GB1440372A - Process for the preparation of tetracyclines - Google Patents

Process for the preparation of tetracyclines

Info

Publication number
GB1440372A
GB1440372A GB3935073A GB3935073A GB1440372A GB 1440372 A GB1440372 A GB 1440372A GB 3935073 A GB3935073 A GB 3935073A GB 3935073 A GB3935073 A GB 3935073A GB 1440372 A GB1440372 A GB 1440372A
Authority
GB
United Kingdom
Prior art keywords
methylene
formula
complex
tetracycline compound
hydrogen
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
GB3935073A
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.)
Pfizer Inc
Original Assignee
Pfizer Inc
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 Pfizer Inc filed Critical Pfizer Inc
Publication of GB1440372A publication Critical patent/GB1440372A/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J31/00—Catalysts comprising hydrides, coordination complexes or organic compounds
    • B01J31/16—Catalysts comprising hydrides, coordination complexes or organic compounds containing coordination complexes
    • B01J31/24—Phosphines, i.e. phosphorus bonded to only carbon atoms, or to both carbon and hydrogen atoms, including e.g. sp2-hybridised phosphorus compounds such as phosphabenzene, phosphole or anionic phospholide ligands
    • B01J31/2404—Cyclic ligands, including e.g. non-condensed polycyclic ligands, the phosphine-P atom being a ring member or a substituent on the ring
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2231/00—Catalytic reactions performed with catalysts classified in B01J31/00
    • B01J2231/60—Reduction reactions, e.g. hydrogenation
    • B01J2231/64—Reductions in general of organic substrates, e.g. hydride reductions or hydrogenations
    • B01J2231/641—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes
    • B01J2231/645—Hydrogenation of organic substrates, i.e. H2 or H-transfer hydrogenations, e.g. Fischer-Tropsch processes of C=C or C-C triple bonds
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J2531/00—Additional information regarding catalytic systems classified in B01J31/00
    • B01J2531/80—Complexes comprising metals of Group VIII as the central metal
    • B01J2531/82—Metals of the platinum group
    • B01J2531/822—Rhodium

Abstract

1440372 Tetracyclines PFIZER Inc 20 Aug 1973 [1 Feb 1973 8 June 1973] 39350/73 Heading C2C A process comprises treating a tetracycline compound having an exocyclic methylene group and having the formula or an acid addition, alkali metal or amine salt thereof or a polyvalent metal salt complex thereof wherein Y is a hydrogen atom or OH, Z is hydrogen or a chlorine, bromine or fluorine atom, with hydrogen in the presence of a catalyst comprising a complex of rhodium with a tertiary phosphine of the formula PRR<SP>1</SP>R<SP>11</SP> wherein each of R and R<SP>1</SP> is a phenyl or a substituted phenyl group wherein the substituent is a halogen atom or a C 1-4 alkyl or C 1-4 alkoxy, and R<SP>11</SP> is R 1 or a C 1-12 alkyl or benzyl group, in a solvent medium in which the tetracycline compound and catalyst are soluble. The process is preferably carried out at - 20‹ to 100‹ C. and at a pressure of 4000 p.s.i.g. The complex preferably has the formula Rh<SP>1</SP>(PRR<SP>1</SP>R<SP>11</SP>) 3 Cl. The tetracycline compound treated is preferably 6- demethyl - 6 - deoxy - 6 - methylene - 5- hydroxytetracycline or 6-demethyl-6-deoxy-6- methylene - 5 - hydroxytetracycline hydrochloride, the catalytic hydrogenation effecting the reduction of methylene in the 6-position to methyl.
GB3935073A 1973-02-01 1973-08-20 Process for the preparation of tetracyclines Expired GB1440372A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US32851473A 1973-02-01 1973-02-01
US36806073A 1973-06-08 1973-06-08

Publications (1)

Publication Number Publication Date
GB1440372A true GB1440372A (en) 1976-06-23

Family

ID=26986413

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3935073A Expired GB1440372A (en) 1973-02-01 1973-08-20 Process for the preparation of tetracyclines

Country Status (2)

Country Link
AT (1) AT335059B (en)
GB (1) GB1440372A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4288613A (en) 1979-12-03 1981-09-08 Iowa State University Research Foundation, Inc. Cyclopentanone synthesis
US4500458A (en) * 1982-01-19 1985-02-19 Plurichemie Anstalt Process for the preparation of α-6-deoxytetracyclines
USRE32535E (en) * 1982-01-19 1987-10-27 Plurichemie Anstalt Process for the preparation of α-6-deoxytetracyclines

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4288613A (en) 1979-12-03 1981-09-08 Iowa State University Research Foundation, Inc. Cyclopentanone synthesis
US4500458A (en) * 1982-01-19 1985-02-19 Plurichemie Anstalt Process for the preparation of α-6-deoxytetracyclines
USRE32535E (en) * 1982-01-19 1987-10-27 Plurichemie Anstalt Process for the preparation of α-6-deoxytetracyclines

Also Published As

Publication number Publication date
ATA77574A (en) 1976-06-15
AT335059B (en) 1977-02-25

Similar Documents

Publication Publication Date Title
DE3680800D1 (en) METHOD FOR PRODUCING (6R) -TETRAHYDRO-L-BIOPTERIN.
GB1501436A (en) Aralkylamine derivatives
GB2163154A (en) Diamino tetrafluoroethoxy benzene derivatives and their use as couplers in hair dyeing composition
GB1440372A (en) Process for the preparation of tetracyclines
GB1458744A (en) Process for producing a 6-deoxytetracylines
JPH0559295A (en) 1,3-diaminobenzene derivative, preparation thereof, and water-base dye for keratinous fiber containing same
ES472290A1 (en) Diorthosubstituted benzene derivatives, especially for use in a method of therapy, processes for their preparation, and pharmaceutical compositions containing them.
IE38797B1 (en) Process for the preparation of tetracyclines
GB1492349A (en) Homophthalimide derivatives their preparation and use
GB1460409A (en) Process for the manufacture &#39;f di- and triamino naphthalenes
ES453544A1 (en) Preparation of ethylamine derivatives
JPH04504717A (en) hair dye preparations
Groult et al. Reaction of aminoalcohols with butadiene catalysed by palladium complexes
GB1497729A (en) Benzenesulphonyl ureas and process for their manufacture
Andrews et al. Syntheses of. beta.-diamines and. beta.-amino alcohols from. alpha.,. beta.-unsaturated ketones and aldehyde, methylamine, and borohydride reducing agents
JPS51125352A (en) Process for preparing 3-methoxy-alpha trifluoromethylphenyl- acetoxycyclope ntene-5-olderivatives
ES461758A1 (en) Process for the preparation of thiochroman derivatives
JPS51136653A (en) Process for preparing novel organophosphorous compounds
JPS57206661A (en) Acetaminobenzamide derivative
JPS5714571A (en) Production of c-acid or its salt
NL7602794A (en) PROCESS FOR PREPARING N.N-DIMETHYLHYDRAZINE.
ES455490A1 (en) 1- (aralkoxyphenyl) - 2- or -3 - (bis - arylalkylamino)-alkanes process for their manufacture and pharmaceutical preparations containing them
GB767163A (en) New 5:6-dihydro-benzo(c)cinnoline derivatives and a process for their preparation
BE810415A (en) Catalytic hydrogenation of 6-methylenetetracyclines - using rhodium-tert phosphine complex catalyst giving a stereospecific prod. in high yield
ATE28859T1 (en) DERIVATIVES OF AMINONAPHTHACENES AND PROCESS FOR THEIR PRODUCTION.

Legal Events

Date Code Title Description
PS Patent sealed
PE20 Patent expired after termination of 20 years

Effective date: 19930819