RU2331647C2 - Тиенопиримидиндионы и их применение в модулировании аутоиммунного заболевания - Google Patents
Тиенопиримидиндионы и их применение в модулировании аутоиммунного заболевания Download PDFInfo
- Publication number
- RU2331647C2 RU2331647C2 RU2005121494/04A RU2005121494A RU2331647C2 RU 2331647 C2 RU2331647 C2 RU 2331647C2 RU 2005121494/04 A RU2005121494/04 A RU 2005121494/04A RU 2005121494 A RU2005121494 A RU 2005121494A RU 2331647 C2 RU2331647 C2 RU 2331647C2
- Authority
- RU
- Russia
- Prior art keywords
- methyl
- carbonyl
- pyrimidin
- methylethyl
- hydroxy
- Prior art date
Links
- 241000551547 Dione <red algae> Species 0.000 title abstract 4
- RBNBDIMXFJYDLQ-UHFFFAOYSA-N thieno[3,2-d]pyrimidine Chemical compound C1=NC=C2SC=CC2=N1 RBNBDIMXFJYDLQ-UHFFFAOYSA-N 0.000 title abstract 4
- 208000023275 Autoimmune disease Diseases 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract 28
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 9
- 150000003839 salts Chemical class 0.000 claims abstract 9
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 8
- 125000005842 heteroatom Chemical group 0.000 claims abstract 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 125000003118 aryl group Chemical group 0.000 claims abstract 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 5
- 239000012453 solvate Substances 0.000 claims abstract 5
- 239000001257 hydrogen Substances 0.000 claims abstract 4
- 238000000034 method Methods 0.000 claims abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 4
- 125000006413 ring segment Chemical group 0.000 claims abstract 4
- 239000003814 drug Substances 0.000 claims abstract 3
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000004122 cyclic group Chemical class 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 7
- -1 2-pyridinyl Chemical group 0.000 claims 5
- 230000015572 biosynthetic process Effects 0.000 claims 5
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 4
- 238000006243 chemical reaction Methods 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052717 sulfur Chemical group 0.000 claims 4
- 239000011593 sulfur Chemical group 0.000 claims 4
- 229910052799 carbon Inorganic materials 0.000 claims 3
- 125000004982 dihaloalkyl group Chemical group 0.000 claims 3
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000004043 oxo group Chemical group O=* 0.000 claims 3
- 125000001424 substituent group Chemical group 0.000 claims 3
- 125000004385 trihaloalkyl group Chemical group 0.000 claims 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- 230000003993 interaction Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 2
- 210000003819 peripheral blood mononuclear cell Anatomy 0.000 claims 2
- 230000035755 proliferation Effects 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- 125000006555 (C3-C5) cycloalkyl group Chemical group 0.000 claims 1
- NMHRECIQUFFUHV-NRFANRHFSA-N 1-cyclopropyl-6-[(3,5-dimethyl-1h-pyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound CC1=NNC(C)=C1CC1=C(C(=O)N2OC[C@@](C)(O)C2)C(C(=O)N(C)C(=O)N2C3CC3)=C2S1 NMHRECIQUFFUHV-NRFANRHFSA-N 0.000 claims 1
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- PRNXOFBDXNTIFG-HXUWFJFHSA-N 5-[(4r)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[[5-methyl-3-(trifluoromethyl)-1h-pyrazol-4-yl]methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC1=C(C)NN=C1C(F)(F)F PRNXOFBDXNTIFG-HXUWFJFHSA-N 0.000 claims 1
- VFLLHPRZDQOXCE-DEOSSOPVSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC(CC=2C3=CC=CN=C3NC=2)=C1C(=O)N1C[C@](C)(O)CO1 VFLLHPRZDQOXCE-DEOSSOPVSA-N 0.000 claims 1
- YVFBMNCDAFQCEQ-QHCPKHFHSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-(1h-pyrrolo[2,3-b]pyridin-3-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CC=2C3=CC=CN=C3NC=2)=C1C(=O)N1C[C@](C)(O)CO1 YVFBMNCDAFQCEQ-QHCPKHFHSA-N 0.000 claims 1
- UQJFDUVHWVBISL-SFHVURJKSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-(triazol-1-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CN1C=CN=N1 UQJFDUVHWVBISL-SFHVURJKSA-N 0.000 claims 1
- RYCSBKCBICNZBS-MHZLTWQESA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-[(4-pyridin-2-ylphenyl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC(C=C1)=CC=C1C1=CC=CC=N1 RYCSBKCBICNZBS-MHZLTWQESA-N 0.000 claims 1
- SYVOSXMIUPNYLV-VWLOTQADSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-[(5-pyridin-2-ylthiophen-2-yl)methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC(S1)=CC=C1C1=CC=CC=N1 SYVOSXMIUPNYLV-VWLOTQADSA-N 0.000 claims 1
- VDDOEISUJGJOHU-QFIPXVFZSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-yl-6-[[1-(1,3-thiazol-2-yl)pyrazol-4-yl]methyl]thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC(=C1)C=NN1C1=NC=CS1 VDDOEISUJGJOHU-QFIPXVFZSA-N 0.000 claims 1
- VNXZYGDWCBUEDR-VWLOTQADSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propyl-6-(quinolin-4-ylmethyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(CCC)C=2SC(CC=2C3=CC=CC=C3N=CC=2)=C1C(=O)N1C[C@](C)(O)CO1 VNXZYGDWCBUEDR-VWLOTQADSA-N 0.000 claims 1
- YIOZKLDAZRCZTF-VWLOTQADSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[(1-phenylpyrazol-4-yl)methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC(=C1)C=NN1C1=CC=CC=C1 YIOZKLDAZRCZTF-VWLOTQADSA-N 0.000 claims 1
- SOFSLARRWWWVMX-DEOSSOPVSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[[5-methyl-1-pyrimidin-2-yl-3-(trifluoromethyl)pyrazol-4-yl]methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC(C(=N1)C(F)(F)F)=C(C)N1C1=NC=CC=N1 SOFSLARRWWWVMX-DEOSSOPVSA-N 0.000 claims 1
- PRNXOFBDXNTIFG-FQEVSTJZSA-N 5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-6-[[5-methyl-3-(trifluoromethyl)-1h-pyrazol-4-yl]methyl]-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC1=C(C)NN=C1C(F)(F)F PRNXOFBDXNTIFG-FQEVSTJZSA-N 0.000 claims 1
- RHPDPKAYECJJOK-QFIPXVFZSA-N 6-(benzotriazol-1-ylmethyl)-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CN2C3=CC=CC=C3N=N2)=C1C(=O)N1C[C@](C)(O)CO1 RHPDPKAYECJJOK-QFIPXVFZSA-N 0.000 claims 1
- ORBWWPHPDXXVIW-FQEVSTJZSA-N 6-[(2,4-dichloro-1,3-thiazol-5-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1SC(Cl)=NC=1Cl ORBWWPHPDXXVIW-FQEVSTJZSA-N 0.000 claims 1
- UDSVFQFDRPEYFT-SANMLTNESA-N 6-[(3,5-dimethyl-1-pyridin-4-ylpyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC(=C1C)C(C)=NN1C1=CC=NC=C1 UDSVFQFDRPEYFT-SANMLTNESA-N 0.000 claims 1
- FKIUQMBRQLGLAC-QFIPXVFZSA-N 6-[(3,5-dimethyl-1h-pyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1C(C)=NNC=1C FKIUQMBRQLGLAC-QFIPXVFZSA-N 0.000 claims 1
- KWSDOBIBNMXOEI-NRFANRHFSA-N 6-[(3,5-dimethyl-1h-pyrazol-4-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CCC)C=2SC=1CC=1C(C)=NNC=1C KWSDOBIBNMXOEI-NRFANRHFSA-N 0.000 claims 1
- JLYZHDWGRCXGHD-NRFANRHFSA-N 6-[(3-bromothiophen-2-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-(2-methylpropyl)thieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC(C)C)C=2SC=1CC=1SC=CC=1Br JLYZHDWGRCXGHD-NRFANRHFSA-N 0.000 claims 1
- CPRZLKUKNIGNHC-IBGZPJMESA-N 6-[(4,5-dichloro-2-methylimidazol-1-yl)methyl]-1-ethyl-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(CC)C=2SC=1CN1C(C)=NC(Cl)=C1Cl CPRZLKUKNIGNHC-IBGZPJMESA-N 0.000 claims 1
- ZIRDSJWSVSWQOE-QFIPXVFZSA-N 6-[(4-fluorophenyl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C([C@@](C)(O)C1)ON1C(=O)C=1C=2C(=O)N(C)C(=O)N(C(C)C)C=2SC=1CC1=CC=C(F)C=C1 ZIRDSJWSVSWQOE-QFIPXVFZSA-N 0.000 claims 1
- SEBMPNJWZMKGRZ-QHCPKHFHSA-N 6-[(6-chloroimidazo[1,2-a]pyridin-3-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CC=2N3C=C(Cl)C=CC3=NC=2)=C1C(=O)N1C[C@](C)(O)CO1 SEBMPNJWZMKGRZ-QHCPKHFHSA-N 0.000 claims 1
- IXYCVRJQEKQPFU-VWLOTQADSA-N 6-[(8-fluoroquinolin-4-yl)methyl]-5-[(4s)-4-hydroxy-4-methyl-1,2-oxazolidine-2-carbonyl]-3-methyl-1-propan-2-ylthieno[2,3-d]pyrimidine-2,4-dione Chemical compound C1=2C(=O)N(C)C(=O)N(C(C)C)C=2SC(CC=2C3=CC=CC(F)=C3N=CC=2)=C1C(=O)N1C[C@](C)(O)CO1 IXYCVRJQEKQPFU-VWLOTQADSA-N 0.000 claims 1
- 206010062016 Immunosuppression Diseases 0.000 claims 1
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 claims 1
- 125000002619 bicyclic group Chemical group 0.000 claims 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 230000001506 immunosuppresive effect Effects 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- 239000001301 oxygen 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims 1
- 125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims 1
- 208000023504 respiratory system disease Diseases 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 238000002650 immunosuppressive therapy Methods 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
- 0 *N(c([s]c(*[Al])c1C(I)=O)c1C(N1*)=O)C1=O Chemical compound *N(c([s]c(*[Al])c1C(I)=O)c1C(N1*)=O)C1=O 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- 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
-
- 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Immunology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pulmonology (AREA)
- Transplantation (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0300119A SE0300119D0 (sv) | 2003-01-17 | 2003-01-17 | Novel compounds |
| SE0300119-5 | 2003-01-17 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005121494A RU2005121494A (ru) | 2006-02-10 |
| RU2331647C2 true RU2331647C2 (ru) | 2008-08-20 |
Family
ID=20290154
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2005121494/04A RU2331647C2 (ru) | 2003-01-17 | 2004-01-15 | Тиенопиримидиндионы и их применение в модулировании аутоиммунного заболевания |
Country Status (23)
| Country | Link |
|---|---|
| US (2) | US7384951B2 (https=) |
| EP (1) | EP1587812B1 (https=) |
| JP (1) | JP4519121B2 (https=) |
| KR (2) | KR20110125256A (https=) |
| CN (1) | CN100334093C (https=) |
| AT (1) | ATE335748T1 (https=) |
| AU (1) | AU2004206012B2 (https=) |
| BR (1) | BRPI0406801B8 (https=) |
| CA (1) | CA2512441C (https=) |
| DE (1) | DE602004001857T2 (https=) |
| EG (1) | EG25613A (https=) |
| ES (1) | ES2270337T3 (https=) |
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| GB0117583D0 (en) | 2001-07-19 | 2001-09-12 | Astrazeneca Ab | Novel compounds |
| GB0118479D0 (en) | 2001-07-28 | 2001-09-19 | Astrazeneca Ab | Novel compounds |
| RU2332420C2 (ru) * | 2003-01-17 | 2008-08-27 | Астразенека Аб | Тиенопиримидиндионы и их применение в модулировании аутоиммунного заболевания |
| SE0300120D0 (sv) | 2003-01-17 | 2003-01-17 | Astrazeneca Ab | Novel compounds |
| CA2550361C (en) | 2003-12-19 | 2014-04-29 | Prabha Ibrahim | Compounds and methods for development of ret modulators |
| US7498342B2 (en) | 2004-06-17 | 2009-03-03 | Plexxikon, Inc. | Compounds modulating c-kit activity |
| AU2006272951A1 (en) | 2005-05-17 | 2007-02-01 | Plexxikon, Inc. | Pyrrol (2,3-b) pyridine derivatives protein kinase inhibitors |
| CN102206216B (zh) | 2005-06-22 | 2014-11-12 | 普莱希科公司 | 作为蛋白质激酶抑制剂的吡咯并[2,3-b]吡啶衍生物 |
| WO2008063888A2 (en) | 2006-11-22 | 2008-05-29 | Plexxikon, Inc. | Compounds modulating c-fms and/or c-kit activity and uses therefor |
| WO2008079909A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Pyrrolo [2,3-b] pyridines as kinase modulators |
| AU2007336811A1 (en) | 2006-12-21 | 2008-07-03 | Plexxikon, Inc. | Compounds and methods for kinase modulation, and indications therefor |
| PE20081581A1 (es) | 2006-12-21 | 2008-11-12 | Plexxikon Inc | COMPUESTOS PIRROLO[2,3-b]PIRIDINAS COMO MODULADORES DE QUINASA |
| GB0713479D0 (en) * | 2007-07-11 | 2007-08-22 | Syngenta Participations Ag | Substituted aromatic heterocyclic compounds as fungicides |
| JP2010533729A (ja) | 2007-07-17 | 2010-10-28 | プレキシコン，インコーポレーテッド | キナーゼ調節のための化合物と方法、及びそのための適応 |
| WO2010089580A1 (en) | 2009-02-06 | 2010-08-12 | Astrazeneca Ab | Use of a mct1 inhibitor in the treatment of cancers expressing mct1 over mct4 |
| PT2411395E (pt) * | 2009-03-23 | 2013-06-06 | Glenmark Pharmaceuticals Sa | Derivados de furopirimidinadiona como moduladores de trpa1 |
| DK2411397T3 (da) * | 2009-03-23 | 2013-08-05 | Glenmark Pharmaceuticals Sa | Isothiazol-pyrimidindionderivater som modulatorer af TRPA1 |
| KR101739994B1 (ko) | 2009-04-03 | 2017-05-25 | 에프. 호프만-라 로슈 아게 | 프로판-１-술폰산 ｛３-［５-（４-클로로-페닐）-１Ｈ-피롤로［２，３-ｂ］피리딘-３-카르보닐］-２，４-디플루오로-페닐｝-아미드 조성물 및 그의 용도 |
| US8329724B2 (en) | 2009-08-03 | 2012-12-11 | Hoffmann-La Roche Inc. | Process for the manufacture of pharmaceutically active compounds |
| NZ599866A (en) | 2009-11-06 | 2014-09-26 | Plexxikon Inc | Compounds and methods for kinase modulation, and indications therefor |
| KR101911972B1 (ko) | 2011-02-07 | 2018-10-25 | 플렉시콘 인코퍼레이티드 | 키나제 조절을 위한 화합물 및 방법, 및 그에 대한 적응증 |
| TWI558702B (zh) | 2011-02-21 | 2016-11-21 | 普雷辛肯公司 | 醫藥活性物質的固態形式 |
| EP2804852A2 (en) | 2012-01-20 | 2014-11-26 | Regents Of The University Of Minnesota | Therapeutic compounds |
| GB2523211B (en) | 2012-01-27 | 2020-03-18 | Univ Jefferson | MCT protein inhibitor-related prognostic and therapeutic methods |
| US9150570B2 (en) | 2012-05-31 | 2015-10-06 | Plexxikon Inc. | Synthesis of heterocyclic compounds |
| WO2014172627A1 (en) | 2013-04-19 | 2014-10-23 | Thomas Jefferson University | Caveolin-1 related methods for treating glioblastoma with temozolomide |
| MY184561A (en) * | 2013-10-21 | 2021-04-03 | Genosco | Substituted pyrimidine compounds and their use as syk inhibitors |
| CA2974697A1 (en) | 2015-01-22 | 2016-07-28 | The Scripps Research Institute | Pyrimidine-2,4-(1h,3h)-dione derivatives and pharmaceutical compositions thereof and their use as inhibitors of monocarboxylate transporters |
| UY36586A (es) * | 2015-03-26 | 2016-10-31 | Bayer Pharma AG | Heterociclilmetiltienouracilos y uso de los mismos |
| KR101730536B1 (ko) * | 2016-03-17 | 2017-05-02 | 주식회사 골프존 | 스크린 골프 시스템에서 구현되는 컨텐츠 전송 서비스 방법, 컨텐츠 전송 서비스를 위한 모바일 단말기의 제어방법 및 이를 기록한 컴퓨팅 장치에 의해 판독 가능한 기록매체 |
| KR101712836B1 (ko) * | 2016-03-17 | 2017-03-22 | 주식회사 골프존 | 가상 골프 시뮬레이션 장치, 가상 골프를 위한 영상 구현 방법 및 이를 기록한 컴퓨팅 장치에 의해 판독 가능한 기록 매체 |
| KR101712838B1 (ko) * | 2016-03-17 | 2017-03-07 | 주식회사 골프존 | 가상 골프 시뮬레이션 장치, 가상 골프를 위한 영상 구현 방법 및 이를 기록한 컴퓨팅 장치에 의해 판독 가능한 기록 매체 |
| TWI823932B (zh) * | 2018-05-11 | 2023-12-01 | 中國大陸商迪哲（江蘇）醫藥有限公司 | 三唑并嘧啶化合物及其在治療癌症中之用途 |
| CN119080799B (zh) * | 2024-09-27 | 2025-12-05 | 山东大学 | 一种n-羟基噻吩并嘧啶二酮类衍生物及其制备方法与应用 |
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| US6232320B1 (en) | 1998-06-04 | 2001-05-15 | Abbott Laboratories | Cell adhesion-inhibiting antiinflammatory compounds |
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| WO1998054190A1 (en) * | 1997-05-28 | 1998-12-03 | Astra Pharmaceuticals Ltd. | Novel compounds |
| WO2000012514A1 (en) * | 1998-08-28 | 2000-03-09 | Astrazeneca Ab | Novel compounds |
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