SK125999A3 - Pyrrolo[2,3d]pyrimidines and their use as tyrosine kinase inhibitors - Google Patents
Pyrrolo[2,3d]pyrimidines and their use as tyrosine kinase inhibitors Download PDFInfo
- Publication number
- SK125999A3 SK125999A3 SK1259-99A SK125999A SK125999A3 SK 125999 A3 SK125999 A3 SK 125999A3 SK 125999 A SK125999 A SK 125999A SK 125999 A3 SK125999 A3 SK 125999A3
- Authority
- SK
- Slovakia
- Prior art keywords
- alloy
- phenyl
- chromium
- pyrrolo
- pyrimidin
- Prior art date
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- 229940121358 tyrosine kinase inhibitor Drugs 0.000 title description 2
- 239000005483 tyrosine kinase inhibitor Substances 0.000 title description 2
- 150000004943 pyrrolo[2,3-d]pyrimidines Chemical class 0.000 title 1
- -1 2-phenyl-1,3-dioxan-5-yl Chemical group 0.000 claims abstract description 241
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 122
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 88
- 238000000034 method Methods 0.000 claims abstract description 56
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 50
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 37
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 239000001257 hydrogen Substances 0.000 claims abstract description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 22
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 18
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 15
- 230000008569 process Effects 0.000 claims abstract description 15
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 14
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 11
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 10
- 230000002062 proliferating effect Effects 0.000 claims abstract description 10
- 125000003226 pyrazolyl group Chemical group 0.000 claims abstract description 9
- 125000005544 phthalimido group Chemical group 0.000 claims abstract description 7
- 241000124008 Mammalia Species 0.000 claims abstract description 5
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 5
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 5
- 239000000203 mixture Substances 0.000 claims description 187
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 52
- 229910052736 halogen Inorganic materials 0.000 claims description 39
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 34
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 33
- 150000002367 halogens Chemical class 0.000 claims description 33
- 239000011159 matrix material Substances 0.000 claims description 33
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 32
- 239000012071 phase Substances 0.000 claims description 30
- 239000002245 particle Substances 0.000 claims description 29
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 29
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 27
- 239000000843 powder Substances 0.000 claims description 27
- 230000002829 reductive effect Effects 0.000 claims description 27
- 239000006185 dispersion Substances 0.000 claims description 26
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims description 26
- 239000000047 product Substances 0.000 claims description 24
- 201000010099 disease Diseases 0.000 claims description 22
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 22
- 239000010410 layer Substances 0.000 claims description 22
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 21
- 238000004519 manufacturing process Methods 0.000 claims description 21
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 20
- 238000006243 chemical reaction Methods 0.000 claims description 19
- OYRRZWATULMEPF-UHFFFAOYSA-N pyrimidin-4-amine Chemical compound NC1=CC=NC=N1 OYRRZWATULMEPF-UHFFFAOYSA-N 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 16
- 229910021529 ammonia Inorganic materials 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 230000015572 biosynthetic process Effects 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 238000001816 cooling Methods 0.000 claims description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 8
- 125000001544 thienyl group Chemical group 0.000 claims description 8
- 238000012360 testing method Methods 0.000 claims description 7
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 6
- NFSWHYRUVWRUDN-UHFFFAOYSA-N 5-(4-phenoxyphenyl)-7h-pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2NC=C1C(C=C1)=CC=C1OC1=CC=CC=C1 NFSWHYRUVWRUDN-UHFFFAOYSA-N 0.000 claims description 6
- 241000282414 Homo sapiens Species 0.000 claims description 6
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
- 239000008187 granular material Substances 0.000 claims description 6
- 208000026278 immune system disease Diseases 0.000 claims description 6
- 238000002844 melting Methods 0.000 claims description 6
- 230000008018 melting Effects 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 4
- 239000004146 Propane-1,2-diol Substances 0.000 claims description 4
- 125000005605 benzo group Chemical group 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 4
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
- 125000000842 isoxazolyl group Chemical group 0.000 claims description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- 230000001613 neoplastic effect Effects 0.000 claims description 4
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 238000003786 synthesis reaction Methods 0.000 claims description 4
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 230000015556 catabolic process Effects 0.000 claims description 3
- 239000007789 gas Substances 0.000 claims description 3
- 238000012423 maintenance Methods 0.000 claims description 3
- LYBNLOMPRHYDRF-UHFFFAOYSA-N 2-[4-(4-amino-7-cyclopentylpyrrolo[2,3-d]pyrimidin-5-yl)phenoxy]phenol Chemical compound C1=2C(N)=NC=NC=2N(C2CCCC2)C=C1C(C=C1)=CC=C1OC1=CC=CC=C1O LYBNLOMPRHYDRF-UHFFFAOYSA-N 0.000 claims description 2
- PIJBBYHMSXEZMC-UHFFFAOYSA-N 5-[4-(4-amino-7-propan-2-ylpyrrolo[2,3-d]pyrimidin-5-yl)phenoxy]-2-nitrobenzoic acid Chemical compound C12=C(N)N=CN=C2N(C(C)C)C=C1C(C=C1)=CC=C1OC1=CC=C([N+]([O-])=O)C(C(O)=O)=C1 PIJBBYHMSXEZMC-UHFFFAOYSA-N 0.000 claims description 2
- SMKWVLYWUQBZKW-UHFFFAOYSA-N 5-[4-(benzenesulfinyl)phenyl]-7-tert-butylpyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C12=C(N)N=CN=C2N(C(C)(C)C)C=C1C(C=C1)=CC=C1S(=O)C1=CC=CC=C1 SMKWVLYWUQBZKW-UHFFFAOYSA-N 0.000 claims description 2
- PAHKLGUKLSFIBQ-UHFFFAOYSA-N 7-cyclopentyl-5-(2-phenoxyphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C1=2C(N)=NC=NC=2N(C2CCCC2)C=C1C1=CC=CC=C1OC1=CC=CC=C1 PAHKLGUKLSFIBQ-UHFFFAOYSA-N 0.000 claims description 2
- ISMWZGJUONENAM-UHFFFAOYSA-N 7-tert-butyl-5-(4-phenylphenyl)pyrrolo[2,3-d]pyrimidin-4-amine Chemical compound C12=C(N)N=CN=C2N(C(C)(C)C)C=C1C(C=C1)=CC=C1C1=CC=CC=C1 ISMWZGJUONENAM-UHFFFAOYSA-N 0.000 claims description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 2
- 150000003863 ammonium salts Chemical class 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005543 phthalimide group Chemical group 0.000 claims description 2
- 239000002244 precipitate Substances 0.000 claims description 2
- 239000003755 preservative agent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 229910045601 alloy Inorganic materials 0.000 claims 126
- 239000000956 alloy Substances 0.000 claims 126
- 239000011651 chromium Substances 0.000 claims 119
- 229910052804 chromium Inorganic materials 0.000 claims 55
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims 53
- WGLPBDUCMAPZCE-UHFFFAOYSA-N Trioxochromium Chemical compound O=[Cr](=O)=O WGLPBDUCMAPZCE-UHFFFAOYSA-N 0.000 claims 39
- 230000003647 oxidation Effects 0.000 claims 38
- 238000007254 oxidation reaction Methods 0.000 claims 38
- 229910000423 chromium oxide Inorganic materials 0.000 claims 34
- 229910052751 metal Inorganic materials 0.000 claims 24
- 239000002184 metal Substances 0.000 claims 24
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims 21
- 229910052721 tungsten Inorganic materials 0.000 claims 19
- 238000005260 corrosion Methods 0.000 claims 18
- 230000007797 corrosion Effects 0.000 claims 18
- 239000011521 glass Substances 0.000 claims 18
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 claims 17
- 229910052750 molybdenum Inorganic materials 0.000 claims 16
- 239000002243 precursor Substances 0.000 claims 16
- 239000010937 tungsten Substances 0.000 claims 16
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims 15
- 230000000052 comparative effect Effects 0.000 claims 14
- 239000011733 molybdenum Substances 0.000 claims 14
- 239000006060 molten glass Substances 0.000 claims 13
- 238000005245 sintering Methods 0.000 claims 11
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims 10
- 230000001590 oxidative effect Effects 0.000 claims 10
- VNNRSPGTAMTISX-UHFFFAOYSA-N chromium nickel Chemical compound [Cr].[Ni] VNNRSPGTAMTISX-UHFFFAOYSA-N 0.000 claims 8
- 229910052742 iron Inorganic materials 0.000 claims 8
- 238000001757 thermogravimetry curve Methods 0.000 claims 8
- 229910052759 nickel Inorganic materials 0.000 claims 7
- 238000002161 passivation Methods 0.000 claims 7
- 239000011241 protective layer Substances 0.000 claims 7
- 239000003870 refractory metal Substances 0.000 claims 7
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 claims 6
- 238000000137 annealing Methods 0.000 claims 6
- 239000000835 fiber Substances 0.000 claims 6
- 229910018487 Ni—Cr Inorganic materials 0.000 claims 5
- 229910052786 argon Inorganic materials 0.000 claims 5
- 229940117975 chromium trioxide Drugs 0.000 claims 5
- GAMDZJFZMJECOS-UHFFFAOYSA-N chromium(6+);oxygen(2-) Chemical compound [O-2].[O-2].[O-2].[Cr+6] GAMDZJFZMJECOS-UHFFFAOYSA-N 0.000 claims 5
- 229910017052 cobalt Inorganic materials 0.000 claims 5
- 239000010941 cobalt Substances 0.000 claims 5
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims 5
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 5
- 229910000753 refractory alloy Inorganic materials 0.000 claims 5
- 230000035882 stress Effects 0.000 claims 5
- 239000002344 surface layer Substances 0.000 claims 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 4
- 230000003628 erosive effect Effects 0.000 claims 4
- 238000007731 hot pressing Methods 0.000 claims 4
- 239000001301 oxygen Substances 0.000 claims 4
- 229910052763 palladium Inorganic materials 0.000 claims 4
- 230000009471 action Effects 0.000 claims 3
- 238000005516 engineering process Methods 0.000 claims 3
- 239000003365 glass fiber Substances 0.000 claims 3
- 239000011491 glass wool Substances 0.000 claims 3
- 239000012535 impurity Substances 0.000 claims 3
- 238000011065 in-situ storage Methods 0.000 claims 3
- 239000011261 inert gas Substances 0.000 claims 3
- 238000005551 mechanical alloying Methods 0.000 claims 3
- 150000002736 metal compounds Chemical class 0.000 claims 3
- 229910052758 niobium Inorganic materials 0.000 claims 3
- 239000010955 niobium Substances 0.000 claims 3
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 claims 3
- 238000003825 pressing Methods 0.000 claims 3
- 229910052715 tantalum Inorganic materials 0.000 claims 3
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 claims 3
- 230000004584 weight gain Effects 0.000 claims 3
- 235000019786 weight gain Nutrition 0.000 claims 3
- ZSLUVFAKFWKJRC-IGMARMGPSA-N 232Th Chemical compound [232Th] ZSLUVFAKFWKJRC-IGMARMGPSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 229910052684 Cerium Inorganic materials 0.000 claims 2
- 229910000684 Cobalt-chrome Inorganic materials 0.000 claims 2
- 229910052776 Thorium Inorganic materials 0.000 claims 2
- QCWXUUIWCKQGHC-UHFFFAOYSA-N Zirconium Chemical compound [Zr] QCWXUUIWCKQGHC-UHFFFAOYSA-N 0.000 claims 2
- WAIPAZQMEIHHTJ-UHFFFAOYSA-N [Cr].[Co] Chemical compound [Cr].[Co] WAIPAZQMEIHHTJ-UHFFFAOYSA-N 0.000 claims 2
- ZMIGMASIKSOYAM-UHFFFAOYSA-N cerium Chemical compound [Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce][Ce] ZMIGMASIKSOYAM-UHFFFAOYSA-N 0.000 claims 2
- AXTNPHLCOKUMDY-UHFFFAOYSA-N chromium cobalt Chemical compound [Co][Cr][Co] AXTNPHLCOKUMDY-UHFFFAOYSA-N 0.000 claims 2
- SZMZREIADCOWQA-UHFFFAOYSA-N chromium cobalt nickel Chemical compound [Cr].[Co].[Ni] SZMZREIADCOWQA-UHFFFAOYSA-N 0.000 claims 2
- UPHIPHFJVNKLMR-UHFFFAOYSA-N chromium iron Chemical compound [Cr].[Fe] UPHIPHFJVNKLMR-UHFFFAOYSA-N 0.000 claims 2
- OYSYRRRAJPTBHI-UHFFFAOYSA-N chromium molybdenum tungsten Chemical compound [Cr][W][Mo] OYSYRRRAJPTBHI-UHFFFAOYSA-N 0.000 claims 2
- 239000011248 coating agent Substances 0.000 claims 2
- 238000000576 coating method Methods 0.000 claims 2
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- 229910002804 graphite Inorganic materials 0.000 claims 2
- 238000000227 grinding Methods 0.000 claims 2
- 229910052735 hafnium Inorganic materials 0.000 claims 2
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 claims 2
- 230000006872 improvement Effects 0.000 claims 2
- 229910052746 lanthanum Inorganic materials 0.000 claims 2
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 claims 2
- 150000002739 metals Chemical class 0.000 claims 2
- 239000004570 mortar (masonry) Substances 0.000 claims 2
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- 229910052726 zirconium Inorganic materials 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- 229910000714 At alloy Inorganic materials 0.000 claims 1
- HJJXVPUOMJYVPN-UHFFFAOYSA-N C1(CCCC1)N1C=C(C2=C1N=CN=C2N)C2=CC=C(C=C2)OC2=CC=CC=C2.C(C)(C)N2C=C(C1=C2N=CN=C1N)C1=CC=C(C=C1)OC1=CC=CC=C1 Chemical compound C1(CCCC1)N1C=C(C2=C1N=CN=C2N)C2=CC=C(C=C2)OC2=CC=CC=C2.C(C)(C)N2C=C(C1=C2N=CN=C1N)C1=CC=C(C=C1)OC1=CC=CC=C1 HJJXVPUOMJYVPN-UHFFFAOYSA-N 0.000 claims 1
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- OHLUUHNLEMFGTQ-UHFFFAOYSA-N N-methylacetamide Chemical compound CNC(C)=O OHLUUHNLEMFGTQ-UHFFFAOYSA-N 0.000 claims 1
- 229910000990 Ni alloy Inorganic materials 0.000 claims 1
- 229910000831 Steel Inorganic materials 0.000 claims 1
- QXZUUHYBWMWJHK-UHFFFAOYSA-N [Co].[Ni] Chemical compound [Co].[Ni] QXZUUHYBWMWJHK-UHFFFAOYSA-N 0.000 claims 1
- WBWJXRJARNTNBL-UHFFFAOYSA-N [Fe].[Cr].[Co] Chemical compound [Fe].[Cr].[Co] WBWJXRJARNTNBL-UHFFFAOYSA-N 0.000 claims 1
- RMXTYBQNQCQHEU-UHFFFAOYSA-N ac1lawpn Chemical compound [Cr]#[Cr] RMXTYBQNQCQHEU-UHFFFAOYSA-N 0.000 claims 1
- 125000002252 acyl group Chemical group 0.000 claims 1
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- BIJOYKCOMBZXAE-UHFFFAOYSA-N chromium iron nickel Chemical compound [Cr].[Fe].[Ni] BIJOYKCOMBZXAE-UHFFFAOYSA-N 0.000 claims 1
- VNTLIPZTSJSULJ-UHFFFAOYSA-N chromium molybdenum Chemical compound [Cr].[Mo] VNTLIPZTSJSULJ-UHFFFAOYSA-N 0.000 claims 1
- NVIVJPRCKQTWLY-UHFFFAOYSA-N cobalt nickel Chemical compound [Co][Ni][Co] NVIVJPRCKQTWLY-UHFFFAOYSA-N 0.000 claims 1
- XTUHPOUJWWTMNC-UHFFFAOYSA-N cobalt(2+);dioxido(dioxo)chromium Chemical class [Co+2].[O-][Cr]([O-])(=O)=O XTUHPOUJWWTMNC-UHFFFAOYSA-N 0.000 claims 1
- 230000006835 compression Effects 0.000 claims 1
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- CBDHGBOZFSYMEC-UHFFFAOYSA-N tert-butyl n-[4-(4-chloro-7-cyclopentyl-1h-pyrrolo[2,3-d]pyrimidin-4-yl)-2-methoxyphenyl]carbamate Chemical compound C1=C(NC(=O)OC(C)(C)C)C(OC)=CC(C2(Cl)C3=C(N(C=C3)C3CCCC3)NC=N2)=C1 CBDHGBOZFSYMEC-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
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US4083697P | 1997-03-19 | 1997-03-19 | |
PCT/EP1998/001357 WO1998041525A1 (en) | 1997-03-19 | 1998-03-09 | Pyrrolo[2,3d]pyrimidines and their use as tyrosine kinase inhibitors |
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SK125999A3 true SK125999A3 (en) | 2000-05-16 |
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SK1259-99A SK125999A3 (en) | 1997-03-19 | 1998-03-09 | Pyrrolo[2,3d]pyrimidines and their use as tyrosine kinase inhibitors |
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US (1) | US6001839A (xx) |
EP (1) | EP0970084B1 (xx) |
JP (1) | JP2001516353A (xx) |
KR (1) | KR20000076426A (xx) |
CN (1) | CN1134439C (xx) |
AT (1) | ATE242245T1 (xx) |
AU (1) | AU748884B2 (xx) |
BG (1) | BG64282B1 (xx) |
BR (1) | BR9808281A (xx) |
CA (1) | CA2283961A1 (xx) |
DE (1) | DE69815317T2 (xx) |
DK (1) | DK0970084T3 (xx) |
ES (1) | ES2202827T3 (xx) |
HU (1) | HUP0001507A3 (xx) |
ID (1) | ID24653A (xx) |
IL (1) | IL131582A0 (xx) |
NO (1) | NO313962B1 (xx) |
NZ (1) | NZ337529A (xx) |
PL (1) | PL335685A1 (xx) |
PT (1) | PT970084E (xx) |
SK (1) | SK125999A3 (xx) |
TR (1) | TR199902301T2 (xx) |
WO (1) | WO1998041525A1 (xx) |
Families Citing this family (118)
Publication number | Priority date | Publication date | Assignee | Title |
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US7863444B2 (en) | 1997-03-19 | 2011-01-04 | Abbott Laboratories | 4-aminopyrrolopyrimidines as kinase inhibitors |
CA2341409A1 (en) * | 1998-08-31 | 2000-03-09 | Merck And Co., Inc. | Novel angiogenesis inhibitors |
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- 1998-03-09 EP EP98913690A patent/EP0970084B1/en not_active Expired - Lifetime
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DE69815317D1 (de) | 2003-07-10 |
IL131582A0 (en) | 2001-01-28 |
CA2283961A1 (en) | 1998-09-24 |
EP0970084B1 (en) | 2003-06-04 |
ATE242245T1 (de) | 2003-06-15 |
PT970084E (pt) | 2003-10-31 |
PL335685A1 (en) | 2000-05-08 |
BR9808281A (pt) | 2000-05-16 |
CN1134439C (zh) | 2004-01-14 |
HUP0001507A2 (hu) | 2000-10-28 |
JP2001516353A (ja) | 2001-09-25 |
BG103785A (en) | 2000-06-30 |
NO994509L (no) | 1999-09-17 |
NZ337529A (en) | 2000-10-27 |
NO313962B1 (no) | 2003-01-06 |
DK0970084T3 (da) | 2003-09-29 |
ES2202827T3 (es) | 2004-04-01 |
DE69815317T2 (de) | 2005-04-07 |
BG64282B1 (bg) | 2004-08-31 |
TR199902301T2 (xx) | 1999-12-21 |
ID24653A (id) | 2000-07-27 |
KR20000076426A (ko) | 2000-12-26 |
AU748884B2 (en) | 2002-06-13 |
CN1259950A (zh) | 2000-07-12 |
NO994509D0 (no) | 1999-09-17 |
US6001839A (en) | 1999-12-14 |
HUP0001507A3 (en) | 2002-01-28 |
AU6829398A (en) | 1998-10-12 |
WO1998041525A1 (en) | 1998-09-24 |
EP0970084A1 (en) | 2000-01-12 |
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