CA1049539A - Substituted benzofuranyl esters - Google Patents
Substituted benzofuranyl estersInfo
- Publication number
- CA1049539A CA1049539A CA218,030A CA218030A CA1049539A CA 1049539 A CA1049539 A CA 1049539A CA 218030 A CA218030 A CA 218030A CA 1049539 A CA1049539 A CA 1049539A
- Authority
- CA
- Canada
- Prior art keywords
- dihydro
- dimethyl
- spp
- substituted
- methylaminosulfonate
- 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.)
- Expired
Links
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 title abstract 2
- -1 chloro- Chemical class 0.000 claims abstract description 51
- 125000002252 acyl group Chemical group 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000004429 atom Chemical group 0.000 claims abstract description 3
- 229910052751 metal Inorganic materials 0.000 claims abstract description 3
- 239000002184 metal Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 40
- MYMDOKBFMTVEGE-UHFFFAOYSA-N methylsulfamic acid Chemical compound CNS(O)(=O)=O MYMDOKBFMTVEGE-UHFFFAOYSA-N 0.000 claims description 9
- YGNOYUCUPMACDT-UHFFFAOYSA-N dimethylsulfamic acid Chemical compound CN(C)S(O)(=O)=O YGNOYUCUPMACDT-UHFFFAOYSA-N 0.000 claims description 4
- NXFNZLHFBJYCPG-UHFFFAOYSA-N diethylsulfamic acid Chemical compound CCN(CC)S(O)(=O)=O NXFNZLHFBJYCPG-UHFFFAOYSA-N 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- KHXCGHGLDPEALX-UHFFFAOYSA-N (2-ethoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) n-methylsulfamate Chemical group C1=C(OS(=O)(=O)NC)C=C2C(C)(C)C(OCC)OC2=C1 KHXCGHGLDPEALX-UHFFFAOYSA-N 0.000 claims 2
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims 1
- 230000002363 herbicidal effect Effects 0.000 abstract description 8
- 230000012010 growth Effects 0.000 abstract description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 150000003839 salts Chemical class 0.000 description 24
- 239000000243 solution Substances 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000002148 esters Chemical class 0.000 description 15
- 150000001408 amides Chemical class 0.000 description 14
- 239000004480 active ingredient Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 11
- 239000003921 oil Substances 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000002253 acid Substances 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000004009 herbicide Substances 0.000 description 8
- 229940086542 triethylamine Drugs 0.000 description 8
- 150000007513 acids Chemical class 0.000 description 7
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- SBODTLNLBKSNKD-UHFFFAOYSA-N 1-benzofuran-5-yl sulfamate Chemical class NS(=O)(=O)OC1=CC=C2OC=CC2=C1 SBODTLNLBKSNKD-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 150000001340 alkali metals Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000551547 Dione <red algae> Species 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 235000009432 Gossypium hirsutum Nutrition 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 240000008042 Zea mays Species 0.000 description 3
- 235000007244 Zea mays Nutrition 0.000 description 3
- LLYWQQAKIHNRLH-UHFFFAOYSA-N [5-(diethylsulfamoyloxy)-3,3-dimethyl-2h-1-benzofuran-2-yl] methyl carbonate Chemical compound CCN(CC)S(=O)(=O)OC1=CC=C2OC(OC(=O)OC)C(C)(C)C2=C1 LLYWQQAKIHNRLH-UHFFFAOYSA-N 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 239000013078 crystal Substances 0.000 description 3
- 239000006185 dispersion Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 235000012054 meals Nutrition 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- YBBYONHKWMHNRH-UHFFFAOYSA-N 2-methoxy-3,3-dimethyl-2h-1-benzofuran Chemical compound C1=CC=C2C(C)(C)C(OC)OC2=C1 YBBYONHKWMHNRH-UHFFFAOYSA-N 0.000 description 2
- 241000208173 Apiaceae Species 0.000 description 2
- 235000005781 Avena Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 244000000626 Daucus carota Species 0.000 description 2
- 235000002767 Daucus carota Nutrition 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 241000220485 Fabaceae Species 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241000208822 Lactuca Species 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 241000220259 Raphanus Species 0.000 description 2
- 241000220261 Sinapis Species 0.000 description 2
- 241000208292 Solanaceae Species 0.000 description 2
- 235000002634 Solanum Nutrition 0.000 description 2
- 241000207763 Solanum Species 0.000 description 2
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 2
- 244000062793 Sorghum vulgare Species 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
- 239000012346 acetyl chloride Substances 0.000 description 2
- 230000010933 acylation Effects 0.000 description 2
- 238000005917 acylation reaction Methods 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000000729 antidote Substances 0.000 description 2
- 229940075522 antidotes Drugs 0.000 description 2
- 239000003899 bactericide agent Substances 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
- 235000013877 carbamide Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 235000013339 cereals Nutrition 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 230000001276 controlling effect Effects 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000000417 fungicide Substances 0.000 description 2
- 239000003630 growth substance Substances 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 2
- FIYXUOWXHWJDAM-UHFFFAOYSA-N methyl sulfamate Chemical compound COS(N)(=O)=O FIYXUOWXHWJDAM-UHFFFAOYSA-N 0.000 description 2
- JRKMNAVWPZMFPI-UHFFFAOYSA-N methylsulfamoyl acetate Chemical compound CNS(=O)(=O)OC(C)=O JRKMNAVWPZMFPI-UHFFFAOYSA-N 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 239000012074 organic phase Substances 0.000 description 2
- SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical class OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 150000008318 pyrimidones Chemical group 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
- 150000003672 ureas Chemical class 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- KLXRFXPLKJOXOR-UHFFFAOYSA-N (2-hydroxy-1-benzofuran-5-yl) sulfamate Chemical class NS(=O)(=O)OC1=CC=C2OC(O)=CC2=C1 KLXRFXPLKJOXOR-UHFFFAOYSA-N 0.000 description 1
- SMRSBIUTPAOKEB-UHFFFAOYSA-N (2-hydroxy-3,3-dimethyl-2h-1-benzofuran-5-yl) n,n-dimethylsulfamate Chemical compound CN(C)S(=O)(=O)OC1=CC=C2OC(O)C(C)(C)C2=C1 SMRSBIUTPAOKEB-UHFFFAOYSA-N 0.000 description 1
- PGYHBRHWGFEYDZ-UHFFFAOYSA-N (2-hydroxy-3,3-dimethyl-2h-1-benzofuran-5-yl) n-methylsulfamate Chemical compound CNS(=O)(=O)OC1=CC=C2OC(O)C(C)(C)C2=C1 PGYHBRHWGFEYDZ-UHFFFAOYSA-N 0.000 description 1
- NCSQBAQBPRHHFN-UHFFFAOYSA-N (2-methoxy-3,3-dimethyl-2h-1-benzofuran-5-yl) n-methylsulfamate Chemical compound CNS(=O)(=O)OC1=CC=C2OC(OC)C(C)(C)C2=C1 NCSQBAQBPRHHFN-UHFFFAOYSA-N 0.000 description 1
- FMCAFXHLMUOIGG-JTJHWIPRSA-N (2s)-2-[[(2r)-2-[[(2s)-2-[[(2r)-2-formamido-3-sulfanylpropanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxy-2,5-dimethylphenyl)propanoyl]amino]-4-methylsulfanylbutanoic acid Chemical compound O=CN[C@@H](CS)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(=O)N[C@@H](CCSC)C(O)=O)CC1=CC(C)=C(O)C=C1C FMCAFXHLMUOIGG-JTJHWIPRSA-N 0.000 description 1
- FTDGDIFUDKDKAW-UHFFFAOYSA-N 1,1a,5,5a,6,6a-hexahydrocyclopropa[a]indene Chemical group C12C(CC3CC=CC=C13)C2 FTDGDIFUDKDKAW-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical class C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
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- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- OLPRIZQBWZMBAS-UHFFFAOYSA-N thiadiazolidine 1,1-dioxide Chemical class O=S1(=O)CCNN1 OLPRIZQBWZMBAS-UHFFFAOYSA-N 0.000 description 1
- 150000003582 thiophosphoric acids Chemical class 0.000 description 1
- 150000003585 thioureas Chemical group 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 150000003918 triazines Chemical group 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/82—Benzo [b] furans; Hydrogenated benzo [b] furans with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the hetero ring
- C07D307/83—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/78—Benzo [b] furans; Hydrogenated benzo [b] furans
- C07D307/79—Benzo [b] furans; Hydrogenated benzo [b] furans with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D307/80—Radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2402370A DE2402370A1 (de) | 1974-01-18 | 1974-01-18 | Substituierte benzofuranylester |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1049539A true CA1049539A (en) | 1979-02-27 |
Family
ID=5905110
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA218,030A Expired CA1049539A (en) | 1974-01-18 | 1975-01-16 | Substituted benzofuranyl esters |
Country Status (24)
| Country | Link |
|---|---|
| JP (1) | JPS50101533A (de) |
| AT (1) | AT339659B (de) |
| BE (1) | BE823879A (de) |
| BG (1) | BG25979A3 (de) |
| BR (1) | BR7500273A (de) |
| CA (1) | CA1049539A (de) |
| CH (1) | CH595754A5 (de) |
| CS (1) | CS181286B2 (de) |
| DD (1) | DD115561A5 (de) |
| DE (1) | DE2402370A1 (de) |
| DK (1) | DK632474A (de) |
| ES (1) | ES433918A1 (de) |
| FR (1) | FR2258385B1 (de) |
| GB (1) | GB1488575A (de) |
| HU (1) | HU171224B (de) |
| IL (1) | IL46287A (de) |
| IT (1) | IT1050270B (de) |
| LU (1) | LU71663A1 (de) |
| NL (1) | NL7500326A (de) |
| NO (1) | NO750140L (de) |
| PL (1) | PL91954B1 (de) |
| SE (1) | SE7500519L (de) |
| SU (1) | SU519108A3 (de) |
| ZA (1) | ZA75335B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6011024A (en) | 1991-08-28 | 2000-01-04 | Imperial College Of Science Technology & Medicine | Steroid sulphatase inhibitors |
| US6476011B1 (en) | 1991-08-28 | 2002-11-05 | Sterix Limited | Methods for introducing an estrogenic compound |
| US6903084B2 (en) | 1991-08-29 | 2005-06-07 | Sterix Limited | Steroid sulphatase inhibitors |
| GB2331988B (en) * | 1997-12-04 | 2003-04-16 | Imperial College | Polycyclic sulphamate inhibitors or oestrone sulphatase |
| US7335650B2 (en) | 2000-01-14 | 2008-02-26 | Sterix Limited | Composition |
-
1974
- 1974-01-18 DE DE2402370A patent/DE2402370A1/de not_active Withdrawn
- 1974-12-05 DK DK632474A patent/DK632474A/da unknown
- 1974-12-19 IL IL46287A patent/IL46287A/xx unknown
- 1974-12-20 FR FR7442348A patent/FR2258385B1/fr not_active Expired
- 1974-12-23 JP JP49146898A patent/JPS50101533A/ja active Pending
- 1974-12-27 BE BE151944A patent/BE823879A/xx unknown
-
1975
- 1975-01-10 NL NL7500326A patent/NL7500326A/xx not_active Application Discontinuation
- 1975-01-15 BR BR273/75A patent/BR7500273A/pt unknown
- 1975-01-15 CH CH44275A patent/CH595754A5/xx not_active IP Right Cessation
- 1975-01-15 IT IT47690/75A patent/IT1050270B/it active
- 1975-01-15 BG BG028725A patent/BG25979A3/xx unknown
- 1975-01-16 DD DD183665A patent/DD115561A5/xx unknown
- 1975-01-16 HU HU75BA00003190A patent/HU171224B/hu unknown
- 1975-01-16 PL PL1975177378A patent/PL91954B1/pl unknown
- 1975-01-16 LU LU71663A patent/LU71663A1/xx unknown
- 1975-01-16 SU SU2097790A patent/SU519108A3/ru active
- 1975-01-16 CA CA218,030A patent/CA1049539A/en not_active Expired
- 1975-01-17 ES ES433918A patent/ES433918A1/es not_active Expired
- 1975-01-17 ZA ZA00750335A patent/ZA75335B/xx unknown
- 1975-01-17 SE SE7500519A patent/SE7500519L/xx unknown
- 1975-01-17 AT AT33675A patent/AT339659B/de not_active IP Right Cessation
- 1975-01-17 NO NO750140A patent/NO750140L/no unknown
- 1975-01-17 CS CS7500000357A patent/CS181286B2/cs unknown
- 1975-01-17 GB GB2067/75A patent/GB1488575A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| SE7500519L (sv) | 1975-07-21 |
| BG25979A3 (bg) | 1979-01-12 |
| ES433918A1 (es) | 1976-11-16 |
| PL91954B1 (de) | 1977-03-31 |
| ATA33675A (de) | 1977-02-15 |
| IL46287A0 (en) | 1975-03-13 |
| IT1050270B (it) | 1981-03-10 |
| DD115561A5 (de) | 1975-10-12 |
| HU171224B (hu) | 1977-12-28 |
| FR2258385A1 (de) | 1975-08-18 |
| CH595754A5 (de) | 1978-02-28 |
| BE823879A (fr) | 1975-06-27 |
| IL46287A (en) | 1978-03-10 |
| AT339659B (de) | 1977-11-10 |
| FR2258385B1 (de) | 1978-11-03 |
| CS181286B2 (en) | 1978-03-31 |
| LU71663A1 (de) | 1975-06-24 |
| SU519108A3 (ru) | 1976-06-25 |
| AU7660074A (en) | 1976-06-24 |
| ZA75335B (en) | 1976-01-28 |
| GB1488575A (en) | 1977-10-12 |
| DK632474A (de) | 1975-10-13 |
| NO750140L (de) | 1975-08-11 |
| NL7500326A (nl) | 1975-07-22 |
| JPS50101533A (de) | 1975-08-12 |
| BR7500273A (pt) | 1975-11-04 |
| DE2402370A1 (de) | 1975-07-31 |
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