CA2011658A1 - New 1,7-annelated 1h-indole-2-carboxylic acid-n-(1,4-benzodiazepin-3-yl) amides - Google Patents
New 1,7-annelated 1h-indole-2-carboxylic acid-n-(1,4-benzodiazepin-3-yl) amidesInfo
- Publication number
- CA2011658A1 CA2011658A1 CA2011658A CA2011658A CA2011658A1 CA 2011658 A1 CA2011658 A1 CA 2011658A1 CA 2011658 A CA2011658 A CA 2011658A CA 2011658 A CA2011658 A CA 2011658A CA 2011658 A1 CA2011658 A1 CA 2011658A1
- Authority
- CA
- Canada
- Prior art keywords
- lower alkyl
- represents hydrogen
- halogen
- carbon atoms
- annelated
- 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.)
- Granted
Links
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 title 1
- 150000001408 amides Chemical class 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- 229910052739 hydrogen Inorganic materials 0.000 abstract 5
- 239000001257 hydrogen Substances 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 125000005530 alkylenedioxy group Chemical group 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229930192474 thiophene Natural products 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
- C07D471/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/06—Peri-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/06—Peri-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Compounds corresponding to the formula I
(see above formula) in which R1 represents hydrogen, lower alkyl or cycloalkylalkyl with 4-7 carbon atoms, R2 represents hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl, and R3 represents hydrogen, halogen, lower alkyl or lower alkoxy, or R2 and R3 together denote an alkylenedioxy group, R4 represents cycloalkyl with 5 to 6 carbon atoms, thiophene or optionally substituted phenyl, R5 represents hydrogen or halogen, R6 represents hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl, and Z represents an alkylene chain with 2-4 carbon atoms, which can optionally be mono- or disubstituted by lower alkyl or onto which a 5-6-membered carbocyclic ring can optionally be fused, or represents an -X-CH2-CH2- chain, which have pharmacologically valuable properties, are described, together with a method for their preparation.
(see above formula) in which R1 represents hydrogen, lower alkyl or cycloalkylalkyl with 4-7 carbon atoms, R2 represents hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl, and R3 represents hydrogen, halogen, lower alkyl or lower alkoxy, or R2 and R3 together denote an alkylenedioxy group, R4 represents cycloalkyl with 5 to 6 carbon atoms, thiophene or optionally substituted phenyl, R5 represents hydrogen or halogen, R6 represents hydrogen, halogen, lower alkyl, lower alkoxy or trifluoromethyl, and Z represents an alkylene chain with 2-4 carbon atoms, which can optionally be mono- or disubstituted by lower alkyl or onto which a 5-6-membered carbocyclic ring can optionally be fused, or represents an -X-CH2-CH2- chain, which have pharmacologically valuable properties, are described, together with a method for their preparation.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3907389A DE3907389A1 (en) | 1989-03-08 | 1989-03-08 | Novel 1,7-fused 1H-indole-N-(5-alkyl-1,4-benzodiazepin-3-yl)-2-carboxamides |
| DEP3907389.0 | 1989-03-08 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2011658A1 true CA2011658A1 (en) | 1990-09-08 |
| CA2011658C CA2011658C (en) | 2000-05-16 |
Family
ID=6375778
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002011658A Expired - Fee Related CA2011658C (en) | 1989-03-08 | 1990-03-07 | New 1,7-annelated 1h-indole-2-carboxylic acid-n-(1,4-benzodiazepin-3-yl) amides |
Country Status (4)
| Country | Link |
|---|---|
| CA (1) | CA2011658C (en) |
| DD (1) | DD292458A5 (en) |
| DE (1) | DE3907389A1 (en) |
| ZA (1) | ZA901671B (en) |
-
1989
- 1989-03-08 DE DE3907389A patent/DE3907389A1/en not_active Withdrawn
-
1990
- 1990-03-05 ZA ZA901671A patent/ZA901671B/en unknown
- 1990-03-06 DD DD90338440A patent/DD292458A5/en not_active IP Right Cessation
- 1990-03-07 CA CA002011658A patent/CA2011658C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DD292458A5 (en) | 1991-08-01 |
| CA2011658C (en) | 2000-05-16 |
| ZA901671B (en) | 1990-11-28 |
| DE3907389A1 (en) | 1990-09-13 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |