NO116821B - - Google Patents
Download PDFInfo
- Publication number
- NO116821B NO116821B NO159929A NO15992965A NO116821B NO 116821 B NO116821 B NO 116821B NO 159929 A NO159929 A NO 159929A NO 15992965 A NO15992965 A NO 15992965A NO 116821 B NO116821 B NO 116821B
- Authority
- NO
- Norway
- Prior art keywords
- pyridazine
- oxy
- pyridazines
- parts
- cyano
- Prior art date
Links
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000002252 acyl group Chemical group 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000002140 halogenating effect Effects 0.000 claims description 2
- 239000007858 starting material Substances 0.000 claims description 2
- 239000012320 chlorinating reagent Substances 0.000 claims 1
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 19
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 7
- 239000013078 crystal Substances 0.000 description 5
- 239000005457 ice water Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 4
- -1 halogen pyridazines Chemical class 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000007864 aqueous solution Substances 0.000 description 3
- 125000001033 ether group Chemical group 0.000 description 3
- AOOOVEFJANVAOL-UHFFFAOYSA-N 3-chloro-5,6-dimethylpyridazine-4-carbonitrile Chemical compound CC1=NN=C(Cl)C(C#N)=C1C AOOOVEFJANVAOL-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
- BPOOTCDWLTUMAC-UHFFFAOYSA-N 1-(3-chloro-5,6-diphenylpyridazin-4-yl)ethanone Chemical compound C=1C=CC=CC=1C=1C(C(=O)C)=C(Cl)N=NC=1C1=CC=CC=C1 BPOOTCDWLTUMAC-UHFFFAOYSA-N 0.000 description 1
- KYILDXBCZYCVIN-UHFFFAOYSA-N 3-chloro-5,6-diphenylpyridazine-4-carbonitrile Chemical compound C=1C=CC=CC=1C1=C(C#N)C(Cl)=NN=C1C1=CC=CC=C1 KYILDXBCZYCVIN-UHFFFAOYSA-N 0.000 description 1
- IBWYHNOFSKJKKY-UHFFFAOYSA-N 3-chloropyridazine Chemical class ClC1=CC=CN=N1 IBWYHNOFSKJKKY-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- 241001480035 Epidermophyton Species 0.000 description 1
- 241001480037 Microsporum Species 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 230000003569 amebicidal effect Effects 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 229940007078 entamoeba histolytica Drugs 0.000 description 1
- LFVRLXRBMMFAGL-UHFFFAOYSA-N ethyl 3-chloro-5,6-diphenylpyridazine-4-carboxylate Chemical compound C=1C=CC=CC=1C=1C(C(=O)OCC)=C(Cl)N=NC=1C1=CC=CC=C1 LFVRLXRBMMFAGL-UHFFFAOYSA-N 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 230000007306 turnover Effects 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M16/00—Devices for influencing the respiratory system of patients by gas treatment, e.g. mouth-to-mouth respiration; Tracheal tubes
- A61M16/10—Preparation of respiratory gases or vapours
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M16/00—Devices for influencing the respiratory system of patients by gas treatment, e.g. mouth-to-mouth respiration; Tracheal tubes
- A61M16/10—Preparation of respiratory gases or vapours
- A61M16/104—Preparation of respiratory gases or vapours specially adapted for anaesthetics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61M—DEVICES FOR INTRODUCING MEDIA INTO, OR ONTO, THE BODY; DEVICES FOR TRANSDUCING BODY MEDIA OR FOR TAKING MEDIA FROM THE BODY; DEVICES FOR PRODUCING OR ENDING SLEEP OR STUPOR
- A61M16/00—Devices for influencing the respiratory system of patients by gas treatment, e.g. mouth-to-mouth respiration; Tracheal tubes
- A61M16/10—Preparation of respiratory gases or vapours
- A61M16/12—Preparation of respiratory gases or vapours by mixing different gases
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01F—MIXING, e.g. DISSOLVING, EMULSIFYING OR DISPERSING
- B01F35/00—Accessories for mixers; Auxiliary operations or auxiliary devices; Parts or details of general application
- B01F35/80—Forming a predetermined ratio of the substances to be mixed
- B01F35/83—Forming a predetermined ratio of the substances to be mixed by controlling the ratio of two or more flows, e.g. using flow sensing or flow controlling devices
- B01F35/833—Flow control by valves, e.g. opening intermittently
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01F—MEASURING VOLUME, VOLUME FLOW, MASS FLOW OR LIQUID LEVEL; METERING BY VOLUME
- G01F1/00—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow
- G01F1/05—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow by using mechanical effects
- G01F1/20—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow by using mechanical effects by detection of dynamic effects of the flow
- G01F1/22—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow by using mechanical effects by detection of dynamic effects of the flow by variable-area meters, e.g. rotameters
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01F—MEASURING VOLUME, VOLUME FLOW, MASS FLOW OR LIQUID LEVEL; METERING BY VOLUME
- G01F1/00—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow
- G01F1/05—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow by using mechanical effects
- G01F1/20—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow by using mechanical effects by detection of dynamic effects of the flow
- G01F1/28—Measuring the volume flow or mass flow of fluid or fluent solid material wherein the fluid passes through a meter in a continuous flow by using mechanical effects by detection of dynamic effects of the flow by drag-force, e.g. vane type or impact flowmeter
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01F—MEASURING VOLUME, VOLUME FLOW, MASS FLOW OR LIQUID LEVEL; METERING BY VOLUME
- G01F15/00—Details of, or accessories for, apparatus of groups G01F1/00 - G01F13/00 insofar as such details or appliances are not adapted to particular types of such apparatus
- G01F15/06—Indicating or recording devices
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01F—MEASURING VOLUME, VOLUME FLOW, MASS FLOW OR LIQUID LEVEL; METERING BY VOLUME
- G01F5/00—Measuring a proportion of the volume flow
-
- G—PHYSICS
- G05—CONTROLLING; REGULATING
- G05D—SYSTEMS FOR CONTROLLING OR REGULATING NON-ELECTRIC VARIABLES
- G05D11/00—Control of flow ratio
- G05D11/003—Control of flow ratio using interconnected flow control elements
Landscapes
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Engineering & Computer Science (AREA)
- Fluid Mechanics (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pulmonology (AREA)
- Veterinary Medicine (AREA)
- Anesthesiology (AREA)
- Emergency Medicine (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Automation & Control Theory (AREA)
- Investigating Or Analysing Biological Materials (AREA)
- Measuring Volume Flow (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Fremgangsmåte til fremstilling av halogenpyridaziner.
Gjenstanden for foreliggende oppfin-nelse er fremstilling av 6-halogen-, særlig 6-klor-pyridaziner, som i 5-stilling har en fri eller funksjonelt avledet karboksylgruppe eller en acylrest. En funksjonelt avledet karboksylgruppe er f. eks. en forestret eller amidert karboksylgruppe og i første rekke cyangruppen. Med acylrest skal først fortrinsvis forstås acetylgruppen. Oppfinnelsen angår særlig slike 6-halogen-pyridaziner som i 3- og 4-stilling har lavere al-kyl, slik som metylrester, f. eks. 6-klor-5-cyan-3,4-dimetyl-pyridazin med formelen
De kan imidlertid også i disse stillinger ha andre rester slik som fenylrester.
De nevnte forbindelser har fungisid
virkning, f. eks. mot Epidermophyton og Microsporum, og amøbisid virkning, f. eks. mot Entamoeba Histolytica, og kan anven-des som legemiddel. De er også verdifulle som mellomprodukter.
Disse halogenpyridaziner lar seg fremstille etter i og for seg kjente fremgangsmåter. Således kan man behandle 6-oksy-pyridaziner, som i 5-stilling har en fri eller funksjonelt avledet karboksylgruppe eller en acylrest, med halogeneringsmidler. Som slike midler egner seg fortrinsvis halogen-idene av fosforsyre, slik som fosforoksyklorid, fosforpentaklorid eller fosforpenta-bromid. Omsetningen kan utføres i nær-vær eller fravær av fortynningsmidler eller
katalysatorer i åpent eller lukket kar under
trykk. Man arbeider fortrinsvis ved for-høyet temperatur.
De som utgangstoffer anvendte 6-oksy-pyridaziner er kjent eller lar seg fremstille etter i og for seg kjente fremgangsmåter.
Oppfinnelsen beskrives i de følgende eksempler. Mellom vektsdel og volumdel består det samme forhold som mellom gram og cm<3>. Temperaturene er angitt i Celsius-grader.
Eksempel 1:
20 vektsdeler 6-oksy-5-cyan-3,4-dime-tyl-pyridazin opphetes i en time i et bad på 100° sammen med 90 volumdeler fosforoksyklorid. Man avdamper overskudd av fosforoksyklorid i vakuum og tilsetter resten isvann. Den vandige oppløsning stilles
på pH = 7 med 2-n. natronlut, uttrekkes med kloroform, og kloroformresten omkry-stalliseres av ligroin. 6-klor-5-cyan-3,4-di-metyl-pyridazin fåes således i hvite krystaller med smeltepunkt = 81—82°. Utbytte 90 pst.
Eksempel 2:
Man oppheter 5 vektsdeler 6-oksy-5-lumdeler fosforoksyklorid i y2 time til 100°.
karbetoksy-3,4-difenyl-pyridazin og 30 vo-Deretter avdampes i vakuum for overskudd
åv fosforoksyklorid, resten opptas i isvann,
og den vandige oppløsning uttrekkes med eter. Eterresten krystalliserer man fra etylalkohol og får således 6-klor-5-karbet-oksy-3,4-difenyl-pyridazin med formelen
i hvite krystaller med smeltepunkt = 114°.
Utbytte 85 pst.
Eksempel 3:
20 vektsdeler 6-oksy-5-cyan-3,4-difenyl-pyridazin opphetes med 120 volumdeler fosforoksyklorid i y2 time til 100°. Man av-
damper deretter overskudd av fosforoksy-
klorid i vakuum og tilsetter resten isvann.
Den vandige oppløsning utrystes med eter,
eteren fordampes, og eterresten omkrystal-
liseres fra etylalkohol. Man får således 6-klor-5-cyan-3,4-difenyl-pyridazin med formelen
som hvite krystaller med smeltepunkt =
134—135°. Utbytte 75 pst.
Eksempel 4:
17,2 vektsdeler 6-oksy-5-karbetoksy-3,4-d;-(p-klorfenyl)-pyridazin og 100 volumdeler fosforoksyklorid opphetes y2 time til 100°. Man avdamper deretter overskudd av fosforoksyklorid i vakuum, tilsetter resten isvann og uttrekker med eter. Ved omkry-stallisasjon av eterresten fra etylalkohol får man 6-klor-5-karbetoksy-3,4-di-(p-klor-fenyl)-pyridazin med formelen
som hvite krystaller med smeltepunkt =- 137—139°. Utbytte 45 pst.
Eksempel 5:
Man oppheter 5 vektsdeler 6-oksy-5-acetyl-3,4-difenyl-pyridazin og 30 volumdeler fosforoksyklorid y2 time til 100°. Fosforoksyklorid avdampes deretter i vakuum,
resten tilsettes isvann og uttrekkes med kloroform. Etter avdestillasjon av kloro-formen krystalliserer 6-klor-5-acetyl-3,4 difenyl-pyridazin med formelen
fra etylalkohol som hvite krystaller med smeltepunkt = 166—167°. Utbytte 82 pst.
Claims (2)
1. Fremgangsmåte til fremstilling av 6-halogen-pyridaziner, som i 5-stilling har en fri eller funksjonelt avledet karboksyl-
eller acylgruppe, karakterisert ved at man behandler 6-oksy-pyridaziner, som i 5-stil-
ling inneholder en fri eller funksjonelt avledet karboksylgruppe eller en acylrest, med halogeneringsmidler, særlig kloreringsmid-ler.
2. Framgangsmåte ifølge påstand 1, karakterisert ved at man som utgangsstof-
fer anvender 5-cyan-6-oksypyridaziner, særlig slike som i 3- og 4-stilling har en lavere alkylrest.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1493064 | 1964-12-10 | ||
| SE10467/65A SE340533B (no) | 1965-08-11 | 1965-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116821B true NO116821B (no) | 1969-05-27 |
Family
ID=26655772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159929A NO116821B (no) | 1964-12-10 | 1965-10-01 |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT257974B (no) |
| CH (1) | CH432865A (no) |
| DE (1) | DE1498275A1 (no) |
| DK (1) | DK115505B (no) |
| FI (1) | FI40947B (no) |
| FR (1) | FR1459558A (no) |
| GB (1) | GB1067799A (no) |
| NL (1) | NL6514850A (no) |
| NO (1) | NO116821B (no) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105403269B (zh) * | 2015-12-03 | 2018-10-30 | 中国科学院测量与地球物理研究所 | 可调式地表径流监测装置 |
-
1965
- 1965-09-17 AT AT852265A patent/AT257974B/de active
- 1965-09-22 CH CH1310065A patent/CH432865A/de unknown
- 1965-09-22 GB GB40348/65A patent/GB1067799A/en not_active Expired
- 1965-09-28 DK DK499965AA patent/DK115505B/da unknown
- 1965-09-30 FI FI2331/65A patent/FI40947B/fi active
- 1965-10-01 NO NO159929A patent/NO116821B/no unknown
- 1965-10-14 DE DE19651498275 patent/DE1498275A1/de not_active Withdrawn
- 1965-11-16 NL NL6514850A patent/NL6514850A/xx unknown
- 1965-12-10 FR FR41730A patent/FR1459558A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT257974B (de) | 1967-11-10 |
| FR1459558A (fr) | 1966-11-18 |
| GB1067799A (en) | 1967-05-03 |
| NL6514850A (no) | 1966-06-13 |
| FI40947B (no) | 1969-03-31 |
| DK115505B (da) | 1969-10-13 |
| DE1498275A1 (de) | 1968-12-12 |
| DE1498275B2 (no) | 1970-12-17 |
| CH432865A (de) | 1967-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Jensen | The synthesis of 1-phenyl-3-methyl-4-acyl-pyrazolones-5 | |
| NO153520B (no) | Fremgangsmaate til fremstilling av et stabilt prepaat inneholdende prostaglandin. | |
| SU623518A3 (ru) | Способ получени производных оксазола | |
| SU433681A3 (ru) | Способ получения 1,2.4^триазин-5-онов | |
| US3168532A (en) | 1, 5-diarylpyrrole-2-propionic acid compounds | |
| McKillip et al. | Aminimides. I. A general synthesis of aminimides from acyl hydrazides and their pyrolysis | |
| NO116821B (no) | ||
| US3007927A (en) | Triazine derivatives | |
| SU664568A3 (ru) | Способ получени ацилпроизводных эритромициноксима | |
| US3128286A (en) | Process for preparing analogues | |
| JPS5821916B2 (ja) | トリアゾロベンゾチアゾ−ルルイノセイホウ | |
| US2839529A (en) | Isothiazole compounds | |
| US2547714A (en) | Furane amino keto compounds | |
| US2953598A (en) | Acyl hydrazines | |
| NO116631B (no) | ||
| US3417153A (en) | Polynitrobenzofluorides and the method of preparation thereof | |
| US3115518A (en) | Production of cyclohexylideneaminooxyacetic acid, its esters, and its salts | |
| US2467126A (en) | Production of mono-alkyl esters of the addition product of levo-pi-maric acid with maleic anhydride | |
| NO115262B (no) | ||
| SU384331A1 (ru) | Способ получени 1-замещенных карбамоил-4(2-оксиарил)-семинарбазидов | |
| SU133871A1 (ru) | Способ получени альфа-алкил- и альфа-арил-бета-алкоксиакролеинов | |
| JPS5944312B2 (ja) | インダゾ−ル誘導体の製法 | |
| Cook et al. | 495. Studies in the azole series. Part XXI. Experiments with N-alkylamino-nitriles | |
| US2434060A (en) | Tetraacetylribonamide and process of making it | |
| US3770738A (en) | Hydrazides |