SE441675B - 3-(4-kromanylamino)-2-oxazolidinoner - Google Patents
3-(4-kromanylamino)-2-oxazolidinonerInfo
- Publication number
- SE441675B SE441675B SE7806626A SE7806626A SE441675B SE 441675 B SE441675 B SE 441675B SE 7806626 A SE7806626 A SE 7806626A SE 7806626 A SE7806626 A SE 7806626A SE 441675 B SE441675 B SE 441675B
- Authority
- SE
- Sweden
- Prior art keywords
- dried
- amino
- yield
- isopropanol
- washed
- Prior art date
Links
- FZJSEJHZLCPXBL-UHFFFAOYSA-N 3-(3,4-dihydro-2h-chromen-4-ylamino)-1,3-oxazolidin-2-one Chemical class O=C1OCCN1NC1C2=CC=CC=C2OCC1 FZJSEJHZLCPXBL-UHFFFAOYSA-N 0.000 title claims 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 5
- 150000001875 compounds Chemical class 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 26
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- -1 4-chromanylidene Chemical group 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000005984 hydrogenation reaction Methods 0.000 description 2
- AKPUJVVHYUHGKY-UHFFFAOYSA-N hydron;propan-2-ol;chloride Chemical compound Cl.CC(C)O AKPUJVVHYUHGKY-UHFFFAOYSA-N 0.000 description 2
- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 1
- KYCJNIUHWNJNCT-UHFFFAOYSA-N 3-Amino-2-oxazolidone Chemical compound NN1CCOC1=O KYCJNIUHWNJNCT-UHFFFAOYSA-N 0.000 description 1
- MSTDXOZUKAQDRL-UHFFFAOYSA-N 4-Chromanone Chemical compound C1=CC=C2C(=O)CCOC2=C1 MSTDXOZUKAQDRL-UHFFFAOYSA-N 0.000 description 1
- KUAWMWVXZMQZLD-UHFFFAOYSA-N 6-nitro-2,3-dihydrochromen-4-one Chemical compound O1CCC(=O)C2=CC([N+](=O)[O-])=CC=C21 KUAWMWVXZMQZLD-UHFFFAOYSA-N 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000010907 mechanical stirring Methods 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
7806626-3 Uppfinningen skall i det följande beskrivas med några exempel.
Exemgel 1 A. 3-¿_(4-kromanyliden)amino_7-2-oxazolidinon 62 g (0,61 mol) 3-amino~2-oxazolidinon infördes i en 500 ml 3-halsad kolv försedd med termometer, omrörare och återflödeskylare samt behandlades i tur och ordning med 92 ml H20, 8 ml 10-procentig saltsyra och 42 g (0,28 mol) 4-kromanon i 200 ml etanol. Reaktions- blandningen återloppskokades i 36 h, destillerades i vakuum till halva volymen och kyldes i kylskåp över natten. Uppslamningen filtrerades och den vita kristallina substansen tvättades med 50 ml isopropanol och därefter med 200 ml dietyleter samt torkades; smp. 105 - 108°C.
Utbyte: 44 g (68 %).
Filtratet extraherades med 250 ml CHCI3, och CHCl3-extraktet torkades över magnesiumsulfat, filtrerades och destillerades i vakuum. återstoden uppslammades i 100 ml dietyleter, fick stå i 3 h, filtre- rades, och produkten torkades; smp. 50 - 62°C. Utbyte: 9 g (14 %).
De förenade råprodukterna omkristalliserades sedan ur 350 ml isopropa- nol, tvättades med 40 ml isopropanol, 150 ml dietyleter samt torkades; smp. 111 - 113°c. Utbyte: 40 q (62 % .
Analys beräknad för C12H12N2O3: C 62,06; H 5,21; 'N 12,06 Funnen: C 62,02; H 5,24; N 12,06.
B. 3-(4-kromanylamino)#2-oxazolidinontetartohydrat 75 g (0,32 mol) av föreningen enligt A. ovan och 750 ml metanol infördes i ett 2-liters högtryckskärl tillsammans med 9 g 5-procentigt palladium/bariumsulfat samt underkastades hydrering vid ca 2 kg/cm2.
Vätgasupptagningen var 21 volymdelar (teoretisk upptagning: 22 volym- delar vid 27°C). Reduktionsblandningen värmdes under återflöde, filtrerades, hides över natten i kylskåp och filtrerades på nytt.
Den erhållna vita kristallina fasta substansen tvättades med 100 ml kall metanol, dietyleter och torkades; smp. 104 -10506. Utbyte: 69 g (90 %).
Produkten omkristalliserades ur 400 ml metanol, tvättades med 100 ml kall metanol. dietyleter och torkades; smp. 105 - 107°C.
Utbyte: 63 g (82 %).
Analys beräknad för C12H14N2O3.1/4 H20: C 60,36; H 6,12; N 11,73 Funnen: C 60,70; H 6,28; N 11,74. 7806626-5 3 Éxemgel 2 A. 3-Äf(6-nitro-4-kromanyliden)amino_7-2-oxazolidoxon 85 g (0,44 mol) 6-nitro-4-kromanon i 460 ml bensen behandlades med 1 ml saltsyra (isopropanol) lösning under användande av mekanisk omrörning och återloppskokades, tills allt vattnet avlägsnats via en avskiljare. Den torkade lösningen behandlades med 46g(0,46 mol) 3-amino-2-oxazoiiainan och återioppskokaaes 2,6 h. 7,9 ml vatten uppsamlades (teoretiskt: 7,9 ml). Reaktionsblandningen torkades varm, kyldes till 10 - 11°C i 3 h och filtrerades. Den orangefärgade kristallina fasta substansen tvättades med 100 ml bensen, dietyleter och torkaaes, amp. 168 - 17o°c. utbyte= 107 g (sa %>.
Produkten omkristalliserades ur 650 ml nitrometan (Darco), tvätta- des med 100 ml kall nitrometan, dietyleter och torkades; smp. 170 - 1710.
Utbyte: 84 g (69 %).
Analys beräknad för C12H11N3O5: C 51,99; H 4,00; N 15,16 Funnen: C 51,96; H 4,03; N 15,14.
B. 3-¿_(6-amino-4-kromanyl)amino_7¥2-oxazolidinonhydroklorid 37 g (0,13 mol) av föreningen enligt A. ovan, 400 ml isopropanol och 8 g 5-procentigt Pd/C (50 % fuktighet) infördes i ett 1,8-liters tryckkärl och underkastades hydrering vid 3,5 kg/cmz. Vätgasupptag- ningen var 30 volymdelar (teoretisk upptagning: 36 volymdelar vid 26°C) under 22 h. Reduktionsblandningen värmdes under tillsats av ytterligare 500 ml isopropanol Darco och filtrerades. Filtratet inställdes på pH 2 med 30 ml saltsyra (isopropanol) lösning, kyldes över natten och filtrerades. Den gräddfärgade kristallina fasta substansen tvättades med 100 ml isopropanol, dietyleter och torkades; smp. 212 - 214°C under sönderdelning. Utbyte: 32 g (82 %). 30 g av produkten omkristalliserades ur 500 ml metanol (Darco) och tvättades med 50 ml blandning av metanol och eter samt torkades; smp. 212 - 213°c under sönaeraelning. utbyte: 21 g (ss %).
Analys beräknad för C12H15N303.HCl: C 50,44; H 5,64; N 14,71 Funnen: C 50,61: H 5,71; N 14,94.
Claims (3)
1. Förening med formeln o f i -nncl X ~\ i . _ . ,/lo NHN--c I )0 Hzc-CHZ i vilken X betecknar väte eller amino och n 0 eller 1.
2. Förening enligt krav 1 nämligen 3-(4-kromanylamino)- 2-oxazolidinon.
3. Förening enligt krav 1 nämligen 3-[Y6-amino-4- kromanyl)aminqj-2-oxazolidinøn hydroklorid. 7
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/812,124 US4108862A (en) | 1977-07-01 | 1977-07-01 | 3-(4-Chromanylamino)-2-oxazolidinones |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SE7806626L SE7806626L (sv) | 1979-01-02 |
| SE441675B true SE441675B (sv) | 1985-10-28 |
Family
ID=25208583
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SE7806626A SE441675B (sv) | 1977-07-01 | 1978-06-06 | 3-(4-kromanylamino)-2-oxazolidinoner |
Country Status (15)
| Country | Link |
|---|---|
| US (1) | US4108862A (sv) |
| JP (1) | JPS5414973A (sv) |
| AU (1) | AU516600B2 (sv) |
| BE (1) | BE868457A (sv) |
| CA (1) | CA1094077A (sv) |
| CH (1) | CH635098A5 (sv) |
| DE (1) | DE2828952A1 (sv) |
| ES (1) | ES471088A1 (sv) |
| FR (1) | FR2401158A1 (sv) |
| GB (1) | GB2000762B (sv) |
| IE (1) | IE46906B1 (sv) |
| IT (1) | IT1105476B (sv) |
| NL (1) | NL7806216A (sv) |
| SE (1) | SE441675B (sv) |
| ZA (1) | ZA783716B (sv) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0035868A1 (en) * | 1980-03-07 | 1981-09-16 | Takeda Chemical Industries, Ltd. | Bicyclic compounds, their production and use |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4093627A (en) * | 1977-07-01 | 1978-06-06 | Morton-Norwich Products, Inc. | 3-[(4-Chromanylidene)amino]-2-oxazolidinones |
-
1977
- 1977-07-01 US US05/812,124 patent/US4108862A/en not_active Expired - Lifetime
-
1978
- 1978-05-29 IE IE1069/78A patent/IE46906B1/en unknown
- 1978-06-02 AU AU36819/78A patent/AU516600B2/en not_active Expired
- 1978-06-06 SE SE7806626A patent/SE441675B/sv not_active IP Right Cessation
- 1978-06-07 NL NL7806216A patent/NL7806216A/xx not_active Application Discontinuation
- 1978-06-16 GB GB7827163A patent/GB2000762B/en not_active Expired
- 1978-06-21 IT IT49962/78A patent/IT1105476B/it active
- 1978-06-23 ES ES471088A patent/ES471088A1/es not_active Expired
- 1978-06-26 BE BE188842A patent/BE868457A/xx not_active IP Right Cessation
- 1978-06-27 FR FR7819170A patent/FR2401158A1/fr active Granted
- 1978-06-28 CA CA306,386A patent/CA1094077A/en not_active Expired
- 1978-06-28 JP JP7756578A patent/JPS5414973A/ja active Granted
- 1978-06-28 ZA ZA783716A patent/ZA783716B/xx unknown
- 1978-06-29 CH CH711678A patent/CH635098A5/de not_active IP Right Cessation
- 1978-06-30 DE DE19782828952 patent/DE2828952A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| ZA783716B (en) | 1980-02-27 |
| IT7849962A0 (it) | 1978-06-21 |
| CH635098A5 (de) | 1983-03-15 |
| CA1094077A (en) | 1981-01-20 |
| ES471088A1 (es) | 1980-03-01 |
| GB2000762B (en) | 1982-01-06 |
| US4108862A (en) | 1978-08-22 |
| NL7806216A (nl) | 1979-01-03 |
| AU516600B2 (en) | 1981-06-11 |
| IE781069L (en) | 1979-01-01 |
| FR2401158A1 (fr) | 1979-03-23 |
| SE7806626L (sv) | 1979-01-02 |
| JPS5414973A (en) | 1979-02-03 |
| DE2828952A1 (de) | 1979-01-18 |
| IE46906B1 (en) | 1983-11-02 |
| FR2401158B1 (sv) | 1981-07-10 |
| GB2000762A (en) | 1979-01-17 |
| AU3681978A (en) | 1979-12-06 |
| IT1105476B (it) | 1985-11-04 |
| BE868457A (fr) | 1978-12-27 |
| JPS622597B2 (sv) | 1987-01-20 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| NUG | Patent has lapsed |
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