FI4081511T3 - Karboksijohdannaisia, joilla on anti-inflammatorisia ominaisuuksia - Google Patents
Karboksijohdannaisia, joilla on anti-inflammatorisia ominaisuuksia Download PDFInfo
- Publication number
- FI4081511T3 FI4081511T3 FIEP20830293.5T FI20830293T FI4081511T3 FI 4081511 T3 FI4081511 T3 FI 4081511T3 FI 20830293 T FI20830293 T FI 20830293T FI 4081511 T3 FI4081511 T3 FI 4081511T3
- Authority
- FI
- Finland
- Prior art keywords
- methyl
- acrylic acid
- oxadiazol
- yyl
- tai
- Prior art date
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- 230000003110 anti-inflammatory effect Effects 0.000 title 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 title 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 60
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 60
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 57
- 208000011580 syndromic disease Diseases 0.000 claims 21
- 230000001363 autoimmune Effects 0.000 claims 6
- 206010047115 Vasculitis Diseases 0.000 claims 5
- 201000002491 encephalomyelitis Diseases 0.000 claims 4
- 201000001119 neuropathy Diseases 0.000 claims 4
- 230000007823 neuropathy Effects 0.000 claims 4
- 208000033808 peripheral neuropathy Diseases 0.000 claims 4
- -1 3-(3-chloro-4-propoxyphenyl)-1, 2,4-oxadiazol-5-ylyl Chemical group 0.000 claims 3
- 206010072579 Granulomatosis with polyangiitis Diseases 0.000 claims 3
- 208000037902 enteropathy Diseases 0.000 claims 3
- 208000028774 intestinal disease Diseases 0.000 claims 3
- 239000008194 pharmaceutical composition Substances 0.000 claims 3
- 208000023769 AA amyloidosis Diseases 0.000 claims 2
- LEVWYRKDKASIDU-QWWZWVQMSA-N D-cystine Chemical compound OC(=O)[C@H](N)CSSC[C@@H](N)C(O)=O LEVWYRKDKASIDU-QWWZWVQMSA-N 0.000 claims 2
- 208000018428 Eosinophilic granulomatosis with polyangiitis Diseases 0.000 claims 2
- 206010019939 Herpes gestationis Diseases 0.000 claims 2
- 241000725303 Human immunodeficiency virus Species 0.000 claims 2
- 102000015617 Janus Kinases Human genes 0.000 claims 2
- 108010024121 Janus Kinases Proteins 0.000 claims 2
- 208000008223 Pemphigoid Gestationis Diseases 0.000 claims 2
- 206010035664 Pneumonia Diseases 0.000 claims 2
- 206010036105 Polyneuropathy Diseases 0.000 claims 2
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 claims 2
- 208000017442 Retinal disease Diseases 0.000 claims 2
- 206010038923 Retinopathy Diseases 0.000 claims 2
- 108060008682 Tumor Necrosis Factor Proteins 0.000 claims 2
- 102100036922 Tumor necrosis factor ligand superfamily member 13B Human genes 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- 208000007502 anemia Diseases 0.000 claims 2
- 208000006673 asthma Diseases 0.000 claims 2
- 239000000460 chlorine Substances 0.000 claims 2
- 150000001875 compounds Chemical class 0.000 claims 2
- 208000022993 cryopyrin-associated periodic syndrome Diseases 0.000 claims 2
- 229960003067 cystine Drugs 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 208000024908 graft versus host disease Diseases 0.000 claims 2
- 208000015181 infectious disease Diseases 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 230000007824 polyneuropathy Effects 0.000 claims 2
- 102000003390 tumor necrosis factor Human genes 0.000 claims 2
- CVMWJOARFZVMTB-UHFFFAOYSA-N 2-[(4-octyl-1,3-oxazol-2-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCC)C=1N=C(OC=1)CC(C(=O)O)=C CVMWJOARFZVMTB-UHFFFAOYSA-N 0.000 claims 1
- KGSNJGNAUJCVKJ-UHFFFAOYSA-N 2-[(5-octyl-1,3-thiazol-2-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCC)C1=CN=C(S1)CC(C(=O)O)=C KGSNJGNAUJCVKJ-UHFFFAOYSA-N 0.000 claims 1
- RKGYURZPLQRBFO-UHFFFAOYSA-N 2-[(5-octylpyrazin-2-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCC)C=1N=CC(=NC=1)CC(C(=O)O)=C RKGYURZPLQRBFO-UHFFFAOYSA-N 0.000 claims 1
- TYYWEYHTZVWXLQ-UHFFFAOYSA-N 2-[(5-octylpyridin-2-yl)methyl]prop-2-enoic acid 2,2,2-trifluoroacetic acid Chemical compound CCCCCCCCC1=CN=C(C=C1)CC(=C)C(=O)O.C(=O)(C(F)(F)F)O TYYWEYHTZVWXLQ-UHFFFAOYSA-N 0.000 claims 1
- QXJBOWNYFABBIB-UHFFFAOYSA-N 2-[(5-octylpyrimidin-2-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCC)C=1C=NC(=NC=1)CC(C(=O)O)=C QXJBOWNYFABBIB-UHFFFAOYSA-N 0.000 claims 1
- NYGMBNIJQOPMIR-UHFFFAOYSA-N 2-[1-[3-[1-[4-(trifluoromethyl)phenyl]cyclopropyl]-1,2,4-oxadiazol-5-yl]cyclopropyl]prop-2-enoic acid Chemical compound FC(C1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)C1(CC1)C(C(=O)O)=C)(F)F NYGMBNIJQOPMIR-UHFFFAOYSA-N 0.000 claims 1
- HRRKMHFHSHTDBZ-UHFFFAOYSA-N 2-[1-[3-[difluoro-[4-(trifluoromethyl)phenyl]methyl]-1,2,4-oxadiazol-5-yl]cyclopropyl]prop-2-enoic acid Chemical compound FC(C1=NOC(=N1)C1(CC1)C(C(=O)O)=C)(C1=CC=C(C=C1)C(F)(F)F)F HRRKMHFHSHTDBZ-UHFFFAOYSA-N 0.000 claims 1
- ZUKFBHPVYIOEEG-RORPREDISA-N 2-[[3-(1,1,2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-heptadecadeuteriooctyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(C(C(C(C(C(C(C([2H])([2H])[2H])([2H])[2H])([2H])[2H])([2H])[2H])([2H])[2H])([2H])[2H])([2H])[2H])(C1=NOC(=N1)CC(C(=O)O)=C)([2H])[2H] ZUKFBHPVYIOEEG-RORPREDISA-N 0.000 claims 1
- WVBHZKSZRYNFKG-UHFFFAOYSA-N 2-[[3-(4-butoxy-3,5-difluorophenyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)OC1=C(C=C(C=C1F)C1=NOC(=N1)CC(C(=O)O)=C)F WVBHZKSZRYNFKG-UHFFFAOYSA-N 0.000 claims 1
- NSCDNSABHJYRCY-UHFFFAOYSA-N 2-[[3-(4-butoxy-3-fluorophenyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)OC1=C(C=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C)F NSCDNSABHJYRCY-UHFFFAOYSA-N 0.000 claims 1
- KSCMHTKJFWCRHJ-UHFFFAOYSA-N 2-[[3-(4-butoxyphenyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)OC1=CC=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C KSCMHTKJFWCRHJ-UHFFFAOYSA-N 0.000 claims 1
- ITDAOQDLLUGZFB-UHFFFAOYSA-N 2-[[3-(4-butylphenyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)C1=CC=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C ITDAOQDLLUGZFB-UHFFFAOYSA-N 0.000 claims 1
- SOMSYBFZRQOHSF-UHFFFAOYSA-N 2-[[3-(4-pentylphenyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCCC)C1=CC=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C SOMSYBFZRQOHSF-UHFFFAOYSA-N 0.000 claims 1
- XBSUGBPIFXAIAX-UHFFFAOYSA-N 2-[[3-(7,7,8-trifluorooctyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(CCCCCCC1=NOC(=N1)CC(C(=O)O)=C)(CF)F XBSUGBPIFXAIAX-UHFFFAOYSA-N 0.000 claims 1
- DEARRKNFZIAKDM-UHFFFAOYSA-N 2-[[3-(8,8,8-trifluorooctan-2-yl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(CCCCCC(C)C1=NOC(=N1)CC(C(=O)O)=C)(F)F DEARRKNFZIAKDM-UHFFFAOYSA-N 0.000 claims 1
- VUFZPBQQDZIKKH-UHFFFAOYSA-N 2-[[3-(8,8,8-trifluorooctyl)-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(CCCCCCCC1=NOC(=N1)CC(C(=O)O)=C)(F)F VUFZPBQQDZIKKH-UHFFFAOYSA-N 0.000 claims 1
- JFQVEGQTUVGKSY-SNVBAGLBSA-N 2-[[3-[(2R)-octan-2-yl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C[C@H](CCCCCC)C1=NOC(=N1)CC(C(=O)O)=C JFQVEGQTUVGKSY-SNVBAGLBSA-N 0.000 claims 1
- JFQVEGQTUVGKSY-JTQLQIEISA-N 2-[[3-[(2S)-octan-2-yl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C[C@@H](CCCCCC)C1=NOC(=N1)CC(C(=O)O)=C JFQVEGQTUVGKSY-JTQLQIEISA-N 0.000 claims 1
- ZBLVCSRSFBGWKU-UHFFFAOYSA-N 2-[[3-[(3,4-dichlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=CC=1Cl ZBLVCSRSFBGWKU-UHFFFAOYSA-N 0.000 claims 1
- XWOWBSSJDUUYOG-UHFFFAOYSA-N 2-[[3-[(3,5-dichloro-4-fluorophenyl)-difluoromethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(C=C(C=1F)Cl)C(C1=NOC(=N1)CC(C(=O)O)=C)(F)F XWOWBSSJDUUYOG-UHFFFAOYSA-N 0.000 claims 1
- MHVCXSKUJFKOQI-UHFFFAOYSA-N 2-[[3-[(3,5-dichlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C(C=1)Cl MHVCXSKUJFKOQI-UHFFFAOYSA-N 0.000 claims 1
- ANKDURUUGDNUKN-UHFFFAOYSA-N 2-[[3-[(3-butylphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)C=1C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=CC=1 ANKDURUUGDNUKN-UHFFFAOYSA-N 0.000 claims 1
- XTMCGYKFSHIRQQ-UHFFFAOYSA-N 2-[[3-[(3-chloro-4-methoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=CC=1OC XTMCGYKFSHIRQQ-UHFFFAOYSA-N 0.000 claims 1
- LKWADTFRKPGHLB-UHFFFAOYSA-N 2-[[3-[(3-chloro-4-methylphenyl)-difluoromethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(C=CC=1C)C(C1=NOC(=N1)CC(C(=O)O)=C)(F)F LKWADTFRKPGHLB-UHFFFAOYSA-N 0.000 claims 1
- QVOBIOAFDZISLP-UHFFFAOYSA-N 2-[[3-[(3-chloro-4-methylphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=CC=1C QVOBIOAFDZISLP-UHFFFAOYSA-N 0.000 claims 1
- LEQQPCQFZUJRGP-UHFFFAOYSA-N 2-[[3-[(4-bromo-3-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound BrC1=C(C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1)Cl LEQQPCQFZUJRGP-UHFFFAOYSA-N 0.000 claims 1
- GXLVWVFZSLCMJS-UHFFFAOYSA-N 2-[[3-[(4-bromophenyl)-difluoromethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound BrC1=CC=C(C=C1)C(C1=NOC(=N1)CC(C(=O)O)=C)(F)F GXLVWVFZSLCMJS-UHFFFAOYSA-N 0.000 claims 1
- XGDASGQRLNJAMF-UHFFFAOYSA-N 2-[[3-[(4-butoxyphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)OC1=CC=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1 XGDASGQRLNJAMF-UHFFFAOYSA-N 0.000 claims 1
- IVKDJKAYLBNSRL-UHFFFAOYSA-N 2-[[3-[(4-butylphenyl)-difluoromethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)C1=CC=C(C=C1)C(C1=NOC(=N1)CC(C(=O)O)=C)(F)F IVKDJKAYLBNSRL-UHFFFAOYSA-N 0.000 claims 1
- IPOUXAUBCPEGIH-UHFFFAOYSA-N 2-[[3-[(4-butylphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CCC)C1=CC=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1 IPOUXAUBCPEGIH-UHFFFAOYSA-N 0.000 claims 1
- RZVFQPVTKAZAED-UHFFFAOYSA-N 2-[[3-[(4-chloro-3,5-difluorophenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC1=C(C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1F)F RZVFQPVTKAZAED-UHFFFAOYSA-N 0.000 claims 1
- GJPNGWITFUFPJB-UHFFFAOYSA-N 2-[[3-[(4-chlorophenyl)-fluoromethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC1=CC=C(C=C1)C(C1=NOC(=N1)CC(C(=O)O)=C)F GJPNGWITFUFPJB-UHFFFAOYSA-N 0.000 claims 1
- YWEVHXUOROVDGP-UHFFFAOYSA-N 2-[[3-[(4-propylphenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CC)C1=CC=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1 YWEVHXUOROVDGP-UHFFFAOYSA-N 0.000 claims 1
- QXTIPOZICIFENS-UHFFFAOYSA-N 2-[[3-[1-(3,5-dichloro-4-fluorophenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(C=C(C=1F)Cl)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C QXTIPOZICIFENS-UHFFFAOYSA-N 0.000 claims 1
- BMWHFYDBEMBKMQ-UHFFFAOYSA-N 2-[[3-[1-(4-bromo-3,5-dichlorophenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound BrC1=C(C=C(C=C1Cl)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C)Cl BMWHFYDBEMBKMQ-UHFFFAOYSA-N 0.000 claims 1
- YWCCYLKOCAQPOX-UHFFFAOYSA-N 2-[[3-[1-(4-bromo-3-chlorophenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound BrC1=C(C=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C)Cl YWCCYLKOCAQPOX-UHFFFAOYSA-N 0.000 claims 1
- MXXULZUUXSJBAN-UHFFFAOYSA-N 2-[[3-[1-(4-bromophenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound BrC1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C MXXULZUUXSJBAN-UHFFFAOYSA-N 0.000 claims 1
- YJIBCTLHCIVRRZ-UHFFFAOYSA-N 2-[[3-[1-(4-chloro-3-fluorophenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC1=C(C=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C)F YJIBCTLHCIVRRZ-UHFFFAOYSA-N 0.000 claims 1
- BGAHYZSZQVXXRU-UHFFFAOYSA-N 2-[[3-[1-(4-chlorophenyl)cyclobutyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC1=CC=C(C=C1)C1(CCC1)C1=NOC(=N1)CC(C(=O)O)=C BGAHYZSZQVXXRU-UHFFFAOYSA-N 0.000 claims 1
- PRZHLWIQKHVHPP-UHFFFAOYSA-N 2-[[3-[1-(4-cyclopropyloxyphenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C1(CC1)OC1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C PRZHLWIQKHVHPP-UHFFFAOYSA-N 0.000 claims 1
- NDLCPDRMACMJRR-UHFFFAOYSA-N 2-[[3-[1-(4-fluorophenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C NDLCPDRMACMJRR-UHFFFAOYSA-N 0.000 claims 1
- YFQGSNFZZANUSO-UHFFFAOYSA-N 2-[[3-[1-(4-methoxyphenyl)cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound COC1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C YFQGSNFZZANUSO-UHFFFAOYSA-N 0.000 claims 1
- LQWHMOBGCCFNCI-UHFFFAOYSA-N 2-[[3-[1-[4-(difluoromethoxy)phenyl]cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(OC1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C)F LQWHMOBGCCFNCI-UHFFFAOYSA-N 0.000 claims 1
- NPSPASPIBVTRGY-UHFFFAOYSA-N 2-[[3-[1-[4-(trifluoromethoxy)phenyl]cyclopropyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(OC1=CC=C(C=C1)C1(CC1)C1=NOC(=N1)CC(C(=O)O)=C)(F)F NPSPASPIBVTRGY-UHFFFAOYSA-N 0.000 claims 1
- RXOCJZFGDPTMAH-UHFFFAOYSA-N 2-[[3-[2-(4-ethylphenyl)ethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(C)C1=CC=C(C=C1)CCC1=NOC(=N1)CC(C(=O)O)=C RXOCJZFGDPTMAH-UHFFFAOYSA-N 0.000 claims 1
- ILPFGDRJLZQGLG-UHFFFAOYSA-N 2-[[3-[2-(4-propylphenyl)ethyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C(CC)C1=CC=C(C=C1)CCC1=NOC(=N1)CC(C(=O)O)=C ILPFGDRJLZQGLG-UHFFFAOYSA-N 0.000 claims 1
- BVLPQTZGQQCBQS-UHFFFAOYSA-N 2-[[3-[4-(1,1-difluoropentyl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(CCCC)(F)C1=CC=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C BVLPQTZGQQCBQS-UHFFFAOYSA-N 0.000 claims 1
- CGZWCJWERYRBMV-UHFFFAOYSA-N 2-[[3-[4-(2-cyclopropylethyl)phenyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound C1(CC1)CCC1=CC=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C CGZWCJWERYRBMV-UHFFFAOYSA-N 0.000 claims 1
- ACGGZZLJZRONIP-UHFFFAOYSA-N 2-[[3-[4-(4,4,4-trifluorobutoxy)phenyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(CCCOC1=CC=C(C=C1)C1=NOC(=N1)CC(C(=O)O)=C)(F)F ACGGZZLJZRONIP-UHFFFAOYSA-N 0.000 claims 1
- BCRYVNLZVDKJFL-UHFFFAOYSA-N 2-[[3-[[3-chloro-4-(trifluoromethyl)phenyl]methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound ClC=1C=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=CC=1C(F)(F)F BCRYVNLZVDKJFL-UHFFFAOYSA-N 0.000 claims 1
- ZDZWALIKCFUWNE-UHFFFAOYSA-N 2-[[3-[[4-(trifluoromethoxy)phenyl]methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(OC1=CC=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1)(F)F ZDZWALIKCFUWNE-UHFFFAOYSA-N 0.000 claims 1
- VWPHRPOFMKINSQ-UHFFFAOYSA-N 2-[[3-[[4-[1-(trifluoromethyl)cyclopropyl]phenyl]methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(C1(CC1)C1=CC=C(CC2=NOC(=N2)CC(C(=O)O)=C)C=C1)(F)F VWPHRPOFMKINSQ-UHFFFAOYSA-N 0.000 claims 1
- RFIDIECKBLFKNX-UHFFFAOYSA-N 2-[[3-[difluoro-(4-iodophenyl)methyl]-1,2,4-oxadiazol-5-yl]methyl]prop-2-enoic acid Chemical compound FC(C1=NOC(=N1)CC(C(=O)O)=C)(C1=CC=C(C=C1)I)F RFIDIECKBLFKNX-UHFFFAOYSA-N 0.000 claims 1
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Classifications
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- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
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- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
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- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A61P19/00—Drugs for skeletal disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
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- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D277/24—Radicals substituted by oxygen atoms
Landscapes
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- Chemical & Material Sciences (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pyridine Compounds (AREA)
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| PCT/GB2020/053357 WO2021130492A1 (en) | 2019-12-23 | 2020-12-23 | Carboxy derivatives with antiinflammatory properties |
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| MX2021013299A (es) | 2019-04-30 | 2022-01-31 | Sitryx Therapeutics Ltd | Derivados de acido itaconico y usos de estos en el tratamiento de una enfermedad inflamatoria asociada con una respuesta inmunitaria indeseable. |
| WO2020232247A1 (en) | 2019-05-14 | 2020-11-19 | Provention Bio, Inc. | Methods and compositions for preventing type 1 diabetes |
| IL298999A (en) | 2020-06-11 | 2023-02-01 | Provention Bio Inc | Methods and compositions for the prevention of type 1 diabetes |
| EP4192821A1 (en) | 2020-08-05 | 2023-06-14 | Sitryx Therapeutics Limited | Alpha,beta unsaturated methacrylic esters with anti-inflammatory properties |
| EP4330231A1 (en) * | 2021-04-26 | 2024-03-06 | Sitryx Therapeutics Limited | 2-methylene-4-oxo-butanoic acid drivatives for the treatment of inflammation |
| JP2024520444A (ja) | 2021-05-24 | 2024-05-24 | プロヴェンション・バイオ・インコーポレイテッド | １型糖尿病を治療するための方法 |
| EP4359390A1 (en) * | 2021-06-22 | 2024-05-01 | Sitryx Therapeutics Limited | Acrylamide derivatives useful as anti-inflammatory agents |
| CN113499453B (zh) * | 2021-07-20 | 2022-10-21 | 徐州医科大学 | 自噬抑制及抗炎联合温合光热诊疗剂及其制备方法与应用 |
| US20240360067A1 (en) | 2021-08-11 | 2024-10-31 | Sitryx Therapeutics Limited | Derivatives of itaconic acid and their use as anti-inflammatory agents |
| AU2023287566A1 (en) | 2022-06-22 | 2025-01-16 | Sitryx Therapeutics Limited | Oxadiazole derivatives, preparation process thereof and their use in treating inflammatory diseases |
| WO2024089421A1 (en) | 2022-10-25 | 2024-05-02 | Sitryx Therapeutics Limited | Tetrazole derivatives |
| CN120712258A (zh) | 2022-12-15 | 2025-09-26 | 西特瑞治疗有限公司 | 用于治疗或预防炎性疾病或与不良免疫反应相关的疾病的取代吡啶类化合物 |
| KR102864655B1 (ko) * | 2023-01-19 | 2025-09-29 | 대한민국 | 뎅기바이러스 감염에 의한 질환의 예방 또는 치료용 약학적 조성물 |
| CN115819186B (zh) * | 2023-02-14 | 2023-05-16 | 广东银珠医药科技有限公司 | 一种3,5-二氯苯甲醇的新型制备方法 |
| CN117205194A (zh) * | 2023-05-10 | 2023-12-12 | 苏州大学 | 衣康酸或其衍生物在制备预防或治疗急性移植物抗宿主病药物中的应用 |
| CN116725998A (zh) * | 2023-07-20 | 2023-09-12 | 中国科学技术大学 | 特立氟胺在抑制nlrp3炎症小体活化中的应用 |
| CN119792264B (zh) * | 2025-03-14 | 2025-06-10 | 华中科技大学同济医学院附属同济医院 | 丁酰肼在制备预防或治疗copd的药物中的应用 |
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| WO1995011235A1 (en) * | 1993-10-20 | 1995-04-27 | The Upjohn Company | Pyrimidinones as antiarthritic and anti-inflammatories |
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| TW201206429A (en) * | 2010-07-08 | 2012-02-16 | Merck Serono Sa | Substituted oxadiazole derivatives |
| KR101861883B1 (ko) * | 2010-12-06 | 2018-05-28 | 글락소 그룹 리미티드 | Lp-PLA₂에 의해 매개되는 질환 또는 상태의 치료에 사용하기 위한 피리미디논 화합물 |
| KR102085557B1 (ko) | 2013-03-14 | 2020-03-06 | 엘커메스 파마 아일랜드 리미티드 | 푸마레이트의 프로드럭 및 다양한 질환을 치료하는데 있어서의 이들의 용도 |
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| AU2014290368B2 (en) * | 2013-07-18 | 2019-07-11 | Baylor College Of Medicine | Methods and compositions for treatment of muscle wasting, muscle weakness, and/or cachexia |
| CN103923105B (zh) * | 2014-04-17 | 2016-08-24 | 北京大学 | 2-中氮茚甲酰胺类化合物及其制备和用途 |
| EP3416634A4 (en) | 2016-02-15 | 2019-10-09 | Artyomov, Maxim | IMMUNOMODULATORY AGENTS AND METHOD FOR USE THEREOF |
| WO2019036509A1 (en) | 2017-08-14 | 2019-02-21 | Washington University | METHODS AND COMPOSITIONS FOR TREATING DISEASES ASSOCIATED WITH CANCER, INFLAMMATION OR IMMUNE RESPONSE |
| CN110731955B (zh) | 2019-10-28 | 2023-05-02 | 中山大学 | 衣康酸二甲酯在预防和治疗溃疡性结肠炎及其癌变中的应用 |
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