CH622793A5 - - Google Patents
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- Publication number
- CH622793A5 CH622793A5 CH484580A CH484580A CH622793A5 CH 622793 A5 CH622793 A5 CH 622793A5 CH 484580 A CH484580 A CH 484580A CH 484580 A CH484580 A CH 484580A CH 622793 A5 CH622793 A5 CH 622793A5
- Authority
- CH
- Switzerland
- Prior art keywords
- dimethyl
- pyrazole
- amino
- hydrogen
- quinoline
- Prior art date
Links
- -1 hydroxy, thio Chemical group 0.000 claims description 28
- 150000001875 compounds Chemical class 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 13
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000003282 alkyl amino group Chemical group 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 125000004984 dialkylaminoalkoxy group Chemical group 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- OILOPOQPXXGBIR-UHFFFAOYSA-N 4-chloro-1,3-dimethylpyrazole Chemical compound CC1=NN(C)C=C1Cl OILOPOQPXXGBIR-UHFFFAOYSA-N 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 3
- 125000001309 chloro group Chemical class Cl* 0.000 claims 1
- BTUQCUPQFZHMNS-UHFFFAOYSA-N quinoline;dihydrochloride Chemical compound Cl.Cl.N1=CC=CC2=CC=CC=C21 BTUQCUPQFZHMNS-UHFFFAOYSA-N 0.000 description 41
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 18
- 230000008018 melting Effects 0.000 description 18
- 238000002844 melting Methods 0.000 description 18
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 150000002431 hydrogen Chemical group 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical group [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 102000014150 Interferons Human genes 0.000 description 5
- 108010050904 Interferons Proteins 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 229940079322 interferon Drugs 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- XCAAYLUBHIIYOT-UHFFFAOYSA-N quinoline;trihydrochloride Chemical compound Cl.Cl.Cl.N1=CC=CC2=CC=CC=C21 XCAAYLUBHIIYOT-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 241000124008 Mammalia Species 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000000840 anti-viral effect Effects 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 229910052802 copper Inorganic materials 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- PSXRWZBTVAZNSF-UHFFFAOYSA-N hydron;quinoline;chloride Chemical compound Cl.N1=CC=CC2=CC=CC=C21 PSXRWZBTVAZNSF-UHFFFAOYSA-N 0.000 description 4
- 230000003902 lesion Effects 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 241000699666 Mus <mouse, genus> Species 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 241000700605 Viruses Species 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- 238000007912 intraperitoneal administration Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 150000003248 quinolines Chemical class 0.000 description 3
- XTPUVLAADOMKEW-UHFFFAOYSA-N 2-[(2,5-dimethylpyrazol-3-yl)amino]-4-methylbenzoic acid Chemical compound CN1N=C(C)C=C1NC1=CC(C)=CC=C1C(O)=O XTPUVLAADOMKEW-UHFFFAOYSA-N 0.000 description 2
- UOZLJIMLFFSJGV-UHFFFAOYSA-N CC1=NN(C=C1NCCCNC)C Chemical compound CC1=NN(C=C1NCCCNC)C UOZLJIMLFFSJGV-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- FKXRMJUOBSWYFV-UHFFFAOYSA-N N'-(1,3-dimethylpyrazol-4-yl)propane-1,3-diamine Chemical compound Cc1nn(C)cc1NCCCN FKXRMJUOBSWYFV-UHFFFAOYSA-N 0.000 description 2
- CTKNZLYKFBFRNH-UHFFFAOYSA-N N-(1,3-dimethylpyrazol-4-yl)-N',N'-dimethylhexane-1,6-diamine Chemical compound CN1N=C(C(=C1)NCCCCCCN(C)C)C CTKNZLYKFBFRNH-UHFFFAOYSA-N 0.000 description 2
- OSEHWPHOVMDYCX-UHFFFAOYSA-N N-(5-methoxy-1,3-dimethylpyrazol-4-yl)-N',N'-dimethylpropane-1,3-diamine Chemical compound CN1N=C(C(=C1OC)NCCCN(C)C)C OSEHWPHOVMDYCX-UHFFFAOYSA-N 0.000 description 2
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 241000709664 Picornaviridae Species 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 241000700618 Vaccinia virus Species 0.000 description 2
- 241000711975 Vesicular stomatitis virus Species 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 2
- 239000004599 antimicrobial Substances 0.000 description 2
- 239000003443 antiviral agent Substances 0.000 description 2
- 239000012267 brine Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- WASQWSOJHCZDFK-UHFFFAOYSA-N diketene Chemical compound C=C1CC(=O)O1 WASQWSOJHCZDFK-UHFFFAOYSA-N 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 2
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- ZFDGMMZLXSFNFU-UHFFFAOYSA-N 2,5-dimethylpyrazol-3-amine Chemical compound CC=1C=C(N)N(C)N=1 ZFDGMMZLXSFNFU-UHFFFAOYSA-N 0.000 description 1
- UGDAWAQEKLURQI-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethanol;hydrate Chemical compound O.OCCOCCO UGDAWAQEKLURQI-UHFFFAOYSA-N 0.000 description 1
- YCWUYQQRIHWNLH-UHFFFAOYSA-N 2-[(2,5-dimethylpyrazol-3-yl)amino]benzoic acid Chemical compound CN1N=C(C)C=C1NC1=CC=CC=C1C(O)=O YCWUYQQRIHWNLH-UHFFFAOYSA-N 0.000 description 1
- RPGKFFKUTVJVPY-UHFFFAOYSA-N 2-amino-4-methylbenzoic acid Chemical compound CC1=CC=C(C(O)=O)C(N)=C1 RPGKFFKUTVJVPY-UHFFFAOYSA-N 0.000 description 1
- CJNZAXGUTKBIHP-UHFFFAOYSA-N 2-iodobenzoic acid Chemical compound OC(=O)C1=CC=CC=C1I CJNZAXGUTKBIHP-UHFFFAOYSA-N 0.000 description 1
- CNTOCJDGHOHCJF-UHFFFAOYSA-N 3-[(1,3-dimethylpyrazol-4-yl)amino]propan-1-ol Chemical compound CN1N=C(C(=C1)NCCCO)C CNTOCJDGHOHCJF-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- HQQTZCPKNZVLFF-UHFFFAOYSA-N 4h-1,2-benzoxazin-3-one Chemical compound C1=CC=C2ONC(=O)CC2=C1 HQQTZCPKNZVLFF-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- AOCVVDMEYHBLIX-UHFFFAOYSA-N N-(1,3-dimethylpyrazol-4-yl)-N',N'-dimethylethane-1,2-diamine Chemical compound CN(C)CCNc1cn(C)nc1C AOCVVDMEYHBLIX-UHFFFAOYSA-N 0.000 description 1
- CDSUASBWUSMIDL-UHFFFAOYSA-N N-(1,3-dimethylpyrazol-4-yl)-N',N'-dimethylpentane-1,5-diamine Chemical compound CN1N=C(C(=C1)NCCCCCN(C)C)C CDSUASBWUSMIDL-UHFFFAOYSA-N 0.000 description 1
- AGBTUCMLHIJWNZ-UHFFFAOYSA-N N-(1,3-dimethylpyrazol-4-yl)-N',N'-dimethylpropane-1,3-diamine Chemical compound CN(C)CCCNc1cn(C)nc1C AGBTUCMLHIJWNZ-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- WUGQZFFCHPXWKQ-UHFFFAOYSA-N Propanolamine Chemical compound NCCCO WUGQZFFCHPXWKQ-UHFFFAOYSA-N 0.000 description 1
- 102100030852 Run domain Beclin-1-interacting and cysteine-rich domain-containing protein Human genes 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 206010046865 Vaccinia virus infection Diseases 0.000 description 1
- 208000036142 Viral infection Diseases 0.000 description 1
- BLAKAEFIFWAFGH-UHFFFAOYSA-N acetyl acetate;pyridine Chemical compound C1=CC=NC=C1.CC(=O)OC(C)=O BLAKAEFIFWAFGH-UHFFFAOYSA-N 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical class [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009395 breeding Methods 0.000 description 1
- 230000001488 breeding effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 150000001804 chlorine Chemical class 0.000 description 1
- QTMDXZNDVAMKGV-UHFFFAOYSA-L copper(ii) bromide Chemical compound [Cu+2].[Br-].[Br-] QTMDXZNDVAMKGV-UHFFFAOYSA-L 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005530 etching Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 229940071870 hydroiodic acid Drugs 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 230000000055 hyoplipidemic effect Effects 0.000 description 1
- 230000000871 hypocholesterolemic effect Effects 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000006308 propyl amino group Chemical group 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000003578 releasing effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 208000007089 vaccinia Diseases 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 230000009385 viral infection Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Virology (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fodder In General (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/402,657 US4013665A (en) | 1973-10-01 | 1973-10-01 | Antiviral, substituted 1,3-dimethyl-1h-pyrazolo(3,4b)quinolines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH622793A5 true CH622793A5 (en, 2012) | 1981-04-30 |
Family
ID=23592812
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1316374A CH621552A5 (en, 2012) | 1973-10-01 | 1974-09-30 | |
| CH1180A CH619712A5 (en, 2012) | 1973-10-01 | 1980-01-03 | |
| CH484580A CH622793A5 (en, 2012) | 1973-10-01 | 1980-06-24 |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1316374A CH621552A5 (en, 2012) | 1973-10-01 | 1974-09-30 | |
| CH1180A CH619712A5 (en, 2012) | 1973-10-01 | 1980-01-03 |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4013665A (en, 2012) |
| JP (1) | JPS582948B2 (en, 2012) |
| BE (1) | BE820400A (en, 2012) |
| CA (1) | CA1032538A (en, 2012) |
| CH (3) | CH621552A5 (en, 2012) |
| CY (1) | CY1087A (en, 2012) |
| DE (1) | DE2446821A1 (en, 2012) |
| DK (1) | DK516274A (en, 2012) |
| ES (1) | ES430554A1 (en, 2012) |
| FI (1) | FI57414C (en, 2012) |
| FR (1) | FR2245369B1 (en, 2012) |
| GB (1) | GB1488692A (en, 2012) |
| HK (1) | HK59380A (en, 2012) |
| KE (1) | KE3086A (en, 2012) |
| MY (1) | MY8100219A (en, 2012) |
| NL (1) | NL7412959A (en, 2012) |
| NO (1) | NO143223C (en, 2012) |
| SE (1) | SE419760B (en, 2012) |
| ZA (1) | ZA746138B (en, 2012) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL73534A (en) * | 1983-11-18 | 1990-12-23 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinoline-4-amines,their preparation and pharmaceutical compositions containing certain such compounds |
| ZA848968B (en) * | 1983-11-18 | 1986-06-25 | Riker Laboratories Inc | 1h-imidazo(4,5-c)quinolines and 1h-imidazo(4,5-c)quinolin-4-amines |
| WO1992018488A1 (fr) * | 1991-04-10 | 1992-10-29 | Japan Tobacco Inc. | Nouveau derive d'oxazinone |
| US5608067A (en) * | 1993-12-09 | 1997-03-04 | Afonso; Adriano | 4-substituted pyrazoloquinoline derivatives |
| US5786480A (en) * | 1994-04-28 | 1998-07-28 | Schering Corporation | 4-substituted pyrazoloquinoline derivatives |
| US5506236A (en) * | 1994-04-28 | 1996-04-09 | Schering Corporation | 4-substituted pyrazoloquinoline derivatives |
| US5614530A (en) * | 1995-03-10 | 1997-03-25 | Sterling Winthrop Inc. | Substituted N-arylmethyl and heterocyclmethyl-1H-pyrazolo[3,4-b]quinolin-4-amines and compositions and methods of use thereof |
| US6008226A (en) * | 1995-03-10 | 1999-12-28 | Sanofi-Synthelabo | Substituted N-arylmethyl and heterocylylmethyl-1H-pyrazolo[3,4-b]quinolin-4-amines and compositions and methods of use thereof |
| US5488055A (en) * | 1995-03-10 | 1996-01-30 | Sanofi Winthrop Inc. | Substituted N-cycloalkylmethyl-1H-pyrazolo(3,4-b)quinolin-4 amines and compositions and methods of use thereof |
| EP1450801A4 (en) * | 2001-11-27 | 2010-10-27 | Merck Sharp & Dohme | 2-aminoquinoline CONNECTIONS |
| US20050009815A1 (en) * | 2001-11-27 | 2005-01-13 | Devita Robert J. | 4-Aminoquinoline compounds |
| US8080560B2 (en) * | 2004-12-17 | 2011-12-20 | 3M Innovative Properties Company | Immune response modifier formulations containing oleic acid and methods |
| US8889154B2 (en) | 2005-09-15 | 2014-11-18 | Medicis Pharmaceutical Corporation | Packaging for 1-(2-methylpropyl)-1H-imidazo[4,5-c] quinolin-4-amine-containing formulation |
| JP2009543866A (ja) * | 2006-07-18 | 2009-12-10 | ウイラ アイピー プロプライエタリー リミテッド | 免疫応答修飾製剤 |
| AU2007279376B2 (en) * | 2006-07-31 | 2012-09-06 | Wirra Ip Pty Ltd | Immune response modifier compositions and methods |
| EP2350072A1 (en) * | 2008-10-28 | 2011-08-03 | Schering Corporation | Substituted pyrazoloquinolines and derivatives thereof |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1445719A1 (de) * | 1961-03-21 | 1969-01-09 | Bayer Ag | Verfahren zur Herstellung von 4-Chlor- oder 4-Brom-pyrazolo[3,4-]chinolinen |
| DE1152421B (de) * | 1961-03-21 | 1963-08-08 | Bayer Ag | Verfahren zur Herstellung von 4-Hydroxy-pyrazolo[3, 4-b]chinolinen |
| DE1186867B (de) * | 1961-05-03 | 1965-02-11 | Bayer Ag | Verfahren zur Herstellung von heterocyclischen Verbindungen |
| DE1222885B (de) * | 1962-05-25 | 1966-08-18 | Bayer Ag | Optische Aufhellungsmittel |
| US3600393A (en) * | 1969-03-03 | 1971-08-17 | Aldrich Chem Co Inc | Dialkylamino alkylamino pyrazolo (3,4b) quinolines |
| JPS4826797A (en, 2012) * | 1971-08-07 | 1973-04-09 | ||
| US3790576A (en) * | 1972-03-20 | 1974-02-05 | Parke Davis & Co | 9 substituted 4,9-dihydro-1,3,4,4-tetraalkyl-1h-pyrazolo(3,4-b)quinolines |
-
1973
- 1973-10-01 US US05/402,657 patent/US4013665A/en not_active Expired - Lifetime
-
1974
- 1974-09-25 FR FR7432265A patent/FR2245369B1/fr not_active Expired
- 1974-09-26 FI FI2815/74A patent/FI57414C/fi active
- 1974-09-26 ZA ZA00746138A patent/ZA746138B/xx unknown
- 1974-09-26 BE BE148952A patent/BE820400A/xx not_active IP Right Cessation
- 1974-09-27 NO NO743528A patent/NO143223C/no unknown
- 1974-09-30 CA CA210,304A patent/CA1032538A/en not_active Expired
- 1974-09-30 CY CY1087A patent/CY1087A/xx unknown
- 1974-09-30 SE SE7412275A patent/SE419760B/xx unknown
- 1974-09-30 ES ES430554A patent/ES430554A1/es not_active Expired
- 1974-09-30 CH CH1316374A patent/CH621552A5/de not_active IP Right Cessation
- 1974-09-30 GB GB42353/74A patent/GB1488692A/en not_active Expired
- 1974-10-01 DK DK516274A patent/DK516274A/da not_active Application Discontinuation
- 1974-10-01 NL NL7412959A patent/NL7412959A/xx not_active Application Discontinuation
- 1974-10-01 JP JP49112386A patent/JPS582948B2/ja not_active Expired
- 1974-10-01 DE DE19742446821 patent/DE2446821A1/de not_active Ceased
-
1980
- 1980-01-03 CH CH1180A patent/CH619712A5/de not_active IP Right Cessation
- 1980-06-24 CH CH484580A patent/CH622793A5/de not_active IP Right Cessation
- 1980-09-27 KE KE3086A patent/KE3086A/xx unknown
- 1980-10-23 HK HK593/80A patent/HK59380A/xx unknown
-
1981
- 1981-12-30 MY MY219/81A patent/MY8100219A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| HK59380A (en) | 1980-10-31 |
| SE7412275L (en, 2012) | 1975-04-02 |
| AU7379874A (en) | 1976-04-01 |
| NO743528L (en, 2012) | 1975-04-28 |
| FI281574A7 (en, 2012) | 1975-04-02 |
| US4013665A (en) | 1977-03-22 |
| ES430554A1 (es) | 1977-07-01 |
| CY1087A (en) | 1980-12-27 |
| JPS5059396A (en, 2012) | 1975-05-22 |
| NO143223B (no) | 1980-09-22 |
| SE419760B (sv) | 1981-08-24 |
| FR2245369A1 (en, 2012) | 1975-04-25 |
| DE2446821A1 (de) | 1975-04-10 |
| NL7412959A (nl) | 1975-04-03 |
| DK516274A (en, 2012) | 1975-06-30 |
| MY8100219A (en) | 1981-12-31 |
| CA1032538A (en) | 1978-06-06 |
| FR2245369B1 (en, 2012) | 1978-07-28 |
| FI57414B (fi) | 1980-04-30 |
| CH619712A5 (en, 2012) | 1980-10-15 |
| CH621552A5 (en, 2012) | 1981-02-13 |
| FI57414C (fi) | 1980-08-11 |
| ZA746138B (en) | 1975-10-29 |
| JPS582948B2 (ja) | 1983-01-19 |
| GB1488692A (en) | 1977-10-12 |
| NO143223C (no) | 1981-01-02 |
| BE820400A (fr) | 1975-03-26 |
| USB402657I5 (en, 2012) | 1976-04-06 |
| KE3086A (en) | 1980-11-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |