JP2011509960A - 新規なピリダジン誘導体 - Google Patents

Info

Publication number

JP2011509960A

JP2011509960A JP2010542575A JP2010542575A JP2011509960A JP 2011509960 A JP2011509960 A JP 2011509960A JP 2010542575 A JP2010542575 A JP 2010542575A JP 2010542575 A JP2010542575 A JP 2010542575A JP 2011509960 A JP2011509960 A JP 2011509960A

Authority

JP

Japan

Prior art keywords

formula

chloro

compound

pyridazine

methyl

Prior art date

2008-01-16

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.)

Withdrawn

Links

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• 150000004892 pyridazines Chemical class 0.000 title abstract description 27
• 150000001875 compounds Chemical class 0.000 claims abstract description 156
• -1 R 3 is H Chemical group 0.000 claims abstract description 63
• 150000003839 salts Chemical group 0.000 claims abstract description 21
• 239000004480 active ingredient Substances 0.000 claims abstract description 20
• 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 18
• 125000001309 chloro group Chemical group Cl* 0.000 claims abstract description 15
• 230000000855 fungicidal effect Effects 0.000 claims abstract description 12
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 6
• 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
• 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
• 125000001246 bromo group Chemical group Br* 0.000 claims abstract description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
• 239000000203 mixture Substances 0.000 claims description 74
• 238000000034 method Methods 0.000 claims description 30
• 230000003032 phytopathogenic effect Effects 0.000 claims description 24
• 244000005700 microbiome Species 0.000 claims description 15
• 206010028980 Neoplasm Diseases 0.000 claims description 13
• 201000011510 cancer Diseases 0.000 claims description 13
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
• 238000011282 treatment Methods 0.000 claims description 12
• 239000002671 adjuvant Substances 0.000 claims description 10
• 208000015181 infectious disease Diseases 0.000 claims description 10
• 239000000463 material Substances 0.000 claims description 10
• 230000008569 process Effects 0.000 claims description 10
• 238000002360 preparation method Methods 0.000 claims description 9
• MIFYOIXYERDEFA-UHFFFAOYSA-N 3-chloro-4-(2-chloro-6-fluorophenyl)-5-(6-chloropyridin-3-yl)-6-methylpyridazine Chemical compound CC1=NN=C(Cl)C(C=2C(=CC=CC=2F)Cl)=C1C1=CC=C(Cl)N=C1 MIFYOIXYERDEFA-UHFFFAOYSA-N 0.000 claims description 6
• KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 6
• WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 claims description 6
• JMOPKVSTPKVPCM-UHFFFAOYSA-N 5-(6-chloropyridin-3-yl)-3-methoxy-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine Chemical compound FC=1C=C(F)C=C(F)C=1C=1C(OC)=NN=C(C)C=1C1=CC=C(Cl)N=C1 JMOPKVSTPKVPCM-UHFFFAOYSA-N 0.000 claims description 5
• 239000003814 drug Substances 0.000 claims description 5
• 235000018927 edible plant Nutrition 0.000 claims description 5
• 230000002538 fungal effect Effects 0.000 claims description 5
• 238000004519 manufacturing process Methods 0.000 claims description 5
• JHUJOLGJUWFVEW-UHFFFAOYSA-N 3-chloro-5-(6-chloropyridin-3-yl)-6-ethyl-4-(2,4,6-trifluorophenyl)pyridazine Chemical compound C=1C=C(Cl)N=CC=1C=1C(CC)=NN=C(Cl)C=1C1=C(F)C=C(F)C=C1F JHUJOLGJUWFVEW-UHFFFAOYSA-N 0.000 claims description 4
• 239000003937 drug carrier Substances 0.000 claims description 4
• FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 4
• HNUVLXKGSPOLIZ-UHFFFAOYSA-N 3-chloro-5-(5,6-dichloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine Chemical compound C=1N=C(Cl)C(Cl)=CC=1C=1C(C)=NN=C(Cl)C=1C1=C(F)C=C(F)C=C1F HNUVLXKGSPOLIZ-UHFFFAOYSA-N 0.000 claims description 3
• 239000012620 biological material Substances 0.000 claims description 3
• 150000003857 carboxamides Chemical class 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• ZZSFTDMIAMHSCX-UHFFFAOYSA-N 3-chloro-5-(6-chloropyridin-3-yl)-4-(2,6-difluoro-4-methoxyphenyl)-6-methylpyridazine Chemical compound FC1=CC(OC)=CC(F)=C1C1=C(Cl)N=NC(C)=C1C1=CC=C(Cl)N=C1 ZZSFTDMIAMHSCX-UHFFFAOYSA-N 0.000 claims description 2
• JUEUZZSZOUXVIZ-UHFFFAOYSA-N 3-chloro-5-(6-chloropyridin-3-yl)-6-propan-2-yl-4-(2,4,6-trifluorophenyl)pyridazine Chemical compound C=1C=C(Cl)N=CC=1C=1C(C(C)C)=NN=C(Cl)C=1C1=C(F)C=C(F)C=C1F JUEUZZSZOUXVIZ-UHFFFAOYSA-N 0.000 claims description 2
• NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 claims description 2
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
• DKVNPHBNOWQYFE-UHFFFAOYSA-N carbamodithioic acid Chemical compound NC(S)=S DKVNPHBNOWQYFE-UHFFFAOYSA-N 0.000 claims description 2
• 150000002429 hydrazines Chemical class 0.000 claims description 2
• 229910052760 oxygen Inorganic materials 0.000 claims description 2
• 239000001301 oxygen Substances 0.000 claims description 2
• HZGCZRCZOMANHK-UHFFFAOYSA-N pyrimidin-2-ylmethanol Chemical compound OCC1=NC=CC=N1 HZGCZRCZOMANHK-UHFFFAOYSA-N 0.000 claims description 2
• YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 claims description 2
• KXDAEFPNCMNJSK-UHFFFAOYSA-N Benzamide Chemical compound NC(=O)C1=CC=CC=C1 KXDAEFPNCMNJSK-UHFFFAOYSA-N 0.000 claims 3
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims 2
• HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 claims 1
• IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical compound OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 claims 1
• 239000005749 Copper compound Substances 0.000 claims 1
• WLLGXSLBOPFWQV-UHFFFAOYSA-N MGK 264 Chemical compound C1=CC2CC1C1C2C(=O)N(CC(CC)CCCC)C1=O WLLGXSLBOPFWQV-UHFFFAOYSA-N 0.000 claims 1
• 150000001880 copper compounds Chemical class 0.000 claims 1
• XGXNTJHZPBRBHJ-UHFFFAOYSA-N n-phenylpyrimidin-2-amine Chemical compound N=1C=CC=NC=1NC1=CC=CC=C1 XGXNTJHZPBRBHJ-UHFFFAOYSA-N 0.000 claims 1
• PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims 1
• LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims 1
• 239000003905 agrochemical Substances 0.000 abstract description 3
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• 238000009472 formulation Methods 0.000 description 24
• 238000012360 testing method Methods 0.000 description 21
• 241000233866 Fungi Species 0.000 description 17
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
• 239000005648 plant growth regulator Substances 0.000 description 13
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
• PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 11
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• 239000000243 solution Substances 0.000 description 10
• DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
• 206010017533 Fungal infection Diseases 0.000 description 8
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• 0 *c(cc1*)cc(*)c1-c(c(*)nnc1*)c1-c(cc1*)cnc1Cl Chemical compound *c(cc1*)cc(*)c1-c(c(*)nnc1*)c1-c(cc1*)cnc1Cl 0.000 description 6
• GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 6
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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• 239000003826 tablet Substances 0.000 description 5
• 235000007688 Lycopersicon esculentum Nutrition 0.000 description 4
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 4
• JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 4
• IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• 230000009471 action Effects 0.000 description 4
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• HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
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