CH626077A5 - Process for the preparation of isoxazole-4-carboxamide derivatives - Google Patents
Process for the preparation of isoxazole-4-carboxamide derivatives Download PDFInfo
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- CH626077A5 CH626077A5 CH952376A CH952376A CH626077A5 CH 626077 A5 CH626077 A5 CH 626077A5 CH 952376 A CH952376 A CH 952376A CH 952376 A CH952376 A CH 952376A CH 626077 A5 CH626077 A5 CH 626077A5
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- Prior art keywords
- formula
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- isoxazole
- compound
- compounds
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/69—Two or more oxygen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/20—Hypnotics; Sedatives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more 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
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Anesthesiology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pyridine Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Description
626 077 626 077
2 2nd
PATENTANSPRÜCHE 1. Verfahren zur Herstellung neuer Verbindungen der Formel Ib gemäss Patentanspruch 1 herstellt und diese anschliessend oxidiert, wobei in den Formeln Ia und Ib Ri, R2 und R3 die im Patentanspruch 1 gegebenen Bedeutungen haben. 1. A process for the preparation of new compounds of the formula Ib according to claim 1 and then oxidizing them, wherein in the formulas Ia and Ib Ri, R2 and R3 have the meanings given in claim 1.
*Y~ì * Y ~ ì
'n > 'n>
/ C - NH - R- / C - NH - R-
CH, CH,
"St>' "St> '
Die Erfindung betrifft ein Verfahren zur Herstellung neuer Ib Verbindungen der Formel Ib 10 The invention relates to a process for the preparation of new Ib compounds of the formula Ib 10
O O
C - NH - R. C - NH - R.
worin wherein
Ri für eine Alkylgruppe mit 1-4 Kohlenstoffatomen oder eine Cycloalkylgruppe mit 3-6 Kohlenstoffatomen steht, R2 Wasserstoff, Fluor, Chlor oder eine Alkyl- oder eine Ri represents an alkyl group with 1-4 carbon atoms or a cycloalkyl group with 3-6 carbon atoms, R2 represents hydrogen, fluorine, chlorine or an alkyl or
Alkoxygruppe mit jeweils 1—4 Kohlenstoffatomen bedeutet und Alkoxy group each having 1-4 carbon atoms means and
R3 für eine geradkettige Alkylgruppe mit 1-4 Kohlenstoffatomen steht, dadurch gekennzeichnet, dass man eine Verbindung der Formel II R3 represents a straight-chain alkyl group with 1-4 carbon atoms, characterized in that a compound of the formula II
TX ' TX '
"•0 CH. "• 0 CH.
'S"0-= 'S "0- =
Ib Ib
R, R,
0 Lx 0 Lx
" Ö C - N - R. "Ö C - N - R.
Ii II
N. N.
II II
worin wherein
Ri für eine Alkylgruppe mit 1-4 Kohlenstoffatomen oder eine Cycloalkylgruppe mit 3-6 Kohlenstoffatomen steht, R2 Wasserstoff, Fluor, Chlor oder eine Alkyl- oder eine 25 Alkoxygruppe mit jeweils 1—4 Kohlenstoffatomen bedeutet und Ri represents an alkyl group with 1-4 carbon atoms or a cycloalkyl group with 3-6 carbon atoms, R2 represents hydrogen, fluorine, chlorine or an alkyl or a 25 alkoxy group each with 1-4 carbon atoms and
R3 für eine geradkettige Alkylgruppe mit 1-4 Kohlenstoffatomen steht, dadurch gekennzeichnet, dass man eine Verbindung der Formel II R3 represents a straight-chain alkyl group with 1-4 carbon atoms, characterized in that a compound of the formula II
30 30th
O^^CH29 Li6 O ^^ CH29 Li6
R-, R-,
mit einer Verbindung der Formel III with a compound of formula III
Ns Ns
III III
O Li O Li
«« 8 "" 8th
,C - N - R. , C - N - R.
CH26 Li ® CH26 Li ®
II II
O» O"
umsetzt, wobei in den Formeln II und III Ri, R2 und R3 die unter Formel Ib gegebenen Bedeutungen besitzen. is implemented, wherein in the formulas II and III Ri, R2 and R3 have the meanings given under formula Ib.
2. Verfahren zur Herstellung neuer Verbindungen der Formel Ia 2. Process for the preparation of new compounds of formula Ia
40 mit einer Verbindung der Formel III 40 with a compound of formula III
rtu. rtu.
45 45
OHC OHC
III III
0 0
C - NH - R. C - NH - R.
