Synthesis and biological evaluation of new 1, 2-dihydro-4-hydroxy-2-oxo-3-quinolinecarboxamides for treatment of autoimmune disorders: structure-activity …

S Jönsson, G Andersson, T Fex, T Fristedt…

Index: Joensson, Stig; Andersson, Gunnar; Fex, Tomas; Fristedt, Tomas; Hedlund, Gunnar; Jansson, Karl; Abramo, Lisbeth; Fritzson, Ingela; Pekarski, Olga; Runstroem, Anna; Sandin, Helena; Thuvesson, Ingela; Bjoerk, Anders Journal of Medicinal Chemistry, 2004 , vol. 47, # 8 p. 2075 - 2088

Full Text: HTML

Citation Number: 147

Abstract

Roquinimex-related 3-quinolinecarboxamide derivatives were prepared and evaluated for treatment of autoimmune disorders. The compounds were tested in mice for their inhibitory effects on disease development in the acute experimental autoimmune encephalomyelitis model and selected compounds in the beagle dog for induction of proinflammatory reaction. Structure-activity relationships are discussed. Compound 8c, laquinimod, showed ...

 Related Synthetic Route
2-Amino-3-methoxybenzoic acid Structure

3177-80-8

2-Amino-3-metho...

~%

8-methoxy-1-methyl-3,1-benzoxazine-2,4-dione Structure

88187-48-8

8-methoxy-1-met...

1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER Structure

57513-54-9

1,2-DIHYDRO-4-H...

N-Methylaniline Structure

100-61-8

N-Methylaniline

~82%

Roquinimex Structure

84088-42-6

Roquinimex

2-Amino-5-fluorobenzoic acid Structure

446-08-2

2-Amino-5-fluor...

~%

6-fluoro-1-methyl-3,1-benzoxazine-2,4-dione Structure

61352-46-3

6-fluoro-1-meth...

Ethyl chloroformate Structure

541-41-3

Ethyl chloroformate

2-Methyl-3-nitroaniline Structure

603-83-8

2-Methyl-3-nitr...

~99%

N-ETHOXYCARBONYL-3-NITRO-O-TOLUIDINE Structure

381670-28-6

N-ETHOXYCARBONY...

2-Amino-6-chlorobenzoic acid Structure

2148-56-3

2-Amino-6-chlor...

~%

5-Chloro-1-methyl-1H-benzo[d][1,3]oxazine-2,4-dione Structure

40707-01-5

5-Chloro-1-meth...

phosgene Structure

75-44-5

phosgene

N-Phenylanthranilic acid Structure

91-40-7

N-Phenylanthran...

~%

1-PHENYL-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE Structure

20877-86-5

1-PHENYL-1H-BEN...

2-ethoxycarbonylamino-6-nitro-benzoic acid Structure

675575-44-7

2-ethoxycarbony...

~%

5-NITRO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE Structure

20829-97-4

5-NITRO-1H-BENZ...

2-Methyl-3-nitroaniline Structure

603-83-8

2-Methyl-3-nitr...

~%

5-NITRO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE Structure

20829-97-4

5-NITRO-1H-BENZ...

N-ETHOXYCARBONYL-3-NITRO-O-TOLUIDINE Structure

381670-28-6

N-ETHOXYCARBONY...

~%

5-NITRO-1H-BENZO[D][1,3]OXAZINE-2,4-DIONE Structure

20829-97-4

5-NITRO-1H-BENZ...

4-Aminobenzotrifluoride Structure

455-14-1

4-Aminobenzotri...

~%

2-((TERT-BUTOXYCARBONYL)AMINO)-5-(TRIFLUOROMETHYL)BENZOIC ACID Structure

141940-29-6

2-((TERT-BUTOXY...

Di-tert-butyl dicarbonate Structure

24424-99-5

Di-tert-butyl d...

~%

2-((TERT-BUTOXYCARBONYL)AMINO)-5-(TRIFLUOROMETHYL)BENZOIC ACID Structure

141940-29-6

2-((TERT-BUTOXY...

ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE Structure

248282-10-2

ETHYL-5-CHLORO-...

~91%

5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLIC ACID Structure

335640-50-1

5-CHLORO-1,2-DI...

6-Chloro-isatoic anhydride Structure

20829-96-3

6-Chloro-isatoi...

~%

ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE Structure

248282-10-2

ETHYL-5-CHLORO-...

2-Amino-6-chlorobenzoic acid Structure

2148-56-3

2-Amino-6-chlor...

~%

ETHYL-5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLATE Structure

248282-10-2

ETHYL-5-CHLORO-...

5-Methoxy-1H-benzo[d][1,3]oxazine-2,4-dione Structure

67765-42-8

5-Methoxy-1H-be...

methyl iodide Structure

74-88-4

methyl iodide

~%

8-Methoxy-1-Methyl-1H-Benzo[D][1,3]Oxazine-2,4-Dione Structure

91105-97-4

8-Methoxy-1-Met...

2-Amino-6-methoxybenzoic acid Structure

53600-33-2

2-Amino-6-metho...

~%

8-Methoxy-1-Methyl-1H-Benzo[D][1,3]Oxazine-2,4-Dione Structure

91105-97-4

8-Methoxy-1-Met...

2-Fluorobenzonitrile Structure

394-47-8

2-Fluorobenzonitrile

Cyclopropanamine Structure

765-30-0

Cyclopropanamine

~%

2-(Cyclopropylamino)benzonitrile Structure

675575-45-8

2-(Cyclopropyla...

Di-tert-butyl dicarbonate Structure

24424-99-5

Di-tert-butyl d...

Benzo[d][1,3]dioxol-5-amine Structure

14268-66-7

Benzo[d][1,3]di...

~%

TERT-BUTYL BENZO[D][1,3]DIOXOL-5-YLCARBAMATE Structure

333749-47-6

TERT-BUTYL BENZ...

Isatoic anhydride Structure

118-48-9

Isatoic anhydride

~%

1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER Structure

57513-54-9

1,2-DIHYDRO-4-H...

Anthranilic acid Structure

118-92-3

Anthranilic acid

~%

1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINECARBOXYLIC ACID ETHYL ESTER Structure

57513-54-9

1,2-DIHYDRO-4-H...

N-Ethylaniline Structure

103-69-5

N-Ethylaniline

5-CHLORO-1,2-DIHYDRO-4-HYDROXY-1-METHYL-2-OXO-3-QUINOLINE CARBOXYLIC ACID Structure

335640-50-1

5-CHLORO-1,2-DI...

~84%

Laquinimod Structure

248281-84-7

Laquinimod

Benzonitrile, 2-fluoro-6-mercapto- (9CI) Structure

138249-39-5

Benzonitrile, 2...

methyl iodide Structure

74-88-4

methyl iodide

~%

2-fluoro-6-(Methylthio)benzonitrile Structure

119584-71-3

2-fluoro-6-(Met...

2,6-Difluorobenzonitrile Structure

1897-52-5

2,6-Difluoroben...

~%

2-fluoro-6-(Methylthio)benzonitrile Structure

119584-71-3

2-fluoro-6-(Met...

2,6-Difluorobenzonitrile Structure

1897-52-5

2,6-Difluoroben...

~%

Benzonitrile, 2-fluoro-6-mercapto- (9CI) Structure

138249-39-5

Benzonitrile, 2...

N-Methyl-4-(trifluoromethyl)aniline Structure

22864-65-9

N-Methyl-4-(tri...

ethyl 4-hydroxy-5-methoxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylate Structure

248282-13-5

ethyl 4-hydroxy...

~60%

Tasquinimod Structure

254964-60-8

Tasquinimod


Home | MSDS/SDS Database Search | Journals | Product Classification | Biologically Active Compounds | Selling Leads | About Us | Disclaimer

Copyright © 2024 ChemSrc All Rights Reserved