WO2014062511A1 - Therapeutic compounds and compositions - Google Patents
Therapeutic compounds and compositions Download PDFInfo
- Publication number
- WO2014062511A1 WO2014062511A1 PCT/US2013/064601 US2013064601W WO2014062511A1 WO 2014062511 A1 WO2014062511 A1 WO 2014062511A1 US 2013064601 W US2013064601 W US 2013064601W WO 2014062511 A1 WO2014062511 A1 WO 2014062511A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- amino
- phenyl
- methyl
- benzenesulfonamide
- carbonyl
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 217
- 239000000203 mixture Substances 0.000 title claims description 43
- 230000001225 therapeutic effect Effects 0.000 title description 7
- 238000000034 method Methods 0.000 claims abstract description 144
- 206010028980 Neoplasm Diseases 0.000 claims abstract description 71
- 201000011510 cancer Diseases 0.000 claims abstract description 51
- 201000003793 Myelodysplastic syndrome Diseases 0.000 claims abstract description 13
- 201000007224 Myeloproliferative neoplasm Diseases 0.000 claims abstract description 13
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims abstract description 10
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims abstract description 10
- 208000015914 Non-Hodgkin lymphomas Diseases 0.000 claims abstract description 10
- 201000001441 melanoma Diseases 0.000 claims abstract description 8
- 208000002154 non-small cell lung carcinoma Diseases 0.000 claims abstract description 8
- 208000029729 tumor suppressor gene on chromosome 11 Diseases 0.000 claims abstract description 8
- 208000005243 Chondrosarcoma Diseases 0.000 claims abstract description 7
- 208000005017 glioblastoma Diseases 0.000 claims abstract description 6
- 206010039491 Sarcoma Diseases 0.000 claims abstract description 5
- -1 Ci_6 alkyl-OH Chemical group 0.000 claims description 165
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 85
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 80
- 125000000217 alkyl group Chemical group 0.000 claims description 72
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 72
- 230000035772 mutation Effects 0.000 claims description 64
- 125000003118 aryl group Chemical group 0.000 claims description 55
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 51
- 125000000623 heterocyclic group Chemical group 0.000 claims description 46
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 102100037845 Isocitrate dehydrogenase [NADP], mitochondrial Human genes 0.000 claims description 36
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
- 238000011282 treatment Methods 0.000 claims description 35
- 125000001072 heteroaryl group Chemical group 0.000 claims description 33
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 32
- 101000599886 Homo sapiens Isocitrate dehydrogenase [NADP], mitochondrial Proteins 0.000 claims description 31
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 24
- 229940124597 therapeutic agent Drugs 0.000 claims description 19
- 239000008194 pharmaceutical composition Substances 0.000 claims description 18
- 102200116484 rs121913502 Human genes 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 101000960234 Homo sapiens Isocitrate dehydrogenase [NADP] cytoplasmic Proteins 0.000 claims description 17
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 17
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
- 101001042041 Bos taurus Isocitrate dehydrogenase [NAD] subunit beta, mitochondrial Proteins 0.000 claims description 16
- 102000004190 Enzymes Human genes 0.000 claims description 16
- 108090000790 Enzymes Proteins 0.000 claims description 16
- 102100039905 Isocitrate dehydrogenase [NADP] cytoplasmic Human genes 0.000 claims description 16
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 16
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 15
- 239000003814 drug Substances 0.000 claims description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 15
- 102200069690 rs121913500 Human genes 0.000 claims description 15
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 14
- 239000004202 carbamide Substances 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 230000001419 dependent effect Effects 0.000 claims description 14
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 230000009467 reduction Effects 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 10
- 102200069708 rs121913499 Human genes 0.000 claims description 9
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- OEYGXEYESNDHQS-UHFFFAOYSA-N 1-(2-methyl-5-piperidin-1-ylsulfonylphenyl)-3-(3,5,7-trimethyl-1-adamantyl)urea Chemical compound C1=C(NC(=O)NC23CC4(C)CC(C)(CC(C4)(C)C2)C3)C(C)=CC=C1S(=O)(=O)N1CCCCC1 OEYGXEYESNDHQS-UHFFFAOYSA-N 0.000 claims description 7
- CYCFHZPFMAXQRB-UHFFFAOYSA-N 1-(4-chlorophenyl)-3-[5-morpholin-4-ylsulfonyl-2-(2-oxopyrrolidin-1-yl)phenyl]urea Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC1=CC(S(=O)(=O)N2CCOCC2)=CC=C1N1C(=O)CCC1 CYCFHZPFMAXQRB-UHFFFAOYSA-N 0.000 claims description 7
- JADAACJWFPKJSC-UHFFFAOYSA-N 1-[2-(diethylamino)-5-morpholin-4-ylsulfonylphenyl]-3-(3-methylphenyl)urea Chemical compound CCN(CC)C1=CC=C(S(=O)(=O)N2CCOCC2)C=C1NC(=O)NC1=CC=CC(C)=C1 JADAACJWFPKJSC-UHFFFAOYSA-N 0.000 claims description 7
- GUNQZZMJRXGITI-UHFFFAOYSA-N 1-[3-[(2-methoxyphenyl)sulfamoyl]-4-piperidin-1-ylphenyl]-3-[2-(3-prop-1-en-2-ylphenyl)propan-2-yl]urea Chemical compound COC1=CC=CC=C1NS(=O)(=O)C1=CC(NC(=O)NC(C)(C)C=2C=C(C=CC=2)C(C)=C)=CC=C1N1CCCCC1 GUNQZZMJRXGITI-UHFFFAOYSA-N 0.000 claims description 7
- KNPYUBYMGCLBEJ-UHFFFAOYSA-N 1-[5-(azepan-1-ylsulfonyl)-2-chlorophenyl]-3-(4-nitrophenyl)urea Chemical compound C1=CC([N+](=O)[O-])=CC=C1NC(=O)NC1=CC(S(=O)(=O)N2CCCCCC2)=CC=C1Cl KNPYUBYMGCLBEJ-UHFFFAOYSA-N 0.000 claims description 7
- HRKRDXGIYSURLR-UHFFFAOYSA-N 1-[5-[(2,5-dichlorophenyl)sulfamoyl]-2-(diethylamino)phenyl]-3-(4-nitrophenyl)urea Chemical compound CCN(CC)C1=CC=C(S(=O)(=O)NC=2C(=CC=C(Cl)C=2)Cl)C=C1NC(=O)NC1=CC=C([N+]([O-])=O)C=C1 HRKRDXGIYSURLR-UHFFFAOYSA-N 0.000 claims description 7
- DVNJUHFYDMTVCU-UHFFFAOYSA-N 1-[5-[[4-[bis(2-hydroxyethyl)amino]-2-methylphenyl]methylidene]-2-phenylimidazol-4-yl]-3-[5-(hexadecylsulfamoyl)-2-methoxyphenyl]urea Chemical compound CCCCCCCCCCCCCCCCNS(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C(N=C(N=2)C=2C=CC=CC=2)=CC=2C(=CC(=CC=2)N(CCO)CCO)C)=C1 DVNJUHFYDMTVCU-UHFFFAOYSA-N 0.000 claims description 7
- KRYZQVQMDSSVHM-UHFFFAOYSA-N 3-(4-chloro-3-pyrrolidin-1-ylsulfonylphenyl)-1-methyl-1-[(2-methyl-1,3-thiazol-5-yl)methyl]urea Chemical compound C=1C=C(Cl)C(S(=O)(=O)N2CCCC2)=CC=1NC(=O)N(C)CC1=CN=C(C)S1 KRYZQVQMDSSVHM-UHFFFAOYSA-N 0.000 claims description 7
- CTJVLIALFREFQS-UHFFFAOYSA-N 3-(4-ethoxy-3-pyrrolidin-1-ylsulfonylphenyl)-1-methyl-1-(4-methylcyclohexyl)urea Chemical compound C1=C(S(=O)(=O)N2CCCC2)C(OCC)=CC=C1NC(=O)N(C)C1CCC(C)CC1 CTJVLIALFREFQS-UHFFFAOYSA-N 0.000 claims description 7
- YLOIWATYZNZGIC-UHFFFAOYSA-N 3-(4-methoxy-3-piperidin-1-ylsulfonylphenyl)-1-methyl-1-[(2-methyl-1,3-thiazol-5-yl)methyl]urea Chemical compound C1=C(S(=O)(=O)N2CCCCC2)C(OC)=CC=C1NC(=O)N(C)CC1=CN=C(C)S1 YLOIWATYZNZGIC-UHFFFAOYSA-N 0.000 claims description 7
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 claims description 7
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 7
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 7
- LDZOUHCRTQBWTF-UHFFFAOYSA-O n-[4-[[5-[3-(4-butyl-3,5-dimethylpyridin-1-ium-1-yl)propylcarbamoylamino]-2-chlorophenyl]sulfonylamino]anilino]formamide Chemical compound C1=C(C)C(CCCC)=C(C)C=[N+]1CCCNC(=O)NC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(NNC=O)=CC=2)=C1 LDZOUHCRTQBWTF-UHFFFAOYSA-O 0.000 claims description 7
- IJAIFRUQXADQJV-UHFFFAOYSA-N n-[4-[[5-[3-(4-butyl-3,5-dimethylpyridin-1-ium-1-yl)propylcarbamoylamino]-2-chlorophenyl]sulfonylamino]anilino]formamide;chloride Chemical compound [Cl-].C1=C(C)C(CCCC)=C(C)C=[N+]1CCCNC(=O)NC1=CC=C(Cl)C(S(=O)(=O)NC=2C=CC(NNC=O)=CC=2)=C1 IJAIFRUQXADQJV-UHFFFAOYSA-N 0.000 claims description 7
- RIHISJPMISXXNE-UHFFFAOYSA-N n-[5-chloro-3-[[4-chloro-3-(dodecylsulfamoyl)phenyl]carbamoylamino]-2-hydroxyphenyl]acetamide Chemical compound C1=C(Cl)C(S(=O)(=O)NCCCCCCCCCCCC)=CC(NC(=O)NC=2C(=C(NC(C)=O)C=C(Cl)C=2)O)=C1 RIHISJPMISXXNE-UHFFFAOYSA-N 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- VAZOYARPRLVOKK-UHFFFAOYSA-N 1-[5-(butylsulfamoyl)-2-methoxyphenyl]-3-[4-[6-(morpholin-4-ylmethyl)pyridin-3-yl]naphthalen-1-yl]urea Chemical compound CCCCNS(=O)(=O)C1=CC=C(OC)C(NC(=O)NC=2C3=CC=CC=C3C(C=3C=NC(CN4CCOCC4)=CC=3)=CC=2)=C1 VAZOYARPRLVOKK-UHFFFAOYSA-N 0.000 claims description 6
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- 125000004001 thioalkyl group Chemical group 0.000 claims description 5
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- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 3
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- CPRRHERYRRXBRZ-SRVKXCTJSA-N methyl n-[(2s)-1-[[(2s)-1-hydroxy-3-[(3s)-2-oxopyrrolidin-3-yl]propan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]carbamate Chemical compound COC(=O)N[C@@H](CC(C)C)C(=O)N[C@H](CO)C[C@@H]1CCNC1=O CPRRHERYRRXBRZ-SRVKXCTJSA-N 0.000 claims description 3
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 1
- 108010075869 Isocitrate Dehydrogenase Proteins 0.000 abstract description 8
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- 239000003112 inhibitor Substances 0.000 abstract description 7
- 101000960235 Dictyostelium discoideum Isocitrate dehydrogenase [NADP] cytoplasmic Proteins 0.000 abstract description 6
- 125000004421 aryl sulphonamide group Chemical group 0.000 abstract 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 355
- 238000005160 1H NMR spectroscopy Methods 0.000 description 275
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- OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 150
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Classifications
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- C07C311/37—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
- C07C311/38—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton
- C07C311/44—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring having sulfur atoms of sulfonamide groups and amino groups bound to carbon atoms of six-membered rings of the same carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- A61K31/553—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having at least one nitrogen and one oxygen as ring hetero atoms, e.g. loxapine, staurosporine
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- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D267/00—Heterocyclic compounds containing rings of more than six members having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D267/02—Seven-membered rings
- C07D267/08—Seven-membered rings having the hetero atoms in positions 1 and 4
- C07D267/10—Seven-membered rings having the hetero atoms in positions 1 and 4 not condensed with other rings
-
- 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
- C07D295/22—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 hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/14—Nitrogen atoms not forming part of a nitro radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Abstract
Description
Claims
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CN201380062951.5A CN104822373B (en) | 2012-10-15 | 2013-10-11 | Therapeutic compound and composition |
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EP2906212A4 (en) | 2016-06-08 |
MX365747B (en) | 2019-06-12 |
CN104822373A (en) | 2015-08-05 |
AU2013331626B2 (en) | 2018-08-02 |
JP2015536306A (en) | 2015-12-21 |
EP2906212A1 (en) | 2015-08-19 |
JP2018199677A (en) | 2018-12-20 |
AU2013331626A1 (en) | 2015-05-07 |
NZ706999A (en) | 2018-12-21 |
CA2888360A1 (en) | 2014-04-24 |
JP6385352B2 (en) | 2018-09-05 |
US20150299115A1 (en) | 2015-10-22 |
MX2015004762A (en) | 2016-05-24 |
HK1213798A1 (en) | 2016-07-15 |
US10202339B2 (en) | 2019-02-12 |
CN104822373B (en) | 2018-08-28 |
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