NO129795B - - Google Patents

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Info

Publication number: NO129795B
Authority: NO; Norway
Prior art keywords: compound; benzodiazepine; ether; methyl; general formula
Prior art date: 1967-09-06

Application number

NO03463/68A

Other languages

English (en)

Norwegian (no)

Inventor

G Field

L Sternbach

W Zally

Original Assignee

Hoffmann La Roche

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1967-09-06

Filing date

1968-09-05

Publication date

1974-05-27

1968-09-05 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

1974-05-27 Publication of NO129795B publication Critical patent/NO129795B/no

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)

NO03463/68A 1967-09-06 1968-09-05 NO129795B (de)

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 (de)	1974-05-27

Family

ID=27099271

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
NO03463/68A NO129795B (de)	1967-09-06	1968-09-05
NO02899/70A NO129744B (de)	1967-09-06	1970-07-24

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
NO02899/70A NO129744B (de)	1967-09-06	1970-07-24

Country Status (12)

Country	Link
US (1)	US3624073A (de)
AT (1)	AT280295B (de)
CH (1)	CH503040A (de)
DE (1)	DE1795254A1 (de)
DK (2)	DK119166B (de)
ES (1)	ES357870A1 (de)
FI (1)	FI50977C (de)
IE (1)	IE32814B1 (de)
NL (1)	NL6812560A (de)
NO (2)	NO129795B (de)
SE (2)	SE339477B (de)
YU (1)	YU32233B (de)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4022767A (en) *	1975-09-22	1977-05-10	Mcneil Laboratories, Incorporated	2-Aminobenzodiazepine-5-ones
US4002610A (en) *	1975-09-22	1977-01-11	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
RU2519457C2 (ru) *	2010-01-25	2014-06-10	Джейкоб КОБЕЛТ	Устройство и способ распределения жидкости

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 AT AT863368A patent/AT280295B/de not_active IP Right Cessation
- 1968-09-05 ES ES357870A patent/ES357870A1/es not_active Expired
- 1968-09-05 DK DK427168AA patent/DK119166B/da unknown
- 1968-09-05 NO NO03463/68A patent/NO129795B/no unknown
- 1968-09-06 SE SE12062/68A patent/SE339477B/xx unknown
- 1968-09-06 SE SE05364/71A patent/SE365517B/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
NO129744B (de)	1974-05-20
FI50977B (de)	1976-05-31
DK119166B (da)	1970-11-23
DE1795254A1 (de)	1972-02-17
ES357870A1 (es)	1970-04-01
US3624073A (en)	1971-11-30
IE32814L (en)	1969-03-06
SE339477B (de)	1971-10-11
CH503040A (de)	1971-02-15
NL6812560A (de)	1969-03-10
DK122726B (da)	1972-04-04
YU32233B (en)	1974-06-30
AT280295B (de)	1970-04-10
SE365517B (de)	1974-03-25
FI50977C (fi)	1976-09-10
IE32814B1 (en)	1973-12-12
YU205168A (en)	1973-12-31

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