GB1390754A - Penicillin and cephalosporin esters - Google Patents
Penicillin and cephalosporin estersInfo
- Publication number
- GB1390754A GB1390754A GB534574A GB534574A GB1390754A GB 1390754 A GB1390754 A GB 1390754A GB 534574 A GB534574 A GB 534574A GB 534574 A GB534574 A GB 534574A GB 1390754 A GB1390754 A GB 1390754A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- group
- reacting
- prepared
- compound
- 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
- 229930186147 Cephalosporin Natural products 0.000 title abstract 2
- 229930182555 Penicillin Natural products 0.000 title abstract 2
- 229940124587 cephalosporin Drugs 0.000 title 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 title 1
- -1 cephalosporin esters Chemical class 0.000 title 1
- 229940049954 penicillin Drugs 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 7
- 125000003277 amino group Chemical group 0.000 abstract 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 abstract 2
- 239000002253 acid Substances 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 abstract 2
- GQSKFTFPHAXZSA-UHFFFAOYSA-N 3-bromo-2h-furan-5-one Chemical compound BrC1=CC(=O)OC1 GQSKFTFPHAXZSA-UHFFFAOYSA-N 0.000 abstract 1
- PEQYBEMGRNDODV-UHFFFAOYSA-N 4-chloro-4-methyloxolan-2-one Chemical compound ClC1(CC(=O)OC1)C PEQYBEMGRNDODV-UHFFFAOYSA-N 0.000 abstract 1
- 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 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 abstract 1
- HSHGZXNAXBPPDL-HZGVNTEJSA-N 7beta-aminocephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C([O-])=O)N2C(=O)[C@@H]([NH3+])[C@@H]12 HSHGZXNAXBPPDL-HZGVNTEJSA-N 0.000 abstract 1
- NVIAYEIXYQCDAN-CLZZGJSISA-N 7beta-aminodeacetoxycephalosporanic acid Chemical compound S1CC(C)=C(C(O)=O)N2C(=O)[C@@H](N)[C@@H]12 NVIAYEIXYQCDAN-CLZZGJSISA-N 0.000 abstract 1
- 239000004215 Carbon black (E152) Substances 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 238000006136 alcoholysis reaction Methods 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- VIHAEDVKXSOUAT-UHFFFAOYSA-N but-2-en-4-olide Chemical compound O=C1OCC=C1 VIHAEDVKXSOUAT-UHFFFAOYSA-N 0.000 abstract 1
- 150000001780 cephalosporins Chemical class 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 230000007935 neutral effect Effects 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000001424 substituent 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)
Abstract
1390754 Penicillins and cephalosporins BEECHAM GROUP Ltd 23 June 1972 [9 June 1971] 05345/74 Divided out of 1377817 Heading C2C Novel compounds of Formula I and pharmaceutically acceptable acid addition salts of those compounds which contain a basic nitrogen atom wherein X and Y are the same or different and each represents oxygen or sulphur, Z represents a straight or branched, saturated or unsaturated divalent hydrocarbon radical which may be interrupted by a hetero atom, R represents hydrogen or an alkyl, alkenyl, alkynyl, aryl or aralkyl group or a functional substituent, A represents a group of Formula II or III wherein B represents hydrogen or an acetoxy group and R<SP>1</SP> is an organic acylamino group may be prepared (1) by reacting a compound of Formula IX or a reactive esterifying derivative thereof, in which formula A is as defined with respect to Formula I, with a compound of Formula X or a reactive esterifying derivative thereof, in which X, Y, Z and R are as above defined or (2) by reacting a compound of Formula XIII or a silyl derivative thereof wherein H 2 NQ- represents a 6-amino penam-3, a 7-amino-3- methylceph-3-em-4 or a 7-amino-3-acetoxymethylceph-3-em-4 radical and R, X, Y and Z are as above defined with a reactive N-acylating derivative of a compound of Formula XIV wherein R<SP>1</SP>a is an organic acyl group which may carry a protected amino group, removing the silyl group, if present, by hydrolysis or alcoholysis, and if a protected amino group is present, optionally converting it to a free amino group under acid or neutral conditions. The esters of Formula XIII are stated to be novel and may be prepared by reacting 6-aminopenicillanic acid, 7-aminocephalosporanic or 7-aminodesacetoxycephalosporanic acid or N- protected derivatives thereof with the appropriate 3-bromolactone and thereafter removing the protecting group, if present. Crotoriolactone and 3-chloro-3-methyl butyrolactone are prepared by known methods. 3-Bromocrotonolactone is prepared by reacting crotonolactone with N-bromo succinimide and azoisobutyronitrile. Pharmaceutical compositions having antibacterial activity, preferably for oral administration, comprise the compounds of Formula I and a pharmaceutically acceptable carrier.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB534574A GB1390754A (en) | 1971-06-09 | 1971-06-09 | Penicillin and cephalosporin esters |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2943172A GB1377817A (en) | 1971-06-09 | 1971-06-09 | Penicillins and cephalosporins |
| GB1960471A GB1364672A (en) | 1971-06-09 | 1971-06-09 | Penicillins |
| GB534574A GB1390754A (en) | 1971-06-09 | 1971-06-09 | Penicillin and cephalosporin esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1390754A true GB1390754A (en) | 1975-04-16 |
Family
ID=27254615
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB534574A Expired GB1390754A (en) | 1971-06-09 | 1971-06-09 | Penicillin and cephalosporin esters |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1390754A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039086A3 (en) * | 1980-04-30 | 1982-02-10 | Kanebo Ltd. | Novel ampicillin esters and production thereof |
| EP0069962A1 (en) * | 1981-07-15 | 1983-01-19 | Kanebo, Ltd. | Novel ester of 1,1-dioxopenicillanic acid, process for production thereof, and use thereof as beta-lactamase inhibitor |
| EP0070477A1 (en) * | 1981-07-18 | 1983-01-26 | Kanebo, Ltd. | Novel ester of 6-((hexahydro-1H-azepin-1-yl)methyleneamino)penicillanic acid, process for its production, and its use as antibacterial agent |
| US4619785A (en) * | 1982-06-29 | 1986-10-28 | Astra Lakemedel Aktiebolag | Novel synthesis route for bacampicillin |
-
1971
- 1971-06-09 GB GB534574A patent/GB1390754A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039086A3 (en) * | 1980-04-30 | 1982-02-10 | Kanebo Ltd. | Novel ampicillin esters and production thereof |
| EP0061206A1 (en) * | 1980-04-30 | 1982-09-29 | Kanebo, Ltd. | 6-Aminopenicillanic acid esters and their use for producing new ampicillin esters |
| EP0069962A1 (en) * | 1981-07-15 | 1983-01-19 | Kanebo, Ltd. | Novel ester of 1,1-dioxopenicillanic acid, process for production thereof, and use thereof as beta-lactamase inhibitor |
| EP0070477A1 (en) * | 1981-07-18 | 1983-01-26 | Kanebo, Ltd. | Novel ester of 6-((hexahydro-1H-azepin-1-yl)methyleneamino)penicillanic acid, process for its production, and its use as antibacterial agent |
| US4619785A (en) * | 1982-06-29 | 1986-10-28 | Astra Lakemedel Aktiebolag | Novel synthesis route for bacampicillin |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SP | Amendment (slips) printed | ||
| PCNP | Patent ceased through non-payment of renewal fee |