JP2011032210A5 - - Google Patents

Info

Publication number

JP2011032210A5

JP2011032210A5 JP2009179931A JP2009179931A JP2011032210A5 JP 2011032210 A5 JP2011032210 A5 JP 2011032210A5 JP 2009179931 A JP2009179931 A JP 2009179931A JP 2009179931 A JP2009179931 A JP 2009179931A JP 2011032210 A5 JP2011032210 A5 JP 2011032210A5

Authority

JP

Japan

Prior art keywords

formula

compound

group

halogen atom

general formula

Prior art date

2009-07-31

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
• Global Dossier
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• 239000000126 substance Substances 0.000 claims description 9
• DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 claims description 5
• 239000004480 active ingredient Substances 0.000 claims description 3
• 125000005843 halogen group Chemical group 0.000 claims 4
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 4
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 2
• 102000002274 Matrix Metalloproteinases Human genes 0.000 claims 2
• 108010000684 Matrix Metalloproteinases Proteins 0.000 claims 2
• 125000003545 alkoxy group Chemical group 0.000 claims 2
• 125000000217 alkyl group Chemical group 0.000 claims 2
• 229910052799 carbon Inorganic materials 0.000 claims 2
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
• 239000003112 inhibitor Substances 0.000 claims 1
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
• 239000012954 diazonium Substances 0.000 description 9
• 150000001989 diazonium salts Chemical class 0.000 description 9
• 238000006243 chemical reaction Methods 0.000 description 7
• 150000001875 compounds Chemical class 0.000 description 7
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
• 239000007864 aqueous solution Substances 0.000 description 6
• 238000005859 coupling reaction Methods 0.000 description 6
• 239000000203 mixture Substances 0.000 description 6
• 239000000243 solution Substances 0.000 description 6
• 229940125904 compound 1 Drugs 0.000 description 5
• 229940124761 MMP inhibitor Drugs 0.000 description 4
• SMENITZGNXRBHK-UHFFFAOYSA-N phenyl-(2-pyridin-2-ylphenyl)diazene Chemical class C1=CC=CC=C1N=NC1=CC=CC=C1C1=CC=CC=N1 SMENITZGNXRBHK-UHFFFAOYSA-N 0.000 description 4
• USWINTIHFQKJTR-UHFFFAOYSA-N 3-hydroxynaphthalene-2,7-disulfonic acid Chemical compound C1=C(S(O)(=O)=O)C=C2C=C(S(O)(=O)=O)C(O)=CC2=C1 USWINTIHFQKJTR-UHFFFAOYSA-N 0.000 description 3
• -1 5-hydroxy-2- (2-nitro-phenylazo) pyridine 5-Hydroxy-2- (2-nitrophenylazo) pyridine Chemical compound 0.000 description 3
• 239000000987 azo dye Substances 0.000 description 3
• 230000015572 biosynthetic process Effects 0.000 description 3
• 239000007795 chemical reaction product Substances 0.000 description 3
• 239000013078 crystal Substances 0.000 description 3
• 238000004128 high performance liquid chromatography Methods 0.000 description 3
• 150000003839 salts Chemical class 0.000 description 3
• 238000003786 synthesis reaction Methods 0.000 description 3
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
• HBENZIXOGRCSQN-VQWWACLZSA-N (1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylpentan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol Chemical compound N1([C@@H]2CC=3C4=C(C(=CC=3)O)O[C@H]3[C@@]5(OC)CC[C@@]2([C@@]43CC1)C[C@@H]5[C@](C)(O)C(C)(C)CC)CC1CC1 HBENZIXOGRCSQN-VQWWACLZSA-N 0.000 description 2
• PHDIJLFSKNMCMI-ITGJKDDRSA-N (3R,4S,5R,6R)-6-(hydroxymethyl)-4-(8-quinolin-6-yloxyoctoxy)oxane-2,3,5-triol Chemical compound OC[C@@H]1[C@H]([C@@H]([C@H](C(O1)O)O)OCCCCCCCCOC=1C=C2C=CC=NC2=CC=1)O PHDIJLFSKNMCMI-ITGJKDDRSA-N 0.000 description 2
• JNPGUXGVLNJQSQ-BGGMYYEUSA-M (e,3r,5s)-7-[4-(4-fluorophenyl)-1,2-di(propan-2-yl)pyrrol-3-yl]-3,5-dihydroxyhept-6-enoate Chemical compound CC(C)N1C(C(C)C)=C(\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C1 JNPGUXGVLNJQSQ-BGGMYYEUSA-M 0.000 description 2
• VAVHMEQFYYBAPR-ITWZMISCSA-N (e,3r,5s)-7-[4-(4-fluorophenyl)-1-phenyl-2-propan-2-ylpyrrol-3-yl]-3,5-dihydroxyhept-6-enoic acid Chemical compound CC(C)C1=C(\C=C\[C@@H](O)C[C@@H](O)CC(O)=O)C(C=2C=CC(F)=CC=2)=CN1C1=CC=CC=C1 VAVHMEQFYYBAPR-ITWZMISCSA-N 0.000 description 2
• HIHOEGPXVVKJPP-JTQLQIEISA-N 5-fluoro-2-[[(1s)-1-(5-fluoropyridin-2-yl)ethyl]amino]-6-[(5-methyl-1h-pyrazol-3-yl)amino]pyridine-3-carbonitrile Chemical compound N([C@@H](C)C=1N=CC(F)=CC=1)C(C(=CC=1F)C#N)=NC=1NC=1C=C(C)NN=1 HIHOEGPXVVKJPP-JTQLQIEISA-N 0.000 description 2
• GVOISEJVFFIGQE-YCZSINBZSA-N n-[(1r,2s,5r)-5-[methyl(propan-2-yl)amino]-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](N(C)C(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 GVOISEJVFFIGQE-YCZSINBZSA-N 0.000 description 2
• BPHMZLLHNFVNRT-FOCLMDBBSA-N COc(cc1[N+]([O-])=O)ccc1/N=N/c(nc1Cl)ccc1O Chemical compound COc(cc1[N+]([O-])=O)ccc1/N=N/c(nc1Cl)ccc1O BPHMZLLHNFVNRT-FOCLMDBBSA-N 0.000 description 1
• KWDGLQLDCBTKIQ-CCEZHUSRSA-N Cc(cc1)cc([N+]([O-])=O)c1/N=N/C1N=CC(O)=CC1 Chemical compound Cc(cc1)cc([N+]([O-])=O)c1/N=N/C1N=CC(O)=CC1 KWDGLQLDCBTKIQ-CCEZHUSRSA-N 0.000 description 1
• MIFMCJYWIITKHI-CCEZHUSRSA-N [O-][N+](c1cc(Cl)ccc1/N=N/c(nc1)ccc1O)=O Chemical compound [O-][N+](c1cc(Cl)ccc1/N=N/c(nc1)ccc1O)=O MIFMCJYWIITKHI-CCEZHUSRSA-N 0.000 description 1