TWI494314B - ５,７－取代的－咪唑并［１,２－ｃ］嘧啶 - Google Patents

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Publication number

TWI494314B

TWI494314B TW100113047A TW100113047A TWI494314B TW I494314 B TWI494314 B TW I494314B TW 100113047 A TW100113047 A TW 100113047A TW 100113047 A TW100113047 A TW 100113047A TW I494314 B TWI494314 B TW I494314B

Authority

TW

Taiwan

Prior art keywords

pyrazol

alkyl

imidazo

pyrimidin

methyl

Prior art date

2010-04-14

Links

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• 125000000217 alkyl group Chemical group 0.000 claims description 638
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 495
• -1 pyrazol-4-yl Chemical group 0.000 claims description 353
• 150000001875 compounds Chemical class 0.000 claims description 281
• 125000001424 substituent group Chemical group 0.000 claims description 200
• 229910052757 nitrogen Inorganic materials 0.000 claims description 185
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 151
• 238000002360 preparation method Methods 0.000 claims description 133
• 229910052799 carbon Inorganic materials 0.000 claims description 131
• 150000001721 carbon Chemical group 0.000 claims description 125
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 102
• FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 claims description 99
• 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 92
• 150000003839 salts Chemical class 0.000 claims description 92
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 72
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 70
• 229910052739 hydrogen Inorganic materials 0.000 claims description 70
• 239000012453 solvate Substances 0.000 claims description 70
• 239000001257 hydrogen Substances 0.000 claims description 66
• 125000003545 alkoxy group Chemical group 0.000 claims description 61
• PQIOSYKVBBWRRI-UHFFFAOYSA-N methylphosphonyl difluoride Chemical group CP(F)(F)=O PQIOSYKVBBWRRI-UHFFFAOYSA-N 0.000 claims description 61
• 125000001153 fluoro group Chemical group F* 0.000 claims description 56
• 201000010099 disease Diseases 0.000 claims description 54
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 54
• 239000002585 base Substances 0.000 claims description 53
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 44
• 238000000034 method Methods 0.000 claims description 43
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 37
• 229910052786 argon Inorganic materials 0.000 claims description 37
• 238000011282 treatment Methods 0.000 claims description 37
• PQWQQQGKMHENOC-UHFFFAOYSA-N imidazo[1,2-c]pyrimidine Chemical compound C1=NC=CC2=NC=CN21 PQWQQQGKMHENOC-UHFFFAOYSA-N 0.000 claims description 35
• 229910052731 fluorine Inorganic materials 0.000 claims description 31
• 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 29
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 28
• 150000002431 hydrogen Chemical class 0.000 claims description 27
• 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 27
• 125000000304 alkynyl group Chemical group 0.000 claims description 26
• 125000004429 atom Chemical group 0.000 claims description 26
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 26
• 229920006395 saturated elastomer Polymers 0.000 claims description 26
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 23
• 229910052736 halogen Inorganic materials 0.000 claims description 23
• 125000000623 heterocyclic group Chemical group 0.000 claims description 23
• 229910052760 oxygen Inorganic materials 0.000 claims description 23
• 208000023275 Autoimmune disease Diseases 0.000 claims description 22
• 125000005842 heteroatom Chemical group 0.000 claims description 22
