GB1468156A - Phenylethylamine derivatives - Google Patents
Phenylethylamine derivativesInfo
- Publication number
- GB1468156A GB1468156A GB3446573A GB3446573A GB1468156A GB 1468156 A GB1468156 A GB 1468156A GB 3446573 A GB3446573 A GB 3446573A GB 3446573 A GB3446573 A GB 3446573A GB 1468156 A GB1468156 A GB 1468156A
- Authority
- GB
- United Kingdom
- Prior art keywords
- benzyl
- amino
- formula
- ethanol
- benzyloxy
- 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
- 150000007925 phenylethylamine derivatives Chemical class 0.000 title abstract 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 8
- 150000001875 compounds Chemical class 0.000 abstract 8
- -1 2-phenylethyl radicals Chemical class 0.000 abstract 6
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 5
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 4
- 125000006239 protecting group Chemical group 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 239000002253 acid Substances 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000005529 alkyleneoxy group Chemical group 0.000 abstract 2
- 150000001412 amines Chemical class 0.000 abstract 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- WFKAJVHLWXSISD-UHFFFAOYSA-N isobutyramide Chemical compound CC(C)C(N)=O WFKAJVHLWXSISD-UHFFFAOYSA-N 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 abstract 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- UGIGSWZYZVRDAK-UHFFFAOYSA-N 1-(2-methyl-4-phenylmethoxyphenyl)ethanone Chemical compound C1=C(C)C(C(=O)C)=CC=C1OCC1=CC=CC=C1 UGIGSWZYZVRDAK-UHFFFAOYSA-N 0.000 abstract 1
- ZJABPUSDYOXUKS-UHFFFAOYSA-N 1-(2-phenylmethoxyphenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 ZJABPUSDYOXUKS-UHFFFAOYSA-N 0.000 abstract 1
- MHSHMGJHXSPXDH-UHFFFAOYSA-N 2-bromo-1-(2-phenylmethoxyphenyl)ethanone Chemical compound BrCC(=O)C1=CC=CC=C1OCC1=CC=CC=C1 MHSHMGJHXSPXDH-UHFFFAOYSA-N 0.000 abstract 1
- FTQYNEKKQMCMHT-UHFFFAOYSA-N 2-bromo-1-(3-methyl-4-phenylmethoxyphenyl)ethanone Chemical compound CC1=CC(C(=O)CBr)=CC=C1OCC1=CC=CC=C1 FTQYNEKKQMCMHT-UHFFFAOYSA-N 0.000 abstract 1
- 101100234822 Caenorhabditis elegans ltd-1 gene Proteins 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- HVVLEQHREFZCMX-UHFFFAOYSA-N N-[2-[benzyl-[2-[3-(methanesulfonamido)-4-phenylmethoxyphenyl]-2-oxoethyl]amino]ethyl]-2-methylpropanamide Chemical compound C(C1=CC=CC=C1)N(CC(=O)C1=CC(=C(C=C1)OCC1=CC=CC=C1)NS(=O)(=O)C)CCNC(C(C)C)=O HVVLEQHREFZCMX-UHFFFAOYSA-N 0.000 abstract 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 150000005840 aryl radicals Chemical class 0.000 abstract 1
- 239000002585 base Substances 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 230000003197 catalytic effect Effects 0.000 abstract 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- SUCLQLHNWUBQOE-UHFFFAOYSA-N ethyl 5-[2-[benzyl-[2-(2-methylpropanoylamino)ethyl]amino]-1-hydroxyethyl]-2-phenylmethoxybenzoate Chemical compound C(C1=CC=CC=C1)OC1=C(C=C(C=C1)C(CN(CCNC(C(C)C)=O)CC1=CC=CC=C1)O)C(=O)OCC SUCLQLHNWUBQOE-UHFFFAOYSA-N 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 238000007327 hydrogenolysis reaction Methods 0.000 abstract 1
- 125000001841 imino group Chemical group [H]N=* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 229940047889 isobutyramide Drugs 0.000 abstract 1
- QZUOKPUQPUDFNS-UHFFFAOYSA-N n-(2-oxopropyl)-2-phenylacetamide Chemical compound CC(=O)CNC(=O)CC1=CC=CC=C1 QZUOKPUQPUDFNS-UHFFFAOYSA-N 0.000 abstract 1
- RIMVISPKPWYDHK-UHFFFAOYSA-N n-[2-(benzylamino)ethyl]-2-methylpropanamide Chemical compound CC(C)C(=O)NCCNCC1=CC=CC=C1 RIMVISPKPWYDHK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/14—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/04—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C235/12—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and saturated having the nitrogen atom of at least one of the carboxamide groups bound to an acyclic carbon atom of a hydrocarbon radical substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/04—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms
- C07C275/06—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton
- C07C275/16—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to acyclic carbon atoms of an acyclic and saturated carbon skeleton being further substituted by carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/28—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C275/40—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups having nitrogen atoms of urea groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton being further substituted by nitrogen atoms not being part of nitro or nitroso groups
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (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)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (17)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3446573A GB1468156A (en) | 1973-07-19 | 1973-07-19 | Phenylethylamine derivatives |
| IE1410/74A IE39718B1 (en) | 1973-07-19 | 1974-07-03 | Phenylehylamine derivatives |
| ZA00744331A ZA744331B (en) | 1973-07-19 | 1974-07-04 | 1-hydroxyphenyl-2-amidoalkylaminoesthanol derivatives |
| US05/485,994 US3933911A (en) | 1973-07-19 | 1974-07-05 | 1-Aryl-2-amidoalkylaminoethanol derivatives |
| NLAANVRAGE7409453,A NL179974C (nl) | 1973-07-19 | 1974-07-12 | Werkwijze ter bereiding respectievelijk vervaardiging van een farmaceutisch preparaat met beta-adrenergisch stimulerende werking en werkwijze ter bereiding van daarbij bruikbare fenylethylaminederivaten. |
| AU71205/74A AU487297B2 (en) | 1973-07-19 | 1974-07-15 | Phenylethylamine derivatives |
| LU70551A LU70551A1 (en:Method) | 1973-07-19 | 1974-07-17 | |
| CA205,010A CA1043349A (en) | 1973-07-19 | 1974-07-18 | Therapeutic 1-hydroxyaryl-2-amidoalkylaminoethanol derivatives |
| BE146709A BE817826A (fr) | 1973-07-19 | 1974-07-18 | Nouveaux derives de la phenylethylamine |
| SE7409387A SE417197B (sv) | 1973-07-19 | 1974-07-18 | Analogiforfarande for framstellning av fenyletylaminderivat |
| DK388174A DK388174A (en:Method) | 1973-07-19 | 1974-07-18 | |
| FR7425080A FR2237624B1 (en:Method) | 1973-07-19 | 1974-07-18 | |
| JP49083096A JPS5922696B2 (ja) | 1973-07-19 | 1974-07-19 | フエニルエチルアミン誘導体及びその酸付加塩の製法 |
| DE2434911A DE2434911C2 (de) | 1973-07-19 | 1974-07-19 | Phenyläthylamin-Derivate und pharmazeutische Zusammensetzungen |
| CH1002274A CH612915A5 (en:Method) | 1973-07-19 | 1974-07-19 | |
| US05/607,932 US3957870A (en) | 1973-07-19 | 1975-08-26 | Organic compounds |
| US05/662,953 US4041074A (en) | 1973-07-19 | 1976-03-01 | 1-Hydroxyaryl-2-amidoalkylaminoethanol derivatives |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3446573A GB1468156A (en) | 1973-07-19 | 1973-07-19 | Phenylethylamine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1468156A true GB1468156A (en) | 1977-03-23 |
Family
ID=10365995
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3446573A Expired GB1468156A (en) | 1973-07-19 | 1973-07-19 | Phenylethylamine derivatives |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3933911A (en:Method) |
| JP (1) | JPS5922696B2 (en:Method) |
| BE (1) | BE817826A (en:Method) |
| CA (1) | CA1043349A (en:Method) |
| CH (1) | CH612915A5 (en:Method) |
| DE (1) | DE2434911C2 (en:Method) |
| DK (1) | DK388174A (en:Method) |
| FR (1) | FR2237624B1 (en:Method) |
| GB (1) | GB1468156A (en:Method) |
| IE (1) | IE39718B1 (en:Method) |
| LU (1) | LU70551A1 (en:Method) |
| NL (1) | NL179974C (en:Method) |
| SE (1) | SE417197B (en:Method) |
| ZA (1) | ZA744331B (en:Method) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000809A1 (en) * | 1977-08-16 | 1979-02-21 | Imperial Chemical Industries Plc | Anti-inflammatory 1-phenylethanolamine derivatives, pharmaceutical compositions thereof and processes for their manufacture |
| US7964615B2 (en) | 2005-05-20 | 2011-06-21 | Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the β2 adrenergic receptor |
| US8178679B2 (en) | 2007-11-28 | 2012-05-15 | Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the β2 adrenergic receptors |
| US8283342B2 (en) | 2007-02-09 | 2012-10-09 | Almirall S.A. | Napadisylate salt of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the β2 adrenergic receptor |
| US8524908B2 (en) | 2009-03-12 | 2013-09-03 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| US8563731B2 (en) | 2008-12-22 | 2013-10-22 | Almirall, S.A. | Mesylate salt of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]jamino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the β2 adrenergic receptor |
| US9108918B2 (en) | 2011-10-07 | 2015-08-18 | Almirall, S.A. | Process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(R)-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one via a novel intermediate |
| US9346759B2 (en) | 2012-03-20 | 2016-05-24 | Almirall, S.A. | Polymorphic crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one, heminapadisytlate as agonist of the β2 adrenergic receptor |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4086272A (en) * | 1970-07-18 | 1978-04-25 | Pfizer Inc. | Phenyl-alkanolamine, alkylamine and alpha-aminoalkyl ketone derivatives as heart stimulants |
| US4167581A (en) * | 1972-12-15 | 1979-09-11 | Imperial Chemical Industries Limited | Alkanolamine derivatives and pharmaceutical compositions and uses thereof |
| US4131685A (en) * | 1972-12-15 | 1978-12-26 | Imperial Chemical Industries Limited | Pharmaceutical compositions and uses of alkanolamine derivatives |
| US4041075A (en) * | 1973-12-12 | 1977-08-09 | Imperial Chemical Industries Limited | Phenoxy-alkanolamine derivatives |
| US4173583A (en) * | 1975-04-17 | 1979-11-06 | Schering Corporation | Diastereoisomers of 5-(1-hydroxy-2-(1-methyl-3-phenylpropylamino)ethyl)salicylamide |
| GB1508208A (en) * | 1975-12-05 | 1978-04-19 | Ici Ltd | Amide derivatives |
| US4115409A (en) * | 1975-12-05 | 1978-09-19 | Imperial Chemical Industries Limited | Alkanolamine derivatives |
| IE45991B1 (en) * | 1976-12-16 | 1983-01-26 | Ici Ltd | Esters of hydroxy amino amides |
| DE2962383D1 (en) * | 1978-06-15 | 1982-05-06 | Ici Plc | Anti-inflammatory 1-phenyl-2-aminoethanol derivatives, pharmaceutical compositions thereof for topical use, and processes for their manufacture |
| ZA802552B (en) * | 1979-05-21 | 1981-04-29 | Ici Ltd | 1-phenyl-2-aminoethanol derivatives |
| US5238962A (en) * | 1983-03-03 | 1993-08-24 | Hoffmann-La Roche Inc. | Benzamide derivatives |
| GB8607313D0 (en) * | 1986-03-25 | 1986-04-30 | Ici Plc | Pharmaceutical compositions |
| GB8607312D0 (en) * | 1986-03-25 | 1986-04-30 | Ici Plc | Therapeutic agents |
| SE9003057D0 (sv) * | 1990-09-26 | 1990-09-26 | Astra Ab | New process |
| GB0417802D0 (en) * | 2004-08-10 | 2004-09-15 | Novartis Ag | Organic compounds |
| WO2007016190A2 (en) * | 2005-07-28 | 2007-02-08 | Duke University | Antiparkinsonian action of phenylisopropylamines |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1214012A (en) * | 1967-12-21 | 1970-11-25 | Allen & Hanburys Ltd | Phenylethanolamines |
| US3856857A (en) * | 1970-02-13 | 1974-12-24 | En Nom Collectif Science Union | Amino acids and their derivatives |
| GB1301134A (en) * | 1970-07-18 | 1972-12-29 | Pfizer Ltd | SUBSTITUTED 1-PHENYL-2-ALLYLAMINO-ALKANOLS, 1-PHENYL-2-ALLYLAMINO-ALKANES AND alpha-AMINOALKYLPHENYL KETONES |
| US3769317A (en) * | 1971-02-23 | 1973-10-30 | Smith Kline French Lab | Novel ester derivatives of phenylpropanolamine |
-
1973
- 1973-07-19 GB GB3446573A patent/GB1468156A/en not_active Expired
-
1974
- 1974-07-03 IE IE1410/74A patent/IE39718B1/xx unknown
- 1974-07-04 ZA ZA00744331A patent/ZA744331B/xx unknown
- 1974-07-05 US US05/485,994 patent/US3933911A/en not_active Expired - Lifetime
- 1974-07-12 NL NLAANVRAGE7409453,A patent/NL179974C/xx not_active IP Right Cessation
- 1974-07-17 LU LU70551A patent/LU70551A1/xx unknown
- 1974-07-18 SE SE7409387A patent/SE417197B/xx not_active IP Right Cessation
- 1974-07-18 BE BE146709A patent/BE817826A/xx not_active IP Right Cessation
- 1974-07-18 CA CA205,010A patent/CA1043349A/en not_active Expired
- 1974-07-18 DK DK388174A patent/DK388174A/da not_active Application Discontinuation
- 1974-07-18 FR FR7425080A patent/FR2237624B1/fr not_active Expired
- 1974-07-19 CH CH1002274A patent/CH612915A5/xx not_active IP Right Cessation
- 1974-07-19 JP JP49083096A patent/JPS5922696B2/ja not_active Expired
- 1974-07-19 DE DE2434911A patent/DE2434911C2/de not_active Expired
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0000809A1 (en) * | 1977-08-16 | 1979-02-21 | Imperial Chemical Industries Plc | Anti-inflammatory 1-phenylethanolamine derivatives, pharmaceutical compositions thereof and processes for their manufacture |
| US7964615B2 (en) | 2005-05-20 | 2011-06-21 | Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the β2 adrenergic receptor |
| US8242177B2 (en) | 2005-05-20 | 2012-08-14 | Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the β2 adrenergic receptor |
| US8420669B2 (en) | 2005-05-20 | 2013-04-16 | Laboratories Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the BETA2 adrenergic receptor |
| US8283342B2 (en) | 2007-02-09 | 2012-10-09 | Almirall S.A. | Napadisylate salt of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy) hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the β2 adrenergic receptor |
| US8178679B2 (en) | 2007-11-28 | 2012-05-15 | Almirall, S.A. | Derivatives of 4-(2-amino-1-hydroxyethyl)phenol as agonists of the β2 adrenergic receptors |
| US8563731B2 (en) | 2008-12-22 | 2013-10-22 | Almirall, S.A. | Mesylate salt of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]jamino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one as agonist of the β2 adrenergic receptor |
| US8524908B2 (en) | 2009-03-12 | 2013-09-03 | Almirall, S.A. | Process for manufacturing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one |
| US9108918B2 (en) | 2011-10-07 | 2015-08-18 | Almirall, S.A. | Process for preparing 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1(R)-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one via a novel intermediate |
| US9346759B2 (en) | 2012-03-20 | 2016-05-24 | Almirall, S.A. | Polymorphic crystal forms of 5-(2-{[6-(2,2-difluoro-2-phenylethoxy)hexyl]amino}-1-(R)-hydroxyethyl)-8-hydroxyquinolin-2(1H)-one, heminapadisytlate as agonist of the β2 adrenergic receptor |
Also Published As
| Publication number | Publication date |
|---|---|
| IE39718L (en) | 1975-01-19 |
| FR2237624A1 (en:Method) | 1975-02-14 |
| AU7120574A (en) | 1976-01-15 |
| DE2434911C2 (de) | 1984-11-29 |
| NL179974C (nl) | 1986-12-16 |
| US3933911A (en) | 1976-01-20 |
| LU70551A1 (en:Method) | 1974-11-28 |
| DK388174A (en:Method) | 1975-03-17 |
| ZA744331B (en) | 1975-08-27 |
| NL179974B (nl) | 1986-07-16 |
| SE7409387L (en:Method) | 1975-01-20 |
| BE817826A (fr) | 1975-01-20 |
| JPS5047936A (en:Method) | 1975-04-28 |
| CH612915A5 (en:Method) | 1979-08-31 |
| DE2434911A1 (de) | 1975-02-06 |
| CA1043349A (en) | 1978-11-28 |
| NL7409453A (nl) | 1975-01-21 |
| FR2237624B1 (en:Method) | 1978-07-21 |
| JPS5922696B2 (ja) | 1984-05-28 |
| SE417197B (sv) | 1981-03-02 |
| IE39718B1 (en) | 1978-12-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |