GB2001971A - 1-(indol-4-yloxy)-3-amino-2- propanol derivatives - Google Patents
1-(indol-4-yloxy)-3-amino-2- propanol derivativesInfo
- Publication number
- GB2001971A GB2001971A GB7830345A GB7830345A GB2001971A GB 2001971 A GB2001971 A GB 2001971A GB 7830345 A GB7830345 A GB 7830345A GB 7830345 A GB7830345 A GB 7830345A GB 2001971 A GB2001971 A GB 2001971A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- cyano
- alkoxy
- halogen
- alkyl
- 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
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
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- 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
- A61P9/06—Antiarrhythmics
-
- 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
- A61P9/08—Vasodilators for multiple indications
-
- 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
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D209/30—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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
The compounds of formula I <IMAGE> wherein R is a group <IMAGE> wherein A is C2-5 alkylene, X is a bond, oxygen or sulfur, R3 is hydrogen, hydroxy, C1-4 alkoxy, halogen of atomic number of from 9 to 35, cyano, carbamoyl or a group NHCORd, wherein Rd is C1-4 alkyl, and R4 is hydrogen and, when R3 is C1-4 alkoxy, R4 additionally may be C1-4 alkoxy or, when R3 is halogen of atomic number of from 9 to 35, R4 additionally may be halogen of atomic number of from 9 to 35 either i) R1 is hydrogen or methyl and R2 is cyano, CONRaRb, COORc or CH2ORe, wherein Ra, Rb, Rc and Re independently are hydrogen or C1-4 alkyl, or ii) either R1 is methyl and R2 is Cl or Br or R1 is Cl or Br and R2 is hydrogen or methyl, with the provisos that a) X is separated from the nitrogen atom of the 3-amino-2-hydroxy-propoxy chain by at least 2 carbon atoms, b) when X is a bond, P3 is other than hydrogen and c) when R2 is cyano, R additionally may be C3-7 alkyl are useful as alpha - and beta -adrenoceptor blocking, anti-arrhythmic and anti- hypertensive agents and as inhibitors of metabolic effects of emotional stress.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH907777A CH632246A5 (en) | 1977-07-21 | 1977-07-21 | Process for preparing novel 3-aminopropoxyindoles |
| CH907077 | 1977-07-21 | ||
| CH907377 | 1977-07-21 | ||
| CH906577 | 1977-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| GB2001971A true GB2001971A (en) | 1979-02-14 |
| GB2001971B GB2001971B (en) | 1982-02-10 |
Family
ID=27429188
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB7830345A Expired GB2001971B (en) | 1977-07-21 | 1978-07-19 | Organic compounds |
Country Status (18)
| Country | Link |
|---|---|
| JP (1) | JPS5422364A (en) |
| AU (1) | AU523105B2 (en) |
| BE (1) | BE869133A (en) |
| CA (1) | CA1098909A (en) |
| DE (1) | DE2830211A1 (en) |
| DK (1) | DK312878A (en) |
| ES (1) | ES471863A1 (en) |
| FI (1) | FI782229A (en) |
| FR (1) | FR2398058A1 (en) |
| GB (1) | GB2001971B (en) |
| IE (1) | IE47131B1 (en) |
| IL (1) | IL55170A (en) |
| IT (1) | IT1105092B (en) |
| NL (1) | NL7807626A (en) |
| NZ (1) | NZ187909A (en) |
| PT (1) | PT68317A (en) |
| SE (1) | SE435374B (en) |
| SU (1) | SU843740A3 (en) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2905877A1 (en) * | 1979-02-16 | 1980-08-28 | Boehringer Mannheim Gmbh | NEW AMINOPROPANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE3068678D1 (en) * | 1979-08-10 | 1984-08-30 | Sandoz Ag | 3-aminopropoxyaryl derivatives, their preparation and pharmaceutical compositions containing them |
| DE3029980A1 (en) * | 1980-08-08 | 1982-03-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | INDOLDER DERIVATIVES AND METHOD FOR THEIR PRODUCTION |
| DE3030047A1 (en) * | 1980-08-08 | 1982-03-11 | Boehringer Mannheim Gmbh, 6800 Mannheim | NEW AMINOPROPANOL DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| DE3131146A1 (en) * | 1981-08-06 | 1983-02-24 | Boehringer Mannheim Gmbh, 6800 Mannheim | NEW HETEROARYLOXYPROPANOLAMINE, METHOD FOR THE PRODUCTION THEREOF AND MEDICINAL PRODUCTS CONTAINING THESE COMPOUNDS |
| ZA967892B (en) * | 1995-09-21 | 1998-03-18 | Lilly Co Eli | Selective β3 adrenergic agonists. |
| US6022894A (en) | 1996-04-09 | 2000-02-08 | Nps Pharmaceuticals, Inc. | Method of using calcilytic compounds |
| US6818660B2 (en) | 1996-04-09 | 2004-11-16 | Nps Pharmaceuticals, Inc. | Calcilytic compounds |
| ATE215369T1 (en) * | 1996-09-05 | 2002-04-15 | Lilly Co Eli | CARBAZOLE ANALOGUES AS SELECTIVE BETA3-ADRENERGIC AGONISTS |
| TW483881B (en) | 1996-12-03 | 2002-04-21 | Nps Pharma Inc | Calcilytic compounds |
| US7202261B2 (en) | 1996-12-03 | 2007-04-10 | Nps Pharmaceuticals, Inc. | Calcilytic compounds |
| WO2001036412A1 (en) * | 1999-11-15 | 2001-05-25 | Eli Lilly And Company | Process for the preparation of aryloxy propanolamines |
| CN109310651A (en) * | 2016-05-13 | 2019-02-05 | 小利兰·斯坦福大学董事会 | Adrenergic receptor modulation compound and its application method |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1547056A (en) * | 1966-12-13 | 1968-11-22 | Sandoz Sa | Indole derivatives and their preparation |
| FR2019185A1 (en) * | 1968-09-30 | 1970-06-26 | Sandoz Sa | 4-(2-hydroxy-3-amino-propoxy)-indole-2-carboxy- - lic acids and esters and 2-hydroxymethylindoles as beta |
| US3699123A (en) * | 1970-03-24 | 1972-10-17 | Sandoz Ltd | 4-(3-amino-2-hydroxy-propoxy) indole derivatives |
| US4076829A (en) * | 1974-11-16 | 1978-02-28 | Boehringer Mannheim Gmbh | Aminopropanol compounds and compositions for the treatment of cardiac and circulatory diseases |
| DE2508251C2 (en) * | 1975-02-26 | 1983-12-29 | Boehringer Mannheim Gmbh, 6800 Mannheim | Derivatives of indole, processes for their preparation and medicaments containing them |
| DE2633839A1 (en) * | 1975-08-07 | 1977-02-24 | Sandoz Ag | NEW 4-AMINOPROPOXYINDOLDE DERIVATIVES, THEIR PRODUCTION AND USE |
| DE2635209C2 (en) * | 1975-08-15 | 1983-01-27 | Sandoz-Patent-GmbH, 7850 Lörrach | 4- (2-Benzoyloxy-3-tert-butylamino-propoxy) -2-methylindole, its (S) -enantiomer, their acid addition salts, processes for their preparation and medicaments containing these compounds |
-
1978
- 1978-07-10 DE DE19782830211 patent/DE2830211A1/en not_active Ceased
- 1978-07-12 DK DK312878A patent/DK312878A/en not_active Application Discontinuation
- 1978-07-12 FI FI782229A patent/FI782229A/en not_active Application Discontinuation
- 1978-07-12 SE SE7807753A patent/SE435374B/en unknown
- 1978-07-14 IT IT50299/78A patent/IT1105092B/en active
- 1978-07-17 NL NL7807626A patent/NL7807626A/en not_active Application Discontinuation
- 1978-07-19 AU AU38182/78A patent/AU523105B2/en not_active Expired
- 1978-07-19 NZ NZ187909A patent/NZ187909A/en unknown
- 1978-07-19 PT PT68317A patent/PT68317A/en unknown
- 1978-07-19 SU SU782639449A patent/SU843740A3/en active
- 1978-07-19 GB GB7830345A patent/GB2001971B/en not_active Expired
- 1978-07-19 ES ES471863A patent/ES471863A1/en not_active Expired
- 1978-07-19 IE IE1448/78A patent/IE47131B1/en unknown
- 1978-07-19 BE BE189392A patent/BE869133A/en not_active IP Right Cessation
- 1978-07-19 IL IL55170A patent/IL55170A/en unknown
- 1978-07-20 JP JP8781878A patent/JPS5422364A/en active Pending
- 1978-07-20 CA CA307,768A patent/CA1098909A/en not_active Expired
- 1978-07-21 FR FR7821679A patent/FR2398058A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| IL55170A (en) | 1982-07-30 |
| DK312878A (en) | 1979-01-22 |
| SE7807753L (en) | 1979-01-22 |
| IT1105092B (en) | 1985-10-28 |
| IE781448L (en) | 1979-01-21 |
| AU3818278A (en) | 1980-01-24 |
| SE435374B (en) | 1984-09-24 |
| FR2398058B1 (en) | 1982-08-06 |
| JPS5422364A (en) | 1979-02-20 |
| IE47131B1 (en) | 1983-12-28 |
| FR2398058A1 (en) | 1979-02-16 |
| NZ187909A (en) | 1981-04-24 |
| IL55170A0 (en) | 1978-09-29 |
| CA1098909A (en) | 1981-04-07 |
| FI782229A (en) | 1979-01-22 |
| SU843740A3 (en) | 1981-06-30 |
| ES471863A1 (en) | 1979-10-01 |
| DE2830211A1 (en) | 1979-02-01 |
| BE869133A (en) | 1979-01-19 |
| PT68317A (en) | 1978-08-01 |
| NL7807626A (en) | 1979-01-23 |
| IT7850299A0 (en) | 1978-07-14 |
| AU523105B2 (en) | 1982-07-15 |
| GB2001971B (en) | 1982-02-10 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |