ES2385378T3 - Derivados de pirazolilbenzotiazol y su uso como agentes terapéuticos - Google Patents

Info

Publication number

ES2385378T3

ES2385378T3 ES03771002T ES03771002T ES2385378T3 ES 2385378 T3 ES2385378 T3 ES 2385378T3 ES 03771002 T ES03771002 T ES 03771002T ES 03771002 T ES03771002 T ES 03771002T ES 2385378 T3 ES2385378 T3 ES 2385378T3

Authority

ES

Spain

Prior art keywords

pyrazol

benzothiazol

methyl

amino

ylamine

Prior art date

2002-07-24

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

Expired - Lifetime

Links

• Espacenet
• Global Dossier
• Discuss

• YAMYGQRUEXYQIE-UHFFFAOYSA-N 2-(1h-pyrazol-5-yl)-1,3-benzothiazole Chemical class N1N=CC=C1C1=NC2=CC=CC=C2S1 YAMYGQRUEXYQIE-UHFFFAOYSA-N 0.000 title abstract description 15
• 239000003814 drug Substances 0.000 title description 9
• 229940124597 therapeutic agent Drugs 0.000 title description 5
• 150000001875 compounds Chemical class 0.000 claims description 458
• -1 amino, aminosulfinyl Chemical group 0.000 claims description 169
• 239000000203 mixture Substances 0.000 claims description 151
• 210000004027 cell Anatomy 0.000 claims description 127
• 125000001183 hydrocarbyl group Chemical group 0.000 claims description 57
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 54
• 239000001257 hydrogen Substances 0.000 claims description 32
• 229910052739 hydrogen Inorganic materials 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• 206010028980 Neoplasm Diseases 0.000 claims description 30
• 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 30
• 125000004404 heteroalkyl group Chemical group 0.000 claims description 28
• IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 27
• 206010029113 Neovascularisation Diseases 0.000 claims description 26
• 125000001072 heteroaryl group Chemical group 0.000 claims description 25
• 208000035475 disorder Diseases 0.000 claims description 24
• 239000002253 acid Substances 0.000 claims description 22
• 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 22
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 19
• 201000004681 Psoriasis Diseases 0.000 claims description 18
• 229910052736 halogen Inorganic materials 0.000 claims description 18
• 150000002367 halogens Chemical class 0.000 claims description 18
• 229910019142 PO4 Inorganic materials 0.000 claims description 17
• 125000004432 carbon atom Chemical group C* 0.000 claims description 17
• NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 claims description 17
• 239000010452 phosphate Substances 0.000 claims description 17
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 16
• QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 15
• 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 15
• 125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 15
• 125000005842 heteroatom Chemical group 0.000 claims description 15
• ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical compound [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 15
• UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 claims description 15
• XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 claims description 15
• LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 15
• BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 claims description 15
• 150000003573 thiols Chemical class 0.000 claims description 15
• 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 14
• 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 claims description 14
• 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 14
• 150000003462 sulfoxides Chemical class 0.000 claims description 14
• RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims description 14
• 230000033115 angiogenesis Effects 0.000 claims description 13
• 230000003463 hyperproliferative effect Effects 0.000 claims description 13
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 13
• BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 claims description 12
• 125000000623 heterocyclic group Chemical group 0.000 claims description 11
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 11
• 239000012453 solvate Substances 0.000 claims description 10
• 229910052717 sulfur Chemical group 0.000 claims description 10
• NIINYWZQSXMXEO-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazole-6-sulfonamide Chemical compound N1N=C(N)C(C=2SC3=CC(=CC=C3N=2)S(N)(=O)=O)=C1C NIINYWZQSXMXEO-UHFFFAOYSA-N 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• 125000003282 alkyl amino group Chemical group 0.000 claims description 9
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 9
• 239000003795 chemical substances by application Substances 0.000 claims description 9
• 229910052760 oxygen Inorganic materials 0.000 claims description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims description 9
• 239000011593 sulfur Chemical group 0.000 claims description 9
• 210000004881 tumor cell Anatomy 0.000 claims description 9
• CSQQPNHSMIACDK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound CC1=NNC(N)=C1C1=NC2=CC=CC=C2S1 CSQQPNHSMIACDK-UHFFFAOYSA-N 0.000 claims description 8
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
• 201000011510 cancer Diseases 0.000 claims description 8
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
• 210000000554 iris Anatomy 0.000 claims description 8
• GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 claims description 8
• 239000001301 oxygen Chemical group 0.000 claims description 8
• FJMJCOZSZTXBLP-UHFFFAOYSA-N 4-(6-fluoro-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2SC3=CC(F)=CC=C3N=2)=C1C FJMJCOZSZTXBLP-UHFFFAOYSA-N 0.000 claims description 7
• 125000003368 amide group Chemical group 0.000 claims description 7
• 230000001363 autoimmune Effects 0.000 claims description 7
• 210000004087 cornea Anatomy 0.000 claims description 7
• 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 7
• 208000027866 inflammatory disease Diseases 0.000 claims description 7
• 150000002540 isothiocyanates Chemical class 0.000 claims description 7
• 125000000018 nitroso group Chemical group N(=O)* 0.000 claims description 7
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 7
• UQCGAISLUXLXMC-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-pyrrolidin-1-yl-1h-pyrazol-5-amine Chemical compound N=1C2=CC=CC=C2SC=1C=1C(N)=NNC=1N1CCCC1 UQCGAISLUXLXMC-UHFFFAOYSA-N 0.000 claims description 6
• ALALFTRMHTVSLL-UHFFFAOYSA-N 4-(4-fluoro-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound CC1=NNC(N)=C1C1=NC2=C(F)C=CC=C2S1 ALALFTRMHTVSLL-UHFFFAOYSA-N 0.000 claims description 6
• ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 6
• IIKBSVJXNRIRLB-UHFFFAOYSA-N [2-(3-amino-5-methyl-1h-pyrazol-4-yl)-5-fluoro-1,3-benzothiazol-6-yl]methanol Chemical compound N1N=C(N)C(C=2SC3=CC(CO)=C(F)C=C3N=2)=C1C IIKBSVJXNRIRLB-UHFFFAOYSA-N 0.000 claims description 6
• ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 6
• MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 claims description 6
• 201000000596 systemic lupus erythematosus Diseases 0.000 claims description 6
• RVGKCCVUQDDNPV-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazole-6-carboxylic acid Chemical compound N1N=C(N)C(C=2SC3=CC(=CC=C3N=2)C(O)=O)=C1C RVGKCCVUQDDNPV-UHFFFAOYSA-N 0.000 claims description 5
• FUDLGGGXXSVQGI-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-4-fluoro-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=C(F)C=C(S(N)(=O)=O)C=C2S1 FUDLGGGXXSVQGI-UHFFFAOYSA-N 0.000 claims description 5
• QAILLNFYMHQEKZ-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-5-fluoro-n-(2-hydroxyethyl)-1,3-benzothiazole-4-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=C(S(=O)(=O)NCCO)C(F)=CC=C2S1 QAILLNFYMHQEKZ-UHFFFAOYSA-N 0.000 claims description 5
• ZTXBWQWZMYZJIU-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-n-(2-morpholin-4-ylethyl)-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(S(=O)(=O)NCCN3CCOCC3)C=C2S1 ZTXBWQWZMYZJIU-UHFFFAOYSA-N 0.000 claims description 5
• GTWUALXHYHDTPW-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-n-[(4-aminophenyl)methyl]-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(S(=O)(=O)NCC=3C=CC(N)=CC=3)C=C2S1 GTWUALXHYHDTPW-UHFFFAOYSA-N 0.000 claims description 5
• XFXQMZJSCLGLIJ-UHFFFAOYSA-N 2-[[2-(3-amino-5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazol-6-yl]methylamino]ethanol Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(CNCCO)C=C2S1 XFXQMZJSCLGLIJ-UHFFFAOYSA-N 0.000 claims description 5
• BJXYFCFNVPUUND-UHFFFAOYSA-N 3-[[5-amino-4-(1,3-benzothiazol-2-yl)-1h-pyrazol-3-yl]amino]propan-1-ol Chemical compound N1N=C(NCCCO)C(C=2SC3=CC=CC=C3N=2)=C1N BJXYFCFNVPUUND-UHFFFAOYSA-N 0.000 claims description 5
• DQNQLZBDDJZWCD-UHFFFAOYSA-N 3-n-(2-aminoethyl)-4-(1,3-benzothiazol-2-yl)-1h-pyrazole-3,5-diamine Chemical compound NCCNC1=NNC(N)=C1C1=NC2=CC=CC=C2S1 DQNQLZBDDJZWCD-UHFFFAOYSA-N 0.000 claims description 5
• IXSYRRSIOMPVHT-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-5-ethyl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2SC3=CC=CC=C3N=2)=C1CC IXSYRRSIOMPVHT-UHFFFAOYSA-N 0.000 claims description 5
• TYGJLYAMPYVJEC-UHFFFAOYSA-N 4-(5-fluoro-6-methoxy-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound N=1C=2C=C(F)C(OC)=CC=2SC=1C1=C(C)NN=C1N TYGJLYAMPYVJEC-UHFFFAOYSA-N 0.000 claims description 5
• SVURQPBGWDIMSF-UHFFFAOYSA-N 4-(5-fluoro-6-methyl-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound CC1=NNC(N)=C1C1=NC2=CC(F)=C(C)C=C2S1 SVURQPBGWDIMSF-UHFFFAOYSA-N 0.000 claims description 5
• PNNINDSPAQWMTR-UHFFFAOYSA-N 4-(5-methoxy-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound N=1C2=CC(OC)=CC=C2SC=1C=1C(C)=NNC=1N PNNINDSPAQWMTR-UHFFFAOYSA-N 0.000 claims description 5
• WRIQXYKFINZWKB-UHFFFAOYSA-N 4-(6-chloro-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(Cl)C=C2S1 WRIQXYKFINZWKB-UHFFFAOYSA-N 0.000 claims description 5
• VRTQVPLLTFUHCM-UHFFFAOYSA-N 4-(6-methoxy-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=C(C)NN=C1N VRTQVPLLTFUHCM-UHFFFAOYSA-N 0.000 claims description 5
• LPXKPTBYKQEWNS-UHFFFAOYSA-N 4-(7-chloro-4-methoxy-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound N=1C=2C(OC)=CC=C(Cl)C=2SC=1C=1C(C)=NNC=1N LPXKPTBYKQEWNS-UHFFFAOYSA-N 0.000 claims description 5
• IUINLGIEEUGQST-UHFFFAOYSA-N 4-[6-[(dimethylamino)methyl]-1,3-benzothiazol-2-yl]-5-methyl-1h-pyrazol-3-amine Chemical compound S1C2=CC(CN(C)C)=CC=C2N=C1C=1C(C)=NNC=1N IUINLGIEEUGQST-UHFFFAOYSA-N 0.000 claims description 5
• MOTWNZWIXFFOBR-UHFFFAOYSA-N 5-methyl-4-[5-(trifluoromethyl)-1,3-benzothiazol-2-yl]-1h-pyrazol-3-amine Chemical compound CC1=NNC(N)=C1C1=NC2=CC(C(F)(F)F)=CC=C2S1 MOTWNZWIXFFOBR-UHFFFAOYSA-N 0.000 claims description 5
• 206010012689 Diabetic retinopathy Diseases 0.000 claims description 5
• BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Chemical compound NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 claims description 5
• 230000004709 cell invasion Effects 0.000 claims description 5
• BWAHGXAUIRPIHE-UHFFFAOYSA-N ethyl 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazole-5-carboxylate Chemical compound N=1C2=CC(C(=O)OCC)=CC=C2SC=1C=1C(C)=NNC=1N BWAHGXAUIRPIHE-UHFFFAOYSA-N 0.000 claims description 5
• IKOJEQSDJHXFQW-UHFFFAOYSA-N methyl 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazole-7-carboxylate Chemical compound S1C=2C(C(=O)OC)=CC=CC=2N=C1C1=C(C)NN=C1N IKOJEQSDJHXFQW-UHFFFAOYSA-N 0.000 claims description 5
• LDAKZUPMVFBRML-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-1,3-benzothiazole-6-carboxamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(C(N)=O)C=C2S1 LDAKZUPMVFBRML-UHFFFAOYSA-N 0.000 claims description 4
• FPJDFJGMHIJACK-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-5-fluoro-n-(2-hydroxyethyl)-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC(F)=C(S(=O)(=O)NCCO)C=C2S1 FPJDFJGMHIJACK-UHFFFAOYSA-N 0.000 claims description 4
• XWHGEQWOGJBXQD-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-n-(2-hydroxyethyl)-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(S(=O)(=O)NCCO)C=C2S1 XWHGEQWOGJBXQD-UHFFFAOYSA-N 0.000 claims description 4
• UDIKPWYBVUCCQW-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-n-(cyclopropylmethyl)-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(S(=O)(=O)NCC3CC3)C=C2S1 UDIKPWYBVUCCQW-UHFFFAOYSA-N 0.000 claims description 4
• BPOYLASJFDENBE-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-n-(pyridin-4-ylmethyl)-1,3-benzothiazole-6-sulfonamide Chemical compound CC1=NNC(N)=C1C1=NC2=CC=C(S(=O)(=O)NCC=3C=CN=CC=3)C=C2S1 BPOYLASJFDENBE-UHFFFAOYSA-N 0.000 claims description 4
• KIQPZXXFPRZTBR-UHFFFAOYSA-N 2-(3-amino-5-methyl-1h-pyrazol-4-yl)-n-[(4-methoxyphenyl)methyl]-1,3-benzothiazole-6-sulfonamide Chemical compound C1=CC(OC)=CC=C1CNS(=O)(=O)C1=CC=C(N=C(S2)C3=C(NN=C3C)N)C2=C1 KIQPZXXFPRZTBR-UHFFFAOYSA-N 0.000 claims description 4
• DJDXSJPMGTWXON-UHFFFAOYSA-N 2-[[5-amino-4-(1,3-benzothiazol-2-yl)-1h-pyrazol-3-yl]amino]cyclopentan-1-ol Chemical compound N=1C2=CC=CC=C2SC=1C=1C(N)=NNC=1NC1CCCC1O DJDXSJPMGTWXON-UHFFFAOYSA-N 0.000 claims description 4
• IZFBHPLFFRVTAH-UHFFFAOYSA-N 3-n-[2-(1h-imidazol-5-yl)ethyl]-4-(6-methoxy-1,3-benzothiazol-2-yl)-1h-pyrazole-3,5-diamine Chemical compound S1C2=CC(OC)=CC=C2N=C1C1=C(N)NN=C1NCCC1=CN=CN1 IZFBHPLFFRVTAH-UHFFFAOYSA-N 0.000 claims description 4
• IXSBGYGZTFGXPW-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-n-(2-pyrrolidin-1-ylethyl)-1h-pyrazole-3,5-diamine Chemical compound N=1C2=CC=CC=C2SC=1C1=C(N)NN=C1NCCN1CCCC1 IXSBGYGZTFGXPW-UHFFFAOYSA-N 0.000 claims description 4
• ZRHKDIZYIZJVCT-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-n-[2-(1h-indol-3-yl)ethyl]-1h-pyrazole-3,5-diamine Chemical compound C1=CC=C2SC(C=3C(NCCC=4C5=CC=CC=C5NC=4)=NNC=3N)=NC2=C1 ZRHKDIZYIZJVCT-UHFFFAOYSA-N 0.000 claims description 4
• JDXRQOFYLUYCEK-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-n-[3-(dimethylamino)propyl]-1h-pyrazole-3,5-diamine Chemical compound CN(C)CCCNC1=NNC(N)=C1C1=NC2=CC=CC=C2S1 JDXRQOFYLUYCEK-UHFFFAOYSA-N 0.000 claims description 4
• JAHVGBFYMGAVII-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-n-ethyl-1h-pyrazole-3,5-diamine Chemical compound N1N=C(N)C(C=2SC3=CC=CC=C3N=2)=C1NCC JAHVGBFYMGAVII-UHFFFAOYSA-N 0.000 claims description 4
• MQTCPUCKVUOTPF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-n-quinolin-6-yl-1h-pyrazole-3,5-diamine Chemical compound C1=CC=C2SC(C3=C(NC=4C=C5C=CC=NC5=CC=4)NN=C3N)=NC2=C1 MQTCPUCKVUOTPF-UHFFFAOYSA-N 0.000 claims description 4
• FIJKJYNYFHYOLF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-3-piperazin-1-yl-1h-pyrazol-5-amine Chemical compound N=1C2=CC=CC=C2SC=1C1=C(N)NN=C1N1CCNCC1 FIJKJYNYFHYOLF-UHFFFAOYSA-N 0.000 claims description 4
• ZBRUXVVKRSVWTF-UHFFFAOYSA-N 4-(1,3-benzothiazol-2-yl)-5-phenyl-1h-pyrazol-3-amine Chemical compound N=1C2=CC=CC=C2SC=1C=1C(N)=NNC=1C1=CC=CC=C1 ZBRUXVVKRSVWTF-UHFFFAOYSA-N 0.000 claims description 4
• KAMNFXYPIHJODD-UHFFFAOYSA-N 4-(6-bromo-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2SC3=CC(Br)=CC=C3N=2)=C1C KAMNFXYPIHJODD-UHFFFAOYSA-N 0.000 claims description 4
• LVVKTROMUCSVFM-UHFFFAOYSA-N 4-(6-bromo-5-fluoro-1,3-benzothiazol-2-yl)-5-methyl-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2SC3=CC(Br)=C(F)C=C3N=2)=C1C LVVKTROMUCSVFM-UHFFFAOYSA-N 0.000 claims description 4
• OOBXYQWFBLKOGO-UHFFFAOYSA-N 4-[2-[[5-amino-4-(1,3-benzothiazol-2-yl)-1h-pyrazol-3-yl]amino]ethyl]phenol Chemical compound N=1C2=CC=CC=C2SC=1C1=C(N)NN=C1NCCC1=CC=C(O)C=C1 OOBXYQWFBLKOGO-UHFFFAOYSA-N 0.000 claims description 4
• SEUQVSLHPQREFI-UHFFFAOYSA-N 4-[6-[(dimethylamino)methyl]-5-fluoro-1,3-benzothiazol-2-yl]-5-methyl-1h-pyrazol-3-amine Chemical compound N=1C=2C=C(F)C(CN(C)C)=CC=2SC=1C1=C(C)NN=C1N SEUQVSLHPQREFI-UHFFFAOYSA-N 0.000 claims description 4
• KZOFJXBFWNKTMY-UHFFFAOYSA-N 5-methyl-4-(6-methylsulfonyl-1,3-benzothiazol-2-yl)-1h-pyrazol-3-amine Chemical compound N1N=C(N)C(C=2SC3=CC(=CC=C3N=2)S(C)(=O)=O)=C1C KZOFJXBFWNKTMY-UHFFFAOYSA-N 0.000 claims description 4
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