• PWUBONDMIMDOQY-UHFFFAOYSA-N acetonitrile;hydrochloride Chemical compound Cl.CC#N PWUBONDMIMDOQY-UHFFFAOYSA-N 0.000 claims description 21
• 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 21
• 125000001072 heteroaryl group Chemical group 0.000 claims description 21
• 241000124008 Mammalia Species 0.000 claims description 20
• 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 20
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 20
• 208000027866 inflammatory disease Diseases 0.000 claims description 20
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
• 229910052801 chlorine Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 230000003211 malignant effect Effects 0.000 claims description 19
• 230000008878 coupling Effects 0.000 claims description 18
• 238000010168 coupling process Methods 0.000 claims description 18
• 238000005859 coupling reaction Methods 0.000 claims description 18
• 125000004076 pyridyl group Chemical group 0.000 claims description 17
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 16
• 239000003153 chemical reaction reagent Substances 0.000 claims description 16
• 239000011737 fluorine Substances 0.000 claims description 16
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
• 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 15
• 210000000056 organ Anatomy 0.000 claims description 14
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 13
• 229910052763 palladium Inorganic materials 0.000 claims description 13
• 125000000714 pyrimidinyl group Chemical group 0.000 claims description 13
• HNEGJTWNOOWEMH-UHFFFAOYSA-N 1-fluoropropane Chemical group [CH2]CCF HNEGJTWNOOWEMH-UHFFFAOYSA-N 0.000 claims description 12
• 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 12
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 12
• 239000001301 oxygen Substances 0.000 claims description 12
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 11
• 206010052779 Transplant rejections Diseases 0.000 claims description 11
• 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 11
• 125000003566 oxetanyl group Chemical group 0.000 claims description 11
• 230000008569 process Effects 0.000 claims description 11
• QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 11
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 10
• 239000003054 catalyst Substances 0.000 claims description 10
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
• 150000002460 imidazoles Chemical class 0.000 claims description 10
• RAXXELZNTBOGNW-UHFFFAOYSA-O Imidazolium Chemical compound C1=C[NH+]=CN1 RAXXELZNTBOGNW-UHFFFAOYSA-O 0.000 claims description 9
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 9
• 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 9
• 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 9
• QSKPIOLLBIHNAC-UHFFFAOYSA-N 2-chloro-acetaldehyde Chemical compound ClCC=O QSKPIOLLBIHNAC-UHFFFAOYSA-N 0.000 claims description 8
• YUPDWXZOLVVALZ-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 YUPDWXZOLVVALZ-UHFFFAOYSA-N 0.000 claims description 8
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 8
• JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 claims description 8
• 150000001335 aliphatic alkanes Chemical class 0.000 claims description 8
• 230000001363 autoimmune Effects 0.000 claims description 7
• 125000004980 cyclopropylene group Chemical group 0.000 claims description 7
• 239000003446 ligand Substances 0.000 claims description 7
• 239000008194 pharmaceutical composition Substances 0.000 claims description 7
• 239000003814 drug Substances 0.000 claims description 6
• ZTOMUSMDRMJOTH-UHFFFAOYSA-N glutaronitrile Chemical compound N#CCCCC#N ZTOMUSMDRMJOTH-UHFFFAOYSA-N 0.000 claims description 6
• 229910052717 sulfur Inorganic materials 0.000 claims description 6
• 125000006164 6-membered heteroaryl group Chemical group 0.000 claims description 5
• NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 5
• 125000005605 benzo group Chemical group 0.000 claims description 5
• 239000003638 chemical reducing agent Substances 0.000 claims description 5
• 239000012025 fluorinating agent Substances 0.000 claims description 5
• 125000002883 imidazolyl group Chemical group 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
• 150000002825 nitriles Chemical class 0.000 claims description 5
• 125000002971 oxazolyl group Chemical group 0.000 claims description 5
• 125000006239 protecting group Chemical group 0.000 claims description 5
• 125000002098 pyridazinyl group Chemical group 0.000 claims description 5
• 125000003003 spiro group Chemical group 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 4
• LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 4
• 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 claims description 4
• 125000000068 chlorophenyl group Chemical group 0.000 claims description 4
• DOBRDRYODQBAMW-UHFFFAOYSA-N copper(i) cyanide Chemical compound [Cu+].N#[C-] DOBRDRYODQBAMW-UHFFFAOYSA-N 0.000 claims description 4
• 150000002576 ketones Chemical class 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 claims description 4
• 125000006569 (C5-C6) heterocyclic group Chemical group 0.000 claims description 3
• CEARHFAOWJNTGH-UHFFFAOYSA-N 3-[3-methyl-4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound CC1=NN(CCC#N)C=C1C1=NC(C2=CN(C)N=C2)=CC2=NC=CN12 CEARHFAOWJNTGH-UHFFFAOYSA-N 0.000 claims description 3
• GEYUNVRSROHFKM-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]pentanedinitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)CC#N)=N1 GEYUNVRSROHFKM-UHFFFAOYSA-N 0.000 claims description 3
• FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims description 3
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
• 239000007822 coupling agent Substances 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
• 230000036961 partial effect Effects 0.000 claims description 3
• 238000006467 substitution reaction Methods 0.000 claims description 3
• LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• IXDYSBQNTZFBQM-UHFFFAOYSA-N 2-[1-(cyanomethyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC#N)C2)=N1 IXDYSBQNTZFBQM-UHFFFAOYSA-N 0.000 claims description 2
• DTOPBQTXJVBHDA-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 DTOPBQTXJVBHDA-UHFFFAOYSA-N 0.000 claims description 2
• BVAOKWYKPDLRNN-UHFFFAOYSA-N 2-[1-cyclopropylsulfonyl-3-[4-[7-(4-methoxyphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1=CC(OC)=CC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C2CC2)=N1 BVAOKWYKPDLRNN-UHFFFAOYSA-N 0.000 claims description 2
• KRKDHWKSQRYGHL-UHFFFAOYSA-N 2-[1-ethylsulfonyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]azetidin-3-yl]acetonitrile Chemical compound C1N(S(=O)(=O)CC)CC1(CC#N)N1N=CC(C=2N3C=CN=C3C=C(N=2)C2=CN(C)N=C2)=C1 KRKDHWKSQRYGHL-UHFFFAOYSA-N 0.000 claims description 2
• SZRMTPCIRJJRSB-UHFFFAOYSA-N 2-[3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,2-trifluoroethyl)azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC(F)(F)F)C2)=N1 SZRMTPCIRJJRSB-UHFFFAOYSA-N 0.000 claims description 2
• IRBWVTXXHFRLQT-UHFFFAOYSA-N 2-[3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,3,3-tetrafluoropropyl)azetidin-3-yl]acetonitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC(F)(F)C(F)F)C2)=N1 IRBWVTXXHFRLQT-UHFFFAOYSA-N 0.000 claims description 2