CH- - C - CH- - C -
^ R ^ R
0- 0-
Ia umsetzt, wobei in den Formeln II und III Ri, R2 und R3 die unter Formel Ib gegebenen Bedeutungen haben. Ia, wherein in formulas II and III Ri, R2 and R3 have the meanings given under formula Ib.
so Die Erfindung betrifft ferner ein Verfahren zur Herstellung neuer Verbindungen der Formel Ia, The invention further relates to a process for the preparation of new compounds of the formula Ia,
dadurch gekennzeichnet, dass man eine Verbindung der Formel Ib characterized in that a compound of formula Ib
" Ri"i—r "Ri" i — r
XX XX
/ C - NH - R. / C - NH - R.
Rivf Rivf
'n y-"o 'n y- "o
0 0
C - NH - R- C - NH - R-
CH2 - CH2 -
60 60
CH2 * CH2 *
rO rO
Ia Yes
OH OH
KT- KT-
dadurch gekennzeichnet, dass man eine Verbindung der Ib Formel Ib wie oben beschrieben herstellt und diese anschlies-65 send oxidiert, wobei in der Formel la Ri, R2 und R3 die unter Formel Ib gegebenen Bedeutungen haben. characterized in that a compound of Ib formula Ib is prepared as described above and then oxidized 65 send, wherein in the formula la Ri, R2 and R3 have the meanings given under formula Ib.
Bei der Umsetzung der Verbindungen der Formeln II und III verwendet man als Lösungsmittel insbesondere Äther, In the reaction of the compounds of the formulas II and III, the solvent used is in particular ether,
626 077 626 077
wie Diäthyläther oder Tetrahydrofuran, und aliphatische Kohlenwasserstoffe, wie Hexan, Pentan oder Heptan, vorzugsweise jedoch Tetrahydrofuran. Die Reaktionstemperatur kann beispielsweise von —75° bis —55°C vorzugsweise von — 65° bis — 60°C, und die Reaktionsdauer von 1 bis 5, insbesondere 2V2 bis 3V2 Stunden, betragen. such as diethyl ether or tetrahydrofuran, and aliphatic hydrocarbons such as hexane, pentane or heptane, but preferably tetrahydrofuran. The reaction temperature can be, for example, from -75 ° to -55 ° C, preferably from -65 ° to -60 ° C, and the reaction time from 1 to 5, in particular 2V2 to 3V2 hours.
Die Oxidation wird zweckmässigerweise mit Hilfe von Kaliumpermanganat oder vorzugsweise Chromtrioxid in saurem Medium durchgeführt, wobei das saure Medium aus Schwefelsäure, Chlorwasserstoffsäure oder vorzugsweise Essigsäure und Wasser bestehen soll. Die Reaktionstemperatur beträgt von 20 bis 30°C, und die Reaktionsdauer kann von 1-5, insbesondere von IV2 bis 2V2 Stunden betragen. The oxidation is expediently carried out using potassium permanganate or preferably chromium trioxide in an acidic medium, the acidic medium being said to consist of sulfuric acid, hydrochloric acid or preferably acetic acid and water. The reaction temperature is from 20 to 30 ° C, and the reaction time can be from 1-5, especially from IV2 to 2V2 hours.
Die erhaltenen Verbindungen der Formeln Ia und Ib können auf an sich bekannte Weise isoliert und gereinigt werden. Falls erwünscht, können die Verbindungen der Formeln Ia und Ib in ihre Salze übergeführt werden und umgekehrt. The compounds of the formulas Ia and Ib obtained can be isolated and purified in a manner known per se. If desired, the compounds of the formulas Ia and Ib can be converted into their salts and vice versa.
Die Verbindungen der Formel II können hergestellt werden, indem man eine Verbindung der Formel IV The compounds of formula II can be prepared by using a compound of formula IV
VII VII
20 20th
- NH - R- - NH - R-
Diese Endprodukte können z. B. als schlafvermehrende Mittel, als Schwach-Tranquilizer und als Neuroleptika verwendet IV werden. These end products can e.g. B. IV as a sleep-increasing agent, as a weak tranquilizer and as neuroleptics.
Die folgenden Beispiele veranschaulichen die Erfindung. The following examples illustrate the invention.
mit einer Verbindung der Formel V R4LÌ with a compound of formula V R4LÌ
V V
umsetzt, wobei in den Formeln IV und V Ri und R3 die oben angegebenen Bedeutungen haben und R4 für Ci-C4-Alkyl steht. is implemented, wherein in the formulas IV and V Ri and R3 have the meanings given above and R4 is Ci-C4-alkyl.
Dieses Verfahren wird zweckmässigerweise in den gleichen Lösungsmitteln und unter den gleichen Bedingungen wie bei der Umsetzung der Verbindungen der Formeln II und III durchgeführt, wobei Hexan bevorzugt wird. This process is expediently carried out in the same solvents and under the same conditions as in the reaction of the compounds of the formulas II and III, hexane being preferred.
