GB1118306A - Improvements in or relating to lincomycin derivatives and the manufacture thereof - Google Patents

Improvements in or relating to lincomycin derivatives and the manufacture thereof

Info

Publication number
GB1118306A
GB1118306A GB29882/65A GB2988265A GB1118306A GB 1118306 A GB1118306 A GB 1118306A GB 29882/65 A GB29882/65 A GB 29882/65A GB 2988265 A GB2988265 A GB 2988265A GB 1118306 A GB1118306 A GB 1118306A
Authority
GB
United Kingdom
Prior art keywords
compound
formula
carbon atoms
defined above
alkyl
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
GB29882/65A
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.)
Pharmacia and Upjohn Co
Original Assignee
Upjohn 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
Priority claimed from US387776A external-priority patent/US3366624A/en
Priority claimed from US463934A external-priority patent/US3380992A/en
Application filed by Upjohn Co filed Critical Upjohn Co
Publication of GB1118306A publication Critical patent/GB1118306A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • A61K31/70—Carbohydrates; Sugars; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • C07H15/02—Acyclic radicals, not substituted by cyclic structures
    • C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
    • C07H15/16—Lincomycin; Derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
    • C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Organic Chemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Molecular Biology (AREA)
  • Biochemistry (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Biotechnology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Genetics & Genomics (AREA)
  • Epidemiology (AREA)
  • Animal Behavior & Ethology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Saccharide Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

The invention comprises a compound having the general formula <FORM:1118306/C2/1> wherein R is an alkylidene group of not more than 20 carbon atoms, cycloalkylidene of 3 to not more than 8 carbon atoms, or aralkylidene of not more than 12 carbon atoms, R2 and R3 are hydrogen or alkyl of not more than 12 carbon atoms, and Z is a protective hydrocarbyl-oxycarbonyl group removable by hydrogenolysis or trityl (triphenylmethyl), diphenyl-(p-methoxyphenyl) methyl, bis - (p - methoxyphenyl) phenylmethyl, benzyl, or p-nitrobenzyl and W is H, -S-alkyl of not more than 12 carbon atoms or -SCH2CH2OR4, wherein R4 is alkyl of not more than 12 carbon atoms, a compound having the gzneral formula <FORM:1118306/C2/2> wherein R, R2, R3 and W are as defined above, T is H or Z as defined above, and the acid addition salt form of these compounds wherein T represents hydrogen provided that when T, R2 and R3 represent hydrogen and W represents -S-alkyl in the b -position, RH does not represent trans-propyl, the free base and acid-addition salt forms of a compound of the formula <FORM:1118306/C2/3> wherein R, R2 and R3 are as defined above, R1 is alkyl of not more than 20 carbon atoms, cycloalkyl of not more than 8 carbon atoms, or aralkyl of not more than 12 carbon atoms, and alkyl is of not more than 12 carbon atoms, the free base and acid addition salt forms of a compound of the formula <FORM:1118306/C2/4> wherein R, R1, R2 and R3 are as defined above and V is H or -SCH2CH2OR4, wherein R4 is as defined above, the free base and acid addition salt forms of the formula <FORM:1118306/C2/5> wherein R, R1, R2, R3 and alkyl are as defined above, a compound of the formula <FORM:1118306/C2/6> wherein R, R2, R3, Y and Z are as defined above, a compound of the formula <FORM:1118306/C2/7> wherein R, R2, R3 and Y are as defined above, M is H or Z as defined above, or alkyl of not more than 20 carbon atoms, cycloalkyl of not more than 8 carbon atoms or aralkyl of not more than 12 carbon atoms and acid addition salt forms of the compounds wherein M is hydrogen or alkyl of not more than 20 carbon atoms, cycloalkyl of not more than 8 carbon atoms or aralkyl of not more than 12 carbon atoms, a compound of the formula <FORM:1118306/C2/8> wherein Ac is acyl of the formula <FORM:1118306/C2/9> wherein R, R1, R3 and Y are as defined above, the free base and acid addition salt forms of a compound of the formula <FORM:1118306/C2/100> and a process which comprises reacting a compound of the formula <FORM:1118306/C2/111> wherein Z is as defined above with a Wittig reagent of the formula R = P(C6H5)3 wherein R is as defined above, to form a compound of the formula <FORM:1118306/C2/122> hydrogenating this compound over a platinum catalyst to form a compound of the formula <FORM:1118306/C2/133> and with this compound N-acylating a compound of the formula <FORM:1118306/C2/144> wherein R, R3, R4 and Y are as defined above, to form a compound of the formula <FORM:1118306/C2/155> hydrogenating this compound over a palladium catalyst to remove the Z group and alkylating the thus obtained compound to give a compound of the formula <FORM:1118306/C2/166> wherein R, R2, R3, Y and R1 are as define above. Antibacterial compositions comprise the above compounds as the active ingredient together with a pharmaceutically acceptable carrier.
GB29882/65A 1964-08-05 1965-07-14 Improvements in or relating to lincomycin derivatives and the manufacture thereof Expired GB1118306A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US387776A US3366624A (en) 1964-08-05 1964-08-05 Lincomycin derivatives and process for preparing same
US463934A US3380992A (en) 1965-06-14 1965-06-14 Lincomycin derivatives and process for preparing same

Publications (1)

Publication Number Publication Date
GB1118306A true GB1118306A (en) 1968-06-26

Family

ID=27012015

Family Applications (2)

Application Number Title Priority Date Filing Date
GB29882/65A Expired GB1118306A (en) 1964-08-05 1965-07-14 Improvements in or relating to lincomycin derivatives and the manufacture thereof
GB4196/68A Expired GB1118307A (en) 1964-08-05 1965-07-14 Improvements in or relating to antibiotic derivatives and the manufacture thereof

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB4196/68A Expired GB1118307A (en) 1964-08-05 1965-07-14 Improvements in or relating to antibiotic derivatives and the manufacture thereof

Country Status (11)

Country Link
BE (1) BE667948A (en)
BR (1) BR6571854D0 (en)
CH (1) CH478115A (en)
DE (1) DE1620607A1 (en)
DK (1) DK129936B (en)
ES (1) ES316092A1 (en)
FR (2) FR1503519A (en)
GB (2) GB1118306A (en)
IL (2) IL33548A (en)
NL (1) NL6510036A (en)
SE (3) SE324654B (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7018988B2 (en) 2000-03-27 2006-03-28 Applied Research Systems Ars Holding N.V. Pharmaceutically active pyrrolidine derivatives as Bax inhibitors
US7211601B2 (en) 2000-03-27 2007-05-01 Applied Research Systems Ars Holding N.V. Pharmaceutically active pyrrolidine derivatives

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7018988B2 (en) 2000-03-27 2006-03-28 Applied Research Systems Ars Holding N.V. Pharmaceutically active pyrrolidine derivatives as Bax inhibitors
US7211601B2 (en) 2000-03-27 2007-05-01 Applied Research Systems Ars Holding N.V. Pharmaceutically active pyrrolidine derivatives

Also Published As

Publication number Publication date
CH478115A (en) 1969-09-15
SE324569B (en) 1970-06-08
DE1620607A1 (en) 1970-05-14
DK129936C (en) 1975-05-20
SE317377B (en) 1969-11-17
ES316092A1 (en) 1965-11-16
GB1118307A (en) 1968-06-26
DK129936B (en) 1974-12-02
BR6571854D0 (en) 1973-10-25
FR5777M (en) 1968-03-18
BE667948A (en) 1966-02-07
FR1503519A (en) 1967-12-01
IL33548A (en) 1972-04-27
NL6510036A (en) 1966-02-07
IL23907A (en) 1971-05-26
SE324654B (en) 1970-06-08

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