WO2005012249A3 - Adamantyglycine- based inhibitors of dipeptidyl peptidase iv for the treatment of diabetes - Google Patents

Adamantyglycine- based inhibitors of dipeptidyl peptidase iv for the treatment of diabetes Download PDF

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Publication number
WO2005012249A3
WO2005012249A3 PCT/US2004/024257 US2004024257W WO2005012249A3 WO 2005012249 A3 WO2005012249 A3 WO 2005012249A3 US 2004024257 W US2004024257 W US 2004024257W WO 2005012249 A3 WO2005012249 A3 WO 2005012249A3
Authority
WO
WIPO (PCT)
Prior art keywords
diabetes
treatment
dipeptidyl peptidase
adamantyglycine
based inhibitors
Prior art date
Application number
PCT/US2004/024257
Other languages
French (fr)
Other versions
WO2005012249A2 (en
Inventor
Lawrence G Hamann
Ashish Khanna
Mark S Kirby
David R Magnin
Ligaya M Simpkins
James C Sutton
Jeffrey Robl
Original Assignee
Bristol Myers Squibb Co
Lawrence G Hamann
Ashish Khanna
Mark S Kirby
David R Magnin
Ligaya M Simpkins
James C Sutton
Jeffrey Robl
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Bristol Myers Squibb Co, Lawrence G Hamann, Ashish Khanna, Mark S Kirby, David R Magnin, Ligaya M Simpkins, James C Sutton, Jeffrey Robl filed Critical Bristol Myers Squibb Co
Priority to EP04779352A priority Critical patent/EP1658066B9/en
Priority to AT04779352T priority patent/ATE444064T1/en
Priority to JP2006522608A priority patent/JP2007501231A/en
Priority to DE602004023398T priority patent/DE602004023398D1/en
Publication of WO2005012249A2 publication Critical patent/WO2005012249A2/en
Publication of WO2005012249A3 publication Critical patent/WO2005012249A3/en
Priority to NO20060479A priority patent/NO20060479L/en
Priority to IS8274A priority patent/IS8274A/en

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/46—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of non-condensed rings
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P13/00—Drugs for disorders of the urinary system
    • A61P13/12—Drugs for disorders of the urinary system of the kidneys
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P17/00—Drugs for dermatological disorders
    • A61P17/02—Drugs for dermatological disorders for treating wounds, ulcers, burns, scars, keloids, or the like
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P25/00—Drugs for disorders of the nervous system
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P27/00—Drugs for disorders of the senses
    • A61P27/02—Ophthalmic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/04—Anorexiants; Antiobesity agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/06—Antihyperlipidemics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P3/00—Drugs for disorders of the metabolism
    • A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
    • A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P9/00—Drugs for disorders of the cardiovascular system
    • A61P9/12—Antihypertensives
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/45—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings
    • C07C255/47—Carboxylic acid nitriles having cyano groups bound to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of rings being part of condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
    • C07D209/52—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/04—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
    • C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
    • C07D295/182—Radicals derived from carboxylic acids
    • C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/06—Systems containing only non-condensed rings with a five-membered ring
    • C07C2601/08—Systems containing only non-condensed rings with a five-membered ring the ring being saturated
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2602/00—Systems containing two condensed rings
    • C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
    • C07C2602/14—All rings being cycloaliphatic
    • C07C2602/18—All rings being cycloaliphatic the ring system containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/56—Ring systems containing bridged rings
    • C07C2603/58—Ring systems containing bridged rings containing three rings
    • C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
    • C07C2603/74—Adamantanes

Abstract

Compounds are provided having the formula (I) wherein: n is 0, 1 or 2; m is 0, 1 or 2; the sum of n + m less then or equal to 2; the dashed bonds forming a cyclopropyl ring can only be present when Y is CH; X is H or CN; Y is CH, CH2, CHF, CF2, O, S, SO, or SO2; and A is adamantyl. The compounds are inhibitors of dipeptidyl peptidase IV (DPP-IV) and are useful for the treatment of diabetes and related diseases.
PCT/US2004/024257 2003-08-01 2004-07-28 Adamantyglycine- based inhibitors of dipeptidyl peptidase iv for the treatment of diabetes WO2005012249A2 (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
EP04779352A EP1658066B9 (en) 2003-08-01 2004-07-28 Adamantylglycine- based inhibitors of dipeptidyl peptidase iv for the treatment of diabetes
AT04779352T ATE444064T1 (en) 2003-08-01 2004-07-28 ADAMANTYL GLYCINE-BASED DIPEPTIDYLPEPTIDASE IV INHIBITORS FOR THE TREATMENT OF DIABETES
JP2006522608A JP2007501231A (en) 2003-08-01 2004-07-28 Adamantylglycine-based inhibitors and methods of dipeptidyl peptidase IV
DE602004023398T DE602004023398D1 (en) 2003-08-01 2004-07-28 INHIBITORS OF DIPEPTIDYLPEPTIDASE IV ON ADAMANTYL GLYCIN BASE FOR THE TREATMENT OF DIABETES
NO20060479A NO20060479L (en) 2003-08-01 2006-01-30 Adamantylglycine-based inhibitors of Dipeptidyl peptidase IV and methods
IS8274A IS8274A (en) 2003-08-01 2006-01-31 Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
US49183203P 2003-08-01 2003-08-01
US60/491,832 2003-08-01
US10/899,641 2004-07-27
US10/899,641 US6995183B2 (en) 2003-08-01 2004-07-27 Adamantylglycine-based inhibitors of dipeptidyl peptidase IV and methods

Publications (2)

Publication Number Publication Date
WO2005012249A2 WO2005012249A2 (en) 2005-02-10
WO2005012249A3 true WO2005012249A3 (en) 2005-05-06

Family

ID=34118886

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2004/024257 WO2005012249A2 (en) 2003-08-01 2004-07-28 Adamantyglycine- based inhibitors of dipeptidyl peptidase iv for the treatment of diabetes

Country Status (9)

Country Link
US (3) US6995183B2 (en)
EP (2) EP1658066B9 (en)
JP (1) JP2007501231A (en)
AT (1) ATE444064T1 (en)
DE (1) DE602004023398D1 (en)
ES (1) ES2332275T3 (en)
IS (1) IS8274A (en)
NO (1) NO20060479L (en)
WO (1) WO2005012249A2 (en)

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US8883714B2 (en) 2008-04-07 2014-11-11 Arena Pharmaceuticals, Inc. Pharmaceutical compositions comprising GPR119 agonists which act as peptide YY (PYY) secretagogues
US8906901B2 (en) 2005-09-14 2014-12-09 Takeda Pharmaceutical Company Limited Administration of dipeptidyl peptidase inhibitors

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