FR2174746A1 - 1-methyl-4-anlino-5-aza indoles - antiinflammatories - Google Patents

1-methyl-4-anlino-5-aza indoles - antiinflammatories

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Publication number
FR2174746A1
FR2174746A1 FR7208256A FR7208256A FR2174746A1 FR 2174746 A1 FR2174746 A1 FR 2174746A1 FR 7208256 A FR7208256 A FR 7208256A FR 7208256 A FR7208256 A FR 7208256A FR 2174746 A1 FR2174746 A1 FR 2174746A1
Authority
FR
France
Prior art keywords
methyl
antiinflammatories
evapd
hal
degrees
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
FR7208256A
Other languages
French (fr)
Other versions
FR2174746B1 (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.)
Bpifrance Financement SA
Original Assignee
Agence National de Valorisation de la Recherche ANVAR
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 Agence National de Valorisation de la Recherche ANVAR filed Critical Agence National de Valorisation de la Recherche ANVAR
Priority to FR7208256A priority Critical patent/FR2174746A1/en
Publication of FR2174746A1 publication Critical patent/FR2174746A1/en
Application granted granted Critical
Publication of FR2174746B1 publication Critical patent/FR2174746B1/fr
Granted legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)

Abstract

Compounds of formula (I) are new: (where R1 and R2= H, lower alkyl, hydroxyalkyl, or alkoxy, halogen, CF3 or NO2) Antiinflammatories. EXAMPLE (II, hal=Cl) was prepd. by treating 1-methyl-4,5-dihydro-4-oxo-5-aza indole with POCl3 and treating the base with HCl. 20.3 g. (II; hal=Cl)HCl salt, were dissolved in 150 ml. ethylene glycol monomethyl ether and treated with 40.3 g. (III, R1= m-CF3, R2=H). The mixt. was refluxed for 4-5 hrs. The solvent was evapd. in vacuo on a steam bath, and the residue suspended in 120 ml. 10% NaOH. The product was extracted into chloroform, washed, dried and evapd., finishing with prolonged heating at 100 degrees C/10-15mm, to eliminate excess (III). The residue was recrystallised from cyclohexane/benzene (3:1) to give 21.8 g. 1-methyl-4(3-trifluoromethylanilino)-5-azaindole m.pt. 119-120 degrees C.
FR7208256A 1972-03-09 1972-03-09 1-methyl-4-anlino-5-aza indoles - antiinflammatories Granted FR2174746A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7208256A FR2174746A1 (en) 1972-03-09 1972-03-09 1-methyl-4-anlino-5-aza indoles - antiinflammatories

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7208256A FR2174746A1 (en) 1972-03-09 1972-03-09 1-methyl-4-anlino-5-aza indoles - antiinflammatories

Publications (2)

Publication Number Publication Date
FR2174746A1 true FR2174746A1 (en) 1973-10-19
FR2174746B1 FR2174746B1 (en) 1975-04-25

Family

ID=9094930

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7208256A Granted FR2174746A1 (en) 1972-03-09 1972-03-09 1-methyl-4-anlino-5-aza indoles - antiinflammatories

Country Status (1)

Country Link
FR (1) FR2174746A1 (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021123294A1 (en) * 2019-12-18 2021-06-24 Janssen Pharmaceutica Nv Oga inhibitor compounds

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2021123294A1 (en) * 2019-12-18 2021-06-24 Janssen Pharmaceutica Nv Oga inhibitor compounds

Also Published As

Publication number Publication date
FR2174746B1 (en) 1975-04-25

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