CA2230896A1 - Carboxylates de pyrimidine, composes connexes et methodes de traitement des etats inflammatoires - Google Patents
Carboxylates de pyrimidine, composes connexes et methodes de traitement des etats inflammatoires Download PDFInfo
- Publication number
- CA2230896A1 CA2230896A1 CA002230896A CA2230896A CA2230896A1 CA 2230896 A1 CA2230896 A1 CA 2230896A1 CA 002230896 A CA002230896 A CA 002230896A CA 2230896 A CA2230896 A CA 2230896A CA 2230896 A1 CA2230896 A1 CA 2230896A1
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- carboxylate
- mmol
- aminocitraconamido
- compound
- 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.)
- Abandoned
Links
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- 238000000034 method Methods 0.000 title abstract description 31
- ZFCHNZDUMIOWFV-UHFFFAOYSA-N pyrimidine-2-carboxylic acid Chemical class OC(=O)C1=NC=CC=N1 ZFCHNZDUMIOWFV-UHFFFAOYSA-N 0.000 title 1
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 45
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
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- 150000003839 salts Chemical class 0.000 claims description 11
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- 229940126214 compound 3 Drugs 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 229930182912 cyclosporin Natural products 0.000 description 1
- 230000016396 cytokine production Effects 0.000 description 1
- 230000002939 deleterious effect Effects 0.000 description 1
- RCJVRSBWZCNNQT-UHFFFAOYSA-N dichloridooxygen Chemical compound ClOCl RCJVRSBWZCNNQT-UHFFFAOYSA-N 0.000 description 1
- VHQAZEHEYSOONS-UHFFFAOYSA-N diethyl 2-chloropyrimidine-4,5-dicarboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)N=C1C(=O)OCC VHQAZEHEYSOONS-UHFFFAOYSA-N 0.000 description 1
- TZLPKUXKDYPHIZ-UHFFFAOYSA-N diethyl 2-hydrazinylpyrimidine-4,5-dicarboxylate Chemical compound CCOC(=O)C1=CN=C(NN)N=C1C(=O)OCC TZLPKUXKDYPHIZ-UHFFFAOYSA-N 0.000 description 1
- KEYDXTIGCHRNQI-UHFFFAOYSA-N diethyl 2-oxo-1h-pyrimidine-5,6-dicarboxylate Chemical compound CCOC(=O)C=1C=NC(=O)NC=1C(=O)OCC KEYDXTIGCHRNQI-UHFFFAOYSA-N 0.000 description 1
- GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 description 1
- 230000004069 differentiation Effects 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000012636 effector Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 description 1
- JQOYOMIXBUJVDT-UHFFFAOYSA-N ethyl 2-(3,4-dichlorophenyl)-4-hydrazinylpyrimidine-5-carboxylate Chemical compound N1=C(NN)C(C(=O)OCC)=CN=C1C1=CC=C(Cl)C(Cl)=C1 JQOYOMIXBUJVDT-UHFFFAOYSA-N 0.000 description 1
- MHMKUBBBLBAAHH-UHFFFAOYSA-N ethyl 2-(3-nitrophenyl)-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1C1=CC=CC([N+]([O-])=O)=C1 MHMKUBBBLBAAHH-UHFFFAOYSA-N 0.000 description 1
- XNGGOXOLHQANRB-UHFFFAOYSA-N ethyl 2-(ethoxymethylidene)-4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC=C(C(=O)C(F)(F)F)C(=O)OCC XNGGOXOLHQANRB-UHFFFAOYSA-N 0.000 description 1
- XUKSJRKSODTRAU-UHFFFAOYSA-N ethyl 2-[(3,4-dichlorophenyl)methyl]-4-hydrazinylpyrimidine-5-carboxylate Chemical compound N1=C(NN)C(C(=O)OCC)=CN=C1CC1=CC=C(Cl)C(Cl)=C1 XUKSJRKSODTRAU-UHFFFAOYSA-N 0.000 description 1
- ISWSSLXYFANZND-UHFFFAOYSA-N ethyl 2-[(3,4-dichlorophenyl)methyl]-6-oxo-1h-pyrimidine-5-carboxylate Chemical compound N1=C(O)C(C(=O)OCC)=CN=C1CC1=CC=C(Cl)C(Cl)=C1 ISWSSLXYFANZND-UHFFFAOYSA-N 0.000 description 1
- PHGOABBHBPFWAN-UHFFFAOYSA-N ethyl 2-chloro-4-(1,1,2,2,2-pentafluoroethyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)N=C1C(F)(F)C(F)(F)F PHGOABBHBPFWAN-UHFFFAOYSA-N 0.000 description 1
- IEMKQRSOAOPKRJ-UHFFFAOYSA-N ethyl 2-chloropyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(Cl)N=C1 IEMKQRSOAOPKRJ-UHFFFAOYSA-N 0.000 description 1
- CPUUXQXDKMTFPW-UHFFFAOYSA-N ethyl 2-oxo-6-propyl-1h-pyrimidine-5-carboxylate Chemical compound CCCC1=NC(O)=NC=C1C(=O)OCC CPUUXQXDKMTFPW-UHFFFAOYSA-N 0.000 description 1
- WEZMBZKPZTUAFI-UHFFFAOYSA-N ethyl 3-(5-chlorothiophen-2-yl)-3-oxopropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=C(Cl)S1 WEZMBZKPZTUAFI-UHFFFAOYSA-N 0.000 description 1
- VKSDKUXHVLZDHO-UHFFFAOYSA-N ethyl 3-oxo-3-thiophen-2-ylpropanoate Chemical compound CCOC(=O)CC(=O)C1=CC=CS1 VKSDKUXHVLZDHO-UHFFFAOYSA-N 0.000 description 1
- KQWWVLVLVYYYDT-UHFFFAOYSA-N ethyl 3-oxohexanoate Chemical compound CCCC(=O)CC(=O)OCC KQWWVLVLVYYYDT-UHFFFAOYSA-N 0.000 description 1
- OCJKUQIPRNZDTK-UHFFFAOYSA-N ethyl 4,4,4-trifluoro-3-oxobutanoate Chemical compound CCOC(=O)CC(=O)C(F)(F)F OCJKUQIPRNZDTK-UHFFFAOYSA-N 0.000 description 1
- DSULCDCBENGHAX-UHFFFAOYSA-N ethyl 4-chloro-2-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C(F)(F)F)N=C1Cl DSULCDCBENGHAX-UHFFFAOYSA-N 0.000 description 1
- OXCOHZOBYCHKTH-UHFFFAOYSA-N ethyl 4-hydrazinyl-2-(3-nitrophenyl)pyrimidine-5-carboxylate Chemical compound N1=C(NN)C(C(=O)OCC)=CN=C1C1=CC=CC([N+]([O-])=O)=C1 OXCOHZOBYCHKTH-UHFFFAOYSA-N 0.000 description 1
- YINANUGXXFVGSM-UHFFFAOYSA-N ethyl 4-hydrazinyl-2-(trifluoromethyl)pyrimidine-5-carboxylate Chemical compound CCOC(=O)C1=CN=C(C(F)(F)F)N=C1NN YINANUGXXFVGSM-UHFFFAOYSA-N 0.000 description 1
- JSIHCFJCICVJHJ-UHFFFAOYSA-N ethyl 6-oxo-2-phenyl-1h-pyrimidine-5-carboxylate Chemical compound N1C(=O)C(C(=O)OCC)=CN=C1C1=CC=CC=C1 JSIHCFJCICVJHJ-UHFFFAOYSA-N 0.000 description 1
- XYIBRDXRRQCHLP-UHFFFAOYSA-N ethyl acetoacetate Chemical compound CCOC(=O)CC(C)=O XYIBRDXRRQCHLP-UHFFFAOYSA-N 0.000 description 1
- 125000005469 ethylenyl group Chemical group 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- 235000019634 flavors Nutrition 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000012737 fresh medium Substances 0.000 description 1
- 125000002541 furyl group Chemical group 0.000 description 1
- 230000002068 genetic effect Effects 0.000 description 1
- 208000024908 graft versus host disease Diseases 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 238000004128 high performance liquid chromatography Methods 0.000 description 1
- BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 238000000099 in vitro assay Methods 0.000 description 1
- 238000005462 in vivo assay Methods 0.000 description 1
- 230000002757 inflammatory effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229940102223 injectable solution Drugs 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 230000031146 intracellular signal transduction Effects 0.000 description 1
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 102000006240 membrane receptors Human genes 0.000 description 1
- 108020004084 membrane receptors Proteins 0.000 description 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 description 1
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 1
- HGJFHQSQYUYJCQ-UHFFFAOYSA-N methyl 2-chloro-4-(1,1,2,2,2-pentafluoroethyl)pyrimidine-5-carboxylate Chemical compound COC(=O)C1=CN=C(Cl)N=C1C(F)(F)C(F)(F)F HGJFHQSQYUYJCQ-UHFFFAOYSA-N 0.000 description 1
- JUQKVXRLRKKRPL-UHFFFAOYSA-N methyl 3-oxo-3-pyridin-3-ylpropanoate Chemical compound COC(=O)CC(=O)C1=CC=CN=C1 JUQKVXRLRKKRPL-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical group 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 230000008816 organ damage Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- KHPXUQMNIQBQEV-UHFFFAOYSA-L oxaloacetate(2-) Chemical compound [O-]C(=O)CC(=O)C([O-])=O KHPXUQMNIQBQEV-UHFFFAOYSA-L 0.000 description 1
- 125000002971 oxazolyl group Chemical group 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- HCTVWSOKIJULET-LQDWTQKMSA-M phenoxymethylpenicillin potassium Chemical compound [K+].N([C@H]1[C@H]2SC([C@@H](N2C1=O)C([O-])=O)(C)C)C(=O)COC1=CC=CC=C1 HCTVWSOKIJULET-LQDWTQKMSA-M 0.000 description 1
- 239000013641 positive control Substances 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000002062 proliferating effect Effects 0.000 description 1
- 230000009696 proliferative response Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000005470 propylenyl group Chemical group 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 239000003586 protic polar solvent Substances 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- HZMKWGOYWYBPRV-UHFFFAOYSA-N pyrimidine-4,5-dicarboxylic acid Chemical compound OC(=O)C1=CN=CN=C1C(O)=O HZMKWGOYWYBPRV-UHFFFAOYSA-N 0.000 description 1
- IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000003571 reporter gene assay Methods 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 238000011808 rodent model Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910000108 silver(I,III) oxide Inorganic materials 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 210000004988 splenocyte Anatomy 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 108091007196 stromelysin Proteins 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 150000003444 succinic acids Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- JHPCVUYMWCXICY-UHFFFAOYSA-N tert-butyl-[(4-ethyl-2-methylsulfanylpyrimidin-5-yl)methoxy]-dimethylsilane Chemical compound CCC1=NC(SC)=NC=C1CO[Si](C)(C)C(C)(C)C JHPCVUYMWCXICY-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 230000002103 transcriptional effect Effects 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 230000005951 type IV hypersensitivity Effects 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Immunology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Composés s'avérant utiles comme agents anti-inflammatoires d'une manière générale et, plus spécifiquement, pour la prévention et/ou le traitement des maladies immuno-inflammatoires et auto-immunes. Ces composés sont des composés contenant de la pyrimidine et, dans un mode de réalisation, sont des esters de celle-ci. L'invention porte également sur des méthodes de prévention et/ou de traitement des états inflammatoires par administration à un animal en ayant besoin d'une dose efficace d'un composé de cette invention, de préférence sous forme d'une composition pharmaceutique.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US310995P | 1995-09-01 | 1995-09-01 | |
| US60/003,109 | 1995-12-18 | ||
| US08/574,406 | 1995-12-18 | ||
| US08/574,406 US5852028A (en) | 1995-12-18 | 1995-12-18 | Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2230896A1 true CA2230896A1 (fr) | 1997-03-13 |
Family
ID=26671335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002230896A Abandoned CA2230896A1 (fr) | 1995-09-01 | 1996-08-30 | Carboxylates de pyrimidine, composes connexes et methodes de traitement des etats inflammatoires |
Country Status (4)
| Country | Link |
|---|---|
| JP (1) | JPH11512390A (fr) |
| AU (1) | AU726058B2 (fr) |
| CA (1) | CA2230896A1 (fr) |
| WO (1) | WO1997009325A1 (fr) |
Families Citing this family (37)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6245774B1 (en) | 1994-06-21 | 2001-06-12 | Celltech Therapeutics Limited | Tri-substituted phenyl or pyridine derivatives |
| US5935966A (en) * | 1995-09-01 | 1999-08-10 | Signal Pharmaceuticals, Inc. | Pyrimidine carboxylates and related compounds and methods for treating inflammatory conditions |
| US5939421A (en) * | 1997-07-01 | 1999-08-17 | Signal Pharmaceuticals, Inc. | Quinazoline analogs and related compounds and methods for treating inflammatory conditions |
| BR9908004A (pt) * | 1998-02-17 | 2001-12-18 | Tularik Inc | Composto, composição e método para prevençãoou supressão de uma infecção viral |
| ATE266662T1 (de) | 1998-07-22 | 2004-05-15 | Daiichi Suntory Pharma Co Ltd | Nf-kappa b inhibitoren, die indanderivate als aktiven bestandteil enthalten |
| ES2221414T3 (es) | 1998-08-27 | 2004-12-16 | Sumitomo Pharmaceuticals Company, Limited | Derivados de pirimidina. |
| GB9914258D0 (en) * | 1999-06-18 | 1999-08-18 | Celltech Therapeutics Ltd | Chemical compounds |
| AU7315400A (en) | 1999-09-17 | 2001-04-24 | Daiichi Suntory Pharma Co., Ltd | Preventives or remedies for myocarditis, dilated cardiomyopathy and cardiac insufficiency containing NF-kappab inhibitors as the active ingredient |
| EP1317450B1 (fr) | 2000-09-15 | 2006-11-22 | Vertex Pharmaceuticals Incorporated | Composes de pyrazole utiles comme inhibiteurs de proteine kinase |
| US7473691B2 (en) | 2000-09-15 | 2009-01-06 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| US6660731B2 (en) | 2000-09-15 | 2003-12-09 | Vertex Pharmaceuticals Incorporated | Pyrazole compounds useful as protein kinase inhibitors |
| NZ526472A (en) | 2000-12-21 | 2004-04-30 | Vertex Pharma | Pyrazole compounds useful as protein kinase inhibitors |
| MXPA03009378A (es) | 2001-04-13 | 2004-01-29 | Vertex Pharma | Inhibidores de cinasas c-jun n-terminales (jnk) y otras proteinas cinasas. |
| WO2002092087A1 (fr) * | 2001-05-11 | 2002-11-21 | Vertex Pharmaceuticals Incorporated | Derives de pyridine, pyrimidine, pyridazine 2,5-disubstitues et de 1, 2, 4-triazine utilises comme inhibiteurs de p38 |
| KR100874791B1 (ko) | 2001-05-29 | 2008-12-18 | 바이엘 쉐링 파마 악티엔게젤샤프트 | Ｃｄｋ-억제 피리미딘, 그의 제조방법 및 약제로서의 용도 |
| SE0104140D0 (sv) | 2001-12-07 | 2001-12-07 | Astrazeneca Ab | Novel Compounds |
| MY141867A (en) | 2002-06-20 | 2010-07-16 | Vertex Pharma | Substituted pyrimidines useful as protein kinase inhibitors |
| DK1532145T3 (da) | 2002-08-02 | 2007-01-15 | Vertex Pharma | Pyrazolpræparater der er anvendelige som inhibitorer af GSK-3 |
| WO2006115509A2 (fr) | 2004-06-24 | 2006-11-02 | Novartis Vaccines And Diagnostics Inc. | Immuno-potentialisateurs a petites molecules et analyses visant a detecter leur presence |
| PT1853588E (pt) | 2005-02-16 | 2008-08-25 | Astrazeneca Ab | Compostos químicos |
| EP1899323A2 (fr) | 2005-05-16 | 2008-03-19 | AstraZeneca AB | Dérivés de pyrazolylaminopyrimidine utiles comme inhibiteurs de tyrosine kinase |
| WO2007049041A1 (fr) | 2005-10-28 | 2007-05-03 | Astrazeneca Ab | Derives 4-(3-aminopyrazole)pyrimidine et leur utilisation en tant qu’inhibiteurs de tyrosine kinases dans le cadre d’un traitement anticancereux |
| EP1954277B1 (fr) | 2005-11-03 | 2017-01-18 | Vertex Pharmaceuticals Incorporated | Aminopyrimidines utiles en tant qu'inhibiteurs de kinases |
| GB0524427D0 (en) * | 2005-11-30 | 2006-01-11 | 7Tm Pharma As | Use of receptor ligands in threapy |
| AU2007208358A1 (en) | 2006-01-23 | 2007-08-02 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| EP2418210A1 (fr) | 2006-04-13 | 2012-02-15 | Vertex Pharmceuticals Incorporated | Thiophène-carboxamides servant d´inhibiteurs de protéines kinases |
| AU2007268056A1 (en) | 2006-05-23 | 2007-12-06 | Vertex Pharmaceuticals Incorporated | Thiophene-carboxamides useful as inhibitors of protein kinases |
| JP2009538309A (ja) | 2006-05-23 | 2009-11-05 | バーテックス ファーマシューティカルズ インコーポレイテッド | プロテインキナーゼのインヒビターとして有用なチオフェンカルボキサミド |
| JP2009542604A (ja) * | 2006-07-06 | 2009-12-03 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | ４−ヘテロシクロアルキルピリミジン、それらの調製方法及び医薬としての使用 |
| EP3088397B1 (fr) * | 2007-04-11 | 2019-04-10 | Canbas Co. Ltd. | Composés capables de supprimer le point de controle g2 du cycle cellulaire utile pour leur le traitement de cancer. |
| AU2008247592A1 (en) | 2007-05-02 | 2008-11-13 | Vertex Pharmaceuticals Incorporated | Thiazoles and pyrazoles useful as kinase inhibitors |
| UA99459C2 (en) | 2007-05-04 | 2012-08-27 | Астразенека Аб | 9-(pyrazol-3-yl)- 9h-purine-2-amine and 3-(pyraz0l-3-yl)-3h-imidazo[4,5-b]pyridin-5-amine derivatives and their use for the treatment of cancer |
| CN101790532B (zh) | 2007-07-31 | 2013-11-20 | 沃泰克斯药物股份有限公司 | 5-氟-1H-吡唑并[3，4-b]吡啶-3-胺及其衍生物的制备方法 |
| WO2010027921A1 (fr) | 2008-09-03 | 2010-03-11 | Vertex Pharmaceuticals Incorporated | Co-cristaux et formulations pharmaceutiques les comprenant |
| KR20120002581A (ko) | 2009-03-30 | 2012-01-06 | 아스텔라스세이야쿠 가부시키가이샤 | 피리미딘 화합물 |
| CN108148003B (zh) * | 2018-01-16 | 2021-03-26 | 棓诺(苏州)新材料有限公司 | Oled材料中间体苯甲酰嘧啶类化合物的合成方法 |
| CN117180122B (zh) * | 2023-11-02 | 2024-04-09 | 杭州湃肽生化科技有限公司 | 一种舒敏修复组合物及其应用 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4983608A (en) * | 1989-09-05 | 1991-01-08 | Hoechst-Roussell Pharmaceuticals, Inc. | N-substituted-4-pyrimidinamines and pyrimidinediamines |
-
1996
- 1996-08-30 CA CA002230896A patent/CA2230896A1/fr not_active Abandoned
- 1996-08-30 JP JP9511324A patent/JPH11512390A/ja active Pending
- 1996-08-30 AU AU70130/96A patent/AU726058B2/en not_active Ceased
- 1996-08-30 WO PCT/US1996/014089 patent/WO1997009325A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JPH11512390A (ja) | 1999-10-26 |
| WO1997009325A1 (fr) | 1997-03-13 |
| AU7013096A (en) | 1997-03-27 |
| AU726058B2 (en) | 2000-10-26 |
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