FR2354770A1 - Antimicrobial and antifungal indolizino-isoquinoline cpds. - with (10)-nitro and (7)-oxo substits., useful as local antiseptics - Google Patents

Antimicrobial and antifungal indolizino-isoquinoline cpds. - with (10)-nitro and (7)-oxo substits., useful as local antiseptics

Info

Publication number
FR2354770A1
FR2354770A1 FR7618232A FR7618232A FR2354770A1 FR 2354770 A1 FR2354770 A1 FR 2354770A1 FR 7618232 A FR7618232 A FR 7618232A FR 7618232 A FR7618232 A FR 7618232A FR 2354770 A1 FR2354770 A1 FR 2354770A1
Authority
FR
France
Prior art keywords
indolizino
opt
substd
isoquinoline
oxo
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
FR7618232A
Other languages
French (fr)
Other versions
FR2354770B1 (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.)
Rhone Poulenc Industries SA
Original Assignee
Rhone Poulenc Industries SA
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 Rhone Poulenc Industries SA filed Critical Rhone Poulenc Industries SA
Priority to FR7618232A priority Critical patent/FR2354770A1/en
Priority to FR7710763A priority patent/FR2386543A2/en
Priority to NL7706309A priority patent/NL7706309A/en
Priority to IE1208/77A priority patent/IE45091B1/en
Priority to AU26072/77A priority patent/AU2607277A/en
Priority to GB24850/77A priority patent/GB1521949A/en
Priority to ZA00773568A priority patent/ZA773568B/en
Priority to US05/806,344 priority patent/US4137315A/en
Priority to JP7041777A priority patent/JPS537700A/en
Priority to IL52317A priority patent/IL52317A0/en
Priority to SE7706946A priority patent/SE7706946L/en
Priority to PT66674A priority patent/PT66674B/en
Priority to DK265077A priority patent/DK265077A/en
Priority to LU77541A priority patent/LU77541A1/xx
Priority to BE178462A priority patent/BE855710A/en
Priority to DE19772727133 priority patent/DE2727133A1/en
Priority to ES459834A priority patent/ES459834A1/en
Priority to ES462933A priority patent/ES462933A1/en
Publication of FR2354770A1 publication Critical patent/FR2354770A1/en
Application granted granted Critical
Publication of FR2354770B1 publication Critical patent/FR2354770B1/fr
Granted legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
    • C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
    • C07D217/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • 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

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

Indolizino-isoquinolines of formula (I) and their acid addn., metal, and N-base addn. salts are new. In (I) R1 = H and R2 = H, amino or alkyl, opt. branched and opt. substd. on the final C by vinyl, ethynyl, COOH alkoxycarbonyl, CN, dialkoxymethyl, hydroxymethyl, dialkylaminoethyl (the 2 alkyls may complete an opt. N-methylated 5-6 membered satd. heterocycle opt. contg. an additional N, O or S atom) or trialkylammoniomethyl; or R2 is linear alkyl substd. on the final C by aminomethyl. In these cases R3+R4 form a bond. Alternatively, R1 + R4 = bond and R3 + R2 = CH2.CH(OR5)-. R5O=alkoxy substd. on the C atm alpha to R3-substd. N; all alkyl gps. and fragments contain 1-4C. (I) are antimicrobials and antifungals useful as local antiseptics. They are exceptionally low toxicity e.g. acute oral toxicity in mice is >0.75 g/kg. In an example 4-(2-hydroxyethylamino)-10-nitro-7-oxo-7H-indolizino 7,6,5-de isoquinoline was prepd. by reacting the corresp. 4-ethoxy cpd. with ethanolamine.
FR7618232A 1976-06-16 1976-06-16 Antimicrobial and antifungal indolizino-isoquinoline cpds. - with (10)-nitro and (7)-oxo substits., useful as local antiseptics Granted FR2354770A1 (en)

Priority Applications (18)

Application Number Priority Date Filing Date Title
FR7618232A FR2354770A1 (en) 1976-06-16 1976-06-16 Antimicrobial and antifungal indolizino-isoquinoline cpds. - with (10)-nitro and (7)-oxo substits., useful as local antiseptics
FR7710763A FR2386543A2 (en) 1976-06-16 1977-04-08 NEW DERIVATIVES OF NITRO-10 OXO-7 7H-INDOLIZINO (7,6,5-DE) ISOQUINOLEINE, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM
NL7706309A NL7706309A (en) 1976-06-16 1977-06-08 PROCESS FOR PREPARING 10-NITRO-7-OXO-7H-INDOLIZINO- (7,6,5-DE) ISOCHINOLINE, PROCESS FOR PREPARING A PHARMACEUTICAL PREPARATION USING IT AND SUCH PREPARATION AS PREPARED.
IL52317A IL52317A0 (en) 1976-06-16 1977-06-14 New derivatives of 10-nitro-7-oxo-7h-indolizino(7,6,5-de)isoquinoline processes for the preparation thereof and medicinal compositions containing the same
GB24850/77A GB1521949A (en) 1976-06-16 1977-06-14 Derivatives of 10-nitro-7-oxo-7h-indolizino(7,6,5-de)isoquinoline
ZA00773568A ZA773568B (en) 1976-06-16 1977-06-14 New derivatives of 10-nitro-7-oxo-7h-indolizino(7,6,5-de)isoquinoline
US05/806,344 US4137315A (en) 1976-06-16 1977-06-14 Derivatives of 10-nitro-7-oxo-7H-indolizino[7,6,5-de]isoquinoline
JP7041777A JPS537700A (en) 1976-06-16 1977-06-14 Novel 100nitroo77oxoo7 hh indolino *7*6*55d e* isoquinoline derivative
IE1208/77A IE45091B1 (en) 1976-06-16 1977-06-14 New derivatives of 10-nitro-7-oxo-7h-indolizino (7,6,5-de) isoquinoline
AU26072/77A AU2607277A (en) 1976-06-16 1977-06-14 New derivatives of 10-nitro-7-oxo-7-h-indolizino(7,6,5-de) isoquinoline
PT66674A PT66674B (en) 1976-06-16 1977-06-15 NOVEL DERIVATIVES OF NITRO-10 OXO-7H-INDOLIZINO / 7,6,5-DE / ISOQUINOLEINE PREPARATION THEREOF AND COMPOSITIONS CONTAINING SAME
SE7706946A SE7706946L (en) 1976-06-16 1977-06-15 PROCEDURE FOR MAKING A NEW DERIVATIVE OF 10-NITRO-7-OXO-7H-INDOLIZINO (7,6,5-DE) ISOKINOLINE
DK265077A DK265077A (en) 1976-06-16 1977-06-15 PROCEDURE FOR THE PREPARATION OF NOW UNKNOWN DERIVATIVES OF 10-NITRO-7-OXO-7H-INDOLIZINO (7,6,5-DE) ISOQUINOLINE
LU77541A LU77541A1 (en) 1976-06-16 1977-06-15
BE178462A BE855710A (en) 1976-06-16 1977-06-15 NEW DERIVATIVES OF NITRO-10 OXO-7H-INDOLIZINO (7,6,5-DE) ISOQUINOLEINE, THEIR PREPARATION AND THE COMPOSITIONS CONTAINING THEM
DE19772727133 DE2727133A1 (en) 1976-06-16 1977-06-16 NEW DERIVATIVES OF 10-NITRO-7-OXO- 7H-INDOLIZINO-SQUARE CLAMP ON 7,6,5- DE SQUARE BRACKET FOR -ISOCHINOLINE, THEIR PRODUCTION AND COMPOSITIONS OF THIS
ES459834A ES459834A1 (en) 1976-06-16 1977-06-16 Derivatives of 10-nitro-7-oxo-7H-indolizino{8 7,6,5-de{9 isoquinoline
ES462933A ES462933A1 (en) 1976-06-16 1977-10-05 Novel 100nitroo77oxoo7 hh indolino *7*6*55d e* isoquinoline derivative

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7618232A FR2354770A1 (en) 1976-06-16 1976-06-16 Antimicrobial and antifungal indolizino-isoquinoline cpds. - with (10)-nitro and (7)-oxo substits., useful as local antiseptics

Publications (2)

Publication Number Publication Date
FR2354770A1 true FR2354770A1 (en) 1978-01-13
FR2354770B1 FR2354770B1 (en) 1979-03-23

Family

ID=9174456

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7618232A Granted FR2354770A1 (en) 1976-06-16 1976-06-16 Antimicrobial and antifungal indolizino-isoquinoline cpds. - with (10)-nitro and (7)-oxo substits., useful as local antiseptics

Country Status (4)

Country Link
JP (1) JPS537700A (en)
ES (1) ES462933A1 (en)
FR (1) FR2354770A1 (en)
ZA (1) ZA773568B (en)

Also Published As

Publication number Publication date
ES462933A1 (en) 1978-06-01
ZA773568B (en) 1978-05-30
JPS537700A (en) 1978-01-24
FR2354770B1 (en) 1979-03-23

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Legal Events

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