CA2740389A1 - Derives de 3-hydroquinazoline-4-one utilises comme inhibiteurs de stearyl-acp desaturase - Google Patents

Derives de 3-hydroquinazoline-4-one utilises comme inhibiteurs de stearyl-acp desaturase Download PDF

Info

Publication number: CA2740389A1
Authority: CA; Canada
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.): Abandoned

Application number

CA2740389A

Other languages

English (en)

Inventor

Dmitry Koltun

Eric Parkhill

Melanie Boze

Jeff Zablocki

Natalya Vasilevich

Elena Mayboroda

Andrey Glushkov

Andrew Cole

Jeffrey Chisholm

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Gilead Sciences Inc

Ligand Pharmaceuticals Inc

Original Assignee

Gilead Sciences Inc

Ligand Pharmaceuticals Inc

Priority date (The priority date 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 date listed.)

2008-10-15

Filing date

2008-10-15

Publication date

2010-05-20

2008-10-15 Application filed by Gilead Sciences Inc, Ligand Pharmaceuticals Inc filed Critical Gilead Sciences Inc

2010-05-20 Publication of CA2740389A1 publication Critical patent/CA2740389A1/fr

Status Abandoned legal-status Critical Current

Links

108010087894 Fatty acid desaturases Proteins 0.000 title claims abstract description 67
102000016553 Stearoyl-CoA Desaturase Human genes 0.000 title claims abstract description 66
239000003112 inhibitor Substances 0.000 title abstract description 13
150000001875 compounds Chemical class 0.000 claims abstract description 295
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 56
201000010099 disease Diseases 0.000 claims abstract description 41
208000008589 Obesity Diseases 0.000 claims abstract description 15
235000020824 obesity Nutrition 0.000 claims abstract description 15
206010012601 diabetes mellitus Diseases 0.000 claims abstract description 13
206010028980 Neoplasm Diseases 0.000 claims abstract description 10
201000011510 cancer Diseases 0.000 claims abstract description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 410
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 243
DLFVBJFMPXGRIB-UHFFFAOYSA-N thioacetamide Natural products CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 231
-1 heteroaryl amide Chemical class 0.000 claims description 202
125000000217 alkyl group Chemical group 0.000 claims description 125
150000003857 carboxamides Chemical class 0.000 claims description 114
125000003118 aryl group Chemical group 0.000 claims description 86
125000001072 heteroaryl group Chemical group 0.000 claims description 83
125000001424 substituent group Chemical group 0.000 claims description 64
238000000034 method Methods 0.000 claims description 57
229910052739 hydrogen Inorganic materials 0.000 claims description 51
125000000623 heterocyclic group Chemical group 0.000 claims description 46
239000001257 hydrogen Substances 0.000 claims description 45
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
125000003342 alkenyl group Chemical group 0.000 claims description 42
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 38
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 36
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 34
125000003545 alkoxy group Chemical group 0.000 claims description 31
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 31
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 29
150000002431 hydrogen Chemical group 0.000 claims description 29
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 27
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 24
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 24
125000002947 alkylene group Chemical group 0.000 claims description 22
125000000753 cycloalkyl group Chemical group 0.000 claims description 21
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 19
125000002950 monocyclic 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
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical group O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 14
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 14
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 13
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 12
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000000547 substituted alkyl group Chemical group 0.000 claims description 12
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
125000005553 heteroaryloxy group Chemical group 0.000 claims description 10
239000008194 pharmaceutical composition Substances 0.000 claims description 10
208000032928 Dyslipidaemia Diseases 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
241000124008 Mammalia Species 0.000 claims description 7
125000003107 substituted aryl group Chemical group 0.000 claims description 7
101100240528 Caenorhabditis elegans nhr-23 gene Proteins 0.000 claims description 6
206010022489 Insulin Resistance Diseases 0.000 claims description 6
208000032109 Transient ischaemic attack Diseases 0.000 claims description 6
230000002401 inhibitory effect Effects 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-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 6
201000010875 transient cerebral ischemia Diseases 0.000 claims description 6
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
125000002619 bicyclic group Chemical group 0.000 claims description 5
125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 5
230000003247 decreasing effect Effects 0.000 claims description 5
150000002148 esters Chemical class 0.000 claims description 5
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 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
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
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 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
206010020772 Hypertension Diseases 0.000 claims description 4
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 4
125000004663 dialkyl amino group Chemical group 0.000 claims description 4
239000008103 glucose Substances 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
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 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
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
QKYJBOLLEGURPD-UHFFFAOYSA-N n-[3-[2-(2-chlorophenoxy)ethyl]-4-oxoquinazolin-6-yl]-2-hydroxyacetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCOC1=CC=CC=C1Cl QKYJBOLLEGURPD-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
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 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
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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
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 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
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 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
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
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
QDKWLJJOYIFEBS-UHFFFAOYSA-N 1-fluoro-4-$l^{1}-oxidanylbenzene Chemical group [O]C1=CC=C(F)C=C1 QDKWLJJOYIFEBS-UHFFFAOYSA-N 0.000 claims description 3
MVEBVZSYYNMUPL-UHFFFAOYSA-N 2,5-dichloro-n-[2-[6-[(2-hydroxyacetyl)amino]-4-oxoquinazolin-3-yl]ethyl]benzamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCNC(=O)C1=CC(Cl)=CC=C1Cl MVEBVZSYYNMUPL-UHFFFAOYSA-N 0.000 claims description 3
ZFQYHUXDDOLXRV-UHFFFAOYSA-N 2-[[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]amino]-2-oxoacetic acid Chemical compound O=C1C2=CC(NC(=O)C(=O)O)=CC=C2N=CN1CC1=CC=C(Cl)C(Cl)=C1 ZFQYHUXDDOLXRV-UHFFFAOYSA-N 0.000 claims description 3
KEBVMJAQZXAOEQ-UHFFFAOYSA-N 2-amino-n-[3-[(3,4-dichlorophenyl)methyl]-4-oxoquinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)CN)=CC=C2N=CN1CC1=CC=C(Cl)C(Cl)=C1 KEBVMJAQZXAOEQ-UHFFFAOYSA-N 0.000 claims description 3
BDYFZXYBWKZOPY-UHFFFAOYSA-N 2-hydroxy-n-[3-(naphthalen-2-ylmethyl)-4-oxoquinazolin-6-yl]acetamide Chemical compound C1=CC=CC2=CC(CN3C=NC4=CC=C(C=C4C3=O)NC(=O)CO)=CC=C21 BDYFZXYBWKZOPY-UHFFFAOYSA-N 0.000 claims description 3
HNJZSHJKTIKCMX-UHFFFAOYSA-N 2-hydroxy-n-[3-(naphthalen-2-ylmethyl)-4-oxoquinazolin-7-yl]acetamide Chemical compound C1=CC=CC2=CC(CN3C=NC=4C(C3=O)=CC=C(C=4)NC(=O)CO)=CC=C21 HNJZSHJKTIKCMX-UHFFFAOYSA-N 0.000 claims description 3
ZWZRBCCUBALXBX-UHFFFAOYSA-N 2-hydroxy-n-[3-[2-hydroxy-3-(2-methylphenoxy)propyl]-4-oxoquinazolin-6-yl]acetamide Chemical compound CC1=CC=CC=C1OCC(O)CN1C(=O)C2=CC(NC(=O)CO)=CC=C2N=C1 ZWZRBCCUBALXBX-UHFFFAOYSA-N 0.000 claims description 3
KURQHGQZLPQQKS-UHFFFAOYSA-N 2-hydroxy-n-[3-[3-(2-methylphenoxy)propyl]-4-oxoquinazolin-6-yl]acetamide Chemical compound CC1=CC=CC=C1OCCCN1C(=O)C2=CC(NC(=O)CO)=CC=C2N=C1 KURQHGQZLPQQKS-UHFFFAOYSA-N 0.000 claims description 3
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XXYOJKVAQJJWBH-UHFFFAOYSA-N 2-hydroxy-n-[4-oxo-3-(3-phenoxypropyl)quinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC=CC=C1 XXYOJKVAQJJWBH-UHFFFAOYSA-N 0.000 claims description 3
INSJUSFBALZMRM-UHFFFAOYSA-N 2-hydroxy-n-[4-oxo-3-(3-phenylpropyl)quinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCC1=CC=CC=C1 INSJUSFBALZMRM-UHFFFAOYSA-N 0.000 claims description 3
CJWNFVRHXXKSSX-UHFFFAOYSA-N 2-hydroxy-n-[4-oxo-3-[3-[2-(trifluoromethyl)phenoxy]propyl]quinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCOC1=CC=CC=C1C(F)(F)F CJWNFVRHXXKSSX-UHFFFAOYSA-N 0.000 claims description 3
QSNDZZLNZWKAHB-UHFFFAOYSA-N 2-hydroxy-n-[4-oxo-3-[3-[[2-(trifluoromethyl)phenyl]sulfonylamino]propyl]quinazolin-6-yl]acetamide Chemical compound O=C1C2=CC(NC(=O)CO)=CC=C2N=CN1CCCNS(=O)(=O)C1=CC=CC=C1C(F)(F)F QSNDZZLNZWKAHB-UHFFFAOYSA-N 0.000 claims description 3
125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims description 3
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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
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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
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208000006011 Stroke Diseases 0.000 claims description 3
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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
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
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 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
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ICZJIWGFLVKEOG-UHFFFAOYSA-N [2-oxo-2-[[4-oxo-3-(3-phenylpropyl)quinazolin-6-yl]amino]ethyl] acetate Chemical compound O=C1C2=CC(NC(=O)COC(=O)C)=CC=C2N=CN1CCCC1=CC=CC=C1 ICZJIWGFLVKEOG-UHFFFAOYSA-N 0.000 claims description 3
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LLUTVUDHDVDAOY-UHFFFAOYSA-N benzyl n-[3-[2-(2-chlorophenoxy)ethyl]-4-oxoquinazolin-6-yl]carbamate Chemical compound ClC1=CC=CC=C1OCCN1C(=O)C2=CC(NC(=O)OCC=3C=CC=CC=3)=CC=C2N=C1 LLUTVUDHDVDAOY-UHFFFAOYSA-N 0.000 claims description 3
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FUMDPIDLTCAXBG-UHFFFAOYSA-N benzyl n-[3-[3-(2,5-dichlorophenoxy)propyl]-4-oxoquinazolin-7-yl]carbamate Chemical compound ClC1=CC=C(Cl)C(OCCCN2C(C3=CC=C(NC(=O)OCC=4C=CC=CC=4)C=C3N=C2)=O)=C1 FUMDPIDLTCAXBG-UHFFFAOYSA-N 0.000 claims description 3
GPGOYELTXDBALG-UHFFFAOYSA-N benzyl n-[3-[3-(2-chlorophenoxy)propyl]-4-oxoquinazolin-6-yl]carbamate Chemical compound ClC1=CC=CC=C1OCCCN1C(=O)C2=CC(NC(=O)OCC=3C=CC=CC=3)=CC=C2N=C1 GPGOYELTXDBALG-UHFFFAOYSA-N 0.000 claims description 3
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208000029078 coronary artery disease Diseases 0.000 claims description 3
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QJXVYKCSFVWRJO-UHFFFAOYSA-N 3-[(3,4-dichlorophenyl)methyl]-n-(3-hydroxypropyl)-4-oxoquinazoline-7-carboxamide Chemical compound C=1C(C(=O)NCCCO)=CC=C(C2=O)C=1N=CN2CC1=CC=C(Cl)C(Cl)=C1 QJXVYKCSFVWRJO-UHFFFAOYSA-N 0.000 claims description 2
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239000003765 sweetening agent Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
230000009897 systematic effect Effects 0.000 description 1
229940066769 systemic antihistamines substituted alkylamines Drugs 0.000 description 1
238000012385 systemic delivery Methods 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
229960004559 theobromine Drugs 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000037317 transdermal delivery Effects 0.000 description 1
238000011830 transgenic mouse model Methods 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
125000005259 triarylamine group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
229960000281 trometamol Drugs 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
230000003612 virological effect Effects 0.000 description 1
239000003039 volatile agent Substances 0.000 description 1
238000005406 washing Methods 0.000 description 1
230000004584 weight gain Effects 0.000 description 1
235000019786 weight gain Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- 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
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Diabetes (AREA)
Hematology (AREA)
Obesity (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Endocrinology (AREA)
Child & Adolescent Psychology (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA2740389A 2008-10-15 2008-10-15 Derives de 3-hydroquinazoline-4-one utilises comme inhibiteurs de stearyl-acp desaturase Abandoned CA2740389A1 (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
PCT/US2008/079975 WO2010056230A1 (fr)	2008-10-15	2008-10-15	Dérivés de 3-hydroquinazoline-4-one utilisés comme inhibiteurs de stéaryl-acp désaturase

Publications (1)

Publication Number	Publication Date
CA2740389A1 true CA2740389A1 (fr)	2010-05-20

Family

ID=40749129

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA2740389A Abandoned CA2740389A1 (fr)	2008-10-15	2008-10-15	Derives de 3-hydroquinazoline-4-one utilises comme inhibiteurs de stearyl-acp desaturase

Country Status (4)

Country	Link
EP (1)	EP2350029A1 (fr)
JP (1)	JP2012505881A (fr)
CA (1)	CA2740389A1 (fr)
WO (1)	WO2010056230A1 (fr)

Families Citing this family (16)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US8987257B2 (en)	2011-01-31	2015-03-24	Novartis Ag	Heterocyclic derivatives
KR20140090218A (ko)	2011-10-28	2014-07-16	노파르티스 아게	신규 퓨린 유도체 및 질환의 치료에서의 그의 용도
TW201348213A (zh)	2012-04-24	2013-12-01	Chugai Pharmaceutical Co Ltd	喹唑啉二酮衍生物
WO2013161851A1 (fr)	2012-04-24	2013-10-31	中外製薬株式会社	Dérivé de benzamide
CA2895782C (fr) *	2012-12-21	2017-08-22	Gilead Calistoga Llc	Pyrimidine aminoalkyl-quinazolones substituees en tant qu'inhibiteurs de phosphatidylinositol 3-kinase
EP3061749B1 (fr) *	2013-10-23	2019-02-27	Chugai Seiyaku Kabushiki Kaisha	Dérivé de quinazolinone et d'isoquinolinone
SG11201708622UA (en)	2015-02-02	2017-11-29	Forma Therapeutics Inc	3-aryl-4-amido-bicyclic [4,5,0] hydroxamic acids as hdac inhibitors
US10183934B2 (en)	2015-02-02	2019-01-22	Forma Therapeutics, Inc.	Bicyclic [4,6,0] hydroxamic acids as HDAC inhibitors
WO2017218950A1 (fr)	2016-06-17	2017-12-21	Forma Therapeutics, Inc.	Indanes d'acide hydroxamique 2-spiro-5 et 6 utilisés en tant qu'inhibiteurs de hdac
CN117777121A (zh)	2016-10-24	2024-03-29	詹森药业有限公司	化合物及其用途
EA201991650A1 (ru)	2017-01-06	2020-01-20	Юманити Терапьютикс, Инк.	Способы лечения неврологических расстройств
WO2019084157A1 (fr)	2017-10-24	2019-05-02	Yumanity Therapeutics, Inc.	Composés et utilisations de ces composés
AU2019238326B2 (en)	2018-03-23	2025-03-06	Janssen Pharmaceutica Nv	Compounds and uses thereof
JP7742775B2 (ja)	2019-01-24	2025-09-22	ヤンセンファーマシューティカエヌ．ベー．	化合物及びその使用
EA202192047A1 (ru)	2019-11-13	2021-12-08	Юманити Терапьютикс, Инк.	Соединения и их применение
IN202011027502A (fr) *	2020-06-29	2021-12-31	Council Scient Ind Res

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2020073A1 (fr) *	1989-07-03	1991-01-04	Eric E. Allen	Quinazolinones substitues comme antagonistes de l'angiotensine ii
US6638937B2 (en) *	1998-07-06	2003-10-28	Bristol-Myers Squibb Co.	Biphenyl sulfonamides as dual angiotensin endothelin receptor antagonists
US6894057B2 (en) *	2002-03-08	2005-05-17	Warner-Lambert Company	Oxo-azabicyclic compounds
US20040142950A1 (en) *	2003-01-17	2004-07-22	Bunker Amy Mae	Amide and ester matrix metalloproteinase inhibitors
JP4958785B2 (ja) *	2004-09-20	2012-06-20	ゼノン・ファーマシューティカルズ・インコーポレイテッド	複素環誘導体およびステアロイル−ＣｏＡデサチュラーゼインヒビターとしてのそれらの使用
EP2650011A1 (fr) *	2004-12-24	2013-10-16	Spinifex Pharmaceuticals Pty Ltd	Procédé de traitement de la prophylaxie
WO2006125180A1 (fr) *	2005-05-19	2006-11-23	Xenon Pharmaceuticals Inc.	Derives de piperazine: utilisation comme agents therapeutiques

2008
- 2008-10-15 CA CA2740389A patent/CA2740389A1/fr not_active Abandoned
- 2008-10-15 JP JP2011532053A patent/JP2012505881A/ja not_active Withdrawn
- 2008-10-15 EP EP08825468A patent/EP2350029A1/fr not_active Withdrawn
- 2008-10-15 WO PCT/US2008/079975 patent/WO2010056230A1/fr not_active Ceased

Also Published As

Publication number	Publication date
EP2350029A1 (fr)	2011-08-03
WO2010056230A1 (fr)	2010-05-20
JP2012505881A (ja)	2012-03-08

Publication	Publication Date	Title
CA2740389A1 (fr)	2010-05-20	Derives de 3-hydroquinazoline-4-one utilises comme inhibiteurs de stearyl-acp desaturase
US20080255161A1 (en)	2008-10-16	3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS
US8148376B2 (en)	2012-04-03	3, 4-dihydroquinoxalin-2(1H)-ones for use as stearoyl CoA desaturase inhibitors
US7893066B2 (en)	2011-02-22	Pyridol[2,3-B]pyrazinones for use as stearoyl CoA desaturase inhibitors
US20100267748A1 (en)	2010-10-21	HETEROCYCLIC COMPOUNDS USEFUL AS STEAROYL CoA DESATURASE INHIBITORS
US20090105283A1 (en)	2009-04-23	3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS
US8088792B2 (en)	2012-01-03	Triazolopyridinone derivatives for use as stearoyl CoA desaturase inhibitors
CA2681560A1 (fr)	2008-10-16	Derives de pteridinone destines a etre utilises comme des inhibiteurs de stearoyl-coa desaturase
US20090253704A1 (en)	2009-10-08	PYRROLOTRIAZINONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS
WO2009126527A1 (fr)	2009-10-15	Dérivés de 2h-benzo[b][1,4]oxazin-3(4h)-one à utiliser comme inhibiteurs de la stéaroyl-coa désaturase
WO2010045374A1 (fr)	2010-04-22	Dérivés de 3-hydroquinazoline-4-1 à utiliser comme inhibiteurs de la stéaroyl-coa-désaturase
JP2011516546A (ja)	2011-05-26	ステアロイル−ＣｏＡデサチュラーゼのインヒビターとして使用するための二環式窒素含有複素環化合物

Legal Events

Date	Code	Title	Description
2013-12-10	FZDE	Dead	Effective date: 20131015