CA2534313C - Formulations containing an immune response modifier - Google Patents
Formulations containing an immune response modifier Download PDFInfo
- Publication number
- CA2534313C CA2534313C CA2534313A CA2534313A CA2534313C CA 2534313 C CA2534313 C CA 2534313C CA 2534313 A CA2534313 A CA 2534313A CA 2534313 A CA2534313 A CA 2534313A CA 2534313 C CA2534313 C CA 2534313C
- Authority
- CA
- Canada
- Prior art keywords
- alkyl
- amines
- substituted
- aryl
- heteroaryl
- 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.)
- Expired - Fee Related
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- 230000028993 immune response Effects 0.000 title claims abstract description 44
- 239000003607 modifier Substances 0.000 title claims abstract description 42
- 239000000203 mixture Substances 0.000 title claims description 117
- 238000009472 formulation Methods 0.000 title claims description 109
- 239000013011 aqueous formulation Substances 0.000 claims abstract description 32
- 206010039085 Rhinitis allergic Diseases 0.000 claims abstract description 12
- 201000010105 allergic rhinitis Diseases 0.000 claims abstract description 12
- 208000036142 Viral infection Diseases 0.000 claims abstract description 10
- 230000009385 viral infection Effects 0.000 claims abstract description 10
- 208000006673 asthma Diseases 0.000 claims abstract description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 39
- 239000003795 chemical substances by application Substances 0.000 claims description 38
- 230000002708 enhancing effect Effects 0.000 claims description 31
- 239000000243 solution Substances 0.000 claims description 28
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000006184 cosolvent Substances 0.000 claims description 18
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 claims description 15
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 14
- DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 claims description 12
- 229920003123 carboxymethyl cellulose sodium Polymers 0.000 claims description 12
- 229940063834 carboxymethylcellulose sodium Drugs 0.000 claims description 12
- 239000002738 chelating agent Substances 0.000 claims description 11
- 239000003755 preservative agent Substances 0.000 claims description 11
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 10
- 239000000872 buffer Substances 0.000 claims description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 229920002125 Sokalan® Polymers 0.000 claims description 9
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid group Chemical group C(CC(O)(C(=O)O)CC(=O)O)(=O)O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 9
- 229960000686 benzalkonium chloride Drugs 0.000 claims description 8
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 claims description 8
- 239000004310 lactic acid Substances 0.000 claims description 7
- 235000014655 lactic acid Nutrition 0.000 claims description 7
- 239000003002 pH adjusting agent Substances 0.000 claims description 7
- 230000002335 preservative effect Effects 0.000 claims description 7
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- 239000000230 xanthan gum Substances 0.000 claims description 6
- 229920001285 xanthan gum Polymers 0.000 claims description 6
- 235000010493 xanthan gum Nutrition 0.000 claims description 6
- 229940082509 xanthan gum Drugs 0.000 claims description 6
- 235000011187 glycerol Nutrition 0.000 claims description 5
- NVNWHRIYBUUBAJ-UHFFFAOYSA-N n-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]methanesulfonamide Chemical group C1=CC=CC2=C(N(C(COCC)=N3)CC(C)(C)NS(C)(=O)=O)C3=C(N)N=C21 NVNWHRIYBUUBAJ-UHFFFAOYSA-N 0.000 claims description 5
- 229960004063 propylene glycol Drugs 0.000 claims description 5
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 4
- OVBJJZOQPCKUOR-UHFFFAOYSA-L EDTA disodium salt dihydrate Chemical group O.O.[Na+].[Na+].[O-]C(=O)C[NH+](CC([O-])=O)CC[NH+](CC([O-])=O)CC([O-])=O OVBJJZOQPCKUOR-UHFFFAOYSA-L 0.000 claims description 4
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 claims description 4
- 229920003086 cellulose ether Polymers 0.000 claims description 4
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 claims description 4
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 claims description 4
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 claims description 4
- 201000009890 sinusitis Diseases 0.000 claims description 4
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 claims description 3
- 150000004676 glycans Chemical class 0.000 claims description 3
- 229940068918 polyethylene glycol 400 Drugs 0.000 claims description 3
- 229920001282 polysaccharide Polymers 0.000 claims description 3
- 239000005017 polysaccharide Substances 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 claims description 2
- 229960001950 benzethonium chloride Drugs 0.000 claims description 2
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 claims description 2
- 150000007942 carboxylates Chemical group 0.000 claims description 2
- 235000015165 citric acid Nutrition 0.000 claims description 2
- 229960005150 glycerol Drugs 0.000 claims description 2
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 claims description 2
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 229960002216 methylparaben Drugs 0.000 claims description 2
- 229940067107 phenylethyl alcohol Drugs 0.000 claims description 2
- 239000004405 propyl p-hydroxybenzoate Substances 0.000 claims description 2
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 claims description 2
- 229960003415 propylparaben Drugs 0.000 claims description 2
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims description 2
- 229960000281 trometamol Drugs 0.000 claims description 2
- 125000002843 carboxylic acid group Chemical group 0.000 claims 1
- -1 imidazoquinoline amines Chemical class 0.000 abstract description 207
- 229940124669 imidazoquinoline Drugs 0.000 abstract description 42
- 150000001412 amines Chemical class 0.000 abstract description 14
- 239000000539 dimer Substances 0.000 abstract description 5
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 abstract description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract description 4
- LBUJPTNKIBCYBY-UHFFFAOYSA-N tetrahydroquinoline Natural products C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 abstract description 2
- 206010051513 Viral sinusitis Diseases 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 description 227
- 125000004432 carbon atom Chemical group C* 0.000 description 144
- 229910052739 hydrogen Inorganic materials 0.000 description 84
- 239000001257 hydrogen Substances 0.000 description 82
- 125000001072 heteroaryl group Chemical group 0.000 description 81
- 229910052736 halogen Inorganic materials 0.000 description 80
- 125000003342 alkenyl group Chemical group 0.000 description 74
- 125000000623 heterocyclic group Chemical group 0.000 description 70
- 150000001875 compounds Chemical class 0.000 description 67
- 125000001424 substituent group Chemical group 0.000 description 58
- 125000003545 alkoxy group Chemical group 0.000 description 53
- 150000002367 halogens Chemical class 0.000 description 45
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 37
- 125000003118 aryl group Chemical group 0.000 description 33
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 31
- 238000000034 method Methods 0.000 description 27
- 125000002947 alkylene group Chemical group 0.000 description 26
- XSQUKJJJFZCRTK-UHFFFAOYSA-N urea group Chemical group NC(=O)N XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 26
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 25
- 241001465754 Metazoa Species 0.000 description 21
- 150000003839 salts Chemical class 0.000 description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 19
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 17
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 17
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 16
- 125000004450 alkenylene group Chemical group 0.000 description 16
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 16
- 239000000427 antigen Substances 0.000 description 15
- 102000036639 antigens Human genes 0.000 description 15
- 108091007433 antigens Proteins 0.000 description 15
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 125000000304 alkynyl group Chemical group 0.000 description 13
- 239000004202 carbamide Chemical group 0.000 description 13
- 108010058846 Ovalbumin Proteins 0.000 description 12
- 125000004419 alkynylene group Chemical group 0.000 description 12
- 125000000753 cycloalkyl group Chemical group 0.000 description 12
- 125000004663 dialkyl amino group Chemical group 0.000 description 12
- 229940092253 ovalbumin Drugs 0.000 description 12
- 239000000126 substance Substances 0.000 description 11
- 125000003282 alkyl amino group Chemical group 0.000 description 10
- 235000010948 carboxy methyl cellulose Nutrition 0.000 description 10
- 125000001188 haloalkyl group Chemical group 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 10
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 10
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 9
- 125000000732 arylene group Chemical group 0.000 description 9
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- 125000004093 cyano group Chemical group *C#N 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- 125000004043 oxo group Chemical group O=* 0.000 description 9
- 229940124530 sulfonamide Drugs 0.000 description 9
- 150000003456 sulfonamides Chemical group 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 125000005549 heteroarylene group Chemical group 0.000 description 8
- 230000002452 interceptive effect Effects 0.000 description 8
- 238000005507 spraying Methods 0.000 description 8
- 150000003568 thioethers Chemical group 0.000 description 8
- 230000003612 virological effect Effects 0.000 description 8
- HQBUPOAKJGJGCD-UHFFFAOYSA-N 3h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1=NC2=CC=CC=C2C2=C1N=CN2 HQBUPOAKJGJGCD-UHFFFAOYSA-N 0.000 description 7
- 241000124008 Mammalia Species 0.000 description 7
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 7
- 241000700159 Rattus Species 0.000 description 7
- 125000004423 acyloxy group Chemical group 0.000 description 7
- 125000004414 alkyl thio group Chemical group 0.000 description 7
- 150000001408 amides Chemical group 0.000 description 7
- 125000003710 aryl alkyl group Chemical group 0.000 description 7
- 229960001484 edetic acid Drugs 0.000 description 7
- HNQIVZYLYMDVSB-NJFSPNSNSA-N methanesulfonamide Chemical compound [14CH3]S(N)(=O)=O HNQIVZYLYMDVSB-NJFSPNSNSA-N 0.000 description 7
- 239000011780 sodium chloride Substances 0.000 description 7
- 230000001225 therapeutic effect Effects 0.000 description 7
- FQYRLEXKXQRZDH-UHFFFAOYSA-N 4-aminoquinoline Chemical compound C1=CC=C2C(N)=CC=NC2=C1 FQYRLEXKXQRZDH-UHFFFAOYSA-N 0.000 description 6
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 6
- 125000005013 aryl ether group Chemical group 0.000 description 6
- 125000004104 aryloxy group Chemical group 0.000 description 6
- 125000004122 cyclic group Chemical group 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
- 125000005553 heteroaryloxy group Chemical group 0.000 description 6
- 238000001802 infusion Methods 0.000 description 6
- ZNSRMRJLRGFEBS-UHFFFAOYSA-N oxathiaziridine 2,2-dioxide Chemical group O=S1(=O)NO1 ZNSRMRJLRGFEBS-UHFFFAOYSA-N 0.000 description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 125000004438 haloalkoxy group Chemical group 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000001228 spectrum Methods 0.000 description 5
- 238000010998 test method Methods 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UHUHBFMZVCOEOV-UHFFFAOYSA-N 1h-imidazo[4,5-c]pyridin-4-amine Chemical class NC1=NC=CC2=C1N=CN2 UHUHBFMZVCOEOV-UHFFFAOYSA-N 0.000 description 4
- ICSNLGPSRYBMBD-UHFFFAOYSA-N 2-aminopyridine Chemical compound NC1=CC=CC=N1 ICSNLGPSRYBMBD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 4
- 102000004127 Cytokines Human genes 0.000 description 4
- 108090000695 Cytokines Proteins 0.000 description 4
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 4
- JVTAAEKCZFNVCJ-REOHCLBHSA-N L-lactic acid Chemical compound C[C@H](O)C(O)=O JVTAAEKCZFNVCJ-REOHCLBHSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 125000005041 acyloxyalkyl group Chemical group 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- 239000011203 carbon fibre reinforced carbon Chemical group 0.000 description 4
- 229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 4
- 230000003308 immunostimulating effect Effects 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 235000013772 propylene glycol Nutrition 0.000 description 4
- 230000004044 response Effects 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 3
- 125000003341 7 membered heterocyclic group Chemical group 0.000 description 3
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- 102000014150 Interferons Human genes 0.000 description 3
- 108010050904 Interferons Proteins 0.000 description 3
- YQEZLKZALYSWHR-UHFFFAOYSA-N Ketamine Chemical compound C=1C=CC=C(Cl)C=1C1(NC)CCCCC1=O YQEZLKZALYSWHR-UHFFFAOYSA-N 0.000 description 3
- 108060008682 Tumor Necrosis Factor Proteins 0.000 description 3
- 125000005529 alkyleneoxy group Chemical group 0.000 description 3
- 230000000259 anti-tumor effect Effects 0.000 description 3
- 125000005532 aryl alkyleneoxy group Chemical group 0.000 description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 229960001716 benzalkonium Drugs 0.000 description 3
- CYDRXTMLKJDRQH-UHFFFAOYSA-N benzododecinium Chemical compound CCCCCCCCCCCC[N+](C)(C)CC1=CC=CC=C1 CYDRXTMLKJDRQH-UHFFFAOYSA-N 0.000 description 3
- 125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 229940009662 edetate Drugs 0.000 description 3
- 229940124274 edetate disodium Drugs 0.000 description 3
- 125000003709 fluoroalkyl group Chemical group 0.000 description 3
- 125000005114 heteroarylalkoxy group Chemical group 0.000 description 3
- 235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 3
- 229960003299 ketamine Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000006199 nebulizer Substances 0.000 description 3
- 230000010412 perfusion Effects 0.000 description 3
- 239000000546 pharmaceutical excipient Substances 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 210000002345 respiratory system Anatomy 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 3
- 125000001412 tetrahydropyranyl group Chemical group 0.000 description 3
- 210000003437 trachea Anatomy 0.000 description 3
- 102000003390 tumor necrosis factor Human genes 0.000 description 3
- 241000712461 unidentified influenza virus Species 0.000 description 3
- MBIIMZGOLXUTTO-UHFFFAOYSA-N 1-[1-[4-amino-2-(ethoxymethyl)imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-yl]-3-cyclohexylurea Chemical compound CCOCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)NC(=O)NC1CCCCC1 MBIIMZGOLXUTTO-UHFFFAOYSA-N 0.000 description 2
- BXUVSPUTCNMBJE-UHFFFAOYSA-N 1-[3-[4-amino-2-(2-methoxyethyl)imidazo[4,5-c]quinolin-1-yl]-2,2-dimethylpropyl]-3-phenylurea Chemical compound COCCC1=NC2=C(N)N=C3C=CC=CC3=C2N1CC(C)(C)CNC(=O)NC1=CC=CC=C1 BXUVSPUTCNMBJE-UHFFFAOYSA-N 0.000 description 2
- QOFBARJUFKOMTB-UHFFFAOYSA-N 1-[4-amino-2-(ethoxymethyl)-7-[5-(hydroxymethyl)pyridin-3-yl]imidazo[4,5-c]quinolin-1-yl]-2-methylpropan-2-ol Chemical compound C1=CC2=C3N(CC(C)(C)O)C(COCC)=NC3=C(N)N=C2C=C1C1=CN=CC(CO)=C1 QOFBARJUFKOMTB-UHFFFAOYSA-N 0.000 description 2
- HLFGXPKPTDQYBN-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1h-imidazo[4,5-c]quinolin-4-amine Chemical class NC1N=C2C=CC=CC2=C2C1NCN2 HLFGXPKPTDQYBN-UHFFFAOYSA-N 0.000 description 2
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 2
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- COXVTLYNGOIATD-HVMBLDELSA-N CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O Chemical compound CC1=C(C=CC(=C1)C1=CC(C)=C(C=C1)\N=N\C1=C(O)C2=C(N)C(=CC(=C2C=C1)S(O)(=O)=O)S(O)(=O)=O)\N=N\C1=CC=C2C(=CC(=C(N)C2=C1O)S(O)(=O)=O)S(O)(=O)=O COXVTLYNGOIATD-HVMBLDELSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 2
- 206010015866 Extravasation Diseases 0.000 description 2
- 241001427367 Gardena Species 0.000 description 2
- 108010002352 Interleukin-1 Proteins 0.000 description 2
- 102000000589 Interleukin-1 Human genes 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 238000012387 aerosolization Methods 0.000 description 2
- 125000004656 alkyl sulfonylamino group Chemical group 0.000 description 2
- 239000013566 allergen Substances 0.000 description 2
- 125000004657 aryl sulfonyl amino group Chemical group 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 239000001045 blue dye Substances 0.000 description 2
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Classifications
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- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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Landscapes
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- Veterinary Medicine (AREA)
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- Chemical & Material Sciences (AREA)
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- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
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| US49310903P | 2003-08-05 | 2003-08-05 | |
| US60/493,109 | 2003-08-05 | ||
| PCT/US2004/025277 WO2005016275A2 (en) | 2003-08-05 | 2004-08-05 | Formulations containing an immune response modifier |
Publications (2)
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| CA2534313A1 CA2534313A1 (en) | 2005-02-24 |
| CA2534313C true CA2534313C (en) | 2013-03-19 |
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| CA002534625A Abandoned CA2534625A1 (en) | 2003-08-05 | 2004-08-05 | Infection prophylaxis using immune response modifier compounds |
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| CA002534625A Abandoned CA2534625A1 (en) | 2003-08-05 | 2004-08-05 | Infection prophylaxis using immune response modifier compounds |
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| WO (2) | WO2005016273A2 (enExample) |
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| US6756382B2 (en) * | 1999-06-10 | 2004-06-29 | 3M Innovative Properties Company | Amide substituted imidazoquinolines |
| US6677347B2 (en) * | 2000-12-08 | 2004-01-13 | 3M Innovative Properties Company | Sulfonamido ether substituted imidazoquinolines |
| US20040265351A1 (en) | 2003-04-10 | 2004-12-30 | Miller Richard L. | Methods and compositions for enhancing immune response |
| US20040214851A1 (en) * | 2003-04-28 | 2004-10-28 | 3M Innovative Properties Company | Compositions and methods for induction of opioid receptors |
| AU2004266658A1 (en) | 2003-08-12 | 2005-03-03 | 3M Innovative Properties Company | Hydroxylamine substituted imidazo-containing compounds |
| JP2007503268A (ja) * | 2003-08-25 | 2007-02-22 | スリーエム イノベイティブ プロパティズ カンパニー | 免疫応答修飾化合物の送達 |
| US7897597B2 (en) | 2003-08-27 | 2011-03-01 | 3M Innovative Properties Company | Aryloxy and arylalkyleneoxy substituted imidazoquinolines |
| JP2007504269A (ja) * | 2003-09-05 | 2007-03-01 | スリーエム イノベイティブ プロパティズ カンパニー | Ｃｄ５＋ｂ細胞リンパ腫の治療方法 |
| US20090075980A1 (en) * | 2003-10-03 | 2009-03-19 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and Analogs Thereof |
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| US7544697B2 (en) | 2003-10-03 | 2009-06-09 | Coley Pharmaceutical Group, Inc. | Pyrazolopyridines and analogs thereof |
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| AU2004291101A1 (en) | 2003-11-14 | 2005-06-02 | 3M Innovative Properties Company | Oxime substituted imidazo ring compounds |
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| US8541438B2 (en) | 2004-06-18 | 2013-09-24 | 3M Innovative Properties Company | Substituted imidazoquinolines, imidazopyridines, and imidazonaphthyridines |
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| WO2006063072A2 (en) * | 2004-12-08 | 2006-06-15 | 3M Innovative Properties Company | Immunomodulatory compositions, combinations and methods |
| US8034938B2 (en) | 2004-12-30 | 2011-10-11 | 3M Innovative Properties Company | Substituted chiral fused [1,2]imidazo[4,5-c] ring compounds |
| ZA200706251B (en) * | 2004-12-30 | 2008-11-26 | Coley Pharm Group Inc | Immune response modifier formulations and methods |
| AU2005322898B2 (en) | 2004-12-30 | 2011-11-24 | 3M Innovative Properties Company | Chiral fused (1,2)imidazo(4,5-c) ring compounds |
| WO2006084251A2 (en) | 2005-02-04 | 2006-08-10 | Coley Pharmaceutical Group, Inc. | Aqueous gel formulations containing immune reponse modifiers |
| CA2597324C (en) | 2005-02-09 | 2015-06-30 | Coley Pharmaceutical Group, Inc. | Alkyloxy substituted thiazoloquinolines and thiazolonaphthyridines |
| EP1877056A2 (en) | 2005-02-09 | 2008-01-16 | Coley Pharmaceutical Group, Inc. | Oxime and hydroxylamine substituted thiazoloý4,5-c¨ring compounds and methods |
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| EP1851220A2 (en) | 2005-02-23 | 2007-11-07 | 3M Innovative Properties Company | Hydroxyalkyl substituted imidazonaphthyridines |
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- 2004-08-05 CA CA2534313A patent/CA2534313C/en not_active Expired - Fee Related
- 2004-08-05 US US10/595,049 patent/US8221771B2/en not_active Expired - Fee Related
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- 2004-08-05 EP EP04780166A patent/EP1651190B1/en not_active Expired - Lifetime
- 2004-08-05 AU AU2004264330A patent/AU2004264330A1/en not_active Abandoned
- 2004-08-05 JP JP2006522709A patent/JP2007501251A/ja not_active Withdrawn
- 2004-08-05 WO PCT/US2004/025241 patent/WO2005016273A2/en not_active Ceased
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- 2004-08-05 CA CA002534625A patent/CA2534625A1/en not_active Abandoned
- 2004-08-05 JP JP2006522714A patent/JP2007501252A/ja active Pending
- 2004-08-05 AU AU2004264336A patent/AU2004264336B2/en not_active Ceased
- 2004-08-05 WO PCT/US2004/025277 patent/WO2005016275A2/en not_active Ceased
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| CA2534313A1 (en) | 2005-02-24 |
| EP1651190A4 (en) | 2009-07-15 |
| JP2007501252A (ja) | 2007-01-25 |
| US20070292456A1 (en) | 2007-12-20 |
| WO2005016275A2 (en) | 2005-02-24 |
| AU2004264336A1 (en) | 2005-02-24 |
| US20050070460A1 (en) | 2005-03-31 |
| CN1852711A (zh) | 2006-10-25 |
| JP2007501251A (ja) | 2007-01-25 |
| EP1651216A2 (en) | 2006-05-03 |
| WO2005016275A3 (en) | 2005-04-14 |
| US8221771B2 (en) | 2012-07-17 |
| EP1651190A2 (en) | 2006-05-03 |
| WO2005016273A2 (en) | 2005-02-24 |
| AU2004264336B2 (en) | 2010-12-23 |
| EP1651190B1 (en) | 2012-09-19 |
| CA2534625A1 (en) | 2005-02-24 |
| WO2005016273A3 (en) | 2005-12-29 |
| AU2004264330A1 (en) | 2005-02-24 |
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