DD150056A5 - Verfahren zur herstellung von 5(3)-hydroxypyrazolen - Google Patents
Verfahren zur herstellung von 5(3)-hydroxypyrazolen Download PDFInfo
- Publication number
- DD150056A5 DD150056A5 DD78220132A DD22013278A DD150056A5 DD 150056 A5 DD150056 A5 DD 150056A5 DD 78220132 A DD78220132 A DD 78220132A DD 22013278 A DD22013278 A DD 22013278A DD 150056 A5 DD150056 A5 DD 150056A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- halogen
- formula
- phenyl
- alkyl
- preparation
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 16
- 238000002360 preparation method Methods 0.000 claims abstract description 14
- 125000005843 halogen group Chemical group 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims abstract description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 10
- 150000002367 halogens Chemical group 0.000 claims abstract description 9
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims abstract description 3
- BOGSOFADOWIECK-UHFFFAOYSA-N [N].C=1C=NNC=1 Chemical group [N].C=1C=NNC=1 BOGSOFADOWIECK-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000000304 alkynyl group Chemical group 0.000 claims abstract description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract 3
- 238000000034 method Methods 0.000 claims description 17
- 230000008569 process Effects 0.000 claims description 8
- -1 alkali metal salts Chemical class 0.000 claims description 5
- XBYRMPXUBGMOJC-UHFFFAOYSA-N 1,2-dihydropyrazol-3-one Chemical class OC=1C=CNN=1 XBYRMPXUBGMOJC-UHFFFAOYSA-N 0.000 claims description 4
- 229910052783 alkali metal Inorganic materials 0.000 claims description 3
- 239000003513 alkali Substances 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims 1
- HSRJKNPTNIJEKV-UHFFFAOYSA-N Guaifenesin Chemical compound COC1=CC=CC=C1OCC(O)CO HSRJKNPTNIJEKV-UHFFFAOYSA-N 0.000 claims 1
- 239000002798 polar solvent Substances 0.000 claims 1
- 239000000543 intermediate Substances 0.000 abstract description 3
- 230000000895 acaricidal effect Effects 0.000 abstract description 2
- 230000001069 nematicidal effect Effects 0.000 abstract description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 239000000460 chlorine Substances 0.000 description 12
- 239000000243 solution Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 150000002429 hydrazines Chemical class 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- JEXVQSWXXUJEMA-UHFFFAOYSA-N pyrazol-3-one Chemical compound O=C1C=CN=N1 JEXVQSWXXUJEMA-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- XBJYJEIXHKZWOO-UHFFFAOYSA-N 5-chloro-1,2-dihydropyrazol-3-one Chemical compound OC1=CC(Cl)=NN1 XBJYJEIXHKZWOO-UHFFFAOYSA-N 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- PKUWKAXTAVNIJR-UHFFFAOYSA-N O,O-diethyl hydrogen thiophosphate Chemical compound CCOP(O)(=S)OCC PKUWKAXTAVNIJR-UHFFFAOYSA-N 0.000 description 1
- AVKHCKXGKPAGEI-UHFFFAOYSA-N Phenicarbazide Chemical compound NC(=O)NNC1=CC=CC=C1 AVKHCKXGKPAGEI-UHFFFAOYSA-N 0.000 description 1
- 125000005157 alkyl carboxy group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 125000002587 enol group Chemical group 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 230000008570 general process Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000020477 pH reduction Effects 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003580 thiophosphoric acid esters Chemical class 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34
- A01N57/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having alternatively specified atoms bound to the phosphorus atom and not covered by a single one of groups A01N57/10, A01N57/18, A01N57/26, A01N57/34 containing heterocyclic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D231/18—One oxygen or sulfur atom
- C07D231/20—One oxygen atom attached in position 3 or 5
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6509—Six-membered rings
- C07F9/650905—Six-membered rings having the nitrogen atoms in the positions 1 and 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT31190/77A IT1090364B (it) | 1977-12-23 | 1977-12-23 | Esteri fosforici e tiofosforici di 5(3) idrossipirazoli sostituiti in posizione 3(5) insetticidi |
| IT3119177A IT1090365B (it) | 1977-12-23 | 1977-12-23 | 5(3)-idrossi-pirazoli sostituiti in posizione 3(5) e loro procedimento di preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD150056A5 true DD150056A5 (de) | 1981-08-12 |
Family
ID=26328917
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78220132A DD150056A5 (de) | 1977-12-23 | 1978-12-22 | Verfahren zur herstellung von 5(3)-hydroxypyrazolen |
| DD78220135A DD150062A5 (de) | 1977-12-23 | 1978-12-22 | Verfahren zur herstellung von phosphorsaeure-estern von 5(3)-hydroxypyrazolen |
| DD78210125A DD150425A5 (de) | 1977-12-23 | 1978-12-22 | Mittel zur bekaempfung von insekten,acari und nematoda |
Family Applications After (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD78220135A DD150062A5 (de) | 1977-12-23 | 1978-12-22 | Verfahren zur herstellung von phosphorsaeure-estern von 5(3)-hydroxypyrazolen |
| DD78210125A DD150425A5 (de) | 1977-12-23 | 1978-12-22 | Mittel zur bekaempfung von insekten,acari und nematoda |
Country Status (26)
| Country | Link |
|---|---|
| US (3) | US4256902A (el) |
| JP (1) | JPS5495567A (el) |
| AR (1) | AR223157A1 (el) |
| AU (1) | AU4276578A (el) |
| BR (1) | BR7808414A (el) |
| CA (1) | CA1113946A (el) |
| CH (1) | CH639393A5 (el) |
| CS (1) | CS207749B2 (el) |
| DD (3) | DD150056A5 (el) |
| DE (2) | DE2855256A1 (el) |
| DK (1) | DK569478A (el) |
| EG (1) | EG13746A (el) |
| ES (1) | ES476263A1 (el) |
| GB (1) | GB2013182B (el) |
| GR (1) | GR71657B (el) |
| IL (1) | IL56259A (el) |
| IN (1) | IN149776B (el) |
| LU (1) | LU80702A1 (el) |
| NL (1) | NL7812293A (el) |
| NO (1) | NO784274L (el) |
| NZ (1) | NZ189284A (el) |
| OA (1) | OA06140A (el) |
| PL (1) | PL115092B1 (el) |
| PT (1) | PT68967A (el) |
| RO (2) | RO77326A (el) |
| SU (2) | SU1071197A3 (el) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2604174B1 (fr) * | 1986-09-18 | 1989-06-02 | Roussel Uclaf | Nouveaux derives de la 5-pyrazolone, leur procede de preparation et leur utilisation comme herbicides |
| US4855442A (en) * | 1988-04-13 | 1989-08-08 | Monsanto Company | Substituted 3-hydroxy pyrazoles |
| DE3931303A1 (de) * | 1989-09-20 | 1991-03-28 | Desowag Materialschutz Gmbh | Verfahren zum vorbeugenden materialschutz gegenueber staendig und/oder temporaer im boden lebenden schaedlingen, insbesondere termiten |
| DE4315384A1 (de) * | 1992-09-03 | 1994-03-10 | Bayer Ag | Phosphoryloxypyrazolderivate |
| DE59906901D1 (de) * | 1998-11-19 | 2003-10-09 | Basf Ag | Verfahren zur herstellung von 1-substituierten 5-hydroxypyrazolen |
| AR075713A1 (es) | 2009-03-03 | 2011-04-20 | Du Pont | Pirazoles fungicidas |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2439098A (en) * | 1944-12-22 | 1948-04-06 | Eastman Kodak Co | Alkoxy pyrazolone couplers |
| AT184580B (de) * | 1951-04-20 | 1956-02-10 | Geigy Ag J R | Verfahren zur Herstellung neuer, heterocyclischer Phosphorsäure- bzw. Thiophosphorsäureester |
| CH436835A (de) * | 1959-03-06 | 1967-05-31 | Philips Nv | Schädlingsbekämpfungsmittel |
| US3166475A (en) * | 1959-12-29 | 1965-01-19 | Fiordalisi Fernanda Misani | Anti-convulsant pyrazolones |
| US3644374A (en) * | 1969-04-04 | 1972-02-22 | Raoul Buijle | Process for the preparation of acylated amides |
| DE2037853C3 (de) * | 1970-07-30 | 1980-02-14 | Bayer Ag, 5090 Leverkusen | Pyrazole- (thiono)-phosphor(phosphon)saureester, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| DE2060198A1 (de) * | 1970-12-08 | 1972-06-15 | Bayer Ag | Pyrazolo-(thiono)-phosphor(phosphon)-saeureester,Verfahren zu ihrer Herstellung sowie ihre Verwendung als Insektizide und Akarizide |
| BE785785A (fr) * | 1971-07-02 | 1973-01-03 | Bayer Ag | Nouveaux esters d'acides o-pyrazolothiono-phosphoriques (phosphoniques), leur preparation et leur application comme insecticides et acaricide |
| DE2219484A1 (de) * | 1972-04-21 | 1973-10-31 | Bayer Ag | 0-pyrazolo(thiono)-phosphor(phosphon)saeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DD108536A1 (el) * | 1972-12-21 | 1974-09-20 | ||
| DE2608643A1 (de) * | 1976-03-03 | 1977-09-08 | Bayer Ag | O,s-dialkyl-o-pyrazoldithiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
| DE2639258A1 (de) * | 1976-09-01 | 1978-03-02 | Bayer Ag | Tert.-butyl-substituierte pyrazolyl (thiono)(thiol)-phosphor(phosphon)-saeureester bzw. -esteramide, verfahren zu ihrer herstellung und ihre verwendung als insektizide, akarizide und nematizide |
| JPS5547695A (en) * | 1978-09-19 | 1980-04-04 | Takeda Chem Ind Ltd | Pyrazole phosphate, its preparation, and insecticide and miticide |
-
1978
- 1978-12-19 NO NO784274A patent/NO784274L/no unknown
- 1978-12-19 NL NL7812293A patent/NL7812293A/xx not_active Application Discontinuation
- 1978-12-19 DK DK569478A patent/DK569478A/da not_active Application Discontinuation
- 1978-12-20 AR AR274881A patent/AR223157A1/es active
- 1978-12-20 RO RO7895990A patent/RO77326A/ro unknown
- 1978-12-20 EG EG728/78A patent/EG13746A/xx active
- 1978-12-20 CH CH1298278A patent/CH639393A5/it not_active IP Right Cessation
- 1978-12-20 PL PL1978211969A patent/PL115092B1/pl unknown
- 1978-12-20 IL IL56259A patent/IL56259A/xx unknown
- 1978-12-20 RO RO102780A patent/RO81226B/ro unknown
- 1978-12-21 BR BR7808414A patent/BR7808414A/pt unknown
- 1978-12-21 NZ NZ189284A patent/NZ189284A/xx unknown
- 1978-12-21 CS CS788758A patent/CS207749B2/cs unknown
- 1978-12-21 IN IN1358/CAL/78A patent/IN149776B/en unknown
- 1978-12-21 DE DE19782855256 patent/DE2855256A1/de active Granted
- 1978-12-21 GR GR57957A patent/GR71657B/el unknown
- 1978-12-21 DE DE2858748A patent/DE2858748C2/de not_active Expired - Fee Related
- 1978-12-21 GB GB7849730A patent/GB2013182B/en not_active Expired
- 1978-12-21 AU AU42765/78A patent/AU4276578A/en active Pending
- 1978-12-22 CA CA318,485A patent/CA1113946A/en not_active Expired
- 1978-12-22 JP JP15769878A patent/JPS5495567A/ja active Granted
- 1978-12-22 LU LU80702A patent/LU80702A1/xx unknown
- 1978-12-22 DD DD78220132A patent/DD150056A5/de unknown
- 1978-12-22 ES ES476263A patent/ES476263A1/es not_active Expired
- 1978-12-22 OA OA56696A patent/OA06140A/xx unknown
- 1978-12-22 PT PT68967A patent/PT68967A/pt unknown
- 1978-12-22 DD DD78220135A patent/DD150062A5/de unknown
- 1978-12-22 DD DD78210125A patent/DD150425A5/de unknown
- 1978-12-22 SU SU782699555A patent/SU1071197A3/ru active
-
1979
- 1979-06-18 SU SU792776759A patent/SU1001858A3/ru active
-
1980
- 1980-03-12 US US06/129,724 patent/US4256902A/en not_active Expired - Lifetime
-
1982
- 1982-09-29 US US06/426,881 patent/US4459294A/en not_active Expired - Fee Related
-
1983
- 1983-08-18 US US06/524,229 patent/US4492690A/en not_active Expired - Fee Related
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