TW201639827A - ＴＧＦ－β抑制劑 - Google Patents

Info

Publication number

TW201639827A

TW201639827A TW105106227A TW105106227A TW201639827A TW 201639827 A TW201639827 A TW 201639827A TW 105106227 A TW105106227 A TW 105106227A TW 105106227 A TW105106227 A TW 105106227A TW 201639827 A TW201639827 A TW 201639827A

Authority

TW

Taiwan

Prior art keywords

imidazol

alkyl

fluorophenyl

imidazo

haloalkyl

Prior art date

2015-03-02

Links

• Espacenet
• Global Dossier
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• 239000003112 inhibitor Substances 0.000 title claims description 16
• 150000001875 compounds Chemical class 0.000 claims abstract description 378
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 57
• 201000010099 disease Diseases 0.000 claims abstract description 52
• 150000003839 salts Chemical class 0.000 claims abstract description 52
• 229940002612 prodrug Drugs 0.000 claims abstract description 41
• 239000000651 prodrug Substances 0.000 claims abstract description 41
• 239000012453 solvate Substances 0.000 claims abstract description 36
• 150000001204 N-oxides Chemical class 0.000 claims abstract description 32
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 29
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 20
• -1 C 1 -C 6 alkyl Chemical group 0.000 claims description 269
• 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 262
• 229910052736 halogen Inorganic materials 0.000 claims description 197
• 150000002367 halogens Chemical class 0.000 claims description 197
• 125000000217 alkyl group Chemical group 0.000 claims description 189
• 229910052739 hydrogen Inorganic materials 0.000 claims description 187
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 184
• 239000001257 hydrogen Substances 0.000 claims description 183
• 150000002431 hydrogen Chemical class 0.000 claims description 119
• 125000001188 haloalkyl group Chemical group 0.000 claims description 96
• 239000000203 mixture Substances 0.000 claims description 75
• 206010028980 Neoplasm Diseases 0.000 claims description 72
• OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 64
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
• IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 claims description 62
• 229910052757 nitrogen Inorganic materials 0.000 claims description 44
• 229910052717 sulfur Inorganic materials 0.000 claims description 37
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 36
• 125000002619 bicyclic group Chemical group 0.000 claims description 34
• 229910052760 oxygen Inorganic materials 0.000 claims description 30
• 238000011282 treatment Methods 0.000 claims description 29
• 125000003545 alkoxy group Chemical group 0.000 claims description 28
• 201000011510 cancer Diseases 0.000 claims description 27
• 125000004429 atom Chemical group 0.000 claims description 26
• 239000003795 chemical substances by application Substances 0.000 claims description 26
• YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 25
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 21
• 125000005843 halogen group Chemical group 0.000 claims description 20
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 19
• 239000003814 drug Substances 0.000 claims description 18
• 239000002246 antineoplastic agent Substances 0.000 claims description 17
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 17
• 238000006467 substitution reaction Methods 0.000 claims description 17
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• 150000001412 amines Chemical class 0.000 claims description 15
• 229940127089 cytotoxic agent Drugs 0.000 claims description 12
• 230000000694 effects Effects 0.000 claims description 12
• YLXWTAXPOOYRSL-UHFFFAOYSA-N imidazo[1,2-b]pyridazine-3-carbonitrile Chemical compound C1=CC=NN2C(C#N)=CN=C21 YLXWTAXPOOYRSL-UHFFFAOYSA-N 0.000 claims description 12
• 125000003342 alkenyl group Chemical group 0.000 claims description 11
• 239000003085 diluting agent Substances 0.000 claims description 11
• 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
• 102000004190 Enzymes Human genes 0.000 claims description 10
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• SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 10
• 108010063738 Interleukins Proteins 0.000 claims description 10
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• UTCSSFWDNNEEBH-UHFFFAOYSA-N imidazo[1,2-a]pyridine Chemical compound C1=CC=CC2=NC=CN21 UTCSSFWDNNEEBH-UHFFFAOYSA-N 0.000 claims description 10
• 238000004519 manufacturing process Methods 0.000 claims description 10
• 102000005962 receptors Human genes 0.000 claims description 10
• 108020003175 receptors Proteins 0.000 claims description 10
• 125000001425 triazolyl group Chemical group 0.000 claims description 10
• 102100039939 Growth/differentiation factor 8 Human genes 0.000 claims description 9
• IAKHMKGGTNLKSZ-INIZCTEOSA-N (S)-colchicine Chemical compound C1([C@@H](NC(C)=O)CC2)=CC(=O)C(OC)=CC=C1C1=C2C=C(OC)C(OC)=C1OC IAKHMKGGTNLKSZ-INIZCTEOSA-N 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• 229910052731 fluorine Inorganic materials 0.000 claims description 8
• RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 claims description 7
• CBPNZQVSJQDFBE-FUXHJELOSA-N Temsirolimus Chemical compound C1C[C@@H](OC(=O)C(C)(CO)CO)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 CBPNZQVSJQDFBE-FUXHJELOSA-N 0.000 claims description 7
• 230000037361 pathway Effects 0.000 claims description 7
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• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
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• SDUQYLNIPVEERB-QPPQHZFASA-N gemcitabine Chemical compound O=C1N=C(N)C=CN1[C@H]1C(F)(F)[C@H](O)[C@@H](CO)O1 SDUQYLNIPVEERB-QPPQHZFASA-N 0.000 claims description 6
• DREUPRFRJOSEAM-UHFFFAOYSA-N imidazo[1,2-a]pyridine-3-carbonitrile Chemical compound C1=CC=CN2C(C#N)=CN=C21 DREUPRFRJOSEAM-UHFFFAOYSA-N 0.000 claims description 6
• YAMHXTCMCPHKLN-UHFFFAOYSA-N imidazolidin-2-one Chemical compound O=C1NCCN1 YAMHXTCMCPHKLN-UHFFFAOYSA-N 0.000 claims description 6
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