NO781061L - Fremgangsmaate ved fremstilling av thieno-(2,3-c) og (3,2-c)pyridiner - Google Patents
Fremgangsmaate ved fremstilling av thieno-(2,3-c) og (3,2-c)pyridinerInfo
- Publication number
- NO781061L NO781061L NO781061A NO781061A NO781061L NO 781061 L NO781061 L NO 781061L NO 781061 A NO781061 A NO 781061A NO 781061 A NO781061 A NO 781061A NO 781061 L NO781061 L NO 781061L
- Authority
- NO
- Norway
- Prior art keywords
- thieno
- pyridine
- tetrahydro
- radical
- oxo
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- 238000002360 preparation method Methods 0.000 title claims abstract 3
- RQMWVVBHJMUJNZ-UHFFFAOYSA-N 4-chloropyridin-2-amine Chemical compound NC1=CC(Cl)=CC=N1 RQMWVVBHJMUJNZ-UHFFFAOYSA-N 0.000 title 1
- 230000008569 process Effects 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 34
- -1 alkyl radical Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 238000005903 acid hydrolysis reaction Methods 0.000 claims description 4
- 150000005840 aryl radicals Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- KQBJATPSIFMPAB-UHFFFAOYSA-N 5-acetyl-6,7-dihydrothieno[3,2-c]pyridin-4-one Chemical compound O=C1N(C(=O)C)CCC2=C1C=CS2 KQBJATPSIFMPAB-UHFFFAOYSA-N 0.000 claims description 3
- WOHCIBUCSYHYOB-UHFFFAOYSA-N 6-acetyl-4,5-dihydrothieno[2,3-c]pyridin-7-one Chemical compound O=C1N(C(=O)C)CCC2=C1SC=C2 WOHCIBUCSYHYOB-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- HRQPKRZOGMLECX-UHFFFAOYSA-N 1-(5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)ethanone Chemical compound C1N(C(=O)C)CCC2=C1SC=C2 HRQPKRZOGMLECX-UHFFFAOYSA-N 0.000 claims description 2
- ORPWXKFFXAOFCU-UHFFFAOYSA-N 5,6-dihydro-4h-thieno[2,3-c]pyridin-7-one Chemical compound O=C1NCCC2=C1SC=C2 ORPWXKFFXAOFCU-UHFFFAOYSA-N 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical class 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- VEFXTGTZJOWDOF-UHFFFAOYSA-N benzene;hydrate Chemical compound O.C1=CC=CC=C1 VEFXTGTZJOWDOF-UHFFFAOYSA-N 0.000 claims description 2
- 125000005518 carboxamido group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 238000007254 oxidation reaction Methods 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- DXFQBPYXPWUJRJ-UHFFFAOYSA-N 1-(6,7-dihydro-4h-thieno[3,2-c]pyridin-5-yl)ethanone Chemical compound C1N(C(=O)C)CCC2=C1C=CS2 DXFQBPYXPWUJRJ-UHFFFAOYSA-N 0.000 claims 1
- SFNZVNVCJWVPDM-UHFFFAOYSA-N 6,7-dihydro-5h-thieno[3,2-c]pyridin-4-one Chemical compound O=C1NCCC2=C1C=CS2 SFNZVNVCJWVPDM-UHFFFAOYSA-N 0.000 claims 1
- 230000003647 oxidation Effects 0.000 claims 1
- 150000003222 pyridines Chemical class 0.000 abstract 1
- 239000013078 crystal Substances 0.000 description 18
- 238000012360 testing method Methods 0.000 description 14
- 230000015572 biosynthetic process Effects 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 210000003743 erythrocyte Anatomy 0.000 description 9
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 9
- 230000000202 analgesic effect Effects 0.000 description 8
- 241000700159 Rattus Species 0.000 description 7
- 230000003110 anti-inflammatory effect Effects 0.000 description 6
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
- 208000007536 Thrombosis Diseases 0.000 description 5
- 238000009825 accumulation Methods 0.000 description 5
- 230000002785 anti-thrombosis Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- SAALQYKUFCIMHR-UHFFFAOYSA-N propan-2-ol;2-propan-2-yloxypropane Chemical compound CC(C)O.CC(C)OC(C)C SAALQYKUFCIMHR-UHFFFAOYSA-N 0.000 description 5
- JKHOVHTXBVIELL-UHFFFAOYSA-N (3,4,5-trimethoxyphenyl)methyl 4-oxo-5-[(3,4,5-trimethoxyphenyl)methyl]-6,7-dihydrothieno[3,2-c]pyridine-6-carboxylate Chemical compound COC1=C(OC)C(OC)=CC(COC(=O)C2N(C(=O)C=3C=CSC=3C2)CC=2C=C(OC)C(OC)=C(OC)C=2)=C1 JKHOVHTXBVIELL-UHFFFAOYSA-N 0.000 description 4
- XTWYTFMLZFPYCI-KQYNXXCUSA-N 5'-adenylphosphoric acid Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]1O XTWYTFMLZFPYCI-KQYNXXCUSA-N 0.000 description 4
- XTWYTFMLZFPYCI-UHFFFAOYSA-N Adenosine diphosphate Natural products C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP(O)(O)=O)C(O)C1O XTWYTFMLZFPYCI-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 206010030113 Oedema Diseases 0.000 description 4
- 108010058846 Ovalbumin Proteins 0.000 description 4
- DUCFBPDBFHLPIT-UHFFFAOYSA-N benzyl 5-benzyl-4-oxo-6,7-dihydrothieno[3,2-c]pyridine-6-carboxylate Chemical compound C1C=2SC=CC=2C(=O)N(CC=2C=CC=CC=2)C1C(=O)OCC1=CC=CC=C1 DUCFBPDBFHLPIT-UHFFFAOYSA-N 0.000 description 4
- 230000002757 inflammatory effect Effects 0.000 description 4
- 230000002401 inhibitory effect Effects 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000002347 injection Methods 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 229940092253 ovalbumin Drugs 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- 239000002504 physiological saline solution Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- 102000007327 Protamines Human genes 0.000 description 3
- 108010007568 Protamines Proteins 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000002744 anti-aggregatory effect Effects 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- OYJXTOVLKZDGFK-UHFFFAOYSA-N ethanol;2-propan-2-yloxypropane Chemical compound CCO.CC(C)OC(C)C OYJXTOVLKZDGFK-UHFFFAOYSA-N 0.000 description 3
- 238000000338 in vitro Methods 0.000 description 3
- 238000001727 in vivo Methods 0.000 description 3
- 210000004731 jugular vein Anatomy 0.000 description 3
- 235000019359 magnesium stearate Nutrition 0.000 description 3
- 230000000144 pharmacologic effect Effects 0.000 description 3
- 229950008679 protamine sulfate Drugs 0.000 description 3
- 239000000829 suppository Substances 0.000 description 3
- SQUPREJKSMSDSM-UHFFFAOYSA-N 6-acetyl-4-phenyl-4,5-dihydrothieno[2,3-c]pyridin-7-one Chemical compound C1=2C=CSC=2C(=O)N(C(=O)C)CC1C1=CC=CC=C1 SQUPREJKSMSDSM-UHFFFAOYSA-N 0.000 description 2
- 102000008186 Collagen Human genes 0.000 description 2
- 108010035532 Collagen Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700157 Rattus norvegicus Species 0.000 description 2
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 239000004480 active ingredient Substances 0.000 description 2
- 230000002776 aggregation Effects 0.000 description 2
- 238000004220 aggregation Methods 0.000 description 2
- 210000001367 artery Anatomy 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 235000010418 carrageenan Nutrition 0.000 description 2
- 229920001525 carrageenan Polymers 0.000 description 2
- 229920001436 collagen Polymers 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000002513 implantation Methods 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 238000007912 intraperitoneal administration Methods 0.000 description 2
- 239000007928 intraperitoneal injection Substances 0.000 description 2
- 238000002350 laparotomy Methods 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- WEXRUCMBJFQVBZ-UHFFFAOYSA-N pentobarbital Chemical compound CCCC(C)C1(CC)C(=O)NC(=O)NC1=O WEXRUCMBJFQVBZ-UHFFFAOYSA-N 0.000 description 2
- 239000012286 potassium permanganate Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 229910052710 silicon Inorganic materials 0.000 description 2
- 239000010703 silicon Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 230000009885 systemic effect Effects 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 230000002110 toxicologic effect Effects 0.000 description 2
- 231100000027 toxicology Toxicity 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- JFBBIVHGWNLDSF-UHFFFAOYSA-N 1-(4-phenyl-5,7-dihydro-4h-thieno[2,3-c]pyridin-6-yl)ethanone Chemical compound C1=2C=CSC=2CN(C(=O)C)CC1C1=CC=CC=C1 JFBBIVHGWNLDSF-UHFFFAOYSA-N 0.000 description 1
- KPNSVTJZVKVJDN-UHFFFAOYSA-N 4-oxo-5-[(3,4,5-trimethoxyphenyl)methyl]-6,7-dihydrothieno[3,2-c]pyridine-6-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CN2C(C=3C=CSC=3CC2C(O)=O)=O)=C1 KPNSVTJZVKVJDN-UHFFFAOYSA-N 0.000 description 1
- FGYGZWWCDBBOKF-UHFFFAOYSA-N 4-phenyl-5,6-dihydro-4h-thieno[2,3-c]pyridin-7-one Chemical compound C1=2C=CSC=2C(=O)NCC1C1=CC=CC=C1 FGYGZWWCDBBOKF-UHFFFAOYSA-N 0.000 description 1
- ZPIFZGZFOYNURZ-UHFFFAOYSA-N 5-benzyl-4-oxo-6,7-dihydrothieno[3,2-c]pyridine-6-carboxylic acid Chemical compound OC(=O)C1CC=2SC=CC=2C(=O)N1CC1=CC=CC=C1 ZPIFZGZFOYNURZ-UHFFFAOYSA-N 0.000 description 1
- GUPPGBJHJWFJCP-UHFFFAOYSA-N 5-benzyl-6,7-dihydro-4h-thieno[3,2-c]pyridine Chemical compound C1CC=2SC=CC=2CN1CC1=CC=CC=C1 GUPPGBJHJWFJCP-UHFFFAOYSA-N 0.000 description 1
- JYXQOXRDWSBYGS-UHFFFAOYSA-N 5-benzyl-6,7-dihydrothieno[3,2-c]pyridin-4-one Chemical compound C1CC=2SC=CC=2C(=O)N1CC1=CC=CC=C1 JYXQOXRDWSBYGS-UHFFFAOYSA-N 0.000 description 1
- 206010003178 Arterial thrombosis Diseases 0.000 description 1
- 206010003210 Arteriosclerosis Diseases 0.000 description 1
- BSYNRYMUTXBXSQ-UHFFFAOYSA-N Aspirin Chemical compound CC(=O)OC1=CC=CC=C1C(O)=O BSYNRYMUTXBXSQ-UHFFFAOYSA-N 0.000 description 1
- 208000037260 Atherosclerotic Plaque Diseases 0.000 description 1
- 241000283690 Bos taurus Species 0.000 description 1
- 229920002261 Corn starch Polymers 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- NOTFZGFABLVTIG-UHFFFAOYSA-N Cyclohexylethyl acetate Chemical compound CC(=O)OCCC1CCCCC1 NOTFZGFABLVTIG-UHFFFAOYSA-N 0.000 description 1
- 235000019739 Dicalciumphosphate Nutrition 0.000 description 1
- 206010019280 Heart failures Diseases 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 229920001800 Shellac Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 229960001138 acetylsalicylic acid Drugs 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 238000011888 autopsy Methods 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- YMVMLOLCHUVAJB-UHFFFAOYSA-N benzyl 5-benzyl-6,7-dihydro-4h-thieno[3,2-c]pyridine-6-carboxylate Chemical compound C1C=2SC=CC=2CN(CC=2C=CC=CC=2)C1C(=O)OCC1=CC=CC=C1 YMVMLOLCHUVAJB-UHFFFAOYSA-N 0.000 description 1
- 210000000988 bone and bone Anatomy 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000004203 carnauba wax Substances 0.000 description 1
- 235000013869 carnauba wax Nutrition 0.000 description 1
- 235000019994 cava Nutrition 0.000 description 1
- 210000004027 cell Anatomy 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 230000002490 cerebral effect Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 210000001072 colon Anatomy 0.000 description 1
- 239000008120 corn starch Substances 0.000 description 1
- 230000003412 degenerative effect Effects 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- IZEKFCXSFNUWAM-UHFFFAOYSA-N dipyridamole Chemical compound C=12N=C(N(CCO)CCO)N=C(N3CCCCC3)C2=NC(N(CCO)CCO)=NC=1N1CCCCC1 IZEKFCXSFNUWAM-UHFFFAOYSA-N 0.000 description 1
- 229960002768 dipyridamole Drugs 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- IINNWAYUJNWZRM-UHFFFAOYSA-L erythrosin B Chemical compound [Na+].[Na+].[O-]C(=O)C1=CC=CC=C1C1=C2C=C(I)C(=O)C(I)=C2OC2=C(I)C([O-])=C(I)C=C21 IINNWAYUJNWZRM-UHFFFAOYSA-L 0.000 description 1
- AINBZKYUNWUTRE-UHFFFAOYSA-N ethanol;propan-2-ol Chemical compound CCO.CC(C)O AINBZKYUNWUTRE-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 230000014509 gene expression Effects 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 210000000548 hind-foot Anatomy 0.000 description 1
- 238000010562 histological examination Methods 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 210000000936 intestine Anatomy 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000001872 metatarsal bone Anatomy 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 229960001412 pentobarbital Drugs 0.000 description 1
- 230000002093 peripheral effect Effects 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 230000000793 phophlogistic effect Effects 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 210000002435 tendon Anatomy 0.000 description 1
- DBDCNCCRPKTRSD-UHFFFAOYSA-N thieno[3,2-b]pyridine Chemical class C1=CC=C2SC=CC2=N1 DBDCNCCRPKTRSD-UHFFFAOYSA-N 0.000 description 1
- 208000014173 thrombophilia due to thrombin defect Diseases 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000048 toxicity data Toxicity 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 210000001631 vena cava inferior Anatomy 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229940045860 white wax Drugs 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB13209/77A GB1576511A (en) | 1977-03-29 | 1977-03-29 | Thieno(2,3 - c) and (3,2 - c) pyridines process for their preparation and therapeutic applications thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO781061L true NO781061L (no) | 1978-10-02 |
Family
ID=10018826
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO781061A NO781061L (no) | 1977-03-29 | 1978-03-28 | Fremgangsmaate ved fremstilling av thieno-(2,3-c) og (3,2-c)pyridiner |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US4193997A (it) |
| JP (1) | JPS53119892A (it) |
| AR (1) | AR222792A1 (it) |
| AT (1) | AT360015B (it) |
| AU (1) | AU515504B2 (it) |
| BE (1) | BE865358A (it) |
| CA (1) | CA1106377A (it) |
| CH (1) | CH629810A5 (it) |
| DD (1) | DD135387A5 (it) |
| DE (1) | DE2812950A1 (it) |
| DK (1) | DK135578A (it) |
| FI (1) | FI780932A (it) |
| FR (1) | FR2385720A1 (it) |
| GB (1) | GB1576511A (it) |
| GR (1) | GR64817B (it) |
| HU (1) | HU175646B (it) |
| IE (1) | IE46577B1 (it) |
| IL (1) | IL54287A (it) |
| IT (1) | IT1104187B (it) |
| LU (1) | LU79236A1 (it) |
| MX (1) | MX5215E (it) |
| NL (1) | NL7803086A (it) |
| NO (1) | NO781061L (it) |
| NZ (1) | NZ186771A (it) |
| PH (1) | PH15889A (it) |
| PL (1) | PL110774B1 (it) |
| PT (1) | PT67831B (it) |
| SE (1) | SE7803035L (it) |
| SU (1) | SU910122A3 (it) |
| YU (1) | YU70978A (it) |
| ZA (1) | ZA781478B (it) |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AT368504B (de) * | 1977-10-15 | 1982-10-25 | Boehringer Sohn Ingelheim | Verfahren zur herstellung neuer 4-phenyl-thieno- (2,3-c)-piperidine |
| FR2429219A1 (fr) * | 1978-06-22 | 1980-01-18 | Parcor | Medicament a base de derives de la thienopyridone ou de la furopyridone |
| DE3134933A1 (de) * | 1981-09-03 | 1983-03-31 | Hoechst Ag, 6230 Frankfurt | "harnstoffderivate, verfahren zu ihrer herstellung und diese enthaltende medikamente sowie deren verwendung" |
| US4593099A (en) * | 1984-10-10 | 1986-06-03 | Merrell Dow Pharmaceuticals Inc. | (Tetrazolyl) thienopyridinones |
| GB8429087D0 (en) * | 1984-11-16 | 1984-12-27 | Scras | Thienopyridine derivatives |
| US5059692A (en) * | 1989-09-01 | 1991-10-22 | Hiroyoshi Hidaka | Novel compounds exhibiting a vasodilating activity and inhibitory activity for platelet aggregation |
| US5334596A (en) * | 1993-05-11 | 1994-08-02 | Merck & Co., Inc. | Fibrinogen receptor antagonists |
| FR2748026B1 (fr) * | 1996-04-26 | 1998-06-05 | Adir | Nouveaux inhibiteurs de metalloproteases, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| EP1350511B1 (en) * | 2000-12-25 | 2008-09-10 | Daiichi Sankyo Company, Limited | Medicinal compositions containing aspirin |
| CN102417514B (zh) * | 2011-10-20 | 2013-11-27 | 天津药物研究院 | 吡啶衍生物、其制备方法和用途 |
| US10435806B2 (en) * | 2015-10-12 | 2019-10-08 | Prc-Desoto International, Inc. | Methods for electrolytically depositing pretreatment compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2143744A1 (de) * | 1971-09-01 | 1973-03-08 | Hoechst Ag | 3,4-dihydro-2h-isochinolin-1-one und verfahren zu ihrer herstellung |
| US3903095A (en) * | 1972-02-18 | 1975-09-02 | Merck & Co Inc | Certain substituted-thieno{8 3,2-c{9 -pyridines |
| US3845065A (en) * | 1972-02-18 | 1974-10-29 | Merck & Co Inc | 4-oxo-4,5-dihydrothieno(3,2-c)pyridines |
-
1977
- 1977-03-29 GB GB13209/77A patent/GB1576511A/en not_active Expired
-
1978
- 1978-03-10 GR GR55691A patent/GR64817B/el unknown
- 1978-03-10 FR FR7807008A patent/FR2385720A1/fr active Granted
- 1978-03-13 CH CH269178A patent/CH629810A5/fr not_active IP Right Cessation
- 1978-03-14 IE IE512/78A patent/IE46577B1/en unknown
- 1978-03-14 IL IL54287A patent/IL54287A/xx unknown
- 1978-03-14 ZA ZA00781478A patent/ZA781478B/xx unknown
- 1978-03-15 US US05/886,688 patent/US4193997A/en not_active Expired - Lifetime
- 1978-03-15 LU LU79236A patent/LU79236A1/xx unknown
- 1978-03-16 SE SE7803035A patent/SE7803035L/xx unknown
- 1978-03-22 NZ NZ186771A patent/NZ186771A/xx unknown
- 1978-03-22 NL NL7803086A patent/NL7803086A/xx not_active Application Discontinuation
- 1978-03-23 DE DE19782812950 patent/DE2812950A1/de not_active Withdrawn
- 1978-03-23 HU HU78PA1308A patent/HU175646B/hu not_active IP Right Cessation
- 1978-03-24 SU SU782593002A patent/SU910122A3/ru active
- 1978-03-27 DD DD78204412A patent/DD135387A5/xx unknown
- 1978-03-27 YU YU00709/78A patent/YU70978A/xx unknown
- 1978-03-28 CA CA299,760A patent/CA1106377A/en not_active Expired
- 1978-03-28 AT AT216278A patent/AT360015B/de not_active IP Right Cessation
- 1978-03-28 FI FI780932A patent/FI780932A/fi not_active Application Discontinuation
- 1978-03-28 BE BE186303A patent/BE865358A/xx not_active IP Right Cessation
- 1978-03-28 PL PL1978205633A patent/PL110774B1/pl unknown
- 1978-03-28 JP JP3595178A patent/JPS53119892A/ja active Pending
- 1978-03-28 DK DK135578A patent/DK135578A/da active Protection Beyond IP Right Term
- 1978-03-28 MX MX786953U patent/MX5215E/es unknown
- 1978-03-28 PT PT67831A patent/PT67831B/pt unknown
- 1978-03-28 NO NO781061A patent/NO781061L/no unknown
- 1978-03-28 AR AR271579A patent/AR222792A1/es active
- 1978-03-29 IT IT48638/78A patent/IT1104187B/it active
- 1978-03-29 PH PH20948A patent/PH15889A/en unknown
- 1978-03-29 AU AU34566/78A patent/AU515504B2/en not_active Expired
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0127135B1 (en) | Fused tricyclic derivatives of naphthyridinone and pyridone and the corresponding thiones | |
| NO163406B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive imidazokinolinonderivater. | |
| NO781061L (no) | Fremgangsmaate ved fremstilling av thieno-(2,3-c) og (3,2-c)pyridiner | |
| NO152048B (no) | Analogifremgangsmaate ved fremstilling av nye, terapeutisk aktive 5h-2,3-benzodiazepinderivater | |
| IE49077B1 (en) | 5-(4-pyridyl)-6-(4-fluorophenyl)-2,3-dihydroimidazo(2,1-b)thiazole,process for its preparation and medical composition | |
| JP3122792B2 (ja) | 新規な活性化合物 | |
| NO780050L (no) | Fremgangsmaate ved fremstilling av 4,5,6,7-tetrahydrothieno-(2,3-c) og (3,2-c)pyridiner | |
| JPS6126546B2 (it) | ||
| CA1218656A (en) | Pyridothienotriazines | |
| US3843663A (en) | 1,8-naphthyridine compounds | |
| JPH064616B2 (ja) | ２−（ピペラジニル）−２−オキソエチレン−置換フラボノイド誘導体、その製法およびそれを含有する医薬組成物 | |
| US5527796A (en) | Thienothiazine derivatives and their use | |
| GB2125403A (en) | Fused thieno (3,2-6)thiozole-2-anure derivitives | |
| US4187303A (en) | Thiazine derivatives | |
| US4496568A (en) | Antiinflammatory thieno [2,3-c]pyridine derivatives | |
| SK8732000A3 (en) | Potassium channel openers | |
| JPS6345394B2 (it) | ||
| HU185070B (en) | Process for producing 5,6,7,7a-tetrahydro-thieno-bracket-3,2-c-bracket closed-pyridin-2-one-derivatives | |
| SU1145931A3 (ru) | Способ получени производных 5,6,7,7а-тетрагидро-4 @ -тиено/3,2- @ /-пиридинона-2 или их солей | |
| DK147825B (da) | Fremgangsmaade til fremstilling af thieno(3,2-c)pyridinderivater | |
| GB1570500A (en) | Anti-9,10-dihydro-4-(1-methyl-4-piperidylidene)-4h-benzo(4,5) cyclohepta (1,2-b)thiophen-10(9h)-one oxime | |
| NO147561B (no) | Analogifremgangsmaater for fremstilling av 6,11-dihydro-11-oksodibenz(b,e)oksepinalkan-syrer, estere og salter derav | |
| JPH0739423B2 (ja) | ピリミドベンゾチアジン誘導体を含む抗炎症剤 | |
| JPH0625184B2 (ja) | 新規置換ベンゾチアゾリノン、その製法およびそれを含有する医薬組成物 | |
| NO800449L (no) | Analogifremgangsmaate for fremstilling av farmasoeytisk aktive tetrahydropyridin-karboksylsyre-derivater |