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GB1155030A - 7-Amino-Desacetyl-Cephalosporanic Acid Compounds and process for their manufacture - Google Patents

7-Amino-Desacetyl-Cephalosporanic Acid Compounds and process for their manufacture

Info

Publication number
GB1155030A
GB1155030A GB2467568A GB2467568A GB1155030A GB 1155030 A GB1155030 A GB 1155030A GB 2467568 A GB2467568 A GB 2467568A GB 2467568 A GB2467568 A GB 2467568A GB 1155030 A GB1155030 A GB 1155030A
Authority
GB
United Kingdom
Prior art keywords
amino
cephalosporanic acid
desacetyl
free
cephalosporanic
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
GB2467568A
Inventor
Robert Burns Woodward
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.)
Individual
Original Assignee
Individual
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 CH1262365A external-priority patent/CH480355A/en
Priority claimed from CH1697865A external-priority patent/CH497457A/en
Priority claimed from CH1697065A external-priority patent/CH497445A/en
Priority claimed from CH1697365A external-priority patent/CH497448A/en
Priority claimed from CH1698065A external-priority patent/CH497379A/en
Priority claimed from CH1697765A external-priority patent/CH497369A/en
Priority claimed from CH1698165A external-priority patent/CH497461A/en
Priority claimed from CH1697665A external-priority patent/CH497371A/en
Priority claimed from CH1696965A external-priority patent/CH497446A/en
Priority claimed from CH1697565A external-priority patent/CH497456A/en
Priority claimed from CH1697465A external-priority patent/CH497451A/en
Priority claimed from CH1697265A external-priority patent/CH497447A/en
Priority claimed from CH1697965A external-priority patent/CH497460A/en
Application filed by Individual filed Critical Individual
Priority claimed from GB3865466A external-priority patent/GB1155024A/en
Publication of GB1155030A publication Critical patent/GB1155030A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C07D277/06—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/42—Separation; Purification; Stabilisation; Use of additives
    • C07C51/487—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification
    • C07C51/493—Separation; Purification; Stabilisation; Use of additives by treatment giving rise to chemical modification whereby carboxylic acid esters are formed
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/50—Organo-phosphines
    • C07F9/53—Organo-phosphine oxides; Organo-phosphine thioxides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/54—Quaternary phosphonium compounds
    • C07F9/5463—Compounds of the type "quasi-phosphonium", e.g. (C)a-P-(Y)b wherein a+b=4, b>=1 and Y=heteroatom, generally N or O
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
    • C07F9/6539—Five-membered rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Cephalosporin Compounds (AREA)

Abstract

1,155,030. 7-Amino-desacetyl cephalosporanic acid compounds. R. B. WOODWARD. 30 Aug., 1966 [9 Dec., 1965; 13 Jan., 1966], No. 24675/68. Divided out of 1,155,024. Heading C2A. 7-Amino-desacetyl cephalosporanic acid compounds of Formula XIVa in which R a is H or the residue of an alcohol and each of R 1 and R 2 is H or acyl, are prepared by the isomerization of a 7-amino-desacetylisocephalosporanic acid of Formula XIIIa in which R 1 , R 2 and R a have the above meanings, by treatment with a weakly basic agent. The preparation of the 7-aminodesacetyl isocephalosporanic acid compounds is disclosed in Specification 1,155,024). The weakly basic agent may be (a) an organic base such as pyridine, dimethyl aniline, tertiary aliphatic, azacycloaliphatic or tertiary araliphatic such as benzyldimethylamine or (b) the organic salts, e.g sodium acetate, triethylammonium acetate, or N-methyl piperidine acetate. The reaction is preferably in an anhydrous medium and, where appropriate, the weak basic agent may be used as solvent. Using conventional procedures, the resulting compound may have (a) an esterified carboxyl group converted into a free carboxyl group, (b) a free carboxyl group converted to an esterified carboxyl group, (c) an acylated amino group converted into a free NH 2 group, (d) a free amino group converted into an acylated amino group. The invention also relates to 7-amino desacetyl cephalosporanic acids of Formula XIVa in which R 1 and R 2 are hydrogen or acyl and R a is 2,2,2-trichloroethyl. Typical compounds are 7-(2-thienylacetylamino)-cephalosporanic acid 2,2,2-trichloroethyl ester, 7- [D - 5 - (carbo - 2,2,2 - trichloro - ethoxy) - 5- (2,2,2 - - trichloroethoxy - carbonylamino)- valerylamido] - cephalosporanic acid 2,2,2- trichloroethyl ester, 7-[D-5-(2,2,2-trichloroethoxy - carbonylamino) - 5 - carboxy valerylamino] - cephalosporanic acid, 7 - [D - 5 - (carbodiphenylmethoxy) - 5 - (2,2,2 - trichloroethoxycarbonylamino) - valerylamino] - cephalosporanic acid diphenylmethyl ester, 7-[D-5-tertiary butyloxycarbonylamino - 5 - (carbo - 2,2,2 - trichloroethoxy) - valerylamino] - cephalosporanic acid 2,2,2-trichloroethyl ester and cephalosporin C bis-2,2,2-trichloroethyl ester. The free acids may be converted to salts including those of copper, iron, magnesium, zinc and lead.
GB2467568A 1965-09-10 1966-08-30 7-Amino-Desacetyl-Cephalosporanic Acid Compounds and process for their manufacture Expired GB1155030A (en)

Applications Claiming Priority (24)

Application Number Priority Date Filing Date Title
CH1262365A CH480355A (en) 1965-09-10 1965-09-10 Process for the preparation of 3-tert-butyloxycarbonyl-thiazolidine-4-carboxylic acids
CH1697365A CH497448A (en) 1965-12-09 1965-12-09 Actinomyces aureofaciens ls-b-22-ol
CH1698065A CH497379A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1697565A CH497456A (en) 1965-12-09 1965-12-09 Azetidine compounds and process for their manufacture
CH1698165A CH497461A (en) 1965-12-09 1965-12-09 Process for the preparation of 7-amino-deacetylcephalosporanic acid compounds
CH1697065A CH497445A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1697865A CH497457A (en) 1965-12-09 1965-12-09 Process for the prepn. of cpds. where ac = acyl; X = disubstd. C atom; Ra= an alcohol residue; Ro= H or an acyl. Intermediates in the prepn. of phar
CH1697765A CH497369A (en) 1965-12-09 1965-12-09 Alpha-diacylmethyl-alpha-hydroxymethane carboxylic acid esters - intermediates in the synthesis of cephalosporanic acids
CH1697465A CH497451A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH1697265A CH497447A (en) 1965-12-09 1965-12-09 (3)-Acyl-(5)-acyloxy-thiazolidine-(4)-carboxylic acid derivs.
CH1697965A CH497460A (en) 1965-12-09 1965-12-09 Process for the prepn. of cpds. where ac = acyl; X = disubstd. C atom; Ra= an alcohol residue; Ro= H or an acyl. Intermediates in the prepn. of phar
CH1696965A CH497446A (en) 1965-12-09 1965-12-09 2 2-disubst-3-acyl-5-hydrazino-thiazolidine-4-carboxylic acid derivs
CH1697665A CH497371A (en) 1965-12-09 1965-12-09 Protection of carboxyl gps. in penicillin and cephalosporin synthesis
CH45366 1966-01-13
CH45266 1966-01-13
CH44966 1966-01-13
CH45166 1966-01-13
CH44766 1966-01-13
CH44666 1966-01-13
CH44866 1966-01-13
CH45066 1966-01-13
CH153066 1966-02-03
CH152966 1966-02-03
GB3865466A GB1155024A (en) 1965-09-10 1966-08-30 7-Amino-Desacetyl-Isocephalosporanic Acid Compounds and process for their manufacture

Publications (1)

Publication Number Publication Date
GB1155030A true GB1155030A (en) 1969-06-11

Family

ID=27586710

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2467568A Expired GB1155030A (en) 1965-09-10 1966-08-30 7-Amino-Desacetyl-Cephalosporanic Acid Compounds and process for their manufacture

Country Status (1)

Country Link
GB (1) GB1155030A (en)

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