Abstract
In this Chapter a survey and discussion of the chemistry of compounds which antagonize the effects of histamine at H1 receptors are presented. Ellis (1969) has compiled an extensive list of reviews on histamine, 5-hydroxytryptamine, and their antagonists, several of which include some account of the chemical aspects of antihistaminics. Here, attention is drawn in particular to the reviews of Witiak (1970), Doerge (1971), and Melville (1973); an extensive review of earlier work is available in Czech (Protiva, 1955). Developments in the field are presented periodically in Annual Reports in Medicinal Chemistry sponsored by the Division of Medicinal Chemistry of the American Chemical Society, e.g. Tozzi (1972).
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
Preview
Unable to display preview. Download preview PDF.
References
Aaron, T.H., Criep, L.H.: Neohetramine and thephorin: 2 new antihistaminic drugs. Can. med. Ass. J. 59, 438–441 (1948).
Adamson, D.W., Barrett, P.A., Billinghurst, J.W., Green, A.F., Jones, T.S.G.: Geometrical isomers in a series of antihistamines. Nature (Lond.) 168, 204–205 (1951).
Adamson, D.W., Barrett, P.A., Billinghurst, J.W., Jones, T.S.G.: Aminoalkyl tertiary carbinols and derived products. Part V. Antihistamines. The stereochemistry of cis- and trans-3-phenyl-3-pyridylallylamines. J. chem. Soc. 1957, 2315–2326.
Adamson, D.W., Barrett, P.A., Billinghurst, J.W., Jones, J.S.G.: Aminoalkyl tertiary carbinols and derived products. VI. Stereochemistry of some 1-phenyl-1-(2-pyridyl)-prop-1-enes and of some 3-(tertiary amino)-1-phenyl-1-(2-pyridyl)-1-propenes carrying additional substituents. J. chem. Soc. 1958, 312–324.
Adamson, D.W., Billinghurst, J.W.: Aminoalkyl tertiary carbinols and derived products. Part III. 3-Tertiary-amino-1-aryl-1-(2-pyridyl)-propan-1-ols and prop-1-enes. J. chem. Soc. 1950, 1039–1045.
Albert, A., Serjeant, E.P.: Ionization constants of acids and bases, 2nd Ed. London: Chapman & Hall 1971.
Archibald, J.L., Benke, G.A.: Benzamidopiperidines. 2. Heterocyclic compounds related to indoramin. J. med. Chem. 17, 739–744 (1974).
Archibald, J.L., Fairbrother, P., Jackson, J.L.: Benzamidopiperidines. 3. Carbocyclic derivatives related to indoramin. J. med. Chem. 17, 739–744 (1974).
Ash, A.S., Schild, H.O.: Receptors mediating some actions of histamine. Brit. J. Pharmacol. 27, 427–439 (1966).
Augstein, J., Ham, A.L., Leeming, P.R.: Relationship between antihistamine and antidepressant activity in hexahydroindeno-pyridines. J. med. Chem. 15, 466–470 (1972).
Barac, G.: Histamine antihistaminiques et diurèse aqueuse chez le Chien normal et chez le Chien brûlé. C. R. Soc. Biol. 143, 550–553 (1949).
Barouh, V., Dall, H., Patel, D., Hite, G.: Stereochemical aspects of antihistamine action: 4. Absolute configuration of carbinoxamine antipodes. J. med. Chem. 14, 834–836 (1971).
Biel, J.H., Judd, C.I.: Aminoalkyliminobibenzyl compounds. British Patent 980, 231, 13. Jan. 1965, Chem. Abstr., 63, 14, 830d.
Bijlsma, U.G., Harms, A.F., Funcke, A.B.H., Tersteege, H.M., Nauta, W.T.H.: Pharmakologie des β-Dimethylaminoethyl-2-methylbenzhydryläthers. HCl (Bs.5930). Arzneimittel-Forsch. 5, 72–73 (1955).
Boissier, J.R., Ratouis, R., Dumont, C., Taliani, L., Forest, J.: Synthesis and pharmacological properties of new 9,10-Dihydro-9,10-ethanoanthracene derivatives. J. med. Chem. 10, 86–91 (1967).
Borovicka, M., Protiva, M.: Antihistamine substances XLI. Derivatives of 1-aza-2, 3:5, 6-dibenzocycloheptadiene (homoacridan). Chem. Listy 51, 1344–1349 (1957).
Bourquin, J.B.: D’un nouvel antihistaminique de synthèse (antistine) et de ses applications en ophthamologie. Schweiz, med. Wschr. 76, 296–300 (1946).
Bovet, D.: Introduction to antihistamine agents and antergan derivatives. Ann. N.Y. Acad. Sci. 50, 1089–1126 (1950).
Bovet, D., Horclois, R., Walthert, F.: Propriétés anti-histaminiques de la N-p-méthoxybenzyl-N-diméthylaminoéthyl-α-amino-pyridine (RP2786). C. R. Soc. Biol. 138, 99–100 (1944).
Bovet, D., Staub, A.-M.: Action protectrice des éthers phénoliques au cours de l’intoxication histaminique. C. R. Soc. Biol. 124, 547–549 (1937).
Bowden, K., Young, R.C.: Structure-Activity Relations. I. A series of antagonists of acetylcholine and histamine at the postganglionic receptors. J. med. Chem. 13, 225 (1970).
Brack, W.: Über die Bedeutung der sogenannten synthetischen Antihistamine für die Dermatologie. Schweiz, med. Wschr. 76, 316–321 (1946).
Brimblecombe, R.W., Green, D.M., Inch, T.D., Thompson, B.J.: The significance of differences in the potency of enantiomers of anti-acetylcholine drugs. J. Pharm. Pharmacol. 23, 745–757 (1971).
Brittain, R.T., D’Arcy, P.F., Hunt, J.H.: Resolution of chlorpheniramine and the pharmacological properties of its isomers. Nature (Lond.) 183, 734–735 (1959).
Brock, N., Lorenz, D., Veigel, H.: Beitrag zur Wirkung von Antihistamin Substanzen. II. Zur Pharmakologie des Systral. Arzneimittel-Forsch. 4, 262–268 (1954).
Brown, E.A., Fox, L.A., Maher, J.P., Nobili, C., Norton, R.C., Sannella, T.: Clinical evaluation of chlorcyclizine (perazil). Ann. Allergy 8, 32–43 (1950).
Campaigne, E., Lesuer, W.M.: 3-Substituted thiophenes III. Antihistaminics of the N-3-thenylethylenediamine series. J. Amer. chem. Soc. 71, 333–335 (1949).
Cany, J., Huidobro, H.: Etude clinique et expérimentale de l’activité antihistaminique du succinate de doxylamine. Thérapie 15, 159–167 (1960).
Caronna, G., Palazzo, S.: Reazioni con acido azotidrico in soluzione solforica. XIII. Comportamento di alcuni derivati antrachinonici. Gazz. chim. ital. 83, 533–539 (1953).
Casy, A.F.: PMR Spectroscopy in Medicinal and Biological Chemistry. London-New York: Academic Press 1971.
Casy, A.F., Ison, R.R.: Stereochemical influences upon antihistamine activity. Further studies of isomeric 4-amino-1,2-diarylbutenes. J. Pharm. Pharmacol. 22, 270–278 (1970).
Casy, A.F., Parulkar, A.P.: Studies of stereochemical influences upon antihistaminic activity. The synthesis, configuration and antihistaminic properties of some isomeric aminobutenes. Can. J. Chem. 47, 424–427 (1969).
Casy, A.F., Pocha, P.: Studies of the elimination of 1,2-diaryl-4-dimethylaminobutan-2-ols II. The elimination of 1,2-diphenyl-4-dimethylaminobutan-2-ol and related compounds. Tetrahedron 23, 633–637 (1967).
Charpentier, P., Ducrot, R.: Two isomeric 10-(dimethylaminopropyl)phenothiazines and their ethyl homologues. C. R. Acad. Sci. Paris 232, 415–417 (1951).
Charpentier, P., Gaillot, P., Gaudechon, J.: 10-(Diethylaminopropyl)phenothiazine isomers. C. R. Acad. Sci. Paris 232, 2232–2233 (1951).
Chinn, H.I., Smith, P.K.: Motion sickness. Pharmacol. Rev. 7, 33–82 (1955).
Clapp, R.C., Clark, J.H., Vaughan, J.R., English, J.P., Anderson, G.W.: Halogenated thiophene derivatives as antihistamine agents. J. Amer. chem. Soc. 69, 1549 (1947).
Clark, G.R., Palenik, G.J.: Crystal and molecular structure of the antihistamine 2-[(2)-dimethylaminoethyl-2-thenylamino]pyridine hydrochloride. J. Amer. chem. Soc. 94, 4005–4009 (1972).
Cope, A.C., Fenton, S.W.: Cyclic polyolefins. XV. 1-Methylene-2,3,6,7-dibenzcycloheptatriene. J. Amer. chem. Soc. 73, 1673–1678 (1951).
Djerassi, C., Scholz, C.R.: Aryloxyacetamidines and 2-(aryloxymethyl)imidazolines. J. Amer. chem. Soc. 69, 1688–1692 (1947).
Doerge, R.F.: Histamine and antihistaminic agents. In: Wilson, C.O., Gisvold, O., Doerge, R.F. (Eds.): Textbook of Organic Medicinal and Pharmaceutical Chemistry, 6th Ed., pp.677–698. Philadelphia: Lippincott 1971.
Edge, N.D., Wragg, W.R.: Identification of certain antihistamines. J. Pharm. Pharmacol. 5, 279–280 (1953).
Edinburgh Staff: Pharmacological Experiments on Isolated Preparations. 2nd Ed. Edinburgh: Livingstone 1970.
Ehrlich, N.J., Kaplan, M.A.: Evaluation of perazil in allergic rhinitis. Ann. Allergy 8, 682–683 (1950).
Eisenberg, B.C.: New antihistamine; piperidyl maleate compound in allergic rhinitis. Ann. Allergy 20, 523–527 (1962).
Ellis, G.P.: The literature of medicinal chemistry. Prog. Med. Chem. 6, 266–361 (1969).
Engelhardt, E.L., Zell, H.C., Saari, W.S., Christy, M.E., Colton, C.D., Stone, C.A., Stavorski, J.M., Wenger, H.C., Ludden, C.T.: Structure-activity relationships in the cyproheptadine series. J. med. Chem. 8, 829–836 (1965).
Feinstone, W.H., Williams, R.D., Rubin, B.: Antihistamine and antianaphylactic effect of hetramine, a new synthetic pyrimidine compound. Proc. Soc. exp. Biol. (N.Y.) 63, 158–161 (1946).
Folkow, B., Haeger, K., Kahlson, G.: Reactive hyperemia as related to histamine, on drugs antagonizing vasodilation induced by histamine, and on vasodilator properties of adenosine triphosphate. Acta physiol. scand. 15, 264–278 (1948).
Fourneau, E., Bovet, D.: Recherches sur l’action sympathicolytique d’un nouveau dérivé du dioxane. Arch. Int. Pharmacodyn 46, 179–191 (1933).
Friedman, H.L., Tolstoouhov, A.V.: 2-[p-Methoxybenzyl(2-dimethylaminoethyl)amino]-pyrimidine and its hydrochloride. U.S. 2,465,865, Mar. 29, 1949. Chem. Abstracts 43, 6244d (1949).
Funcke, A.B.H., Mulder, D., Dejonge, M.C., Tersteege, H.M., Harms, A.F., Nauta, W.Th.: 3-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-xyloxy)tropane citrate (dibenzheptropine citrate, Brontine). Arch. int. Pharmacodyn. 148, 135–162 (1964).
Gay, L.N., Carliner, P.E.: The prevention and treatment of motion sickness. I. Sea Sickness. Bull. Johns Hopk. Hosp. 84, 470–487 (1949a).
Gay, L.N., Carliner, P.E.: The prevention and treatment of motion sickness. I. Sea Sickness. Science 109, 395 (1949b).
Gerald, M.C., Sethi, O.P., Muhi-Eldeen, Z., Mahishi, N., Witiak, D.T.: Pharmacological studies of the stereoselective antihistaminic and anticholinergic properties of L(S)- and D(R)-3-ethylamino-1-phenylpyrrolidine. Arch. int. Pharmacodyn. Ther. 192, 78–87 (1971).
Girard, J.P.: Propriétés antianaphylactiques du 9-(N-méthyl-pipéridyliden-4′)thioxanthen (BP400) et du lysozyme, comparées à celle de la prednisone. Med. Exptl. (Basel) 9, 400–408 (1963a).
Girard, J.P.: Essais cliniques d’une nouvelle substance anti-allergique, 9-(N-méthyl-pipéridyliden-4)-thioxanthen (BP400). J. Suisse Med. 93, 446–449 (1963b).
Green, A.F.: The antagonism of histamine and the anaphylactic response by phenylpyridyl-allylamines. Brit. J. Pharmacol. 8, 171–176 (1953).
Halpern, B.N.: Les antihistaminiques de synthèse. Essai de chimiothérapie des états allergiques. Arch. int. Pharmacodyn 68, 339–408 (1942).
Halpern, B.N.: Recherches sur une nouvelle série chimique de corps doués de propriétés antihistaminiques et antianaphylatiques: les dérivés de la thiodiphénylamine. Bull. Soc. chem. Biol. 29, 309–318 (1947).
Halpern, B.N., Ducrot, R.: Recherches expérimentales sur une nouvelle série chimique de corps doues de propriétés antihistaminiques puissantes: les dérivés de la thiophénylamine (T.D.A.). C.R. Soc. Biol. 140, 361–363 (1946).
Halpern, B.N., Stiffel, C., Liacopoulos-Briot, M., Conovici, L.: Recherches sur un nouvel antihistaminique de synthèse, la cinnarazine. Arch. int. Pharmacodyn 142, 170–184 (1963).
Halpern, B.N., Walthert, F.: Conditionnement de l’antagonisme histamine-antihistaminiques sur la corne utérine de cobaye par l’équilibre ionique du milieu de survie. C.R. Soc. Biol. 139, 402–404 (1945).
Ham, N.S.: Solution conformation of antihistamines. J. pharm. Sci. 60, 1764–1765 (1971).
Ham, N.S., Casy, A.F., Ison, R.R.: Solution conformations of histamine and some related derivatives. J. med. Chem. 16, 470–475 (1973).
Hanna, P.E., Ahmed, A.E.: Conformationally restricted analogs of histamine H1 receptor antagonists trans- and cis-1,5-diphenyl-3-dimethylaminopyrrolidine. J. med. Chem. 16, 963–968 (1973).
Hanna, P.E., Ahmed, A.E., Grund, V.R., Merriman, R.L.: 1,5-Diphenyl-3-dimethylamino-pyrrolidine: a long-acting histamine antagonist. J. pharm. Sci. 62, 512–514 (1973).
Hanna, P.E., Borchardt, R.T.: Histamine N-methyltransferase. Inhibition and potentiation by trans- and cis-1,5-diphenyl-3-dimethylaminopyrrolidine. J. med. Chem. 17, 471–473 (1974).
Hanna, P.E., Grund, V.R., Anders, M.W.: Conformationally restricted analogs of histamine H1 receptor antagonists. 2-Phenyl- and 2-benzyl-1,2,3,4-tetrahydro-4-dimethylamino-isoquinoline. J. med. Chem. 17, 1020–1023 (1974).
