ES378092A1 - Carboxylic esters of hydroxyphenylalkanolamines - Google Patents
Carboxylic esters of hydroxyphenylalkanolaminesInfo
- Publication number
- ES378092A1 ES378092A1 ES378092A ES378092A ES378092A1 ES 378092 A1 ES378092 A1 ES 378092A1 ES 378092 A ES378092 A ES 378092A ES 378092 A ES378092 A ES 378092A ES 378092 A1 ES378092 A1 ES 378092A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- formula
- acyl
- hydrogen
- alcoholic
- 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
- 150000001733 carboxylic acid esters Chemical class 0.000 title 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 14
- 125000002252 acyl group Chemical group 0.000 abstract 6
- 150000001875 compounds Chemical class 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 3
- 230000001476 alcoholic effect Effects 0.000 abstract 3
- -1 phenoxyacetyl Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 229910052783 alkali metal Inorganic materials 0.000 abstract 2
- 150000001340 alkali metals Chemical class 0.000 abstract 2
- 239000012458 free base Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 abstract 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 2
- AOWPVIWVMWUSBD-RNFRBKRXSA-N [(3r)-3-hydroxybutyl] (3r)-3-hydroxybutanoate Chemical compound C[C@@H](O)CCOC(=O)C[C@@H](C)O AOWPVIWVMWUSBD-RNFRBKRXSA-N 0.000 abstract 1
- 125000003158 alcohol group Chemical group 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052763 palladium Inorganic materials 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052697 platinum Inorganic materials 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pyridine Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
A process for preparing esters of alpha-aminomethyl-3- (hydroxy or hydroxymethyl) -4-hydroxybenzyl alcohols having, in the base form **(See formula)** where R is hydrogen (only in Formula II), alcoholic having from 1 to 4 carbon atoms, or cycloalcohyl having from 3 to 6 carbon atoms; R'is hydrogen or alcoholic having 1 to 3 carbon atoms; Y is an acyl member that is alkanoyl having 1 to 22 carbon atoms; alkenoyl having one or two double bonds and having 4 to 22 carbon atoms, (see formula) having a total of 4 to 10 carbon atoms of which 3 to 7 are ring carbon atoms in the cycloalkyl and where n is zero, one or two, phenoxyacetyl, naphthalenecarbonyl, pyridinecarbonyl groups, (see formula) where n is zero, one or two and phenyl is unsubstituted or substituted in position 1-3 by alcoholic having 1 to 4 carbon atoms, alkoxy having 1 to 4 carbon atoms, halogen, trifluoromethyl, dialkoxylamino having 2 to 8 carbon atoms, or alkanoylamino having 1 to 6 carbon atoms; and Y1 and Y2 are the same or different and are hydrogen or one of the acyl members defined by Y, and where in formula I at least one of Y and Y1 contain not less than four carbon atoms when R is tert-butyl or cycloalkoxy and not less than seven carbon atoms when R is an alcohol other than tert-butyl, and in formula II at least one of Y and Y1 contain not less than four carbon atoms; or an acid addition salt thereof, characterized by preparing the compound where Y2 is hydrogen by reducing an ketone ester having formula III or IV in the free base form **(See formula)** by treatment with an alkali metal borhydride in a lower alkanol or by catalytic hydrogenation in the presence of platinum or palladium, said borhydride of said alkali metal necessarily being used when Y or Y1 contain in the reduction product an olefinic double bond, and, if desired, acylating the compound obtained as an acid addition salt (strong) to obtain the corresponding compound where Y2 is acyl, and, if desired, preferably hydrolyzing a compound obtained of formula II, where Y, Y1 and Y2 are each acyl, to obtain the corresponding compound where Y1 is hydrogen and Y and Y2 are each acyl, and, if desired, converting a free base product obtained into an acid addition salt thereof. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US81237069A | 1969-04-01 | 1969-04-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES378092A1 true ES378092A1 (en) | 1973-01-01 |
Family
ID=25209368
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES378092A Expired ES378092A1 (en) | 1969-04-01 | 1970-03-31 | Carboxylic esters of hydroxyphenylalkanolamines |
Country Status (17)
| Country | Link |
|---|---|
| JP (2) | JPS5314544B1 (en) |
| AT (1) | AT300762B (en) |
| BE (1) | BE748178A (en) |
| CH (1) | CH522589A (en) |
| DE (1) | DE2015573C3 (en) |
| DK (1) | DK131459B (en) |
| ES (1) | ES378092A1 (en) |
| FI (1) | FI54796C (en) |
| FR (1) | FR2042295B1 (en) |
| GB (1) | GB1298771A (en) |
| IE (1) | IE34583B1 (en) |
| IL (2) | IL42029A (en) |
| NL (1) | NL171155C (en) |
| NO (1) | NO129903B (en) |
| PH (2) | PH9407A (en) |
| SE (2) | SE381039B (en) |
| ZA (1) | ZA702065B (en) |
Families Citing this family (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4138581A (en) | 1969-04-01 | 1979-02-06 | Sterling Drugs Inc. | 3(Hydroxy or hydroxymethyl)-4(hydroxy)-α-(aminomethyl)benzyl alcohols |
| US3809714A (en) * | 1972-08-31 | 1974-05-07 | Interx Research Corp | Novel ester of ((methylamino)methyl) benzyl alcohol |
| 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 |
| 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 |
| JPS50111037A (en) * | 1974-01-15 | 1975-09-01 | ||
| US3957849A (en) * | 1974-09-09 | 1976-05-18 | Zoecon Corporation | Cyclopropane esters |
| US4000315A (en) * | 1974-09-09 | 1976-12-28 | Zoecon Corporation | Cyclopropane esters for the control of mites |
| DE3163871D1 (en) * | 1980-07-09 | 1984-07-05 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives; preparation, compositions and intermediates |
| CY1271A (en) * | 1980-07-09 | 1985-03-08 | Draco Ab | Therapeutically active derivatives of phenylethanol amines |
| FI61474C (en) * | 1981-03-06 | 1982-08-10 | Star Oy Ab | FAR OIL FRAMSTAELLNING AV SYRAADDITIONSSALTER AV 3,4-DIACYLOXI-ALPHA - ((METHYLAMINO) -METHYL) -BENYL ALCOHOL |
| FR2541999B1 (en) * | 1983-03-04 | 1986-09-19 | Bristol Myers Co | PHENETHANOLAMINES AND THEIR USES |
| US4614830A (en) * | 1985-08-09 | 1986-09-30 | Sterling Drug Inc. | Esterification process |
| IT1229846B (en) * | 1989-04-20 | 1991-09-13 | Simes | ESTERS OF CATECOLAMINS. |
| US5118683A (en) * | 1990-06-13 | 1992-06-02 | Schering Corporation | Esters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| US5011845A (en) * | 1990-06-13 | 1991-04-30 | Schering Corporation | Cyclic diesters of 4-hydroxy-1,3-benzenedimethanol and compositions and methods employing such compounds |
| CA2758774C (en) | 2009-04-15 | 2015-02-03 | Research Triangle Institute | Monoamine reuptake inhibitors |
| CA2800220C (en) | 2010-05-21 | 2019-04-30 | Research Triangle Institute | Phenylmorpholines and analogues thereof |
| CA2800219C (en) | 2010-05-21 | 2019-03-12 | Research Triangle Institute | 1 - phenylmorpholine derivatives as hydroxybupropion analogues for treating drug dependence |
| US9784726B2 (en) | 2013-01-08 | 2017-10-10 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatment |
| CN108997261B (en) * | 2017-06-07 | 2022-01-07 | 东莞市凯法生物医药有限公司 | Compound and preparation method and application thereof |
| GB201714734D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714736D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201714740D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| GB201903832D0 (en) | 2019-03-20 | 2019-05-01 | Atrogi Ab | New compounds and methods |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
| CN120583945A (en) | 2023-01-20 | 2025-09-02 | 阿托基公司 | Beta2-adrenergic receptor agonists for the treatment or prevention of muscle wasting |
| GB202302225D0 (en) | 2023-02-16 | 2023-04-05 | Atrogi Ab | New medical uses |
| GB202303229D0 (en) | 2023-03-06 | 2023-04-19 | Atrogi Ab | New medical uses |
| GB202403169D0 (en) | 2024-03-05 | 2024-04-17 | Atrogi Ab | New medical uses |
| WO2025238248A1 (en) | 2024-05-17 | 2025-11-20 | Atrogi Ab | USE OF β2-ADRENERGIC RECEPTOR AGONISTS IN TREATING MUSCLE WASTING |
-
1970
- 1970-03-20 NO NO01048/70A patent/NO129903B/no unknown
- 1970-03-20 GB GB03690/70A patent/GB1298771A/en not_active Expired
- 1970-03-24 IL IL42029A patent/IL42029A/en unknown
- 1970-03-24 IL IL34148A patent/IL34148A/en unknown
- 1970-03-25 PH PH11270*UA patent/PH9407A/en unknown
- 1970-03-26 ZA ZA702065A patent/ZA702065B/en unknown
- 1970-03-26 CH CH467070A patent/CH522589A/en not_active IP Right Cessation
- 1970-03-27 BE BE748178D patent/BE748178A/en not_active IP Right Cessation
- 1970-03-31 ES ES378092A patent/ES378092A1/en not_active Expired
- 1970-03-31 DK DK160470AA patent/DK131459B/en not_active IP Right Cessation
- 1970-03-31 SE SE7004367A patent/SE381039B/en unknown
- 1970-04-01 AT AT296170A patent/AT300762B/en not_active IP Right Cessation
- 1970-04-01 FI FI908/70A patent/FI54796C/en active
- 1970-04-01 DE DE2015573A patent/DE2015573C3/en not_active Expired
- 1970-04-01 NL NLAANVRAGE7004671,A patent/NL171155C/en not_active IP Right Cessation
- 1970-04-01 IE IE394/70A patent/IE34583B1/en unknown
- 1970-04-01 JP JP2779370A patent/JPS5314544B1/ja active Pending
- 1970-04-01 FR FR707011697A patent/FR2042295B1/fr not_active Expired
-
1972
- 1972-07-14 PH PH13731A patent/PH14377A/en unknown
-
1973
- 1973-03-23 SE SE7304162A patent/SE413503B/en unknown
- 1973-07-31 JP JP8630073A patent/JPS5414096B1/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DK131459B (en) | 1975-07-21 |
| JPS5414096B1 (en) | 1979-06-05 |
| PH14377A (en) | 1981-06-17 |
| DE2015573B2 (en) | 1978-03-16 |
| NL7004671A (en) | 1970-10-05 |
| IL34148A0 (en) | 1970-07-19 |
| FR2042295A1 (en) | 1971-02-12 |
| NL171155B (en) | 1982-09-16 |
| SE381039B (en) | 1975-11-24 |
| NO129903B (en) | 1974-06-10 |
| IL42029A (en) | 1974-01-14 |
| PH9407A (en) | 1975-11-06 |
| DK131459C (en) | 1975-12-08 |
| NL171155C (en) | 1983-02-16 |
| BE748178A (en) | 1970-09-28 |
| IL34148A (en) | 1974-01-14 |
| FI54796C (en) | 1979-03-12 |
| DE2015573A1 (en) | 1970-10-08 |
| ZA702065B (en) | 1971-01-27 |
| FR2042295B1 (en) | 1974-06-14 |
| SE413503B (en) | 1980-06-02 |
| IE34583L (en) | 1970-10-01 |
| GB1298771A (en) | 1972-12-06 |
| JPS5314544B1 (en) | 1978-05-18 |
| CH522589A (en) | 1972-06-30 |
| DE2015573C3 (en) | 1978-11-02 |
| FI54796B (en) | 1978-11-30 |
| IE34583B1 (en) | 1975-06-25 |
| AT300762B (en) | 1972-08-10 |
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