GB1318944A - Hexahydrobenzindole derivatives - Google Patents
Hexahydrobenzindole derivativesInfo
- Publication number
- GB1318944A GB1318944A GB4715970A GB4715970A GB1318944A GB 1318944 A GB1318944 A GB 1318944A GB 4715970 A GB4715970 A GB 4715970A GB 4715970 A GB4715970 A GB 4715970A GB 1318944 A GB1318944 A GB 1318944A
- Authority
- GB
- United Kingdom
- Prior art keywords
- indoles
- benz
- compounds
- indolinyl
- benzoyl
- 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
- ICISUXWQUUKZMT-UHFFFAOYSA-N 2,3,3a,4,5,9b-hexahydro-1h-benzo[g]indole Chemical class C1CC2=CC=CC=C2C2C1CCN2 ICISUXWQUUKZMT-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 3
- 150000001412 amines Chemical class 0.000 abstract 2
- UTCMYCAFVUUNBK-UHFFFAOYSA-N benzo[cd]indole Chemical class C1=CC(C=N2)=C3C2=CC=CC3=C1 UTCMYCAFVUUNBK-UHFFFAOYSA-N 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- DNXIKVLOVZVMQF-UHFFFAOYSA-N (3beta,16beta,17alpha,18beta,20alpha)-17-hydroxy-11-methoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]-yohimban-16-carboxylic acid, methyl ester Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(C(=O)OC)C(O)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 DNXIKVLOVZVMQF-UHFFFAOYSA-N 0.000 abstract 1
- OVXDVWVMKICYBN-UHFFFAOYSA-N 1-(2a,3,4,5,5a,6-hexahydro-2H-benzo[cd]indol-1-yl)ethanone Chemical group C(C)(=O)N1CC2C=3C(CC=CC1=3)CCC2 OVXDVWVMKICYBN-UHFFFAOYSA-N 0.000 abstract 1
- FUHUCCZDQAURLS-UHFFFAOYSA-N 1-benzoyl-8-methyl-2,2a,3,4-tetrahydrobenzo[cd]indol-5-one Chemical group C(C1=CC=CC=C1)(=O)N1CC2C=3C(=CC=C(C13)C)C(CC2)=O FUHUCCZDQAURLS-UHFFFAOYSA-N 0.000 abstract 1
- YYXHPIFGGUHJGM-UHFFFAOYSA-N 1-nitroso-2H-benzo[cd]indole Chemical class N(=O)N1CC2=C3C(C=CC=C13)=CC=C2 YYXHPIFGGUHJGM-UHFFFAOYSA-N 0.000 abstract 1
- SSKDVCULXAVNIR-UHFFFAOYSA-N 2-(1-benzoyl-7-methyl-2,3-dihydroindol-3-yl)propanoic acid Chemical compound C(C1=CC=CC=C1)(=O)N1CC(C2=CC=CC(=C12)C)C(C(=O)O)C SSKDVCULXAVNIR-UHFFFAOYSA-N 0.000 abstract 1
- BNEVEZKWKCEQQI-UHFFFAOYSA-N 2-(7-methyl-2,3-dihydro-1h-indol-3-yl)propanoic acid Chemical compound C1=CC=C(C)C2=C1C(C(C)C(O)=O)CN2 BNEVEZKWKCEQQI-UHFFFAOYSA-N 0.000 abstract 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- KGWPHCDTOLQQEP-UHFFFAOYSA-N 7-methylindole Chemical group CC1=CC=CC2=C1NC=C2 KGWPHCDTOLQQEP-UHFFFAOYSA-N 0.000 abstract 1
- 229910010082 LiAlH Inorganic materials 0.000 abstract 1
- LCQMZZCPPSWADO-UHFFFAOYSA-N Reserpilin Natural products COC(=O)C1COCC2CN3CCc4c([nH]c5cc(OC)c(OC)cc45)C3CC12 LCQMZZCPPSWADO-UHFFFAOYSA-N 0.000 abstract 1
- QEVHRUUCFGRFIF-SFWBKIHZSA-N Reserpine Natural products O=C(OC)[C@@H]1[C@H](OC)[C@H](OC(=O)c2cc(OC)c(OC)c(OC)c2)C[C@H]2[C@@H]1C[C@H]1N(C2)CCc2c3c([nH]c12)cc(OC)cc3 QEVHRUUCFGRFIF-SFWBKIHZSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 230000008485 antagonism Effects 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Chemical group CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- FHKVFVCJZLNCPU-UHFFFAOYSA-N methyl N'-(2H-benzo[cd]indol-1-yl)carbamimidothioate Chemical class CSC(NN1CC2=C3C(C=CC=C13)=CC=C2)=N FHKVFVCJZLNCPU-UHFFFAOYSA-N 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 210000004400 mucous membrane Anatomy 0.000 abstract 1
- BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 abstract 1
- 229960003147 reserpine Drugs 0.000 abstract 1
- MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 abstract 1
- 230000001624 sedative effect Effects 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
- 150000003585 thioureas Chemical class 0.000 abstract 1
- 230000000699 topical effect Effects 0.000 abstract 1
- 239000005526 vasoconstrictor agent Substances 0.000 abstract 1
Classifications
-
- 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
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/90—Benzo [c, d] indoles; Hydrogenated benzo [c, d] indoles
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1585869A CH517757A (de) | 1969-10-24 | 1969-10-24 | Verfahren zur Herstellung neuer Imidazolin- Verbindungen |
| CH1018270 | 1970-07-06 | ||
| CH1018370A CH528524A (de) | 1970-07-06 | 1970-07-06 | Verfahren zur Herstellung neuer Benz(cd)indol-Derivate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1318944A true GB1318944A (en) | 1973-05-31 |
Family
ID=27176385
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4715970A Expired GB1318944A (en) | 1969-10-24 | 1970-10-05 | Hexahydrobenzindole derivatives |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3674801A (https=) |
| JP (1) | JPS4833748B1 (https=) |
| BE (1) | BE757879A (https=) |
| DE (1) | DE2051062A1 (https=) |
| DK (1) | DK126944B (https=) |
| FR (1) | FR2070159B1 (https=) |
| GB (1) | GB1318944A (https=) |
| IL (1) | IL35504A (https=) |
| NL (1) | NL7015541A (https=) |
| NO (1) | NO129523B (https=) |
| PL (1) | PL81057B1 (https=) |
| SE (1) | SE377125B (https=) |
| SU (1) | SU461496A3 (https=) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI206974A7 (https=) * | 1973-07-16 | 1975-01-17 | Sandoz Ag | |
| JPS54151990A (en) * | 1978-04-17 | 1979-11-29 | Beiersdorf Ag | Novel condensated nitrogenncontained heterocyclic compound and its manufacture |
| US5302612A (en) * | 1990-02-26 | 1994-04-12 | Eli Lilly And Company | 6-substituted-hexahydrobenz[cd]indoles |
| US5229409A (en) * | 1990-08-15 | 1993-07-20 | Eli Lilly And Company | 6-substituted-tetrahydrobenz[cd]indoles |
| US5244912A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5364856A (en) * | 1991-03-28 | 1994-11-15 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,3,4,5-tetrahydrobenz[CD]indoles |
| US5244911A (en) * | 1991-03-28 | 1993-09-14 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz(cd)indoles and pharmaceutical use thereof |
| US5347013A (en) * | 1991-03-28 | 1994-09-13 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[cd]indoles |
| US5648356A (en) * | 1991-03-28 | 1997-07-15 | Eli Lilly And Company | 6-heterocyclic-4-amino-1,2,2a,3,4,5-hexahydrobenz[CD]indoles |
-
0
- BE BE757879D patent/BE757879A/xx unknown
-
1970
- 1970-10-05 GB GB4715970A patent/GB1318944A/en not_active Expired
- 1970-10-14 US US80748A patent/US3674801A/en not_active Expired - Lifetime
- 1970-10-15 SU SU1487459A patent/SU461496A3/ru active
- 1970-10-17 DE DE19702051062 patent/DE2051062A1/de active Pending
- 1970-10-21 SE SE7014152A patent/SE377125B/xx unknown
- 1970-10-21 IL IL35504A patent/IL35504A/en unknown
- 1970-10-22 PL PL1970144024A patent/PL81057B1/pl unknown
- 1970-10-22 DK DK539470AA patent/DK126944B/da unknown
- 1970-10-23 FR FR7038325A patent/FR2070159B1/fr not_active Expired
- 1970-10-23 JP JP45093394A patent/JPS4833748B1/ja active Pending
- 1970-10-23 NO NO04013/70A patent/NO129523B/no unknown
- 1970-10-23 NL NL7015541A patent/NL7015541A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IL35504A (en) | 1973-10-25 |
| NL7015541A (https=) | 1971-04-27 |
| NO129523B (https=) | 1974-04-22 |
| SU461496A3 (ru) | 1975-02-25 |
| IL35504A0 (en) | 1970-12-24 |
| FR2070159A1 (https=) | 1971-09-10 |
| SE377125B (https=) | 1975-06-23 |
| US3674801A (en) | 1972-07-04 |
| DK126944B (da) | 1973-09-03 |
| BE757879A (fr) | 1971-04-22 |
| DE2051062A1 (de) | 1971-05-06 |
| JPS4833748B1 (https=) | 1973-10-16 |
| FR2070159B1 (https=) | 1973-12-21 |
| PL81057B1 (en) | 1975-08-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PLNP | Patent lapsed through nonpayment of renewal fees |