IP Library Patent Application 11642975
Patent Application
App. No. 11/642,975

Fluorenes and carbazoles as ligands of the EP2 receptor

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Quick Facts
Patent No.
US None
App. No.
11/642,975
Abstract

The present invention relates to carbazoles/fluorenes, to processes for their preparation and to their use for preparing pharmaceutical agents for the treatment of disorders connected to the EP 2 receptor.

Claims (276)

1 . A compound of the general formula D

where

Y is a 5-12-membered, mono- or bicyclic aryl or heteroaryl radical which may optionally be mono- or polysubstituted by

a C 1 -C 6 -alkyl which may be straight or branched, saturated or unsaturated, and may optionally be mono- or polysubstituted by R 1 where R 1 is the —O—C 1 -C 6 -alkyl group, cyano, —N(C 1 -C 6 -alkyl) 2 , —NH—C 1 -C 6 -alkyl, —C 4 -C 8 -cycloamine, —NH 2 , —CO—CH 3 —, —SO 2 —NH 2 , —C 1 -C 6 -alkyl, —SO 2 —NH—CO—C 1 -C 6 -alkyl, —SO 2 —NH—C 1 -C 6 -alkyl, —SO 2 —C 1 -C 6 -alkyl, —NH—CO—C 1 -C 6 -alkyl, NO 2 , —OH, —COOH or halogen,

R 1 where R 1 is as defined above,

a saturated or unsaturated 4-8-membered heterocycle which optionally bears 1-3 nitrogen or oxygen atoms and is optionally substituted by —OCH 3 , —COCH 3 , —C 1 -C 6 -alkyl, —C 1 -C 2 -alkyl-O—CH 3 or a keto group,

an —SO 2 —NH 2 , —SO 2 -CH 3 , —NH—CO—CH 3 group, NO 2 , —OH, —COOH or halogen,

a fused 5-7-membered carbocycle optionally substituted by a keto group,

a 6-12-membered, mono- or bicyclic heterocycle which may be saturated or unsaturated, is interrupted once or more than once by nitrogen, oxygen or sulfur, and is optionally mono- or polysubstituted by

R 1 , where R 1 is as defined above,

an oxygen or a keto group,

Z is a carbon or nitrogen radical,

X is an —OH, —NH 2 group, an —O—C 1 -C 6 -alkyl, —N(C 1 -C 6 -alkyl) 2 , —NH—C 1 -C 6 -alkyl, C 4 -C 8 -cycloamine, —NH—SO 2 —C 1 -C 6 -alkyl or a saturated or unsaturated —C 3 -C 8 -cycloalkyl radical which may optionally be substituted,

n is 1-7,

m is 1-4 and their salts with physiologically acceptable bases and their cyclodextrin clathrates.

2 . A compound as claimed in claim 1 where

Y is a 5-12-membered, mono- or bicyclic aryl or heteroaryl radical which may optionally be mono- or polysubstituted by

a C 1 -C 6 -alkyl which may be straight or branched, saturated or unsaturated, and may optionally be mono- or polysubstituted by R 2 , where R 2 is the —O—C 1 -C 3 -alkyl group, cyano, —N(C 1 -C 3 -alkyl) 2 , NH—C 1 -C 3 -alkyl, —NH 2 , —CO—CH 3 -, —C 1 -C 3 -alkyl, —SO 2 —NH 2 , —SO 2 —NH—CO—C 1 -C 3 -alkyl, SO 2 —NHC 1 -C 3 -alkyl, —SO 2 —C 1 -C 3 -alkyl, —NH—CO—C 1 -C 3 -alkyl, NO 2 , —OH, —COOH, —C 4 -C 6 -cycloamine or halogen,

R 2 , where R 2 is as defined above,

a saturated or unsaturated 5-7-membered heterocycle which optionally bears 1-3 nitrogen or oxygen atoms and is optionally substituted by —OCH 3 , —C 1 -C 3 -alkyl, —C 1 -C 2 -alkyl-OCH 3 or a keto group,

an —SO 2 —NH 2 , —SO 2 -CH 3 , —NH—CO—CH 3 group, —NO 2 , —OH, —COOH or halogen,

a fused 5-7-membered carbocycle optionally substituted by a keto group,

a 6-12-membered, mono- or bicyclic heterocycle which may be saturated or unsaturated, is interrupted once or more than once by nitrogen, oxygen or sulfur, and is optionally mono- or polysubstituted by an —OCH 3 , —CO—CH 3 group, —C 1 -C 3 -alkyl, cyano, oxygen or a keto group,

Z is a carbon or nitrogen radical,

X is an OH or NH 2 group,

an —O—C 1 -C 6 -alkyl, —N(C 1 -C 6 -alkyl) 2 , —NH—C 1 -C 6 -alkyl, —C 4 -C 8 -cycloamine, —NH—SO 2 —C 1 -C 6 -alkyl or a saturated or unsaturated —C 3 -C 8 -cycloalkyl radical which may optionally be substituted,

n is 2-5,

m is 1-3.

3 . A compound as claimed in claim 1 where

Y is a 6-12-membered mono- or bicyclic aryl radical which may optionally be mono- or polysubstituted and which is optionally mono- or polysubstituted by

a C 1 -C 6 -alkyl which may be straight or branched, saturated or unsaturated, and may optionally be mono- or polysubstituted by R 3 , where R 3 is the —OCH 3 group, —CO—CH 3 , cyano, —NH 2 , —N(CH 3 ) 2 , —NHCH 3 , —SO 2 —NH 2 , —SO 2 —NH—CO—CH 3 , —SO 2 —NH—CH 3 , —SO 2 —CH 3 , —NH—CO—CH 3 , —NO 2 , —OH, —COOH or halogen,

R 3 , where R 3 is as defined above,

an —SO 2 —NH 2 , —SO 2 —CH 3 , —NH—CO—CH 3 group, NO 2 , —OH, —COOH or halogen,

or the group

represent the group

z is a carbon or a nitrogen radical,

x is a hydroxyl group, —N(CH 3 ) 2 , —NH—CH 3 , —NHSO 2 —CH 3 ,

n is 3-5,

m is 1-2.

4 . A compound as claimed in claim 1 selected from a group which comprises the following compounds:

(R/S)[2-(4-m-tolyloxybutoxy)-9H-fluoren-9-yl]acetic acid

(R/S) {2-[4-(3-hydroxy-5-methoxyphenoxy)butoxy]-9H-fluoren-9-yl}acetic acid

(R/S) {2-[4-(3-hydroxyphenoxy)butoxy]-9H-fluoren-9-yl}acetic acid

(R/S) {2-[4-(3-acetylaminophenoxy)butoxy]-9H-fluoren-9-yl}acetic acid

ethyl {2-[4-(3-hydroxyphenoxy)butoxy]carbazol-9-yl}acetate

ethyl [2-(4-m-tolyloxybutoxy)carbazol-9-yl]acetate

ethyl {2-[4-(3-acetylaminophenoxy)butoxy]carbazol-9-yl}acetate

ethyl {2-[4-(3-hydroxy-5-methoxyphenoxy)butoxy]carbazol-9-yl}acetate

methyl 3-[4-(9-ethoxycarbonylmethyl-9H-carbazol-2-yloxy)butoxy]benzoate

ethyl 3-{2-[4-(3-hydroxyphenoxy)butoxy]carbazol-9-yl}propionate

ethyl 3-[2-(4-m-tolyloxybutoxy)carbazol-9-yl]propionate

ethyl 3-{2-[4-(3-acetylaminophenoxy)butoxy]carbazol-9-yl}propionate

ethyl 3-{2-[4-(3-hydroxy-5-methoxyphenoxy)butoxy]carbazol-9-yl}propionate

methyl 3-{4-[9-(2-ethoxycarbonylethyl)-9H-carbazol-2-yloxy]butoxy}benzoate

{2-[4-(3-hydroxyphenoxy)butoxy]carbazol-9-yl}acetic acid

[2-(4-m-tolyloxybutoxy)carbazol-9-yl]acetic acid

{2-[4-(3-acetylaminophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-hydroxy-5-methoxyphenoxy)butoxy]carbazol-9-yl}acetic acid

3-[4-(9-carboxymethyl-9H-carbazol-2-yloxy)butoxy]benzoic acid

3-{2-[4-(3-hydroxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-[2-(4-m-tolyloxybutoxy)carbazol-9-yl]propionic acid

3-{2-[4-(3-acetylaminophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-hydroxy-5-methoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{4-[9-(2-carboxyethyl)-9H-carbazol-2-yloxy]butoxy}benzoic acid

{2-[4-(2-acetylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-acetylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(4-nitrophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-nitrophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-oxoindan-4-yloxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(4-chlorophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-fluorophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3,5-dimethoxyphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-fluorophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-pyrrol-1-ylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-isopropylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(4-pyrrol-1-ylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-isoxazol-5-ylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-isoxazol-5-yl-4-methylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-acetylbenzofuran-7-yloxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-morpholin-4-ylphenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(6-methoxynaphthalen-2-yloxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(2-chlorophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(3-chlorophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(4-fluorophenoxy)butoxy]carbazol-9-yl}acetic acid

{2-[4-(4-[1,2,4]triazol-1-ylphenoxy)butoxy]carbazol-9-yl}acetic acid

(2-{4-[2-(1H-pyrazol-3-yl)phenoxy]butoxy}carbazol-9-yl)acetic acid

3-[2-(4-phenoxybutoxy)carbazol-9-yl]propionic acid

3-{2-[4-(2-acetylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-acetylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-acetylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-acetylaminophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-methoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-nitrophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-nitrophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-oxoindan-4-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(1-oxoindan-5-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-chlorophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-methoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-[2-(4-o-tolyloxybutoxy)carbazol-9-yl]propionic acid

3-[2-(4-p-tolyloxybutoxy)carbazol-9-yl]propionic acid

3-{2-[4-(3-methoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(naphthalen-2-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(1-oxoindan-4-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(5-oxo-5,6,7,8-tetrahydronaphthalen-1-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-fluorophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3,5-dimethoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-imidazol-1-ylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-oxoindan-5-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3,4-dimethoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-fluorophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-pyrrol-1-ylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(benzo[1,3]dioxol-5-yloxy)butoxy]carbazol-9-yl}propionic acid

3-(2-{4-[4-(2-oxopropyl)phenoxy]butoxy}carbazol-9-yl)propionic acid

3-{2-[4-(3-dimethylaminophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-methoxymethylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-dimethylaminomethylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-(2-{4-[4-(2-methoxyethyl)phenoxy]butoxy}carbazol-9-yl)propionic acid

3-{2-[4-(2,3-dimethoxyphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-isoxazol-5-ylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-oxo-1,2,3,4-tetrahydroquinolin-6-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-methylbenzothiazol-5-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-methanesulfonylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-sulfamoylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-methoxynaphthalen-2-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-isoxazol-5-yl-4-methylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-acetylbenzofuran-7-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(1-acetylnaphthalen-2-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-morpholin-4-ylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(6-methoxynaphthalen-2-yloxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-cyanomethylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-cyanophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-cyanophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(2-chlorophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(3-chlorophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-fluorophenoxy)butoxy]carbazol-9-yl}propionic acid

3-{2-[4-(4-[1 ,2,4]triazol-1-ylphenoxy)butoxy]carbazol-9-yl}propionic acid

3-(2-{4-[2-(1H-pyrazol-3-yl)phenoxy]butoxy}carbazol-9-yl)propionic acid

[2-(3-phenoxypropoxy)carbazol-9-yl]acetic acid

{2-[3-(2-acetylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-acetylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-acetylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-acetylaminophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-methoxyphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-nitrophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-nitrophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-oxoindan-4-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(1-oxoindan-5-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-chlorophenoxy)propoxy]carbazol-9-yl}acetic acid

[2-(3-o-tolyloxypropoxy)carbazol-9-yl]acetic acid

[2-(3-m-tolyloxypropoxy)carbazol-9-yl]acetic acid

[2-(3-p-to1y1oxypropoxy)carbazo1-9-yl]acetic acid

{2-[3-(3-methoxyphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(naphthalen-1-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-acetylarninophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(1-oxoindan-4-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(5-oxo-5,6,7,8-tetrahydronaphthalen-1-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-fluorophenoxy)propoxy]carbazol-9-yl }acetic acid

{2-[3-(3,5-dimethoxyphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-imidazol-1-ylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-oxoindan-5-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3,4-dimethoxyphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-acetylaminophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(7-methoxynaphthalen-2-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-fluorophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-pyrrol-1-ylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(benzo[1,3]dioxol-5-yloxy)propoxy]carbazol-9-yl}acetic acid

(2-{3-[4-(2-oxopropyl)phenoxy]propoxy}carbazol-9-yl)acetic acid

{2-[3-(4-methoxynaphthalen-1-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-isopropyiphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-isopropylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-dimethylarninophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-dimethylaminomethylphenoxy)propoxy]carbazol-9-yl}acetic acid

(2-{3-[4-(2-methoxyethyl)phenoxy]propoxy}carbazol-9-yl)acetic acid

{2-[3-(2,3-dimethoxyphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-isoxazol-5-ylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-methylbenzothiazol-5-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-methanesulfonylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-methoxynaphthalen-2-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(7-methoxynaphthalen-1-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-isoxazol-5-yl-4-methylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-acetylbenzofuran-7-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-morpholin-4-ylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-acetylnaphthalen-1-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(1-acetylnaphthalen-2-yloxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-morpholin-4-ylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-methanesulfonylphenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-cyanophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(2-chlorophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(3-chlorophenoxy)propoxy]carbazol-9-yl}acetic acid

{2-[3-(4-fluorophenoxy)propoxy]carbazol-9-yl}acetic acid

(2-{3-[2-(1H-pyrazol-3-yl)phenoxy]propoxy}carbazol-9-yl)acetic acid

[2-(5-phenoxypentyloxy)carbazol-9-yl]acetic acid

{2-[5-(2-acetylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-acetylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-acetylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-acetylarninophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-methoxyphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-cyanophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-nitrophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-nitrophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-nitrophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-oxoindan-4-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(1-oxoindan-5-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-chlorophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-methoxyphenoxy)pentyloxy]carbazol-9-yl}acetic acid

[2-(5-o-tolyloxypentyloxy)carbazol-9-yl]acetic acid

[2-(5-m-tolyloxypentyloxy)carbazol-9-yl]acetic acid

[2-(5-p-tolyloxypentyloxy)carbazol-9-yl]acetic acid

{2-[5-(3-methoxyphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(naphthalen-1-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-acetylaminophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(1-oxoindan-4-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(5-oxo-5,6,7,8-tetrahydronaphthalen-1-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-fluorophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3,5-dimethoxyphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-imidazol-1-ylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-oxoindan-5-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3,4-dimethoxyphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-acetylaminophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-fluorophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-pyrrol-1-ylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(benzo[1,3]dioxol-5-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-isopropylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(indan-5-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-methoxynaphthalen-1-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-isopropylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-isopropylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-dimethylaminophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-dimethylaminomethylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

(2-{5-[4-(2-methoxyethyl)phenoxy]pentyloxy}carbazol-9-yl)acetic acid

{2-[5-(2,3-dimethoxyphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-isoxazol-5-ylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-oxo-1,2,3 ,4-tetrahydroquinolin-6-yloxy)pentyloxy]carbazol-9-yl }acetic acid

{2-[5-(6-cyanonaphthalen-2-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-methanesulfonylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-isoxazol-5-yl-4-methylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-morpholin-4-ylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-acetylnaphthalen-1-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(3-morpholin-4-ylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(6-methoxynaphthalen-2-yloxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-cyanomethylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-methanesulfonylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-cyanophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-cyanophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(2-chlorophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-fluorophenoxy)pentyloxy]carbazol-9-yl}acetic acid

{2-[5-(4-[1 ,2,4]triazol-1-ylphenoxy)pentyloxy]carbazol-9-yl}acetic acid

(2-{5-[2-(1H-pyrazol-3-yl)phenoxy]pentyloxy}carbazol-9-yl)acetic acid

3-[2-(4-m-tolyloxybutoxy)carbazol-9-yl]propionic acid

3-{2-[4-(3-acetylaminophenoxy)butoxy]carbazol-9-yl}propionic acid

N-ethyl-2-[2-(4-m-tolyloxybutoxy)carbazol-9-yl]acetamide

N,N-diethyl-2-[2-(4-m-tolyloxybutoxy)carbazol-9-yl]acetamide

N-{2-[2-(4-m-tolyloxybutoxy)carbazol-9-yl]acetyl}methanesulfonamide.

5 . The use of the compounds as claimed in claim 1 for producing medicaments which comprise at least one of the compounds of the formula D.

6 . The medicament as claimed in claim 5 comprising suitable formulation and carrier substances.

7 . The use of the medicament as claimed in claim 5 , characterized in that the medicament is used for the treatment and prophylaxis of disorders.

8 . The use as claimed in claim 7 for the treatment and prophylaxis of disorders connected to the EP 2 receptor.

9 . The use as claimed in claim 7 for the treatment and prophylaxis of fertility disorders.

10 . The use as claimed in claim 7 for the treatment and prophylaxis of menstrual complaints.

11 . The use as claimed in claim 7 for the treatment and prophylaxis of endometriosis.

12 . The use of the compounds as claimed in claim 1 for modulating the EP 2 receptor.

13 . The use as claimed in claim 7 for the treatment and prophylaxis of pain.

14 . The use as claimed in claim 7 for the treatment and prophylaxis of a disorder which is caused by elevated intraocular pressure.

15 . A method for fertility control comprising administering a compound as claimed in claim 1 .

16 . The use as claimed in claim 7 for the treatment and prophylaxis of osteoporosis.

17 . The use as claimed in claim 7 for the treatment and prophylaxis of inflammatory disorders.

18 . The use as claimed in claim 17 , characterized in that the inflammatory disorder is multiple sclerosis.

19 . The use of the compounds of the general formula D as claimed in claim 1 in the form of a pharmaceutical preparation for enteral, parenteral, vaginal and oral administration.

20 . A process for preparing the compounds as claimed in claim 1 , characterized in that

a bromoalkyl side chain is inserted in a hydroxyfluorene or hydroxycarbazole derivative of type A in step 1,

an aryl ether is introduced into compounds of type B in step 2, and

an ester hydrolysis to give the end compounds D is effected in step 3.

21 . An intermediate of the general formula A, B and C.

Assignments (2)
CHANGE OF NAME Recorded Nov 14, 2007
From: SCHERING AKTIENGESELLSCHAFT
To: BAYER SCHERING PHARMA AKTIENGESELLSCHAFT
Reel/Frame 020110/0334 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 30, 2007
From: BRAUER, NICO; BUCHMANN, BERND; HUWE, CHRISTOPH; LINDENTHAL, BERNHARD; LANGER, GERNOT; PETERS, OLAF; SCHUBERT, GERD; BOTHE, ULRICH; TOSCHI, LUISELLA; PETERS-KOTTIG, MICHAELE
To: BAYER SCHERING PHARMA AG
Reel/Frame 019247/0490 →