FR2211249A1 - Cyclopropyl-substd. indomethacine analogues - anti-inflammatory, anti-pyretics, anti-arthritic and dermatologically active - Google Patents

Cyclopropyl-substd. indomethacine analogues - anti-inflammatory, anti-pyretics, anti-arthritic and dermatologically active

Info

Publication number
FR2211249A1
FR2211249A1 FR7345774A FR7345774A FR2211249A1 FR 2211249 A1 FR2211249 A1 FR 2211249A1 FR 7345774 A FR7345774 A FR 7345774A FR 7345774 A FR7345774 A FR 7345774A FR 2211249 A1 FR2211249 A1 FR 2211249A1
Authority
FR
France
Prior art keywords
alkyl
cyclopropyl
co2h
halo
phenyl
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.)
Withdrawn
Application number
FR7345774A
Other languages
French (fr)
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.)
Merck and Co Inc
Original Assignee
Merck and Co 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 Merck and Co Inc filed Critical Merck and Co Inc
Publication of FR2211249A1 publication Critical patent/FR2211249A1/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C07D209/16—Tryptamines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/06—Compounds containing nitro groups bound to a carbon skeleton having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
    • C07C205/07—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms
    • C07C205/11—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by halogen atoms having nitro groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/12—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/04—Indoles; Hydrogenated indoles
    • C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
    • C07D209/18—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D209/26—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with an acyl radical attached to the ring nitrogen atom

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Indole Compounds (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

Indomethacine derivs., useful as fabrifuges, are of formula (I) (where R1 may be H or R5CO-, R5 being (halo)-phenyl, alkyl thiophenyl, alkyl sulphinylphenyl, alkyl sulphonyl-phenyl, (halo)alkyl phenyl, alkoxy-phenyl, nitrophenyl, aminophenyl, alkyl aminophenyl, di(alkyl)aminophenyl, (halo)styryl, alkyl thiostyryl, alkyl sulphinylstyryl, alkyl sulphonylstyryl, halo(alkyl)styryl, alkyl styryl or alkoxystyryl; R2 may me alkyl or cyclopropyl; R3 may be -CO2H, -CH(R7)-N(R6)2, R6 and R7 being H or alkyl; R4 may be H, alkyl, alkoxy, halogen, cyclopropyl, -CN or di-(alkyl)amino and R8 may be H or alkyl with the proviso that either R2 or R4 be cyclopropyl; all alkyl, alkoxy being lower), are made by (A) when R3 is -CO2H and R1 is H, reacting (II) with an alpha-bromocarboxylic acid, (B) when R3 is -CO2H and R1 is R5CO, heating a cpd. (III), (C) when R3 is -CO2H or -CH(R7)OH, reacting a cpd. (IV) in the presence of H3PO4 and (D) when R3 is -CH(R7)N(R6)2, reducing a cpd. (V) in the presence of a lower alkanal (when R6 is a lower alkyl) and in the absence of an alkanal (where R6 = H).
FR7345774A 1972-12-21 1973-12-20 Cyclopropyl-substd. indomethacine analogues - anti-inflammatory, anti-pyretics, anti-arthritic and dermatologically active Withdrawn FR2211249A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US31749672A 1972-12-21 1972-12-21

Publications (1)

Publication Number Publication Date
FR2211249A1 true FR2211249A1 (en) 1974-07-19

Family

ID=23233909

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7345774A Withdrawn FR2211249A1 (en) 1972-12-21 1973-12-20 Cyclopropyl-substd. indomethacine analogues - anti-inflammatory, anti-pyretics, anti-arthritic and dermatologically active

Country Status (4)

Country Link
JP (1) JPS4988868A (en)
DE (1) DE2363608A1 (en)
FR (1) FR2211249A1 (en)
NL (1) NL7316677A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2438651A1 (en) * 1978-10-12 1980-05-09 Glaxo Group Ltd NOVEL INDOLE DERIVATIVES USEFUL AS MEDICAMENTS, METHODS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2488606A1 (en) * 1980-08-12 1982-02-19 Glaxo Group Ltd INDOLIC DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATIONS AS MEDICAMENTS
US4839377A (en) * 1980-08-12 1989-06-13 Glaxo Group Limited 5-substituted 3-aminoalkyl indoles

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP6090666B2 (en) * 2013-05-20 2017-03-08 国立大学法人富山大学 Indole derivatives and hypoglycemic agents.

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2438651A1 (en) * 1978-10-12 1980-05-09 Glaxo Group Ltd NOVEL INDOLE DERIVATIVES USEFUL AS MEDICAMENTS, METHODS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
FR2488606A1 (en) * 1980-08-12 1982-02-19 Glaxo Group Ltd INDOLIC DERIVATIVES, THEIR PREPARATION AND THEIR APPLICATIONS AS MEDICAMENTS
US4839377A (en) * 1980-08-12 1989-06-13 Glaxo Group Limited 5-substituted 3-aminoalkyl indoles

Also Published As

Publication number Publication date
NL7316677A (en) 1974-06-25
JPS4988868A (en) 1974-08-24
DE2363608A1 (en) 1974-06-27

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