DK2723741T3 - Substituerede imidazopyridinyl-aminopyridinforbindelser - Google Patents

Substituerede imidazopyridinyl-aminopyridinforbindelser Download PDF

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DK2723741T3
DK2723741T3 DK12802947.7T DK12802947T DK2723741T3 DK 2723741 T3 DK2723741 T3 DK 2723741T3 DK 12802947 T DK12802947 T DK 12802947T DK 2723741 T3 DK2723741 T3 DK 2723741T3
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substituted
unsubstituted
phenyl
alkyl
cancer
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Mark A Ashwell
Chris Brassard
Anton Filikov
Jason Hill
Steffi Koerner
Jean-Marc Lapierre
Yanbin Liu
Nivedita Namdev
Robert Nicewonger
Rocio Palma
Manish Tandon
David Vensel
Akihisa Matsuda
Shin Iimura
Kenichi Yoshida
Takanori Yamazaki
Takahiro Kitamura
Takeshi Isoyama
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Arqule Inc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
    • A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
    • A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
    • A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
    • A61K31/444—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a six-membered ring with nitrogen as a ring heteroatom, e.g. amrinone
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K31/00—Medicinal preparations containing organic active ingredients
    • A61K31/33—Heterocyclic compounds
    • A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
    • A61K31/535—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one oxygen as the ring hetero atoms, e.g. 1,2-oxazines
    • A61K31/5375—1,4-Oxazines, e.g. morpholine
    • A61K31/5377—1,4-Oxazines, e.g. morpholine not condensed and containing further heterocyclic rings, e.g. timolol
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P35/00—Antineoplastic agents
    • A61P35/04—Antineoplastic agents specific for metastasis
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
    • C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D498/08—Bridged systems

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  • Chemical & Material Sciences (AREA)
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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Claims (15)

1. Forbindelse med formel I:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvor: X er NRnRn', ORo, SRs eller
hvor
er linket til imidazopyridinylringen med formel I i den position, der er vist med H**H . J Ro og Rs hver især uafhængigt er usubstitueret eller substitueret C6-Ci0 aryl; Rn er (CH2)mFlhc eller usubstitueret eller substitueret C6-Ci0 aryl; Rn' er H; eller Rn og Rn' sammen med nitrogenatomet, som de er bundet til, danner en usubstitueret eller substitueret morpholin; m er 1,2,3 eller 4; Rhc er usubstitueret eller substitueret heterocyklus omfattende en 6-leddet ring og 1 eller 2 heteroatomer udvalgt fra N, O og S; og RPh er substitueret C3-C6 alkyl eller usubstitueret C4-C6 alkyl; hvor: det substituerede aryl og den substituerede heterocyklus er substitueret i en eller flere ringpositioner med alkyl, alkenyl, akynyl, halogen, hydroxyl, alkoxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, carboxylat, alkylcarbonyl, alkylaminocarbonyl, aralkylaminocarbonyl, alke-nylaminocarbonyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, alkenylcar-bonyl, alkoxycarbonyl, aminocarbonyl, alkylthiocarbonyl, phosphat, phospho- nato, phosphinato, amino (herunder alkylamino, dialkylamino, arylamino, dia-rylamino og alkylarylamino), acylamino (herunder alkylcarbonylamino, arylcarbonylamino, carbamoyl og ureido), amidino, imino, sulfhydryl, al-kylthio, arylthio, thiocarboxylat, sulfater, alkylsulfinyl, sulfonato, sulfamoyl, sulfonamido, nitro, trifluormethyl, cyano, azido, heterocyclyl, alkylaryl eller en aromatisk eller heteroaromatisk enhed; det substituerede morpholin er substitueret med en eller flere grupper, hvoraf hver uafhængigt er udvalgt fra hydroxyl, halogen (herunder fluorin, chlorin, bromin og iodin), cyano, nitro, usubstitueret amino, usubstitueret eller substitueret C-i-Ce alkylamino, usubstitueret eller substitueret di-CrC6 alkylamino, usubstitueret eller substitueret CrC6 alkyl (herunder methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, s-pentyl, og n-hexyl) og usubstitueret eller substitueret C-|-C6 alkoxy (herunder methoxy, ethoxy, n-propyloxy, i-propyloxy, n-butoxy og t-butoxy); det substituerede alkoxy er substitueret med alkenyl, alkynyl, halogen, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycar-bonyloxy, carboxylat, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aminocar-bonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl, phosphat, phosphonato, phosphinato, amino (herunder alkylamino, dialkylamino, arylamino, diarylamino, og alkylarylamino), acylamino (herunder alkylcarbonylamino, arylcarbonylamino, carbamoyl og ureido), amidino, imino, sulfhydryl, alkylthio, arylthio, thiocarboxylat, sulfater, alkylsulfinyl, sulfonat, sulfamoyl, sulfonamido, nitro, trifluormethyl, cyano, azido, heterocyclyl, alkylaryl eller en aromatisk eller heteroaromatisk enhed; og det substituerede alkyl, den substituerede alkylamino eller substituerede dial-kyamino har substituenter, der erstatter et eller flere hydrogenatomer på et eller flere carboner af hydrocarbon-backbonet, hvor substituenterne er alkyl, alkenyl, alkynyl, halogen, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, carboxylat, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl, phosphat, phosphonato, phosphinato, amino (herunder alkylamino, dialkylamino, arylamino, diarylamino og alkylarylamino), acylamino (herunder alkylcarbonylamino, arylcarbonylamino, carbamoyl og ureido), amidino, imino, sulfhydryl, alkylthio, arylthio, thiocarboxylat, sulfater, alkylsulfinyl, sulfonato, sulfamoyl, sulfonamido, nitro, trifluormethyl, cyano, azido, heterocyclyl, alkylaryl eller en aromatisk eller heteroaromatisk enhed.
2. Forbindelse ifølge krav 1, hvor X er NRnRn'; Rn' er H; RN er (CH2)mRhc; m er 1 eller 2; og Rhc er usubstitueret eller substitueret heterocyklus udvalgt fra gruppen bestående af pyrrolidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, isoxazolidinyl, triazolidinyl, tetrahyrofuranyl, piperidinyl, piperazinyl og morp-holinyl.
3. Forbindelse ifølge krav 1, hvor X er NRnRn'; Rn' er H; og RN er usubstitueret phenyl eller phenyl substitueret med en substituent udvalgt fra gruppen bestående af hydroxyl, halogen, cyano, nitro, usubstitueret amino, usubstitueret eller substitueret CrC6 alkyl, usubstitueret eller substitueret CrC6 alkoxy og usubstitueret eller substitueret heterocyklus omfattende en 5- eller 6-leddet ring og 1-3 heteroatomer udvalgt fra N, O og S.
4. Forbindelse ifølge krav 1, hvor X er NRnRn'; og RN og RN' sammen med nitrogenatomet, som de er bundet til, danner et usubstitueret morpholin eller et morpholin substitueret med en substituent udvalgt fra gruppen bestående af hydroxyl, halogen, cyano, nitro, usubstitueret amino, usubstitueret eller substitueret CrC6 alkyl og usubstitueret eller substitueret CrC6 alkoxy.
5. Forbindelse ifølge krav 1, hvor X er OR0; og R0 er usubstitueret phenyl eller phenyl substitueret med en substituent udvalgt fra gruppen bestående af hydroxyl, halogen, cyano, nitro, usubstitueret amino, usubstitueret eller substitueret CrC6 alkyl, usubstitueret eller substitueret CrC6 alkoxy og usubstitueret eller substitueret heterocyklus omfattende en 5- eller 6-leddet ring og 1 -3 heteroatomer udvalgt fra N, O og S.
6. Forbindelse ifølge krav 1, hvor X er ORs; og Rs er usubstitueret phenyl eller phenyl substitueret med en substituent udvalgt fra gruppen bestående af hydroxyl, halogen, cyano, nitro, usubstitueret amino, usubstitueret eller substitueret CrC6 alkyl, usubstitueret eller substitueret CrC6 alkoxy og usubstitueret eller substitueret heterocyklus omfattende en 5- eller 6-leddet ring og 1-3 heteroatomer udvalgt fra N, O og S.
7. Forbindelse ifølge krav 1, udvalgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt eller ester deraf.
8. Forbindelse med formel II:
eller et farmaceutisk acceptabelt salt eller ester deraf, hvor: Ri er (CH2)0-OH eller C(0)Ft2; R-Γ er H; eller Ri og R-Γ sammen med nitrogenatomet, som de er bundet til, danner en ring udvalgt fra gruppen bestående af
og
hvor nitrogenatomet, der er vist med er nitrogenatomet, som Ri og R-Γ er bundet til; o er 1,2, 3 eller 4; R2 er
tert-butyl, usubstitueret eller substitueret C3-C8 carbocyklus eller usubstitue-ret eller substitueret heterocyklus omfattende en 6-leddet ring og 1 eller 2 heteroatomer udvalgt fra N, O og S; n er 0,1,2 eller 3; Rio er H, usubstitueret eller substitueret CrC6 alkyl eller C(0)Rn; Ru er usubstitueret eller substitueret CrC6 alkyl; Rc og Rc' ved hver forekomst uafhængigt er H eller usubstitueret methyl; R3 er NR12R12', C(0)NR6R6', NR7'C(0)R7 eller NR7'S(0)2R7; R6 og R6' hver især uafhængigt er H eller usubstitueret eller substitueret Cr C6 alkyl, eller R6 og R6' sammen med nitrogenatomet, som de er bundet til, danner en usubstitueret eller substitueret heterocyklus omfattende en 5- eller 6-leddet ring og eventuelt 1 eller 2 yderligere heteroatomer udvalgt fra N, O og S; R7 er usubstitueret eller substitueret CrC6 alkyl; R/ er H eller usubstitueret eller substitueret CrC6 alkyl; R-I2 og R-i2' hver især er H, eller Ri2 og Ri2', sammen med nitrogenatomet, som de er bundet til, danner en usubstitueret eller substitueret heterocyklus omfattende en 6-leddet ring og eventuelt 1 eller 2 yderligere heteroatomer udvalgt fra N, O og S; R4 er C(0)R8 eller S(0)2Rr; Rr er usubstitueret eller substitueret C1-C6 alkyl; R8 er usubstitueret eller substitueret C2-C6 alkyl eller usubstitueret eller substitueret C3-C8 carbocyklus; R5 og Rs' hver især uafhængigt er H, usubstitueret eller substitueret CrC6 alkyl eller C(0)NR9R9', forudsat at R5 og R5' ikke begge er H; R9 og R9' hver især uafhængigt er H eller usubstitueret eller substitueret Cr C6 al kyl; Raza er H eller OH; Rp er C(0)NRqRq'; og Rq og Rq· hver især uafhængigt er H eller usubstitueret eller substitueret Cr C6 al kyl, hvor: den substituerede carbocyklus og substituerede heterocyklus er substitueret i en eller flere ringpositioner med alkyl, alkenyl, akynyl, halogen, hydroxyl, al-koxy, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycar-bonyloxy, carboxylat, alkylcarbonyl, alkylaminocarbonyl, aralkylaminocar-bonyl, alkenylaminocarbonyl, alkylcarbonyl, arylcarbonyl, aralkylcarbonyl, alkenylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylthiocarbonyl, phosphat, phosphonato, phosphinato, amino (herunder alkylamino, dialkylamino, arylamino, diarylamino og alkylarylamino), acylamino (herunder alkylcar-bonylamino, arylcarbonylamino, carbamoyl og ureido), amidino, imino, sulfhydryl, alkylthio, arylthio, thiocarboxylat, sulfater, alkylsulfinyl, sulfonato, sulfamoyl, sulfonamido, nitro, trifluormethyl, cyano, azido, heterocyclyl, alky-laryl eller en aromatisk eller heteroaromatisk enhed; og det substituerede alkyl har substituenter, som erstatter et eller flere hydrogenatomer på et eller flere carboner af hydrocarbon-backbonet, hvor substi-tuenterne er alkyl, alkenyl, alkynyl, halogen, hydroxyl, alkylcarbonyloxy, arylcarbonyloxy, alkoxycarbonyloxy, aryloxycarbonyloxy, carboxylat, alkylcarbonyl, arylcarbonyl, alkoxycarbonyl, aminocarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, alkylthiocarbonyl, alkoxyl, phosphat, phosphonato, phosphinato, amino (herunder alkylamino, dialkylamino, arylamino, diarylamino og alkylarylamino), acylamino (herunder alkylcarbonylamino, arylcarbonylamino, carbamoyl og ureido), amidino, imino, sulfhydryl, al- kylthio, arylthio, thiocarboxylat, sulfater, alkylsulfinyl, sulfonato, sulfamoyl, sulfonamido, nitro, trifluormethyl, cyano, azido, heterocyclyl, alkylaryl eller en aromatisk eller heteroaromatisk enhed.
9. Forbindelse ifølge krav 8, hvor Ri og R-Γ sammen med nitrogenatomet, som de er bundet til, danner
eller hvor R-ι og R-Γ sammen med nitrogenatomet, som de er bundet til, danner
10. Forbindelse ifølge krav 8, hvor R-ι' er H, og Ri er (CFI2)o-OFI.
11. Forbindelse ifølge krav 8, hvor R-Γ er H, og Ri er C(0)R2.
12. Forbindelse ifølge krav 11, hvor R2 er
n er 0 eller 1; Rc og Rc' hver især er usubstitueret methyl; R-m er H, methyl, ethyl, propyl eller C(0)Rn; og Ru er methyl, ethyl eller propyl; eller hvor R2 er tert-butyl eller usubstitueret eller substitueret C3-C8 carbocyklus udvalgt fra gruppen bestående af cyclopropyl, cyclobutyl, cyclopentyl, cyclo-hexyl og cycloheptyl; eller hvor R2 er usubstitueret eller substitueret heterocyklus udvalgt fra gruppen bestående af pyrrolidinyl, imidazolidinyl, pyrazolidinyl, oxazolidinyl, isoxazo-lidinyl, triazolidinyl, tetrahyrofuranyl, piperidinyl, piperazinyl, morpholinyl, tetrahydropyranyl og dioxanyl.
13. Forbindelse ifølge krav 8 udvalgt fra gruppen bestående af:
eller et farmaceutisk acceptabelt salt eller ester deraf.
14. Farmaceutisk sammensætning omfattende en terapeutisk virksom mængde af en forbindelse ifølge krav 1 eller krav 8 eller et salt eller ester deraf og et farmaceutisk acceptabelt bærestof eller hjælpestof.
15. Forbindelse ifølge krav 1 eller krav 8 eller et salt eller ester deraf til anvendelse i en fremgangsmåde til behandling af en celleproliferativ lidelse, hvor forbindelsen er til indgivelse i kombination med et farmaceutisk acceptabelt bærestof eller hjælpestof.
DK12802947.7T 2011-06-24 2012-06-21 Substituerede imidazopyridinyl-aminopyridinforbindelser DK2723741T3 (da)

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