CH417612A - Procedimento per l'ottenimento di 1,4-benzodiazepin-2-oni - Google Patents
Procedimento per l'ottenimento di 1,4-benzodiazepin-2-oniInfo
- Publication number
- CH417612A CH417612A CH895063A CH895063A CH417612A CH 417612 A CH417612 A CH 417612A CH 895063 A CH895063 A CH 895063A CH 895063 A CH895063 A CH 895063A CH 417612 A CH417612 A CH 417612A
- Authority
- CH
- Switzerland
- Prior art keywords
- ones
- group
- amino
- aralkyl
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 4
- RGGLEJFUEMKQSH-UHFFFAOYSA-N 1,4-benzodiazepin-2-one Chemical class O=C1C=NC=C2C=CC=CC2=N1 RGGLEJFUEMKQSH-UHFFFAOYSA-N 0.000 title description 4
- 239000002904 solvent Substances 0.000 claims description 7
- -1 N-monosubstituted 2-amino-5-chlorobenzophenone Chemical class 0.000 claims description 3
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 150000001370 alpha-amino acid derivatives Chemical class 0.000 claims description 2
- 235000008206 alpha-amino acids Nutrition 0.000 claims description 2
- 150000004820 halides Chemical class 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- PUBNSQUKVSQJPG-UHFFFAOYSA-N 2-amino-2-methylpropanoyl chloride;hydrochloride Chemical compound Cl.CC(C)(N)C(Cl)=O PUBNSQUKVSQJPG-UHFFFAOYSA-N 0.000 description 1
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical compound C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 description 1
- ZGUNAGUHMKGQNY-ZETCQYMHSA-N L-alpha-phenylglycine zwitterion Chemical compound OC(=O)[C@@H](N)C1=CC=CC=C1 ZGUNAGUHMKGQNY-ZETCQYMHSA-N 0.000 description 1
- ROHFNLRQFUQHCH-YFKPBYRVSA-N L-leucine Chemical compound CC(C)C[C@H](N)C(O)=O ROHFNLRQFUQHCH-YFKPBYRVSA-N 0.000 description 1
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 1
- KZSNJWFQEVHDMF-BYPYZUCNSA-N L-valine Chemical compound CC(C)[C@H](N)C(O)=O KZSNJWFQEVHDMF-BYPYZUCNSA-N 0.000 description 1
- ROHFNLRQFUQHCH-UHFFFAOYSA-N Leucine Natural products CC(C)CC(N)C(O)=O ROHFNLRQFUQHCH-UHFFFAOYSA-N 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical compound ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- KZSNJWFQEVHDMF-UHFFFAOYSA-N Valine Natural products CC(C)C(N)C(O)=O KZSNJWFQEVHDMF-UHFFFAOYSA-N 0.000 description 1
- 235000004279 alanine Nutrition 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 235000001014 amino acid Nutrition 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 229940125681 anticonvulsant agent Drugs 0.000 description 1
- 239000001961 anticonvulsive agent Substances 0.000 description 1
- 229940125717 barbiturate Drugs 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hcl hcl Chemical compound Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 239000004474 valine Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
- A61K31/551—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole having two nitrogen atoms, e.g. dilazep
- A61K31/5513—1,4-Benzodiazepines, e.g. diazepam or clozapine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Procedimento per 1'ottenimento di 1,4-benzodiazepin-2-oni
La presente invenzione ha per oggetto un proce dimento per 1'ottenimento di 1,4 - benzodiazepin-2-oni di formula I:
dove R, e un alchil- o aralchil- gruppo, R2 e un alchil o aralchil- gruppo, R3 e idrogeno o un alchil- o aral chil- gruppo oppure Bove R2 e R3 sono insieme un gruppo aliciclico, caratterizzato dal fatto che i derivati N-monosostituiti del 2-ammino-5-clorobenzofenone vengono fatti reagire in un solvente con 1'alogenuro di un a-amminoacido salificato. 1 prodotti N-monosostituiti del 2-ammino-5-cloro benzofenone hanno la formula Il:
dove R1 e un alchil- o aralchil- gruppo, e possono es-
sere preparati per alchilazione di una opportuna am mide del 2-ammino-5-clorobenzofenone e successiva idrolisi. Ad una soluzione di N-alchil- o aralchil-2-ammi no-5-clorobenzofenone in un solvente clorurato, si ag giunge il cloruro cloridrato di un a-amminoacido, e la sospensione viene agitata ad una temperatura e per un tempo opportuni. Dopo evaporazione della soluzione e cristallizzazione del residuo da un solvente, si otten gono gli 1,4 - benzodiazepin-2-oni indicati. I solventi piü opportuni sono i solventi clorurati come cloroformio, tetracloruro di carbonio, dicloroeta no, tetracloruro di etilene, ecc. Gli a-amminoacidi usati possono essere per esem pio leucina, valina, alanina, fenilalanina, fenilglicina, acido a-amminobutirrico e amminoacidi delle serie nor- ed iso-, ecc. La temperatura ed il tempo di reazione possono variare e dipendono dalla natura degli a-amminoacidi.
Esempio:
A 0,05 moli di N-metil-2-ammino-5-clorobenzofe none sciolte in 50 cc. di tetracloruro di carbonio ani dro, si aggiungono 0,08 moli di cloruro cloridrato del 1'acido a-ammino-iso-butirrico. La sospensione viene bollita a ricadere per 24 ore. Dopo raffreddamento, si Lava la soluzione con alcali diluito, si evapora il sol vente cos! ottenuto, si cristallizza da una miscela di etanolo-acqua. I prodotti indicati possono essere usati come po tenzianti dell'azione di barbiturici e come anticonvul sivanti.
Claims (1)
- RIVENDICAZIONE Procedimento per 1'ottenimento di 1,4 - benzodia zepin-2-oni di formula I:dove R, e un alchil- o aralchil- gruppo, Rz e un alchil o aralchil- gruppo, R3 e idrogeno o un alchil- o aral chil- gruppo oppure dove R2 e R3 sono insieme un gruppo aliciclico, caratterizzato dal fatto che i derivati N-monosostituiti del 2-ammino-5-clorobenzofenone vengono fatti reagire in un solvente con 1'alogenuro di un a-amminoacido sahficato.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH895063A CH417612A (it) | 1963-07-17 | 1963-07-17 | Procedimento per l'ottenimento di 1,4-benzodiazepin-2-oni |
| ES0301656A ES301656A1 (es) | 1963-07-17 | 1964-07-03 | Procedimiento de obtenciën de 1,4-benzodiazopin-2-onas |
| BR160942/64A BR6460942D0 (pt) | 1963-07-17 | 1964-07-17 | Processo para a obtencao de 1,4 benzo diazopin-2 ona |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH895063A CH417612A (it) | 1963-07-17 | 1963-07-17 | Procedimento per l'ottenimento di 1,4-benzodiazepin-2-oni |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH417612A true CH417612A (it) | 1966-07-31 |
Family
ID=4346647
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH895063A CH417612A (it) | 1963-07-17 | 1963-07-17 | Procedimento per l'ottenimento di 1,4-benzodiazepin-2-oni |
Country Status (3)
| Country | Link |
|---|---|
| BR (1) | BR6460942D0 (it) |
| CH (1) | CH417612A (it) |
| ES (1) | ES301656A1 (it) |
-
1963
- 1963-07-17 CH CH895063A patent/CH417612A/it unknown
-
1964
- 1964-07-03 ES ES0301656A patent/ES301656A1/es not_active Expired
- 1964-07-17 BR BR160942/64A patent/BR6460942D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES301656A1 (es) | 1965-01-16 |
| BR6460942D0 (pt) | 1973-07-19 |
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