BRPI0809551A2 - Derivados de 3-hidroquinazolin-4-ona para uso como inbidores de estearoil coa desaturase - Google Patents

Info

Publication number

BRPI0809551A2

BRPI0809551A2 BRPI0809551-5A BRPI0809551A BRPI0809551A2 BR PI0809551 A2 BRPI0809551 A2 BR PI0809551A2 BR PI0809551 A BRPI0809551 A BR PI0809551A BR PI0809551 A2 BRPI0809551 A2 BR PI0809551A2

Authority

BR

Brazil

Prior art keywords

oxo

methyl

hydroquinazolin

dichlorophenyl

dihydroquinazolin

Prior art date

2007-04-11

Links

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• 239000003112 inhibitor Substances 0.000 title description 15
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 434
• -1 heteroaryl amide Chemical class 0.000 claims description 331
• 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 243
• 150000001875 compounds Chemical class 0.000 claims description 207
• 125000000217 alkyl group Chemical group 0.000 claims description 135
• 125000003118 aryl group Chemical group 0.000 claims description 86
• 125000001072 heteroaryl group Chemical group 0.000 claims description 84
• DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 84
• 125000001424 substituent group Chemical group 0.000 claims description 64
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 52
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 49
• 229910052739 hydrogen Inorganic materials 0.000 claims description 46
• 239000001257 hydrogen Substances 0.000 claims description 45
• 125000000623 heterocyclic group Chemical group 0.000 claims description 43
• 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 43
• 238000000034 method Methods 0.000 claims description 41
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 41
• 125000003342 alkenyl group Chemical group 0.000 claims description 40
• 201000010099 disease Diseases 0.000 claims description 37
• 125000000304 alkynyl group Chemical group 0.000 claims description 32
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 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 group 0.000 claims description 29
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 23
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 21
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 20
• XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 20
• KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 20
• 125000002947 alkylene group Chemical group 0.000 claims description 18
• 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims description 16
• 125000002950 monocyclic group Chemical group 0.000 claims description 16
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
• 208000008589 Obesity Diseases 0.000 claims description 14
• 235000020824 obesity Nutrition 0.000 claims description 14
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
• 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 12
• 206010012601 diabetes mellitus Diseases 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 208000001072 type 2 diabetes mellitus Diseases 0.000 claims description 12
• 125000004423 acyloxy group Chemical group 0.000 claims description 11
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 11
• 125000004442 acylamino group Chemical group 0.000 claims description 10
• 125000004104 aryloxy group Chemical group 0.000 claims description 10
• PUJDIJCNWFYVJX-UHFFFAOYSA-N benzyl carbamate Chemical compound NC(=O)OCC1=CC=CC=C1 PUJDIJCNWFYVJX-UHFFFAOYSA-N 0.000 claims description 10
• 125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
• 208000032928 Dyslipidaemia Diseases 0.000 claims description 9
• 206010028980 Neoplasm Diseases 0.000 claims description 9
• JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 8
• 208000017170 Lipid metabolism disease Diseases 0.000 claims description 8
• 108010087894 Fatty acid desaturases Proteins 0.000 claims description 7
• 241000124008 Mammalia Species 0.000 claims description 7
• 125000002619 bicyclic group Chemical group 0.000 claims description 7
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 6
• 206010022489 Insulin Resistance Diseases 0.000 claims description 6
• 208000032109 Transient ischaemic attack Diseases 0.000 claims description 6
• 201000011510 cancer Diseases 0.000 claims description 6
• 150000002148 esters Chemical class 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
• 125000003107 substituted aryl group Chemical group 0.000 claims description 6
• 201000010875 transient cerebral ischemia Diseases 0.000 claims description 6
• GHLDYRRXZNMZEI-UHFFFAOYSA-N 1,4-dihydroquinazolin-6-ylcarbamic acid Chemical compound N1C=NCC2=CC(NC(=O)O)=CC=C21 GHLDYRRXZNMZEI-UHFFFAOYSA-N 0.000 claims description 5
• 101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims description 5
• 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
• 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 5
• ZPNOFXLIUYCILJ-UHFFFAOYSA-N n-[3-[3-(2-fluorophenoxy)propyl]-4-oxoquinazolin-7-yl]-2-hydroxyacetamide Chemical compound C=1C(NC(=O)CO)=CC=C(C2=O)C=1N=CN2CCCOC1=CC=CC=C1F ZPNOFXLIUYCILJ-UHFFFAOYSA-N 0.000 claims description 5
• 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
• 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 claims description 4
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
• 208000002705 Glucose Intolerance Diseases 0.000 claims description 4
• 206010020772 Hypertension Diseases 0.000 claims description 4
• 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 4
• 125000002618 bicyclic heterocycle group Chemical group 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
• 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
• 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
• NATUMQMREIDLNK-UHFFFAOYSA-N n-[3-[2-(2-chlorophenoxy)ethyl]-4-oxoquinazolin-7-yl]-2-hydroxyacetamide Chemical compound C=1C(NC(=O)CO)=CC=C(C2=O)C=1N=CN2CCOC1=CC=CC=C1Cl NATUMQMREIDLNK-UHFFFAOYSA-N 0.000 claims description 4
• VAJCDSSORKOZGI-UHFFFAOYSA-N n-[3-[2-(3-chlorophenoxy)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCOC1=CC=CC(Cl)=C1 VAJCDSSORKOZGI-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
• VRZJMJLEEDFBAO-UHFFFAOYSA-N n-[3-[5-(2,5-dichlorophenoxy)pentyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCCCOC1=CC(Cl)=CC=C1Cl VRZJMJLEEDFBAO-UHFFFAOYSA-N 0.000 claims description 4
• 201000009104 prediabetes syndrome Diseases 0.000 claims description 4
• 125000003161 (C1-C6) alkylene group Chemical group 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
• 208000002249 Diabetes Complications Diseases 0.000 claims description 3
• 206010012655 Diabetic complications Diseases 0.000 claims description 3
• 208000032382 Ischaemic stroke 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
• 208000006011 Stroke Diseases 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
• HZDYPOREEKDJJF-UHFFFAOYSA-N [2-[[3-[3-(2-fluorophenoxy)propyl]-4-oxoquinazolin-6-yl]amino]-2-oxoethyl] acetate Chemical compound O=C1C2=CC(NC(=O)COC(=O)C)=CC=C2N=CN1CCCOC1=CC=CC=C1F HZDYPOREEKDJJF-UHFFFAOYSA-N 0.000 claims description 3
• QRFSRYLIFCVTFQ-UHFFFAOYSA-N benzyl n-[3-[(3-methoxyphenyl)methyl]-4-oxoquinazolin-6-yl]carbamate Chemical compound COC1=CC=CC(CN2C(C3=CC(NC(=O)OCC=4C=CC=CC=4)=CC=C3N=C2)=O)=C1 QRFSRYLIFCVTFQ-UHFFFAOYSA-N 0.000 claims description 3
• OMLSHDULJUEBDA-UHFFFAOYSA-N benzyl n-[3-[[4-fluoro-3-(trifluoromethyl)phenyl]methyl]-4-oxoquinazolin-6-yl]carbamate Chemical compound C1=C(C(F)(F)F)C(F)=CC=C1CN1C(=O)C2=CC(NC(=O)OCC=3C=CC=CC=3)=CC=C2N=C1 OMLSHDULJUEBDA-UHFFFAOYSA-N 0.000 claims description 3
• 208000026106 cerebrovascular disease Diseases 0.000 claims description 3
• 208000029078 coronary artery disease Diseases 0.000 claims description 3
• 208000019622 heart disease Diseases 0.000 claims description 3
• 230000002401 inhibitory effect Effects 0.000 claims description 3
• 230000000302 ischemic effect Effects 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• GCVCPWKQNCZKDL-UHFFFAOYSA-N n-[3-[2-(4-chlorophenoxy)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCOC1=CC=C(Cl)C=C1 GCVCPWKQNCZKDL-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 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 3
• 239000000651 prodrug Substances 0.000 claims description 3
• 229940002612 prodrug Drugs 0.000 claims description 3
• 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
• 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 2
• 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 2
• 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 2
• PJMUWESHQUJWJQ-UHFFFAOYSA-N [2-[[3-[1-(3,4-dichlorophenyl)ethyl]-4-oxoquinazolin-7-yl]amino]-2-oxoethyl] acetate Chemical compound C1=NC2=CC(NC(=O)COC(C)=O)=CC=C2C(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 PJMUWESHQUJWJQ-UHFFFAOYSA-N 0.000 claims description 2
• GXLVMWAYEGFSIW-UHFFFAOYSA-N [2-[[3-[[4-chloro-3-(trifluoromethyl)phenyl]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(C(F)(F)F)=C1 GXLVMWAYEGFSIW-UHFFFAOYSA-N 0.000 claims description 2
• ABTKFZJCNLNRCZ-UHFFFAOYSA-N [2-[[3-[[4-fluoro-3-(trifluoromethyl)phenyl]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(C(F)(F)F)=C1 ABTKFZJCNLNRCZ-UHFFFAOYSA-N 0.000 claims description 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
• PLLMZYHSSGPIPW-UHFFFAOYSA-N n-[3-[(3,4-difluorophenyl)methyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CC1=CC=C(F)C(F)=C1 PLLMZYHSSGPIPW-UHFFFAOYSA-N 0.000 claims description 2
• VVTGCFSFGWYQTR-UHFFFAOYSA-N n-[3-[(4-chlorophenyl)methyl]-4-oxoquinazolin-6-yl]-2-phenoxyacetamide Chemical compound C1=CC(Cl)=CC=C1CN1C(=O)C2=CC(NC(=O)COC=3C=CC=CC=3)=CC=C2N=C1 VVTGCFSFGWYQTR-UHFFFAOYSA-N 0.000 claims description 2
• 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 2
• 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 2
• KJKRJIJOIPCXSK-UHFFFAOYSA-N n-[3-[3-[(2,5-dichlorophenyl)sulfonylamino]propyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCNS(=O)(=O)C1=CC(Cl)=CC=C1Cl KJKRJIJOIPCXSK-UHFFFAOYSA-N 0.000 claims description 2
• MONRWRVYLOHUFA-UHFFFAOYSA-N pentylurea Chemical compound CCCCCNC(N)=O MONRWRVYLOHUFA-UHFFFAOYSA-N 0.000 claims description 2
• 125000001475 halogen functional group Chemical group 0.000 claims 12
• 125000004043 oxo group Chemical group O=* 0.000 claims 2
• 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
• QHBZNQNBFUIDQR-UHFFFAOYSA-N 2-(2-chlorophenoxy)propanamide Chemical compound NC(=O)C(C)OC1=CC=CC=C1Cl QHBZNQNBFUIDQR-UHFFFAOYSA-N 0.000 claims 1
• 102000016553 Stearoyl-CoA Desaturase Human genes 0.000 claims 1
• CKANCWVLJIOYEH-UHFFFAOYSA-N [2-[[3-[1-(3,4-dichlorophenyl)propyl]-4-oxoquinazolin-6-yl]amino]-2-oxoethyl] acetate Chemical compound C1=NC2=CC=C(NC(=O)COC(C)=O)C=C2C(=O)N1C(CC)C1=CC=C(Cl)C(Cl)=C1 CKANCWVLJIOYEH-UHFFFAOYSA-N 0.000 claims 1
• 125000005164 aryl thioalkyl group Chemical group 0.000 claims 1
• CTUJXHSXIAJYII-UHFFFAOYSA-N benzyl n-[3-(naphthalen-2-ylmethyl)-4-oxoquinazolin-6-yl]carbamate Chemical compound C=1C=C2N=CN(CC=3C=C4C=CC=CC4=CC=3)C(=O)C2=CC=1NC(=O)OCC1=CC=CC=C1 CTUJXHSXIAJYII-UHFFFAOYSA-N 0.000 claims 1
• BMFOQJHODDTXBF-UHFFFAOYSA-N benzyl n-[3-[(3,4-dichlorophenyl)methyl]-2-methyl-4-oxoquinazolin-7-yl]carbamate Chemical compound C=1C=C2C(=O)N(CC=3C=C(Cl)C(Cl)=CC=3)C(C)=NC2=CC=1NC(=O)OCC1=CC=CC=C1 BMFOQJHODDTXBF-UHFFFAOYSA-N 0.000 claims 1
• HFTPWWWEDCJNRU-UHFFFAOYSA-N benzyl n-[3-[(3,4-dimethylphenyl)methyl]-4-oxoquinazolin-6-yl]carbamate Chemical compound C1=C(C)C(C)=CC=C1CN1C(=O)C2=CC(NC(=O)OCC=3C=CC=CC=3)=CC=C2N=C1 HFTPWWWEDCJNRU-UHFFFAOYSA-N 0.000 claims 1
• SXHQLLQDYKSKDN-UHFFFAOYSA-N benzyl n-[3-[1-(3,4-dichlorophenyl)ethyl]-4-oxoquinazolin-7-yl]carbamate Chemical compound C1=NC2=CC(NC(=O)OCC=3C=CC=CC=3)=CC=C2C(=O)N1C(C)C1=CC=C(Cl)C(Cl)=C1 SXHQLLQDYKSKDN-UHFFFAOYSA-N 0.000 claims 1
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