JP5123667B2 - 炎症の治療においてcxcr2阻害剤として使用される縮合二環式カルボキサミド誘導体 - Google Patents
炎症の治療においてcxcr2阻害剤として使用される縮合二環式カルボキサミド誘導体 Download PDFInfo
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- JP5123667B2 JP5123667B2 JP2007548720A JP2007548720A JP5123667B2 JP 5123667 B2 JP5123667 B2 JP 5123667B2 JP 2007548720 A JP2007548720 A JP 2007548720A JP 2007548720 A JP2007548720 A JP 2007548720A JP 5123667 B2 JP5123667 B2 JP 5123667B2
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- naphthalene
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- ylmethoxy
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- NWJAMBOSAHUMGO-HNNXBMFYSA-N methyl (2s)-2-[(1-bromonaphthalene-2-carbonyl)amino]-3-methylbutanoate Chemical compound C1=CC=CC2=C(Br)C(C(=O)N[C@H](C(=O)OC)C(C)C)=CC=C21 NWJAMBOSAHUMGO-HNNXBMFYSA-N 0.000 description 1
- LLAKTTUWILQNQN-VIFPVBQESA-N methyl (2s)-2-[(1-bromonaphthalene-2-carbonyl)amino]propanoate Chemical compound C1=CC=CC2=C(Br)C(C(=O)N[C@@H](C)C(=O)OC)=CC=C21 LLAKTTUWILQNQN-VIFPVBQESA-N 0.000 description 1
- OWKBIGRJPAFRSH-KRWDZBQOSA-N methyl (2s)-2-[(1-hydroxynaphthalene-2-carbonyl)amino]-2-methylbutanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@](C)(CC)C(=O)OC)=CC=C21 OWKBIGRJPAFRSH-KRWDZBQOSA-N 0.000 description 1
- PJRBGMKXRNHBJI-KRWDZBQOSA-N methyl (2s)-2-[(4-fluoro-1-hydroxynaphthalene-2-carbonyl)amino]-2-methylbutanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)N[C@@](C)(CC)C(=O)OC)=CC(F)=C21 PJRBGMKXRNHBJI-KRWDZBQOSA-N 0.000 description 1
- RZFITFUEUUNQMZ-UHFFFAOYSA-N methyl 1-[(1-bromonaphthalene-2-carbonyl)amino]cyclopentane-1-carboxylate Chemical compound C=1C=C2C=CC=CC2=C(Br)C=1C(=O)NC1(C(=O)OC)CCCC1 RZFITFUEUUNQMZ-UHFFFAOYSA-N 0.000 description 1
- QOGRBPCPBHIJMS-UHFFFAOYSA-N methyl 1-[(4-chloro-1-hydroxynaphthalene-2-carbonyl)amino]cyclopentane-1-carboxylate Chemical compound C=1C(Cl)=C2C=CC=CC2=C(O)C=1C(=O)NC1(C(=O)OC)CCCC1 QOGRBPCPBHIJMS-UHFFFAOYSA-N 0.000 description 1
- IUMURXPYQGKDSC-UHFFFAOYSA-N methyl 1-[(4-fluoro-1-hydroxynaphthalene-2-carbonyl)amino]cyclopentane-1-carboxylate Chemical compound C=1C(F)=C2C=CC=CC2=C(O)C=1C(=O)NC1(C(=O)OC)CCCC1 IUMURXPYQGKDSC-UHFFFAOYSA-N 0.000 description 1
- APSXVMCETQYMKS-UHFFFAOYSA-N methyl 2-[(1-hydroxynaphthalene-2-carbonyl)amino]-2,3-dimethylbutanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(C)(C(=O)OC)C(C)C)=CC=C21 APSXVMCETQYMKS-UHFFFAOYSA-N 0.000 description 1
- SOKBGCXVZROSHW-UHFFFAOYSA-N methyl 2-[(1-hydroxynaphthalene-2-carbonyl)amino]-2-methyl-3-phenylpropanoate Chemical compound C=1C=C2C=CC=CC2=C(O)C=1C(=O)NC(C)(C(=O)OC)CC1=CC=CC=C1 SOKBGCXVZROSHW-UHFFFAOYSA-N 0.000 description 1
- OWKBIGRJPAFRSH-UHFFFAOYSA-N methyl 2-[(1-hydroxynaphthalene-2-carbonyl)amino]-2-methylbutanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(C)(CC)C(=O)OC)=CC=C21 OWKBIGRJPAFRSH-UHFFFAOYSA-N 0.000 description 1
- UGXJSZMUYRHNTM-UHFFFAOYSA-N methyl 2-[(4-chloro-1-hydroxynaphthalene-2-carbonyl)amino]-2-methylbutanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(C)(CC)C(=O)OC)=CC(Cl)=C21 UGXJSZMUYRHNTM-UHFFFAOYSA-N 0.000 description 1
- MVNLRBUMZNMEQW-UHFFFAOYSA-N methyl 2-[(4-chloro-1-hydroxynaphthalene-2-carbonyl)amino]-2-methylpropanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(C)(C)C(=O)OC)=CC(Cl)=C21 MVNLRBUMZNMEQW-UHFFFAOYSA-N 0.000 description 1
- PJRBGMKXRNHBJI-UHFFFAOYSA-N methyl 2-[(4-fluoro-1-hydroxynaphthalene-2-carbonyl)amino]-2-methylbutanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(C)(CC)C(=O)OC)=CC(F)=C21 PJRBGMKXRNHBJI-UHFFFAOYSA-N 0.000 description 1
- MSQHONHTLDYQJS-UHFFFAOYSA-N methyl 2-[(4-fluoro-1-hydroxynaphthalene-2-carbonyl)amino]-2-methylpropanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(C)(C)C(=O)OC)=CC(F)=C21 MSQHONHTLDYQJS-UHFFFAOYSA-N 0.000 description 1
- UWRIHQAAGMRKDA-UHFFFAOYSA-N methyl 2-[(5-fluoro-1-hydroxynaphthalene-2-carbonyl)amino]-2-methylpropanoate Chemical compound FC1=CC=CC2=C(O)C(C(=O)NC(C)(C)C(=O)OC)=CC=C21 UWRIHQAAGMRKDA-UHFFFAOYSA-N 0.000 description 1
- UBTOIUUBQNUOEU-UHFFFAOYSA-N methyl 2-[(5-fluoro-3-hydroxy-1-benzothiophene-2-carbonyl)amino]-2-methylpropanoate Chemical compound C1=C(F)C=C2C(O)=C(C(=O)NC(C)(C)C(=O)OC)SC2=C1 UBTOIUUBQNUOEU-UHFFFAOYSA-N 0.000 description 1
- RMRKMQWBHUWLBH-UHFFFAOYSA-N methyl 2-[[1-[(4-bromophenyl)methoxy]naphthalene-2-carbonyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC=C2C=CC=CC2=C1OCC1=CC=C(Br)C=C1 RMRKMQWBHUWLBH-UHFFFAOYSA-N 0.000 description 1
- IRULRXMBNRCSLB-UHFFFAOYSA-N methyl 2-[[1-[(6-methoxypyridin-3-yl)methoxy]naphthalene-2-carbonyl]amino]-2-methylbutanoate Chemical compound COC(=O)C(C)(CC)NC(=O)C1=CC=C2C=CC=CC2=C1OCC1=CC=C(OC)N=C1 IRULRXMBNRCSLB-UHFFFAOYSA-N 0.000 description 1
- DNZMZLAMLLYLJP-UHFFFAOYSA-N methyl 2-[[1-[1-(1,3-benzothiazol-2-yl)ethoxy]naphthalene-2-carbonyl]amino]-2-methylpropanoate Chemical compound C1=CC=C2SC(C(C)OC3=C4C=CC=CC4=CC=C3C(=O)NC(C)(C)C(=O)OC)=NC2=C1 DNZMZLAMLLYLJP-UHFFFAOYSA-N 0.000 description 1
- VAUBJHRVPDNDTM-UHFFFAOYSA-N methyl 2-[[1-[[4-chloro-2-(trifluoromethyl)quinolin-6-yl]methoxy]naphthalene-2-carbonyl]amino]-2-methylpropanoate Chemical compound N1=C(C(F)(F)F)C=C(Cl)C2=CC(COC3=C4C=CC=CC4=CC=C3C(=O)NC(C)(C)C(=O)OC)=CC=C21 VAUBJHRVPDNDTM-UHFFFAOYSA-N 0.000 description 1
- SPPXVAXLCRWGMD-UHFFFAOYSA-N methyl 2-[[4-fluoro-1-[[4-(trifluoromethyl)phenyl]methoxy]naphthalene-2-carbonyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C1=CC(F)=C2C=CC=CC2=C1OCC1=CC=C(C(F)(F)F)C=C1 SPPXVAXLCRWGMD-UHFFFAOYSA-N 0.000 description 1
- HMNQEFLBWLHDMW-UHFFFAOYSA-N methyl 2-[[5-fluoro-3-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]-1-benzothiophene-2-carbonyl]amino]-2-methylpropanoate Chemical compound COC(=O)C(C)(C)NC(=O)C=1SC2=CC=C(F)C=C2C=1OCC1=CC=C(C(F)(F)F)N=C1 HMNQEFLBWLHDMW-UHFFFAOYSA-N 0.000 description 1
- HMZHEECHJWHZJX-UHFFFAOYSA-N methyl 2-amino-2-methylpropanoate Chemical compound COC(=O)C(C)(C)N HMZHEECHJWHZJX-UHFFFAOYSA-N 0.000 description 1
- WMRZOCHEQXFKJW-UHFFFAOYSA-N methyl 2-methyl-2-[[1-[[6-(2,2,2-trifluoroethoxy)pyridin-3-yl]methoxy]naphthalene-2-carbonyl]amino]butanoate Chemical compound COC(=O)C(C)(CC)NC(=O)C1=CC=C2C=CC=CC2=C1OCC1=CC=C(OCC(F)(F)F)N=C1 WMRZOCHEQXFKJW-UHFFFAOYSA-N 0.000 description 1
- GNTNEHNDHXTTLJ-UHFFFAOYSA-N methyl 4,4,4-trifluoro-2-[(1-hydroxynaphthalene-2-carbonyl)amino]butanoate Chemical compound C1=CC=CC2=C(O)C(C(=O)NC(CC(F)(F)F)C(=O)OC)=CC=C21 GNTNEHNDHXTTLJ-UHFFFAOYSA-N 0.000 description 1
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
- IIHIJFJSXPDTNO-UHFFFAOYSA-N methyl cyclopentanecarboxylate Chemical compound COC(=O)C1CCCC1 IIHIJFJSXPDTNO-UHFFFAOYSA-N 0.000 description 1
- BHIWKHZACMWKOJ-UHFFFAOYSA-N methyl isobutyrate Chemical compound COC(=O)C(C)C BHIWKHZACMWKOJ-UHFFFAOYSA-N 0.000 description 1
- MGJXBDMLVWIYOQ-UHFFFAOYSA-N methylazanide Chemical compound [NH-]C MGJXBDMLVWIYOQ-UHFFFAOYSA-N 0.000 description 1
- 230000006724 microglial activation Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 230000028550 monocyte chemotaxis Effects 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- ZJRBAYHTVHTAAC-UHFFFAOYSA-N n-[1-(methanesulfonamido)-2-methyl-1-oxopropan-2-yl]-1-[[6-(trifluoromethyl)pyridin-3-yl]methoxy]naphthalene-2-carboxamide Chemical compound CS(=O)(=O)NC(=O)C(C)(C)NC(=O)C1=CC=C2C=CC=CC2=C1OCC1=CC=C(C(F)(F)F)N=C1 ZJRBAYHTVHTAAC-UHFFFAOYSA-N 0.000 description 1
- 210000002569 neuron Anatomy 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- OOFGXDQWDNJDIS-UHFFFAOYSA-N oxathiolane Chemical class C1COSC1 OOFGXDQWDNJDIS-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- NXJCBFBQEVOTOW-UHFFFAOYSA-L palladium(2+);dihydroxide Chemical compound O[Pd]O NXJCBFBQEVOTOW-UHFFFAOYSA-L 0.000 description 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 1
- VEDDBHYQWFOITD-UHFFFAOYSA-N para-bromobenzyl alcohol Chemical compound OCC1=CC=C(Br)C=C1 VEDDBHYQWFOITD-UHFFFAOYSA-N 0.000 description 1
- 230000001991 pathophysiological effect Effects 0.000 description 1
- 235000019371 penicillin G benzathine Nutrition 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000001428 peripheral nervous system Anatomy 0.000 description 1
- 230000008782 phagocytosis Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000030786 positive chemotaxis Effects 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000160 potassium phosphate Inorganic materials 0.000 description 1
- 235000011009 potassium phosphates Nutrition 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 238000002953 preparative HPLC Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 108060006633 protein kinase Proteins 0.000 description 1
- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000007115 recruitment Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- CDAISMWEOUEBRE-UHFFFAOYSA-N scyllo-inosotol Natural products OC1C(O)C(O)C(O)C(O)C1O CDAISMWEOUEBRE-UHFFFAOYSA-N 0.000 description 1
