GB1502038A - Pyrido (3,4-b)indole derivatives - Google Patents
Pyrido (3,4-b)indole derivativesInfo
- Publication number
- GB1502038A GB1502038A GB38464/76A GB3486476A GB1502038A GB 1502038 A GB1502038 A GB 1502038A GB 38464/76 A GB38464/76 A GB 38464/76A GB 3486476 A GB3486476 A GB 3486476A GB 1502038 A GB1502038 A GB 1502038A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- qch
- pyrido
- aug
- prepared
- 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
- AIFRHYZBTHREPW-UHFFFAOYSA-N β-carboline Chemical class N1=CC=C2C3=CC=CC=C3NC2=C1 AIFRHYZBTHREPW-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 abstract 1
- 238000010306 acid treatment Methods 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 230000001430 anti-depressive effect Effects 0.000 abstract 1
- 239000000935 antidepressant agent Substances 0.000 abstract 1
- 229940005513 antidepressants Drugs 0.000 abstract 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002475 indoles Chemical class 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
1502038 Pyrido[3,4 - b]indole derivatives ENDO LABORATORIES Inc 20 Aug 1976 [22 Aug 1975 22 June 1976] 34864/76 Heading C2C The invention comprises compounds of formula and their pharmaceutically suitable salts, wherein one of R 1 and R 3 is Me or Et and the other is H, Me or Et; and R 2 is H, C 1-3 alkyl, allyl or propargyl, provided that the total no. of C atoms in R 1 +R 2 +R 3 is #4. In examples, these compounds are prepared by reducing with BH 3 or NaBH 4 , followed by acid treatment, of the 4a,9a-dehydro analogues in which the 2- substituent is R 2 , MeCO or EtCO, or by hydrolysis of the corresponding 2-cyano compounds (for R 2 =H). Starting materials otherwise prepared are the corresponding 3,4 - dihydropyrido[3,4-b)indoles and their quaternary salts, 2-acyl analogues of the compounds of the invention, and compounds of formulae QCH:CRNO 2 , QCH 2 CHRNH 2 and QCH 2 CHRNHCOR<SP>1</SP>, where R is H, Me or Et, and R<SP>1</SP> is Me or Et. Therapeutic compositions having antidepressant activity comprise compounds of the above formula and may be administered orally, parenterally or rectally.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60687175A | 1975-08-22 | 1975-08-22 | |
| US05/695,361 US4091102A (en) | 1975-08-22 | 1976-06-22 | Anti-depressant trans-hexahydropyrido[3,4-b]indoles |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1502038A true GB1502038A (en) | 1978-02-22 |
Family
ID=27085353
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38464/76A Expired GB1502038A (en) | 1975-08-22 | 1976-08-20 | Pyrido (3,4-b)indole derivatives |
Country Status (20)
| Country | Link |
|---|---|
| JP (1) | JPS5225799A (en) |
| AR (1) | AR212633A1 (en) |
| AU (1) | AU497249B2 (en) |
| CA (1) | CA1058617A (en) |
| DD (1) | DD126298A5 (en) |
| DE (1) | DE2637503A1 (en) |
| DK (1) | DK374976A (en) |
| ES (1) | ES450876A1 (en) |
| FI (1) | FI762384A7 (en) |
| FR (1) | FR2321289A1 (en) |
| GB (1) | GB1502038A (en) |
| GR (1) | GR61611B (en) |
| IE (1) | IE43528B1 (en) |
| IL (1) | IL50322A (en) |
| LU (1) | LU75637A1 (en) |
| NL (1) | NL7609293A (en) |
| NO (1) | NO762869L (en) |
| PH (1) | PH12211A (en) |
| PT (1) | PT65505B (en) |
| SE (1) | SE7607882L (en) |
-
1976
- 1976-07-09 SE SE7607882A patent/SE7607882L/en unknown
- 1976-08-19 DK DK374976A patent/DK374976A/en unknown
- 1976-08-19 CA CA259,410A patent/CA1058617A/en not_active Expired
- 1976-08-20 LU LU75637A patent/LU75637A1/xx unknown
- 1976-08-20 IL IL50322A patent/IL50322A/en unknown
- 1976-08-20 DE DE19762637503 patent/DE2637503A1/en not_active Withdrawn
- 1976-08-20 AU AU17009/76A patent/AU497249B2/en not_active Expired
- 1976-08-20 NO NO762869A patent/NO762869L/no unknown
- 1976-08-20 PH PH18807A patent/PH12211A/en unknown
- 1976-08-20 FR FR7625337A patent/FR2321289A1/en not_active Withdrawn
- 1976-08-20 FI FI762384A patent/FI762384A7/fi not_active Application Discontinuation
- 1976-08-20 DD DD194413A patent/DD126298A5/xx unknown
- 1976-08-20 ES ES450876A patent/ES450876A1/en not_active Expired
- 1976-08-20 NL NL7609293A patent/NL7609293A/en not_active Application Discontinuation
- 1976-08-20 IE IE1873/76A patent/IE43528B1/en unknown
- 1976-08-20 AR AR264394A patent/AR212633A1/en active
- 1976-08-20 GB GB38464/76A patent/GB1502038A/en not_active Expired
- 1976-08-20 PT PT65505A patent/PT65505B/en unknown
- 1976-08-21 JP JP51099240A patent/JPS5225799A/en active Pending
- 1976-08-21 GR GR51521A patent/GR61611B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| FR2321289A1 (en) | 1977-03-18 |
| IL50322A0 (en) | 1976-10-31 |
| ES450876A1 (en) | 1977-12-01 |
| NO762869L (en) | 1977-02-23 |
| DE2637503A1 (en) | 1977-03-03 |
| PH12211A (en) | 1978-11-29 |
| PT65505A (en) | 1976-09-01 |
| AR212633A1 (en) | 1978-08-31 |
| AU1700976A (en) | 1978-02-23 |
| AU497249B2 (en) | 1978-12-07 |
| DD126298A5 (en) | 1977-07-06 |
| NL7609293A (en) | 1977-02-24 |
| JPS5225799A (en) | 1977-02-25 |
| PT65505B (en) | 1978-10-10 |
| DK374976A (en) | 1977-02-23 |
| LU75637A1 (en) | 1977-03-31 |
| IL50322A (en) | 1979-07-25 |
| CA1058617A (en) | 1979-07-17 |
| GR61611B (en) | 1978-12-02 |
| IE43528L (en) | 1977-02-22 |
| SE7607882L (en) | 1977-02-23 |
| IE43528B1 (en) | 1981-03-25 |
| FI762384A7 (en) | 1977-02-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| 429A | Application made for amendment of specification (sect. 29/1949) | ||
| 429H | Application (made) for amendment of specification now open to opposition (sect. 29/1949) | ||
| 429D | Case decided by the comptroller ** specification amended (sect. 29/1949) | ||
| SPA | Amended specification published | ||
| PCNP | Patent ceased through non-payment of renewal fee |