DE1006424B - Verfahren zur Herstellung neuer Pyridazincarbonsaeureester - Google Patents
Verfahren zur Herstellung neuer PyridazincarbonsaeureesterInfo
- Publication number
- DE1006424B DE1006424B DEC10929A DEC0010929A DE1006424B DE 1006424 B DE1006424 B DE 1006424B DE C10929 A DEC10929 A DE C10929A DE C0010929 A DEC0010929 A DE C0010929A DE 1006424 B DE1006424 B DE 1006424B
- Authority
- DE
- Germany
- Prior art keywords
- parts
- carboxylic acid
- volume
- dihydro
- solution
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 4
- RUUOPSRRIKJHNH-UHFFFAOYSA-N pyridazine-3-carboxylic acid Chemical class OC(=O)C1=CC=CN=N1 RUUOPSRRIKJHNH-UHFFFAOYSA-N 0.000 title claims description 3
- 239000002253 acid Substances 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 3
- 150000001735 carboxylic acids Chemical class 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000004702 methyl esters Chemical class 0.000 claims 1
- 239000000243 solution Substances 0.000 description 19
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 150000002148 esters Chemical class 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
- GYHBVAHWGBJKHA-UHFFFAOYSA-N 6-methylpyran-2,4-dione Chemical compound CC1=CC(=O)CC(=O)O1 GYHBVAHWGBJKHA-UHFFFAOYSA-N 0.000 description 2
- YXHKONLOYHBTNS-UHFFFAOYSA-N Diazomethane Chemical compound C=[N+]=[N-] YXHKONLOYHBTNS-UHFFFAOYSA-N 0.000 description 2
- CWRVKFFCRWGWCS-UHFFFAOYSA-N Pentrazole Chemical compound C1CCCCC2=NN=NN21 CWRVKFFCRWGWCS-UHFFFAOYSA-N 0.000 description 2
- 239000003929 acidic solution Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 230000003555 analeptic effect Effects 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 2
- 239000005457 ice water Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 2
- 229960005152 pentetrazol Drugs 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 235000010288 sodium nitrite Nutrition 0.000 description 2
- RAIPHJJURHTUIC-UHFFFAOYSA-N 1,3-thiazol-2-amine Chemical compound NC1=NC=CS1 RAIPHJJURHTUIC-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002269 analeptic agent Substances 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 150000008049 diazo compounds Chemical class 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 230000003301 hydrolyzing effect Effects 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 239000004081 narcotic agent Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical group C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH807228X | 1954-04-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1006424B true DE1006424B (de) | 1957-04-18 |
Family
ID=4538174
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEC10929A Pending DE1006424B (de) | 1954-04-15 | 1955-03-16 | Verfahren zur Herstellung neuer Pyridazincarbonsaeureester |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US2792396A (esLanguage) |
| BE (1) | BE537354A (esLanguage) |
| CH (1) | CH327122A (esLanguage) |
| DE (1) | DE1006424B (esLanguage) |
| FR (1) | FR1161343A (esLanguage) |
| GB (1) | GB807228A (esLanguage) |
| NL (1) | NL89278C (esLanguage) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3224999A (en) * | 1963-09-10 | 1965-12-21 | Monsanto Co | Process of promoting low hysteresis of rubber using arylenebismethylimides |
| FR2676733B1 (fr) * | 1991-05-22 | 1993-10-01 | Fabre Medicament Pierre | Derives de phenyl-1 dihydro-1,4 hydroxy-3 oxo-4 pyridazines, leur preparation et leur application en therapeutique. |
-
0
- BE BE537354D patent/BE537354A/xx unknown
- NL NL89278D patent/NL89278C/xx active
-
1954
- 1954-04-15 CH CH327122D patent/CH327122A/de unknown
-
1955
- 1955-03-16 DE DEC10929A patent/DE1006424B/de active Pending
- 1955-03-21 FR FR1161343D patent/FR1161343A/fr not_active Expired
- 1955-03-24 US US496616A patent/US2792396A/en not_active Expired - Lifetime
- 1955-04-14 GB GB10834/55A patent/GB807228A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR1161343A (fr) | 1958-08-26 |
| NL89278C (esLanguage) | |
| CH327122A (de) | 1958-01-15 |
| GB807228A (en) | 1959-01-14 |
| BE537354A (esLanguage) | |
| US2792396A (en) | 1957-05-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1302858B (esLanguage) | ||
| DE1147234B (de) | Verfahren zur Herstellung von 1-Isopropyl-4-hydroxy-6-benzyl-pyrazolo[3, 4-d]pyrimidin | |
| DE1006424B (de) | Verfahren zur Herstellung neuer Pyridazincarbonsaeureester | |
| DE1212984B (de) | Verfahren zur Herstellung von basisch substituierten Cumaronen | |
| DE954332C (de) | Verfahren zur Herstellung neuer Ester | |
| DE870553C (de) | Verfahren zur Herstellung von Thiosemicarbazonen | |
| AT229496B (de) | Verfahren zur Darstellung des neuen Nicotinsäureesters des Dihydrohydroxycodeinons | |
| DE951994C (de) | Verfahren zur Herstellung von Pyridazonverbindungen | |
| AT218006B (de) | Verfahren zur Herstellung von neuen 2-Acyl-4-aminophenoläthern und ihren Salzen | |
| AT215993B (de) | Verfahren zur Herstellung von neuen 4-Oxo-2-(halogenalkyl)-2,3-dihydro-[benzo-1,3-oxazinen] | |
| AT204552B (de) | Verfahren zur Herstellung von neuen, heterocyclischen Bis-sulfonamiden | |
| AT233564B (de) | Verfahren zur Herstellung von neuen Derivaten hydrierter Pyridone | |
| DE1445957A1 (de) | Verfahren zur Herstellung von neuen 2-Imino-thiazolinderivaten und ihren Saeureadditionssalzen | |
| AT218519B (de) | Verfahren zur Herstellung von neuen Pyrazol-Derivaten | |
| CH641792A5 (de) | Verfahren zur herstellung von 1,2,3-thiadiazol-5-yl-harnstoffen. | |
| AT211829B (de) | Verfahren zur Herstellung von neuen 3-Aminothiophen-2-carbonsäureestern und den entsprechenden freien Carbonsäuren | |
| AT233559B (de) | Verfahren zur Herstellung neuer 5-Nitrofuran-Derivate | |
| DE1695909C3 (de) | Verfahren zur Herstellung von 1-(5-Nitro-2-thiazolyl)-2-oxo-imidazolidinen | |
| DE1143515B (de) | Verfahren zur Herstellung von Arylaminopyrazolen | |
| AT212838B (de) | Verfahren zur Herstellung der neuen Sulfamyl-3,4-dihydro-pyrido[2,3-e]-1,2,4-thiadiazin-1,1-dioxyde | |
| AT234685B (de) | Verfahren zur Herstellung neuer 3-Phenyl-sydnonimine | |
| DE918146C (de) | Verfahren zur Herstellung von aminoalkyl-substituierten 2-Nitro-4amino-toluolen und 2-Cyan-4-amino-toluolen | |
| AT206899B (de) | Verfahren zur Herstellung von neuen, substituierten 3,5-Dioxo-tetrahydro-1,2,6-thiadiazin-1,1-dioxyden | |
| DEC0009320MA (esLanguage) | ||
| DE1049384B (de) | Verfahren zur Herstellung eines therapeutisch wirksamen Aminobenzolsulfonamids und seiner Salze |