RU2332996C2 - Производные гидразонпиразола и их применение в качестве лекарственного средства - Google Patents
Производные гидразонпиразола и их применение в качестве лекарственного средства Download PDFInfo
- Publication number
- RU2332996C2 RU2332996C2 RU2004119957/04A RU2004119957A RU2332996C2 RU 2332996 C2 RU2332996 C2 RU 2332996C2 RU 2004119957/04 A RU2004119957/04 A RU 2004119957/04A RU 2004119957 A RU2004119957 A RU 2004119957A RU 2332996 C2 RU2332996 C2 RU 2332996C2
- Authority
- RU
- Russia
- Prior art keywords
- pyrazol
- hydrazono
- diamine
- ylamine
- phenylhydrazono
- Prior art date
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- 150000001875 compounds Chemical class 0.000 claims abstract 51
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 31
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 14
- 230000033115 angiogenesis Effects 0.000 claims abstract 5
- 125000006545 (C1-C9) alkyl group Chemical group 0.000 claims 59
- -1 3,5-diaminopyrazol-4-ylidene Chemical group 0.000 claims 57
- 229910052739 hydrogen Inorganic materials 0.000 claims 55
- 239000001257 hydrogen Substances 0.000 claims 55
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 54
- 125000001424 substituent group Chemical group 0.000 claims 42
- 239000000203 mixture Substances 0.000 claims 35
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 34
- 229910052736 halogen Inorganic materials 0.000 claims 30
- 150000002367 halogens Chemical group 0.000 claims 30
- 125000003545 alkoxy group Chemical group 0.000 claims 27
- 150000002431 hydrogen Chemical class 0.000 claims 21
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 18
- 238000000034 method Methods 0.000 claims 15
- 208000035475 disorder Diseases 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 12
- 230000002401 inhibitory effect Effects 0.000 claims 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 11
- 150000003839 salts Chemical class 0.000 claims 11
- 239000012453 solvate Substances 0.000 claims 11
- 125000005638 hydrazono group Chemical group 0.000 claims 10
- 230000003463 hyperproliferative effect Effects 0.000 claims 9
- 125000004414 alkyl thio group Chemical group 0.000 claims 8
- 125000000623 heterocyclic group Chemical group 0.000 claims 8
- 239000000546 pharmaceutical excipient Substances 0.000 claims 8
- 125000004076 pyridyl group Chemical group 0.000 claims 8
- 125000003226 pyrazolyl group Chemical group 0.000 claims 7
- SWMNDJWTLOCMPN-UHFFFAOYSA-N 4-[(3-methylsulfonylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CS(=O)(=O)C1=CC=CC(NN=C2C(=NN=C2N)N)=C1 SWMNDJWTLOCMPN-UHFFFAOYSA-N 0.000 claims 6
- 206010061218 Inflammation Diseases 0.000 claims 6
- 102000001253 Protein Kinase Human genes 0.000 claims 6
- 125000002947 alkylene group Chemical group 0.000 claims 6
- 230000004709 cell invasion Effects 0.000 claims 6
- 230000012292 cell migration Effects 0.000 claims 6
- 239000003937 drug carrier Substances 0.000 claims 6
- 230000004054 inflammatory process Effects 0.000 claims 6
- 102000006495 integrins Human genes 0.000 claims 6
- 108010044426 integrins Proteins 0.000 claims 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 6
- 108060006633 protein kinase Proteins 0.000 claims 6
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 6
- 125000003342 alkenyl group Chemical group 0.000 claims 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims 5
- 125000004415 heterocyclylalkyl group Chemical group 0.000 claims 5
- 239000002904 solvent Substances 0.000 claims 5
- DENZGEANZCUSLQ-UHFFFAOYSA-N 1-[3-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]phenyl]ethanethione Chemical compound CC(=S)C1=CC=CC(NN=C2C(=NN=C2N)N)=C1 DENZGEANZCUSLQ-UHFFFAOYSA-N 0.000 claims 4
- XBBUTOFNIPUCSQ-UHFFFAOYSA-N 1-benzyl-4-phenyldiazenylpyrazole-3,5-diamine Chemical compound NC1=C(N=NC=2C=CC=CC=2)C(N)=NN1CC1=CC=CC=C1 XBBUTOFNIPUCSQ-UHFFFAOYSA-N 0.000 claims 4
- ATPMQLROPXAZQD-UHFFFAOYSA-N 2-[3-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]phenyl]sulfonylethanol Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(S(=O)(=O)CCO)=C1 ATPMQLROPXAZQD-UHFFFAOYSA-N 0.000 claims 4
- GFXPRGHVUQBRIH-UHFFFAOYSA-N 2-[[5-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]pyridin-2-yl]-(2-hydroxyethyl)amino]ethanol Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(N(CCO)CCO)N=C1 GFXPRGHVUQBRIH-UHFFFAOYSA-N 0.000 claims 4
- HTZSGNXPBRUKAJ-UHFFFAOYSA-N 3-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]-n-ethylbenzenesulfonamide Chemical compound CCNS(=O)(=O)C1=CC=CC(NN=C2C(=NN=C2N)N)=C1 HTZSGNXPBRUKAJ-UHFFFAOYSA-N 0.000 claims 4
- FJBAGQFQPZKKMW-UHFFFAOYSA-N 3-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]-n-methylbenzenesulfonamide Chemical compound CNS(=O)(=O)C1=CC=CC(NN=C2C(=NN=C2N)N)=C1 FJBAGQFQPZKKMW-UHFFFAOYSA-N 0.000 claims 4
- YLUOVVHTIJCVGM-UHFFFAOYSA-N 4-(1h-indazol-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(NN=C2)C2=C1 YLUOVVHTIJCVGM-UHFFFAOYSA-N 0.000 claims 4
- SYDRIGRFPHLLIL-UHFFFAOYSA-N 4-(1h-pyrazol-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=NNC=C1 SYDRIGRFPHLLIL-UHFFFAOYSA-N 0.000 claims 4
- LXBFAVNHXSASKP-UHFFFAOYSA-N 4-(2,1,3-benzothiadiazol-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC2=NSN=C2C=C1 LXBFAVNHXSASKP-UHFFFAOYSA-N 0.000 claims 4
- NZCBFZLZEYASLT-UHFFFAOYSA-N 4-(2h-benzotriazol-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC2=NNN=C2C=C1 NZCBFZLZEYASLT-UHFFFAOYSA-N 0.000 claims 4
- BLWACJKMLGVWSD-UHFFFAOYSA-N 4-(isoquinolin-5-yldiazenyl)-1-methylpyrazole-3,5-diamine Chemical compound CN1N=C(N)C(N=NC=2C3=CC=NC=C3C=CC=2)=C1N BLWACJKMLGVWSD-UHFFFAOYSA-N 0.000 claims 4
- WXIDXRYWMCOAMZ-UHFFFAOYSA-N 4-(isoquinolin-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC2=CN=CC=C12 WXIDXRYWMCOAMZ-UHFFFAOYSA-N 0.000 claims 4
- PLHRCOBFPLCLTB-UHFFFAOYSA-N 4-(phthalazin-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC2=CN=NC=C12 PLHRCOBFPLCLTB-UHFFFAOYSA-N 0.000 claims 4
- JXSAUZNHZQMFRG-UHFFFAOYSA-N 4-(quinazolin-6-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(N=CN=C2)C2=C1 JXSAUZNHZQMFRG-UHFFFAOYSA-N 0.000 claims 4
- AFVJBKNXMOEEDH-UHFFFAOYSA-N 4-(quinolin-3-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CN=C(C=CC=C2)C2=C1 AFVJBKNXMOEEDH-UHFFFAOYSA-N 0.000 claims 4
- VJTFGXNTVJAVKH-UHFFFAOYSA-N 4-(quinolin-5-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC2=NC=CC=C12 VJTFGXNTVJAVKH-UHFFFAOYSA-N 0.000 claims 4
- VGUAVKPBURZYFP-UHFFFAOYSA-N 4-(quinolin-6-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(N=CC=C2)C2=C1 VGUAVKPBURZYFP-UHFFFAOYSA-N 0.000 claims 4
- HVLNCWLDCPOSJM-UHFFFAOYSA-N 4-(quinolin-8-ylhydrazinylidene)pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC2=CC=CN=C12 HVLNCWLDCPOSJM-UHFFFAOYSA-N 0.000 claims 4
- LAUVWKRSNDAGJJ-UHFFFAOYSA-N 4-[(1,1-dioxo-1-benzothiophen-6-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(C=CS2(=O)=O)C2=C1 LAUVWKRSNDAGJJ-UHFFFAOYSA-N 0.000 claims 4
- FGKNJBGUMSBLLY-UHFFFAOYSA-N 4-[(1-methylbenzotriazol-5-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C=1C=C2N(C)N=NC2=CC=1NN=C1C(N)=NN=C1N FGKNJBGUMSBLLY-UHFFFAOYSA-N 0.000 claims 4
- SHISAUBIDDYUEF-UHFFFAOYSA-N 4-[(2,2,3,3-tetrafluoro-1,4-benzodioxin-6-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(OC(F)(F)C(F)(F)O2)C2=C1 SHISAUBIDDYUEF-UHFFFAOYSA-N 0.000 claims 4
- VGTFEMDPDAWVHL-UHFFFAOYSA-N 4-[(2,2-difluoro-1,3-benzodioxol-5-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(OC(F)(F)O2)C2=C1 VGTFEMDPDAWVHL-UHFFFAOYSA-N 0.000 claims 4
- JEQORHSNDXKPOB-UHFFFAOYSA-N 4-[(2,6-dichloropyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(Cl)N=C1Cl JEQORHSNDXKPOB-UHFFFAOYSA-N 0.000 claims 4
- BNZCQPDHOFTAOI-UHFFFAOYSA-N 4-[(2,6-dimethoxypyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound COC1=NC(OC)=CC=C1NN=C1C(N)=NN=C1N BNZCQPDHOFTAOI-UHFFFAOYSA-N 0.000 claims 4
- KUTLYOMFYHFOCV-UHFFFAOYSA-N 4-[(2-methyl-4-morpholin-4-ylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CC1=CC(N2CCOCC2)=CC=C1NN=C1C(N)=NN=C1N KUTLYOMFYHFOCV-UHFFFAOYSA-N 0.000 claims 4
- IDSDDJPKGOZETE-UHFFFAOYSA-N 4-[(2-methyl-5-nitrophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CC1=CC=C([N+]([O-])=O)C=C1NN=C1C(N)=NN=C1N IDSDDJPKGOZETE-UHFFFAOYSA-N 0.000 claims 4
- VLZPUXIGSQGLID-UHFFFAOYSA-N 4-[(2-methylbenzotriazol-5-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C=1C2=NN(C)N=C2C=CC=1NN=C1C(N)=NN=C1N VLZPUXIGSQGLID-UHFFFAOYSA-N 0.000 claims 4
- JCFVYHNWYLZMOJ-UHFFFAOYSA-N 4-[(3-chloro-4-morpholin-4-ylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1Cl)=CC=C1N1CCOCC1 JCFVYHNWYLZMOJ-UHFFFAOYSA-N 0.000 claims 4
- RNSZEDRJCFFWBL-UHFFFAOYSA-N 4-[(3-methylbenzotriazol-5-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=C2N(C)N=NC2=CC=C1NN=C1C(N)=NN=C1N RNSZEDRJCFFWBL-UHFFFAOYSA-N 0.000 claims 4
- ILUBMGCQMKKYJO-UHFFFAOYSA-N 4-[(4-anilinophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1)=CC=C1NC1=CC=CC=C1 ILUBMGCQMKKYJO-UHFFFAOYSA-N 0.000 claims 4
- CYVYICZTQSDTOS-UHFFFAOYSA-N 4-[(4-benzylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1)=CC=C1CC1=CC=CC=C1 CYVYICZTQSDTOS-UHFFFAOYSA-N 0.000 claims 4
- UKADBJVNJWDGOZ-UHFFFAOYSA-N 4-[(4-methoxy-3-nitrophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=C([N+]([O-])=O)C(OC)=CC=C1NN=C1C(N)=NN=C1N UKADBJVNJWDGOZ-UHFFFAOYSA-N 0.000 claims 4
- HYVDTUJBZBTGKJ-UHFFFAOYSA-N 4-[(4-methylpyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CC1=CC=NC=C1NN=C1C(N)=NN=C1N HYVDTUJBZBTGKJ-UHFFFAOYSA-N 0.000 claims 4
- LVAXTFMEIFHCBR-UHFFFAOYSA-N 4-[(4-methylsulfonylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=CC(S(=O)(=O)C)=CC=C1NN=C1C(N)=NN=C1N LVAXTFMEIFHCBR-UHFFFAOYSA-N 0.000 claims 4
- ZVGKPZWQFQKOTD-UHFFFAOYSA-N 4-[(4-phenylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(C=2C=CC=CC=2)C=C1 ZVGKPZWQFQKOTD-UHFFFAOYSA-N 0.000 claims 4
- MBDCGUWTYFSKPK-UHFFFAOYSA-N 4-[(4-piperidin-1-ylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(N2CCCCC2)C=C1 MBDCGUWTYFSKPK-UHFFFAOYSA-N 0.000 claims 4
- VNPYJZGIYBYVCZ-UHFFFAOYSA-N 4-[(6-chloropyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(Cl)N=C1 VNPYJZGIYBYVCZ-UHFFFAOYSA-N 0.000 claims 4
- KJJQTZARCNGDPP-UHFFFAOYSA-N 4-[(6-fluoropyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(F)N=C1 KJJQTZARCNGDPP-UHFFFAOYSA-N 0.000 claims 4
- BHLUYAROZQEDOZ-UHFFFAOYSA-N 4-[(6-methoxypyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=NC(OC)=CC=C1NN=C1C(N)=NN=C1N BHLUYAROZQEDOZ-UHFFFAOYSA-N 0.000 claims 4
- IROJQICVHPPBRP-UHFFFAOYSA-N 4-[(6-morpholin-4-ylpyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(N2CCOCC2)N=C1 IROJQICVHPPBRP-UHFFFAOYSA-N 0.000 claims 4
- KKYMGLKCALSWMO-UHFFFAOYSA-N 4-[(6-piperidin-1-ylpyridin-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(N2CCCCC2)N=C1 KKYMGLKCALSWMO-UHFFFAOYSA-N 0.000 claims 4
- VUVGJXROVOASCQ-UHFFFAOYSA-N 4-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]-n-ethylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NCC)=CC=C1NN=C1C(N)=NN=C1N VUVGJXROVOASCQ-UHFFFAOYSA-N 0.000 claims 4
- CKWHIDHJZNTSFQ-UHFFFAOYSA-N 4-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]-n-methylbenzenesulfonamide Chemical compound C1=CC(S(=O)(=O)NC)=CC=C1NN=C1C(N)=NN=C1N CKWHIDHJZNTSFQ-UHFFFAOYSA-N 0.000 claims 4
- USDDAUQNOXISQF-UHFFFAOYSA-N 4-[[2,3-difluoro-4-(trifluoromethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(C(F)(F)F)C(F)=C1F USDDAUQNOXISQF-UHFFFAOYSA-N 0.000 claims 4
- YPCLLZPOBUFZFR-UHFFFAOYSA-N 4-[[3-(diethylaminomethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound CCN(CC)CC1=CC=CC(NN=C2C(=NN=C2N)N)=C1 YPCLLZPOBUFZFR-UHFFFAOYSA-N 0.000 claims 4
- ZXCCFKRQIFPALL-UHFFFAOYSA-N 4-[[3-(morpholin-4-ylmethyl)-5-(trifluoromethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC(CN2CCOCC2)=CC(C(F)(F)F)=C1 ZXCCFKRQIFPALL-UHFFFAOYSA-N 0.000 claims 4
- ZMIQHAQOBHYLAA-UHFFFAOYSA-N 4-[[3-(morpholin-4-ylmethyl)-5-nitrophenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC(CN2CCOCC2)=CC([N+]([O-])=O)=C1 ZMIQHAQOBHYLAA-UHFFFAOYSA-N 0.000 claims 4
- WGHKLKZBVIICCR-UHFFFAOYSA-N 4-[[3-(morpholin-4-ylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(CN2CCOCC2)=C1 WGHKLKZBVIICCR-UHFFFAOYSA-N 0.000 claims 4
- WHPMUGPULQQXBI-UHFFFAOYSA-N 4-[[3-(piperidin-1-ylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(CN2CCCCC2)=C1 WHPMUGPULQQXBI-UHFFFAOYSA-N 0.000 claims 4
- VAJBUYAUWRFIRT-UHFFFAOYSA-N 4-[[3-(pyrrolidin-1-ylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(CN2CCCC2)=C1 VAJBUYAUWRFIRT-UHFFFAOYSA-N 0.000 claims 4
- PTGIUDNMMLWFCI-UHFFFAOYSA-N 4-[[3-(trifluoromethoxy)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(OC(F)(F)F)=C1 PTGIUDNMMLWFCI-UHFFFAOYSA-N 0.000 claims 4
- SVZYIZZHGRDLDA-UHFFFAOYSA-N 4-[[3-(trifluoromethylsulfonyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(S(=O)(=O)C(F)(F)F)=C1 SVZYIZZHGRDLDA-UHFFFAOYSA-N 0.000 claims 4
- HOYGPQALOHHUTF-UHFFFAOYSA-N 4-[[3-[(4-methylpiperazin-1-yl)methyl]phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1CN(C)CCN1CC1=CC=CC(NN=C2C(=NN=C2N)N)=C1 HOYGPQALOHHUTF-UHFFFAOYSA-N 0.000 claims 4
- FTPKBUBZDIJYJG-UHFFFAOYSA-N 4-[[3-[(dimethylamino)methyl]phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound CN(C)CC1=CC=CC(NN=C2C(=NN=C2N)N)=C1 FTPKBUBZDIJYJG-UHFFFAOYSA-N 0.000 claims 4
- HRFHJUXFZAIGHZ-UHFFFAOYSA-N 4-[[3-[2-(2-methoxyethoxy)ethoxymethyl]phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound COCCOCCOCC1=CC=CC(NN=C2C(=NN=C2N)N)=C1 HRFHJUXFZAIGHZ-UHFFFAOYSA-N 0.000 claims 4
- KKIQMAZVFOEUPD-UHFFFAOYSA-N 4-[[3-fluoro-4-(morpholin-4-ylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1F)=CC=C1CN1CCOCC1 KKIQMAZVFOEUPD-UHFFFAOYSA-N 0.000 claims 4
- QIDWETIPOWISMD-UHFFFAOYSA-N 4-[[3-fluoro-5-(trifluoromethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC(F)=CC(C(F)(F)F)=C1 QIDWETIPOWISMD-UHFFFAOYSA-N 0.000 claims 4
- WRRTWGQFLSZBFW-UHFFFAOYSA-N 4-[[4-(2-morpholin-4-ylethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1)=CC=C1CCN1CCOCC1 WRRTWGQFLSZBFW-UHFFFAOYSA-N 0.000 claims 4
- KDAGZCFSQPZWAL-UHFFFAOYSA-N 4-[[4-(diethoxyphosphorylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=CC(CP(=O)(OCC)OCC)=CC=C1NN=C1C(N)=NN=C1N KDAGZCFSQPZWAL-UHFFFAOYSA-N 0.000 claims 4
- YZBFMEVYGFYHPT-UHFFFAOYSA-N 4-[[4-(morpholin-4-ylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1)=CC=C1CN1CCOCC1 YZBFMEVYGFYHPT-UHFFFAOYSA-N 0.000 claims 4
- WDKIOMUEDUOZCK-UHFFFAOYSA-N 4-[[4-(piperidin-1-ylmethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1)=CC=C1CN1CCCCC1 WDKIOMUEDUOZCK-UHFFFAOYSA-N 0.000 claims 4
- NSYWAIJQKAUUSD-UHFFFAOYSA-N 4-[[4-(trifluoromethylsulfonyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(S(=O)(=O)C(F)(F)F)C=C1 NSYWAIJQKAUUSD-UHFFFAOYSA-N 0.000 claims 4
- XLSVRHLNTHJXKB-UHFFFAOYSA-N 4-[[4-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]phenyl]methylamino]-1,2,5-thiadiazole-3-carboxamide Chemical compound NC(=O)C1=NSN=C1NCC(C=C1)=CC=C1NN=C1C(N)=NN=C1N XLSVRHLNTHJXKB-UHFFFAOYSA-N 0.000 claims 4
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- HUOCLFAYXHVEID-UHFFFAOYSA-N CCCC(CC(C1=NNC2=CC(F)=CC=C2)=NN=C1N)S(N)(=O)=O Chemical compound CCCC(CC(C1=NNC2=CC(F)=CC=C2)=NN=C1N)S(N)(=O)=O HUOCLFAYXHVEID-UHFFFAOYSA-N 0.000 claims 1
- 201000009030 Carcinoma Diseases 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- QQQIAJCEOKVDKX-UHFFFAOYSA-N FC=1C=C(C=CC1F)NN=C1C(=NN=C1C)NC Chemical compound FC=1C=C(C=CC1F)NN=C1C(=NN=C1C)NC QQQIAJCEOKVDKX-UHFFFAOYSA-N 0.000 claims 1
- 150000001412 amines Chemical class 0.000 claims 1
- 125000005605 benzo group Chemical group 0.000 claims 1
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 230000010261 cell growth Effects 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000842 isoxazolyl group Chemical group 0.000 claims 1
- YFZXAGXMBFZVOZ-UHFFFAOYSA-N methyl 4-[(4z)-5-amino-4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-yl]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1C1=NN=C(N)C1=NNC1=CC=CC(F)=C1 YFZXAGXMBFZVOZ-UHFFFAOYSA-N 0.000 claims 1
- 125000002757 morpholinyl group Chemical group 0.000 claims 1
- QCCVYSKGXCVTMP-UHFFFAOYSA-N n-[[5-amino-4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]butane-1-sulfonamide Chemical compound CCCCS(=O)(=O)NCC1=NN=C(N)C1=NNC1=CC=CC(F)=C1 QCCVYSKGXCVTMP-UHFFFAOYSA-N 0.000 claims 1
- 125000001624 naphthyl group Chemical group 0.000 claims 1
- 125000003386 piperidinyl group Chemical group 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
- 201000010099 disease Diseases 0.000 abstract 2
- 230000001028 anti-proliverative effect Effects 0.000 abstract 1
- 230000006907 apoptotic process Effects 0.000 abstract 1
- 230000004071 biological effect Effects 0.000 abstract 1
- 230000006378 damage Effects 0.000 abstract 1
- 230000009025 developmental regulation Effects 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 150000003217 pyrazoles Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 230000004614 tumor growth Effects 0.000 abstract 1
- 0 CC(C)N=C1C(N(C)*)=NN=C1* Chemical compound CC(C)N=C1C(N(C)*)=NN=C1* 0.000 description 1
Classifications
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Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33526501P | 2001-11-30 | 2001-11-30 | |
| US60/335,265 | 2001-11-30 | ||
| US10/077,238 US7105503B2 (en) | 2000-04-07 | 2002-02-15 | Pyrazole compounds |
| US10/077,238 | 2002-02-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2004119957A RU2004119957A (ru) | 2005-07-20 |
| RU2332996C2 true RU2332996C2 (ru) | 2008-09-10 |
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| Application Number | Title | Priority Date | Filing Date |
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| RU2004119957/04A RU2332996C2 (ru) | 2001-11-30 | 2002-10-18 | Производные гидразонпиразола и их применение в качестве лекарственного средства |
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| Country | Link |
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| US (3) | US7875728B2 (https=) |
| EP (1) | EP1450791A1 (https=) |
| JP (1) | JP2005519878A (https=) |
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| AU (2) | AU2002333114B2 (https=) |
| CA (1) | CA2468562C (https=) |
| MX (1) | MXPA04005204A (https=) |
| RU (1) | RU2332996C2 (https=) |
| WO (1) | WO2003045379A1 (https=) |
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| CY2010012I2 (el) | 2000-05-25 | 2020-05-29 | Novartis Ag | Μιμητικα θρομβοποιητινης |
| RU2332996C2 (ru) | 2001-11-30 | 2008-09-10 | КьюЭлТи Инк. | Производные гидразонпиразола и их применение в качестве лекарственного средства |
| TWI280128B (en) | 2002-05-22 | 2007-05-01 | Smithkline Beecham Corp | 3'-[(2Z)-[1-(3,4- dimethylphenyl)-1,5-dihydro-3-methyl-5-oxo-4H-pyrazol-4-ylidene]hydrazino]-2'-hydroxy-[1,1'-biphenyl]-3-carboxylic acid bis-(monoethanolamine) |
| TW200526638A (en) | 2003-10-22 | 2005-08-16 | Smithkline Beecham Corp | 2-(3,4-dimethylphenyl)-4-{[2-hydroxy-3'-(1H-tetrazol-5-yl)biphenyl-3-yl]-hydrazono}-5-methyl-2,4-dihydropyrazol-3-one choline |
| GB0419416D0 (en) * | 2004-09-01 | 2004-10-06 | Inst Of Ex Botany Ascr | 4-Arylazo-3,5-Diamino-Pyrazole compounds and use thereof |
| ECSP077628A (es) | 2007-05-03 | 2008-12-30 | Smithkline Beechman Corp | Nueva composición farmacéutica |
| GB0908614D0 (en) | 2009-05-19 | 2009-06-24 | Tayside Flow Technologies Ltd | A vascular graft |
| MX2011012668A (es) | 2009-05-29 | 2011-12-16 | Glaxosmithkline Llc | Metodos de administracion de compuestos agonistas de trombopoyetina. |
| RU2546005C2 (ru) | 2009-09-15 | 2015-04-10 | Кью Эл Ти ИНК. | Фармацевтические составы, содержащие 9-цис-ретиниловые сложные эфиры в липидном наполнителе |
| US9173856B2 (en) | 2010-04-19 | 2015-11-03 | Qlt Inc. | Therapeutic regimen and methods for treating or ameliorating visual disorders associated with an endogenous retinoid deficiency |
| CA2865935C (en) | 2012-03-01 | 2021-12-14 | Qlt Inc. | Therapeutic regimens and methods for improving visual function in visual disorders associated with an endogenous retinoid deficiency |
| CN104958288B (zh) * | 2015-06-26 | 2017-08-11 | 苏州大学 | 一种血小板抑制剂及其在制备抗血小板疾病药物中的应用 |
| KR102128509B1 (ko) * | 2018-12-19 | 2020-07-01 | 한국과학기술연구원 | 말단 아민기에 아릴 또는 헤테로아릴기가 치환된 신규한 히드라존 유도체 및 이의 용도 |
| KR102356644B1 (ko) * | 2020-06-19 | 2022-01-28 | 한국과학기술연구원 | 신규한 옥소피리다지닐-페닐-카르보노하이드라조노일 디시아나이드 화합물 및 이의 용도 |
| EP4169916A4 (en) * | 2020-06-19 | 2024-07-10 | Korea Institute of Science and Technology | CARBONOHYDRAZONOYL DICYANIDE COMPOUND COMPRISING AT LEAST TWO TYPES OF ARYL OR HETEROARYL LINKED BY A NOVEL LINKER, AND USE THEREOF |
| KR102633087B1 (ko) * | 2020-06-19 | 2024-02-05 | 한국과학기술연구원 | 신규한 융합헤테로고리-카르보노하이드라조노일 디시아나이드 화합물 및 이의 용도 |
| CN113583110B (zh) * | 2021-08-19 | 2023-07-21 | 华南农业大学 | 一种苯并三唑半抗原、人工抗原和抗体及其制备方法与应用 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| SU1162799A1 (ru) * | 1982-07-09 | 1985-06-23 | Витебский государственный медицинский институт | Способ получени 4-арилгидразонов пиразолидинтриона-3,4,5 |
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|---|---|---|---|---|
| CH373842A (de) * | 1959-09-11 | 1963-12-15 | Geigy Ag J R | Verfahren zur Herstellung von in Wasser dispergierbaren, schwer löslichen Azofarbstoffen |
| NL127251C (https=) * | 1965-01-15 | |||
| DE2248738A1 (de) * | 1972-10-05 | 1974-04-11 | Bayer Ag | Kationische diazacyaninfarbstoffe |
| US4562248A (en) * | 1983-11-25 | 1985-12-31 | Eastman Kodak Company | Azo dyes from unsubstituted or substituted 3-amino-pyridine and aryl or heterocyclic couplers |
| CA2369076A1 (en) | 2000-02-05 | 2001-08-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compositions useful as inhibitors of erk |
| HUP0202332A2 (en) | 2000-02-05 | 2002-10-28 | Vertex Pharma | Pyrazole compositions useful as inhibitors of erk |
| WO2001056557A2 (en) | 2000-02-05 | 2001-08-09 | Vertex Pharmaceuticals Incorporated | Compositions useful as inhibitors of erk |
| US6436915B1 (en) * | 2000-04-07 | 2002-08-20 | Kinetek Pharmaceuticals, Inc. | Pyrazole compounds |
| US6214813B1 (en) * | 2000-04-07 | 2001-04-10 | Kinetek Pharmaceuticals, Inc. | Pyrazole compounds |
| GB0102687D0 (en) | 2001-02-02 | 2001-03-21 | Pharmacia & Upjohn Spa | Oxazolyl-pyrazole derivatives active as kinase inhibitors,process for their preparation and pharmaceutical compositions comprising them |
| RU2332996C2 (ru) | 2001-11-30 | 2008-09-10 | КьюЭлТи Инк. | Производные гидразонпиразола и их применение в качестве лекарственного средства |
| EP1456180B1 (en) | 2001-12-21 | 2007-10-03 | Vernalis (Cambridge) Limited | 3-(2,4)dihydroxyphenyl-4-phenylpyrazoles and their medical use |
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- 2002-10-18 JP JP2003546881A patent/JP2005519878A/ja not_active Ceased
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- 2002-10-18 WO PCT/CA2002/001583 patent/WO2003045379A1/en not_active Ceased
- 2002-10-18 US US10/497,046 patent/US7875728B2/en not_active Expired - Fee Related
- 2002-10-18 MX MXPA04005204A patent/MXPA04005204A/es unknown
- 2002-10-18 EP EP02803715A patent/EP1450791A1/en not_active Withdrawn
- 2002-10-18 AU AU2002333114A patent/AU2002333114B2/en not_active Ceased
- 2002-10-18 CN CNA02827752XA patent/CN1671379A/zh active Pending
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2008
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1162799A1 (ru) * | 1982-07-09 | 1985-06-23 | Витебский государственный медицинский институт | Способ получени 4-арилгидразонов пиразолидинтриона-3,4,5 |
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| ДРОБЕНКО А.Д. Химия гетероциклических соединний. - 1967, 713-715. * |
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|---|---|
| AU2002333114A1 (en) | 2003-06-10 |
| MXPA04005204A (es) | 2005-11-04 |
| CN1671379A (zh) | 2005-09-21 |
| WO2003045379A1 (en) | 2003-06-05 |
| AU2002333114B2 (en) | 2008-09-04 |
| EP1450791A1 (en) | 2004-09-01 |
| US8445694B2 (en) | 2013-05-21 |
| CA2468562C (en) | 2011-12-20 |
| US7875728B2 (en) | 2011-01-25 |
| US20140107125A1 (en) | 2014-04-17 |
| AU2008252075A1 (en) | 2009-01-08 |
| US20050272709A1 (en) | 2005-12-08 |
| US20110237783A1 (en) | 2011-09-29 |
| JP2005519878A (ja) | 2005-07-07 |
| RU2004119957A (ru) | 2005-07-20 |
| CA2468562A1 (en) | 2003-06-05 |
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