038773 trisodium citrate Drugs 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- 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
- C07D307/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Obesity (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP57030921A JPS58148882A (ja) | 1982-02-26 | 1982-02-26 | フリルオキサゾリル酢酸誘導体及びその製法 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1169536A3 true SU1169536A3 (ru) | 1985-07-23 |
Family
ID=12317149
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU833555401A SU1169536A3 (ru) | 1982-02-26 | 1983-02-25 | Способ получени производных фурилоксазолилуксусной кислоты или их фармацевтически приемлемых солей |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US4642313A (enExample) |
| EP (1) | EP0087782B1 (enExample) |
| JP (1) | JPS58148882A (enExample) |
| KR (1) | KR900001423B1 (enExample) |
| AT (1) | ATE19879T1 (enExample) |
| BG (1) | BG39977A3 (enExample) |
| CA (1) | CA1194483A (enExample) |
| DE (1) | DE3363575D1 (enExample) |
| DK (1) | DK82583A (enExample) |
| ES (1) | ES520136A0 (enExample) |
| HK (1) | HK87188A (enExample) |
| HU (1) | HU193648B (enExample) |
| SG (1) | SG10688G (enExample) |
| SU (1) | SU1169536A3 (enExample) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59152382A (ja) * | 1983-02-18 | 1984-08-31 | Tanabe Seiyaku Co Ltd | フリルオキサゾリル酢酸誘導体 |
| SE9302332D0 (sv) * | 1993-07-06 | 1993-07-06 | Ab Astra | New compounds |
| AU682792B2 (en) * | 1994-10-13 | 1997-10-16 | Cv Therapeutics, Inc. | Method of manufacturing non-absorbable synthetic sulfated polysaccharides |
| US7071174B1 (en) | 1994-10-13 | 2006-07-04 | Cv Therapeutics, Inc. | Method and composition for inhibiting cholesterol esterase |
| WO2002083111A2 (en) * | 2001-04-16 | 2002-10-24 | Tanabe Seiyaku Co., Ltd. | Imidazole, thiazole and oxazole derivatives and their use for the manufacture of a medicament for the treatment and/or prevention of pollakiuria or urinary incontinence |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IE32084B1 (en) * | 1967-06-07 | 1973-04-04 | Wyeth John & Brother Ltd | Thiazole derivatives |
| FI53314C (fi) * | 1967-06-14 | 1978-04-10 | Wyeth John & Brother Ltd | Foerfarande foer framstaellning av farmaceutiskt anvaendbar 2-(fenyleller p-klorfenyl) oxazol-4-yl (aettiksyra -acetatsalt eller -acetamid) |
| GB1245087A (en) * | 1967-10-26 | 1971-09-02 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| US3578671A (en) * | 1967-11-06 | 1971-05-11 | Wyeth John & Brother Ltd | Oxazoles |
| FR2068418A1 (en) * | 1969-10-27 | 1971-08-27 | Innothera Lab Sa | 2-substd-5-amino isoxazole derivs |
| AR208400A1 (es) * | 1974-03-13 | 1976-12-27 | Yoshitomi Pharmaceutical | Un metodo para producir nuevos acidos 5-alcoxi-4-oxazolalcanoicos 2-substituidos y sus esteres |
| JPS51110039A (ja) * | 1975-02-28 | 1976-09-29 | Yoshitomi Pharmaceutical | Ketsuchushishitsutaishakaizenzai |
| GB1542315A (en) * | 1976-08-13 | 1979-03-14 | Wyeth John & Brother Ltd | Process for preparing oxazoles |
| JPS5677268A (en) * | 1979-11-28 | 1981-06-25 | Yoshitomi Pharmaceut Ind Ltd | Oxazoleacetic acid derivative |
| JPS57188587A (en) * | 1981-05-15 | 1982-11-19 | Tanabe Seiyaku Co Ltd | Thienyloxazolylacetic acid derivative and its preparation |
-
1982
- 1982-02-26 JP JP57030921A patent/JPS58148882A/ja active Granted
-
1983
- 1983-02-10 US US06/465,544 patent/US4642313A/en not_active Expired - Fee Related
- 1983-02-22 CA CA000422117A patent/CA1194483A/en not_active Expired
- 1983-02-23 DK DK82583A patent/DK82583A/da not_active Application Discontinuation
- 1983-02-24 BG BG059855A patent/BG39977A3/xx unknown
- 1983-02-25 DE DE8383101872T patent/DE3363575D1/de not_active Expired
- 1983-02-25 ES ES520136A patent/ES520136A0/es active Granted
- 1983-02-25 SU SU833555401A patent/SU1169536A3/ru active
- 1983-02-25 KR KR1019830000770A patent/KR900001423B1/ko not_active Expired
- 1983-02-25 AT AT83101872T patent/ATE19879T1/de active
- 1983-02-25 EP EP83101872A patent/EP0087782B1/en not_active Expired
- 1983-02-25 HU HU83658A patent/HU193648B/hu not_active IP Right Cessation
-
1988
- 1988-02-06 SG SG106/88A patent/SG10688G/en unknown
- 1988-10-27 HK HK871/88A patent/HK87188A/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| Машковский М.Д. Лекарственные средства. М., Медицина, 1978, т. 2, с. 12. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US4642313A (en) | 1987-02-10 |
| HU193648B (en) | 1987-11-30 |
| ES8403891A1 (es) | 1984-04-01 |
| HK87188A (en) | 1988-11-04 |
| DK82583D0 (da) | 1983-02-23 |
| JPS58148882A (ja) | 1983-09-05 |
| KR840003632A (ko) | 1984-09-15 |
| JPS635027B2 (enExample) | 1988-02-01 |
| CA1194483A (en) | 1985-10-01 |
| EP0087782A1 (en) | 1983-09-07 |
| KR900001423B1 (ko) | 1990-03-09 |
| DE3363575D1 (en) | 1986-06-26 |
| EP0087782B1 (en) | 1986-05-21 |
| SG10688G (en) | 1988-07-01 |
| ES520136A0 (es) | 1984-04-01 |
| BG39977A3 (en) | 1986-09-15 |
| ATE19879T1 (de) | 1986-06-15 |
| DK82583A (da) | 1983-08-27 |
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