CH617669A5 - - Google Patents
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- Publication number
- CH617669A5 CH617669A5 CH360379A CH360379A CH617669A5 CH 617669 A5 CH617669 A5 CH 617669A5 CH 360379 A CH360379 A CH 360379A CH 360379 A CH360379 A CH 360379A CH 617669 A5 CH617669 A5 CH 617669A5
- Authority
- CH
- Switzerland
- Prior art keywords
- formula
- alkyl
- compounds
- iii
- acid hydrazide
- Prior art date
Links
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical compound OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 21
- 238000000034 method Methods 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 6
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 claims description 5
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 5
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000003495 polar organic solvent Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 2
- -1 glyoxylic acid ester Chemical class 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- FAQJJMHZNSSFSM-UHFFFAOYSA-N phenylglyoxylic acid Chemical compound OC(=O)C(=O)C1=CC=CC=C1 FAQJJMHZNSSFSM-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- OXOYOSITARWPAX-UHFFFAOYSA-N 2-(4-methylsulfonylphenyl)-2-oxoacetic acid Chemical compound CS(=O)(=O)C1=CC=C(C(=O)C(O)=O)C=C1 OXOYOSITARWPAX-UHFFFAOYSA-N 0.000 description 1
- XJFMJJZJSWBNOC-UHFFFAOYSA-N 2-oxo-2-[4-(trifluoromethoxy)phenyl]acetic acid Chemical compound OC(=O)C(=O)C1=CC=C(OC(F)(F)F)C=C1 XJFMJJZJSWBNOC-UHFFFAOYSA-N 0.000 description 1
- BFNNILAMSKQDRN-UHFFFAOYSA-N 2h-1,2,4-triazin-5-one Chemical class O=C1C=NNC=N1 BFNNILAMSKQDRN-UHFFFAOYSA-N 0.000 description 1
- GAIDCDVTAJLEAE-UHFFFAOYSA-N 4-amino-1,2,4-triazin-5-one Chemical class NN1C=NN=CC1=O GAIDCDVTAJLEAE-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- MEICCQSGNMMNSQ-UHFFFAOYSA-N C(C)(=O)NN=C(C(=O)NN)C1=CC(=C(C=C1)OC)OC.C(C)(=O)NN=C(C(=O)NN)C1=CC(=CC=C1)OC Chemical compound C(C)(=O)NN=C(C(=O)NN)C1=CC(=C(C=C1)OC)OC.C(C)(=O)NN=C(C(=O)NN)C1=CC(=CC=C1)OC MEICCQSGNMMNSQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- NCTUXXSKHKWKKI-UHFFFAOYSA-N N-[(1-hydrazinyl-1-oxohexan-2-ylidene)amino]acetamide Chemical group CCCCC(C(=O)NN)=NNC(C)=O NCTUXXSKHKWKKI-UHFFFAOYSA-N 0.000 description 1
- FZXSDRVGRMEYAI-UHFFFAOYSA-N N-[(2-hydrazinyl-2-oxo-1-phenylethylidene)amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=CC=C1 FZXSDRVGRMEYAI-UHFFFAOYSA-N 0.000 description 1
- ITAQSHHUJHREGB-UHFFFAOYSA-N N-[[1-(4-chlorophenyl)-2-hydrazinyl-2-oxoethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=C(Cl)C=C1 ITAQSHHUJHREGB-UHFFFAOYSA-N 0.000 description 1
- LJHOJPRFUASVRU-UHFFFAOYSA-N N-[[1-(4-fluorophenyl)-2-hydrazinyl-2-oxoethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=C(F)C=C1 LJHOJPRFUASVRU-UHFFFAOYSA-N 0.000 description 1
- DYPDUNMXUFSXJB-UHFFFAOYSA-N N-[[2-hydrazinyl-1-(3-methylphenyl)-2-oxoethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=CC(C)=C1 DYPDUNMXUFSXJB-UHFFFAOYSA-N 0.000 description 1
