CA1071189A - Procede pour la production de nouveaux produits chimiques et procede pour la production de composes de 6-(p-hydroxyphenylglycilamido)-penam ou de 7-(p-hydroxyphenylglycilamido)-cephem - Google Patents
Procede pour la production de nouveaux produits chimiques et procede pour la production de composes de 6-(p-hydroxyphenylglycilamido)-penam ou de 7-(p-hydroxyphenylglycilamido)-cephemInfo
- Publication number
- CA1071189A CA1071189A CA254,379A CA254379A CA1071189A CA 1071189 A CA1071189 A CA 1071189A CA 254379 A CA254379 A CA 254379A CA 1071189 A CA1071189 A CA 1071189A
- Authority
- CA
- Canada
- Prior art keywords
- hydroxyphenylglycylamido
- preparing
- compounds
- mmoles
- cephem
- 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 abstract description 8
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 150000002148 esters Chemical class 0.000 claims abstract description 15
- -1 phos-phite amide Chemical class 0.000 claims abstract description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 11
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 claims abstract description 9
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000000034 method Methods 0.000 claims abstract description 8
- 150000001412 amines Chemical class 0.000 claims abstract description 7
- RJFPBECTFIUTHB-INEUFUBQSA-N (6r,7r)-7-azaniumyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound S1CC=C(C(O)=O)N2C(=O)[C@@H](N)[C@H]21 RJFPBECTFIUTHB-INEUFUBQSA-N 0.000 claims abstract description 5
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical group [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 claims description 12
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 3
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 claims 3
- RHEFYFUGIMENJN-GLGOKHISSA-N (2,5-dioxopyrrolidin-3-yl) (2R)-2-amino-2-(4-trimethylsilyloxyphenyl)acetate Chemical compound C[Si](OC1=CC=C([C@@H](N)C(=O)OC2C(=O)NC(C2)=O)C=C1)(C)C RHEFYFUGIMENJN-GLGOKHISSA-N 0.000 abstract description 5
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 14
- 238000001914 filtration Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000002255 enzymatic effect Effects 0.000 description 5
- 229910052739 hydrogen Inorganic materials 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- OLSFRDLMFAOSIA-UHFFFAOYSA-N 2-chloro-1,3,2-dioxaphospholane Chemical compound ClP1OCCO1 OLSFRDLMFAOSIA-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 4
- 235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 4
- YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 4
- 238000001962 electrophoresis Methods 0.000 description 4
- 238000002329 infrared spectrum Methods 0.000 description 4
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 4
- LSQZJLSUYDQPKJ-UHFFFAOYSA-N p-Hydroxyampicillin Natural products O=C1N2C(C(O)=O)C(C)(C)SC2C1NC(=O)C(N)C1=CC=C(O)C=C1 LSQZJLSUYDQPKJ-UHFFFAOYSA-N 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229930182555 Penicillin Natural products 0.000 description 3
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000010933 acylation Effects 0.000 description 3
- 238000005917 acylation reaction Methods 0.000 description 3
- LSQZJLSUYDQPKJ-NJBDSQKTSA-N amoxicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=C(O)C=C1 LSQZJLSUYDQPKJ-NJBDSQKTSA-N 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 235000013350 formula milk Nutrition 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 229940049954 penicillin Drugs 0.000 description 3
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 239000005051 trimethylchlorosilane Substances 0.000 description 3
- VFERFGLYBXDICV-MRXNPFEDSA-N (1,3-dioxoisoindol-4-yl) (2R)-2-amino-2-(4-trimethylsilyloxyphenyl)acetate Chemical compound C[Si](OC1=CC=C([C@@H](N)C(=O)OC2=C3C(C(=O)NC3=O)=CC=C2)C=C1)(C)C VFERFGLYBXDICV-MRXNPFEDSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000010647 peptide synthesis reaction Methods 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- MLOZJRLUNNFSGD-IOJJLOCKSA-N (6r)-7-amino-8-oxo-3-(2h-triazol-4-ylsulfanylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound S([C@@H]1C(C(N1C=1C(O)=O)=O)N)CC=1CSC=1C=NNN=1 MLOZJRLUNNFSGD-IOJJLOCKSA-N 0.000 description 1
- CFMZSMGAMPBRBE-UHFFFAOYSA-N 2-hydroxyisoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(O)C(=O)C2=C1 CFMZSMGAMPBRBE-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 239000002021 butanolic extract Substances 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- LIKFHECYJZWXFJ-UHFFFAOYSA-N dimethyldichlorosilane Chemical compound C[Si](C)(Cl)Cl LIKFHECYJZWXFJ-UHFFFAOYSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000003949 imides Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- XTAZYLNFDRKIHJ-UHFFFAOYSA-N n,n-dioctyloctan-1-amine Chemical compound CCCCCCCCN(CCCCCCCC)CCCCCCCC XTAZYLNFDRKIHJ-UHFFFAOYSA-N 0.000 description 1
- FEMOMIGRRWSMCU-UHFFFAOYSA-N ninhydrin Chemical compound C1=CC=C2C(=O)C(O)(O)C(=O)C2=C1 FEMOMIGRRWSMCU-UHFFFAOYSA-N 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- DRTZAIDVOGUYSP-UHFFFAOYSA-N pyridin-1-ium;chloride;hydrochloride Chemical compound Cl.Cl.C1=CC=NC=C1 DRTZAIDVOGUYSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
- 229910001488 sodium perchlorate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB25447/75A GB1546077A (en) | 1975-06-13 | 1975-06-13 | Chemical compounds process for preparing said compounds and process for preparing 6-(p-hydroxyphenyl-glycylamido)-penam or 7-(p-hydroxyphenyl-glycylamido)-cephem compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1071189A true CA1071189A (fr) | 1980-02-05 |
Family
ID=10227825
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA254,379A Expired CA1071189A (fr) | 1975-06-13 | 1976-06-09 | Procede pour la production de nouveaux produits chimiques et procede pour la production de composes de 6-(p-hydroxyphenylglycilamido)-penam ou de 7-(p-hydroxyphenylglycilamido)-cephem |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS52260A (fr) |
| BR (1) | BR7603793A (fr) |
| CA (1) | CA1071189A (fr) |
| DE (1) | DE2626280A1 (fr) |
| DK (1) | DK263976A (fr) |
| ES (2) | ES448787A1 (fr) |
| FI (1) | FI761627A7 (fr) |
| GB (1) | GB1546077A (fr) |
| NL (1) | NL7606360A (fr) |
| PT (1) | PT65212B (fr) |
| SE (1) | SE7606567L (fr) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9410480B2 (en) | 2008-12-23 | 2016-08-09 | Thyssenkrupp Uhde Gmbh | Method for use of the synthesis gas that comes from a gasifier |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0379892A (ja) * | 1989-08-21 | 1991-04-04 | Yoshihisa Miura | チャック付きフェルール |
-
1975
- 1975-06-13 GB GB25447/75A patent/GB1546077A/en not_active Expired
-
1976
- 1976-06-08 FI FI761627A patent/FI761627A7/fi not_active Application Discontinuation
- 1976-06-09 CA CA254,379A patent/CA1071189A/fr not_active Expired
- 1976-06-10 SE SE7606567A patent/SE7606567L/xx unknown
- 1976-06-11 DK DK263976A patent/DK263976A/da not_active Application Discontinuation
- 1976-06-11 PT PT65212A patent/PT65212B/pt unknown
- 1976-06-11 ES ES448787A patent/ES448787A1/es not_active Expired
- 1976-06-11 DE DE19762626280 patent/DE2626280A1/de not_active Withdrawn
- 1976-06-11 BR BR7603793A patent/BR7603793A/pt unknown
- 1976-06-11 NL NL7606360A patent/NL7606360A/xx not_active Application Discontinuation
- 1976-06-14 JP JP51069639A patent/JPS52260A/ja active Pending
-
1977
- 1977-08-01 ES ES461244A patent/ES461244A1/es not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9410480B2 (en) | 2008-12-23 | 2016-08-09 | Thyssenkrupp Uhde Gmbh | Method for use of the synthesis gas that comes from a gasifier |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS52260A (en) | 1977-01-05 |
| SE7606567L (sv) | 1976-12-14 |
| FI761627A7 (fr) | 1976-12-14 |
| PT65212A (en) | 1976-07-01 |
| DK263976A (da) | 1976-12-14 |
| DE2626280A1 (de) | 1976-12-30 |
| NL7606360A (nl) | 1976-12-15 |
| ES461244A1 (es) | 1978-05-01 |
| BR7603793A (pt) | 1977-02-08 |
| GB1546077A (en) | 1979-05-16 |
| ES448787A1 (es) | 1978-01-01 |
| PT65212B (en) | 1977-11-23 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US6034237A (en) | 3-imino-cephalosporins | |
| US5401841A (en) | Process for the production of cephalosporines | |
| US4254029A (en) | Process for preparing β-lactam antibiotics | |
| US4098796A (en) | P-trimethylsilyloxyphenyl glycyloxyphthalimide | |
| US4178294A (en) | p-Trimethylsilyloxyphenyl glycyloxy succinimide | |
| EP0369687B1 (fr) | Solvates d'un antibiotique de bêta-lactame | |
| US4977257A (en) | DMF solvates of a β-lactam antibiotic | |
| FI74709B (fi) | Trimetylsilyloxikarbonyl-7- aminodecefalosporansyra-trimetylsilylester foer anvaendning som mellanprodukt och foerfarande foer framstaellning av denna. | |
| GB2078725A (en) | N-chlorocarbonyl Lactams | |
| US4304717A (en) | Process for the preparation of reactive penicillanic acid and cephalosporanic acid derivatives | |
| US4959495A (en) | Process for the preparation of intermediates used to produce aminothiazoloximino cephalosporins | |
| KR100472048B1 (ko) | 아즈트레오남의 신규제조방법 | |
| JPS6338355B2 (fr) | ||
| US4082745A (en) | Process for the preparation of phosphorus derivatives of secondary ammonium salts of penam and cephem compounds | |
| KR950013571B1 (ko) | (6r, 7r)-7-[(z)-2-(2-아미노티아졸-4-일)-2-(2-카르복시프로프-2-옥시이미노)아세트아미도]-3-(1-피리디늄메틸)세프-3-엠-4-카르복실레이트 이염산염의 제조방법 | |
| KR800000789B1 (ko) | 신규 아미노산류의 제조방법 | |
| DE2626280A1 (de) | Neue phenylglycinderivate, verfahren zur herstellung derselben und verfahren zur herstellung von 6-(p-hydroxyphenylglycylamido)-penam- oder 7-(p-hydroxyphenylglycylamido)-cephemverbindungen | |
| US4301072A (en) | Process for preparing aminopenicillins | |
| KR950013567B1 (ko) | 세펨유도체의 제조방법 | |
| JPS6328075B2 (fr) | ||
| US4231954A (en) | Dane salt and process for preparing aminopenicillins therefrom | |
| US4202817A (en) | Process for the production of penam and cephem derivatives | |
| US3943126A (en) | Process for acylating a 7-aminocephalosporin | |
| KR830002204B1 (ko) | 카나마이신 a 유도체의 제조 방법 | |
| KR810000858B1 (ko) | β-락탐계 항생물질의 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |