FR2431491A1 - 5-Amino-alkoxy-acetyl or styryl-carbonyl benzofuran and indole derivs. - have cardiovascular esp. antiarrhythmic and diuretic activity - Google Patents

5-Amino-alkoxy-acetyl or styryl-carbonyl benzofuran and indole derivs. - have cardiovascular esp. antiarrhythmic and diuretic activity

Info

Publication number
FR2431491A1
FR2431491A1 FR7821290A FR7821290A FR2431491A1 FR 2431491 A1 FR2431491 A1 FR 2431491A1 FR 7821290 A FR7821290 A FR 7821290A FR 7821290 A FR7821290 A FR 7821290A FR 2431491 A1 FR2431491 A1 FR 2431491A1
Authority
FR
France
Prior art keywords
acetyl
para
methyl
styrylcarbonyl
nr2r3
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Withdrawn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
FR7821290A
Other languages
French (fr)
Inventor
T Imbert
A Lacour
M Turin
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.)
Synthelabo SA
Original Assignee
Delalande 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 Delalande SA filed Critical Delalande SA
Priority to FR7821290A priority Critical patent/FR2431491A1/en
Publication of FR2431491A1 publication Critical patent/FR2431491A1/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Withdrawn legal-status Critical Current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
    • C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
    • C07D209/32—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
    • C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
    • C07D307/80—Radicals substituted by oxygen atoms

Landscapes

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

Abstract

5-Aminoalkoxy-acetyl or styryl-carbonyl substd. benzofurans and indoles of formula (I) and their acid addition salts are new: (where (a) X = O, R1 = 2-methyl; A = -(CH2)2- or -(CH2)3; NR2R3=dimethylamino, diethylamino, pyrrolidino, piperidino, morpholino, hexamethyleneimino, or 4-methylpiperazino, and -COR in position 3 = acetyl or a styrylcarbonyl gp. (A) and R4 = H, para-Cl, para-hydroxy, para-methyl, ortho, meta or para-methoxy or 3,4,5-trimethoxy; (b) X = O, R1 = 2-methyl; A = -(CH2)2-; NR2R3 = guanidino (-NH-C(NH)-NH2) or imidazoline-2-amino and -COR in position 3 = acetyl or para-methoxy-styrylcarbonyl; (c) X = O; R1 = 2-methyl; A = -CH2-CH(OH)-CH2-; NR2R3 = isopropylamino; -COR in position 3 = acetyl or para-R5-styrylcarbonyl and R5 = Cl, methyl, methoxy or H; (d) X = O; R1 = H; A = -(CH2)2-; NR2R3 = piperidino; -COR in position 3 = acetyl or para-R6-styrylcarbonyl and R6 = methyl or methoxy; (e) X = -NCH3-; R1 = 2-methyl; A = -(CH2)2-; NR2R3 = dimethylamino, diethylamino or piperidino and -COR in position 3 = acetyl or para-R6-styrylcarbonyl and (f) X = O, R1 = 3-methyl; A = -CH2)2-= -NR2R3 = dimethylamino, diethylamino or piperidino and -COR in position 2 = acetyl or para-R6-styrylcarbonyl. Intermediates (VI) and (VII) are also new cpds. (I) are cardiovascular agents especially antiarrhythmics and diuretics which may be administered orally 10-300 mg. 2-6 times daily or parenterally (5-50 mg., 1-4 times daily). Curing tests and toxicity tests (LD50 i.v. in mice 26-74 mg./kg. in tested cpds.) are described.
FR7821290A 1978-07-18 1978-07-18 5-Amino-alkoxy-acetyl or styryl-carbonyl benzofuran and indole derivs. - have cardiovascular esp. antiarrhythmic and diuretic activity Withdrawn FR2431491A1 (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
FR7821290A FR2431491A1 (en) 1978-07-18 1978-07-18 5-Amino-alkoxy-acetyl or styryl-carbonyl benzofuran and indole derivs. - have cardiovascular esp. antiarrhythmic and diuretic activity

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR7821290A FR2431491A1 (en) 1978-07-18 1978-07-18 5-Amino-alkoxy-acetyl or styryl-carbonyl benzofuran and indole derivs. - have cardiovascular esp. antiarrhythmic and diuretic activity

Publications (1)

Publication Number Publication Date
FR2431491A1 true FR2431491A1 (en) 1980-02-15

Family

ID=9210853

Family Applications (1)

Application Number Title Priority Date Filing Date
FR7821290A Withdrawn FR2431491A1 (en) 1978-07-18 1978-07-18 5-Amino-alkoxy-acetyl or styryl-carbonyl benzofuran and indole derivs. - have cardiovascular esp. antiarrhythmic and diuretic activity

Country Status (1)

Country Link
FR (1) FR2431491A1 (en)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0058977A1 (en) * 1981-02-25 1982-09-01 Hoechst-Roussel Pharmaceuticals Incorporated 1,2-Benzisoxazoloxyethylamines, their intermediates, a process for their preparation, pharmaceutical composition containing the same and their use as diuretics
US5192799A (en) * 1987-12-11 1993-03-09 Mitsui Petrochemical Industries, Ltd. Coumaran group containing amine compounds and their acid addition salts and quaternary ammonium salts and the use thereof as anti arrhythmic agents and as psychotropic agents
EP1942896A2 (en) * 2005-11-04 2008-07-16 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (flap) inhibitors
US7977359B2 (en) 2005-11-04 2011-07-12 Amira Pharmaceuticals, Inc. 5-lipdxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en) 2005-11-04 2013-03-19 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US8546431B2 (en) 2008-10-01 2013-10-01 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US8697730B2 (en) 2007-10-26 2014-04-15 Panmira Pharmaceuticals, Llc 5-lipoxygenase activating protein (FLAP) inhibitor
US8772495B2 (en) 2008-05-23 2014-07-08 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein inhibitor
WO2023227696A1 (en) * 2022-05-25 2023-11-30 Katholieke Universiteit Leuven New derivatives for treating trpm3 mediated disorders

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1415355A (en) * 1963-12-02 1965-10-22 Haessle Ab Benzofuran derivatives and process for obtaining
FR5157M (en) * 1965-12-23 1967-07-17

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1415355A (en) * 1963-12-02 1965-10-22 Haessle Ab Benzofuran derivatives and process for obtaining
FR5157M (en) * 1965-12-23 1967-07-17

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0058977A1 (en) * 1981-02-25 1982-09-01 Hoechst-Roussel Pharmaceuticals Incorporated 1,2-Benzisoxazoloxyethylamines, their intermediates, a process for their preparation, pharmaceutical composition containing the same and their use as diuretics
US5192799A (en) * 1987-12-11 1993-03-09 Mitsui Petrochemical Industries, Ltd. Coumaran group containing amine compounds and their acid addition salts and quaternary ammonium salts and the use thereof as anti arrhythmic agents and as psychotropic agents
EP1942896A2 (en) * 2005-11-04 2008-07-16 Amira Pharmaceuticals, Inc. 5-lipoxygenase-activating protein (flap) inhibitors
EP1942896A4 (en) * 2005-11-04 2010-06-02 Amira Pharmaceuticals Inc 5-lipoxygenase-activating protein (flap) inhibitors
US7977359B2 (en) 2005-11-04 2011-07-12 Amira Pharmaceuticals, Inc. 5-lipdxygenase-activating protein (FLAP) inhibitors
US8399666B2 (en) 2005-11-04 2013-03-19 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US8710081B2 (en) 2005-11-04 2014-04-29 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US8841295B2 (en) 2005-11-04 2014-09-23 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
US8697730B2 (en) 2007-10-26 2014-04-15 Panmira Pharmaceuticals, Llc 5-lipoxygenase activating protein (FLAP) inhibitor
US8772495B2 (en) 2008-05-23 2014-07-08 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein inhibitor
US8546431B2 (en) 2008-10-01 2013-10-01 Panmira Pharmaceuticals, Llc 5-lipoxygenase-activating protein (FLAP) inhibitors
WO2023227696A1 (en) * 2022-05-25 2023-11-30 Katholieke Universiteit Leuven New derivatives for treating trpm3 mediated disorders

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