SU461502A3 - Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов - Google Patents

Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов

Info

Publication number: SU461502A3
Authority: SU; USSR - Soviet Union
Prior art keywords: aryl; benzodiazepin; obtaining; dyons; diones
Prior art date: 1971-12-29

Application number

SU1955543A

Other languages

English (en)

Inventor

Бауер Адольф

Гейнц Вебер Карл

Даннеберг Петер

Иосеф Кун Франц

Original Assignee

К.Х.Берингер Зон (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.)

1971-12-29

Filing date

1972-12-20

Publication date

1975-02-25

1972-12-20 Application filed by К.Х.Берингер Зон (Фирма) filed Critical К.Х.Берингер Зон (Фирма)

1975-02-25 Application granted granted Critical

1975-02-25 Publication of SU461502A3 publication Critical patent/SU461502A3/ru

Links

238000000034 method Methods 0.000 title description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 description 2
239000007800 oxidant agent Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
239000012286 potassium permanganate Substances 0.000 description 2
239000002904 solvent Substances 0.000 description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 description 1
229940053197 benzodiazepine derivative antiepileptics Drugs 0.000 description 1
125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
235000019439 ethyl acetate Nutrition 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000203 mixture Substances 0.000 description 1
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
-1 nitro, amino Chemical group 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Medicinal Preparation (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)

Description

(54) СПОСОБ ПОЛУЧЕНИЯ 1-АРИЛ-ЗЯ-1,4БЕНЗОДИАЗЕПИН-2 ,5-(1Я, 4Я)-ДИОНОВ

Предлагаетс способ получени новых производных бензодиазепина с ценными фармакологическими свойствами.

Основанный на известной реакции способ позвол ет получать новые соединени , обладающие лучшими свойствами, чем у известных соединений подобного действи .

Описываетс способ получени 1-арил-ЗЯ1 ,4-бензодиазепин-2,5- (1 Я, 4Я) -дионов общей формулы 1

R, О

где RI означает фенильный радикал, незамещенный или замещенный в орто-, мета- или пара-положении атомом фтора, хлора или брома, трифторметильной или нитрогруппой, или а-пиридильный радикал;

Кг - атом водорода, фтора, хлора или брома , трифторметил, нитро-, амино-, циано- или оксигруппа,

заключающийс в том, что соединение общей формулы 2

где R) и R2 имеют указанные значени , подвергают взаимодействию с сильным окисл ющим средством, целевой продукт выдел ют известными приемами.

В качестве окисл ющего средства примен ют , например, хромовую кислоту/серную кислоту, пермангапат кали или активированную двуокись марганца.

Дл окислени хромовой кислотой/серной кислотой и перманганатом кали особенно пригодны смешивающиес с водой растворители , которые даже при указанных услови х реакции не могут окисл тьс , например ацетон , метилэтилкетон, лед на уксусна кислота , диоксан, тетрагидрофуран или смеси этих растворителей.

Кроме того, окисление с активированной двуокисью марганца можно удовлетворительно осуществл ть при применении уксусного эфира, диэтилового эфира, метиленхловида или хлороформа.

SU1955543A 1971-12-29 1972-12-20 Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов SU461502A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE2165311A DE2165311A1 (de)	1971-12-29	1971-12-29	Neue 1-aryl-3h-1,4-benzodiazepin2,5-(1h,4h)-dione

Publications (1)

Publication Number	Publication Date
SU461502A3 true SU461502A3 (ru)	1975-02-25

Family

ID=5829591

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
SU1860137*7A SU452098A3 (ru)	1971-12-29	1972-12-20	Способ получени 1-арил-3н-1,4 -бензодиазепин-2,5-(1н,4н)-дионов
SU1955543A SU461502A3 (ru)	1971-12-29	1972-12-20	Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов

Family Applications Before (1)

Application Number	Title	Priority Date	Filing Date
SU1860137*7A SU452098A3 (ru)	1971-12-29	1972-12-20	Способ получени 1-арил-3н-1,4 -бензодиазепин-2,5-(1н,4н)-дионов

Country Status (23)

Country	Link
JP (1)	JPS4885587A (ru)
AT (2)	AT327912B (ru)
BE (1)	BE793460A (ru)
BG (2)	BG20375A3 (ru)
CA (1)	CA1028702A (ru)
CH (2)	CH583208A5 (ru)
DD (1)	DD106384A5 (ru)
DE (1)	DE2165311A1 (ru)
DK (1)	DK129655B (ru)
ES (2)	ES410057A1 (ru)
FI (1)	FI54920C (ru)
FR (1)	FR2166204B1 (ru)
GB (1)	GB1395772A (ru)
HU (1)	HU165306B (ru)
IE (1)	IE37815B1 (ru)
IL (1)	IL41198A (ru)
NL (1)	NL7217795A (ru)
NO (1)	NO138089C (ru)
PL (2)	PL85284B1 (ru)
RO (1)	RO62852A (ru)
SE (1)	SE405120B (ru)
SU (2)	SU452098A3 (ru)
ZA (1)	ZA729073B (ru)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1319144C (en) *	1986-11-14	1993-06-15	Quirico Branca	Tetrahydronaphthalene derivatives
RU2687556C1 (ru) *	2018-12-24	2019-05-15	Акционерное общество "Федеральный научно-производственный центр "Алтай"	Способ получения 7-хлор-1,3-дигидро-1-метил-5-фенил-2Н-1,4-бензодиазепин-2-она

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AT280290B (de) *	1967-11-24	1970-04-10	Boehringer Sohn Ingelheim	Verfahren zur Herstellung von neuen 1-Phenyl-4-alkyl-3H-1,4-benzodiazepin-2,5-[1H,4H]-dionen

0
- BE BE793460D patent/BE793460A/xx unknown
1971
- 1971-12-29 DE DE2165311A patent/DE2165311A1/de active Pending
1972
- 1972-12-19 AT AT1080772A patent/AT327912B/de not_active IP Right Cessation
- 1972-12-19 RO RO7200073207A patent/RO62852A/ro unknown
- 1972-12-19 AT AT228574*1A patent/AT324345B/de not_active IP Right Cessation
- 1972-12-20 SU SU1860137*7A patent/SU452098A3/ru active
- 1972-12-20 SU SU1955543A patent/SU461502A3/ru active
- 1972-12-21 DK DK641872AA patent/DK129655B/da unknown
- 1972-12-26 JP JP47129704A patent/JPS4885587A/ja active Pending
- 1972-12-26 BG BG025578A patent/BG20375A3/xx unknown
- 1972-12-26 BG BG022240A patent/BG19805A3/xx unknown
- 1972-12-27 CH CH250676A patent/CH583208A5/xx not_active IP Right Cessation
- 1972-12-27 CH CH1887672A patent/CH587830A5/xx not_active IP Right Cessation
- 1972-12-27 ES ES410057A patent/ES410057A1/es not_active Expired
- 1972-12-27 DD DD168055*A patent/DD106384A5/xx unknown
- 1972-12-27 ZA ZA729073A patent/ZA729073B/xx unknown
- 1972-12-28 PL PL1972159831A patent/PL85284B1/pl unknown
- 1972-12-28 CA CA160,145A patent/CA1028702A/en not_active Expired
- 1972-12-28 HU HUBO5306A patent/HU165306B/hu unknown
- 1972-12-28 PL PL1972175731A patent/PL84244B1/pl unknown
- 1972-12-28 SE SE7217089A patent/SE405120B/xx unknown
- 1972-12-28 IL IL41198A patent/IL41198A/en unknown
- 1972-12-28 NO NO4808/72A patent/NO138089C/no unknown
- 1972-12-28 FI FI3686/72A patent/FI54920C/fi active
- 1972-12-28 GB GB5988172A patent/GB1395772A/en not_active Expired
- 1972-12-29 IE IE1805/72A patent/IE37815B1/xx unknown
- 1972-12-29 NL NL7217795A patent/NL7217795A/xx not_active Application Discontinuation
- 1972-12-29 FR FR7247013A patent/FR2166204B1/fr not_active Expired
1974
- 1974-04-16 ES ES425329A patent/ES425329A1/es not_active Expired

Also Published As

Publication number	Publication date
DD106384A5 (ru)	1974-06-12
ES410057A1 (es)	1976-04-01
FI54920B (fi)	1978-12-29
SE405120B (sv)	1978-11-20
CH583208A5 (ru)	1976-12-31
NO138089B (no)	1978-03-20
NL7217795A (ru)	1973-07-03
HU165306B (ru)	1974-08-28
BE793460A (fr)	1973-06-28
CA1028702A (en)	1978-03-28
DK129655C (ru)	1975-04-07
IE37815B1 (en)	1977-10-26
FI54920C (fi)	1979-04-10
FR2166204B1 (ru)	1977-01-14
ES425329A1 (es)	1976-11-01
RO62852A (fr)	1977-11-15
SU452098A3 (ru)	1974-11-30
BG19805A3 (bg)	1975-10-10
PL85284B1 (en)	1976-04-30
FR2166204A1 (ru)	1973-08-10
DK129655B (da)	1974-11-04
NO138089C (no)	1978-06-28
JPS4885587A (ru)	1973-11-13
CH587830A5 (ru)	1977-05-13
ZA729073B (en)	1974-09-25
ATA1080772A (de)	1975-05-15
PL84244B1 (en)	1976-03-31
AT324345B (de)	1975-08-25
DE2165311A1 (de)	1973-07-12
IL41198A0 (en)	1973-02-28
BG20375A3 (bg)	1975-11-05
GB1395772A (en)	1975-05-29
AT327912B (de)	1976-02-25
IE37815L (en)	1973-06-29
IL41198A (en)	1976-08-31

Publication	Publication Date	Title
SU461502A3 (ru)	1975-02-25	Способ получени 1-арил-3н-1, 4-бензодиазепин-2,5-(1н,4н)дионов
US3951954A (en)	1976-04-20	Novel oxofuryl ester derivatives of penicillin and cephalosporin
Galvez et al.	1981	Functional derivatives of thiophene. I. Synthesis and 1H‐NMR spectra in the 2‐aminothiophene series
JP2957699B2 (ja)	1999-10-06	７α―アルコキシセフェム誘導体の製造方法
Tatsugi et al.	1986	A convenient one-pot synthesis of acenaphthenequinones from 1-acenaphthenones by NBS-DMSO oxidation.
JPH0826236B2 (ja)	1996-03-13	アゾメチン又はインドアニリン系色素の製造方法
SU559645A3 (ru)	1977-05-25	Способ получени производных тиадиазолилмочевины
US3282968A (en)	1966-11-01	2, 3-dicyano-5-sulfonyl-6-substituted para-benzoquinone and the corresponding hydroquinone
US3935239A (en)	1976-01-27	Process for producing aromatic α-diketones
Uemura et al.	1976	The reaction of arylthallium (III) compounds with metal nitrite. Synthesis of nitroarenes.
SU644775A1 (ru)	1979-01-30	Способ получени нтарной кислоты или ее алкилзамещенных
Jarvis et al.	1981	Thermolysis of. alpha.-azido sulfides, sulfoxides, and sulfones: dependence of mechanism on oxidation state of sulfur
Koster et al.	1978	Chlorination of the cephem dihydrothiazine ring. Factors influencing C-2 substitution vs. degradation to isothiazoles1
Sataty	1972	1, 4, 5-Thiadiazepines—II: A novel ring contraction giving 1, 4-thiazine derivatives
SU932801A1 (ru)	1983-01-30	Способ получени 4,5-диоксобензо-2,1,3-тиадиазола
Baciocchi et al.	1992	Halogenation and oxidation of 2, 5-bis (ethoxycarbonyl)-3, 4-dialkylpyrroles. A possible route to side-chain functionalized 3, 4-dialkylpyrroles
SU428608A3 (ru)	1974-05-15	Способ получения сложных эфиров сульфоксида з-формил-7-ациламино-аз-цефалоспорановой кислоты 12
Grehn	1977	A method for nitration of thiazoles
Sasaki et al.	1970	Studies on Reactions of Isoprenoids. XI. Stereochemistry of the Ritter Reaction Products of Camphene with Unsaturated Nitriles
US5189228A (en)	1993-02-23	Tetranitronoradamantane
SU453404A1 (ru)	1974-12-15	Способ получения пиразол-3-карбоновых кислот
SU829629A1 (ru)	1981-05-15	Способ получени 3-фенил-5-алкил-4-НиТРОизОКСАзОлОВ
CH629811A5 (de)	1982-05-14	Verfahren zur herstellung von neuen alkoxylierten beta-lactamen.
CH618702A5 (ru)	1980-08-15
Suzuki et al.	1980	NON-CONVENTIONAL NITRATION OF 2, 5-DIMETHYLTH IOPHENE AND ITS 3, 4-DIBROMO DERIVATIVE