JP2009512676A - ムスカリン性受容体アンタゴニストの医薬組成物 - Google Patents

Info

Publication number

JP2009512676A

JP2009512676A JP2008536146A JP2008536146A JP2009512676A JP 2009512676 A JP2009512676 A JP 2009512676A JP 2008536146 A JP2008536146 A JP 2008536146A JP 2008536146 A JP2008536146 A JP 2008536146A JP 2009512676 A JP2009512676 A JP 2009512676A

Authority

JP

Japan

Prior art keywords

compound

hydroxy

azabicyclo

methyl

phenylacetamide

Prior art date

2005-10-19

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Withdrawn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

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• 229940121948 Muscarinic receptor antagonist Drugs 0.000 title claims abstract description 47
• 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 19
• 239000003149 muscarinic antagonist Substances 0.000 title claims description 33
• 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims abstract description 30
• 239000000203 mixture Substances 0.000 claims abstract description 29
• 239000003246 corticosteroid Substances 0.000 claims abstract description 25
• 229960001334 corticosteroids Drugs 0.000 claims abstract description 22
• 102000002574 p38 Mitogen-Activated Protein Kinases Human genes 0.000 claims abstract description 22
• 108010068338 p38 Mitogen-Activated Protein Kinases Proteins 0.000 claims abstract description 22
• 229940124748 beta 2 agonist Drugs 0.000 claims abstract description 18
• 238000000034 method Methods 0.000 claims abstract description 17
• 239000002829 mitogen activated protein kinase inhibitor Substances 0.000 claims abstract description 17
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 10
• 101150030891 MRAS gene Proteins 0.000 claims abstract description 6
• 150000001875 compounds Chemical class 0.000 claims description 753
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 248
• -1 cyano, hydroxy Chemical group 0.000 claims description 172
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 150
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 77
• 125000000217 alkyl group Chemical group 0.000 claims description 52
• 150000003839 salts Chemical class 0.000 claims description 51
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 30
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 28
• 229910052736 halogen Inorganic materials 0.000 claims description 28
• 150000002367 halogens Chemical class 0.000 claims description 28
• 239000001257 hydrogen Substances 0.000 claims description 28
• 229910052739 hydrogen Inorganic materials 0.000 claims description 28
• 239000001301 oxygen Substances 0.000 claims description 28
• 229910052760 oxygen Inorganic materials 0.000 claims description 28
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 24
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 20
• 239000002253 acid Substances 0.000 claims description 20
• 125000001072 heteroaryl group Chemical group 0.000 claims description 20
• 239000011593 sulfur Chemical group 0.000 claims description 20
• 229910052717 sulfur Inorganic materials 0.000 claims description 20
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000004343 1-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C([H])([H])[H] 0.000 claims description 15
• 125000003119 4-methyl-3-pentenyl group Chemical group [H]\C(=C(/C([H])([H])[H])C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 15
• 239000012453 solvate Substances 0.000 claims description 14
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 13
• 150000002148 esters Chemical class 0.000 claims description 13
• 150000001204 N-oxides Chemical class 0.000 claims description 12
• 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
• 125000004447 heteroarylalkenyl group Chemical group 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 239000002207 metabolite Substances 0.000 claims description 12
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
• 229910052757 nitrogen Chemical group 0.000 claims description 12
• 125000001844 prenyl group Chemical group [H]C([*])([H])C([H])=C(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 12
• 229940095064 tartrate Drugs 0.000 claims description 12
• 239000000812 cholinergic antagonist Substances 0.000 claims description 10
• LLAPDLPYIYKTGQ-UHFFFAOYSA-N 1-aminoethyl Chemical group C[CH]N LLAPDLPYIYKTGQ-UHFFFAOYSA-N 0.000 claims description 9
• 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 claims description 9
• QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 9
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 9
• DGYIJVNZSDYBOE-UHFFFAOYSA-N [CH2]C1=CC=NC=C1 Chemical group [CH2]C1=CC=NC=C1 DGYIJVNZSDYBOE-UHFFFAOYSA-N 0.000 claims description 9
• 239000004305 biphenyl Substances 0.000 claims description 9
• 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 9
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 8
• 125000001931 aliphatic group Chemical group 0.000 claims description 8
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 8
• 239000000043 antiallergic agent Substances 0.000 claims description 8
• 125000005018 aryl alkenyl group Chemical group 0.000 claims description 8
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 8
• 125000000392 cycloalkenyl group Chemical group 0.000 claims description 8
• 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 8
• 125000004446 heteroarylalkyl group Chemical group 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 8
• 229940002612 prodrug Drugs 0.000 claims description 8
• 239000000651 prodrug Substances 0.000 claims description 8
• 229920006395 saturated elastomer Polymers 0.000 claims description 8
• 125000001424 substituent group Chemical group 0.000 claims description 8
• 229940052760 dopamine agonists Drugs 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 6
• 241000124008 Mammalia Species 0.000 claims description 5
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 4
• KPPVNWGJXFMGAM-UUILKARUSA-N (e)-2-methyl-1-(6-methyl-3,4-dihydro-2h-quinolin-1-yl)but-2-en-1-one Chemical compound CC1=CC=C2N(C(=O)C(/C)=C/C)CCCC2=C1 KPPVNWGJXFMGAM-UUILKARUSA-N 0.000 claims description 4
• RGICCULPCWNRAB-UHFFFAOYSA-N 2-[2-(2-hexoxyethoxy)ethoxy]ethanol Chemical compound CCCCCCOCCOCCOCCO RGICCULPCWNRAB-UHFFFAOYSA-N 0.000 claims description 4
• ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 125000003342 alkenyl group Chemical group 0.000 claims description 4
• 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 4
• 125000003282 alkyl amino group Chemical group 0.000 claims description 4
• 125000004429 atom Chemical group 0.000 claims description 4
• 208000010668 atopic eczema Diseases 0.000 claims description 4
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
• 229910052794 bromium Inorganic materials 0.000 claims description 4
• 238000003763 carbonization Methods 0.000 claims description 4
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 4
• 239000000460 chlorine Substances 0.000 claims description 4
• 229910052801 chlorine Inorganic materials 0.000 claims description 4
• 229910052731 fluorine Inorganic materials 0.000 claims description 4
• 239000011737 fluorine Substances 0.000 claims description 4
• 230000002757 inflammatory effect Effects 0.000 claims description 4
• 239000011630 iodine Substances 0.000 claims description 4
• 229910052740 iodine Inorganic materials 0.000 claims description 4
• 239000003199 leukotriene receptor blocking agent Substances 0.000 claims description 4
• BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 4
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
• 125000006507 2,4-difluorobenzyl group Chemical group [H]C1=C(F)C([H])=C(F)C(=C1[H])C([H])([H])* 0.000 claims description 3
• HUPVBFQYJHFONM-UHFFFAOYSA-N 2-(4-fluorophenyl)acetamide Chemical compound NC(=O)CC1=CC=C(F)C=C1 HUPVBFQYJHFONM-UHFFFAOYSA-N 0.000 claims description 3
• YZUZRUFGZYMJPR-UHFFFAOYSA-N 2-cyclohexyl-2-hydroxy-2-phenylacetamide Chemical compound C=1C=CC=CC=1C(O)(C(=O)N)C1CCCCC1 YZUZRUFGZYMJPR-UHFFFAOYSA-N 0.000 claims description 3
• 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 3
• 230000000172 allergic effect Effects 0.000 claims description 3
• 230000001363 autoimmune Effects 0.000 claims description 3
• 229940121647 egfr inhibitor Drugs 0.000 claims description 3
• 229940049920 malate Drugs 0.000 claims description 3
• 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
• 239000003848 thrombocyte activating factor antagonist Substances 0.000 claims 2
• 239000000546 pharmaceutical excipient Substances 0.000 abstract description 16
• 239000003085 diluting agent Substances 0.000 abstract description 15
• 239000003937 drug carrier Substances 0.000 abstract description 12
• 239000004480 active ingredient Substances 0.000 abstract description 11
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• 208000035475 disorder Diseases 0.000 abstract description 7
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• LOKCTEFSRHRXRJ-UHFFFAOYSA-I dipotassium trisodium dihydrogen phosphate hydrogen phosphate dichloride Chemical compound P(=O)(O)(O)[O-].[K+].P(=O)(O)([O-])[O-].[Na+].[Na+].[Cl-].[K+].[Cl-].[Na+] LOKCTEFSRHRXRJ-UHFFFAOYSA-I 0.000 description 30
• 239000002953 phosphate buffered saline Substances 0.000 description 30
• KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 21
• AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 20
• NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 16
• QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
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• 239000003981 vehicle Substances 0.000 description 15
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 14
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