Die Verbindungen der Formeln III, IV und V sind entweder bekannt oder können auf an sich bekannte Weise aus bekannten Ausgangsverbindungen hergestellt werden. The compounds of the formulas III, IV and V are either known or can be prepared in a manner known per se from known starting compounds.
Die Verbindungen der Formeln Ia und Ib können als Zwischenprodukte zur Herstellung pharmazeutisch aktiver Substanzen der Formel VII, wie z. B. nach dem folgenden Reaktionsschema verwendet werden: The compounds of formulas Ia and Ib can be used as intermediates for the preparation of pharmaceutically active substances of formula VII, such as. B. can be used according to the following reaction scheme:
C - NH - R. C - NH - R.
^ O^^CH-, ~ C ^ O ^^ CH-, ~ C
Z ti o Z ti o
Ia Yes
25 25th
Beispiel 1 example 1
3-Äthyl-5-(ß-hydroxyphenäthyl)-N-methyl-isoxazol-4-carboxamid (Verbindung der Formel Ib) 30 Eine Suspension von 58,5 g 3-Äthyl-N,5-dimethyl-isoxazol-4-carboxamid in 1 Liter Tetrahydrofuran wird auf — 65 °C abgekühlt und mit 478 ml einer 1,6 molaren n-Butyllithium-Lösung in Hexan (0,765 Mol) tropfenweise versetzt, wobei die Temperatur zwischen — 600 und — 700 C gehalten wird. 3s Nach beendeter Zugabe wird die Suspension während 1V2 Stunden bei — 600 bis — 700 C gerührt und danach mit 37,2 g Benzaldehyd in 375 ml Tetrahydrofuran tropfenweise versetzt, wobei die Temperatur von —60° bis —70°C betragen soll. Nach beendeter Zugabe wird das Gemisch während 40 IV2 Stunden bei —60° bis —70°C gerührt, auf —30°C erwärmt und danach mit einer gesättigten wässerigen Ammoniumchlorid-Lösung versetzt. Das Gemisch wird durch Zugabe von Tetrahydrofuran weiter verdünnt und die gebildeten Schichten abgetrennt. Die Tetrahydrofuran-Schicht wird 45 2mal mit einer 50%igen wässerigen Kochsalz-Lösung und lmal mit konzentrierter wässeriger Kochsalz-Lösung gewaschen, danach über wasserfreiem Magnesiumsulfat getrocknet, abfiltriert und im Vakuum eingedampft. Der feste Rückstand wird mit Äther verrieben und abfiltriert, wobei die Titeiso Verbindung vom Smp. 135-137°C erhalten wird. 3-ethyl-5- (ß-hydroxyphenethyl) -N-methyl-isoxazole-4-carboxamide (compound of formula Ib) 30 A suspension of 58.5 g of 3-ethyl-N, 5-dimethyl-isoxazole-4-carboxamide in 1 liter of tetrahydrofuran is cooled to -65 ° C. and 478 ml of a 1.6 molar n-butyllithium solution in hexane (0.765 mol) are added dropwise, the temperature being kept between -600 and -700 C. 3s After the addition has ended, the suspension is stirred for 1 1/2 hours at -600 to -700 C and then 37.2 g of benzaldehyde in 375 ml of tetrahydrofuran are added dropwise, the temperature being said to be from -60 ° to -70 ° C. When the addition is complete, the mixture is stirred at -60 ° to -70 ° C for 40 IV2 hours, warmed to -30 ° C and then mixed with a saturated aqueous ammonium chloride solution. The mixture is further diluted by adding tetrahydrofuran and the layers formed are separated off. The tetrahydrofuran layer is washed twice with a 50% aqueous sodium chloride solution and once with concentrated aqueous sodium chloride solution, then dried over anhydrous magnesium sulfate, filtered off and evaporated in vacuo. The solid residue is triturated with ether and filtered off, giving the Titeiso compound of mp. 135-137 ° C.
Ringschluss Ring closure
O O
Beispiel 2 Example 2
3-Äthyl-N-methyl-5-phenacyl-4-isoxazol-carboxamid 55 (Verbindung der Formel Ia) 3-ethyl-N-methyl-5-phenacyl-4-isoxazole-carboxamide 55 (compound of the formula Ia)
Eine Lösung von 29 g 3-Äthyl-5-(ß-hydroxyphenäthyl)-N-methyl-isoxazol-4-carboxamid in 500 ml Essigsäure wird bei Raumtemperatur tropfenweise mit 12,5 g Chromtrioxid in 125 ml Wasser versetzt. Die gebildete Lösung wird während 60 2 Stunden bei Raumtemperatur gerührt und danach ein Teil VX der Essigsäure im Vakuum entfernt. Der Rückstand wird in Eiswasser geschüttet und mit Methylenchlorid extrahiert. Die Methylenchlorid-Schicht wird mit einer 2N wässerigen Natriumhydroxid-Lösung gewaschen, über wasserfreiem 65 Magnesiumsulfat getrocknet, filtriert und im Vakuum eingedampft. Der feste Rückstand wird mit Äther verrieben und aus Äthanol umkristallisiert. Hierbei erhält man die Titelverbindung vom Smp. 134-136°C. A solution of 29 g of 3-ethyl-5- (ß-hydroxyphenethyl) -N-methyl-isoxazole-4-carboxamide in 500 ml of acetic acid is added dropwise at room temperature with 12.5 g of chromium trioxide in 125 ml of water. The solution formed is stirred for 60 hours at room temperature and then a portion of VX of the acetic acid is removed in vacuo. The residue is poured into ice water and extracted with methylene chloride. The methylene chloride layer is washed with a 2N aqueous sodium hydroxide solution, dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo. The solid residue is triturated with ether and recrystallized from ethanol. This gives the title compound of mp. 134-136 ° C.
B B
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60232475A | 1975-08-06 | 1975-08-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH626077A5 true CH626077A5 (en) | 1981-10-30 |
Family
ID=24410893
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH952376A CH626077A5 (en) | 1975-08-06 | 1976-07-26 | Process for the preparation of isoxazole-4-carboxamide derivatives |
Country Status (16)
| Country | Link |
|---|---|
| AT (1) | ATA579476A (en) |
| AU (1) | AU507216B2 (en) |
| BE (1) | BE844882A (en) |
| CA (1) | CA1064935A (en) |
| CH (1) | CH626077A5 (en) |
| DE (1) | DE2633819A1 (en) |
| DK (1) | DK342876A (en) |
| ES (1) | ES450507A1 (en) |
| FI (1) | FI762152A (en) |
| FR (2) | FR2361886A1 (en) |
| GB (1) | GB1563336A (en) |
| IE (1) | IE43698B1 (en) |
| NO (1) | NO762643L (en) |
| NZ (1) | NZ181683A (en) |
| PH (1) | PH11844A (en) |
| ZA (1) | ZA764732B (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2801190A1 (en) * | 1977-01-19 | 1978-07-20 | Sandoz Ag | 3- (ALPHA-IMINOBENZYL) -4-HYDROXY-2 (1H) - PYRIDONE DERIVATIVE |
-
1976
- 1976-07-26 CH CH952376A patent/CH626077A5/en not_active IP Right Cessation
- 1976-07-28 FI FI762152A patent/FI762152A/fi not_active Application Discontinuation
- 1976-07-28 DE DE19762633819 patent/DE2633819A1/en not_active Withdrawn
- 1976-07-29 NO NO762643A patent/NO762643L/no unknown
- 1976-07-29 DK DK342876A patent/DK342876A/en unknown
- 1976-08-04 GB GB32459/76A patent/GB1563336A/en not_active Expired
- 1976-08-04 NZ NZ181683A patent/NZ181683A/en unknown
- 1976-08-04 CA CA258,375A patent/CA1064935A/en not_active Expired
- 1976-08-04 IE IE1724/76A patent/IE43698B1/en unknown
- 1976-08-04 BE BE169559A patent/BE844882A/en unknown
- 1976-08-04 PH PH18753A patent/PH11844A/en unknown
- 1976-08-05 AT AT0579476A patent/ATA579476A/en not_active Application Discontinuation
- 1976-08-05 ES ES450507A patent/ES450507A1/en not_active Expired
- 1976-08-05 AU AU16612/76A patent/AU507216B2/en not_active Ceased
- 1976-08-06 ZA ZA00764732A patent/ZA764732B/en unknown
- 1976-08-06 FR FR7624026A patent/FR2361886A1/en not_active Withdrawn
-
1977
- 1977-02-01 FR FR7702710A patent/FR2360585A1/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| AU507216B2 (en) | 1980-02-07 |
| FI762152A (en) | 1977-02-07 |
| ATA579476A (en) | 1981-06-15 |
| BE844882A (en) | 1977-02-04 |
| ZA764732B (en) | 1978-03-29 |
| NZ181683A (en) | 1979-01-11 |
| CA1064935A (en) | 1979-10-23 |
| IE43698B1 (en) | 1981-05-06 |
| AU1661276A (en) | 1978-02-09 |
| DK342876A (en) | 1977-02-07 |
| FR2360585A1 (en) | 1978-03-03 |
| ES450507A1 (en) | 1977-12-16 |
| FR2360585B1 (en) | 1980-02-15 |
| DE2633819A1 (en) | 1977-02-24 |
| NO762643L (en) | 1977-02-08 |
| PH11844A (en) | 1978-07-21 |
| GB1563336A (en) | 1980-03-26 |
| IE43698L (en) | 1977-02-06 |
| FR2361886A1 (en) | 1978-03-17 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased |