JP2010514758A5 - - Google Patents

Info

Publication number

JP2010514758A5

JP2010514758A5 JP2009543946A JP2009543946A JP2010514758A5 JP 2010514758 A5 JP2010514758 A5 JP 2010514758A5 JP 2009543946 A JP2009543946 A JP 2009543946A JP 2009543946 A JP2009543946 A JP 2009543946A JP 2010514758 A5 JP2010514758 A5 JP 2010514758A5

Authority

JP

Japan

Prior art keywords

group

substituted

dihydroxy

formula

pyran

Prior art date

2007-12-27

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.)

Granted

Links

• Espacenet
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• -1 aryl alkyl C 5 Chemical compound 0.000 claims description 30
• 125000003277 amino group Chemical group 0.000 claims description 22
• VQFKFAKEUMHBLV-BYSUZVQFSA-N 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine Chemical class CCCCCCCCCCCCCCCCCCCCCCCCCC(=O)N[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@H]1O[C@H](CO)[C@H](O)[C@H](O)[C@H]1O VQFKFAKEUMHBLV-BYSUZVQFSA-N 0.000 claims description 20
• 239000000126 substance Substances 0.000 claims description 19
• 125000001424 substituent group Chemical group 0.000 claims description 17
• 125000000217 alkyl group Chemical group 0.000 claims description 15
• 125000003396 thiol group Chemical group [H]S* 0.000 claims description 15
• 150000003839 salts Chemical class 0.000 claims description 14
• 229910052736 halogen Inorganic materials 0.000 claims description 13
• 150000002367 halogens Chemical class 0.000 claims description 13
• 125000003368 amide group Chemical group 0.000 claims description 12
• 125000001072 heteroaryl group Chemical group 0.000 claims description 11
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
• 239000008194 pharmaceutical composition Substances 0.000 claims description 10
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
• 125000001188 haloalkyl group Chemical group 0.000 claims description 9
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
• 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 125000003118 aryl group Chemical group 0.000 claims description 6
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 6
• 208000023275 Autoimmune disease Diseases 0.000 claims description 5
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
• 150000001875 compounds Chemical class 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 4
• UMGDCJDMYOKAJW-UHFFFAOYSA-N aminothiocarboxamide Natural products NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
• ILRSCQWREDREME-UHFFFAOYSA-N dodecanamide Chemical compound CCCCCCCCCCCC(N)=O ILRSCQWREDREME-UHFFFAOYSA-N 0.000 claims description 4
• FKVMWDZRDMCIAJ-UHFFFAOYSA-N undecanamide Chemical compound CCCCCCCCCCC(N)=O FKVMWDZRDMCIAJ-UHFFFAOYSA-N 0.000 claims description 4
• 206010067584 Type 1 diabetes mellitus Diseases 0.000 claims description 3
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
• 201000006417 multiple sclerosis Diseases 0.000 claims description 3
• 230000028327 secretion Effects 0.000 claims description 3
• 108090000695 Cytokines Proteins 0.000 claims description 2
• 102000004127 Cytokines Human genes 0.000 claims description 2
• 210000003719 b-lymphocyte Anatomy 0.000 claims description 2
• 210000004443 dendritic cell Anatomy 0.000 claims description 2
• YRIDQLUIJWIYTQ-CMKFUXGOSA-N n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-11-hydroxyundecanamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCO)CO[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O YRIDQLUIJWIYTQ-CMKFUXGOSA-N 0.000 claims description 2
• BLEPUQBZGDNRHC-CMKFUXGOSA-N n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-11-sulfanylundecanamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCS)CO[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O BLEPUQBZGDNRHC-CMKFUXGOSA-N 0.000 claims description 2
• VBYGAGMOQCNOGC-HVXYMDBUSA-N n-[(2s,3s,4r)-3,4-dihydroxy-1-[(2s,3r,4s,5r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoctadecan-2-yl]-12-hydroxydodecanamide Chemical compound CCCCCCCCCCCCCC[C@@H](O)[C@@H](O)[C@@H](NC(=O)CCCCCCCCCCCO)CO[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O VBYGAGMOQCNOGC-HVXYMDBUSA-N 0.000 claims description 2
• LTHCSWBWNVGEFE-UHFFFAOYSA-N octanamide Chemical compound CCCCCCCC(N)=O LTHCSWBWNVGEFE-UHFFFAOYSA-N 0.000 claims description 2
• 125000006239 protecting group Chemical group 0.000 claims description 2
• 230000001225 therapeutic effect Effects 0.000 claims description 2
• 229960005486 vaccine Drugs 0.000 claims description 2
• CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims 3
• CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical group Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims 1
• 238000010511 deprotection reaction Methods 0.000 claims 1
• 150000002254 galactosylceramides Chemical class 0.000 claims 1
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims 1
• 150000003852 triazoles Chemical class 0.000 description 10
• 0 C*([n]1nnc(SS=*)c1)=C Chemical compound C*([n]1nnc(SS=*)c1)=C 0.000 description 4
• 125000003837 (C1-C20) alkyl group Chemical group 0.000 description 2
• 108090000978 Interleukin-4 Proteins 0.000 description 2
• QPGGZMQVQYITSV-DATVVERSSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-2-(4-heptyltriazol-1-yl)-3,4-dihydroxyoctadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C([C@@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)N1N=NC(CCCCCCC)=C1)O[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O QPGGZMQVQYITSV-DATVVERSSA-N 0.000 description 1
• RNDXMEKYKSSAMK-IUAYPLKUSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-2-(4-hexadecyltriazol-1-yl)-3,4-dihydroxyoctadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 RNDXMEKYKSSAMK-IUAYPLKUSA-N 0.000 description 1
• JFQQZWBTSXQLTC-DHSWYTMZSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-2-(4-hexyltriazol-1-yl)-3,4-dihydroxyoctadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound C([C@@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)N1N=NC(CCCCCC)=C1)O[C@H]1OC(CO)[C@H](O)[C@H](O)[C@H]1O JFQQZWBTSXQLTC-DHSWYTMZSA-N 0.000 description 1
• AVDUUWCJJJVSKA-IAYFSJKOSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-3,4-dihydroxy-2-(4-pentacosyltriazol-1-yl)octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 AVDUUWCJJJVSKA-IAYFSJKOSA-N 0.000 description 1
• YLAIBGQPPXWHSD-WGUQISDVSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-3,4-dihydroxy-2-(4-tetracosyltriazol-1-yl)octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 YLAIBGQPPXWHSD-WGUQISDVSA-N 0.000 description 1
• KCRBJQLTYCOVMS-JYWCXLKKSA-N (2s,3r,4s,5r)-2-[(2s,3s,4r)-3,4-dihydroxy-2-(4-tricosyltriazol-1-yl)octadecoxy]-6-(hydroxymethyl)oxane-3,4,5-triol Chemical compound N1=NC(CCCCCCCCCCCCCCCCCCCCCCC)=CN1[C@H]([C@H](O)[C@H](O)CCCCCCCCCCCCCC)CO[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)C(CO)O1 KCRBJQLTYCOVMS-JYWCXLKKSA-N 0.000 description 1
• 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 1
• 125000006732 (C1-C15) alkyl group Chemical group 0.000 description 1
• 125000000923 (C1-C30) alkyl group Chemical group 0.000 description 1
• 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
• XUHWMOZKLZBMMU-UHFFFAOYSA-N 4-(6-phenylhexyl)-2H-triazole Chemical compound C1(=CC=CC=C1)CCCCCCC=1N=NNC=1 XUHWMOZKLZBMMU-UHFFFAOYSA-N 0.000 description 1
• LRICDRQZYJXCKY-UHFFFAOYSA-N C1(=CC=CC=C1)CCCCCCCC=1N=NNC1 Chemical compound C1(=CC=CC=C1)CCCCCCCC=1N=NNC1 LRICDRQZYJXCKY-UHFFFAOYSA-N 0.000 description 1
• YFFHTFRKLOPKKB-UHFFFAOYSA-N C1(=CC=CC=C1)CCCCCCCCC=1N=NNC1 Chemical compound C1(=CC=CC=C1)CCCCCCCCC=1N=NNC1 YFFHTFRKLOPKKB-UHFFFAOYSA-N 0.000 description 1
• 102100037850 Interferon gamma Human genes 0.000 description 1
• 108010074328 Interferon-gamma Proteins 0.000 description 1
• 239000003814 drug Substances 0.000 description 1
• 230000001105 regulatory effect Effects 0.000 description 1
• 229940124597 therapeutic agent Drugs 0.000 description 1