IP Library Granted Patent US 7,501,405
Granted Patent B2
US 7,501,405 · App. 11/254,125 · Granted Mar 10, 2009

Combination therapy using an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent for the treatment of metabolic syndrome and related diseases and disorders

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Quick Facts
Patent No.
US 7,501,405
App. No.
11/254,125
Granted
Mar 10, 2009
Kind
B2
Abstract

Combination therapy comprising the administration of an 11β-hydroxysteroid dehydrogenase type 1 inhibitor and an antihypertensive agent useful for treating, preventing and reducing the risk of developing insulin resistance, dyslipidemia, obesity, hypertension and other related diseases and disorders.

Claims (25)

1. A combination therapy which comprises an 11β-hydroxysteroid dehydrogenase type 1 (11β-HSD1) inhibitor and an antihypertensive agent, wherein the 11β-HSD1 inhibitor is of the Formula (IIa):

wherein

R 1 is aryl, arylC 1 -C 6 alkyl, hetaryl or hetarylC 1 -C 6 alkyl optionally substituted with one or more of R 6 independently;

R 2 is halo, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylC 1 -C 6 -alkyl, trihalomethyl, aryl, arylC 1 -C 6 alkyl, C 1 -C 6 alkyloxyC 1 -C 6 alkyl, arylC 1 -C 6 alkyloxyC 1 -C 6 -alkyl, C 1 -C 6 alkylNR 5 C 1 -C 6 alkyl, arylC 1 -C 6 alkylNR 5 C 1 -C 6 alkyl, hetaryl or hetarylC 1 -C 6 alkyl wherein the alkyl, alkenyl, alkynyl, cycloalkyl and aryl groups independently are optionally substituted with one or more R 7 ;

R 3 and R 4 together with the nitrogen to which they are attached, are forming a saturated or partially saturated bicyclic/bridge ring system containing from 7 to 12 carbon atoms and from 0 to 2 additional heteroatoms selected from nitrogen, oxygen or sulphur, the ring system optionally being substituted with at least one of C 1 -C 6 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, hetarylC 1 -C 6 alkyl, hydroxy, oxo, C 1 -C 6 alkyloxy, arylC 1 -C 6 alkyloxy or hetarylC 1 -C 6 alkyloxy,

wherein the alkyl and aryl groups independently are optionally substituted with one ore more of R 9 ;

R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 hetcycloalkyl, C 3 -C 10 -cycloalkylC 1 -C 6 alkyl, C 3 -C 10 hetcycloalkylC 1 - alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl or hetarylC 1 -C 6 alkyl wherein the alkyl, alkenyl, alkynyl, aryl, hetaryl, cycloalkyl and hetcycloalkyl groups independently are optionally substituted with one or more of R 9 ;

R 6 and R 7 independently are hydrogen, hydroxy, oxo, halo, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 alkyloxy, trihalomethyl, trihalomethoxy, NR 10 R 11 , arylC 1 -C 6 alkyloxy, hetarylC 1 -C 6 alkyloxy, C 1 -C 6 alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, arylC 1 -C 6 alkylcarbonyl, C 1 -C 6 alkyloxycarbonyl, aryloxycarbonyl, arylC 1 -C 6 alkyloxycarbonyl, C 1 -C 6 alkylcarboxy, arylcarboxy or arylC 1 -C 6 alkylcarboxy;

R 9 independently is hydrogen, C 1 -C 6 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, hetarylC 1 -C 6 alkyl, hydroxy, oxo, cyano, NR 10 R 11 , C 1 -C 6 alkyloxy, aryloxy, arylC 1 -C 6 alkyloxy, hetaryloxy, hetarylC 1 -C 6 alkyloxy, C 1 -C 6 alkyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, arylC 1 -C 6 alkylcarbonyl, hetarylC 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarboxy, arylcarboxy or arylC 1 -C 6 alkylcarboxy;

R 10 and R 11 independently are hydrogen, C 1 -C 8 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, C 3 -C 10 cycloalkyl, C 3 -C 10 hetcycloalkyl, C 3 -C 10 cycloalkylC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarboxyC 1 -C 6 alkyl; or

R 10 and R 11 together with the nitrogen to which they are attached, are forming a saturated or partially saturated cyclic, bicyclic or tricyclic ring system containing from 4 to 10 carbon atoms and from 0 to 2 additional heteroatoms selected from nitrogen, oxygen or sulphur, the ring system optionally being substituted with at least one of C 1 -C 8 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, hetarylC 1 -C 6 alkyl, hydroxy, oxo, cyano, C 1 -C 6 alkyloxy, arylC 1 -C 6 alkyloxy, hetarylC 1 -C 6 alkyloxy, C 1 -C 6 alkyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, arylC 1 -C 6 alkylcarbonyl, hetarylC 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarboxy, arylcarboxy or arylC 1 - 6 alkylcarboxy; or

a salt thereof with a pharmaceutically acceptable acid or base, or optical isomer or mixture of optical isomers, racemic mixture, or tautomeric form thereof.

2. The combination according to claim 1 , wherein the 11β-HSD1 inhibitor is of the Formula (IIa) wherein:

R 1 is aryl or hetaryl optionally substituted with one or more R 6 independently;

R 2 is halo, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 cycloalkylC 1 -C 6 -alkyl, aryl, arylC 1 -C 6 alkyl, C 1 -C 6 alkyloxyC 1 -C 6 alkyl, arylC 1 -C 6 alkyloxyC 1 -C 6 alkyl, C 1 -C 6 -alkylNR 5 C 1 -C 6 alkyl, arylC 1 -C 6 alkylNR 5 C 1 -C 6 alkyl, hetaryl or hetarylC 1 -C 6 alkyl where the alkyl, alkenyl, alkynyl, cycloalkyl and aryl groups independently are optionally substituted with one or more R 7 ;

R 5 is C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 10 cycloalkyl, C 3 -C 10 hetcycloalkyl, C 3 -C 10 -cycloalkylC 1 -C 6 alkyl, C 3 -C 10 hetcycloalkylC 1 -C 6 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl or hetarylC 1 -C 6 alkyl wherein the alkyl, alkenyl, alkynyl, aryl, hetaryl, cycloalkyl and hetcycloalkyl groups independently are optionally substituted with one or more of R 9 ;

R 6 and R 7 independently are hydrogen, hydroxy, oxo, halo, nitro, cyano, C 1 -C 6 alkyl, C 1 -C 6 -alkyloxy, trihalomethyl, trihalomethoxy, NR 10 R 11 , arylC 1 -C 6 alkyloxy, hetarylC 1 -C 6 alkyloxy, C 1 -C 6 alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, arylC 1 -C 6 alkylcarbonyl, C 1 -C 6 alkyloxycarbonyl, aryloxycarbonyl, arylC 1 -C 6 alkyloxycarbonyl, C 1 -C 6 alkylcarboxy, arylcarboxy or arylC 1 -C 6 alkylcarboxy;

R 9 independently is hydrogen, C 1 -C 6 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, hetarylC 1 -C 6 -alkyl, hydroxy, oxo, cyano, NR 10 R 11 , C 1 -C 6 alkyloxy, aryloxy, arylC 1 -C 6 alkyloxy, hetaryloxy, hetarylC 1 -C 6 alkyloxy, C 1 -C 6 alkyloxyC 1 -C 6 alkyl, C 1 -C 6 alkyl-carbonyl, arylcarbonyl, hetarylcarbonyl, arylC 1 -C 6 alkylcarbonyl, hetarylC 1 -C 6 alkyl-carbonyl, C 1 -C 6 alkylcarboxy, arylcarboxy or arylC 1 -C 6 alkylcarboxy;

R 10 and R11 independently are hydrogen, C 1 -C 8 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, C 3 -C 10 -cycloalkyl, C 3 -C 10 heteycloalkyl, C 3 -C 10 cycloalkylC 1 -C 6 alkyl, C 1 -C 6 alkylcarboxyC 1 -C 6 alkyl; or

R 10 and R 11 together with the nitrogen to which they are attached, are forming a saturated or partially saturated cyclic, bicyclic or tricyclic ring system containing from 4 to 10 carbon atoms and from 0 to 2 additional heteroatoms selected from nitrogen, oxygen or sulphur, the ring system optionally being substituted with at least one of C 1 -C 8 alkyl, aryl, hetaryl, arylC 1 -C 6 alkyl, hetarylC 1 -C 6 alkyl, hydroxy, oxo, cyano, C 1 -C 6 alkyloxy, arylC 1 -C 6 alkyloxy, hetaryl C 1 -C 6 alkyloxy, C 1 -C 6 alkyloxyC 1 -C 6 alkyl, C 1 -C 6 alkylcarbonyl, arylcarbonyl, hetarylcarbonyl, arylC 1 -C 6 alkylcarbonyl, hetarylC 1 -C 6 alkylcarbonyl, C 1 -C 6 alkylcarboxy, arylcarboxy or arylC 1-6 alkylcarboxy; or

a salt thereof with a pharmaceutically acceptable acid or base, or optical isomer or mixture of optical isomers, racemic mixture, a prodrug thereof, or tautomeric form thereof.

3. The combination according to claim 1 , wherein the 11β-HSD1 inhibitor is selected from:

[1-(4-Methoxy-phenyl)-5-methyl-1H-pyrazol-4-yl]-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone;

1-[1-(4-Chloro-phenyl)-5-propyl-1H-pyrazol-4-yl]-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone; or [1-(3,5-Dichloro-phenyl)-5-propyl-1H-pyrazol-4-yl]-(1,3,3-trimethyl-6-aza-bicyclo[3.2.1]oct-6-yl)-methanone;

a salt thereof with a pharmaceutically acceptable acid or base, or optical isomer or mixture of optical isomers, racemic mixture, or tautomeric form thereof.

Assignments (12)
CORRECTIVE ASSIGNMENT TO CORRECT THE RECEIVING PARTY DATA PREVIOUSLY RECORDED AT REEL: 036254 FRAME: 0792. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Sep 24, 2015
From: M&F TTP HOLDINGS LLC, AS COLLATERAL AGENT
To: VTVX HOLDINGS II LLC
Reel/Frame 036675/0399 →
RELEASE OF SECURITY INTEREST Recorded Aug 3, 2015
From: M&F TTP HOLDINGS LLC, AS COLLATERAL AGENT
To: VTVX HOLDINGS I LLC
Reel/Frame 036254/0792 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jul 31, 2015
From: VTVX HOLDINGS II LLC
To: VTV THERAPEUTICS LLC
Reel/Frame 036242/0362 →
CHANGE OF NAME Recorded Jul 30, 2015
From: HIGH POINT PHARMACEUTICALS, LLC
To: VTVX HOLDINGS II LLC
Reel/Frame 036236/0159 →
SECURITY INTEREST Recorded Feb 26, 2015
From: HIGH POINT PHARMACEUTICALS, LLC
To: M&F TTP HOLDINGS LLC, AS COLLATERAL AGENT
Reel/Frame 035103/0029 →
NOTICE OF RELEASE OF SECURITY INTEREST IN PATENTS FOR REEL/FRAME 030982/0793 Recorded Apr 7, 2014
From: M&F TTP HOLDINGS LLC
To: HIGH POINT PHARMACEUTICALS, LLC
Reel/Frame 032621/0867 →
SECURITY AGREEMENT Recorded Aug 9, 2013
From: HIGH POINT PHARMACEUTICALS, LLC
To: M&F TTP HOLDINGS LLC C/O MACANDREWS & FORBES HOLDINGS INC.
Reel/Frame 030982/0793 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 27, 2009
From: TRANSTECH PHARMA, INC.
To: HIGH POINT PHARMACEUTICALS, LLC
Reel/Frame 022596/0244 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 20, 2009
From: NOVO NORDISK A/S
To: TRANSTECH PHARMA, INC.
Reel/Frame 022566/0174 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Oct 30, 2008
From: TRANSTECH PHARMA, INC.
To: HIGH POINT PHARMACEUTICALS, LLC
Reel/Frame 021760/0499 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded May 30, 2008
From: NOVO NORDISK A/S
To: TRANSTECH PHARMA, INC.
Reel/Frame 021018/0022 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Feb 2, 2006
From: KAMPEN, GITA CAMILLA TEJLGAARD; ANDERSEN, HENRIK SUNE
To: NOVO NORDISK A/S
Reel/Frame 017231/0827 →