JP2012505881A - ステアロイル−ＣｏＡデサチュラーゼの阻害剤として使用するための３−ヒドロキナゾリン−４−オン誘導体 - Google Patents

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Publication number

JP2012505881A

JP2012505881A JP2011532053A JP2011532053A JP2012505881A JP 2012505881 A JP2012505881 A JP 2012505881A JP 2011532053 A JP2011532053 A JP 2011532053A JP 2011532053 A JP2011532053 A JP 2011532053A JP 2012505881 A JP2012505881 A JP 2012505881A

Authority

JP

Japan

Prior art keywords

oxo

methyl

hydroquinazolin

dihydroquinazolin

dichlorophenyl

Prior art date

2008-10-15

Legal status (The legal status 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 status listed.)

Withdrawn

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• 108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 67
• 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract 6
• 239000003112 inhibitor Substances 0.000 title abstract description 17
• 150000001875 compounds Chemical class 0.000 claims abstract description 291
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 54
• 201000010099 disease Diseases 0.000 claims abstract description 40
• 208000008589 Obesity Diseases 0.000 claims abstract description 14
• 235000020824 obesity Nutrition 0.000 claims abstract description 14
• 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 13
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
• 206010028980 Neoplasm Diseases 0.000 claims abstract description 9
• 201000011510 cancer Diseases 0.000 claims abstract description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 314
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 184
• -1 CF 3 Chemical group 0.000 claims description 150
• 125000000217 alkyl group Chemical group 0.000 claims description 136
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 106
• 125000001072 heteroaryl group Chemical group 0.000 claims description 84
• 125000003118 aryl group Chemical group 0.000 claims description 81
• 125000001424 substituent group Chemical group 0.000 claims description 65
• 238000000034 method Methods 0.000 claims description 56
• 125000000623 heterocyclic group Chemical group 0.000 claims description 51
• 229910052739 hydrogen Inorganic materials 0.000 claims description 51
• 239000001257 hydrogen Substances 0.000 claims description 45
• 125000003342 alkenyl group Chemical group 0.000 claims description 42
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 37
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 36
• 125000000304 alkynyl group Chemical group 0.000 claims description 35
• 125000003545 alkoxy group Chemical group 0.000 claims description 32
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 31
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 29
• 150000002431 hydrogen Chemical class 0.000 claims description 26
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 125000002947 alkylene group Chemical group 0.000 claims description 22
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 21
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 20
• 125000002950 monocyclic group Chemical group 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 19
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
• 150000003839 salts Chemical class 0.000 claims description 13
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 13
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 12
• 125000004423 acyloxy group Chemical group 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 11
• 125000004442 acylamino group Chemical group 0.000 claims description 11
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 11
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 9
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• JMSDMPBPEGROHI-JTQLQIEISA-N n-[3-[(1s)-1-(3,4-dichlorophenyl)ethyl]-4-oxoquinazolin-7-yl]-2-hydroxyacetamide Chemical compound C1([C@H](C)N2C(C3=CC=C(NC(=O)CO)C=C3N=C2)=O)=CC=C(Cl)C(Cl)=C1 JMSDMPBPEGROHI-JTQLQIEISA-N 0.000 claims description 7
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 6
• 206010022489 Insulin Resistance Diseases 0.000 claims description 6
• LRZFEBJUJIQVDQ-UHFFFAOYSA-N methyl 2-(dimethylamino)acetate Chemical compound COC(=O)CN(C)C LRZFEBJUJIQVDQ-UHFFFAOYSA-N 0.000 claims description 6
• JMSDMPBPEGROHI-SNVBAGLBSA-N n-[3-[(1r)-1-(3,4-dichlorophenyl)ethyl]-4-oxoquinazolin-7-yl]-2-hydroxyacetamide Chemical compound C1([C@@H](C)N2C(C3=CC=C(NC(=O)CO)C=C3N=C2)=O)=CC=C(Cl)C(Cl)=C1 JMSDMPBPEGROHI-SNVBAGLBSA-N 0.000 claims description 6
• AJRHFFKPSZMWPO-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-n-(2-methoxyethyl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C(=O)NCCOC)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C(Cl)=C1 AJRHFFKPSZMWPO-UHFFFAOYSA-N 0.000 claims description 5
• WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 150000002148 esters Chemical class 0.000 claims description 5
• TZIVVDOZEHUUFW-UHFFFAOYSA-N n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)C)=CC=C2N=CN1CC1=CC=C(Cl)C(Cl)=C1 TZIVVDOZEHUUFW-UHFFFAOYSA-N 0.000 claims description 5
• 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 4
• SRCWQMIQDMSABI-UHFFFAOYSA-N 2-hydroxy-n-[4-oxo-3-[(3-phenylphenyl)methyl]quinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CC(C=1)=CC=CC=1C1=CC=CC=C1 SRCWQMIQDMSABI-UHFFFAOYSA-N 0.000 claims description 4
• BYILTFWWHCOZOG-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-n-methyl-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C(=O)NC)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C=C1 BYILTFWWHCOZOG-UHFFFAOYSA-N 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 4
• 239000008103 glucose Substances 0.000 claims description 4
• 230000000302 ischemic effect Effects 0.000 claims description 4
• AYWPACLSVIRDFY-UHFFFAOYSA-N n-(3-benzyl-4-oxoquinazolin-6-yl)-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CC1=CC=CC=C1 AYWPACLSVIRDFY-UHFFFAOYSA-N 0.000 claims description 4
• UXWAENYXNXUWHG-SNVBAGLBSA-N n-[3-[(1r)-1-[4-chloro-3-(trifluoromethyl)phenyl]ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound C1([C@@H](C)N2C(C3=CC(NC(=O)CO)=CC=C3N=C2)=O)=CC=C(Cl)C(C(F)(F)F)=C1 UXWAENYXNXUWHG-SNVBAGLBSA-N 0.000 claims description 4
• XBWXBBIHXFRYOE-UHFFFAOYSA-N n-[3-[(3,4-dimethylphenyl)methyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound C1=C(C)C(C)=CC=C1CN1C(=O)C2=CC(NC(=O)CO)=CC=C2N=C1 XBWXBBIHXFRYOE-UHFFFAOYSA-N 0.000 claims description 4
• WYCXEKKLBAECDV-UHFFFAOYSA-N n-[3-[(4-chlorophenyl)methyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CC1=CC=C(Cl)C=C1 WYCXEKKLBAECDV-UHFFFAOYSA-N 0.000 claims description 4
• UVNYGTQVNXJYOX-UHFFFAOYSA-N n-[3-[1-(3,4-dichlorophenyl)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound C1=NC2=CC=C(NC(=O)CO)C=C2C(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 UVNYGTQVNXJYOX-UHFFFAOYSA-N 0.000 claims description 4
• JMSDMPBPEGROHI-UHFFFAOYSA-N n-[3-[1-(3,4-dichlorophenyl)ethyl]-4-oxoquinazolin-7-yl]-2-hydroxyacetamide Chemical compound C1=NC2=CC(NC(=O)CO)=CC=C2C(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 JMSDMPBPEGROHI-UHFFFAOYSA-N 0.000 claims description 4
• IBALPTMGUFTXFW-UHFFFAOYSA-N n-[3-[1-(3,4-dichlorophenyl)propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound C1=NC2=CC=C(NC(=O)CO)C=C2C(=O)N1C(CC)C1=CC=C(Cl)C(Cl)=C1 IBALPTMGUFTXFW-UHFFFAOYSA-N 0.000 claims description 4
• GWQNYIBHBLIXEJ-UHFFFAOYSA-N n-[3-[2-(2,4-dichlorophenyl)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCC1=CC=C(Cl)C=C1Cl GWQNYIBHBLIXEJ-UHFFFAOYSA-N 0.000 claims description 4
• TVJUKCVZGFXXNM-UHFFFAOYSA-N n-[3-[2-(2,5-dichlorophenoxy)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCOC1=CC(Cl)=CC=C1Cl TVJUKCVZGFXXNM-UHFFFAOYSA-N 0.000 claims description 4
• REYFHLSLYNRKPX-UHFFFAOYSA-N n-[3-[2-(3-chlorophenyl)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCC1=CC=CC(Cl)=C1 REYFHLSLYNRKPX-UHFFFAOYSA-N 0.000 claims description 4
• HMSNCISXSUECEB-UHFFFAOYSA-N n-[3-[2-(4-chlorophenyl)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCC1=CC=C(Cl)C=C1 HMSNCISXSUECEB-UHFFFAOYSA-N 0.000 claims description 4
• IYONCBOKLGDXMJ-UHFFFAOYSA-N n-[3-[2-[(2,5-dichlorophenyl)sulfonylamino]ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCNS(=O)(=O)C1=CC(Cl)=CC=C1Cl IYONCBOKLGDXMJ-UHFFFAOYSA-N 0.000 claims description 4
• RORPUVRZXYZASA-UHFFFAOYSA-N n-[3-[3-(2,3-dichlorophenoxy)propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC=CC(Cl)=C1Cl RORPUVRZXYZASA-UHFFFAOYSA-N 0.000 claims description 4
• ZYBXKSWALPWWQQ-UHFFFAOYSA-N n-[3-[3-(2,5-dichlorophenoxy)propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC(Cl)=CC=C1Cl ZYBXKSWALPWWQQ-UHFFFAOYSA-N 0.000 claims description 4
• KVZYMEFWOBVJHL-UHFFFAOYSA-N n-[3-[3-(2,5-dichlorophenoxy)propyl]-4-oxoquinazolin-7-yl]-2-hydroxyacetamide Chemical compound C=1C(NC(=O)CO)=CC=C(C2=O)C=1N=CN2CCCOC1=CC(Cl)=CC=C1Cl KVZYMEFWOBVJHL-UHFFFAOYSA-N 0.000 claims description 4
• MFMVQNBXIYJAHT-UHFFFAOYSA-N n-[3-[3-(2-chlorophenoxy)propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC=CC=C1Cl MFMVQNBXIYJAHT-UHFFFAOYSA-N 0.000 claims description 4
• OLWNATBKNXAMAW-UHFFFAOYSA-N n-[3-[3-(2-chlorophenyl)propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCC1=CC=CC=C1Cl OLWNATBKNXAMAW-UHFFFAOYSA-N 0.000 claims description 4
• AUMYINXCQGKYQO-UHFFFAOYSA-N n-[3-[3-(4-chlorophenoxy)propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC=C(Cl)C=C1 AUMYINXCQGKYQO-UHFFFAOYSA-N 0.000 claims description 4
• ZYHAOOUJIRAVKM-UHFFFAOYSA-N n-[3-[3-[2-chloro-5-(trifluoromethyl)phenoxy]propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC(C(F)(F)F)=CC=C1Cl ZYHAOOUJIRAVKM-UHFFFAOYSA-N 0.000 claims description 4
• BAJKEXWWSBUXGL-UHFFFAOYSA-N n-[3-[4-(2,5-dichlorophenoxy)butyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCCOC1=CC(Cl)=CC=C1Cl BAJKEXWWSBUXGL-UHFFFAOYSA-N 0.000 claims description 4
• IDYGCGYCHOUWQB-UHFFFAOYSA-N n-[3-[[4-chloro-3-(trifluoromethyl)phenyl]methyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CC1=CC=C(Cl)C(C(F)(F)F)=C1 IDYGCGYCHOUWQB-UHFFFAOYSA-N 0.000 claims description 4
• DTWKOBGWCSHUPS-UHFFFAOYSA-N n-[3-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CC1=CC=C(F)C(C(F)(F)F)=C1 DTWKOBGWCSHUPS-UHFFFAOYSA-N 0.000 claims description 4
• MMKMXVBTEKTDST-JOCHJYFZSA-N (2r)-n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]-2-hydroxy-3-phenylpropanamide Chemical compound C([C@@H](O)C(=O)NC=1C=C2C(=O)N(CC=3C=C(Cl)C(Cl)=CC=3)C=NC2=CC=1)C1=CC=CC=C1 MMKMXVBTEKTDST-JOCHJYFZSA-N 0.000 claims description 3
• LJELBFFGTXYBQG-NRFANRHFSA-N (2s)-n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]-2-hydroxy-2-phenylacetamide Chemical compound O=C([C@@H](O)C=1C=CC=CC=1)NC(C=C1C2=O)=CC=C1N=CN2CC1=CC=C(Cl)C(Cl)=C1 LJELBFFGTXYBQG-NRFANRHFSA-N 0.000 claims description 3
• MMKMXVBTEKTDST-QFIPXVFZSA-N (2s)-n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]-2-hydroxy-3-phenylpropanamide Chemical compound C([C@H](O)C(=O)NC=1C=C2C(=O)N(CC=3C=C(Cl)C(Cl)=CC=3)C=NC2=CC=1)C1=CC=CC=C1 MMKMXVBTEKTDST-QFIPXVFZSA-N 0.000 claims description 3
• PXJFUCIUENRSIV-JOCHJYFZSA-N (3r)-n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]-3-hydroxy-3-phenylpropanamide Chemical compound C([C@@H](O)C=1C=CC=CC=1)C(=O)NC(C=C1C2=O)=CC=C1N=CN2CC1=CC=C(Cl)C(Cl)=C1 PXJFUCIUENRSIV-JOCHJYFZSA-N 0.000 claims description 3
• PXJFUCIUENRSIV-QFIPXVFZSA-N (3s)-n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]-3-hydroxy-3-phenylpropanamide Chemical compound C([C@H](O)C=1C=CC=CC=1)C(=O)NC(C=C1C2=O)=CC=C1N=CN2CC1=CC=C(Cl)C(Cl)=C1 PXJFUCIUENRSIV-QFIPXVFZSA-N 0.000 claims description 3
• ARJNHXXVYRQJFB-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-4-oxo-n-(2-phenoxyethyl)quinazoline-7-carboxamide Chemical compound C1=C(Cl)C(Cl)=CC=C1CN1C(=O)C2=CC=C(C(=O)NCCOC=3C=CC=CC=3)C=C2N=C1 ARJNHXXVYRQJFB-UHFFFAOYSA-N 0.000 claims description 3
• QNTSLBNOEPZBQR-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-n-(2-hydroxyethyl)-4-oxoquinazoline-6-carboxamide Chemical compound O=C1C2=CC(C(=O)NCCO)=CC=C2N=CN1CC1=CC=C(Cl)C(Cl)=C1 QNTSLBNOEPZBQR-UHFFFAOYSA-N 0.000 claims description 3
• ZTHOZRWAOVJGQG-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-n-(2-hydroxyethyl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C(=O)NCCO)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C(Cl)=C1 ZTHOZRWAOVJGQG-UHFFFAOYSA-N 0.000 claims description 3
• CAZKMGVRHZMRHJ-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-n-(2-methoxyethyl)-4-oxoquinazoline-6-carboxamide Chemical compound O=C1C2=CC(C(=O)NCCOC)=CC=C2N=CN1CC1=CC=C(Cl)C(Cl)=C1 CAZKMGVRHZMRHJ-UHFFFAOYSA-N 0.000 claims description 3
• APLCAWDYNWTGSR-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-n-methyl-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C(=O)NC)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C(Cl)=C1 APLCAWDYNWTGSR-UHFFFAOYSA-N 0.000 claims description 3
• ULZIBTBULAXSCE-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-n-(2-hydroxyethyl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C(=O)NCCO)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C=C1 ULZIBTBULAXSCE-UHFFFAOYSA-N 0.000 claims description 3
• SHJBXYZPUFWDMV-UHFFFAOYSA-N 3-[(4-chlorophenyl)methyl]-n-[(4-fluorophenyl)methyl]-4-oxoquinazoline-7-carboxamide Chemical compound C1=CC(F)=CC=C1CNC(=O)C1=CC=C2C(=O)N(CC=3C=CC(Cl)=CC=3)C=NC2=C1 SHJBXYZPUFWDMV-UHFFFAOYSA-N 0.000 claims description 3
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 3
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
• 201000001320 Atherosclerosis Diseases 0.000 claims description 3
• 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 3
• 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims description 3
• 208000002249 Diabetes Complications Diseases 0.000 claims description 3
• 206010012655 Diabetic complications Diseases 0.000 claims description 3
• 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
• 208000017442 Retinal disease Diseases 0.000 claims description 3
• 206010038923 Retinopathy Diseases 0.000 claims description 3
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
• WFPYLTJBIPXIMX-UHFFFAOYSA-N [2-[[3-[(3,4-difluorophenyl)methyl]-4-oxoquinazolin-6-yl]amino]-2-oxoethyl] acetate Chemical compound O=C1C2=CC(NC(=O)COC(=O)C)=CC=C2N=CN1CC1=CC=C(F)C(F)=C1 WFPYLTJBIPXIMX-UHFFFAOYSA-N 0.000 claims description 3
• UTWFKZFGFBWHOZ-UHFFFAOYSA-N [2-[[3-[(3,4-dimethylphenyl)methyl]-4-oxoquinazolin-6-yl]amino]-2-oxoethyl] acetate Chemical compound O=C1C2=CC(NC(=O)COC(=O)C)=CC=C2N=CN1CC1=CC=C(C)C(C)=C1 UTWFKZFGFBWHOZ-UHFFFAOYSA-N 0.000 claims description 3
• NWFYTGSYBSYCOU-UHFFFAOYSA-N [2-[[3-[(3-chloro-4-fluorophenyl)methyl]-4-oxoquinazolin-6-yl]amino]-2-oxoethyl] acetate Chemical compound O=C1C2=CC(NC(=O)COC(=O)C)=CC=C2N=CN1CC1=CC=C(F)C(Cl)=C1 NWFYTGSYBSYCOU-UHFFFAOYSA-N 0.000 claims description 3
• BNEZMTZHTOUGNZ-UHFFFAOYSA-N [2-[[3-[(4-chlorophenyl)methyl]-4-oxoquinazolin-6-yl]amino]-2-oxoethyl] acetate Chemical compound O=C1C2=CC(NC(=O)COC(=O)C)=CC=C2N=CN1CC1=CC=C(Cl)C=C1 BNEZMTZHTOUGNZ-UHFFFAOYSA-N 0.000 claims description 3
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