JP2013536193A5 - - Google Patents
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- JP2013536193A5 JP2013536193A5 JP2013524226A JP2013524226A JP2013536193A5 JP 2013536193 A5 JP2013536193 A5 JP 2013536193A5 JP 2013524226 A JP2013524226 A JP 2013524226A JP 2013524226 A JP2013524226 A JP 2013524226A JP 2013536193 A5 JP2013536193 A5 JP 2013536193A5
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- JP
- Japan
- Prior art keywords
- membered
- nitrogen
- sulfur
- oxygen
- optionally substituted
- 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.)
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- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 352
- 229910052757 nitrogen Inorganic materials 0.000 claims description 281
- 229910052760 oxygen Inorganic materials 0.000 claims description 262
- 229910052717 sulfur Inorganic materials 0.000 claims description 262
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 251
- 239000001301 oxygen Chemical group 0.000 claims description 251
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 250
- 239000011593 sulfur Chemical group 0.000 claims description 249
- 125000005842 heteroatom Chemical group 0.000 claims description 248
- 150000001875 compounds Chemical class 0.000 claims description 175
- 125000001931 aliphatic group Chemical group 0.000 claims description 163
- 229910052739 hydrogen Inorganic materials 0.000 claims description 161
- 239000001257 hydrogen Substances 0.000 claims description 161
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 146
- 125000000623 heterocyclic group Chemical group 0.000 claims description 130
- 125000002723 alicyclic group Chemical group 0.000 claims description 128
- 125000001313 C5-C10 heteroaryl group Chemical group 0.000 claims description 121
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 110
- 125000000217 alkyl group Chemical group 0.000 claims description 92
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 81
- 229910052736 halogen Inorganic materials 0.000 claims description 51
- 150000002367 halogens Chemical class 0.000 claims description 51
- 150000002431 hydrogen Chemical class 0.000 claims description 48
- 125000003118 aryl group Chemical group 0.000 claims description 40
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 30
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- 150000003839 salts Chemical class 0.000 claims description 29
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 28
- 125000004429 atom Chemical group 0.000 claims description 24
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 23
- 125000001188 haloalkyl group Chemical group 0.000 claims description 19
- 125000001624 naphthyl group Chemical group 0.000 claims description 18
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims description 17
- -1 heterocyclyl nitrogen Chemical group 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims description 6
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
- 150000002780 morpholines Chemical class 0.000 claims description 6
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 5
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 3
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 claims description 3
- 125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 3
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 3
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 3
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
- 230000002062 proliferating effect Effects 0.000 claims description 3
- 229920006395 saturated elastomer Polymers 0.000 claims description 3
- 102000010400 1-phosphatidylinositol-3-kinase activity proteins Human genes 0.000 claims description 2
- 101000605630 Homo sapiens Phosphatidylinositol 3-kinase catalytic subunit type 3 Proteins 0.000 claims description 2
- 108091007960 PI3Ks Proteins 0.000 claims description 2
- 102100038329 Phosphatidylinositol 3-kinase catalytic subunit type 3 Human genes 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 230000000694 effects Effects 0.000 claims description 2
- 230000002401 inhibitory effect Effects 0.000 claims description 2
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 1
- 125000004354 sulfur functional group Chemical group 0.000 claims 1
- 0 CCc(c(NC(C)=O)c1)ccc1-c1cc(C(c(cc2)ccc2Cl)N(C)C)c(*(N)NC=N)[s]1 Chemical compound CCc(c(NC(C)=O)c1)ccc1-c1cc(C(c(cc2)ccc2Cl)N(C)C)c(*(N)NC=N)[s]1 0.000 description 6
- TVEXGJYMHHTVKP-UHFFFAOYSA-N 6-oxabicyclo[3.2.1]oct-3-en-7-one Chemical compound C1C2C(=O)OC1C=CC2 TVEXGJYMHHTVKP-UHFFFAOYSA-N 0.000 description 5
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 2
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
- 208000024172 Cardiovascular disease Diseases 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
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- 230000002757 inflammatory effect Effects 0.000 description 2
- 229910052711 selenium Inorganic materials 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
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- 208000003174 Brain Neoplasms Diseases 0.000 description 1
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- 208000026310 Breast neoplasm Diseases 0.000 description 1
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- ZVBVUPVLCMPBBU-UHFFFAOYSA-N CC(Nc1cc(-c2cc(C(c3ccccc3)N3C(CO)CCC3)c(-c3nnc[nH]3)[s]2)ccn1)=O Chemical compound CC(Nc1cc(-c2cc(C(c3ccccc3)N3C(CO)CCC3)c(-c3nnc[nH]3)[s]2)ccn1)=O ZVBVUPVLCMPBBU-UHFFFAOYSA-N 0.000 description 1
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- LWNADROKZGHQNJ-UHFFFAOYSA-N CCOC(c1c(Cc2ccccc2)[s]c(-c2c(N)nc(Nc(c(C3CCN(Cc4c(C(O)=O)nc(-c5ccncc5)[s]4)CC3)c3)ccc3S(N)(=O)=O)[s]2)n1)=O Chemical compound CCOC(c1c(Cc2ccccc2)[s]c(-c2c(N)nc(Nc(c(C3CCN(Cc4c(C(O)=O)nc(-c5ccncc5)[s]4)CC3)c3)ccc3S(N)(=O)=O)[s]2)n1)=O LWNADROKZGHQNJ-UHFFFAOYSA-N 0.000 description 1
- YGLXNHDCECOXJF-UHFFFAOYSA-N CCOC(c1c(Nc(cccc2)c2N)nc(-c2ccncc2)[s]1)=O Chemical compound CCOC(c1c(Nc(cccc2)c2N)nc(-c2ccncc2)[s]1)=O YGLXNHDCECOXJF-UHFFFAOYSA-N 0.000 description 1
- URNMXNVOLWQODN-UHFFFAOYSA-N COC(c1c(-c2ccccc2)[s]c(N2CCOCC2)c1C(OC)=O)=O Chemical compound COC(c1c(-c2ccccc2)[s]c(N2CCOCC2)c1C(OC)=O)=O URNMXNVOLWQODN-UHFFFAOYSA-N 0.000 description 1
- LIRLOKQRIUYQTA-UHFFFAOYSA-N COC(c1c(C(c2ccccc2)=O)[s]c(N2CCOCC2)c1C(OC)=O)=O Chemical compound COC(c1c(C(c2ccccc2)=O)[s]c(N2CCOCC2)c1C(OC)=O)=O LIRLOKQRIUYQTA-UHFFFAOYSA-N 0.000 description 1
- KMHLYFVZYMSJIL-UHFFFAOYSA-N COC(c1c(N2CCOCC2)[s]c(N2CCOCC2)c1C(OC)=O)=O Chemical compound COC(c1c(N2CCOCC2)[s]c(N2CCOCC2)c1C(OC)=O)=O KMHLYFVZYMSJIL-UHFFFAOYSA-N 0.000 description 1
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- GCEBGUNLHLTBFG-UHFFFAOYSA-N Cc1cc(Nc2nc(-c3nc(C(N)=O)c(NC4CCCCC4)[s]3)ccn2)cc(C)c1 Chemical compound Cc1cc(Nc2nc(-c3nc(C(N)=O)c(NC4CCCCC4)[s]3)ccn2)cc(C)c1 GCEBGUNLHLTBFG-UHFFFAOYSA-N 0.000 description 1
- YLSWDXMFMDFPGV-UHFFFAOYSA-O Cc1n[n](ccc(CNCc(ccc(O)c2)c2OC)c2)c2c1-c1nc(Cc(cc2)ccc2Cl)c(C(NC=[NH2+])=N)[s]1 Chemical compound Cc1n[n](ccc(CNCc(ccc(O)c2)c2OC)c2)c2c1-c1nc(Cc(cc2)ccc2Cl)c(C(NC=[NH2+])=N)[s]1 YLSWDXMFMDFPGV-UHFFFAOYSA-O 0.000 description 1
- 206010008342 Cervix carcinoma Diseases 0.000 description 1
- WPFVNRJLEFHHAW-UHFFFAOYSA-N Clc1ccc(CC2N=C(c3ccncc3)SC2c2ncc[nH]2)cc1 Chemical compound Clc1ccc(CC2N=C(c3ccncc3)SC2c2ncc[nH]2)cc1 WPFVNRJLEFHHAW-UHFFFAOYSA-N 0.000 description 1
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- 208000005718 Stomach Neoplasms Diseases 0.000 description 1
- 208000007536 Thrombosis Diseases 0.000 description 1
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- 230000001154 acute effect Effects 0.000 description 1
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- 230000036783 anaphylactic response Effects 0.000 description 1
- 208000003455 anaphylaxis Diseases 0.000 description 1
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37259410P | 2010-08-11 | 2010-08-11 | |
| US61/372,594 | 2010-08-11 | ||
| US201161438375P | 2011-02-01 | 2011-02-01 | |
| US61/438,375 | 2011-02-01 | ||
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- 2011-08-11 SG SG10201506238SA patent/SG10201506238SA/en unknown
- 2011-08-11 TW TW100128796A patent/TW201217365A/zh unknown
- 2011-08-11 PE PE2013000258A patent/PE20131304A1/es not_active Application Discontinuation
- 2011-08-11 EA EA201390214A patent/EA201390214A1/ru unknown
- 2011-08-11 MA MA35714A patent/MA34797B1/fr unknown
- 2011-08-11 SG SG2013009964A patent/SG187795A1/en unknown
- 2011-08-11 US US13/207,696 patent/US8796271B2/en active Active
- 2011-08-11 CA CA2807971A patent/CA2807971A1/en not_active Abandoned
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- 2011-08-11 BR BR112013003358A patent/BR112013003358A2/pt not_active IP Right Cessation
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- 2011-08-11 UY UY0001033554A patent/UY33554A/es not_active Application Discontinuation
- 2011-08-11 CN CN2011800492087A patent/CN103153300A/zh active Pending
- 2011-08-11 NZ NZ607087A patent/NZ607087A/en not_active IP Right Cessation
- 2011-08-11 MX MX2013001660A patent/MX2013001660A/es not_active Application Discontinuation
- 2011-08-11 AU AU2011289377A patent/AU2011289377A1/en not_active Abandoned
- 2011-08-11 KR KR1020137006232A patent/KR20130098334A/ko not_active Withdrawn
- 2011-08-11 US US13/207,753 patent/US8796268B2/en active Active
- 2011-08-11 WO PCT/US2011/047407 patent/WO2012021696A1/en not_active Ceased
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2013
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- 2013-02-11 DO DO2013000034A patent/DOP2013000034A/es unknown
- 2013-02-25 CR CR20130084A patent/CR20130084A/es unknown
- 2013-03-07 CO CO13046171A patent/CO6690755A2/es not_active Application Discontinuation
- 2013-03-11 EC ECSP13012485 patent/ECSP13012485A/es unknown
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2014
- 2014-07-29 US US14/445,373 patent/US20150175593A1/en not_active Abandoned
- 2014-07-29 US US14/445,376 patent/US20150175563A1/en not_active Abandoned
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