IE37511B1 - Dopamine derivatives - Google Patents
Dopamine derivativesInfo
- Publication number
- IE37511B1 IE37511B1 IE563/73A IE56373A IE37511B1 IE 37511 B1 IE37511 B1 IE 37511B1 IE 563/73 A IE563/73 A IE 563/73A IE 56373 A IE56373 A IE 56373A IE 37511 B1 IE37511 B1 IE 37511B1
- Authority
- IE
- Ireland
- Prior art keywords
- methoxylated
- prepared
- hydrogen
- compounds
- methyl
- Prior art date
Links
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical class NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 title abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 6
- 239000001257 hydrogen Substances 0.000 abstract 6
- 229910052739 hydrogen Inorganic materials 0.000 abstract 6
- UMYZWICEDUEWIM-UHFFFAOYSA-N 1-(3,4-dimethoxyphenyl)propan-2-one Chemical compound COC1=CC=C(CC(C)=O)C=C1OC UMYZWICEDUEWIM-UHFFFAOYSA-N 0.000 abstract 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 3
- ANOUKFYBOAKOIR-UHFFFAOYSA-N 3,4-dimethoxyphenylethylamine Chemical compound COC1=CC=C(CCN)C=C1OC ANOUKFYBOAKOIR-UHFFFAOYSA-N 0.000 abstract 2
- LYUQWQRTDLVQGA-UHFFFAOYSA-N 3-phenylpropylamine Chemical class NCCCC1=CC=CC=C1 LYUQWQRTDLVQGA-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 abstract 2
- WUAXWQRULBZETB-UHFFFAOYSA-N homoveratric acid Chemical compound COC1=CC=C(CC(O)=O)C=C1OC WUAXWQRULBZETB-UHFFFAOYSA-N 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000005932 reductive alkylation reaction Methods 0.000 abstract 2
- 230000002829 reductive effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000000467 secondary amino group Chemical class [H]N([*:1])[*:2] 0.000 abstract 2
- KWTSXDURSIMDCE-UHFFFAOYSA-N 1-phenylpropan-2-amine Chemical class CC(N)CC1=CC=CC=C1 KWTSXDURSIMDCE-UHFFFAOYSA-N 0.000 abstract 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 abstract 1
- XMZQWZJMTBCUFT-UHFFFAOYSA-N 3-bromopropylbenzene Chemical class BrCCCC1=CC=CC=C1 XMZQWZJMTBCUFT-UHFFFAOYSA-N 0.000 abstract 1
- WECUIGDEWBNQJJ-UHFFFAOYSA-N 4-phenylbutan-2-amine Chemical class CC(N)CCC1=CC=CC=C1 WECUIGDEWBNQJJ-UHFFFAOYSA-N 0.000 abstract 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 abstract 1
- BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical class NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000007513 acids Chemical class 0.000 abstract 1
- 230000029936 alkylation Effects 0.000 abstract 1
- 238000005804 alkylation reaction Methods 0.000 abstract 1
- 150000001408 amides Chemical class 0.000 abstract 1
- AKGGYBADQZYZPD-UHFFFAOYSA-N benzylacetone Chemical class CC(=O)CCC1=CC=CC=C1 AKGGYBADQZYZPD-UHFFFAOYSA-N 0.000 abstract 1
- 229910000085 borane Inorganic materials 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 229910052500 inorganic mineral Inorganic materials 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 150000005217 methyl ethers Chemical class 0.000 abstract 1
- 239000011707 mineral Substances 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- QCCDLTOVEPVEJK-UHFFFAOYSA-N phenylacetone Chemical class CC(=O)CC1=CC=CC=C1 QCCDLTOVEPVEJK-UHFFFAOYSA-N 0.000 abstract 1
- 150000007925 phenylethylamine derivatives Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 abstract 1
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)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Cardiology (AREA)
- Epidemiology (AREA)
- Heart & Thoracic Surgery (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (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.
[GB1392674A]
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US24346672A | 1972-04-12 | 1972-04-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| IE37511B1 true IE37511B1 (en) | 1977-08-03 |
Family
ID=22918877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE563/73A IE37511B1 (en) | 1972-04-12 | 1973-04-10 | 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) | CH569691A5 (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) |
Families Citing this family (19)
| 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 |
| ZA825227B (en) * | 1981-07-22 | 1984-03-28 | Syntex Inc | Substituted pyrrolidine cardiovascular system regulators antihypertensives |
| JPS6061523A (en) * | 1983-09-16 | 1985-04-09 | Shionogi & Co Ltd | Oral dobutamine pharmaceutical |
| ZA881076B (en) * | 1987-02-24 | 1989-10-25 | Lilly Co Eli | Dobutamine salts |
| JPH0383364U (en) * | 1989-12-18 | 1991-08-23 | ||
| AU658188B2 (en) * | 1991-05-20 | 1995-04-06 | Tsumura & Co. | Phellodendrine analogs and allergy type IV suppressor containing the same as active ingredient |
| DE69404063T2 (en) * | 1993-04-13 | 1998-01-22 | Duphar Int Res | Manufacture of dobutamine compounds |
| EP0620208B1 (en) * | 1993-04-13 | 1997-07-09 | Duphar International Research B.V | Production of dobutamine compounds |
| DK1546088T3 (en) | 2002-10-03 | 2015-03-30 | Novaremed Ltd | RELATIONSHIPS FOR USING THE TREATMENT OF AUTO-IMMUNE DISEASES, IMMUNOALLERGIC DISEASES AND ORGAN OR TISSUE TRANSPLANT AID |
| CA2560922C (en) | 2004-03-26 | 2014-01-07 | New Era Biotech, Ltd. | Improvements in or relating to compounds for use in the treatment of aids and other viral diseases and hiv-related infections and compositions containing such compounds, methods of treating such diseases and infections and methods of making such compounds and compositions |
| GB0804213D0 (en) | 2008-03-06 | 2008-04-16 | New Era Biotech Ltd | A method of printing or preventing pain |
| JP2013501006A (en) | 2009-07-31 | 2013-01-10 | コグニション セラピューティクス インク． | Cognitive decline inhibitors |
| US8802734B2 (en) | 2009-09-09 | 2014-08-12 | Novaremed Limited | Method of treating or preventing pain |
| CA2846604A1 (en) * | 2011-08-25 | 2013-02-28 | Cognition Therapeutics, Inc. | Compositions and methods for treating neurodegenerative disease |
| EP4023294A1 (en) | 2014-01-31 | 2022-07-06 | Cognition Therapeutics, Inc. | Isoindoline compositions and methods for treating alzheimer's disease |
| KR102614814B1 (en) | 2017-05-15 | 2023-12-20 | 카그니션 테라퓨틱스, 인코퍼레이티드 | Composition for treating neurodegenerative diseases |
| 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 |
| CN117326958B (en) * | 2023-09-21 | 2025-07-11 | 锦州奥鸿药业有限责任公司 | A preparation method of high-purity dobutamine hydrochloride |
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 GB GB1683573A patent/GB1392674A/en not_active Expired
- 1973-04-09 DE DE2317710A patent/DE2317710C2/en not_active Expired
- 1973-04-09 CY CY963A patent/CY963A/en unknown
- 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 SU SU1908277A patent/SU496719A3/en active
- 1973-04-11 CH CH517473A patent/CH569691A5/xx not_active IP Right Cessation
- 1973-04-11 CA CA168,428A patent/CA1018188A/en not_active Expired
- 1973-04-11 NL NLAANVRAGE7305097,A patent/NL174459C/en not_active IP Right Cessation
- 1973-04-11 YU YU00976/73A patent/YU36483B/en unknown
- 1973-04-11 KR KR7300573A patent/KR790000113B1/en not_active Expired
- 1973-04-11 AT AT318773A patent/AT323719B/en not_active IP Right Cessation
- 1973-04-11 BE BE1004956A patent/BE798051A/en not_active IP Right Cessation
- 1973-04-11 AU AU54385/73A patent/AU472734B2/en not_active Expired
- 1973-04-11 BG BG023268A patent/BG23001A3/en unknown
- 1973-04-11 DK DK196773A patent/DK142750C/en not_active IP Right Cessation
- 1973-04-11 CH CH1112475A patent/CH580563A5/xx not_active IP Right Cessation
- 1973-04-12 HU HUEI469A patent/HU166213B/hu unknown
- 1973-04-12 HU HUEI552A patent/HU167597B/hu unknown
- 1973-04-12 JP JP48041750A patent/JPS5825656B2/en not_active Expired
- 1973-04-12 CS CS77171A patent/CS190448B2/en unknown
- 1973-04-12 IL IL42016A patent/IL42016A/en unknown
- 1973-04-12 CS CS732601A patent/CS190406B2/en unknown
- 1973-04-12 AR AR247523A patent/AR203822A1/en active
- 1973-04-12 PL PL1973183808A patent/PL94207B1/pl unknown
- 1973-04-12 PH PH14508A patent/PH11041A/en unknown
- 1973-04-12 RO RO7383749A patent/RO70892A/en unknown
- 1973-04-12 RO RO7374457A patent/RO65105A/en unknown
- 1973-04-12 ES ES413639A patent/ES413639A1/en not_active Expired
- 1973-04-12 PL PL1973161874A patent/PL90695B1/pl unknown
- 1973-04-12 DD DD73170118A patent/DD107670B3/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
Also Published As
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