JP2005519878A5 - - Google Patents

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Publication number

JP2005519878A5

JP2005519878A5 JP2003546881A JP2003546881A JP2005519878A5 JP 2005519878 A5 JP2005519878 A5 JP 2005519878A5 JP 2003546881 A JP2003546881 A JP 2003546881A JP 2003546881 A JP2003546881 A JP 2003546881A JP 2005519878 A5 JP2005519878 A5 JP 2005519878A5

Authority

JP

Japan

Prior art keywords

pyrazol

hydrazono

ylamine

pyrazole

alkyl

Prior art date

2002-10-18

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Ceased

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• 125000000217 alkyl group Chemical group 0.000 claims description 264
• 125000003118 aryl group Chemical group 0.000 claims description 212
• 125000001424 substituent group Chemical group 0.000 claims description 140
• 125000005843 halogen group Chemical group 0.000 claims description 137
• 125000004415 heterocyclylalkyl group Chemical group 0.000 claims description 124
• 125000001188 haloalkyl group Chemical group 0.000 claims description 111
• 125000000623 heterocyclic group Chemical group 0.000 claims description 101
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 68
• 125000004438 haloalkoxy group Chemical group 0.000 claims description 57
• -1 3-methoxy-5-trifluoromethylphenyl Chemical group 0.000 claims description 55
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
• 125000003226 pyrazolyl group Chemical group 0.000 claims description 15
• 125000004076 pyridyl group Chemical group 0.000 claims description 11
• 125000003386 piperidinyl group Chemical group 0.000 claims description 10
• 125000002757 morpholinyl group Chemical group 0.000 claims description 9
• 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
• 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 7
• 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 6
• 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 6
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 6
• 125000004193 piperazinyl group Chemical group 0.000 claims description 5
• 125000000335 thiazolyl group Chemical group 0.000 claims description 5
• 125000002047 benzodioxolyl group Chemical group O1OC(C2=C1C=CC=C2)* 0.000 claims description 4
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
• 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
• 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
• 125000002541 furyl group Chemical group 0.000 claims description 3
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 3
• 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
• 125000001544 thienyl group Chemical group 0.000 claims description 3
• 229910052739 hydrogen Inorganic materials 0.000 claims 193
• 239000001257 hydrogen Substances 0.000 claims 193
• 150000001875 compounds Chemical class 0.000 claims 160
• 150000002431 hydrogen Chemical class 0.000 claims 126
• 125000003710 aryl alkyl group Chemical group 0.000 claims 116
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 67
• 239000008194 pharmaceutical composition Substances 0.000 claims 61
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 49
• 125000002947 alkylene group Chemical group 0.000 claims 48
• 125000003545 alkoxy group Chemical group 0.000 claims 40
• 239000000203 mixture Substances 0.000 claims 36
• 239000000546 pharmaceutical excipient Substances 0.000 claims 30
• 239000003085 diluting agent Substances 0.000 claims 29
• 239000003937 drug carrier Substances 0.000 claims 29
• 150000003839 salts Chemical class 0.000 claims 20
• 125000004995 haloalkylthio group Chemical group 0.000 claims 18
• 125000005164 aryl thioalkyl group Chemical group 0.000 claims 15
• 239000012453 solvate Substances 0.000 claims 14
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 13
• 125000006517 heterocyclyl carbonyl group Chemical group 0.000 claims 11
• 125000002768 hydroxyalkyl group Chemical group 0.000 claims 10
• 230000003463 hyperproliferative effect Effects 0.000 claims 10
• 125000003342 alkenyl group Chemical group 0.000 claims 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims 9
• AKQZEFRALAUBFS-UHFFFAOYSA-N ilamine Natural products COC(C)C(O)(C(=O)OCC1=CCN2CCCC12)C(C)(C)O AKQZEFRALAUBFS-UHFFFAOYSA-N 0.000 claims 9
• 201000010099 disease Diseases 0.000 claims 8
• 125000004450 alkenylene group Chemical group 0.000 claims 7
• 125000004414 alkyl thio group Chemical group 0.000 claims 6
• 230000033115 angiogenesis Effects 0.000 claims 5
• 208000035475 disorder Diseases 0.000 claims 5
• 239000003814 drug Substances 0.000 claims 5
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 5
• 238000004519 manufacturing process Methods 0.000 claims 5
• TZPCPCOGYXZHMH-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-pyridin-3-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2C=NC=CC=2)C1=NNC1=CC=CC=C1 TZPCPCOGYXZHMH-UHFFFAOYSA-N 0.000 claims 4
• PRFCJSJLZZUTMW-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-pyridin-4-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CN=CC=2)C1=NNC1=CC=CC=C1 PRFCJSJLZZUTMW-UHFFFAOYSA-N 0.000 claims 4
• FFTPRBGYDRYEPQ-UHFFFAOYSA-N (4e)-4-[(3,4-difluorophenyl)hydrazinylidene]-5-pyridin-3-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2C=NC=CC=2)C1=NNC1=CC=C(F)C(F)=C1 FFTPRBGYDRYEPQ-UHFFFAOYSA-N 0.000 claims 4
• MEJLRQLLZPMRLF-UHFFFAOYSA-N (4e)-4-[(3-fluoro-4-methoxyphenyl)hydrazinylidene]-5-pyridin-4-ylpyrazol-3-amine Chemical compound C1=C(F)C(OC)=CC=C1NN=C1C(C=2C=CN=CC=2)=NN=C1N MEJLRQLLZPMRLF-UHFFFAOYSA-N 0.000 claims 4
• RJQGSADMYLSRSH-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-(3-methylphenyl)pyrazol-3-amine Chemical compound CC1=CC=CC(C=2C(C(N)=NN=2)=NNC=2C=C(F)C=CC=2)=C1 RJQGSADMYLSRSH-UHFFFAOYSA-N 0.000 claims 4
• CTYKHPMLHJVKHX-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-(4-methoxyphenyl)pyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1C1=NN=C(N)C1=NNC1=CC=CC(F)=C1 CTYKHPMLHJVKHX-UHFFFAOYSA-N 0.000 claims 4
• BLWZYZFDMGHETD-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-(4-methylphenyl)pyrazol-3-amine Chemical compound C1=CC(C)=CC=C1C1=NN=C(N)C1=NNC1=CC=CC(F)=C1 BLWZYZFDMGHETD-UHFFFAOYSA-N 0.000 claims 4
• JSENNZWOEPJIPS-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-[3-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=C(C=CC=2)C(F)(F)F)C1=NNC1=CC=CC(F)=C1 JSENNZWOEPJIPS-UHFFFAOYSA-N 0.000 claims 4
• IWCGBBQUCCAVGA-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-[4-(trifluoromethoxy)phenyl]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CC(OC(F)(F)F)=CC=2)C1=NNC1=CC=CC(F)=C1 IWCGBBQUCCAVGA-UHFFFAOYSA-N 0.000 claims 4
• VVBFKBYTQJBTPB-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-pyridin-4-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CN=CC=2)C1=NNC1=CC=CC(F)=C1 VVBFKBYTQJBTPB-UHFFFAOYSA-N 0.000 claims 4
• MFXHPOJRBWDBBP-UHFFFAOYSA-N (4e)-5-(3-chlorophenyl)-4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=C(Cl)C=CC=2)C1=NNC1=CC=CC(F)=C1 MFXHPOJRBWDBBP-UHFFFAOYSA-N 0.000 claims 4
• MSTYMZUSMKYHJL-UHFFFAOYSA-N (4e)-5-(4-chlorophenyl)-4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CC(Cl)=CC=2)C1=NNC1=CC=CC(F)=C1 MSTYMZUSMKYHJL-UHFFFAOYSA-N 0.000 claims 4
• OUKNLVQNIFYFDZ-UHFFFAOYSA-N (4e)-5-(furan-2-yl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound NC1=NN=C(C=2OC=CC=2)\C1=N\NC1=CC=CC=C1 OUKNLVQNIFYFDZ-UHFFFAOYSA-N 0.000 claims 4
• QLNDTNYYPMNYCP-UHFFFAOYSA-N 2-[3-[(2e)-2-(3-amino-5-pyridin-4-ylpyrazol-4-ylidene)hydrazinyl]phenyl]sulfonylethanol Chemical compound NC1=NN=C(C=2C=CN=CC=2)C1=NNC1=CC=CC(S(=O)(=O)CCO)=C1 QLNDTNYYPMNYCP-UHFFFAOYSA-N 0.000 claims 4
• UDGCBOJAGBIKAE-UHFFFAOYSA-N 3-[2-(3-amino-5-morpholin-4-ylpyrazol-4-ylidene)hydrazinyl]benzenesulfonamide Chemical compound C=1C=CC(S(N)(=O)=O)=CC=1NN=C1C(N)=NN=C1N1CCOCC1 UDGCBOJAGBIKAE-UHFFFAOYSA-N 0.000 claims 4
• LBAPEKNSFCQQPK-UHFFFAOYSA-N 4-(phenylhydrazinylidene)-5-thiophen-3-ylpyrazol-3-amine Chemical compound NC1=NN=C(C2=CSC=C2)C1=NNC1=CC=CC=C1 LBAPEKNSFCQQPK-UHFFFAOYSA-N 0.000 claims 4
• VXVMOKZIUFRCLT-UHFFFAOYSA-N 4-[(3-fluoro-4-methoxyphenyl)hydrazinylidene]pyrazol-3-amine Chemical compound C1=C(F)C(OC)=CC=C1NN=C1C(N)=NN=C1 VXVMOKZIUFRCLT-UHFFFAOYSA-N 0.000 claims 4
• VMFBFJXRWNIGBQ-UHFFFAOYSA-N 4-[(3-fluorophenyl)hydrazinylidene]-5-(furan-2-yl)pyrazol-3-amine Chemical compound NC1=NN=C(C=2OC=CC=2)C1=NNC1=CC=CC(F)=C1 VMFBFJXRWNIGBQ-UHFFFAOYSA-N 0.000 claims 4
• YCCNOGZZWLCVPN-UHFFFAOYSA-N 4-[(3-fluorophenyl)hydrazinylidene]-5-(morpholin-4-ylmethyl)pyrazol-3-amine Chemical compound C=1C=CC(F)=CC=1NN=C1C(N)=NN=C1CN1CCOCC1 YCCNOGZZWLCVPN-UHFFFAOYSA-N 0.000 claims 4
• VFMJZFJEDNQJJN-UHFFFAOYSA-N 4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-amine Chemical compound NC1=NN=CC1=NNC1=CC=CC(F)=C1 VFMJZFJEDNQJJN-UHFFFAOYSA-N 0.000 claims 4
• LEVYJSOULZVOQU-UHFFFAOYSA-N 4-[[3-(morpholin-4-ylmethyl)phenyl]hydrazinylidene]-5-pyridin-4-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CN=CC=2)C1=NNC(C=1)=CC=CC=1CN1CCOCC1 LEVYJSOULZVOQU-UHFFFAOYSA-N 0.000 claims 4
• KVHNGYMZTQXLOZ-UHFFFAOYSA-N 4-[[4-fluoro-3-(trifluoromethyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(F)C(C(F)(F)F)=C1 KVHNGYMZTQXLOZ-UHFFFAOYSA-N 0.000 claims 4
• JNLYBOGJWDTFMR-UHFFFAOYSA-N 5-(3-nitrophenyl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=C(C=CC=2)[N+]([O-])=O)C1=NNC1=CC=CC=C1 JNLYBOGJWDTFMR-UHFFFAOYSA-N 0.000 claims 4
• RCBOHFIBUYSRBK-UHFFFAOYSA-N 5-(4-nitrophenyl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CC(=CC=2)[N+]([O-])=O)C1=NNC1=CC=CC=C1 RCBOHFIBUYSRBK-UHFFFAOYSA-N 0.000 claims 4
• NFYORNMHVKCDFC-UHFFFAOYSA-N 5-methyl-4-[(3-nitrophenyl)diazenyl]-1H-pyrazol-3-amine Chemical compound NC1=C(C(=NN1)C)N=NC1=CC(=CC=C1)[N+](=O)[O-] NFYORNMHVKCDFC-UHFFFAOYSA-N 0.000 claims 4
• 206010061218 Inflammation Diseases 0.000 claims 4
• 210000004027 cell Anatomy 0.000 claims 4
• 230000004054 inflammatory process Effects 0.000 claims 4
• CCHHAHOTQJKUNT-UHFFFAOYSA-N n-[(3-amino-5-but-3-enylpyrazol-4-ylidene)amino]pyridin-3-amine Chemical compound NC1=NN=C(CCC=C)C1=NNC1=CC=CN=C1 CCHHAHOTQJKUNT-UHFFFAOYSA-N 0.000 claims 4
• WOQXKYAYBQWQCG-UHFFFAOYSA-N n-[(3-amino-5-methylpyrazol-4-ylidene)amino]isoquinolin-5-amine Chemical compound CC1=NN=C(N)C1=NNC1=CC=CC2=CN=CC=C12 WOQXKYAYBQWQCG-UHFFFAOYSA-N 0.000 claims 4
• GQLHFSCTSCWIRR-UHFFFAOYSA-N n-[(3-amino-5-methylpyrazol-4-ylidene)amino]phthalazin-5-amine Chemical compound CC1=NN=C(N)C1=NNC1=CC=CC2=CN=NC=C12 GQLHFSCTSCWIRR-UHFFFAOYSA-N 0.000 claims 4
• IFIWAXWPHZTQAL-UHFFFAOYSA-N n-[(e)-(3-amino-5-pyridin-4-ylpyrazol-4-ylidene)amino]isoquinolin-5-amine Chemical compound C=1C=CC2=CN=CC=C2C=1NN=C1C(N)=NN=C1C1=CC=NC=C1 IFIWAXWPHZTQAL-UHFFFAOYSA-N 0.000 claims 4
• ZBHCUEQBXAPHAA-UHFFFAOYSA-N n-[(e)-[3-amino-5-[(4-methoxyphenyl)methyl]pyrazol-4-ylidene]amino]pyridin-3-amine Chemical compound C1=CC(OC)=CC=C1CC1=NN=C(N)C1=NNC1=CC=CN=C1 ZBHCUEQBXAPHAA-UHFFFAOYSA-N 0.000 claims 4
• BKGMBCUNSUZOGU-UHFFFAOYSA-N n-[[(4z)-5-amino-4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-yl]methyl]-2-chloro-6-methylpyridine-3-carboxamide Chemical compound ClC1=NC(C)=CC=C1C(=O)NCC1=NN=C(N)C1=NNC1=CC=CC(F)=C1 BKGMBCUNSUZOGU-UHFFFAOYSA-N 0.000 claims 4
• 125000003884 phenylalkyl group Chemical group 0.000 claims 4
• 206010029113 Neovascularisation Diseases 0.000 claims 3
• INSWERQZXYQHHB-UHFFFAOYSA-N n-[(e)-(3-amino-5-pyridin-4-ylpyrazol-4-ylidene)amino]pyridin-3-amine Chemical compound NC1=NN=C(C=2C=CN=CC=2)C1=NNC1=CC=CN=C1 INSWERQZXYQHHB-UHFFFAOYSA-N 0.000 claims 3
• 125000001113 thiadiazolyl group Chemical group 0.000 claims 3
• IFGLKCAHWDTUSU-UHFFFAOYSA-N (3,5-diamino-4-phenyldiazenylpyrazol-1-yl)-phenylmethanone Chemical compound NC1=C(N=NC=2C=CC=CC=2)C(N)=NN1C(=O)C1=CC=CC=C1 IFGLKCAHWDTUSU-UHFFFAOYSA-N 0.000 claims 2
• YDBNPZSBUNZAOA-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-(3,4,5-trimethoxyphenyl)pyrazol-3-amine Chemical compound COC1=C(OC)C(OC)=CC(C=2C(C(N)=NN=2)=NNC=2C=CC=CC=2)=C1 YDBNPZSBUNZAOA-UHFFFAOYSA-N 0.000 claims 2
• JFTGDOYWQZQAKJ-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-[2-(1,2,4-triazol-1-yl)propan-2-yl]pyrazol-3-amine Chemical compound C1=NC=NN1C(C)(C)C1=NN=C(N)C1=NNC1=CC=CC=C1 JFTGDOYWQZQAKJ-UHFFFAOYSA-N 0.000 claims 2
• QJUMCCRSNZGICL-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-[2-(trifluoromethoxy)phenyl]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C(=CC=CC=2)OC(F)(F)F)C1=NNC1=CC=CC=C1 QJUMCCRSNZGICL-UHFFFAOYSA-N 0.000 claims 2
• KQIRTQLHKZNPFZ-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-[4-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CC(=CC=2)C(F)(F)F)C1=NNC1=CC=CC=C1 KQIRTQLHKZNPFZ-UHFFFAOYSA-N 0.000 claims 2
• YVMZJHWAYVGCDJ-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-[4-(trifluoromethylsulfanyl)phenyl]pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CC(SC(F)(F)F)=CC=2)C1=NNC1=CC=CC=C1 YVMZJHWAYVGCDJ-UHFFFAOYSA-N 0.000 claims 2
• ZZMXYYFUWQSFEW-UHFFFAOYSA-N (4e)-4-(phenylhydrazinylidene)-5-thiophen-2-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2SC=CC=2)\C1=N\NC1=CC=CC=C1 ZZMXYYFUWQSFEW-UHFFFAOYSA-N 0.000 claims 2
• SUDNIPQPLNFBEW-UHFFFAOYSA-N (4e)-4-[(3,4-difluorophenyl)hydrazinylidene]-5-[(2-morpholin-4-ylethylamino)methyl]pyrazol-3-amine Chemical compound C=1C=C(F)C(F)=CC=1NN=C1C(N)=NN=C1CNCCN1CCOCC1 SUDNIPQPLNFBEW-UHFFFAOYSA-N 0.000 claims 2
• UZDHFBYJCWAOSA-UHFFFAOYSA-N (4e)-4-[(3,4-difluorophenyl)hydrazinylidene]-5-pyridin-4-ylpyrazol-3-amine Chemical compound NC1=NN=C(C=2C=CN=CC=2)C1=NNC1=CC=C(F)C(F)=C1 UZDHFBYJCWAOSA-UHFFFAOYSA-N 0.000 claims 2
• QYXKURQTXGOGPS-UHFFFAOYSA-N (4e)-4-[(3,4-difluorophenyl)hydrazinylidene]-n-ethyl-5-methylpyrazol-3-amine Chemical compound CCNC1=NN=C(C)\C1=N/NC1=CC=C(F)C(F)=C1 QYXKURQTXGOGPS-UHFFFAOYSA-N 0.000 claims 2
• VSRJENFZFZKAJS-UHFFFAOYSA-N (4e)-4-[(3,4-difluorophenyl)hydrazinylidene]-n-methyl-5-pyridin-4-ylpyrazol-3-amine Chemical compound CNC1=NN=C(C=2C=CN=CC=2)C1=NNC1=CC=C(F)C(F)=C1 VSRJENFZFZKAJS-UHFFFAOYSA-N 0.000 claims 2
• ILGBBXVCGYONHF-UHFFFAOYSA-N (4e)-4-[(3,5-difluorophenyl)hydrazinylidene]-5-(2-phenylethyl)pyrazol-3-amine Chemical compound C=1C(F)=CC(F)=CC=1NN=C1C(N)=NN=C1CCC1=CC=CC=C1 ILGBBXVCGYONHF-UHFFFAOYSA-N 0.000 claims 2
• MJUKGZPWBMTPDL-UHFFFAOYSA-N (4e)-4-[(3-chlorophenyl)hydrazinylidene]-5-(2-phenylethyl)pyrazol-3-amine Chemical compound C=1C=CC(Cl)=CC=1NN=C1C(N)=NN=C1CCC1=CC=CC=C1 MJUKGZPWBMTPDL-UHFFFAOYSA-N 0.000 claims 2
• JTNRMZCRNQNDDV-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-(2-methylfuran-3-yl)pyrazol-3-amine Chemical compound O1C=CC(C=2C(C(N)=NN=2)=NNC=2C=C(F)C=CC=2)=C1C JTNRMZCRNQNDDV-UHFFFAOYSA-N 0.000 claims 2
• HBYITLHIDBVVIE-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-(2-phenylethyl)pyrazol-3-amine Chemical compound C=1C=CC(F)=CC=1NN=C1C(N)=NN=C1CCC1=CC=CC=C1 HBYITLHIDBVVIE-UHFFFAOYSA-N 0.000 claims 2
• KPAWZHBZOUPWOJ-UHFFFAOYSA-N (4e)-4-[(3-fluorophenyl)hydrazinylidene]-5-n,5-n-dimethylpyrazole-3,5-diamine Chemical compound CN(C)C1=NN=C(N)C1=NNC1=CC=CC(F)=C1 KPAWZHBZOUPWOJ-UHFFFAOYSA-N 0.000 claims 2
• WJDWIJFTYTUPCS-UHFFFAOYSA-N (4e)-4-[(6-chloropyridin-3-yl)hydrazinylidene]-5-n,5-n-dimethylpyrazole-3,5-diamine Chemical compound CN(C)C1=NN=C(N)C1=NNC1=CC=C(Cl)N=C1 WJDWIJFTYTUPCS-UHFFFAOYSA-N 0.000 claims 2
• LAYBPTPWKYGAOP-UHFFFAOYSA-N (4e)-4-[(6-fluoropyridin-3-yl)hydrazinylidene]-5-n,5-n-dimethylpyrazole-3,5-diamine Chemical compound CN(C)C1=NN=C(N)C1=NNC1=CC=C(F)N=C1 LAYBPTPWKYGAOP-UHFFFAOYSA-N 0.000 claims 2
• OZINSXJBLUBVGA-UHFFFAOYSA-N (4e)-5-(2,5-dimethylfuran-3-yl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound O1C(C)=CC(C=2C(C(N)=NN=2)=NNC=2C=CC=CC=2)=C1C OZINSXJBLUBVGA-UHFFFAOYSA-N 0.000 claims 2
• YGIADHDYZCAGCJ-UHFFFAOYSA-N (4e)-5-(2-chloro-6-methylpyridin-4-yl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound ClC1=NC(C)=CC(C=2C(C(N)=NN=2)=NNC=2C=CC=CC=2)=C1 YGIADHDYZCAGCJ-UHFFFAOYSA-N 0.000 claims 2
• ZPEOSHYDLAYPLW-UHFFFAOYSA-N (4e)-5-(3-fluoro-4-methylphenyl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound C1=C(F)C(C)=CC=C1C1=NN=C(N)C1=NNC1=CC=CC=C1 ZPEOSHYDLAYPLW-UHFFFAOYSA-N 0.000 claims 2
• ZTQFOYSYQJROBY-UHFFFAOYSA-N (4e)-5-(4-chloro-3-nitrophenyl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound NC1=NN=C(C=2C=C(C(Cl)=CC=2)[N+]([O-])=O)C1=NNC1=CC=CC=C1 ZTQFOYSYQJROBY-UHFFFAOYSA-N 0.000 claims 2
• VTAOTWNTJNRLFD-UHFFFAOYSA-N (4e)-5-(4-fluoro-3-methylphenyl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound C1=C(F)C(C)=CC(C=2C(C(N)=NN=2)=NNC=2C=CC=CC=2)=C1 VTAOTWNTJNRLFD-UHFFFAOYSA-N 0.000 claims 2
• AVOVQBASOARMBG-UHFFFAOYSA-N (4e)-5-(4-methylthiadiazol-5-yl)-4-(phenylhydrazinylidene)pyrazol-3-amine Chemical compound N1=NSC(C=2C(C(N)=NN=2)=NNC=2C=CC=CC=2)=C1C AVOVQBASOARMBG-UHFFFAOYSA-N 0.000 claims 2
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• ZCEIXBFAYDUGHP-UHFFFAOYSA-N 4-[(2,3,4,5,6-pentafluorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=C(F)C(F)=C(F)C(F)=C1F ZCEIXBFAYDUGHP-UHFFFAOYSA-N 0.000 claims 2
• LEVNSQBSJWGBPB-UHFFFAOYSA-N 4-[(2,3,4-trifluorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(F)C(F)=C1F LEVNSQBSJWGBPB-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• UHKWZJPIWZBMBQ-UHFFFAOYSA-N 4-[(2,6-difluorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=C(F)C=CC=C1F UHKWZJPIWZBMBQ-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• ZUAKKGRBCCBNST-UHFFFAOYSA-N 4-[(2-bromophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC=C1Br ZUAKKGRBCCBNST-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• RLJNJAWAAPGXLH-UHFFFAOYSA-N 4-[(2-propan-2-ylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CC(C)C1=CC=CC=C1NN=C1C(N)=NN=C1N RLJNJAWAAPGXLH-UHFFFAOYSA-N 0.000 claims 2
• CIVHPCTUPSAMHN-UHFFFAOYSA-N 4-[(2z)-2-(3-amino-5-pyrrolidin-1-ylpyrazol-4-ylidene)hydrazinyl]benzenesulfonamide Chemical compound C=1C=C(S(N)(=O)=O)C=CC=1NN=C1C(N)=NN=C1N1CCCC1 CIVHPCTUPSAMHN-UHFFFAOYSA-N 0.000 claims 2
• OVKFPWXRSHFTPD-UHFFFAOYSA-N 4-[(2z)-2-[3-amino-5-(4-methylpiperazin-1-yl)pyrazol-4-ylidene]hydrazinyl]benzenesulfonamide Chemical compound C1CN(C)CCN1C1=NN=C(N)C1=NNC1=CC=C(S(N)(=O)=O)C=C1 OVKFPWXRSHFTPD-UHFFFAOYSA-N 0.000 claims 2
• LFHCKFDGKBZVTA-UHFFFAOYSA-N 4-[(3,4-dichlorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(Cl)C(Cl)=C1 LFHCKFDGKBZVTA-UHFFFAOYSA-N 0.000 claims 2
• WZRHAXSZFLFKOJ-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)hydrazinylidene]-5-(morpholin-4-ylmethyl)pyrazol-3-amine Chemical compound C=1C=C(F)C(F)=CC=1NN=C1C(N)=NN=C1CN1CCOCC1 WZRHAXSZFLFKOJ-UHFFFAOYSA-N 0.000 claims 2
• NONAXIPALYRROA-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)hydrazinylidene]-5-methylpyrazol-3-amine Chemical compound CC1=NN=C(N)C1=NNC1=CC=C(F)C(F)=C1 NONAXIPALYRROA-UHFFFAOYSA-N 0.000 claims 2
• LLVAMVRACVTTTO-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)hydrazinylidene]pyrazol-3-amine Chemical compound NC1=NN=CC1=NNC1=CC=C(F)C(F)=C1 LLVAMVRACVTTTO-UHFFFAOYSA-N 0.000 claims 2
• PWEAHERYYKPSFD-UHFFFAOYSA-N 4-[(3,4-difluorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(F)C(F)=C1 PWEAHERYYKPSFD-UHFFFAOYSA-N 0.000 claims 2
• KLEFDCUJYZYHSA-UHFFFAOYSA-N 4-[(3,4-dimethoxyphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=C(OC)C(OC)=CC=C1NN=C1C(N)=NN=C1N KLEFDCUJYZYHSA-UHFFFAOYSA-N 0.000 claims 2
• GLBXAOTUZCTMKS-UHFFFAOYSA-N 4-[(3,5-dichlorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC(Cl)=CC(Cl)=C1 GLBXAOTUZCTMKS-UHFFFAOYSA-N 0.000 claims 2
• SJGTVWJCHMOQAW-UHFFFAOYSA-N 4-[(3,5-difluorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC(F)=CC(F)=C1 SJGTVWJCHMOQAW-UHFFFAOYSA-N 0.000 claims 2
• BITQYWJQUDAZDZ-UHFFFAOYSA-N 4-[(3-bromophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(Br)=C1 BITQYWJQUDAZDZ-UHFFFAOYSA-N 0.000 claims 2
• NRJOBBUFSUBINP-UHFFFAOYSA-N 4-[(3-chloro-4-methoxyphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=C(Cl)C(OC)=CC=C1NN=C1C(N)=NN=C1N NRJOBBUFSUBINP-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• XESXQAOHYMNIFG-UHFFFAOYSA-N 4-[(3-ethylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CCC1=CC=CC(NN=C2C(=NN=C2N)N)=C1 XESXQAOHYMNIFG-UHFFFAOYSA-N 0.000 claims 2
• ZUHNSFRXVSRTDR-UHFFFAOYSA-N 4-[(3-fluoro-4-methoxyphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=C(F)C(OC)=CC=C1NN=C1C(N)=NN=C1N ZUHNSFRXVSRTDR-UHFFFAOYSA-N 0.000 claims 2
• VHPBXKINPYICLL-UHFFFAOYSA-N 4-[(3-fluorophenyl)hydrazinylidene]-5-(3-morpholin-4-ylpropyl)pyrazol-3-amine Chemical compound C=1C=CC(F)=CC=1NN=C1C(N)=NN=C1CCCN1CCOCC1 VHPBXKINPYICLL-UHFFFAOYSA-N 0.000 claims 2
• OSOIRDCVQFNKBI-UHFFFAOYSA-N 4-[(3-iodophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(I)=C1 OSOIRDCVQFNKBI-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• DYCXXNQEOSLRPA-UHFFFAOYSA-N 4-[(3-methylsulfanylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound CSC1=CC=CC(NN=C2C(=NN=C2N)N)=C1 DYCXXNQEOSLRPA-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• JDBCFQBKQVPUGW-UHFFFAOYSA-N 4-[(3-phenoxyphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(OC=2C=CC=CC=2)=C1 JDBCFQBKQVPUGW-UHFFFAOYSA-N 0.000 claims 2
• LHMIWKGTHVHONG-UHFFFAOYSA-N 4-[(3-phenylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC(C=2C=CC=CC=2)=C1 LHMIWKGTHVHONG-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• HNFHHGGCNGLDDX-UHFFFAOYSA-N 4-[(4-bromonaphthalen-1-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(Br)C2=CC=CC=C12 HNFHHGGCNGLDDX-UHFFFAOYSA-N 0.000 claims 2
• HEXGYJPHYGRRER-UHFFFAOYSA-N 4-[(4-fluorophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(F)C=C1 HEXGYJPHYGRRER-UHFFFAOYSA-N 0.000 claims 2
• AGBHWUBSXNFLGS-UHFFFAOYSA-N 4-[(4-iodophenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(I)C=C1 AGBHWUBSXNFLGS-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• XMZFUSOZTUPHRA-UHFFFAOYSA-N 4-[(4-methoxyphenyl)hydrazinylidene]-5-methylpyrazol-3-amine Chemical compound C1=CC(OC)=CC=C1NN=C1C(N)=NN=C1C XMZFUSOZTUPHRA-UHFFFAOYSA-N 0.000 claims 2
• ACTGZYZTMAGKBM-UHFFFAOYSA-N 4-[(4-methyl-3-morpholin-4-ylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=C(N2CCOCC2)C(C)=CC=C1NN=C1C(N)=NN=C1N ACTGZYZTMAGKBM-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• VFJGWZNENMTFCI-UHFFFAOYSA-N 4-[(4-methylsulfanylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C1=CC(SC)=CC=C1NN=C1C(N)=NN=C1N VFJGWZNENMTFCI-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• UUGZLZHDMUQIEJ-UHFFFAOYSA-N 4-[(4-morpholin-4-ylsulfonylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(S(=O)(=O)N2CCOCC2)C=C1 UUGZLZHDMUQIEJ-UHFFFAOYSA-N 0.000 claims 2
• NZKMCRKXUOELFN-UHFFFAOYSA-N 4-[(4-phenoxyphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC(C=C1)=CC=C1OC1=CC=CC=C1 NZKMCRKXUOELFN-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• BKMLNKMFMALHGR-UHFFFAOYSA-N 4-[(4-pyrrolidin-1-ylsulfonylphenyl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=C(S(=O)(=O)N2CCCC2)C=C1 BKMLNKMFMALHGR-UHFFFAOYSA-N 0.000 claims 2
• AVZANNIQDODVPK-UHFFFAOYSA-N 4-[(4z)-5-amino-4-[(3-fluorophenyl)hydrazinylidene]pyrazol-3-yl]benzoic acid Chemical compound NC1=NN=C(C=2C=CC(=CC=2)C(O)=O)C1=NNC1=CC=CC(F)=C1 AVZANNIQDODVPK-UHFFFAOYSA-N 0.000 claims 2
• LCDNRLOMCIALHQ-UHFFFAOYSA-N 4-[(5-methoxy-1,3-benzothiazol-2-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound N=1C2=CC(OC)=CC=C2SC=1NN=C1C(N)=NN=C1N LCDNRLOMCIALHQ-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• VAAUYDWUHKXQLY-UHFFFAOYSA-N 4-[(9-ethylcarbazol-3-yl)hydrazinylidene]pyrazole-3,5-diamine Chemical compound C=1C=C2N(CC)C3=CC=CC=C3C2=CC=1NN=C1C(N)=NN=C1N VAAUYDWUHKXQLY-UHFFFAOYSA-N 0.000 claims 2
• ADMCEWNYPAOKFP-UHFFFAOYSA-N 4-[2-(3,5-diaminopyrazol-4-ylidene)hydrazinyl]-n-(2,6-dimethylpyrimidin-4-yl)benzenesulfonamide Chemical compound CC1=NC(C)=CC(NS(=O)(=O)C=2C=CC(NN=C3C(=NN=C3N)N)=CC=2)=N1 ADMCEWNYPAOKFP-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• VEUAEELGXHDJTG-UHFFFAOYSA-N 4-[[2-(benzenesulfonyl)phenyl]hydrazinylidene]pyrazole-3,5-diamine Chemical compound NC1=NN=C(N)C1=NNC1=CC=CC=C1S(=O)(=O)C1=CC=CC=C1 VEUAEELGXHDJTG-UHFFFAOYSA-N 0.000 claims 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
• 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 2
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