JPS6030666B2 - 光学活性メルカプトカルボン酸の製造法 - Google Patents
光学活性メルカプトカルボン酸の製造法Info
- Publication number
- JPS6030666B2 JPS6030666B2 JP55115053A JP11505380A JPS6030666B2 JP S6030666 B2 JPS6030666 B2 JP S6030666B2 JP 55115053 A JP55115053 A JP 55115053A JP 11505380 A JP11505380 A JP 11505380A JP S6030666 B2 JPS6030666 B2 JP S6030666B2
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- reaction
- manufacturing
- optically active
- Prior art date
- 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
Links
- 238000004519 manufacturing process Methods 0.000 title claims description 19
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 title claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 34
- 150000001875 compounds Chemical class 0.000 claims description 21
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 12
- 239000002585 base Substances 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229910000037 hydrogen sulfide Inorganic materials 0.000 claims description 7
- 238000006460 hydrolysis reaction Methods 0.000 claims description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical group [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 5
- 125000005843 halogen group Chemical group 0.000 claims description 5
- 230000007062 hydrolysis Effects 0.000 claims description 5
- 239000013067 intermediate product Substances 0.000 claims description 4
- 239000007810 chemical reaction solvent Substances 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 239000012298 atmosphere Substances 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- 238000000034 method Methods 0.000 description 14
- 239000002994 raw material Substances 0.000 description 9
- 239000002253 acid Substances 0.000 description 8
- 230000003287 optical effect Effects 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- -1 mercapto compound Chemical class 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
- 235000011114 ammonium hydroxide Nutrition 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- 229910052725 zinc Inorganic materials 0.000 description 4
- 239000011701 zinc Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical class OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 3
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 150000003862 amino acid derivatives Chemical class 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002825 nitriles Chemical group 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000006340 racemization Effects 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007086 side reaction Methods 0.000 description 2
- 235000010005 Catalpa ovata Nutrition 0.000 description 1
- 240000004528 Catalpa ovata Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000124033 Salix Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 238000010306 acid treatment Methods 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- HIVLDXAAFGCOFU-UHFFFAOYSA-N ammonium hydrosulfide Chemical compound [NH4+].[SH-] HIVLDXAAFGCOFU-UHFFFAOYSA-N 0.000 description 1
- 229940030600 antihypertensive agent Drugs 0.000 description 1
- 239000002220 antihypertensive agent Substances 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-N carbamothioic s-acid Chemical compound NC(S)=O GNVMUORYQLCPJZ-UHFFFAOYSA-N 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- VDQVEACBQKUUSU-UHFFFAOYSA-M disodium;sulfanide Chemical compound [Na+].[Na+].[SH-] VDQVEACBQKUUSU-UHFFFAOYSA-M 0.000 description 1
- 150000002019 disulfides Chemical class 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- UQDJGEHQDNVPGU-UHFFFAOYSA-N serine phosphoethanolamine Chemical compound [NH3+]CCOP([O-])(=O)OCC([NH3+])C([O-])=O UQDJGEHQDNVPGU-UHFFFAOYSA-N 0.000 description 1
- 229910052979 sodium sulfide Inorganic materials 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 125000000101 thioether group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/38—Acyl halides
- C07C53/46—Acyl halides containing halogen outside the carbonyl halide group
- C07C53/50—Acyl halides containing halogen outside the carbonyl halide group of acids containing three or more carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C53/00—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen
- C07C53/15—Saturated compounds having only one carboxyl group bound to an acyclic carbon atom or hydrogen containing halogen
- C07C53/19—Acids containing three or more carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55115053A JPS6030666B2 (ja) | 1980-08-20 | 1980-08-20 | 光学活性メルカプトカルボン酸の製造法 |
| GB8124198A GB2082174B (en) | 1980-08-20 | 1981-08-07 | Process for preparation of an optically active -mercaptoalkanoic acid |
| DE19813132332 DE3132332A1 (de) | 1980-08-20 | 1981-08-17 | Verfahren zur herstellung einer optisch aktiven ss-mercaptoalkansaeure |
| NL8103863A NL191943C (nl) | 1980-08-20 | 1981-08-18 | Werkwijze voor het bereiden van een optisch actief beta-mercaptoalkaanzuur. |
| US06/294,028 US4384139A (en) | 1980-08-20 | 1981-08-18 | Process for preparation of an optically active β-mercaptoalkanoic acid |
| IT49121/81A IT1171468B (it) | 1980-08-20 | 1981-08-18 | Procedimento per la preparazione di un acido beta-mercapto-alcancico otticamente attivo |
| FR8115949A FR2488888A1 (fr) | 1980-08-20 | 1981-08-19 | Procede pour la preparation d'un acide b-mercaptoalcanoique optiquement actif a partir d'un acide b-hydroxyalcanoique optiquement actif |
| IE1902/81A IE51505B1 (en) | 1980-08-20 | 1981-08-19 | Process for preparation of an optically active beta-mercaptoalkanoic acid |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP55115053A JPS6030666B2 (ja) | 1980-08-20 | 1980-08-20 | 光学活性メルカプトカルボン酸の製造法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5738768A JPS5738768A (en) | 1982-03-03 |
| JPS6030666B2 true JPS6030666B2 (ja) | 1985-07-17 |
Family
ID=14653005
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP55115053A Expired JPS6030666B2 (ja) | 1980-08-20 | 1980-08-20 | 光学活性メルカプトカルボン酸の製造法 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4384139A (en, 2012) |
| JP (1) | JPS6030666B2 (en, 2012) |
| DE (1) | DE3132332A1 (en, 2012) |
| FR (1) | FR2488888A1 (en, 2012) |
| GB (1) | GB2082174B (en, 2012) |
| IE (1) | IE51505B1 (en, 2012) |
| IT (1) | IT1171468B (en, 2012) |
| NL (1) | NL191943C (en, 2012) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0471058U (en, 2012) * | 1990-08-10 | 1992-06-23 | ||
| JPH05219282A (ja) * | 1991-09-18 | 1993-08-27 | Aisin Seiki Co Ltd | ファクシミリ装置 |
| JPH0670358U (ja) * | 1993-02-26 | 1994-09-30 | 村田機械株式会社 | 画像記録装置のカッター配置構造 |
| JPH0783672A (ja) * | 1993-09-13 | 1995-03-28 | Hitachi Cable Ltd | 光ファイバジャイロ |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3139238A1 (de) * | 1981-10-02 | 1983-04-21 | Basf Ag, 6700 Ludwigshafen | Optisch aktive bausteine fuer die synthese der seitenkette von (r,r,r)-(alpha)-tocopherol sowie verfahren zu deren herstellung |
| DE3148448A1 (de) | 1981-12-08 | 1983-07-28 | Merck Patent Gmbh, 6100 Darmstadt | "perhydrophenanthrenderivate, verfahren zu ihrer herstellung, diese enthaltende fluessigkristalline dielektrika und elektrooptisches anzeigeelement" |
| US5241086A (en) * | 1989-05-02 | 1993-08-31 | Rhone-Poulenc Chimie | Process for the preparation of brominated compounds, especially from alcohols |
| US5256818A (en) * | 1990-11-19 | 1993-10-26 | Tetsuzo Tomioka | Method for making β-mercaptopropionic acid |
| US5391820A (en) * | 1994-04-13 | 1995-02-21 | Hampshire Chemical Corp. | Preparation of 3-mercaptopropionitrile and 3-mercaptopropionic acid |
| WO2004026824A1 (en) * | 2002-09-19 | 2004-04-01 | Novartis Ag | Process for preparing intermediates |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE652715A (en, 2012) * | 1963-09-04 | |||
| US3449416A (en) * | 1965-04-20 | 1969-06-10 | Union Carbide Corp | Process for the preparation of acid halides |
| NL6508594A (en, 2012) * | 1965-07-03 | 1967-01-04 | ||
| DE2354098B2 (de) * | 1973-10-29 | 1976-05-13 | Akzo Gmbh, 5600 Wuppertal | Verfahren zur herstellung von mercaptocarbonsaeuren |
| US4129595A (en) * | 1978-03-29 | 1978-12-12 | Chevron Research Company | Preparation of chloroacetyl chloride |
| JPS54151912A (en) * | 1978-05-18 | 1979-11-29 | Santen Pharmaceutical Co Ltd | Manufacture of photoactive sulfur contained carboxylic acid |
| US4294775A (en) * | 1980-03-03 | 1981-10-13 | Ethyl Corporation | Resolution of acylated D,L-alkyl substituted alkanoic acids |
-
1980
- 1980-08-20 JP JP55115053A patent/JPS6030666B2/ja not_active Expired
-
1981
- 1981-08-07 GB GB8124198A patent/GB2082174B/en not_active Expired
- 1981-08-17 DE DE19813132332 patent/DE3132332A1/de active Granted
- 1981-08-18 US US06/294,028 patent/US4384139A/en not_active Expired - Lifetime
- 1981-08-18 NL NL8103863A patent/NL191943C/xx not_active IP Right Cessation
- 1981-08-18 IT IT49121/81A patent/IT1171468B/it active
- 1981-08-19 FR FR8115949A patent/FR2488888A1/fr active Granted
- 1981-08-19 IE IE1902/81A patent/IE51505B1/en not_active IP Right Cessation
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0471058U (en, 2012) * | 1990-08-10 | 1992-06-23 | ||
| JPH05219282A (ja) * | 1991-09-18 | 1993-08-27 | Aisin Seiki Co Ltd | ファクシミリ装置 |
| JPH0670358U (ja) * | 1993-02-26 | 1994-09-30 | 村田機械株式会社 | 画像記録装置のカッター配置構造 |
| JPH0783672A (ja) * | 1993-09-13 | 1995-03-28 | Hitachi Cable Ltd | 光ファイバジャイロ |
Also Published As
| Publication number | Publication date |
|---|---|
| IE811902L (en) | 1982-02-20 |
| GB2082174B (en) | 1984-09-12 |
| FR2488888B1 (en, 2012) | 1984-11-02 |
| US4384139A (en) | 1983-05-17 |
| DE3132332C2 (en, 2012) | 1989-12-14 |
| GB2082174A (en) | 1982-03-03 |
| NL191943C (nl) | 1996-11-04 |
| FR2488888A1 (fr) | 1982-02-26 |
| IT8149121A0 (it) | 1981-08-18 |
| NL191943B (nl) | 1996-07-01 |
| NL8103863A (nl) | 1982-03-16 |
| IE51505B1 (en) | 1987-01-07 |
| DE3132332A1 (de) | 1982-04-15 |
| IT1171468B (it) | 1987-06-10 |
| JPS5738768A (en) | 1982-03-03 |
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