- PSVJPACUHFNSMQ-UHFFFAOYSA-N N-[[2-hydrazinyl-1-(4-methoxyphenyl)-2-oxoethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=C(OC)C=C1 PSVJPACUHFNSMQ-UHFFFAOYSA-N 0.000 description 1
- FBPJKWLUIVZMHX-UHFFFAOYSA-N N-[[2-hydrazinyl-2-oxo-1-[3-(trifluoromethyl)phenyl]ethylidene]amino]propanamide Chemical compound CCC(=O)NN=C(C(=O)NN)C1=CC=CC(C(F)(F)F)=C1 FBPJKWLUIVZMHX-UHFFFAOYSA-N 0.000 description 1
- 125000005598 acylhydrazone group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001411 amidrazones Chemical class 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- XCGGOUSHHFTILQ-UHFFFAOYSA-N ethyl 2-(acetylhydrazinylidene)-2-phenylacetate Chemical compound CCOC(=O)C(=NNC(C)=O)C1=CC=CC=C1 XCGGOUSHHFTILQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000004438 haloalkoxy group Chemical group 0.000 description 1
- 125000001188 haloalkyl group Chemical group 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- GMMXCUJVWPKZDL-UHFFFAOYSA-N n-[(2-hydrazinyl-2-oxo-1-phenylethylidene)amino]acetamide Chemical compound CC(=O)NN=C(C(=O)NN)C1=CC=CC=C1 GMMXCUJVWPKZDL-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- UJTMLNARSPORHR-UHFFFAOYSA-N oc2h5 Chemical compound C=C=[O+] UJTMLNARSPORHR-UHFFFAOYSA-N 0.000 description 1
- 125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002351 wastewater Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
- C07C251/88—Hydrazones having also the other nitrogen atom doubly-bound to a carbon atom, e.g. azines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C251/72—Hydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2364474A DE2364474C3 (de) | 1973-12-24 | 1973-12-24 | Verfahren zur Herstellung von 4-Aminol,2,4-triazin-5-onen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH617669A5 true CH617669A5 (en]) | 1980-06-13 |
Family
ID=5901917
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1709074A CH615428A5 (en]) | 1973-12-24 | 1974-12-20 | |
| CH360379A CH617669A5 (en]) | 1973-12-24 | 1979-04-17 |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH1709074A CH615428A5 (en]) | 1973-12-24 | 1974-12-20 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3959372A (en]) |
| JP (1) | JPS5747907B2 (en]) |
| AT (1) | AT337707B (en]) |
| BE (1) | BE823760A (en]) |
| BR (1) | BR7410769D0 (en]) |
| CH (2) | CH615428A5 (en]) |
| CS (1) | CS179931B2 (en]) |
| DD (1) | DD118645A5 (en]) |
| DE (1) | DE2364474C3 (en]) |
| DK (1) | DK137726C (en]) |
| FR (1) | FR2256163B1 (en]) |
| GB (1) | GB1447337A (en]) |
| HU (1) | HU172753B (en]) |
| IE (1) | IE40343B1 (en]) |
| IL (1) | IL46298A (en]) |
| IT (1) | IT1027955B (en]) |
| LU (1) | LU71540A1 (en]) |
| NL (1) | NL186513C (en]) |
| PL (1) | PL92416B1 (en]) |
| SU (1) | SU553933A3 (en]) |
| YU (1) | YU341974A (en]) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0167905U (en]) * | 1987-10-28 | 1989-05-01 | ||
| CN103254146B (zh) * | 2013-05-31 | 2015-08-12 | 江苏省农用激素工程技术研究中心有限公司 | 苯嗪草酮的制备方法 |
| CN113896689B (zh) * | 2020-06-22 | 2024-02-27 | 北京颖泰嘉和生物科技股份有限公司 | 苯嗪草酮的制备方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH375369A (de) * | 1958-09-23 | 1964-02-29 | Hoffmann La Roche | Verfahren zur Herstellung substituierter Aminosäurehydrazide |
| US3886211A (en) * | 1968-12-10 | 1975-05-27 | Ciba Geigy Corp | Carboxylic acid hydrazide derivatives |
-
1973
- 1973-12-24 DE DE2364474A patent/DE2364474C3/de not_active Expired
-
1974
- 1974-12-11 US US05/531,637 patent/US3959372A/en not_active Expired - Lifetime
- 1974-12-20 IT IT30909/74A patent/IT1027955B/it active
- 1974-12-20 LU LU71540A patent/LU71540A1/xx unknown
- 1974-12-20 DD DD183284A patent/DD118645A5/xx unknown
- 1974-12-20 IL IL46298A patent/IL46298A/xx unknown
- 1974-12-20 CH CH1709074A patent/CH615428A5/de not_active IP Right Cessation
- 1974-12-20 SU SU2086134A patent/SU553933A3/ru active
- 1974-12-23 AT AT1029074A patent/AT337707B/de not_active IP Right Cessation
- 1974-12-23 YU YU03419/74A patent/YU341974A/xx unknown
- 1974-12-23 HU HU74BA00003181A patent/HU172753B/hu unknown
- 1974-12-23 PL PL1974176819A patent/PL92416B1/pl unknown
- 1974-12-23 BR BR10769/74A patent/BR7410769D0/pt unknown
- 1974-12-23 GB GB5538574A patent/GB1447337A/en not_active Expired
- 1974-12-23 IE IE2656/74A patent/IE40343B1/xx unknown
- 1974-12-23 BE BE151855A patent/BE823760A/xx not_active IP Right Cessation
- 1974-12-23 DK DK677174A patent/DK137726C/da not_active IP Right Cessation
- 1974-12-23 CS CS7400008974A patent/CS179931B2/cs unknown
- 1974-12-23 NL NLAANVRAGE7416797,A patent/NL186513C/xx not_active IP Right Cessation
- 1974-12-24 JP JP49147710A patent/JPS5747907B2/ja not_active Expired
- 1974-12-24 FR FR7442657A patent/FR2256163B1/fr not_active Expired
-
1979
- 1979-04-17 CH CH360379A patent/CH617669A5/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CH615428A5 (en]) | 1980-01-31 |
| IL46298A (en) | 1978-01-31 |
| PL92416B1 (en]) | 1977-04-30 |
| DE2364474C3 (de) | 1979-10-11 |
| GB1447337A (en) | 1976-08-25 |
| NL7416797A (nl) | 1975-06-26 |
| IE40343L (en) | 1975-06-24 |
| IL46298A0 (en) | 1975-03-13 |
| NL186513C (nl) | 1990-12-17 |
| CS179931B2 (en) | 1977-12-30 |
| DK137726B (da) | 1978-04-24 |
| DD118645A5 (en]) | 1976-03-12 |
| DK677174A (en]) | 1975-08-25 |
| BR7410769D0 (pt) | 1975-09-02 |
| DE2364474B2 (de) | 1979-02-15 |
| DK137726C (da) | 1978-10-02 |
| HU172753B (hu) | 1978-12-28 |
| IT1027955B (it) | 1978-12-20 |
| AT337707B (de) | 1977-07-11 |
| JPS5095222A (en]) | 1975-07-29 |
| FR2256163A1 (en]) | 1975-07-25 |
| ATA1029074A (de) | 1976-11-15 |
| DE2364474A1 (de) | 1975-06-26 |
| FR2256163B1 (en]) | 1978-07-21 |
| US3959372A (en) | 1976-05-25 |
| JPS5747907B2 (en]) | 1982-10-13 |
| LU71540A1 (en]) | 1975-08-20 |
| IE40343B1 (en) | 1979-05-09 |
| YU341974A (en) | 1982-02-28 |
| SU553933A3 (ru) | 1977-04-05 |
| BE823760A (fr) | 1975-06-23 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |