GB1118307A - Improvements in or relating to antibiotic derivatives and the manufacture thereof - Google Patents

Improvements in or relating to antibiotic derivatives and the manufacture thereof

Info

Publication number
GB1118307A
GB1118307A GB4196/68A GB419668A GB1118307A GB 1118307 A GB1118307 A GB 1118307A GB 4196/68 A GB4196/68 A GB 4196/68A GB 419668 A GB419668 A GB 419668A GB 1118307 A GB1118307 A GB 1118307A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
compound
alkyl
formula
group
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
GB4196/68A
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 GB1118307A publication Critical patent/GB1118307A/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

Abstract

The invention comprises the free base and acid addition salt forms of a compound of the formula <FORM:1118307/C2/1> wherein R2 and R3 are hydrogen or alkyl of not more than 12 carbon atoms and Y is hydrogen, -S-alkyl of not more than 12 carbon atoms, -S-CH2CH2OH or -S-CH2CH2O alkyl, wherein alkyl is of not more than 12 carbon atoms, a compound of the formula <FORM:1118307/C2/2> wherein Ac is alkanoyl or aralkanoyl of not more than 12 carbon atoms and R3 and Y are as defined above, a process which comprises reacting <FORM:1118307/C2/3> with acetone to form a compound of the formula <FORM:1118307/C2/4> oxidizing the latter with chromic acid to form a compound of the formula <FORM:1118307/C2/5> converting the obtained compound to a compound of the formula <FORM:1118307/C2/6> by a borohydride reduction, and removing either the isopropylidene group first by acid hydrolysis, and then the Ac group by hydrazinolysis or alternatively removing the Ac group first by hydrazinolysis and then the isopropylidene group by acid hydrolysis to form a compound of the formula <FORM:1118307/C2/7> wherein R3, Ac and Y are as defined above and a process which comprises removing the Ac group from a compound of the general formula <FORM:1118307/C2/8> wherein R12 is alkyl of 3-12 carbon atoms, -CH2CH2OH or -CH2CH2OR4, wherein R4 is alkyl of not more than 12 carbon atoms and Ac is alkanoyl, aralkanoyl of not more than 12 carbon atoms or acyl of the general formula <FORM:1118307/C2/9> wherein Z is a protective hydrocarbyloxycarbonyl group which is removable by hydrogenolysis, R is alkylidene 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 and R1 is hydrogen, alkyl of not more than 20 carbon atoms, cycloalkyl of 3 to not more than 8 carbon atoms, or aralkyl of not more than 12 carbon atoms, by hydrazinolysis to form a compound having the general formula <FORM:1118307/C2/100>
GB4196/68A 1964-08-05 1965-07-14 Improvements in or relating to antibiotic derivatives and the manufacture thereof Expired GB1118307A (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
GB1118307A true GB1118307A (en) 1968-06-26

Family

ID=27012015

Family Applications (2)

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
GB29882/65A Expired GB1118306A (en) 1964-08-05 1965-07-14 Improvements in or relating to lincomycin derivatives and the manufacture thereof

Family Applications After (1)

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

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) GB1118307A (en)
IL (2) IL33548A (en)
NL (1) NL6510036A (en)
SE (3) SE317377B (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
BR0109900A (en) 2000-03-27 2003-06-03 Applied Research Systems Pharmaceutically active pyrolidine derivatives, use of pyrolidine derivatives, pharmaceutical composition and process for preparing a pyrolidine derivative
IL151911A0 (en) 2000-03-27 2003-04-10 Applied Research Systems Pyrolidine derivatives, their preparation and pharmaceutical compositions containing them

Also Published As

Publication number Publication date
NL6510036A (en) 1966-02-07
ES316092A1 (en) 1965-11-16
SE317377B (en) 1969-11-17
FR5777M (en) 1968-03-18
GB1118306A (en) 1968-06-26
IL33548A (en) 1972-04-27
CH478115A (en) 1969-09-15
IL23907A (en) 1971-05-26
BE667948A (en) 1966-02-07
FR1503519A (en) 1967-12-01
DK129936B (en) 1974-12-02
SE324654B (en) 1970-06-08
DK129936C (en) 1975-05-20
BR6571854D0 (en) 1973-10-25
SE324569B (en) 1970-06-08
DE1620607A1 (en) 1970-05-14

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