ES346057A1 - 1-(2' 3' 4'-trisubstituted phenyl)-2-amino-alkanols-(1) and salts thereof - Google Patents
1-(2' 3' 4'-trisubstituted phenyl)-2-amino-alkanols-(1) and salts thereofInfo
- Publication number
- ES346057A1 ES346057A1 ES346057A ES346057A ES346057A1 ES 346057 A1 ES346057 A1 ES 346057A1 ES 346057 A ES346057 A ES 346057A ES 346057 A ES346057 A ES 346057A ES 346057 A1 ES346057 A1 ES 346057A1
- Authority
- ES
- Spain
- Prior art keywords
- alkyl
- formula
- compound
- reducing
- diphenylmethylenedioxyacetophenone
- 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.)
- Expired
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/13—Amines
- A61K31/135—Amines having aromatic rings, e.g. ketamine, nortriptyline
Landscapes
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Racemic and optically active compounds of the general formula (R 1 = H, acyl R 2 =C 1-5 alkyl or alkoxy, C 5-6 cycloalkyl R 3 = H, C 1-4 alkyl K 4 = C 1-8 alkyl, cyoloalkyl containing up to 7 carbon atoms, benzodioxan-2-yl-(C 1-3 alkyl) or wherein Z = C 2-6 alkylene n = 0, 1 R 5,6 = H, OH, C 1-4 alkyl or alkoxy or R 5 + 6 = OCH 2 O provided that R 4 is not Pri if R 1 = H, R 2 = Me, MeO and R 3 = H, Me, Et) and their salts are prepared by (a) reducing a compound of the formula (R1 = R 1 or protecting group or OR1R1O = acetal group R11 = H or protecting group) (b) reducing a compound of the formula (R 7 = CO, CHOH) in the presence of R 4 NH 2 or, when R, = CHOH, condensing the two reactants and reducing the product (c) reacting a compound of the formula (E = oxiranyl or alkyloxiranyl and/or 2 halo-1- hydroxyalkyl) with R 4 R11NH (d) reacting a compound of the formula under reducing conditions with R 8 R 9 CO (R 8 = H or straight chain C 1-4 alkyl, R 9 = alkyl, sum of carbon atoms in R 8 + 9 is not more than 7, or R 9 = 1,4-benzodioxan-2-yl, 1,4-benzodioxan- 2 - ylmethyl, 1,4 - benzodioxan - 2 - ylethyl or wherein Z1 = alkylene, sum of carbon atoms in Z1 and R 8 is not more than 5, or R 8 + 9 = alkylene containing up to 6 carbon atoms) (e) -when R 3 = H-reducing a compound of the formula or (f) reacting a compound of the formula with a reactive ester of R 4 OH, optionally followed in each case by salt formation and/or resolution. The preparation of starting materials for processes (a)-(f) by standard methods and of 2 - ethoxy - 3,4 - diphenylmethylenedioxyacetophenone, 3 - allyloxy - 4 - methoxyacetophenone, 2 - allyl - 3 - hydroxy - 4 - methoxyacetophenone- 2 - propyl - 3 - hydroxy - 4 - methoxyacetophenone, 2 - propyl - 3 - acetoxy - 4 - methoxybromoacetophenone, [alpha] - bromo - 2 - methyl - 3,4 - dimethoxyacetophenone, 2 - hydroxy - 3,4 - diphenylmethylenedioxyacetophenone, 2 - methoxy - 3,4 - diphenylmethylenedioxyacetophenone, [alpha] - bromo- 2 - methoxy - 3,4 - diphenylmethylenedioxyacetophenone, 2 - methoxy - 3,4 - diphenylmethylenedioxybutyrophenone and [alpha] - bromo - 2 - methoxy- 3,4 - diphenylmethylenedioxybutyrophenone is described. The compounds of the invention are sympathomimetics, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEB0089417 | 1966-10-18 | ||
| DEB0089476 | 1966-10-20 | ||
| DEB0090062 | 1966-11-29 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES346057A1 true ES346057A1 (en) | 1969-03-16 |
Family
ID=27209389
Family Applications (6)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES346057A Expired ES346057A1 (en) | 1966-10-18 | 1967-10-14 | 1-(2' 3' 4'-trisubstituted phenyl)-2-amino-alkanols-(1) and salts thereof |
| ES360963A Expired ES360963A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-hydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360964A Expired ES360964A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360962A Expired ES360962A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360965A Expired ES360965A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360961A Expired ES360961A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
Family Applications After (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES360963A Expired ES360963A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-hydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360964A Expired ES360964A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360962A Expired ES360962A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360965A Expired ES360965A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
| ES360961A Expired ES360961A1 (en) | 1966-10-18 | 1968-11-30 | Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3657244A (en) |
| AT (3) | AT285582B (en) |
| BE (1) | BE705312A (en) |
| CH (4) | CH490323A (en) |
| DE (2) | DE1543372A1 (en) |
| DK (1) | DK130070B (en) |
| ES (6) | ES346057A1 (en) |
| FR (1) | FR7338M (en) |
| GB (1) | GB1204195A (en) |
| NL (1) | NL158480B (en) |
| SE (2) | SE368196B (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3969410A (en) * | 1972-01-12 | 1976-07-13 | Boehringer Ingelheim Gmbh | 1-(2'-Alkyl-3',4'-dihydroxy-phenyl)-2-(phenylalkyl-amino)-alkanols-(1) and salts thereof |
| US4042713A (en) * | 1966-10-18 | 1977-08-16 | Boehringer Ingelheim Gmbh | Pharmaceutical compositions containing a 1-(2-alkyl-3,4-dihydroxy-phenyl)-2-(phenylalkyl-amino)-alkanol-(1) and method of use |
| US4336400A (en) * | 1969-04-01 | 1982-06-22 | Sterling Drug Inc. | 3-(Hydroxy or hydroxymethyl)-4-hydroxy-alpha(aminomethyl)benzyl alcohols and methods of use |
| US4138581A (en) * | 1969-04-01 | 1979-02-06 | Sterling Drugs Inc. | 3(Hydroxy or hydroxymethyl)-4(hydroxy)-α-(aminomethyl)benzyl alcohols |
| DE1962497C3 (en) * | 1969-12-12 | 1979-09-20 | C.H. Boehringer Sohn, 6507 Ingelheim | Naphthylalkyl-a-hydroxyphenethyl-amines, their preparation and pharmaceuticals containing them |
| US4147799A (en) * | 1971-06-24 | 1979-04-03 | Kyowa Hakko Kogyo Co., Ltd. | Process for reducing blood pressure and blocking β-adrenergic receptor |
| US3868461A (en) * | 1972-11-22 | 1975-02-25 | Interx Research Corp | Ester of 3,4-dihydroxy-alpha (isopropylamino) methyl benzyl alcohol, composition and anti-asthma use thereof |
| US3908017A (en) * | 1973-04-26 | 1975-09-23 | Interx Research Corp | Sympathomimetic compositions containing an ester of -3-hydroxy-{60 -{8 (methylamino)methyl{8 benzyl alcohol and methods of use |
| US4046913A (en) * | 1973-08-18 | 1977-09-06 | Boehringer Ingelheim Gmbh | 1-(M-alkanoyloxy-phenyl)-1-hydroxy-2-(N-lower alkyl-amino)-ethanes and salts thereof |
| US4192805A (en) * | 1975-11-27 | 1980-03-11 | Nicholas International Limited | Process of preparing amino ethanols |
| US4287212A (en) * | 1976-04-30 | 1981-09-01 | American Hoechst Corporation | 2-Aryl-1,2-dialkylcycloalkylamines |
| US4115585A (en) * | 1976-05-17 | 1978-09-19 | Instituto Luso Farmaco D'italia S.R.L. | Esters of 1-(p-hydroxyphenyl)-2-(1'-methyl-2'-phenoxyethylamino)-1-propanol |
| US4094983A (en) * | 1977-01-17 | 1978-06-13 | Interx Research Corporation | Method for reducing intraocular pressure in warm-blooded animals |
| US4590210A (en) * | 1979-03-09 | 1986-05-20 | Langham Maurice E | Compositions for treatment of ocular hypertension |
| US4275074A (en) * | 1979-03-09 | 1981-06-23 | Graham J. Dobbie | Catecholamine treatment of ocular hypertension |
| JPS55124742A (en) * | 1979-03-20 | 1980-09-26 | Kyowa Hakko Kogyo Co Ltd | Novel aminoalcohol derivative |
| JPS6241829Y2 (en) * | 1980-03-28 | 1987-10-26 | ||
| ATE7689T1 (en) | 1980-07-09 | 1984-06-15 | Aktiebolaget Draco | 1-(DIHYDROXYPHENYL)-2-AMINO-AETHANOL DERIVATIVES, PROCESSES AND MEANS FOR THEIR PREPARATION, AND AGENTS CONTAINING THESE DERIVATIVES. |
| DE3128117A1 (en) * | 1980-07-29 | 1982-03-11 | Yamanouchi Pharmaceutical Co., Ltd., Tokyo | NEW PHENYL-AETHYLAMINE DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF |
| US4472427A (en) * | 1980-12-23 | 1984-09-18 | Merck & Co., Inc. | (Aralkylamino-2-OR-propoxy)heterocyclic compounds |
| ES502470A0 (en) * | 1981-05-13 | 1982-04-01 | Ferrer Int | PROCEDURE FOR OBTAINING NEW AMINODERIVATIVES IN POSITION 1, FROM 1- (3 ', 4'-METHYLENDIOXIPHENYL) PROPAN-2-OL |
| US4461914A (en) * | 1983-02-01 | 1984-07-24 | American Cyanamid Company | Method for the preparation of 1-(4'-amino-3',5'-dichlorophenyl)-2-alkyl(or dialkyl)aminoethanols |
| LU85856A1 (en) * | 1984-04-17 | 1986-06-11 | Glaxo Group Ltd | PHENETHANOLAMINE COMPOUNDS |
| US4699928A (en) * | 1984-07-13 | 1987-10-13 | Merrell Dow Pharmaceuticals Inc. | Fluoroallylamine derivatives |
| US4843160A (en) * | 1984-10-01 | 1989-06-27 | The Dow Chemical Company | Preparation of alpha-aminoalkylphenols |
| US5068432A (en) * | 1988-03-30 | 1991-11-26 | Aldrich Chemical Company, Inc. | Process for producing optically pure 2-phenoxyphenylalkylamines |
| JPH02124884A (en) * | 1988-07-08 | 1990-05-14 | Zhongguo Yixuekexueyuan Yaowo Yanjiusuo | N-substituted amide derivative |
| DE10246374A1 (en) * | 2002-10-04 | 2004-04-15 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New 4-(2-alkylamino-1-hydroxyethyl)-3-alkoxy-benzene-1,2-diol derivatives, are beta-mimetics having a long duration of action, useful e.g. for treating asthma, chronic obstructive pulmonary disease or arrhythmia |
| US6951888B2 (en) | 2002-10-04 | 2005-10-04 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Betamimetics with a prolonged duration of activity, processes for preparing them, and their use as pharmaceutical compositions |
| DE10253220A1 (en) * | 2002-11-15 | 2004-05-27 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | New 2-(N-phenylalkyl-amino)-1-phenyl-ethanol derivatives, are beta-adrenergic agents especially useful for treating inflammatory and obstructive respiratory diseases such as asthma or COPD |
| CN110743544B (en) * | 2019-11-07 | 2023-02-24 | 西安凯立新材料股份有限公司 | Palladium-carbon catalyst for preparing alpha-phenylethyl alcohol by selective hydrogenation of acetophenone and preparation method and application thereof |
-
1966
- 1966-10-18 DE DE19661543372 patent/DE1543372A1/en active Pending
- 1966-10-20 DE DE1543374A patent/DE1543374C3/en not_active Expired
-
1967
- 1967-10-14 ES ES346057A patent/ES346057A1/en not_active Expired
- 1967-10-16 CH CH1442267A patent/CH490323A/en not_active IP Right Cessation
- 1967-10-16 CH CH513370A patent/CH507200A/en not_active IP Right Cessation
- 1967-10-16 US US713265A patent/US3657244A/en not_active Expired - Lifetime
- 1967-10-16 AT AT934967A patent/AT285582B/en not_active IP Right Cessation
- 1967-10-16 CH CH452872A patent/CH548365A/en not_active IP Right Cessation
- 1967-10-16 AT AT1165269A patent/AT288357B/en not_active IP Right Cessation
- 1967-10-16 AT AT1165369A patent/AT288358B/en not_active IP Right Cessation
- 1967-10-16 CH CH513470A patent/CH523219A/en not_active IP Right Cessation
- 1967-10-17 DK DK516167AA patent/DK130070B/en not_active IP Right Cessation
- 1967-10-18 SE SE14280/67A patent/SE368196B/xx unknown
- 1967-10-18 GB GB47491/67A patent/GB1204195A/en not_active Expired
- 1967-10-18 BE BE705312D patent/BE705312A/xx not_active IP Right Cessation
- 1967-10-18 SE SE7106612A patent/SE380792B/en unknown
- 1967-10-18 NL NL6714161.A patent/NL158480B/en not_active IP Right Cessation
-
1968
- 1968-01-18 FR FR136547A patent/FR7338M/fr not_active Expired
- 1968-11-30 ES ES360963A patent/ES360963A1/en not_active Expired
- 1968-11-30 ES ES360964A patent/ES360964A1/en not_active Expired
- 1968-11-30 ES ES360962A patent/ES360962A1/en not_active Expired
- 1968-11-30 ES ES360965A patent/ES360965A1/en not_active Expired
- 1968-11-30 ES ES360961A patent/ES360961A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1543374C3 (en) | 1973-10-04 |
| SE380792B (en) | 1975-11-17 |
| ES360963A1 (en) | 1970-11-16 |
| SE368196B (en) | 1974-06-24 |
| ES360961A1 (en) | 1970-11-16 |
| ES360964A1 (en) | 1970-10-16 |
| FR7338M (en) | 1969-10-13 |
| ES360965A1 (en) | 1970-11-16 |
| DE1543374B2 (en) | 1973-02-22 |
| AT288358B (en) | 1971-03-10 |
| GB1204195A (en) | 1970-09-03 |
| US3657244A (en) | 1972-04-18 |
| AT285582B (en) | 1970-11-10 |
| CH523219A (en) | 1972-05-31 |
| AT288357B (en) | 1971-03-10 |
| BE705312A (en) | 1968-04-18 |
| CH507200A (en) | 1971-05-15 |
| ES360962A1 (en) | 1970-11-16 |
| NL6714161A (en) | 1968-04-19 |
| DE1543374A1 (en) | 1972-04-20 |
| DK130070C (en) | 1975-05-26 |
| CH490323A (en) | 1970-05-15 |
| CH548365A (en) | 1974-04-30 |
| NL158480B (en) | 1978-11-15 |
| DE1543372A1 (en) | 1971-04-01 |
| DK130070B (en) | 1974-12-16 |
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