ES277871A1 - A method of preparation of an antibiotic composite of cephalosporine (Machine-translation by Google Translate, not legally binding) - Google Patents

A method of preparation of an antibiotic composite of cephalosporine (Machine-translation by Google Translate, not legally binding)

Info

Publication number
ES277871A1
ES277871A1 ES277871A ES277871A ES277871A1 ES 277871 A1 ES277871 A1 ES 277871A1 ES 277871 A ES277871 A ES 277871A ES 277871 A ES277871 A ES 277871A ES 277871 A1 ES277871 A1 ES 277871A1
Authority
ES
Spain
Prior art keywords
cephalosporin
general formula
radical
heteromonocyclic
see formula
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
ES277871A
Other languages
Spanish (es)
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.)
Eli Lilly and Co
Original Assignee
Eli Lilly and Co
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
Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co
Publication of ES277871A1 publication Critical patent/ES277871A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
    • A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
    • C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
    • C07D501/14—Compounds having a nitrogen atom directly attached in position 7
    • C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
    • C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
    • C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
    • C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
    • C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Shafts, Cranks, Connecting Bars, And Related Bearings (AREA)
  • Fertilizing (AREA)

Abstract

A method of preparing a cephalosporin antibiotic compound having the general formula ** (See formula) ** wherein R1, in isolation, is -OH, C1-C8 acyloxy, or tertiary amino, R2 is -OH when R1 is -OH, R2 is -OH when R1 is C1-C8 acyloxy, R2 is -O- when R1 is tertiary amino, R1 and R2 when taken together, are -O-, n is 0 or 1, R3 is C1-C8 alcohol, and R4 is a heteromonocyclic radical containing O, S and/or N; characterized in that (A) acylating a compound having the bicyclic ring structure of cephalosporin C and having the general formula represented by one of the ** (See formula) ** wherein R1 'is -OH or a C1-C8 acyloxy radical, and Am4 is a tertiary amino radical; with an acylating agent having at least one constituent radical of the general formula ** (See formula) ** wherein R3, R4 and n are as defined above; or (B) acylating a compound having the bicyclic ring structure of cephalosporin C and having the general formula ** (See formula) ** with an acylating agent having at least one constituent radical of the general formula ** (See formula) ** wherein R3, R4 and n are as defined above; and the product is heated with acidulated water to form the corresponding heteromonocyclic acyl derivative of the nucleus of the cephalosporin Cc compounds, the product is refluxed in solution with an excess of tertiary amine corresponding to Am + as defined above, to form the corresponding heteromonocyclic derivative of the nuclei of the cephalosporin CA compounds, or the product is treated with citric acetyl esterase in a buffered aqueous medium to form the corresponding heteromonocyclic derivative of the nuclei of the desacetylcephalosporin C compounds. (Machine-translation by Google Translate, not legally binding)
ES277871A 1961-06-08 1962-07-01 A method of preparation of an antibiotic composite of cephalosporine (Machine-translation by Google Translate, not legally binding) Expired ES277871A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US11561261A 1961-06-08 1961-06-08

Publications (1)

Publication Number Publication Date
ES277871A1 true ES277871A1 (en) 1962-12-01

Family

ID=22362437

Family Applications (1)

Application Number Title Priority Date Filing Date
ES277871A Expired ES277871A1 (en) 1961-06-08 1962-07-01 A method of preparation of an antibiotic composite of cephalosporine (Machine-translation by Google Translate, not legally binding)

Country Status (14)

Country Link
BE (1) BE618663A (en)
BR (1) BR6239733D0 (en)
CA (1) CA984379A (en)
CH (1) CH409967A (en)
DE (2) DE1445684A1 (en)
DK (1) DK129199B (en)
ES (1) ES277871A1 (en)
FI (1) FI43597C (en)
FR (1) FR2899M (en)
GB (1) GB982252A (en)
LU (1) LU41846A1 (en)
NO (2) NO122749B (en)
OA (1) OA02701A (en)
SE (2) SE322513B (en)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB1082943A (en) * 1963-03-27 1967-09-13 Glaxo Lab Ltd Derivatives of 7-aminocephalosporanic acid
US3492297A (en) * 1965-07-01 1970-01-27 Merck & Co Inc Guanidino cephalosporins
GB1195203A (en) * 1966-06-24 1970-06-17 Glaxo Lab Ltd Cephalosporins

Also Published As

Publication number Publication date
DE1445684A1 (en) 1968-12-05
NO133074B (en) 1975-11-24
SE357204B (en) 1973-06-18
GB982252A (en) 1965-02-03
NO122749B (en) 1971-08-09
DK129199C (en) 1975-01-27
DE1445701A1 (en) 1969-08-28
FI43597C (en) 1971-05-10
BE618663A (en) 1962-12-14
FI43597B (en) 1971-02-01
CA984379A (en) 1976-02-24
SE322513B (en) 1970-04-13
CH409967A (en) 1966-03-31
LU41846A1 (en) 1962-12-07
DK129199B (en) 1974-09-09
OA02701A (en) 1970-12-15
NO133074C (en) 1976-03-03
FR2899M (en) 1964-11-09
BR6239733D0 (en) 1973-06-14

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