UA76142C2 - 4-anilinoquinoline-3-carboxamides and pharmaceutically acceptable salts thereof and pharmaceutical composition containing them - Google Patents
4-anilinoquinoline-3-carboxamides and pharmaceutically acceptable salts thereof and pharmaceutical composition containing them Download PDFInfo
- Publication number
- UA76142C2 UA76142C2 UA2003109525A UA2003109525A UA76142C2 UA 76142 C2 UA76142 C2 UA 76142C2 UA 2003109525 A UA2003109525 A UA 2003109525A UA 2003109525 A UA2003109525 A UA 2003109525A UA 76142 C2 UA76142 C2 UA 76142C2
- Authority
- UA
- Ukraine
- Prior art keywords
- quinolinecarboxamide
- methoxy
- dimethoxy
- methylanilino
- amino
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 7
- 150000003839 salts Chemical class 0.000 title claims description 18
- MOXCMUMGZFALMQ-UHFFFAOYSA-N 4-anilinoquinoline-3-carboxamide Chemical class NC(=O)C1=CN=C2C=CC=CC2=C1NC1=CC=CC=C1 MOXCMUMGZFALMQ-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 177
- BLTDCIWCFCUQCB-UHFFFAOYSA-N quionoline-3-carboxamide Natural products C1=CC=CC2=CC(C(=O)N)=CN=C21 BLTDCIWCFCUQCB-UHFFFAOYSA-N 0.000 claims description 69
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 68
- -1 tetrahydronaphthenyl Chemical group 0.000 claims description 44
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 239000001257 hydrogen Substances 0.000 claims description 36
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 34
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 28
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 19
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical group C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 18
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 16
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 13
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 229920006395 saturated elastomer Polymers 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 claims description 7
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 6
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- 238000011282 treatment Methods 0.000 claims description 5
- 150000003852 triazoles Chemical class 0.000 claims description 5
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical group CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 4
- QZVCPJMBGNCFMQ-UHFFFAOYSA-N 4-(2-ethylanilino)-7-(3-hydroxypropoxy)-6-methoxyquinoline-3-carboxamide Chemical compound CCC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(OCCCO)=C(OC)C=C12 QZVCPJMBGNCFMQ-UHFFFAOYSA-N 0.000 claims description 4
- VYMIAEOEKQAWIO-UHFFFAOYSA-N 4-[(3-carbamoyl-6,7-dimethoxyquinolin-4-yl)amino]-3-methylbenzoic acid Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(C(O)=O)C=C1C VYMIAEOEKQAWIO-UHFFFAOYSA-N 0.000 claims description 4
- IPNZFZHYLZTMDR-UHFFFAOYSA-N 6-(2-aminoethoxy)-4-(2-ethylanilino)-7-methoxyquinoline-3-carboxamide Chemical compound CCC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=C(OCCN)C=C12 IPNZFZHYLZTMDR-UHFFFAOYSA-N 0.000 claims description 4
- LDKOYZUGKAJTLV-UHFFFAOYSA-N 7-(3-aminopropoxy)-4-(2-ethylanilino)-6-methoxyquinoline-3-carboxamide Chemical compound CCC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(OCCCN)=C(OC)C=C12 LDKOYZUGKAJTLV-UHFFFAOYSA-N 0.000 claims description 4
- 201000010099 disease Diseases 0.000 claims description 4
- 229940079593 drug Drugs 0.000 claims description 4
- 125000001041 indolyl group Chemical group 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- LVNDIBAYGHYXPG-UHFFFAOYSA-N 4-(1h-indol-5-ylamino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C1=C2NC=CC2=CC(NC=2C(C(N)=O)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 LVNDIBAYGHYXPG-UHFFFAOYSA-N 0.000 claims description 3
- LNWYUEIMWXMEIU-UHFFFAOYSA-N 4-(2,4-dichloroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(Cl)C=C1Cl LNWYUEIMWXMEIU-UHFFFAOYSA-N 0.000 claims description 3
- SJVAZYDFKAJFAQ-UHFFFAOYSA-N 4-(2-ethylanilino)-6-methoxy-7-(2-methoxyethoxy)quinoline-3-carboxamide Chemical compound CCC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(OCCOC)=C(OC)C=C12 SJVAZYDFKAJFAQ-UHFFFAOYSA-N 0.000 claims description 3
- GOCFOHLPCOEMMP-UHFFFAOYSA-N 4-(2-hydroxy-4-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(C)C=C1O GOCFOHLPCOEMMP-UHFFFAOYSA-N 0.000 claims description 3
- ABYXYSOCLNAKRB-UHFFFAOYSA-N 4-[3-(hydroxymethyl)-2-methylanilino]quinoline-3-carboxamide Chemical compound CC1=C(CO)C=CC=C1NC1=C(C(N)=O)C=NC2=CC=CC=C12 ABYXYSOCLNAKRB-UHFFFAOYSA-N 0.000 claims description 3
- HHJGCHJPKWHXGS-UHFFFAOYSA-N 6,7-dichloro-4-(2-methylanilino)quinoline-3-carboxamide Chemical compound CC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(Cl)=C(Cl)C=C12 HHJGCHJPKWHXGS-UHFFFAOYSA-N 0.000 claims description 3
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 3
- YIKSCQDJHCMVMK-UHFFFAOYSA-N Oxamide Chemical compound NC(=O)C(N)=O YIKSCQDJHCMVMK-UHFFFAOYSA-N 0.000 claims description 3
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004639 dihydroindenyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- OTDROJSZOLDVRM-UHFFFAOYSA-N methyl 4-[(3-carbamoyl-6,7-dimethoxyquinolin-4-yl)amino]-3-methylbenzoate Chemical compound CC1=CC(C(=O)OC)=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=C(OC)C=C12 OTDROJSZOLDVRM-UHFFFAOYSA-N 0.000 claims description 3
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 3
- 239000012453 solvate Substances 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- PZRIFMDPEYDQKG-UHFFFAOYSA-N 4-(1h-indazol-5-ylamino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C1=C2NN=CC2=CC(NC=2C(C(N)=O)=CN=C3C=C(C(=CC3=2)OC)OC)=C1 PZRIFMDPEYDQKG-UHFFFAOYSA-N 0.000 claims description 2
- LAJVUASLPHMQCC-UHFFFAOYSA-N 4-(2,3-dichloroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC(Cl)=C1Cl LAJVUASLPHMQCC-UHFFFAOYSA-N 0.000 claims description 2
- JWIQTGFSQBQVKV-UHFFFAOYSA-N 4-(2,3-dihydro-1h-inden-1-ylamino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C1CC2=CC=CC=C2C1NC1=C(C=C(C(OC)=C2)OC)C2=NC=C1C(N)=O JWIQTGFSQBQVKV-UHFFFAOYSA-N 0.000 claims description 2
- DFSWRTVMHOJXER-UHFFFAOYSA-N 4-(2,4-dimethoxyanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound COC1=CC(OC)=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=C(OC)C=C12 DFSWRTVMHOJXER-UHFFFAOYSA-N 0.000 claims description 2
- KFXGPOSMSOKDEI-UHFFFAOYSA-N 4-(2,4-dimethoxyanilino)-7-methoxyquinoline-3-carboxamide Chemical compound COC1=CC(OC)=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=CC=C12 KFXGPOSMSOKDEI-UHFFFAOYSA-N 0.000 claims description 2
- KVTYOPXIKMJGST-UHFFFAOYSA-N 4-(2,4-dimethylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(C)C=C1C KVTYOPXIKMJGST-UHFFFAOYSA-N 0.000 claims description 2
- HQOIHZQTMAAPCH-UHFFFAOYSA-N 4-(2,4-dimethylanilino)-6-methoxyquinoline-3-carboxamide Chemical compound C12=CC(OC)=CC=C2N=CC(C(N)=O)=C1NC1=CC=C(C)C=C1C HQOIHZQTMAAPCH-UHFFFAOYSA-N 0.000 claims description 2
- QOUCPKGOWFRLLG-UHFFFAOYSA-N 4-(2,5-dichloroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC(Cl)=CC=C1Cl QOUCPKGOWFRLLG-UHFFFAOYSA-N 0.000 claims description 2
- YMHNYVNOYXPQLO-UHFFFAOYSA-N 4-(2,5-difluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC(F)=CC=C1F YMHNYVNOYXPQLO-UHFFFAOYSA-N 0.000 claims description 2
- IBFRHJHBIQWZLN-UHFFFAOYSA-N 4-(2,5-dimethylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC(C)=CC=C1C IBFRHJHBIQWZLN-UHFFFAOYSA-N 0.000 claims description 2
- QEWGYVBDABGLDV-UHFFFAOYSA-N 4-(2,6-difluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=C(F)C=CC=C1F QEWGYVBDABGLDV-UHFFFAOYSA-N 0.000 claims description 2
- KBFOSSKDEKQLIC-UHFFFAOYSA-N 4-(2-bromo-4-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(F)C=C1Br KBFOSSKDEKQLIC-UHFFFAOYSA-N 0.000 claims description 2
- ZMYHYVJCHGKVBS-UHFFFAOYSA-N 4-(2-bromo-4-fluoroanilino)-7-methoxyquinoline-3-carboxamide Chemical compound NC(=O)C=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(F)C=C1Br ZMYHYVJCHGKVBS-UHFFFAOYSA-N 0.000 claims description 2
- XLPZSPXNJSFWDP-UHFFFAOYSA-N 4-(2-bromo-4-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(C)C=C1Br XLPZSPXNJSFWDP-UHFFFAOYSA-N 0.000 claims description 2
- UOEIHNPLKZKXFL-UHFFFAOYSA-N 4-(2-bromo-4-methylanilino)-7-methoxyquinoline-3-carboxamide Chemical compound NC(=O)C=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(C)C=C1Br UOEIHNPLKZKXFL-UHFFFAOYSA-N 0.000 claims description 2
- BEGKILNSQXLQLG-UHFFFAOYSA-N 4-(2-bromoanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC=C1Br BEGKILNSQXLQLG-UHFFFAOYSA-N 0.000 claims description 2
- PWBMISDQEYRREB-UHFFFAOYSA-N 4-(2-chloro-4-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(F)C=C1Cl PWBMISDQEYRREB-UHFFFAOYSA-N 0.000 claims description 2
- HBWPCUHTARMVOQ-UHFFFAOYSA-N 4-(2-chloroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC=C1Cl HBWPCUHTARMVOQ-UHFFFAOYSA-N 0.000 claims description 2
- PQLGLQSBHOQGHX-UHFFFAOYSA-N 4-(2-ethoxyanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound CCOC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=C(OC)C=C12 PQLGLQSBHOQGHX-UHFFFAOYSA-N 0.000 claims description 2
- HDMSFPYJNUNZII-UHFFFAOYSA-N 4-(2-ethoxyanilino)-7-methoxyquinoline-3-carboxamide Chemical compound CCOC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=CC=C12 HDMSFPYJNUNZII-UHFFFAOYSA-N 0.000 claims description 2
- MWALMIORTLWXTA-UHFFFAOYSA-N 4-(2-ethylanilino)-7-methoxy-6-(thiophen-3-ylmethoxy)quinoline-3-carboxamide Chemical compound CCC1=CC=CC=C1NC(C1=C2)=C(C(N)=O)C=NC1=CC(OC)=C2OCC1=CSC=C1 MWALMIORTLWXTA-UHFFFAOYSA-N 0.000 claims description 2
- PTVOXKKZUPVNAK-UHFFFAOYSA-N 4-(2-fluoro-4-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(C)C=C1F PTVOXKKZUPVNAK-UHFFFAOYSA-N 0.000 claims description 2
- DRLAQNVAPJIJNS-UHFFFAOYSA-N 4-(2-fluoro-5-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC(C)=CC=C1F DRLAQNVAPJIJNS-UHFFFAOYSA-N 0.000 claims description 2
- UZANVGMPALOCQJ-UHFFFAOYSA-N 4-(2-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC=C1F UZANVGMPALOCQJ-UHFFFAOYSA-N 0.000 claims description 2
- GPMLQCARONVLSL-UHFFFAOYSA-N 4-(2-methylanilino)quinoline-3-carboxamide Chemical compound CC1=CC=CC=C1NC1=C(C(N)=O)C=NC2=CC=CC=C12 GPMLQCARONVLSL-UHFFFAOYSA-N 0.000 claims description 2
- PBJYETCPHRTRBG-UHFFFAOYSA-N 4-(3-chloro-2-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC(Cl)=C1C PBJYETCPHRTRBG-UHFFFAOYSA-N 0.000 claims description 2
- ZWCBMLUUBWYSGZ-UHFFFAOYSA-N 4-(3-chloro-4-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(F)C(Cl)=C1 ZWCBMLUUBWYSGZ-UHFFFAOYSA-N 0.000 claims description 2
- PDHPVHXEKOECNM-UHFFFAOYSA-N 4-(3-chloroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC(Cl)=C1 PDHPVHXEKOECNM-UHFFFAOYSA-N 0.000 claims description 2
- YXLJPFPPJKMUSW-UHFFFAOYSA-N 4-(3-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC(F)=C1 YXLJPFPPJKMUSW-UHFFFAOYSA-N 0.000 claims description 2
- RWSDZEDXPXJFII-UHFFFAOYSA-N 4-(3-hydroxy-2-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=CC(O)=C1C RWSDZEDXPXJFII-UHFFFAOYSA-N 0.000 claims description 2
- BMTOWXRBCGQVGA-UHFFFAOYSA-N 4-(3-hydroxy-4-methoxyanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C1=C(O)C(OC)=CC=C1NC1=C(C(N)=O)C=NC2=CC(OC)=C(OC)C=C12 BMTOWXRBCGQVGA-UHFFFAOYSA-N 0.000 claims description 2
- XPCWRQZEJYHNBZ-UHFFFAOYSA-N 4-(4-bromo-2-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(Br)C=C1C XPCWRQZEJYHNBZ-UHFFFAOYSA-N 0.000 claims description 2
- XZGGOZYDAVVFDA-UHFFFAOYSA-N 4-(4-bromo-2-methylanilino)-7-methoxyquinoline-3-carboxamide Chemical compound NC(=O)C=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(Br)C=C1C XZGGOZYDAVVFDA-UHFFFAOYSA-N 0.000 claims description 2
- SSSQBBWJMZYDLU-UHFFFAOYSA-N 4-(4-chloro-2-fluoroanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(Cl)C=C1F SSSQBBWJMZYDLU-UHFFFAOYSA-N 0.000 claims description 2
- AAXMLNCCWGCCNS-UHFFFAOYSA-N 4-(4-chloro-2-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(Cl)C=C1C AAXMLNCCWGCCNS-UHFFFAOYSA-N 0.000 claims description 2
- BBCCNXPVBPOPCW-UHFFFAOYSA-N 4-(4-chloro-2-methylanilino)-6-methoxyquinoline-3-carboxamide Chemical compound C12=CC(OC)=CC=C2N=CC(C(N)=O)=C1NC1=CC=C(Cl)C=C1C BBCCNXPVBPOPCW-UHFFFAOYSA-N 0.000 claims description 2
- BLLJJPXVWLUKEZ-UHFFFAOYSA-N 4-(4-chloro-2-methylanilino)-7-methoxyquinoline-3-carboxamide Chemical compound NC(=O)C=1C=NC2=CC(OC)=CC=C2C=1NC1=CC=C(Cl)C=C1C BLLJJPXVWLUKEZ-UHFFFAOYSA-N 0.000 claims description 2
- PDRUYGJKOGAVPR-UHFFFAOYSA-N 4-(4-fluoro-2-methylanilino)-6,7-dimethoxyquinoline-3-carboxamide Chemical compound C=12C=C(OC)C(OC)=CC2=NC=C(C(N)=O)C=1NC1=CC=C(F)C=C1C PDRUYGJKOGAVPR-UHFFFAOYSA-N 0.000 claims description 2
- BCLLANOSBAQYKP-UHFFFAOYSA-N 4-(4-fluoro-2-methylanilino)-6-methoxyquinoline-3-carboxamide Chemical compound C12=CC(OC)=CC=C2N=CC(C(N)=O)=C1NC1=CC=C(F)C=C1C BCLLANOSBAQYKP-UHFFFAOYSA-N 0.000 claims description 2
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Classifications
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- 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
- A61K31/47—Quinolines; Isoquinolines
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- 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
- C07D231/12—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 only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom 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
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
- C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Diabetes (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Pulmonology (AREA)
- Rheumatology (AREA)
- Emergency Medicine (AREA)
- Physical Education & Sports Medicine (AREA)
- Psychiatry (AREA)
- Pain & Pain Management (AREA)
- Hospice & Palliative Care (AREA)
- Obesity (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Quinoline Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
SE0101675A SE0101675D0 (sv) | 2001-05-11 | 2001-05-11 | Novel composition |
PCT/SE2002/000875 WO2002092571A1 (en) | 2001-05-11 | 2002-05-06 | Novel 4-anilinoquinoline-3-carboxamides |
Publications (1)
Publication Number | Publication Date |
---|---|
UA76142C2 true UA76142C2 (en) | 2006-07-17 |
Family
ID=20284085
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
UA2003109525A UA76142C2 (en) | 2001-05-11 | 2002-06-05 | 4-anilinoquinoline-3-carboxamides and pharmaceutically acceptable salts thereof and pharmaceutical composition containing them |
Country Status (25)
Country | Link |
---|---|
US (2) | US7037925B2 (xx) |
EP (1) | EP1387830A1 (xx) |
JP (1) | JP2004533452A (xx) |
KR (1) | KR20040007547A (xx) |
CN (1) | CN1286815C (xx) |
AR (1) | AR037489A1 (xx) |
BG (1) | BG108325A (xx) |
BR (1) | BR0209431A (xx) |
CA (1) | CA2446717A1 (xx) |
CZ (1) | CZ20033034A3 (xx) |
EE (1) | EE200300544A (xx) |
HU (1) | HUP0401339A2 (xx) |
IL (1) | IL158517A0 (xx) |
IS (1) | IS7016A (xx) |
MX (1) | MXPA03010207A (xx) |
MY (1) | MY134136A (xx) |
NO (1) | NO20034992D0 (xx) |
NZ (1) | NZ529302A (xx) |
PL (1) | PL366766A1 (xx) |
RU (1) | RU2281940C2 (xx) |
SE (1) | SE0101675D0 (xx) |
SK (1) | SK13712003A3 (xx) |
UA (1) | UA76142C2 (xx) |
WO (1) | WO2002092571A1 (xx) |
ZA (1) | ZA200308350B (xx) |
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ES2400339T3 (es) | 2002-07-15 | 2013-04-09 | Symphony Evolution, Inc. | Compuestos, composiciones farmacéuticas de los mismos y su uso en el tratamiento del cáncer |
SE0301373D0 (sv) | 2003-05-09 | 2003-05-09 | Astrazeneca Ab | Novel compounds |
TWI328009B (en) * | 2003-05-21 | 2010-08-01 | Glaxo Group Ltd | Quinoline derivatives as phosphodiesterase inhibitors |
WO2005009971A1 (ja) | 2003-07-24 | 2005-02-03 | Astellas Pharma Inc. | キノロン誘導体又はその塩 |
JP4638436B2 (ja) | 2003-09-26 | 2011-02-23 | エグゼリクシス, インコーポレイテッド | c−Metモジュレーターおよびその使用 |
GB0322722D0 (en) * | 2003-09-27 | 2003-10-29 | Glaxo Group Ltd | Compounds |
EP1711495A2 (en) | 2004-01-23 | 2006-10-18 | Amgen Inc. | Quinoline, quinazoline, pyridine and pyrimidine counds and their use in the treatment of inflammation, angiogenesis and cancer |
SE0400284D0 (sv) * | 2004-02-10 | 2004-02-10 | Astrazeneca Ab | Novel compounds |
EP1755680A1 (en) | 2004-05-03 | 2007-02-28 | Novartis AG | Combinations comprising a s1p receptor agonist and a jak3 kinase inhibitor |
MX2007004403A (es) | 2004-10-12 | 2007-04-27 | Astrazeneca Ab | Derivados de quinazolina. |
AU2005299018B2 (en) * | 2004-10-19 | 2011-07-07 | F. Hoffmann-La Roche Ag | Quinoline derivatives |
AU2006307657B2 (en) | 2005-10-28 | 2010-10-28 | Astrazeneca Ab | 4- (3-aminopyrazole) pyrimidine derivatives for use as tyrosine kinase inhibitors in the treatment of cancer |
JP2009528336A (ja) * | 2006-03-02 | 2009-08-06 | アストラゼネカ アクチボラグ | キノリン誘導体 |
UY30183A1 (es) | 2006-03-02 | 2007-10-31 | Astrazeneca Ab | Derivados de quinolina |
ES2427247T3 (es) * | 2006-03-13 | 2013-10-30 | Kyorin Pharmaceutical Co., Ltd. | Aminoquinolonas como inhibidores de GSK-3 |
RS51483B (en) * | 2006-04-14 | 2011-04-30 | Astrazeneca Ab | 4-ANILOXOQINOLINE-3-CARBOXamide KAO INHIBITOR CSF-1R Kinase |
WO2007139496A1 (en) * | 2006-05-30 | 2007-12-06 | Clanotech Ab | Quinoline derivatives acting as tyrosine kinase inhibitors |
TW200829555A (en) * | 2006-11-10 | 2008-07-16 | Astrazeneca Ab | Chemical compounds |
CL2008000191A1 (es) * | 2007-01-25 | 2008-08-22 | Astrazeneca Ab | Compuestos derivados de 4-amino-cinnotina-3-carboxamida; inhibidores de csf-1r quinasa; su proceso de preparacion; y su uso para tratar el cancer. |
CN102351880B (zh) * | 2007-09-11 | 2014-11-12 | 杏林制药株式会社 | 作为gsk-3 抑制剂的氰基氨基喹诺酮和四唑并氨基喹诺酮 |
MX2010002662A (es) | 2007-09-12 | 2010-04-09 | Activx Biosciences Inc | Aminoquinolonas espirociclicas como inhibidores de gsk-3. |
PT2323993E (pt) | 2008-04-16 | 2015-10-12 | Portola Pharm Inc | 2,6-diamino-pirimidina-5-il-carboxamidas como inibidores de quinasses syk ou jak |
US8138339B2 (en) | 2008-04-16 | 2012-03-20 | Portola Pharmaceuticals, Inc. | Inhibitors of protein kinases |
EP2310375A1 (en) * | 2008-05-07 | 2011-04-20 | AstraZeneca AB | Chemical compounds |
WO2010058846A1 (ja) * | 2008-11-21 | 2010-05-27 | アステラス製薬株式会社 | 4,6-ジアミノニコチンアミド化合物 |
TWI577664B (zh) | 2009-01-16 | 2017-04-11 | 艾克塞里克斯公司 | N-(4-{〔6,7-雙(甲氧基)喹啉-4-基〕氧基}苯基)-n’-(4-氟苯基)環丙烷-1,1-二甲醯胺蘋果酸鹽、包含其之醫藥組合物及其用途 |
EP2406266B1 (en) | 2009-03-11 | 2013-12-25 | Kyorin Pharmaceutical Co., Ltd. | 7-cycloalkylaminoquinolones as gsk-3 inhibitors |
AR076550A1 (es) | 2009-05-06 | 2011-06-22 | Portola Pharm Inc | Inhibidores de la janus tirosina kinasa (jak) |
UA108618C2 (uk) | 2009-08-07 | 2015-05-25 | Застосування c-met-модуляторів в комбінації з темозоломідом та/або променевою терапією для лікування раку | |
MX342879B (es) | 2010-07-30 | 2016-10-14 | Oncotherapy Science Inc * | Derivados de quinolina e inhibidores de cinasa de cremallera de leucina embrionica materna que los contienen. |
UY33549A (es) * | 2010-08-10 | 2012-01-31 | Glaxo Group Ltd | Quinolil aminas como agentes inhibidores de las quinasas |
US9102625B2 (en) | 2010-11-01 | 2015-08-11 | Portola Pharmaceuticals, Inc. | Nicotinamides as JAK kinase modulators |
JP6026441B2 (ja) | 2011-03-04 | 2016-11-16 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドGlaxosmithkline Intellectual Property Development Limited | キナーゼ阻害剤としてのアミノキノリン |
TWI547494B (zh) | 2011-08-18 | 2016-09-01 | 葛蘭素史克智慧財產發展有限公司 | 作為激酶抑制劑之胺基喹唑啉類 |
MX363551B (es) | 2011-11-23 | 2019-03-27 | Portola Pharmaceuticals Inc Star | Compuestos derivados de pirazina como inhibidores de cinasa. |
TWI592417B (zh) | 2012-09-13 | 2017-07-21 | 葛蘭素史克智慧財產發展有限公司 | 胺基喹唑啉激酶抑制劑之前藥 |
AR092530A1 (es) | 2012-09-13 | 2015-04-22 | Glaxosmithkline Llc | Compuesto de amino-quinolina, composicion farmaceutica que lo comprende y uso de dicho compuesto para la preparacion de un medicamento |
AU2014216178B2 (en) | 2013-02-15 | 2018-06-28 | KALA BIO, Inc. | Therapeutic compounds and uses thereof |
EP2958895B1 (en) | 2013-02-20 | 2020-08-19 | Kala Pharmaceuticals, Inc. | Therapeutic compounds and uses thereof |
US9688688B2 (en) | 2013-02-20 | 2017-06-27 | Kala Pharmaceuticals, Inc. | Crystalline forms of 4-((4-((4-fluoro-2-methyl-1H-indol-5-yl)oxy)-6-methoxyquinazolin-7-yl)oxy)-1-(2-oxa-7-azaspiro[3.5]nonan-7-yl)butan-1-one and uses thereof |
AR094707A1 (es) | 2013-02-21 | 2015-08-19 | Glaxosmithkline Ip Dev Ltd | Compuesto de quinazolin-4-amina, composición farmacéutica que lo comprende y su uso para el tratamiento de una enfermedad mediada por la quinasa rip2 |
CN106061261B (zh) | 2013-11-01 | 2018-04-24 | 卡拉制药公司 | 治疗化合物的结晶形式及其用途 |
US9890173B2 (en) | 2013-11-01 | 2018-02-13 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
WO2016125187A1 (en) * | 2015-02-03 | 2016-08-11 | Council Of Scientific & Industrial Research | Novel quinoline derivatives and preparation thereof |
EP3509421A4 (en) | 2016-09-08 | 2020-05-20 | Kala Pharmaceuticals, Inc. | CRYSTALLINE FORMS OF THERAPEUTIC COMPOUNDS AND USES THEREOF |
AU2017324713B2 (en) | 2016-09-08 | 2020-08-13 | KALA BIO, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
CA3036340A1 (en) | 2016-09-08 | 2018-03-15 | Kala Pharmaceuticals, Inc. | Crystalline forms of therapeutic compounds and uses thereof |
US10723701B2 (en) | 2016-10-18 | 2020-07-28 | Beijing Konruns Pharmaceutical Co., Ltd. | Quinolyl-substituted carboxylic acid compound or pharmaceutically acceptable salt thereof, pharmaceutical composition of the same, and use of the same |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3037925A (en) * | 1958-04-09 | 1962-06-05 | Smith Corp A O | Cathodically protected structure and method of making same |
UA73073C2 (uk) | 1997-04-03 | 2005-06-15 | Уайт Холдінгз Корпорейшн | Заміщені 3-ціанохіноліни, спосіб їх одержання та фармацевтична композиція |
KR20010089171A (ko) * | 1998-08-21 | 2001-09-29 | 추후제출 | 퀴나졸린 유도체 |
-
2001
- 2001-05-11 SE SE0101675A patent/SE0101675D0/xx unknown
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2002
- 2002-05-03 AR ARP020101633A patent/AR037489A1/es not_active Application Discontinuation
- 2002-05-06 US US10/477,254 patent/US7037925B2/en not_active Expired - Fee Related
- 2002-05-06 HU HU0401339A patent/HUP0401339A2/hu unknown
- 2002-05-06 NZ NZ529302A patent/NZ529302A/en unknown
- 2002-05-06 EP EP02733657A patent/EP1387830A1/en not_active Withdrawn
- 2002-05-06 EE EEP200300544A patent/EE200300544A/xx unknown
- 2002-05-06 CA CA002446717A patent/CA2446717A1/en not_active Abandoned
- 2002-05-06 SK SK13712003A patent/SK13712003A3/sk unknown
- 2002-05-06 IL IL15851702A patent/IL158517A0/xx unknown
- 2002-05-06 KR KR10-2003-7014579A patent/KR20040007547A/ko not_active Application Discontinuation
- 2002-05-06 BR BR0209431-2A patent/BR0209431A/pt not_active IP Right Cessation
- 2002-05-06 CZ CZ20033034A patent/CZ20033034A3/cs unknown
- 2002-05-06 WO PCT/SE2002/000875 patent/WO2002092571A1/en active IP Right Grant
- 2002-05-06 JP JP2002589457A patent/JP2004533452A/ja active Pending
- 2002-05-06 PL PL02366766A patent/PL366766A1/xx unknown
- 2002-05-06 RU RU2003131679/04A patent/RU2281940C2/ru not_active IP Right Cessation
- 2002-05-06 MX MXPA03010207A patent/MXPA03010207A/es unknown
- 2002-05-06 CN CNB02809722XA patent/CN1286815C/zh not_active Expired - Fee Related
- 2002-05-09 MY MYPI20021680A patent/MY134136A/en unknown
- 2002-06-05 UA UA2003109525A patent/UA76142C2/uk unknown
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2003
- 2003-10-27 ZA ZA200308350A patent/ZA200308350B/en unknown
- 2003-11-05 IS IS7016A patent/IS7016A/is unknown
- 2003-11-07 BG BG108325A patent/BG108325A/bg unknown
- 2003-11-10 NO NO20034992A patent/NO20034992D0/no not_active Application Discontinuation
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2006
- 2006-03-06 US US11/368,914 patent/US20060173034A1/en not_active Abandoned
Also Published As
Publication number | Publication date |
---|---|
JP2004533452A (ja) | 2004-11-04 |
IS7016A (is) | 2003-11-05 |
RU2003131679A (ru) | 2005-05-10 |
CN1507434A (zh) | 2004-06-23 |
US20060173034A1 (en) | 2006-08-03 |
AR037489A1 (es) | 2004-11-17 |
SK13712003A3 (en) | 2004-10-05 |
RU2281940C2 (ru) | 2006-08-20 |
IL158517A0 (en) | 2004-05-12 |
BR0209431A (pt) | 2004-08-03 |
EP1387830A1 (en) | 2004-02-11 |
MY134136A (en) | 2007-11-30 |
SE0101675D0 (sv) | 2001-05-11 |
WO2002092571A1 (en) | 2002-11-21 |
BG108325A (bg) | 2004-11-30 |
CZ20033034A3 (en) | 2004-06-16 |
CA2446717A1 (en) | 2002-11-21 |
PL366766A1 (en) | 2005-02-07 |
ZA200308350B (en) | 2005-01-27 |
NZ529302A (en) | 2004-08-27 |
EE200300544A (et) | 2004-02-16 |
NO20034992D0 (no) | 2003-11-10 |
MXPA03010207A (es) | 2004-03-10 |
CN1286815C (zh) | 2006-11-29 |
HUP0401339A2 (hu) | 2004-12-28 |
KR20040007547A (ko) | 2004-01-24 |
US20040248923A1 (en) | 2004-12-09 |
HU0401339D0 (en) | 2004-08-30 |
US7037925B2 (en) | 2006-05-02 |
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