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 activityInfo
- 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- Withdrawn
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
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.
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)
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)
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 |
-
1978
- 1978-07-18 FR FR7821290A patent/FR2431491A1/en not_active Withdrawn
Patent Citations (2)
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)
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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Legal Events
Date | Code | Title | Description |
---|---|---|---|
ST | Notification of lapse |