HRP20030083A2 - Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids - Google Patents
Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids Download PDFInfo
- Publication number
- HRP20030083A2 HRP20030083A2 HR20030083A HRP20030083A HRP20030083A2 HR P20030083 A2 HRP20030083 A2 HR P20030083A2 HR 20030083 A HR20030083 A HR 20030083A HR P20030083 A HRP20030083 A HR P20030083A HR P20030083 A2 HRP20030083 A2 HR P20030083A2
- Authority
- HR
- Croatia
- Prior art keywords
- phenylamino
- benzamide
- iodo
- difluoro
- hydroxy
- Prior art date
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- 150000002148 esters Chemical class 0.000 title claims description 7
- QAMBBWKIAJFFRF-UHFFFAOYSA-N n-hydroxy-2-(4-iodoanilino)benzamide Chemical class ONC(=O)C1=CC=CC=C1NC1=CC=C(I)C=C1 QAMBBWKIAJFFRF-UHFFFAOYSA-N 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 155
- 238000000034 method Methods 0.000 claims description 134
- -1 (phenyl)carbonyl Chemical group 0.000 claims description 68
- SUDAHWBOROXANE-SECBINFHSA-N PD 0325901 Chemical compound OC[C@@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-SECBINFHSA-N 0.000 claims description 66
- 125000000217 alkyl group Chemical group 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 60
- 239000000843 powder Substances 0.000 claims description 60
- 230000005855 radiation Effects 0.000 claims description 50
- 239000000460 chlorine Substances 0.000 claims description 37
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 34
- 208000002193 Pain Diseases 0.000 claims description 30
- 239000013078 crystal Substances 0.000 claims description 28
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 27
- 229910052731 fluorine Inorganic materials 0.000 claims description 27
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 238000012916 structural analysis Methods 0.000 claims description 26
- 239000011737 fluorine Substances 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 150000002431 hydrogen Chemical class 0.000 claims description 23
- 150000003839 salts Chemical class 0.000 claims description 23
- SUDAHWBOROXANE-VIFPVBQESA-N PD 0325901-Cl Chemical compound OC[C@H](O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F SUDAHWBOROXANE-VIFPVBQESA-N 0.000 claims description 22
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 20
- 230000036407 pain Effects 0.000 claims description 20
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 17
- 206010028980 Neoplasm Diseases 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 208000000094 Chronic Pain Diseases 0.000 claims description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 206010061218 Inflammation Diseases 0.000 claims description 8
- 206010003246 arthritis Diseases 0.000 claims description 8
- 229910052794 bromium Inorganic materials 0.000 claims description 8
- 230000004054 inflammatory process Effects 0.000 claims description 8
- 208000004296 neuralgia Diseases 0.000 claims description 8
- 208000021722 neuropathic pain Diseases 0.000 claims description 8
- 230000002062 proliferating effect Effects 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000005842 heteroatom Chemical group 0.000 claims description 7
- 239000003112 inhibitor Substances 0.000 claims description 7
- 230000011278 mitosis Effects 0.000 claims description 7
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 7
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 6
- GQAZGSHVSAGDOJ-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F GQAZGSHVSAGDOJ-UHFFFAOYSA-N 0.000 claims description 6
- ASLGKYRJGJLPAE-UHFFFAOYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-n-(2,3-dihydroxypropoxy)-3,4-difluorobenzamide Chemical compound OCC(O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl ASLGKYRJGJLPAE-UHFFFAOYSA-N 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 208000004550 Postoperative Pain Diseases 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- ASLGKYRJGJLPAE-QMMMGPOBSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-n-[(2s)-2,3-dihydroxypropoxy]-3,4-difluorobenzamide Chemical compound OC[C@H](O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl ASLGKYRJGJLPAE-QMMMGPOBSA-N 0.000 claims description 5
- UVQPYTNHXUMIMH-UHFFFAOYSA-N 5-chloro-n-(2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1F UVQPYTNHXUMIMH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 206010019280 Heart failures Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 5
- 125000004122 cyclic group Chemical group 0.000 claims description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
- 201000008482 osteoarthritis Diseases 0.000 claims description 5
- 208000037803 restenosis Diseases 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 4
- ZEZXICVAWOUQSB-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-4-fluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Cl ZEZXICVAWOUQSB-UHFFFAOYSA-N 0.000 claims description 4
- ZSUYOTZRXQOCRA-UHFFFAOYSA-N 3,4,5-trifluoro-n-(2-hydroxyethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(F)C=C1C(=O)NOCCO ZSUYOTZRXQOCRA-UHFFFAOYSA-N 0.000 claims description 4
- CKIRZXDWDRUDIR-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxy-2-methylpropoxy)benzamide Chemical compound CC(C)(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F CKIRZXDWDRUDIR-UHFFFAOYSA-N 0.000 claims description 4
- XBBYDBSSUSYRRN-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-[2-(2,2,2-trifluoroethylamino)ethoxy]benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCCNCC(F)(F)F XBBYDBSSUSYRRN-UHFFFAOYSA-N 0.000 claims description 4
- HSZHWOFEZWWCOB-UHFFFAOYSA-N 4-fluoro-n-(3-hydroxypropoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCCCO HSZHWOFEZWWCOB-UHFFFAOYSA-N 0.000 claims description 4
- YZVHIDUDGXLOLY-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(3-hydroxypropoxy)benzamide Chemical compound OCCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl YZVHIDUDGXLOLY-UHFFFAOYSA-N 0.000 claims description 4
- XXSSGBYXSKOLAM-UHFFFAOYSA-N 5-bromo-n-(2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(O)CONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1F XXSSGBYXSKOLAM-UHFFFAOYSA-N 0.000 claims description 4
- ASLGKYRJGJLPAE-MRVPVSSYSA-N 5-chloro-2-(2-chloro-4-iodoanilino)-n-[(2r)-2,3-dihydroxypropoxy]-3,4-difluorobenzamide Chemical compound OC[C@@H](O)CONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl ASLGKYRJGJLPAE-MRVPVSSYSA-N 0.000 claims description 4
- DAVWVMNCZOSIBH-UHFFFAOYSA-N 5-chloro-n-(1,3-dihydroxypropan-2-yloxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(CO)ONC(=O)C1=CC(Cl)=C(F)C(F)=C1NC1=CC=C(I)C=C1F DAVWVMNCZOSIBH-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
- 150000001408 amides Chemical class 0.000 claims description 4
- 239000002246 antineoplastic agent Substances 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 4
- 210000004072 lung Anatomy 0.000 claims description 4
- AEAMPCCYDKGXCC-UHFFFAOYSA-N n-(1,3-dihydroxypropan-2-yloxy)-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound OCC(CO)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F AEAMPCCYDKGXCC-UHFFFAOYSA-N 0.000 claims description 4
- ASOKITCGBKGOAH-UHFFFAOYSA-N n-[(2,2-dimethyl-1,3-dioxolan-4-yl)methoxy]-3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzamide Chemical compound O1C(C)(C)OCC1CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F ASOKITCGBKGOAH-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 238000001959 radiotherapy Methods 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 3
- XBBDXCSMZAFUCG-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4,5-trifluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl XBBDXCSMZAFUCG-UHFFFAOYSA-N 0.000 claims description 3
- VEFHUCQYLJVXTF-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxy-2-methylpropoxy)benzamide Chemical compound CC(C)(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl VEFHUCQYLJVXTF-UHFFFAOYSA-N 0.000 claims description 3
- ZDTUJTKFWCTQTA-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl ZDTUJTKFWCTQTA-UHFFFAOYSA-N 0.000 claims description 3
- QTAXLCPBGMRXPB-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-4,5-difluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(F)=C(F)C=C1NC1=CC=C(I)C=C1Cl QTAXLCPBGMRXPB-UHFFFAOYSA-N 0.000 claims description 3
- OLTJOKGXRQIKDW-UHFFFAOYSA-N 2-(2-chloro-4-iodoanilino)-4-fluoro-n-(3-hydroxypropoxy)benzamide Chemical compound OCCCONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1Cl OLTJOKGXRQIKDW-UHFFFAOYSA-N 0.000 claims description 3
- TVXWDBIJYZFGCG-UHFFFAOYSA-N 3,4,5-trifluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(F)=C(F)C(F)=C1NC1=CC=C(I)C=C1F TVXWDBIJYZFGCG-UHFFFAOYSA-N 0.000 claims description 3
- HIMTUIUWQDFWDV-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(1-hydroxy-2-methylpropan-2-yl)oxybenzamide Chemical compound OCC(C)(C)ONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F HIMTUIUWQDFWDV-UHFFFAOYSA-N 0.000 claims description 3
- PWJVGVUKOYIXGI-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(3-hydroxypropoxy)benzamide Chemical compound OCCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F PWJVGVUKOYIXGI-UHFFFAOYSA-N 0.000 claims description 3
- JXQALZUQMVXFAC-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-[2-(methylamino)ethoxy]benzamide Chemical compound CNCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F JXQALZUQMVXFAC-UHFFFAOYSA-N 0.000 claims description 3
- ZUNRTXWQUYMXIM-UHFFFAOYSA-N 3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-[2-hydroxy-3-(methylamino)propoxy]benzamide Chemical compound CNCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F ZUNRTXWQUYMXIM-UHFFFAOYSA-N 0.000 claims description 3
- OKAOLVGZYFXUAV-UHFFFAOYSA-N 3,4-difluoro-2-(4-iodo-2-methylanilino)-n-[2-(methylamino)ethoxy]benzamide Chemical compound CNCCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C OKAOLVGZYFXUAV-UHFFFAOYSA-N 0.000 claims description 3
- DADGHVDWQXEJGZ-UHFFFAOYSA-N 3,4-difluoro-n-(1-hydroxy-2-methylpropan-2-yl)oxy-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOC(C)(C)CO DADGHVDWQXEJGZ-UHFFFAOYSA-N 0.000 claims description 3
- KGDZSEGBJANPRB-UHFFFAOYSA-N 3,4-difluoro-n-(2-hydroxy-3-methoxypropoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound COCC(O)CONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C KGDZSEGBJANPRB-UHFFFAOYSA-N 0.000 claims description 3
- RAISTQMUTLJEBJ-UHFFFAOYSA-N 3,4-difluoro-n-[[1-(hydroxymethyl)cyclopropyl]methoxy]-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=CC=C1C(=O)NOCC1(CO)CC1 RAISTQMUTLJEBJ-UHFFFAOYSA-N 0.000 claims description 3
- NZLBVPZBNGBXPI-UHFFFAOYSA-N 4,5-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(F)=C(F)C=C1NC1=CC=C(I)C=C1F NZLBVPZBNGBXPI-UHFFFAOYSA-N 0.000 claims description 3
- UYABRWWTZQZEDR-UHFFFAOYSA-N 4,5-difluoro-n-(2-hydroxyethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C(F)C=C1C(=O)NOCCO UYABRWWTZQZEDR-UHFFFAOYSA-N 0.000 claims description 3
- FQELXZARENTIKS-UHFFFAOYSA-N 4-fluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC=C(F)C=C1NC1=CC=C(I)C=C1F FQELXZARENTIKS-UHFFFAOYSA-N 0.000 claims description 3
- KQBLIJZTHLEFFL-UHFFFAOYSA-N 4-fluoro-n-(2-hydroxyethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=CC=C1C(=O)NOCCO KQBLIJZTHLEFFL-UHFFFAOYSA-N 0.000 claims description 3
- JAJYJOVHOFOWJR-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(1-hydroxy-2-methylpropan-2-yl)oxybenzamide Chemical compound OCC(C)(C)ONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl JAJYJOVHOFOWJR-UHFFFAOYSA-N 0.000 claims description 3
- YEGYPQZEUQHTBQ-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxy-3-methoxypropoxy)benzamide Chemical compound COCC(O)CONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl YEGYPQZEUQHTBQ-UHFFFAOYSA-N 0.000 claims description 3
- HRABIHHENHSTBS-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl HRABIHHENHSTBS-UHFFFAOYSA-N 0.000 claims description 3
- HSOHARZKALUJED-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-(3,3,3-trifluoro-2-hydroxypropoxy)benzamide Chemical compound FC(F)(F)C(O)CONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl HSOHARZKALUJED-UHFFFAOYSA-N 0.000 claims description 3
- TXDMESHIQKQZPC-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-3,4-difluoro-n-[[1-(hydroxymethyl)cyclopropyl]methoxy]benzamide Chemical compound C=1C(Br)=C(F)C(F)=C(NC=2C(=CC(I)=CC=2)Cl)C=1C(=O)NOCC1(CO)CC1 TXDMESHIQKQZPC-UHFFFAOYSA-N 0.000 claims description 3
- KLWVQBQQPZPQCK-UHFFFAOYSA-N 5-bromo-2-(2-chloro-4-iodoanilino)-n-[2-(dimethylamino)ethoxy]-3,4-difluorobenzamide Chemical compound CN(C)CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1Cl KLWVQBQQPZPQCK-UHFFFAOYSA-N 0.000 claims description 3
- JGUJNCYXMKPUNI-UHFFFAOYSA-N 5-bromo-3,4-difluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1F JGUJNCYXMKPUNI-UHFFFAOYSA-N 0.000 claims description 3
- HUXIPGAKZFWFMM-UHFFFAOYSA-N 5-bromo-3,4-difluoro-n-(2-hydroxyethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=C(F)C(F)=C(Br)C=C1C(=O)NOCCO HUXIPGAKZFWFMM-UHFFFAOYSA-N 0.000 claims description 3
- CQPSMBQJOXWKER-UHFFFAOYSA-N 5-bromo-4-fluoro-2-(2-fluoro-4-iodoanilino)-n-(2-hydroxyethoxy)benzamide Chemical compound OCCONC(=O)C1=CC(Br)=C(F)C=C1NC1=CC=C(I)C=C1F CQPSMBQJOXWKER-UHFFFAOYSA-N 0.000 claims description 3
- YMCDQJQIFPNVQN-UHFFFAOYSA-N 5-bromo-4-fluoro-n-(2-hydroxyethoxy)-2-(4-iodo-2-methylanilino)benzamide Chemical compound CC1=CC(I)=CC=C1NC1=CC(F)=C(Br)C=C1C(=O)NOCCO YMCDQJQIFPNVQN-UHFFFAOYSA-N 0.000 claims description 3
- QIPKGNZZELMQAF-UHFFFAOYSA-N 5-bromo-n-(2,3-dihydroxypropoxy)-3,4-difluoro-2-(2-fluoroanilino)benzamide Chemical compound OCC(O)CONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=CC=C1F QIPKGNZZELMQAF-UHFFFAOYSA-N 0.000 claims description 3
- JHYXQASFNXYVPM-UHFFFAOYSA-N 5-bromo-n-[2-(diethylamino)ethoxy]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CCN(CC)CCONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C JHYXQASFNXYVPM-UHFFFAOYSA-N 0.000 claims description 3
- IBZPDAZZGTZKNJ-UHFFFAOYSA-N 5-bromo-n-[2-(dimethylamino)propoxy]-3,4-difluoro-2-(4-iodo-2-methylanilino)benzamide Chemical compound CN(C)C(C)CONC(=O)C1=CC(Br)=C(F)C(F)=C1NC1=CC=C(I)C=C1C IBZPDAZZGTZKNJ-UHFFFAOYSA-N 0.000 claims description 3
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- IHIXIJGXTJIKRB-UHFFFAOYSA-N trisodium vanadate Chemical compound [Na+].[Na+].[Na+].[O-][V]([O-])([O-])=O IHIXIJGXTJIKRB-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
- C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
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- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/16—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/18—Radicals substituted by singly bound oxygen or sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
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US21937200P | 2000-07-19 | 2000-07-19 | |
PCT/US2001/022331 WO2002006213A2 (fr) | 2000-07-19 | 2001-07-12 | Esters oxygenes d'acides 4-iodophenylamino benzhydroxamiques |
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HR20030083A HRP20030083A2 (en) | 2000-07-19 | 2003-02-06 | Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids |
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WO2010068738A1 (fr) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mutations de mek conférant une résistance aux inhibiteurs de mek |
WO2011106298A1 (fr) | 2010-02-25 | 2011-09-01 | Dana-Farber Cancer Institute, Inc. | Mutations de braf conférant une résistance aux inhibiteurs de braf |
EP3028699A1 (fr) | 2010-02-25 | 2016-06-08 | Dana-Farber Cancer Institute, Inc. | Mutations braf conférant une résistance aux inhibiteurs de braf |
WO2013169858A1 (fr) | 2012-05-08 | 2013-11-14 | The Broad Institute, Inc. | Méthodes de diagnostic et de traitement chez des patients ayant ou présentant un risque de développer une résistance à une thérapie anticancéreuse |
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