ES443372A1 - A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 3-CEFEM-4-CARBOXYL ACID. - Google Patents
A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 3-CEFEM-4-CARBOXYL ACID.Info
- Publication number
- ES443372A1 ES443372A1 ES443372A ES443372A ES443372A1 ES 443372 A1 ES443372 A1 ES 443372A1 ES 443372 A ES443372 A ES 443372A ES 443372 A ES443372 A ES 443372A ES 443372 A1 ES443372 A1 ES 443372A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- see formula
- salt
- produce
- 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
- 239000002253 acid Substances 0.000 title abstract 4
- 238000000034 method Methods 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 abstract 7
- 150000001875 compounds Chemical class 0.000 abstract 6
- 150000002148 esters Chemical class 0.000 abstract 4
- 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 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- IKWLIQXIPRUIDU-ZCFIWIBFSA-N (6r)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical class OC(=O)C1=CCS[C@@H]2CC(=O)N12 IKWLIQXIPRUIDU-ZCFIWIBFSA-N 0.000 abstract 1
- LLCOQBODWBFTDD-UHFFFAOYSA-N 1h-triazol-1-ium-4-thiolate Chemical compound SC1=CNN=N1 LLCOQBODWBFTDD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
Abstract
A procedure for the preparation of derivatives of 3-cephem-4-carboxylic acid of the formula: **(See formula)** where X is H or a radical of formula **(See formula)** where Z is H, an amino group blocking group, especially a radical of formula **(See formula)** where R is haloalkyl lower or lower alkyl of 1 to 20 carbon atoms or aryl, preferably **(See formula)** where n is an integer from 0 to 6 and R2 and R3 are the same or different and each represents H, C1, Br, F, NO2, lower alkyl or lower alkoxy; whose procedure is characterized by the following consecutive stages: A) treatment of a compound of formula I **(See formula)** where M is H or a cation, Y is a radical of formula: **(See formula)** where M and Z are as defined above, with 5-mercapto-1,2,3-triazole of formula **(See formula)** or a salt thereof, to produce a compound of the formula **(See formula)** where Y and M are those defined above and, when it is desired to produce compound I where X is H, B) cleaving the 7-amide linkage by known methods to produce 7-amino-3- [S- (1,2,3-triazol-5-yl) thiomethyl] -3-cephem-4-carboxylic acid (VI) or, when it is desired to produce compound I where X is D - (-) - (p-hydroxyphenyl) glycyl, C) acylating compound VI or an ester is readily cleavable or a salt thereof with an acylating derivative of an acid of formula **(See formula)** where B represents an amino protecting group, to produce, after removing the protecting group from the amino group, a compound of formula LX or an easily cleavable ester or a pharmaceutically acceptable salt thereof and, if desired, before or after removing Group B: (a) converting the product in the form of free acid or salt thereof to the corresponding easily cleavable ester or pharmaceutically acceptable salt thereof or (b) converting the product into easily cleavable ester or salt thereof into the corresponding free acid or pharmaceutically acceptable salt thereof. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US53266374A | 1974-12-13 | 1974-12-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES443372A1 true ES443372A1 (en) | 1977-12-01 |
Family
ID=24122664
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES443372A Expired ES443372A1 (en) | 1974-12-13 | 1975-12-10 | A PROCEDURE FOR THE PREPARATION OF DERIVATIVES OF 3-CEFEM-4-CARBOXYL ACID. |
Country Status (21)
| Country | Link |
|---|---|
| JP (2) | JPS6117837B2 (en) |
| AT (1) | AT343803B (en) |
| AU (1) | AU8688075A (en) |
| BE (1) | BE836428A (en) |
| DD (1) | DD123191A5 (en) |
| DE (1) | DE2556105A1 (en) |
| DK (1) | DK564175A (en) |
| ES (1) | ES443372A1 (en) |
| FI (1) | FI753518A7 (en) |
| FR (1) | FR2294179A1 (en) |
| GR (1) | GR58533B (en) |
| IL (1) | IL48644A0 (en) |
| IN (1) | IN143474B (en) |
| LU (1) | LU74003A1 (en) |
| NL (1) | NL7514391A (en) |
| NO (1) | NO754196L (en) |
| NZ (1) | NZ179268A (en) |
| OA (1) | OA05182A (en) |
| RO (1) | RO68147A (en) |
| SE (1) | SE7514034L (en) |
| ZA (1) | ZA757744B (en) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3819621A (en) * | 1970-12-30 | 1974-06-25 | Fujisawa Pharmaceutical Co | 3-substituted-thiomethyl-3-cephem-4-carboxylic acid derivatives |
| JPS4945879A (en) * | 1972-09-09 | 1974-05-01 | ||
| KR780000197B1 (en) * | 1972-12-26 | 1978-05-26 | Bristol Myers Co | Method for preparing antibacterial agent |
-
1975
- 1975-11-18 NZ NZ179268A patent/NZ179268A/en unknown
- 1975-11-19 IN IN2201/CAL/1975A patent/IN143474B/en unknown
- 1975-11-24 GR GR49447A patent/GR58533B/en unknown
- 1975-11-24 AU AU86880/75A patent/AU8688075A/en not_active Expired
- 1975-12-09 BE BE162568A patent/BE836428A/en unknown
- 1975-12-09 RO RO7584141A patent/RO68147A/en unknown
- 1975-12-10 ES ES443372A patent/ES443372A1/en not_active Expired
- 1975-12-10 ZA ZA757744A patent/ZA757744B/en unknown
- 1975-12-10 AT AT938875A patent/AT343803B/en not_active IP Right Cessation
- 1975-12-10 IL IL48644A patent/IL48644A0/en unknown
- 1975-12-10 NL NL7514391A patent/NL7514391A/en not_active Application Discontinuation
- 1975-12-11 DK DK564175A patent/DK564175A/en unknown
- 1975-12-11 NO NO754196A patent/NO754196L/no unknown
- 1975-12-11 SE SE7514034A patent/SE7514034L/en unknown
- 1975-12-12 DE DE19752556105 patent/DE2556105A1/en active Pending
- 1975-12-12 OA OA55690A patent/OA05182A/en unknown
- 1975-12-12 JP JP50147480A patent/JPS6117837B2/ja not_active Expired
- 1975-12-12 FI FI753518A patent/FI753518A7/fi not_active Application Discontinuation
- 1975-12-12 FR FR7538216A patent/FR2294179A1/en not_active Withdrawn
- 1975-12-12 LU LU74003A patent/LU74003A1/xx unknown
- 1975-12-15 DD DD190154A patent/DD123191A5/xx unknown
-
1985
- 1985-04-25 JP JP60087656A patent/JPS615083A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6117837B2 (en) | 1986-05-09 |
| NO754196L (en) | 1976-06-15 |
| RO68147A (en) | 1980-01-15 |
| IN143474B (en) | 1977-12-03 |
| ATA938875A (en) | 1977-10-15 |
| JPS615083A (en) | 1986-01-10 |
| GR58533B (en) | 1977-10-31 |
| FR2294179A1 (en) | 1976-07-09 |
| DD123191A5 (en) | 1976-12-05 |
| ZA757744B (en) | 1976-11-24 |
| AT343803B (en) | 1978-06-26 |
| BE836428A (en) | 1976-06-09 |
| OA05182A (en) | 1981-01-31 |
| DK564175A (en) | 1976-06-14 |
| AU8688075A (en) | 1977-06-02 |
| NZ179268A (en) | 1978-04-28 |
| DE2556105A1 (en) | 1976-06-24 |
| IL48644A0 (en) | 1976-02-29 |
| NL7514391A (en) | 1976-06-15 |
| FI753518A7 (en) | 1976-06-14 |
| LU74003A1 (en) | 1976-11-11 |
| SE7514034L (en) | 1976-06-14 |
| JPS5182294A (en) | 1976-07-19 |
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