GB1426717A - Penicillins - Google Patents
PenicillinsInfo
- Publication number
- GB1426717A GB1426717A GB1169272A GB1169272A GB1426717A GB 1426717 A GB1426717 A GB 1426717A GB 1169272 A GB1169272 A GB 1169272A GB 1169272 A GB1169272 A GB 1169272A GB 1426717 A GB1426717 A GB 1426717A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compound
- reacting
- formula
- acid
- defined above
- 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 6
- 150000002960 penicillins Chemical class 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 18
- -1 furfuryl Chemical group 0.000 abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 6
- 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 5
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 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 abstract 3
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 3
- 229910052736 halogen Chemical group 0.000 abstract 3
- 150000002367 halogens Chemical group 0.000 abstract 3
- 229940049954 penicillin Drugs 0.000 abstract 3
- RCNOGGGBSSVMAS-UHFFFAOYSA-N 2-thiophen-3-ylacetic acid Chemical compound OC(=O)CC=1C=CSC=1 RCNOGGGBSSVMAS-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 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
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 230000001851 biosynthetic effect Effects 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- 125000002541 furyl group Chemical group 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 229910052698 phosphorus Inorganic materials 0.000 abstract 2
- 239000011574 phosphorus Substances 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- DZWGARLOQIOXRG-UHFFFAOYSA-N (2-benzylthiophen-3-yl) acetate Chemical compound C(C)(=O)OC1=C(SC=C1)CC1=CC=CC=C1 DZWGARLOQIOXRG-UHFFFAOYSA-N 0.000 abstract 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 1
- PHYMAVMHBUVBON-UHFFFAOYSA-N [1-(1-chloroethyl)cyclopentyl] hydrogen carbonate Chemical compound CC(C1(CCCC1)OC(=O)O)Cl PHYMAVMHBUVBON-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 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
- NSJSJULNRQZOEU-UHFFFAOYSA-N benzyl n-(1-hydroxyethyl)-n-methylcarbamate Chemical compound CC(O)N(C)C(=O)OCC1=CC=CC=C1 NSJSJULNRQZOEU-UHFFFAOYSA-N 0.000 abstract 1
- 235000011089 carbon dioxide Nutrition 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 abstract 1
- JYWJULGYGOLCGW-UHFFFAOYSA-N chloromethyl chloroformate Chemical compound ClCOC(Cl)=O JYWJULGYGOLCGW-UHFFFAOYSA-N 0.000 abstract 1
- RTFGZMKXMSDULM-UHFFFAOYSA-N chloromethyl ethyl carbonate Chemical compound CCOC(=O)OCCl RTFGZMKXMSDULM-UHFFFAOYSA-N 0.000 abstract 1
- UCSVAARRMAMTIF-UHFFFAOYSA-N chloromethyl phenyl carbonate Chemical compound ClCOC(=O)OC1=CC=CC=C1 UCSVAARRMAMTIF-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- LMAWFMWCKHRTKK-UHFFFAOYSA-N ethoxycarbonyloxymethyl 2-thiophen-3-ylacetate Chemical compound C(C)OC(=O)OCOC(CC1=CSC=C1)=O LMAWFMWCKHRTKK-UHFFFAOYSA-N 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- HQNKGHHMBPHQNG-UHFFFAOYSA-N phenoxycarbonyloxymethyl 2-phenylacetate Chemical compound O(C1=CC=CC=C1)C(=O)OCOC(CC1=CC=CC=C1)=O HQNKGHHMBPHQNG-UHFFFAOYSA-N 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
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 125000004076 pyridyl group Chemical group 0.000 abstract 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical compound OC(=O)C(C(O)=O)C1=CC=CC=C1 WWYDYZMNFQIYPT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1169272A GB1426717A (en) | 1972-03-13 | 1972-03-13 | Penicillins |
| DE2312041A DE2312041A1 (de) | 1972-03-13 | 1973-03-10 | Penicilline, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel |
| FR7308754A FR2201870A1 (enrdf_load_stackoverflow) | 1972-03-13 | 1973-03-12 | |
| AU53209/73A AU5320973A (en) | 1972-03-13 | 1973-03-12 | Penicillins |
| JP48028906A JPS49289A (enrdf_load_stackoverflow) | 1972-03-13 | 1973-03-12 | |
| AT214273A AT332540B (de) | 1972-03-13 | 1973-03-12 | Verfahren zur herstellung neuer penicilline |
| NL7303489A NL7303489A (enrdf_load_stackoverflow) | 1972-03-13 | 1973-03-13 | |
| DK543774A DK543774A (enrdf_load_stackoverflow) | 1972-03-13 | 1974-10-17 | |
| NO750668A NO750668L (enrdf_load_stackoverflow) | 1972-03-13 | 1975-02-27 | |
| AT632575A AT332974B (de) | 1972-03-13 | 1975-08-14 | Verfahren zur herstellung neuer penicilline |
| SE7512141A SE7512141L (sv) | 1972-03-13 | 1975-10-30 | Nya organiska foreningar |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1169272A GB1426717A (en) | 1972-03-13 | 1972-03-13 | Penicillins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1426717A true GB1426717A (en) | 1976-03-03 |
Family
ID=9990955
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1169272A Expired GB1426717A (en) | 1972-03-13 | 1972-03-13 | Penicillins |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPS49289A (enrdf_load_stackoverflow) |
| AT (1) | AT332540B (enrdf_load_stackoverflow) |
| AU (1) | AU5320973A (enrdf_load_stackoverflow) |
| DE (1) | DE2312041A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2201870A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1426717A (enrdf_load_stackoverflow) |
| NL (1) | NL7303489A (enrdf_load_stackoverflow) |
| NO (1) | NO750668L (enrdf_load_stackoverflow) |
| SE (1) | SE7512141L (enrdf_load_stackoverflow) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323499A (en) | 1981-01-05 | 1982-04-06 | Pfizer Inc. | 6-(2-Aryl-2-(1,1-dioxopenicillanoyloxy-methoxycarbonyl)acetamido penicillanic acids |
| US4606865A (en) * | 1982-09-20 | 1986-08-19 | Astra Lakemedel Aktiebolag | Methods for the preparation of α-bromodiethylcarbonate |
| US4614829A (en) * | 1983-08-26 | 1986-09-30 | Societe Nationale Des Poudres Et Explosifs | Process for the preparation of α-chlorinated chloroformates |
| US4619785A (en) * | 1982-06-29 | 1986-10-28 | Astra Lakemedel Aktiebolag | Novel synthesis route for bacampicillin |
| US4960881A (en) * | 1984-02-16 | 1990-10-02 | Societe Nationale Des Poudres Et Explosifs | α-chlorinated carbonates, their method of manufacture and application in the protection of the amine functions of amino acids |
| WO2004067536A3 (en) * | 2003-01-28 | 2004-12-23 | Sandoz Ag | Carboxylic acid esters to improve bioavailability of pharmaceutical compounds |
| US7091197B2 (en) | 2002-08-23 | 2006-08-15 | Pfizer Inc. | Beta-lactamase inhibitor prodrug |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2482587A1 (fr) * | 1980-05-14 | 1981-11-20 | Poudres & Explosifs Ste Nale | Procede de synthese de chloroformiates a-chlores et nouveaux chloroformiates a-chlores |
| 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 |
| GB8400024D0 (en) * | 1984-01-03 | 1984-02-08 | Glaxo Group Ltd | Cephalosporin antibiotics |
| FR2559766B1 (fr) * | 1984-02-16 | 1986-05-16 | Poudres & Explosifs Ste Nale | Procede de preparation de derives de l'acide carbamique |
| 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 |
-
1972
- 1972-03-13 GB GB1169272A patent/GB1426717A/en not_active Expired
-
1973
- 1973-03-10 DE DE2312041A patent/DE2312041A1/de active Pending
- 1973-03-12 AT AT214273A patent/AT332540B/de not_active IP Right Cessation
- 1973-03-12 JP JP48028906A patent/JPS49289A/ja active Pending
- 1973-03-12 AU AU53209/73A patent/AU5320973A/en not_active Expired
- 1973-03-12 FR FR7308754A patent/FR2201870A1/fr not_active Withdrawn
- 1973-03-13 NL NL7303489A patent/NL7303489A/xx unknown
-
1975
- 1975-02-27 NO NO750668A patent/NO750668L/no unknown
- 1975-10-30 SE SE7512141A patent/SE7512141L/ not_active Application Discontinuation
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4323499A (en) | 1981-01-05 | 1982-04-06 | Pfizer Inc. | 6-(2-Aryl-2-(1,1-dioxopenicillanoyloxy-methoxycarbonyl)acetamido penicillanic acids |
| 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 |
| US4614829A (en) * | 1983-08-26 | 1986-09-30 | Societe Nationale Des Poudres Et Explosifs | Process for the preparation of α-chlorinated chloroformates |
| US4960881A (en) * | 1984-02-16 | 1990-10-02 | Societe Nationale Des Poudres Et Explosifs | α-chlorinated carbonates, their method of manufacture and application in the protection of the amine functions of amino acids |
| US7091197B2 (en) | 2002-08-23 | 2006-08-15 | Pfizer Inc. | Beta-lactamase inhibitor prodrug |
| WO2004067536A3 (en) * | 2003-01-28 | 2004-12-23 | Sandoz Ag | Carboxylic acid esters to improve bioavailability of pharmaceutical compounds |
Also Published As
| Publication number | Publication date |
|---|---|
| NL7303489A (enrdf_load_stackoverflow) | 1973-09-17 |
| NO750668L (enrdf_load_stackoverflow) | 1973-09-14 |
| AT332540B (de) | 1976-10-11 |
| AU5320973A (en) | 1974-09-12 |
| FR2201870A1 (enrdf_load_stackoverflow) | 1974-05-03 |
| ATA214273A (de) | 1976-01-15 |
| DE2312041A1 (de) | 1973-10-11 |
| JPS49289A (enrdf_load_stackoverflow) | 1974-01-05 |
| SE7512141L (sv) | 1975-10-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |