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The Chemistry of Anxiolytics

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Psychotropic Agents

Part of the book series: Handbook of Experimental Pharmacology ((HEP,volume 55 / 2))

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Abstract

The anxiolytics are a group of CNS-active agents which in the last 25 years have played an ever-increasing role in the physician’s armamentarium. They are mild sedatives with pronounced activity in anxiety, tension, and neuroses, including psychosomatic disorders. They generally do not act in psychoses, but are sometimes used in combination with neuroleptics to relieve anxiety in depressed psychotics. Several chemically completely unrelated classes of compounds are known to possess antianxiety properties and are discussed below. Although this chapter deals mainly with anxiolytics used in the United States, the sections on benzodiazepines (B.IV and B.V) include drugs used solely in other countries.

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References

  • Anonymous: Tranquilizer’s five-week scale-up. Chemical Week 70–71 (1956)

    Google Scholar 

  • Archer, G.A., Sternbach, L.H.: Quinazolines and 1,4-benzodiazepines. XVI. Synthesis and transformations of 5-phenyl-1,4-benzodiazepine-2-thiones. J. Org. Chem. 29, 231–233 (1964)

    Article  CAS  Google Scholar 

  • Bell, S.C., Childress, S.J.: A rearrangement of 5-aryl-1,3-dihydro-2H-1,4-benzodiazepine-2-one 4-oxides. J. Org. Chem. 27, 1691–1695 (1962)

    Article  CAS  Google Scholar 

  • Bell, S.C., McCaully, R.J., Gochman, C., Childress, S.J., Gluckman, M.L: 3-Substituted 1,4-benzodiazepin-2-ones. J. Med. Chem. 11, 457–461 (1968)

    Article  PubMed  CAS  Google Scholar 

  • Benconi, F., Tagliabue, R., Molteni, L.: 1-Propargyl 1,4-benzodiazepin-2-ones. Belgian Pat. 803315, assigned to Dr. L. Zambeletti S.P.A. (1973)

    Google Scholar 

  • Berger, F.M.: Anticonvulsant action of 2-substituted-1,3-propanediols. Proc. Soc. Exp. Biol. Med. 71, 270–271 (1949)

    PubMed  CAS  Google Scholar 

  • Berger, F.M.: The pharmacological properties of 2-methyl-2-n-propyl-1,3-propanediol dicarbamate (Miltown), a new interneuronal blocking agent. J. Pharmacol. Exp. Ther. 112, 412–423 (1954)

    Google Scholar 

  • Berger, F.M., Ludwig, B.J.: N-Monosubstituted-2,2-dialkyl-1,3-propanediols dicarbamates. U.S. Pat. 2937119(1960)

    Google Scholar 

  • Berger, F.M., Ludwig, B.J.: Meprobamate and related compounds. Psychopharmacological Agents, vol. 1, pp. 103–135. (Ed. M. Gordon) New York: Academic Press 1964

    Google Scholar 

  • Berger, F.M., Kletzkin, M., Margolin, S.: Pharmacologic properties of a new tranquilizing agent 2-methyl-2-propyl-trimethylenebutylcarbamate carbamate (Tybamate). Med. Exp. 10, 327–344 (1964)

    PubMed  CAS  Google Scholar 

  • Ferrari, G., Casagrande, C.: 1,4-Benzodiazepine derivatives. U.S. Pat. 3799920 (1974)

    Google Scholar 

  • Fischer, E., Mering, v.: Über eine neue Klasse von Schlafmitteln, Ther. Ggw. 44, 97 (1903).

    Google Scholar 

  • Fischer, E., Mering, v.: Über eine neue Klasse von Schlafmitteln, Chem. Zentralbl. 74, I, 1155 (1903)

    Google Scholar 

  • Fryer, R.I., Schmidt, R.A., Sternbach, L.H.: Quinazolines and benzodiazepines. XVII. Synthesis of 1,3-dihydro-5-pyridyl-2H-1,4-benzodiazepine derivatives. J. Pharm. Sci. 53, 264–268 (1964)

    Article  PubMed  CAS  Google Scholar 

  • Hauptmann, K.H., Weber, K.H., Zeile, K., Danneberg, P., Giesemann, K.: 1,5-Benzodiazepine derivatives. South African Pat. 6800803 (1968); Chem. Abstr. 70, 106579 (1969)

    Google Scholar 

  • Hester, J.B., Jr., Duchamp, D.J., Chidester, C.G.: A synthetic approach to new 1,4-benzodiazepine derivatives. Tetrahedron Letters 20, 1609–1612 (1971)

    Article  Google Scholar 

  • Jacobson, E.: Benactyzine. Psychopharmacological Agents, Vol. 1, pp. 287–300. (Ed. M. Gordon) New York-London: Academic Press 1964

    Google Scholar 

  • Kaegi, H.H.: Synthesis of 7-chloro-2,3-dihydro-l-methyl-5-phenyl-1H-1,4-benzodiazepine-514C hydrochloride. J. Labelled Comp. 4, 363–367 (1968)

    Article  CAS  Google Scholar 

  • Ludwig, B.J., Piech, E.C.: Some anticonsulvant agents derived from 1,3-propanediols. J. Am. Chem. Soc. 73, 5779–5781 (1951)

    Article  CAS  Google Scholar 

  • McMillan, F.H., Pattison, I.: Process for the production of 1-cycloalkyl derivatives of 1,4-benzodiazepine. U.S. Pat. 3192199 (1965)

    Google Scholar 

  • Meguro, K., Kuwada, Y.: Syntheses and structures of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine and some isomeric 1,4,5-benzotriazocines. Tetrahedron Letters 4039–4042 (1970)

    Google Scholar 

  • Miyadera, T., Terada, A., Fukunaga, M., Kawano, Y., Kamioa, T., Tamura, C., Takagi, H., Tachikawa, R.: Anxiolytic sedatives. 1. Synthesis and pharmacology of benzo[6,7]-l,4-diazepino[5,4-b]oxazole derivatives and analogs. J. Med. Chem. 14, 520–526 (1971)

    Article  PubMed  CAS  Google Scholar 

  • Morren, H., Denayer, R., Trolin, S., Grivsky, E., Linz, R., Strubbe, H., Dony, G., Marico, J.: Nouveaux derives 1,4-disubstitués de la piperazine. Etude de leurs proprietés antihistaminiques. Ind. Chim. Belg. 19, 1176–1196 (1954)

    CAS  Google Scholar 

  • Morren, H.G., Bienfet, V., Reyntjens, A.M.: Piperazine derivatives (except phenothiazines), Psychopharmacological Agents, Vol. 1, pp. 251–285. (Ed. M. Gordon) New York: Academic Press 1964

    Google Scholar 

  • Randall, L.O.: Pharmacology of methaminodiazepoxide. Dis. Nerv. Syst. 21, 7–10 (1960).

    PubMed  Google Scholar 

  • Randall, L.O.: Pharmacology of methaminodiazepoxide. Pharmacology of chlordiazepoxide. Dis. Nerv. Syst. 22, 7–15 (1962)

    Google Scholar 

  • Rieder, J., Rentsch, G.: Metabolismus und Pharmakokinetik des neuen Psychopharmakons 7-Chlor-2,3-dihydro-l-methyl-5-phenyl-1H-1,4-benzodiazepin (Ro 5–4556) beim Menschen. Arzneim. Forsch. 18, 1545–1556 (1968)

    CAS  Google Scholar 

  • Rossi, S., Pirola, O., Maggi, R.: 1,2,4,5-Tetrahydro-2,4-dioxo-3H-1,5-benzodiazepines. Chim. industria 51, 479–483 (1969)

    CAS  Google Scholar 

  • Roussel Uclaf. Benzo-1,5-diazepines C.N.S. depressants. Belg. Pat. 707667 (1968)

    Google Scholar 

  • Schmitt, J., Comoy, P., Suquet, M., Boitard, J., Le Meur, J., Basselier, J.-J., Brunaud, M., Salle, J.: Sur un no veau myorelaxant de la classe des benzodiazepines: Le tetrazepam. Chim. Ther. 2, 254–259 (1967)

    CAS  Google Scholar 

  • Schmitt, J., Comoy, P., Suquet, M., Callet, G., Le Meur, J., Clim, T., Brunaud, M., Mercier, J., Salle, J., Siou, G.: Sur le nouvelles benzodiazépines hydrosolubles douées d’une puissante activité sur le syste’me nerveux central. Chim. Ther. 4, 239–245 (1969)

    CAS  Google Scholar 

  • Schwartz, M.A., Carbone, J.J.: Metabolism of 14C-medazepam hydrochloride in dog, rat and man. Biochem. Pharmacol. 19, 343–361 (1970)

    Article  PubMed  CAS  Google Scholar 

  • Sternbach, L.H.: The benzodiazepine story. Progress in Drug Research. Vol. 22, pp. 229–267. (Ed. E. Jucker) Basel-Stuttgart: Birkhäuser 1978

    Google Scholar 

  • Sternbach, L.H., Reeder, E.: Quinazolines and 1,4-benzodiazepines. II. The rearrangement of 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide into 2-amino derivatives of 7-chloro-5-phenyl-3H-l,4-benzodiazepine 4-oxide. J. Org. Chem. 26, 1111–1118 (1961a)

    Article  CAS  Google Scholar 

  • Sternbach, L.H., Reeder, E.: Quinazolines and 1,4-benzodiazepines. IV. Transformations of 7-chloro-2-methyl-amino-5-phenyl-3H-l,4-benzodiazepine 4-oxide. J. Org. Chem. 26, 4936–4941 (1961b)

    Article  CAS  Google Scholar 

  • Sternbach, L.H., Fryer, R.I., Keller, O., Metlesics, W., Sach, G., Steiger, N.: Quinazolines and 1,4-benzodiazepines. X. Nitro-substituted 5-phenyl-1,4-benzodiazepine derivatives. J. Med. Chem. 6, 261–265 (1963)

    Article  PubMed  CAS  Google Scholar 

  • Sternbach, L.H., Randall, L.O., Gustafson, S.: 1,4-Benzodiazepines (chlordiazepoxide and related compounds). Psychopharmacol. Agents 1, 137–224 (1964)

    Google Scholar 

  • Sternbach, L.H., Archer, G.A., Earley, J.V., Fryer, R.I., Reeder, E., Wasyliw, N., Randall, L.O., Banziger, R.: Quinazolines and 1,4-benzodiazepines. XXV. Structure-activity relationships of aminoalkyl-substituted l,4-benzodiazepin-2-ones. J. Med. Chem. 8, 815–821 (1965)

    Article  PubMed  CAS  Google Scholar 

  • Sternbach, L.H., Randall, L.O., Banziger, R., Lehr, H.: Structure-activity relationships in the 1,4-benzodiazepine series. Med. Res. Ser. 2, 237–264 (1968)

    CAS  Google Scholar 

  • Surrey, A.R., Webb, W.G., Gesler, R.M.: Central nervous system depressants. The preparation of some 2-aryl-4-metathiazanones. J. Am. Chem. Soc. 80, 3469–3471 (1958)

    Article  CAS  Google Scholar 

  • Weber, K.H., Bauer, A., Hauptmann, H.H.: N-Aryl- and N-Heteroaryl-1H-1,5-benzodiazepin- 2,4-[3H,5H]-dione. Liebigs Ann. Chem. 756, 128–138 (1972)

    Article  CAS  Google Scholar 

  • Wuest, H.M.: 1-Cycloalkylmethyl derivatives of 1,4-benzodiazepine. U.S. Pat. 3192220 (1965)

    Google Scholar 

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Authors
  1. L. H. Sternbach
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Editors and Affiliations

  1. Institut für Pharmakologie, Bayer AG, Aprather Weg 18a, D-5600, Wuppertal 1, Germany

    F. Hoffmeister

  2. Institut für Arzneimittel des Bundesgesundheitsamtes, Stauffenbergstraße 13, D-1000, Berlin 30, Germany

    G. Stille

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© 1981 Springer-Verlag Berlin Heidelberg

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Sternbach, L.H. (1981). The Chemistry of Anxiolytics. In: Hoffmeister, F., Stille, G. (eds) Psychotropic Agents. Handbook of Experimental Pharmacology, vol 55 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-67767-0_1

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  • DOI: https://doi.org/10.1007/978-3-642-67767-0_1

  • Publisher Name: Springer, Berlin, Heidelberg

  • Print ISBN: 978-3-642-67769-4

  • Online ISBN: 978-3-642-67767-0

  • eBook Packages: Springer Book Archive

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