GB1449861A - Benzodiazepine and benzodiazocine derivatives - Google Patents

Benzodiazepine and benzodiazocine derivatives

Info

Publication number
GB1449861A
GB1449861A GB4838973A GB4838973A GB1449861A GB 1449861 A GB1449861 A GB 1449861A GB 4838973 A GB4838973 A GB 4838973A GB 4838973 A GB4838973 A GB 4838973A GB 1449861 A GB1449861 A GB 1449861A
Authority
GB
United Kingdom
Prior art keywords
carbon atoms
bromo
prepared
alkyl
alkoxy
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
Application number
GB4838973A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
ER Squibb and Sons LLC
Original Assignee
ER Squibb and Sons LLC
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.)
Filing date
Publication date
Application filed by ER Squibb and Sons LLC filed Critical ER Squibb and Sons LLC
Publication of GB1449861A publication Critical patent/GB1449861A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/72—Nitrogen atoms
    • C07D213/73—Unsubstituted amino or imino radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
    • C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
    • C07C29/147—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of carboxylic acids or derivatives thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/01—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton
    • C07C323/09—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and halogen atoms, or nitro or nitroso groups bound to the same carbon skeleton having sulfur atoms of thio groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
    • C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
    • C07C323/19—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to acyclic carbon atoms of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/09—Preparation of carboxylic acids or their salts, halides or anhydrides from carboxylic acid esters or lactones
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

1449861 Benzodiazepine and benzodiazocine derivatives E R SQUIBB & SONS Inc 17 Oct 1973 [24 Oct 1972 8 March 1973] 48389/73 Heading C2C Novel compounds of the Formula I wherein m is 1 or 2; R is the same or different and is hydrogen, F, Cl, or Br, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, alkylthio of from 1 to 4 carbon atoms, benzyl, phenethyl, phenyl, phenylthio, or mono-substituted phenyl wherein the substituent is F, Cl, Br, I, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, or trifluoromethyl; provided that when R is halogen, R is in the 3- and/or 5-positions with respect to the pyridyl nitrogen as the 1-position; R<SP>1</SP> is hydrogen, F, Cl, Br, I, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms, alkylthio of from 1 to 4 carbon atoms, alkylsulphonyl wherein the alkyl radical has from 1 to 4 carbon atoms, phenyl, phenyloxy, sulphamoyl, dialkylamidosulphonyl wherein each alkyl radical has from 1 to 4 carbon atoms, trifluoromethyl, mono-substituted phenyl or mono-substituted phenyloxy wherein the substituent is F, Cl, Br or I, alkyl of from 1 to 4 carbon atoms, alkoxy of from 1 to 4 carbon atoms or trifluoromethyl, and n is 2 or 3 and pharmaceutically acceptable salts thereof may be prepared by cyclizing, by the action of base and a copper catalyst, a compound IV or V Compounds of the Formula IV are prepared by reacting a 2-amino pyridine with a 2-bromophenethylbromide or a 3-(2-bromophenyl)- propylbromide. Treatment of an amine IV with base yields the corresponding imine V. The intermediate 2-bromophenethylbromides and 3 - (2 - bromophenyl)propylbromides are prepared by bromination of the corresponding 2-bromophenethanol or 3-(2-bromophenyl)propanol. 2 - Bromophenethanol and 2 - bromo - 4- chlorophenethanol are prepared by treating the corresponding 2-bromobenzylbromide with sodium cyanide to yield the corresponding 2- bromophenylacetonitrile which on ethanolysis yields the ethyl 2-bromophenylacetate which in the case of 4-chloro compound is hydrolysed to 2-bromo-4-chlorophenylacetic acid and then in both cases reduced to the required corresponding ethanol. 2-Bromobenzylbromide is prepared by bromination of 2-bromobenzylalcohol. 3 - (2 - Bromo - 4 - methylthiophenyl) - 1- propanol is prepared by reducing 2-bromo-4- nitrobenzoic acid to 2-bromo-4-aminobenzoic acid followed by diazotization and treatment with sodium methylmercaptide to yield 2- bromo - 4 - methylthiobenzoic acid which is converted to its methyl ester and reduced to 2- bromo - 4 - methylthiobenzylalcohol which is brominated to 2 - bromo - 4 - methylthiobenzylbromide converted to its Grignard reagent and then treated with ethylene oxide to yield the required compound. Pharmaceutical compositions of the compounds I when administered orally or parenterally show muscle relaxant and stimulant activity.
GB4838973A 1972-10-24 1973-10-17 Benzodiazepine and benzodiazocine derivatives Expired GB1449861A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US29998672A 1972-10-24 1972-10-24
US00339258A US3825549A (en) 1972-10-24 1973-03-08 Certain dihydropyrido(2,1-b)(1,3)benzodi-azepines and benzodiazocines

