SU568370A3 - Способ получени производных пенициллановой кислоты и их солей - Google Patents
Способ получени производных пенициллановой кислоты и их солейInfo
- Publication number
- SU568370A3 SU568370A3 SU7502182608A SU2182608A SU568370A3 SU 568370 A3 SU568370 A3 SU 568370A3 SU 7502182608 A SU7502182608 A SU 7502182608A SU 2182608 A SU2182608 A SU 2182608A SU 568370 A3 SU568370 A3 SU 568370A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- salts
- acid derivatives
- ethyl acetate
- penicillanic acid
- solution
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 title description 7
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical class OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- VJRSKMNIDFYNNE-UHFFFAOYSA-N 2-(2-oxo-1,3-dithiol-4-yl)acetyl chloride Chemical compound ClC(=O)CC1=CSC(=O)S1 VJRSKMNIDFYNNE-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- WACQKHWOTAEEFS-UHFFFAOYSA-N cyclohexane;ethyl acetate Chemical compound CCOC(C)=O.C1CCCCC1 WACQKHWOTAEEFS-UHFFFAOYSA-N 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- KGIOWIIAPHYCIH-UHFFFAOYSA-N 2-(2-oxo-1,3-dithiol-4-yl)acetic acid Chemical compound OC(=O)CC1=CSC(=O)S1 KGIOWIIAPHYCIH-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- SBBFXXFKKORHMX-UHFFFAOYSA-N ethyl 4-ethoxycarbothioylsulfanyl-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)CSC(=S)OCC SBBFXXFKKORHMX-UHFFFAOYSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- -1 organic acid salt Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- IOLCXVTUBQKXJR-UHFFFAOYSA-M potassium bromide Chemical compound [K+].[Br-] IOLCXVTUBQKXJR-UHFFFAOYSA-M 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 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 description 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 229930194542 Keto Natural products 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- KSZVHVUMUSIKTC-UHFFFAOYSA-N acetic acid;propan-2-one Chemical compound CC(C)=O.CC(O)=O KSZVHVUMUSIKTC-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000000908 ammonium hydroxide Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229950005228 bromoform Drugs 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- SKCNIGRBPJIUBQ-UHFFFAOYSA-N chloroform;ethyl acetate Chemical compound ClC(Cl)Cl.CCOC(C)=O SKCNIGRBPJIUBQ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000010502 orange oil Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- JCBJVAJGLKENNC-UHFFFAOYSA-M potassium ethyl xanthate Chemical compound [K+].CCOC([S-])=S JCBJVAJGLKENNC-UHFFFAOYSA-M 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- VYPDUQYOLCLEGS-UHFFFAOYSA-M sodium;2-ethylhexanoate Chemical compound [Na+].CCCCC(CC)C([O-])=O VYPDUQYOLCLEGS-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 235000012712 vegetable carbon Nutrition 0.000 description 1
- 239000004108 vegetable carbon Substances 0.000 description 1
- 235000013311 vegetables Nutrition 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C329/00—Thiocarbonic acids; Halides, esters or anhydrides thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7435972A FR2289190A1 (fr) | 1974-10-28 | 1974-10-28 | Nouveaux derives de l'acide penicillanique, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU568370A3 true SU568370A3 (ru) | 1977-08-05 |
Family
ID=9144483
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU7502182608A SU568370A3 (ru) | 1974-10-28 | 1975-10-23 | Способ получени производных пенициллановой кислоты и их солей |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US3969342A (enExample) |
| JP (1) | JPS5176286A (enExample) |
| AR (1) | AR211255A1 (enExample) |
| AT (1) | AT340052B (enExample) |
| BE (1) | BE834907A (enExample) |
| CA (1) | CA1038859A (enExample) |
| CS (1) | CS188974B2 (enExample) |
| DE (1) | DE2548232A1 (enExample) |
| DK (1) | DK482375A (enExample) |
| ES (1) | ES442135A1 (enExample) |
| FI (1) | FI753009A7 (enExample) |
| FR (1) | FR2289190A1 (enExample) |
| GB (1) | GB1472488A (enExample) |
| HU (1) | HU170061B (enExample) |
| IL (1) | IL48371A (enExample) |
| LU (1) | LU73650A1 (enExample) |
| NL (1) | NL7512290A (enExample) |
| NO (1) | NO753597L (enExample) |
| OA (1) | OA05140A (enExample) |
| PH (1) | PH10976A (enExample) |
| SE (1) | SE7511996L (enExample) |
| SU (1) | SU568370A3 (enExample) |
| ZA (1) | ZA756743B (enExample) |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3577408A (en) * | 1968-10-15 | 1971-05-04 | American Home Prod | Tetrahydro-2-oxofuran penicillins |
| US3734904A (en) * | 1971-07-23 | 1973-05-22 | American Home Prod | 6-(1-aminothiocycloalkanoyl amino)penicillanic acids |
| US3821198A (en) * | 1972-05-03 | 1974-06-28 | Squibb & Sons Inc | Derivatives of 6-amino penicillanic acid |
| US3873524A (en) * | 1973-11-30 | 1975-03-25 | American Home Prod | 4-oxo-thiazol ino/idine-5-ylideneacetamido penicillanic acids |
-
1974
- 1974-10-28 FR FR7435972A patent/FR2289190A1/fr active Granted
-
1975
- 1975-10-20 OA OA55641A patent/OA05140A/xx unknown
- 1975-10-20 NL NL7512290A patent/NL7512290A/xx not_active Application Discontinuation
- 1975-10-23 SU SU7502182608A patent/SU568370A3/ru active
- 1975-10-24 CA CA238,300A patent/CA1038859A/fr not_active Expired
- 1975-10-24 US US05/625,503 patent/US3969342A/en not_active Expired - Lifetime
- 1975-10-27 AR AR260953A patent/AR211255A1/es active
- 1975-10-27 SE SE7511996A patent/SE7511996L/xx unknown
- 1975-10-27 PH PH17700A patent/PH10976A/en unknown
- 1975-10-27 LU LU73650A patent/LU73650A1/xx unknown
- 1975-10-27 DK DK482375A patent/DK482375A/da unknown
- 1975-10-27 IL IL48371A patent/IL48371A/xx unknown
- 1975-10-27 BE BE161284A patent/BE834907A/xx unknown
- 1975-10-27 ZA ZA00756743A patent/ZA756743B/xx unknown
- 1975-10-27 NO NO753597A patent/NO753597L/no unknown
- 1975-10-27 HU HURO865A patent/HU170061B/hu unknown
- 1975-10-27 GB GB4413675A patent/GB1472488A/en not_active Expired
- 1975-10-27 JP JP50128446A patent/JPS5176286A/ja active Pending
- 1975-10-28 AT AT819675A patent/AT340052B/de not_active IP Right Cessation
- 1975-10-28 CS CS757267A patent/CS188974B2/cs unknown
- 1975-10-28 FI FI753009A patent/FI753009A7/fi not_active Application Discontinuation
- 1975-10-28 DE DE19752548232 patent/DE2548232A1/de active Pending
- 1975-10-28 ES ES442135A patent/ES442135A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2289190A1 (fr) | 1976-05-28 |
| CS188974B2 (en) | 1979-03-30 |
| AT340052B (de) | 1977-11-25 |
| OA05140A (fr) | 1981-01-31 |
| PH10976A (en) | 1977-10-18 |
| ATA819675A (de) | 1977-03-15 |
| NO753597L (enExample) | 1976-04-29 |
| AU8605175A (en) | 1977-05-05 |
| DE2548232A1 (de) | 1976-05-06 |
| AR211255A1 (es) | 1977-11-15 |
| IL48371A (en) | 1978-07-31 |
| BE834907A (fr) | 1976-04-27 |
| ES442135A1 (es) | 1977-04-01 |
| JPS5176286A (enExample) | 1976-07-01 |
| GB1472488A (en) | 1977-05-04 |
| DK482375A (da) | 1976-04-29 |
| ZA756743B (en) | 1976-10-27 |
| LU73650A1 (enExample) | 1976-08-19 |
| FR2289190B1 (enExample) | 1978-07-21 |
| US3969342A (en) | 1976-07-13 |
| NL7512290A (nl) | 1976-05-03 |
| HU170061B (enExample) | 1977-03-28 |
| SE7511996L (sv) | 1976-04-29 |
| FI753009A7 (enExample) | 1976-04-29 |
| IL48371A0 (en) | 1975-12-31 |
| CA1038859A (fr) | 1978-09-19 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4886792A (en) | 10-dihydro-10-deoxo-11-azaerythronolide a compounds, methods and intermediates for the manufacture thereof and their use in pharmaceuticals and in the manufacture thereof | |
| JPH0362711B2 (enExample) | ||
| EP0005614B1 (en) | Lithium pseudomonate, process for its isolation and its hydrolysis | |
| SU458131A3 (ru) | Способ получени шифровых оснований 7-амино-3-дезацфетоксицефалоспорановой кислоты | |
| US3714156A (en) | Lactam process | |
| SU568370A3 (ru) | Способ получени производных пенициллановой кислоты и их солей | |
| US3976641A (en) | Cephalosporin intermediates and process therefor | |
| SU558644A3 (ru) | Способ получени имидазолов или их солей | |
| US2926167A (en) | Process of esterifying ib-hydroxy | |
| SU574158A3 (ru) | Способ получени цефалексина или его солей | |
| KR830001969B1 (ko) | 6―｛D―(―) α-(4―에틸-2. 3-디옥소-1 피페라지노카보닐아미노) 페닐(또는 하이드록시페닐)아세트아미도 페니실란산 및 그 염의 제조방법 | |
| US2478047A (en) | Alpha-amino-beta, beta-diethoxypropionic acid and process for preparation | |
| US2966484A (en) | Chemical compounds | |
| US3047578A (en) | Substituted reserpine and process of making the same | |
| PL98296B1 (pl) | Sposob otrzymywania estrow acetoksymetylowych cefalosporyn | |
| US3923796A (en) | Certain 6,7-dioxo-2H-pyrrolo-{8 2,1-b{9 thiazines | |
| US3049551A (en) | Novobiocin intermediate and process therefor | |
| US3875154A (en) | Certain 5-thia-1-azabicyclo{8 4.2.0{9 octenes | |
| US3148192A (en) | Halogenated 20alpha-yohimbane compounds | |
| US3303195A (en) | Methylated deserpidine | |
| SU552903A3 (ru) | Способ получени производных 6-трихлорацетамидопенициллановой кислоты | |
| US2990407A (en) | Co cha | |
| US4513145A (en) | 2-Methylchromone derivatives and process for their preparation | |
| KR830001970B1 (ko) | 세파로스포린 유도체의 제조방법 | |
| CA1047484A (en) | Penicillins |