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
- 125000002883 imidazolyl group Chemical group 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
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 239000008194 pharmaceutical composition Substances 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 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
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
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- 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
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
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Landscapes
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Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| 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 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2635504T3 true ES2635504T3 (es) | 2017-10-04 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10701773.3T Active ES2635504T3 (es) | 2009-01-21 | 2010-01-21 | Derivados de N2-(3-piridilo o fenil)-N4-(4-piperidil)-2,4-pirimidinadiamina útiles en el tratamiento de enfermedades inflamatorias, toimmunitarias o proliferativas |
Country Status (6)
| Country | Link |
|---|---|
| US (2) | US8377924B2 (https=) |
| EP (1) | EP2389373B1 (https=) |
| JP (2) | JP5781943B2 (https=) |
| CA (1) | CA2749837C (https=) |
| ES (1) | ES2635504T3 (https=) |
| WO (1) | WO2010090875A1 (https=) |
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| WO2005013996A2 (en) * | 2003-08-07 | 2005-02-17 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents |
| US20110130415A1 (en) | 2009-12-01 | 2011-06-02 | Rajinder Singh | Protein kinase c inhibitors and uses thereof |
| EP2595982B1 (en) | 2010-07-21 | 2018-06-13 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| SG10201509157QA (en) * | 2010-11-09 | 2015-12-30 | Fujian Haixi Pharmaceuticals Inc | Compound for increasing kinase active and application thereof |
| SMT202400031T1 (it) | 2011-04-22 | 2024-03-13 | Signal Pharm Llc | Diamminocarbossammide e diamminocarbonitrile pirimidine sostituite, loro composizioni e metodi di trattamento con esse |
| ES2658395T3 (es) | 2012-04-04 | 2018-03-09 | Rigel Pharmaceuticals, Inc. | Inhibidores de proteína cinasa C y usos de los mismos |
| EP2928891B1 (en) | 2012-12-04 | 2019-02-20 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| CA2904610A1 (en) | 2013-03-14 | 2014-09-25 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
| EP3082819B1 (en) | 2013-12-20 | 2020-06-17 | Signal Pharmaceuticals, LLC | Substituted diaminopyrimidyl compounds, compositions thereof, and methods of treatment therewith |
| 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 |
| MX2016012574A (es) | 2014-03-28 | 2017-09-26 | Calitor Sciences Llc | Compuestos heteroarilo sustituidos y metodos de uso. |
| EP3206691B1 (en) | 2014-10-14 | 2018-09-19 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| BR112017012795A2 (pt) | 2014-12-16 | 2018-01-02 | Signal Pharmaceuticals, Llc | Formulações de 2-(terc-butilamino)-4-((1r,3r,4r)-3- hidroxi-4-metilciclo-hexilamino)-pirimidina-5- carboxamida |
| EP3233808B1 (en) | 2014-12-16 | 2021-07-14 | Signal Pharmaceuticals, LLC | Medical uses comprising methods for measurement of inhibition of c-jun n-terminal kinase in skin |
| WO2016123291A1 (en) | 2015-01-29 | 2016-08-04 | Signal Pharmaceuticals, Llc | Isotopologues of 2-(tert-butylamino)-4-((1r,3r,4r)-3-hydroxy-4-methylcyclohexylamino)-pyrimidine-5-carboxamide |
| CN108137559B (zh) * | 2015-07-09 | 2021-11-02 | 默克专利有限公司 | 用作btk抑制剂的嘧啶衍生物及其用途 |
| CA3208587A1 (en) | 2015-07-24 | 2017-02-02 | Celgene Corporation | Methods of synthesis of (1r,2r,5r)-5-amino-2-methylcyclohexanol hydrochloride and intermediates useful therein |
| WO2017044434A1 (en) | 2015-09-11 | 2017-03-16 | Sunshine Lake Pharma Co., Ltd. | Substituted heteroaryl compounds and methods of use |
| 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 |
| CN110621316B (zh) | 2017-04-21 | 2024-01-26 | Epizyme股份有限公司 | 用ehmt2抑制剂进行的组合疗法 |
| CN110869017B (zh) | 2017-05-12 | 2023-05-05 | 英安塔制药有限公司 | 细胞凋亡信号调节激酶1抑制剂及其使用方法 |
| WO2018218051A1 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| WO2018218044A2 (en) | 2017-05-25 | 2018-11-29 | Enanta Pharmaceuticals Inc | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
| US10253018B2 (en) | 2017-05-25 | 2019-04-09 | Enanta Pharmaceuticals, Inc. | Apoptosis signal-regulating kinase 1 inhibitors and methods of use thereof |
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| GB9523675D0 (en) | 1995-11-20 | 1996-01-24 | Celltech Therapeutics Ltd | Chemical compounds |
| ATE407678T1 (de) * | 2001-10-17 | 2008-09-15 | Boehringer Ingelheim Pharma | Pyrimidinderivate, arzneimittel enthaltend diese verbindungen, deren verwendung und verfahren zu ihrer herstellung |
| TWI329105B (en) | 2002-02-01 | 2010-08-21 | Rigel Pharmaceuticals Inc | 2,4-pyrimidinediamine compounds and their uses |
| ES2445208T3 (es) | 2002-07-29 | 2014-02-28 | Rigel Pharmaceuticals, Inc. | Compuestos de 2,4-pirimidindiamina para uso en métodos para tratar o prevenir enfermedades autoinmunitarias |
| CA2505546A1 (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 |
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| BRPI0413018B8 (pt) * | 2003-07-30 | 2021-05-25 | Rigel Pharmaceuticals Inc | composto, e, uso de um composto |
| WO2005013996A2 (en) | 2003-08-07 | 2005-02-17 | Rigel Pharmaceuticals, Inc. | 2,4-pyrimidinediamine compounds and uses as anti-proliferative agents |
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| US20050164323A1 (en) | 2003-12-24 | 2005-07-28 | Wyeth | Methods of treating asthma |
| JP2007532506A (ja) * | 2004-04-08 | 2007-11-15 | ノバルティス アクチエンゲゼルシャフト | 自己免疫疾患および拒絶反応の処置のためのタンパク質キナーゼｃ阻害剤 |
| EP1883302A4 (en) * | 2005-05-03 | 2009-05-20 | Rigel Pharmaceuticals Inc | JAK KINASE HEMMER AND ITS USE |
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| TWI546290B (zh) * | 2008-06-27 | 2016-08-21 | 賽基艾維洛米斯研究股份有限公司 | 雜芳基化合物及其用途 |
| EP2595982B1 (en) * | 2010-07-21 | 2018-06-13 | Rigel Pharmaceuticals, Inc. | Protein kinase c inhibitors and uses thereof |
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| US20100204208A1 (en) | 2010-08-12 |
| US20130210810A1 (en) | 2013-08-15 |
| JP5781943B2 (ja) | 2015-09-24 |
| EP2389373B1 (en) | 2017-05-17 |
| US9149475B2 (en) | 2015-10-06 |
| CA2749837A1 (en) | 2010-08-12 |
| JP2015110629A (ja) | 2015-06-18 |
| US8377924B2 (en) | 2013-02-19 |
| JP2012515724A (ja) | 2012-07-12 |
| WO2010090875A1 (en) | 2010-08-12 |
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