GB907646A - Method of production of new derivatives of diazepin - Google Patents
Method of production of new derivatives of diazepinInfo
- Publication number
- GB907646A GB907646A GB195460A GB195460A GB907646A GB 907646 A GB907646 A GB 907646A GB 195460 A GB195460 A GB 195460A GB 195460 A GB195460 A GB 195460A GB 907646 A GB907646 A GB 907646A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- alkyl
- substituents
- alkoxy
- atom
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- LRANPJDWHYRCER-UHFFFAOYSA-N 1,2-diazepine Chemical class N1C=CC=CC=N1 LRANPJDWHYRCER-UHFFFAOYSA-N 0.000 title 1
- -1 alkyl radical Chemical class 0.000 abstract 5
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 abstract 1
- RUKISNQKOIKZGT-UHFFFAOYSA-N 2-nitrodiphenylamine Chemical compound [O-][N+](=O)C1=CC=CC=C1NC1=CC=CC=C1 RUKISNQKOIKZGT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 230000002152 alkylating effect Effects 0.000 abstract 1
- CREXVNNSNOKDHW-UHFFFAOYSA-N azaniumylideneazanide Chemical group N[N] CREXVNNSNOKDHW-UHFFFAOYSA-N 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 125000004122 cyclic group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000004820 halides Chemical class 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
Landscapes
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The invention comprises 5-substituted 5-dibenzo-(b:e)(1:4)-diazepins of the formula <FORM:0907646/IV (b)/1> and mono- and bis-quaternary compounds and acid addition salts thereof, wherein R1 represents hydrogen, a C1-5 alkyl radical or an unsubstituted or halo- or C1-3 alkoxy-substituted aryl or aralkyl radical, R2 and R3 are each a hydrogen or halogen atom or an alkyl, alkoxy or alkylmercapto group of 1-3 carbon atoms, X is a straight or branched hydrocarbon chain of 1-5 carbon atoms and Y is a dialkylamino group or a cyclic alkyleneamine group which may be connected to X at the N atom or at one of the carbon atoms (in the latter case the N-atom bears an alkyl substituent) and which may contain further hetero atoms; it comprises also the preparation of these compounds by reacting an o-acylaminodiphenylamine, in which one o-position in ring B is unsubstituted, with a dehydrating condensation agent, e.g. phosphorus pentoxide, halides or oxyhalides or a polyphosphoric acid and, if a salt or quaternary compound is desired, treating the product with an organic or inorganic acid or a quaternising agent. The examples describe products wherein the 5-substituents are b -dimethylaminoethyl, g -dimethylaminopropyl, b -diethylaminoethyl, g -diethylaminopropyl, b -piperidinoethyl, g -piperidinopropyl, g -pyrrolidinopropyl, b -N1-methylpiperazinoethyl, g -N1-methylpiperazinopropyl, g -morpholinopropyl, and piperidinoisopropyl groups and which may additionally be substituted by methyl, ethyl, isopropyl, chloro, methoxy, phenyl, p-methoxyphenyl, benzyl and methylmercapto substituents. o-Acylamino-diphenylamines used as starting materials in the examples are made by alkylating an o-nitrodiphenylamine which is optionally substituted by a halogen, alkyl, alkoxy or alkylmercapto substituent, to introduce a group Y-X- corresponding to the above 5-substituents, on the amino nitrogen atom, reducing to the corresponding o-amino-diphenylamine and acylating the o-amino radical with a group R1CO-.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH6867059A CH375728A (en) | 1959-01-23 | 1959-01-23 | Process for the production of new diazepine derivatives |
| CH8233659 | 1959-12-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB907646A true GB907646A (en) | 1962-10-10 |
Family
ID=25737965
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB195460A Expired GB907646A (en) | 1959-01-23 | 1960-01-19 | Method of production of new derivatives of diazepin |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB907646A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2513249A1 (en) * | 1981-09-24 | 1983-03-25 | Robins Co Inc A H | (AMINOALKYL) -5 PHENYL-11 5H-DIBENZO (B, E) (1,4) DIAZEPINES USEFUL AS ANTIDEPRESSANT MEDICINES AND INTERMEDIATES FOR THEIR PREPARATION |
| US4447361A (en) * | 1981-09-24 | 1984-05-08 | A. H. Robins Company, Inc. | Aryl substituted pyrido[1,4]benzodiazepines |
| US4495183A (en) * | 1981-09-24 | 1985-01-22 | A. H. Robins Company, Incorporated | Aryl substituted pyrido[1,4]benzodiazepines for treatment of depression |
| EP0099614A3 (en) * | 1982-07-02 | 1985-05-29 | A.H. Robins Company, Incorporated | Nitro, amino and aroylamino-n-phenylpyridinamines and their use in a process for preparing pyrido(1,4)benzodiazapines |
| US4556667A (en) * | 1981-09-24 | 1985-12-03 | A. H. Robins Company, Incorporated | Aryl substituted pyrido[1,4]benzodiazepines and their use as antidepressives |
| US4694003A (en) * | 1981-09-24 | 1987-09-15 | A. H. Robins Company, Incorporated | Method of treating depression with 5-(aminoalkyl)-11-phenyl-5H-dibenzo(b,e)(1,4) diazepines |
| US5922887A (en) * | 1995-05-19 | 1999-07-13 | Smithkline Beecham Spa | Diaryldiamine derivatives and their use as delta opiod (ANT)-agonists |
-
1960
- 1960-01-19 GB GB195460A patent/GB907646A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2513249A1 (en) * | 1981-09-24 | 1983-03-25 | Robins Co Inc A H | (AMINOALKYL) -5 PHENYL-11 5H-DIBENZO (B, E) (1,4) DIAZEPINES USEFUL AS ANTIDEPRESSANT MEDICINES AND INTERMEDIATES FOR THEIR PREPARATION |
| DE3149923A1 (en) * | 1981-09-24 | 1983-04-14 | A. H. Robins Co. Inc., 23220 Richmond, Va. | 5- (AMINOALKYL) -11-PHENYL-5H-DIBENZO (B, E), (1,4) DIAZEPINE, METHOD FOR THE PRODUCTION THEREOF AND PHARMACEUTICAL PREPARATIONS THAT CONTAIN THESE COMPOUNDS |
| US4447361A (en) * | 1981-09-24 | 1984-05-08 | A. H. Robins Company, Inc. | Aryl substituted pyrido[1,4]benzodiazepines |
| US4495183A (en) * | 1981-09-24 | 1985-01-22 | A. H. Robins Company, Incorporated | Aryl substituted pyrido[1,4]benzodiazepines for treatment of depression |
| US4556667A (en) * | 1981-09-24 | 1985-12-03 | A. H. Robins Company, Incorporated | Aryl substituted pyrido[1,4]benzodiazepines and their use as antidepressives |
| US4694003A (en) * | 1981-09-24 | 1987-09-15 | A. H. Robins Company, Incorporated | Method of treating depression with 5-(aminoalkyl)-11-phenyl-5H-dibenzo(b,e)(1,4) diazepines |
| AU576010B2 (en) * | 1981-09-24 | 1988-08-11 | A.H. Robins Company, Incorporated | Benzamido diphenylamine compounds |
| EP0099614A3 (en) * | 1982-07-02 | 1985-05-29 | A.H. Robins Company, Incorporated | Nitro, amino and aroylamino-n-phenylpyridinamines and their use in a process for preparing pyrido(1,4)benzodiazapines |
| US5922887A (en) * | 1995-05-19 | 1999-07-13 | Smithkline Beecham Spa | Diaryldiamine derivatives and their use as delta opiod (ANT)-agonists |
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