GB1497722A - Octahydrobenzo(c)(1,6)naphthyridines - Google Patents
Octahydrobenzo(c)(1,6)naphthyridinesInfo
- Publication number
- GB1497722A GB1497722A GB4516/75A GB451675A GB1497722A GB 1497722 A GB1497722 A GB 1497722A GB 4516/75 A GB4516/75 A GB 4516/75A GB 451675 A GB451675 A GB 451675A GB 1497722 A GB1497722 A GB 1497722A
- Authority
- GB
- United Kingdom
- Prior art keywords
- alkoxy
- compounds
- alkyl
- represent
- substituents
- 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
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
1497722 2 - Methyl - 6 - phenyl - octahydrobenzo[c][1,6]naphthyridines SANDOZ Ltd 3 Feb 1975 [5 Feb 1974] 4516/75 Heading C2C Novel compounds I and salts thereof in which R 1 is H, OH or C 1-4 alkoxy and (a) R 2 is H, C 1-4 alkyl, C 1-4 alkoxy, OH, halogen, NO 2 NH 2 , NMe 2 or C 1-5 alkanoylamino and R 3 and R 4 are H (b) R 2 is C 1-4 alkyl, C 1-4 alkoxy, OH, halogen or NO 2 , R 3 is C 1-4 alkyl, C 1-4 alkoxy, OH or Cl and R 4 is H (c) R 2 , R 3 and R<SP>4</SP> are C 1-4 alkoxy (d) R 2 , R 3 nd R 4 are C 1-4 alkyl or (e) R 2 , R 3 and R 4 are OH with the provisos that (i) when R 1 is OH in the 9 position, each of R 2 , R 3 and R 4 is other than C 1-4 alkoxy (ii) when one of R 2 and R 3 is C 1-4 alkoxy, the other is not OH (iii) R 1 is other than H when R 2 , R 3 and R 4 represent as substituents 4-methyl, 3,4,5- trimethoxy, 3,4,5-trihydroxy, 3,4-dimethoxy or 3,4-dichloro and (iv) R 1 is other than 8-OH when R 2 , R 3 and R 4 represent as substituents 4-chloro or 4-acetylamino or represent no substituent; are prepared by reducing a compound II where R 6 is H, OH, C 1-4 alkoxy or benzyloxy and if desired converting the compound obtained into a salt. Compounds I (R 1 = OH) are also produced by ether splitting of the corresponding C 1-4 alkyl or benzyl ether. Compounds I (R 2 , R 3 and/or R 4 or OH) are also produced by hydrogenolysis of the corresponding benzyloxy compounds. Compounds II are obtained by cyclization of the corresponding cis 4-benzoylamino-1- methyl - 3 - phenyl piperidine according to Bischler-Napieralski and, for compounds where R 2 is NH 2 , NMe 2 or C 1-5 acylamino, reducing the corresponding compound where R 2 is NO 2 followed by acylation or reductive methylation. Compounds I (excluding those where R 1 is 9-OMe and R 2 , R 3 and R 4 represent as substituents 4-dimethylamino, 3,4-dimethoxy, 3,4- dichloro or 3,4-dihydroxy and where R 1 is 8-OMe and R 2 , R 3 and R 4 represent as substituents 3,4,5-trimethoxy, 4-fluoro or 4- methoxy) have bronchospasmolytic activity and form with a carrier or diluent a pharmaceutical composition which may be administered orally or by inhalation.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH155074 | 1974-02-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1497722A true GB1497722A (en) | 1978-01-12 |
Family
ID=4213026
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4516/75A Expired GB1497722A (en) | 1974-02-05 | 1975-02-03 | Octahydrobenzo(c)(1,6)naphthyridines |
| GB30857/77A Expired GB1497723A (en) | 1974-02-05 | 1975-02-03 | Octahydrobenzo-(c)(1,6)-naphthyridine derivative |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB30857/77A Expired GB1497723A (en) | 1974-02-05 | 1975-02-03 | Octahydrobenzo-(c)(1,6)-naphthyridine derivative |
Country Status (19)
| Country | Link |
|---|---|
| JP (1) | JPS50108297A (en) |
| AT (1) | AT351536B (en) |
| BE (1) | BE825124A (en) |
| CA (1) | CA1055944A (en) |
| DD (1) | DD117216A5 (en) |
| DE (1) | DE2503156A1 (en) |
| DK (1) | DK136189B (en) |
| ES (1) | ES434406A1 (en) |
| FI (1) | FI750205A (en) |
| FR (1) | FR2259611B1 (en) |
| GB (2) | GB1497722A (en) |
| HU (1) | HU169923B (en) |
| IL (1) | IL46553A (en) |
| NL (1) | NL7501159A (en) |
| NO (1) | NO750263L (en) |
| NZ (1) | NZ176550A (en) |
| PH (1) | PH11824A (en) |
| SE (1) | SE7500859L (en) |
| ZA (1) | ZA75743B (en) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8800397D0 (en) * | 1988-01-08 | 1988-02-10 | Sandoz Ltd | Improvements in/relating to organic compounds |
| MY105344A (en) * | 1990-05-16 | 1994-09-30 | Byk Gulden Lomberg Chemische Fabrik | New sulphonyl compounds |
-
1975
- 1975-01-27 DK DK24275AA patent/DK136189B/en unknown
- 1975-01-27 SE SE7500859A patent/SE7500859L/xx unknown
- 1975-01-27 DE DE19752503156 patent/DE2503156A1/en active Pending
- 1975-01-27 FI FI750205A patent/FI750205A/fi not_active Application Discontinuation
- 1975-01-29 NO NO750263A patent/NO750263L/no unknown
- 1975-01-31 NL NL7501159A patent/NL7501159A/en not_active Application Discontinuation
- 1975-02-03 ES ES434406A patent/ES434406A1/en not_active Expired
- 1975-02-03 PH PH16771A patent/PH11824A/en unknown
- 1975-02-03 DD DD183969A patent/DD117216A5/xx unknown
- 1975-02-03 NZ NZ176550A patent/NZ176550A/en unknown
- 1975-02-03 IL IL46553A patent/IL46553A/en unknown
- 1975-02-03 HU HUSA2741A patent/HU169923B/hu unknown
- 1975-02-03 GB GB4516/75A patent/GB1497722A/en not_active Expired
- 1975-02-03 GB GB30857/77A patent/GB1497723A/en not_active Expired
- 1975-02-03 BE BE153007A patent/BE825124A/en unknown
- 1975-02-04 JP JP50014021A patent/JPS50108297A/ja active Pending
- 1975-02-04 CA CA219,303A patent/CA1055944A/en not_active Expired
- 1975-02-04 AT AT79975A patent/AT351536B/en not_active IP Right Cessation
- 1975-02-05 FR FR7503547A patent/FR2259611B1/fr not_active Expired
- 1975-02-05 ZA ZA00750743A patent/ZA75743B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ZA75743B (en) | 1976-09-29 |
| GB1497723A (en) | 1978-01-12 |
| DK136189B (en) | 1977-08-29 |
| DK136189C (en) | 1978-01-30 |
| BE825124A (en) | 1975-08-04 |
| ATA79975A (en) | 1979-01-15 |
| FI750205A (en) | 1975-08-06 |
| CA1055944A (en) | 1979-06-05 |
| AT351536B (en) | 1979-07-25 |
| PH11824A (en) | 1978-07-19 |
| FR2259611A1 (en) | 1975-08-29 |
| NZ176550A (en) | 1978-09-25 |
| DD117216A5 (en) | 1976-01-05 |
| DE2503156A1 (en) | 1975-08-07 |
| ES434406A1 (en) | 1977-03-01 |
| JPS50108297A (en) | 1975-08-26 |
| DK24275A (en) | 1975-09-29 |
| SE7500859L (en) | 1975-08-06 |
| IL46553A0 (en) | 1975-04-25 |
| AU7784375A (en) | 1976-08-05 |
| IL46553A (en) | 1977-12-30 |
| HU169923B (en) | 1977-02-28 |
| FR2259611B1 (en) | 1980-01-11 |
| NL7501159A (en) | 1975-08-07 |
| NO750263L (en) | 1975-09-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] |