SU495840A3 - Способ получени сульфоксида пенициллина - Google Patents
Способ получени сульфоксида пенициллинаInfo
- Publication number
- SU495840A3 SU495840A3 SU1959496A SU1959496A SU495840A3 SU 495840 A3 SU495840 A3 SU 495840A3 SU 1959496 A SU1959496 A SU 1959496A SU 1959496 A SU1959496 A SU 1959496A SU 495840 A3 SU495840 A3 SU 495840A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- broth
- penicillin
- amount
- oxidant
- diluted
- Prior art date
Links
- FCZNNHHXCFARDY-WQRUCBPWSA-N (2s,5r,6r)-3,3-dimethyl-4,7-dioxo-6-[(2-phenylacetyl)amino]-4$l^{4}-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid Chemical compound N([C@H]1[C@@H]2N(C1=O)[C@H](C(S2=O)(C)C)C(O)=O)C(=O)CC1=CC=CC=C1 FCZNNHHXCFARDY-WQRUCBPWSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 238000000034 method Methods 0.000 claims description 13
- 239000002253 acid Substances 0.000 claims description 10
- 229930182555 Penicillin Natural products 0.000 claims description 9
- 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 claims description 9
- 239000007800 oxidant agent Substances 0.000 claims description 9
- 238000000855 fermentation Methods 0.000 claims description 8
- 230000004151 fermentation Effects 0.000 claims description 8
- 239000000203 mixture Substances 0.000 claims description 8
- 229940049954 penicillin Drugs 0.000 claims description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000007788 liquid Substances 0.000 claims description 5
- 230000001590 oxidative effect Effects 0.000 claims description 5
- 150000003462 sulfoxides Chemical class 0.000 claims description 5
- 239000007787 solid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 3
- 239000003960 organic solvent Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 2
- 101100502683 Ustilago maydis (strain 521 / FGSC 9021) fer6 gene Proteins 0.000 claims 1
- 239000012736 aqueous medium Substances 0.000 claims 1
- 244000005700 microbiome Species 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 238000002425 crystallisation Methods 0.000 description 5
- 230000008025 crystallization Effects 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 238000007254 oxidation reaction Methods 0.000 description 3
- -1 penicillin sulfoxides Chemical class 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 150000002960 penicillins Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- OVXWHHYDMKASOR-UHFFFAOYSA-N 1-methylcyclohexa-2,4-diene-1-sulfonic acid Chemical compound OS(=O)(=O)C1(C)CC=CC=C1 OVXWHHYDMKASOR-UHFFFAOYSA-N 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 101150042033 Copg1 gene Proteins 0.000 description 1
- 241000238424 Crustacea Species 0.000 description 1
- 101100114422 Drosophila melanogaster gammaCOP gene Proteins 0.000 description 1
- 101100223892 Escherichia coli sulI gene Proteins 0.000 description 1
- 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 1
- 102000004877 Insulin Human genes 0.000 description 1
- 108090001061 Insulin Proteins 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 241000228143 Penicillium Species 0.000 description 1
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 description 1
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 1
- 241000534944 Thia Species 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- VBBRYJMZLIYUJQ-UHFFFAOYSA-N cyclopropanone Chemical compound O=C1CC1 VBBRYJMZLIYUJQ-UHFFFAOYSA-N 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Substances N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- FUJCRWPEOMXPAD-UHFFFAOYSA-N lithium oxide Chemical compound [Li+].[Li+].[O-2] FUJCRWPEOMXPAD-UHFFFAOYSA-N 0.000 description 1
- 229910001947 lithium oxide Inorganic materials 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 229940056360 penicillin g Drugs 0.000 description 1
- 150000004965 peroxy acids Chemical class 0.000 description 1
- WCMIIGXFCMNQDS-IDYPWDAWSA-M piperacillin sodium Chemical compound [Na+].O=C1C(=O)N(CC)CCN1C(=O)N[C@H](C=1C=CC=CC=1)C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 WCMIIGXFCMNQDS-IDYPWDAWSA-M 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/04—Preparation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US288459A US3904605A (en) | 1972-09-12 | 1972-09-12 | Penicillin oxidation process |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU495840A3 true SU495840A3 (ru) | 1975-12-15 |
Family
ID=23107189
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1959496A SU495840A3 (ru) | 1972-09-12 | 1973-09-11 | Способ получени сульфоксида пенициллина |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3904605A (en:Method) |
| JP (1) | JPS4962495A (en:Method) |
| KR (1) | KR780000146B1 (en:Method) |
| AR (1) | AR201835A1 (en:Method) |
| AT (1) | AT330348B (en:Method) |
| AU (1) | AU472678B2 (en:Method) |
| BE (1) | BE804710A (en:Method) |
| BG (1) | BG21231A3 (en:Method) |
| CA (1) | CA1007635A (en:Method) |
| CH (1) | CH583737A5 (en:Method) |
| DD (1) | DD107049A5 (en:Method) |
| DE (1) | DE2344812A1 (en:Method) |
| ES (1) | ES418639A1 (en:Method) |
| FR (1) | FR2198948B1 (en:Method) |
| GB (1) | GB1388979A (en:Method) |
| HU (1) | HU166395B (en:Method) |
| IE (1) | IE38106B1 (en:Method) |
| IL (1) | IL43065A (en:Method) |
| NL (1) | NL7312145A (en:Method) |
| PH (1) | PH9481A (en:Method) |
| PL (1) | PL89405B1 (en:Method) |
| RO (1) | RO63002A (en:Method) |
| SU (1) | SU495840A3 (en:Method) |
| ZA (1) | ZA735720B (en:Method) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4354971A (en) * | 1981-06-22 | 1982-10-19 | Eli Lilly And Company | Non-extractive penicillin V recovery process |
| US7028687B1 (en) | 1999-08-26 | 2006-04-18 | Precious Life, Llc | Escape hood |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3047467A (en) * | 1957-08-02 | 1962-07-31 | Beecham Res Lab | Process for the preparation of penicillins |
| US3025290A (en) * | 1959-06-09 | 1962-03-13 | Doyle Frank Peter | Synthetic penicillin and salts thereof |
| US3197466A (en) * | 1961-10-30 | 1965-07-27 | Smith Kline French Lab | Penicillin sulfoxides and process |
| US3586667A (en) * | 1967-12-22 | 1971-06-22 | Lilly Co Eli | Penicillin esterification process |
| US3647787A (en) * | 1969-07-02 | 1972-03-07 | Lilly Co Eli | Process improvement for converting penicillin sulfoxide esters to cephem compounds |
-
1972
- 1972-09-12 US US288459A patent/US3904605A/en not_active Expired - Lifetime
-
1973
- 1973-08-20 IE IE1445/73A patent/IE38106B1/xx unknown
- 1973-08-21 GB GB3960373A patent/GB1388979A/en not_active Expired
- 1973-08-21 ZA ZA00735720A patent/ZA735720B/xx unknown
- 1973-08-23 CA CA179,462A patent/CA1007635A/en not_active Expired
- 1973-08-24 IL IL43065A patent/IL43065A/en unknown
- 1973-08-24 PH PH14949*UA patent/PH9481A/en unknown
- 1973-08-27 AU AU59661/73A patent/AU472678B2/en not_active Expired
- 1973-09-03 NL NL7312145A patent/NL7312145A/xx not_active Application Discontinuation
- 1973-09-05 DE DE19732344812 patent/DE2344812A1/de active Pending
- 1973-09-07 AR AR249970A patent/AR201835A1/es active
- 1973-09-10 ES ES418639A patent/ES418639A1/es not_active Expired
- 1973-09-11 AT AT786773A patent/AT330348B/de not_active IP Right Cessation
- 1973-09-11 BE BE1005350A patent/BE804710A/xx unknown
- 1973-09-11 JP JP48102573A patent/JPS4962495A/ja active Pending
- 1973-09-11 HU HUEI495A patent/HU166395B/hu unknown
- 1973-09-11 SU SU1959496A patent/SU495840A3/ru active
- 1973-09-12 KR KR7301518A patent/KR780000146B1/ko not_active Expired
- 1973-09-12 DD DD173425A patent/DD107049A5/xx unknown
- 1973-09-12 FR FR7332798A patent/FR2198948B1/fr not_active Expired
- 1973-09-12 CH CH1308673A patent/CH583737A5/xx not_active IP Right Cessation
- 1973-09-12 BG BG024528A patent/BG21231A3/xx unknown
- 1973-09-12 RO RO7300076059A patent/RO63002A/ro unknown
- 1973-09-12 PL PL1973165173A patent/PL89405B1/pl unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL89405B1 (en:Method) | 1976-11-30 |
| AU5966173A (en) | 1975-02-27 |
| HU166395B (en:Method) | 1975-03-28 |
| JPS4962495A (en:Method) | 1974-06-17 |
| US3904605A (en) | 1975-09-09 |
| RO63002A (fr) | 1978-05-15 |
| IE38106L (en) | 1974-03-12 |
| PH9481A (en) | 1976-01-08 |
| FR2198948A1 (en:Method) | 1974-04-05 |
| KR780000146B1 (en) | 1978-05-02 |
| CA1007635A (en) | 1977-03-29 |
| GB1388979A (en) | 1975-04-03 |
| AT330348B (de) | 1976-06-25 |
| CH583737A5 (en:Method) | 1977-01-14 |
| FR2198948B1 (en:Method) | 1977-08-05 |
| IE38106B1 (en) | 1977-12-21 |
| BG21231A3 (bg) | 1976-03-20 |
| ES418639A1 (es) | 1976-02-16 |
| NL7312145A (en:Method) | 1974-03-14 |
| DE2344812A1 (de) | 1974-03-21 |
| BE804710A (fr) | 1974-03-11 |
| IL43065A0 (en) | 1973-11-28 |
| IL43065A (en) | 1976-01-30 |
| AU472678B2 (en) | 1976-06-03 |
| ZA735720B (en) | 1975-04-30 |
| AR201835A1 (es) | 1975-04-24 |
| DD107049A5 (en:Method) | 1974-07-12 |
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