CH599947A5 - 4-phenyl-2-morpholinones - Google Patents
4-phenyl-2-morpholinonesInfo
- Publication number
- CH599947A5 CH599947A5 CH715476A CH715476A CH599947A5 CH 599947 A5 CH599947 A5 CH 599947A5 CH 715476 A CH715476 A CH 715476A CH 715476 A CH715476 A CH 715476A CH 599947 A5 CH599947 A5 CH 599947A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- formula
- group
- atom
- och3
- Prior art date
Links
- PQJKFWVFRHRHDV-UHFFFAOYSA-N 4-phenylmorpholin-2-one Chemical class C1COC(=O)CN1C1=CC=CC=C1 PQJKFWVFRHRHDV-UHFFFAOYSA-N 0.000 title abstract 2
- -1 phenylthiomethyl Chemical group 0.000 claims abstract description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 39
- 238000000034 method Methods 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 9
- VSEAAEQOQBMPQF-UHFFFAOYSA-N morpholin-3-one Chemical class O=C1COCCN1 VSEAAEQOQBMPQF-UHFFFAOYSA-N 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical class CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 4
- 125000005843 halogen group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 150000007529 inorganic bases Chemical class 0.000 claims description 2
- 239000002904 solvent Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 2
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 claims 1
- 150000008041 alkali metal carbonates Chemical class 0.000 claims 1
- 239000002585 base Substances 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 claims 1
- ORTFAQDWJHRMNX-UHFFFAOYSA-M oxidooxomethyl Chemical compound [O-][C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-M 0.000 claims 1
- 230000001315 anti-hyperlipaemic effect Effects 0.000 abstract 1
- 230000000871 hypocholesterolemic effect Effects 0.000 abstract 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 22
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 description 19
- 150000001875 compounds Chemical class 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000007787 solid Substances 0.000 description 8
- HVYWMOMLDIMFJA-DPAQBDIFSA-N cholesterol Chemical compound C1C=C2C[C@@H](O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2 HVYWMOMLDIMFJA-DPAQBDIFSA-N 0.000 description 7
- 241001465754 Metazoa Species 0.000 description 6
- 210000002966 serum Anatomy 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- PLGXEPHZCXBYLP-UHFFFAOYSA-N (-)-munitagine Chemical compound C1C2=CC=C(OC)C(O)=C2C2CC(C=C(C(=C3)O)OC)=C3C1N2C PLGXEPHZCXBYLP-UHFFFAOYSA-N 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 150000003626 triacylglycerols Chemical class 0.000 description 4
- MTJPIKUTDCMUNT-UHFFFAOYSA-N 6-[(4-chlorophenoxy)methyl]-4-phenylmorpholin-2-one Chemical compound C1=CC(Cl)=CC=C1OCC1OC(=O)CN(C=2C=CC=CC=2)C1 MTJPIKUTDCMUNT-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000700159 Rattus Species 0.000 description 3
- 210000004369 blood Anatomy 0.000 description 3
- 239000008280 blood Substances 0.000 description 3
- 235000012000 cholesterol Nutrition 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- 206010003210 Arteriosclerosis Diseases 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 208000011775 arteriosclerosis disease Diseases 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- KNHUKKLJHYUCFP-UHFFFAOYSA-N clofibrate Chemical compound CCOC(=O)C(C)(C)OC1=CC=C(Cl)C=C1 KNHUKKLJHYUCFP-UHFFFAOYSA-N 0.000 description 2
- 229960001214 clofibrate Drugs 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 230000002265 prevention Effects 0.000 description 2
- OGJKMZVUJJYWKO-CYBMUJFWSA-N stepharine Chemical compound C([C@H]1NCCC=2C=C(C(=C3C=21)OC)OC)C13C=CC(=O)C=C1 OGJKMZVUJJYWKO-CYBMUJFWSA-N 0.000 description 2
- SBGNJMTZRNVDLY-UHFFFAOYSA-N 1-anilino-3-(4-chlorophenoxy)propan-2-ol Chemical compound C=1C=C(Cl)C=CC=1OCC(O)CNC1=CC=CC=C1 SBGNJMTZRNVDLY-UHFFFAOYSA-N 0.000 description 1
- KSLSZOOZWRMSAP-UHFFFAOYSA-N 2-[(4-chlorophenoxy)methyl]oxirane Chemical compound C1=CC(Cl)=CC=C1OCC1OC1 KSLSZOOZWRMSAP-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
- IEDBNTAKVGBZEP-VMPITWQZSA-N N-trans-sinapoyltyramine Chemical compound COC1=C(O)C(OC)=CC(\C=C\C(=O)NCCC=2C=CC(O)=CC=2)=C1 IEDBNTAKVGBZEP-VMPITWQZSA-N 0.000 description 1
- KLTRAKZQWILICF-UHFFFAOYSA-N [4-(4-heptylphenoxy)carbonylphenyl] 4-nitrobenzoate Chemical compound C1=CC(CCCCCCC)=CC=C1OC(=O)C(C=C1)=CC=C1OC(=O)C1=CC=C([N+]([O-])=O)C=C1 KLTRAKZQWILICF-UHFFFAOYSA-N 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- PQJJJMRNHATNKG-UHFFFAOYSA-N ethyl bromoacetate Chemical class CCOC(=O)CBr PQJJJMRNHATNKG-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 230000002496 gastric effect Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- ZXALBIGVBSYIGH-UHFFFAOYSA-N n-(3-acetyl-7-chloro-2-methyl-1-benzofuran-5-yl)-2,4,5-trimethylbenzenesulfonamide Chemical compound C1=C2C(C(=O)C)=C(C)OC2=C(Cl)C=C1NS(=O)(=O)C1=CC(C)=C(C)C=C1C ZXALBIGVBSYIGH-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/30—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings
- C07D265/32—1,4-Oxazines; Hydrogenated 1,4-oxazines not condensed with other rings with oxygen atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Obesity (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Hematology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP50068926A JPS51146479A (en) | 1975-06-06 | 1975-06-06 | Process for preparing new morpholinone derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH599947A5 true CH599947A5 (en) | 1978-06-15 |
Family
ID=13387735
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH715476A CH599947A5 (en) | 1975-06-06 | 1976-06-04 | 4-phenyl-2-morpholinones |
Country Status (7)
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS52109087U (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1976-02-13 | 1977-08-19 |
-
1975
- 1975-06-06 JP JP50068926A patent/JPS51146479A/ja active Granted
-
1976
- 1976-05-31 PT PT65158A patent/PT65158B/pt unknown
- 1976-06-03 AT AT408976A patent/AT346354B/de not_active IP Right Cessation
- 1976-06-04 CH CH715476A patent/CH599947A5/de not_active IP Right Cessation
- 1976-06-04 DD DD193197A patent/DD125207A5/xx unknown
- 1976-06-04 LU LU75096A patent/LU75096A1/xx unknown
- 1976-06-04 ES ES448562A patent/ES448562A1/es not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| LU75096A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-01-24 |
| ATA408976A (de) | 1978-03-15 |
| PT65158B (en) | 1977-10-13 |
| ES448562A1 (es) | 1977-07-01 |
| DD125207A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-04-06 |
| JPS5242797B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1977-10-26 |
| AT346354B (de) | 1978-11-10 |
| JPS51146479A (en) | 1976-12-16 |
| PT65158A (en) | 1976-06-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |