GB1426869A - Penicillins - Google Patents
PenicillinsInfo
- Publication number
- GB1426869A GB1426869A GB1168772A GB1168772A GB1426869A GB 1426869 A GB1426869 A GB 1426869A GB 1168772 A GB1168772 A GB 1168772A GB 1168772 A GB1168772 A GB 1168772A GB 1426869 A GB1426869 A GB 1426869A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- compound
- defined above
- group
- reacting
- 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 2
- 150000001875 compounds Chemical class 0.000 abstract 8
- -1 amino, methoxy, hydroxy halogen Chemical group 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 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 abstract 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000002252 acyl 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
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 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
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000001624 naphthyl group Chemical group 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 1
- 150000002894 organic compounds Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical class CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001544 thienyl group Chemical group 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
-
- 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)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1426869 Organic compounds ASTRA LAKEMEDEL AB 12 March 1973 [13 March 1972] 11687/72 Heading C2C [Also in Division A5] Novel penicillins of Formula I and therapeutically acceptable salts thereof wherein R<SP>1</SP> is phenyl, naphthyl, phenoxy or a heterocyclic group, such groups being optionally substituted with one or more amino, methoxy, hydroxy halogen or phenyl groups; R<SP>3</SP> is H or CH 3 ; R<SP>4</SP> is C 1 -C 8 alkyl, C 3 -C 7 cycloalkyl, phenyl or benzyl, such groups being optionally substituted with one or more azido, amino, substituted amino, nitro or C 1 -C 4 alkoxy groups; X is H, azido or hydroxy; and n is 0 or 1; provided that X is not H or azido when n is 1, R<SP>4</SP> is an unsubstituted C 1 -C 8 alkyl group and R<SP>1</SP> is thienyl, furyl, phenyl or hydroxy and/or halogen-substituted phenyl, are prepared (a) by reacting a compound of formula wherein R<SP>1</SP>' is R<SP>1</SP> as defined above or a protected R<SP>1</SP> group, X<SP>1</SP> is X as defined above or a protected X group; n is 0 or 1 and -COZ is an acid chloride or equivalent group, with a compound of formula wherein R<SP>3</SP> and R<SP>4</SP> are as defined above and, if necessary, removing the protecting groups; or (b) by reacting a natural penicillin of Formula X wherein R.CO is the acyl group of the natural penicillin and M is H or an alkali metal cation, with a compound of formula wherein R<SP>3</SP> and R<SP>4</SP> are as defined above and Y<SP>1</SP> is halogen or an equivalent group to form an ester of formula wherein RCO, R<SP>3</SP> and R<SP>4</SP> are as defined above, which ester is reacted with a phosphorus halide, reacting the resulting imino halide with an alcohol and reacting the resulting imino ether with a compound of formula wherein R<SP>1</SP>', X<SP>1</SP>, n and -COZ are as defined above, and, if necessary, removing the protecting groups; or (c) by reacting a compound of formula wherein n is 0 or 1, and R<SP>1</SP>' and X<SP>1</SP> are as defined above with a compound of formula wherein Y<SP>1</SP> is halogen or an equivalent group and R<SP>3</SP> and R<SP>4</SP> are as defined above. The compound X may be in the form of its tetrabutylammonium salt. Pharmaceutical compositions comprise a compound of Formula I or a therapeutically acceptable salt thereof with a pharmaceutically acceptable diluent. Other antibiotics may be present in the compositions (see Division A5).
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1168772A GB1426869A (en) | 1972-03-13 | 1972-03-13 | Penicillins |
| DE19732311346 DE2311346A1 (en) | 1972-03-13 | 1973-03-08 | PENICILLIN AND METHOD FOR MANUFACTURING THEREOF |
| JP48028905A JPS49288A (en) | 1972-03-13 | 1973-03-12 | |
| AT213873A AT325203B (en) | 1972-03-13 | 1973-03-12 | METHOD OF MANUFACTURING NEW PENICILLINES |
| CA165,830A CA1029011A (en) | 1972-03-13 | 1973-03-12 | ESTERS OF .alpha.-SUBSTITUTED ACETAMINOPENICILLANIC ACIDS |
| AT770674A AT325774B (en) | 1972-03-13 | 1973-03-12 | METHOD OF MANUFACTURING NEW PENICILLINES |
| NL7303435A NL7303435A (en) | 1972-03-13 | 1973-03-12 | |
| FR7308758A FR2181812B1 (en) | 1972-03-13 | 1973-03-12 | |
| AU53211/73A AU484047B2 (en) | 1972-03-13 | 1973-03-12 | Penicillins |
| CH366773A CH590869A5 (en) | 1972-03-13 | 1973-03-13 | |
| US05/504,177 US3980793A (en) | 1972-03-13 | 1974-09-09 | Carbonate esters of penicillins and compositions and methods for treatment of bacterial infections |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1168772A GB1426869A (en) | 1972-03-13 | 1972-03-13 | Penicillins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1426869A true GB1426869A (en) | 1976-03-03 |
Family
ID=9990848
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1168772A Expired GB1426869A (en) | 1972-03-13 | 1972-03-13 | Penicillins |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS49288A (en) |
| AT (2) | AT325203B (en) |
| CA (1) | CA1029011A (en) |
| CH (1) | CH590869A5 (en) |
| DE (1) | DE2311346A1 (en) |
| FR (1) | FR2181812B1 (en) |
| GB (1) | GB1426869A (en) |
| NL (1) | NL7303435A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2123821A (en) * | 1982-06-29 | 1984-02-08 | Astra Laekemedel Ab | ???-Halogeno diethyl carbonates and their use in the preparation of antibiotics |
| GB2168050A (en) * | 1982-06-29 | 1986-06-11 | Astra Laekemedel Ab | Intermediates useful 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 (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7401782A (en) * | 1973-02-14 | 1974-08-16 | ||
| US8846723B2 (en) | 2010-07-29 | 2014-09-30 | Eastman Chemical Company | Esters of O-substituted hydroxy carboxylic acids and preparations thereof |
| US8613940B2 (en) * | 2010-09-03 | 2013-12-24 | Eastman Chemical Company | Carbonate derivatives as skin care |
| US8329938B2 (en) | 2011-02-21 | 2012-12-11 | Eastman Chemical Company | Hydroxyalkanoic acid and hydroxyalkanoice acid oligomer esters of retinol |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3873521A (en) * | 1970-09-17 | 1975-03-25 | Astra Laekemedel Ab | Esters of {60 -amino penicillins |
-
1972
- 1972-03-13 GB GB1168772A patent/GB1426869A/en not_active Expired
-
1973
- 1973-03-08 DE DE19732311346 patent/DE2311346A1/en active Pending
- 1973-03-12 NL NL7303435A patent/NL7303435A/xx unknown
- 1973-03-12 AT AT213873A patent/AT325203B/en not_active IP Right Cessation
- 1973-03-12 JP JP48028905A patent/JPS49288A/ja active Pending
- 1973-03-12 AT AT770674A patent/AT325774B/en not_active IP Right Cessation
- 1973-03-12 FR FR7308758A patent/FR2181812B1/fr not_active Expired
- 1973-03-12 CA CA165,830A patent/CA1029011A/en not_active Expired
- 1973-03-13 CH CH366773A patent/CH590869A5/xx not_active IP Right Cessation
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2123821A (en) * | 1982-06-29 | 1984-02-08 | Astra Laekemedel Ab | ???-Halogeno diethyl carbonates and their use in the preparation of antibiotics |
| GB2168050A (en) * | 1982-06-29 | 1986-06-11 | Astra Laekemedel Ab | Intermediates useful in the preparation of antibiotics |
| GB2168699A (en) * | 1982-06-29 | 1986-06-25 | Astra Laekemedel Ab | alpha -Bromodiethyl carbonate and its 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 |
|---|---|
| CH590869A5 (en) | 1977-08-31 |
| CA1029011A (en) | 1978-04-04 |
| FR2181812B1 (en) | 1976-12-03 |
| AT325774B (en) | 1975-11-10 |
| DE2311346A1 (en) | 1973-10-25 |
| NL7303435A (en) | 1973-09-17 |
| JPS49288A (en) | 1974-01-05 |
| AU5321173A (en) | 1974-09-12 |
| FR2181812A1 (en) | 1973-12-07 |
| AT325203B (en) | 1975-10-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |