ES360962A1 - Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding) - Google Patents
Procedure for the obtaining of 3,4-dihydroxyphenylalkanolamines. (Machine-translation by Google Translate, not legally binding)Info
- Publication number
- ES360962A1 ES360962A1 ES360962A ES360962A ES360962A1 ES 360962 A1 ES360962 A1 ES 360962A1 ES 360962 A ES360962 A ES 360962A ES 360962 A ES360962 A ES 360962A ES 360962 A1 ES360962 A1 ES 360962A1
- Authority
- ES
- Spain
- Prior art keywords
- group
- carbon atoms
- hydrogen atom
- formula
- groups
- 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
- 238000000034 method Methods 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 239000002253 acid Substances 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 abstract 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 125000002252 acyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- -1 methylenedioxy group Chemical group 0.000 abstract 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 abstract 1
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)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (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
Procedure for obtaining compounds that have the general formula: **(See formula)** in which, R1 represents a hydrogen atom or an acyl group, R2 an alkyl or alkoxy group containing 1 to 5 carbon atoms, which may be straight or branched, or a cycloalkyl group with 5 or 6 carbon atoms, R3 represents a hydrogen atom or a lower alkyl group, and R4 a straight or branched alkyl group with 1 to 8 carbon atoms, a cycloalkyl group with a maximum of 7 carbon atoms, a benzodioxanyl-2-alkyl group, in which the alkyl group contains 1 to 3 carbon atoms or the group **(See formula)** in which Z represents a straight or branched alkylene group, containing from 2 to 6 carbon atoms, n the numbers 0 or 1, R5 and R6, which may be the same or different, hydrogen atoms, hydroxy groups, lower alkyl or lower alkoxy or together a methylenedioxy group, with the restriction that it does not represent an isopropyl group in case R1 represents a hydrogen atom, and furthermore, that R2 represents a methyl or methoxy group, and R3 a hydrogen atom, a methyl or ethyl group, discretionally in the form of pure stereo isomers or pairs of diastereomeric antipodes and their acid addition salts characterized by: react a compound whose formula is **(See formula)** in which E designates the groups (see formula) or -CHOH-CHX - R3 (V) and X designates a chlorine, bromine or iodine atom with an amine of formula HNR''R4, remove from the compound the protection groups, if any, acylate the phenolic free OH groups, if desired, optionally, transform the free bases obtained first into their acid addition salts, the acid addition salts obtained firstly in salts with other acids or in free bases. (Machine-translation by Google Translate, not legally binding)
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 |
|---|---|
| ES360962A1 true ES360962A1 (en) | 1970-11-16 |
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 |
| 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) |
| 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) |
| 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) |
| 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) |
| 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) |
Family Applications Before (4)
| 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 |
| 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) |
| 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) |
| 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) |
Family Applications After (1)
| 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) |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3657244A (en) |
| AT (3) | AT285582B (en) |
| BE (1) | BE705312A (en) |
| CH (4) | CH548365A (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) | SE380792B (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| 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 | ||
| DE3163871D1 (en) | 1980-07-09 | 1984-07-05 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates |
| 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 |
| AU582573B2 (en) * | 1984-04-17 | 1989-04-06 | Glaxo Group Limited | 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 |
| 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 |
| 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 |
| 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 CH452872A patent/CH548365A/en not_active IP Right Cessation
- 1967-10-16 US US713265A patent/US3657244A/en not_active Expired - Lifetime
- 1967-10-16 CH CH1442267A patent/CH490323A/en not_active IP Right Cessation
- 1967-10-16 AT AT934967A patent/AT285582B/en not_active IP Right Cessation
- 1967-10-16 AT AT1165269A patent/AT288357B/en not_active IP Right Cessation
- 1967-10-16 CH CH513470A patent/CH523219A/en not_active IP Right Cessation
- 1967-10-16 AT AT1165369A patent/AT288358B/en not_active IP Right Cessation
- 1967-10-16 CH CH513370A patent/CH507200A/en not_active IP Right Cessation
- 1967-10-17 DK DK516167AA patent/DK130070B/en not_active IP Right Cessation
- 1967-10-18 SE SE7106612A patent/SE380792B/en 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 SE14280/67A patent/SE368196B/xx 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 ES360964A patent/ES360964A1/en not_active Expired
- 1968-11-30 ES ES360961A patent/ES360961A1/en not_active Expired
- 1968-11-30 ES ES360965A patent/ES360965A1/en not_active Expired
- 1968-11-30 ES ES360962A patent/ES360962A1/en not_active Expired
- 1968-11-30 ES ES360963A patent/ES360963A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT288358B (en) | 1971-03-10 |
| FR7338M (en) | 1969-10-13 |
| DE1543374B2 (en) | 1973-02-22 |
| ES346057A1 (en) | 1969-03-16 |
| DK130070C (en) | 1975-05-26 |
| AT288357B (en) | 1971-03-10 |
| DK130070B (en) | 1974-12-16 |
| DE1543372A1 (en) | 1971-04-01 |
| CH548365A (en) | 1974-04-30 |
| ES360963A1 (en) | 1970-11-16 |
| NL158480B (en) | 1978-11-15 |
| CH507200A (en) | 1971-05-15 |
| SE380792B (en) | 1975-11-17 |
| CH523219A (en) | 1972-05-31 |
| DE1543374C3 (en) | 1973-10-04 |
| ES360964A1 (en) | 1970-10-16 |
| GB1204195A (en) | 1970-09-03 |
| NL6714161A (en) | 1968-04-19 |
| ES360965A1 (en) | 1970-11-16 |
| CH490323A (en) | 1970-05-15 |
| DE1543374A1 (en) | 1972-04-20 |
| ES360961A1 (en) | 1970-11-16 |
| US3657244A (en) | 1972-04-18 |
| SE368196B (en) | 1974-06-24 |
| AT285582B (en) | 1970-11-10 |
| BE705312A (en) | 1968-04-18 |
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