- XIIOFHFUYBLOLW-UHFFFAOYSA-N selpercatinib Chemical compound OC(COC=1C=C(C=2N(C=1)N=CC=2C#N)C=1C=NC(=CC=1)N1CC2N(C(C1)C2)CC=1C=NC(=CC=1)OC)(C)C XIIOFHFUYBLOLW-UHFFFAOYSA-N 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- AWUCVROLDVIAJX-GSVOUGTGSA-N sn-glycerol 3-phosphate Chemical compound OC[C@@H](O)COP(O)(O)=O AWUCVROLDVIAJX-GSVOUGTGSA-N 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- BBMHARZCALWXSL-UHFFFAOYSA-M sodium dihydrogenphosphate monohydrate Chemical compound O.[Na+].OP(O)([O-])=O BBMHARZCALWXSL-UHFFFAOYSA-M 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 238000003746 solid phase reaction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YZKDXIFGPWUKTI-UHFFFAOYSA-N tert-butyl 2-amino-2-methylpropanoate;hydrochloride Chemical compound Cl.CC(C)(C)OC(=O)C(C)(C)N YZKDXIFGPWUKTI-UHFFFAOYSA-N 0.000 description 1
- UOUFRTFWWBCVPV-UHFFFAOYSA-N tert-butyl 4-(2,4-dioxo-1H-thieno[3,2-d]pyrimidin-3-yl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CC1)n1c(=O)[nH]c2ccsc2c1=O UOUFRTFWWBCVPV-UHFFFAOYSA-N 0.000 description 1
- CTEDVGRUGMPBHE-UHFFFAOYSA-N tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCC(CO)CC1 CTEDVGRUGMPBHE-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- 230000000472 traumatic effect Effects 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- 239000001226 triphosphate Substances 0.000 description 1
- 235000011178 triphosphate Nutrition 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229960000281 trometamol Drugs 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003519 ventilatory effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/68—One oxygen atom attached in position 4
-
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
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- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
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- A61P1/18—Drugs for disorders of the alimentary tract or the digestive system for pancreatic disorders, e.g. pancreatic enzymes
-
- A—HUMAN NECESSITIES
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- C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
- C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
- C07D317/54—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/10—1,4-Dioxanes; Hydrogenated 1,4-dioxanes
- C07D319/14—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems
- C07D319/16—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D319/20—1,4-Dioxanes; Hydrogenated 1,4-dioxanes condensed with carbocyclic rings or ring systems condensed with one six-membered ring with substituents attached to the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
- C07D333/70—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 2
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
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| Application Number | Priority Date | Filing Date | Title |
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| EP04031009A EP1676834A1 (en) | 2004-12-30 | 2004-12-30 | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| EP04031009.6 | 2004-12-30 | ||
| PCT/EP2005/013624 WO2006069656A1 (en) | 2004-12-30 | 2005-12-17 | Fused bicyclic carboxamide derivatives for use as cxcr2 inhibitors in the treatment of inflammation |
Publications (3)
| Publication Number | Publication Date |
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| JP2008526695A JP2008526695A (ja) | 2008-07-24 |
| JP2008526695A5 JP2008526695A5 (enExample) | 2009-02-12 |
| JP5123667B2 true JP5123667B2 (ja) | 2013-01-23 |
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| JP2007548720A Expired - Fee Related JP5123667B2 (ja) | 2004-12-30 | 2005-12-17 | 炎症の治療においてcxcr2阻害剤として使用される縮合二環式カルボキサミド誘導体 |
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| EP (2) | EP1676834A1 (enExample) |
| JP (1) | JP5123667B2 (enExample) |
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| CA (1) | CA2592430A1 (enExample) |
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| NO (1) | NO20073932L (enExample) |
| NZ (1) | NZ556192A (enExample) |
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| WO2005115384A2 (en) * | 2004-05-25 | 2005-12-08 | Metabolex, Inc. | Bicyclic, substituted triazoles as modulators of ppar and methods of their preparation |
| EP1676834A1 (en) | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| DK2044028T3 (da) | 2006-01-27 | 2012-08-20 | Fibrogen Inc | Cyanoisoquinolinforbindelser til stabilisering af den hypoxiinducerende faktor (HIF) |
| BRPI0710527B8 (pt) | 2006-04-04 | 2021-05-25 | Fibrogen Inc | compostos de pirrolo- e tiazolo-piridina e composição farmacêutica que os compreende |
| EP2040690B1 (en) * | 2006-06-28 | 2014-08-06 | Sanofi | Inhibitors of cxcr2 |
| JP5237938B2 (ja) | 2006-06-28 | 2013-07-17 | サノフイ | 新規なcxcr2阻害剤 |
| JP5352454B2 (ja) * | 2006-06-28 | 2013-11-27 | サノフイ | Cxcr2アンンタゴニスト |
| JP5352455B2 (ja) * | 2006-06-30 | 2013-11-27 | サノフイ | Cxcr2阻害剤 |
| EP2094697A1 (en) * | 2006-11-23 | 2009-09-02 | Novartis AG | 5-sulfanylmethyl-pyrazolo [1,5-a]pyrimidin-7-ol derivatives as cxcr2 antagonists |
| ATE484505T1 (de) * | 2006-11-23 | 2010-10-15 | Novartis Ag | 5-sulfanylmethylä1,2,4ütriazolä1,5-aüpyrimidin- - olderivate als cxcr2-antagonisten |
| WO2008066558A2 (en) * | 2006-11-30 | 2008-06-05 | Dow Agrosciences Llc | Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines |
| WO2008151211A1 (en) * | 2007-06-05 | 2008-12-11 | Sanofi-Aventis | Substituted benzoylamino-indan-2-carboxylic acids and related compounds |
| CN102272117B (zh) | 2008-11-14 | 2015-06-17 | 菲布罗根有限公司 | 作为hif羟化酶抑制剂的苯并噻喃衍生物 |
| AU2013203591B2 (en) * | 2009-05-01 | 2017-01-19 | University Court Of The University Of Dundee | Treatment or prophylaxis of proliferative conditions |
| GB0907551D0 (en) * | 2009-05-01 | 2009-06-10 | Univ Dundee | Treatment or prophylaxis of proliferative conditions |
| WO2012079154A1 (en) * | 2010-12-14 | 2012-06-21 | Dalhousie University | Selective estrogen receptor modulators |
| CA2869232A1 (en) * | 2012-06-19 | 2013-12-27 | F. Hoffmann-La Roche Ag | New bicyclic thiophenylamide compounds |
| CA2878804A1 (en) * | 2012-09-12 | 2014-03-20 | F. Hoffmann-La Roche Ag | Non-annulated thiophenylamides as inhibitors of fatty acid binding protein(fabp) 4 and/or 5 |
| WO2014114603A1 (en) * | 2013-01-24 | 2014-07-31 | F. Hoffmann-La Roche Ag | Substituted thiazole compounds |
| EP2951159B1 (en) | 2013-01-24 | 2018-08-22 | Fibrogen, Inc. | Crystalline forms of {[1-cyano-5-(4-chlorophenoxy)-4-hydroxy-isoquinoline-3-carbonyl]-amino}-acetic acid |
| JP2017513812A (ja) * | 2014-02-28 | 2017-06-01 | ザ ロイヤル インスティチューション フォー ジ アドヴァンスメント オブ ラーニング/マギル ユニヴァーシティ | 免疫療法用のapc活性剤としてのtc−ptp阻害剤 |
| PL3925607T3 (pl) * | 2014-04-15 | 2023-10-30 | Vertex Pharmaceuticals Incorporated | Kompozycje farmaceutyczne do leczenia chorób, w których pośredniczy mukowiscydozowy przezbłonowy regulator przewodnictwa |
| JP2017527542A (ja) * | 2014-07-31 | 2017-09-21 | グラクソスミスクライン、インテレクチュアル、プロパティー、ディベロップメント、リミテッドGlaxosmithkline Intellectual Property Development Limited | 化学療法誘発末梢神経障害(cipn)の予防および/または治療のためのcxcr2アンタゴニストの使用 |
| CN105906608B (zh) * | 2016-05-03 | 2018-10-19 | 中山大学 | 8-氨基喹啉-松果体素杂联体及其药物组合物 |
| CN106187974B (zh) * | 2016-07-01 | 2018-01-12 | 广州军区广州总医院 | 具有抗肿瘤作用的鱼藤素断环结构与氨基酸衍生物的合成方法 |
| SI3717646T1 (sl) | 2017-12-01 | 2025-08-29 | The Texas A&M University System | Antisense zdravljenje angelmanovega sindroma |
| CA3091027A1 (en) | 2018-02-02 | 2019-08-08 | Maverix Oncology, Inc. | Small molecule drug conjugates of gemcitabine monophosphate |
| GB201807924D0 (en) | 2018-05-16 | 2018-06-27 | Ctxt Pty Ltd | Compounds |
| CA3106092A1 (en) | 2018-07-09 | 2020-01-16 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Anthelminthic heterocyclic compounds |
| CN119285648A (zh) | 2019-03-19 | 2025-01-10 | 勃林格殷格翰动物保健有限公司 | 驱虫的氮杂-苯并噻吩和氮杂-苯并呋喃化合物 |
| WO2021113808A1 (en) * | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Cftr-modulating arylamides |
| WO2021113806A1 (en) * | 2019-12-05 | 2021-06-10 | Genzyme Corporation | Arylamides and methods of use thereof |
| JP7662644B2 (ja) | 2019-12-18 | 2025-04-15 | シーティーエックスティー・ピーティーワイ・リミテッド | 化合物 |
| PH12022553222A1 (en) | 2020-05-29 | 2024-02-12 | Boehringer Ingelheim Animal Health Usa Inc | Anthelmintic heterocyclic compounds |
| CN111559991B (zh) * | 2020-06-01 | 2022-01-25 | 河南省锐达医药科技有限公司 | 一种萘胺类化合物及其盐的制备方法和应用 |
| PE20250675A1 (es) | 2021-11-01 | 2025-03-04 | Boehringer Ingelheim Vetmedica Gmbh | Compuestos de pirrolopiridazina como antihelminticos |
| CN115385865B (zh) * | 2022-06-29 | 2023-06-16 | 深圳大学 | 一种具有cxcr2抑制活性的小分子抑制剂及其制备方法与应用 |
| CN116041300B (zh) * | 2023-02-20 | 2024-04-26 | 沈阳药科大学 | 一种2,2-二甲基苯并吡喃类衍生物及其制备方法和应用 |
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| US4962224A (en) * | 1987-12-23 | 1990-10-09 | American Home Products Corporation | N-naphthoylglycines as aldose reductase inhibitors |
| US4994477A (en) * | 1988-03-24 | 1991-02-19 | Abbott Laboratories | Heterocyclic renin inhibitors |
| US6531467B2 (en) * | 1996-09-12 | 2003-03-11 | Idun Pharmaceuticals, Inc. | Inhibition of inflammation using interleukin-1β-converting enzyme (ICE)/CED-3 family inhibitors |
| GB9716657D0 (en) * | 1997-08-07 | 1997-10-15 | Zeneca Ltd | Chemical compounds |
| IT1317826B1 (it) | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| DE10006139A1 (de) * | 2000-02-11 | 2001-08-16 | Merck Patent Gmbh | Indol-3-yl-Derivate |
| FR2825706B1 (fr) | 2001-06-06 | 2003-12-12 | Pf Medicament | Nouveaux derives de benzothienyle ou d'indole, leur preparation et leur utilisation comme inhibiteurs de proteines prenyl transferase |
| US6673791B2 (en) * | 2001-07-30 | 2004-01-06 | Boehringer Ingelheim (Canada) Ltd. | Non-nucleoside reverse transcriptase inhibitors |
| GB2389580A (en) * | 2002-06-12 | 2003-12-17 | Bayer Ag | 2-Naphthamide PGI2 antagonists |
| WO2004108681A1 (en) * | 2003-06-06 | 2004-12-16 | Fibrogen, Inc. | Nitrogen-containing heteroaryl compounds and their use in increasing endogenous erythropoietin |
| JP2007501844A (ja) * | 2003-08-08 | 2007-02-01 | トランス テック ファーマ,インコーポレイテッド | アリール及びヘテロアリール化合物、組成物並びに使用方法 |
| EP1670804A2 (en) | 2003-09-10 | 2006-06-21 | GPC Biotech AG | Heterobicyclic compounds as pharmaceutically active agents |
| US20050085531A1 (en) | 2003-10-03 | 2005-04-21 | Hodge Carl N. | Thiophene-based compounds exhibiting ATP-utilizing enzyme inhibitory activity, and compositions, and uses thereof |
| ATE370941T1 (de) | 2003-11-20 | 2007-09-15 | Lilly Co Eli | Modulatoren des vitamin-d-rezeptors |
| GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
| WO2006040646A1 (en) | 2004-10-14 | 2006-04-20 | Pfizer, Inc. | Benzimidazole or indole amides as inhibitors of pin1 |
| CN101098852A (zh) | 2004-11-09 | 2008-01-02 | 史密丝克莱恩比彻姆公司 | 糖原磷酸化酶抑制剂化合物和其药物组合物 |
| EP1676834A1 (en) | 2004-12-30 | 2006-07-05 | Sanofi-Aventis Deutschland GmbH | Fused bicyclic carboxamide derivates for use as CXCR2 inhibitors in the treatment of inflammation |
| AR055319A1 (es) | 2005-03-17 | 2007-08-15 | Wyeth Corp | Derivados de isoquinoleina, composiciones farmaceuticas y usos |
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Also Published As
| Publication number | Publication date |
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| ATE543795T1 (de) | 2012-02-15 |
| US8283479B2 (en) | 2012-10-09 |
| IL184173A (en) | 2011-10-31 |
| RU2404962C2 (ru) | 2010-11-27 |
| CN101094830A (zh) | 2007-12-26 |
| BRPI0519452A2 (pt) | 2009-01-27 |
| ZA200704089B (en) | 2008-09-25 |
| KR20070091634A (ko) | 2007-09-11 |
| JP2008526695A (ja) | 2008-07-24 |
| NZ556192A (en) | 2010-06-25 |
| RU2007128949A (ru) | 2009-02-10 |
| MA29113B1 (fr) | 2007-12-03 |
| EP1676834A1 (en) | 2006-07-05 |
| NO20073932L (no) | 2007-08-09 |
| EP1836158B1 (en) | 2012-02-01 |
| EP1836158A1 (en) | 2007-09-26 |
| US20080090854A1 (en) | 2008-04-17 |
| CA2592430A1 (en) | 2006-07-06 |
| PE20060855A1 (es) | 2006-10-10 |
| WO2006069656A1 (en) | 2006-07-06 |
| TW200639141A (en) | 2006-11-16 |
| AR055830A1 (es) | 2007-09-12 |
| US20110184177A1 (en) | 2011-07-28 |
| UY29322A1 (es) | 2006-07-31 |
| MX2007007068A (es) | 2007-08-08 |
| IL184173A0 (en) | 2007-10-31 |
| US7919628B2 (en) | 2011-04-05 |
| AU2005321609B2 (en) | 2011-02-17 |
| AU2005321609A1 (en) | 2006-07-06 |
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