GB1587084A - Thiophene derivatives - Google Patents
Thiophene derivatives Download PDFInfo
- Publication number
- GB1587084A GB1587084A GB35098/77A GB3509877A GB1587084A GB 1587084 A GB1587084 A GB 1587084A GB 35098/77 A GB35098/77 A GB 35098/77A GB 3509877 A GB3509877 A GB 3509877A GB 1587084 A GB1587084 A GB 1587084A
- Authority
- GB
- United Kingdom
- Prior art keywords
- amino
- group
- formula
- compound
- hydrochloride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 150000003577 thiophenes Chemical class 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 19
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 13
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 15
- -1 carboxy, formyl Chemical group 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 125000003277 amino group Chemical group 0.000 claims description 10
- 150000002923 oximes Chemical class 0.000 claims description 8
- 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 claims description 7
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 4
- 239000002168 alkylating agent Substances 0.000 claims description 3
- 239000012435 aralkylating agent Substances 0.000 claims description 3
- QJXLLLDJKRNMEL-UHFFFAOYSA-N methyl 4-amino-5-methylthiophene-3-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C1=CSC(C)=C1N QJXLLLDJKRNMEL-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- UEGHDHJPAIWDJC-UHFFFAOYSA-N 4-amino-5-methylthiophene-3-carboxylic acid Chemical compound CC=1SC=C(C(O)=O)C=1N UEGHDHJPAIWDJC-UHFFFAOYSA-N 0.000 claims description 2
- 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 claims description 2
- 229920002261 Corn starch Polymers 0.000 claims description 2
- 230000002152 alkylating effect Effects 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 239000008120 corn starch Substances 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims 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 claims description 2
- RBLGLDWTCZMLRW-UHFFFAOYSA-K dicalcium;phosphate;dihydrate Chemical compound O.O.[Ca+2].[Ca+2].[O-]P([O-])([O-])=O RBLGLDWTCZMLRW-UHFFFAOYSA-K 0.000 claims 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 claims 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 claims 2
- 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 claims 1
- 235000019359 magnesium stearate Nutrition 0.000 claims 1
- 239000007916 tablet composition Substances 0.000 claims 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 230000000055 hyoplipidemic effect Effects 0.000 abstract 1
- DWWREQRWOXEVGY-UHFFFAOYSA-N n-(thiolan-3-ylidene)hydroxylamine Chemical class ON=C1CCSC1 DWWREQRWOXEVGY-UHFFFAOYSA-N 0.000 abstract 1
- DKGYESBFCGKOJC-UHFFFAOYSA-N thiophen-3-amine Chemical class NC=1C=CSC=1 DKGYESBFCGKOJC-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 54
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 48
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 24
- 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 18
- 239000000243 solution Substances 0.000 description 18
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 16
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000203 mixture Substances 0.000 description 12
- 241000700159 Rattus Species 0.000 description 10
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 235000012000 cholesterol Nutrition 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 8
- 239000000194 fatty acid Substances 0.000 description 8
- 229930195729 fatty acid Natural products 0.000 description 8
- 150000004665 fatty acids Chemical class 0.000 description 8
- 150000002632 lipids Chemical class 0.000 description 8
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 235000019198 oils Nutrition 0.000 description 8
- 239000008346 aqueous phase Substances 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 6
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
- 239000008280 blood Substances 0.000 description 6
- 210000004369 blood Anatomy 0.000 description 6
- 230000000875 corresponding effect Effects 0.000 description 6
- 229960001760 dimethyl sulfoxide Drugs 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 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 5
- 229910052783 alkali metal Inorganic materials 0.000 description 5
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000008103 glucose Substances 0.000 description 5
- 210000003494 hepatocyte Anatomy 0.000 description 5
- 230000004132 lipogenesis Effects 0.000 description 5
- 210000004185 liver Anatomy 0.000 description 5
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 241000534944 Thia Species 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 210000004027 cell Anatomy 0.000 description 4
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 4
- 230000007062 hydrolysis Effects 0.000 description 4
- 238000006460 hydrolysis reaction Methods 0.000 description 4
- 235000012054 meals Nutrition 0.000 description 4
- LDTLDBDUBGAEDT-UHFFFAOYSA-N methyl 3-sulfanylpropanoate Chemical compound COC(=O)CCS LDTLDBDUBGAEDT-UHFFFAOYSA-N 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 235000004279 alanine Nutrition 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 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
- 230000004136 fatty acid synthesis Effects 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- QRLVDLBMBULFAL-UHFFFAOYSA-N Digitonin Natural products CC1CCC2(OC1)OC3C(O)C4C5CCC6CC(OC7OC(CO)C(OC8OC(CO)C(O)C(OC9OCC(O)C(O)C9OC%10OC(CO)C(O)C(OC%11OC(CO)C(O)C(O)C%11O)C%10O)C8O)C(O)C7O)C(O)CC6(C)C5CCC4(C)C3C2C QRLVDLBMBULFAL-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
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 229930194542 Keto Natural products 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-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
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 229930182558 Sterol Natural products 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000003524 antilipemic agent Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000007796 conventional method Methods 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
- 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 2
- 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 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- ORSIRXYHFPHWTN-UHFFFAOYSA-N ethyl 2-bromopentanoate Chemical compound CCCC(Br)C(=O)OCC ORSIRXYHFPHWTN-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
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- 238000010253 intravenous injection Methods 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
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- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 2
- 239000002609 medium Substances 0.000 description 2
- 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 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
- 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 2
- OFBRZVXWOABKSL-UHFFFAOYSA-N methyl 4-oxo-5-propan-2-ylthiolane-3-carboxylate Chemical class 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
- 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
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 150000003432 sterols Chemical class 0.000 description 2
- 235000003702 sterols Nutrition 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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- 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
- KSUMIKVERTTYSH-UHFFFAOYSA-N 2-propylthiophene;hydrochloride Chemical compound Cl.CCCC1=CC=CS1 KSUMIKVERTTYSH-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
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 244000215068 Acacia senegal Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000024172 Cardiovascular disease Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000084 Gum arabic Polymers 0.000 description 1
- 239000008002 Krebs-Henseleit bicarbonate buffer Substances 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical class C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- 239000000205 acacia gum Substances 0.000 description 1
- 235000010489 acacia gum Nutrition 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000000538 analytical sample Substances 0.000 description 1
- IMNFDUFMRHMDMM-UHFFFAOYSA-N anhydrous n-heptane Natural products CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 1
- 230000003579 anti-obesity Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 229910052788 barium Inorganic materials 0.000 description 1
- 229910001863 barium hydroxide Inorganic materials 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000007963 capsule composition Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000001923 cyclic compounds Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-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
- 239000012530 fluid Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000007928 intraperitoneal injection Substances 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 239000012280 lithium aluminium hydride Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 125000005905 mesyloxy group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 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 1
- AAMVDSWOJNQRRJ-UHFFFAOYSA-N methyl 4-hydroxyimino-5-methylthiolane-3-carboxylate Chemical compound COC(=O)C1CSC(C)C1=NO AAMVDSWOJNQRRJ-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
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 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
- 238000006467 substitution reaction Methods 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 125000004953 trihalomethyl group Chemical group 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005303 weighing 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)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US71685476A | 1976-08-23 | 1976-08-23 | |
| US71685376A | 1976-08-23 | 1976-08-23 | |
| US82052177A | 1977-08-01 | 1977-08-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1587084A true GB1587084A (en) | 1981-03-25 |
Family
ID=27418961
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB35098/77A Expired GB1587084A (en) | 1976-08-23 | 1977-08-22 | Thiophene derivatives |
Country Status (21)
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998046588A3 (en) * | 1997-04-11 | 1999-01-07 | Neorx Corp | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| US6166090A (en) | 1993-05-13 | 2000-12-26 | Neorx Corporation | Prevention and treatment of pathologies associated with abnormally proliferative 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 |
| US7625410B2 (en) | 2001-05-02 | 2009-12-01 | Boston Scientific Scimed, Inc. | Stent device and method |
| CN101959875A (zh) * | 2008-02-29 | 2011-01-26 | 日产化学工业株式会社 | 噻吩化合物及其中间体的制造方法 |
| US7923571B2 (en) | 2004-12-29 | 2011-04-12 | Bayer Cropscience Ag | Process for preparing substituted 2-alkoxycarbonyl-3-aminothiophenes |
| US8067022B2 (en) | 1992-09-25 | 2011-11-29 | Boston Scientific Scimed, Inc. | Therapeutic inhibitor of vascular smooth muscle cells |
| US8097642B2 (en) | 1995-02-15 | 2012-01-17 | Boston Scientific Scimed, Inc. | Therapeutic inhibitor of vascular smooth muscle cells |
| WO2024079734A1 (en) | 2022-10-14 | 2024-04-18 | Adama Agan Ltd. | Process for the preparation of substituted aminothiophene |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6232765Y2 (enrdf_load_stackoverflow) * | 1981-02-28 | 1987-08-21 |
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 |
| US2502424A (en) * | 1944-12-23 | 1950-04-04 | Parke Davis & Co | 3-acylamino-4-carboalkoxy-2-omega-ralkylthiophenes |
| US2502423A (en) * | 1944-12-23 | 1950-04-04 | Parke Davis & Co | 4-carbalkoxy-3-keto-2-substituted tetrahydrothiophene oximes |
-
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 NO NO772917A patent/NO148673C/no unknown
- 1977-08-22 IT IT26845/77A patent/IT1143757B/it active
- 1977-08-22 ES ES461796A patent/ES461796A1/es not_active Expired
- 1977-08-22 BE BE180354A patent/BE858012A/xx not_active IP Right Cessation
- 1977-08-22 MC MC771256A patent/MC1156A1/xx unknown
- 1977-08-22 DK DK372177A patent/DK150484C/da active
- 1977-08-22 HU HU77HO2009A patent/HU179484B/hu not_active IP Right Cessation
- 1977-08-22 FI FI772494A patent/FI66859C/fi not_active IP Right Cessation
- 1977-08-22 LU LU78003A patent/LU78003A1/xx unknown
- 1977-08-22 DE DE2737738A patent/DE2737738C2/de not_active Expired
- 1977-08-22 IE IE1751/77A patent/IE45470B1/en unknown
- 1977-08-22 NZ NZ184981A patent/NZ184981A/xx unknown
- 1977-08-22 NL NL7709246A patent/NL7709246A/xx not_active Application Discontinuation
- 1977-08-22 AU AU28092/77A patent/AU509956B2/en not_active Expired
- 1977-08-22 AT AT607477A patent/AT359486B/de not_active IP Right Cessation
- 1977-08-22 GB GB35098/77A patent/GB1587084A/en not_active Expired
- 1977-08-22 AR AR268888A patent/AR222453A1/es active
- 1977-08-22 IL IL52792A patent/IL52792A/xx unknown
- 1977-08-22 JP JP9963877A patent/JPS5340755A/ja active Granted
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8067022B2 (en) | 1992-09-25 | 2011-11-29 | Boston Scientific Scimed, Inc. | Therapeutic inhibitor of vascular smooth muscle cells |
| US6569441B2 (en) | 1993-01-28 | 2003-05-27 | Neorx Corporation | Therapeutic inhibitor of vascular smooth muscle cells |
| US6166090A (en) | 1993-05-13 | 2000-12-26 | Neorx Corporation | Prevention and treatment of pathologies associated with abnormally proliferative 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 |
| US8097642B2 (en) | 1995-02-15 | 2012-01-17 | Boston Scientific Scimed, Inc. | Therapeutic inhibitor of vascular smooth muscle cells |
| US8158670B2 (en) | 1995-02-15 | 2012-04-17 | Boston Scientific Scimed, Inc. | Therapeutic inhibitor of vascular smooth muscle cells |
| US6734208B2 (en) | 1997-04-11 | 2004-05-11 | Neorx Corporation | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| WO1998046588A3 (en) * | 1997-04-11 | 1999-01-07 | Neorx Corp | Compounds and therapies for the prevention of vascular and non-vascular pathologies |
| US7625410B2 (en) | 2001-05-02 | 2009-12-01 | Boston Scientific Scimed, Inc. | Stent device and method |
| US7923571B2 (en) | 2004-12-29 | 2011-04-12 | Bayer Cropscience Ag | Process for preparing substituted 2-alkoxycarbonyl-3-aminothiophenes |
| CN101959875A (zh) * | 2008-02-29 | 2011-01-26 | 日产化学工业株式会社 | 噻吩化合物及其中间体的制造方法 |
| CN101959875B (zh) * | 2008-02-29 | 2013-10-16 | 日产化学工业株式会社 | 噻吩化合物及其中间体的制造方法 |
| CN103360290A (zh) * | 2008-02-29 | 2013-10-23 | 日产化学工业株式会社 | 噻吩化合物及其中间体的制造方法 |
| CN103435593B (zh) * | 2008-02-29 | 2015-01-28 | 日产化学工业株式会社 | 噻吩化合物及其中间体的制造方法 |
| CN103360290B (zh) * | 2008-02-29 | 2015-04-01 | 日产化学工业株式会社 | 噻吩化合物及其中间体的制造方法 |
| WO2024079734A1 (en) | 2022-10-14 | 2024-04-18 | Adama Agan Ltd. | Process for the preparation of substituted aminothiophene |
Also Published As
| Publication number | Publication date |
|---|---|
| IL52792A0 (en) | 1977-10-31 |
| BE858012A (fr) | 1978-02-22 |
| MC1156A1 (fr) | 1978-04-17 |
| AR222453A1 (es) | 1981-05-29 |
| IT1143757B (it) | 1986-10-22 |
| NL7709246A (nl) | 1978-02-27 |
| FR2365566A1 (fr) | 1978-04-21 |
| DK150484C (da) | 1987-10-05 |
| NO772917L (no) | 1978-02-24 |
| NZ184981A (en) | 1980-08-26 |
| HU179484B (en) | 1982-10-28 |
| ES461796A1 (es) | 1978-12-16 |
| FI66859B (fi) | 1984-08-31 |
| AU509956B2 (en) | 1980-06-05 |
| NO148673C (no) | 1983-11-23 |
| IL52792A (en) | 1981-06-29 |
| DE2737738A1 (de) | 1978-03-09 |
| FI66859C (fi) | 1984-12-10 |
| ATA607477A (de) | 1980-04-15 |
| CH628628A5 (en) | 1982-03-15 |
| AT359486B (de) | 1980-11-10 |
| NO148673B (no) | 1983-08-15 |
| IE45470B1 (en) | 1982-09-08 |
| AU2809277A (en) | 1979-03-01 |
| JPS6121235B2 (enrdf_load_stackoverflow) | 1986-05-26 |
| IE45470L (en) | 1978-02-23 |
| DK150484B (da) | 1987-03-09 |
| DE2737738C2 (de) | 1987-01-29 |
| FR2365566B1 (enrdf_load_stackoverflow) | 1980-12-26 |
| LU78003A1 (enrdf_load_stackoverflow) | 1978-09-14 |
| DK372177A (da) | 1978-02-24 |
| FI772494A7 (fi) | 1978-02-24 |
| JPS5340755A (en) | 1978-04-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 704A | Declaration that licence is not available as of right for an excepted use (par. 4a/1977) | ||
| 732 | Registration of transactions, instruments or events in the register (sect. 32/1977) | ||
| PCNP | Patent ceased through non-payment of renewal fee |