IL42790A - 4a-aryl-trans-decahydroisoquinolines their preparation and pharmaceutical compositions containing them - Google Patents
4a-aryl-trans-decahydroisoquinolines their preparation and pharmaceutical compositions containing themInfo
- Publication number
- IL42790A IL42790A IL42790A IL4279073A IL42790A IL 42790 A IL42790 A IL 42790A IL 42790 A IL42790 A IL 42790A IL 4279073 A IL4279073 A IL 4279073A IL 42790 A IL42790 A IL 42790A
- Authority
- IL
- Israel
- Prior art keywords
- compound
- trans
- formula
- decahydroisoquinoline
- administering
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines
- C07D217/04—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems 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 carbon atoms of the nitrogen-containing ring
- C07D217/24—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring 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 atoms of the carbocyclic ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
Claims (30)
1. A compound of the formula A · v/herein R1 is hydrogen, Cj-Cg alkyl, benzyl, phenethyl, or cycloalkylmethyl of the formula -CH2CH < (CH2)n in which n is an integer in the range 2 R is divalent oxygen , A is hydrogen or hydroxy ; Claim 1 (continued) in which 3 R is hydrogen, hydroxy.or methoxy; 4 R is 'hydroxy or methoxy j
2. A compound according to claim 1 which is dextrorotatory.
3. A compound according to claim 1 which is laevorotatory.
4. The compound of claim 1 which is N-methyl-4a-phenyl-trans-decahydroisoquinoline.
5. The laevo isomer of the compound of claim 4.
6. The dextro isomer of the compound of claim 4.
7. The compound of claim 1 which is N-methyl-4a( methoxyphenyl)-trans-decahydroisoquinoline.
8. · The compound of claim 1 which is N-methyl-4a-(m-hydroxyphenyl)-trans-decahydroisoquinoline.
9. The compound of claim 1 which is N-methyl- a-phenyl-Sa-hydroxy-trans-decahydroisoquinoline.
10. The compound of claim 1 which is N-cyclohexyl-methyl-a-phenyl-trans-decahydroisoquinoline.
11. The compound of claim 1 which is N-phenethyl- a (m-metho:yphenyl)-trans-decahydroisoquinoline.
12. The compound of claim 1 which is N-phenethyl-i+a (m-hydroxyphenyl)-trans-decahydroisoquinoline .
13. A process for preparing a compound of the formula wherein H R is hydrogen, C-j-C^ al-kyl, benzyl, phenethyl, or cycloalkylmethyl of the formula -CH,CH :(CH2)n in which n is an integer in the range 2-5» Ar1 is in which 7 . R is hydrogen or'methoxy and K is methoxy. said process comprising the sequential steps of (a) contacting a compound of the formula with an anhydrouc alcohol of the formula RD0H, wherein R^ is alkyl of 1-4 carbons, in the presence of anhydrous HC1, under inert, anhydrous conditions at a temperature in the range of 50-120°C to form the corresponding diketo derivative of the formula (b) heating the diketo product of step (a) with sodium hydride and a halide R^Br or R"" I to form the corresponding N-substituted derivative of the formula contacting the N-substituted >roduct of step (b) V7ith hydrogen in the presence of a reducing catalyst to form the correspond inn; trnriD diheto derivative of tne formula (d) refluxing the trans derivative of step (c) with lithium aluminum hydride to form the desired product
14. , A process for the preparation of a compound the formula which comprises the sequential steps of (a) heating a compound of the formula with chloroperbenzoic acid to produce an epoxy compound of the formula 42790/2 heating the epoxy product of step (a) with lithium aluminum hydride to form the desired product wherein R is hydrogen, C-^-Cg alkyl, benzyl, phenethyl, or cycloalkylmethyl of the formula -CH^CH < (CH2)n in which n is an integer in the range 2-5» Ar is in which R is hydrogen or methoxy and o R is methoxy. 42790/2
15.» An analgesic composition comprising an effective analgesic amount of a compound of claim 1 and a pharmaceutically acceptable carrier.
16. The composition of claim 15 in which the compound is N-methy 1-^a-phenyl-trans-decahydroisoquinoline .
17. The composition of claim 15 in which the compound is N-methyl-¾a-(m-methoxyphenyl)-trans-decahydroiso-quinollne.
18. ·. The composition of claim 15 in which the compound is N-methyl-¾a-(m-hydroxyphenyl)-trans-decahydroiso-quinoline.
19. ·, The composition of claim 15 in which the compound is N-methy1-^a-pheny l-8a-hydroxy-trans-decahydroiso-quinoline .
20.. The composition of claim 15 in which the compound is N-cyclohex lmethyl-i+a-phenyl-trans-decahydroiso-quinoline.
21.. The composition of claim 15 in which the compound is N-phenethyl- a-(m-methoxyphenyl)-trans-decahydro- isoquinoline.
22. The composition of claim 15 in which the* compound is N-phenethyl- a-(m-hydroxyphenyl)-trans-decahydro- 42790/2
23. A method of producing analgesia which consists essentially of administering to a warm-blooded animal an effective amount of a compound of claim 1.
24. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an effective amount of_a- compounds of claim .
25.. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an effective amount of a compound of claim 7.
26. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an effective amount of a compound of claim 3.
27. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an effective amount of a compound of claim 9.
28. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an effective amount of a compound*l.of claim 10.
29. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an effective amount of a compound of claim 11.
30. A method of producing analgesia which consists essentially in administering to a warm-blooded animal an
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27380672A | 1972-07-20 | 1972-07-20 | |
| US36584373A | 1973-06-01 | 1973-06-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL42790A0 IL42790A0 (en) | 1973-10-25 |
| IL42790A true IL42790A (en) | 1976-11-30 |
Family
ID=26956443
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL42790A IL42790A (en) | 1972-07-20 | 1973-07-19 | 4a-aryl-trans-decahydroisoquinolines their preparation and pharmaceutical compositions containing them |
| IL48667A IL48667A (en) | 1972-07-20 | 1973-07-19 | 4a-aryl-1,3-diketo-trans-decahydroisoquinolines and 4a-aryl-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinolines and their preparation |
| IL48667A IL48667A0 (en) | 1972-07-20 | 1975-12-15 | 4alpha-aryl-1,3-diketo-trans-decahydroisoquinolines and 4alpha-aryl-1,3-diketo-1,2,3,4,4alpha,5,6,7-octahydroisoquinolines and their preparation |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL48667A IL48667A (en) | 1972-07-20 | 1973-07-19 | 4a-aryl-1,3-diketo-trans-decahydroisoquinolines and 4a-aryl-1,3-diketo-1,2,3,4,4a,5,6,7-octahydroisoquinolines and their preparation |
| IL48667A IL48667A0 (en) | 1972-07-20 | 1975-12-15 | 4alpha-aryl-1,3-diketo-trans-decahydroisoquinolines and 4alpha-aryl-1,3-diketo-1,2,3,4,4alpha,5,6,7-octahydroisoquinolines and their preparation |
Country Status (13)
| Country | Link |
|---|---|
| JP (1) | JPS4985075A (en) |
| AR (1) | AR208650A1 (en) |
| CA (1) | CA1024149A (en) |
| DE (2) | DE2351599A1 (en) |
| ES (1) | ES417127A1 (en) |
| FR (1) | FR2193600B1 (en) |
| GB (2) | GB1436377A (en) |
| HU (1) | HU167738B (en) |
| IE (1) | IE37929B1 (en) |
| IL (3) | IL42790A (en) |
| LU (1) | LU68066A1 (en) |
| NL (1) | NL7310078A (en) |
| SE (1) | SE7602150L (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SE7509337L (en) * | 1974-09-23 | 1976-03-24 | Du Pont | PAINING ASSOCIATIONS |
| BG30927A3 (en) * | 1977-12-27 | 1981-09-15 | Eli Lilly And Company | Method for obtaining of trans- 4- alpha- phenyl- octahydro- 1h- 2- pyridine |
| KR950002885B1 (en) * | 1990-06-05 | 1995-03-28 | 토레이가부시키가이샤 | Indole derivatives |
| CA2112744A1 (en) * | 1991-07-05 | 1993-01-21 | Vittorrio Vecchietti | Hydroisoquinoline derivatives |
| IT1307327B1 (en) * | 1995-09-12 | 2001-10-30 | Smithkline Beecham Spa | REPLACED HYDROISOKINOLINIC DERIVATIVES |
-
1973
- 1973-07-18 DE DE19732351599 patent/DE2351599A1/en active Pending
- 1973-07-18 CA CA176,763A patent/CA1024149A/en not_active Expired
- 1973-07-18 DE DE19732336559 patent/DE2336559A1/en active Pending
- 1973-07-19 FR FR7326508A patent/FR2193600B1/fr not_active Expired
- 1973-07-19 IL IL42790A patent/IL42790A/en unknown
- 1973-07-19 IE IE1229/73A patent/IE37929B1/en unknown
- 1973-07-19 HU HUDU206A patent/HU167738B/hu unknown
- 1973-07-19 GB GB3938775A patent/GB1436377A/en not_active Expired
- 1973-07-19 NL NL7310078A patent/NL7310078A/xx not_active Application Discontinuation
- 1973-07-19 AR AR249168A patent/AR208650A1/en active
- 1973-07-19 GB GB3443873A patent/GB1436376A/en not_active Expired
- 1973-07-19 IL IL48667A patent/IL48667A/en unknown
- 1973-07-20 ES ES417127A patent/ES417127A1/en not_active Expired
- 1973-07-20 LU LU68066A patent/LU68066A1/xx unknown
- 1973-07-20 JP JP48082484A patent/JPS4985075A/ja active Pending
-
1975
- 1975-12-15 IL IL48667A patent/IL48667A0/en unknown
-
1976
- 1976-02-23 SE SE7602150A patent/SE7602150L/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1436377A (en) | 1976-05-19 |
| ES417127A1 (en) | 1976-04-01 |
| IE37929B1 (en) | 1977-11-09 |
| CA1024149A (en) | 1978-01-10 |
| AU5820773A (en) | 1975-01-23 |
| IL48667A0 (en) | 1976-02-29 |
| FR2193600A1 (en) | 1974-02-22 |
| NL7310078A (en) | 1974-01-22 |
| DE2351599A1 (en) | 1974-01-31 |
| LU68066A1 (en) | 1973-09-26 |
| IL48667A (en) | 1976-11-30 |
| IL42790A0 (en) | 1973-10-25 |
| HU167738B (en) | 1975-12-25 |
| DE2336559A1 (en) | 1974-01-31 |
| FR2193600B1 (en) | 1976-10-22 |
| IE37929L (en) | 1974-01-20 |
| AR208650A1 (en) | 1977-02-28 |
| GB1436376A (en) | 1976-05-19 |
| JPS4985075A (en) | 1974-08-15 |
| SE7602150L (en) | 1976-02-23 |
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