HRP20010732A2 - Substituted bicyclic heteroaryl compounds as integrin antagonists - Google Patents

Info

Publication number

HRP20010732A2

HRP20010732A2 HR20010732A HRP20010732A HRP20010732A2 HR P20010732 A2 HRP20010732 A2 HR P20010732A2 HR 20010732 A HR20010732 A HR 20010732A HR P20010732 A HRP20010732 A HR P20010732A HR P20010732 A2 HRP20010732 A2 HR P20010732A2

Authority

HR

Croatia

Prior art keywords

alkyl

group

ny3y4

image

aryl

Prior art date

1999-04-12

Links

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• 108010044426 integrins Proteins 0.000 title description 18
• 102000006495 integrins Human genes 0.000 title description 18
• 239000005557 antagonist Substances 0.000 title 1
• 150000001875 compounds Chemical class 0.000 claims abstract description 256
• -1 heteroaryldiyl Chemical group 0.000 claims abstract description 115
• 125000000217 alkyl group Chemical group 0.000 claims abstract description 107
• 239000002253 acid Chemical group 0.000 claims abstract description 62
• 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 55
• 150000003839 salts Chemical class 0.000 claims abstract description 55
• 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 34
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims abstract description 30
• 239000000651 prodrug Substances 0.000 claims abstract description 30
• 229940002612 prodrug Drugs 0.000 claims abstract description 30
• 125000002947 alkylene group Chemical group 0.000 claims abstract description 28
• 229910052760 oxygen Inorganic materials 0.000 claims abstract description 27
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 26
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 25
• 125000003342 alkenyl group Chemical group 0.000 claims abstract description 24
• 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 17
• 239000012453 solvate Substances 0.000 claims abstract description 17
• 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
• 125000000304 alkynyl group Chemical group 0.000 claims abstract description 15
• 229920006395 saturated elastomer Polymers 0.000 claims abstract description 12
• 125000004450 alkenylene group Chemical group 0.000 claims abstract description 10
• 125000002993 cycloalkylene group Chemical group 0.000 claims abstract description 10
• 150000004677 hydrates Chemical class 0.000 claims abstract description 10
• 125000004419 alkynylene group Chemical group 0.000 claims abstract description 9
• 125000000732 arylene group Chemical group 0.000 claims abstract description 9
• 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
• 125000006588 heterocycloalkylene group Chemical group 0.000 claims abstract description 8
• 125000002619 bicyclic group Chemical group 0.000 claims abstract description 6
• 125000005724 cycloalkenylene group Chemical group 0.000 claims abstract description 6
• 125000003118 aryl group Chemical group 0.000 claims description 79
• 239000000203 mixture Substances 0.000 claims description 62
• 239000001257 hydrogen Substances 0.000 claims description 56
• 229910052739 hydrogen Inorganic materials 0.000 claims description 56
• 238000000034 method Methods 0.000 claims description 50
• 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 28
• 150000002431 hydrogen Chemical group 0.000 claims description 26
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 21
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 18
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
• 125000001424 substituent group Chemical group 0.000 claims description 18
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
• 125000003545 alkoxy group Chemical group 0.000 claims description 15
• 125000000524 functional group Chemical group 0.000 claims description 15
• 238000002360 preparation method Methods 0.000 claims description 14
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 13
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 11
• 230000021164 cell adhesion Effects 0.000 claims description 10
• 239000011203 carbon fibre reinforced carbon Substances 0.000 claims description 9
• 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 9
• 229910052736 halogen Inorganic materials 0.000 claims description 9
• 150000002367 halogens Chemical class 0.000 claims description 9
• 239000003112 inhibitor Substances 0.000 claims description 9
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims description 8
• 238000004519 manufacturing process Methods 0.000 claims description 8
• 125000004043 oxo group Chemical group O=* 0.000 claims description 8
• 125000004414 alkyl thio group Chemical group 0.000 claims description 7
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
• 125000005843 halogen group Chemical group 0.000 claims description 7
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 7
• 239000000543 intermediate Substances 0.000 claims description 7
• 230000001404 mediated effect Effects 0.000 claims description 7
• 241001465754 Metazoa Species 0.000 claims description 6
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 6
• 125000004122 cyclic group Chemical group 0.000 claims description 6
• 239000001301 oxygen Substances 0.000 claims description 6
• 239000005977 Ethylene Substances 0.000 claims description 5
• 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
• 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
• 125000005015 aryl alkynyl group Chemical group 0.000 claims description 5
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
• 238000002560 therapeutic procedure Methods 0.000 claims description 5
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical group C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 4
• 101150020251 NR13 gene Proteins 0.000 claims description 4
• 125000002252 acyl group Chemical group 0.000 claims description 4
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
• 125000005530 alkylenedioxy group Chemical group 0.000 claims description 4
• 125000003435 aroyl group Chemical group 0.000 claims description 4
• 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 claims description 4
• 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
• 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 4
• 125000005161 aryl oxy carbonyl group Chemical group 0.000 claims description 4
• 125000005110 aryl thio group Chemical group 0.000 claims description 4
• 125000004104 aryloxy group Chemical group 0.000 claims description 4
• 208000006673 asthma Diseases 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 125000005312 heteroarylalkynyl group Chemical group 0.000 claims description 4
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
• HZKFOQAVQRXXIS-UHFFFAOYSA-N 3-[5-[[2-(2-anilino-1,3-benzoxazol-6-yl)acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound C1=NC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C=CC=CC=2)O2)C2=C1 HZKFOQAVQRXXIS-UHFFFAOYSA-N 0.000 claims description 3
• KPHMACREDSGBEK-UHFFFAOYSA-N 3-[5-[[2-[2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound C1=NC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C(=CC=CC=2)C)O2)C2=C1 KPHMACREDSGBEK-UHFFFAOYSA-N 0.000 claims description 3
• QEBMPSSBGWOGFB-UHFFFAOYSA-N 3-[5-[[2-[4-methyl-2-(2-methylanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound C1=NC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC(C)=C(N=C(NC=2C(=CC=CC=2)C)O2)C2=C1 QEBMPSSBGWOGFB-UHFFFAOYSA-N 0.000 claims description 3
• DDVHIBFDBPGRSV-UHFFFAOYSA-N 3-[6-[[2-(2-anilino-1,3-benzoxazol-6-yl)acetyl]amino]pyridin-3-yl]butanoic acid Chemical compound N1=CC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C=CC=CC=2)O2)C2=C1 DDVHIBFDBPGRSV-UHFFFAOYSA-N 0.000 claims description 3
• 125000004442 acylamino group Chemical group 0.000 claims description 3
• 125000005239 aroylamino group Chemical group 0.000 claims description 3
• 125000005135 aryl sulfinyl group Chemical group 0.000 claims description 3
• 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 3
• 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 229940079593 drug Drugs 0.000 claims description 3
• 239000003814 drug Substances 0.000 claims description 3
• 125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 3
• RAHZWNYVWXNFOC-UHFFFAOYSA-N sulfur dioxide Inorganic materials O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 claims description 3
• 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
• 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
• FFIFGJCAAORBLY-UHFFFAOYSA-N 3-[5-[[2-[2-(2-chloroanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-2-yl]butanoic acid Chemical compound C1=NC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C(=CC=CC=2)Cl)O2)C2=C1 FFIFGJCAAORBLY-UHFFFAOYSA-N 0.000 claims description 2
• AOLBSYQVGHVHAG-UHFFFAOYSA-N 3-[6-[[2-[2-(2-chloroanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-3-yl]butanoic acid Chemical compound N1=CC(C(CC(O)=O)C)=CC=C1NC(=O)CC1=CC=C(N=C(NC=2C(=CC=CC=2)Cl)O2)C2=C1 AOLBSYQVGHVHAG-UHFFFAOYSA-N 0.000 claims description 2
• PEDWWPLZSFETTA-UHFFFAOYSA-N 3-[6-[[2-[2-(3-methoxyanilino)-1,3-benzoxazol-6-yl]acetyl]amino]pyridin-3-yl]butanoic acid Chemical compound COC1=CC=CC(NC=2OC3=CC(CC(=O)NC=4N=CC(=CC=4)C(C)CC(O)=O)=CC=C3N=2)=C1 PEDWWPLZSFETTA-UHFFFAOYSA-N 0.000 claims description 2
• MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
• DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 2
• CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 claims description 2
• 125000005518 carboxamido group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 208000027866 inflammatory disease Diseases 0.000 claims description 2
• KIWSYRHAAPLJFJ-DNZSEPECSA-N n-[(e,2z)-4-ethyl-2-hydroxyimino-5-nitrohex-3-enyl]pyridine-3-carboxamide Chemical compound [O-][N+](=O)C(C)C(/CC)=C/C(=N/O)/CNC(=O)C1=CC=CN=C1 KIWSYRHAAPLJFJ-DNZSEPECSA-N 0.000 claims description 2
• 239000000825 pharmaceutical preparation Substances 0.000 claims description 2
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 2
• 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 2
• 125000004434 sulfur atom Chemical group 0.000 claims description 2
• UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 2
• 125000004070 6 membered heterocyclic group Chemical group 0.000 claims 1
• DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims 1
• 125000003275 alpha amino acid group Chemical group 0.000 claims 1
• 150000001555 benzenes Chemical class 0.000 claims 1
• 108010000134 Vascular Cell Adhesion Molecule-1 Proteins 0.000 abstract description 17
• 108010067306 Fibronectins Proteins 0.000 abstract description 13
• 102000016359 Fibronectins Human genes 0.000 abstract description 13
• 102100023543 Vascular cell adhesion protein 1 Human genes 0.000 abstract description 13
• 230000003993 interaction Effects 0.000 abstract description 9
• 125000003107 substituted aryl group Chemical group 0.000 abstract description 4
• 108010008212 Integrin alpha4beta1 Proteins 0.000 abstract description 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 92
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 81
• 239000000243 solution Substances 0.000 description 81
• 230000000052 comparative effect Effects 0.000 description 64
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
• 238000006243 chemical reaction Methods 0.000 description 54
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
• 150000002148 esters Chemical class 0.000 description 40
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 36
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 33
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
• 210000004027 cell Anatomy 0.000 description 29
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 27
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 27
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 25
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 24
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 24
• 239000002585 base Substances 0.000 description 22
• 125000004432 carbon atom Chemical group C* 0.000 description 22
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• 239000007787 solid Substances 0.000 description 18
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 18
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• 238000010992 reflux Methods 0.000 description 16
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• 235000019198 oils Nutrition 0.000 description 15
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 14
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 13
• 238000004587 chromatography analysis Methods 0.000 description 13
• 229910052801 chlorine Inorganic materials 0.000 description 12
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• 229910052799 carbon Inorganic materials 0.000 description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
• 229910052763 palladium Inorganic materials 0.000 description 9
• 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 9
• 150000003254 radicals Chemical class 0.000 description 9
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• 125000001309 chloro group Chemical group Cl* 0.000 description 8
• 239000000706 filtrate Substances 0.000 description 8
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• 238000012360 testing method Methods 0.000 description 8
• RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 8
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• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
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• BDNKZNFMNDZQMI-UHFFFAOYSA-N 1,3-diisopropylcarbodiimide Chemical compound CC(C)N=C=NC(C)C BDNKZNFMNDZQMI-UHFFFAOYSA-N 0.000 description 5
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 5
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• 238000004809 thin layer chromatography Methods 0.000 description 5
• 210000001519 tissue Anatomy 0.000 description 5
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 4
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