NO116821B - - Google Patents
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- 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
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- 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. Process for the preparation of halogen pyridazines.
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 The object of the present invention is the preparation of 6-halo-, especially 6-chloro-pyridazines, which have a free or functionally derived carboxyl group or an acyl residue in the 5-position. A functionally derived carboxyl group is e.g. an esterified or amidated carboxyl group and primarily the cyano group. By acyl residue, the acetyl group should first preferably be understood. The invention relates in particular to such 6-halo-pyridazines which have lower alkyl in the 3- and 4-position, such as methyl residues, e.g. 6-chloro-5-cyano-3,4-dimethyl-pyridazine with the formula
De kan imidlertid også i disse stillinger ha andre rester slik som fenylrester. However, they can also have other residues such as phenyl residues in these positions.
De nevnte forbindelser har fungisid The compounds mentioned are fungicidal
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. effect, e.g. against Epidermophyton and Microsporum, and amoebicidal effect, e.g. against Entamoeba Histolytica, and can be used as medicine. They are also valuable as intermediates.
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 These halopyridazines can be prepared according to methods known per se. Thus, 6-oxy-pyridazines, which in the 5-position have a free or functionally derived carboxyl group or an acyl residue, can be treated with halogenating agents. The halogenides of phosphoric acid, such as phosphorus oxychloride, phosphorus pentachloride or phosphorus pentabromide, are preferably suitable as such agents. The turnover can be carried out in the presence or absence of diluents or
katalysatorer i åpent eller lukket kar under catalysts in an open or closed vessel below
trykk. Man arbeider fortrinsvis ved for-høyet temperatur. Print. One preferably works at too high a temperature.
De som utgangstoffer anvendte 6-oksy-pyridaziner er kjent eller lar seg fremstille etter i og for seg kjente fremgangsmåter. The 6-oxy-pyridazines used as starting materials are known or can be prepared according to methods known per se.
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. The invention is described in the following examples. Between weight part and volume part there is the same relationship as between gram and cm<3>. Temperatures are given in degrees Celsius.
Eksempel 1: Example 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 20 parts by weight of 6-oxy-5-cyano-3,4-dimethyl-pyridazine are heated for one hour in a bath at 100° together with 90 parts by volume of phosphorus oxychloride. Excess phosphorous oxychloride is evaporated in a vacuum and ice water is added to the remainder. The aqueous solution is placed
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. at pH = 7 with 2-n. caustic soda, is extracted with chloroform, and the chloroform residue is recrystallized from ligroin. 6-chloro-5-cyano-3,4-dimethyl-pyridazine is thus obtained in white crystals with melting point = 81-82°. Yield 90 per cent.
Eksempel 2: Example 2:
Man oppheter 5 vektsdeler 6-oksy-5-lumdeler fosforoksyklorid i y2 time til 100°. 5 parts by weight of 6-oxy-5-lum parts of phosphorus oxychloride are heated for y2 hours to 100°.
karbetoksy-3,4-difenyl-pyridazin og 30 vo-Deretter avdampes i vakuum for overskudd carbethoxy-3,4-diphenyl-pyridazine and 30 vo- Then evaporated in vacuo for excess
åv fosforoksyklorid, resten opptas i isvann, of phosphorus oxychloride, the remainder is taken up in ice water,
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 and the aqueous solution is extracted with ether. The ether residue is crystallized from ethyl alcohol and thus 6-chloro-5-carbethoxy-3,4-diphenyl-pyridazine is obtained with the formula
i hvite krystaller med smeltepunkt = 114°. in white crystals with melting point = 114°.
Utbytte 85 pst. Dividend 85 per cent.
Eksempel 3: Example 3:
20 vektsdeler 6-oksy-5-cyan-3,4-difenyl-pyridazin opphetes med 120 volumdeler fosforoksyklorid i y2 time til 100°. Man av- 20 parts by weight of 6-oxy-5-cyano-3,4-diphenyl-pyridazine are heated with 120 parts by volume of phosphorus oxychloride for y2 hours to 100°. One off-
damper deretter overskudd av fosforoksy- then vaporizes excess phosphorus oxy-
klorid i vakuum og tilsetter resten isvann. chloride in vacuo and add ice water to the remainder.
Den vandige oppløsning utrystes med eter, The aqueous solution is shaken with ether,
eteren fordampes, og eterresten omkrystal- the ether evaporates, and the ether residue recrystallizes
liseres fra etylalkohol. Man får således 6-klor-5-cyan-3,4-difenyl-pyridazin med formelen is lysed from ethyl alcohol. Thus, 6-chloro-5-cyano-3,4-diphenyl-pyridazine is obtained with the formula
som hvite krystaller med smeltepunkt = as white crystals with melting point =
134—135°. Utbytte 75 pst. 134-135°. Dividend 75 per cent.
Eksempel 4: Example 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 17.2 parts by weight of 6-oxy-5-carbethoxy-3,4-d;-(p-chlorophenyl)-pyridazine and 100 parts by volume of phosphorus oxychloride are heated to 100° for 2 hours. Excess phosphorus oxychloride is then evaporated in a vacuum, the remainder is added to ice water and extracted with ether. Recrystallization of the ether residue from ethyl alcohol yields 6-chloro-5-carbethoxy-3,4-di-(p-chloro-phenyl)-pyridazine with the formula
som hvite krystaller med smeltepunkt =- 137—139°. Utbytte 45 pst. as white crystals with melting point =- 137—139°. Dividend 45 per cent.
Eksempel 5: Example 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 5 parts by weight of 6-oxy-5-acetyl-3,4-diphenyl-pyridazine and 30 parts by volume of phosphorus oxychloride are heated to 100° for 2 hours. Phosphorus oxychloride is then evaporated in vacuo, the remainder is added to ice water and extracted with chloroform. After distillation of the chloroform, 6-chloro-5-acetyl-3,4-diphenyl-pyridazine crystallizes with the formula
fra etylalkohol som hvite krystaller med smeltepunkt = 166—167°. Utbytte 82 pst. from ethyl alcohol as white crystals with melting point = 166—167°. Dividend 82 per cent.
Claims (2)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE1493064 | 1964-12-10 | ||
| SE10467/65A SE340533B (en) | 1965-08-11 | 1965-08-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116821B true NO116821B (en) | 1969-05-27 |
Family
ID=26655772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO159929A NO116821B (en) | 1964-12-10 | 1965-10-01 |
Country Status (9)
| Country | Link |
|---|---|
| AT (1) | AT257974B (en) |
| CH (1) | CH432865A (en) |
| DE (1) | DE1498275A1 (en) |
| DK (1) | DK115505B (en) |
| FI (1) | FI40947B (en) |
| FR (1) | FR1459558A (en) |
| GB (1) | GB1067799A (en) |
| NL (1) | NL6514850A (en) |
| NO (1) | NO116821B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN105403269B (en) * | 2015-12-03 | 2018-10-30 | 中国科学院测量与地球物理研究所 | Adjustable rainwash monitoring device |
-
1965
- 1965-09-17 AT AT852265A patent/AT257974B/en active
- 1965-09-22 CH CH1310065A patent/CH432865A/en unknown
- 1965-09-22 GB GB40348/65A patent/GB1067799A/en not_active Expired
- 1965-09-28 DK DK499965AA patent/DK115505B/en 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/en not_active Withdrawn
- 1965-11-16 NL NL6514850A patent/NL6514850A/xx unknown
- 1965-12-10 FR FR41730A patent/FR1459558A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AT257974B (en) | 1967-11-10 |
| FR1459558A (en) | 1966-11-18 |
| GB1067799A (en) | 1967-05-03 |
| NL6514850A (en) | 1966-06-13 |
| FI40947B (en) | 1969-03-31 |
| DK115505B (en) | 1969-10-13 |
| DE1498275A1 (en) | 1968-12-12 |
| DE1498275B2 (en) | 1970-12-17 |
| CH432865A (en) | 1967-03-31 |
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