JPWO2021130492A5 - - Google Patents
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- JPWO2021130492A5 JPWO2021130492A5 JP2022538727A JP2022538727A JPWO2021130492A5 JP WO2021130492 A5 JPWO2021130492 A5 JP WO2021130492A5 JP 2022538727 A JP2022538727 A JP 2022538727A JP 2022538727 A JP2022538727 A JP 2022538727A JP WO2021130492 A5 JPWO2021130492 A5 JP WO2021130492A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- acrylic acid
- oxadiazol
- phenyl
- cyclopropyl
- Prior art date
- 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 51
- 150000003839 salts Chemical class 0.000 claims 29
- 125000000217 alkyl group Chemical group 0.000 claims 17
- 239000012453 solvate Substances 0.000 claims 15
- 239000003112 inhibitor Substances 0.000 claims 12
- 125000005843 halogen group Chemical group 0.000 claims 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 11
- 239000003795 chemical substances by application Substances 0.000 claims 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 10
- 208000011580 syndromic disease Diseases 0.000 claims 10
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 9
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 9
- 230000001363 autoimmune Effects 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 230000001684 chronic effect Effects 0.000 claims 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 6
- 238000002560 therapeutic procedure Methods 0.000 claims 6
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- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 4
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- 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 2
- 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 2
- 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 2
- XKFOEZLFLIDKMU-UHFFFAOYSA-N 2-[[5-[(4-chlorophenyl)-difluoromethyl]-1,2,4-oxadiazol-3-yl]methyl]prop-2-enoic acid Chemical compound ClC1=CC=C(C=C1)C(C1=NC(=NO1)CC(C(=O)O)=C)(F)F XKFOEZLFLIDKMU-UHFFFAOYSA-N 0.000 claims 2
- MSYGAHOHLUJIKV-UHFFFAOYSA-N 3,5-dimethyl-1-(3-nitrophenyl)-1h-pyrazole-4-carboxylic acid ethyl ester Chemical compound CC1=C(C(=O)OCC)C(C)=NN1C1=CC=CC([N+]([O-])=O)=C1 MSYGAHOHLUJIKV-UHFFFAOYSA-N 0.000 claims 2
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- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims 2
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- 208000011200 Kawasaki disease Diseases 0.000 claims 2
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- 208000012192 Mucous membrane pemphigoid Diseases 0.000 claims 2
- 102000002233 Myelin-Oligodendrocyte Glycoprotein Human genes 0.000 claims 2
- 108010000123 Myelin-Oligodendrocyte Glycoprotein Proteins 0.000 claims 2
- 208000009525 Myocarditis Diseases 0.000 claims 2
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- 206010064911 Pulmonary arterial hypertension Diseases 0.000 claims 2
- 206010037660 Pyrexia Diseases 0.000 claims 2
- 102000013530 TOR Serine-Threonine Kinases Human genes 0.000 claims 2
- 108010065917 TOR Serine-Threonine Kinases Proteins 0.000 claims 2
- 206010052779 Transplant rejections Diseases 0.000 claims 2
- 102000011017 Type 4 Cyclic Nucleotide Phosphodiesterases Human genes 0.000 claims 2
- 108010037584 Type 4 Cyclic Nucleotide Phosphodiesterases Proteins 0.000 claims 2
- 206010046851 Uveitis Diseases 0.000 claims 2
- 108010073929 Vascular Endothelial Growth Factor A Proteins 0.000 claims 2
- 102000005789 Vascular Endothelial Growth Factors Human genes 0.000 claims 2
- 108010019530 Vascular Endothelial Growth Factors Proteins 0.000 claims 2
- 208000027094 acute motor and sensory axonal neuropathy Diseases 0.000 claims 2
- 125000000304 alkynyl group Chemical group 0.000 claims 2
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- 201000004612 anterior uveitis Diseases 0.000 claims 2
- 230000001494 anti-thymocyte effect Effects 0.000 claims 2
- 201000008937 atopic dermatitis Diseases 0.000 claims 2
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- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 201000005667 central retinal vein occlusion Diseases 0.000 claims 2
- 201000005795 chronic inflammatory demyelinating polyneuritis Diseases 0.000 claims 2
- 201000009805 cryptogenic organizing pneumonia Diseases 0.000 claims 2
- 208000004921 cutaneous lupus erythematosus Diseases 0.000 claims 2
- 230000007812 deficiency Effects 0.000 claims 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims 2
- 206010014599 encephalitis Diseases 0.000 claims 2
- 208000037902 enteropathy Diseases 0.000 claims 2
- 230000009610 hypersensitivity Effects 0.000 claims 2
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- 230000000366 juvenile effect Effects 0.000 claims 2
- 230000001404 mediated effect Effects 0.000 claims 2
- 206010063344 microscopic polyangiitis Diseases 0.000 claims 2
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- 208000008338 non-alcoholic fatty liver disease Diseases 0.000 claims 2
- 239000000041 non-steroidal anti-inflammatory agent Substances 0.000 claims 2
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- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 claims 2
- 229940124597 therapeutic agent Drugs 0.000 claims 2
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- 208000001072 type 2 diabetes mellitus Diseases 0.000 claims 2
- RUDATBOHQWOJDD-UZVSRGJWSA-N ursodeoxycholic acid Chemical compound C([C@H]1C[C@@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)CC1 RUDATBOHQWOJDD-UZVSRGJWSA-N 0.000 claims 2
- 229960001661 ursodiol Drugs 0.000 claims 2
- YLOCGHYTXIINAI-XKUOMLDTSA-N (2s)-2-amino-3-(4-hydroxyphenyl)propanoic acid;(2s)-2-aminopentanedioic acid;(2s)-2-aminopropanoic acid;(2s)-2,6-diaminohexanoic acid Chemical compound C[C@H](N)C(O)=O.NCCCC[C@H](N)C(O)=O.OC(=O)[C@@H](N)CCC(O)=O.OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 YLOCGHYTXIINAI-XKUOMLDTSA-N 0.000 claims 1
- 125000006583 (C1-C3) haloalkyl group Chemical group 0.000 claims 1
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims 1
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- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 claims 1
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 claims 1
- 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 1
- YJWKQZKHPRCDCS-UHFFFAOYSA-N 2-[(3-cycloheptyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C1(CCCCCC1)C1=NOC(=N1)CC(C(=O)O)=C YJWKQZKHPRCDCS-UHFFFAOYSA-N 0.000 claims 1
- DMEDLJNQDIWYHB-UHFFFAOYSA-N 2-[(3-cyclohexyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C1(CCCCC1)C1=NOC(=N1)CC(C(=O)O)=C DMEDLJNQDIWYHB-UHFFFAOYSA-N 0.000 claims 1
- WWKFRXPVBBUVMY-UHFFFAOYSA-N 2-[(3-cyclooctyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C1(CCCCCCC1)C1=NOC(=N1)CC(C(=O)O)=C WWKFRXPVBBUVMY-UHFFFAOYSA-N 0.000 claims 1
- GDVQXNIGPNNLRD-UHFFFAOYSA-N 2-[(3-nonyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCCC)C1=NOC(=N1)CC(C(=O)O)=C GDVQXNIGPNNLRD-UHFFFAOYSA-N 0.000 claims 1
- XHGHQGWWJGBTOW-UHFFFAOYSA-N 2-[(3-oct-3-ynyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C(CC#CCCCC)C1=NOC(=N1)CC(C(=O)O)=C XHGHQGWWJGBTOW-UHFFFAOYSA-N 0.000 claims 1
- AYCVWQFTTHGTBH-UHFFFAOYSA-N 2-[(3-oct-7-ynyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCC#C)C1=NOC(=N1)CC(C(=O)O)=C AYCVWQFTTHGTBH-UHFFFAOYSA-N 0.000 claims 1
- JFQVEGQTUVGKSY-UHFFFAOYSA-N 2-[(3-octan-2-yl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound CC(CCCCCC)C1=NOC(=N1)CC(C(=O)O)=C JFQVEGQTUVGKSY-UHFFFAOYSA-N 0.000 claims 1
- ZUKFBHPVYIOEEG-UHFFFAOYSA-N 2-[(3-octyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCC)C1=NOC(=N1)CC(C(=O)O)=C ZUKFBHPVYIOEEG-UHFFFAOYSA-N 0.000 claims 1
- HQNIYWZYASCJCL-UHFFFAOYSA-N 2-[(3-undecyl-1,2,4-oxadiazol-5-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCCCCC)C1=NOC(=N1)CC(C(=O)O)=C HQNIYWZYASCJCL-UHFFFAOYSA-N 0.000 claims 1
- MDCSOFJAPKZXTB-UHFFFAOYSA-N 2-[(4,5-dibutyl-1,3-oxazol-2-yl)methyl]prop-2-enoic acid Chemical compound C(CCC)C=1N=C(OC=1CCCC)CC(C(=O)O)=C MDCSOFJAPKZXTB-UHFFFAOYSA-N 0.000 claims 1
- 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
- VINPNCPPRVDALI-UHFFFAOYSA-N 2-[(5-methyl-4-octyl-1,3-oxazol-2-yl)methyl]prop-2-enoic acid Chemical compound CC1=C(N=C(O1)CC(C(=O)O)=C)CCCCCCCC VINPNCPPRVDALI-UHFFFAOYSA-N 0.000 claims 1
- IECGQSROBXYODT-UHFFFAOYSA-N 2-[(5-octyl-1,2-oxazol-3-yl)methyl]prop-2-enoic acid Chemical compound C(CCCCCCC)C1=CC(=NO1)CC(C(=O)O)=C IECGQSROBXYODT-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
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- 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
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- 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
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- JBQFMFAJLBCHKZ-UHFFFAOYSA-N 2-[[3-(4-butoxy-3-chlorophenyl)-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)Cl JBQFMFAJLBCHKZ-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
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- 229960000951 mycophenolic acid Drugs 0.000 claims 1
- HPNSFSBZBAHARI-RUDMXATFSA-N mycophenolic acid Chemical compound OC1=C(C\C=C(/C)CCC(O)=O)C(OC)=C(C)C2=C1C(=O)OC2 HPNSFSBZBAHARI-RUDMXATFSA-N 0.000 claims 1
- 208000010125 myocardial infarction Diseases 0.000 claims 1
- 230000002151 myoclonic effect Effects 0.000 claims 1
- 201000003631 narcolepsy Diseases 0.000 claims 1
- 230000002956 necrotizing effect Effects 0.000 claims 1
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- 208000008795 neuromyelitis optica Diseases 0.000 claims 1
- 230000003472 neutralizing effect Effects 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 206010053219 non-alcoholic steatohepatitis Diseases 0.000 claims 1
- 235000020824 obesity Nutrition 0.000 claims 1
- ZXERDUOLZKYMJM-ZWECCWDJSA-N obeticholic acid Chemical compound C([C@@]12C)C[C@@H](O)C[C@H]1[C@@H](CC)[C@@H](O)[C@@H]1[C@@H]2CC[C@]2(C)[C@@H]([C@H](C)CCC(O)=O)CC[C@H]21 ZXERDUOLZKYMJM-ZWECCWDJSA-N 0.000 claims 1
- 229960001601 obeticholic acid Drugs 0.000 claims 1
- 208000015200 ocular cicatricial pemphigoid Diseases 0.000 claims 1
- 201000005737 orchitis Diseases 0.000 claims 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 claims 1
- 229910052760 oxygen Inorganic materials 0.000 claims 1
- GTUJJVSZIHQLHA-XPWFQUROSA-N pApA Chemical compound C1=NC2=C(N)N=CN=C2N1[C@@H]([C@@H]1O)O[C@H](COP(O)(O)=O)[C@H]1OP(O)(=O)OC[C@H]([C@@H](O)[C@H]1O)O[C@H]1N1C(N=CN=C2N)=C2N=C1 GTUJJVSZIHQLHA-XPWFQUROSA-N 0.000 claims 1
- 201000005580 palindromic rheumatism Diseases 0.000 claims 1
- 201000007407 panuveitis Diseases 0.000 claims 1
- 208000012111 paraneoplastic syndrome Diseases 0.000 claims 1
- 230000037361 pathway Effects 0.000 claims 1
- 201000001976 pemphigus vulgaris Diseases 0.000 claims 1
- 229960001476 pentoxifylline Drugs 0.000 claims 1
- 208000025487 periodic fever syndrome Diseases 0.000 claims 1
- 230000002093 peripheral effect Effects 0.000 claims 1
- 239000008177 pharmaceutical agent Substances 0.000 claims 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 claims 1
- 229940043441 phosphoinositide 3-kinase inhibitor Drugs 0.000 claims 1
- 238000001126 phototherapy Methods 0.000 claims 1
- 229960003073 pirfenidone Drugs 0.000 claims 1
- ISWRGOKTTBVCFA-UHFFFAOYSA-N pirfenidone Chemical compound C1=C(C)C=CC(=O)N1C1=CC=CC=C1 ISWRGOKTTBVCFA-UHFFFAOYSA-N 0.000 claims 1
- 238000002616 plasmapheresis Methods 0.000 claims 1
- 201000006292 polyarteritis nodosa Diseases 0.000 claims 1
- 208000005987 polymyositis Diseases 0.000 claims 1
- 230000002980 postoperative effect Effects 0.000 claims 1
- 239000003450 potassium channel blocker Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 230000002265 prevention Effects 0.000 claims 1
- 208000018290 primary dysautonomia Diseases 0.000 claims 1
- 201000000742 primary sclerosing cholangitis Diseases 0.000 claims 1
- 230000008569 process Effects 0.000 claims 1
- 230000000750 progressive effect Effects 0.000 claims 1
- 230000035755 proliferation Effects 0.000 claims 1
- 235000019260 propionic acid Nutrition 0.000 claims 1
- 229940095574 propionic acid Drugs 0.000 claims 1
- 239000003207 proteasome inhibitor Substances 0.000 claims 1
- 201000003651 pulmonary sarcoidosis Diseases 0.000 claims 1
- 150000003212 purines Chemical class 0.000 claims 1
- 208000009954 pyoderma gangrenosum Diseases 0.000 claims 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 claims 1
- 239000002516 radical scavenger Substances 0.000 claims 1
- 238000001959 radiotherapy Methods 0.000 claims 1
- 208000002574 reactive arthritis Diseases 0.000 claims 1
- 208000009169 relapsing polychondritis Diseases 0.000 claims 1
- 230000000552 rheumatic effect Effects 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 206010039083 rhinitis Diseases 0.000 claims 1
- 229960004181 riluzole Drugs 0.000 claims 1
- 150000003873 salicylate salts Chemical class 0.000 claims 1
- 201000000306 sarcoidosis Diseases 0.000 claims 1
- 201000000980 schizophrenia Diseases 0.000 claims 1
- 208000010157 sclerosing cholangitis Diseases 0.000 claims 1
- 201000001223 septic arthritis Diseases 0.000 claims 1
- 230000001568 sexual effect Effects 0.000 claims 1
- 201000009890 sinusitis Diseases 0.000 claims 1
- 150000003410 sphingosines Chemical class 0.000 claims 1
- 210000000278 spinal cord Anatomy 0.000 claims 1
- LXMSZDCAJNLERA-ZHYRCANASA-N spironolactone Chemical compound C([C@@H]1[C@]2(C)CC[C@@H]3[C@@]4(C)CCC(=O)C=C4C[C@H]([C@@H]13)SC(=O)C)C[C@@]21CCC(=O)O1 LXMSZDCAJNLERA-ZHYRCANASA-N 0.000 claims 1
- 208000026082 sterile multifocal osteomyelitis with periostitis and pustulosis Diseases 0.000 claims 1
- 150000003431 steroids Chemical class 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 229940037128 systemic glucocorticoids Drugs 0.000 claims 1
- UTNUDOFZCWSZMS-YFHOEESVSA-N teriflunomide Chemical compound C\C(O)=C(/C#N)C(=O)NC1=CC=C(C(F)(F)F)C=C1 UTNUDOFZCWSZMS-YFHOEESVSA-N 0.000 claims 1
- 229960000331 teriflunomide Drugs 0.000 claims 1
- DTXLBRAVKYTGFE-UHFFFAOYSA-J tetrasodium;2-(1,2-dicarboxylatoethylamino)-3-hydroxybutanedioate Chemical compound [Na+].[Na+].[Na+].[Na+].[O-]C(=O)C(O)C(C([O-])=O)NC(C([O-])=O)CC([O-])=O DTXLBRAVKYTGFE-UHFFFAOYSA-J 0.000 claims 1
- 229960003433 thalidomide Drugs 0.000 claims 1
- 229960000278 theophylline Drugs 0.000 claims 1
- 208000008732 thymoma Diseases 0.000 claims 1
- 230000000699 topical effect Effects 0.000 claims 1
- 208000009174 transverse myelitis Diseases 0.000 claims 1
- 229940121358 tyrosine kinase inhibitor Drugs 0.000 claims 1
- 239000005483 tyrosine kinase inhibitor Substances 0.000 claims 1
- 150000004917 tyrosine kinase inhibitor derivatives Chemical class 0.000 claims 1
- 208000019553 vascular disease Diseases 0.000 claims 1
- 235000019166 vitamin D Nutrition 0.000 claims 1
- 239000011710 vitamin D Chemical class 0.000 claims 1
- 150000003710 vitamin D derivatives Chemical class 0.000 claims 1
- 229940046008 vitamin d Drugs 0.000 claims 1
- 208000005494 xerophthalmia Diseases 0.000 claims 1
Claims (19)
- 式(I)の化合物であって、
または
RA1が、C1-10アルキル、C2-10アルケニル、C2-10アルキニル、-(CH2)0-6-C3-10シクロアルキル、-(CH2)0-6-C5-10スピロシクロアルキル、-(CH2)0-6-アリール、およびO-アリールからなる群から選択され、
RA1が、任意にハロ、C1-6アルキル、C1-6ハロアルキル、ヒドロキシ、シアノ、OG1、S(O)0-2G1、SF5、(CH2)0-3C3-7シクロアルキル、および5~7員ヘテロシクリルからなる群から選択される1つ以上の置換基で置換され、前記C3-7シクロアルキルおよび前記5~7員ヘテロシクリルが、任意にハロ、C1-3アルキル、およびC1-3ハロアルキルから選択される1つ以上の基で置換され、同じ炭素原子と結合する2つのアルキル基が、任意に連結して、C3-7シクロアルキル環を形成し、C3-10シクロアルキル基が、任意にフェニル環に縮合し、前記フェニル環が、任意に1つ以上のハロ原子で置換されるか、またはRA1が、任意にC1-2ハロアルキル、C1-2ハロアルコキシ、もしくは1つ以上のハロ原子で置換される1つのフェニル環で任意に置換され、
G1が、C1-6アルキル、C3-7シクロアルキル、C1-6ハロアルキル、または(CH2)0-1フェニルであり、G1が、任意にハロ、C1-2アルキル、C1-2ハロアルキル、ヒドロキシ、シアノ、ニトロ、C1-2アルコキシ、およびC1-2ハロアルコキシからなる群から選択される1つ以上の置換基で置換され、
RA2が、ハロ、C1-6アルキル、C2-6アルケニル、C2-6アルキニル、C1-6ハロアルキル、ヒドロキシ、シアノ、ニトロ、NR1R2、OG2、およびS(O)0-2G2からなる群から選択され、
G2が、C1-6アルキル、C3-7シクロアルキル、C1-6ハロアルキル、またはフェニルであり、それが、任意にハロ、C1-2アルキル、C1-2ハロアルキル、ヒドロキシ、シアノ、ニトロ、C1-2アルコキシ、およびC1-2ハロアルコキシからなる群から選択される1つ以上の置換基で置換され、
R1およびR2が独立して、HまたはC1-2アルキルであるか、または一緒になって、R1およびR2が組み合わされて、5~7員複素環を形成し得、
またはRA2が、非存在であり、
RCおよびRDが各々独立して、H、C1-2アルキル、ヒドロキシ、フルオロ、またはC1-2アルコキシであるか、またはRCおよびRDが連結して、C3-5シクロアルキル環を形成し得、
基RA1およびRA2の炭素原子の総数が、それらの任意の置換基を含んで一緒に、6~14であり、
あるいはその薬学的に許容される塩および/または溶媒和物。 - RA1が、-(CH2)0-2-フェニルであり、ここで、RA1が、1つのOG1基で置換され、G1が、C1-6アルキルである、請求項1~3のいずれか一項に記載の化合物、あるいはその薬学的に許容される塩および/または溶媒和物。
- RA2が、非存在であり、RCが、Hであり、そして、RDが、Hである、請求項1~4のいずれか一項に記載の化合物、あるいはその薬学的に許容される塩および/または溶媒和物。
- 2-((3-オクチル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-オクチル-1,3,4-オキサジアゾール-2-イル)メチル)アクリル酸、
2-((5-オクチル-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((3-(4-クロロベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-クロロフェネチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-ヘプチル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-クロロフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(オクタン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(ナフタレン-2-イルメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-クロロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(8,8,8-トリフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(2-メチルヘプタン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((1-オクチル-1H-1,2,4-トリアゾール-3-イル)メチル)アクリル酸、
2-((3-(3,4-ジクロロベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(tert-ブチル)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3,5-ジクロロベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(7,7,8,8,8-ペンタフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブチルフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((4’-クロロ-[1,1’-ビフェニル]-4-イル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(3-クロロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-(トリフルオロメチル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ペンチルフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(2-クロロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-クロロフェニル)シクロブチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(2-メチルオクタン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-ブチルフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ペンチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-ブチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(2-(4-クロロフェニル)プロパン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(7,7-ジフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(シクロヘキシルメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-(4-クロロフェニル)プロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(オクチル-d17)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(オクタ-7-イン-1-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-プロピルフェネチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-オクチル-1,3,4-チアジアゾール-2-イル)メチル)アクリル酸、
2-((4-オクチルチアゾール-2-イル)メチル)アクリル酸、
2-((4-オクチルオキサゾール-2-イル)メチル)アクリル酸、
(R)-2-((3-(オクタン-2-イル1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-エチルフェネチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(トリフルオロメチル)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
(S)-2-((3-(オクタン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-フルオロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-メトキシフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(トリフルオロメトキシ)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(7,7,8-トリフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1-(トリフルオロメチル)シクロプロピル)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-(トリフルオロメトキシ)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-ブロモフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブトキシベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-クロロ-3-フルオロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-ノニル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(8,8,8-トリフルオロオクタン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-オクチルチアゾール-2-イル)メチル)アクリル酸、
2-((3-ウンデシル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(オクタ-3-イン-1-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(8,8-ジフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-オクチルオキサゾール-2-イル)メチル)アクリル酸、
2-((3-(9,9,9-トリフルオロノニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブトキシフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(ジスピロ[3.1.36.14]デカン-2-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-シクロオクチル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-シクロヘキシル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-シクロヘプチル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(アダマンタン-1-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(3,5-ジクロロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(6-メチルヘプチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ネオペンチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-プロピルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1,1-ジフルオロプロピル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1-プロピルシクロプロピル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(3,3,3-トリフルオロプロピル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((4-クロロフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(5,5,5-トリフルオロペンチル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(2-シクロプロピルエチル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-(ペンタフルオロ-λ6-スルファネイル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-(ジフルオロメトキシ)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1,1-ジフルオロペンチル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-ブトキシフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1,1,2,2-テトラフルオロエトキシ)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-(1,1,2,2-テトラフルオロエトキシ)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-(1,1-ジフルオロオクチル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((5-((4-クロロフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((5-((4-ブロモフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((3-(1-(4-((トリフルオロメチル)チオ)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(6,6,8,8,8-ペンタフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1,1-ジフルオロオクチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-((4-クロロフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((3-((4-ブロモフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((4-ブチルフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(ジフルオロ(4-(トリフルオロメチル)フェニル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1,1-ジフルオロペンチル)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(ジフルオロ(4-(トリフルオロメトキシ)フェニル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-(4-ブチルベンジル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((5-(4-ブトキシフェニル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((5-(ジフルオロ(4-(トリフルオロメチル)フェニル)メチル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((3-(4-(1,1-ジフルオロブチル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-(1-(4-(トリフルオロメトキシ)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-3-イル)メチル)アクリル酸、
2-((3-(4-(ベンジルオキシ)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((4-(4-ブチルフェニル)オキサゾール-2-イル)メチル)アクリル酸、
2-((5-オクチルイソオキサゾール-3-イル)メチル)アクリル酸、
2-((4-(1-(4-(トリフルオロメチル)フェニル)シクロプロピル)オキサゾール-2-イル)メチル)アクリル酸、
2-((4-オクチルピリジン-2-イル)メチル)アクリル酸トリフルオロ酢酸塩、
2-((5-オクチルピリジン-2-イル)メチル)アクリル酸トリフルオロ酢酸塩、
2-((5-オクチルピリミジン-2-イル)メチル)アクリル酸、
2-((5-オクチルピラジン-2-イル)メチル)アクリル酸、
2-((6-オクチルピリダジン-3-イル)メチル)アクリル酸、
2-((5-メチル-4-オクチルオキサゾール-2-イル)メチル)アクリル酸、
2-(ヒドロキシ(3-オクチル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((5-ブチル-4-(4-クロロフェニル)オキサゾール-2-イル)メチル)アクリル酸、
2-(メトキシ(3-オクチル-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-シクロブトキシフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-シクロペンチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-シクロプロポキシフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-シクロペンチルフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-ヨードフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブロモフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ヨードフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(ジフルオロ(4-ヨードフェニル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(ペンタフルオロ-λ6-スルファネイル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(ペンタフルオロ-λ6-スルファネイル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((4,5-ジブチルオキサゾール-2-イル)メチル)アクリル酸、
2,2-((3-(ジフルオロ(4-(ペンタフルオロ-λ6-スルファネイル)フェニル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2,2-((3-(ジフルオロ(4-フルオロフェニル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブチルフェノキシ)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((4-(4-ブチルベンジル)オキサゾール-2-イル)メチル)アクリル酸、
2-((3-(4-シクロブチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブトキシ-3-フルオロフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-クロロ-4-プロポキシフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-シクロブチルフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(ピロリジン-1-イル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(3,5-ジクロロ-4-フルオロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3,5-ジクロロ-4-フルオロベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-クロロ-3,5-ジフルオロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(3-クロロ-4-(トリフルオロメチル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-クロロ-4-(トリフルオロメチル)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(4-ブロモ-3-クロロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブロモ-3-クロロベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(3-クロロ-4-メトキシフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(1-(3-クロロ-4-メチルフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-シクロブトキシフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-シクロペンチルオキシフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
(R)-2-((3-(4-(sec-ブトキシ)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
(S)-2-((3-(4-(sec-ブトキシ)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(4,4,4-トリフルオロブトキシ)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(1-プロピルシクロプロピル)ベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4,6-ジクロロ-2,3-ジヒドロ-1H-インデン-1-イル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-プロポキシフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((3-クロロ-4-メトキシフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((3-クロロ-4-メチルフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((4-クロロフェニル)フルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((3,5-ジクロロ-4-フルオロフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-((4-ブロモ-3-クロロフェニル)ジフルオロメチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(ジフルオロ(4-((トリフルオロメチル)チオ)フェニル)メチル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-(1-(3-(1-(4-(トリフルオロメチル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)シクロプロピル)アクリル酸、
3-メチル-2-メチレン-3-(3-(1-(4-(トリフルオロメチル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)ブタン酸、
2-((3-(1-(4-((トリフルオロメチル)スルフィニル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-((トリフルオロメチル)チオ)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-(3-メトキシプロポキシ)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブトキシ-3-クロロフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブトキシ-3-(トリフルオロメチル)フェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-ブトキシ-3,5-ジフルオロフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-クロロ-4-メトキシベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(4-クロロ-3,5-ジフルオロベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((3-(3-クロロ-4-メチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
2-((6-(4-クロロベンジル)ピリジン-2-イル)メチル)アクリル酸トリフルオロ酢酸塩、
2-(1-(3-(ジフルオロ(4-(トリフルオロメチル)フェニル)メチル)-1,2,4-オキサジアゾール-5-イル)シクロプロピル)アクリル酸、
2-メチレン-3-(3-(1-(4-(トリフルオロメチル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)ブタン酸、
2-((6-(1-(4-クロロフェニル)シクロプロピル)ピリジン-2-イル)メチル)アクリル酸、および
2-((3-(1-(4-ブロモ-3,5-ジクロロフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、
あるいはその薬学的に許容される塩および/または溶媒和物からなる群から選択される、請求項1に記載の化合物。 - 2-((3-(4-ブチルベンジル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、あるいはその薬学的に許容される塩および/または溶媒和物である、請求項5に記載の化合物。
- 2-((3-(1-(4-ブロモフェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、あるいはその薬学的に許容される塩および/または溶媒和物である、請求項5に記載の化合物。
- 2-((3-(4-ブトキシフェニル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、あるいはその薬学的に許容される塩および/または溶媒和物である、請求項5に記載の化合物。
- 2-((3-(1-(4-((トリフルオロメチル)チオ)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、あるいはその薬学的に許容される塩および/または溶媒和物である、請求項5に記載の化合物。
- 2-((3-(1-(4-(ペンタフルオロ-λ6-スルファネイル)フェニル)シクロプロピル)-1,2,4-オキサジアゾール-5-イル)メチル)アクリル酸、あるいはその薬学的に許容される塩および/または溶媒和物である、請求項5に記載の化合物。
- 請求項1~11のいずれか一項に記載の化合物あるいはその薬学的に許容される塩および/または溶媒和物を含む、薬剤として使用するための、薬学的組成物。
- 炎症性疾患もしくは望ましくない免疫応答に関連する疾患の治療または予防に使用するための、請求項1~11のいずれか一項に記載の化合物あるいはその薬学的に許容される塩および/または溶媒和物を含む、薬学的組成物。
- 前記炎症性疾患または望ましくない免疫応答に関連する疾患が、乾癬(慢性プラーク、紅皮症、膿疱性、滴状、逆および爪変異を含む)、喘息、慢性閉塞性肺疾患(COPD、慢性気管支炎および肺気腫を含む)、心不全(左心室不全を含む)、心筋梗塞、狭心症、他のアテローム性動脈硬化症および/またはアテローム血栓症関連障害(末梢血管疾患および虚血性脳卒中を含む)、ミトコンドリアおよび神経変性疾患、自己免疫腫瘍随伴性網膜症、移植拒絶反応(抗体媒介型およびT細胞媒介型を含む)、多発性硬化症、横断性脊髄炎、虚血再灌流傷害、AGE誘発性のゲノム損傷、炎症性腸疾患、原発性硬化性胆管炎(PSC)、PSC-自己免疫性肝炎重複症候群、非アルコール性脂肪性肝疾患(非アルコール性脂肪性肝炎)、リウマチ性、環状肉芽腫、皮膚エリテマトーデス(CLE)、全身性エリテマトーデス(SLE)、ループス腎炎、薬剤誘導性ループス、自己免疫性心筋炎または心筋心膜炎、ドレスラー症候群、巨細胞性心筋炎、心膜切開後症候群、薬剤性過敏症症候群(過敏性心筋炎を含む)、湿疹、サルコイドーシス、結節性紅斑、急性散在性脳脊髄炎(ADEM)、視神経脊髄炎スペクトラム障害、MOG(ミエリンオリゴデンドロサイト糖タンパク質)抗体関連障害(MOG-EMを含む)、視神経炎、CLIPPERS(ステロイドに反応する橋血管周囲の増強を伴う慢性リンパ球性炎症)、びまん性脊髄破砕性硬化症、アジソン病、円形脱毛症、強直性脊椎炎、他の脊椎関節炎(乾癬、炎症性腸疾患、反応性関節炎または若年発症型に関連する末梢脊椎関節炎を含む)、抗リン脂質抗体症候群、自己免疫性溶血性貧血、自己免疫性肝炎、自己免疫性内耳疾患、類天疱瘡(水疱性類天疱瘡、粘膜類天疱瘡、瘢痕性類天疱瘡、妊娠性類天疱瘡または類天疱瘡、眼性瘢痕性類天疱瘡を含む)、線状IgA病、ベーチェット病、セリアック病、シャーガス病、皮膚筋炎、I型糖尿病、子宮内膜症、グッドパスチャー症候群、グレーブス病、ギランバレー症候群およびそのサブタイプ(急性炎症性脱髄性多発神経障害、AIDP、急性運動軸索ニューロパシー(AMAN)、急性運動および感覚軸索ニューロパシー(AMSAN)、咽頭-頸部-腕神経叢変異体、ミラーフィッシャー変異体およびビッカースタッフ脳幹脳炎を含む)、進行性炎症性ニューロパシー、橋本病、化膿性汗腺炎、封入体筋炎、壊死性ミオパチー、川崎病、IgA腎症、ヘノッホシェーンライン紫斑病、特発性血小板減少性紫斑病、血栓性血小板減少性紫斑病(TTP)、エヴァンス症候群、間質性膀胱炎、混合性結合組織病、未分化結合組織病、モルフィア、重症筋無力症(MuSK抗体陽性および血清陰性変異体を含む)、ナルコレプシー、神経筋緊張症、尋常性天疱瘡、悪性貧血、乾癬性関節炎、多発性筋炎、原発性胆汁性胆管炎(原発性胆汁性肝硬変としても知られる)、関節リウマチ、パリンドローム性リウマチ、統合失調症、自己免疫(髄膜)脳炎症候群、強皮症、シェーグレン症候群、全身硬直症候群、リウマチ性多発筋痛、巨細胞性動脈炎(側頭動脈炎)、高安動脈炎、結節性多発動脈炎、川崎病、多発血管炎性肉芽腫症(GPA;以前はウェゲナー肉芽腫症として知られていた)、多発血管炎を伴う好酸球性肉芽腫症(EGPA;以前はチャーグ-ストラウス症候群として知られていた)、顕微鏡的多発動脈炎/多発血管炎、低補体性蕁麻疹性血管炎、過敏性血管炎、クリオグロブリン血症、閉塞性血栓血管炎(バージャー病)、血管炎、白血球破砕性血管炎、白斑、急性散在性脳脊髄炎、副腎白質ジストロフィー、アレキサンダー病、アルパー病、バロ同心硬化症またはマールブルグ病、特発性器質化肺炎(以前は、肺炎を組織化する閉塞性気管支炎として知られていた)、カナバン病、中枢神経系血管炎症候群、シャルコー・マリー・トゥース病、中枢神経系髄鞘形成不全を伴う小児運動失調、慢性炎症性脱髄性多発神経障害(CIDP)、糖尿病性網膜症、グロボイド細胞白質ジストロフィー(クラッベ病)、移植片対宿主病(GVHD)(急性および慢性形態、ならびに腸GVHDを含む)、C型肝炎(HCV)感染または合併症、単純ヘルペスウイルス感染または合併症、ヒト免疫不全ウイルス(HIV)感染または合併症、扁平苔癬、平山病、嚢胞性線維症、肺動脈性肺高血圧症(PAH、特発性PAHを含む)、肺サルコイドーシス、特発性肺線維症、小児喘息、アトピー性皮膚炎、アレルギー性皮膚炎、接触性皮膚炎、アレルギー性鼻炎、鼻炎、副鼻腔炎、結膜炎、アレルギー性結膜炎、乾性角結膜炎、ドライアイ、眼球乾燥症、緑内障、黄斑浮腫、糖尿病性黄斑浮腫、網膜中心静脈閉塞症(CRVO)、黄斑変性症(乾性および/または湿性加齢性黄斑変性症、AMDを含む)、術後白内障炎症、ブドウ膜炎(後部、前部、中間および汎ブドウ膜炎を含む)、虹彩毛様体炎、強膜炎、角膜移植片および角膜細胞移植片拒絶反応、グルテン感受性腸症(セリアック病)、疱疹状皮膚炎、好酸球性食道炎、アカラシア、自己免疫性自律神経失調症、自己免疫性脳脊髄炎、自己免疫性食道炎、自己免疫性精巣炎、自己免疫性膵炎、大動脈炎および血管周囲炎、自己免疫性網膜症、自己免疫性蕁麻疹、ベーチェット病、(特発性)キャッスルマン病、コーガン症候群、IgG4関連疾患、後腹膜線維症、全身性若年性特発性関節炎(スティル病)を含む若年性特発性関節炎、成人発症スティル病、木質結膜炎、ムーレン潰瘍、急性痘瘡状苔癬状粃糠疹(PLEVA、ムッハ・ハーベルマン病としても知られる)、多巣性運動ニューロパシー(MMN)、小児急性発症神経精神症候群(PANS)(連鎖球菌感染症(PANDAS)に関連する小児自己免疫性神経精神障害を含む)、傍腫瘍性症候群(傍腫瘍性小脳変性症、ランバート・イートン筋麻酔症候群、辺縁系脳炎、脳幹脳炎、眼球クローヌス・ミオクローヌス運動失調、抗NMDA受容体脳炎、胸腺腫関連多臓器自己免疫を含む)、静脈周囲脳脊髄炎、反射性交感神経性ジストロフィー、再発性多発性軟骨炎、精子および精巣自己免疫、スザック症候群、トロサハント症候群、フォークト・小柳・原田症候群、抗シンテターゼ症候群、自己免疫性腸症、免疫調節不全多発性内分泌障害腸症X連鎖(IPEX)、顕微鏡的大腸炎、自己免疫性リンパ増殖症候群(ALPS)、自己免疫性多内分泌腺症-カンジダ症-外胚葉性ジストロフィー症候群(APEX)、痛風、偽痛風、アミロイド(AAまたは続発性アミロイドーシスを含む)、好酸球性筋膜炎(シュルマン症候群)、プロゲステロン過敏症(プロゲステロン皮膚炎を含む)、家族性地中海熱(FMF)、腫瘍壊死因子(TNF)受容体関連周期性発熱症候群(TRAPS)、周期性発熱を伴う高免疫グロブリン血症D(HIDS)、PAPA(化膿性関節炎、壊疽性膿皮症、重度嚢胞性痒疹)症候群、インターロイキン1受容体アンタゴニスト(DIRA)の欠乏、インターロイキン36受容体アンタゴニスト(DITRA)の欠乏、クリオピリン関連周期症候群(CAPS)(家族性寒冷自己炎症症候群[FCAS]、マックルウェルズ症候群、新生児期発症多臓器炎症性疾患[NOMID]を含む)、NLRP12関連自己炎症性疾患(NLRP12AD)、周期性熱アフタ性口内炎(PFAPA)、脂肪異栄養症および高温を伴う慢性非定型好中球性皮膚症(CANDLE)、マジード症候群、ブラウ症候群(若年性全身性肉芽腫症としても知られる)、マクロファージ活性化症候群、慢性再発性多発性骨髄炎(CRMO)、家族性寒冷自己炎症症候群、変異型アデノシンデアミナーゼ2および単一遺伝子性インターフェロン症(アイカルディ・グティエール症候群、脳白質ジストロフィーを伴う網膜血管障害、脊椎軟骨異形成症、乳児期に発症するSTING[インターフェロン遺伝子の刺激因子]関連血管障害、プロテアソーム関連自己炎症症候群、家族性凍瘡、遺伝性対側性色異常症を含む)、シュニッツラー症候群;家族性円柱腫症、先天性B細胞リンパ球増加症、OTULIN関連自己炎症性症候群、2型糖尿病、インスリン抵抗性およびメタボリックシンドローム(肥満関連の炎症を含む)、アテローム性動脈硬化症、および、腎炎症性疾患、からなる群から選択される疾患であるか、またはそれに関連する、請求項13に記載の薬学的組成物。
- さらなる治療剤であって、コルチコステロイド(糖質コルチコイド)、レチノイド、アントラリン、ビタミンD類似体、カルシニューリン阻害剤、光線療法または光化学療法または他の形態の紫外線照射療法、シクロスポリン、チオプリン、メトトレキサート、抗TNFα剤、ホスホジエステラーゼ-4(PDE4)阻害剤、抗IL-17剤、抗IL12/IL-23剤、抗IL-23剤、JAK(ヤヌスキナーゼ)阻害剤、血漿交換、静脈内免疫グロブリン(IVIG)、シクロホスファミド、抗CD20 B細胞枯渇剤、アントラサイクリン類似体、クラドリビン、スフィンゴシン1-リン酸受容体修飾因子またはスフィンゴシン類似体、インターフェロンベータ製剤(インターフェロンベータ1b/1aを含む)、グラチラマー、抗CD3療法、抗CD52標的剤、レフルノミド、テリフルノミド、金化合物、ラキニモド、カリウムチャネル遮断剤、ミコフェノール酸、ミコフェノール酸モフェチル、プリン類縁物質、mTOR(ラパマイシンの機械的標的)経路阻害剤、抗胸腺細胞グロブリン(ATG)、IL-2受容体(CD25)阻害剤、抗IL-6受容体または抗IL-6剤、ブルトン型チロシンキナーゼ(BTK)阻害剤、チロシンキナーゼ阻害剤、ウルソデオキシコール酸、ヒドロキシクロロキン、クロロキン、B細胞活性化因子(BAFF、BLyS、Bリンパ球刺激剤としても知られる)阻害剤、APRIL(増殖誘導リガンド)およびBLySの両方を標的とする融合タンパク質を含む他のB細胞標的療法、汎阻害剤を含むPI3K阻害剤、またはアイソフォームを含むp110δおよび/もしくはp110γを標的とする阻害剤、インターフェロンα受容体阻害剤、T細胞共刺激遮断剤、サリドマイドおよびその誘導体、ダプソン、クロファジミン、ロイコトリエンアンタゴニスト、テオフィリン、抗IgE療法、抗IL-5剤、長時間作用型ムスカリン剤、PDE4阻害剤、リルゾール、フリーラジカルスカベンジャー、プロテアソーム阻害剤、C5に指向するものを含む補体カスケード阻害剤、免疫吸着剤、抗胸腺細胞グロブリン、5-アミノサリチル酸およびその誘導体、α4β1および/またはα4β7インテグリンを標的とするものを含む抗インテグリン剤、抗CD11-α剤、サリチラートを含む非ステロイド性抗炎症剤(NSAID)、プロピオン酸、酢酸、オキシカム、フェナメート、選択的または比較性選択的COX-2阻害剤、コルヒチン、IL-4受容体阻害剤、局所/接触免疫療法、抗IL-1受容体療法、IL-1β阻害剤、IL-1中和療法、クロラムブシル、免疫調節特性および/またはNRF2を調節する能力を有する特定の抗生物質、抗アンドロゲン療法、ペントキシフィリン、ウルソデオキシコール酸、オベチコール酸、フィブラート、嚢胞性線維症膜コンダクタンス(CFTR)制御因子、VEGF(血管内皮増殖因子)阻害剤、ピルフェニドン、およびミゾリビン、から選択される治療剤と組み合わせて使用するための、請求項12~14のいずれか一項に記載の薬学的組成物。
- 下記に示す、式(II)の化合物、式(III)の化合物、式(V)の化合物、式(VIII)の化合物、式(XVI)の化合物、および式(XXIV)の化合物からなる群から選択される化合物であって、
式(II)の化合物は、
式(III)の化合物は、
RA1が、C1-10アルキル(ただしメチルでない)、C2-10アルケニル、C2-10アルキニル、-(CH2)0-6-C3-10シクロアルキル、-(CH2)0-6-C5-10スピロシクロアルキル、-(CH2)0-6-アリール、およびO-アリールからなる群から選択され、ここで、RA1は、任意に請求項1~5のいずれか一項で定義されたとおりに置換され、
式(V)の化合物は、
式(VIII)の化合物は、
式中、RA1、RC、およびRDが、請求項1~5のいずれか一項で定義されるとおりであり、R3、R11、およびR12が独立して、任意にハロで置換されるC1-4アルキルを表す、化合物、またはその塩であり;
式(XVI)の化合物は、
式中、RA1およびRA2が、請求項1~5のいずれか一項で定義され、Pが、パラ-メトキシベンジルである、化合物、またはその塩であり;そして
式(XXIV)の化合物は、
式中、RA1が、請求項1~5のいずれか一項で定義される、化合物、またはその塩である、
化合物。 - 式(I)の化合物、
(a)式(II)の化合物、
で示される化合物またはその塩中のエステル部分を加水分解すること;または
(b)式(XVI)の化合物、
で示される化合物またはその塩を脱保護すること;または
(c)式(XXIV)の化合物、
で示される化合物またはその塩を、金属触媒の存在下で一酸化炭素と反応させ、続いて加水分解し、式(I)の化合物を得ること、
を含む、プロセス。 - 式(I)の化合物またはその薬学的に許容される塩および/または溶媒和物が、式(I)の化合物である、請求項1~15のいずれか一項に記載の化合物または薬学的組成物。
- 式(I)の化合物またはその薬学的に許容される塩および/または溶媒和物が、式(I)の化合物の薬学的に許容される塩である、請求項1~15のいずれか一項に記載の化合物または薬学的組成物。
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WO2020232247A1 (en) | 2019-05-14 | 2020-11-19 | Provention Bio, Inc. | Methods and compositions for preventing type 1 diabetes |
BR112022025381A2 (pt) | 2020-06-11 | 2023-01-24 | Provention Bio Inc | Métodos e composições para prevenir diabetes tipo 1 |
US20240245691A1 (en) * | 2021-04-26 | 2024-07-25 | Sitryx Therapeutics Limited | 2-methylene-4-oxo-butanoic acid derivatives for the treatment of inflammation |
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 |
WO2023017269A1 (en) | 2021-08-11 | 2023-02-16 | Sitryx Therapeutics Limited | Derivatives of itaconic acid and their use as anti-inflammatory agents |
WO2023247958A1 (en) | 2022-06-22 | 2023-12-28 | 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 |
WO2024127030A1 (en) | 2022-12-15 | 2024-06-20 | Sitryx Therapeutics Limited | Substituted pyridines for use in treating or preventing inflammatory diseases or diseases associated with an undesirable immune response |
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 |
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TW201206429A (en) * | 2010-07-08 | 2012-02-16 | Merck Serono Sa | Substituted oxadiazole derivatives |
DK2970101T3 (en) | 2013-03-14 | 2018-08-20 | Alkermes Pharma Ireland Ltd | PRO-DRUGS OF FUMARATES AND THEIR USE IN TREATING DIFFERENT DISEASES |
US20160016916A1 (en) | 2013-03-15 | 2016-01-21 | Karyopharm Therapeutics Inc. | Exo Olefin-Containing Nuclear Transport Modulators and Uses Thereof |
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WO2019036509A1 (en) | 2017-08-14 | 2019-02-21 | Washington University | METHODS AND COMPOSITIONS FOR TREATING DISEASES ASSOCIATED WITH CANCER, INFLAMMATION OR IMMUNE RESPONSE |
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