JP2011526594A5 - - Google Patents
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- Publication number
- JP2011526594A5 JP2011526594A5 JP2011515438A JP2011515438A JP2011526594A5 JP 2011526594 A5 JP2011526594 A5 JP 2011526594A5 JP 2011515438 A JP2011515438 A JP 2011515438A JP 2011515438 A JP2011515438 A JP 2011515438A JP 2011526594 A5 JP2011526594 A5 JP 2011526594A5
- Authority
- JP
- Japan
- Prior art keywords
- dihydroxy
- isoxazole
- phenyl
- carboxylic acid
- acid ethylamide
- Prior art date
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims description 20
- -1 cyclohexanecarbonyl-amino Chemical group 0.000 claims description 13
- FPGYLUIGKHTKQV-UHFFFAOYSA-N chembl1940917 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C=1SC=CC=1C FPGYLUIGKHTKQV-UHFFFAOYSA-N 0.000 claims description 4
- NRDHRUUAIBGJLZ-UHFFFAOYSA-N chembl1940919 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C(C)(C)C NRDHRUUAIBGJLZ-UHFFFAOYSA-N 0.000 claims description 4
- ZAHKLNMQDKMBCL-UHFFFAOYSA-N chembl1940921 Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NC=1C(C(=O)NCC)=NOC=1C1=CC(Cl)=C(O)C=C1O ZAHKLNMQDKMBCL-UHFFFAOYSA-N 0.000 claims description 4
- CLGCYNQGBOFRIU-UHFFFAOYSA-N chembl1940924 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)CCN1CCOCC1 CLGCYNQGBOFRIU-UHFFFAOYSA-N 0.000 claims description 4
- NBPOVHXUKYASOM-UHFFFAOYSA-N chembl1940926 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C(C)(C)C NBPOVHXUKYASOM-UHFFFAOYSA-N 0.000 claims description 4
- UOWFKIGORLIVGO-UHFFFAOYSA-N chembl1941063 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C=1SC=CC=1C UOWFKIGORLIVGO-UHFFFAOYSA-N 0.000 claims description 4
- TZYANCKBMDGFOB-UHFFFAOYSA-N 4-[(4-aminocyclohexanecarbonyl)amino]-5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1CCC(N)CC1 TZYANCKBMDGFOB-UHFFFAOYSA-N 0.000 claims description 3
- HAMKBSLGCXVDLO-UHFFFAOYSA-N 4-[[4-(aminomethyl)cyclohexanecarbonyl]amino]-5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1CCC(CN)CC1 HAMKBSLGCXVDLO-UHFFFAOYSA-N 0.000 claims description 3
- JFZARAAVWNISTG-UHFFFAOYSA-N 4-amino-5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1N JFZARAAVWNISTG-UHFFFAOYSA-N 0.000 claims description 3
- MUZNLZVOKJVBPC-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-4-[(4-methoxycyclohexanecarbonyl)amino]-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1CCC(OC)CC1 MUZNLZVOKJVBPC-UHFFFAOYSA-N 0.000 claims description 3
- SLBKTQWZSYURPV-UHFFFAOYSA-N 5-(5-chloro-2,4-dihydroxyphenyl)-N-ethyl-4-[[3-(hydroxymethyl)-1,2-oxazol-5-yl]methylamino]-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NCC1=CC(CO)=NO1 SLBKTQWZSYURPV-UHFFFAOYSA-N 0.000 claims description 3
- IYYXMUJIVUJPBD-UHFFFAOYSA-N N-[5-(5-chloro-2,4-dihydroxyphenyl)-3-(4-methylpiperazine-1-carbonyl)-1,2-oxazol-4-yl]-4-methoxybenzamide Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=C(C=2C(=CC(O)=C(Cl)C=2)O)ON=C1C(=O)N1CCN(C)CC1 IYYXMUJIVUJPBD-UHFFFAOYSA-N 0.000 claims description 3
- UWKWOTCLGZNOKY-UHFFFAOYSA-N chembl1940913 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C1=CC=C(Br)C=C1 UWKWOTCLGZNOKY-UHFFFAOYSA-N 0.000 claims description 3
