ES2635504T3 - Derivados de N2-(3-piridilo o fenil)-N4-(4-piperidil)-2,4-pirimidinadiamina útiles en el tratamiento de enfermedades inflamatorias, toimmunitarias o proliferativas - Google Patents
Derivados de N2-(3-piridilo o fenil)-N4-(4-piperidil)-2,4-pirimidinadiamina útiles en el tratamiento de enfermedades inflamatorias, toimmunitarias o proliferativas Download PDFInfo
- Publication number
- ES2635504T3 ES2635504T3 ES10701773.3T ES10701773T ES2635504T3 ES 2635504 T3 ES2635504 T3 ES 2635504T3 ES 10701773 T ES10701773 T ES 10701773T ES 2635504 T3 ES2635504 T3 ES 2635504T3
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- Prior art keywords
- substituted
- alkyl
- iii
- hydrogen
- heteroaryl
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- -1 4-piperidyl Chemical group 0.000 title abstract description 114
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 title 1
- 201000010099 disease Diseases 0.000 title 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title 1
- 230000002757 inflammatory effect Effects 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title 1
- 230000002062 proliferating effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract description 96
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 75
- 125000000623 heterocyclic group Chemical group 0.000 abstract description 71
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 60
- 239000001257 hydrogen Substances 0.000 abstract description 60
- 125000000547 substituted alkyl group Chemical group 0.000 abstract description 55
- 125000003118 aryl group Chemical group 0.000 abstract description 45
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 44
- 125000002252 acyl group Chemical group 0.000 abstract description 33
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 32
- 125000003545 alkoxy group Chemical group 0.000 abstract description 31
- 125000000266 alpha-aminoacyl group Chemical group 0.000 abstract description 30
- 125000000304 alkynyl group Chemical group 0.000 abstract description 27
- 229910052736 halogen Inorganic materials 0.000 abstract description 27
- 150000002367 halogens Chemical group 0.000 abstract description 27
- 125000003342 alkenyl group Chemical group 0.000 abstract description 26
- 150000001875 compounds Chemical class 0.000 abstract description 24
- 125000005415 substituted alkoxy group Chemical group 0.000 abstract description 23
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract description 23
- 125000003107 substituted aryl group Chemical group 0.000 abstract description 22
- 125000004093 cyano group Chemical group *C#N 0.000 abstract description 21
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract description 20
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract description 19
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 18
- 125000004442 acylamino group Chemical group 0.000 abstract description 17
- 150000001733 carboxylic acid esters Chemical group 0.000 abstract description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract description 12
- 125000004466 alkoxycarbonylamino group Chemical group 0.000 abstract description 9
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract description 9
- 125000006598 aminocarbonylamino group Chemical group 0.000 abstract description 8
- 150000003839 salts Chemical class 0.000 abstract description 5
- 125000004414 alkyl thio group Chemical group 0.000 abstract 2
- 125000004001 thioalkyl group Chemical group 0.000 description 40
- 125000001424 substituent group Chemical group 0.000 description 28
- 125000000392 cycloalkenyl group Chemical group 0.000 description 25
- 150000002431 hydrogen Chemical class 0.000 description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- XSCHRSMBECNVNS-UHFFFAOYSA-N benzopyrazine Natural products N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 13
- 229910052731 fluorine Inorganic materials 0.000 description 12
- 239000011737 fluorine Substances 0.000 description 12
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 125000001153 fluoro group Chemical group F* 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- 238000003556 assay Methods 0.000 description 8
- 125000005309 thioalkoxy group Chemical group 0.000 description 8
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 7
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 6
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 6
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 6
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 6
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 6
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 description 6
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 238000006467 substitution reaction Methods 0.000 description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 6
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 5
- 125000004181 carboxyalkyl group Chemical group 0.000 description 5
- 125000004470 heterocyclooxy group Chemical group 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 5
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 5
- 125000005296 thioaryloxy group Chemical group 0.000 description 5
- 125000005404 thioheteroaryloxy group Chemical group 0.000 description 5
- 125000000033 alkoxyamino group Chemical group 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 4
- 125000005842 heteroatom Chemical group 0.000 description 4
- 125000002349 hydroxyamino group Chemical group [H]ON([H])[*] 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 4
- 125000005255 oxyaminoacyl group Chemical group 0.000 description 4
- 229910052717 sulfur Chemical group 0.000 description 4
- 125000004953 trihalomethyl group Chemical group 0.000 description 4
- BAXOFTOLAUCFNW-UHFFFAOYSA-N 1H-indazole Chemical compound C1=CC=C2C=NNC2=C1 BAXOFTOLAUCFNW-UHFFFAOYSA-N 0.000 description 3
- VEPOHXYIFQMVHW-XOZOLZJESA-N 2,3-dihydroxybutanedioic acid (2S,3S)-3,4-dimethyl-2-phenylmorpholine Chemical compound OC(C(O)C(O)=O)C(O)=O.C[C@H]1[C@@H](OCCN1C)c1ccccc1 VEPOHXYIFQMVHW-XOZOLZJESA-N 0.000 description 3
- VLRSADZEDXVUPG-UHFFFAOYSA-N 2-naphthalen-1-ylpyridine Chemical compound N1=CC=CC=C1C1=CC=CC2=CC=CC=C12 VLRSADZEDXVUPG-UHFFFAOYSA-N 0.000 description 3
- VHMICKWLTGFITH-UHFFFAOYSA-N 2H-isoindole Chemical compound C1=CC=CC2=CNC=C21 VHMICKWLTGFITH-UHFFFAOYSA-N 0.000 description 3
- GDRVFDDBLLKWRI-UHFFFAOYSA-N 4H-quinolizine Chemical compound C1=CC=CN2CC=CC=C21 GDRVFDDBLLKWRI-UHFFFAOYSA-N 0.000 description 3
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 3
- 239000005977 Ethylene Substances 0.000 description 3
- WRYCSMQKUKOKBP-UHFFFAOYSA-N Imidazolidine Chemical compound C1CNCN1 WRYCSMQKUKOKBP-UHFFFAOYSA-N 0.000 description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000004104 aryloxy group Chemical group 0.000 description 3
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 description 3
- 125000002541 furyl group Chemical group 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 3
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 3
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 3
- LPAGFVYQRIESJQ-UHFFFAOYSA-N indoline Chemical compound C1=CC=C2NCCC2=C1 LPAGFVYQRIESJQ-UHFFFAOYSA-N 0.000 description 3
- HOBCFUWDNJPFHB-UHFFFAOYSA-N indolizine Chemical compound C1=CC=CN2C=CC=C21 HOBCFUWDNJPFHB-UHFFFAOYSA-N 0.000 description 3
- ZLTPDFXIESTBQG-UHFFFAOYSA-N isothiazole Chemical compound C=1C=NSC=1 ZLTPDFXIESTBQG-UHFFFAOYSA-N 0.000 description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 3
- 125000004043 oxo group Chemical group O=* 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical compound C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 3
- CPNGPNLZQNNVQM-UHFFFAOYSA-N pteridine Chemical compound N1=CN=CC2=NC=CN=C21 CPNGPNLZQNNVQM-UHFFFAOYSA-N 0.000 description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 3
- 150000003254 radicals Chemical class 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- 150000001204 N-oxides Chemical class 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- 150000001336 alkenes Chemical class 0.000 description 2
- 150000001345 alkine derivatives Chemical class 0.000 description 2
- 125000005133 alkynyloxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 description 2
- 125000004404 heteroalkyl group Chemical group 0.000 description 2
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 125000004076 pyridyl group Chemical group 0.000 description 2
- 125000006413 ring segment Chemical group 0.000 description 2
- 239000011593 sulfur Chemical group 0.000 description 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 2
- 125000005323 thioketone group Chemical group 0.000 description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 1
- 125000005988 1,1-dioxo-thiomorpholinyl group Chemical group 0.000 description 1
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical compound C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 1
- WJFKNYWRSNBZNX-UHFFFAOYSA-N 10H-phenothiazine Chemical compound C1=CC=C2NC3=CC=CC=C3SC2=C1 WJFKNYWRSNBZNX-UHFFFAOYSA-N 0.000 description 1
- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
- BFMGOJBQXYYXLG-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-morpholin-4-ylethoxy)phenyl]-5-fluoro-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=NC(NC=2C=C(C(OCCN3CCOCC3)=CC=2)N2C(=CC=C2C)C)=NC=C1F BFMGOJBQXYYXLG-UHFFFAOYSA-N 0.000 description 1
- RQHZHEIDLQGEFL-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-5-fluoro-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C1C(C)(C)N(C)C(C)(C)CC1NC1=NC(NC=2C=C(C(OCCN3CCCC3)=CC=2)N2C(=CC=C2C)C)=NC=C1F RQHZHEIDLQGEFL-UHFFFAOYSA-N 0.000 description 1
- QIPDYHFWFMMPQM-UHFFFAOYSA-N 2-n-[3-(2,5-dimethylpyrrol-1-yl)-4-(2-pyrrolidin-1-ylethoxy)phenyl]-5-fluoro-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound CC1=CC=C(C)N1C1=CC(NC=2N=C(NC3CC(C)(C)NC(C)(C)C3)C(F)=CN=2)=CC=C1OCCN1CCCC1 QIPDYHFWFMMPQM-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- DFVSXLDAJLVVLH-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-morpholin-4-ylethoxy)phenyl]-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 DFVSXLDAJLVVLH-UHFFFAOYSA-N 0.000 description 1
- JAUBLXVJBSZVSH-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-morpholin-4-ylethoxy)phenyl]-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCOCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 JAUBLXVJBSZVSH-UHFFFAOYSA-N 0.000 description 1
- VTKJXOMDTPRGOL-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrol-1-ylethoxy)phenyl]-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2C=CC=C2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 VTKJXOMDTPRGOL-UHFFFAOYSA-N 0.000 description 1
- BUUNPQCCBUNUSR-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrol-1-ylethoxy)phenyl]-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2C=CC=C2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 BUUNPQCCBUNUSR-UHFFFAOYSA-N 0.000 description 1
- HTGWTCFYVDIVPK-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrolidin-1-ylethoxy)phenyl]-4-n-(1,2,2,6,6-pentamethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)N(C)C(C)(C)C1 HTGWTCFYVDIVPK-UHFFFAOYSA-N 0.000 description 1
- BFCNQMNRCLSWEV-UHFFFAOYSA-N 5-fluoro-2-n-[3-methoxy-5-(2-pyrrolidin-1-ylethoxy)phenyl]-4-n-(2,2,6,6-tetramethylpiperidin-4-yl)pyrimidine-2,4-diamine Chemical compound C=1C(OCCN2CCCC2)=CC(OC)=CC=1NC(N=1)=NC=C(F)C=1NC1CC(C)(C)NC(C)(C)C1 BFCNQMNRCLSWEV-UHFFFAOYSA-N 0.000 description 1
- FUFZNHHSSMCXCZ-UHFFFAOYSA-N 5-piperidin-4-yl-3-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=CC=CC(C=2N=C(ON=2)C2CCNCC2)=C1 FUFZNHHSSMCXCZ-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 1
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 description 1
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 1
- 229910006067 SO3−M Inorganic materials 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- QKDLQFSLLCQTOH-UHFFFAOYSA-N Trichodonin Natural products C1C(O)C2C3(COC(=O)C)C(C=O)C(C)(C)CCC3OC(=O)C22C(=O)C(=C)C1C2 QKDLQFSLLCQTOH-UHFFFAOYSA-N 0.000 description 1
- DGEZNRSVGBDHLK-UHFFFAOYSA-N [1,10]phenanthroline Chemical compound C1=CN=C2C3=NC=CC=C3C=CC2=C1 DGEZNRSVGBDHLK-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000003725 azepanyl group Chemical group 0.000 description 1
- 125000002393 azetidinyl group Chemical group 0.000 description 1
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- WCZVZNOTHYJIEI-UHFFFAOYSA-N cinnoline Chemical compound N1=NC=CC2=CC=CC=C21 WCZVZNOTHYJIEI-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000004465 cycloalkenyloxy group Chemical group 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
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- 125000005290 ethynyloxy group Chemical group C(#C)O* 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000004446 heteroarylalkyl group Chemical group 0.000 description 1
- 125000005885 heterocycloalkylalkyl group Chemical group 0.000 description 1
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- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
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- 230000007246 mechanism Effects 0.000 description 1
- 125000005322 morpholin-1-yl group Chemical group 0.000 description 1
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- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
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- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
- YAAWASYJIRZXSZ-UHFFFAOYSA-N pyrimidine-2,4-diamine Chemical compound NC1=CC=NC(N)=N1 YAAWASYJIRZXSZ-UHFFFAOYSA-N 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
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- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
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- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 1
- 125000004632 tetrahydrothiopyranyl group Chemical group S1C(CCCC1)* 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
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Applications Claiming Priority (5)
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| US14627309P | 2009-01-21 | 2009-01-21 | |
| US146273P | 2009-01-21 | ||
| US26416509P | 2009-11-24 | 2009-11-24 | |
| US264165P | 2009-11-24 | ||
| PCT/US2010/021662 WO2010090875A1 (en) | 2009-01-21 | 2010-01-21 | Derivatives of n2-(3-pyridil or phenyl)-n4-(4-piperidyl)-2,4-pyrimidinediamine useful in the treatment of inflammatory, autoimmune or proliferative diseases |
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|---|---|
| ES2635504T3 true ES2635504T3 (es) | 2017-10-04 |
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| Country | Link |
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| US (2) | US8377924B2 (enExample) |
| EP (1) | EP2389373B1 (enExample) |
| JP (2) | JP5781943B2 (enExample) |
| CA (1) | CA2749837C (enExample) |
| ES (1) | ES2635504T3 (enExample) |
| WO (1) | WO2010090875A1 (enExample) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DK1663242T3 (da) * | 2003-08-07 | 2011-08-01 | Rigel Pharmaceuticals Inc | 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler |
| US20110130415A1 (en) * | 2009-12-01 | 2011-06-02 | Rajinder Singh | Protein kinase c inhibitors and uses thereof |
| CA2801781C (en) * | 2010-07-21 | 2018-02-27 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| EP2638036B1 (en) * | 2010-11-09 | 2017-08-16 | Betta Pharmaceuticals Co., Ltd. | Compound for increasing kinase active and application thereof |
| TWI548621B (zh) * | 2011-04-22 | 2016-09-11 | 標誌製藥公司 | 經取代之二胺基甲醯胺及二胺基甲腈嘧啶、其組合物、及以該等治療之方法 |
| US9321763B2 (en) | 2012-04-04 | 2016-04-26 | Rigel Pharmaceuticals, Inc. | Protein kinase C inhibitors and uses thereof |
| EP2928891B1 (en) | 2012-12-04 | 2019-02-20 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| US9169249B2 (en) | 2013-03-14 | 2015-10-27 | Rigel Pharmaceuticals, Inc. | Protein kinase C inhibitors and uses thereof |
| RU2016129380A (ru) | 2013-12-20 | 2018-01-25 | СИГНАЛ ФАРМАСЬЮТИКАЛЗ, ЭлЭлСи | Замещенные диаминопиримидильные соединения, их композиции и способы лечения с их участием |
| NZ715903A (en) | 2014-01-30 | 2017-06-30 | Signal Pharm Llc | Solid forms of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide, compositions thereof and methods of their use |
| US9399637B2 (en) | 2014-03-28 | 2016-07-26 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| US10059689B2 (en) | 2014-10-14 | 2018-08-28 | Calitor Sciences, Llc | Substituted heteroaryl compounds and methods of use |
| US9513297B2 (en) | 2014-12-16 | 2016-12-06 | Signal Pharmaceuticals, Llc | Methods for measurement of inhibition of c-Jun N-terminal kinase in skin |
| EP3712134B1 (en) | 2014-12-16 | 2023-11-29 | Signal Pharmaceuticals, LLC | Salts of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methycyclohexylamino)-pyrimidine-5-carboxamide |
| EP3250557B1 (en) | 2015-01-29 | 2024-11-20 | Signal Pharmaceuticals, LLC | Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide |
| JP6853234B2 (ja) * | 2015-07-09 | 2021-03-31 | メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ | Ｂｔｋ阻害剤としてのピリミジン誘導体及びその使用 |
| EP3325432B1 (en) | 2015-07-24 | 2020-09-02 | Celgene Corporation | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein |
| EP3347097B1 (en) | 2015-09-11 | 2021-02-24 | Sunshine Lake Pharma Co., Ltd. | Substituted aminopyrimidine derivatives as modulators of the kinases jak, flt3 and aurora |
| WO2017075418A1 (en) | 2015-10-30 | 2017-05-04 | Board Of Trustees Of The University Of Arkansas | Inhibitors of oxidized low-density lipoprotein receptor 1 and methods of use thereof |
| WO2018195450A1 (en) | 2017-04-21 | 2018-10-25 | Epizyme, Inc. | Combination therapies with ehmt2 inhibitors |
| PL3621615T3 (pl) | 2017-05-12 | 2024-03-25 | Enanta Pharmaceuticals, Inc. | Inhibitory regulujące sygnał apoptozy kinazy 1 i sposoby ich stosowania |
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| WO2019099311A1 (en) | 2017-11-19 | 2019-05-23 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
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| IL278368B2 (en) | 2018-05-02 | 2024-06-01 | Enanta Pharm Inc | Tetrazole containing apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
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| EP4401735A4 (en) * | 2021-09-16 | 2025-07-16 | Lomond Therapeutics Inc | COMPOUNDS COMPRISING N-ARYLPYRIMIDIN-2-AMINE DERIVATIVES AS THERAPEUTIC AGENTS |
| CN119462522A (zh) * | 2023-08-08 | 2025-02-18 | 浙江大学 | N2-3-氟-5-取代苯基-2-氨基嘧啶类衍生物、其制备方法及医药用途 |
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| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| JP4460292B2 (ja) * | 2001-10-17 | 2010-05-12 | ベーリンガー インゲルハイム ファルマ ゲゼルシャフト ミット ベシュレンクテル ハフツング ウント コンパニー コマンディトゲゼルシャフト | ピリミジン誘導体、これらの化合物を含む医薬組成物、その使用及びその調製方法 |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| IL166241A0 (en) | 2002-07-29 | 2006-01-15 | Rigel Pharmaceuticals Inc | Method of treating or preventing autoimmune diseases with 2,4-pyrimidinedinediamine compounds |
| WO2004043386A2 (en) | 2002-11-08 | 2004-05-27 | Tolerrx, Inc. | Molecules preferentially associated with effector t cells and methods of their use |
| UA80767C2 (en) * | 2002-12-20 | 2007-10-25 | Pfizer Prod Inc | Pyrimidine derivatives for the treatment of abnormal cell growth |
| JP4665760B2 (ja) | 2003-06-25 | 2011-04-06 | 日本電気株式会社 | 電子計算機、半導体集積回路、制御方法、プログラムの生成方法、及びプログラム |
| ES2421139T3 (es) | 2003-07-30 | 2013-08-29 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para su uso en el tratamiento o la prevención de enfermedades autoinmunitarias |
| DK1663242T3 (da) * | 2003-08-07 | 2011-08-01 | Rigel Pharmaceuticals Inc | 2,4-Pyrimidindiamin-forbindelser og anvendelse som antiproliferative midler |
| CN1863773A (zh) | 2003-10-09 | 2006-11-15 | 埃科特莱茵药品有限公司 | 四氢吡啶衍生物 |
| KR20060127415A (ko) | 2003-12-24 | 2006-12-12 | 와이어쓰 | 천식의 치료방법 |
| US20070232658A1 (en) * | 2004-04-08 | 2007-10-04 | Jurgen Wagner | Protein Kinase C Inhibitors for the Treatment of Autoimmune Diseases and of Transplant Rejiction |
| JP2008540436A (ja) * | 2005-05-03 | 2008-11-20 | ライジェル ファーマシューティカルズ， インコーポレイテッド | Ｊａｋキナーゼインヒビターおよびそれらの使用 |
| JP2010522765A (ja) | 2007-03-28 | 2010-07-08 | アレイ バイオファーマ、インコーポレイテッド | 受容体チロシンキナーゼとしてのイミダゾ［１，２−ａ］ピリジン化合物 |
| CN101903357A (zh) * | 2007-07-17 | 2010-12-01 | 里格尔药品股份有限公司 | 作为pkc抑制剂的环状胺取代的嘧啶二胺 |
| AU2009262068C1 (en) * | 2008-06-27 | 2015-07-02 | Celgene Car Llc | Heteroaryl compounds and uses thereof |
| CA2801781C (en) * | 2010-07-21 | 2018-02-27 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
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| JP2012515724A (ja) | 2012-07-12 |
| EP2389373B1 (en) | 2017-05-17 |
| WO2010090875A1 (en) | 2010-08-12 |
| US9149475B2 (en) | 2015-10-06 |
| US20130210810A1 (en) | 2013-08-15 |
| US8377924B2 (en) | 2013-02-19 |
| JP2015110629A (ja) | 2015-06-18 |
| EP2389373A1 (en) | 2011-11-30 |
| CA2749837A1 (en) | 2010-08-12 |
| CA2749837C (en) | 2017-07-11 |
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