GB1597912A - 1,phenyl-2,3,4,5-tetrahydro-1h-3-benzazepine-dione derivatives - Google Patents
1,phenyl-2,3,4,5-tetrahydro-1h-3-benzazepine-dione derivatives Download PDFInfo
- Publication number
- GB1597912A GB1597912A GB20952/80A GB2095280A GB1597912A GB 1597912 A GB1597912 A GB 1597912A GB 20952/80 A GB20952/80 A GB 20952/80A GB 2095280 A GB2095280 A GB 2095280A GB 1597912 A GB1597912 A GB 1597912A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hydrogen
- compounds according
- carbons
- compounds
- tetrahydro
- 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
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/16—Benzazepines; Hydrogenated benzazepines
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/04—Compounds containing oxirane rings containing only hydrogen and carbon atoms in addition to the ring oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
PATENT SPECIFICAT 1
( 21) Application No 20952/80 ( 22) Filed 10 Jan.
( 62) Divided out of No 1597911 ( 31) Convention Application No 760500 ( 32) Filed 19 Jan 1977 in ( 33) United States of America (US) ( 44) Complete Specification published 16 Sept 1981 ( 51) INT CL 3 C 07 D 223/16 ( 52) Index at acceptance ( 72) ON 1978 C 2 C 1732 213 220 226 22 Y 250 251 25 Y 29 X 29 Y 30 Y 351 352 386 409 40 Y 635 760 AA TY Inventor KENNETH GEORGE HOLDEN ( 54) 1-PHENYL-2,3,4,5-TETRAHYDRO 1 H-3BENZAZEPINEDIONE DERIVATIVES ( 71) We, SMITHKLINE CORPORATION, of 1500 Spring Garden Street, Philadelphia, Pennsylvania 19101, United States of America, a corporation organized under the laws of the Commonwealth of Pennsylvania, one of the United States of America, do hereby declare the invention, for which we pray that a patent may be granted to us, and the method by which it is to be performed, to be particularly described in and by the following statement:-
This invention concerns 1 phenyl2,3,4,5 tetrahydro 1 H 3 benzazepines which are useful as intermediates for preparing compounds which act as dopaminergic agents with pronounced activity at central nervous system receptors.
According to the present invention there are provided compounds of the formula:
O in which R' is hydrogen, lower alkyl containing 1-5 carbons, e g methyl hydroxyethyl, lower alkenyl containing 3-5 carbons, benzyl, phenethyl, carbobenzoxy or lower alkanoyl containing 1-5 carbons; and R 2 is hydrogen, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl methoxy or hydroxy, and acid addition salts thereof.
The compounds of the present invention are of value in preparing compounds described and claimed in British Patent Application 953/78 (Serial No 1597711) The compounds of Formula I can be prepared by oxidation of an appropriate compound of formula H O o H O R.
II where R' and R 2 are as hereinbefore defined The oxidation can be effected using 2,3 dichloro 5,6 dicyano 1,4 benzoquinone, for example in solution in methanol.
The following Example is given by way of illustration Temperatures are in degrees Centigrade,.
EXAMPLE
To a suspension of 7,8 dihydroxy I phenyl 2,3,4,5 tetrahydro 1 H 3benzazepine hydrobromide ( 34 g, 0 101 mole, U S Patent Specification No.
3,393,192) in methanol ( 275 ml) was added a solution of 2,3 di chloro 5,6 dicyano 1,4 benzoquinone ( 25 2 g, 0 111 mole) in methanol ( 125 ml) The addition was carried out rapidly with stirring at O under an argon atmosphere After stirring at 0 for 1 hour the reaction mixture was filtered and the orange precipitate was washed with cold methanol ( 75 ml), ethyl acetate ( 100 ml) and then diethyl ether ( 100 ml) After drying at room temperature under vacuum, 1 phenyl 2,3,4,5tetrahydro IH 3 benzazepine 7,8 dione hydrobromide ( 32 8 g, 0 98 mole, 97 %) was obtained, mp 164-165 (dec).
Anal Calc'd for C,6 Hs NO 2 H Br l/4 H 2:
C, 56 34; H, 4 84; N, 4 11 Found: C, 56 02; H, 4 76; N, 4 01.
c m 0 r0 44 z M ( 11) 1 597 912 1.597 912
Claims (2)
1 Compounds of the formula ood lNR 1 0 PI . in which R' is hydrogen, lower alkyl containing 1-5 carbons, hydroxyethyl, lower alkenyl containing 3-5 carbons, benzyl, phenylethyl, carbobenzoxy or lower alkanoyl containing 1-5 carbons; and R 2 is hydrogen, fluoro, chloro, bromo, iodo, trifluoromethyl, methyl, methoxy, or hydroxy, and acid addition salts thereof.
2 Printed for Her Majiesty's Stationery Office, by the Courier Press, Leamington Spa, 1981 Published by The Patent Office 25 Southampton Buildings, London, WC 2 A l AY, from which copies may be obtained.
2 Compounds according to claim 1, in which R' is hydrogen.
3 Compounds according to claim I or claim 2, in which R 2 is hydrogen.
4 Compounds according to claim I or claim 3, in which R' is methyl.
Compounds according to claim 1, as hereinbefore described in the Example.
6 A process for preparing a compound according to claim I substantially as hereinbefore described in the Example 7 Compounds according to any of claims 1 to 5, when prepared by a process according to claim 6.
J A CLAISSE, Chartered Patent Agent.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US76050077A | 1977-01-19 | 1977-01-19 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1597912A true GB1597912A (en) | 1981-09-16 |
Family
ID=25059291
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB20952/80A Expired GB1597912A (en) | 1977-01-19 | 1978-01-10 | 1,phenyl-2,3,4,5-tetrahydro-1h-3-benzazepine-dione derivatives |
GB953/78A Expired GB1597911A (en) | 1977-01-19 | 1978-01-10 | Benzazepines |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB953/78A Expired GB1597911A (en) | 1977-01-19 | 1978-01-10 | Benzazepines |
Country Status (15)
Country | Link |
---|---|
JP (1) | JPS6040423B2 (en) |
AU (1) | AU510459B2 (en) |
BE (1) | BE862878A (en) |
CA (1) | CA1090334A (en) |
CH (2) | CH642634A5 (en) |
DE (1) | DE2802086A1 (en) |
DK (1) | DK19978A (en) |
FR (2) | FR2378017A1 (en) |
GB (2) | GB1597912A (en) |
HU (1) | HU175836B (en) |
IE (1) | IE46761B1 (en) |
LU (1) | LU78873A1 (en) |
NL (1) | NL7800637A (en) |
SE (1) | SE437265B (en) |
ZA (1) | ZA777444B (en) |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5481290A (en) * | 1977-11-17 | 1979-06-28 | Smithkline Corp | Benzazepin compound |
US4171359A (en) * | 1978-04-12 | 1979-10-16 | Smithkline Corporation | Benz-tetrasubstituted 1-phenyl-2,3,4,5-tetrahydro-1H-3-benzazepines |
US4251525A (en) * | 1979-05-25 | 1981-02-17 | Smithkline Corporation | 3-Allyl-7,8-dihydroxy-6-halo-1-(4-hydroxyphenyl)-2,3,4,5-tetrahydro-1H-3-benzazepine derivatives |
DE3065940D1 (en) * | 1979-07-10 | 1984-01-26 | Smithkline Beckman Corp | Synergistic antihypertensive compositions |
CN1823059A (en) * | 2003-05-22 | 2006-08-23 | 先灵公司 | Selective D1/dD receptor antagonists for the treatment of obesity and CNS disorders |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH555831A (en) * | 1967-02-17 | 1974-11-15 | Scherico Ltd | 1-Phenyl-tetrahydro-benzazepin derivs - with antibacterial, antidepressive and hypotensive activity, prepd. by ring-closure of di-(beta-phenyl) ethyl amine using dehydrating agents |
US3609139A (en) * | 1969-04-01 | 1971-09-28 | Sandoz Ag | Substituted dibenzdiazonines |
GB1561305A (en) * | 1975-07-02 | 1980-02-20 | Smithkline Corp | Benzazepine derivatives and pharmeceutical compositions containing them |
US4011319A (en) * | 1975-07-02 | 1977-03-08 | Smithkline Corporation | Pharmaceutical compositions and methods involving benzazepine derivatives |
-
1977
- 1977-12-14 ZA ZA00777444A patent/ZA777444B/en unknown
-
1978
- 1978-01-10 GB GB20952/80A patent/GB1597912A/en not_active Expired
- 1978-01-10 GB GB953/78A patent/GB1597911A/en not_active Expired
- 1978-01-13 FR FR7800998A patent/FR2378017A1/en active Granted
- 1978-01-13 BE BE184290A patent/BE862878A/en not_active IP Right Cessation
- 1978-01-16 AU AU32465/78A patent/AU510459B2/en not_active Expired
- 1978-01-16 LU LU78873A patent/LU78873A1/en unknown
- 1978-01-16 SE SE7800455A patent/SE437265B/en not_active IP Right Cessation
- 1978-01-16 DK DK19978A patent/DK19978A/en not_active Application Discontinuation
- 1978-01-16 CA CA294,973A patent/CA1090334A/en not_active Expired
- 1978-01-18 HU HU78SI1612A patent/HU175836B/en unknown
- 1978-01-18 JP JP53004769A patent/JPS6040423B2/en not_active Expired
- 1978-01-18 NL NL7800637A patent/NL7800637A/en not_active Application Discontinuation
- 1978-01-18 CH CH52578A patent/CH642634A5/en not_active IP Right Cessation
- 1978-01-18 DE DE19782802086 patent/DE2802086A1/en not_active Withdrawn
- 1978-01-18 IE IE111/78A patent/IE46761B1/en unknown
- 1978-06-02 FR FR7816583A patent/FR2384759A1/en active Granted
-
1982
- 1982-06-09 CH CH357382A patent/CH640228A5/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NL7800637A (en) | 1978-07-21 |
AU510459B2 (en) | 1980-06-26 |
BE862878A (en) | 1978-07-13 |
IE46761B1 (en) | 1983-09-21 |
JPS5390281A (en) | 1978-08-08 |
SE437265B (en) | 1985-02-18 |
IE780111L (en) | 1978-07-19 |
JPS6040423B2 (en) | 1985-09-11 |
GB1597911A (en) | 1981-09-16 |
ZA777444B (en) | 1978-10-25 |
SE7800455L (en) | 1978-07-20 |
DK19978A (en) | 1978-07-20 |
FR2378017B1 (en) | 1981-07-10 |
CH642634A5 (en) | 1984-04-30 |
HU175836B (en) | 1980-10-28 |
CH640228A5 (en) | 1983-12-30 |
AU3246578A (en) | 1979-07-26 |
FR2384759B1 (en) | 1980-07-18 |
DE2802086A1 (en) | 1978-07-20 |
CA1090334A (en) | 1980-11-25 |
FR2384759A1 (en) | 1978-10-20 |
FR2378017A1 (en) | 1978-08-18 |
LU78873A1 (en) | 1978-06-09 |
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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 |