NO312898B1 - Nye pyrimidon-derivater med fungicid aktivitet - Google Patents
Nye pyrimidon-derivater med fungicid aktivitet Download PDFInfo
- Publication number
- NO312898B1 NO312898B1 NO19971470A NO971470A NO312898B1 NO 312898 B1 NO312898 B1 NO 312898B1 NO 19971470 A NO19971470 A NO 19971470A NO 971470 A NO971470 A NO 971470A NO 312898 B1 NO312898 B1 NO 312898B1
- Authority
- NO
- Norway
- Prior art keywords
- arom
- methyl
- group
- hydroxy
- propyl
- Prior art date
Links
- 230000000855 fungicidal effect Effects 0.000 title description 5
- 150000008318 pyrimidones Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 144
- 238000000034 method Methods 0.000 claims abstract description 80
- 150000003839 salts Chemical class 0.000 claims abstract description 24
- 238000011282 treatment Methods 0.000 claims abstract description 23
- 208000031888 Mycoses Diseases 0.000 claims abstract description 16
- 239000012453 solvate Substances 0.000 claims abstract description 13
- 206010017533 Fungal infection Diseases 0.000 claims abstract description 10
- 230000008569 process Effects 0.000 claims abstract description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 91
- -1 polymethylene chain Polymers 0.000 claims description 63
- QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 claims description 52
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
- 239000000203 mixture Substances 0.000 claims description 38
- 239000001257 hydrogen Substances 0.000 claims description 26
- 229910052739 hydrogen Inorganic materials 0.000 claims description 26
- 239000002253 acid Substances 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical group 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
- 241001465754 Metazoa Species 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims description 6
- 238000011321 prophylaxis Methods 0.000 claims description 6
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 6
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 5
- 125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
- 125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 5
- 101100516568 Caenorhabditis elegans nhr-7 gene Proteins 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 4
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 4
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 150000002905 orthoesters Chemical class 0.000 claims description 4
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- HRMGALKSLBVZTP-MPBGBICISA-N 7-bromo-3-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]quinazolin-4-one Chemical compound C([C@@](O)([C@H](N1C(C2=CC=C(Br)C=C2N=C1)=O)C)C=1C(=CC(F)=CC=1)F)N1C=NC=N1 HRMGALKSLBVZTP-MPBGBICISA-N 0.000 claims description 3
- 239000003905 agrochemical Substances 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000004943 pyrimidin-6-yl group Chemical group N1=CN=CC=C1* 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- JLJNPNJUCJBBID-JBEBIEQOSA-N 3-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-6-(4-fluorophenyl)thieno[3,2-d]pyrimidin-4-one Chemical compound S1C=2C(=O)N([C@H](C)[C@](O)(CN3N=CN=C3)C=3C(=CC(F)=CC=3)F)C=NC=2C=C1C1=CC=C(F)C=C1 JLJNPNJUCJBBID-JBEBIEQOSA-N 0.000 claims description 2
- YVSHSNVCDHMWRD-MPBGBICISA-N 3-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-7-iodoquinazolin-4-one Chemical compound C([C@@](O)([C@H](N1C(C2=CC=C(I)C=C2N=C1)=O)C)C=1C(=CC(F)=CC=1)F)N1C=NC=N1 YVSHSNVCDHMWRD-MPBGBICISA-N 0.000 claims description 2
- SKPJJXUPZWECHZ-OYLFLEFRSA-N 6-(4-fluorophenyl)-3-[(2r,3r)-3-(2-fluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound S1C=2C(=O)N([C@H](C)[C@](O)(CN3N=CN=C3)C=3C(=CC=CC=3)F)C=NC=2C=C1C1=CC=C(F)C=C1 SKPJJXUPZWECHZ-OYLFLEFRSA-N 0.000 claims description 2
- FFYOYKVTRBNPDK-ZUOKHONESA-N 7-chloro-3-[(2r,3r)-3-(2-fluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]quinazolin-4-one Chemical compound C([C@@](O)([C@H](N1C(C2=CC=C(Cl)C=C2N=C1)=O)C)C=1C(=CC=CC=1)F)N1C=NC=N1 FFYOYKVTRBNPDK-ZUOKHONESA-N 0.000 claims description 2
- 101100294115 Caenorhabditis elegans nhr-4 gene Proteins 0.000 claims description 2
- UHIXWHUVLCAJQL-MPBGBICISA-N albaconazole Chemical compound C([C@@](O)([C@H](N1C(C2=CC=C(Cl)C=C2N=C1)=O)C)C=1C(=CC(F)=CC=1)F)N1C=NC=N1 UHIXWHUVLCAJQL-MPBGBICISA-N 0.000 claims description 2
- 125000004674 methylcarbonyl group Chemical group CC(=O)* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- NNNPFIIPSHWMIR-SGANQWHYSA-N 3-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]-6-(4-methylsulfonylphenyl)thieno[3,2-d]pyrimidin-4-one Chemical compound S1C=2C(=O)N([C@H](C)[C@](O)(CN3N=CN=C3)C=3C(=CC(F)=CC=3)F)C=NC=2C=C1C1=CC=C(S(C)(=O)=O)C=C1 NNNPFIIPSHWMIR-SGANQWHYSA-N 0.000 claims 1
- FSKFOGDDOUMDPE-JBEBIEQOSA-N 6-(4-chlorophenyl)-3-[(2r,3r)-3-(2,4-difluorophenyl)-3-hydroxy-4-(1,2,4-triazol-1-yl)butan-2-yl]thieno[3,2-d]pyrimidin-4-one Chemical compound S1C=2C(=O)N([C@H](C)[C@](O)(CN3N=CN=C3)C=3C(=CC(F)=CC=3)F)C=NC=2C=C1C1=CC=C(Cl)C=C1 FSKFOGDDOUMDPE-JBEBIEQOSA-N 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 11
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- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 229910052763 palladium Inorganic materials 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
- UNEIHNMKASENIG-UHFFFAOYSA-N para-chlorophenylpiperazine Chemical compound C1=CC(Cl)=CC=C1N1CCNCC1 UNEIHNMKASENIG-UHFFFAOYSA-N 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
- 229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 235000010413 sodium alginate Nutrition 0.000 description 1
- 239000000661 sodium alginate Substances 0.000 description 1
- 229940005550 sodium alginate Drugs 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
- 229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229960002668 sodium chloride Drugs 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- XDFGPVSVSMWVQE-UHFFFAOYSA-M sodium;dodecanoic acid;hydrogen sulfate Chemical compound [Na+].OS([O-])(=O)=O.CCCCCCCCCCCC(O)=O XDFGPVSVSMWVQE-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000008223 sterile water Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 239000003351 stiffener Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 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
- XGOSYNSWSRUASG-UHFFFAOYSA-H trisodium;2-[[2-[bis(carboxylatomethyl)amino]-3-[(4,4-diphenylcyclohexyl)oxy-oxidophosphoryl]oxypropyl]-[2-[bis(carboxylatomethyl)amino]ethyl]amino]acetate;gadolinium(3+) Chemical compound [Na+].[Na+].[Na+].[Gd+3].C1CC(OP([O-])(=O)OCC(CN(CCN(CC([O-])=O)CC([O-])=O)CC(=O)[O-])N(CC([O-])=O)CC([O-])=O)CCC1(C=1C=CC=CC=1)C1=CC=CC=C1 XGOSYNSWSRUASG-UHFFFAOYSA-H 0.000 description 1
- 210000001215 vagina Anatomy 0.000 description 1
- 239000000522 vaginal cream Substances 0.000 description 1
- 239000000003 vaginal tablet Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000009736 wetting Methods 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- 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
- C07D403/06—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 carbon chain containing only aliphatic carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES9501564A ES2107376B1 (es) | 1995-08-02 | 1995-08-02 | Nuevos derivados de pirimidona con actividad antifungica. |
ES9600646A ES2120885B1 (es) | 1996-03-15 | 1996-03-15 | Nuevas tienopirimidonas con actividad antifungica. |
PCT/EP1996/003420 WO1997005130A1 (en) | 1995-08-02 | 1996-08-02 | New pyrimidone derivatives with antifungal activity |
Publications (3)
Publication Number | Publication Date |
---|---|
NO971470L NO971470L (no) | 1997-04-01 |
NO971470D0 NO971470D0 (no) | 1997-04-01 |
NO312898B1 true NO312898B1 (no) | 2002-07-15 |
Family
ID=26154906
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19971470A NO312898B1 (no) | 1995-08-02 | 1997-04-01 | Nye pyrimidon-derivater med fungicid aktivitet |
Country Status (16)
Country | Link |
---|---|
US (1) | US5807854A (de) |
EP (1) | EP0783501B9 (de) |
JP (1) | JP4049207B2 (de) |
KR (1) | KR100423590B1 (de) |
AT (1) | ATE198593T1 (de) |
AU (1) | AU6870396A (de) |
BR (1) | BR9606547A (de) |
CA (1) | CA2201477C (de) |
DE (1) | DE69611512T2 (de) |
DK (1) | DK0783501T3 (de) |
ES (1) | ES2153975T3 (de) |
GR (1) | GR3035621T3 (de) |
MX (1) | MX9702382A (de) |
NO (1) | NO312898B1 (de) |
PT (1) | PT783501E (de) |
WO (1) | WO1997005130A1 (de) |
Families Citing this family (31)
Publication number | Priority date | Publication date | Assignee | Title |
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AU5871000A (en) * | 1999-06-11 | 2001-01-02 | Paul G. Abrams | High dose radionuclide complexes for bone marrow suppression |
US7094885B2 (en) * | 1999-07-11 | 2006-08-22 | Neorx Corporation | Skeletal-targeted radiation to treat bone-associated pathologies |
ES2159488B1 (es) * | 2000-03-07 | 2002-04-16 | Uriach & Cia Sa J | Procedimiento para la preparacion de derivados de pirimidona con actividad antifungica. |
JP2004501913A (ja) | 2000-06-23 | 2004-01-22 | ブリストル−マイヤーズ スクイブ ファーマ カンパニー | ヘテロアリール−フェニル置換Xa因子阻害剤 |
WO2002062398A2 (en) | 2001-01-08 | 2002-08-15 | Neorx Corporation | Radioactively labelled conjugates of phosphonates |
PA8539401A1 (es) * | 2001-02-14 | 2002-10-28 | Warner Lambert Co | Quinazolinas como inhibidores de mmp-13 |
HUP0303249A3 (en) | 2001-02-22 | 2007-03-28 | Sankyo Co | Water-soluble triazole fungicide compounds and pharmaceutical compositions containing them |
US8329924B2 (en) * | 2001-06-11 | 2012-12-11 | Vertex Pharmaceuticals (Canada) Incorporated | Compounds and methods for the treatment or prevention of Flavivirus infections |
SK288015B6 (sk) * | 2001-06-11 | 2012-11-05 | Virochem Pharma Inc. | Thiophene derivatives as antiviral agents for flavivirus infection |
AU2002364552A1 (en) | 2001-12-13 | 2003-06-30 | Dow Global Technologies Inc. | Treatment of osteomyelitis with radiopharmaceuticals |
EP1534070A4 (de) * | 2002-08-20 | 2008-07-09 | Doren M Pinnel | Verfahren zur behandlung von pilzinfektionen |
CN100413861C (zh) | 2002-12-10 | 2008-08-27 | 维勒凯姆制药股份有限公司 | 用于治疗或预防黄病毒感染的化合物 |
JP5055263B2 (ja) * | 2005-03-30 | 2012-10-24 | ダエウン ファーマシューティカル カンパニー リミテッド | 抗真菌性トリアゾール誘導体 |
JP5132069B2 (ja) * | 2006-03-31 | 2013-01-30 | 三井化学アグロ株式会社 | 3−(ジヒドロ(又はテトラヒドロ)イソキノリン−1−イル)キノリン化合物を含む医薬用抗真菌剤 |
EP2009009A1 (de) * | 2007-06-26 | 2008-12-31 | Palau Pharma, S.A. | Antifungale Kristallverbindungen |
EP1887004A1 (de) * | 2006-08-07 | 2008-02-13 | Palau Pharma, S.A. | Kristalline Formen von (1R,2R)-7-Chloro-3-[2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]chinazolin-4(3H)-on |
BRPI0716026A2 (pt) * | 2006-08-07 | 2013-08-06 | Stiefel Laboratories | compostos antiféngicos cristalinos |
NZ576780A (en) | 2006-11-15 | 2011-12-22 | Virochem Pharma Inc | Thiophene analogues for the treatment or prevention of flavivirus infections |
UY30892A1 (es) | 2007-02-07 | 2008-09-02 | Smithkline Beckman Corp | Inhibidores de la actividad akt |
US20080255161A1 (en) * | 2007-04-11 | 2008-10-16 | Dmitry Koltun | 3-HYDROQUINAZOLIN-4-ONE DERIVATIVES FOR USE AS STEAROYL CoA DESATURASE INHIBITORS |
EP2257555B1 (de) | 2008-03-03 | 2012-07-04 | National Chemical Laboratory | Thieno[2,3-d]-pyrimidin-4(3h)-on-verbindungen mit antimykotischen eigenschaften und verfahren dafür |
ES2548998T3 (es) * | 2009-05-29 | 2015-10-22 | Palau Pharma, S.A. | Composiciones antifúngicas de azol |
US9655363B2 (en) * | 2013-02-04 | 2017-05-23 | Syngenta Participations Ag | Microbiocides |
TW201636329A (zh) | 2015-02-02 | 2016-10-16 | 佛瑪治療公司 | 作為hdac抑制劑之雙環[4,6,0]異羥肟酸 |
US10112915B2 (en) | 2015-02-02 | 2018-10-30 | Forma Therapeutics, Inc. | 3-aryl bicyclic [4,5,0] hydroxamic acids as HDAC inhibitors |
EA025187B1 (ru) * | 2015-04-17 | 2016-11-30 | Тагир Аббасели оглы Сулейманов | Производное дитиокарбамата 2-((4-(4-метилпиперазин-1-ил)фенил)амино)-2-оксоетил4-этилпиперазин-1-карбодитиоат, обладающее антифунгальной активностью |
WO2017009751A1 (en) | 2015-07-15 | 2017-01-19 | Pfizer Inc. | Pyrimidine derivatives |
US10555935B2 (en) | 2016-06-17 | 2020-02-11 | Forma Therapeutics, Inc. | 2-spiro-5- and 6-hydroxamic acid indanes as HDAC inhibitors |
CN110997646B (zh) | 2017-08-10 | 2023-06-20 | 住友化学株式会社 | 环氧醇化合物的制造方法 |
CN111018839B (zh) * | 2019-12-02 | 2022-12-23 | 中国人民解放军第二军医大学 | 三氮唑醇类衍生物及其制备方法和应用 |
WO2023118082A1 (en) | 2021-12-22 | 2023-06-29 | Palau Pharma, S.L.U. | Multiparticulate albaconazole composition |
Family Cites Families (4)
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US4482558A (en) * | 1982-06-18 | 1984-11-13 | Pfizer Inc. | Antifungal amide and urea derivatives of (3-amino-2-aryl-2-hydroxyprop-1-yl)-1H-1,2,4-triazoles |
EP0293500A1 (de) * | 1987-06-01 | 1988-12-07 | American Cyanamid Company | 3-Heteroalkyl-2,4-quinazolinedione, 3-Heteroaryl-1,2,3-benzotriazin-4(3H)-one, 3-Heteroarylalkyl-4-quinazolinon |
GB8819308D0 (en) * | 1988-08-13 | 1988-09-14 | Pfizer Ltd | Triazole antifungal agents |
TW218017B (de) * | 1992-04-28 | 1993-12-21 | Takeda Pharm Industry Co Ltd |
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1996
- 1996-08-02 BR BR9606547A patent/BR9606547A/pt not_active IP Right Cessation
- 1996-08-02 ES ES96929201T patent/ES2153975T3/es not_active Expired - Lifetime
- 1996-08-02 DE DE69611512T patent/DE69611512T2/de not_active Expired - Lifetime
- 1996-08-02 MX MX9702382A patent/MX9702382A/es unknown
- 1996-08-02 AT AT96929201T patent/ATE198593T1/de active
- 1996-08-02 EP EP96929201A patent/EP0783501B9/de not_active Expired - Lifetime
- 1996-08-02 KR KR1019970701515A patent/KR100423590B1/ko not_active IP Right Cessation
- 1996-08-02 US US08/809,967 patent/US5807854A/en not_active Expired - Lifetime
- 1996-08-02 CA CA002201477A patent/CA2201477C/en not_active Expired - Lifetime
- 1996-08-02 JP JP50725497A patent/JP4049207B2/ja not_active Expired - Lifetime
- 1996-08-02 WO PCT/EP1996/003420 patent/WO1997005130A1/en active IP Right Grant
- 1996-08-02 PT PT96929201T patent/PT783501E/pt unknown
- 1996-08-02 DK DK96929201T patent/DK0783501T3/da active
- 1996-08-02 AU AU68703/96A patent/AU6870396A/en not_active Abandoned
-
1997
- 1997-04-01 NO NO19971470A patent/NO312898B1/no not_active IP Right Cessation
-
2001
- 2001-03-23 GR GR20010400466T patent/GR3035621T3/el unknown
Also Published As
Publication number | Publication date |
---|---|
GR3035621T3 (en) | 2001-06-29 |
PT783501E (pt) | 2001-04-30 |
BR9606547A (pt) | 1997-10-14 |
WO1997005130A1 (en) | 1997-02-13 |
MX9702382A (es) | 1998-02-28 |
ATE198593T1 (de) | 2001-01-15 |
JP4049207B2 (ja) | 2008-02-20 |
KR970705558A (ko) | 1997-10-09 |
AU6870396A (en) | 1997-02-26 |
EP0783501B1 (de) | 2001-01-10 |
ES2153975T3 (es) | 2001-03-16 |
EP0783501A1 (de) | 1997-07-16 |
CA2201477C (en) | 2005-05-03 |
US5807854A (en) | 1998-09-15 |
JPH10508317A (ja) | 1998-08-18 |
DE69611512T2 (de) | 2001-05-31 |
DK0783501T3 (da) | 2001-01-29 |
NO971470L (no) | 1997-04-01 |
NO971470D0 (no) | 1997-04-01 |
DE69611512D1 (de) | 2001-02-15 |
CA2201477A1 (en) | 1997-02-13 |
EP0783501B9 (de) | 2001-07-25 |
KR100423590B1 (ko) | 2004-09-10 |
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MK1K | Patent expired |