- QBSZQEVMVGSPFZ-UHFFFAOYSA-N chembl1940914 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C1=CC=C(OC)C=C1 QBSZQEVMVGSPFZ-UHFFFAOYSA-N 0.000 claims description 3
- MQYOAYAUVZORFG-UHFFFAOYSA-N chembl1940915 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C1=CC=C(OC)C(OC)=C1 MQYOAYAUVZORFG-UHFFFAOYSA-N 0.000 claims description 3
- WASBTDRFRYYYRL-UHFFFAOYSA-N chembl1940916 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C1=CC(OC)=C(OC)C(OC)=C1 WASBTDRFRYYYRL-UHFFFAOYSA-N 0.000 claims description 3
- WEAJPAPZLYQPRZ-UHFFFAOYSA-N chembl1940918 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(C)=O WEAJPAPZLYQPRZ-UHFFFAOYSA-N 0.000 claims description 3
- VIEGTSLOUDDFCN-UHFFFAOYSA-N chembl1940920 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC(=O)C=C VIEGTSLOUDDFCN-UHFFFAOYSA-N 0.000 claims description 3
- QCKQEYDGLASTLI-UHFFFAOYSA-N chembl1940923 Chemical compound C1=CC(OC)=CC=C1C(=O)NC1=C(C=2C(=CC(O)=C(Cl)C=2)O)ON=C1C(=O)N1CC(F)(F)C1 QCKQEYDGLASTLI-UHFFFAOYSA-N 0.000 claims description 3
- KBNLPGKGXMPKID-UHFFFAOYSA-N chembl1940925 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(C)=O KBNLPGKGXMPKID-UHFFFAOYSA-N 0.000 claims description 3
- NNPUKYHSBUTURK-IYARVYRRSA-N chembl1940928 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C(=O)NC1=C(C=2C(=CC(O)=C(C(C)C)C=2)O)ON=C1C(=O)NCC NNPUKYHSBUTURK-IYARVYRRSA-N 0.000 claims description 3
- ZSKNESXDGZRCNG-UHFFFAOYSA-N chembl1940929 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1CCC(C(F)(F)F)CC1 ZSKNESXDGZRCNG-UHFFFAOYSA-N 0.000 claims description 3
- WURSGCMBSCSYOG-UHFFFAOYSA-N chembl1941050 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)CCN1CCOCC1 WURSGCMBSCSYOG-UHFFFAOYSA-N 0.000 claims description 3
- BYAGRVGRUDLLDR-UHFFFAOYSA-N chembl1941052 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1=CC=C(OC)C=C1 BYAGRVGRUDLLDR-UHFFFAOYSA-N 0.000 claims description 3
- OOHHYUCVSBGXHT-UHFFFAOYSA-N chembl1941082 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC1CCCCC1 OOHHYUCVSBGXHT-UHFFFAOYSA-N 0.000 claims description 3
- FPBCOFYFVBCSPA-UHFFFAOYSA-N chembl1941083 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NC1CCN(C)CC1 FPBCOFYFVBCSPA-UHFFFAOYSA-N 0.000 claims description 3
- PYLUIBKRCIOZQM-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-4-[methyl-(4-morpholin-4-ylbenzoyl)amino]-1,2-oxazole-3-carboxamide hydrochloride Chemical compound Cl.C(C)NC(=O)C1=NOC(=C1N(C(C1=CC=C(C=C1)N1CCOCC1)=O)C)C1=C(C=C(C(=C1)C(C)C)O)O PYLUIBKRCIOZQM-UHFFFAOYSA-N 0.000 claims description 2
- VJPGZONQVSCVJS-UHFFFAOYSA-N CCNC(=O)C1=NOC=C1C1=CC(C(C)C)=C(O)C=C1O Chemical compound CCNC(=O)C1=NOC=C1C1=CC(C(C)C)=C(O)C=C1O VJPGZONQVSCVJS-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- ZHOPMAPGOGTAOR-UHFFFAOYSA-N chembl1940931 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1CCC(C(C)(C)C)CC1 ZHOPMAPGOGTAOR-UHFFFAOYSA-N 0.000 claims description 2
- UDIGLEOGQYIBNW-UHFFFAOYSA-N chembl1941080 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NCC=1SC=CC=1C UDIGLEOGQYIBNW-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 16
- 238000000034 method Methods 0.000 claims 7
- 230000015572 biosynthetic process Effects 0.000 claims 6
- 238000003786 synthesis reaction Methods 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 5
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 5
- 125000003342 alkenyl group Chemical group 0.000 claims 4
- 125000003118 aryl group Chemical group 0.000 claims 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims 4
- 125000001188 haloalkyl group Chemical group 0.000 claims 4
- 125000005843 halogen group Chemical group 0.000 claims 4
- 125000001072 heteroaryl group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 206010028980 Neoplasm Diseases 0.000 claims 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 3
- 201000011510 cancer Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- 229910052739 hydrogen Inorganic materials 0.000 claims 3
- 239000001257 hydrogen Substances 0.000 claims 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 3
- 208000023275 Autoimmune disease Diseases 0.000 claims 2
- 201000006474 Brain Ischemia Diseases 0.000 claims 2
- 206010008120 Cerebral ischaemia Diseases 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 208000030852 Parasitic disease Diseases 0.000 claims 2
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 206010008118 cerebral infarction Diseases 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000004770 neurodegeneration Effects 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229910052760 oxygen Inorganic materials 0.000 claims 2
- 230000001575 pathological effect Effects 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 229910052717 sulfur Inorganic materials 0.000 claims 2
- UXYRXGFUANQKTA-UHFFFAOYSA-N 1,2-oxazole-3-carboxylic acid Chemical compound OC(=O)C=1C=CON=1 UXYRXGFUANQKTA-UHFFFAOYSA-N 0.000 claims 1
- 208000024827 Alzheimer disease Diseases 0.000 claims 1
- 102000014461 Ataxins Human genes 0.000 claims 1
- 108010078286 Ataxins Proteins 0.000 claims 1
- 206010008025 Cerebellar ataxia Diseases 0.000 claims 1
- 206010012289 Dementia Diseases 0.000 claims 1
- 102100034051 Heat shock protein HSP 90-alpha Human genes 0.000 claims 1
- 101001016865 Homo sapiens Heat shock protein HSP 90-alpha Proteins 0.000 claims 1
- 208000023105 Huntington disease Diseases 0.000 claims 1
- 208000012902 Nervous system disease Diseases 0.000 claims 1
- 208000009182 Parasitemia Diseases 0.000 claims 1
- 208000018737 Parkinson disease Diseases 0.000 claims 1
- 208000009415 Spinocerebellar Ataxias Diseases 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001263 acyl chlorides Chemical class 0.000 claims 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims 1
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
- 125000004103 aminoalkyl group Chemical group 0.000 claims 1
- 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims 1
- 201000004562 autosomal dominant cerebellar ataxia Diseases 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 210000000481 breast Anatomy 0.000 claims 1
- SURLAOAQRDUOFO-UHFFFAOYSA-N chembl1941081 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NCC1=CC=C(OC)C=C1 SURLAOAQRDUOFO-UHFFFAOYSA-N 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- 230000000694 effects Effects 0.000 claims 1
- 208000024519 eye neoplasm Diseases 0.000 claims 1
- 230000036541 health Effects 0.000 claims 1
- 125000005842 heteroatom Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 claims 1
- 210000004558 lewy body Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000004792 malaria Diseases 0.000 claims 1
- 210000001767 medulla oblongata Anatomy 0.000 claims 1
- 208000037819 metastatic cancer Diseases 0.000 claims 1
- 208000011575 metastatic malignant neoplasm Diseases 0.000 claims 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 201000000585 muscular atrophy Diseases 0.000 claims 1
- 210000003739 neck Anatomy 0.000 claims 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims 1
- 201000008106 ocular cancer Diseases 0.000 claims 1
- 210000000496 pancreas Anatomy 0.000 claims 1
- 210000004303 peritoneum Anatomy 0.000 claims 1
- 210000004224 pleura Anatomy 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 210000002307 prostate Anatomy 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 1
- 210000003932 urinary bladder Anatomy 0.000 claims 1
- 210000004291 uterus Anatomy 0.000 claims 1
- JLLYLQLDYORLBB-UHFFFAOYSA-N 5-bromo-n-methylthiophene-2-sulfonamide Chemical compound CNS(=O)(=O)C1=CC=C(Br)S1 JLLYLQLDYORLBB-UHFFFAOYSA-N 0.000 description 2
- LHNUEBNTPQPHKG-UHFFFAOYSA-N methyl 5-[[[5-(5-chloro-2,4-dihydroxyphenyl)-3-(ethylcarbamoyl)-1,2-oxazol-4-yl]amino]methyl]-1,2-oxazole-3-carboxylate Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(Cl)C=2)O)=C1NCC1=CC(C(=O)OC)=NO1 LHNUEBNTPQPHKG-UHFFFAOYSA-N 0.000 description 2
- GHTDODSYDCPOCW-UHFFFAOYSA-N 1h-indole-6-carboxylic acid Chemical compound OC(=O)C1=CC=C2C=CNC2=C1 GHTDODSYDCPOCW-UHFFFAOYSA-N 0.000 description 1
- CXSJCULPCNWMCT-UHFFFAOYSA-N 4-(adamantane-1-carbonylamino)-5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-1,2-oxazole-3-carboxamide Chemical compound C1C(C2)CC(C3)CC2CC13C(=O)NC=1C(C(=O)NCC)=NOC=1C1=CC(C(C)C)=C(O)C=C1O CXSJCULPCNWMCT-UHFFFAOYSA-N 0.000 description 1
- VCJCQTZWCRSVKF-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-4-[(3,4-dimethoxybenzoyl)amino]-N-ethyl-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1=CC=C(OC)C(OC)=C1 VCJCQTZWCRSVKF-UHFFFAOYSA-N 0.000 description 1
- ANIDUTPIZUBSKJ-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-4-(prop-2-enoylamino)-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C=C ANIDUTPIZUBSKJ-UHFFFAOYSA-N 0.000 description 1
- VMSGVWMEXHKVJW-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-4-[(3,4,5-trimethoxybenzoyl)amino]-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1=CC(OC)=C(OC)C(OC)=C1 VMSGVWMEXHKVJW-UHFFFAOYSA-N 0.000 description 1
- DILNMOLOZGRZPP-UHFFFAOYSA-N 5-(2,4-dihydroxy-5-propan-2-ylphenyl)-N-ethyl-4-[(4-methoxyphenyl)sulfonylamino]-1,2-oxazole-3-carboxamide Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NS(=O)(=O)C1=CC=C(OC)C=C1 DILNMOLOZGRZPP-UHFFFAOYSA-N 0.000 description 1
- CCPBQNNFEFGOGY-UHFFFAOYSA-N 5-[5-(2,4-dihydroxy-5-propan-2-ylphenyl)-3-(ethylcarbamoyl)-1,2-oxazol-4-yl]-3-N-ethyl-2H-1,2-oxazole-3,5-dicarboxamide Chemical compound C(C)NC(=O)C1=NOC(=C1C1(C=C(NO1)C(=O)NCC)C(=O)N)C1=C(C=C(C(=C1)C(C)C)O)O CCPBQNNFEFGOGY-UHFFFAOYSA-N 0.000 description 1
- UGWIQBFFHSHNDU-UHFFFAOYSA-N CC(C)C1=C(C=C(C(=C1)C2=C(C(=NO2)C(=O)O)NC(=O)C3CCC(CC3)C(C)(C)C)O)O Chemical compound CC(C)C1=C(C=C(C(=C1)C2=C(C(=NO2)C(=O)O)NC(=O)C3CCC(CC3)C(C)(C)C)O)O UGWIQBFFHSHNDU-UHFFFAOYSA-N 0.000 description 1
- BPRBSCGWXBOORS-UHFFFAOYSA-N OC1=C(C=C(C(=C1)O)C(C)C)C1=C(C(=NO1)C(=O)O)N(C(C1=CC=C(C=C1)N1CCOCC1)=O)C Chemical compound OC1=C(C=C(C(=C1)O)C(C)C)C1=C(C(=NO1)C(=O)O)N(C(C1=CC=C(C=C1)N1CCOCC1)=O)C BPRBSCGWXBOORS-UHFFFAOYSA-N 0.000 description 1
- FREXQSXQFGJSPD-UHFFFAOYSA-N chembl1940927 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)C1CCCCC1 FREXQSXQFGJSPD-UHFFFAOYSA-N 0.000 description 1
- IAVMWVMXDJRTHT-UHFFFAOYSA-N chembl1941051 Chemical compound CCNC(=O)C1=NOC(C=2C(=CC(O)=C(C(C)C)C=2)O)=C1NC(=O)CCN1CCN(C)CC1 IAVMWVMXDJRTHT-UHFFFAOYSA-N 0.000 description 1
- XWBDWHCCBGMXKG-UHFFFAOYSA-N ethanamine;hydron;chloride Chemical compound Cl.CCN XWBDWHCCBGMXKG-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP08159692 | 2008-07-04 | ||
| EP08159692.6 | 2008-07-04 | ||
| PCT/EP2009/058205 WO2010000748A1 (en) | 2008-07-04 | 2009-06-30 | 5-phenyl-isoxazole-3-carboxamides modulating hsp90 with antitumoral activities |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2011526594A JP2011526594A (ja) | 2011-10-13 |
| JP2011526594A5 true JP2011526594A5 (https=) | 2014-03-27 |
| JP5640002B2 JP5640002B2 (ja) | 2014-12-10 |
Family
ID=40019071
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2011515438A Expired - Fee Related JP5640002B2 (ja) | 2008-07-04 | 2009-06-30 | 抗腫瘍活性を有する、ｈｓｐ９０調節性５−フェニル−イソオキサゾール−３−カルボキシアミド |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US8383616B2 (https=) |
| EP (1) | EP2310377B1 (https=) |
| JP (1) | JP5640002B2 (https=) |
| KR (1) | KR20110050615A (https=) |
| CN (1) | CN102083804A (https=) |
| AR (1) | AR072793A1 (https=) |
| AU (1) | AU2009265745B2 (https=) |
| BR (1) | BRPI0913834A2 (https=) |
| CA (1) | CA2729710A1 (https=) |
| EA (1) | EA019793B1 (https=) |
| IL (1) | IL210200A0 (https=) |
| MX (1) | MX2010013913A (https=) |
| MY (1) | MY150604A (https=) |
| NZ (1) | NZ590861A (https=) |
| SG (1) | SG192464A1 (https=) |
| TW (1) | TWI450898B (https=) |
| WO (1) | WO2010000748A1 (https=) |
| ZA (1) | ZA201100007B (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8236838B2 (en) * | 2008-04-21 | 2012-08-07 | Institute For Oneworld Health | Compounds, compositions and methods comprising isoxazole derivatives |
| US8343976B2 (en) | 2009-04-20 | 2013-01-01 | Institute For Oneworld Health | Compounds, compositions and methods comprising pyrazole derivatives |
| US8920675B2 (en) | 2010-10-27 | 2014-12-30 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
| KR101275264B1 (ko) * | 2011-08-24 | 2013-06-17 | 포항공과대학교 산학협력단 | 샤프로닌 단백질의 조절 물질 탐색 방법 |
| CN103724269B (zh) * | 2012-10-11 | 2016-12-21 | 中国科学院上海药物研究所 | 苯基1,2-异噁唑或苯基1,2-吡唑类化合物及其用途 |
| WO2015143004A1 (en) * | 2014-03-18 | 2015-09-24 | Synta Pharmaceuticals Corp. | Targeted therapeutics |
| WO2016054560A1 (en) * | 2014-10-02 | 2016-04-07 | Flatley Discovery Lab | Isoxazole compounds and methods for the treatment of cystic fibrosis |
| AU2015371251B2 (en) | 2014-12-23 | 2020-06-11 | Dana-Farber Cancer Institute, Inc. | Inhibitors of cyclin-dependent kinase 7 (CDK7) |
| CN104725329B (zh) * | 2015-01-13 | 2017-01-18 | 陕西科技大学 | 一种具有抗肿瘤活性的异恶唑羧酸类化合物及其合成方法 |
| HK1246645A1 (zh) | 2015-03-27 | 2018-09-14 | 达纳-法伯癌症研究所股份有限公司 | 细胞周期蛋白依赖性激酶的抑制剂 |
| CN104803934B (zh) * | 2015-05-04 | 2018-01-02 | 陕西科技大学 | 一种具有抗肿瘤活性的苯基异噁唑羧酸类化合物及其合成方法与应用 |
| IT201700081419A1 (it) * | 2017-07-18 | 2019-01-18 | Rare Partners Srl | Derivati isossazolici come induttori di emoglobina fetale in precursori eritroidi derivati da pazienti beta-talassemici |
| US12187701B2 (en) | 2018-06-25 | 2025-01-07 | Dana-Farber Cancer Institute, Inc. | Taire family kinase inhibitors and uses thereof |
| JP7660063B2 (ja) | 2018-12-28 | 2025-04-10 | ダナ－ファーバー キャンサー インスティテュート， インコーポレイテッド | サイクリン依存性キナーゼ７のインヒビターおよびそれらの使用 |
| CN117105880B (zh) * | 2022-10-17 | 2025-08-26 | 上海康斯维克生物医药有限公司 | 用作诱发抗原特异性反应的脲类化合物、其荧光标记物及制备方法和用途 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE420878T1 (de) * | 2000-02-18 | 2009-01-15 | Kyowa Hakko Kirin Co Ltd | Isoxazol- und thiazolverbindungen und ihre verwendung als medikamente |
| EA009919B1 (ru) * | 2003-02-11 | 2008-04-28 | Вернэлис (Кембридж) Лимитед | Соединения изоксазола |
| KR101394245B1 (ko) * | 2005-12-30 | 2014-05-14 | 에스케이바이오팜 주식회사 | 아이속사졸 유도체 및 이의 용도 |
| GB0603880D0 (en) * | 2006-02-27 | 2006-04-05 | Novartis Ag | Organic compounds |
| CN101636162A (zh) * | 2007-03-01 | 2010-01-27 | 诺瓦提斯公司 | 5-(2,4-二羟基-5-异丙基-苯基)-4-(4-吗啉-4-基甲基-苯基)-异唑-3-甲酸乙基酰胺的酸加成盐、水合物和多晶型物以及包含这些形式的制剂 |
-
2009
- 2009-06-17 TW TW098120258A patent/TWI450898B/zh not_active IP Right Cessation
- 2009-06-30 EA EA201170139A patent/EA019793B1/ru not_active IP Right Cessation
- 2009-06-30 NZ NZ590861A patent/NZ590861A/xx not_active IP Right Cessation
- 2009-06-30 EP EP09772448.8A patent/EP2310377B1/en not_active Not-in-force
- 2009-06-30 SG SG2013051305A patent/SG192464A1/en unknown
- 2009-06-30 WO PCT/EP2009/058205 patent/WO2010000748A1/en not_active Ceased
- 2009-06-30 CN CN2009801255931A patent/CN102083804A/zh active Pending
- 2009-06-30 JP JP2011515438A patent/JP5640002B2/ja not_active Expired - Fee Related
- 2009-06-30 MY MYPI20105887 patent/MY150604A/en unknown
- 2009-06-30 KR KR1020117000312A patent/KR20110050615A/ko not_active Ceased
- 2009-06-30 US US13/001,652 patent/US8383616B2/en not_active Expired - Fee Related
- 2009-06-30 MX MX2010013913A patent/MX2010013913A/es active IP Right Grant
- 2009-06-30 AU AU2009265745A patent/AU2009265745B2/en not_active Ceased
- 2009-06-30 BR BRPI0913834A patent/BRPI0913834A2/pt not_active IP Right Cessation
- 2009-06-30 CA CA2729710A patent/CA2729710A1/en not_active Abandoned
- 2009-07-03 AR ARP090102496A patent/AR072793A1/es unknown
-
2010
- 2010-12-23 IL IL210200A patent/IL210200A0/en unknown
-
2011
- 2011-01-03 ZA ZA2011/00007A patent/ZA201100007B/en unknown
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