KR20230154221A - 트리아졸릴-메틸 치환된 알파-d-갈락토피라노시드 유도체 - Google Patents

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Publication number

KR20230154221A

KR20230154221A KR1020237033375A KR20237033375A KR20230154221A KR 20230154221 A KR20230154221 A KR 20230154221A KR 1020237033375 A KR1020237033375 A KR 1020237033375A KR 20237033375 A KR20237033375 A KR 20237033375A KR 20230154221 A KR20230154221 A KR 20230154221A

Authority

KR

South Korea

Prior art keywords

triazol

methyl

pyran

hydroxymethyl

difluorophenyl

Prior art date

2021-03-03

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.)

Pending

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• 150000001875 compounds Chemical class 0.000 claims abstract description 165
• 150000003839 salts Chemical class 0.000 claims abstract description 32
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• -1 [1,2,3]triazole-1,4-diyl Chemical group 0.000 claims description 198
• 125000001153 fluoro group Chemical group F* 0.000 claims description 48
• 230000002265 prevention Effects 0.000 claims description 43
• 125000002619 bicyclic group Chemical group 0.000 claims description 41
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 41
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 40
• 125000001424 substituent group Chemical group 0.000 claims description 37
• JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 33
• 238000000034 method Methods 0.000 claims description 33
• 125000002950 monocyclic group Chemical group 0.000 claims description 31
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
• BHDLTOUYJMTTTM-UHFFFAOYSA-N oxan-3-ol Chemical compound OC1CCCOC1 BHDLTOUYJMTTTM-UHFFFAOYSA-N 0.000 claims description 30
• 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 27
• 238000011282 treatment Methods 0.000 claims description 27
• 201000010099 disease Diseases 0.000 claims description 26
• 229910052739 hydrogen Inorganic materials 0.000 claims description 26
• 239000001257 hydrogen Substances 0.000 claims description 26
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
• 125000004430 oxygen atom Chemical group O* 0.000 claims description 23
• 206010016654 Fibrosis Diseases 0.000 claims description 22
• 229910052757 nitrogen Inorganic materials 0.000 claims description 20
• 229910052736 halogen Inorganic materials 0.000 claims description 19
• 150000002367 halogens Chemical class 0.000 claims description 19
• 206010028980 Neoplasm Diseases 0.000 claims description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
• 208000037765 diseases and disorders Diseases 0.000 claims description 16
• 230000004761 fibrosis Effects 0.000 claims description 16
• 208000020832 chronic kidney disease Diseases 0.000 claims description 15
• 230000002757 inflammatory effect Effects 0.000 claims description 14
• 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 14
• 208000035475 disorder Diseases 0.000 claims description 12
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
• 208000024172 Cardiovascular disease Diseases 0.000 claims description 11
• 125000001246 bromo group Chemical group Br* 0.000 claims description 11
• 201000011510 cancer Diseases 0.000 claims description 11
• 208000027866 inflammatory disease Diseases 0.000 claims description 11
• 208000019423 liver disease Diseases 0.000 claims description 11
• 210000000056 organ Anatomy 0.000 claims description 11
• 208000029523 Interstitial Lung disease Diseases 0.000 claims description 10
• 208000016222 Pancreatic disease Diseases 0.000 claims description 10
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 10
• 229920006395 saturated elastomer Polymers 0.000 claims description 10
• 208000023275 Autoimmune disease Diseases 0.000 claims description 9
• KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 8
• 208000018522 Gastrointestinal disease Diseases 0.000 claims description 8
• 125000000217 alkyl group Chemical group 0.000 claims description 8
• 239000003814 drug Substances 0.000 claims description 8
• 125000006163 5-membered heteroaryl group Chemical group 0.000 claims description 7
• 230000033115 angiogenesis Effects 0.000 claims description 7
• 230000002062 proliferating effect Effects 0.000 claims description 7
• 208000009304 Acute Kidney Injury Diseases 0.000 claims description 6
• 208000033626 Renal failure acute Diseases 0.000 claims description 6
• 206010052779 Transplant rejections Diseases 0.000 claims description 6
• 230000002159 abnormal effect Effects 0.000 claims description 6
• 201000011040 acute kidney failure Diseases 0.000 claims description 6
• 208000033808 peripheral neuropathy Diseases 0.000 claims description 6
• 208000019693 Lung disease Diseases 0.000 claims description 5
• 210000004556 brain Anatomy 0.000 claims description 5
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• 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
• 208000024691 pancreas disease Diseases 0.000 claims description 5
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• 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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