Publications (1)

Publication Number Publication Date
GB1449861A true GB1449861A (en) 1976-09-15

Family

ID=26971513

Family Applications (1)

Application Number Title Priority Date Filing Date
GB4838973A Expired GB1449861A (en) 1972-10-24 1973-10-17 Benzodiazepine and benzodiazocine derivatives

Country Status (6)

Country Link
US (1) US3825549A (en)
JP (1) JPS4975595A (en)
CA (1) CA1016167A (en)
DE (2) DE2365309A1 (en)
FR (1) FR2203640B1 (en)
GB (1) GB1449861A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3150522A1 (en) * 1981-09-24 1983-04-07 A. H. Robins Co. Inc., 23220 Richmond, Va. Phenyl-substituted pyrido[1,4]benzodiazepines, intermediates and processes for their preparation, and their use as antidepressive agents

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ZA86171B (en) * 1985-01-16 1986-08-27 Hoffmann La Roche Polycyclic salts
US4990648A (en) * 1988-12-22 1991-02-05 Ici Americas Inc. Process for producing an alkylthiobenzoate
US4925970A (en) * 1988-12-22 1990-05-15 Brown Richard W Process for producing cyclohexadiene thioether

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3150522A1 (en) * 1981-09-24 1983-04-07 A. H. Robins Co. Inc., 23220 Richmond, Va. Phenyl-substituted pyrido[1,4]benzodiazepines, intermediates and processes for their preparation, and their use as antidepressive agents

Also Published As

Publication number Publication date
CA1016167A (en) 1977-08-23
DE2352918A1 (en) 1974-05-02
DE2365309A1 (en) 1974-05-30
FR2203640A1 (en) 1974-05-17
FR2203640B1 (en) 1978-07-28
JPS4975595A (en) 1974-07-20
US3825549A (en) 1974-07-23

Similar Documents

Publication Publication Date Title
US3711495A (en) Isoxazalin-3-yl-substituted-5-nitroimidazoles
IL127296A0 (en) Novel heterocyclic compounds process for their preparation and pharmaceutical compositions containing them and their use in the treatment of diabetes and related diseases
GB1351430A (en) Substituted 1,2,4-triazole derivatives
GB1358680A (en) Pyrrolo-3,4-b-pyrazine derivatives
GB1193035A (en) Substituted Imidazo Pyrazinones
GB1221324A (en) New processes for the production of benzazepine derivatives
NZ514662A (en) Amine derivatives
ES428107A1 (en) 2-1-piperazinyl-quinoxaline compounds having pharmaceutical activity
GB1307205A (en) Isoindoline derivatives
GB1478364A (en) 3-5-nitro-2-imidazolyl-pyrazoles
IE35909L (en) Acetoxylidides
GB1449861A (en) Benzodiazepine and benzodiazocine derivatives
GB1297386A (en)
KOSASAYAMA et al. Cyclic guanidines. IV. Synthesis of hypoglycemic N-benzhydryl bicyclic guanidines
GB1447426A (en) Pyrrolo 3,4-d- pyrimidines and methods for their preparation
US3682949A (en) 2-aryl-5(or 4-)nitroimidazoles
GB1259007A (en)
GB1337371A (en) 3-amino-imidazo-1,5-a- pyridines processes for their preparation and pharmaceutical compositions incorporating them
GB1511006A (en) Pyrazolopyridines
US4091219A (en) Amino derivatives of 1,2,3,4-tetrahydro-2-oxopyrido[2,3-b]-pyrazine carboxylic acids and esters
GB1469197A (en) Preparation of 1-aminoalkyl triazolobenzodiazepines
GB1373276A (en) 2-aryl-amino-imidazoline-2 compounds
GB1397060A (en) 1,4-dighiino 2,3-c pyrrole derivatives
US3715364A (en) Nitroimidazole carboxamides
CA2296586A1 (en) New 2,3-benzodiazepine derivatives

Legal Events

Date Code Title Description
PS Patent sealed [section 19, patents act 1949]
PCNP Patent ceased through non-payment of renewal fee