JP2006507302A5 - - Google Patents
Download PDFInfo
- Publication number
- 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.)
- Withdrawn
Links
- 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
- 208000010507 Adenocarcinoma of Lung Diseases 0.000 claims 1
- 102000012936 Angiostatins Human genes 0.000 claims 1
- 108010079709 Angiostatins Proteins 0.000 claims 1
- 108010062540 Chorionic Gonadotropin Proteins 0.000 claims 1
- 102000011022 Chorionic Gonadotropin Human genes 0.000 claims 1
- 206010009944 Colon cancer Diseases 0.000 claims 1
- 208000001333 Colorectal Neoplasms Diseases 0.000 claims 1
- 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
- 108090000266 Cyclin-dependent kinases Proteins 0.000 claims 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 claims 1
- 206010012442 Dermatitis contact Diseases 0.000 claims 1
- 201000009273 Endometriosis Diseases 0.000 claims 1
- 108010079345 Follicle Stimulating Hormone Proteins 0.000 claims 1
- 102000012673 Follicle Stimulating Hormone Human genes 0.000 claims 1
- 108700012941 GNRH1 Proteins 0.000 claims 1
- 239000000579 Gonadotropin-Releasing Hormone Substances 0.000 claims 1
- 102000006992 Interferon-alpha Human genes 0.000 claims 1
- 108010047761 Interferon-alpha Proteins 0.000 claims 1
- 102000013462 Interleukin-12 Human genes 0.000 claims 1
- 108010065805 Interleukin-12 Proteins 0.000 claims 1
- 208000031671 Large B-Cell Diffuse Lymphoma Diseases 0.000 claims 1
- 206010058467 Lung neoplasm malignant Diseases 0.000 claims 1
- 108010073521 Luteinizing Hormone Proteins 0.000 claims 1
- 102000009151 Luteinizing Hormone Human genes 0.000 claims 1
- 229940124761 MMP inhibitor Drugs 0.000 claims 1
- 208000001344 Macular Edema Diseases 0.000 claims 1
- 206010025415 Macular oedema Diseases 0.000 claims 1
- 206010027202 Meningitis bacterial Diseases 0.000 claims 1
- 108010057021 Menotropins Proteins 0.000 claims 1
- 208000033776 Myeloid Acute Leukemia Diseases 0.000 claims 1
- 108010016731 PPAR gamma Proteins 0.000 claims 1
- 229930012538 Paclitaxel Natural products 0.000 claims 1
- 206010061902 Pancreatic neoplasm Diseases 0.000 claims 1
- 102100038825 Peroxisome proliferator-activated receptor gamma Human genes 0.000 claims 1
- 229940080774 Peroxisome proliferator-activated receptor gamma agonist Drugs 0.000 claims 1
- 206010060862 Prostate cancer Diseases 0.000 claims 1
- 208000000236 Prostatic Neoplasms Diseases 0.000 claims 1
- 201000004681 Psoriasis Diseases 0.000 claims 1
- 208000007135 Retinal Neovascularization Diseases 0.000 claims 1
- 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
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 1
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 1
- 239000000556 agonist Substances 0.000 claims 1
- 125000002947 alkylene group Chemical group 0.000 claims 1
- 125000005275 alkylenearyl group Chemical group 0.000 claims 1
- 230000033115 angiogenesis Effects 0.000 claims 1
- 230000003110 anti-inflammatory effect Effects 0.000 claims 1
- 239000002220 antihypertensive agent Substances 0.000 claims 1
- FZCSTZYAHCUGEM-UHFFFAOYSA-N aspergillomarasmine B Natural products OC(=O)CNC(C(O)=O)CNC(C(O)=O)CC(O)=O FZCSTZYAHCUGEM-UHFFFAOYSA-N 0.000 claims 1
- 201000009904 bacterial meningitis Diseases 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims 1
- 210000000988 bone and bone Anatomy 0.000 claims 1
- 210000004556 brain Anatomy 0.000 claims 1
- 201000008275 breast carcinoma Diseases 0.000 claims 1
- OZVBMTJYIDMWIL-AYFBDAFISA-N bromocriptine Chemical group C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N[C@]2(C(=O)N3[C@H](C(N4CCC[C@H]4[C@]3(O)O2)=O)CC(C)C)C(C)C)C2)=C3C2=C(Br)NC3=C1 OZVBMTJYIDMWIL-AYFBDAFISA-N 0.000 claims 1
- 229960002802 bromocriptine Drugs 0.000 claims 1
- 230000002490 cerebral effect Effects 0.000 claims 1
- 229940015047 chorionic gonadotropin Drugs 0.000 claims 1
- 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
- 229960003608 clomifene Drugs 0.000 claims 1
- 229960005537 combretastatin A-4 Drugs 0.000 claims 1
- HVXBOLULGPECHP-UHFFFAOYSA-N combretastatin A4 Natural products C1=C(O)C(OC)=CC=C1C=CC1=CC(OC)=C(OC)C(OC)=C1 HVXBOLULGPECHP-UHFFFAOYSA-N 0.000 claims 1
- 208000010247 contact dermatitis Diseases 0.000 claims 1
- 229940111134 coxibs Drugs 0.000 claims 1
- 239000003255 cyclooxygenase 2 inhibitor Substances 0.000 claims 1
- 230000001419 dependent effect Effects 0.000 claims 1
- 230000009977 dual effect Effects 0.000 claims 1
- 229940125436 dual inhibitor Drugs 0.000 claims 1
- 210000000981 epithelium Anatomy 0.000 claims 1
- 239000002834 estrogen receptor modulator Substances 0.000 claims 1
- RWTNPBWLLIMQHL-UHFFFAOYSA-N fexofenadine Chemical compound C1=CC(C(C)(C(O)=O)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 RWTNPBWLLIMQHL-UHFFFAOYSA-N 0.000 claims 1
- 210000002950 fibroblast Anatomy 0.000 claims 1
- 229940028334 follicle stimulating hormone Drugs 0.000 claims 1
- 238000001415 gene therapy Methods 0.000 claims 1
- 208000005017 glioblastoma Diseases 0.000 claims 1
- 102000006495 integrins Human genes 0.000 claims 1
- 108010044426 integrins Proteins 0.000 claims 1
- 229940117681 interleukin-12 Drugs 0.000 claims 1
- 230000000302 ischemic effect Effects 0.000 claims 1
- 210000000867 larynx Anatomy 0.000 claims 1
- 210000004072 lung Anatomy 0.000 claims 1
- 201000005249 lung adenocarcinoma Diseases 0.000 claims 1
- 201000005202 lung cancer Diseases 0.000 claims 1
- 208000020816 lung neoplasm Diseases 0.000 claims 1
- 229940040129 luteinizing hormone Drugs 0.000 claims 1
- 210000004324 lymphatic system Anatomy 0.000 claims 1
- 201000010230 macular retinal edema Diseases 0.000 claims 1
- 208000015486 malignant pancreatic neoplasm Diseases 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 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
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 201000008968 osteosarcoma Diseases 0.000 claims 1
- 229960001592 paclitaxel Drugs 0.000 claims 1
- 201000002528 pancreatic cancer Diseases 0.000 claims 1
- 208000008443 pancreatic carcinoma Diseases 0.000 claims 1
- 230000007170 pathology Effects 0.000 claims 1
- 229940043138 pentosan polysulfate Drugs 0.000 claims 1
- 238000002428 photodynamic therapy Methods 0.000 claims 1
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 1
- 201000011461 pre-eclampsia Diseases 0.000 claims 1
- 239000002599 prostaglandin synthase inhibitor Substances 0.000 claims 1
- 229960004622 raloxifene Drugs 0.000 claims 1
- 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
- 201000006845 reticulosarcoma Diseases 0.000 claims 1
- 208000029922 reticulum cell sarcoma Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 208000007442 rickets Diseases 0.000 claims 1
- 208000000587 small cell lung carcinoma Diseases 0.000 claims 1
- 229950001248 squalamine Drugs 0.000 claims 1
- 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
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US42231302P | 2002-10-30 | 2002-10-30 | |
| PCT/US2003/034100 WO2004041164A2 (en) | 2002-10-30 | 2003-10-24 | Kinase inhibitors |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2006507302A JP2006507302A (ja) | 2006-03-02 |
| JP2006507302A5 true JP2006507302A5 (enExample) | 2006-08-03 |
Family
ID=32312490
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2004550143A Withdrawn JP2006507302A (ja) | 2002-10-30 | 2003-10-24 | キナーゼ阻害剤 |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1558609A4 (enExample) |
| JP (1) | JP2006507302A (enExample) |
| AU (1) | AU2003285007A1 (enExample) |
| CA (1) | CA2503715A1 (enExample) |
| WO (1) | WO2004041164A2 (enExample) |
Families Citing this family (30)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102558155A (zh) | 2003-01-14 | 2012-07-11 | 阿伦纳药品公司 | 作为代谢调节剂的芳基和杂芳基衍生物及其所涉及的疾病如糖尿病和高血糖症的预防和治疗 |
| 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 |
| HRP20090093T3 (en) * | 2004-06-04 | 2009-03-31 | Arena Pharmaceuticals Inc. | Substituted aryl and heteroaryl derivatives as modulators of metabolism and the prophylaxis and treatment of disorders related thereto |
| MX2007006777A (es) | 2004-12-06 | 2007-08-06 | Avigen Inc | Ibudilast para tratar dolor neuropatico y sindromes asociados. |
| 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 |
| JP2008542219A (ja) * | 2005-05-25 | 2008-11-27 | インゲニウム ファーマシューティカルズ ジーエムビーエイチ | 疼痛処置法 |
| EP1968596A4 (en) * | 2005-12-22 | 2010-12-01 | Icagen Inc | ANTAGONISTS OF CALCIUM CHANNEL |
| ES2378704T3 (es) * | 2006-01-27 | 2012-04-17 | Array Biopharma, Inc. | Activadores de la glucocinasa |
| US20080051380A1 (en) | 2006-08-25 | 2008-02-28 | Auerbach Alan H | Methods and compositions for treating cancer |
| AP2009005010A0 (en) | 2007-04-18 | 2009-10-31 | Pfizer Prod Inc | Sulfonyl amide derivatives for the treatment of abnormal cell growth |
| JP5566880B2 (ja) | 2007-04-24 | 2014-08-06 | インゲニウム ファーマシューティカルズ ジーエムビーエイチ | プロテインキナーゼの阻害剤としての４，６−二置換アミノピリミジン誘導体 |
| UA101166C2 (ru) | 2007-09-21 | 2013-03-11 | Аррей Биофарма Инк. | Производные пиридин-2-иламино-1,2,4-тиадиазола как активаторы глюкокиназы для лечения сахарного диабета |
| GB0811955D0 (en) | 2008-06-30 | 2008-07-30 | Pci Biotech As | Method |
| US20100113479A1 (en) * | 2008-10-30 | 2010-05-06 | Anusuya Choudhury | Process for the preparation of tri-substituted pyridine and tri-substituted pyrimidine derivatives useful as gdir agonists |
| BR112012029647A2 (pt) | 2010-05-21 | 2016-08-02 | Chemilia Ab | novos derivados de pirimidinas |
| MX2013003184A (es) | 2010-09-22 | 2013-06-07 | Arena Pharm Inc | Moduladores del receptor gpr119 y el tratamiento de transtornos relacionados con el mismo. |
| JP5886411B2 (ja) | 2011-03-24 | 2016-03-16 | ノビガ・リサーチ・エービーＮｏｖｉｇａ Ｒｅｓｅａｒｃｈ ＡＢ | 新規のピリミジン誘導体 |
| WO2012149528A1 (en) * | 2011-04-29 | 2012-11-01 | Exelixis, Inc. | Inhibitors of inducible form of 6-phosphofructose-2-kinase |
| AU2016205361C1 (en) | 2015-01-06 | 2021-04-08 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| PL3310760T3 (pl) | 2015-06-22 | 2023-03-06 | Arena Pharmaceuticals, Inc. | Krystaliczna sól L-argininy kwasu (R)-2-(7-(4-cyklopentylo-3-(trifluorometylo)benzyloksy)- 1,2,3,4-tetrahydrocyklo-penta[b]indol-3-ilo)octowego do zastosowania w zaburzeniach związanych z receptorem S1P1 |
| TWI620748B (zh) * | 2016-02-05 | 2018-04-11 | National Health Research Institutes | 氨基噻唑化合物及其用途 |
| CN119606965A (zh) | 2016-07-29 | 2025-03-14 | 詹森药业有限公司 | 治疗前列腺癌的方法 |
| KR20190116416A (ko) | 2017-02-16 | 2019-10-14 | 아레나 파마슈티칼스, 인크. | 원발 담즙성 담관염을 치료하기 위한 화합물 및 방법 |
| 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 |
| AU2019280822A1 (en) | 2018-06-06 | 2021-01-07 | Arena Pharmaceuticals, Inc. | Methods of treating conditions related to the S1P1 receptor |
| DK3643713T3 (da) * | 2018-10-23 | 2025-11-03 | Iomx Therapeutics Ag | Heterocykliske kinaseinhibitorer og deres anvendelse |
| 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 |
|---|---|---|---|---|
| NZ513639A (en) * | 1999-04-15 | 2004-02-27 | Bristol Myers Squibb Co | Cyclic protein tyrosine kinase inhibitors |
| US20020137755A1 (en) * | 2000-12-04 | 2002-09-26 | Bilodeau Mark T. | Tyrosine kinase inhibitors |
| AU3113902A (en) * | 2000-12-21 | 2002-07-01 | Bristol Myers Squibb Co | Thiazolyl inhibitors of tec family tyrosine kinases |
-
2003
- 2003-10-24 AU AU2003285007A patent/AU2003285007A1/en not_active Abandoned
- 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 WO PCT/US2003/034100 patent/WO2004041164A2/en not_active Ceased
- 2003-10-24 EP EP03779322A patent/EP1558609A4/en not_active Withdrawn
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AU2015317327B9 (en) | Pyridinyl quinolinone derivatives as mutant-isocitrate dehydrogenase inhibitors | |
| JP5261575B2 (ja) | 化学化合物 | |
| JP2003512353A5 (enExample) | ||
| JP6013375B2 (ja) | キナーゼ阻害剤としてのチアゾリルフェニル−ベンゼンスルホンアミド誘導体 | |
| ES2255621T3 (es) | Inhibidores de tirosina quinasa. | |
| CA3002610C (en) | N-substituted indole derivatives as pge2 receptor modulators | |
| JP2006206609A5 (enExample) | ||
| US20190345138A1 (en) | Heterocyclic amides as kinase inhibitors | |
| JP2011526616A5 (enExample) | ||
| JP2009541311A5 (enExample) | ||
| JP2014528450A5 (enExample) | ||
| JP2013544256A5 (enExample) | ||
| CA2671982A1 (en) | Methods of using mek inhibitors | |
| JP5538528B2 (ja) | 新規なｇｐｒ１１９アゴニスト | |
| TW201838966A (zh) | 取代的二氫茚－４－甲醯胺及其類似物以及其使用方法 | |
| JP2017525757A5 (enExample) | ||
| CA2677481A1 (en) | Triazole compounds that modulate hsp90 activity | |
| MX2009001427A (es) | Derivados de 2-(heterociclilbencil)-piridazinona. | |
| RU2018138047A (ru) | Гетероциклические вещества - агонисты gpr119 | |
| JP5922128B2 (ja) | ヒスタミンｈ４受容体リガンドとしてのベンザゾール誘導体 | |
| JP2025515484A (ja) | Ｋｉｆ１８ａを阻害するための化合物 | |
| US10752612B2 (en) | PLK4 inhibitors | |
| JP2019505595A5 (enExample) | ||
| JP2012531456A5 (enExample) | ||
| CN101987848A (zh) | 新的二氢吲哚酮化合物、它们的制备方法以及包含它们的药物组合物 |