NO744054L - - Google Patents
Info
- Publication number
- NO744054L NO744054L NO744054A NO744054A NO744054L NO 744054 L NO744054 L NO 744054L NO 744054 A NO744054 A NO 744054A NO 744054 A NO744054 A NO 744054A NO 744054 L NO744054 L NO 744054L
- Authority
- NO
- Norway
- Prior art keywords
- compounds
- formula
- hydroxy
- pyrrolidone
- above meaning
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 32
- 238000000034 method Methods 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000003960 organic solvent Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 239000011737 fluorine Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 150000002894 organic compounds Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- -1 benzene and toluene Chemical compound 0.000 description 6
- 239000000932 sedative agent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 230000001624 sedative effect Effects 0.000 description 5
- LAQHRWLJPYPTHH-UHFFFAOYSA-N 5-hydroxy-1-methyl-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound CN1C(=O)CCC1(O)C1=CC=CC(C(F)(F)F)=C1 LAQHRWLJPYPTHH-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 230000000147 hypnotic effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 239000010410 layer Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- 230000007306 turnover Effects 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000000370 acceptor Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 2
- 235000019341 magnesium sulphate Nutrition 0.000 description 2
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229940125723 sedative agent Drugs 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- NNMBNYHMJRJUBC-UHFFFAOYSA-N 1-bromo-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Br)=C1 NNMBNYHMJRJUBC-UHFFFAOYSA-N 0.000 description 1
- WKMUVMVUOFWZMN-UHFFFAOYSA-N 1-ethyl-5-hydroxy-5-(3-methylphenyl)pyrrolidin-2-one Chemical compound CCN1C(=O)CCC1(O)C1=CC=CC(C)=C1 WKMUVMVUOFWZMN-UHFFFAOYSA-N 0.000 description 1
- ZZYOSARVKQOTEO-UHFFFAOYSA-N 1-ethyl-5-hydroxy-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound CCN1C(=O)CCC1(O)C1=CC=CC(C(F)(F)F)=C1 ZZYOSARVKQOTEO-UHFFFAOYSA-N 0.000 description 1
- KYEACNNYFNZCST-UHFFFAOYSA-N 1-methylpyrrolidine-2,5-dione Chemical compound CN1C(=O)CCC1=O KYEACNNYFNZCST-UHFFFAOYSA-N 0.000 description 1
- GLNOAEGCWGDNDG-UHFFFAOYSA-N 4-oxo-4-[3-(trifluoromethyl)phenyl]butanoic acid Chemical compound OC(=O)CCC(=O)C1=CC=CC(C(F)(F)F)=C1 GLNOAEGCWGDNDG-UHFFFAOYSA-N 0.000 description 1
- BXEICYMOFZJJED-UHFFFAOYSA-N 5-(2-fluoro-5-methylphenyl)-5-hydroxy-1-methylpyrrolidin-2-one Chemical compound CN1C(=O)CCC1(O)C1=CC(C)=CC=C1F BXEICYMOFZJJED-UHFFFAOYSA-N 0.000 description 1
- VUYGZEKSCURUEE-UHFFFAOYSA-N 5-[4-chloro-3-(trifluoromethyl)phenyl]-5-hydroxy-1-methylpyrrolidin-2-one Chemical compound CN1C(=O)CCC1(O)C1=CC=C(Cl)C(C(F)(F)F)=C1 VUYGZEKSCURUEE-UHFFFAOYSA-N 0.000 description 1
- DPENLYNWCONGTA-UHFFFAOYSA-N 5-[4-fluoro-3-(trifluoromethyl)phenyl]-5-hydroxy-1-methylpyrrolidin-2-one Chemical compound CN1C(=O)CCC1(O)C1=CC=C(F)C(C(F)(F)F)=C1 DPENLYNWCONGTA-UHFFFAOYSA-N 0.000 description 1
- YVSSROZPEKIDFD-UHFFFAOYSA-N 5-hydroxy-1-methyl-5-(3-methylphenyl)pyrrolidin-2-one Chemical compound CN1C(=O)CCC1(O)C1=CC=CC(C)=C1 YVSSROZPEKIDFD-UHFFFAOYSA-N 0.000 description 1
- JAGWISCUMYKWDJ-UHFFFAOYSA-N 5-hydroxy-5-(3-methylphenyl)pyrrolidin-2-one Chemical compound CC1=CC=CC(C2(O)NC(=O)CC2)=C1 JAGWISCUMYKWDJ-UHFFFAOYSA-N 0.000 description 1
