CH642062A5 - Sels de benzene- et thiophenecarbothioates de 2-aminoalkyle utiles notamment comme mucolytiques et composition pharmaceutique les contenant. - Google Patents
Sels de benzene- et thiophenecarbothioates de 2-aminoalkyle utiles notamment comme mucolytiques et composition pharmaceutique les contenant. Download PDFInfo
- Publication number
- CH642062A5 CH642062A5 CH716879A CH716879A CH642062A5 CH 642062 A5 CH642062 A5 CH 642062A5 CH 716879 A CH716879 A CH 716879A CH 716879 A CH716879 A CH 716879A CH 642062 A5 CH642062 A5 CH 642062A5
- Authority
- CH
- Switzerland
- Prior art keywords
- aminoethyl
- monohydrochloride
- hydrochloride
- compounds
- chloride
- Prior art date
Links
- 239000003172 expectorant agent Substances 0.000 title claims description 6
- 229940066491 mucolytics Drugs 0.000 title claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 23
- -1 4-chlorobenzenecarbothioate 2-aminoethyl hydrochloride Chemical compound 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 239000000443 aerosol Substances 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- GUCJNQQVGFVQJB-UHFFFAOYSA-N Cl.NCCOC(=S)C1=CC=CS1 Chemical compound Cl.NCCOC(=S)C1=CC=CS1 GUCJNQQVGFVQJB-UHFFFAOYSA-N 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- ZSCGMTWBDWARBZ-UHFFFAOYSA-N o-(2-aminoethyl) benzenecarbothioate;hydrochloride Chemical compound Cl.NCCOC(=S)C1=CC=CC=C1 ZSCGMTWBDWARBZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004480 active ingredient Substances 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000000725 suspension Substances 0.000 claims description 3
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000006199 nebulizer Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000005507 spraying Methods 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 14
- 241001465754 Metazoa Species 0.000 description 9
- 230000000510 mucolytic effect Effects 0.000 description 9
- 210000002784 stomach Anatomy 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
- 210000003097 mucus Anatomy 0.000 description 6
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 6
- OGMADIBCHLQMIP-UHFFFAOYSA-N 2-aminoethanethiol;hydron;chloride Chemical compound Cl.NCCS OGMADIBCHLQMIP-UHFFFAOYSA-N 0.000 description 5
- JGYPCVMXENEIIE-UHFFFAOYSA-N Cl.NCCOC(=S)C1=CC=C(Cl)C=C1 Chemical compound Cl.NCCOC(=S)C1=CC=C(Cl)C=C1 JGYPCVMXENEIIE-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 238000001953 recrystallisation Methods 0.000 description 5
- 229930006000 Sucrose Natural products 0.000 description 4
- 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 4
- 238000001914 filtration Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000001424 substituent group Chemical group 0.000 description 4
- 239000005720 sucrose Substances 0.000 description 4
- PWKSKIMOESPYIA-BYPYZUCNSA-N L-N-acetyl-Cysteine Chemical compound CC(=O)N[C@@H](CS)C(O)=O PWKSKIMOESPYIA-BYPYZUCNSA-N 0.000 description 3
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 3
- 239000008367 deionised water Substances 0.000 description 3
- 229910021641 deionized water Inorganic materials 0.000 description 3
- YVJCCFYYZBHAMK-UHFFFAOYSA-N 2-aminoethane-1,1-diol;hydrochloride Chemical compound [Cl-].[NH3+]CC(O)O YVJCCFYYZBHAMK-UHFFFAOYSA-N 0.000 description 2
- GMEDUXHKSSWXSL-UHFFFAOYSA-N 3-sulfanylpropylazanium;chloride Chemical compound Cl.NCCCS GMEDUXHKSSWXSL-UHFFFAOYSA-N 0.000 description 2
- RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 2
- NQUVCRCCRXRJCK-UHFFFAOYSA-N 4-methylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1 NQUVCRCCRXRJCK-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- OIPBLEAVMUGWDR-UHFFFAOYSA-N O-(2-aminoethyl) 4-methoxybenzenecarbothioate hydrochloride Chemical compound Cl.COC1=CC=C(C(=S)OCCN)C=C1 OIPBLEAVMUGWDR-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- MXMOTZIXVICDSD-UHFFFAOYSA-N anisoyl chloride Chemical compound COC1=CC=C(C(Cl)=O)C=C1 MXMOTZIXVICDSD-UHFFFAOYSA-N 0.000 description 2
- 150000001555 benzenes Chemical class 0.000 description 2
- 230000005540 biological transmission Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 229910001629 magnesium chloride Inorganic materials 0.000 description 2
- 230000029058 respiratory gaseous exchange Effects 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- MLFIYYDKLNZLAO-UHFFFAOYSA-N 2-aminoethane-1,1-diol Chemical compound NCC(O)O MLFIYYDKLNZLAO-UHFFFAOYSA-N 0.000 description 1
- VKPPFDPXZWFDFA-UHFFFAOYSA-N 2-chloroethanamine Chemical compound NCCCl VKPPFDPXZWFDFA-UHFFFAOYSA-N 0.000 description 1
- BUHYMJLFRZAFBF-UHFFFAOYSA-N 3,4,5-trimethoxybenzoyl chloride Chemical compound COC1=CC(C(Cl)=O)=CC(OC)=C1OC BUHYMJLFRZAFBF-UHFFFAOYSA-N 0.000 description 1
- RGAKSNQOIIYQRM-UHFFFAOYSA-N 3,4-dimethylbenzoyl chloride Chemical compound CC1=CC=C(C(Cl)=O)C=C1C RGAKSNQOIIYQRM-UHFFFAOYSA-N 0.000 description 1
- RUJYJCANMOTJMO-UHFFFAOYSA-N 3-(trifluoromethyl)benzoyl chloride Chemical compound FC(F)(F)C1=CC=CC(C(Cl)=O)=C1 RUJYJCANMOTJMO-UHFFFAOYSA-N 0.000 description 1
- HPAMEKLXNVFXPO-UHFFFAOYSA-N 4-(2-aminoethoxycarbothioyl)benzoic acid Chemical compound NCCOC(=S)C1=CC=C(C(O)=O)C=C1 HPAMEKLXNVFXPO-UHFFFAOYSA-N 0.000 description 1
- OYEQKMASMPBQMP-UHFFFAOYSA-N 4-carbonochloridoylbenzoic acid Chemical compound OC(=O)C1=CC=C(C(Cl)=O)C=C1 OYEQKMASMPBQMP-UHFFFAOYSA-N 0.000 description 1
- CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000694440 Colpidium aqueous Species 0.000 description 1
- 102000009338 Gastric Mucins Human genes 0.000 description 1
- 108010009066 Gastric Mucins Proteins 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
- 208000019693 Lung disease Diseases 0.000 description 1
- APNAOCORQYFRQO-UHFFFAOYSA-N O-(2-aminoethyl) 4-methylbenzenecarbothioate hydrochloride Chemical compound Cl.CC1=CC=C(C(=S)OCCN)C=C1 APNAOCORQYFRQO-UHFFFAOYSA-N 0.000 description 1
- 208000001649 Pica Diseases 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 229960004308 acetylcysteine Drugs 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000004176 azorubin Substances 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 229940006460 bromide ion Drugs 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 230000000762 glandular Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000003434 inspiratory effect Effects 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 150000002632 lipids Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- DHRRIBDTHFBPNG-UHFFFAOYSA-L magnesium dichloride hexahydrate Chemical compound O.O.O.O.O.O.[Mg+2].[Cl-].[Cl-] DHRRIBDTHFBPNG-UHFFFAOYSA-L 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007923 nasal drop Substances 0.000 description 1
- 229940100662 nasal drops Drugs 0.000 description 1
- HEPUEHGDWDOZJZ-UHFFFAOYSA-N o-(3-aminopropyl) benzenecarbothioate;hydrochloride Chemical compound Cl.NCCCOC(=S)C1=CC=CC=C1 HEPUEHGDWDOZJZ-UHFFFAOYSA-N 0.000 description 1
- LWASMSFEDTYCKN-UHFFFAOYSA-N o-(3-aminopropyl) thiophene-2-carbothioate;hydrochloride Chemical compound Cl.NCCCOC(=S)C1=CC=CS1 LWASMSFEDTYCKN-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229940068886 polyethylene glycol 300 Drugs 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive 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
-
- 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
- A61P11/10—Expectorants
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (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)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Compounds Containing Sulfur Atoms (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US93274778A | 1978-08-10 | 1978-08-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH642062A5 true CH642062A5 (fr) | 1984-03-30 |
Family
ID=25462846
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH716879A CH642062A5 (fr) | 1978-08-10 | 1979-08-03 | Sels de benzene- et thiophenecarbothioates de 2-aminoalkyle utiles notamment comme mucolytiques et composition pharmaceutique les contenant. |
Country Status (17)
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1170862B (it) * | 1981-03-31 | 1987-06-03 | Sigma Tau Ind Farmaceuti | Mercaptoacil-carnitine procedimento per la loro preparazione e loro uso terapeutico |
| JP3635780B2 (ja) * | 1996-04-08 | 2005-04-06 | 株式会社デンソー | ハニカム構造体の成形装置及び成形方法 |
| CN110597249B (zh) * | 2019-08-23 | 2022-08-05 | 深圳市优必选科技股份有限公司 | 一种机器人及其回充定位方法和装置 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2342142A (en) * | 1937-09-09 | 1944-02-22 | Squibb & Sons Inc | Esters of sulphur-containing benzoic acids and process of preparing them |
| US3328442A (en) * | 1963-12-18 | 1967-06-27 | Massachusetts College Of Pharm | Anti-radiation compounds and their preparation |
| DE2335079C3 (de) * | 1973-02-21 | 1979-02-15 | Laboratories Made S.A., Madrid | Aminoalkylderivate der 3,5-Dimethylbenzoesäure sowie deren Salze und Verfahren zu deren Herstellung |
| US4210666A (en) * | 1978-08-10 | 1980-07-01 | A. H. Robins Company, Inc. | Mucolytic thiophenecarboxamido alkyl mercaptans |
| IL57881A (en) * | 1978-08-10 | 1982-12-31 | Robins Co Inc A H | Pharmaceutical compositions containing benzamidoalkyl merccaptans |
-
1979
- 1979-07-20 IL IL57859A patent/IL57859A/xx unknown
- 1979-08-03 CH CH716879A patent/CH642062A5/fr not_active IP Right Cessation
- 1979-08-03 PH PH22851A patent/PH16277A/en unknown
- 1979-08-08 IE IE1520/79A patent/IE48794B1/en unknown
- 1979-08-08 GB GB7927694A patent/GB2028325B/en not_active Expired
- 1979-08-08 EG EG487/79A patent/EG14416A/xx active
- 1979-08-09 FR FR7920412A patent/FR2433016A1/fr active Granted
- 1979-08-09 DE DE19792932402 patent/DE2932402A1/de active Granted
- 1979-08-09 ES ES483269A patent/ES483269A1/es not_active Expired
- 1979-08-09 CA CA333,424A patent/CA1125297A/en not_active Expired
- 1979-08-09 AU AU49756/79A patent/AU520791B2/en not_active Ceased
- 1979-08-09 DK DK333879A patent/DK159655C/da not_active IP Right Cessation
- 1979-08-09 FI FI792474A patent/FI69060C/fi not_active IP Right Cessation
- 1979-08-09 IT IT68643/79A patent/IT1118828B/it active
- 1979-08-09 BE BE0/196671A patent/BE878169A/xx not_active IP Right Cessation
- 1979-08-10 ZA ZA00794171A patent/ZA794171B/xx unknown
- 1979-08-10 JP JP10212879A patent/JPS5536486A/ja active Granted
-
1980
- 1980-02-14 FR FR8003290A patent/FR2453150A1/fr active Granted
-
1987
- 1987-10-27 JP JP62271595A patent/JPS63119423A/ja active Granted
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |