NO327708B1 - Pyrazolforbindelser nyttige som proteinkinaseinhibitorer - Google Patents
Pyrazolforbindelser nyttige som proteinkinaseinhibitorer Download PDFInfo
- Publication number
- NO327708B1 NO327708B1 NO20031191A NO20031191A NO327708B1 NO 327708 B1 NO327708 B1 NO 327708B1 NO 20031191 A NO20031191 A NO 20031191A NO 20031191 A NO20031191 A NO 20031191A NO 327708 B1 NO327708 B1 NO 327708B1
- Authority
- NO
- Norway
- Prior art keywords
- ring
- alkyl
- phenyl
- optionally substituted
- halo
- Prior art date
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- 239000003909 protein kinase inhibitor Substances 0.000 title abstract description 11
- 229940045988 antineoplastic drug protein kinase inhibitors Drugs 0.000 title abstract description 6
- 150000003217 pyrazoles Chemical class 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 104
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 55
- 201000010099 disease Diseases 0.000 claims abstract description 47
- 102000002254 Glycogen Synthase Kinase 3 Human genes 0.000 claims abstract description 43
- 108010014905 Glycogen Synthase Kinase 3 Proteins 0.000 claims abstract description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 42
- 206010012601 diabetes mellitus Diseases 0.000 claims abstract description 15
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 14
- 208000024827 Alzheimer disease Diseases 0.000 claims abstract description 12
- 125000000714 pyrimidinyl group Chemical group 0.000 claims abstract description 8
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 217
- 201000006417 multiple sclerosis Diseases 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 239000000203 mixture Substances 0.000 claims description 38
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 34
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000001424 substituent group Chemical group 0.000 claims description 31
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000004429 atom Chemical group 0.000 claims description 29
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 27
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 20
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 19
- 229910052757 nitrogen Chemical group 0.000 claims description 19
- 230000000694 effects Effects 0.000 claims description 18
- 125000001475 halogen functional group Chemical group 0.000 claims description 18
- 125000005843 halogen group Chemical group 0.000 claims description 18
- 201000011510 cancer Diseases 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 125000005605 benzo group Chemical group 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 239000003814 drug Substances 0.000 claims description 11
- 125000005842 heteroatom Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 8
- 239000012472 biological sample Substances 0.000 claims description 8
- 208000035475 disorder Diseases 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 239000011593 sulfur Chemical group 0.000 claims description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
- 125000001624 naphthyl group Chemical group 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
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- 125000001309 chloro group Chemical group Cl* 0.000 claims description 6
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- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 210000003800 pharynx Anatomy 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 229940079593 drug Drugs 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 5
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 5
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 5
- 201000000980 schizophrenia Diseases 0.000 claims description 5
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
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- 206010020880 Hypertrophy Diseases 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 210000000481 breast Anatomy 0.000 claims description 4
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- 208000030507 AIDS Diseases 0.000 claims description 3
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims description 3
- 208000003200 Adenoma Diseases 0.000 claims description 3
- 206010001233 Adenoma benign Diseases 0.000 claims description 3
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- 125000006165 cyclic alkyl group Chemical group 0.000 claims description 3
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- 201000005249 lung adenocarcinoma Diseases 0.000 claims description 3
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- 210000002229 urogenital system Anatomy 0.000 claims description 3
- PKORYTIUMAOPED-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinazoline Chemical compound C1=CC=C2NCNCC2=C1 PKORYTIUMAOPED-UHFFFAOYSA-N 0.000 claims description 2
- 206010004593 Bile duct cancer Diseases 0.000 claims description 2
- 208000010667 Carcinoma of liver and intrahepatic biliary tract Diseases 0.000 claims description 2
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- 206010073069 Hepatic cancer Diseases 0.000 claims description 2
- 201000007180 bile duct carcinoma Diseases 0.000 claims description 2
- 210000004556 brain Anatomy 0.000 claims description 2
- 210000000133 brain stem Anatomy 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims description 2
- 208000029742 colonic neoplasm Diseases 0.000 claims description 2
- 206010073071 hepatocellular carcinoma Diseases 0.000 claims description 2
- 201000002250 liver carcinoma Diseases 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims 2
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- 238000004128 high performance liquid chromatography Methods 0.000 description 152
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- -1 nucleoside triphosphate Chemical class 0.000 description 79
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PCT/US2001/028940 WO2002022607A1 (fr) | 2000-09-15 | 2001-09-14 | Composes pyrazole utiles en tant qu'inhibiteurs de proteine kinase |
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NO20031188A NO20031188L (no) | 2000-09-15 | 2003-03-14 | Pyrazolforbindelser nyttige som proteinkinaseinhibitorer |
NO20031191A NO327708B1 (no) | 2000-09-15 | 2003-03-14 | Pyrazolforbindelser nyttige som proteinkinaseinhibitorer |
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NO20031188A NO20031188L (no) | 2000-09-15 | 2003-03-14 | Pyrazolforbindelser nyttige som proteinkinaseinhibitorer |
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EP (8) | EP1317447B1 (fr) |
JP (9) | JP2004509118A (fr) |
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CN (3) | CN1473161A (fr) |
AP (1) | AP2003002762A0 (fr) |
AT (8) | ATE327990T1 (fr) |
AU (9) | AU2001294558A1 (fr) |
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