• NOTRLIIDQVQFTF-UHFFFAOYSA-N 2-[3-[4-[7-(2-methoxypyrimidin-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(trifluoromethylsulfonyl)azetidin-3-yl]acetonitrile Chemical compound C1=NC(OC)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(C2)S(=O)(=O)C(F)(F)F)=N1 NOTRLIIDQVQFTF-UHFFFAOYSA-N 0.000 claims description 2
• PFGSXEGYUMDTOQ-UHFFFAOYSA-N 2-[3-[4-[7-(2-methyl-1,3-thiazol-5-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-1-(2,2,2-trifluoroethyl)azetidin-3-yl]acetonitrile Chemical compound S1C(C)=NC=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C2(CC#N)CN(CC(F)(F)F)C2)=N1 PFGSXEGYUMDTOQ-UHFFFAOYSA-N 0.000 claims description 2
• KLNXUTSCUIBQGB-UHFFFAOYSA-N 2-bromo-2-fluoroacetaldehyde Chemical compound FC(Br)C=O KLNXUTSCUIBQGB-UHFFFAOYSA-N 0.000 claims description 2
• AVAHZUUYBFUOPN-UHFFFAOYSA-N 2-chloro-2-fluoroacetaldehyde Chemical compound FC(Cl)C=O AVAHZUUYBFUOPN-UHFFFAOYSA-N 0.000 claims description 2
• HSSAMVTVTVHIPM-UHFFFAOYSA-N 2-methyl-3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(CC(C)C#N)C=C1C1=NC(C=2C=CC(=CC=2)N2CCOCC2)=CC2=NC=CN12 HSSAMVTVTVHIPM-UHFFFAOYSA-N 0.000 claims description 2
• ABNBEHYCFTZPKW-UHFFFAOYSA-N 3-(2,2-difluorocyclopropyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2C(C2)(F)F)=N1 ABNBEHYCFTZPKW-UHFFFAOYSA-N 0.000 claims description 2
• XVZYEWRMSHBLGW-UHFFFAOYSA-N 3-(2-chlorophenyl)-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C(=CC=CC=2)Cl)=N1 XVZYEWRMSHBLGW-UHFFFAOYSA-N 0.000 claims description 2
• OYSMCZSDTIWOJT-UHFFFAOYSA-N 3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]-3-pyridin-4-ylpropanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C=2C=CN=CC=2)=N1 OYSMCZSDTIWOJT-UHFFFAOYSA-N 0.000 claims description 2
• COIHEXKIXPEXTH-UHFFFAOYSA-N 3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]butanenitrile Chemical compound C1=NN(C(CC#N)C)C=C1C1=NC(C=2C=CC(=CC=2)N2CCOCC2)=CC2=NC=CN12 COIHEXKIXPEXTH-UHFFFAOYSA-N 0.000 claims description 2
• CUYRFHRUCXVFPJ-UHFFFAOYSA-N 3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(CCC#N)C=C1C1=NC(C=2C=CC(=CC=2)N2CCOCC2)=CC2=NC=CN12 CUYRFHRUCXVFPJ-UHFFFAOYSA-N 0.000 claims description 2
• NPBKLGISHBMOCJ-UHFFFAOYSA-N 3-[5-methyl-4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(CCC#N)C(C)=C1C1=NC(C2=CN(C)N=C2)=CC2=NC=CN12 NPBKLGISHBMOCJ-UHFFFAOYSA-N 0.000 claims description 2
• JMUWHIMQRSJDOC-UHFFFAOYSA-N 3-cyclopentyl-3-[4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CCCC2)=N1 JMUWHIMQRSJDOC-UHFFFAOYSA-N 0.000 claims description 2
• JMXKOCMTQQASFL-UHFFFAOYSA-N 3-cyclopropyl-3-[3-methyl-4-[7-(1-methylpyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound CC1=NN(C(CC#N)C2CC2)C=C1C(N1C=CN=C1C=1)=NC=1C=1C=NN(C)C=1 JMXKOCMTQQASFL-UHFFFAOYSA-N 0.000 claims description 2
• CIKUAIFCICQYFL-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(2-methyl-3,4-dihydro-1h-isoquinolin-6-yl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C=1C=C2CN(C)CCC2=CC=1C(N=1)=CC2=NC=CN2C=1C(=C1)C=NN1C(CC#N)C1CC1 CIKUAIFCICQYFL-UHFFFAOYSA-N 0.000 claims description 2
• DRESRNCKODYTMN-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-(4-morpholin-4-ylphenyl)imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=C(C=2N3C=CN=C3C=C(N=2)C=2C=CC(=CC=2)N2CCOCC2)C=NN1C(CC#N)C1CC1 DRESRNCKODYTMN-UHFFFAOYSA-N 0.000 claims description 2
• QANAXEPXPBKJEM-UHFFFAOYSA-N 3-cyclopropyl-3-[4-[7-[1-(2-propan-2-yloxyethyl)pyrazol-4-yl]imidazo[1,2-c]pyrimidin-5-yl]pyrazol-1-yl]propanenitrile Chemical compound C1=NN(CCOC(C)C)C=C1C1=CC2=NC=CN2C(C2=CN(N=C2)C(CC#N)C2CC2)=N1 QANAXEPXPBKJEM-UHFFFAOYSA-N 0.000 claims description 2
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