SU466660A3 - Способ получени производных бензодиазепина - Google Patents

Способ получени производных бензодиазепина

Info

Publication number: SU466660A3
Authority: SU; USSR - Soviet Union
Prior art keywords: methyl; dioxolan; mmol; dihydro; solution
Prior art date: 1970-12-23

Application number

SU1728346A

Other languages

English (en)

Russian (ru)

Inventor

Йе-Фонг Нинг Роберт (Кнр)

Хенрик Штернбах Лео (Сша)

Original Assignee

Ф.Хоффманн Ля Рош И Ко.Аг (Фирма)

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.)

1970-12-23

Filing date

1971-12-22

Publication date

1975-04-05

1971-12-22 Application filed by Ф.Хоффманн Ля Рош И Ко.Аг (Фирма) filed Critical Ф.Хоффманн Ля Рош И Ко.Аг (Фирма)

1975-04-05 Application granted granted Critical

1975-04-05 Publication of SU466660A3 publication Critical patent/SU466660A3/ru

Links

238000000034 method Methods 0.000 title claims 4
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 title claims 2
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims description 3
239000001257 hydrogen Substances 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
239000011260 aqueous acid Substances 0.000 claims 1
238000006243 chemical reaction Methods 0.000 claims 1
125000001475 halogen functional group Chemical group 0.000 claims 1
125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
230000007062 hydrolysis Effects 0.000 claims 1
238000006460 hydrolysis reaction Methods 0.000 claims 1
239000003960 organic solvent Substances 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
239000000243 solution Substances 0.000 description 22
239000000203 mixture Substances 0.000 description 16
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 description 14
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 13
UIOAQJNADLELPQ-UHFFFAOYSA-N C[C]1OCCO1 Chemical group C[C]1OCCO1 UIOAQJNADLELPQ-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
-1 5- (2-methyl-1,3 dioxol-2-yl) -3-phenyl-2,1-benzoxazole Chemical compound 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
229960001413 acetanilide Drugs 0.000 description 7
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
229910021529 ammonia Inorganic materials 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
125000003541 2-chlorobenzoyl group Chemical group ClC1=C(C(=O)*)C=CC=C1 0.000 description 4
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 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
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
238000009835 boiling Methods 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
238000010992 reflux Methods 0.000 description 4
235000011121 sodium hydroxide Nutrition 0.000 description 4
235000009518 sodium iodide Nutrition 0.000 description 4
PNVPNXKRAUBJGW-UHFFFAOYSA-N (2-chloroacetyl) 2-chloroacetate Chemical compound ClCC(=O)OC(=O)CCl PNVPNXKRAUBJGW-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 3
239000012965 benzophenone Substances 0.000 description 3
239000010410 layer Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
150000003839 salts Chemical class 0.000 description 3
HTWIZMNMTWYQRN-UHFFFAOYSA-N 2-methyl-1,3-dioxolane Chemical compound CC1OCCO1 HTWIZMNMTWYQRN-UHFFFAOYSA-N 0.000 description 2
HHXVQNVADPECCD-UHFFFAOYSA-N 2-methyl-2-(4-nitrophenyl)-1,3-dioxolane Chemical compound C=1C=C([N+]([O-])=O)C=CC=1C1(C)OCCO1 HHXVQNVADPECCD-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 2
239000005457 ice water Substances 0.000 description 2
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
239000003208 petroleum Substances 0.000 description 2
SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000012047 saturated solution Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
238000003756 stirring Methods 0.000 description 2
KTZQTRPPVKQPFO-UHFFFAOYSA-N 1,2-benzoxazole Chemical compound C1=CC=C2C=NOC2=C1 KTZQTRPPVKQPFO-UHFFFAOYSA-N 0.000 description 1
ABADUMLIAZCWJD-UHFFFAOYSA-N 1,3-dioxole Chemical compound C1OC=CO1 ABADUMLIAZCWJD-UHFFFAOYSA-N 0.000 description 1
BASMANVIUSSIIM-UHFFFAOYSA-N 1-chloro-2-(chloromethyl)benzene Chemical compound ClCC1=CC=CC=C1Cl BASMANVIUSSIIM-UHFFFAOYSA-N 0.000 description 1
MRDUURPIPLIGQX-UHFFFAOYSA-N 2-(2-chlorophenyl)acetonitrile Chemical compound ClC1=CC=CC=C1CC#N MRDUURPIPLIGQX-UHFFFAOYSA-N 0.000 description 1
YXNAWCUIZOCJNG-UHFFFAOYSA-N 2-iodo-n-phenylacetamide Chemical compound ICC(=O)NC1=CC=CC=C1 YXNAWCUIZOCJNG-UHFFFAOYSA-N 0.000 description 1
PCMWVURKIXMPLA-UHFFFAOYSA-N 2-oxo-5-phenyl-1,3-dihydro-1,4-benzodiazepine-7-carbaldehyde Chemical compound C12=CC(C=O)=CC=C2NC(=O)CN=C1C1=CC=CC=C1 PCMWVURKIXMPLA-UHFFFAOYSA-N 0.000 description 1
LYINTWKRUWVLBA-UHFFFAOYSA-N 2-phenyl-1,3-dioxolane Chemical compound O1CCOC1C1=CC=CC=C1 LYINTWKRUWVLBA-UHFFFAOYSA-N 0.000 description 1
UQZIVIVFXNMLLC-UHFFFAOYSA-N 2h-1,4-benzodiazepine Chemical compound C1C=NC=C2C=CC=CC2=N1 UQZIVIVFXNMLLC-UHFFFAOYSA-N 0.000 description 1
FJLFPNLOFYIETF-UHFFFAOYSA-N 5-(1,3-dioxolan-2-yl)-3-phenyl-2,1-benzoxazole Chemical compound O1CCOC1C1=CC2=C(C=3C=CC=CC=3)ON=C2C=C1 FJLFPNLOFYIETF-UHFFFAOYSA-N 0.000 description 1
NPRKPMGGWYKYRS-UHFFFAOYSA-N 5-(2-methyl-1,3-dioxolan-2-yl)-3-phenyl-2,1-benzoxazole Chemical compound C1=CC2=NOC(C=3C=CC=CC=3)=C2C=C1C1(C)OCCO1 NPRKPMGGWYKYRS-UHFFFAOYSA-N 0.000 description 1
IFPLKLPCDRAOIM-UHFFFAOYSA-N 5-phenyl-7-propanoyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C(CC)(=O)C=1C=CC2=C(C(=NCC(N2)=O)C2=CC=CC=C2)C1 IFPLKLPCDRAOIM-UHFFFAOYSA-N 0.000 description 1
OZOWKVGUJMKRON-UHFFFAOYSA-N 7-(2-methyl-1,3-dioxolan-2-yl)-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one Chemical compound C=1C=C2NC(=O)CN=C(C=3C=CC=CC=3)C2=CC=1C1(C)OCCO1 OZOWKVGUJMKRON-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 1
WCJUGFNKUJSBLI-UHFFFAOYSA-N O=C(C(C1OCCO1)(C(NC1=CC=CC=C1)=O)Cl)C1=CC=CC=C1 Chemical compound O=C(C(C1OCCO1)(C(NC1=CC=CC=C1)=O)Cl)C1=CC=CC=C1 WCJUGFNKUJSBLI-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
IDVPXBIYMFWUEF-UHFFFAOYSA-N [2-amino-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]-phenylmethanone Chemical compound C=1C=C(N)C(C(=O)C=2C=CC=CC=2)=CC=1C1(C)OCCO1 IDVPXBIYMFWUEF-UHFFFAOYSA-N 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
229940045348 brown mixture Drugs 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
SPWVRYZQLGQKGK-UHFFFAOYSA-N dichloromethane;hexane Chemical compound ClCCl.CCCCCC SPWVRYZQLGQKGK-UHFFFAOYSA-N 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
DLLJVQNYBYOKGS-UHFFFAOYSA-N ethoxyethane;pentane Chemical compound CCCCC.CCOCC DLLJVQNYBYOKGS-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000007788 liquid Substances 0.000 description 1
230000008018 melting Effects 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
MNWBNISUBARLIT-UHFFFAOYSA-N sodium cyanide Chemical compound [Na+].N#[C-] MNWBNISUBARLIT-UHFFFAOYSA-N 0.000 description 1
239000007787 solid Substances 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000000725 suspension Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C247/00—Compounds containing azido groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/20—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings condensed with carbocyclic rings or ring systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/14—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D317/28—Radicals substituted by nitrogen atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

SU1728346A 1970-12-23 1971-12-22 Способ получени производных бензодиазепина SU466660A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US10111770A	1970-12-23	1970-12-23

Publications (1)

Publication Number	Publication Date
SU466660A3 true SU466660A3 (ru)	1975-04-05

Family

ID=22283112

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1728346A SU466660A3 (ru)	1970-12-23	1971-12-22	Способ получени производных бензодиазепина

Country Status (5)

Country	Link
AT (4)	ATA847174A (cs)
CS (1)	CS158717B2 (cs)
IL (1)	IL38416A (cs)
SU (1)	SU466660A3 (cs)
ZA (2)	ZA717837B (cs)

1971
- 1971-11-22 ZA ZA717837A patent/ZA717837B/xx unknown
- 1971-12-21 IL IL38416A patent/IL38416A/xx unknown
- 1971-12-21 ZA ZA718528A patent/ZA718528B/xx unknown
- 1971-12-22 AT AT847174*1A patent/ATA847174A/de unknown
- 1971-12-22 SU SU1728346A patent/SU466660A3/ru active
- 1971-12-22 CS CS892371A patent/CS158717B2/cs unknown
1974
- 1974-10-21 AT AT847374*1A patent/AT326133B/de active
- 1974-10-22 AT AT847674*1A patent/AT326135B/de active
- 1974-10-22 AT AT847574*1A patent/AT326134B/de active

Also Published As

Publication number	Publication date
IL38416A0 (en)	1972-02-29
ATA847674A (de)	1975-02-15
ATA847174A (de)	1975-01-15
CS158717B2 (cs)	1974-11-25
ZA718528B (en)	1972-09-27
AT326134B (de)	1975-11-25
ATA847574A (de)	1975-02-15
AT326135B (de)	1975-11-25
AT326133B (de)	1975-11-25
ATA847374A (de)	1975-02-15
IL38416A (en)	1975-04-25
ZA717837B (en)	1972-08-30

Publication	Publication Date	Title
US3400128A (en)	1968-09-03	Heterocyclic intermediates
US3297755A (en)	1967-01-10	2-chloro-5-trifluoromethylbenzo-phenone compounds
US3121075A (en)	1964-02-11	Aminobenzodiazepines
SU466660A3 (ru)	1975-04-05	Способ получени производных бензодиазепина
US3131178A (en)	1964-04-28	Process for producing s-phenyl-l
US3784542A (en)	1974-01-08	Benzodiazepin-2-ones
FR2618777A1 (fr)	1989-02-03	Benzazepines a action therapeutique
US3121114A (en)	1964-02-11	Certificate of correction
SU520917A3 (ru)	1976-07-05	Способ получени производных бензодиазепина
CA1114373A (en)	1981-12-15	Benzodiazepine derivatives
US4247463A (en)	1981-01-27	Process for the preparation of imidazobenzodiazepines
US3203990A (en)	1965-08-31	2-amino-2'-halo-5-nitro benzophenones
SU421195A3 (ru)	1974-03-25	Способ получения производных бензодиазепина
US3120521A (en)	1964-02-04	2-methyl-7-trifluoromethyl-4h-3, 1 benzoxazine-4-one
US3144439A (en)	1964-08-11	Process for production of benzo-
US3197467A (en)	1965-07-27	Process for preparing 1, 3-dihydro-3-hydroxy-2h-1, 4-benzodiazepin-2-ones
US3686308A (en)	1972-08-22	5-lower alkanoyl-2-glycylamino-benzophenones
PL99162B1 (pl)	1978-06-30	Sposob wytwarzania pochodnych benzodwuazepiny
SU430552A1 (ru)	1974-05-30	Способ получения производных бензодиазепина
US3886214A (en)	1975-05-27	Benzodiazepin-2-ones and processes for the preparation thereof
US3721666A (en)	1973-03-20	1-(phenyl or pyridyl)-4-(alkyl or alkenyl)-3h-1,4-benzodiazepine-2,5-(1h,4h)-diones
US3311612A (en)	1967-03-28	Process for preparing
US3117965A (en)	1964-01-14	Substituted-i
US3900501A (en)	1975-08-19	Benzophenone intermediates for 7-lower alkanoyl benzodiazepines
CA1202023A (en)	1986-03-18	Benzodiazepines