NO753159L - - Google Patents

Info

Publication number: NO753159L
Authority: NO; Norway
Prior art keywords: phenyl; malonic acid; chloro; acid ethyl; benzodiazepine
Prior art date: 1971-03-01

Application number

NO753159A

Other languages

English (en)

Norwegian (no)

Inventor

K-H Weber

A Bauer

Original Assignee

Boehringer Sohn Ingelheim

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.)

1971-03-01

Filing date

1975-09-16

Publication date

1972-09-04

1971-03-01 Priority claimed from AT174471A external-priority patent/AT308755B/de

1972-09-04 Publication of NO753159L publication Critical patent/NO753159L/no

1975-09-16 Application filed by Boehringer Sohn Ingelheim filed Critical Boehringer Sohn Ingelheim

1975-09-16 Priority to NO753159A priority Critical patent/NO753159L/no

Links

238000000034 method Methods 0.000 claims description 28
239000002253 acid Substances 0.000 claims description 23
-1 alkyl radical Chemical class 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 4
150000001266 acyl halides Chemical class 0.000 claims description 3
SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
YUDRVAHLXDBKSR-UHFFFAOYSA-N [CH]1CCCCC1 Chemical compound [CH]1CCCCC1 YUDRVAHLXDBKSR-UHFFFAOYSA-N 0.000 claims description 2
CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 2
229910052739 hydrogen Inorganic materials 0.000 claims description 2
239000001257 hydrogen Substances 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
238000002360 preparation method Methods 0.000 claims description 2
239000003795 chemical substances by application Substances 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
238000007363 ring formation reaction Methods 0.000 description 24
238000006243 chemical reaction Methods 0.000 description 22
238000007127 saponification reaction Methods 0.000 description 21
NBKNFNAHFNVUOW-UHFFFAOYSA-N 3-ethoxy-3-oxopropanoic acid;hydrochloride Chemical compound Cl.CCOC(=O)CC(O)=O NBKNFNAHFNVUOW-UHFFFAOYSA-N 0.000 description 19
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
239000002904 solvent Substances 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
238000005917 acylation reaction Methods 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
239000003921 oil Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
ZBFPPOKYYPQMBZ-UHFFFAOYSA-N 1-acetyl-7-chloro-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C(=O)C)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 ZBFPPOKYYPQMBZ-UHFFFAOYSA-N 0.000 description 2
GQFDPYJUUFYOFM-UHFFFAOYSA-N 1-benzoyl-7-bromo-5-phenyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C=2C=CC=CC=2)C2=CC(Br)=CC=C2N1C(=O)C1=CC=CC=C1 GQFDPYJUUFYOFM-UHFFFAOYSA-N 0.000 description 2
RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 description 2
XGTITDAWBWGDIQ-UHFFFAOYSA-N 7-chloro-2,4-dioxo-5-phenyl-1,5-benzodiazepine-1-carbaldehyde Chemical compound C12=CC(Cl)=CC=C2N(C=O)C(=O)CC(=O)N1C1=CC=CC=C1 XGTITDAWBWGDIQ-UHFFFAOYSA-N 0.000 description 2
FVNSAGQEFPPDKP-UHFFFAOYSA-N 7-chloro-5-phenyl-1-propanoyl-1,5-benzodiazepine-2,4-dione Chemical compound O=C1CC(=O)N(C(=O)CC)C2=CC=C(Cl)C=C2N1C1=CC=CC=C1 FVNSAGQEFPPDKP-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
230000010933 acylation Effects 0.000 description 2
239000000203 mixture Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
238000000746 purification Methods 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
235000011121 sodium hydroxide Nutrition 0.000 description 2
239000007858 starting material Substances 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
UNFHOAZOCIELCW-UHFFFAOYSA-N 1,5-dihydro-1,5-benzodiazepine-2,4-dione Chemical class N1C(=O)CC(=O)NC2=CC=CC=C21 UNFHOAZOCIELCW-UHFFFAOYSA-N 0.000 description 1
OLWCZFFGCONJFQ-UHFFFAOYSA-N 2,4-diphenyl-1h-benzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC(C=3C=CC=CC=3)=C2N1 OLWCZFFGCONJFQ-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
230000001773 anti-convulsant effect Effects 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
JYYOBHFYCIDXHH-UHFFFAOYSA-N carbonic acid;hydrate Chemical compound O.OC(O)=O JYYOBHFYCIDXHH-UHFFFAOYSA-N 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
230000020176 deacylation Effects 0.000 description 1
238000005947 deacylation reaction Methods 0.000 description 1
QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 1
239000012467 final product Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
239000003158 myorelaxant agent Substances 0.000 description 1
XRYSCSFJNUNNAU-UHFFFAOYSA-N n-chloro-n-phenylaniline Chemical compound C=1C=CC=CC=1N(Cl)C1=CC=CC=C1 XRYSCSFJNUNNAU-UHFFFAOYSA-N 0.000 description 1
125000001209 o-nitrophenyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])[N+]([O-])=O 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
238000010992 reflux Methods 0.000 description 1
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1

Landscapes

Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NO753159A 1971-03-01 1975-09-16 NO753159L (da)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
NO753159A NO753159L (da)	1971-03-01	1975-09-16

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
AT174471A AT308755B (de)	1971-03-01	1971-03-01	Verfahren zur Herstellung von 1-Acyl-5-phenyl-1H-1,5-benzodiazepin-2,4-(3H,5H)-dionen
NO62472		1972-02-29
NO753159A NO753159L (da)	1971-03-01	1975-09-16

Publications (1)

Publication Number	Publication Date
NO753159L true NO753159L (da)	1972-09-04

Family

ID=27147860

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO753159A NO753159L (da)	1971-03-01	1975-09-16

Country Status (1)

Country	Link
NO (1)	NO753159L (da)

1975
- 1975-09-16 NO NO753159A patent/NO753159L/no unknown

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