FR2516921A1 - Haloalkyl-8-4h-(1) benzopyran-4-ones, et procedes de preparation - Google Patents
Haloalkyl-8-4h-(1) benzopyran-4-ones, et procedes de preparation Download PDFInfo
- Publication number
- FR2516921A1 FR2516921A1 FR8122019A FR8122019A FR2516921A1 FR 2516921 A1 FR2516921 A1 FR 2516921A1 FR 8122019 A FR8122019 A FR 8122019A FR 8122019 A FR8122019 A FR 8122019A FR 2516921 A1 FR2516921 A1 FR 2516921A1
- Authority
- FR
- France
- Prior art keywords
- formula
- phenyl
- halogen
- lower alkyl
- methyl
- 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.)
- Granted
Links
- 238000002360 preparation method Methods 0.000 title claims description 9
- 238000000034 method Methods 0.000 title claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 21
- 150000002367 halogens Chemical class 0.000 claims abstract description 21
- -1 RADICAL PHENYL Chemical class 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 6
- 239000000575 pesticide Substances 0.000 claims abstract description 3
- 230000015572 biosynthetic process Effects 0.000 claims abstract 2
- 238000003786 synthesis reaction Methods 0.000 claims abstract 2
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- 239000000543 intermediate Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 150000002431 hydrogen Chemical group 0.000 claims description 9
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical class O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 claims description 5
- 150000002576 ketones Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- OTAFHZMPRISVEM-UHFFFAOYSA-N chromone Chemical class C1=CC=C2C(=O)C=COC2=C1 OTAFHZMPRISVEM-UHFFFAOYSA-N 0.000 claims description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 3
- 229930040373 Paraformaldehyde Natural products 0.000 claims description 3
- 238000009833 condensation Methods 0.000 claims description 3
- 230000005494 condensation Effects 0.000 claims description 3
- 229920006324 polyoxymethylene Polymers 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- 229910052708 sodium Inorganic materials 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical group [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052737 gold Inorganic materials 0.000 claims description 2
- 239000010931 gold Substances 0.000 claims description 2
- 150000004678 hydrides Chemical class 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- AIJULSRZWUXGPQ-UHFFFAOYSA-N Methylglyoxal Chemical class CC(=O)C=O AIJULSRZWUXGPQ-UHFFFAOYSA-N 0.000 claims 2
- 125000004076 pyridyl group Chemical group 0.000 claims 2
- SUNMBRGCANLOEG-UHFFFAOYSA-N 1,3-dichloroacetone Chemical class ClCC(=O)CCl SUNMBRGCANLOEG-UHFFFAOYSA-N 0.000 claims 1
- WAUNFWSVXRPCDQ-UHFFFAOYSA-N 1-(bromomethyl)-2-methoxybenzene Chemical compound COC1=CC=CC=C1CBr WAUNFWSVXRPCDQ-UHFFFAOYSA-N 0.000 claims 1
- YRNDGUSDBCARGC-UHFFFAOYSA-N 2-methoxyacetophenone Chemical class COCC(=O)C1=CC=CC=C1 YRNDGUSDBCARGC-UHFFFAOYSA-N 0.000 claims 1
- 101100532679 Caenorhabditis elegans scc-1 gene Proteins 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract 1
- 229940127557 pharmaceutical product Drugs 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 33
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- MTZQAGJQAFMTAQ-UHFFFAOYSA-N ethyl benzoate Chemical compound CCOC(=O)C1=CC=CC=C1 MTZQAGJQAFMTAQ-UHFFFAOYSA-N 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 description 4
- 229940095102 methyl benzoate Drugs 0.000 description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 238000007265 chloromethylation reaction Methods 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000013067 intermediate product Substances 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
- 235000017557 sodium bicarbonate Nutrition 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- JNXISTMARPWKRJ-UHFFFAOYSA-N 1-[5-(chloromethyl)-2-hydroxyphenyl]ethanone Chemical compound CC(=O)C1=CC(CCl)=CC=C1O JNXISTMARPWKRJ-UHFFFAOYSA-N 0.000 description 1
- MYFDIQHPLHDIJG-UHFFFAOYSA-N 1-chloro-3-(3-hydroxyphenyl)propan-2-one Chemical compound OC1=CC=CC(CC(=O)CCl)=C1 MYFDIQHPLHDIJG-UHFFFAOYSA-N 0.000 description 1
- UYDGECQHZQNTQS-UHFFFAOYSA-N 2-amino-4,6-dimethylpyridine-3-carboxamide Chemical compound CC1=CC(C)=C(C(N)=O)C(N)=N1 UYDGECQHZQNTQS-UHFFFAOYSA-N 0.000 description 1
- DTFKRVXLBCAIOZ-UHFFFAOYSA-N 2-methylanisole Chemical compound COC1=CC=CC=C1C DTFKRVXLBCAIOZ-UHFFFAOYSA-N 0.000 description 1
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241001331845 Equus asinus x caballus Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- CVQUWLDCFXOXEN-UHFFFAOYSA-N Pyran-4-one Chemical class O=C1C=COC=C1 CVQUWLDCFXOXEN-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- VJGNLOIQCWLBJR-UHFFFAOYSA-M benzyl(tributyl)azanium;chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CC1=CC=CC=C1 VJGNLOIQCWLBJR-UHFFFAOYSA-M 0.000 description 1
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000010779 crude oil Substances 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 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
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- WHSXTWFYRGOBGO-UHFFFAOYSA-N o-cresotic acid Natural products CC1=CC=CC(C(O)=O)=C1O WHSXTWFYRGOBGO-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- IMACFCSSMIZSPP-UHFFFAOYSA-N phenacyl chloride Chemical compound ClCC(=O)C1=CC=CC=C1 IMACFCSSMIZSPP-UHFFFAOYSA-N 0.000 description 1
- 239000012256 powdered iron Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229960002317 succinimide Drugs 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
- C07C65/21—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing ether groups, groups, groups, or groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/28—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only
- C07D311/30—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 2 only not hydrogenated in the hetero ring, e.g. flavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/22—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4
- C07D311/26—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3
- C07D311/34—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only
- C07D311/36—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring with oxygen or sulfur atoms directly attached in position 4 with aromatic rings attached in position 2 or 3 with aromatic rings attached in position 3 only not hydrogenated in the hetero ring, e.g. isoflavones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- 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
- C07D409/04—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 directly linked by a ring-member-to-ring-member bond
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrane Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Priority Applications (28)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8122019A FR2516921A1 (fr) | 1981-11-25 | 1981-11-25 | Haloalkyl-8-4h-(1) benzopyran-4-ones, et procedes de preparation |
| ZA828435A ZA828435B (en) | 1981-11-25 | 1982-11-16 | Haloalkyl-8-4h-(1)-benzopyran-4-ones and manufacturing procedures |
| IL67290A IL67290A0 (en) | 1981-11-25 | 1982-11-17 | 8-haloalkyl-4h-(1)-benzopyran-4-ones and their manufacture |
| IN847/DEL/82A IN158942B (enExample) | 1981-11-25 | 1982-11-18 | |
| IE2753/82A IE56916B1 (en) | 1981-11-25 | 1982-11-18 | 8-haloalkyl-4h-(1)-benzopyran-4-ones and manufacturing procedures |
| AU90728/82A AU563066B2 (en) | 1981-11-25 | 1982-11-19 | 8-haloalkyl-4h-benzo(b)pyran-4-ones |
| HU823763A HU194549B (en) | 1981-11-25 | 1982-11-23 | Process for producing 8-bromo-1-4-alkyl-4h-square bracket opened-1-square bracket closed-pyran-4-ones |
| PT75885A PT75885A (fr) | 1981-11-25 | 1982-11-23 | Procede de preparation d'haloalkyl-8-4h-<1>-benzopyran-4-ones |
| PT75886A PT75886A (fr) | 1981-11-25 | 1982-11-23 | Procede de preparation d'acides <oxo-4-4h<1>-benzopyran-8-yl> |
| AT82402136T ATE49760T1 (de) | 1981-11-25 | 1982-11-24 | 8-haloalkyl-4h-(1)-benzopyran-4-onen und verfahren zur herstellung. |
| NZ202595A NZ202595A (en) | 1981-11-25 | 1982-11-24 | 8-haloalkyl-4h-(1)-benzopyran-4-ones |
| MA19862A MA19649A1 (fr) | 1981-11-25 | 1982-11-24 | Procede de preparation d'haloalkyl-8-4h (1)-benzopyran-4-ones |
| NO823939A NO162463C (no) | 1981-11-25 | 1982-11-24 | Mellomprodukter for fremstilling av derivater av (okso-4-4h-(1)-benzopyran-8-yl)-eddiksyre. |
| DK522982A DK166778B1 (da) | 1981-11-25 | 1982-11-24 | 8-brommethyl-4-oe1aa-benzopyran-4-on-forbindelser og fremgangsmaader til fremstilling deraf |
| ES517636A ES8308322A1 (es) | 1981-11-25 | 1982-11-24 | Procedimiento de preparacion de haloalcohil-8-4h-(1)-benzo-piran-4-onas. |
| FR8219641A FR2536396A2 (fr) | 1981-11-25 | 1982-11-24 | Haloalkyl-8-4h-(1)-benzopyranones-4, et procedes de preparation |
| MX905882A MX155927A (es) | 1981-11-25 | 1982-11-24 | Procedimiento para preparar 8-bromoalquil 4-h-(1)benzopiran-4 onas |
| EP82402136A EP0080419B1 (fr) | 1981-11-25 | 1982-11-24 | Haloalkyl-8-4H-(1)-benzopyran-4-ones, et procédés de préparation |
| SU823515153A SU1189344A3 (ru) | 1981-11-25 | 1982-11-24 | Способ получени 8-бромметил-4-бензопиранонов |
| DE8282402136T DE3280092D1 (de) | 1981-11-25 | 1982-11-24 | 8-haloalkyl-4h-(1)-benzopyran-4-onen und verfahren zur herstellung. |
| CS828425A CS236696B2 (en) | 1981-11-25 | 1982-11-24 | Manufacturing process of 8-halogenalkyl-4h-(1)-benzopyran-4- |
| AR82291414A AR243249A1 (es) | 1981-11-25 | 1982-11-25 | Procedimiento para obtener derivados de acidos ¡oxo-4-4h-(1)-benzopiran-8-il¿alcanoicos, intermediarios de aplicacion exclusiva a dicho procedimiento y proceso para prepararlos. |
| JP57205581A JPS5896038A (ja) | 1981-11-25 | 1982-11-25 | ８―ブロモアルキル―４ｈ―〔１〕―ベンゾピラン―４―オン及びその製造法 |
| CA000416341A CA1197511A (fr) | 1981-11-25 | 1982-11-25 | Haloalkyl-8-4h-¬1|-benzopyran-4-ones, et procede de preparation |
| DD82245220A DD204920A5 (de) | 1981-11-25 | 1982-11-25 | Verfahren zur herstellung von 8-halogenalkyl-4h-(1)-benzopyran-4-onen |
| YU2648/82A YU43808B (en) | 1981-11-25 | 1982-11-25 | Process for obtaining haloalkyl-8-4h(1)-benzopyrane-4-one |
| OA57849A OA07256A (fr) | 1981-11-25 | 1982-11-25 | Halaolkyl-8-4H-(1)-benzopyran-4-ones,et procédés de préparation. |
| SU833644104A SU1232146A3 (ru) | 1981-11-25 | 1983-09-20 | Способ получени 8-4Н-(1)-бромметил-4-бензопиранонов |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8122019A FR2516921A1 (fr) | 1981-11-25 | 1981-11-25 | Haloalkyl-8-4h-(1) benzopyran-4-ones, et procedes de preparation |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FR2516921A1 true FR2516921A1 (fr) | 1983-05-27 |
| FR2516921B1 FR2516921B1 (enExample) | 1984-02-10 |
Family
ID=9264330
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FR8122019A Granted FR2516921A1 (fr) | 1981-11-25 | 1981-11-25 | Haloalkyl-8-4h-(1) benzopyran-4-ones, et procedes de preparation |
Country Status (24)
| Country | Link |
|---|---|
| EP (1) | EP0080419B1 (enExample) |
| JP (1) | JPS5896038A (enExample) |
| AR (1) | AR243249A1 (enExample) |
| AT (1) | ATE49760T1 (enExample) |
| AU (1) | AU563066B2 (enExample) |
| CA (1) | CA1197511A (enExample) |
| CS (1) | CS236696B2 (enExample) |
| DD (1) | DD204920A5 (enExample) |
| DE (1) | DE3280092D1 (enExample) |
| DK (1) | DK166778B1 (enExample) |
| ES (1) | ES8308322A1 (enExample) |
| FR (1) | FR2516921A1 (enExample) |
| HU (1) | HU194549B (enExample) |
| IE (1) | IE56916B1 (enExample) |
| IL (1) | IL67290A0 (enExample) |
| IN (1) | IN158942B (enExample) |
| MA (1) | MA19649A1 (enExample) |
| NO (1) | NO162463C (enExample) |
| NZ (1) | NZ202595A (enExample) |
| OA (1) | OA07256A (enExample) |
| PT (2) | PT75886A (enExample) |
| SU (2) | SU1189344A3 (enExample) |
| YU (1) | YU43808B (enExample) |
| ZA (1) | ZA828435B (enExample) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5002603A (en) * | 1989-12-04 | 1991-03-26 | Board Of Trustees Operating Michigan State University | Method and compositions for stimulating vesicular-arbuscular mycorrhizal fungi |
| WO1998027080A1 (en) * | 1996-12-19 | 1998-06-25 | Agrevo Uk Limited | Chromones useful as fungicides |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270567B (de) * | 1961-05-19 | 1968-06-20 | Klinge Co Chem Pharm Fab | Verfahren zur Herstellung von basisch substituierten Flavonen |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HU168753B (enExample) * | 1974-05-03 | 1976-07-28 | ||
| FR2326919A2 (fr) * | 1975-10-10 | 1977-05-06 | Lipha | Nouveaux acides inferieurs substitues par un radical chromonyle, leurs derives et leurs applications |
| FR2291745A1 (fr) * | 1974-11-20 | 1976-06-18 | Lipha | Nouveaux acides inferieurs substitues par un radical chromonyl, leurs derives et leurs applications |
| US3966770A (en) * | 1975-03-25 | 1976-06-29 | Smithkline Corporation | 4-Hydroxy-α-[(3,4-methylenedioxyphenyl)isopropylaminoethyl]-3-(methylsulfonylmethyl)benzyl alcohol |
| FR2392018A1 (fr) * | 1977-05-27 | 1978-12-22 | Seuref Ag | Derives de la 2,3-diphenyl-chromone, leur procede de preparation et leur application therapeutique |
| FR2517142A1 (fr) * | 1981-11-20 | 1983-05-27 | Efcis | Bascule bistable a stockage non volatil et a repositionnement statique |
-
1981
- 1981-11-25 FR FR8122019A patent/FR2516921A1/fr active Granted
-
1982
- 1982-11-16 ZA ZA828435A patent/ZA828435B/xx unknown
- 1982-11-17 IL IL67290A patent/IL67290A0/xx not_active IP Right Cessation
- 1982-11-18 IE IE2753/82A patent/IE56916B1/en not_active IP Right Cessation
- 1982-11-18 IN IN847/DEL/82A patent/IN158942B/en unknown
- 1982-11-19 AU AU90728/82A patent/AU563066B2/en not_active Ceased
- 1982-11-23 PT PT75886A patent/PT75886A/pt unknown
- 1982-11-23 PT PT75885A patent/PT75885A/pt unknown
- 1982-11-23 HU HU823763A patent/HU194549B/hu not_active IP Right Cessation
- 1982-11-24 NZ NZ202595A patent/NZ202595A/en unknown
- 1982-11-24 AT AT82402136T patent/ATE49760T1/de not_active IP Right Cessation
- 1982-11-24 NO NO823939A patent/NO162463C/no unknown
- 1982-11-24 ES ES517636A patent/ES8308322A1/es not_active Expired
- 1982-11-24 MA MA19862A patent/MA19649A1/fr unknown
- 1982-11-24 SU SU823515153A patent/SU1189344A3/ru active
- 1982-11-24 EP EP82402136A patent/EP0080419B1/fr not_active Expired - Lifetime
- 1982-11-24 DE DE8282402136T patent/DE3280092D1/de not_active Expired - Lifetime
- 1982-11-24 CS CS828425A patent/CS236696B2/cs unknown
- 1982-11-24 DK DK522982A patent/DK166778B1/da not_active IP Right Cessation
- 1982-11-25 JP JP57205581A patent/JPS5896038A/ja active Granted
- 1982-11-25 YU YU2648/82A patent/YU43808B/xx unknown
- 1982-11-25 CA CA000416341A patent/CA1197511A/fr not_active Expired
- 1982-11-25 DD DD82245220A patent/DD204920A5/de unknown
- 1982-11-25 OA OA57849A patent/OA07256A/xx unknown
- 1982-11-25 AR AR82291414A patent/AR243249A1/es active
-
1983
- 1983-09-20 SU SU833644104A patent/SU1232146A3/ru active
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1270567B (de) * | 1961-05-19 | 1968-06-20 | Klinge Co Chem Pharm Fab | Verfahren zur Herstellung von basisch substituierten Flavonen |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| ST | Notification of lapse |