HRP20221043T1 - Derivat oksi-fluoropiperidina kao inhibitor kinaze - Google Patents
Derivat oksi-fluoropiperidina kao inhibitor kinaze Download PDFInfo
- Publication number
- HRP20221043T1 HRP20221043T1 HRP20221043TT HRP20221043T HRP20221043T1 HR P20221043 T1 HRP20221043 T1 HR P20221043T1 HR P20221043T T HRP20221043T T HR P20221043TT HR P20221043 T HRP20221043 T HR P20221043T HR P20221043 T1 HRP20221043 T1 HR P20221043T1
- Authority
- HR
- Croatia
- Prior art keywords
- oxy
- pyrrolo
- amino
- prop
- pyrazol
- Prior art date
Links
- 229940043355 kinase inhibitor Drugs 0.000 title 1
- 239000003757 phosphotransferase inhibitor Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 9
- 239000000126 substance Substances 0.000 claims 9
- 150000003839 salts Chemical class 0.000 claims 7
- HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 claims 5
- 201000010099 disease Diseases 0.000 claims 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 3
- JWLPUQHGINAEID-LSDHHAIUSA-N 1-[(3R,4S)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@@H]1F)C(C=C)=O JWLPUQHGINAEID-LSDHHAIUSA-N 0.000 claims 2
- JWLPUQHGINAEID-HUUCEWRRSA-N C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O Chemical compound C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O JWLPUQHGINAEID-HUUCEWRRSA-N 0.000 claims 2
- 206010028980 Neoplasm Diseases 0.000 claims 2
- 125000000217 alkyl group Chemical group 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
- -1 morpholino, tetrahydropyranyl Chemical group 0.000 claims 2
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims 2
- 125000003386 piperidinyl group Chemical group 0.000 claims 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 1
- KZKRRZFCAYOXQE-UHFFFAOYSA-N 1$l^{2}-azinane Chemical group C1CC[N]CC1 KZKRRZFCAYOXQE-UHFFFAOYSA-N 0.000 claims 1
- SGJIYRCDJHFJIF-ZIAGYGMSSA-N 1-[(3R,4R)-3-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound FC(CN1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)F SGJIYRCDJHFJIF-ZIAGYGMSSA-N 0.000 claims 1
- SWPIHBPVVYEOLI-CHWSQXEVSA-N 1-[(3R,4R)-4-fluoro-3-[[2-(1,2-oxazol-4-ylamino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@H]1[C@@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC=1C=NOC=1)NC=C2 SWPIHBPVVYEOLI-CHWSQXEVSA-N 0.000 claims 1
- HBAFQIAOOXMYKV-JKSUJKDBSA-N 1-[(3R,4S)-3-[[2-[(1-cyclopropylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound C1(CC1)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@@H]1F)C(C=C)=O HBAFQIAOOXMYKV-JKSUJKDBSA-N 0.000 claims 1
- ZTNAQVIBRDLDAA-WCQYABFASA-N 1-[(3R,4S)-3-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-fluoro-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound FC(CN1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2F)O[C@@H]1CN(CC[C@@H]1F)C(C=C)=O)F ZTNAQVIBRDLDAA-WCQYABFASA-N 0.000 claims 1
- FKKDZJVASSEXKZ-UONOGXRCSA-N 1-[(3R,4S)-3-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound FC(CN1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2C)O[C@@H]1CN(CC[C@@H]1F)C(C=C)=O)F FKKDZJVASSEXKZ-UONOGXRCSA-N 0.000 claims 1
- GVDLYXPBEGLLFM-VQTJNVASSA-N 1-[(3R,4S)-4-fluoro-3-[[2-(4-morpholin-4-ylanilino)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@@H]1[C@@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC1=CC=C(C=C1)N1CCOCC1)NC=C2 GVDLYXPBEGLLFM-VQTJNVASSA-N 0.000 claims 1
- NFABHXGDHDFKDI-QWHCGFSZSA-N 1-[(3R,4S)-4-fluoro-3-[[2-[(3-methyl-1,2-thiazol-5-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@@H]1[C@@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC1=CC(=NS1)C)NC=C2 NFABHXGDHDFKDI-QWHCGFSZSA-N 0.000 claims 1
- XUFSWKMZWKGAET-ZWKOTPCHSA-N 1-[(3R,4S)-4-fluoro-3-[[2-[[1-(oxan-4-yl)pyrazol-4-yl]amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@@H]1[C@@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)C1CCOCC1)NC=C2 XUFSWKMZWKGAET-ZWKOTPCHSA-N 0.000 claims 1
- PLFNXUCAGLXHER-OCCSQVGLSA-N 1-[(3S,4R)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-fluoro-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2F)O[C@H]1CN(CC[C@H]1F)C(C=C)=O PLFNXUCAGLXHER-OCCSQVGLSA-N 0.000 claims 1
- ZROSJPSOILHJQV-CABCVRRESA-N 1-[(3S,4R)-3-[[2-[(1-ethylpyrazol-4-yl)amino]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2C)O[C@H]1CN(CC[C@H]1F)C(C=C)=O ZROSJPSOILHJQV-CABCVRRESA-N 0.000 claims 1
- FKKDZJVASSEXKZ-KGLIPLIRSA-N 1-[(3S,4R)-3-[[2-[[1-(2,2-difluoroethyl)pyrazol-4-yl]amino]-5-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]-4-fluoropiperidin-1-yl]prop-2-en-1-one Chemical compound FC(CN1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2C)O[C@H]1CN(CC[C@H]1F)C(C=C)=O)F FKKDZJVASSEXKZ-KGLIPLIRSA-N 0.000 claims 1
- QFQRXEOQBMETNG-MSOLQXFVSA-N 1-[(3S,4R)-4-fluoro-3-[[2-[(1-piperidin-4-ylpyrazol-4-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@H]1[C@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)C1CCNCC1)NC=C2 QFQRXEOQBMETNG-MSOLQXFVSA-N 0.000 claims 1
- NFABHXGDHDFKDI-OLZOCXBDSA-N 1-[(3S,4R)-4-fluoro-3-[[2-[(3-methyl-1,2-thiazol-5-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@H]1[C@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC1=CC(=NS1)C)NC=C2 NFABHXGDHDFKDI-OLZOCXBDSA-N 0.000 claims 1
- YMKKYSADUBPRCK-CABCVRRESA-N 1-[(3S,4R)-4-fluoro-3-[[2-[[1-(2-hydroxyethyl)pyrazol-4-yl]amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@H]1[C@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)CCO)NC=C2 YMKKYSADUBPRCK-CABCVRRESA-N 0.000 claims 1
- JMGAJIMHWVWABN-OLZOCXBDSA-N 1-[(3S,4R)-4-fluoro-3-[[5-methyl-2-[(3-methyl-1,2-thiazol-5-yl)amino]-7H-pyrrolo[2,3-d]pyrimidin-4-yl]oxy]piperidin-1-yl]prop-2-en-1-one Chemical compound F[C@H]1[C@H](CN(CC1)C(C=C)=O)OC=1C2=C(N=C(N=1)NC1=CC(=NS1)C)NC=C2C JMGAJIMHWVWABN-OLZOCXBDSA-N 0.000 claims 1
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- 125000004777 2-fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
- 208000023275 Autoimmune disease Diseases 0.000 claims 1
- JWLPUQHGINAEID-GJZGRUSLSA-N C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@@H]1F)C(C=C)=O Chemical compound C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@@H]1F)C(C=C)=O JWLPUQHGINAEID-GJZGRUSLSA-N 0.000 claims 1
- JWLPUQHGINAEID-CABCVRRESA-N C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@H]1F)C(C=C)=O Chemical compound C(C)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@H]1F)C(C=C)=O JWLPUQHGINAEID-CABCVRRESA-N 0.000 claims 1
- HJTWMCDGJVEOQY-HZPDHXFCSA-N C(C=C)(=O)N1C[C@H]([C@@H](CC1)F)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)C1CC1)NC=C2C#N Chemical compound C(C=C)(=O)N1C[C@H]([C@@H](CC1)F)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)C1CC1)NC=C2C#N HJTWMCDGJVEOQY-HZPDHXFCSA-N 0.000 claims 1
- KGSIPBDDGJCGDZ-HUUCEWRRSA-N C(C=C)(=O)N1C[C@H]([C@@H](CC1)F)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)CC)NC=C2C#N Chemical compound C(C=C)(=O)N1C[C@H]([C@@H](CC1)F)OC=1C2=C(N=C(N=1)NC=1C=NN(C=1)CC)NC=C2C#N KGSIPBDDGJCGDZ-HUUCEWRRSA-N 0.000 claims 1
- HBAFQIAOOXMYKV-CVEARBPZSA-N C1(CC1)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@H]1F)C(C=C)=O Chemical compound C1(CC1)N1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@H]1F)C(C=C)=O HBAFQIAOOXMYKV-CVEARBPZSA-N 0.000 claims 1
- WWQMEXIPGWLRIA-VXGBXAGGSA-N ClC1=CNC=2N=C(N=C(C=21)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)NC1=CC(=NS1)C Chemical compound ClC1=CNC=2N=C(N=C(C=21)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)NC1=CC(=NS1)C WWQMEXIPGWLRIA-VXGBXAGGSA-N 0.000 claims 1
- FYIVGGGCUXWCBN-HUUCEWRRSA-N ClC1=CNC=2N=C(N=C(C=21)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)NC=1C=NN(C=1)C1CC1 Chemical compound ClC1=CNC=2N=C(N=C(C=21)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)NC=1C=NN(C=1)C1CC1 FYIVGGGCUXWCBN-HUUCEWRRSA-N 0.000 claims 1
- KVAOLQZONLRAQP-ZIAGYGMSSA-N ClC1=CNC=2N=C(N=C(C=21)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)NC=1C=NN(C=1)CC Chemical compound ClC1=CNC=2N=C(N=C(C=21)O[C@@H]1CN(CC[C@H]1F)C(C=C)=O)NC=1C=NN(C=1)CC KVAOLQZONLRAQP-ZIAGYGMSSA-N 0.000 claims 1
- KVAOLQZONLRAQP-KGLIPLIRSA-N ClC1=CNC=2N=C(N=C(C=21)O[C@H]1CN(CC[C@H]1F)C(C=C)=O)NC=1C=NN(C=1)CC Chemical compound ClC1=CNC=2N=C(N=C(C=21)O[C@H]1CN(CC[C@H]1F)C(C=C)=O)NC=1C=NN(C=1)CC KVAOLQZONLRAQP-KGLIPLIRSA-N 0.000 claims 1
- SGJIYRCDJHFJIF-KGLIPLIRSA-N FC(CN1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@H]1F)C(C=C)=O)F Chemical compound FC(CN1N=CC(=C1)NC=1N=C(C2=C(N=1)NC=C2)O[C@H]1CN(CC[C@H]1F)C(C=C)=O)F SGJIYRCDJHFJIF-KGLIPLIRSA-N 0.000 claims 1
- HGMQKBYKDSYJQL-GOEBONIOSA-N S1C=NC2=C1C=C(C=C2)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@@H]1F)C(C=C)=O Chemical compound S1C=NC2=C1C=C(C=C2)NC=1N=C(C2=C(N=1)NC=C2)O[C@@H]1CN(CC[C@@H]1F)C(C=C)=O HGMQKBYKDSYJQL-GOEBONIOSA-N 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001246 bromo group Chemical group Br* 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 229910052736 halogen Inorganic materials 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- 230000003463 hyperproliferative effect Effects 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000001786 isothiazolyl group Chemical group 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- 230000001404 mediated effect Effects 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 230000002062 proliferating effect Effects 0.000 claims 1
- 125000003226 pyrazolyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
Classifications
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Immunology (AREA)
- Epidemiology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Claims (7)
1. Spoj predstavljeno sljedećom kemijskom formulom 1, ili njegova farmaceutski prihvatljiva sol:
[image]
naznačeno time što, u kemijskoj formuli 1,
R1 je pirazolil, izooksazolil, izotiazolil, fenil, ili benzotiazolil, gdje je R1 nesupstituiran ili supstituiran sa Ra,
Ra je C1-5 alkil, C1-5 haloalkil, C3-6 cikloalkil, C1-5 hidroksialkil, morfolino, tetrahidropiranil, ili piperidinil, i
R2 je vodik, C1-5 alkil, halogen, ili cijano.
2. Spoj ili njegova farmaceutski prihvatljiva sol u skladu sa patentnim zahtjevom 1,
naznačeno time što je Ra metil, etil, propil, izopropil, butil, izobutil, pentil, izopentil, neopentil, fluorometil, difluorometil, trifluorometil, 2-fluoroetil, 2,2-difluoroetil, 2,2,2-trifluoroetil, ciklopropil, ciklobutil, ciklopentil, cikloheksil, hidroksimetil, 2-hidroksietil, morfolino, tetrahidropiranil, ili piperidinil.
3. Spoj ili njegova farmaceutski prihvatljiva sol u skladu sa patentnim zahtjevom 1,
naznačeno time što je R2 vodik, metil, etil, propil, izopropil, butil, izobutil, pentil, izopentil, neopentil, fluoro, kloro, bromo, ili cijano.
4. Spoj ili njegova farmaceutski prihvatljiva sol u skladu sa patentnim zahtjevom 1,
naznačeno time što je kemijska formula 1 predstavljena sljedećom kemijskom formulom 1-1:
[image]
pri čemu, u kemijskoj formuli 1-1,
Ra i R2 su kao što je definirano u patentnom zahtjevu 1.
5. Spoj ili njegova farmaceutski prihvatljiva sol u skladu sa patentnim zahtjevom 1,
naznačeno time što je kemijska formula 1 predstavljena sljedećom kemijskom formulom 1-2:
[image]
pri čemu, u kemijskoj formuli 1-2,
Ra i R2 su kao što je definirano u patentnom zahtjevu 1.
6. Spoj ili njegova farmaceutski prihvatljiva sol u skladu sa patentnim zahtjevom 1,
naznačeno time što su spojevi predstavljeni kemijskom formulom 1 bilo koji spoj odabran iz grupe koja se sastoji od sljedećih:
1) 1-(trans-3-((2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
2) 1-(trans-3-((2-((1-(2,2-difluoroetil)-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
3) 1-(trans-3-((2-(1-cilklopropil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
4) 1-(cis-3-((2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
5) 1-((3S,4R)-3-((2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
6) 1-((3S,4R)-3-((2-((1-(2,2-difluoroetil)-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
7) 1-((3S,4R)-4-fluoro-3-((2-((3-metilizotiazol-5-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
8) 1-((3S,4R)-3-((2-((1-cilklopropil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
9) 1-(trans-3-((5-kloro-2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
10) 1-(trans-3-((5-kloro-2-((1-cilklopropil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
11) 1-(trans-3-((5-kloro-2-((3-metilizotiazol-5-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
12) 4-((trans-1-akriloil-4-fluoropiperidin-3-il)oksi)-2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-5-karbonitril,
13) 4-((trans-1-akriloil-4-fluoropiperidin-3-il)oksi)-2-((1-cilklopropil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-5-karbonitril,
14) 4-((trans-1-akriloil-4-fluoropiperidin-3-il)oksi)-2-(1-(2,2-difluoroetil)-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-5-karbonitril,
15) 1-(cis-3-((2-(1-etil-1H-pirazol-4-il)amino)-5-fluoro-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
16) 1-(cis-3-((2-((1-(2,2-difluoroetil)-1H-pirazol-4-il)amino)-5-fluoro-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
17) 1-(cis-3-((2-(1-etil-1H-pirazol-4-il)amino)-5-metil-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
18) 1-(cis-3-((2-((1-(2,2-difluoroetil)-1H-pirazol-4-il)amino)-5-metil-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
19) 1-((3S,4R)-3-((2-((1-etil-1H-pirazol-4-il)amino)-5-metil-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
20) 1-((3S,4R)-3-((2-((1-(2,2-difluoroetil)-1H-pirazol-4-il)amino)-5-metil-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
21) 1-((3S,4R)-4-fluoro-3-((5-metil-2-((3-metilizotiazol-5-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
22) 1-((3S,4R)-3-(2-((1-cilklopropil-1H-pirazol-4-il)amino)-5-metil-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
23) 1-(trans-4-fluoro-3-((2-(izoksazol-4-ilamino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
24) 1-((3R,4R)-3-((2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
25) 1-((3S,4S)-3-((2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
26) 1-((3S,4R)-3-((5-kloro-2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
27) 1-((3S,4R)-3-((2-((1-etil-1H-pirazol-4-il)amino)-5-fluoro-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
28) 1-((3R,4S)-3-((2-((1-etil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
29) 1-((3R,4S)-4-fluoro-3-((2-(izoksazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
30) 1-((3S,4R)-4-fluoro-3-((2-((1-(2-hidroksietil)-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
31) 1-((3R,4S)-4-fluoro-3-((2-((4-morfolinofenil)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
32) 1-((3R,4S)-4-fluoro-3-((2-((3-metilizotiazol-5-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
33) 1-((3R,4S)-4-fluoro-3-((2-((1-(tetrahidro-2H-piran-4-il)-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on,
34) 1-((3R,4S)-3-((2-(benzo[d]tiazol-6-ilamino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on,
35) 1-((3R,4S)-3-((2-((1-cilklopropil-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)-4-fluoropiperidin-1-il)prop-2-en-1-on, i
36) 1-((3S,4R)-4-fluoro-3-((2-((1-(piperidin-4-il)-1H-pirazol-4-il)amino)-7H-pirolo[2,3-d]pirimidin-4-il)oksi)piperidin-1-il)prop-2-en-1-on.
7. Farmaceutska kompozicija za uporabu u prevenciji ili liječenju upalne bolesti, autoimune bolesti, proliferativne bolesti, hiperproliferativne bolesti, bolest posredovana imunitetom, raka ili tumora, naznačena time što sadrži spoj u skladu sa bilo kojim od patentnih zahtjeva 1 do 6 ili njegovu farmaceutski prihvatljivu sol.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR20170183061 | 2017-12-28 | ||
| PCT/KR2018/016814 WO2019132562A1 (ko) | 2017-12-28 | 2018-12-28 | 카이네이즈 저해제로서의 옥시-플루오로피페리딘 유도체 |
| EP18896304.5A EP3733673B1 (en) | 2017-12-28 | 2018-12-28 | Oxy-fluoropiperidine derivative as kinase inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20221043T1 true HRP20221043T1 (hr) | 2022-11-11 |
Family
ID=67067864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20221043TT HRP20221043T1 (hr) | 2017-12-28 | 2018-12-28 | Derivat oksi-fluoropiperidina kao inhibitor kinaze |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US11339167B2 (hr) |
| EP (1) | EP3733673B1 (hr) |
| JP (1) | JP6995428B2 (hr) |
| KR (2) | KR102318929B1 (hr) |
| CN (1) | CN111527091B (hr) |
| AU (1) | AU2018394997B2 (hr) |
| BR (1) | BR112020013141B1 (hr) |
| CA (1) | CA3084962C (hr) |
| CL (1) | CL2020001752A1 (hr) |
| CO (1) | CO2020007162A2 (hr) |
| DO (1) | DOP2020000112A (hr) |
| EC (1) | ECSP20035590A (hr) |
| ES (1) | ES2922633T3 (hr) |
| HR (1) | HRP20221043T1 (hr) |
| HU (1) | HUE059580T2 (hr) |
| IL (1) | IL275207B (hr) |
| LT (1) | LT3733673T (hr) |
| MA (1) | MA51431B1 (hr) |
| MX (1) | MX2020006799A (hr) |
| MY (1) | MY194468A (hr) |
| NZ (1) | NZ764644A (hr) |
| PE (1) | PE20201146A1 (hr) |
| PH (1) | PH12020551013A1 (hr) |
| PL (1) | PL3733673T3 (hr) |
| PT (1) | PT3733673T (hr) |
| RS (1) | RS63515B1 (hr) |
| RU (1) | RU2758370C1 (hr) |
| SA (1) | SA520412335B1 (hr) |
| SG (1) | SG11202004917UA (hr) |
| SI (1) | SI3733673T1 (hr) |
| TN (1) | TN2020000082A1 (hr) |
| WO (1) | WO2019132562A1 (hr) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR20200036004A (ko) | 2017-08-01 | 2020-04-06 | 세라밴스 바이오파마 알앤디 아이피, 엘엘씨 | Jak 키나아제 억제제로서 피라졸로 및 트리아졸로 비시클릭 화합물 |
| KR102318929B1 (ko) * | 2017-12-28 | 2021-10-28 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 옥시-플루오로피페리딘 유도체 |
| KR102577242B1 (ko) | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-메틸피페리딘 유도체 |
| CN113498352A (zh) | 2019-01-23 | 2021-10-12 | 施万生物制药研发Ip有限责任公司 | 作为jak抑制剂的咪唑并[1,5-a]吡啶、1,2,4-三唑并[4,3-a]吡啶和咪唑并[1,5-a]吡嗪 |
| WO2021108803A1 (en) | 2019-11-26 | 2021-06-03 | Theravance Biopharma R&D Ip, Llc | Fused pyrimidine pyridinone compounds as jak inhibitors |
| WO2021147952A1 (zh) * | 2020-01-21 | 2021-07-29 | 江苏先声药业有限公司 | 嘧啶并吡咯类化合物 |
| WO2021147953A1 (zh) * | 2020-01-21 | 2021-07-29 | 江苏先声药业有限公司 | 嘧啶并五元环类衍生物及其应用 |
| WO2022062601A1 (zh) * | 2020-09-22 | 2022-03-31 | 江苏先声药业有限公司 | 嘧啶并吡咯类化合物 |
| CN114315838A (zh) * | 2020-09-30 | 2022-04-12 | 江苏先声药业有限公司 | 嘧啶并吡咯类化合物 |
| WO2023165562A1 (zh) * | 2022-03-02 | 2023-09-07 | 南京明德新药研发有限公司 | 含氮杂环类化合物及其应用 |
Family Cites Families (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7301023B2 (en) | 2001-05-31 | 2007-11-27 | Pfizer Inc. | Chiral salt resolution |
| US7705004B2 (en) * | 2007-08-17 | 2010-04-27 | Portola Pharmaceuticals, Inc. | Protein kinase inhibitors |
| CN103224497A (zh) | 2008-04-22 | 2013-07-31 | 波托拉医药品公司 | 蛋白激酶抑制剂 |
| JP5369183B2 (ja) | 2008-07-16 | 2013-12-18 | ファーマサイクリックス，インク． | 固形腫瘍の治療用のブルートンのチロシンキナーゼの阻害剤 |
| KR101705158B1 (ko) | 2009-05-05 | 2017-02-09 | 다나-파버 캔서 인스티튜트 인크. | Ｅｇｆｒ 억제제 및 질환 치료방법 |
| DK2975042T3 (en) | 2010-06-23 | 2019-01-21 | Hanmi Science Co Ltd | Novel fused pyrimidine derivatives to inhibit tyrosine kinase activity |
| MD20140023A2 (ro) | 2011-09-22 | 2014-06-30 | Pfizer Inc. | Derivaţi de pirolpirimidină şi purină |
| RU2018104702A (ru) | 2012-08-06 | 2019-02-22 | Ацея Байосайенсиз Инк. | Новые соединения пирролопиримидина в качестве ингибиторов протеинкиназ |
| EP2945636B1 (en) | 2013-01-16 | 2017-06-28 | Signal Pharmaceuticals, LLC | Substituted pyrrolopyrimidine compounds, compositions thereof, and methods of treatment therewith |
| KR20150113195A (ko) | 2013-03-05 | 2015-10-07 | 에프. 호프만-라 로슈 아게 | 브루톤 티로신 키나아제의 억제제 |
| US9840517B2 (en) | 2013-09-18 | 2017-12-12 | Beijing Hanmi Pharmaceutical Co., Ltd. | Compound inhibiting activities of BTK and/or JAK3 kinases |
| MD4649C1 (ro) | 2013-12-05 | 2020-04-30 | Pfizer Inc. | Pirol[2,3-d]pirimidinil, pirol[2,3-b]pirazinil şi pirol[2,3-d]piridinil acrilamide |
| CN105777756B (zh) * | 2014-07-02 | 2019-03-01 | 广东东阳光药业有限公司 | 杂芳化合物及其在药物中的应用 |
| CN105732637B (zh) | 2014-12-30 | 2020-04-21 | 广东东阳光药业有限公司 | 杂芳化合物及其在药物中的应用 |
| JP2018537502A (ja) | 2015-12-16 | 2018-12-20 | サウザーン リサーチ インスチチュート | ピロロピリミジン化合物、キナーゼｌｒｒｋ２阻害剤としての使用、及びその調製方法 |
| EP3950691A1 (en) | 2016-06-30 | 2022-02-09 | Daewoong Pharmaceutical Co., Ltd. | Pyrazolopyrimidine derivatives as kinase inhibitor |
| KR102032418B1 (ko) | 2017-06-15 | 2019-10-16 | 한국화학연구원 | 접합 피리미딘 유도체, 이의 제조방법 및 이를 유효성분으로 포함하는 브루톤티로신 키나제 활성 관련 질환의 예방 또는 치료용 약학적 조성물 |
| KR102577241B1 (ko) | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-플루오로피페리딘 유도체 |
| KR102318929B1 (ko) * | 2017-12-28 | 2021-10-28 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 옥시-플루오로피페리딘 유도체 |
| KR102577242B1 (ko) | 2017-12-28 | 2023-09-11 | 주식회사 대웅제약 | 카이네이즈 저해제로서의 아미노-메틸피페리딘 유도체 |
-
2018
- 2018-12-28 KR KR1020180171938A patent/KR102318929B1/ko active IP Right Grant
- 2018-12-28 IL IL275207A patent/IL275207B/en unknown
- 2018-12-28 MY MYPI2020003057A patent/MY194468A/en unknown
- 2018-12-28 US US16/770,638 patent/US11339167B2/en active Active
- 2018-12-28 TN TNP/2020/000082A patent/TN2020000082A1/en unknown
- 2018-12-28 PE PE2020000779A patent/PE20201146A1/es unknown
- 2018-12-28 AU AU2018394997A patent/AU2018394997B2/en active Active
- 2018-12-28 SI SI201830723T patent/SI3733673T1/sl unknown
- 2018-12-28 MX MX2020006799A patent/MX2020006799A/es unknown
- 2018-12-28 CA CA3084962A patent/CA3084962C/en active Active
- 2018-12-28 BR BR112020013141-5A patent/BR112020013141B1/pt active IP Right Grant
- 2018-12-28 NZ NZ764644A patent/NZ764644A/en unknown
- 2018-12-28 RS RS20220792A patent/RS63515B1/sr unknown
- 2018-12-28 PL PL18896304.5T patent/PL3733673T3/pl unknown
- 2018-12-28 ES ES18896304T patent/ES2922633T3/es active Active
- 2018-12-28 PT PT188963045T patent/PT3733673T/pt unknown
- 2018-12-28 MA MA51431A patent/MA51431B1/fr unknown
- 2018-12-28 RU RU2020124578A patent/RU2758370C1/ru active
- 2018-12-28 HU HUE18896304A patent/HUE059580T2/hu unknown
- 2018-12-28 SG SG11202004917UA patent/SG11202004917UA/en unknown
- 2018-12-28 LT LTEPPCT/KR2018/016814T patent/LT3733673T/lt unknown
- 2018-12-28 EP EP18896304.5A patent/EP3733673B1/en active Active
- 2018-12-28 CN CN201880084457.1A patent/CN111527091B/zh active Active
- 2018-12-28 WO PCT/KR2018/016814 patent/WO2019132562A1/ko unknown
- 2018-12-28 JP JP2020532893A patent/JP6995428B2/ja active Active
- 2018-12-28 HR HRP20221043TT patent/HRP20221043T1/hr unknown
-
2020
- 2020-06-10 DO DO2020000112A patent/DOP2020000112A/es unknown
- 2020-06-11 CO CONC2020/0007162A patent/CO2020007162A2/es unknown
- 2020-06-25 SA SA520412335A patent/SA520412335B1/ar unknown
- 2020-06-26 CL CL2020001752A patent/CL2020001752A1/es unknown
- 2020-06-28 PH PH12020551013A patent/PH12020551013A1/en unknown
- 2020-06-29 EC ECSENADI202035590A patent/ECSP20035590A/es unknown
-
2021
- 2021-05-24 KR KR1020210066213A patent/KR102592083B1/ko active IP Right Grant
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20221043T1 (hr) | Derivat oksi-fluoropiperidina kao inhibitor kinaze | |
| HRP20171999T1 (hr) | Novi derivati aminopirimidina | |
| HRP20200781T1 (hr) | DERIVATI PIRAZOLO[1,5-a]PIRAZIN-4-ILA KAO INHIBITORI JAK | |
| JP2012529522A5 (hr) | ||
| RU2498983C2 (ru) | Соединения фениламинопиримидина и их применения | |
| HRP20171696T1 (hr) | 3,4-dihidroizokinolin-2(1h)-ilni spojevi | |
| HRP20191364T1 (hr) | Sik-inhibitori tipa heteroarila | |
| RU2020123547A (ru) | Соединения и композиции для модуляции киназной активности мутантов egfr | |
| HRP20170112T1 (hr) | Supstituirani spojevi piridin-2-karboksamida kao kinazni inhibitori signalne regulacije apoptoze | |
| HRP20171913T1 (hr) | Aminopirimidinilni spojevi kao inhibitori jak | |
| HRP20170017T1 (hr) | Inhibitori tirozin kinaze | |
| JP2012501313A5 (hr) | ||
| ES2638179T3 (es) | Compuestos de pirrolopirimidina sustituidos, composiciones de los mismos, y métodos de tratamiento con los mismos | |
| JP2019081762A5 (hr) | ||
| RU2014125211A (ru) | Фтор-18 и углерод-11 меченые радиолиганды для томографии с позитронной эмиссией (рет), визуализирующей lrrk2 | |
| AR065556A1 (es) | Derivados de 3-(( 1,2,4) triazolo (4,3-a) piridin -7-il) benzamida | |
| PE20140502A1 (es) | Pirimidinas sustituidas de diaminocarboxamida y diaminocarbonitrilo, composiciones de las mismas y metodos de tratamiento con las mismas | |
| PE20220253A1 (es) | Benzamidas sustituidas con 1,3-tiazol-2-ilo | |
| HRP20240161T1 (hr) | Inhibitor atr i njegova primjena | |
| HRP20140611T1 (hr) | Inhibitori kinaze p70 s6 | |
| JP2014505037A5 (hr) | ||
| HRP20201430T1 (hr) | Spojevi 6-heterociklil-4-morfolin-4-ilpiridin-2-ona korisni za liječenje karcinoma i dijabetesa | |
| PE20081379A1 (es) | Composiciones farmaceuticas que comprende nilotinib | |
| JP2016527238A5 (hr) | ||
| HRP20211957T1 (hr) | Analozi 1,4-disupstituiranog piridazina i postupci za liječenje stanja povezanih s nedostatkom smn |