JP2010500994A5 - - Google Patents
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- JP2010500994A5 JP2010500994A5 JP2009524671A JP2009524671A JP2010500994A5 JP 2010500994 A5 JP2010500994 A5 JP 2010500994A5 JP 2009524671 A JP2009524671 A JP 2009524671A JP 2009524671 A JP2009524671 A JP 2009524671A JP 2010500994 A5 JP2010500994 A5 JP 2010500994A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- phenyl
- methyloxy
- sulfonyl
- bis
- 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.)
- Pending
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- 150000001875 compounds Chemical class 0.000 claims description 16
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims description 15
- 108091007960 PI3Ks Proteins 0.000 claims description 15
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 695
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 358
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 353
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 338
- -1 lower alkanyl Chemical group 0.000 claims 152
- 125000001072 heteroaryl group Chemical group 0.000 claims 46
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 43
- BEBCJVAWIBVWNZ-UHFFFAOYSA-N glycinamide Chemical compound NCC(N)=O BEBCJVAWIBVWNZ-UHFFFAOYSA-N 0.000 claims 40
- 125000000217 alkyl group Chemical group 0.000 claims 35
- 125000001475 halogen functional group Chemical group 0.000 claims 34
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims 33
- 229910052739 hydrogen Inorganic materials 0.000 claims 33
- 239000001257 hydrogen Substances 0.000 claims 33
- KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 30
- 125000003118 aryl group Chemical group 0.000 claims 28
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 23
- 125000000753 cycloalkyl group Chemical group 0.000 claims 22
- 125000003342 alkenyl group Chemical group 0.000 claims 21
- 125000003107 substituted aryl group Chemical group 0.000 claims 21
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 19
- 150000002431 hydrogen Chemical class 0.000 claims 19
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 18
- 125000001188 haloalkyl group Chemical group 0.000 claims 17
- 239000000203 mixture Substances 0.000 claims 16
- 125000000304 alkynyl group Chemical group 0.000 claims 15
- 150000001408 amides Chemical class 0.000 claims 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 15
- 125000004262 quinoxalin-2-yl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N=C1* 0.000 claims 15
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 14
- 125000004438 haloalkoxy group Chemical group 0.000 claims 12
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- 125000003545 alkoxy group Chemical group 0.000 claims 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 10
- 125000004093 cyano group Chemical group *C#N 0.000 claims 10
- 150000003839 salts Chemical class 0.000 claims 10
- 239000012453 solvate Substances 0.000 claims 9
- 241001024304 Mino Species 0.000 claims 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 8
- 230000035772 mutation Effects 0.000 claims 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 8
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 8
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 8
- 206010028980 Neoplasm Diseases 0.000 claims 7
- 201000011510 cancer Diseases 0.000 claims 7
- 125000004446 heteroarylalkyl group Chemical group 0.000 claims 7
- 229940124530 sulfonamide Drugs 0.000 claims 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 6
- 125000003282 alkyl amino group Chemical group 0.000 claims 5
- 229910052799 carbon Inorganic materials 0.000 claims 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 5
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 4
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 4
- SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 claims 4
- 125000004103 aminoalkyl group Chemical group 0.000 claims 4
- 125000004104 aryloxy group Chemical group 0.000 claims 4
- 150000003456 sulfonamides Chemical class 0.000 claims 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 3
- 108010091528 Proto-Oncogene Proteins B-raf Proteins 0.000 claims 3
- 125000002252 acyl group Chemical group 0.000 claims 3
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims 3
- VALZSZJVEFACEZ-UHFFFAOYSA-N azetidine-3-carboxamide Chemical compound NC(=O)C1CNC1 VALZSZJVEFACEZ-UHFFFAOYSA-N 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
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims 3
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims 3
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 2
- IRHDSXMLSTVXEQ-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 IRHDSXMLSTVXEQ-UHFFFAOYSA-N 0.000 claims 2
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims 2
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims 2
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims 2
- 125000004208 3-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C([H])C(*)=C1[H] 0.000 claims 2
- HAKUWOSPROHOHW-UHFFFAOYSA-N 8-cyclopentyl-2-(ethylamino)-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C2CCCC2)C2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 HAKUWOSPROHOHW-UHFFFAOYSA-N 0.000 claims 2
- HIHMKBKMKSYHII-UHFFFAOYSA-N 8-ethyl-2-(ethylamino)-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(CC)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CC=C1 HIHMKBKMKSYHII-UHFFFAOYSA-N 0.000 claims 2
- 208000032791 BCR-ABL1 positive chronic myelogenous leukemia Diseases 0.000 claims 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims 2
- 208000010833 Chronic myeloid leukaemia Diseases 0.000 claims 2
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 claims 2
- 208000033761 Myelogenous Chronic BCR-ABL Positive Leukemia Diseases 0.000 claims 2
- 229910002651 NO3 Inorganic materials 0.000 claims 2
- DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 2
- 230000003213 activating effect Effects 0.000 claims 2
- 150000001298 alcohols Chemical class 0.000 claims 2
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 2
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims 2
- 125000004965 chloroalkyl group Chemical group 0.000 claims 2
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims 2
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 2
- 125000005343 heterocyclic alkyl group Chemical group 0.000 claims 2
- 125000000623 heterocyclic group Chemical group 0.000 claims 2
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 201000001441 melanoma Diseases 0.000 claims 2
- 125000004043 oxo group Chemical group O=* 0.000 claims 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 2
- 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 2
- 125000005415 substituted alkoxy group Chemical group 0.000 claims 2
- 125000000547 substituted alkyl group Chemical group 0.000 claims 2
- IADUEWIQBXOCDZ-UHFFFAOYSA-N (2S)-azetidine-2-carboxylic acid Natural products OC(=O)C1CCN1 IADUEWIQBXOCDZ-UHFFFAOYSA-N 0.000 claims 1
- DBTDBYINUJMLRZ-UHFFFAOYSA-N (3,3-difluoroazetidin-1-yl)-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]methanone Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1C(=O)N1CC(F)(F)C1 DBTDBYINUJMLRZ-UHFFFAOYSA-N 0.000 claims 1
- AMKMWZPNFOTRDH-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)phenyl]methanone Chemical compound C1C(N)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F AMKMWZPNFOTRDH-UHFFFAOYSA-N 0.000 claims 1
- ZZJMLFCTJLGTEI-UHFFFAOYSA-N (3-aminoazetidin-1-yl)-[4-(2-fluoro-4-iodoanilino)thiophen-3-yl]methanone Chemical compound C1C(N)CN1C(=O)C1=CSC=C1NC1=CC=C(I)C=C1F ZZJMLFCTJLGTEI-UHFFFAOYSA-N 0.000 claims 1
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims 1
- DSIBSRXKQRYPJP-UHFFFAOYSA-N 1,2-oxazole-5-carboxamide Chemical compound NC(=O)C1=CC=NO1 DSIBSRXKQRYPJP-UHFFFAOYSA-N 0.000 claims 1
- OIEUKOXYYRCJOB-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-hydroxyazetidine-2-carboxamide Chemical compound ONC(=O)C1CCN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F OIEUKOXYYRCJOB-UHFFFAOYSA-N 0.000 claims 1
- VGQZTOCHLVGGBK-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-hydroxyazetidine-3-carboxamide Chemical compound C1C(C(=O)NO)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F VGQZTOCHLVGGBK-UHFFFAOYSA-N 0.000 claims 1
- UJXSKQZZTUMIPR-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-methyl-n-prop-2-enylazetidine-3-carboxamide Chemical compound C1C(C(=O)N(CC=C)C)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F UJXSKQZZTUMIPR-UHFFFAOYSA-N 0.000 claims 1
- OUZFPOWROZRFOA-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]-n-methylazetidine-3-carboxamide Chemical compound C1C(C(=O)NC)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F OUZFPOWROZRFOA-UHFFFAOYSA-N 0.000 claims 1
- JNRJARCELIUHEU-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]azetidin-3-one Chemical compound C=1C=C(I)C=C(F)C=1NC1=C(F)C(F)=CC=C1C(=O)N1CC(=O)C1 JNRJARCELIUHEU-UHFFFAOYSA-N 0.000 claims 1
- QYQLVTVZLMBZKM-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]azetidine-2-carboxylic acid Chemical compound OC(=O)C1CCN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F QYQLVTVZLMBZKM-UHFFFAOYSA-N 0.000 claims 1
- KDMCTGAOBPQHRZ-UHFFFAOYSA-N 1-[3,4-difluoro-2-(2-fluoro-4-iodoanilino)benzoyl]azetidine-3-carboxylic acid Chemical compound C1C(C(=O)O)CN1C(=O)C1=CC=C(F)C(F)=C1NC1=CC=C(I)C=C1F KDMCTGAOBPQHRZ-UHFFFAOYSA-N 0.000 claims 1
- 125000004486 1-methylpiperidin-3-yl group Chemical group CN1CC(CCC1)* 0.000 claims 1
- 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- HTJOVUNXGJONIS-UHFFFAOYSA-N 2-(benzylamino)-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NCC1=CC=CC=C1 HTJOVUNXGJONIS-UHFFFAOYSA-N 0.000 claims 1
- JMNLUUPZYOLBHN-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-6-(1H-pyrazol-5-yl)-8H-pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1NC2=NC(NCC)=NC(C)=C2C=C1C=1C=CNN=1 JMNLUUPZYOLBHN-UHFFFAOYSA-N 0.000 claims 1
- ZHRYNYKDUYSRGB-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1N1C=CC=N1 ZHRYNYKDUYSRGB-UHFFFAOYSA-N 0.000 claims 1
- HSEBQNPXSICMIB-UHFFFAOYSA-N 2-(ethylamino)-4-methyl-8-propan-2-yl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C1=CC=CS1 HSEBQNPXSICMIB-UHFFFAOYSA-N 0.000 claims 1
- QRJXSWSAFBXPGH-UHFFFAOYSA-N 2-(ethylamino)-6-(furan-3-yl)-4-methyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(NCC)=NC(C)=C2C=C1C=1C=COC=1 QRJXSWSAFBXPGH-UHFFFAOYSA-N 0.000 claims 1
- CBBFWSMELCDMPZ-UHFFFAOYSA-N 2-(methylamino)acetamide Chemical compound CNCC(N)=O CBBFWSMELCDMPZ-UHFFFAOYSA-N 0.000 claims 1
- KTFDYVNEGTXQCV-UHFFFAOYSA-N 2-Thiophenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CS1 KTFDYVNEGTXQCV-UHFFFAOYSA-N 0.000 claims 1
- GWQBQZWHKVNWAQ-UHFFFAOYSA-N 2-[4-(4-benzylpiperazin-1-yl)anilino]-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC=C1 GWQBQZWHKVNWAQ-UHFFFAOYSA-N 0.000 claims 1
- AAZQBTDBIDQFOT-UHFFFAOYSA-N 2-[4-(4-benzylpiperazin-1-yl)anilino]-8-ethyl-4-methyl-6-thiophen-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3SC=CC=3)C(=O)N(CC)C2=NC=1NC(C=C1)=CC=C1N(CC1)CCN1CC1=CC=CC=C1 AAZQBTDBIDQFOT-UHFFFAOYSA-N 0.000 claims 1
- FPWGZOOQOSVFNF-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-6-phenyl-8-propan-2-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(C=2C=CC=CC=2)C(=O)N2C(C)C)C2=N1 FPWGZOOQOSVFNF-UHFFFAOYSA-N 0.000 claims 1
- GXWZBYLDKUHYMM-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(C2=NNC=C2)C(=O)N2C(C)C)C2=N1 GXWZBYLDKUHYMM-UHFFFAOYSA-N 0.000 claims 1
- FMKRGZMYBBIDRU-UHFFFAOYSA-N 2-[4-(4-ethylpiperazin-1-yl)anilino]-4-methyl-8-propan-2-yl-6-pyrazol-1-ylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1CN(CC)CCN1C(C=C1)=CC=C1NC1=NC(C)=C(C=C(N2N=CC=C2)C(=O)N2C(C)C)C2=N1 FMKRGZMYBBIDRU-UHFFFAOYSA-N 0.000 claims 1
- LCQNZXBWUQGXRT-UHFFFAOYSA-N 2-[4-[2-(diethylamino)ethoxy]anilino]-8-ethyl-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound C1=CC(OCCN(CC)CC)=CC=C1NC1=NC(C)=C(C=C(C=2C=CC=CC=2)C(=O)N2CC)C2=N1 LCQNZXBWUQGXRT-UHFFFAOYSA-N 0.000 claims 1
- HZRBHCGEYZORAK-UHFFFAOYSA-N 2-amino-4-methyl-8-propan-2-yl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1N(C(C)C)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 HZRBHCGEYZORAK-UHFFFAOYSA-N 0.000 claims 1
- QSWPHEWUFGXYPX-UHFFFAOYSA-N 2-amino-8-cyclopentyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound O=C1C(C2=NNC=C2)=CC=2C(C)=NC(N)=NC=2N1C1CCCC1 QSWPHEWUFGXYPX-UHFFFAOYSA-N 0.000 claims 1
- RGHYDLZMTYDBDT-UHFFFAOYSA-N 2-amino-8-ethyl-4-methyl-6-(1H-pyrazol-5-yl)-7-pyrido[2,3-d]pyrimidinone Chemical compound O=C1N(CC)C2=NC(N)=NC(C)=C2C=C1C=1C=CNN=1 RGHYDLZMTYDBDT-UHFFFAOYSA-N 0.000 claims 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims 1
- PCVGVJIERNKFME-UHFFFAOYSA-N 2-anilino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(Br)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 PCVGVJIERNKFME-UHFFFAOYSA-N 0.000 claims 1
- ZSBCYLLGJGQANG-UHFFFAOYSA-N 2-anilino-8-cyclopentyl-4-methyl-6-(1h-pyrazol-5-yl)pyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C=2N(C3CCCC3)C(=O)C(C3=NNC=C3)=CC=2C(C)=NC=1NC1=CC=CC=C1 ZSBCYLLGJGQANG-UHFFFAOYSA-N 0.000 claims 1
- VWDQGKGGOXAPIQ-UHFFFAOYSA-N 2-anilino-8-ethyl-4-methyl-6-phenylpyrido[2,3-d]pyrimidin-7-one Chemical compound N=1C(C)=C2C=C(C=3C=CC=CC=3)C(=O)N(CC)C2=NC=1NC1=CC=CC=C1 VWDQGKGGOXAPIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims 1
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Families Citing this family (91)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SI1934174T1 (sl) * | 2005-10-07 | 2011-08-31 | Exelixis Inc | Inhibitorji MEK in postopki za njihovo uporabo |
| EA016945B1 (ru) * | 2005-10-07 | 2012-08-30 | Экселиксис, Инк. | ПИРИДОПИРИМИДИНОНОВЫЕ ИНГИБИТОРЫ PI3Kα |
| AU2013201011B2 (en) * | 2005-10-07 | 2016-04-21 | Exelixis, Inc. | N- (3-amino-quinoxalin-2-yl) -sulfonamide derivatives and their use as phosphatidylinositol 3-kinase inhibitors |
| US7989622B2 (en) * | 2005-10-07 | 2011-08-02 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors and methods of their use |
| GB0601962D0 (en) | 2006-01-31 | 2006-03-15 | Ucb Sa | Therapeutic agents |
| CN101528231A (zh) | 2006-08-16 | 2009-09-09 | 埃克塞利希斯股份有限公司 | 在癌症的治疗中使用pi3k和mek调控剂 |
| PT2074122E (pt) | 2006-09-15 | 2011-08-24 | Pfizer Prod Inc | Compostos de pirido(2,3-d)-pirimidinona e sua utilização como inibidores de pi3 |
| PL2101759T3 (pl) | 2006-12-14 | 2019-05-31 | Exelixis Inc | Sposoby stosowania inhibitorów MEK |
| JP5508027B2 (ja) * | 2007-02-22 | 2014-05-28 | メルク セローノ ソシエテ アノニム | キノキサリン化合物及びその使用 |
| WO2008124085A2 (en) * | 2007-04-03 | 2008-10-16 | Exelixis, Inc. | Methods of using combinations of mek and jak-2 inhibitors |
| MY150697A (en) * | 2007-04-10 | 2014-02-28 | Exelixis Inc | Methods of treating cancer using pyridopyrimdinone inhibitors of p13k alpha |
| CA2683784A1 (en) * | 2007-04-11 | 2008-10-23 | Exelixis, Inc. | Pyrido[2,3-d]pyrimidin-7-one compounds as inhibitors of pi3k-alpha for the treatment of cancer |
| CN101711249A (zh) * | 2007-04-11 | 2010-05-19 | 埃克塞里艾克西斯公司 | 作为PI3K-α的抑制剂用于治疗癌症的吡啶并[2,3-D]嘧啶-7-酮化合物 |
| WO2008127594A2 (en) | 2007-04-11 | 2008-10-23 | Exelixis, Inc. | Combination therapies comprising quinoxaline inhibitors of pi3k-alpha for use in the treatment of cancer |
| WO2009017838A2 (en) * | 2007-08-01 | 2009-02-05 | Exelixis, Inc. | Combinations of jak-2 inhibitors and other agents |
| WO2009139886A2 (en) * | 2008-05-14 | 2009-11-19 | University Of Pittsburgh-Of The Commonwealth System Of Higher Education | Targeting an hiv-1 nef-host cell kinase complex |
| GB0815947D0 (en) | 2008-09-02 | 2008-10-08 | Univ Dundee | Compounds |
| US8476431B2 (en) * | 2008-11-03 | 2013-07-02 | Itellikine LLC | Benzoxazole kinase inhibitors and methods of use |
| US8673908B2 (en) | 2008-11-10 | 2014-03-18 | Kyowa Hakko Kirin Co., Ltd. | Kynurenine production inhibitor |
| WO2010068738A1 (en) | 2008-12-10 | 2010-06-17 | Dana-Farber Cancer Institute, Inc. | Mek mutations conferring resistance to mek inhibitors |
| JP5728683B2 (ja) | 2009-09-04 | 2015-06-03 | バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ | チロシンスレオニンキナーゼ阻害剤としての置換アミノキノキサリン |
| US20120245180A1 (en) * | 2009-09-28 | 2012-09-27 | Glaxosmithkline Llc | Combination |
| CA2776944A1 (en) * | 2009-10-12 | 2011-05-12 | F. Hoffmann-La Roche Ag | Combinations of a pi3k inhibitor and a mek inhibitor |
| UY33221A (es) * | 2010-02-09 | 2011-09-30 | Univ California | MÉTODOS PARA TRATAR CÁNCER USANDO INHIBIDORES DE PI3K Y mTOR EN COMBINACIÓN CON INHIBIDORES DE AUTOFAGIA |
| ES2576061T3 (es) | 2010-02-25 | 2016-07-05 | Dana-Farber Cancer Institute, Inc. | Mutaciones de BRAF que confieren resistencia a inhibidores de BRAF |
| BR112012022801B8 (pt) | 2010-03-09 | 2019-10-29 | Dana Farber Cancer Inst Inc | método de identificar um indivíduo que tem câncer que é provável beneficiar-se do tratamento com uma terapia de combinação com um inibidor de raf e um segundo inibidor e uso de um inibidor de raf e um segundo inibidor para a fabricação de um medicamento para tratar câncer |
| EP2598660B1 (en) | 2010-07-26 | 2017-03-15 | Biomatrica, INC. | Compositions for stabilizing dna, rna and proteins in blood and other biological samples during shipping and storage at ambient temperatures |
| WO2012018639A2 (en) | 2010-07-26 | 2012-02-09 | Biomatrica, Inc. | Compositions for stabilizing dna, rna and proteins in saliva and other biological samples during shipping and storage at ambient temperatures |
| EP2616442B8 (en) | 2010-09-14 | 2018-10-17 | Exelixis, Inc. | Inhibitors of pi3k-delta and methods of their use and manufacture |
| KR20130141528A (ko) * | 2010-10-20 | 2013-12-26 | 메르크 세로노 에스에이 제네바 | 치환 ｎ-(3-아미노-퀴녹살린-2-일)-술폰아미드 및 이들의 중간체인 ｎ-(3-클로로-퀴녹살린-2-일)술폰아미드의 제조 방법 |
| DE102010048800A1 (de) | 2010-10-20 | 2012-05-10 | Merck Patent Gmbh | Chinoxalinderivate |
| WO2012065057A2 (en) * | 2010-11-12 | 2012-05-18 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors and methods of their use |
| AU2011329666A1 (en) * | 2010-11-19 | 2013-05-30 | Glaxosmithkline Intellectual Property (No.2) Limited | Method of treatment with BRaf inhibitor |
| US8754114B2 (en) | 2010-12-22 | 2014-06-17 | Incyte Corporation | Substituted imidazopyridazines and benzimidazoles as inhibitors of FGFR3 |
| CN102718750B (zh) * | 2011-03-31 | 2015-03-11 | 中国人民解放军军事医学科学院毒物药物研究所 | 含吖啶环的氨基吡啶类衍生物及其用途 |
| EP2758057B1 (en) | 2011-09-22 | 2017-05-31 | Exelixis, Inc. | Method for treating osteoporosis |
| CN107375289A (zh) | 2011-11-01 | 2017-11-24 | 埃克塞利希斯股份有限公司 | 用于治疗淋巴组织增生性恶性肿瘤的作为磷脂酰肌醇3‑激酶抑制剂的化合物 |
| WO2013067306A1 (en) * | 2011-11-02 | 2013-05-10 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors for the treatment of childhood cancers |
| CN103204825B (zh) | 2012-01-17 | 2015-03-04 | 上海科州药物研发有限公司 | 作为蛋白激酶抑制剂的苯并噻唑化合物及其制备方法和用途 |
| WO2013135612A1 (en) | 2012-03-14 | 2013-09-19 | Bayer Intellectual Property Gmbh | Substituted imidazopyridazines |
| US20150141470A1 (en) | 2012-05-08 | 2015-05-21 | The Broad Institute, Inc. | Diagnostic and treatment methods in patients having or at risk of developing resistance to cancer therapy |
| RS58514B1 (sr) | 2012-06-13 | 2019-04-30 | Incyte Holdings Corp | Supstituisana triciklična jedinjenja kao inhibitori fgfr |
| US9388185B2 (en) | 2012-08-10 | 2016-07-12 | Incyte Holdings Corporation | Substituted pyrrolo[2,3-b]pyrazines as FGFR inhibitors |
| KR102204520B1 (ko) | 2012-10-12 | 2021-01-20 | 엑셀리시스, 인코포레이티드 | 암의 치료에 사용하기 위한 화합물의 신규 제조 방법 |
| US20150265679A1 (en) | 2012-11-02 | 2015-09-24 | The United States Of America, As Represented By Secretary, Department Of Health And Human Services | Method of reducing adverse effects in a cancer patient undregoing treatment with a mek inhibitor |
| US9266892B2 (en) | 2012-12-19 | 2016-02-23 | Incyte Holdings Corporation | Fused pyrazoles as FGFR inhibitors |
| US9725703B2 (en) | 2012-12-20 | 2017-08-08 | Biomatrica, Inc. | Formulations and methods for stabilizing PCR reagents |
| CA2905123A1 (en) | 2013-03-15 | 2014-09-18 | Genentech, Inc. | Methods of treating cancer and preventing cancer drug resistance |
| PH12015502383B1 (en) | 2013-04-19 | 2023-02-03 | Incyte Holdings Corp | Bicyclic heterocycles as fgfr inhibitors |
| AP2015008898A0 (en) | 2013-06-11 | 2015-12-31 | Bayer Pharma AG | Prodrug derivatives of substituted triazolopyridines |
| WO2015002729A2 (en) | 2013-06-13 | 2015-01-08 | Biomatrica, Inc. | Cell stabilization |
| RU2715236C2 (ru) | 2014-03-26 | 2020-02-26 | Астекс Терапьютикс Лтд | Комбинации |
| ES2786373T3 (es) | 2014-06-10 | 2020-10-09 | Biomatrica Inc | Estabilización de trombocitos a temperaturas ambiente |
| US20170114323A1 (en) | 2014-06-19 | 2017-04-27 | Whitehead Institute For Biomedical Research | Uses of kinase inhibitors for inducing and maintaining pluripotency |
| CA2954879C (en) * | 2014-07-16 | 2022-09-06 | Development Center For Biotechnology | Quinoxaline compounds, method for preparing the same and use thereof |
| US10851105B2 (en) | 2014-10-22 | 2020-12-01 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| TWI719960B (zh) | 2015-02-10 | 2021-03-01 | 英商阿斯迪克治療公司 | 新穎組成物 |
| TWI712601B (zh) | 2015-02-20 | 2020-12-11 | 美商英塞特公司 | 作為fgfr抑制劑之雙環雜環 |
| MA41551A (fr) | 2015-02-20 | 2017-12-26 | Incyte Corp | Hétérocycles bicycliques utilisés en tant qu'inhibiteurs de fgfr4 |
| US9580423B2 (en) | 2015-02-20 | 2017-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR4 inhibitors |
| AR105483A1 (es) | 2015-06-30 | 2017-10-11 | Exelixis Inc | Sal de fumarato cristalina de (s)-[3,4-difluoro-2-(2-fluoro-4-yodofenilamino)fenil][3-hidroxi-3-(piperidin-2-il)azetidin-1-il]-metanona |
| KR20250047404A (ko) | 2015-12-08 | 2025-04-03 | 바이오매트리카 인코포레이티드 | 적혈구 침강 속도의 감소 |
| WO2017205795A1 (en) | 2016-05-26 | 2017-11-30 | The Regents Of The University Of California | Compounds and methods for hematopoietic regeneration |
| WO2018183936A1 (en) * | 2017-03-31 | 2018-10-04 | The Broad Institute, Inc. | Compounds and methods useful for treating or preventing cancers |
| US11896591B2 (en) | 2017-05-22 | 2024-02-13 | University Of Virginia Patent Foundation | Compositions and methods for preparing and using mitochondrial uncouplers |
| AR111960A1 (es) | 2017-05-26 | 2019-09-04 | Incyte Corp | Formas cristalinas de un inhibidor de fgfr y procesos para su preparación |
| EP3717450A4 (en) * | 2017-11-29 | 2022-01-26 | The Regents of the University of California | Compounds and methods for hematopoietic regeneration |
| AU2019262579B2 (en) | 2018-05-04 | 2024-09-12 | Incyte Corporation | Salts of an FGFR inhibitor |
| HRP20241288T1 (hr) | 2018-05-04 | 2024-12-06 | Incyte Corporation | Čvrsti oblici fgfr inhibitora i postupci za njihovu proizvodnju |
| ES2929406T3 (es) * | 2018-05-21 | 2022-11-29 | Nerviano Medical Sciences Srl | Compuestos de piridonas heterocondensadas y su uso como inhibidores de IDH |
| CA3120351A1 (en) * | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Aryl-aniline and heteroaryl-aniline compounds for treatment of skin cancers |
| EP4233834A3 (en) * | 2018-11-20 | 2023-10-25 | NFlection Therapeutics, Inc. | Aryl-aniline and heteroaryl-aniline compounds for treatment of birthmarks |
| WO2020106305A1 (en) * | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Thienyl-aniline compounds for treatment of dermal disorders |
| WO2020106308A1 (en) | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Naphthyridinone-aniline compounds for treatment of dermal disorders |
| WO2020106306A1 (en) * | 2018-11-20 | 2020-05-28 | Nflection Therapeutics, Inc. | Cyanoaryl-aniline compounds for treatment of dermal disorders |
| US11628162B2 (en) | 2019-03-08 | 2023-04-18 | Incyte Corporation | Methods of treating cancer with an FGFR inhibitor |
| US11591329B2 (en) | 2019-07-09 | 2023-02-28 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| WO2021067374A1 (en) | 2019-10-01 | 2021-04-08 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CA3157361A1 (en) | 2019-10-14 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| WO2021076728A1 (en) | 2019-10-16 | 2021-04-22 | Incyte Corporation | Bicyclic heterocycles as fgfr inhibitors |
| CN115038700B (zh) | 2019-11-08 | 2025-07-25 | 内尔维亚诺医疗科学公司 | 偕二取代的杂环化合物及其作为idh抑制剂的用途 |
| JP7832891B2 (ja) | 2019-12-04 | 2026-03-18 | インサイト・コーポレイション | Ｆｇｆｒ阻害剤の誘導体 |
| CA3163875A1 (en) | 2019-12-04 | 2021-06-10 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US12012409B2 (en) | 2020-01-15 | 2024-06-18 | Incyte Corporation | Bicyclic heterocycles as FGFR inhibitors |
| ES2836551A1 (es) * | 2020-08-11 | 2021-06-25 | Molik Candelo Holmes | Fármaco andreaquivi C34H34N6O6S |
| WO2022221170A1 (en) | 2021-04-12 | 2022-10-20 | Incyte Corporation | Combination therapy comprising an fgfr inhibitor and a nectin-4 targeting agent |
| US12371667B2 (en) | 2021-05-13 | 2025-07-29 | Washington University | Enhanced methods for inducing and maintaining naive human pluripotent stem cells |
| US11939331B2 (en) | 2021-06-09 | 2024-03-26 | Incyte Corporation | Tricyclic heterocycles as FGFR inhibitors |
| CA3220155A1 (en) | 2021-06-09 | 2022-12-15 | Incyte Corporation | Tricyclic heterocycles as fgfr inhibitors |
| US12447163B2 (en) * | 2021-07-16 | 2025-10-21 | Jazz Pharmaceuticals Therapeutics, Inc. | Liposomal formulations of Bcl inhibitors |
| IL312977A (en) | 2021-11-23 | 2024-07-01 | Nflection Therapeutics Inc | Formulations of pyrrolopyridine-aniline compounds |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1998033798A2 (en) | 1997-02-05 | 1998-08-06 | Warner Lambert Company | Pyrido[2,3-d]pyrimidines and 4-amino-pyrimidines as inhibitors of cell proliferation |
| BR9810385A (pt) * | 1997-07-01 | 2000-09-05 | Warner Lambert Co | Derivados de ácido benzóico 2-(4-bromo ou 4-iodo fenilamino) e sua utilização como inibidores de mek |
| US7019002B2 (en) * | 2001-12-11 | 2006-03-28 | Pharmacia & Upjohn, S.P.A. | Pyridopyrimidinones derivatives as telomerase inhibitors |
| ATE373659T1 (de) * | 2004-05-04 | 2007-10-15 | Warner Lambert Co | Pyrrolylsubstituierte pyrido(2,3-d)pyrimidin-7- one und derivate davon als therapeutische mittel |
| EP1799699A1 (en) * | 2004-10-13 | 2007-06-27 | Wyeth | Analogs of 17-hydroxywortmannin as pi3k inhibitors |
| ZA200703912B (en) * | 2004-10-20 | 2008-09-25 | Serono Lab | 3-arylamino pyridine derivatives |
| US8071597B2 (en) | 2005-08-26 | 2011-12-06 | Merck Serono Sa | Pyrazine compounds and uses as PI3K inhibitors |
| US7989622B2 (en) | 2005-10-07 | 2011-08-02 | Exelixis, Inc. | Phosphatidylinositol 3-kinase inhibitors and methods of their use |
| SI1934174T1 (sl) * | 2005-10-07 | 2011-08-31 | Exelixis Inc | Inhibitorji MEK in postopki za njihovo uporabo |
| CN102746298A (zh) | 2005-10-07 | 2012-10-24 | 埃克塞里艾克西斯公司 | PI3Kα的吡啶并嘧啶酮抑制剂 |
| EA016945B1 (ru) | 2005-10-07 | 2012-08-30 | Экселиксис, Инк. | ПИРИДОПИРИМИДИНОНОВЫЕ ИНГИБИТОРЫ PI3Kα |
| CN101528231A (zh) * | 2006-08-16 | 2009-09-09 | 埃克塞利希斯股份有限公司 | 在癌症的治疗中使用pi3k和mek调控剂 |
| PL2101759T3 (pl) * | 2006-12-14 | 2019-05-31 | Exelixis Inc | Sposoby stosowania inhibitorów MEK |
| MY150697A (en) | 2007-04-10 | 2014-02-28 | Exelixis Inc | Methods of treating cancer using pyridopyrimdinone inhibitors of p13k alpha |
| CA2683784A1 (en) | 2007-04-11 | 2008-10-23 | Exelixis, Inc. | Pyrido[2,3-d]pyrimidin-7-one compounds as inhibitors of pi3k-alpha for the treatment of cancer |
| CN101711249A (zh) | 2007-04-11 | 2010-05-19 | 埃克塞里艾克西斯公司 | 作为PI3K-α的抑制剂用于治疗癌症的吡啶并[2,3-D]嘧啶-7-酮化合物 |
| WO2008127594A2 (en) | 2007-04-11 | 2008-10-23 | Exelixis, Inc. | Combination therapies comprising quinoxaline inhibitors of pi3k-alpha for use in the treatment of cancer |
| AR073524A1 (es) | 2008-09-30 | 2010-11-10 | Exelixis Inc | Piridopirimidinonas inhibidores de pi3k a y m tor |
| UY33221A (es) | 2010-02-09 | 2011-09-30 | Univ California | MÉTODOS PARA TRATAR CÁNCER USANDO INHIBIDORES DE PI3K Y mTOR EN COMBINACIÓN CON INHIBIDORES DE AUTOFAGIA |
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2007
- 2007-08-16 CN CNA200780038496XA patent/CN101528231A/zh not_active Withdrawn
- 2007-08-16 JP JP2009524671A patent/JP2010500994A/ja active Pending
- 2007-08-16 CN CN201510204883.2A patent/CN104784695A/zh active Pending
- 2007-08-16 EP EP07811344A patent/EP2056829B9/en active Active
- 2007-08-16 AU AU2007284562A patent/AU2007284562B2/en not_active Ceased
- 2007-08-16 AT AT07811344T patent/ATE539752T1/de active
- 2007-08-16 CA CA002658725A patent/CA2658725A1/en not_active Abandoned
- 2007-08-16 US US12/373,257 patent/US20100075947A1/en not_active Abandoned
- 2007-08-16 WO PCT/US2007/018057 patent/WO2008021389A2/en not_active Ceased
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2012
- 2012-08-07 US US13/568,649 patent/US8642584B2/en active Active
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2013
- 2013-05-14 JP JP2013102030A patent/JP2013151570A/ja not_active Withdrawn
- 2013-12-07 US US14/099,939 patent/US20140100215A1/en not_active Abandoned
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2014
- 2014-03-28 JP JP2014067502A patent/JP2014122243A/ja active Pending
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2016
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