SK280976B6 - O-nitrofenylcyklopropylketón a spôsob jeho výroby - Google Patents
O-nitrofenylcyklopropylketón a spôsob jeho výroby Download PDFInfo
- Publication number
- SK280976B6 SK280976B6 SK694-93A SK69493A SK280976B6 SK 280976 B6 SK280976 B6 SK 280976B6 SK 69493 A SK69493 A SK 69493A SK 280976 B6 SK280976 B6 SK 280976B6
- Authority
- SK
- Slovakia
- Prior art keywords
- ketone
- solvent
- nitrobenzoyl
- dihydro
- furanone
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 34
- QNQWJIPOLNMFSY-UHFFFAOYSA-N cyclopropyl-(2-nitrophenyl)methanone Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1CC1 QNQWJIPOLNMFSY-UHFFFAOYSA-N 0.000 title claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 12
- 238000004519 manufacturing process Methods 0.000 claims abstract description 11
- -1 o-nitrobenzoyl halide Chemical class 0.000 claims abstract description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 8
- 229910000039 hydrogen halide Inorganic materials 0.000 claims abstract description 6
- 239000012433 hydrogen halide Substances 0.000 claims abstract description 6
- 239000011777 magnesium Substances 0.000 claims abstract description 5
- 229910052749 magnesium Inorganic materials 0.000 claims abstract description 5
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 47
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
- HMOJKUDFFLOQTN-UHFFFAOYSA-N (2-aminophenyl)-cyclopropylmethanone Chemical compound NC1=CC=CC=C1C(=O)C1CC1 HMOJKUDFFLOQTN-UHFFFAOYSA-N 0.000 claims description 6
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
- 239000002585 base Substances 0.000 claims description 6
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 229910000042 hydrogen bromide Inorganic materials 0.000 claims description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims 2
- 229910001854 alkali hydroxide Inorganic materials 0.000 claims 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 claims 1
- 239000001095 magnesium carbonate Substances 0.000 claims 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 claims 1
- DENGFQGYWOTGAK-UHFFFAOYSA-N magnesium;hydrobromide Chemical compound [Mg].Br DENGFQGYWOTGAK-UHFFFAOYSA-N 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- OMQHDIHZSDEIFH-UHFFFAOYSA-N 3-Acetyldihydro-2(3H)-furanone Chemical compound CC(=O)C1CCOC1=O OMQHDIHZSDEIFH-UHFFFAOYSA-N 0.000 abstract description 4
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 abstract description 3
- RHDGNLCLDBVESU-UHFFFAOYSA-N but-3-en-4-olide Chemical compound O=C1CC=CO1 RHDGNLCLDBVESU-UHFFFAOYSA-N 0.000 abstract description 3
- 239000004009 herbicide Substances 0.000 abstract description 3
- 150000002576 ketones Chemical class 0.000 abstract description 3
- HJJMZFWWAYITCI-UHFFFAOYSA-N 3-(2-nitrobenzoyl)oxolan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1C(=O)OCC1 HJJMZFWWAYITCI-UHFFFAOYSA-N 0.000 abstract description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 17
- 239000000047 product Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 7
- 238000002955 isolation Methods 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 6
- 238000004128 high performance liquid chromatography Methods 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 5
- 238000004458 analytical method Methods 0.000 description 5
- 230000020176 deacylation Effects 0.000 description 5
- 238000005947 deacylation reaction Methods 0.000 description 5
- 239000012074 organic phase Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- BWWHTIHDQBHTHP-UHFFFAOYSA-N 2-nitrobenzoyl chloride Chemical compound [O-][N+](=O)C1=CC=CC=C1C(Cl)=O BWWHTIHDQBHTHP-UHFFFAOYSA-N 0.000 description 3
- IAMWJPYZDMLFMP-UHFFFAOYSA-N 3-(2-nitrobenzoyl)-3h-furan-2-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)C1C(=O)OC=C1 IAMWJPYZDMLFMP-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 230000002378 acidificating effect Effects 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 239000002699 waste material Substances 0.000 description 3
- DQOZBWRNTWGQKC-UHFFFAOYSA-N 4-bromo-1-(2-nitrophenyl)butan-1-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)CCCBr DQOZBWRNTWGQKC-UHFFFAOYSA-N 0.000 description 2
- VSDZBKACHGJLHP-UHFFFAOYSA-N 4-chloro-1-(2-nitrophenyl)butan-1-one Chemical compound [O-][N+](=O)C1=CC=CC=C1C(=O)CCCCl VSDZBKACHGJLHP-UHFFFAOYSA-N 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000908 ammonium hydroxide Substances 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- BNOVYBVKWYHEMQ-UHFFFAOYSA-N (4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(N)=O)=N1 BNOVYBVKWYHEMQ-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 241000196324 Embryophyta Species 0.000 description 1
- 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 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 description 1
- 238000006114 decarboxylation reaction Methods 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- HHFAWKCIHAUFRX-UHFFFAOYSA-N ethoxide Chemical compound CC[O-] HHFAWKCIHAUFRX-UHFFFAOYSA-N 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000026030 halogenation Effects 0.000 description 1
- 238000005658 halogenation reaction Methods 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004811 liquid chromatography Methods 0.000 description 1
- CRGZYKWWYNQGEC-UHFFFAOYSA-N magnesium;methanolate Chemical compound [Mg+2].[O-]C.[O-]C CRGZYKWWYNQGEC-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000010815 organic waste Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- OJXASOYYODXRPT-UHFFFAOYSA-N sulfamoylurea Chemical class NC(=O)NS(N)(=O)=O OJXASOYYODXRPT-UHFFFAOYSA-N 0.000 description 1
- 150000003613 toluenes Chemical class 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- 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
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/26—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D307/30—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D307/32—Oxygen atoms
- C07D307/33—Oxygen atoms in position 2, the oxygen atom being in its keto or unsubstituted enol form
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/45—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by at least one doubly—bound oxygen atom, not being part of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Plural Heterocyclic Compounds (AREA)
- Furan Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US90925892A | 1992-07-06 | 1992-07-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SK69493A3 SK69493A3 (en) | 1994-06-08 |
| SK280976B6 true SK280976B6 (sk) | 2000-10-09 |
Family
ID=25426905
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SK694-93A SK280976B6 (sk) | 1992-07-06 | 1993-06-30 | O-nitrofenylcyklopropylketón a spôsob jeho výroby |
Country Status (21)
| Country | Link |
|---|---|
| US (2) | US5364968A (cs) |
| EP (1) | EP0577945B1 (cs) |
| JP (1) | JP3626763B2 (cs) |
| KR (1) | KR100284119B1 (cs) |
| CN (1) | CN1040640C (cs) |
| AT (1) | ATE141254T1 (cs) |
| AU (1) | AU665096B2 (cs) |
| BR (1) | BR9302740A (cs) |
| CA (1) | CA2099537C (cs) |
| CZ (2) | CZ286391B6 (cs) |
| DE (1) | DE69303996T2 (cs) |
| DK (1) | DK0577945T3 (cs) |
| ES (1) | ES2090764T3 (cs) |
| GR (1) | GR3020804T3 (cs) |
| HU (1) | HU214818B (cs) |
| IL (1) | IL106216A (cs) |
| MX (1) | MX9303956A (cs) |
| SG (1) | SG47553A1 (cs) |
| SK (1) | SK280976B6 (cs) |
| TW (1) | TW226362B (cs) |
| ZA (1) | ZA934818B (cs) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CZ289916B6 (cs) * | 1993-11-30 | 2002-04-17 | American Cyanamid Company | Způsob výroby o-aminofenylketonů |
| US5414136A (en) * | 1994-04-29 | 1995-05-09 | American Cyanamid | Method for the preparation of 4-halo-2'-nitrobutyrophenone compounds |
| US5492884A (en) * | 1994-04-29 | 1996-02-20 | American Cyanamid Company | 1-[2-(cyclopropylcarbonyl)-4-fluorophenyl]sulfamoyl)-3-(4,6-dimethoxy-2-pyrimidinyl) urea and its herbicidal method of use |
| US6127576A (en) * | 1996-12-20 | 2000-10-03 | American Cyanamid Company | Aminophenyl ketone derivatives and a method for the preparation thereof |
| US5856576A (en) * | 1997-02-04 | 1999-01-05 | American Cyanamid Company | Aryne intermediates and a process for the preparation thereof |
| ES2151270T3 (es) * | 1997-05-14 | 2000-12-16 | Basf Ag | Procedimiento para la obtencion de polimeros de estireno expandibles que contienen particulas de grafito. |
| IL140925A0 (en) * | 1998-07-23 | 2002-02-10 | Nissan Chemical Ind Ltd | Process for producing 2-aminobenzophenone compound |
| US6369276B1 (en) | 1998-11-19 | 2002-04-09 | Eagleview Technologies, Inc. | Catalyst structure for ketone production and method of making and using the same |
| US6392099B1 (en) | 1998-11-19 | 2002-05-21 | Eagleview Technologies, Inc. | Method and apparatus for the preparation of ketones |
| RU2150271C1 (ru) * | 1999-10-13 | 2000-06-10 | Тверская медакадемия | Способ лечения хронического гастрита, язвенной болезни желудка и двенадцатиперстной кишки |
| US6545185B1 (en) | 2001-03-29 | 2003-04-08 | Eagleview Technologies, Inc. | Preparation of ketones from aldehydes |
| CN109206323A (zh) * | 2017-07-07 | 2019-01-15 | 上海现代制药股份有限公司 | 一种萘胺药物中间体的制备方法 |
| KR102538844B1 (ko) * | 2018-12-21 | 2023-06-01 | 주식회사 엘지화학 | 방향족 비닐 화합물-비닐시안 화합물 공중합체의 제조방법 및 이를 포함하는 열가소성 수지 조성물의 제조방법 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3268533A (en) * | 1964-06-11 | 1966-08-23 | American Home Prod | 4-aminophenylcyclopropyl ketones |
| FR2244473A1 (en) * | 1973-09-26 | 1975-04-18 | Biosedra Lab | Cyclopropyl phenyl ketones - with anticonvulsant, diuretic, antiinflammatory and hypotensive activity |
| FI60559C (fi) * | 1975-07-17 | 1982-02-10 | Sumitomo Chemical Co | Foerfarande foer framstaellning av ny-(tertiaer amino)-orto-aminobutyrofenonfoereningar |
| US5009699A (en) * | 1990-06-22 | 1991-04-23 | American Cyanamid Company | 1-{[O-(cyclopropylcarbonyl)phenyl]sulfamoyl}-3-(4,6-dimethoxy-2-pyrimidinyl)urea herbicidal composition and use |
| US5107023A (en) * | 1990-06-22 | 1992-04-21 | American Cyanamid Company | 0-Aminophenyl cyclopropyl ketone intermediate |
| IE75693B1 (en) * | 1990-07-10 | 1997-09-10 | Janssen Pharmaceutica Nv | HIV-inhibiting benzeneacetamide derivatives |
-
1993
- 1993-05-06 DK DK93107325.8T patent/DK0577945T3/da active
- 1993-05-06 EP EP93107325A patent/EP0577945B1/en not_active Expired - Lifetime
- 1993-05-06 AT AT93107325T patent/ATE141254T1/de not_active IP Right Cessation
- 1993-05-06 SG SG1996002814A patent/SG47553A1/en unknown
- 1993-05-06 DE DE69303996T patent/DE69303996T2/de not_active Expired - Lifetime
- 1993-05-06 ES ES93107325T patent/ES2090764T3/es not_active Expired - Lifetime
- 1993-05-13 TW TW082103751A patent/TW226362B/zh active
- 1993-06-11 CN CN93106624A patent/CN1040640C/zh not_active Expired - Fee Related
- 1993-06-28 CZ CZ19931288A patent/CZ286391B6/cs not_active IP Right Cessation
- 1993-06-30 MX MX9303956A patent/MX9303956A/es not_active IP Right Cessation
- 1993-06-30 JP JP18337393A patent/JP3626763B2/ja not_active Expired - Fee Related
- 1993-06-30 SK SK694-93A patent/SK280976B6/sk unknown
- 1993-07-02 BR BR9302740A patent/BR9302740A/pt not_active IP Right Cessation
- 1993-07-02 IL IL10621693A patent/IL106216A/en not_active IP Right Cessation
- 1993-07-02 CA CA002099537A patent/CA2099537C/en not_active Expired - Fee Related
- 1993-07-05 HU HU9301949A patent/HU214818B/hu not_active IP Right Cessation
- 1993-07-05 KR KR1019930012545A patent/KR100284119B1/ko not_active Expired - Fee Related
- 1993-07-05 ZA ZA934818A patent/ZA934818B/xx unknown
- 1993-07-05 AU AU41759/93A patent/AU665096B2/en not_active Ceased
- 1993-12-02 US US08/161,382 patent/US5364968A/en not_active Expired - Lifetime
-
1994
- 1994-08-09 US US08/287,733 patent/US5453545A/en not_active Expired - Lifetime
-
1996
- 1996-08-16 GR GR960400232T patent/GR3020804T3/el unknown
-
1999
- 1999-07-12 CZ CZ19992462A patent/CZ286450B6/cs not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPH0672967A (ja) | 1994-03-15 |
| CN1040640C (zh) | 1998-11-11 |
| GR3020804T3 (en) | 1996-11-30 |
| DK0577945T3 (da) | 1996-09-02 |
| EP0577945B1 (en) | 1996-08-14 |
| ZA934818B (en) | 1994-01-20 |
| SG47553A1 (en) | 1998-04-17 |
| ATE141254T1 (de) | 1996-08-15 |
| AU665096B2 (en) | 1995-12-14 |
| TW226362B (cs) | 1994-07-11 |
| CZ286391B6 (cs) | 2000-03-15 |
| US5364968A (en) | 1994-11-15 |
| IL106216A0 (en) | 1993-11-15 |
| IL106216A (en) | 1998-10-30 |
| HUT66804A (en) | 1994-12-28 |
| CZ286450B6 (en) | 2000-04-12 |
| US5453545A (en) | 1995-09-26 |
| AU4175993A (en) | 1994-01-13 |
| HK1001050A1 (en) | 1998-05-22 |
| CA2099537A1 (en) | 1994-01-07 |
| CN1083045A (zh) | 1994-03-02 |
| SK69493A3 (en) | 1994-06-08 |
| MX9303956A (es) | 1994-01-31 |
| KR100284119B1 (ko) | 2001-04-02 |
| JP3626763B2 (ja) | 2005-03-09 |
| EP0577945A1 (en) | 1994-01-12 |
| HU214818B (hu) | 1998-10-28 |
| HU9301949D0 (en) | 1993-09-28 |
| DE69303996T2 (de) | 1997-02-27 |
| CA2099537C (en) | 2003-09-23 |
| ES2090764T3 (es) | 1996-10-16 |
| KR940005547A (ko) | 1994-03-21 |
| DE69303996D1 (de) | 1996-09-19 |
| CZ128893A3 (en) | 1994-02-16 |
| BR9302740A (pt) | 1994-02-16 |
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