GB1425571A - Penicillins and cephaosporins - Google Patents
Penicillins and cephaosporinsInfo
- Publication number
- GB1425571A GB1425571A GB1168672A GB1168672A GB1425571A GB 1425571 A GB1425571 A GB 1425571A GB 1168672 A GB1168672 A GB 1168672A GB 1168672 A GB1168672 A GB 1168672A GB 1425571 A GB1425571 A GB 1425571A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- reacting
- defined above
- salt
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 4
- 150000002960 penicillins Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 8
- 150000003839 salts Chemical class 0.000 abstract 5
- -1 alkali metal cation Chemical class 0.000 abstract 4
- 229930186147 Cephalosporin Natural products 0.000 abstract 3
- 229940124587 cephalosporin Drugs 0.000 abstract 3
- 150000001780 cephalosporins Chemical class 0.000 abstract 3
- 125000006239 protecting group Chemical group 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- LRRZEFHRNAFQFH-UHFFFAOYSA-N [2-(ethoxycarbonyloxymethyl)phenyl] acetate Chemical compound C(C)(=O)OC1=C(C=CC=C1)COC(=O)OCC LRRZEFHRNAFQFH-UHFFFAOYSA-N 0.000 abstract 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- RTFGZMKXMSDULM-UHFFFAOYSA-N chloromethyl ethyl carbonate Chemical compound CCOC(=O)OCCl RTFGZMKXMSDULM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229940049953 phenylacetate Drugs 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- JFOZPCWVLIBFCH-UHFFFAOYSA-M potassium;2-phenylacetate Chemical compound [K+].[O-]C(=O)CC1=CC=CC=C1 JFOZPCWVLIBFCH-UHFFFAOYSA-M 0.000 abstract 1
- 239000007787 solid Substances 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65613—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. cephalosporins and analogs
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Cephalosporin Compounds (AREA)
Abstract
1425571 Penicillins and cephalosporins ASTRA LAKEMEDEL AB 13 March 1973 [13 March 1972] 11686/72 Heading C2C [Also in Division A5] Novel penicillins and cephalosporins of formula or pharmaceutically acceptable salts thereof, wherein R<SP>1</SP> is an organic radical, R<SP>2</SP> is wherein R<SP>5</SP> is hydrogen; alkanoyloxy; 1- pyridinium; a group -SR<SP>6</SP>, wherein R<SP>6</SP> is CH 3 or a heterocyclic group; or azido; R<SP>3</SP> is wherein R<SP>7</SP> is an alkyl, phenyl or a benzyl group, and wherein these groups are optionally substituted with one or more amino or substituted amino groups; R<SP>8</SP> is H or CH 3 and R<SP>4</SP> is alkoxy; are prepared (a) by reacting a compound of formula or a salt thereof, wherein R<SP>1</SP> , R<SP>2</SP> and R<SP>4</SP> are R<SP>1</SP>, R<SP>2</SP> and R<SP>4</SP> as defined above or are amino or carboxy groups appropriately protected, with a compound of formula R<SP>3</SP>Y, wherein R<SP>3</SP> is as defined above and Y is halogen or a sulphonic acid residue and, if necessary, removing the protecting groups; or (b) by reacting a salt of an acid of formula wherein R<SP>21</SP> and R<SP>4</SP> have the meanings given above with a compound of formula R<SP>3</SP>Y as in (a), reacting the resulting ester of formula wherein R<SP>21</SP>, R<SP>3</SP> and R<SP>4</SP> are as defined above, with a compound of formula R<SP>11</SP>-CO-Z, wherein R<SP>11</SP> is as defined above, and -CO-Z is a reactive acylating group, and, if necessary, removing any protecting groups; or (c) by reacting a compound of formula wherein RCO is the acyl group in the side chain of a natural penicillin or cephalosporin, R<SP>21</SP> and R<SP>4</SP> are as defined above and M is H or an alkali metal cation, with a compound of formula R<SP>3</SP>Y, defined as above, reacting the resulting ester with a phosphorus halide to give an imino halide, which is reacted with a lower alcohol to give an iminoether which is reacted with a compound R<SP>11</SP>-COZ, wherein R<SP>11</SP> and COZ are as defined above, treating with water or alcohol and, if necessary, removing the protecting groups. The salt of method (a) and (b) may be the tetrabutylammonium salt. Ethoxycarbonyloxymethylphenyl acetate is prepared by reacting potassium phenylacetate with chloromethylethylcarbonate. Phenylmalonic acid ethoxycarbonyloxymethyl monoester is prepared by reacting ethoxycarbonyloxymethyl phenyl acetate with solid CO 2 in the presence of n-butyllithium. Pharmaceutical compositions comprise a compound of Formula I or a pharmaceutically acceptable salt thereof with a pharmaceutically acceptable carrier. Other antibiotics may also be present (see Division A5).
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1168672A GB1425571A (en) | 1972-03-13 | 1972-03-13 | Penicillins and cephaosporins |
| DE19732311005 DE2311005A1 (en) | 1972-03-13 | 1973-03-06 | BETA-LACTAM DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND PHARMACEUTICAL PRODUCTS CONTAINING THEM |
| AU53210/73A AU5321073A (en) | 1972-03-13 | 1973-03-12 | Penicillins and cephalosporins |
| FR7308759A FR2181813B1 (en) | 1972-03-13 | 1973-03-12 | |
| AT213773A AT330955B (en) | 1972-03-13 | 1973-03-12 | PROCESS FOR MANUFACTURING NEW BETA-LACTAMEN |
| JP48028903A JPS4924988A (en) | 1972-03-13 | 1973-03-12 | |
| NL7303484A NL7303484A (en) | 1972-03-13 | 1973-03-13 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1168672A GB1425571A (en) | 1972-03-13 | 1972-03-13 | Penicillins and cephaosporins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1425571A true GB1425571A (en) | 1976-02-18 |
Family
ID=9990827
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1168672A Expired GB1425571A (en) | 1972-03-13 | 1972-03-13 | Penicillins and cephaosporins |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4924988A (en) |
| AT (1) | AT330955B (en) |
| AU (1) | AU5321073A (en) |
| DE (1) | DE2311005A1 (en) |
| FR (1) | FR2181813B1 (en) |
| GB (1) | GB1425571A (en) |
| NL (1) | NL7303484A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048320A (en) * | 1975-01-17 | 1977-09-13 | Beecham Group Limited | Penicillins |
| GB2123821A (en) * | 1982-06-29 | 1984-02-08 | Astra Laekemedel Ab | ???-Halogeno diethyl carbonates and their use in the preparation of antibiotics |
| US4606865A (en) * | 1982-09-20 | 1986-08-19 | Astra Lakemedel Aktiebolag | Methods for the preparation of α-bromodiethylcarbonate |
| US4619785A (en) * | 1982-06-29 | 1986-10-28 | Astra Lakemedel Aktiebolag | Novel synthesis route for bacampicillin |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL68992A (en) * | 1982-06-29 | 1991-06-10 | Astra Laekemedel Ab | Alpha-bromo diethyl carbonate and process for the preparation of ethoxycarbonyloxy esters of penicillanic acids |
| US4916230A (en) * | 1984-07-02 | 1990-04-10 | Merck & Co., Inc. | Process for preparing novel N-(acyloxy-alkoxy)carbonyl derivatives useful as bioreversible prodrug moieties for primary and secondary amine functions in drugs |
| JPH066333B2 (en) * | 1986-07-21 | 1994-01-26 | 池田物産株式会社 | Method of manufacturing floor car pet for vehicle |
| ES2054502T3 (en) * | 1990-08-21 | 1994-08-01 | Glaxo Spa | ESTERS OF ACID 10- (1-HYDROXYETHYL) -11-OXO-1-AZATRICICLO (7.2.0.0 (3.8)) - UNDEC-2-EN-2-CARBOXILICO AND A PROCEDURE FOR ITS PREPARATION. |
| US6153135A (en) * | 1993-01-08 | 2000-11-28 | Novitsky; Charles | Method for producing vacuum insulating and construction material |
-
1972
- 1972-03-13 GB GB1168672A patent/GB1425571A/en not_active Expired
-
1973
- 1973-03-06 DE DE19732311005 patent/DE2311005A1/en active Pending
- 1973-03-12 AT AT213773A patent/AT330955B/en not_active IP Right Cessation
- 1973-03-12 JP JP48028903A patent/JPS4924988A/ja active Pending
- 1973-03-12 FR FR7308759A patent/FR2181813B1/fr not_active Expired
- 1973-03-12 AU AU53210/73A patent/AU5321073A/en not_active Expired
- 1973-03-13 NL NL7303484A patent/NL7303484A/xx unknown
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4048320A (en) * | 1975-01-17 | 1977-09-13 | Beecham Group Limited | Penicillins |
| GB2123821A (en) * | 1982-06-29 | 1984-02-08 | Astra Laekemedel Ab | ???-Halogeno diethyl carbonates and their use in the preparation of antibiotics |
| US4619785A (en) * | 1982-06-29 | 1986-10-28 | Astra Lakemedel Aktiebolag | Novel synthesis route for bacampicillin |
| US4606865A (en) * | 1982-09-20 | 1986-08-19 | Astra Lakemedel Aktiebolag | Methods for the preparation of α-bromodiethylcarbonate |
| US4820857A (en) * | 1982-09-20 | 1989-04-11 | Astra Lakemedel Aktiebolag | α-bromodiethylcarbonate |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2311005A1 (en) | 1973-10-31 |
| FR2181813A1 (en) | 1973-12-07 |
| FR2181813B1 (en) | 1976-12-03 |
| JPS4924988A (en) | 1974-03-05 |
| ATA213773A (en) | 1975-10-15 |
| AT330955B (en) | 1976-07-26 |
| AU5321073A (en) | 1974-09-12 |
| NL7303484A (en) | 1973-09-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |