KR20170122799A - TGF-β 억제제 - Google Patents

Info

Publication number

KR20170122799A

KR20170122799A KR1020177027381A KR20177027381A KR20170122799A KR 20170122799 A KR20170122799 A KR 20170122799A KR 1020177027381 A KR1020177027381 A KR 1020177027381A KR 20177027381 A KR20177027381 A KR 20177027381A KR 20170122799 A KR20170122799 A KR 20170122799A

Authority

KR

South Korea

Prior art keywords

alkyl

imidazol

imidazo

haloalkyl

pyridine

Prior art date

2015-03-02

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

Links

• Espacenet
• Global Dossier
• Discuss

• 102000004887 Transforming Growth Factor beta Human genes 0.000 title claims abstract description 18
• 108090001012 Transforming Growth Factor beta Proteins 0.000 title claims abstract description 18
• ZRKFYGHZFMAOKI-QMGMOQQFSA-N tgfbeta Chemical compound C([C@H](NC(=O)[C@H](C(C)C)NC(=O)CNC(=O)[C@H](CCC(O)=O)NC(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CC(C)C)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@H]([C@@H](C)O)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](C)NC(=O)[C@H](CO)NC(=O)[C@H](CCC(N)=O)NC(=O)[C@@H](NC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)[C@@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CCSC)C(C)C)[C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](C)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H]([C@@H](C)O)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](C)C(=O)N[C@@H](CC(C)C)C(=O)N1[C@@H](CCC1)C(=O)N1[C@@H](CCC1)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CO)C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(C)C)C(O)=O)C1=CC=C(O)C=C1 ZRKFYGHZFMAOKI-QMGMOQQFSA-N 0.000 title claims abstract description 17
• 239000003112 inhibitor Substances 0.000 title claims description 31
• 150000001875 compounds Chemical class 0.000 claims abstract description 371
• 238000000034 method Methods 0.000 claims abstract description 117
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 69
• 150000003839 salts Chemical class 0.000 claims abstract description 50
• 201000010099 disease Diseases 0.000 claims abstract description 49
• 229940002612 prodrug Drugs 0.000 claims abstract description 43
• 239000000651 prodrug Substances 0.000 claims abstract description 43
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 33
• 239000012453 solvate Substances 0.000 claims abstract description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 310
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 227
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 192
• 125000000217 alkyl group Chemical group 0.000 claims description 188
• 229910052739 hydrogen Inorganic materials 0.000 claims description 181
• 239000001257 hydrogen Substances 0.000 claims description 180
• 229910052736 halogen Inorganic materials 0.000 claims description 161
• 150000002367 halogens Chemical class 0.000 claims description 160
• 206010057190 Respiratory tract infections Diseases 0.000 claims description 122
• 150000002431 hydrogen Chemical class 0.000 claims description 120
• 239000000243 solution Substances 0.000 claims description 104
• 125000001188 haloalkyl group Chemical group 0.000 claims description 96
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 84
• 239000000203 mixture Substances 0.000 claims description 76
• 125000000336 imidazol-5-yl group Chemical group [H]N1C([H])=NC([H])=C1[*] 0.000 claims description 74
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 60
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 59
• PJESVVYWPFAJCS-UHFFFAOYSA-N pyridazine-3-carbonitrile Chemical compound N#CC1=CC=CN=N1 PJESVVYWPFAJCS-UHFFFAOYSA-N 0.000 claims description 48
• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 44
• 229910052757 nitrogen Inorganic materials 0.000 claims description 43
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 42
• 206010028980 Neoplasm Diseases 0.000 claims description 39
• 125000002619 bicyclic group Chemical group 0.000 claims description 34
• 102100039939 Growth/differentiation factor 8 Human genes 0.000 claims description 33
• 229910052717 sulfur Inorganic materials 0.000 claims description 33
• 229910052760 oxygen Inorganic materials 0.000 claims description 31
• 125000003545 alkoxy group Chemical group 0.000 claims description 30
• 108010056852 Myostatin Proteins 0.000 claims description 28
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 27
• 201000011510 cancer Diseases 0.000 claims description 27
• 125000004429 atom Chemical group 0.000 claims description 25
• 238000011282 treatment Methods 0.000 claims description 25
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 24
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
• 239000003795 chemical substances by application Substances 0.000 claims description 19
• 239000002246 antineoplastic agent Substances 0.000 claims description 18
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 17
• 230000015572 biosynthetic process Effects 0.000 claims description 16
• 238000003786 synthesis reaction Methods 0.000 claims description 15
• 150000001408 amides Chemical class 0.000 claims description 14
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 13
• 125000003342 alkenyl group Chemical group 0.000 claims description 12
• 102000004190 Enzymes Human genes 0.000 claims description 11
• 108090000790 Enzymes Proteins 0.000 claims description 11
• 229940127089 cytotoxic agent Drugs 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 230000000694 effects Effects 0.000 claims description 11
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 238000002360 preparation method Methods 0.000 claims description 11
• 101100519207 Mus musculus Pdcd1 gene Proteins 0.000 claims description 10
• 229940088598 enzyme Drugs 0.000 claims description 10
• ULZZPSONFYHMKY-UHFFFAOYSA-N 6-[5-(4-fluoro-3-methylphenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=CN(C=1C1=CC=C2C=NNC2=C1)C)C ULZZPSONFYHMKY-UHFFFAOYSA-N 0.000 claims description 9
• 239000012664 BCL-2-inhibitor Substances 0.000 claims description 8
• 229940123711 Bcl2 inhibitor Drugs 0.000 claims description 8
• 239000004037 angiogenesis inhibitor Substances 0.000 claims description 8
• 208000011580 syndromic disease Diseases 0.000 claims description 8
• CJNVIIQOYLDXLF-UHFFFAOYSA-N 5-[4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1)C CJNVIIQOYLDXLF-UHFFFAOYSA-N 0.000 claims description 6
• 102100039498 Cytotoxic T-lymphocyte protein 4 Human genes 0.000 claims description 6
• NKANXQFJJICGDU-QPLCGJKRSA-N Tamoxifen Chemical compound C=1C=CC=CC=1C(/CC)=C(C=1C=CC(OCCN(C)C)=CC=1)/C1=CC=CC=C1 NKANXQFJJICGDU-QPLCGJKRSA-N 0.000 claims description 6
• 230000002496 gastric effect Effects 0.000 claims description 6
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical group O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 6
• 208000017169 kidney disease Diseases 0.000 claims description 6
• 230000037361 pathway Effects 0.000 claims description 6
• 229960004641 rituximab Drugs 0.000 claims description 6
• 239000000126 substance Substances 0.000 claims description 6
• 125000001425 triazolyl group Chemical group 0.000 claims description 6
• NTQODZHOLXYINM-UHFFFAOYSA-N 5-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 NTQODZHOLXYINM-UHFFFAOYSA-N 0.000 claims description 5
• AEMRATBUIXJFLD-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1-methylbenzimidazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C=1C=CC2=C(N(C=N2)C)C=1 AEMRATBUIXJFLD-UHFFFAOYSA-N 0.000 claims description 5
• BFIPITLAVPWQPQ-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C1=CC=C2C=NNC2=C1 BFIPITLAVPWQPQ-UHFFFAOYSA-N 0.000 claims description 5
• ICBOPMCVTUHGHV-UHFFFAOYSA-N 6-[4-(4-fluoro-3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC1=C(C=C(C=C1)C=1N=CNC=1C1=CC=C2C=NNC2=C1)C ICBOPMCVTUHGHV-UHFFFAOYSA-N 0.000 claims description 5
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
• 208000001132 Osteoporosis Diseases 0.000 claims description 5
• 208000032839 leukemia Diseases 0.000 claims description 5
• 230000001404 mediated effect Effects 0.000 claims description 5
• SGDBTWWWUNNDEQ-LBPRGKRZSA-N melphalan Chemical compound OC(=O)[C@@H](N)CC1=CC=C(N(CCCl)CCCl)C=C1 SGDBTWWWUNNDEQ-LBPRGKRZSA-N 0.000 claims description 5
• 229960001924 melphalan Drugs 0.000 claims description 5
• PNDPGZBMCMUPRI-HVTJNCQCSA-N 10043-66-0 Chemical compound [131I][131I] PNDPGZBMCMUPRI-HVTJNCQCSA-N 0.000 claims description 4
• RPDOYLXGZVEPIP-UHFFFAOYSA-N 5-[3-methyl-5-(3-methylphenyl)imidazol-4-yl]-1H-indazole Chemical compound CN1C=NC(=C1C=1C=C2C=NNC2=CC=1)C=1C=C(C=CC=1)C RPDOYLXGZVEPIP-UHFFFAOYSA-N 0.000 claims description 4
• NTTUJGGLUCSPCH-UHFFFAOYSA-N 5-[4-(3,4-difluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1F)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 NTTUJGGLUCSPCH-UHFFFAOYSA-N 0.000 claims description 4
• DLEZDTFBZFAKFN-UHFFFAOYSA-N 5-[4-(3-fluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 DLEZDTFBZFAKFN-UHFFFAOYSA-N 0.000 claims description 4
• HVLQWAFKHOUABL-UHFFFAOYSA-N 5-[4-(3-methylphenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound C1(=CC(=CC=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1)C HVLQWAFKHOUABL-UHFFFAOYSA-N 0.000 claims description 4
• SZNIJWCNFIVOBU-UHFFFAOYSA-N 5-[5-(3-chlorophenyl)-3-methylimidazol-4-yl]-1H-indazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CN(C=1C=1C=C2C=NNC2=CC=1)C SZNIJWCNFIVOBU-UHFFFAOYSA-N 0.000 claims description 4
• RIHHVSWLZUEDHV-UHFFFAOYSA-N 5-[5-(4-fluorophenyl)-1H-imidazol-4-yl]-1H-indazole Chemical compound FC1=CC=C(C=C1)C=1N=CNC=1C=1C=C2C=NNC2=CC=1 RIHHVSWLZUEDHV-UHFFFAOYSA-N 0.000 claims description 4
• GPKMHNBZFLYQJK-UHFFFAOYSA-N 6-[3-methyl-5-(3-methylphenyl)imidazol-4-yl]-1H-indazole Chemical compound CN1C=NC(=C1C1=CC=C2C=NNC2=C1)C=1C=C(C=CC=1)C GPKMHNBZFLYQJK-UHFFFAOYSA-N 0.000 claims description 4
• LJBLSXZRCXOCHC-UHFFFAOYSA-N 6-[4-(3-chlorophenyl)-1H-imidazol-5-yl]-1,3-benzothiazole Chemical compound ClC=1C=C(C=CC=1)C=1N=CNC=1C1=CC2=C(N=CS2)C=C1 LJBLSXZRCXOCHC-UHFFFAOYSA-N 0.000 claims description 4
• SCIUZYVNHFPRJI-UHFFFAOYSA-N 6-[4-(3-fluorophenyl)-1H-imidazol-5-yl]-1H-indazole Chemical compound FC=1C=C(C=CC=1)C=1N=CNC=1C1=CC=C2C=NNC2=C1 SCIUZYVNHFPRJI-UHFFFAOYSA-N 0.000 claims description 4
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• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
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• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
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• PHKIAIZZFBUIRE-UHFFFAOYSA-N 1-methyl-6-[4-(3-methylphenyl)-1H-imidazol-5-yl]benzimidazole Chemical compound CN1C=NC2=C1C=C(C=C2)C1=C(N=CN1)C=1C=C(C=CC=1)C PHKIAIZZFBUIRE-UHFFFAOYSA-N 0.000 claims description 3
• KKVYYGGCHJGEFJ-UHFFFAOYSA-N 1-n-(4-chlorophenyl)-6-methyl-5-n-[3-(7h-purin-6-yl)pyridin-2-yl]isoquinoline-1,5-diamine Chemical compound N=1C=CC2=C(NC=3C(=CC=CN=3)C=3C=4N=CNC=4N=CN=3)C(C)=CC=C2C=1NC1=CC=C(Cl)C=C1 KKVYYGGCHJGEFJ-UHFFFAOYSA-N 0.000 claims description 3
• UEJJHQNACJXSKW-UHFFFAOYSA-N 2-(2,6-dioxopiperidin-3-yl)-1H-isoindole-1,3(2H)-dione Chemical compound O=C1C2=CC=CC=C2C(=O)N1C1CCC(=O)NC1=O UEJJHQNACJXSKW-UHFFFAOYSA-N 0.000 claims description 3
• 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 3
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