BE807526A - 2-(2-(Hetero)arylvinyl)-3-aminoquinoxalines - with anti-inflammatory activity - Google Patents
2-(2-(Hetero)arylvinyl)-3-aminoquinoxalines - with anti-inflammatory activityInfo
- Publication number
- BE807526A BE807526A BE1005516A BE1005516A BE807526A BE 807526 A BE807526 A BE 807526A BE 1005516 A BE1005516 A BE 1005516A BE 1005516 A BE1005516 A BE 1005516A BE 807526 A BE807526 A BE 807526A
- Authority
- BE
- Belgium
- Prior art keywords
- substd
- lower alkyl
- phenyl
- quinoxaline
- opt
- Prior art date
Links
- 230000003110 anti-inflammatory effect Effects 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 5
- -1 piperidino, morpholino Chemical group 0.000 abstract 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 4
- 125000002768 hydroxyalkyl group Chemical group 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004076 pyridyl group Chemical group 0.000 abstract 2
- 125000001544 thienyl group Chemical group 0.000 abstract 2
- RIISWWQHDDJRBJ-UHFFFAOYSA-N 2-chloro-3-(2-phenylethenyl)quinoxaline Chemical compound ClC1=NC2=CC=CC=C2N=C1C=CC1=CC=CC=C1 RIISWWQHDDJRBJ-UHFFFAOYSA-N 0.000 abstract 1
- YJELPRGDOSBSKK-UHFFFAOYSA-N 3-(2-phenylethenyl)-1h-quinoxalin-2-one Chemical compound O=C1NC2=CC=CC=C2N=C1C=CC1=CC=CC=C1 YJELPRGDOSBSKK-UHFFFAOYSA-N 0.000 abstract 1
- 201000005569 Gout Diseases 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- QKINXVHKTOLHMA-UHFFFAOYSA-N N-[3-(4-methylpiperazin-1-yl)propyl]-3-(2-phenylethenyl)quinoxalin-2-amine Chemical compound CN1CCN(CC1)CCCNC1=NC2=CC=CC=C2N=C1C=CC1=CC=CC=C1 QKINXVHKTOLHMA-UHFFFAOYSA-N 0.000 abstract 1
- 229910019213 POCl3 Inorganic materials 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 238000010534 nucleophilic substitution reaction Methods 0.000 abstract 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 201000000596 systemic lupus erythematosus Diseases 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Compounds of formula (I) and their acid-addn. salts are new: where X is NH(CH2)3NRR1, lower dialkylamino, piperidino, morpholino, or piperazino opt. 4-substd. by lower alkyl or lower hydroxyalkyl; R and R1 are H, lower alkyl or lower hydroxyalkyl, or NRR1 is piperidino, morpholino, or piperazino opt. 4-substd. by lower alkyl or lower hydroxyalkyl; R2 and R3 are H, lower alkyl, lower alkoxy, hexafluoro-2-hydroxy-2-propyl or Cl; R4 is phenyl, thienyl, pyridyl or phenyl substd. by lower alkyl, lower alkoxy, halogen or CF3. Anti-inflammatories, e.g. for treating gout and systemic lupus erythematosus. (I) where R4 is opt. substd. phenyl can be prepd. by reacting 2-hydroxy-3-styryl-quinoxaline (or a ring-substd. deriv. thereof) with POCl3, followed by nucleophilic substitution of the resulting 2-chloro-3-styryl-quinoxaline. When R4 is thienyl or pyridyl, the corresp. 2-chloropyridylethylene- or 2-chlorothienylethylene-quinoxaline is used. (I; R4=phenyl) can also be prepd. by reacting the corresp. 2-methyl cpd. with benzaldehyde in the presence of acid. The residue was recrystd. from i-PrOH to give 145g. 2 3-(4-methyl-1-piperazinyl) propylamino -3-styrylquinoxaline, m.p. 145-147 degrees C.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US30816872A | 1972-11-20 | 1972-11-20 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BE807526A true BE807526A (en) | 1974-05-20 |
Family
ID=23192851
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BE1005516A BE807526A (en) | 1972-11-20 | 1973-11-20 | 2-(2-(Hetero)arylvinyl)-3-aminoquinoxalines - with anti-inflammatory activity |
Country Status (1)
| Country | Link |
|---|---|
| BE (1) | BE807526A (en) |
-
1973
- 1973-11-20 BE BE1005516A patent/BE807526A/en unknown
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