HUE033070T2 - Nitrogén-tartalmú spiro-gyûrûs vegyület és ennek gyógyászati alkalmazása - Google Patents

Info

Publication number

HUE033070T2

HUE033070T2 HUE10804531A HUE10804531A HUE033070T2 HU E033070 T2 HUE033070 T2 HU E033070T2 HU E10804531 A HUE10804531 A HU E10804531A HU E10804531 A HUE10804531 A HU E10804531A HU E033070 T2 HUE033070 T2 HU E033070T2

Authority

HU

Hungary

Prior art keywords

compound

vagy vagy

mixture

salt

pharmaceutically acceptable

Prior art date

2009-07-31

Links

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• 230000001225 therapeutic effect Effects 0.000 title claims description 14
• 239000000126 substance Substances 0.000 claims description 132
• -1 αcosyl Chemical group 0.000 claims description 105
• 150000003839 salts Chemical class 0.000 claims description 94
• 239000012453 solvate Substances 0.000 claims description 93
• 238000006243 chemical reaction Methods 0.000 claims description 72
• 238000002360 preparation method Methods 0.000 claims description 35
• 239000007787 solid Substances 0.000 claims description 33
• 125000000217 alkyl group Chemical group 0.000 claims description 27
• 229920006395 saturated elastomer Polymers 0.000 claims description 27
• 239000003795 chemical substances by application Substances 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 25
• 102000015617 Janus Kinases Human genes 0.000 claims description 24
• 108010024121 Janus Kinases Proteins 0.000 claims description 24
• 108091000080 Phosphotransferase Proteins 0.000 claims description 20
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 102000020233 phosphotransferase Human genes 0.000 claims description 20
• 230000005764 inhibitory process Effects 0.000 claims description 19
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 18
• 125000005843 halogen group Chemical group 0.000 claims description 18
• 238000002054 transplantation Methods 0.000 claims description 17
• 239000003814 drug Substances 0.000 claims description 16
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
• 201000004681 Psoriasis Diseases 0.000 claims description 14
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• 230000002265 prevention Effects 0.000 claims description 13
• 125000001424 substituent group Chemical group 0.000 claims description 13
• 208000026935 allergic disease Diseases 0.000 claims description 12
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 11
• 206010039073 rheumatoid arthritis Diseases 0.000 claims description 11
• 238000004519 manufacturing process Methods 0.000 claims description 9
• 229910052739 hydrogen Inorganic materials 0.000 claims description 8
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 7
• 229940079593 drug Drugs 0.000 claims description 6
• 239000001257 hydrogen Substances 0.000 claims description 6
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• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
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• 230000000552 rheumatic effect Effects 0.000 claims 1
• HIEHAIZHJZLEPQ-UHFFFAOYSA-M sodium;naphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 HIEHAIZHJZLEPQ-UHFFFAOYSA-M 0.000 claims 1
• 239000007921 spray Substances 0.000 claims 1
• 150000003573 thiols Chemical class 0.000 claims 1
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 297
• 239000000203 mixture Substances 0.000 description 243
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• 239000000243 solution Substances 0.000 description 172
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• 238000000034 method Methods 0.000 description 30
• 239000000706 filtrate Substances 0.000 description 29
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 28
• UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 28
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• 230000035484 reaction time Effects 0.000 description 26
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• 230000014759 maintenance of location Effects 0.000 description 25
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 25
• VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 24
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 22
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 22
• 102100033444 Tyrosine-protein kinase JAK2 Human genes 0.000 description 22
• WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 21
• 102100025387 Tyrosine-protein kinase JAK3 Human genes 0.000 description 21
• JTNCEQNHURODLX-UHFFFAOYSA-N 2-phenylethanimidamide Chemical compound NC(=N)CC1=CC=CC=C1 JTNCEQNHURODLX-UHFFFAOYSA-N 0.000 description 19
• 101000934996 Homo sapiens Tyrosine-protein kinase JAK3 Proteins 0.000 description 19
• 229910000343 potassium bisulfate Inorganic materials 0.000 description 19
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 18
• 239000002585 base Substances 0.000 description 18
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