NO129795B - - Google Patents
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- Publication number
- NO129795B NO129795B NO03463/68A NO346368A NO129795B NO 129795 B NO129795 B NO 129795B NO 03463/68 A NO03463/68 A NO 03463/68A NO 346368 A NO346368 A NO 346368A NO 129795 B NO129795 B NO 129795B
- Authority
- NO
- Norway
- Prior art keywords
- compound
- benzodiazepine
- ether
- methyl
- general formula
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 4
- 229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 3
- 125000002524 organometallic group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 claims 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- -1 phenyl compound Chemical class 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 150000001557 benzodiazepines Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- ANRQGKOBLBYXFM-UHFFFAOYSA-M phenylmagnesium bromide Chemical compound Br[Mg]C1=CC=CC=C1 ANRQGKOBLBYXFM-UHFFFAOYSA-M 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- MHOLPEJAZVBJBA-UHFFFAOYSA-N 5,7-dichloro-1-methyl-2,3-dihydro-1,4-benzodiazepine Chemical compound ClC1=NCCN(C2=C1C=C(C=C2)Cl)C MHOLPEJAZVBJBA-UHFFFAOYSA-N 0.000 description 1
- IBVMEUYCJJYUGS-UHFFFAOYSA-N 7-chloro-2-(methylamino)-3,4-dihydro-1,4-benzodiazepin-5-one Chemical compound O=C1NCC(NC)=NC2=CC=C(Cl)C=C21 IBVMEUYCJJYUGS-UHFFFAOYSA-N 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- YLCXGBZIZBEVPZ-UHFFFAOYSA-N Medazepam Chemical compound C12=CC(Cl)=CC=C2N(C)CCN=C1C1=CC=CC=C1 YLCXGBZIZBEVPZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- SNIYGPDAYLBEMK-UHFFFAOYSA-M [I-].[Mg+]C1=CC=CC=C1 Chemical compound [I-].[Mg+]C1=CC=CC=C1 SNIYGPDAYLBEMK-UHFFFAOYSA-M 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- DBYQHFPBWKKZAT-UHFFFAOYSA-N lithium;benzene Chemical compound [Li+].C1=CC=[C-]C=C1 DBYQHFPBWKKZAT-UHFFFAOYSA-N 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 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 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/06—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4
- C07D243/10—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 4 condensed with carbocyclic rings or ring systems
- C07D243/14—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines
- C07D243/16—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals
- C07D243/18—1,4-Benzodiazepines; Hydrogenated 1,4-benzodiazepines substituted in position 5 by aryl radicals substituted in position 2 by nitrogen, oxygen or sulfur atoms
- C07D243/20—Nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US66571667A | 1967-09-06 | 1967-09-06 | |
| US71825968A | 1968-04-02 | 1968-04-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO129795B true NO129795B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-27 |
Family
ID=27099271
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO03463/68A NO129795B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-09-06 | 1968-09-05 | |
| NO02899/70A NO129744B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-09-06 | 1970-07-24 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO02899/70A NO129744B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1967-09-06 | 1970-07-24 |
Country Status (12)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4002610A (en) * | 1975-09-22 | 1977-01-11 | Mcneil Laboratories, Incorporated | 2-Aminobenzodiazepine-5-ones |
| US4022767A (en) * | 1975-09-22 | 1977-05-10 | Mcneil Laboratories, Incorporated | 2-Aminobenzodiazepine-5-ones |
| US5308430A (en) * | 1990-01-30 | 1994-05-03 | Makoto Saito | Reinforcing fiber sheet, method of manufacturing the same, and the method of reinforcing structure with the reinforcing fiber sheet |
| US5962337A (en) * | 1995-06-29 | 1999-10-05 | Pharmacopeia, Inc. | Combinatorial 1,4-benzodiazepin-2,5-dione library |
| CA2787981C (en) * | 2010-01-25 | 2014-12-30 | Jacob Kobelt | Apparatus and method for distributing fluid |
-
1968
- 1968-04-02 US US718259A patent/US3624073A/en not_active Expired - Lifetime
- 1968-08-09 CH CH1196968A patent/CH503040A/de not_active IP Right Cessation
- 1968-08-26 IE IE1040/68A patent/IE32814B1/xx unknown
- 1968-08-29 DE DE19681795254 patent/DE1795254A1/de active Pending
- 1968-09-02 YU YU2051/68A patent/YU32233B/xx unknown
- 1968-09-03 FI FI682478A patent/FI50977C/fi active
- 1968-09-04 NL NL6812560A patent/NL6812560A/xx unknown
- 1968-09-05 NO NO03463/68A patent/NO129795B/no unknown
- 1968-09-05 AT AT863368A patent/AT280295B/de not_active IP Right Cessation
- 1968-09-05 DK DK427168AA patent/DK119166B/da unknown
- 1968-09-05 ES ES357870A patent/ES357870A1/es not_active Expired
- 1968-09-06 SE SE05364/71A patent/SE365517B/xx unknown
- 1968-09-06 SE SE12062/68A patent/SE339477B/xx unknown
-
1969
- 1969-09-25 DK DK511869AA patent/DK122726B/da unknown
-
1970
- 1970-07-24 NO NO02899/70A patent/NO129744B/no unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU205168A (en) | 1973-12-31 |
| NL6812560A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1969-03-10 |
| YU32233B (en) | 1974-06-30 |
| FI50977C (fi) | 1976-09-10 |
| NO129744B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-05-20 |
| SE339477B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1971-10-11 |
| DK122726B (da) | 1972-04-04 |
| IE32814B1 (en) | 1973-12-12 |
| SE365517B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1974-03-25 |
| US3624073A (en) | 1971-11-30 |
| AT280295B (de) | 1970-04-10 |
| DE1795254A1 (de) | 1972-02-17 |
| FI50977B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1976-05-31 |
| CH503040A (de) | 1971-02-15 |
| ES357870A1 (es) | 1970-04-01 |
| IE32814L (en) | 1969-03-06 |
| DK119166B (da) | 1970-11-23 |
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