GB1313907A - Process for the cleavage of protected carboxy groups - Google Patents

Process for the cleavage of protected carboxy groups

Info

Publication number
GB1313907A
GB1313907A GB3404770A GB3404770A GB1313907A GB 1313907 A GB1313907 A GB 1313907A GB 3404770 A GB3404770 A GB 3404770A GB 3404770 A GB3404770 A GB 3404770A GB 1313907 A GB1313907 A GB 1313907A
Authority
GB
United Kingdom
Prior art keywords
amino
acids
hydrogen
carboxylic acids
carboxylic acid
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
Application number
GB3404770A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Novartis AG
Original Assignee
Ciba Geigy AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from CH1766869A external-priority patent/CH527849A/en
Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG
Publication of GB1313907A publication Critical patent/GB1313907A/en
Expired legal-status Critical Current

Links

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)
  • Cephalosporin Compounds (AREA)

Abstract

1313907 Esters of penicillanic acids and cephalosporanic acids CIBA-GEIGY AG 14 July 1970 [16 July 1969 27 Nov 1969 15 Jan 1970] 34047/70 Heading C2A The invention comprises 2-iodoethyl or 2- bromoethyl esters of penicillanic acids or cephalosporanic acids or 1-sulphoxides thereof, e.g. 6-amino-penam-3-carboxylic acids or 7- amino-cephem-4-carboxylic acids or 6-N-R- amino - 2 - R 1 - 2 - R 2 - penam - 3 - carboxylic acids or the 1-oxides thereof, where R is hydrogen or acyl and R 1 and R 2 are optionally substituted methyl groups or 7-N-R-amino-3- R 1 -ceph(2)em-4-carboxylic acid or 7-N-R-amino- 3 - R 1 - ceph - 3 - em - 4 - carboxylic acids or 6 - N - R<SP>1</SP> - amino - 2,2 - dimethyl - penam - 3- carboxylic acids or 1-oxides thereof or 7-N-R<SP>1</SP>- amino - 3 -Ra - methyl - ceph(2)em -4 - carboxylic acids or 7 - N - R<SP>1</SP> - amino - 3 - Ra - methylceph(3)em - 4 - carboxylic acid. In these formulµ, R<SP>1</SP> is hydrogen or an acyl radical contained in a pharmacologically active N-acyl derivative of a 6-aminopenicillanic acid or a 7-aminocephalosporanic acid compound or an easily eliminated acyl residue of a carboxylic acid semi-ester, Ra is hydrogen or hydroxy, C 1 -C 7 alkoxy or C 1 -C 7 alkanoyloxy or a 6-NR<SP>11</SP> - amino - 2,2 - dimethyl - penam - 3 - carboxylic acid or a 1-oxide thereof or a 7-N-R<SP>11</SP>- amino - 3 - Ra<SP>1</SP> - methyl - ceph(2)em - 4 - carboxylic acid or a 7-N-R<SP>11</SP>-amino-3-Ra<SP>1</SP>-methylceph(3)em-4-carboxylic acid, wherein R<SP>11</SP> is hydrogen or an acyl radical contained in a pharmacologically active or biosynthetically available 6 - N - acylamino - penicillanic acid or 7-aminocephalosporanic acid or a readily eliminated acyl residue of a carboxylic acid semi-ester, Ra<SP>1</SP> is hydrogen or acetyloxy. The invention also provides a process for the manufacture of 6-amino-penam-3-carboxylic acids or 7-aminocephem - 4 - carboxylic acids having free carboxyl groups by chemical reduction of the 2-iodoethyl esters of these compounds. Suitable reducing agents are reducing metals or metal compounds; metals, metal alloys or amalgams together with an agent yielding hydrogen; or chromium II salts in aqueous media also containing organic solvents. Preferably the reaction is carried out between - 10‹ and + 30‹ C.
GB3404770A 1969-07-16 1970-07-14 Process for the cleavage of protected carboxy groups Expired GB1313907A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US84235969A 1969-07-16 1969-07-16
CH1766869A CH527849A (en) 1969-07-16 1969-11-27 6-amino-en-3-and 7-amino-ceph-4-carboxylic - acids
CH51770 1970-01-15

Publications (1)

Publication Number Publication Date
GB1313907A true GB1313907A (en) 1973-04-18

Family

ID=27172173

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3404770A Expired GB1313907A (en) 1969-07-16 1970-07-14 Process for the cleavage of protected carboxy groups

Country Status (5)

Country Link
CA (1) CA921907A (en)
DE (1) DE2033787A1 (en)
FR (1) FR2059519B1 (en)
GB (1) GB1313907A (en)
NL (1) NL7010475A (en)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1491655A (en) * 1965-09-10 1967-08-11 Process for the temporary protection of acid groups

Also Published As

Publication number Publication date
NL7010475A (en) 1971-01-19
FR2059519A1 (en) 1971-06-04
DE2033787A1 (en) 1971-02-04
FR2059519B1 (en) 1974-08-09
CA921907A (en) 1973-02-27

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Legal Events

Date Code Title Description
PS Patent sealed
PLNP Patent lapsed through nonpayment of renewal fees