DD281602A5 - Verfahren zur herstellung von 3,4-dihydro-2-alkyl-3-oxo-n-aryl-2-h-(1)benzothieno-(3,2,-e)-1,2-thiazin-4-carboxamid-1,1-dioxiden - Google Patents

Verfahren zur herstellung von 3,4-dihydro-2-alkyl-3-oxo-n-aryl-2-h-(1)benzothieno-(3,2,-e)-1,2-thiazin-4-carboxamid-1,1-dioxiden Download PDF

Info

Publication number: DD281602A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; alkyl; compound; hydrogen; methyl
Prior art date: 1987-06-10

Application number

DD88316546A

Other languages

German (de)

English (en)

Inventor

Anthony Marfat

Original Assignee

��@��Kk��

Priority date (The priority date 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 date listed.)

1987-06-10

Filing date

1988-06-08

Publication date

1990-08-15

1988-06-08 Application filed by ��@��Kk�� filed Critical ��@��Kk��

1990-08-15 Publication of DD281602A5 publication Critical patent/DD281602A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 16
238000002360 preparation method Methods 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 60
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 17
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 17
-1 nitro, hydroxyl Chemical group 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 10
150000002367 halogens Chemical group 0.000 claims abstract description 10
125000000217 alkyl group Chemical group 0.000 claims abstract description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 7
125000005059 halophenyl group Chemical group 0.000 claims abstract description 3
125000001424 substituent group Chemical group 0.000 claims abstract description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 3
238000006243 chemical reaction Methods 0.000 claims description 9
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims description 6
239000011541 reaction mixture Substances 0.000 claims description 6
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 3
125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
125000004199 4-trifluoromethylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C(F)(F)F 0.000 claims description 3
239000001569 carbon dioxide Substances 0.000 claims description 3
229910002092 carbon dioxide Inorganic materials 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 2
230000018044 dehydration Effects 0.000 claims 1
238000006297 dehydration reaction Methods 0.000 claims 1
150000003180 prostaglandins Chemical class 0.000 abstract description 8
201000010099 disease Diseases 0.000 abstract description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 7
229940094443 oxytocics prostaglandins Drugs 0.000 abstract description 7
150000002617 leukotrienes Chemical class 0.000 abstract description 6
230000002757 inflammatory effect Effects 0.000 abstract description 3
HAHIGNPNCWKCOD-UHFFFAOYSA-N 2H-thiazine-4-carboxamide Chemical class S1NC=C(C=C1)C(=O)N HAHIGNPNCWKCOD-UHFFFAOYSA-N 0.000 abstract 1
239000000867 Lipoxygenase Inhibitor Chemical class 0.000 abstract 1
230000001754 anti-pyretic effect Effects 0.000 abstract 1
239000002221 antipyretic Chemical class 0.000 abstract 1
229940125716 antipyretic agent Drugs 0.000 abstract 1
238000004519 manufacturing process Methods 0.000 abstract 1
239000008177 pharmaceutical agent Substances 0.000 abstract 1
239000002599 prostaglandin synthase inhibitor Chemical class 0.000 abstract 1
150000004897 thiazines Chemical class 0.000 abstract 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 21
IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 18
239000002904 solvent Substances 0.000 description 13
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
239000000243 solution Substances 0.000 description 10
238000005160 1H NMR spectroscopy Methods 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
238000004458 analytical method Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
239000012948 isocyanate Substances 0.000 description 8
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RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical group CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical group CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000012429 reaction media Substances 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
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BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
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KGIJOOYOSFUGPC-XRXZHELTSA-N 5-hydroxyeicosatetraenoic acid Natural products CCCCCC=CCC=CCC=C\C=C\C(O)CCCC(O)=O KGIJOOYOSFUGPC-XRXZHELTSA-N 0.000 description 3
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UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 3
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
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238000006210 cyclodehydration reaction Methods 0.000 description 3
239000000203 mixture Substances 0.000 description 3
MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229940114079 arachidonic acid Drugs 0.000 description 2
235000021342 arachidonic acid Nutrition 0.000 description 2
208000006673 asthma Diseases 0.000 description 2
125000005605 benzo group Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
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239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000003937 drug carrier Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000007789 gas Substances 0.000 description 2
238000011534 incubation Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
229910052943 magnesium sulfate Inorganic materials 0.000 description 2
235000019341 magnesium sulphate Nutrition 0.000 description 2
230000037361 pathway Effects 0.000 description 2
239000008194 pharmaceutical composition Substances 0.000 description 2
230000002685 pulmonary effect Effects 0.000 description 2
239000007787 solid Substances 0.000 description 2
229940124530 sulfonamide Drugs 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
239000008096 xylene Substances 0.000 description 2
SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
CZQIJQFTRGDODI-UHFFFAOYSA-N 1-bromo-4-isocyanatobenzene Chemical compound BrC1=CC=C(N=C=O)C=C1 CZQIJQFTRGDODI-UHFFFAOYSA-N 0.000 description 1
DSVGFKBFFICWLZ-UHFFFAOYSA-N 1-fluoro-4-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C=C1 DSVGFKBFFICWLZ-UHFFFAOYSA-N 0.000 description 1
FZCFUPBIPMLIPI-UHFFFAOYSA-N 1-isocyanato-2-methyl-4-nitrobenzene Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N=C=O FZCFUPBIPMLIPI-UHFFFAOYSA-N 0.000 description 1
QZTWVDCKDWZCLV-UHFFFAOYSA-N 1-isocyanato-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(N=C=O)C=C1 QZTWVDCKDWZCLV-UHFFFAOYSA-N 0.000 description 1
125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
HNENEALJPWJWJY-UHFFFAOYSA-N 2,4-difluoro-1-isocyanatobenzene Chemical compound FC1=CC=C(N=C=O)C(F)=C1 HNENEALJPWJWJY-UHFFFAOYSA-N 0.000 description 1
RCNOGGGBSSVMAS-UHFFFAOYSA-N 2-thiophen-3-ylacetic acid Chemical compound OC(=O)CC=1C=CSC=1 RCNOGGGBSSVMAS-UHFFFAOYSA-N 0.000 description 1
208000016557 Acute basophilic leukemia Diseases 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
108091003079 Bovine Serum Albumin Proteins 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
239000006145 Eagle's minimal essential medium Substances 0.000 description 1
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 1
206010020751 Hypersensitivity Diseases 0.000 description 1
206010021143 Hypoxia Diseases 0.000 description 1
208000022559 Inflammatory bowel disease Diseases 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
241000124008 Mammalia Species 0.000 description 1
208000007101 Muscle Cramp Diseases 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
208000008469 Peptic Ulcer Diseases 0.000 description 1
201000004681 Psoriasis Diseases 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
208000005392 Spasm Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
208000026935 allergic disease Diseases 0.000 description 1
230000000172 allergic effect Effects 0.000 description 1
230000007815 allergy Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
230000001857 anti-mycotic effect Effects 0.000 description 1
239000002543 antimycotic Substances 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000002585 base Substances 0.000 description 1
239000011324 bead Substances 0.000 description 1
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 1
230000003115 biocidal effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
239000003710 calcium ionophore Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000006285 cell suspension Substances 0.000 description 1
238000005119 centrifugation Methods 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
CJAONIOAQZUHPN-KKLWWLSJSA-N ethyl 12-[[2-[(2r,3r)-3-[2-[(12-ethoxy-12-oxododecyl)-methylamino]-2-oxoethoxy]butan-2-yl]oxyacetyl]-methylamino]dodecanoate Chemical compound CCOC(=O)CCCCCCCCCCCN(C)C(=O)CO[C@H](C)[C@@H](C)OCC(=O)N(C)CCCCCCCCCCCC(=O)OCC CJAONIOAQZUHPN-KKLWWLSJSA-N 0.000 description 1
BLHLJVCOVBYQQS-UHFFFAOYSA-N ethyllithium Chemical compound [Li]CC BLHLJVCOVBYQQS-UHFFFAOYSA-N 0.000 description 1
239000012894 fetal calf serum Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
230000002496 gastric effect Effects 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
230000007954 hypoxia Effects 0.000 description 1
239000005457 ice water Substances 0.000 description 1
208000027866 inflammatory disease Diseases 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 1
WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 1
230000001404 mediated effect Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
208000010125 myocardial infarction Diseases 0.000 description 1
230000007935 neutral effect Effects 0.000 description 1
125000006501 nitrophenyl group Chemical group 0.000 description 1
229940021182 non-steroidal anti-inflammatory drug Drugs 0.000 description 1
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230000020477 pH reduction Effects 0.000 description 1
208000011906 peptic ulcer disease Diseases 0.000 description 1
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239000002798 polar solvent Substances 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
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239000000741 silica gel Substances 0.000 description 1
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239000002356 single layer Substances 0.000 description 1
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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
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 carbon atoms of the hetero ring
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/14—Antitussive agents
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Engineering & Computer Science (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pulmonology (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Vascular Medicine (AREA)
Urology & Nephrology (AREA)
Immunology (AREA)
Pain & Pain Management (AREA)
Rheumatology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Hydrogenated Pyridines (AREA)
Thiazole And Isothizaole Compounds (AREA)

DD88316546A 1987-06-10 1988-06-08 Verfahren zur herstellung von 3,4-dihydro-2-alkyl-3-oxo-n-aryl-2-h-(1)benzothieno-(3,2,-e)-1,2-thiazin-4-carboxamid-1,1-dioxiden DD281602A5 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
PCT/US1987/001357 WO1988009793A1 (en)	1987-06-10	1987-06-10	3,4-DIHYDRO-2-ALKYL-3-OXO-N-ARYL-2H-[1]BENZOTHIENO[3,2-e]-1,2-THIAZINE-4-CARBOXAMIDE-1,1-DIOXIDES
EP88304975A EP0294994B1 (en)	1987-06-10	1988-06-01	3-4-Dihydro-2-alkyl-3-oxo-N-aryl-2H-[1]benzothieno[3,2-el]-1,2-thiazine-4-carboxamide-1,1-dioxides

Publications (1)

Publication Number	Publication Date
DD281602A5 true DD281602A5 (de)	1990-08-15

Family

ID=55448100

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD88316546A DD281602A5 (de)	1987-06-10	1988-06-08	Verfahren zur herstellung von 3,4-dihydro-2-alkyl-3-oxo-n-aryl-2-h-(1)benzothieno-(3,2,-e)-1,2-thiazin-4-carboxamid-1,1-dioxiden

Country Status (28)

Country	Link
US (1)	US4914101A (pl)
EP (1)	EP0294994B1 (pl)
JP (1)	JPH078874B2 (pl)
KR (1)	KR900006758B1 (pl)
CN (1)	CN1019576B (pl)
AT (1)	ATE105561T1 (pl)
AU (1)	AU593743B2 (pl)
CA (1)	CA1300625C (pl)
CZ (1)	CZ281857B6 (pl)
DD (1)	DD281602A5 (pl)
DE (1)	DE3889497T2 (pl)
DK (1)	DK313388A (pl)
EG (1)	EG18525A (pl)
ES (1)	ES2051846T3 (pl)
FI (1)	FI89802C (pl)
HU (1)	HU203762B (pl)
IE (1)	IE63214B1 (pl)
IL (1)	IL86602A (pl)
MX (1)	MX174093B (pl)
MY (1)	MY103572A (pl)
NO (2)	NO176277C (pl)
NZ (1)	NZ224956A (pl)
PH (1)	PH25187A (pl)
PL (1)	PL158994B1 (pl)
PT (1)	PT87678B (pl)
WO (1)	WO1988009793A1 (pl)
YU (1)	YU46767B (pl)
ZA (1)	ZA884115B (pl)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0455830B1 (en) *	1989-11-30	1996-06-26	Nippon Hypox Laboratories Incorporated	Medicine containing thiazine dioxide derivative
US6340659B1 (en)	1995-12-13	2002-01-22	The Lubrizol Corporation	Metal salts of lactones as lubricant additives
JP4250344B2 (ja)	2001-01-29	2009-04-08	インターナショナル・ビジネス・マシーンズ・コーポレーション	ワークフローシステム、ワークフローサーバ、および記憶媒体
US8741299B2 (en) *	2011-06-20	2014-06-03	The Feinstein Institute For Medical Research	Method for treating pathologies associated with hypoxia using MIF inhibitors
US9666805B2 (en) *	2014-11-25	2017-05-30	Northwestern University	Bithiophene sulfonamide-based molecular and polymeric semiconductors

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3591584A (en) *	1968-08-27	1971-07-06	Pfizer	Benzothiazine dioxides
CA1066711A (en) *	1974-08-26	1979-11-20	Hoffmann-La Roche Limited	Thiophene derivatives
LU78009A1 (de) *	1977-08-22	1979-05-23	Hoffmann La Roche	Verfahren zur herstellung von thiazinderivaten
AU518216B2 (en) *	1977-09-06	1981-09-17	Hafslund Nycomed Pharma Aktiengesellschaft	Thienothiazine derivatives
DE2838377A1 (de) *	1978-09-02	1980-03-20	Thomae Gmbh Dr K	Neue 4-hydroxy-2h eckige klammer auf 1 eckige klammer zu benzothieno eckige klammer auf 2,3-e eckige klammer zu -1,2- thiazin-3-carboxamid-1,1-dioxide sowie deren salze, deren verwendung und verfahren zu ihrer herstellung
AU5811280A (en) *	1979-06-13	1980-12-18	F. Hoffmann-La Roche Ag	Thiazine derivatives
ZA803401B (en) *	1979-06-13	1981-05-27	Hoffmann La Roche	Thiazine derivatives

1987
- 1987-06-10 US US07/382,161 patent/US4914101A/en not_active Expired - Lifetime
- 1987-06-10 HU HU873899A patent/HU203762B/hu not_active IP Right Cessation
- 1987-06-10 WO PCT/US1987/001357 patent/WO1988009793A1/en not_active Ceased
- 1987-06-10 MX MX011827A patent/MX174093B/es unknown
1988
- 1988-06-01 ES ES88304975T patent/ES2051846T3/es not_active Expired - Lifetime
- 1988-06-01 DE DE3889497T patent/DE3889497T2/de not_active Expired - Fee Related
- 1988-06-01 AT AT8888304975T patent/ATE105561T1/de not_active IP Right Cessation
- 1988-06-01 EP EP88304975A patent/EP0294994B1/en not_active Expired - Lifetime
- 1988-06-02 IL IL86602A patent/IL86602A/xx not_active IP Right Cessation
- 1988-06-06 MY MYPI88000605A patent/MY103572A/en unknown
- 1988-06-06 JP JP13920488A patent/JPH078874B2/ja not_active Expired - Lifetime
- 1988-06-07 CZ CS883925A patent/CZ281857B6/cs not_active IP Right Cessation
- 1988-06-08 PH PH37029A patent/PH25187A/en unknown
- 1988-06-08 PT PT87678A patent/PT87678B/pt not_active IP Right Cessation
- 1988-06-08 DD DD88316546A patent/DD281602A5/de not_active IP Right Cessation
- 1988-06-08 CA CA000568893A patent/CA1300625C/en not_active Expired - Lifetime
- 1988-06-08 PL PL1988272928A patent/PL158994B1/pl unknown
- 1988-06-09 IE IE173388A patent/IE63214B1/en not_active IP Right Cessation
- 1988-06-09 KR KR1019880006909A patent/KR900006758B1/ko not_active Expired
- 1988-06-09 ZA ZA884115A patent/ZA884115B/xx unknown
- 1988-06-09 CN CN88103539A patent/CN1019576B/zh not_active Expired
- 1988-06-09 AU AU17535/88A patent/AU593743B2/en not_active Ceased
- 1988-06-09 NZ NZ224956A patent/NZ224956A/xx unknown
- 1988-06-09 YU YU111988A patent/YU46767B/sh unknown
- 1988-06-09 DK DK313388A patent/DK313388A/da not_active Application Discontinuation
- 1988-06-09 EG EG32188A patent/EG18525A/xx active
1989
- 1989-02-08 NO NO890531A patent/NO176277C/no unknown
- 1989-02-09 FI FI890620A patent/FI89802C/fi not_active IP Right Cessation
1992
- 1992-07-03 NO NO922636A patent/NO922636D0/no unknown

Also Published As

Publication number	Publication date
JPH078874B2 (ja)	1995-02-01
IE63214B1 (en)	1995-04-05
ES2051846T3 (es)	1994-07-01
IE881733L (en)	1988-12-10
ZA884115B (en)	1990-02-28
NO890531L (no)	1989-02-08
MX11827A (es)	1993-04-01
CN1019576B (zh)	1992-12-23
EG18525A (en)	1994-04-30
NO922636L (no)	1989-02-08
PL272928A1 (en)	1989-07-10
AU593743B2 (en)	1990-02-15
KR890000500A (ko)	1989-03-15
US4914101A (en)	1990-04-03
KR900006758B1 (ko)	1990-09-20
EP0294994A1 (en)	1988-12-14
NO922636D0 (no)	1992-07-03
PL158994B1 (pl)	1992-10-30
FI890620A7 (fi)	1989-02-09
NO890531D0 (no)	1989-02-08
JPS6413093A (en)	1989-01-17
HU203762B (en)	1991-09-30
DK313388A (da)	1988-12-11
CN88103539A (zh)	1988-12-28
AU1753588A (en)	1988-12-15
HUT54376A (en)	1991-02-28
CZ281857B6 (cs)	1997-03-12
YU111988A (en)	1989-12-31
EP0294994B1 (en)	1994-05-11
YU46767B (sh)	1994-05-10
FI89802C (fi)	1993-11-25
MX174093B (es)	1994-04-21
CA1300625C (en)	1992-05-12
PH25187A (en)	1991-03-27
NO176277B (no)	1994-11-28
IL86602A (en)	1992-06-21
FI89802B (fi)	1993-08-13
PT87678A (pt)	1988-07-01
DK313388D0 (da)	1988-06-09
PT87678B (pt)	1992-10-30
NO176277C (no)	1995-03-08
DE3889497D1 (de)	1994-06-16
NZ224956A (en)	1990-07-26
ATE105561T1 (de)	1994-05-15
FI890620A0 (fi)	1989-02-09
MY103572A (en)	1993-08-28
DE3889497T2 (de)	1994-08-25
WO1988009793A1 (en)	1988-12-15
IL86602A0 (en)	1988-11-30
CZ392588A3 (en)	1996-11-13

Legal Events

Date	Code	Title	Description
1996-08-14	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0353557B1 (de)	1992-09-16	Tetrahydro-1-benz-[c,d]-indol-propionsäure-sulfonamide
US4182769A (en)	1980-01-08	Anti-inflammatory 1-substituted-4,5-diaryl-2-(substituted-thio) imidazoles and their corresponding sulfoxides and sulfones
CH628035A5 (de)	1982-02-15	Verfahren zur herstellung von neuen sulfonylbenzimidazolen.
DD253823A5 (de)	1988-02-03	Verfahren zur herstellung neuartiger thienopyridone
CH629203A5 (de)	1982-04-15	Verfahren zur herstellung von thiazolinylbenzimidazolen.
DE3850308T2 (de)	1994-10-06	Tetrahydroisochinolin-2-yl-Derivate als Thromboxan A2-Antagonisten.
DE2730832A1 (de)	1978-01-19	Thieno-(2,3-c)- und -(3,2-c)pyridine, verfahren zu ihrer herstellung und sie enthaltende arzneimittel
DE3889497T2 (de)	1994-08-25	3,4-Dihydro-2-alkyl-3-oxo-N-aryl-2H-[1]benzothieno[3,2-e]-1,2-thiazine-4-carboxamid-1,1-dioxide.
DE3509333A1 (de)	1986-09-18	Substituierte benzimidazolderivate, verfahren zu ihrer herstellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung als magensaeuresekretionshemmer
DE68927599T2 (de)	1997-05-15	Hydantoin-Derivate
DD283817A5 (de)	1990-10-24	Verfahren zur herstellung heterocyclischer nitromethanderivate
DE60129445T2 (de)	2008-04-24	Quinolin-derivate als antientzündungsmittel
EP0242767B1 (de)	1991-09-11	N-dihydroindolylethylsulfonamide
EP0008367B1 (de)	1983-08-10	N-Arylsulfonylpyrrole, ihre Herstellung und diese enthaltende therapeutische Mittel
DE19832009A1 (de)	2000-01-20	2,5-Substituierte Benzolsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung und sie enthaltende pharamazeutische Präparate
DE2832358C2 (pl)	1989-12-07
EP0322692B1 (de)	1991-03-06	Heterocyclisch substituierte Alkylsulfonamide, Verfahren zu ihrer Herstellung sowie Arzneimittel
EP0424722B1 (de)	1994-07-06	Substituierte (Chinolin-2-yl-methoxy)phenyl-thioharnstoffe
EP0729954B1 (de)	2003-09-03	Substituierte Thiophenylsulfonylharnstoffe und -thioharnstoffe, Verfahren zu ihrer Herstellung, ihre Verwendung als Medikament oder Diagnostikum sowie sie enthaltendes Medikament
DD234265A5 (de)	1986-03-26	Verfahren zur herstellung von spiro-3-hetero-azolonen
EP0045521A1 (de)	1982-02-10	Pyrazolobenzazepine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2310016A1 (de)	1973-09-13	Thienopyrimidine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel
CH605749A5 (en)	1978-10-13	2-Aminoalkyl-3-phenyl isoindole derivs
DE3804636A1 (de)	1989-08-24	Heterocyclisch substituierte alkylsulfonamide, verfahren zu ihrer herstellung sowie arzneimittel