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FR2315296A1 - Antibacterial fusidinic acid derivs. - with a 16-beta-hydrocarbyl(oxy, thio or sulphinyl) substit. (NL281276) - Google Patents

Antibacterial fusidinic acid derivs. - with a 16-beta-hydrocarbyl(oxy, thio or sulphinyl) substit. (NL281276)

Info

Publication number
FR2315296A1
FR2315296A1 FR7618949A FR7618949A FR2315296A1 FR 2315296 A1 FR2315296 A1 FR 2315296A1 FR 7618949 A FR7618949 A FR 7618949A FR 7618949 A FR7618949 A FR 7618949A FR 2315296 A1 FR2315296 A1 FR 2315296A1
Authority
FR
France
Prior art keywords
acid
beta
desacetoxy
alpha
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.)
Granted
Application number
FR7618949A
Other languages
French (fr)
Other versions
FR2315296B1 (en
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.)
SARATH
Original Assignee
SARATH
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 GB26989/75A external-priority patent/GB1523803A/en
Application filed by SARATH filed Critical SARATH
Publication of FR2315296A1 publication Critical patent/FR2315296A1/en
Application granted granted Critical
Publication of FR2315296B1 publication Critical patent/FR2315296B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J13/00—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17
    • C07J13/007—Normal steroids containing carbon, hydrogen, halogen or oxygen having a carbon-to-carbon double bond from or to position 17 with double bond in position 17 (20)
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
    • A61P31/04—Antibacterial agents
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J31/00—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring
    • C07J31/003—Normal steroids containing one or more sulfur atoms not belonging to a hetero ring the S atom directly linked to a ring carbon atom of the cyclopenta(a)hydrophenanthrene skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J41/00—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring
    • C07J41/0033—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005
    • C07J41/0055—Normal steroids containing one or more nitrogen atoms not belonging to a hetero ring not covered by C07J41/0005 the 17-beta position being substituted by an uninterrupted chain of at least three carbon atoms which may or may not be branched, e.g. cholane or cholestane derivatives, optionally cyclised, e.g. 17-beta-phenyl or 17-beta-furyl derivatives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07J—STEROIDS
    • C07J43/00—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton
    • C07J43/003—Normal steroids having a nitrogen-containing hetero ring spiro-condensed or not condensed with the cyclopenta(a)hydrophenanthrene skeleton not condensed

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Communicable Diseases (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Oncology (AREA)
  • Pharmacology & Pharmacy (AREA)
  • General Chemical & Material Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Steroid Compounds (AREA)

Abstract

Fusidinic acid derivs. of formula (I) and their pharmaceutically acceptable salts and easily hydrolysable esters are new: (C24 and C25 are joined by a single or double bond, Q1 and Q2 are H HO or O. A=O, S or SO. R1 = opt. branched 1-8C alkyl, 2-6C alkenyl or alkynyl, 3-7C cycloalkyl, aryl, aralkyl, heterocyclyl-alkyl or 5-6 membered heterocycle contg. O.S or N atoms; and all these gps. may be substd.). Prepn. is by reacting the 16 alpha-halo analogue, in which the 21-COOH is esterified, with R1AH then hydrolysing. (I) are useful for treating bacterial infections in humans and animals. They are more stable than fusidinic acid itself and are practically non-toxic. They may be administered in usual oral, parenteral or topical forms for an adult dose of 0.25-5, pref. 0.5-3g/day. A specifically claimed cpd., 16-desacetoxy-16 beta-isopropylthiofusidinic acid, was prepd. from 3-O-acetyl-16-desacetoxy-16 alpha-bromofusidinic acid p-nitrobenzyl ester, by reaction with isopropyl mercaptan, then hydrolysis with NaOH.
FR7618949A 1975-06-25 1976-06-22 Antibacterial fusidinic acid derivs. - with a 16-beta-hydrocarbyl(oxy, thio or sulphinyl) substit. (NL281276) Granted FR2315296A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB26989/75A GB1523803A (en) 1975-06-25 1975-06-25 16-ethers of fusidic acid derivatives
GB4622975 1975-11-07

Publications (2)

Publication Number Publication Date
FR2315296A1 true FR2315296A1 (en) 1977-01-21
FR2315296B1 FR2315296B1 (en) 1980-11-07

Family

ID=26258548

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7618949A Granted FR2315296A1 (en) 1975-06-25 1976-06-22 Antibacterial fusidinic acid derivs. - with a 16-beta-hydrocarbyl(oxy, thio or sulphinyl) substit. (NL281276)

Country Status (18)

Country Link
JP (1) JPS523051A (en)
AT (1) AT345979B (en)
AU (1) AU500027B2 (en)
CA (1) CA1064906A (en)
DE (1) DE2628360C2 (en)
DK (1) DK143905C (en)
ES (1) ES449257A1 (en)
FI (1) FI55852C (en)
FR (1) FR2315296A1 (en)
GR (1) GR60362B (en)
IE (1) IE43478B1 (en)
IT (1) IT1062245B (en)
LU (1) LU75239A1 (en)
NL (1) NL7606983A (en)
NZ (1) NZ181107A (en)
PT (1) PT65261A (en)
SE (1) SE7607322L (en)
SU (1) SU799670A3 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2357574A1 (en) * 1976-07-05 1978-02-03 Sarath NEW 16-ACYLTHIO DERIVATIVES OF FUSIDIC ACID, USEFUL IN PARTICULAR AS ANTIMICROBIALS AND THEIR PREPARATION PROCESS

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4548922A (en) * 1983-06-06 1985-10-22 Beth Israel Hospital Drug administration
US5372996A (en) * 1989-03-10 1994-12-13 Endorecherche, Inc. Method of treatment of androgen-related diseases
AU5851690A (en) * 1989-07-07 1991-02-06 Endorecherche Inc. Method of treatment of androgen-related diseases
RU2141967C1 (en) * 1992-05-21 1999-11-27 Андорешерш Инк. INHIBITORS OF TESTOSTERONE 5α-REDUCTASE, PHARMACEUTICAL COMPOSITION, METHOD OF INHIBITION OF TESTOSTERONE 5α-REDUCTASE ACTIVITY

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2357574A1 (en) * 1976-07-05 1978-02-03 Sarath NEW 16-ACYLTHIO DERIVATIVES OF FUSIDIC ACID, USEFUL IN PARTICULAR AS ANTIMICROBIALS AND THEIR PREPARATION PROCESS

Also Published As

Publication number Publication date
DE2628360C2 (en) 1986-11-06
IE43478B1 (en) 1981-03-11
JPS523051A (en) 1977-01-11
DE2628360A1 (en) 1977-01-13
SU799670A3 (en) 1981-01-23
DK285776A (en) 1976-12-26
DK143905C (en) 1982-04-19
NL7606983A (en) 1976-12-28
IT1062245B (en) 1983-09-20
GR60362B (en) 1978-05-19
SE7607322L (en) 1976-12-26
PT65261A (en) 1976-07-01
AU500027B2 (en) 1979-05-10
ATA438776A (en) 1978-02-15
PT65261B (en) 1977-12-07
AU1525076A (en) 1978-01-05
FI761863A (en) 1976-12-26
FI55852B (en) 1979-06-29
AT345979B (en) 1978-10-10
JPS6350360B2 (en) 1988-10-07
IE43478L (en) 1976-12-25
NZ181107A (en) 1978-11-13
FR2315296B1 (en) 1980-11-07
CA1064906A (en) 1979-10-23
DK143905B (en) 1981-10-26
LU75239A1 (en) 1977-03-16
ES449257A1 (en) 1977-12-16
FI55852C (en) 1979-10-10

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Legal Events

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TP Transmission of property
ST Notification of lapse