ES361431A1 - Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions - Google Patents
Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic ConditionsInfo
- Publication number
- ES361431A1 ES361431A1 ES361431A ES361431A ES361431A1 ES 361431 A1 ES361431 A1 ES 361431A1 ES 361431 A ES361431 A ES 361431A ES 361431 A ES361431 A ES 361431A ES 361431 A1 ES361431 A1 ES 361431A1
- Authority
- ES
- Spain
- Prior art keywords
- formula
- compound
- necessary
- followed
- replacement
- 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
- 239000004044 bronchoconstricting agent Substances 0.000 title 1
- 230000002741 bronchospastic effect Effects 0.000 title 1
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 6
- BGTOWKSIORTVQH-UHFFFAOYSA-N cyclopentanone Chemical compound O=C1CCCC1 BGTOWKSIORTVQH-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KOJXGMJOTRYLBD-UHFFFAOYSA-N 1-[3,5-bis(phenylmethoxy)phenyl]ethanone Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)C)=CC=1OCC1=CC=CC=C1 KOJXGMJOTRYLBD-UHFFFAOYSA-N 0.000 abstract 1
- DHQIBPUGSWVDOH-UHFFFAOYSA-N 3,5-bis(phenylmethoxy)benzoic acid Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)O)=CC=1OCC1=CC=CC=C1 DHQIBPUGSWVDOH-UHFFFAOYSA-N 0.000 abstract 1
- GWIBCCZNAYLLCD-UHFFFAOYSA-N 3,5-bis(phenylmethoxy)benzoyl chloride Chemical compound C=1C(OCC=2C=CC=CC=2)=CC(C(=O)Cl)=CC=1OCC1=CC=CC=C1 GWIBCCZNAYLLCD-UHFFFAOYSA-N 0.000 abstract 1
- 101100037762 Caenorhabditis elegans rnh-2 gene Proteins 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229940124630 bronchodilator Drugs 0.000 abstract 1
- 239000000168 bronchodilator agent Substances 0.000 abstract 1
- SHQSVMDWKBRBGB-UHFFFAOYSA-N cyclobutanone Chemical compound O=C1CCC1 SHQSVMDWKBRBGB-UHFFFAOYSA-N 0.000 abstract 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 abstract 1
- APHYVLPIZUVDTK-UHFFFAOYSA-N ethyl 3,5-dihydroxybenzoate Chemical compound CCOC(=O)C1=CC(O)=CC(O)=C1 APHYVLPIZUVDTK-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 239000007858 starting material Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/004—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reaction with organometalhalides
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/45—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation
- C07C45/48—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by condensation involving decarboxylation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/63—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by introduction of halogen; by substitution of halogen atoms by other halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
- C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
- C07C45/673—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by change of size of the carbon skeleton
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Epidemiology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Compounds of the general formula (R = tert.-butyl, cyclobutyl, cyclopentyl R5 = OH, C 1-5 alkanoyloxy) and their salts are prepared by (a) reducing a compound of the formula (R3 = H or group replaceable by H) in the presence of RNH 2 , followed by replacement of R3 if necessary (b) reacting a compound of the formula with RR4NH (R4=H, aralkyl), followed by replacement of R3'4, if necessary (c) reducing a compound of the formula followed by replacement of R3'4 if necessary or (d) hydrogenating a compound of the formula reacting the product with cyclobutanone or cyclopentanone, further hydrogenating the reaction mixture and replacing R3 if necessary optionally followed in each case by salt formation. The preparation of starting materials for processes (a), (b), (c) and (d) by standard methods and of ethyl 3,5-dihydroxybenzoate, 3,5- dibenzyloxybenzoic acid, 3,5-dibenzyloxybenzoyl chloride, 3,5 - dibenzyloxy - # - bromoacetophenone, 3,5 - dibenzyloxy - # - chloroacetophenone and 3,5-dibenzyloxyacetophenone is described. The compounds of the invention are bronchodilators, and may be administered in the form of pharmaceutical preparations containing them in association with a carrier.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE14182/66A SE335359B (en) | 1966-10-19 | 1966-10-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES361431A1 true ES361431A1 (en) | 1970-11-01 |
Family
ID=20298669
Family Applications (5)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES346131A Expired ES346131A1 (en) | 1966-10-19 | 1967-10-16 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
| ES361431A Expired ES361431A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
| ES361432A Expired ES361432A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
| ES361429A Expired ES361429A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
| ES361433A Expired ES361433A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES346131A Expired ES346131A1 (en) | 1966-10-19 | 1967-10-16 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES361432A Expired ES361432A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
| ES361429A Expired ES361429A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
| ES361433A Expired ES361433A1 (en) | 1966-10-19 | 1968-12-14 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
Country Status (13)
| Country | Link |
|---|---|
| AT (4) | AT287678B (en) |
| BE (1) | BE704932A (en) |
| CH (1) | CH510625A (en) |
| DE (2) | DE1793759C3 (en) |
| DK (2) | DK128491B (en) |
| ES (5) | ES346131A1 (en) |
| FI (1) | FI50786C (en) |
| FR (1) | FR8011M (en) |
| GB (1) | GB1199630A (en) |
| IT (1) | IT8048168A0 (en) |
| NL (2) | NL151693B (en) |
| NO (1) | NO120686B (en) |
| SE (1) | SE335359B (en) |
Families Citing this family (20)
| 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 |
| DE3163114D1 (en) * | 1980-07-09 | 1984-05-17 | Draco Ab | Therapeutically active derivatives of phenylethanol amines |
| CY1273A (en) | 1980-07-09 | 1985-03-08 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives;preparation,compositions and intermediates |
| US4853381A (en) * | 1984-04-17 | 1989-08-01 | Glaxo Group Limited | Ethanolamine compounds |
| US4581225A (en) * | 1984-04-25 | 1986-04-08 | Eli Lilly And Company | Sustained release intranasal formulation and method of use thereof |
| EP0213108A3 (en) * | 1985-06-26 | 1987-07-15 | Kurt Dr. Burghart | Pharmaceutical preparation containing an antihypotonic as the active agent |
| WO2013081565A1 (en) | 2011-11-21 | 2013-06-06 | Mahmut Bilgic | Pharmaceutical compositions comprising roflumilast and terbutaline |
| 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 |
| EP3600275A1 (en) | 2017-03-27 | 2020-02-05 | Ilko Ilaç Sanayi Ve Ticaret Anonim Sirketi | Stabilized pharmaceutical syrup composition comprising terbutaline sulphate and ambroxol hydrochloride |
| GB201714734D0 (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 |
| GB201714745D0 (en) | 2017-09-13 | 2017-10-25 | Atrogi Ab | New compounds and uses |
| CN110057932B (en) * | 2019-04-22 | 2022-03-15 | 上海旭东海普药业有限公司 | Method for analyzing terbutaline sulfate related substances by high performance liquid chromatography |
| CN111440078A (en) * | 2020-04-26 | 2020-07-24 | 梯尔希（南京）药物研发有限公司 | Preparation method of terbutaline derivative |
| CN113264839B (en) * | 2021-04-27 | 2022-08-30 | 苏州弘森药业股份有限公司 | Method for preparing levo-terbutaline by using chiral prosthetic group |
| GB202205895D0 (en) | 2022-04-22 | 2022-06-08 | Atrogi Ab | New medical uses |
| WO2024153813A1 (en) | 2023-01-20 | 2024-07-25 | Atrogi Ab | Beta 2-adrenergic receptor agonists for 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 |
-
1966
- 1966-10-19 SE SE14182/66A patent/SE335359B/xx unknown
-
1967
- 1967-10-10 AT AT09420/69A patent/AT287678B/en active
- 1967-10-10 AT AT09421/69A patent/AT287679B/en active
- 1967-10-10 AT AT915967A patent/AT286964B/en not_active IP Right Cessation
- 1967-10-10 AT AT941969A patent/AT288356B/en not_active IP Right Cessation
- 1967-10-11 BE BE704932D patent/BE704932A/xx not_active IP Right Cessation
- 1967-10-12 CH CH1425567A patent/CH510625A/en not_active IP Right Cessation
- 1967-10-16 ES ES346131A patent/ES346131A1/en not_active Expired
- 1967-10-17 DE DE1793759A patent/DE1793759C3/en not_active Expired
- 1967-10-17 FR FR124741A patent/FR8011M/fr not_active Expired
- 1967-10-17 DE DE1643296A patent/DE1643296C3/en not_active Expired
- 1967-10-18 GB GB47505/67A patent/GB1199630A/en not_active Expired
- 1967-10-18 DK DK518567AA patent/DK128491B/en unknown
- 1967-10-18 NO NO170180A patent/NO120686B/no unknown
- 1967-10-19 NL NL676714191A patent/NL151693B/en not_active IP Right Cessation
- 1967-10-19 FI FI672811A patent/FI50786C/en active
-
1968
- 1968-12-14 ES ES361431A patent/ES361431A1/en not_active Expired
- 1968-12-14 ES ES361432A patent/ES361432A1/en not_active Expired
- 1968-12-14 ES ES361429A patent/ES361429A1/en not_active Expired
- 1968-12-14 ES ES361433A patent/ES361433A1/en not_active Expired
-
1975
- 1975-11-27 NL NL7513854A patent/NL7513854A/en unknown
-
1976
- 1976-10-18 DK DK468876A patent/DK468876A/en unknown
-
1980
- 1980-03-14 IT IT8048168A patent/IT8048168A0/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| SE335359B (en) | 1971-05-24 |
| IT8048168A0 (en) | 1980-03-14 |
| NL6714191A (en) | 1968-04-22 |
| CH510625A (en) | 1971-07-31 |
| DE1643296B2 (en) | 1973-10-25 |
| DE1793759B2 (en) | 1978-05-11 |
| DE1643296C3 (en) | 1974-06-12 |
| NO120686B (en) | 1970-11-23 |
| ES346131A1 (en) | 1969-05-16 |
| NL151693B (en) | 1976-12-15 |
| AT287679B (en) | 1971-02-10 |
| ES361429A1 (en) | 1970-11-01 |
| NL7513854A (en) | 1976-03-31 |
| FI50786C (en) | 1976-07-12 |
| DE1793759C3 (en) | 1979-01-11 |
| DK468876A (en) | 1976-10-18 |
| AT287678B (en) | 1971-02-10 |
| GB1199630A (en) | 1970-07-22 |
| ES361433A1 (en) | 1970-11-01 |
| AT288356B (en) | 1971-03-10 |
| DE1793759A1 (en) | 1973-08-16 |
| DK128491B (en) | 1974-05-13 |
| AT286964B (en) | 1971-01-11 |
| DE1643296A1 (en) | 1971-09-30 |
| BE704932A (en) | 1968-02-15 |
| ES361432A1 (en) | 1970-11-01 |
| FR8011M (en) | 1970-07-27 |
| FI50786B (en) | 1976-03-31 |
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