FI71935C - Förfarande för framställning av 6-fenyl-11H-pyrido/2,3-b//1,4/bensodia zepiner med antidepressiv verkan. - Google Patents
Förfarande för framställning av 6-fenyl-11H-pyrido/2,3-b//1,4/bensodia zepiner med antidepressiv verkan. Download PDFInfo
- Publication number
- FI71935C FI71935C FI813976A FI813976A FI71935C FI 71935 C FI71935 C FI 71935C FI 813976 A FI813976 A FI 813976A FI 813976 A FI813976 A FI 813976A FI 71935 C FI71935 C FI 71935C
- Authority
- FI
- Finland
- Prior art keywords
- formula
- pyrido
- phenyl
- compound
- benzodiazepine
- Prior art date
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- 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
- A61P25/24—Antidepressants
-
- 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
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Psychiatry (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (8)
1. Förfarande för framställning av 6-fenyl-11H-pyrido-/2,3-b7-/T,j[/bensodiazepiner med antidepressiv verkan enligt formeln Ar. /(H)n |Cf(BlnV'", I Z N Λ ° ' R väri: 1 1 2 1 R betecknar väte, lägre alkyl eller -alk -NR R , väri R 2 12 och R betecknar envar väte, lägre alkyl, eller R och R bildar tillsammans med den närliggande kväveatomen en heterocyklisk grupp som utgörs av 1-piperidinyl eller 4-morfolino, Ar betecknar fenyl sora kan vara substituerad med halogen, lägre alkyl, lägre alkoxi eller nitro, alk^ betecknar lägre alkylen, företrädesvis etylen eller propylen, Z betecknar väte eller halogen, n betecknar 0 eller 1, och när n betecknar 0, betecknar den prickade linjen en dubbelbindning, och syraadditionssalter därav, kännetecknat av att en blandning av ett 2-halogen-3-aminopyridin med formeln H-N halo'"' N ' och ett (aminofenyl)arylmetanon med formeln 0 II ' Ar z—fO III väri Z och Ar har ovan angivna betydelser, eller en reak-tionsprodukt därav med formeln II 51 71935 Ar % / ;c ii .-. / H N H väri Z och Ar har ovan angivna betydelser, uppvärms under en sadan tidsperiod och under sädana förhällanden att reak-tionsvattnet avgär och det sker en cyklisering till 11H-pyrido/2,3-b/ /1,4/bensodiazepin med formeln Ar - H väri Ar och Z har ovan angivna betydelser, varefter, om sä önskas en eller flera av följande bireaktioner utförs: 1. en förening med formeln Ia reduceras med natriumbor-cyanohydrin tili en förening med formeln m H V- 7 /"-pT Ny-\ n AO) Ia-' i N J H 2. en förening med formeln Ia eller formeln Ia-1 omsätts med ett halo-alk Q-reagens, väri Q betecknar -N-(lägre alkyl)2r 1-piperidinyl, 4-morfolino, 1-ftalimido, O j; -N-C-O-lägre alkyl eller halogen, varvid man erhäller en förening med formeln Ar /(H)n alkl.Q 52 7 1 9 3 5 3. en förening med formeln Ib,väri Q betecknar ftalimido, omsätts med alkoholhydrazinhydrat och en syra, varvid man erhäller en förening med formeln Ar /(H)n ^->5) alk1-NH2 4. en förening med formeln Ie omsätts med trietylortoformat under en sadan tidsperiod som räcker tili för att bilda en metanimidester med formeln Ar>NW ^iH)n , &»X°) alk1-N=CH-OC2H5 och därefter reduceras metanimidestern med natriumborhydrid, varvid man erhäller en förening med formeln Ar / n Vn X le I! ¥ alk -N-CH3 5. en förening med formeln Ie omsätts med etylkloroformat (och trietylamin) med därpä följande reducering med litium-aluminiumhydrid, varvid man erhäller en förening med formeln 53 7 1 9 3 5 Ar H alk1-N-CH3 6. en förening med formeln I överförs till ett farma-ceutiskt acceptabelt syraadditionssalt.
2. Förfarande enligt patentkravet 1, känneteck-n a t av att man framställer 8-klor-N,N-dimetyl-6-fenyl- 11H-pyrido/2,3-b/ /1, 4/bensodiazepin-11-propanamin eller ett farmaceutiskt acceptabelt salt därav.
3. Förfarande enligt patentkravet 1, känneteck-n a t av att man framställer N,N-dimetyl-6-fenyl-11H-pyrido/2,3-b7 /1,£/benzodiazepin-11-propanamin eller ett farmaceutiskt acceptabelt salt därav.
4. Förfarande enligt patentkravet 1, känneteck-n a t av att man framställer N,N-dimetyl-6-fenyl-11H-pyridc72,3-b7 /1 , 4^7bensodiazepin-1 1-etanamin eller ett farmaceutiskt acceptabelt salt därav.
5. Förfarande enligt patentkravet 1, känneteck-n a t av att man framställer N-mety1-6-fenyl-11H-pyrido-/2,3-bJ /1^/bensodiazepin-l1-propanamin eller ett farmaceutiskt acceptabelt salt därav.
6. Förfarande enligt patentkravet 1, känneteck-n a t av att man framställer 6-(4—fluorfenyl)-N,N-di-metyl-11H-pyrido/2,3-b/ /1,4/bensoazepin-11-propanamin eller ett farmaceutiskt acceptabelt salt därav.
7. Förfarande enligt patentkravet 1, känneteck-n a t av att man framställer 6-(2-klorfenyl)-N,N-dimetyl-
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FI861412A FI77232C (sv) | 1981-09-24 | 1986-04-01 | Som mellanprodukt vid framställning av 6-fenyl-11H-pyrido/2,3-b//1,4/b entsodiazepiner användbara 2-/(3-amino-2-pyridinyl)amino/fenylarylmeta nonderivat. |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30508081A | 1981-09-24 | 1981-09-24 | |
| US30508081 | 1981-09-24 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI813976L FI813976L (fi) | 1983-03-25 |
| FI71935B FI71935B (fi) | 1986-11-28 |
| FI71935C true FI71935C (sv) | 1987-03-09 |
Family
ID=23179241
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI813976A FI71935C (sv) | 1981-09-24 | 1981-12-10 | Förfarande för framställning av 6-fenyl-11H-pyrido/2,3-b//1,4/bensodia zepiner med antidepressiv verkan. |
Country Status (27)
| Country | Link |
|---|---|
| JP (1) | JPS5865290A (sv) |
| KR (1) | KR890000764B1 (sv) |
| BE (1) | BE891666A (sv) |
| CA (1) | CA1199324A (sv) |
| CH (1) | CH651833A5 (sv) |
| DE (1) | DE3150522A1 (sv) |
| DK (3) | DK186282A (sv) |
| EG (1) | EG15904A (sv) |
| ES (6) | ES8303348A1 (sv) |
| FI (1) | FI71935C (sv) |
| FR (1) | FR2515183B1 (sv) |
| GR (1) | GR78473B (sv) |
| HU (2) | HU189426B (sv) |
| IE (1) | IE52493B1 (sv) |
| IL (1) | IL64284A (sv) |
| IN (1) | IN156080B (sv) |
| IT (1) | IT1146728B (sv) |
| LU (1) | LU83865A1 (sv) |
| NL (1) | NL8200549A (sv) |
| NO (1) | NO157700C (sv) |
| NZ (1) | NZ198999A (sv) |
| PH (2) | PH17847A (sv) |
| PL (6) | PL143596B1 (sv) |
| PT (1) | PT74286B (sv) |
| SE (2) | SE448629B (sv) |
| YU (1) | YU46128B (sv) |
| ZA (1) | ZA817866B (sv) |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3825549A (en) * | 1972-10-24 | 1974-07-23 | Squibb & Sons Inc | Certain dihydropyrido(2,1-b)(1,3)benzodi-azepines and benzodiazocines |
| DE2424811C3 (de) * | 1974-05-22 | 1981-08-20 | Dr. Karl Thomae Gmbh, 7950 Biberach | Pyrido-benzodiazepinone, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| SE422799B (sv) * | 1975-05-28 | 1982-03-29 | Merck & Co Inc | Analogiforfarande for framstellning av 1,3-dihydroimidazo (4,5-b)pyridin-2-oner |
-
1981
- 1981-11-05 SE SE8106573A patent/SE448629B/sv not_active IP Right Cessation
- 1981-11-12 NO NO813839A patent/NO157700C/no unknown
- 1981-11-12 ZA ZA817866A patent/ZA817866B/xx unknown
- 1981-11-13 IN IN1261/CAL/81A patent/IN156080B/en unknown
- 1981-11-13 IL IL64284A patent/IL64284A/xx unknown
- 1981-11-17 GR GR66553A patent/GR78473B/el unknown
- 1981-11-18 PH PH26507A patent/PH17847A/en unknown
- 1981-11-25 IE IE2769/81A patent/IE52493B1/en unknown
- 1981-12-09 IT IT68605/81A patent/IT1146728B/it active
- 1981-12-10 FI FI813976A patent/FI71935C/sv not_active IP Right Cessation
- 1981-12-15 ES ES507971A patent/ES8303348A1/es not_active Expired
- 1981-12-15 HU HU843212A patent/HU189426B/hu not_active IP Right Cessation
- 1981-12-15 HU HU813777A patent/HU187393B/hu not_active IP Right Cessation
- 1981-12-21 DE DE19813150522 patent/DE3150522A1/de not_active Withdrawn
- 1981-12-23 PL PL1981253538A patent/PL143596B1/pl unknown
- 1981-12-23 FR FR8124111A patent/FR2515183B1/fr not_active Expired
- 1981-12-23 PL PL1981253540A patent/PL143322B1/pl unknown
- 1981-12-23 PL PL1981253539A patent/PL143597B1/pl unknown
- 1981-12-23 PL PL1981241409A patent/PL139381B1/pl unknown
- 1981-12-23 PL PL1981234426A patent/PL138859B1/pl unknown
- 1981-12-23 PL PL1981241410A patent/PL137068B1/pl unknown
- 1981-12-30 BE BE0/206969A patent/BE891666A/fr not_active IP Right Cessation
-
1982
- 1982-01-05 LU LU83865A patent/LU83865A1/fr unknown
- 1982-01-12 EG EG11/82A patent/EG15904A/xx active
- 1982-01-14 JP JP57004813A patent/JPS5865290A/ja active Pending
- 1982-01-15 PT PT74286A patent/PT74286B/pt unknown
- 1982-01-18 CA CA000394367A patent/CA1199324A/en not_active Expired
- 1982-02-02 KR KR8200420A patent/KR890000764B1/ko active
- 1982-02-12 NL NL8200549A patent/NL8200549A/nl not_active Application Discontinuation
- 1982-02-18 NZ NZ198999A patent/NZ198999A/en unknown
- 1982-03-23 YU YU62582A patent/YU46128B/sh unknown
- 1982-04-15 CH CH2288/82A patent/CH651833A5/fr not_active IP Right Cessation
- 1982-04-26 DK DK186282A patent/DK186282A/da not_active Application Discontinuation
- 1982-09-29 ES ES516052A patent/ES8402295A1/es not_active Expired
- 1982-09-29 ES ES516051A patent/ES516051A0/es active Granted
-
1983
- 1983-10-19 ES ES526562A patent/ES526562A0/es active Granted
- 1983-10-19 ES ES526563A patent/ES8604531A1/es not_active Expired
-
1984
- 1984-08-17 PH PH31120A patent/PH20536A/en unknown
-
1985
- 1985-05-21 ES ES543328A patent/ES8607726A1/es not_active Expired
-
1986
- 1986-02-17 SE SE8600688A patent/SE455305B/sv not_active IP Right Cessation
-
1987
- 1987-08-03 DK DK403487A patent/DK403487A/da not_active Application Discontinuation
- 1987-08-03 DK DK403387A patent/DK403387A/da not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: A.H. ROBINS COMPANY, INCORPORATED |