ZA200300348B - Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids. - Google Patents
Oxygenated esters of 4-iodo phenylamino benzhydroxamic acids. Download PDFInfo
- Publication number
- ZA200300348B ZA200300348B ZA200300348A ZA200300348A ZA200300348B ZA 200300348 B ZA200300348 B ZA 200300348B ZA 200300348 A ZA200300348 A ZA 200300348A ZA 200300348 A ZA200300348 A ZA 200300348A ZA 200300348 B ZA200300348 B ZA 200300348B
- Authority
- ZA
- South Africa
- Prior art keywords
- phenylamino
- benzamide
- iodo
- difluoro
- hydroxy
- Prior art date
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- 150000002148 esters Chemical class 0.000 title description 10
- 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
- -1 (phenyl)carbonyl Chemical group 0.000 claims description 286
- 150000001875 compounds Chemical class 0.000 claims description 168
- 238000000034 method Methods 0.000 claims description 110
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims description 95
- 239000000203 mixture Substances 0.000 claims description 90
- 125000000217 alkyl group Chemical group 0.000 claims description 77
- 229910052739 hydrogen Inorganic materials 0.000 claims description 60
- 239000001257 hydrogen Substances 0.000 claims description 60
- 239000000843 powder Substances 0.000 claims description 52
- 230000005855 radiation Effects 0.000 claims description 50
- 239000000460 chlorine Substances 0.000 claims description 45
- 238000002441 X-ray diffraction Methods 0.000 claims description 43
- 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 42
- 208000002193 Pain Diseases 0.000 claims description 35
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 32
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 31
- 238000011282 treatment Methods 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 28
- 229910052731 fluorine Chemical group 0.000 claims description 28
- 239000011737 fluorine Chemical group 0.000 claims description 26
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 23
- 206010028980 Neoplasm Diseases 0.000 claims description 22
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 19
- 230000036407 pain Effects 0.000 claims description 19
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 229910052801 chlorine Inorganic materials 0.000 claims description 17
- 125000001153 fluoro group Chemical group F* 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 16
- 201000010099 disease Diseases 0.000 claims description 16
- 208000037265 diseases, disorders, signs and symptoms 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
- 208000000094 Chronic Pain Diseases 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 15
- 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 14
- 238000004519 manufacturing process Methods 0.000 claims description 13
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
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- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 11
- 125000003342 alkenyl group Chemical group 0.000 claims description 10
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- 230000002062 proliferating effect Effects 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
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- 208000004550 Postoperative Pain Diseases 0.000 claims description 9
- 125000000623 heterocyclic group Chemical group 0.000 claims description 9
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- 125000001424 substituent group Chemical group 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 7
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 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
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- 125000004663 dialkyl amino group Chemical group 0.000 claims description 5
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 5
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 5
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- 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 3
- 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 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
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- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-N sodium;hydron;carbonate Chemical class [Na+].OC(O)=O UIIMBOGNXHQVGW-UHFFFAOYSA-N 0.000 description 1
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- DKPFODGZWDEEBT-QFIAKTPHSA-N taxane Chemical class C([C@]1(C)CCC[C@@H](C)[C@H]1C1)C[C@H]2[C@H](C)CC[C@@H]1C2(C)C DKPFODGZWDEEBT-QFIAKTPHSA-N 0.000 description 1
- FNERLWQYDWLBIB-UHFFFAOYSA-N tert-butyl 3-aminooxy-3-hydroxy-2,2-dimethylpropanoate Chemical compound CC(C)(C)OC(=O)C(C)(C)C(O)ON FNERLWQYDWLBIB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BOSNEKRDBDBXIN-LBPRGKRZSA-N tert-butyl n-[(2s)-1-[tert-butyl(dimethyl)silyl]oxy-3-hydroxypropan-2-yl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@@H](CO)CO[Si](C)(C)C(C)(C)C BOSNEKRDBDBXIN-LBPRGKRZSA-N 0.000 description 1
- QDYCZPAIJAPPNC-LBPRGKRZSA-N tert-butyl n-[(2s)-1-aminooxy-3-[tert-butyl(dimethyl)silyl]oxypropan-2-yl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)[C@@H](CON)CO[Si](C)(C)C(C)(C)C QDYCZPAIJAPPNC-LBPRGKRZSA-N 0.000 description 1
- KXSOWEYOPZWNPX-UHFFFAOYSA-N tert-butyl n-[2-[[3,4-difluoro-2-(4-iodo-2-methylanilino)benzoyl]amino]oxyethyl]-n-methylcarbamate Chemical compound CC(C)(C)OC(=O)N(C)CCONC(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1C KXSOWEYOPZWNPX-UHFFFAOYSA-N 0.000 description 1
- FGTJJHCZWOVVNH-UHFFFAOYSA-N tert-butyl-[tert-butyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound CC(C)(C)[Si](C)(C)O[Si](C)(C)C(C)(C)C FGTJJHCZWOVVNH-UHFFFAOYSA-N 0.000 description 1
- MHYGQXWCZAYSLJ-UHFFFAOYSA-N tert-butyl-chloro-diphenylsilane Chemical compound C=1C=CC=CC=1[Si](Cl)(C(C)(C)C)C1=CC=CC=C1 MHYGQXWCZAYSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000003554 tetrahydropyrrolyl group Chemical group 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
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- 229910052905 tridymite Inorganic materials 0.000 description 1
- JOHWNGGYGAVMGU-UHFFFAOYSA-N trifluorochlorine Chemical compound FCl(F)F JOHWNGGYGAVMGU-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- 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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
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- 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
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Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
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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