US 8,541,462 B2Granted

Tetrahydrocarbazole derivatives as ligands of G-protein coupled receptors

AssigneeAEterna Zentaris GmbH

InventorsTilmann Schuster, Klaus Paulini, Peter Schmidt, Silke Baasner, Emmanuel Polymeropoulos, Eckhard Guenther, Michael Teifel

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Abstract

The present invention provides novel tetrahydrocarbazole compounds according to formula (I) as ligands of G-protein coupled receptors (GPCR) which are useful in the treatment and/or prophylaxis of physiological and/or pathological conditions in mammals mediated by GPCR or of physiological and/or pathological conditions which can be treated by modulation of these receptors.

Claims20

Dependent claims

A method of treating a condition in a subject in need of such treatment, the method comprising administering a therapeutically effective amount of at least one tetrahydrocarbazole to the subject to treat the condition,

wherein the condition is a benign tumor disease, a malignant tumor disease, male fertility control, controlled ovarian stimulation in in vitro fertilization (COS/ART), prostate cancer, breast cancer, endometrial cancer, ovarian cancer, benign prostate hyperplasia (BPH), endometriosis, uterine fibroids, uterine myomas, endometrium hyperplasia, pubertas praecox, polycystic ovary syndrome, or a hormone-dependent tumor disease,
wherein the at least one tetrahydrocarbozole is selected from the group consisting of:
Compound 31 (S)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-1-[5-(3-ethyl-ureido)-[1,3,4]oxadiazol-2-yl]-2-methyl-butyl}-amide;
Compound 36 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(morpholin-4-ylmethyl)-carbamoyl]-butyl}amide
Compound 51 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(2-diethylamino-ethylcarbamoyl)-2-methyl-butyl]-amide;
Compound 52 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(tetrahydro-pyran-4-ylmethyl)-thiocarbamoyl]-butyl}-amide;
Compound 54 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(2-morpholin-4-yl-ethylthiocarbamoyl)-butyl]-amide;
Compound 60 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(pyridin-4-ylmethyl)-thiocarbamoyl]-butyl}-amide;
Compound 69 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(3-hydroxy-4-methoxy-phenylcarbamoyl)-2-methyl-butyl]-amide;
Compound 71 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(2-hydroxy-4-methoxy-phenylcarbamoyl)-2-methyl-butyl]-amide;
Compound 73 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(4-hydroxy-cyclohexylcarbamoyl)-2-methyl-butyl]-amide;
Compound 74 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(3-imidazol-1-yl-propylthiocarbamoyl)-2-methyl-butyl]-amide;
Compound 114 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(4-[1,2,4]triazol-1-yl-butylthiocarbamoyl)-butyl]-amide;
Compound 118 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-thiocarbamoyl]-butyl}-amide;
Compound 137 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(quinolin-6-ylcarbamoyl)-butyl]-amide;
Compound 144 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(N′-phenyl-hydrazinocarbonyl)-butyl]-amide;
Compound 164
Compound 167
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid {(S)-1-[(3-
ethyl-ureido)-methyl]-2-methyl-butyl}-amide;
Compound 173
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid {(S)-1-[(3-
ethyl-thioureido)-methyl]-2-methyl-butyl}-amide;
Compound 178
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(2-tert-
butyl-2H-tetrazol-5-ylcarbamoyl)-2-methyl-butyl]-amide;
Compound 183
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid (S)-2-methyl-
1-[(pyrimidin-5-ylmethyl)-carbamoyl]-butyl}-amide;
Compound 188
1-tert-butyl-4-(3-{(S)-2-[((R)-3-{(S)-2-[2-(2-fluoro-
phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-3-methyl-pentanoylamino}-propyl)-4H-
tetrazol-1-ium;
Trifluoro-acetate;
Compound 190
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(3-pyridin-4-ylmethyl-ureidomethyl)-butyl]-amide;
Compound 205
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-butyl]-amide;
Compound 219
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(morpholin-4-ylcarbamoyl)-butyl]-amide;
Compound 230
(R)-3-[(S)-3-Methyl-2-(2-pyridin-3-yl-acetylamino)-
pentanoylamino]-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid ((S)-2-
methyl-1-thiocarbamoyl-butyl)-amide;
Compound 236
(R)-3-[(S)-3-Methyl-2-(2-pyridin-4-yl-acetylamino)-
pentanoylamino]-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid ((S)-2-
methyl-1-thiocarbamoyl-butyl)-amide;
Compound 239
(R)-3-{(S)-2-[3-(4-Methoxy-benzyl)-ureido]-3-methyl-
pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid ((S)-2-
methyl-1-thiocarbamoyl-butyl)-amide;
Compound 242
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(N′-
benzoyl-hydrazinocarbonyl)-2-methyl-butyl]-amide;
Compound 244
(R)-3-{(S)-2-[3-(2-Fluoro-benzyl)-ureido]-3-methyl-
pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(N′-phenyl-hydrazinocarbonyl)-butyl]-amide;
Compound 249
(R)-3-{(2S,3S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-
3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(1S,2S)-
2-methyl-1-(4-phenyl-thiazol-2-yl)-butyl]-amide;
Compound 250
(R)-3-{(2S, 3S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-
pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid {(1S,2S)-1-
[4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methyl-butyl}-amide;
Compound 251
2-{(1R,2S)-1-[((R)-3-{(2S,3S)-2-[2-(2-Fluoro-
phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-2-methyl-butyl}-thiazole-4-carboxylic acid ethyl ester;
Compound 256
2-{(1S,2S)-1-[((R)-3-{(2S,3S)-2-[2-(2-Fluoro-
phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-2-methyl-butyl}-thiazole-4-carboxylic acid;
and
Compound 258
2-{(1S,2S)-1-[((R)-3-{(2S,3S)-2-[3-(2-Fluoro-
benzyl)-ureido]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-2-methyl-butyl}-thiazole-4-carboxylic acid ethyl ester.

107 more elements

Dependencies are inferred from the claim text.

Facts

Application: 13/358,055Filed 25 Jan 2012 · division
Priority: EP 0710709427 Apr 2007
Published: US 2012/0122763 A117 May 2012
Granted: 24 Sep 2013
Term ends: Not estimatedThe source records don’t support an estimate.

Classification50 codes

C07K 5/06191
Dipeptides: containing heteroatoms different from O, S, or N
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…

Family

Application60/914,424Us provisional application · filed 27 Apr 2007
Application12/109,479Parent of this division · filed 25 Apr 2008
US 2012/0122763 A1Pre-grant publication · published 17 May 2012
US 8,148,546 B2Parent of this division
US 2009/0170783 A1Published application
US 8,541,462 B2This patent

From the US filing history. Foreign family members aren’t listed.

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Abstract

wherein the condition is a benign tumor disease, a malignant tumor disease, male fertility control, controlled ovarian stimulation in in vitro fertilization (COS/ART), prostate cancer, breast cancer, endometrial cancer, ovarian cancer, benign prostate hyperplasia (BPH), endometriosis, uterine fibroids, uterine myomas, endometrium hyperplasia, pubertas praecox, polycystic ovary syndrome, or a hormone-dependent tumor disease,
wherein the at least one tetrahydrocarbozole is selected from the group consisting of:
Compound 31 (S)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-1-[5-(3-ethyl-ureido)-[1,3,4]oxadiazol-2-yl]-2-methyl-butyl}-amide;
Compound 36 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(morpholin-4-ylmethyl)-carbamoyl]-butyl}amide
Compound 51 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(2-diethylamino-ethylcarbamoyl)-2-methyl-butyl]-amide;
Compound 52 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(tetrahydro-pyran-4-ylmethyl)-thiocarbamoyl]-butyl}-amide;
Compound 54 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(2-morpholin-4-yl-ethylthiocarbamoyl)-butyl]-amide;
Compound 60 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(pyridin-4-ylmethyl)-thiocarbamoyl]-butyl}-amide;
Compound 69 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(3-hydroxy-4-methoxy-phenylcarbamoyl)-2-methyl-butyl]-amide;
Compound 71 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(2-hydroxy-4-methoxy-phenylcarbamoyl)-2-methyl-butyl]-amide;
Compound 73 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(4-hydroxy-cyclohexylcarbamoyl)-2-methyl-butyl]-amide;
Compound 74 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(3-imidazol-1-yl-propylthiocarbamoyl)-2-methyl-butyl]-amide;
Compound 114 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(4-[1,2,4]triazol-1-yl-butylthiocarbamoyl)-butyl]-amide;
Compound 118 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid {(S)-2-methyl-1-[(5-methyl-[1,3,4]oxadiazol-2-ylmethyl)-thiocarbamoyl]-butyl}-amide;
Compound 137 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(quinolin-6-ylcarbamoyl)-butyl]-amide;
Compound 144 (R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-methyl-1-(N′-phenyl-hydrazinocarbonyl)-butyl]-amide;
Compound 164
Compound 167
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid {(S)-1-[(3-
ethyl-ureido)-methyl]-2-methyl-butyl}-amide;
Compound 173
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid {(S)-1-[(3-
ethyl-thioureido)-methyl]-2-methyl-butyl}-amide;
Compound 178
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(2-tert-
butyl-2H-tetrazol-5-ylcarbamoyl)-2-methyl-butyl]-amide;
Compound 183
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid (S)-2-methyl-
1-[(pyrimidin-5-ylmethyl)-carbamoyl]-butyl}-amide;
Compound 188
1-tert-butyl-4-(3-{(S)-2-[((R)-3-{(S)-2-[2-(2-fluoro-
phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-3-methyl-pentanoylamino}-propyl)-4H-
tetrazol-1-ium;
Trifluoro-acetate;
Compound 190
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(3-pyridin-4-ylmethyl-ureidomethyl)-butyl]-amide;
Compound 205
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(3-pyridin-4-ylmethyl-thioureidomethyl)-butyl]-amide;
Compound 219
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(morpholin-4-ylcarbamoyl)-butyl]-amide;
Compound 230
(R)-3-[(S)-3-Methyl-2-(2-pyridin-3-yl-acetylamino)-
pentanoylamino]-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid ((S)-2-
methyl-1-thiocarbamoyl-butyl)-amide;
Compound 236
(R)-3-[(S)-3-Methyl-2-(2-pyridin-4-yl-acetylamino)-
pentanoylamino]-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid ((S)-2-
methyl-1-thiocarbamoyl-butyl)-amide;
Compound 239
(R)-3-{(S)-2-[3-(4-Methoxy-benzyl)-ureido]-3-methyl-
pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid ((S)-2-
methyl-1-thiocarbamoyl-butyl)-amide;
Compound 242
(R)-3-{(S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-
methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-1-(N′-
benzoyl-hydrazinocarbonyl)-2-methyl-butyl]-amide;
Compound 244
(R)-3-{(S)-2-[3-(2-Fluoro-benzyl)-ureido]-3-methyl-
pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(S)-2-
methyl-1-(N′-phenyl-hydrazinocarbonyl)-butyl]-amide;
Compound 249
(R)-3-{(2S,3S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-
3-methyl-pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid [(1S,2S)-
2-methyl-1-(4-phenyl-thiazol-2-yl)-butyl]-amide;
Compound 250
(R)-3-{(2S, 3S)-2-[2-(2-Fluoro-phenyl)-acetylamino]-3-methyl-
pentanoylamino}-8-trifluoromethyl-2,3,4,9-
tetrahydro-1H-carbazole-3-carboxylic acid {(1S,2S)-1-
[4-(4-methoxy-phenyl)-thiazol-2-yl]-2-methyl-butyl}-amide;
Compound 251
2-{(1R,2S)-1-[((R)-3-{(2S,3S)-2-[2-(2-Fluoro-
phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-2-methyl-butyl}-thiazole-4-carboxylic acid ethyl ester;
Compound 256
2-{(1S,2S)-1-[((R)-3-{(2S,3S)-2-[2-(2-Fluoro-
phenyl)-acetylamino]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-2-methyl-butyl}-thiazole-4-carboxylic acid;
and
Compound 258
2-{(1S,2S)-1-[((R)-3-{(2S,3S)-2-[3-(2-Fluoro-
benzyl)-ureido]-3-methyl-pentanoylamino}-8-
trifluoromethyl-2,3,4,9-tetrahydro-1H-carbazole-3-
carbonyl)-amino]-2-methyl-butyl}-thiazole-4-carboxylic acid ethyl ester.

107 more elements

Facts

Application

13/358,055Filed 25 Jan 2012 · division

Priority

EP 0710709427 Apr 2007

Published

US 2012/0122763 A117 May 2012

Granted

24 Sep 2013

Term ends

Not estimatedThe source records don’t support an estimate.

Classification50 codes

C07K 5/06191
Dipeptides: containing heteroatoms different from O, S, or N
A61P 1/00
Drugs for disorders of the alimentary tract or the digestive system
A61P 1/02
Drugs for disorders of the alimentary tract or the digestive system: stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
A61P 1/04
Drugs for disorders of the alimentary tract or the digestive system: for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of…

Family

Application60/914,424Us provisional application · filed 27 Apr 2007

Application12/109,479Parent of this division · filed 25 Apr 2008

US 2012/0122763 A1Pre-grant publication · published 17 May 2012

US 8,148,546 B2Parent of this division

US 2009/0170783 A1Published application

US 8,541,462 B2This patent

From the US filing history. Foreign family members aren’t listed.