GB1464377A - Penicillanic and cephalosporanic acid derivatives - Google Patents
Penicillanic and cephalosporanic acid derivativesInfo
- Publication number
- GB1464377A GB1464377A GB1018973A GB1018973A GB1464377A GB 1464377 A GB1464377 A GB 1464377A GB 1018973 A GB1018973 A GB 1018973A GB 1018973 A GB1018973 A GB 1018973A GB 1464377 A GB1464377 A GB 1464377A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- formula
- group
- ester
- penicillanic
- 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
- RBKMMJSQKNKNEV-RITPCOANSA-N penicillanic acid Chemical compound OC(=O)[C@H]1C(C)(C)S[C@@H]2CC(=O)N21 RBKMMJSQKNKNEV-RITPCOANSA-N 0.000 title abstract 2
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical class S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 title 1
- 239000002253 acid Substances 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000002148 esters Chemical group 0.000 abstract 4
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- 230000000844 anti-bacterial effect Effects 0.000 abstract 2
- -1 azido, carbamoyloxy Chemical group 0.000 abstract 2
- 150000001768 cations Chemical class 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 125000000842 isoxazolyl group Chemical group 0.000 abstract 2
- 229910052751 metal Inorganic materials 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- CFGDUGSIBUXRMR-UHFFFAOYSA-N 1,2-dihydropyrrol-2-ide Chemical compound C=1C=[C-]NC=1 CFGDUGSIBUXRMR-UHFFFAOYSA-N 0.000 abstract 1
- LQUMUKHHUVGAQC-UHFFFAOYSA-N 2-(3-chloro-1,2-oxazol-5-yl)acetic acid Chemical compound OC(=O)CC1=CC(Cl)=NO1 LQUMUKHHUVGAQC-UHFFFAOYSA-N 0.000 abstract 1
- HAIYJMDKRRQFAJ-UHFFFAOYSA-N 3-chloro-5-methyl-1,2-oxazole Chemical compound CC1=CC(Cl)=NO1 HAIYJMDKRRQFAJ-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
- 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
- ATTZFSUZZUNHBP-UHFFFAOYSA-N Piperonyl sulfoxide Chemical compound CCCCCCCCS(=O)C(C)CC1=CC=C2OCOC2=C1 ATTZFSUZZUNHBP-UHFFFAOYSA-N 0.000 abstract 1
- 150000008065 acid anhydrides Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- 150000001540 azides Chemical class 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 150000001718 carbodiimides Chemical class 0.000 abstract 1
- 239000001569 carbon dioxide Substances 0.000 abstract 1
- 229910002092 carbon dioxide Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 230000000249 desinfective effect Effects 0.000 abstract 1
- 201000011243 gastrointestinal stromal tumor Diseases 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000002883 imidazolyl group Chemical group 0.000 abstract 1
- 230000000269 nucleophilic effect Effects 0.000 abstract 1
- 125000001715 oxadiazolyl group Chemical group 0.000 abstract 1
- 239000000546 pharmaceutical excipient 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 230000001681 protective effect Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical group OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 abstract 1
- 125000003831 tetrazolyl group Chemical group 0.000 abstract 1
- 125000001113 thiadiazolyl group Chemical group 0.000 abstract 1
- 150000007970 thio esters Chemical class 0.000 abstract 1
- 238000005406 washing Methods 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
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1464377 Isoxazolyl penicillanic and cephalosporanic derivatives GIST-BROCADES NV 1 March 1974 [2 March 1973 15 Jan 1974] 10189/73 and 01836/74 Addition to 1364453 Heading C2C Novel compounds of the Formula (I) in which the symbol Q represents the group wherein X denotes H, OH or alkanoyl or the residue of a nucleophilic agent such as azido, carbamoyloxy, or -SZ, where Z is a tetrazolyl, thiadiazolyl, oxadiazolyl, isoxazolyl, or imidazolyl group, optionally carrying lower alkyl groups; R is -OH or -OCH 3 , Cl or Br; R<SP>1</SP> is H, Cl or Br; R<SP>2</SP> is H, Cl, Br, or amino, C 1-6 alkoxycarbamylamino, phenyl (C 1-6 ) alkoxycarbonylamino, (optionally having p-methoxy or p-nitro substituted) or a sulphonic acid group optionally transformed into an alkali metal, alkaline earth metal or amine salt, or R<SP>2</SP> represents a carbamoyl group, and E denotes a H atom, a salt-forming cation, or a pharmaceutically-acceptable ester residue, can be obtained (A) by reacting a 6-aminopenicillanic or 7- aminocephalosporanic acid containing structures of Formulµ II, III and IV, in (which X may also represent a protected group which can be easily converted to X as above and E represents an easily removable protective ester residue) with an active ester, acid halide, acid anhydride, acid azide, active thio ester or azolide, derived from an acid of Formula (VIII) where R* and R<SP>2</SP>* are as defined for R and R<SP>2</SP> or are groups which may be easily converted into R and R<SP>2</SP>, or with an acid of Formula VIII in the presence of a carbodiimide, or (B) reacting an ester of 6-isocyanto-penicillanic acid or a 7-isocyanato-cephalosporanic acid derivative with (i) an acid of general Formula VIII in an inert organic solvent medium, or (ii) an organometal compound A-Me<SP>I</SP> or A-Me<SP>II</SP>-Hal, where A is a group of general formula Me is a metal atom (I and II representing its valency) and Hal denotes halogen, in an anhydrous organic solvent under conditions favouring a reaction of Grignard, Reformatsky or analogous type, and removing the metal residue from the product, or (C) heating a penicillanic acid sulphoxide of formula where Q<SP>11</SP> is a group of Formula (IV) or of the formula and E is H or a salt forming cation, up to 160 degrees in the presence of a suitable catalyst, optionally followed by conversion of the product to other derivatives included above. 3 - Chloro - isoxazole - 5 - yl - acetic acid is prepared by reacting 3-chloro-5-methylisoxazole with n-butyl-lithium and carbon dioxide. Antibacterial compositions comprise a bactericidal amount of one or more compounds of Formula (I) in association with a physiologically acceptable carrier or excipient, and can be administered topically, orally or parenterally. Disinfecting compositions comprises compounds of Formula (I) in association with a suitable inert carrier for application by washing or spraying.
Priority Applications (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1018973A GB1464377A (en) | 1973-03-02 | 1973-03-02 | Penicillanic and cephalosporanic acid derivatives |
| BE141582A BE811798A (en) | 1973-03-02 | 1974-03-01 | NEW ACIDS AND DERIVATIVES OF PENICILLANIC AND CEPHALOSPORANIC ACIDS |
| AU66202/74A AU6620274A (en) | 1973-03-02 | 1974-03-01 | Penicillanic and cephalosporanic acid derivatives |
| NL7402778A NL7402778A (en) | 1973-03-02 | 1974-03-01 | |
| DE2409949A DE2409949A1 (en) | 1973-03-02 | 1974-03-01 | PENICILLANIC ACID AND CEPHALOSPORIC ACID DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND ANTIBACTERICIDAL PREPARATIONS CONTAINING THESE COMPOUNDS |
| FR7407098A FR2219775A1 (en) | 1973-03-02 | 1974-03-01 | Isoxazolylacetamido penicillanic and cephalosporanic acids - partic. active against Gram-positive bacteria |
| ES423827A ES423827A1 (en) | 1973-03-02 | 1974-03-02 | Procedure for preparing derivatives of penicilanico and cefalosporanic acids. (Machine-translation by Google Translate, not legally binding) |
| ES423828A ES423828A1 (en) | 1973-03-02 | 1974-03-02 | Procedure for preparing derivatives of aminopenicilanico 6-substitute acids and aminocephalosparanico 7-substitute. (Machine-translation by Google Translate, not legally binding) |
| JP49024712A JPS5029591A (en) | 1973-03-02 | 1974-03-02 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1018973A GB1464377A (en) | 1973-03-02 | 1973-03-02 | Penicillanic and cephalosporanic acid derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1464377A true GB1464377A (en) | 1977-02-09 |
Family
ID=9963200
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1018973A Expired GB1464377A (en) | 1973-03-02 | 1973-03-02 | Penicillanic and cephalosporanic acid derivatives |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE811798A (en) |
| GB (1) | GB1464377A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4394504A (en) | 1981-10-07 | 1983-07-19 | American Home Products Corporation | Cephalosporin derivatives |
| EP0219990A1 (en) * | 1985-09-26 | 1987-04-29 | Biogal Gyogyszergyar | Process for the preparation of 3-chloro-5-isoxazoleacetic acid |
-
1973
- 1973-03-02 GB GB1018973A patent/GB1464377A/en not_active Expired
-
1974
- 1974-03-01 BE BE141582A patent/BE811798A/en unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4394504A (en) | 1981-10-07 | 1983-07-19 | American Home Products Corporation | Cephalosporin derivatives |
| EP0219990A1 (en) * | 1985-09-26 | 1987-04-29 | Biogal Gyogyszergyar | Process for the preparation of 3-chloro-5-isoxazoleacetic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| BE811798A (en) | 1974-09-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |