CH621339A5 - - Google Patents
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- Publication number
- CH621339A5 CH621339A5 CH815175A CH815175A CH621339A5 CH 621339 A5 CH621339 A5 CH 621339A5 CH 815175 A CH815175 A CH 815175A CH 815175 A CH815175 A CH 815175A CH 621339 A5 CH621339 A5 CH 621339A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dihydrocarbostyril
- colorless
- formula
- ethoxycarbonyl
- radical
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 75
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 49
- 238000006243 chemical reaction Methods 0.000 claims description 49
- 238000000034 method Methods 0.000 claims description 28
- FVXYRXMYPXVHNY-UHFFFAOYSA-N 3-propoxy-3,4-dihydro-1H-quinolin-2-one Chemical compound C(CC)OC1C(NC2=CC=CC=C2C1)=O FVXYRXMYPXVHNY-UHFFFAOYSA-N 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 16
- 238000002360 preparation method Methods 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- ISLSKIAOFFDGGX-UHFFFAOYSA-N 3-ethoxy-3,4-dihydro-1H-quinolin-2-one Chemical compound C(C)OC1C(NC2=CC=CC=C2C1)=O ISLSKIAOFFDGGX-UHFFFAOYSA-N 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- CAZJQXRQQJEBMX-UHFFFAOYSA-N 3-butoxy-3,4-dihydro-1H-quinolin-2-one Chemical compound C(CCC)OC1C(NC2=CC=CC=C2C1)=O CAZJQXRQQJEBMX-UHFFFAOYSA-N 0.000 claims description 4
- 230000009467 reduction Effects 0.000 claims description 3
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- YNZNESKPSHZISM-UHFFFAOYSA-N 3-propoxy-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)C(OCCC)=CC2=C1 YNZNESKPSHZISM-UHFFFAOYSA-N 0.000 claims 4
- TZOYXRMEFDYWDQ-UHFFFAOYSA-N 3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2NC(=O)CCC2=C1 TZOYXRMEFDYWDQ-UHFFFAOYSA-N 0.000 claims 2
- 230000018044 dehydration Effects 0.000 claims 2
- 238000006297 dehydration reaction Methods 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 101150099461 CTL2 gene Proteins 0.000 claims 1
- 101150116431 Slc44a2 gene Proteins 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 239000013078 crystal Substances 0.000 description 289
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 57
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 46
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 45
- 239000002904 solvent Substances 0.000 description 45
- 239000000203 mixture Substances 0.000 description 40
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 39
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- -1 alkyl radical Chemical class 0.000 description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 239000012230 colorless oil Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000003054 catalyst Substances 0.000 description 24
- 208000007536 Thrombosis Diseases 0.000 description 21
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 20
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 18
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 18
- 230000004520 agglutination Effects 0.000 description 17
- 238000010992 reflux Methods 0.000 description 16
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 15
- 239000012295 chemical reaction liquid Substances 0.000 description 15
- 235000011121 sodium hydroxide Nutrition 0.000 description 15
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 15
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 238000009835 boiling Methods 0.000 description 14
- 125000001424 substituent group Chemical group 0.000 description 14
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 10
- 210000004623 platelet-rich plasma Anatomy 0.000 description 10
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 10
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 10
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 102000008186 Collagen Human genes 0.000 description 8
- 108010035532 Collagen Proteins 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 8
- 150000001298 alcohols Chemical class 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 229920001436 collagen Polymers 0.000 description 8
- 238000004821 distillation Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 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 7
- 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 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 7
- 210000004369 blood Anatomy 0.000 description 7
- 239000008280 blood Substances 0.000 description 7
- 201000010099 disease Diseases 0.000 description 7
- 230000002401 inhibitory effect Effects 0.000 description 7
- 239000003208 petroleum Substances 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000013543 active substance Substances 0.000 description 6
- 229910052783 alkali metal Inorganic materials 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 6
- 210000004204 blood vessel Anatomy 0.000 description 6
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 5
- 208000005189 Embolism Diseases 0.000 description 5
- 150000007513 acids Chemical class 0.000 description 5
- 239000000010 aprotic solvent Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 235000008504 concentrate Nutrition 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 239000010410 layer Substances 0.000 description 5
- 229910052763 palladium Inorganic materials 0.000 description 5
- 235000011118 potassium hydroxide Nutrition 0.000 description 5
- 230000035484 reaction time Effects 0.000 description 5
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 5
- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
- 235000009518 sodium iodide Nutrition 0.000 description 5
- 239000012265 solid product Substances 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 150000007514 bases Chemical class 0.000 description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 229910017052 cobalt Inorganic materials 0.000 description 4
- 239000010941 cobalt Substances 0.000 description 4
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000011734 sodium Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 3
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 241000283973 Oryctolagus cuniculus Species 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 3
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
- 150000001340 alkali metals Chemical class 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 230000023555 blood coagulation Effects 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 238000006704 dehydrohalogenation reaction Methods 0.000 description 3
- 208000035475 disorder Diseases 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 239000003937 drug carrier Substances 0.000 description 3
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910001511 metal iodide Inorganic materials 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 235000005985 organic acids Nutrition 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 3
- 235000011007 phosphoric acid Nutrition 0.000 description 3
- 229910052697 platinum Inorganic materials 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229960003975 potassium Drugs 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 235000017550 sodium carbonate Nutrition 0.000 description 3
- 239000011343 solid material Substances 0.000 description 3
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 2
- ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
- WNEODWDFDXWOLU-QHCPKHFHSA-N 3-[3-(hydroxymethyl)-4-[1-methyl-5-[[5-[(2s)-2-methyl-4-(oxetan-3-yl)piperazin-1-yl]pyridin-2-yl]amino]-6-oxopyridin-3-yl]pyridin-2-yl]-7,7-dimethyl-1,2,6,8-tetrahydrocyclopenta[3,4]pyrrolo[3,5-b]pyrazin-4-one Chemical compound C([C@@H](N(CC1)C=2C=NC(NC=3C(N(C)C=C(C=3)C=3C(=C(N4C(C5=CC=6CC(C)(C)CC=6N5CC4)=O)N=CC=3)CO)=O)=CC=2)C)N1C1COC1 WNEODWDFDXWOLU-QHCPKHFHSA-N 0.000 description 2
- MSSJTTFHXMTEHT-UHFFFAOYSA-N 3-ethoxy-1H-quinolin-2-one Chemical compound C(C)OC=1C(=NC2=CC=CC=C2C1)O MSSJTTFHXMTEHT-UHFFFAOYSA-N 0.000 description 2
- UTTJAIFHRUAFED-UHFFFAOYSA-N 5-hydroxy-3,4-dihydro-2(1h)-quinolinone Chemical compound N1C(=O)CCC2=C1C=CC=C2O UTTJAIFHRUAFED-UHFFFAOYSA-N 0.000 description 2
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- 206010061216 Infarction Diseases 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
- 229930006000 Sucrose Natural products 0.000 description 2
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 2
- 150000001339 alkali metal compounds Chemical class 0.000 description 2
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- 239000000725 suspension Substances 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 230000002537 thrombolytic effect Effects 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- DGCFCIXSJPYNLX-UHFFFAOYSA-N trichloromethylsulfonyl trichloromethanesulfonate Chemical compound ClC(Cl)(Cl)S(=O)(=O)OS(=O)(=O)C(Cl)(Cl)Cl DGCFCIXSJPYNLX-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/227—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
- C07D215/20—Oxygen atoms
- C07D215/24—Oxygen atoms attached in position 8
- C07D215/26—Alcohols; Ethers thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP49072473A JPS511481A (ja) | 1974-06-24 | 1974-06-24 | Karubokishiarukokishi 3*44 jihidorokarubosuchirirujudotaino seizoho |
| JP49072472A JPS511480A (ja) | 1974-06-24 | 1974-06-24 | Etokishikaruboniruarukokishi 3*44 jihidorokarubosuchirirujudotaino seizoho |
| JP49077660A JPS516970A (en) | 1974-07-05 | 1974-07-05 | Shianoetokishi 3*44 jihidorokarubosuchirirujudotaino seizoho |
| JP49077661A JPS5182279A (en) | 1974-07-05 | 1974-07-05 | Karubokishetokishi 3*44 jihidorokarubosuchirirujudotainoseizoho |
| JP49094376A JPS5123271A (ja) | 1974-08-16 | 1974-08-16 | Karubamoiruarukokishi 3*44 jihidorokarubosuchirirujudotaiseizoho |
| JP50053028A JPS51128978A (en) | 1975-04-30 | 1975-04-30 | Process for preparing carbostyril derivatives |
| JP50053027A JPS51128977A (en) | 1975-04-30 | 1975-04-30 | Process for preparing carbostyril derivatives |
| JP50053026A JPS51128976A (en) | 1975-04-30 | 1975-04-30 | Process for preparing carbostyril derivatives |
| JP50058134A JPS51133283A (en) | 1975-05-15 | 1975-05-15 | A process for preparing carbostyril derivatives |
| JP50058128A JPS51133277A (en) | 1975-05-15 | 1975-05-15 | A process for preparing novel carbostyril derivatives |
| JP50058129A JPS51133278A (en) | 1975-05-15 | 1975-05-15 | A process for preparing novel carbostyril derivatives |
| JP50058135A JPS51133284A (en) | 1975-05-15 | 1975-05-15 | A process for preparing carbostyril derivatives |
| JP50058127A JPS51133276A (en) | 1975-05-15 | 1975-05-15 | Process for preparing carbostyril derivatives |
| JP50058874A JPS51136677A (en) | 1975-05-16 | 1975-05-16 | Process for preparation of carbostyril derivatives |
| JP50058872A JPS604173B2 (ja) | 1975-05-16 | 1975-05-16 | カルボスチリル誘導体の製法 |
| JP50066729A JPS51141864A (en) | 1975-06-02 | 1975-06-02 | Process for preparing oxyindole derivatives. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH621339A5 true CH621339A5 (en, 2012) | 1981-01-30 |
Family
ID=27585697
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH815175A CH621339A5 (en, 2012) | 1974-06-24 | 1975-06-23 |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US4070470A (en, 2012) |
| CA (1) | CA1048497A (en, 2012) |
| CH (1) | CH621339A5 (en, 2012) |
| DE (2) | DE2527937C2 (en, 2012) |
| DK (1) | DK150155C (en, 2012) |
| FI (1) | FI59246C (en, 2012) |
| FR (1) | FR2276043A1 (en, 2012) |
| GB (1) | GB1505305A (en, 2012) |
| IE (1) | IE41172B1 (en, 2012) |
| NL (1) | NL162376C (en, 2012) |
| NO (1) | NO149106C (en, 2012) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4313947A (en) * | 1974-06-24 | 1982-02-02 | Otsuka Pharmaceutical Co., Ltd. | Platelet aggregation inhibiting 2-oxyindoles, their compositions and method of use |
| IE46852B1 (en) * | 1977-06-10 | 1983-10-05 | Otsuka Pharma Co Ltd | Novel carbostyril derivatives |
| SU843739A3 (ru) * | 1978-02-17 | 1981-06-30 | Карл Томэ Гмбх (Фирма) | Способ получени карбостириловыхили ОКСиНдОлОВыХ пРОизВОдНыХ |
| AT374184B (de) * | 1978-02-17 | 1984-03-26 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen carbostyril- und oxindolderivaten |
| AT374185B (de) * | 1978-02-17 | 1984-03-26 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen carbostyril- und oxindolderivaten |
| JPS5535019A (en) * | 1978-09-01 | 1980-03-11 | Otsuka Pharmaceut Co Ltd | Carbostyryl derivative |
| DE2909035A1 (de) * | 1979-03-08 | 1980-09-18 | Hoechst Ag | 8-oxo-5,6,7,8-tetrahydro-2-chinolon und verfahren zu dessen herstellung |
| DE2909779A1 (de) * | 1979-03-13 | 1980-09-18 | Thomae Gmbh Dr K | Neue indolderivate, deren herstellung und deren verwendung als arzneimittel |
| AT375925B (de) * | 1979-07-14 | 1984-09-25 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen carbostyrilderivaten |
| AT376209B (de) * | 1979-07-14 | 1984-10-25 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen carbostyrilderivaten |
| JPS56122356A (en) * | 1980-02-29 | 1981-09-25 | Otsuka Pharmaceut Co Ltd | Carbostyril derivative |
| AT383594B (de) * | 1980-02-29 | 1987-07-27 | Otsuka Pharma Co Ltd | Verfahren zum herstellen von neuen carbostyrilderivaten und ihren salzen |
| ATE9329T1 (de) * | 1980-06-18 | 1984-09-15 | May & Baker Limited | Indol- und indolin-derivate. |
| FI77852C (fi) * | 1981-02-17 | 1989-05-10 | Otsuka Pharma Co Ltd | Foerfarande foer framstaellning av nya, saosom hjaertmediciner anvaendbara substituerade amid- och (maettad heterocykel)karbonylkarbostyrilderivat. |
| DE3124699A1 (de) * | 1981-06-24 | 1983-01-13 | Basf Ag, 6700 Ludwigshafen | Neue 2-aryl-3,4-diaza-bicyclo(4.n.0.)alken-(2)-one-(5),verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
| US4442111A (en) * | 1981-07-25 | 1984-04-10 | Dr. Karl Thomae Gesellschaft Mit Beschrankter Haftung | Antithrombotic sulfimino and sulfoximino indolinones-2 |
| DE3300522A1 (de) * | 1982-01-21 | 1983-07-28 | Sandoz-Patent-GmbH, 7850 Lörrach | 3,3-dialkyl- und 3,3-alkylen-indolinderivate, verfahren zu ihrer herstellung und pharmazeutische praeparate sie enthaltend |
| US4578381A (en) * | 1982-07-05 | 1986-03-25 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivatives |
| US4551459A (en) * | 1983-02-16 | 1985-11-05 | Syntex (U.S.A.) Inc. | Method of treating heart failure using (2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-b]quinazolinyl)oxyalkylamides |
| US4490371A (en) * | 1983-02-16 | 1984-12-25 | Syntex (U.S.A.) Inc. | N,N-Disubstituted-(2-oxo-1,2,3,5-tetrahydroimidazo-[2,1-B]quinazolinyl)oxyalkylamides |
| US4663320A (en) * | 1983-02-16 | 1987-05-05 | Syntex (U.S.A.) Inc. | (2-oxo-1,2,3,5-tetrahydroimidazo[2,1-b]quinoazolinyl)oxyalkylamides, compositions and the use thereof |
| DE3310891A1 (de) * | 1983-03-25 | 1984-09-27 | Boehringer Mannheim Gmbh, 6800 Mannheim | Neue indolinon-(2)-derivate, verfahren zu ihrer herstellung, diese verbindungen enthaltende arzneimittel und zwischenprodukte |
| DE3317653A1 (de) * | 1983-05-14 | 1984-11-15 | Gödecke AG, 1000 Berlin | 2-alkylthio-1-aminoalkyl-2-pyrrolin-3-carbonitrile, verfahren zu deren herstellung sowie deren verwendung bei der prophylaxe und therapie thrombotischer zustaende |
| US4657929A (en) * | 1983-10-25 | 1987-04-14 | Fisons Plc | Compounds |
| US4582909A (en) * | 1984-02-02 | 1986-04-15 | Warner-Lambert Company | Benzobicyclic lactam acids and derivatives as cognition activators |
| JPS60193991A (ja) * | 1984-02-15 | 1985-10-02 | シンテツクス（ユー・エス・エイ）インコーポレイテツド | イミダゾキナゾリニルオキシアルキルアミド誘導体 |
| US4670434A (en) * | 1985-11-14 | 1987-06-02 | Syntex (U.S.A.) Inc. | (2-oxo-3-methylene-1,2,3,5-tetrahydroimidazo[2,1-b]quinazolinyl)oxyalkylamides useful as cyclic AMP phosphodiesterase inhibitors |
| DK167187A (da) | 1986-04-02 | 1987-10-03 | Otsuka Pharma Co Ltd | Carbostyrilderivater og salte deraf, fremgangsmaade til fremstilling af saadanne forbindelser og laegemiddel indeholdende disse |
| DE3803775A1 (de) * | 1988-02-09 | 1989-08-17 | Boehringer Mannheim Gmbh | Neue substituierte lactame, verfahren zu ihrer herstellung und arzneimittel, die diese verbindungen enthalten |
| US5227381A (en) * | 1988-05-02 | 1993-07-13 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivative |
| JP2753622B2 (ja) | 1988-05-02 | 1998-05-20 | 大塚製薬株式会社 | カルボスチリル誘導体 |
| US5506239A (en) * | 1991-08-23 | 1996-04-09 | Otsuka Pharmaceutical Co., Ltd. | Carbostyril derivative and platelets aggregation inhibitory agent |
| JP2002509928A (ja) | 1998-03-31 | 2002-04-02 | ワーナー−ランバート・カンパニー | セリンプロテアーゼ阻害剤としてのキノロン |
| DE19839499A1 (de) * | 1998-08-29 | 2000-03-02 | Merck Patent Gmbh | 2-Oxo-2H-chinolinderivate |
| GB201520568D0 (en) | 2015-11-23 | 2016-01-06 | Immunocore Ltd | Peptides |
| GB201520550D0 (en) | 2015-11-23 | 2016-01-06 | Immunocore Ltd & Adaptimmune Ltd | Peptides |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1216878B (de) * | 1963-04-02 | 1966-05-18 | Cassella Farbwerke Mainkur Ag | Verfahren zur Herstellung von coronargefaesserweiternden Derivaten des 7-Hydroxy-2-oxo-1, 2-dihydrochinolins |
| GB1058822A (en) * | 1963-07-30 | 1967-02-15 | Ici Ltd | 3-amino-2-hydroxypropoxy heterocyclic derivatives |
| CH481104A (de) * | 1967-01-25 | 1969-11-15 | Geigy Ag J R | Verfahren zur Herstellung von neuen Indolderivaten |
| US3749731A (en) * | 1971-07-08 | 1973-07-31 | Warner Lambert Co | 2-oxo-n-(2-thiazolyl)-3-indoline-carboxamide |
| DE2331223C2 (de) * | 1972-06-19 | 1984-11-22 | Kohjin Co., Ltd., Tokio / Tokyo | S-substituierte-2-Thioadenosine, deren 5'-Monophosphate, Verfahren zu deren Herstellung und Arzneimittel, welche diese enthalten |
| CH578526A5 (en, 2012) * | 1972-06-23 | 1976-08-13 | Sandoz Ag | |
| AR207554A1 (es) * | 1972-12-02 | 1976-10-15 | Otsuka Pharma Co Ltd | Procedimiento para producir derivados de 3-alquil-5-((3,4-dihidro-5-carbostiril)oximetil)-oxazolidinona-(2) |
-
1975
- 1975-06-19 FI FI751842A patent/FI59246C/fi not_active IP Right Cessation
- 1975-06-19 US US05/588,475 patent/US4070470A/en not_active Expired - Lifetime
- 1975-06-23 CA CA75229940A patent/CA1048497A/en not_active Expired
- 1975-06-23 DK DK283175A patent/DK150155C/da not_active IP Right Cessation
- 1975-06-23 DE DE2527937A patent/DE2527937C2/de not_active Expired
- 1975-06-23 DE DE2559509A patent/DE2559509C2/de not_active Expired
- 1975-06-23 IE IE1392/75A patent/IE41172B1/xx unknown
- 1975-06-23 CH CH815175A patent/CH621339A5/de not_active IP Right Cessation
- 1975-06-23 NL NL7507462.A patent/NL162376C/xx not_active IP Right Cessation
- 1975-06-23 GB GB26597/75A patent/GB1505305A/en not_active Expired
- 1975-06-23 NO NO75752220A patent/NO149106C/no unknown
- 1975-06-24 FR FR7519670A patent/FR2276043A1/fr active Granted
-
1977
- 1977-06-15 US US05/806,926 patent/US4216220A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| FR2276043B1 (en, 2012) | 1978-03-24 |
| US4216220A (en) | 1980-08-05 |
| DK150155B (da) | 1986-12-22 |
| NO752220L (en, 2012) | 1975-12-30 |
| DK283175A (da) | 1975-12-25 |
| GB1505305A (en) | 1978-03-30 |
| NO149106C (no) | 1984-02-22 |
| US4070470A (en) | 1978-01-24 |
| DE2559509A1 (de) | 1976-12-30 |
| FI59246C (fi) | 1981-07-10 |
| NL162376C (nl) | 1980-05-16 |
| NL162376B (nl) | 1979-12-17 |
| DE2559509C2 (de) | 1983-02-17 |
| DE2527937C2 (de) | 1983-09-08 |
| IE41172L (en) | 1975-12-24 |
| FI751842A7 (en, 2012) | 1975-12-25 |
| FR2276043A1 (fr) | 1976-01-23 |
| FI59246B (fi) | 1981-03-31 |
| NL7507462A (nl) | 1975-12-30 |
| DE2527937A1 (de) | 1976-01-08 |
| IE41172B1 (en) | 1979-11-07 |
| DK150155C (da) | 1987-11-09 |
| CA1048497A (en) | 1979-02-13 |
| NO149106B (no) | 1983-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |