FI66859C - Foerfarande foer framstaellning av 4-aminotiofen-3-karboxylsyraderivat med fysiologisk verkan - Google Patents
Foerfarande foer framstaellning av 4-aminotiofen-3-karboxylsyraderivat med fysiologisk verkan Download PDFInfo
- Publication number
- FI66859C FI66859C FI772494A FI772494A FI66859C FI 66859 C FI66859 C FI 66859C FI 772494 A FI772494 A FI 772494A FI 772494 A FI772494 A FI 772494A FI 66859 C FI66859 C FI 66859C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- solution
- ethyl
- carbomethoxy
- methanol
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 4
- 150000001875 compounds Chemical class 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- -1 methyl ester hydrochloride Chemical class 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 78
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
- 239000000243 solution Substances 0.000 description 34
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 20
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 14
- 239000000203 mixture Substances 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 12
- 239000008346 aqueous phase Substances 0.000 description 12
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 10
- 239000012230 colorless oil Substances 0.000 description 10
- 239000011541 reaction mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 241000700159 Rattus Species 0.000 description 9
- 150000002632 lipids Chemical class 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 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 8
- 239000000284 extract Substances 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 7
- 229960003767 alanine Drugs 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- 235000004279 alanine Nutrition 0.000 description 6
- 235000014113 dietary fatty acids Nutrition 0.000 description 6
- 239000000194 fatty acid Substances 0.000 description 6
- 229930195729 fatty acid Natural products 0.000 description 6
- 150000004665 fatty acids Chemical class 0.000 description 6
- 239000012074 organic phase Substances 0.000 description 6
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 210000003494 hepatocyte Anatomy 0.000 description 5
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 230000004136 fatty acid synthesis Effects 0.000 description 4
- 239000008103 glucose Substances 0.000 description 4
- 230000004132 lipogenesis Effects 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 235000012000 cholesterol Nutrition 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
- 239000002285 corn oil Substances 0.000 description 3
- 235000005687 corn oil Nutrition 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 235000019198 oils Nutrition 0.000 description 3
- 239000003960 organic solvent Substances 0.000 description 3
- 150000002923 oximes Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- SIHCENGFXNSHNG-UHFFFAOYSA-N 2-(2-carboxyethylsulfanyl)propanoic acid Chemical compound OC(=O)C(C)SCCC(O)=O SIHCENGFXNSHNG-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 150000004292 cyclic ethers Chemical class 0.000 description 2
- 235000005911 diet Nutrition 0.000 description 2
- 230000037213 diet Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000007062 hydrolysis Effects 0.000 description 2
- 238000006460 hydrolysis reaction Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 210000004185 liver Anatomy 0.000 description 2
- 210000005229 liver cell Anatomy 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- QDKGGYGIXLSTDT-UHFFFAOYSA-N methyl 3-(2-methoxy-2-oxo-1-phenylethyl)sulfanylpropanoate Chemical compound COC(=O)CCSC(C(=O)OC)C1=CC=CC=C1 QDKGGYGIXLSTDT-UHFFFAOYSA-N 0.000 description 2
- BIRPWHGWIZZJGC-UHFFFAOYSA-N methyl 4-acetamido-5-ethylthiophene-3-carboxylate Chemical compound CCC=1SC=C(C(=O)OC)C=1NC(C)=O BIRPWHGWIZZJGC-UHFFFAOYSA-N 0.000 description 2
- IFDLYTVTWMMYFZ-UHFFFAOYSA-N methyl 4-amino-5-ethylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.CCC=1SC=C(C(=O)OC)C=1N IFDLYTVTWMMYFZ-UHFFFAOYSA-N 0.000 description 2
- QJXLLLDJKRNMEL-UHFFFAOYSA-N methyl 4-amino-5-methylthiophene-3-carboxylate;hydrochloride Chemical group Cl.COC(=O)C1=CSC(C)=C1N QJXLLLDJKRNMEL-UHFFFAOYSA-N 0.000 description 2
- JBGSZTPWSVLJJW-UHFFFAOYSA-N methyl 4-amino-5-phenylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=CSC(C=2C=CC=CC=2)=C1N JBGSZTPWSVLJJW-UHFFFAOYSA-N 0.000 description 2
- VGVKSIJTGAHDQX-UHFFFAOYSA-N methyl 4-amino-5-propan-2-ylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=CSC(C(C)C)=C1N VGVKSIJTGAHDQX-UHFFFAOYSA-N 0.000 description 2
- BPGYXWDXHQSGHM-UHFFFAOYSA-N methyl 4-amino-5-propylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.CCCC=1SC=C(C(=O)OC)C=1N BPGYXWDXHQSGHM-UHFFFAOYSA-N 0.000 description 2
- AAMVDSWOJNQRRJ-UHFFFAOYSA-N methyl 4-hydroxyimino-5-methylthiolane-3-carboxylate Chemical compound COC(=O)C1CSC(C)C1=NO AAMVDSWOJNQRRJ-UHFFFAOYSA-N 0.000 description 2
- RAWYOFQTXRJKNS-UHFFFAOYSA-N methyl 4-hydroxyimino-5-phenylthiolane-3-carboxylate Chemical compound ON=C1C(C(=O)OC)CSC1C1=CC=CC=C1 RAWYOFQTXRJKNS-UHFFFAOYSA-N 0.000 description 2
- ISZVLVQGQLASQS-UHFFFAOYSA-N methyl 4-hydroxyimino-5-propan-2-ylthiolane-3-carboxylate Chemical compound COC(=O)C1CSC(C(C)C)C1=NO ISZVLVQGQLASQS-UHFFFAOYSA-N 0.000 description 2
- OFBRZVXWOABKSL-UHFFFAOYSA-N methyl 4-oxo-5-propan-2-ylthiolane-3-carboxylate Chemical compound COC(=O)C1CSC(C(C)C)C1=O OFBRZVXWOABKSL-UHFFFAOYSA-N 0.000 description 2
- XAKJQFQGSGODID-UHFFFAOYSA-N methyl 4-oxo-5-propylthiolane-3-carboxylate Chemical compound CCCC1SCC(C(=O)OC)C1=O XAKJQFQGSGODID-UHFFFAOYSA-N 0.000 description 2
- OYCIREINXSPWPZ-UHFFFAOYSA-N methyl 5-ethyl-4-(ethylamino)thiophene-3-carboxylate;hydrochloride Chemical compound Cl.CCNC1=C(CC)SC=C1C(=O)OC OYCIREINXSPWPZ-UHFFFAOYSA-N 0.000 description 2
- RUCXHNGFLVBCSH-UHFFFAOYSA-N methyl 5-ethyl-4-hydroxyiminothiolane-3-carboxylate Chemical compound CCC1SCC(C(=O)OC)C1=NO RUCXHNGFLVBCSH-UHFFFAOYSA-N 0.000 description 2
- GYRUOPDPCRVSED-UHFFFAOYSA-N methyl 5-ethyl-4-oxothiolane-3-carboxylate Chemical compound CCC1SCC(C(=O)OC)C1=O GYRUOPDPCRVSED-UHFFFAOYSA-N 0.000 description 2
- HLNPATHSTGXZRT-UHFFFAOYSA-N methyl 5-methyl-4-oxothiolane-3-carboxylate Chemical compound COC(=O)C1CSC(C)C1=O HLNPATHSTGXZRT-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- FXAMMSSTJFKATB-UHFFFAOYSA-N 2-(2-carboxyethylsulfanyl)-3-methylbutanoic acid Chemical compound C(C)(C)C(C(=O)O)SCCC(=O)O FXAMMSSTJFKATB-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- KPGXRSRHYNQIFN-UHFFFAOYSA-N 2-oxoglutaric acid Chemical compound OC(=O)CCC(=O)C(O)=O KPGXRSRHYNQIFN-UHFFFAOYSA-N 0.000 description 1
- JAQKNILFSHWHDS-UHFFFAOYSA-N 3-amino-2-methyl-2H-thiophene-3-carboxylic acid Chemical compound NC1(C(SC=C1)C)C(=O)O JAQKNILFSHWHDS-UHFFFAOYSA-N 0.000 description 1
- ZXGGUYQIMVTIEC-UHFFFAOYSA-N 4-amino-5-phenylthiophene-3-carboxylic acid Chemical compound OC(=O)C1=CSC(C=2C=CC=CC=2)=C1N ZXGGUYQIMVTIEC-UHFFFAOYSA-N 0.000 description 1
- BIHFTJJDONUPIN-UHFFFAOYSA-N 4-amino-5-propan-2-ylthiophene-3-carboxylic acid Chemical compound CC(C)C=1SC=C(C(O)=O)C=1N BIHFTJJDONUPIN-UHFFFAOYSA-N 0.000 description 1
- NWERDHCQVWJODH-UHFFFAOYSA-N 4-amino-5-propylthiophene-3-carboxylic acid Chemical compound CCCC=1SC=C(C(O)=O)C=1N NWERDHCQVWJODH-UHFFFAOYSA-N 0.000 description 1
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- 201000001320 Atherosclerosis Diseases 0.000 description 1
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- 208000024172 Cardiovascular disease Diseases 0.000 description 1
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- BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
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- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
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- 229910052791 calcium Inorganic materials 0.000 description 1
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- 239000012043 crude product Substances 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- UVYVLBIGDKGWPX-KUAJCENISA-N digitonin Chemical compound O([C@@H]1[C@@H]([C@]2(CC[C@@H]3[C@@]4(C)C[C@@H](O)[C@H](O[C@H]5[C@@H]([C@@H](O)[C@@H](O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)CO7)O)[C@H](O)[C@@H](CO)O6)O[C@H]6[C@@H]([C@@H](O[C@H]7[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O7)O)[C@@H](O)[C@@H](CO)O6)O)[C@@H](CO)O5)O)C[C@@H]4CC[C@H]3[C@@H]2[C@@H]1O)C)[C@@H]1C)[C@]11CC[C@@H](C)CO1 UVYVLBIGDKGWPX-KUAJCENISA-N 0.000 description 1
- UVYVLBIGDKGWPX-UHFFFAOYSA-N digitonine Natural products CC1C(C2(CCC3C4(C)CC(O)C(OC5C(C(O)C(OC6C(C(OC7C(C(O)C(O)CO7)O)C(O)C(CO)O6)OC6C(C(OC7C(C(O)C(O)C(CO)O7)O)C(O)C(CO)O6)O)C(CO)O5)O)CC4CCC3C2C2O)C)C2OC11CCC(C)CO1 UVYVLBIGDKGWPX-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 1
- XIMFCGSNSKXPBO-UHFFFAOYSA-N ethyl 2-bromobutanoate Chemical compound CCOC(=O)C(Br)CC XIMFCGSNSKXPBO-UHFFFAOYSA-N 0.000 description 1
- ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- KQDJZZWCYTXUDE-UHFFFAOYSA-N hydron;thiophene;chloride Chemical compound Cl.C=1C=CSC=1 KQDJZZWCYTXUDE-UHFFFAOYSA-N 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical class [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 235000012254 magnesium hydroxide Nutrition 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- WZLILWQALWZCCL-UHFFFAOYSA-N methyl 2-(3-methoxy-3-oxopropyl)sulfanylpentanoate Chemical compound CCCC(C(=O)OC)SCCC(=O)OC WZLILWQALWZCCL-UHFFFAOYSA-N 0.000 description 1
- NHFBYYMNJUMVOT-UHFFFAOYSA-N methyl 2-bromo-2-phenylacetate Chemical compound COC(=O)C(Br)C1=CC=CC=C1 NHFBYYMNJUMVOT-UHFFFAOYSA-N 0.000 description 1
- FXAHJEIFGYJINY-UHFFFAOYSA-N methyl 3-amino-5-methylthiophene-2-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C=1SC(C)=CC=1N FXAHJEIFGYJINY-UHFFFAOYSA-N 0.000 description 1
- LISZJZABYLSBPM-UHFFFAOYSA-N methyl 4-hydroxyimino-5-propylthiolane-3-carboxylate Chemical compound CCCC1SCC(C(=O)OC)C1=NO LISZJZABYLSBPM-UHFFFAOYSA-N 0.000 description 1
- KCSVQSYESUPMQQ-UHFFFAOYSA-N methyl 4-oxo-5-phenylthiolane-3-carboxylate Chemical compound O=C1C(C(=O)OC)CSC1C1=CC=CC=C1 KCSVQSYESUPMQQ-UHFFFAOYSA-N 0.000 description 1
- QTQSEMLEAOXRDL-UHFFFAOYSA-N methyl 5-ethyl-4-(ethylamino)thiophene-3-carboxylate Chemical compound CCNC1=C(CC)SC=C1C(=O)OC QTQSEMLEAOXRDL-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 235000020824 obesity Nutrition 0.000 description 1
- 230000010412 perfusion Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 108010021724 tonin Proteins 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
Classifications
-
- 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
- C07D333/26—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 hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Obesity (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Diabetes (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Child & Adolescent Psychology (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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71685376A | 1976-08-23 | 1976-08-23 | |
| US71685476A | 1976-08-23 | 1976-08-23 | |
| US71685376 | 1976-08-23 | ||
| US71685476 | 1976-08-23 | ||
| US82052177A | 1977-08-01 | 1977-08-01 | |
| US82052177 | 1977-08-01 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI772494A7 FI772494A7 (fi) | 1978-02-24 |
| FI66859B FI66859B (fi) | 1984-08-31 |
| FI66859C true FI66859C (fi) | 1984-12-10 |
Family
ID=27418961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI772494A FI66859C (fi) | 1976-08-23 | 1977-08-22 | Foerfarande foer framstaellning av 4-aminotiofen-3-karboxylsyraderivat med fysiologisk verkan |
Country Status (21)
| Country | Link |
|---|---|
| JP (1) | JPS5340755A (en, 2012) |
| AR (1) | AR222453A1 (en, 2012) |
| AT (1) | AT359486B (en, 2012) |
| AU (1) | AU509956B2 (en, 2012) |
| BE (1) | BE858012A (en, 2012) |
| CH (1) | CH628628A5 (en, 2012) |
| DE (1) | DE2737738C2 (en, 2012) |
| DK (1) | DK150484C (en, 2012) |
| ES (1) | ES461796A1 (en, 2012) |
| FI (1) | FI66859C (en, 2012) |
| FR (1) | FR2365566A1 (en, 2012) |
| GB (1) | GB1587084A (en, 2012) |
| HU (1) | HU179484B (en, 2012) |
| IE (1) | IE45470B1 (en, 2012) |
| IL (1) | IL52792A (en, 2012) |
| IT (1) | IT1143757B (en, 2012) |
| LU (1) | LU78003A1 (en, 2012) |
| MC (1) | MC1156A1 (en, 2012) |
| NL (1) | NL7709246A (en, 2012) |
| NO (1) | NO148673C (en, 2012) |
| NZ (1) | NZ184981A (en, 2012) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6232765Y2 (en, 2012) * | 1981-02-28 | 1987-08-21 | ||
| US6515009B1 (en) | 1991-09-27 | 2003-02-04 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| US5811447A (en) | 1993-01-28 | 1998-09-22 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| US6251920B1 (en) | 1993-05-13 | 2001-06-26 | Neorx Corporation | Prevention and treatment of cardiovascular pathologies |
| US6491938B2 (en) | 1993-05-13 | 2002-12-10 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| CA2162586C (en) | 1993-05-13 | 2006-01-03 | David J. Grainger | Prevention and treatment of pathologies associated with abnormally proliferative smooth muscle cells |
| AU6959898A (en) | 1997-04-11 | 1998-11-11 | David J. Grainger | Compounds and therapies for the prevention of vascular and non-vascular pathol ogies |
| US6613083B2 (en) | 2001-05-02 | 2003-09-02 | Eckhard Alt | Stent device and method |
| DE102004063191A1 (de) | 2004-12-29 | 2006-07-13 | Bayer Cropscience Ag | Verfahren zur Herstellung von substituierten 2-Alkoxycarbonyl-3-aminothiophenen |
| PL2246343T3 (pl) | 2008-02-29 | 2016-12-30 | Sposób wytwarzania związku tiofenowego i jego związku pośredniego | |
| AR130733A1 (es) | 2022-10-14 | 2025-01-15 | Adama Agan Ltd | Proceso para la preparación de aminotiofeno sustituido |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2502421A (en) * | 1944-08-28 | 1950-04-04 | Parke Davis & Co | Tetrahydrothiophenes |
| US2443598A (en) * | 1944-12-23 | 1948-06-22 | Parke Davis & Co | 3-amino-4-carbethoxy-2-alkyl derivatives of thiophene |
| US2502423A (en) * | 1944-12-23 | 1950-04-04 | Parke Davis & Co | 4-carbalkoxy-3-keto-2-substituted tetrahydrothiophene oximes |
| US2502424A (en) * | 1944-12-23 | 1950-04-04 | Parke Davis & Co | 3-acylamino-4-carboalkoxy-2-omega-ralkylthiophenes |
-
1977
- 1977-08-03 CH CH954377A patent/CH628628A5/de not_active IP Right Cessation
- 1977-08-19 FR FR7725379A patent/FR2365566A1/fr active Granted
- 1977-08-22 LU LU78003A patent/LU78003A1/xx unknown
- 1977-08-22 MC MC771256A patent/MC1156A1/xx unknown
- 1977-08-22 FI FI772494A patent/FI66859C/fi not_active IP Right Cessation
- 1977-08-22 JP JP9963877A patent/JPS5340755A/ja active Granted
- 1977-08-22 ES ES461796A patent/ES461796A1/es not_active Expired
- 1977-08-22 AT AT607477A patent/AT359486B/de not_active IP Right Cessation
- 1977-08-22 DK DK372177A patent/DK150484C/da active
- 1977-08-22 IL IL52792A patent/IL52792A/xx unknown
- 1977-08-22 AR AR268888A patent/AR222453A1/es active
- 1977-08-22 NL NL7709246A patent/NL7709246A/xx not_active Application Discontinuation
- 1977-08-22 DE DE2737738A patent/DE2737738C2/de not_active Expired
- 1977-08-22 HU HU77HO2009A patent/HU179484B/hu not_active IP Right Cessation
- 1977-08-22 IT IT26845/77A patent/IT1143757B/it active
- 1977-08-22 NO NO772917A patent/NO148673C/no unknown
- 1977-08-22 NZ NZ184981A patent/NZ184981A/xx unknown
- 1977-08-22 AU AU28092/77A patent/AU509956B2/en not_active Expired
- 1977-08-22 BE BE180354A patent/BE858012A/xx not_active IP Right Cessation
- 1977-08-22 GB GB35098/77A patent/GB1587084A/en not_active Expired
- 1977-08-22 IE IE1751/77A patent/IE45470B1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FI772494A7 (fi) | 1978-02-24 |
| DK150484C (da) | 1987-10-05 |
| AT359486B (de) | 1980-11-10 |
| NL7709246A (nl) | 1978-02-27 |
| DE2737738C2 (de) | 1987-01-29 |
| IL52792A0 (en) | 1977-10-31 |
| DK372177A (da) | 1978-02-24 |
| DK150484B (da) | 1987-03-09 |
| ATA607477A (de) | 1980-04-15 |
| JPS5340755A (en) | 1978-04-13 |
| HU179484B (en) | 1982-10-28 |
| DE2737738A1 (de) | 1978-03-09 |
| FR2365566A1 (fr) | 1978-04-21 |
| GB1587084A (en) | 1981-03-25 |
| LU78003A1 (en, 2012) | 1978-09-14 |
| IE45470L (en) | 1978-02-23 |
| JPS6121235B2 (en, 2012) | 1986-05-26 |
| AU509956B2 (en) | 1980-06-05 |
| NZ184981A (en) | 1980-08-26 |
| AU2809277A (en) | 1979-03-01 |
| AR222453A1 (es) | 1981-05-29 |
| FR2365566B1 (en, 2012) | 1980-12-26 |
| IE45470B1 (en) | 1982-09-08 |
| BE858012A (fr) | 1978-02-22 |
| ES461796A1 (es) | 1978-12-16 |
| NO148673B (no) | 1983-08-15 |
| MC1156A1 (fr) | 1978-04-17 |
| IL52792A (en) | 1981-06-29 |
| CH628628A5 (en) | 1982-03-15 |
| NO772917L (no) | 1978-02-24 |
| NO148673C (no) | 1983-11-23 |
| FI66859B (fi) | 1984-08-31 |
| IT1143757B (it) | 1986-10-22 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: F. HOFFMANN-LA ROCHE AG |