GB1072108A - Penicillanic acid, its salts and esters - Google Patents
Penicillanic acid, its salts and estersInfo
- Publication number
- GB1072108A GB1072108A GB2194364A GB2194364A GB1072108A GB 1072108 A GB1072108 A GB 1072108A GB 2194364 A GB2194364 A GB 2194364A GB 2194364 A GB2194364 A GB 2194364A GB 1072108 A GB1072108 A GB 1072108A
- Authority
- GB
- United Kingdom
- Prior art keywords
- treatment
- salts
- esters
- penicillanic acid
- derivatives
- 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
- 150000002148 esters Chemical class 0.000 title abstract 4
- 150000003839 salts Chemical class 0.000 title abstract 4
- 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 3
- 150000001299 aldehydes Chemical class 0.000 abstract 2
- 150000002576 ketones Chemical class 0.000 abstract 2
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 abstract 1
- 229930182555 Penicillin Natural products 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- -1 acyl anhydride Chemical class 0.000 abstract 1
- 150000001266 acyl halides Chemical class 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000012954 diazonium Substances 0.000 abstract 1
- 150000001989 diazonium salts Chemical class 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 150000002960 penicillins Chemical class 0.000 abstract 1
- 150000003141 primary amines Chemical class 0.000 abstract 1
- 150000003335 secondary amines Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention relates to penicillanic acid having the formula <FORM:1072108/C2/1> its salts and esters. These compounds are prepared by hydrogenation, particularly catalytic hydrogenation, of a 6-halopenicillanic acid, or a salt or ester thereof of formula <FORM:1072108/C2/2> where Hal is chloro, bromo or iodo and M is H, a cation, alkyl or aryl. Penicillanic acid, its salts and esters are converted to (a) penicillins by treatment with an acyl halide or acyl anhydride, (b) 6-azo derivatives by treatment with diazonium salts, (c) 6-alkyl and 6-aryl derivatives by treatment with a reactive halide, (d) 6-alkylidene and 6-arylidene derivatives by treatment with ketones and aldehydes and (e) Mannich bases by treatment with aldehydes and ketones in the presence of primary or secondary amines.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US28395463A | 1963-05-29 | 1963-05-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1072108A true GB1072108A (en) | 1967-06-14 |
Family
ID=23088289
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2194364A Expired GB1072108A (en) | 1963-05-29 | 1964-05-27 | Penicillanic acid, its salts and esters |
Country Status (2)
| Country | Link |
|---|---|
| BE (1) | BE648188A (en) |
| GB (1) | GB1072108A (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2405950A1 (en) * | 1977-05-09 | 1979-05-11 | Ciba Geigy Ag | NEW 1 PENICILLANIC ACID OXIDES USEFUL IN THE SYNTHESIS OF DRUGS |
| US4234579A (en) * | 1977-06-07 | 1980-11-18 | Pfizer Inc. | Penicillanic acid 1,1-dioxides as β-lactamase inhibitors |
| US4241050A (en) * | 1978-09-01 | 1980-12-23 | Pfizer Inc. | Penam 1,1-dioxides as beta-lactamase inhibitors |
| US4256733A (en) | 1979-09-26 | 1981-03-17 | Pfizer Inc. | Acetoxymethyl penam compounds as β-lactamase inhibitors |
| US4276285A (en) * | 1977-06-07 | 1981-06-30 | Pfizer Inc. | Combinations of penicillanic acid 1,1-dioxide with 7-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-[4-hydroxyphenyl]acetamido)-3-([1-methyl-5-tetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid |
| US4340539A (en) | 1980-01-21 | 1982-07-20 | Bristol-Myers Company | Derivatives of 6-bromo penicillanic acid |
| US4420426A (en) | 1979-03-05 | 1983-12-13 | Pfizer Inc. | 6-Alpha-halopenicillanic acid 1,1-dioxides |
| US4714761A (en) * | 1979-03-05 | 1987-12-22 | Pfizer Inc. | 6,6-dihalopenicillanic acid 1,1-dioxides and process |
-
1964
- 1964-05-21 BE BE648188D patent/BE648188A/xx unknown
- 1964-05-27 GB GB2194364A patent/GB1072108A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2405950A1 (en) * | 1977-05-09 | 1979-05-11 | Ciba Geigy Ag | NEW 1 PENICILLANIC ACID OXIDES USEFUL IN THE SYNTHESIS OF DRUGS |
| US4331676A (en) | 1977-05-09 | 1982-05-25 | Ciba-Geigy Corporation | Thia-aza compounds with a β-lactam ring |
| US4234579A (en) * | 1977-06-07 | 1980-11-18 | Pfizer Inc. | Penicillanic acid 1,1-dioxides as β-lactamase inhibitors |
| US4276285A (en) * | 1977-06-07 | 1981-06-30 | Pfizer Inc. | Combinations of penicillanic acid 1,1-dioxide with 7-(D-2-[4-ethylpiperazin-2,3-dione-1-carboxamido]-2-[4-hydroxyphenyl]acetamido)-3-([1-methyl-5-tetrazolyl]thiomethyl)-3-desacetoxymethylcephalosporanic acid |
| US4241050A (en) * | 1978-09-01 | 1980-12-23 | Pfizer Inc. | Penam 1,1-dioxides as beta-lactamase inhibitors |
| US4420426A (en) | 1979-03-05 | 1983-12-13 | Pfizer Inc. | 6-Alpha-halopenicillanic acid 1,1-dioxides |
| US4714761A (en) * | 1979-03-05 | 1987-12-22 | Pfizer Inc. | 6,6-dihalopenicillanic acid 1,1-dioxides and process |
| US4256733A (en) | 1979-09-26 | 1981-03-17 | Pfizer Inc. | Acetoxymethyl penam compounds as β-lactamase inhibitors |
| US4340539A (en) | 1980-01-21 | 1982-07-20 | Bristol-Myers Company | Derivatives of 6-bromo penicillanic acid |
Also Published As
| Publication number | Publication date |
|---|---|
| BE648188A (en) | 1964-09-16 |
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