HU200588B - Process for producing keto esters - Google Patents
Process for producing keto esters Download PDFInfo
- Publication number
- HU200588B HU200588B HU562085A HU562085A HU200588B HU 200588 B HU200588 B HU 200588B HU 562085 A HU562085 A HU 562085A HU 562085 A HU562085 A HU 562085A HU 200588 B HU200588 B HU 200588B
- Authority
- HU
- Hungary
- Prior art keywords
- optionally substituted
- formula
- alkyl
- phenyl
- alkenyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract description 10
- 125000000468 ketone group Chemical group 0.000 title 1
- 238000002360 preparation method Methods 0.000 claims abstract description 11
- 150000001875 compounds Chemical class 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 239000001257 hydrogen Substances 0.000 claims abstract description 6
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 5
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 3
- -1 nitro-phenoxy, phenyl Chemical group 0.000 claims description 14
- 239000011777 magnesium Substances 0.000 claims description 8
- 229910052749 magnesium Inorganic materials 0.000 claims description 8
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052744 lithium Inorganic materials 0.000 claims description 4
- 150000002641 lithium Chemical group 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 150000002902 organometallic compounds Chemical class 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 2
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 3
- 150000003891 oxalate salts Chemical class 0.000 claims 3
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 150000002736 metal compounds Chemical class 0.000 claims 1
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 239000000417 fungicide Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical class OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 abstract 1
- 241000233866 Fungi Species 0.000 abstract 1
- 101100134925 Gallus gallus COR6 gene Proteins 0.000 abstract 1
- 125000004442 acylamino group Chemical group 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000004438 haloalkoxy group Chemical group 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 150000002825 nitriles Chemical class 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 125000005017 substituted alkenyl group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 125000004426 substituted alkynyl group Chemical group 0.000 abstract 1
- 239000012808 vapor phase Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- 239000000203 mixture Substances 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000000284 extract Substances 0.000 description 5
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- TWDVUMVJBKRSEU-UHFFFAOYSA-N 1-(2-bromophenyl)-2-phenylethanol Chemical compound C=1C=CC=C(Br)C=1C(O)CC1=CC=CC=C1 TWDVUMVJBKRSEU-UHFFFAOYSA-N 0.000 description 3
- 239000007818 Grignard reagent Substances 0.000 description 3
- 238000005481 NMR spectroscopy Methods 0.000 description 3
- 239000003480 eluent Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 150000004795 grignard reagents Chemical class 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- FRBANDMAHCQSMS-UHFFFAOYSA-N 1-bromo-2-(2-phenylethenyl)benzene Chemical group BrC1=CC=CC=C1C=CC1=CC=CC=C1 FRBANDMAHCQSMS-UHFFFAOYSA-N 0.000 description 2
- BYHXJDDDSHSQKQ-UHFFFAOYSA-N 1-bromo-2-(2-phenylethyl)benzene Chemical compound BrC1=CC=CC=C1CCC1=CC=CC=C1 BYHXJDDDSHSQKQ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- AQRLNPVMDITEJU-UHFFFAOYSA-N triethylsilane Chemical compound CC[SiH](CC)CC AQRLNPVMDITEJU-UHFFFAOYSA-N 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- FRBANDMAHCQSMS-ZHACJKMWSA-N 1-bromo-2-[(e)-2-phenylethenyl]benzene Chemical group BrC1=CC=CC=C1\C=C\C1=CC=CC=C1 FRBANDMAHCQSMS-ZHACJKMWSA-N 0.000 description 1
- NDOPHXWIAZIXPR-UHFFFAOYSA-N 2-bromobenzaldehyde Chemical compound BrC1=CC=CC=C1C=O NDOPHXWIAZIXPR-UHFFFAOYSA-N 0.000 description 1
- 125000006276 2-bromophenyl group Chemical group [H]C1=C([H])C(Br)=C(*)C([H])=C1[H] 0.000 description 1
- 238000003747 Grignard reaction Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- USFRYJRPHFMVBZ-UHFFFAOYSA-M benzyl(triphenyl)phosphanium;chloride Chemical compound [Cl-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C=1C=CC=CC=1)CC1=CC=CC=C1 USFRYJRPHFMVBZ-UHFFFAOYSA-M 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000004440 column chromatography Methods 0.000 description 1
- 125000002933 cyclohexyloxy group Chemical group C1(CCCCC1)O* 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 150000002642 lithium compounds Chemical class 0.000 description 1
- SCEZYJKGDJPHQO-UHFFFAOYSA-M magnesium;methanidylbenzene;chloride Chemical compound [Mg+2].[Cl-].[CH2-]C1=CC=CC=C1 SCEZYJKGDJPHQO-UHFFFAOYSA-M 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- FRGVAJRTNQISSH-UHFFFAOYSA-N methyl 2-oxo-2-(2-phenoxyphenyl)acetate Chemical compound COC(=O)C(=O)C1=CC=CC=C1OC1=CC=CC=C1 FRGVAJRTNQISSH-UHFFFAOYSA-N 0.000 description 1
- QPXNOLLNTSDXKJ-VAWYXSNFSA-N methyl 2-oxo-2-[2-[(e)-2-phenylethenyl]phenyl]acetate Chemical compound COC(=O)C(=O)C1=CC=CC=C1\C=C\C1=CC=CC=C1 QPXNOLLNTSDXKJ-VAWYXSNFSA-N 0.000 description 1
- QPXNOLLNTSDXKJ-QXMHVHEDSA-N methyl 2-oxo-2-[2-[(z)-2-phenylethenyl]phenyl]acetate Chemical compound COC(=O)C(=O)C1=CC=CC=C1\C=C/C1=CC=CC=C1 QPXNOLLNTSDXKJ-QXMHVHEDSA-N 0.000 description 1
- MZRVEZGGRBJDDB-UHFFFAOYSA-N n-Butyllithium Substances [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003901 oxalic acid esters Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Lubricants (AREA)
Abstract
Die Erfindung betrifft als Fungizide nuetzliche Derivate von Acrylsaeure und Verfahren zu deren Herstellung. Mit der Erfindung werden Fungizide bereitgestellt, die in das Pflanzengewebe eindringen und sie koennen so fluechtig sein, dass sie in der Dampfphase gegen auf den Pflanzen befindliche Pilze wirksam sind. Sie koennen sowohl in der Landwirtschaft als auch in der Industrie eingesetzt werden. Die Aufgabe der Erfindung besteht darin, als Fungizide nuetzliche Verbindungen und deren Herstellungsverfahren zur Verfuegung zu stellen, die vielseitig einsetzbar sind. Die erfindungsgemaessen Verbindungen besitzen die allgemeine Formel und Stereoisomere davon, worin X, Y und Z, die gleich oder unterschiedlich sein koennen, Wasserstoff- oder Halogenatome, oder wahlweise substituierte Alkyl-, wahlweise substituierte Alkenyl-, wahlweise substituierte Aryl-, wahlweise substituierte Alkynyl-, Halogenalkyl-, Alkoxy-, Halogenalkoxy-, wahlweise substituierte Aryloxy-, wahlweise substituierte Arylalkoxy-, wahlweise substituierte Acyloxy, wahlweise substituierte Amino-, wahlweise substituierte Arylazo-, Acylamino-, Nitro-, Nitril-, CO2R3-, CONR4R5-, COR6-, CR7NR8- oder NCR9R10-Gruppen sind; oder sich die Gruppen X und Y, wenn sie sich in benachbarten Stellungen am Phenylring befinden, zur Bildung eines kondensierten Ringes vereinigen koennen, der entweder aromatisch oder aliphatisch ist und wahlweise ein oder mehrere Heteroatome enthaelt; und R1, R2, R3, R4, R5, R6, R7, R8, R9 und R10, die gleich oder unterschiedlich sein koennen, Wasserstoffatome oder Alkyl-, Cycloalkyl-, Alkenyl-, Alkynyl-, wahlweise substituierte Aryl-, wahlweise substituierte Aralkyl- oder Cycloalkylalkylgruppen sind; und Metallkomplexe davon. Formel
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8426473A GB8426473D0 (en) | 1984-10-19 | 1984-10-19 | Fungicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU200588B true HU200588B (en) | 1990-07-28 |
Family
ID=10568441
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU562085A HU200588B (en) | 1984-10-19 | 1985-10-16 | Process for producing keto esters |
| HU561985A HU200586B (en) | 1984-10-19 | 1985-10-16 | Process for producing beta-hydroxyacrylic acid esters |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU561985A HU200586B (en) | 1984-10-19 | 1985-10-16 | Process for producing beta-hydroxyacrylic acid esters |
Country Status (9)
| Country | Link |
|---|---|
| DD (2) | DD260491A5 (de) |
| GB (1) | GB8426473D0 (de) |
| GE (1) | GEP19971045B (de) |
| HU (2) | HU200588B (de) |
| LT (2) | LT2162B (de) |
| LV (1) | LV5120A3 (de) |
| SU (1) | SU1600628A3 (de) |
| UA (1) | UA6299A1 (de) |
| ZA (1) | ZA857814B (de) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6428654B1 (en) * | 2000-04-05 | 2002-08-06 | Hercules Incorporated | Fungicidal method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3025368A1 (de) | 1980-07-04 | 1982-01-28 | Hoechst Ag, 6000 Frankfurt | Verfahren zur synthese von strobilurin |
-
1984
- 1984-10-19 GB GB8426473A patent/GB8426473D0/en active Pending
-
1985
- 1985-10-09 ZA ZA857814A patent/ZA857814B/xx unknown
- 1985-10-16 HU HU562085A patent/HU200588B/hu not_active IP Right Cessation
- 1985-10-16 HU HU561985A patent/HU200586B/hu not_active IP Right Cessation
- 1985-10-17 DD DD29984785A patent/DD260491A5/de unknown
- 1985-10-17 DD DD85281843A patent/DD241998A5/de unknown
- 1985-10-18 UA UA4027600A patent/UA6299A1/uk unknown
-
1986
- 1986-06-04 SU SU864027600A patent/SU1600628A3/ru active
-
1992
- 1992-12-07 LV LV920256A patent/LV5120A3/xx unknown
-
1993
- 1993-03-05 LT LTRP393A patent/LT2162B/xx not_active IP Right Cessation
- 1993-09-09 LT LTIP960A patent/LT3867B/lt not_active IP Right Cessation
-
1994
- 1994-01-20 GE GEAP19941733A patent/GEP19971045B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| LV5120A3 (lv) | 1993-06-10 |
| DD241998A5 (de) | 1987-01-14 |
| LTIP960A (en) | 1995-03-27 |
| LT2162B (lt) | 1993-10-15 |
| LT3867B (en) | 1996-04-25 |
| GB8426473D0 (en) | 1984-11-28 |
| GEP19971045B (en) | 1997-11-26 |
| UA6299A1 (uk) | 1994-12-29 |
| HU200586B (en) | 1990-07-28 |
| DD260491A5 (de) | 1988-09-28 |
| SU1600628A3 (ru) | 1990-10-15 |
| ZA857814B (en) | 1986-06-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| HPC4 | Succession in title of patentee |
Owner name: ZENECA LTD. OF IMPERIAL CHEMICAL HOUSE, GB |
|
| HMM4 | Cancellation of final prot. due to non-payment of fee |