CA1226286A - 1,4-thiazine derivative - Google Patents

1,4-thiazine derivative

Info

Publication number: CA1226286A
Authority: CA; Canada
Prior art keywords: general formula; compound; thiazin; methyl; pyridinyl
Prior art date: 1983-09-16
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

Application number

CA000463160A

Other languages

English (en)

French (fr)

Inventor

Muneaki Takase

Kimitomo Yoshioka

Hiroaki Yamazaki

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Zenyaku Kogyo KK

Original Assignee

Zenyaku Kogyo 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.)

1983-09-16

Filing date

1984-09-14

Publication date

1987-09-01

1984-09-14 Application filed by Zenyaku Kogyo KK filed Critical Zenyaku Kogyo KK

1987-09-01 Application granted granted Critical

1987-09-01 Publication of CA1226286A publication Critical patent/CA1226286A/en

Status Expired legal-status Critical Current

Links

125000000183 1,4-thiazinyl group Chemical class S1C(C=NC=C1)* 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 66
238000000034 method Methods 0.000 claims abstract description 38
238000002360 preparation method Methods 0.000 claims abstract description 19
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 8
238000003756 stirring Methods 0.000 claims abstract description 8
239000011593 sulfur Substances 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims abstract description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
239000002253 acid Substances 0.000 claims abstract description 6
125000005843 halogen group Chemical group 0.000 claims abstract description 6
125000004076 pyridyl group Chemical group 0.000 claims abstract description 6
239000002904 solvent Substances 0.000 claims abstract description 6
150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract description 5
150000003839 salts Chemical class 0.000 claims abstract description 5
239000011701 zinc Substances 0.000 claims abstract description 3
229910052725 zinc Inorganic materials 0.000 claims abstract description 3
150000000192 1,4-thiazines Chemical class 0.000 claims abstract 4
125000000217 alkyl group Chemical group 0.000 claims abstract 4
150000004897 thiazines Chemical class 0.000 claims abstract 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 14
238000006243 chemical reaction Methods 0.000 claims description 11
LJCZNYWLQZZIOS-UHFFFAOYSA-N 2,2,2-trichlorethoxycarbonyl chloride Chemical group ClC(=O)OCC(Cl)(Cl)Cl LJCZNYWLQZZIOS-UHFFFAOYSA-N 0.000 claims description 7
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 7
GYYVFGWKPDSNLK-UHFFFAOYSA-N 5-methyl-4h-1,4-thiazin-3-one Chemical compound CC1=CSCC(=O)N1 GYYVFGWKPDSNLK-UHFFFAOYSA-N 0.000 claims description 7
235000019253 formic acid Nutrition 0.000 claims description 7
WZLDCQZXQZZCJI-UHFFFAOYSA-N 5-methyl-6-pyridin-4-yl-4h-1,4-thiazin-3-one Chemical compound S1CC(=O)NC(C)=C1C1=CC=NC=C1 WZLDCQZXQZZCJI-UHFFFAOYSA-N 0.000 claims description 5
239000000126 substance Substances 0.000 claims description 5
238000010438 heat treatment Methods 0.000 claims description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 10
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 5
DXUBQSHWVKRJQF-UHFFFAOYSA-N 2,2,2-trichloroethyl 4-(3-methyl-5-oxo-4h-1,4-thiazin-2-yl)-4h-pyridine-1-carboxylate Chemical compound S1CC(=O)NC(C)=C1C1C=CN(C(=O)OCC(Cl)(Cl)Cl)C=C1 DXUBQSHWVKRJQF-UHFFFAOYSA-N 0.000 claims 3
239000000496 cardiotonic agent Substances 0.000 abstract description 3
239000000546 pharmaceutical excipient Substances 0.000 abstract 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 32
239000000243 solution Substances 0.000 description 21
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000000694 effects Effects 0.000 description 15
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 14
238000001228 spectrum Methods 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
230000037396 body weight Effects 0.000 description 10
238000004458 analytical method Methods 0.000 description 8
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FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
230000002776 aggregation Effects 0.000 description 7
238000004220 aggregation Methods 0.000 description 7
229910052943 magnesium sulfate Inorganic materials 0.000 description 7
235000019341 magnesium sulphate Nutrition 0.000 description 7
239000011541 reaction mixture Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
210000003540 papillary muscle Anatomy 0.000 description 6
239000007787 solid Substances 0.000 description 6
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 6
150000003544 thiamines Chemical class 0.000 description 6
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 6
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical class CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 5
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
238000011161 development Methods 0.000 description 5
239000000284 extract Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
SQEQHIUHGBSTSE-UHFFFAOYSA-N 4,5-dimethyl-6-pyridin-4-yl-1,4-thiazin-3-one Chemical compound CN1C(=O)CSC(C=2C=CN=CC=2)=C1C SQEQHIUHGBSTSE-UHFFFAOYSA-N 0.000 description 4
235000018936 Vitellaria paradoxa Nutrition 0.000 description 4
-1 acetic Chemical class 0.000 description 4
229960002105 amrinone Drugs 0.000 description 4
RNLQIBCLLYYYFJ-UHFFFAOYSA-N amrinone Chemical compound N1C(=O)C(N)=CC(C=2C=CN=CC=2)=C1 RNLQIBCLLYYYFJ-UHFFFAOYSA-N 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
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239000008280 blood Substances 0.000 description 4
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239000006227 byproduct Substances 0.000 description 4
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238000000354 decomposition reaction Methods 0.000 description 4
238000006073 displacement reaction Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
239000003814 drug Substances 0.000 description 4
229940093499 ethyl acetate Drugs 0.000 description 4
235000019439 ethyl acetate Nutrition 0.000 description 4
239000000706 filtrate Substances 0.000 description 4
238000001819 mass spectrum Methods 0.000 description 4
210000003205 muscle Anatomy 0.000 description 4
239000002245 particle Substances 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000010898 silica gel chromatography Methods 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
230000035488 systolic blood pressure Effects 0.000 description 4
238000010998 test method Methods 0.000 description 4
238000012360 testing method Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
241000700159 Rattus Species 0.000 description 3
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
229920000180 alkyd Polymers 0.000 description 3
230000017531 blood circulation Effects 0.000 description 3
210000000038 chest Anatomy 0.000 description 3
238000002474 experimental method Methods 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000000047 product Substances 0.000 description 3
210000002460 smooth muscle Anatomy 0.000 description 3
229960000278 theophylline Drugs 0.000 description 3
230000002861 ventricular Effects 0.000 description 3
ITQTTZVARXURQS-UHFFFAOYSA-N 3-methylpyridine Chemical compound CC1=CC=CN=C1 ITQTTZVARXURQS-UHFFFAOYSA-N 0.000 description 2
RNKPJWGEFSZOMA-UHFFFAOYSA-N 5-methyl-6-piperidin-4-yl-4h-1,4-thiazin-3-one Chemical compound S1CC(=O)NC(C)=C1C1CCNCC1 RNKPJWGEFSZOMA-UHFFFAOYSA-N 0.000 description 2
INWCDSFOPZCQIO-UHFFFAOYSA-N 5-methyl-6-pyridin-4-yl-4h-1,4-thiazin-3-one;hydrochloride Chemical compound Cl.S1CC(=O)NC(C)=C1C1=CC=NC=C1 INWCDSFOPZCQIO-UHFFFAOYSA-N 0.000 description 2
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 2
KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 2
241000282326 Felis catus Species 0.000 description 2
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 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
231100000403 acute toxicity Toxicity 0.000 description 2
230000007059 acute toxicity Effects 0.000 description 2
210000000621 bronchi Anatomy 0.000 description 2
230000007883 bronchodilation Effects 0.000 description 2
239000001110 calcium chloride Substances 0.000 description 2
229910001628 calcium chloride Inorganic materials 0.000 description 2
125000004122 cyclic group Chemical group 0.000 description 2
230000006378 damage Effects 0.000 description 2
239000012153 distilled water Substances 0.000 description 2
239000008103 glucose Substances 0.000 description 2
238000011597 hartley guinea pig Methods 0.000 description 2
238000005259 measurement Methods 0.000 description 2
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 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
125000003386 piperidinyl group Chemical group 0.000 description 2
239000000843 powder Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
208000010110 spontaneous platelet aggregation Diseases 0.000 description 2
239000007858 starting material Substances 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
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210000001519 tissue Anatomy 0.000 description 2
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JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
KEQXNNJHMWSZHK-UHFFFAOYSA-L 1,3,2,4$l^{2}-dioxathiaplumbetane 2,2-dioxide Chemical compound [Pb+2].[O-]S([O-])(=O)=O KEQXNNJHMWSZHK-UHFFFAOYSA-L 0.000 description 1
QXQAPNSHUJORMC-UHFFFAOYSA-N 1-chloro-4-propylbenzene Chemical compound CCCC1=CC=C(Cl)C=C1 QXQAPNSHUJORMC-UHFFFAOYSA-N 0.000 description 1
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical class OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 description 1
125000000453 2,2,2-trichloroethyl group Chemical group [H]C([H])(*)C(Cl)(Cl)Cl 0.000 description 1
PKRSYEPBQPFNRB-UHFFFAOYSA-N 2-phenoxybenzoic acid Chemical compound OC(=O)C1=CC=CC=C1OC1=CC=CC=C1 PKRSYEPBQPFNRB-UHFFFAOYSA-N 0.000 description 1
SGDYNMJTXCTTAF-UHFFFAOYSA-N 3,6-dihydro-2h-thiazine Chemical class C1NSCC=C1 SGDYNMJTXCTTAF-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
GUKPBENPDTXBMO-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;5-methyl-6-pyridin-4-yl-4h-1,4-thiazin-3-one Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1.S1CC(=O)NC(C)=C1C1=CC=NC=C1 GUKPBENPDTXBMO-UHFFFAOYSA-N 0.000 description 1
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 1
XQMVBICWFFHDNN-UHFFFAOYSA-N 5-amino-4-chloro-2-phenylpyridazin-3-one;(2-ethoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) methanesulfonate Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1.C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 XQMVBICWFFHDNN-UHFFFAOYSA-N 0.000 description 1
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241000586542 Aonidiella citrina Species 0.000 description 1
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COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
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238000005481 NMR spectroscopy Methods 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000282320 Panthera leo Species 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
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150000001298 alcohols Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
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SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
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FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 1
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239000012043 crude product Substances 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical compound C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
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229960001412 pentobarbital Drugs 0.000 description 1
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239000001103 potassium chloride Substances 0.000 description 1
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GNSKLFRGEWLPPA-UHFFFAOYSA-M potassium dihydrogen phosphate Chemical compound [K+].OP(O)([O-])=O GNSKLFRGEWLPPA-UHFFFAOYSA-M 0.000 description 1
238000012746 preparative thin layer chromatography Methods 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
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238000000926 separation method Methods 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
230000000153 supplemental effect Effects 0.000 description 1
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230000009885 systemic effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
210000005062 tracheal ring Anatomy 0.000 description 1
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229910052844 willemite Inorganic materials 0.000 description 1
DGVVWUTYPXICAM-UHFFFAOYSA-N β‐Mercaptoethanol Chemical compound OCCS DGVVWUTYPXICAM-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- 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
- 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
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Life Sciences & Earth Sciences (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Hematology (AREA)
Hospice & Palliative Care (AREA)
Diabetes (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pulmonology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CA000463160A 1983-09-16 1984-09-14 1,4-thiazine derivative Expired CA1226286A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP58170862A JPS6061580A (ja)	1983-09-16	1983-09-16	新規１，４−チアジン誘導体とその製造法
JP170862/1983		1983-09-16

Publications (1)

Publication Number	Publication Date
CA1226286A true CA1226286A (en)	1987-09-01

Family

ID=15912686

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000463160A Expired CA1226286A (en)	1983-09-16	1984-09-14	1,4-thiazine derivative

Country Status (5)

Country	Link
US (1)	US4565813A (2)
EP (1)	EP0138058B1 (2)
JP (1)	JPS6061580A (2)
CA (1)	CA1226286A (2)
DE (1)	DE3473453D1 (2)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0233287B1 (en) *	1984-10-04	1991-01-30	Zenyaku Kogyo Kabushikikaisha	1,4-thiazine derivatives, process for their preparation, and cardiotonics containing the same
WO1991018893A1 (fr) *	1990-06-01	1991-12-12	Zenyaku Kogyo Kabushiki Kaisha	Nouveau derive de 1,4-thiazine et cardiotonique contenant ce compose comme ingredient actif
JP3386235B2 (ja) *	1994-06-30	2003-03-17	株式会社リコー	転写紙案内装置

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1266464A (fr) *	1956-07-20	1961-07-17	Sterling Drug Inc	Procédé de préparation des 2-aryl-4-métathiazanones et de certains de leurs dérivés
CS216535B2 (en) *	1978-10-16	1982-11-26	Lilly Co Eli	Fungicide means and means for regulation of the water plants growth and method of making the active substances
US4476311A (en) *	1980-03-12	1984-10-09	The Purdue Frederick Company	Analgesic 4-carboxy-pyrrolidin-2-one compound

1983
- 1983-09-16 JP JP58170862A patent/JPS6061580A/ja active Granted
1984
- 1984-09-12 DE DE8484110868T patent/DE3473453D1/de not_active Expired
- 1984-09-12 EP EP84110868A patent/EP0138058B1/en not_active Expired
- 1984-09-14 US US06/650,530 patent/US4565813A/en not_active Expired - Fee Related
- 1984-09-14 CA CA000463160A patent/CA1226286A/en not_active Expired

Also Published As

Publication number	Publication date
JPH0121830B2 (2)	1989-04-24
US4565813A (en)	1986-01-21
EP0138058B1 (en)	1988-08-17
JPS6061580A (ja)	1985-04-09
DE3473453D1 (de)	1988-09-22
EP0138058A1 (en)	1985-04-24

Legal Events

Date	Code	Title	Description
2004-09-14	MKEX	Expiry

Publication	Publication Date	Title
DE3218584A1 (de)	1982-12-23	1,2-diaminocyclobuten-3,4-dione, verfahren zu deren herstellung und pharmazeutische mittel, die diese verbindungen enthalten
DE3306006C2 (2)	1992-02-06
FR2573075A1 (fr)	1986-05-16	Nouvelles (pyridyl-2)-1 piperazines, leur procede de preparation et leur application en therapeutique
DE68925270T2 (de)	1996-06-13	Pyrrolo[3,2-e]pyrazolo[1,5-a]pyrimidinderivate und diese enthaltende Arzneimittel
Anglada et al.	1988	Inhibitors of gastric acid secretion: N-sulphonyl formamidines in a series of new histamine H2-receptor antagonists
CN107200734B (zh)	2019-12-24	奎宁环衍生物及其制备方法和用途
CS262690B2 (en)	1989-03-14	Process for preparing 1-/hydroxystyryl/-5h-2,3-benzodiazepines
SU1574177A3 (ru)	1990-06-23	Способ получени производных 4,5-дигидрооксазолов
CH640227A5 (de)	1983-12-30	Aminoalkoxyphenyl-derivate.
CS199568B2 (en)	1980-07-31	Method of producing substituted derivatives of alpha aminooxycarboxylic acids hydrazides and addition salts thereof with acids
EP0138058B1 (en)	1988-08-17	Novel 1,4-thiazine derivative
Takatani et al.	1989	Platelet activating factor (PAF) antagonists: synthesis and structure-activity studies of novel PAF analogs modified in the phosphorylcholine moiety
DE3825242A1 (de)	1989-02-09	Durch schwefelhaltige gruppen substituierte histidinylamino-verbindungen
WO1999032115A1 (en)	1999-07-01	Modulators of ryanodine receptors comprising 2-(aryl)-4,7-dioxobenzothiazoles and analogues thereof
EP0252422B1 (en)	1991-07-24	Pyridazinone derivatives and salts thereof
CS273185B2 (en)	1991-03-12	Method of ephidophylotoxin's derivatives production that contain nitrogen
EP0573392A1 (de)	1993-12-08	Thiosemicarbazonderivate und ihre Anwendung als Arzneimittelwirkstoff
EP0211157B1 (de)	1991-01-02	Isoxazolderivate, Verfahren zu ihrer Herstellung und diese enthaltende pharmazeutischen Präparate
SU1493105A3 (ru)	1989-07-07	Способ получени гетероциклических соединений
EP0174458A1 (de)	1986-03-19	Verwendung von 4H-1,4 Benzothiazinen bei der Prophylaxe und Therapie von Erkrankungen der Atemwege, Entzündungen/Rheuma, thromboembolischen Erkrankungen, Ischämien und Infarkten, Herzrhythmusstörungen, Arteriosklerose und Dermatosen, Arzneimittel zu diesem Zweck sowie Wirkstoffe, die in diesen Arnzeimitteln enthalten sind
CN113214238A (zh)	2021-08-06	一类具有酰化哌嗪结构的吲哚恶二唑衍生物的制备和用途
KR0169357B1 (ko)	1999-01-15	신규한 2-이미다졸론유도체 및 그의 제조방법
PT88923B (pt)	1993-01-29	Processo para a preparacao de derivados de acillabdano e de composicoes farmaceuticas que os contem
FR2542741A1 (fr)	1984-09-21	3,4-diamino-1,2,5-thiadiazoles substitues possedant une activite antagoniste du recepteur-h2 de l'histamine
US3468889A (en)	1969-09-23	O-and/or s-nicotinoyl diacylthiamines and acylation process for preparing the same