- AVRJMHGSIAZZQT-UHFFFAOYSA-N 5-hydroxy-5-[3-(trifluoromethyl)phenyl]pyrrolidin-2-one Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(O)CCC(=O)N1 AVRJMHGSIAZZQT-UHFFFAOYSA-N 0.000 description 1
- DWWHQIRKVUZDAP-UHFFFAOYSA-N 6-hydroxy-1-methyl-6-(3-methylphenyl)piperidin-2-one Chemical compound CN1C(=O)CCCC1(O)C1=CC=CC(C)=C1 DWWHQIRKVUZDAP-UHFFFAOYSA-N 0.000 description 1
- MCXWOCVEWGIMOZ-UHFFFAOYSA-N 6-hydroxy-1-methyl-6-[3-(trifluoromethyl)phenyl]piperidin-2-one Chemical compound CN1C(=O)CCCC1(O)C1=CC=CC(C(F)(F)F)=C1 MCXWOCVEWGIMOZ-UHFFFAOYSA-N 0.000 description 1
- CUBMCOYIIWRJGZ-UHFFFAOYSA-N 6-hydroxy-6-[3-(trifluoromethyl)phenyl]piperidin-2-one Chemical compound C=1C=CC(C(F)(F)F)=CC=1C1(O)CCCC(=O)N1 CUBMCOYIIWRJGZ-UHFFFAOYSA-N 0.000 description 1
- 239000007818 Grignard reagent Substances 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- 241000906446 Theraps Species 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000001914 calming effect Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000003169 central nervous system Anatomy 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 150000004795 grignard reagents Chemical class 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000003326 hypnotic agent Substances 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Pyrrole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US41737473A | 1973-11-19 | 1973-11-19 | |
| US46837774A | 1974-05-09 | 1974-05-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO744054L true NO744054L (de) | 1975-06-16 |
Family
ID=27023717
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO744054A NO744054L (de) | 1973-11-19 | 1974-11-11 |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS5083367A (de) |
| AU (1) | AU7548374A (de) |
| DD (1) | DD114603A5 (de) |
| DE (1) | DE2453356A1 (de) |
| DK (1) | DK586174A (de) |
| FI (1) | FI325174A (de) |
| FR (1) | FR2251325A1 (de) |
| IL (1) | IL46074A0 (de) |
| NL (1) | NL7414908A (de) |
| NO (1) | NO744054L (de) |
| SE (1) | SE7414131L (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2737195A1 (de) | 1977-08-18 | 1979-03-01 | Hoechst Ag | Benzolsulfonamidderivate und verfahren zu ihrer herstellung |
| DE3431257A1 (de) * | 1984-08-24 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Neue (delta)-butyrolactame, pharmakologisch aktive zusammensetzungen derselben, verfahren zu ihrer herstellung und ihre medizinische verwendung |
-
1974
- 1974-11-08 FI FI3251/74A patent/FI325174A/fi unknown
- 1974-11-11 DE DE19742453356 patent/DE2453356A1/de active Pending
- 1974-11-11 NO NO744054A patent/NO744054L/no unknown
- 1974-11-11 SE SE7414131A patent/SE7414131L/xx unknown
- 1974-11-11 DK DK586174A patent/DK586174A/da unknown
- 1974-11-15 NL NL7414908A patent/NL7414908A/xx unknown
- 1974-11-18 AU AU75483/74A patent/AU7548374A/en not_active Expired
- 1974-11-18 JP JP49132131A patent/JPS5083367A/ja active Pending
- 1974-11-18 DD DD182426A patent/DD114603A5/xx unknown
- 1974-11-18 FR FR7437901A patent/FR2251325A1/fr not_active Withdrawn
- 1974-11-18 IL IL46074A patent/IL46074A0/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5083367A (de) | 1975-07-05 |
| NL7414908A (nl) | 1975-05-21 |
| DE2453356A1 (de) | 1975-05-22 |
| DD114603A5 (de) | 1975-08-12 |
| FR2251325A1 (en) | 1975-06-13 |
| SE7414131L (de) | 1975-05-20 |
| DK586174A (de) | 1975-07-21 |
| AU7548374A (en) | 1976-05-20 |
| FI325174A (de) | 1975-05-20 |
| IL46074A0 (en) | 1975-02-10 |
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