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GB1011843A - D-(-)-ª‡-aminobenzylpenicillin trihydrate - Google Patents

D-(-)-ª‡-aminobenzylpenicillin trihydrate

Info

Publication number
GB1011843A
GB1011843A GB1115564A GB1115564A GB1011843A GB 1011843 A GB1011843 A GB 1011843A GB 1115564 A GB1115564 A GB 1115564A GB 1115564 A GB1115564 A GB 1115564A GB 1011843 A GB1011843 A GB 1011843A
Authority
GB
United Kingdom
Prior art keywords
water
alkyl
sulphonate
aminobenzylpenicillin
trihydrate
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
GB1115564A
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.)
Bristol Myers Co
Original Assignee
Bristol Myers 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
Family has litigation
First worldwide family litigation filed litigation Critical https://patents.darts-ip.com/?family=25702636&utm_source=google_patent&utm_medium=platform_link&utm_campaign=public_patent_search&patent=GB1011843(A) "Global patent litigation dataset” by Darts-ip is licensed under a Creative Commons Attribution 4.0 International License.
Priority claimed from US266807A external-priority patent/US3157640A/en
Application filed by Bristol Myers Co filed Critical Bristol Myers Co
Publication of GB1011843A publication Critical patent/GB1011843A/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
    • C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
    • C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
    • C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
    • C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
    • C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
    • C07D499/68—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with aromatic rings as additional substituents on the carbon chain
    • 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
    • A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
    • A61K31/425—Thiazoles
    • A61K31/429—Thiazoles condensed with heterocyclic ring systems
    • A61K31/43—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/587—Unsaturated compounds containing a keto groups being part of a ring
    • C07C49/687—Unsaturated compounds containing a keto groups being part of a ring containing halogen
    • C07C49/697—Unsaturated compounds containing a keto groups being part of a ring containing halogen containing six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms

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)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

The invention relates to D-(-)a -aminobenzylpenicillin trihydrate. This compound is prepared by contacting an acid addition salt of D-(-)-a -aminopenicillin with an amine of general formula <FORM:1011843/C2/1> wherein R is an aliphatic group having 10 to 15 carbon atoms, R1 is hydrogen or C1-C6 alkyl and R2, R3 and R4 are each alkyl and wherein R2, R3 and R4 contain in aggregate from 11 to 14 carbon atoms, in a water-immiscible organic solvent containing at least 3 moles of water per mole of D-(-)-a aminobenzylpenicillin at a temperature below 60 DEG C. and recovering the precipitate of D-(-)-a -aminopenicillin trihydrate. The acid addition salt may be with inorganic or organic acids especially aryl sulphonic acids of formula R5SO3H wherein R5 is <FORM:1011843/C2/2> or <FORM:1011843/C2/3> in which R6, R7, R8 and R9 are hydrogen, C1-C12 alkyl, C1-C6 alkoxy, C1-C6 alkylthio, nitro, C1-C6 alkanoylamino, C1-C6 alkanoyloxy, sulphanyl, chloro, iodo, bromo, fluoro, trifluoromethyl, C1-C6 alkylsulphonyl, benzyl, carbo C1-C6 alkoxy, phenethyl, cycloheptyl, cyclohexyl, and cyclopentyl, especially the p-nonylbenzene sulphonate and p-toluene sulphonate or the p-cymene sulphonate. The preferred water-immiscible solvent is methylisobutylketone. The penicillin is insoluble in water, stable on storage, resistant to destruction by acids and is a potent antibacterial agent for pharmaceutical and veterinary use, e.g. treating mastitis in cattle. It may be incorporated into animal feeds or formulated into pharmaceutical compositions. Specification 873,049 is referred to.
GB1115564A 1963-03-21 1964-03-17 D-(-)-ª‡-aminobenzylpenicillin trihydrate Expired GB1011843A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US266807A US3157640A (en) 1963-03-21 1963-03-21 D-(-)-alpha-aminobenzylpenicillin trihydrate
CH800963A CH451120A (en) 1963-03-21 1963-06-28 Process for the preparation of tricyclic amines

Publications (1)

Publication Number Publication Date
GB1011843A true GB1011843A (en) 1965-12-01

Family

ID=25702636

Family Applications (6)

Application Number Title Priority Date Filing Date
GB1115564A Expired GB1011843A (en) 1963-03-21 1964-03-17 D-(-)-ª‡-aminobenzylpenicillin trihydrate
GB1190666A Expired GB1065606A (en) 1963-03-21 1964-06-26 Novel 5-(3-alkoxy-propylidene)-dibenzocycloheptatriene derivatives and a process for the preparation thereof
GB1190366A Expired GB1065604A (en) 1963-03-21 1964-06-26 Novel 5-(chloro-propylidene)-dibenzocycloheptatriene derivatives and a process for the preparation thereof
GB1190466A Expired GB1065605A (en) 1963-03-21 1964-06-26 Novel 5-propenylidene-debenzocycloheptatriene derivatives and a process for the preparation thereof
GB1190266A Expired GB1065603A (en) 1963-03-21 1964-06-26 Novel 5-(amino-propyl)-dibenzocycloheptatriene derivatives and a process for the preparation thereof
GB2648964A Expired GB1065602A (en) 1963-03-21 1964-06-26 Novel substituted 5-(amino-propylidene)-dibenzo[a,d]-cyclohepta[1,4,6]trienes and the manufacture thereof

Family Applications After (5)

Application Number Title Priority Date Filing Date
GB1190666A Expired GB1065606A (en) 1963-03-21 1964-06-26 Novel 5-(3-alkoxy-propylidene)-dibenzocycloheptatriene derivatives and a process for the preparation thereof
GB1190366A Expired GB1065604A (en) 1963-03-21 1964-06-26 Novel 5-(chloro-propylidene)-dibenzocycloheptatriene derivatives and a process for the preparation thereof
GB1190466A Expired GB1065605A (en) 1963-03-21 1964-06-26 Novel 5-propenylidene-debenzocycloheptatriene derivatives and a process for the preparation thereof
GB1190266A Expired GB1065603A (en) 1963-03-21 1964-06-26 Novel 5-(amino-propyl)-dibenzocycloheptatriene derivatives and a process for the preparation thereof
GB2648964A Expired GB1065602A (en) 1963-03-21 1964-06-26 Novel substituted 5-(amino-propylidene)-dibenzo[a,d]-cyclohepta[1,4,6]trienes and the manufacture thereof

Country Status (10)

Country Link
BE (2) BE645315A (en)
BR (1) BR6460323D0 (en)
CH (1) CH451120A (en)
DE (3) DE1768747A1 (en)
DK (2) DK119205C (en)
FR (1) FR3431M (en)
GB (6) GB1011843A (en)
IL (1) IL21558A (en)
NL (1) NL6407095A (en)
SE (2) SE328276B (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4758577A (en) * 1984-04-05 1988-07-19 Merck & Co., Inc. 4-(5H-dibenzo[a,d]cyclohepten-5-yl)piperidine compounds for treating cardiovascular disorders

Also Published As

Publication number Publication date
GB1065605A (en) 1967-04-19
DK119205B (en) 1970-11-30
CH451120A (en) 1968-05-15
NL6407095A (en) 1964-12-29
GB1065604A (en) 1967-04-19
DE1468034A1 (en) 1968-12-19
GB1065606A (en) 1967-04-19
IL21558A (en) 1968-01-25
SE328276B (en) 1970-09-14
DE1768747A1 (en) 1972-04-20
BR6460323D0 (en) 1973-08-09
BE649716A (en) 1964-12-28
FR3431M (en) 1965-07-12
SE337368B (en) 1971-08-09
BE645315A (en) 1964-09-17
GB1065603A (en) 1967-04-19
DE1768746A1 (en) 1972-05-10
DK127058B (en) 1973-09-17
DK119205C (en) 1970-11-30
GB1065602A (en) 1967-04-19

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