GB1199630A - Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions - Google Patents
Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic ConditionsInfo
- Publication number
- GB1199630A GB1199630A GB47505/67A GB4750567A GB1199630A GB 1199630 A GB1199630 A GB 1199630A GB 47505/67 A GB47505/67 A GB 47505/67A GB 4750567 A GB4750567 A GB 4750567A GB 1199630 A GB1199630 A GB 1199630A
- Authority
- GB
- United Kingdom
- 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
- ULSIYEODSMZIPX-UHFFFAOYSA-N phenylethanolamine Chemical class NCC(O)C1=CC=CC=C1 ULSIYEODSMZIPX-UHFFFAOYSA-N 0.000 title abstract 2
- 239000004044 bronchoconstricting agent Substances 0.000 title 1
- 230000002741 bronchospastic effect Effects 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
- 241000509579 Draco Species 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
Abstract
1,199,630. Phenylethanolamine derivatives. DRACO, LUNDS FARMACEVTISKA A.B. 18 Oct., 1967 [19 Oct., 1966], No. 47505/67. Heading C2C. Compounds of the general formula (R = tert.-butyl, cyclobutyl, cyclopentyl; R<SP>5</SP> = OH, C 1-5 alkanoyloxy) and their salts are prepared by (a) reducing a compound of the formula (R<SP>3</SP> = H or group replaceable by H) in the presence of RNH 2 , followed by replacement of R<SP>3</SP> if necessary; (b) reacting a compound of the formula with RR<SP>4</SP>NH (R<SP>4</SP>=H, aralkyl), followed by replacement of R<SP>3</SP>'<SP>4</SP>, if necessary; (c) reducing a compound of the formula followed by replacement of R<SP>3</SP>'<SP>4</SP> if necessary; or (d) hydrogenating a compound of the formula reacting the product with cyclobutanone or cyclopentanone, further hydrogenating the reaction mixture and replacing R<SP>3</SP> 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 |
|---|---|
| GB1199630A true GB1199630A (en) | 1970-07-22 |
Family
ID=20298669
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47505/67A Expired GB1199630A (en) | 1966-10-19 | 1967-10-18 | Phenylethanolamine Derivatives Effective in the Treatment of Bronchospastic Conditions |
Country Status (13)
| Country | Link |
|---|---|
| AT (4) | AT288356B (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) |
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046144A1 (en) * | 1980-07-09 | 1982-02-17 | Aktiebolaget Draco | Therapeutically active derivatives of phenylethanol amines |
| US4853381A (en) * | 1984-04-17 | 1989-08-01 | Glaxo Group Limited | Ethanolamine compounds |
| US10288602B2 (en) | 2013-01-08 | 2019-05-14 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatement |
| CN110057932A (en) * | 2019-04-22 | 2019-07-26 | 上海旭东海普药业有限公司 | Method of the efficient liquid phase chromatographic analysis bricalin in relation to substance |
| 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 |
| CN113264839A (en) * | 2021-04-27 | 2021-08-17 | 苏州弘森药业股份有限公司 | Method for preparing levo-terbutaline by using chiral prosthetic group |
| US11357757B2 (en) | 2017-09-13 | 2022-06-14 | Atrogi Ab | Heteroaryl substituted beta-hydroxyethylamines for use in treating hyperglycaemia |
| US11427539B2 (en) | 2017-09-13 | 2022-08-30 | Atrogi Ab | Beta-hydroxy heterocyclic amines and their use in the treatment of hyperglycaemia |
| US11648216B2 (en) | 2017-09-13 | 2023-05-16 | Atrogi Ab | Fluorophenyl beta-hydroxyethylamines and their use in the treatment of hyperglycaemia |
| US11793774B2 (en) | 2017-09-13 | 2023-10-24 | Atrogi Ab | Chiral beta-hydroxyethylamines and their use in the treatment of hyperglycemia |
| WO2023203223A1 (en) | 2022-04-22 | 2023-10-26 | Atrogi Ab | Combinations of beta 2-adrenergic receptor agonists and beta 3-adrenergic receptor agonists, and medical uses thereof |
Families Citing this family (6)
| 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 |
| CY1273A (en) | 1980-07-09 | 1985-03-08 | Draco Ab | 1-(dihydroxyphenyl)-2-amino-ethanol derivatives;preparation,compositions and intermediates |
| 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 |
| 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 |
-
1966
- 1966-10-19 SE SE14182/66A patent/SE335359B/xx unknown
-
1967
- 1967-10-10 AT AT941969A patent/AT288356B/en not_active IP Right Cessation
- 1967-10-10 AT AT915967A patent/AT286964B/en not_active IP Right Cessation
- 1967-10-10 AT AT09421/69A patent/AT287679B/en active
- 1967-10-10 AT AT09420/69A patent/AT287678B/en active
- 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 DE DE1643296A patent/DE1643296C3/en not_active Expired
- 1967-10-17 FR FR124741A patent/FR8011M/fr 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 FI FI672811A patent/FI50786C/en active
- 1967-10-19 NL NL676714191A patent/NL151693B/en not_active IP Right Cessation
-
1968
- 1968-12-14 ES ES361429A patent/ES361429A1/en not_active Expired
- 1968-12-14 ES ES361432A patent/ES361432A1/en not_active Expired
- 1968-12-14 ES ES361433A patent/ES361433A1/en not_active Expired
- 1968-12-14 ES ES361431A patent/ES361431A1/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
Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0046144A1 (en) * | 1980-07-09 | 1982-02-17 | Aktiebolaget Draco | Therapeutically active derivatives of phenylethanol amines |
| US4853381A (en) * | 1984-04-17 | 1989-08-01 | Glaxo Group Limited | Ethanolamine compounds |
| US10288602B2 (en) | 2013-01-08 | 2019-05-14 | Atrogi Ab | Screening method, a kit, a method of treatment and a compound for use in a method of treatement |
| US11357757B2 (en) | 2017-09-13 | 2022-06-14 | Atrogi Ab | Heteroaryl substituted beta-hydroxyethylamines for use in treating hyperglycaemia |
| US11427539B2 (en) | 2017-09-13 | 2022-08-30 | Atrogi Ab | Beta-hydroxy heterocyclic amines and their use in the treatment of hyperglycaemia |
| US11648216B2 (en) | 2017-09-13 | 2023-05-16 | Atrogi Ab | Fluorophenyl beta-hydroxyethylamines and their use in the treatment of hyperglycaemia |
| US11793774B2 (en) | 2017-09-13 | 2023-10-24 | Atrogi Ab | Chiral beta-hydroxyethylamines and their use in the treatment of hyperglycemia |
| CN110057932A (en) * | 2019-04-22 | 2019-07-26 | 上海旭东海普药业有限公司 | Method of the efficient liquid phase chromatographic analysis bricalin in relation to substance |
| 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 |
| CN113264839A (en) * | 2021-04-27 | 2021-08-17 | 苏州弘森药业股份有限公司 | Method for preparing levo-terbutaline by using chiral prosthetic group |
| WO2023203223A1 (en) | 2022-04-22 | 2023-10-26 | Atrogi Ab | Combinations of beta 2-adrenergic receptor agonists and beta 3-adrenergic receptor agonists, and medical uses thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| AT287678B (en) | 1971-02-10 |
| ES361433A1 (en) | 1970-11-01 |
| DK128491B (en) | 1974-05-13 |
| IT8048168A0 (en) | 1980-03-14 |
| DE1793759B2 (en) | 1978-05-11 |
| AT288356B (en) | 1971-03-10 |
| ES361429A1 (en) | 1970-11-01 |
| NL6714191A (en) | 1968-04-22 |
| AT286964B (en) | 1971-01-11 |
| DE1643296B2 (en) | 1973-10-25 |
| NL151693B (en) | 1976-12-15 |
| DE1643296C3 (en) | 1974-06-12 |
| ES361432A1 (en) | 1970-11-01 |
| SE335359B (en) | 1971-05-24 |
| ES346131A1 (en) | 1969-05-16 |
| ES361431A1 (en) | 1970-11-01 |
| FI50786B (en) | 1976-03-31 |
| NO120686B (en) | 1970-11-23 |
| DE1793759A1 (en) | 1973-08-16 |
| CH510625A (en) | 1971-07-31 |
| DE1793759C3 (en) | 1979-01-11 |
| FI50786C (en) | 1976-07-12 |
| FR8011M (en) | 1970-07-27 |
| NL7513854A (en) | 1976-03-31 |
| BE704932A (en) | 1968-02-15 |
| AT287679B (en) | 1971-02-10 |
| DK468876A (en) | 1976-10-18 |
| DE1643296A1 (en) | 1971-09-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLE | Entries relating assignments, transmissions, licences in the register of patents | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| PE20 | Patent expired after termination of 20 years |