IP Library › Granted Patent US 7,750,040
Granted Patent B2
US 7,750,040 · App. 11/572,801 · Granted Jul 6, 2010

Thiophene derivatives

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Quick Facts
Patent No.
US 7,750,040
App. No.
11/572,801
Granted
Jul 6, 2010
Kind
B2
Abstract

The invention relates to novel thiophene derivatives, their preparation and their use as pharmaceutically active compounds. Said compounds particularly act as immunosuppressive agents.

Claims (118)

1. A compound of Formula (I)

wherein

A represents —CH 2 CH 2 —, —CH═CH—, —CH 2 —O—, or —CH 2 NH—;

R 1 represents hydrogen, alkyl or halogen; and in the case A represents —CH 2 —CH 2 — or —CH 2 NH—, R 1 in addition represents alkoxy;

R 2 represents hydrogen, alkoxy, fluoro-alkoxy, hydroxy-alkoxy, hydroxy-alkyl, di-(hydroxy-alkyl)-alkyl, di-(hydroxy-alkyl)-alkoxy, 1-glyceryl or 2-glyceryl;

R 3 represents hydrogen, alkyl, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy or halogen; and in the case A represents —CH 2 —CH 2 — or —CH 2 NH—, R 3 in addition represents alkoxy;

X represents C—R 4 ;

R 4 represents hydrogen, alkyl, alkoxy, or halogen; and

R 5 represents methyl or ethyl;

in free or an optically pure enantiomer, a mixture of enantiomers, a racemate, a diastereomer, a mixture of diastereomers, a diastereomeric racemate, a mixture of diastereomeric racemates, or a salt form.

2. A compound according to claim 1 , wherein

A represents —CH 2 CH 2 —, —CH═CH—, or —NH—CH 2 —;

R 1 represents hydrogen, alkyl or halogen;

R 3 represents hydrogen, alkyl, mono- or di-alkylamino, trifluoromethyl, trifluoromethoxy or halogen; and

R 3 represents methyl.

3. A compound according to claim 1 or 2 , wherein A represents —CH═CH—.

4. A compound according to claim 1 or 2 , wherein A represents —NH—CH 2 —.

5. A compound according to claim 1 or 2 , wherein A represents —CH 2 CH 2 —.

6. A compound according to claim 1 or 2 , wherein A represents —CH 2 NH—.

7. A compound according to claim 1 or 2 , wherein R 4 represents a methoxy group, and R 1 represents hydrogen.

8. A compound according to claim 1 or 2 , wherein R 4 represents a methoxy group, and R 1 and R 3 both represent hydrogen.

9. A compound according to claim 1 or 2 , wherein R 2 represents hydroxy-alkoxy, hydroxy-alkyl, di-(hydroxy-alkyl)-alkoxy, di-(hydroxy-alkyl)-alkyl, 1-glyceryl, or 2-glyceryl.

10. A compound according to claim 9 , wherein R 2 represents an (S)-1-glyceryl group.

11. A compound according to claim 1 or 2 , wherein R 4 represents hydrogen, R 1 and R 3 both represent a methyl group, and R 2 represents hydroxy-alkoxy, hydroxy-alkyl, di-(hydroxy-alkyl)-alkoxy, di-(hydroxy-alkyl)-alkyl, 1-glyceryl, or 2-glyceryl.

12. A compound of Formula (II)

according to claim 1 or 2 .

13. A compound of Formula (III)

according to claim 1 or 2 .

14. A compound according to claim 1 selected from the group consisting of:

(1aS,5aR)-1,1,2-Trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 2,4-dimethoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-ethoxy-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 2-methyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((S)-2,3-dihydroxy-propoxy)-3,5-dimethyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R)-2,3-dihydroxy-propoxy)-3,5-dimethyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((S)-2,3-dihydroxy-propoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R)-2,3-dihydroxy-propoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((S)-2,3-dihydroxy-propoxy)-3-methyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R)-2,3-dihydroxy-propoxy)-3-methyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((S)-2,3-dihydroxy-propoxy)-3-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R)-2,3-dihydroxy-propoxy)-3-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((S)-2,3-dihydroxy-propoxy)-2-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R)-2,3-dihydroxy-propoxy)-2-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((S)-2,3-dihydroxy-propoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R)-2,3-dihydroxy-propoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-3,5-dimethyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-3-methyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-3-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-2-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-hydroxy-ethoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-3,5-dimethyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-3-methyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-3-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-2-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-((R/S)-2-hydroxy-propoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-propoxy)-3,5-dimethyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-propoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-propoxy)-3-methyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-propoxy)-3-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-propoxy)-2-chloro-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-propoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-fluoro-ethoxy)-3,5-dimethyl-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-fluoro-ethoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 2-chloro-4-(2-fluoro-ethoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(2-fluoro-ethoxy)-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-fluoro-propoxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 2-methoxy-4-propoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 2-methoxy-4-isopropoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-isobutoxy-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(6-hydroxy-hexyloxy)-2-methoxy-benzylamide,

(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalene-4-carboxylic acid 4-(3-hydroxy-2-hydroxymethyl-propoxy)-3,5-dimethyl-benzylamide,

3-(2-methoxy-phenyl)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]penta-len-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-2-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-(2-hydroxy-ethoxy)-2-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((R)-2,3-dihydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4′-yl)-propan-1-one,

3-[4-(2-hydroxy-ethoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-(2-(R/S)-hydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-(2-(2-fluoroethoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one, and

3-[4-(3-hydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one.

15. A compound according to claim 1 selected from the group consisting of:

3-[4-(3-Hydroxy-2-hydroxymethyl-propoxy)-3,5-dimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-3-ethyl-5-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((R)-2,3-dihydroxy-propoxy)-3-ethyl-5-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-ethyl-4-(2-hydroxy-ethoxy)-5-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-3,5-diethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-((S)-2,3-dihydroxy-propoxy)-5-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-((R)-2,3-dihydroxy-propoxy)-5-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-(2-hydroxy-ethoxy)-5-methyl-phenyl]-1-(1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-(2-hydroxy-propoxy)-5-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-((S)-2,3-dihydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[2-chloro-4-((S)-2,3-dihydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4′-yl)-propan-1-one,

3-[2-chloro-4-((R)-2,3-dihydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[2-chloro-4-(2-hydroxy-ethoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[2-chloro-4-(3-hydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[2-chloro-4-(2-hydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-3-methyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-2,3,5-trimethyl-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3,5-dichloro-4-((S)-2,3-dihydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3,5-dichloro-4-((R)-2,3-dihydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3,5-dichloro-4-(2-hydroxy-propoxy)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-((S)-2,3-dihydroxy-propoxy)-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-((R)-2,3-dihydroxy-propoxy)-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-chloro-4-(2-hydroxy-ethoxy)-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-3-fluoro-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((R)-2,3-dihydroxy-propoxy)-3-fluoro-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[3-fluoro-4-(2-hydroxy-ethoxy)-5-methoxy-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-(3-hydroxy-propyl)-phenyl]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((S)-2,3-dihydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aR,5aS)-2-ethyl-1,1-dimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

3-[4-((R)-2,3-dihydroxy-propoxy)-3,5-dimethyl-phenyl]-1-((1aR,5aS)-2-ethyl-1,1-dimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-propan-1-one,

1-((1aR,5aS)-2-ethyl-1,1-dimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-3-[4-(3-hydroxy-propoxy)-3,5-dimethyl-phenyl]-propan-1-one,

1-((1aR,5aS)-2-ethyl-1,1-dimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-3-[4-(2-hydroxy-propoxy)-3,5-dimethyl-phenyl]-propan-1-one,

2-(2-methoxy-phenylamino)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone,

2-(3,5-dimethyl-phenylamino)-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone, and

2-[4-(2-hydroxy-ethyl)-phenylamino]-1-((1aS,5aR)-1,1,2-trimethyl-1,1a,5,5a-tetrahydro-3-thia-cyclopropa[a]pentalen-4-yl)-ethanone.

16. A pharmaceutical composition comprising a compound according to claim 1 and a pharmaceutically acceptable carrier material.

Assignments (1)
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2007
From: BOLLI, MARTIN; BUR, DANIEL; CLOZEL, MARTINE; FISCHLI, WALTER; LEHMANN, DAVID; MUELLER, CLAUS; NAYLER, OLIVER; SCHERZ, MICHAEL; WELLER, THOMAS; MATHYS, BORIS
To: ACTELION PHARMACEUTICALS LTD.
Reel/Frame 018848/0706 →
Priority Claims (1)
WO PCT/EP2004/008501 · Jul 29, 2004 · international
Continuity (1)
Related Publication 20080064740A1 · Mar 13, 2008