GB1392674A - Dopamine derivatives - Google Patents
Dopamine derivativesInfo
- Publication number
- GB1392674A GB1392674A GB1683573A GB1683573A GB1392674A GB 1392674 A GB1392674 A GB 1392674A GB 1683573 A GB1683573 A GB 1683573A GB 1683573 A GB1683573 A GB 1683573A GB 1392674 A GB1392674 A GB 1392674A
- Authority
- GB
- United Kingdom
- Prior art keywords
- methoxylated
- prepared
- hydrogen
- compounds
- methyl
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/01—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms
- C07C211/26—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to acyclic carbon atoms of an unsaturated carbon skeleton containing at least one six-membered aromatic ring
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- 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
- C07C45/46—Friedel-Crafts reactions
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicinal Preparation (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1392674 Dopamine derivatives ELI LILLY & CO 9 April 1973 [12 April 1972] 16835/73 Heading C2C The invention comprises dopamine derivatives of Formula (I) in which R and R 1 are H or CH 3 , at least one being H; R 2 and R 3 are H or OH at least one being OH; n is 1 or 2; and when n is 1 and R 2 and R 3 are both OH, then either R or R 1 is CH 3 ; and the pharmaceutically acceptable addition salts thereof with mineral acids. They may be prepared by reacting a compound of Formula (II) in which R 1 is hydrogen, R 2 <SP>1</SP> and R 3 <SP>1</SP> are H or CH 3 O- at least one being methoxy, n is 1 or 2; and when n is 1 and R2<SP>1</SP> and R 3 <SP>1</SP> are both CH 3 O, then R or R 1 is CH 3 ; with hydrobromic acid and optionally converting to pharmaceutically acceptable salts. The methyl ethers used as starting materials may be prepared as follows: (a) the compounds of Formula II in which R is methyl and R 1 is hydrogen are prepared by the reductive alkylation of a methoxylated phenylethylamine or a methoxylated phenyl propyl amine with 3,4-dimethoxyphenylacetone; (b) the compounds in which R is methyl and R 1 is hydrogen may also be prepared by reacting 3,4- dimethoxyphenylacetone with a methoxylated phenethylamine or a methoxylated phenylpropylamine in the presence of p-toluene sulphonic acid to form the imine which is then reduced to the secondary amine; (c) the compounds in which R is hydrogen and R 1 is methyl may be prepared by the reductive alkylation of 3,4-dimethoxyphenylethylamine with the desired mono- or dimethoxylated phenyl butane-3-one (n=2) or the mono- or di-methoxylated phenylacetone (n = 1); (d) the compounds in which R is hydrogen and R 1 is methyl may also be prepared by the condensation of 3,4-dimethoxyphenylacetic acid with a methoxylated 1 -phenyl-3-aminobutane (n=2) or with a methoxylated 1-phenyl-2- aminopropane (n =1) to form as an intermediate the methoxylated amide which is reduced under nitrogen with borane to provide the secondary amine; and (e) the compounds in which R and R 1 are both hydrogen may be prepared by the alkylation of 3,4-dimethoxyphenylethylamine with a methoxylated phenyl-n-propyl bromide (n=2) or with a methoxylated phenyethyl bromide (n= 1). The products of Formula (I) are used in pharmaceutical agents.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24346672A | 1972-04-12 | 1972-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1392674A true GB1392674A (en) | 1975-04-30 |
Family
ID=22918877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1683573A Expired GB1392674A (en) | 1972-04-12 | 1973-04-09 | Dopamine derivatives |
Country Status (31)
| Country | Link |
|---|---|
| JP (2) | JPS5825656B2 (en) |
| KR (1) | KR790000113B1 (en) |
| AR (1) | AR203822A1 (en) |
| AT (1) | AT323719B (en) |
| AU (1) | AU472734B2 (en) |
| BE (1) | BE798051A (en) |
| BG (1) | BG23001A3 (en) |
| CA (1) | CA1018188A (en) |
| CH (2) | CH580563A5 (en) |
| CS (2) | CS190448B2 (en) |
| CY (1) | CY963A (en) |
| DD (1) | DD107670B3 (en) |
| DE (1) | DE2317710C2 (en) |
| DK (1) | DK142750C (en) |
| ES (1) | ES413639A1 (en) |
| FR (1) | FR2182947B1 (en) |
| GB (1) | GB1392674A (en) |
| HK (1) | HK50178A (en) |
| HU (2) | HU166213B (en) |
| IE (1) | IE37511B1 (en) |
| IL (1) | IL42016A (en) |
| KE (1) | KE2870A (en) |
| MY (1) | MY7800381A (en) |
| NL (1) | NL174459C (en) |
| PH (1) | PH11041A (en) |
| PL (2) | PL94207B1 (en) |
| RO (2) | RO70892A (en) |
| SE (1) | SE399064B (en) |
| SU (1) | SU496719A3 (en) |
| YU (2) | YU36483B (en) |
| ZA (1) | ZA732136B (en) |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146529A (en) * | 1983-09-16 | 1985-04-24 | Shionogi & Co | Oral dobutamine preparation |
| EP0620208A1 (en) * | 1993-04-13 | 1994-10-19 | Duphar International Research B.V | Production of dobutamine compounds |
| US5442120A (en) * | 1993-04-13 | 1995-08-15 | Duphar International Research B.V. | Production of dobutamine compounds |
| WO2005092305A2 (en) * | 2004-03-26 | 2005-10-06 | New Era Biotech Ltd | Compounds for treating aids and other diseases |
| US8309606B2 (en) | 2002-10-03 | 2012-11-13 | Novaremed Limited | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| US8802734B2 (en) | 2009-09-09 | 2014-08-12 | Novaremed Limited | Method of treating or preventing pain |
| US8883853B2 (en) | 2008-03-06 | 2014-11-11 | Novaremed Limited | N-substituted benzenepropanamide or benzenepropenamide derivatives for use in the treatment of pain and inflammation |
| CN114524734A (en) * | 2021-12-27 | 2022-05-24 | 嘉实（湖南）医药科技有限公司 | Preparation method of novel dobutamine hydrochloride |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH585693A5 (en) * | 1974-02-08 | 1977-03-15 | Ciba Geigy Ag | |
| US4342692A (en) * | 1980-10-20 | 1982-08-03 | Usv Pharmaceutical Corporation | Pyrrolidines |
| NO822514L (en) * | 1981-07-22 | 1983-01-24 | Syntex Inc | PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVITY 2,5-SUBSTITUTED PYRROLIDE INGREDIENTS |
| ZA881076B (en) * | 1987-02-24 | 1989-10-25 | Lilly Co Eli | Dobutamine salts |
| JPH0383364U (en) * | 1989-12-18 | 1991-08-23 | ||
| EP0613879A4 (en) * | 1991-05-20 | 1995-05-03 | Tsumura & Co | Phellodendrine analogs and allergy type iv suppressor containing the same as active ingredient. |
| ES2547730T3 (en) | 2009-07-31 | 2015-10-08 | Cognition Therapeutics, Inc. | Cognitive impairment inhibitors |
| AU2012298614A1 (en) * | 2011-08-25 | 2014-04-10 | Cognition Therapeutics, Inc. | Compositions and methods for treating neurodegenerative disease |
| AU2015210852B2 (en) | 2014-01-31 | 2019-01-24 | Cognition Therapeutics, Inc. | Isoindoline compositions and methods for treating neurodegenerative disease |
| CA3061787A1 (en) | 2017-05-15 | 2018-11-22 | Cognition Therapeutics, Inc. | Compositions for treating neurodegenerative diseases |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2276619A (en) * | 1942-03-17 | N-phentlaliphatic-dihtoroxyphentnl |
-
1973
- 1973-03-28 ZA ZA732136A patent/ZA732136B/en unknown
- 1973-04-09 DE DE2317710A patent/DE2317710C2/en not_active Expired
- 1973-04-09 CY CY963A patent/CY963A/en unknown
- 1973-04-09 GB GB1683573A patent/GB1392674A/en not_active Expired
- 1973-04-10 IE IE563/73A patent/IE37511B1/en unknown
- 1973-04-10 SE SE7305032A patent/SE399064B/en unknown
- 1973-04-10 FR FR7312845A patent/FR2182947B1/fr not_active Expired
- 1973-04-11 BE BE1004956A patent/BE798051A/en not_active IP Right Cessation
- 1973-04-11 CH CH1112475A patent/CH580563A5/xx not_active IP Right Cessation
- 1973-04-11 DK DK196773A patent/DK142750C/en not_active IP Right Cessation
- 1973-04-11 NL NLAANVRAGE7305097,A patent/NL174459C/en not_active IP Right Cessation
- 1973-04-11 CH CH517473A patent/CH569691A5/xx not_active IP Right Cessation
- 1973-04-11 BG BG26268A patent/BG23001A3/xx unknown
- 1973-04-11 CA CA168,428A patent/CA1018188A/en not_active Expired
- 1973-04-11 AT AT318773A patent/AT323719B/en not_active IP Right Cessation
- 1973-04-11 AU AU54385/73A patent/AU472734B2/en not_active Expired
- 1973-04-11 YU YU00976/73A patent/YU36483B/en unknown
- 1973-04-11 KR KR7300573A patent/KR790000113B1/en active
- 1973-04-11 SU SU1908277A patent/SU496719A3/en active
- 1973-04-12 RO RO7383749A patent/RO70892A/en unknown
- 1973-04-12 PH PH14508A patent/PH11041A/en unknown
- 1973-04-12 CS CS77171A patent/CS190448B2/en unknown
- 1973-04-12 HU HUEI469A patent/HU166213B/hu unknown
- 1973-04-12 PL PL1973183808A patent/PL94207B1/pl unknown
- 1973-04-12 PL PL1973161874A patent/PL90695B1/pl unknown
- 1973-04-12 JP JP48041750A patent/JPS5825656B2/en not_active Expired
- 1973-04-12 RO RO7374457A patent/RO65105A/en unknown
- 1973-04-12 CS CS732601A patent/CS190406B2/en unknown
- 1973-04-12 HU HUEI552A patent/HU167597B/hu unknown
- 1973-04-12 AR AR247523A patent/AR203822A1/en active
- 1973-04-12 ES ES413639A patent/ES413639A1/en not_active Expired
- 1973-04-12 DD DD73170118A patent/DD107670B3/en unknown
- 1973-04-12 IL IL42016A patent/IL42016A/en unknown
-
1978
- 1978-08-10 KE KE2870A patent/KE2870A/en unknown
- 1978-09-07 HK HK501/78A patent/HK50178A/en unknown
- 1978-12-30 MY MY381/78A patent/MY7800381A/en unknown
-
1979
- 1979-12-28 YU YU3212/79A patent/YU37113B/en unknown
-
1982
- 1982-08-27 JP JP57149025A patent/JPS58131945A/en active Granted
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2146529A (en) * | 1983-09-16 | 1985-04-24 | Shionogi & Co | Oral dobutamine preparation |
| EP0620208A1 (en) * | 1993-04-13 | 1994-10-19 | Duphar International Research B.V | Production of dobutamine compounds |
| US5442120A (en) * | 1993-04-13 | 1995-08-15 | Duphar International Research B.V. | Production of dobutamine compounds |
| US8309606B2 (en) | 2002-10-03 | 2012-11-13 | Novaremed Limited | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| US7754771B2 (en) | 2004-03-26 | 2010-07-13 | Novaremed Limited | Compounds for the treatment of AIDS and other viral diseases |
| US7674829B2 (en) | 2004-03-26 | 2010-03-09 | Novaremed Limited | Compounds for the treatment of AIDS and other viral diseases |
| WO2005092305A3 (en) * | 2004-03-26 | 2006-03-02 | New Era Biotech Ltd | Compounds for treating aids and other diseases |
| US8252843B2 (en) | 2004-03-26 | 2012-08-28 | Novaremed Limited | Compounds for the treatment of AIDS and other viral diseases |
| WO2005092305A2 (en) * | 2004-03-26 | 2005-10-06 | New Era Biotech Ltd | Compounds for treating aids and other diseases |
| US8883853B2 (en) | 2008-03-06 | 2014-11-11 | Novaremed Limited | N-substituted benzenepropanamide or benzenepropenamide derivatives for use in the treatment of pain and inflammation |
| US8802734B2 (en) | 2009-09-09 | 2014-08-12 | Novaremed Limited | Method of treating or preventing pain |
| CN114524734A (en) * | 2021-12-27 | 2022-05-24 | 嘉实（湖南）医药科技有限公司 | Preparation method of novel dobutamine hydrochloride |
| CN114524734B (en) * | 2021-12-27 | 2024-04-26 | 嘉实（湖南）医药科技有限公司 | Preparation method of dobutamine hydrochloride |
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1392674A (en) | Dopamine derivatives | |
| GB1535967A (en) | Antilipidemic para-(aryl(alkyl or alkenyl)-amino)-benzoic acid derivatives | |
| GB1337280A (en) | 5-phenyl-isoxazole-3-carboxylic acids and their derivatives | |
| GB1256733A (en) | ||
| GB1256750A (en) | ||
| GB1489711A (en) | 1-phenoxyphenyl-piperazine derivatives process for their preparation and pharmaceutical compositions containing the | |
| GB1168080A (en) | New N-Propynyl Methylamines and their Salts, and process for preparation thereof | |
| GB1095184A (en) | Phenylalanine derivatives | |
| GB1024816A (en) | Basic ethers of substituted hydroxy benzoic acids and process for making same | |
| GB1221734A (en) | Substituted phenyl morpholines, their preparation, and pharmaceutical compositions containing them | |
| GB1392584A (en) | Anilides and the production thereof | |
| ES381534A2 (en) | A procedure for the preparation of new derivatives of 1-phenyl-2-aminoetanol. (Machine-translation by Google Translate, not legally binding) | |
| GB1431078A (en) | Mannich bases, a process for their preparation and their use in the preparation of polyurethanes | |
| GB1352288A (en) | Imidazole derivatives | |
| DK212186A (en) | PHENOXYETHYLAMINE DERIVATIVES AND INTERMEDIATES FOR PREPARING THEREOF | |
| GB1095912A (en) | Trans indolomorphinans and preparation thereof | |
| GB1340637A (en) | Dibenzocycloheptadioxolan derivatives | |
| GB1090717A (en) | Acryloyl phenols | |
| JPS5522699A (en) | Novel 3-amino-1-benzylpyrrolidine derivative | |
| GB1250270A (en) | ||
| GB1440380A (en) | Pyrrolidine derivatives | |
| GB1330129A (en) | Benzyloxybenzoic acid derivatives and pharmaceutical preparation containing them | |
| GB1026408A (en) | Piperidine derivatives and their manufacture and use | |
| GB1469745A (en) | Phenylethylamine derivatives | |
| GB1437799A (en) | Benzimidazolinone compounds |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746B | Proceeding under section 46(3) patents act 1977 | ||
| 746D | Case decided by the comptroller (sect. 46(3)/1977) | ||
| PE20 | Patent expired after termination of 20 years |
Effective date: 19930408 |