ES385834A1 - [NOVEL] ESTERS OF alpha-CARBOXYBENZYLPENCILLIN - Google Patents
[NOVEL] ESTERS OF alpha-CARBOXYBENZYLPENCILLINInfo
- Publication number
- ES385834A1 ES385834A1 ES385834A ES385834A ES385834A1 ES 385834 A1 ES385834 A1 ES 385834A1 ES 385834 A ES385834 A ES 385834A ES 385834 A ES385834 A ES 385834A ES 385834 A1 ES385834 A1 ES 385834A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- formula
- alcohol
- phenylalkyl
- alcoholylthio
- 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
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- 125000003884 phenylalkyl group Chemical group 0.000 abstract 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 3
- 229910052794 bromium Inorganic materials 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 239000000460 chlorine Substances 0.000 abstract 3
- 229910052731 fluorine Inorganic materials 0.000 abstract 3
- 239000011737 fluorine Substances 0.000 abstract 3
- 125000001424 substituent group Chemical group 0.000 abstract 3
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- CZGCEKJOLUNIFY-UHFFFAOYSA-N 4-Chloronitrobenzene Chemical group [O-][N+](=O)C1=CC=C(Cl)C=C1 CZGCEKJOLUNIFY-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- -1 N, N-di- (n-propyl) -sulfamyl Chemical group 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 125000005083 alkoxyalkoxy group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 229960003669 carbenicillin Drugs 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- WWYDYZMNFQIYPT-UHFFFAOYSA-N ru78191 Chemical class 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
- 229910052717 sulfur Inorganic materials 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
Abstract
A procedure for preparing α-carboxybenzylpenicillin monoesters having the formula and the pharmaceutically acceptable salts thereof, where: R1 is (1) hydrogen, (2) alcohol, alkoxyalkoxy, and alcoholylthioalcoyl, each containing up to 6 carbon atoms. (3) cycloalkoxy of 3 to 6 carbon atoms, or (4) mono- and disubstituted phenylalkyl or phenylalkyl wherein said substituent is alcohol containing up to 3 carbon atoms, chlorine, bromine, fluorine or alkoxy and alcoholylthio each containing up to 2 carbon atoms; and R3 is (1) alcohol of up to 6 carbon atoms, (2) cycloaicoyl of 3 to 8 carbon atoms, (3) phenyl, phenylalkyl and mono- and disubstituted phenyl and phenylalkyl where said portion of alcohol is composed of 1 to 3 carbon atoms and each of said substituents is chlorine, bromine, fluorine, alkoxy or alcoholylthio each of which has up to 2 carbon atoms, trifluoromethyl or N, N-di- (n-propyl) -sulfamyl, (4) phenylheteroalcoyl and substituted phenylheteroalcoyl of the formula: **(See formula)** where the substituents X1 and X2 are each hydrogen, chlorine, bromine, fluorine, alcohol containing up to 3 carbon atoms, and alkoxy or alcoholylthio each having up to 2 carbon atoms, Z is O or S and p is an integer from 1 to 3, characterized by the fact that a 6-aminopenicyllanic acid ester of the formula is acylated **(See formula)** wherein R1 and R3 are as previously defined, with an activated phenylmalonic acid of the formula Ø (COOH) CO-Act wherein Act represents p-nitrophenyl chloride, anhydride, or ester. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US88039569A | 1969-11-26 | 1969-11-26 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES385834A1 true ES385834A1 (en) | 1973-12-16 |
Family
ID=25376176
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES385834A Expired ES385834A1 (en) | 1969-11-26 | 1970-11-24 | [NOVEL] ESTERS OF alpha-CARBOXYBENZYLPENCILLIN |
| ES414805A Expired ES414805A1 (en) | 1969-11-26 | 1973-05-16 | A PROCEDURE TO PREPARE MONOSTERS OF ALPHA-CARBOXY-BENZYLPENICILLIN. |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES414805A Expired ES414805A1 (en) | 1969-11-26 | 1973-05-16 | A PROCEDURE TO PREPARE MONOSTERS OF ALPHA-CARBOXY-BENZYLPENICILLIN. |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS518956B1 (en) |
| BE (1) | BE759498A (en) |
| DE (1) | DE2058110C3 (en) |
| ES (2) | ES385834A1 (en) |
| FR (1) | FR2073418B1 (en) |
| GB (2) | GB1294028A (en) |
| SE (1) | SE380025B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3862933A (en) * | 1972-07-12 | 1975-01-28 | Pfizer | Process for making esters of 6-(alpha-(carboxy)aryla-cetamido)penicillanic acids |
| HU168914B (en) * | 1974-07-30 | 1976-08-28 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1138745A (en) * | 1966-09-08 | 1969-01-01 | Beecham Group Ltd | Penicillins |
| IE32597B1 (en) * | 1968-01-05 | 1973-10-03 | Pfizer | Acylpenicillins and process for their preparation |
-
0
- BE BE759498D patent/BE759498A/en not_active IP Right Cessation
-
1970
- 1970-07-17 GB GB3465970A patent/GB1294028A/en not_active Expired
- 1970-11-24 ES ES385834A patent/ES385834A1/en not_active Expired
- 1970-11-24 SE SE1592570A patent/SE380025B/xx unknown
- 1970-11-25 GB GB5616170A patent/GB1308830A/en not_active Expired
- 1970-11-26 JP JP10372670A patent/JPS518956B1/ja active Pending
- 1970-11-26 DE DE19702058110 patent/DE2058110C3/en not_active Expired
- 1970-11-26 FR FR7042592A patent/FR2073418B1/fr not_active Expired
-
1973
- 1973-05-16 ES ES414805A patent/ES414805A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1294028A (en) | 1972-10-25 |
| ES414805A1 (en) | 1976-03-16 |
| DE2058110C3 (en) | 1975-10-16 |
| GB1308830A (en) | 1973-03-07 |
| SE380025B (en) | 1975-10-27 |
| JPS518956B1 (en) | 1976-03-22 |
| FR2073418A1 (en) | 1971-10-01 |
| BE759498A (en) | 1971-05-26 |
| DE2058110B2 (en) | 1975-01-30 |
| DE2058110A1 (en) | 1971-06-09 |
| FR2073418B1 (en) | 1974-08-30 |
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