KR20190082985A - 소염제 2-옥소티아졸 및 2-옥소옥사졸 - Google Patents
소염제 2-옥소티아졸 및 2-옥소옥사졸 Download PDFInfo
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- KR20190082985A KR20190082985A KR1020197018997A KR20197018997A KR20190082985A KR 20190082985 A KR20190082985 A KR 20190082985A KR 1020197018997 A KR1020197018997 A KR 1020197018997A KR 20197018997 A KR20197018997 A KR 20197018997A KR 20190082985 A KR20190082985 A KR 20190082985A
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- Prior art keywords
- alkyl
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- alkenyl group
- Prior art date
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- CZWWCTHQXBMHDA-UHFFFAOYSA-N 3h-1,3-thiazol-2-one Chemical class OC1=NC=CS1 CZWWCTHQXBMHDA-UHFFFAOYSA-N 0.000 title claims description 15
- XYVMOLOUBJBNBF-UHFFFAOYSA-N 3h-1,3-oxazol-2-one Chemical class OC1=NC=CO1 XYVMOLOUBJBNBF-UHFFFAOYSA-N 0.000 title description 3
- 230000003110 anti-inflammatory effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 221
- 150000001875 compounds Chemical class 0.000 claims abstract description 110
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 64
- 125000005843 halogen group Chemical group 0.000 claims abstract description 55
- 125000003118 aryl group Chemical group 0.000 claims abstract description 51
- 150000003839 salts Chemical class 0.000 claims abstract description 33
- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims abstract description 31
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 31
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 29
- 150000002148 esters Chemical class 0.000 claims abstract description 26
- 125000004122 cyclic group Chemical group 0.000 claims abstract description 25
- 239000012453 solvate Substances 0.000 claims abstract description 25
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 22
- 229940002612 prodrug Drugs 0.000 claims abstract description 22
- 239000000651 prodrug Substances 0.000 claims abstract description 22
- 208000037976 chronic inflammation Diseases 0.000 claims abstract description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 21
- 238000011282 treatment Methods 0.000 claims abstract description 21
- 150000001204 N-oxides Chemical class 0.000 claims abstract description 20
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 20
- 208000037893 chronic inflammatory disorder Diseases 0.000 claims abstract description 20
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 19
- 125000004429 atom Chemical group 0.000 claims abstract description 16
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 claims abstract description 14
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 14
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims abstract description 12
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims abstract description 12
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims abstract description 10
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 claims abstract description 10
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 10
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims abstract description 9
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims abstract description 9
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims abstract description 9
- 230000002378 acidificating effect Effects 0.000 claims abstract description 7
- 125000003831 tetrazolyl group Chemical group 0.000 claims abstract description 7
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 claims abstract description 5
- 238000000034 method Methods 0.000 claims description 63
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 23
- 201000010099 disease Diseases 0.000 claims description 20
- 239000002253 acid Chemical group 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 13
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 12
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 125000001117 oleyl 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])/C([H])=C([H])\C([H])([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 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 9
- 201000004681 Psoriasis Diseases 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 8
- 125000006720 (C1-C6) alkyl (C6-C10) aryl group Chemical group 0.000 claims description 6
- 230000001684 chronic effect Effects 0.000 claims description 5
- 230000002757 inflammatory effect Effects 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 238000002560 therapeutic procedure Methods 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 4
- 208000027866 inflammatory disease Diseases 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 206010012438 Dermatitis atopic Diseases 0.000 claims description 3
- 206010012442 Dermatitis contact Diseases 0.000 claims description 3
- 208000019872 Drug Eruptions Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 241000220317 Rosa Species 0.000 claims description 3
- 206010039793 Seborrhoeic dermatitis Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 206010003246 arthritis Diseases 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 125000000962 organic group Chemical group 0.000 claims description 3
- 230000002685 pulmonary effect Effects 0.000 claims description 3
- 208000008742 seborrheic dermatitis Diseases 0.000 claims description 3
- 208000017520 skin disease Diseases 0.000 claims description 3
- 208000024172 Cardiovascular disease Diseases 0.000 claims description 2
- 208000002029 allergic contact dermatitis Diseases 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 150000003852 triazoles Chemical class 0.000 claims description 2
- 210000003169 central nervous system Anatomy 0.000 claims 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims 1
- 210000003928 nasal cavity Anatomy 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 59
- 239000000243 solution Substances 0.000 description 55
- -1 2-oxooleyl side chains Chemical group 0.000 description 52
- 239000000203 mixture Substances 0.000 description 48
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
- 230000008569 process Effects 0.000 description 34
- 239000003921 oil Substances 0.000 description 32
- 235000019198 oils Nutrition 0.000 description 32
- 238000006243 chemical reaction Methods 0.000 description 30
- 235000019439 ethyl acetate Nutrition 0.000 description 26
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- 239000002904 solvent Substances 0.000 description 23
- 239000012230 colorless oil Substances 0.000 description 22
- 239000003208 petroleum Substances 0.000 description 22
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 21
- 239000012267 brine Substances 0.000 description 21
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 21
- 239000007787 solid Substances 0.000 description 21
- 239000000047 product Substances 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- 239000012044 organic layer Substances 0.000 description 18
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 239000007864 aqueous solution Substances 0.000 description 14
- 239000011541 reaction mixture Substances 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- CSJLBAMHHLJAAS-UHFFFAOYSA-N diethylaminosulfur trifluoride Chemical compound CCN(CC)S(F)(F)F CSJLBAMHHLJAAS-UHFFFAOYSA-N 0.000 description 12
- 238000002844 melting Methods 0.000 description 12
- 230000008018 melting Effects 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 11
- 229940088598 enzyme Drugs 0.000 description 11
- 206010061218 Inflammation Diseases 0.000 description 10
- 230000004054 inflammatory process Effects 0.000 description 10
- 238000010898 silica gel chromatography Methods 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 9
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 9
- 230000005764 inhibitory process Effects 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- 229910019093 NaOCl Inorganic materials 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- YZXBAPSDXZZRGB-DOFZRALJSA-N arachidonic acid Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC(O)=O YZXBAPSDXZZRGB-DOFZRALJSA-N 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 8
- 239000003937 drug carrier Substances 0.000 description 8
- 150000002978 peroxides Chemical class 0.000 description 8
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 229910010082 LiAlH Inorganic materials 0.000 description 7
- 108010064785 Phospholipases Proteins 0.000 description 7
- 102000015439 Phospholipases Human genes 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000010410 layer Substances 0.000 description 7
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- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- ZKWFSTHEYLJLEL-UHFFFAOYSA-N morpholine-4-carboxamide Chemical compound NC(=O)N1CCOCC1 ZKWFSTHEYLJLEL-UHFFFAOYSA-N 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 6
- 229920006395 saturated elastomer Polymers 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 5
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 5
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 5
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 5
- 150000001299 aldehydes Chemical class 0.000 description 5
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- LDRPSTLEZAJXJW-UHFFFAOYSA-N 1-(1,3-thiazol-2-yl)hexadecan-1-one Chemical compound CCCCCCCCCCCCCCCC(=O)C1=NC=CS1 LDRPSTLEZAJXJW-UHFFFAOYSA-N 0.000 description 4
- RWGFFVCDSGOWFT-UHFFFAOYSA-N 1-(1,3-thiazol-2-yl)pentan-1-one Chemical compound CCCCC(=O)C1=NC=CS1 RWGFFVCDSGOWFT-UHFFFAOYSA-N 0.000 description 4
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide Chemical compound CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 description 4
- AOYPVCZZUFRAFK-UHFFFAOYSA-N 5-phenyl-1-(1,3-thiazol-2-yl)pentan-1-one Chemical compound N=1C=CSC=1C(=O)CCCCC1=CC=CC=C1 AOYPVCZZUFRAFK-UHFFFAOYSA-N 0.000 description 4
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- ZIIUUSVHCHPIQD-UHFFFAOYSA-N 2,4,6-trimethyl-N-[3-(trifluoromethyl)phenyl]benzenesulfonamide Chemical compound CC1=CC(C)=CC(C)=C1S(=O)(=O)NC1=CC=CC(C(F)(F)F)=C1 ZIIUUSVHCHPIQD-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
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- ZRALSGWEFCBTJO-UHFFFAOYSA-N guanidine group Chemical group NC(=N)N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 3
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- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 3
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- RZLQCNYCMRDLBA-KTKRTIGZSA-N (z)-1-morpholin-4-yloctadec-9-en-1-one Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)N1CCOCC1 RZLQCNYCMRDLBA-KTKRTIGZSA-N 0.000 description 2
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- PITPMKYQIWBNKL-UHFFFAOYSA-N 1-(1,3-thiazol-2-yl)hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCC(O)C1=NC=CS1 PITPMKYQIWBNKL-UHFFFAOYSA-N 0.000 description 2
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- JFAROODSPDQMGZ-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxy-6-phenylhexanenitrile Chemical compound CC(C)(C)[Si](C)(C)OC(C#N)CCCCC1=CC=CC=C1 JFAROODSPDQMGZ-UHFFFAOYSA-N 0.000 description 2
- UUEIWLHMAACUIK-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxy-6-phenylhexanethioamide Chemical compound CC(C)(C)[Si](C)(C)OC(C(N)=S)CCCCC1=CC=CC=C1 UUEIWLHMAACUIK-UHFFFAOYSA-N 0.000 description 2
- MSHKLPXVEBNONW-UHFFFAOYSA-N 2-[tert-butyl(dimethyl)silyl]oxyheptadecanenitrile Chemical compound CCCCCCCCCCCCCCCC(C#N)O[Si](C)(C)C(C)(C)C MSHKLPXVEBNONW-UHFFFAOYSA-N 0.000 description 2
- LZEGFRREKFOHLK-UHFFFAOYSA-N 2-fluoro-5-(4-hexoxyphenyl)pentanal Chemical compound CCCCCCOC1=CC=C(CCCC(F)C=O)C=C1 LZEGFRREKFOHLK-UHFFFAOYSA-N 0.000 description 2
- ZMGWPPVMKBCNJF-UHFFFAOYSA-N 2-fluorohexadecane Chemical compound CCCCCCCCCCCCCCC(C)F ZMGWPPVMKBCNJF-UHFFFAOYSA-N 0.000 description 2
- UYLXPKNRAKOGSY-UHFFFAOYSA-N 3-(4-hexoxyphenyl)propanal Chemical compound CCCCCCOC1=CC=C(CCC=O)C=C1 UYLXPKNRAKOGSY-UHFFFAOYSA-N 0.000 description 2
- NSHQWPSMUKLQLC-UHFFFAOYSA-N 4-(4-hexoxyphenyl)butanal Chemical compound CCCCCCOC1=CC=C(CCCC=O)C=C1 NSHQWPSMUKLQLC-UHFFFAOYSA-N 0.000 description 2
- PGUKLHNMLPULTB-UHFFFAOYSA-N 4-(4-octylphenoxy)butanal Chemical compound CCCCCCCCC1=CC=C(OCCCC=O)C=C1 PGUKLHNMLPULTB-UHFFFAOYSA-N 0.000 description 2
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- C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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Landscapes
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Applications Claiming Priority (3)
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| US24833809P | 2009-10-02 | 2009-10-02 | |
| US61/248,338 | 2009-10-02 | ||
| PCT/EP2010/064687 WO2011039365A1 (en) | 2009-10-02 | 2010-10-01 | Anti inflammatory 2-oxothiazoles and 2 -oxooxazoles |
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| KR1020127011173A Ceased KR20120089701A (ko) | 2009-10-02 | 2010-10-01 | 소염제 2-옥소티아졸 및 2-옥소옥사졸 |
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| KR1020127011173A Ceased KR20120089701A (ko) | 2009-10-02 | 2010-10-01 | 소염제 2-옥소티아졸 및 2-옥소옥사졸 |
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| GB201221329D0 (en) * | 2012-11-27 | 2013-01-09 | Avexxin As | Dermatitis treatment |
| CA2899137C (en) * | 2013-01-29 | 2021-07-13 | Avexxin As | Antiinflammatory and antitumor 2-oxothiazoles and 2-oxothiophenes compounds |
| GB201307331D0 (en) * | 2013-04-23 | 2013-05-29 | Norwegian Univ Sci & Tech Ntnu | Compound |
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| JP7169584B2 (ja) * | 2018-01-30 | 2022-11-11 | 公立大学法人横浜市立大学 | オーキシン生合成阻害活性を有する新規化合物、その製造方法及びその用途 |
| GB201806663D0 (en) | 2018-04-24 | 2018-06-06 | Avexxin As | 2-Oxothiazole compositions for treatment of fibrotic disease |
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| AU2010302584A1 (en) | 2012-05-24 |
| AU2010302584B2 (en) | 2015-09-10 |
| KR20120089701A (ko) | 2012-08-13 |
| KR101997163B1 (ko) | 2019-07-08 |
| CN104892542A (zh) | 2015-09-09 |
| KR101907535B1 (ko) | 2018-10-15 |
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| CN103772312A (zh) | 2014-05-07 |
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| CN102647984B (zh) | 2015-03-25 |
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| US20170166539A1 (en) | 2017-06-15 |
| DK2482815T3 (en) | 2018-06-06 |
| KR20170038941A (ko) | 2017-04-07 |
| IN2012DN02982A (enExample) | 2015-07-31 |
| HK1197551A1 (zh) | 2015-01-23 |
| HK1210157A1 (en) | 2016-04-15 |
| CN103772312B (zh) | 2016-08-17 |
| CN102647984A (zh) | 2012-08-22 |
| CA2782797A1 (en) | 2011-04-07 |
| EP3431084A1 (en) | 2019-01-23 |
| JP6012468B2 (ja) | 2016-10-25 |
| EP2482815A1 (en) | 2012-08-08 |
| KR20180114228A (ko) | 2018-10-17 |
| EP2482815B1 (en) | 2018-05-02 |
| WO2011039365A1 (en) | 2011-04-07 |
| US9597318B2 (en) | 2017-03-21 |
| JP2013506639A (ja) | 2013-02-28 |
| CA2782797C (en) | 2018-08-07 |
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