JP2006507302A5 - - Google Patents
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- JP2006507302A5 JP2006507302A5 JP2004550143A JP2004550143A JP2006507302A5 JP 2006507302 A5 JP2006507302 A5 JP 2006507302A5 JP 2004550143 A JP2004550143 A JP 2004550143A JP 2004550143 A JP2004550143 A JP 2004550143A JP 2006507302 A5 JP2006507302 A5 JP 2006507302A5
- Authority
- JP
- Japan
- Prior art keywords
- amino
- pyrimidin
- compound
- carbonitrile
- thiazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- QSBMSTSCSFSHFR-UHFFFAOYSA-N 5-phenyl-n-[6-(piperidin-4-ylmethoxy)pyrimidin-4-yl]-1,3-thiazol-2-amine Chemical compound C1CNCCC1COC(N=CN=1)=CC=1NC(S1)=NC=C1C1=CC=CC=C1 QSBMSTSCSFSHFR-UHFFFAOYSA-N 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 claims 38
- 238000000034 method Methods 0.000 claims 36
- 206010028980 Neoplasm Diseases 0.000 claims 16
- 201000011510 cancer Diseases 0.000 claims 15
- 150000003839 salts Chemical class 0.000 claims 15
- 125000000623 heterocyclic group Chemical group 0.000 claims 14
- 125000003118 aryl group Chemical group 0.000 claims 12
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 11
- 125000001424 substituent group Chemical group 0.000 claims 11
- 229910052736 halogen Inorganic materials 0.000 claims 9
- 150000002367 halogens Chemical class 0.000 claims 9
- 239000003607 modifier Substances 0.000 claims 9
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims 8
- 241000124008 Mammalia Species 0.000 claims 8
- 125000000304 alkynyl group Chemical group 0.000 claims 6
- -1 2-morpholin-4-ylethyl Chemical group 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 4
- 125000006663 (C1-C6) perfluoroalkyl group Chemical group 0.000 claims 4
- 239000004037 angiogenesis inhibitor Substances 0.000 claims 4
- 229940121369 angiogenesis inhibitor Drugs 0.000 claims 4
- 201000010099 disease Diseases 0.000 claims 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 4
- 239000003112 inhibitor Substances 0.000 claims 4
- DNUTZBZXLPWRJG-UHFFFAOYSA-M piperidine-1-carboxylate Chemical compound [O-]C(=O)N1CCCCC1 DNUTZBZXLPWRJG-UHFFFAOYSA-M 0.000 claims 4
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims 4
- 125000006664 (C1-C3) perfluoroalkyl group Chemical group 0.000 claims 3
- LMCLAVRZNUMBHA-UHFFFAOYSA-N 2-[(2-methyl-6-piperidin-4-yloxypyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OC2CCNCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 LMCLAVRZNUMBHA-UHFFFAOYSA-N 0.000 claims 3
- 102100032187 Androgen receptor Human genes 0.000 claims 3
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 3
- 229940122440 HIV protease inhibitor Drugs 0.000 claims 3
- 229940121710 HMGCoA reductase inhibitor Drugs 0.000 claims 3
- 229940123468 Transferase inhibitor Drugs 0.000 claims 3
- 125000003342 alkenyl group Chemical group 0.000 claims 3
- 108010080146 androgen receptors Proteins 0.000 claims 3
- 230000001028 anti-proliverative effect Effects 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000002254 cytotoxic agent Substances 0.000 claims 3
- 229940127089 cytotoxic agent Drugs 0.000 claims 3
- 231100000599 cytotoxic agent Toxicity 0.000 claims 3
- 239000003937 drug carrier Substances 0.000 claims 3
- 102000015694 estrogen receptors Human genes 0.000 claims 3
- 108010038795 estrogen receptors Proteins 0.000 claims 3
- 239000003102 growth factor Substances 0.000 claims 3
- 239000004030 hiv protease inhibitor Substances 0.000 claims 3
- 239000002471 hydroxymethylglutaryl coenzyme A reductase inhibitor Substances 0.000 claims 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 3
- 229910052760 oxygen Inorganic materials 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 102000027483 retinoid hormone receptors Human genes 0.000 claims 3
- 108091008679 retinoid hormone receptors Proteins 0.000 claims 3
- 239000003419 rna directed dna polymerase inhibitor Substances 0.000 claims 3
- 229910052717 sulfur Inorganic materials 0.000 claims 3
- 239000003558 transferase inhibitor Substances 0.000 claims 3
- QWTMSTGFUNYRJX-UHFFFAOYSA-N 2-[(6-piperidin-4-yloxy-2-propan-2-ylpyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OC2CCNCC2)=NC(C(C)C)=NC=1NC1=NC=C(C#N)S1 QWTMSTGFUNYRJX-UHFFFAOYSA-N 0.000 claims 2
- PQKRBHFNUGEZEQ-UHFFFAOYSA-N 2-[[2-methyl-6-(morpholin-2-ylmethoxy)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OCC2OCCNC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 PQKRBHFNUGEZEQ-UHFFFAOYSA-N 0.000 claims 2
- YKOCOBQSAHSNNH-UHFFFAOYSA-N 2-[[2-methyl-6-(oxolan-3-ylamino)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NC1CCOC1 YKOCOBQSAHSNNH-UHFFFAOYSA-N 0.000 claims 2
- KRKUIWZXGWIIKJ-UHFFFAOYSA-N 2-[[2-methyl-6-(piperidin-4-ylmethoxy)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OCC2CCNCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 KRKUIWZXGWIIKJ-UHFFFAOYSA-N 0.000 claims 2
- NDGRIVZUQDOJBP-VIFPVBQESA-N 2-[[2-methyl-6-[(3s)-pyrrolidin-3-yl]oxypyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(O[C@@H]2CNCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 NDGRIVZUQDOJBP-VIFPVBQESA-N 0.000 claims 2
- BHXHDXIVJVSHQH-UHFFFAOYSA-N 2-[[6-(3-morpholin-4-ylpropylamino)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound S1C(C#N)=CN=C1NC1=CC(NCCCN2CCOCC2)=NC=N1 BHXHDXIVJVSHQH-UHFFFAOYSA-N 0.000 claims 2
- NIPLEYWULBKSHR-UHFFFAOYSA-N 5-phenyl-n-(6-piperidin-4-yloxypyrimidin-4-yl)-1,3-thiazol-2-amine Chemical compound C1CNCCC1OC1=CC(NC=2SC(=CN=2)C=2C=CC=CC=2)=NC=N1 NIPLEYWULBKSHR-UHFFFAOYSA-N 0.000 claims 2
- 206010006187 Breast cancer Diseases 0.000 claims 2
- 208000026310 Breast neoplasm Diseases 0.000 claims 2
- 206010012689 Diabetic retinopathy Diseases 0.000 claims 2
- 102100025306 Integrin alpha-IIb Human genes 0.000 claims 2
- 101710149643 Integrin alpha-IIb Proteins 0.000 claims 2
- 206010033266 Ovarian Hyperstimulation Syndrome Diseases 0.000 claims 2
- 108090000412 Protein-Tyrosine Kinases Proteins 0.000 claims 2
- 102000004022 Protein-Tyrosine Kinases Human genes 0.000 claims 2
- NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims 2
- 206010064930 age-related macular degeneration Diseases 0.000 claims 2
- 239000005557 antagonist Substances 0.000 claims 2
- 229940079593 drug Drugs 0.000 claims 2
- 239000003814 drug Substances 0.000 claims 2
- 208000030533 eye disease Diseases 0.000 claims 2
- 125000005842 heteroatom Chemical group 0.000 claims 2
- 208000027866 inflammatory disease Diseases 0.000 claims 2
- 208000002780 macular degeneration Diseases 0.000 claims 2
- 125000002950 monocyclic group Chemical group 0.000 claims 2
- 229910052757 nitrogen Inorganic materials 0.000 claims 2
- 230000016087 ovulation Effects 0.000 claims 2
- 230000002265 prevention Effects 0.000 claims 2
- 238000001959 radiotherapy Methods 0.000 claims 2
- 230000004936 stimulating effect Effects 0.000 claims 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- 230000000451 tissue damage Effects 0.000 claims 2
- 231100000827 tissue damage Toxicity 0.000 claims 2
- VEEGZPWAAPPXRB-BJMVGYQFSA-N (3e)-3-(1h-imidazol-5-ylmethylidene)-1h-indol-2-one Chemical compound O=C1NC2=CC=CC=C2\C1=C/C1=CN=CN1 VEEGZPWAAPPXRB-BJMVGYQFSA-N 0.000 claims 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims 1
- AJXHBPDYXACVLJ-UHFFFAOYSA-N 2-[(6-piperidin-4-yloxypyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile Chemical compound S1C(C#N)=CN=C1NC1=CC(OC2CCNCC2)=NC=N1 AJXHBPDYXACVLJ-UHFFFAOYSA-N 0.000 claims 1
- OQZMLPYKCSMWCP-UHFFFAOYSA-N 2-[(6-piperidin-4-ylsulfanylpyrimidin-4-yl)amino]-1,3-thiazole-5-carbonitrile Chemical compound S1C(C#N)=CN=C1NC1=CC(SC2CCNCC2)=NC=N1 OQZMLPYKCSMWCP-UHFFFAOYSA-N 0.000 claims 1
- JUCRVOPOJXROMZ-UHFFFAOYSA-N 2-[2-[[6-[(5-cyano-1,3-thiazol-2-yl)amino]-2-methylpyrimidin-4-yl]amino]piperidin-1-yl]-n-propan-2-ylacetamide Chemical compound CC(C)NC(=O)CN1CCCCC1NC1=CC(NC=2SC(=CN=2)C#N)=NC(C)=N1 JUCRVOPOJXROMZ-UHFFFAOYSA-N 0.000 claims 1
- JNWJVIYRMGXYLR-UHFFFAOYSA-N 2-[4-[[6-[(5-cyano-1,3-thiazol-2-yl)amino]-2-methylpyrimidin-4-yl]oxymethyl]piperidin-1-yl]acetic acid Chemical compound C=1C(OCC2CCN(CC(O)=O)CC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 JNWJVIYRMGXYLR-UHFFFAOYSA-N 0.000 claims 1
- UZQYCXNCJRHTFJ-UHFFFAOYSA-N 2-[5-methyl-6-(piperidin-4-ylamino)pyrimidin-4-yl]oxy-1,3-thiazole-5-carbonitrile Chemical compound N1=CN=C(OC=2SC(=CN=2)C#N)C(C)=C1NC1CCNCC1 UZQYCXNCJRHTFJ-UHFFFAOYSA-N 0.000 claims 1
- JJCMGNMUYUTOCB-UHFFFAOYSA-N 2-[[2-methyl-6-(2-morpholin-4-ylethoxy)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OCCN2CCOCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 JJCMGNMUYUTOCB-UHFFFAOYSA-N 0.000 claims 1
- WNVVVMNKLMNWAH-UHFFFAOYSA-N 2-[[2-methyl-6-(2-morpholin-4-ylethylamino)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NCCN1CCOCC1 WNVVVMNKLMNWAH-UHFFFAOYSA-N 0.000 claims 1
- VGBXWUIRJDXYGD-UHFFFAOYSA-N 2-[[2-methyl-6-(2-morpholin-4-ylethylsulfanyl)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(SCCN2CCOCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 VGBXWUIRJDXYGD-UHFFFAOYSA-N 0.000 claims 1
- RRGNLSPIERWMSN-UHFFFAOYSA-N 2-[[2-methyl-6-(2-piperidin-1-ylethoxy)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OCCN2CCCCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 RRGNLSPIERWMSN-UHFFFAOYSA-N 0.000 claims 1
- ZLPLVZIVZNTCLE-UHFFFAOYSA-N 2-[[2-methyl-6-(3-morpholin-4-ylpropoxy)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(OCCCN2CCOCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 ZLPLVZIVZNTCLE-UHFFFAOYSA-N 0.000 claims 1
- FNGOZGCBJZSAPH-UHFFFAOYSA-N 2-[[2-methyl-6-(oxan-4-ylamino)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NC1CCOCC1 FNGOZGCBJZSAPH-UHFFFAOYSA-N 0.000 claims 1
- VPMQRJXWAPWEEL-UHFFFAOYSA-N 2-[[2-methyl-6-(piperidin-4-ylamino)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NC1CCNCC1 VPMQRJXWAPWEEL-UHFFFAOYSA-N 0.000 claims 1
- MJTVIEHXCFQDDI-UHFFFAOYSA-N 2-[[2-methyl-6-(piperidin-4-ylmethylamino)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NCC1CCNCC1 MJTVIEHXCFQDDI-UHFFFAOYSA-N 0.000 claims 1
- NDGRIVZUQDOJBP-SECBINFHSA-N 2-[[2-methyl-6-[(3r)-pyrrolidin-3-yl]oxypyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(O[C@H]2CNCC2)=NC(C)=NC=1NC1=NC=C(C#N)S1 NDGRIVZUQDOJBP-SECBINFHSA-N 0.000 claims 1
- PXYDNYQZIPUIKI-UHFFFAOYSA-N 2-[[6-(1,4-dioxan-2-ylmethylamino)-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NCC1COCCO1 PXYDNYQZIPUIKI-UHFFFAOYSA-N 0.000 claims 1
- QINGBMINRYJAMY-UHFFFAOYSA-N 2-[[6-(3-imidazol-1-ylpropylamino)-2-methylpyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound C=1C(NC=2SC(=CN=2)C#N)=NC(C)=NC=1NCCCN1C=CN=C1 QINGBMINRYJAMY-UHFFFAOYSA-N 0.000 claims 1
- KIXFMPQMRGLLJE-UHFFFAOYSA-N 2-[[6-(piperidin-4-ylmethoxy)pyrimidin-4-yl]amino]-1,3-thiazole-5-carbonitrile Chemical compound S1C(C#N)=CN=C1NC1=CC(OCC2CCNCC2)=NC=N1 KIXFMPQMRGLLJE-UHFFFAOYSA-N 0.000 claims 1
- 208000031261 Acute myeloid leukaemia Diseases 0.000 claims 1
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- HVXBOLULGPECHP-WAYWQWQTSA-N Combretastatin A4 Chemical compound C1=C(O)C(OC)=CC=C1\C=C/C1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-WAYWQWQTSA-N 0.000 claims 1
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- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
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- 206010041067 Small cell lung cancer Diseases 0.000 claims 1
- UIRKNQLZZXALBI-MSVGPLKSSA-N Squalamine Chemical compound C([C@@H]1C[C@H]2O)[C@@H](NCCCNCCCCN)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@H](C)CC[C@H](C(C)C)OS(O)(=O)=O)[C@@]2(C)CC1 UIRKNQLZZXALBI-MSVGPLKSSA-N 0.000 claims 1
- UIRKNQLZZXALBI-UHFFFAOYSA-N Squalamine Natural products OC1CC2CC(NCCCNCCCCN)CCC2(C)C2C1C1CCC(C(C)CCC(C(C)C)OS(O)(=O)=O)C1(C)CC2 UIRKNQLZZXALBI-UHFFFAOYSA-N 0.000 claims 1
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- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 claims 1
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- YSRXZZKWZJOLNZ-UHFFFAOYSA-N n-(2-methyl-6-piperidin-4-yloxypyrimidin-4-yl)-5-phenyl-1,3-thiazol-2-amine Chemical compound C=1C(OC2CCNCC2)=NC(C)=NC=1NC(S1)=NC=C1C1=CC=CC=C1 YSRXZZKWZJOLNZ-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
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- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
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- GZUITABIAKMVPG-UHFFFAOYSA-N raloxifene Chemical compound C1=CC(O)=CC=C1C1=C(C(=O)C=2C=CC(OCCN3CCCCC3)=CC=2)C2=CC=C(O)C=C2S1 GZUITABIAKMVPG-UHFFFAOYSA-N 0.000 claims 1
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- 230000003637 steroidlike Effects 0.000 claims 1
- 210000002784 stomach Anatomy 0.000 claims 1
- 229960001603 tamoxifen Drugs 0.000 claims 1
- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 claims 1
- GGHSPLOGDCKWKX-UHFFFAOYSA-N tert-butyl 2-[[6-[(5-cyano-1,3-thiazol-2-yl)amino]-2-methylpyrimidin-4-yl]oxymethyl]morpholine-4-carboxylate Chemical compound C=1C(OCC2OCCN(C2)C(=O)OC(C)(C)C)=NC(C)=NC=1NC1=NC=C(C#N)S1 GGHSPLOGDCKWKX-UHFFFAOYSA-N 0.000 claims 1
- HLFUHRZVPXEVOJ-UHFFFAOYSA-N tert-butyl 4-[[6-[(5-phenyl-1,3-thiazol-2-yl)amino]pyrimidin-4-yl]oxymethyl]piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1COC1=CC(NC=2SC(=CN=2)C=2C=CC=CC=2)=NC=N1 HLFUHRZVPXEVOJ-UHFFFAOYSA-N 0.000 claims 1
- 229960003433 thalidomide Drugs 0.000 claims 1
- COKMIXFXJJXBQG-NRFANRHFSA-N tirofiban Chemical group C1=CC(C[C@H](NS(=O)(=O)CCCC)C(O)=O)=CC=C1OCCCCC1CCNCC1 COKMIXFXJJXBQG-NRFANRHFSA-N 0.000 claims 1
- 229960003425 tirofiban Drugs 0.000 claims 1
- 229960000575 trastuzumab Drugs 0.000 claims 1
- 208000027930 type IV hypersensitivity disease Diseases 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
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|---|---|---|---|
| US42231302P | 2002-10-30 | 2002-10-30 | |
| PCT/US2003/034100 WO2004041164A2 (en) | 2002-10-30 | 2003-10-24 | Kinase inhibitors |
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| Publication Number | Publication Date |
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| JP2006507302A JP2006507302A (ja) | 2006-03-02 |
| JP2006507302A5 true JP2006507302A5 (enExample) | 2006-08-03 |
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| JP (1) | JP2006507302A (enExample) |
| AU (1) | AU2003285007A1 (enExample) |
| CA (1) | CA2503715A1 (enExample) |
| WO (1) | WO2004041164A2 (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| HRP20050696B1 (en) | 2003-01-14 | 2008-10-31 | Arena Pharmaceuticals Inc. | 1,2,3-trisubstituted aryl and heteroaryl derivatives as modulators of metabolism and the prpphylaxis and treatment of disorders related thereto such as diabetes and hyperglycemia |
| US8168568B1 (en) | 2003-03-10 | 2012-05-01 | The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | Combinatorial therapy for protein signaling diseases |
| AR045047A1 (es) * | 2003-07-11 | 2005-10-12 | Arena Pharm Inc | Derivados arilo y heteroarilo trisustituidos como moduladores del metabolismo y de la profilaxis y tratamiento de desordenes relacionados con los mismos |
| UA92150C2 (ru) * | 2004-06-04 | 2010-10-11 | Арена Фармасьютикалз, Инк. | Замещенные производные арила и гетероарила как модуляторы метаболизма и для профилактики и лечения связанных с ним расстройств |
| BRPI0518829A2 (pt) | 2004-12-06 | 2008-12-09 | Avigen Inc | mÉtodo para o tratamento de dor neuropÁtica e sÍndromes associadas |
| MY148521A (en) * | 2005-01-10 | 2013-04-30 | Arena Pharm Inc | Substituted pyridinyl and pyrimidinyl derivatives as modulators of metabolism and the treatment of disorders related thereto |
| WO2006117608A1 (en) | 2005-04-29 | 2006-11-09 | Ferring International Center S.A. | Treatment or prevention of ovarian hyperstimulation syndrome (ohss) using a dopamine agonist |
| EP1901747A2 (en) * | 2005-05-25 | 2008-03-26 | Ingenium Pharmaceuticals AG | Pyrimidine-based cdk inhibitors for treating pain |
| EP1968596A4 (en) * | 2005-12-22 | 2010-12-01 | Icagen Inc | ANTAGONISTS OF CALCIUM CHANNEL |
| ATE539748T1 (de) * | 2006-01-27 | 2012-01-15 | Array Biopharma Inc | Glucokinaseaktivatoren |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| JP4782239B2 (ja) | 2007-04-18 | 2011-09-28 | ファイザー・プロダクツ・インク | 異常細胞増殖治療のためのスルホニルアミド誘導体 |
| US8507498B2 (en) | 2007-04-24 | 2013-08-13 | Ingenium Pharmaceuticals Gmbh | 4, 6-disubstituted aminopyrimidine derivatives as inhibitors of protein kinases |
| BRPI0816881A2 (pt) | 2007-09-21 | 2015-03-17 | Array Biopharma Inc | Composto, composição farmacêutica, uso de um composto, e, métodos para tratar doenças ou distúrbios e para preparar um composto. |
| GB0811955D0 (en) | 2008-06-30 | 2008-07-30 | Pci Biotech As | Method |
| WO2010059384A1 (en) * | 2008-10-30 | 2010-05-27 | Janssen Pharmaceutica Nv | Process for the preparation of tri-substituted pyridine and tri-substituted pyrimidine derivatives useful as gdir agonists |
| WO2011144742A1 (en) | 2010-05-21 | 2011-11-24 | Chemilia Ab | Novel pyrimidine derivatives |
| MX2013003184A (es) | 2010-09-22 | 2013-06-07 | Arena Pharm Inc | Moduladores del receptor gpr119 y el tratamiento de transtornos relacionados con el mismo. |
| EP2688883B1 (en) | 2011-03-24 | 2016-05-18 | Noviga Research AB | Pyrimidine derivatives |
| WO2012149528A1 (en) * | 2011-04-29 | 2012-11-01 | Exelixis, Inc. | Inhibitors of inducible form of 6-phosphofructose-2-kinase |
| US11007175B2 (en) | 2015-01-06 | 2021-05-18 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| BR112017027656B1 (pt) | 2015-06-22 | 2023-12-05 | Arena Pharmaceuticals, Inc. | Hábito cristalino de placa livre de sal de l-arginina de ácido (r)-2-(7-(4- ciclopentil-3-(trifluorometil)benzilóxi)- 1,2,3,4-tetra-hidrociclo-penta[b]indol-3- il)acético, composição farmacêutica que o compreende, seus usos e método de preparação do mesmo |
| TWI620748B (zh) * | 2016-02-05 | 2018-04-11 | National Health Research Institutes | 氨基噻唑化合物及其用途 |
| WO2018023017A1 (en) | 2016-07-29 | 2018-02-01 | Janssen Pharmaceutica Nv | Methods of treating prostate cancer |
| CA3053418A1 (en) | 2017-02-16 | 2018-08-23 | Arena Pharmaceuticals, Inc. | Compounds and methods for treatment of primary biliary cholangitis |
| TWI667236B (zh) | 2017-06-13 | 2019-08-01 | 財團法人國家衛生研究院 | 作為蛋白激酶抑制劑的胺基噻唑化合物 |
| BR112020024762A2 (pt) | 2018-06-06 | 2021-03-23 | Arena Pharmaceuticals, Inc. | métodos de tratamento de condições relacionadas ao receptor s1p1 |
| EP3643713B1 (en) | 2018-10-23 | 2025-07-30 | iOmx Therapeutics AG | Heterocyclic kinase inhibitors and uses thereof |
| CN111116575B (zh) * | 2019-12-18 | 2021-06-15 | 浙江工业大学 | 一种5-氟-2,4-嘧啶二胺类化合物及其制备与应用 |
| CN111388656B (zh) * | 2020-04-17 | 2021-01-15 | 广州医科大学附属第三医院（广州重症孕产妇救治中心、广州柔济医院） | Kallistatin蛋白在制备防治OHSS的药物中的应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2308833A3 (en) * | 1999-04-15 | 2011-09-28 | Bristol-Myers Squibb Company | Cyclic protein tyrosine kinase inhibitors |
| US20020137755A1 (en) * | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| HUP0303538A2 (hu) * | 2000-12-21 | 2005-02-28 | Bristol-Myers Squibb Co. | Tirozin kinázok Tec családjának tiazolil-vegyület inhibitorai és ezeket tartalmazó gyógyszerkészítmények |
-
2003
- 2003-10-24 EP EP03779322A patent/EP1558609A4/en not_active Withdrawn
- 2003-10-24 WO PCT/US2003/034100 patent/WO2004041164A2/en not_active Ceased
- 2003-10-24 CA CA002503715A patent/CA2503715A1/en not_active Abandoned
- 2003-10-24 JP JP2004550143A patent/JP2006507302A/ja not_active Withdrawn
- 2003-10-24 AU AU2003285007A patent/AU2003285007A1/en not_active Abandoned
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