GB982252A - New cephalosporin compounds and method for preparing same - Google Patents

New cephalosporin compounds and method for preparing same

Info

Publication number
GB982252A
GB982252A GB20911/62A GB2091162A GB982252A GB 982252 A GB982252 A GB 982252A GB 20911/62 A GB20911/62 A GB 20911/62A GB 2091162 A GB2091162 A GB 2091162A GB 982252 A GB982252 A GB 982252A
Authority
GB
United Kingdom
Prior art keywords
general formula
radical
cephalosporin
heteromonocyclic
compounds
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
GB20911/62A
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 GB982252A publication Critical patent/GB982252A/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)
  • Life Sciences & Earth Sciences (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Epidemiology (AREA)
  • Medicinal Chemistry (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Cephalosporin Compounds (AREA)
  • Fertilizing (AREA)
  • Shafts, Cranks, Connecting Bars, And Related Bearings (AREA)

Abstract

Cephalosporins of the general formula <FORM:0982252/C2/1> wherein R1, taken alone, 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 tertiaryamino; R1 and R2, when taken together, are -O-; n is 0 or 1; R3 is C1-C6 alkylene: and R4 is a heteromonocyclic radical containing in the ring at least one atom of oxygen, nitrogen or sulphur, and the pharmaceutically acceptable salts, esters and amides thereof, such as 7 - b - (21 - furyl)propionamido -, 7 - (21 - furyl) acetamido -, 7 - (21 - thienyl)acetamido -, 7 - (y - 21 - thienyl - n - butyramido) -, 7 - (11-pyrazoleacetamido) -, and 7 - (N1 - pyrrylacetamido) - cephalosporanic acid, may be prepared by (A) acylating a compound having the bicyclic ring structure of cephalosporin C and having a general formula represented by one of <FORM:0982252/C2/2> wherein R11 is -OH or a C1-C8 acyloxy radical, and Am+ is a tertiary amino radical, with an acylating agent having at least one constituent radical of the general formula <FORM:0982252/C2/3> or (B) acylating a compound having the general formula <FORM:0982252/C2/4> with an acylating agent having at least one constituent radical of the general formula <FORM:0982252/C2/5> and heating the product with acidified water to form the corresponding heteromonocyclic acyl derivative of the nuclei of cephalosporin CC compounds, refluxing the product in solution with an excess of a tertiary amine corresponding to Am+ as defined above to form the corresponding heteromonocyclic derivative of the nuclei of cephalosporin CA compounds, or treating the product with citrus acetylesterase in a buffered aqueous medium to form the corresponding heteromonocyclic derivative of the nuclei of desacetylcephanosporin C compounds. A pharmaceutical composition comprises a cephalosporin of the first formula shown above and a pharmaceutical carrier. Specification 810,196 is referred to.
GB20911/62A 1961-06-08 1962-05-30 New cephalosporin compounds and method for preparing same Expired GB982252A (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
GB982252A true GB982252A (en) 1965-02-03

Family

ID=22362437

Family Applications (1)

Application Number Title Priority Date Filing Date
GB20911/62A Expired GB982252A (en) 1961-06-08 1962-05-30 New cephalosporin compounds and method for preparing same

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)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492297A (en) * 1965-07-01 1970-01-27 Merck & Co Inc Guanidino cephalosporins
US3624225A (en) * 1966-06-24 1971-11-30 Glaxo Lab Ltd Cephalosporin compositions

Families Citing this family (1)

* 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

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3492297A (en) * 1965-07-01 1970-01-27 Merck & Co Inc Guanidino cephalosporins
US3624225A (en) * 1966-06-24 1971-11-30 Glaxo Lab Ltd Cephalosporin compositions

Also Published As

Publication number Publication date
ES277871A1 (en) 1962-12-01
BR6239733D0 (en) 1973-06-14
NO122749B (en) 1971-08-09
CH409967A (en) 1966-03-31
DE1445701A1 (en) 1969-08-28
NO133074C (en) 1976-03-03
FI43597B (en) 1971-02-01
LU41846A1 (en) 1962-12-07
DK129199C (en) 1975-01-27
OA02701A (en) 1970-12-15
SE357204B (en) 1973-06-18
NO133074B (en) 1975-11-24
FR2899M (en) 1964-11-09
DE1445684A1 (en) 1968-12-05
FI43597C (en) 1971-05-10
CA984379A (en) 1976-02-24
BE618663A (en) 1962-12-14
DK129199B (en) 1974-09-09
SE322513B (en) 1970-04-13

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