FR2463765A1 - Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire - Google Patents
Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire Download PDFInfo
- Publication number
- FR2463765A1 FR2463765A1 FR7920907A FR7920907A FR2463765A1 FR 2463765 A1 FR2463765 A1 FR 2463765A1 FR 7920907 A FR7920907 A FR 7920907A FR 7920907 A FR7920907 A FR 7920907A FR 2463765 A1 FR2463765 A1 FR 2463765A1
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- FR
- France
- Prior art keywords
- group
- lower alkyl
- base
- isomers
- ethyl acetate
- 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.)
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- 210000000748 cardiovascular system Anatomy 0.000 title claims abstract description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical class C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 title abstract description 5
- 229940054051 antipsychotic indole derivative Drugs 0.000 title 1
- 239000003814 drug Substances 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 20
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 239000002904 solvent Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 125000001041 indolyl group Chemical group 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000002619 bicyclic group Chemical group 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical group 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000002252 acyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims description 2
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 150000007524 organic acids Chemical class 0.000 claims description 2
- 235000005985 organic acids Nutrition 0.000 claims description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 7
- 239000013543 active substance Substances 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 1
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- 239000000126 substance Substances 0.000 claims 1
- 108700026220 vif Genes Proteins 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 37
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 28
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- -1 alkyl radical Chemical class 0.000 description 14
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 13
- 230000000694 effects Effects 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
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- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 238000011282 treatment Methods 0.000 description 4
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- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 239000010413 mother solution Substances 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 239000002540 palm oil Substances 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 229960002275 pentobarbital sodium Drugs 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 230000036470 plasma concentration Effects 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 150000003138 primary alcohols Chemical group 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 229960003712 propranolol Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000002685 pulmonary effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000029058 respiratory gaseous exchange Effects 0.000 description 1
- 230000033764 rhythmic process Effects 0.000 description 1
- 210000003752 saphenous vein Anatomy 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000006794 tachycardia Effects 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 210000003437 trachea Anatomy 0.000 description 1
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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (8)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7920907A FR2463765A1 (fr) | 1979-08-17 | 1979-08-17 | Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire |
| JP11045680A JPS5699413A (en) | 1979-08-17 | 1980-08-13 | Cardiovascularly active indole derivative |
| DE8080401180T DE3067264D1 (en) | 1979-08-17 | 1980-08-13 | Indole derivatives, process for their preparation and medicaments containing them |
| EP80401180A EP0025727B1 (fr) | 1979-08-17 | 1980-08-13 | Dérivés de l'indole, procédé pour leur préparation et médicaments les contenant |
| CA000359075A CA1161849A (en) | 1979-08-17 | 1980-08-15 | Derivatives of indole active on the cardiovascular system |
| US06/178,550 US4404217A (en) | 1979-08-17 | 1980-08-15 | 3-Indolyl alkylene amino propanols and cardiovascular compositions thereof |
| CA000426344A CA1164464A (en) | 1979-08-17 | 1983-04-20 | Derivatives of indole active on the cardiovascular system |
| US06/530,699 US4510315A (en) | 1979-08-17 | 1983-09-09 | 4[3-(1,1-Dimethyl-2-3(3-indolyl)ethylamino)-2-hydroxypropoxy]indole |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7920907A FR2463765A1 (fr) | 1979-08-17 | 1979-08-17 | Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2463765A1 true FR2463765A1 (fr) | 1981-02-27 |
| FR2463765B1 FR2463765B1 (OSRAM) | 1983-01-21 |
Family
ID=9228923
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR7920907A Granted FR2463765A1 (fr) | 1979-08-17 | 1979-08-17 | Nouveaux derives de l'indole actifs sur le systeme cardiovasculaire |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US4404217A (OSRAM) |
| EP (1) | EP0025727B1 (OSRAM) |
| JP (1) | JPS5699413A (OSRAM) |
| CA (1) | CA1161849A (OSRAM) |
| DE (1) | DE3067264D1 (OSRAM) |
| FR (1) | FR2463765A1 (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2505337A1 (fr) * | 1981-05-07 | 1982-11-12 | Bristol Myers Co | Nouveaux thienyl- et benzothienyl-tert-butylaminophenoxypropanols utiles comme medicaments b-bloquants selectifs |
| FR2638747A1 (fr) * | 1988-11-08 | 1990-05-11 | Synthelabo | Derives de phenyloxypropanolamines, leur preparation et leur application en therapeutique |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3119796A1 (de) * | 1981-05-19 | 1982-12-23 | Hoechst Ag, 6000 Frankfurt | Substituierte tryptaminderivate von thienyloxpropanolaminen, verfahren zu ihrer herstellung, pharmazeutische praeparate auf basis dieser verbindungen sowie ihre verwendung |
| FR2523964B1 (fr) * | 1982-03-23 | 1985-09-27 | Sanofi Sa | Nouveaux derives de la tryptamine actifs notamment sur le systeme cardiovasculaire et procede pour leur preparation |
| FR2543952B1 (fr) * | 1982-09-03 | 1986-02-21 | Bristol Myers Co | Composes hydrocarbones heterocycliques appartenant aux series indoliques et leur application pharmacologique |
| NZ208337A (en) * | 1983-06-10 | 1988-10-28 | Bristol Myers Co | 2-(2-hydroxy-3-((2-(ar-hydroxy-1h-aminopropoxy-yl)ethyl benzonitriles and pharmaceutical compositions |
| FR2589863B1 (fr) * | 1985-11-12 | 1988-07-29 | Sanofi Sa | Derives d'hydroxy-4 indole, leur procede de preparation et leur utilisation |
| FR2601008B1 (fr) * | 1986-07-03 | 1990-03-30 | Sanofi Sa | Procede de synthese stereospecifique de derives de l'indole |
| US5189179A (en) * | 1990-08-29 | 1993-02-23 | Merrell Dow Pharmaceuticals Inc. | Serotonin 5ht1a agonists |
| US5436264A (en) * | 1993-08-19 | 1995-07-25 | Syntex (U.S.A.) Inc. | N-aryloxyalkyl tryptamine α1 -adrenergic receptor antagonists |
| AU3386199A (en) * | 1998-04-08 | 1999-10-25 | American Home Products Corporation | N-aryloxyethyl-indoly-alkylamines for the treatment of depression (5-ht1a receptor active agents) |
| US6121307A (en) * | 1998-04-08 | 2000-09-19 | American Home Products Corp. | N-aryloxyethyl-indoly-alkylamines for the treatment of depression |
| DE10306941A1 (de) * | 2003-02-18 | 2004-08-26 | Merck Patent Gmbh | Benzofuranoxyethylamine |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2001633A (en) * | 1977-07-13 | 1979-02-07 | Bristol Myers Co | Anti-hypertensive 3-indolyl- tertiary butylaminopropanols |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH585199A5 (OSRAM) * | 1972-09-15 | 1977-02-28 | Siegfried Ag | |
| US4234595A (en) * | 1977-07-13 | 1980-11-18 | Mead Johnson & Company | 3-Indolyl-tertiary butylaminopropanols |
-
1979
- 1979-08-17 FR FR7920907A patent/FR2463765A1/fr active Granted
-
1980
- 1980-08-13 JP JP11045680A patent/JPS5699413A/ja active Pending
- 1980-08-13 DE DE8080401180T patent/DE3067264D1/de not_active Expired
- 1980-08-13 EP EP80401180A patent/EP0025727B1/fr not_active Expired
- 1980-08-15 US US06/178,550 patent/US4404217A/en not_active Expired - Lifetime
- 1980-08-15 CA CA000359075A patent/CA1161849A/en not_active Expired
-
1983
- 1983-09-09 US US06/530,699 patent/US4510315A/en not_active Expired - Fee Related
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2001633A (en) * | 1977-07-13 | 1979-02-07 | Bristol Myers Co | Anti-hypertensive 3-indolyl- tertiary butylaminopropanols |
Non-Patent Citations (1)
| Title |
|---|
| CA1966 * |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2505337A1 (fr) * | 1981-05-07 | 1982-11-12 | Bristol Myers Co | Nouveaux thienyl- et benzothienyl-tert-butylaminophenoxypropanols utiles comme medicaments b-bloquants selectifs |
| FR2638747A1 (fr) * | 1988-11-08 | 1990-05-11 | Synthelabo | Derives de phenyloxypropanolamines, leur preparation et leur application en therapeutique |
| EP0370852A1 (fr) * | 1988-11-08 | 1990-05-30 | Synthelabo | Dérivés de phényloxypropanolamines, leur préparation et leur application en thérapeutique |
| US5001132A (en) * | 1988-11-08 | 1991-03-19 | Synthelabo | Phenyloxypropanolamine derivatives and their application in therapeutics |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0025727B1 (fr) | 1984-03-28 |
| FR2463765B1 (OSRAM) | 1983-01-21 |
| CA1161849A (en) | 1984-02-07 |
| JPS5699413A (en) | 1981-08-10 |
| US4510315A (en) | 1985-04-09 |
| DE3067264D1 (en) | 1984-05-03 |
| US4404217A (en) | 1983-09-13 |
| EP0025727A1 (fr) | 1981-03-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| TP | Transmission of property | ||
| ST | Notification of lapse |