Hansson, E., Schmiterlöw, C.G.: A comparison of the distribution, excretion and metabolism of a tertiary promethazine and a quaternary (Aprobit) phenothiazine compound labelled with sulphur-35. Arch. int. Pharmacodyn. 131, 309–324 (1961).
Hanze, A.R., Strube, R.E., Greig, M.E.: Dibenzo [b,e] [1,4] diazepines. J. med. Chem. 6, 767–771 (1963).
Hörlein, U.: Zur Kenntnis der Tetrahydrocarbolin-Verbindungen (I. Mitteil.). Chem. Ber. 87, 463–472 (1954).
Hoppe, J.O., Lands, A.M.: Toxicologic properties of N′-2(pyridyl)-N′-(3-thenyl)-N,N-dimethyle-thylenediamine hydrochloride (thenfadil, WIN 2848), a new antihistaminic drug. J. Pharmacol, exp. Ther. 97, 371–380 (1949).
Horáková, Z., Votava, Z.: Local anaesthetic action of phenothiazine, homophenothiazine, and homoacridan derivatives. Physiol, bohemoslov. 8, 260–267 (1959).
Horclois, R.J.: 2-Aminopyridine antihistaminic compounds. U.S. Patent 2,489,777, 29 Nov. 1949. Chem. Abstr. 44, P7353c (1950).
Huebner, C.F., Donoghue, E., Wenk, P., Sury, E., Nelson, J.A.: A new class of highly active antihistaminics. J. Amer. chem. Soc. 82, 2077–2078 (1960).
Hunziker, F., Kuenzle, F., Schmutz, J.: Siebengliedrige Heterozyklen. II. Über die 5-Stellung basisch substituierter 5H-Dibenzo[b,e]-1,4-diazepine. Helv. chim. Acta 46, 2337–2346 (1963).
Huttrer, C.P.: Chemistry of antihistaminic substances. Enzymologia 12, 277–332 (1948).
Huttrer, C.P.: Recent progress in histamine and antihistamine research. Experientia (Basel) 5, 53–65 (1949).
Huttrer, C.P., Djerassi, C., Beears, W.L., Mayer, R.L., Scholz, C.R.: Heterocyclic amines with antihistaminic activity. J. Amer. chem. Soc. 68, 1999–2002 (1946).
Ison, R.R.: Stereochemical studies of antihistaminic agents. Ph.D. Thesis, University of Alberta, 1970.
Ison, R.R., Casy, A.F.: Structural influences upon antihistamine activity; 3-amino-1-aryl-1-(2-pyridyl)propenes and related compounds. J. Pharm. Pharmacol. 23, 848–856 (1971a).
Ison, R.R., Casy, A.F.: Studies of antihistaminics. Dehydration of some substituted 4-aminobutan-2-ols. J. chem. Soc. (Org) 3048–3051 (1971b).
Ison, R.R., Franks, F.M., Soh, K.S.: The binding of conformationally restricted antihistamines to histamine receptors. J. Pharm. Pharmacol. 25, 887–894 (1973).
Iupac. Tentative rules for the nomenclature of organic chemistry. Section E. Fundamental stereochemistry. J. Org. Chem. 35, 2849–2867 (1970).
James, M.N.G., Williams, G.J.B.: Crystal structure of dl-brompheniramine maleate [1-(p-bromophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamine maleate]. J. med. Chem. 14, 670–675 (1971).
James, M.N.G., Williams, G.J.B.: Structural studies on histamine H1 effector molecules. The crystal structure of the antihistamine drug (+)—chlorpheniramine maleate [(+)-S-1-(p-chlorophenyl)-1(2-pyridyl)-3-N,N-dimethylpropylamine maleate]. Can. J. Chem. 52, 1872–1879 (1974a).
James, M.N.G., Williams, G.J.B.: The crystal and molecular structure of the antihistaminic drug triprolidine hydrochloride monohydrate [trans-1-(p-tolyl)-1-(2-pyridyl)-3-(1-pyrrolidino)-prop-1-ene]. Can. J. Chem. 52, 1880–1888 (1974b).
Jarrousse, M.J., Régnier, M.T.: Séparation et activité physiologique des deux isomers optiques du diméthylaminoéthoxy-(p-tolylphenylméthane). Ann. pharm, franç. 9, 321–325 (1951).
Jerchel, D., Fischer, H., Kracht, M.: Zur Darstellung der Benzimidazole. Ann. Chem. 575, 162–173 (1952).
Jilek, J.O., Seidlova, V., Svatek, E., Prouva, M., Pomykacek, J., Sedivy, Z.: Neurotrope und psychotrope Substanzen. 5. Mitt. Synthese neuer Aminoderivate von 10,11-Dihydrodibenzo [a,d] cyclohepten und 10,11-Dihydrodibenzo [b,f]thiepin, und 6, 11-Dihydrodibenzo [b,e]-thiepin. Mschr. Chem. 96, 182–207 (1965).
Jucker, E., Ebnother, A.: Antihistamines. Swiss Patent 401,055. 30 April 1966. Chem. Abstr. 65, 3825h (1966).
Judd, A.R., Henderson, A.R.: The use of antihistaminic drugs in human tuberculosis. Ann. Allergy 7, 306–317 (1949).
Knoll, A.-G.: 4-(N-Phenylbenzylamino)-1-alkylpiperidines substituted in the aromatic radicals. British Patent 700,097.25 November 1953, Chem. Abstr. 49, 6318 (1955).
Kuntzman, R., Jacobson, M., Tsai, I., Burns, J.J., Burchall, J., Koch, A.: Certain aspects of drugs binding to nonplasma proteins as illustrated by studies with cyclizine, chlorcyclizine, and polymyxin B. Ann. New York Acad. Sci. 226, 131–147 (1973).
Kunz, W.: Neue Arzneimittel (V). Teil II. Arch. Pharm. 287, 463–482 (1954).
Kutter, E., Hansch, C.: Steric parameters in drug design. Monoamine oxidase inhibitors and antihistamines. J. Med. Chem. 12, 647–652 (1969).
LaBelle, A., Tislow, R.: Prophenpyridamine (Trimeton) and chloroprophenpyridamine (Chlortrimeton). J. Pharmacol, exp. Ther. 113, 72 – 88 (1955).
Lands, A.M., Hoppe, J.O., Siegmund, O.H., Ludueña, F.P.: Pharmacological properties of 3 new antihistaminic drugs. J. Pharmacol, exp. Ther. 95, 45–52 (1949).
Lee, H.M., Anderson, R.C., Harris, P.N.: Antihistaminic action of “pyronil”. Proc. Soc. exp. Biol. (N.Y.) 80, 458–462 (1952).
Lehmann, G.: Pharmacological properties of a new antihistaminic, 2-methyl-9-phenyl-2, 3, 4, 9-tetrahydro-1-pyridindene (thephorin) and derivatives. J. Pharmacol, exp. Ther. 92, 249–259 (1948).
Lehmann, G., Randall, L.O., Hagen, E.: The antihistamine, antiadrenaline and antiacetylcholine action of thephorin. Arch. int. Pharmacodyn. 78, 253–267 (1949).
Leonard, F., Huttrer, C.P.: Histamine Antagonists. Washington D.C.: Chemical Biological Coordination Center, National Research Council 1950.
Loew, E.R., Kaiser, M.E., Moore, V.: Synthetic benzohydryl alkamine ethers effective in preventing fatal experimental asthma in guinea pigs exposed to atomized histamine. J. Pharmacol, exp. Ther. 83, 120–129 (1945).
Loew, E.R., MacMillan, R., Kaiser, M.E.: Antihistamine properties of Benadryl(2-dimethylaminoethyl benzohydryl ether hydrochloride). J. Pharmacol, exp. Ther. 86, 229–238 (1946).
Lovejoy, H.B., Feinberg, S.M., Canterbury, E.A.: Local inhibition of histamine flare in man; method of bioassay of antihistamine drugs. J. Allergy 20, 350–357 (1949).
Marshall, P.B.: Some chemical and physical properties associated with histamine antagonism. Brit. J. Pharmacol. 10, 270–278 (1955).
Martindale: Extra Pharmacopoeia. 26th Ed. London: Pharmaceutical Press 1972.
McGavack, T.H., Shearman, A.H., Weissberg, J., Fucks, A.M., Schulman, P.M., Drekter, I.J.: Newer antihistaminics. IV. Some pharmacologic and therapeutic effects of β-(p-bromobenzhydryloxy)ethyldimethylamine hydrochloride, a derivative of diphenylhydramine hydrochloride. J. Allergy 22, 31–46 (1951).
Melville, K.I.: Antihistamine drugs. In: Schachter, M. (Ed.): Histamine and Antihistaminics. International Encyclopedia of Pharmacology and Therapeutics, Section 74, Vol.1. Oxford: Pergamon 1973.
Metys, J., Metysová, J.: Derivat des 4,9-Dihydrothieno(2,3-b)benzo[e]thiepins: Ein neuer Typ des wirksamen Antihistaminikums. Acta biol. med. germ. 15, 871–873 (1965).
Metysová, J., Metys, J., Votava, Z.: Pharmakologische Eigenschaften der 6,11-Dihydrodibenz [b, e]thiepin-Derivate. Arzneimittel-Forsch. 13, 1039–1043 (1963).
Metysová, J., Metys, J., Votava, Z.: Pharmakologische Eigenschaften der 6,11-Dihydrodibenzo[b.e]thiepin-Derivate. II. Arzneimittel-Forsch. 15, 524–527 (1965).
Miescher, K., Klarer, W.: Imidazolines. U.S. 2,449,241. Sept. 14 1948. Chem. Abstr. 43, 692d (1949).
Mietzsch, F.: Die Entwicklung der Antihistaminmittel und zentral dämpfenden Mittel. Angew. Chem. 66, 363–367 (1954).
Mills, J.: 1-(p-Chlorophenyl)-2-phenyl-4-(pyrrolidino)butenes. U.S. 2,655,509 13 Oct. 1953. Chem. Abstr. 48, P 13726 c (1954).
Morren, H., Trolin, S., Denayer, R., Grivsky, E., Maricq, J.: Nouvelles substances antihistaminiques à action prolongée: les 1, 4 bis (aracoyl)-pipérazines. Bull. Soc. chim. Belges 60, 282–295 (1951).
P’An, S.Y., Gardocki, J.F., Reilly, J.C.: Pharmacological properties of two new antihistamines of prolonged action. J. Amer, pharm. Ass. 43, 653–656 (1954).
Paris Correspondent: Antagonists of histamine. J. Amer. med. Ass. 129, 1219–1220 (1945).
Plati, J.T, Wenner, W.: Heterocyclic amines U.S. 2,470,108 and 2,470,109 17 May 1949. Chem. Abstr. 43, 5808 f (1949a).
Plati, J.T., Wenner, W.: Reaction of acetophenone with formaldehyde and methylamine hydrochloride. J. org. Chem. 14, 543–549 (1949b).
Protiva, M.: Chemie Antihistaminovych Latek a Histaminove Skupiny. Prague: Ceskoslovensker Akademic Ved. 1955.
Protiva, M.: Recent progress on the pharmaco-chemical research on antihistamine drugs and psychotropic agents—derivatives of tricyclic systems having a seven- or eight-membered middle ring. Farmaco, Ed. sci. 21, 78–104 (1966).
Protiva, M., Borovicka, M., Hach, V., Votava, Z., Metysova-Sramkova, J., Horakova, Z.: Über pharmakodynamisch interessante Aminoalkylderivate von Acridan- und Phenthiazin-homologen. Experientia. (Basel) 13, 291–292 (1957).
Protiva, M., Rajsner, M., Adlerova, E., Seidlova, V., Vejdelek, Z.J.: Neurotropic and psychotropic substances. I. New types of 6,11-dihydrodibenzo[b,e]thiepine derivatives and analogues. Coll. Czech. Chem. Commun. 29, 2161–2181 (1964).
Reid, W.B., Wright, J.B., Kolloff, H.G., Hunter, J.H.: Histamine antagonists. II. N-(Pyrrolidylalkyl)phenothiazines. J. Amer. chem. Soc. 70, 3100–3102 (1948).
Rekker, R.F., Timmerman, H., Harms, A.F., Nauta, W.Th.: The antihistaminic and anticholinergic activities of optically active diphenylhydramine derivatives. Arzneimittel-Forsch. 21, 688–691 (1971).
Rekker, R.F., Timmerman, H., Harms, A.F., Nauta, W.Th.: Changes in antihistaminic and anticholinergic activities of diphenhydramine derivatives on quaternization and the role of an asymmetric centre. Chim. Therap. 7, 279–282 (1972).
Reuse, J.J.: Comparisons of various histamine antagonists. Brit. J. Pharmacol. 3, 174–180 (1948).
Rieveschl, G.R.: Dialkylaminoalkyl benzhydryl ethers. U.S. 2,421,714 June 3 1947. Chem. Abstr. 41, 5550h (1947).
Rieveschl, G.R., Huber, W.F.: Abstracts, 109 th Meeting, American Chemical Society, 1946, p.50K.
Römer, D., Cerletti, A.: Konstitution und Wirkung von „Antaminica“einer Wirkstoffgruppe aus der Reihe substituierter Tricyclen. Arch. exp. Path. Pharmakol. 250, 174–175 (1965).
Rometsh, R.: Stereoisomers of α-phenyl-α-(2-piperidyl) acetic acid. U.S. 2,838,519 10 June 1958. Chem. Abstr. 52, 16, 374c (1958).
Roncevich, A.: Allergic rhinitis and its control by antihistamines: clinical trial of Tavegyl (meclastine). Curr. Ther. Res. 11, 625–633 (1969).
Roszkowski, A.P., Govier, W.M.: Comparison of racemic carbinoxamine with its optically active isomers. Pharmacologist 1, 60 (1959).
Roth, F.E.: Antihistamine activity of the optical isomers of pheniramine and its chlor- and brom-substituted derivatives. Chemotherapia 3, 120–127 (1961).
Roth, F.E., Govier, W.M.: Comparative pharmacology of chlorpheniramine (chlor-trimeton) and its optical isomers. J. Pharmacol, exp. Ther. 124, 347–349 (1958).
Sabbah, A.: Etude chimique et pharmacologique d’un nouvel anti-histaminique. Le dimaléate d’azatadine dans les maladies par hypersensibilité. Vie méd. 41, 5401–5404 (1969).
Saijo, S.: Antihistaminic agents V. N,N-Dimethyl-3-(2-pyridyl)-propylamine derivatives. J. Pharm. Soc. Japan 72, 1529–1531 (1952).
Schenker, E., Herbst, H.: Phenothiazine und Azaphenothiazine als Heilmittel. Progr. Drug Res. 5, 269–627 (1963).
Schild, H.O.: pA, A new scale for the measurement of drug antagonism. Brit. J. Pharmacol. 2, 189–206 (1947).
Schindler, O.: Klinische Untersuchungen mit der Antihistaminsubstanz Antistin Ciba. Schweiz, med. Wschr. 76, 300–305 (1946).
Schindler, W., Häfliger, F.: Über Derivate des Iminodibenzyls. Helv. chim. Acta 37, 472–483 (1954).
Schlichtegroll, A., von: Pharmacology of various thiophenylpyridylamines. Arzneimittel-Forsch. 7, 237–252 (1957).
Schmid, H.J., Hunger, A., Hoffmann, K.: Sterische und elektrostatische Effekte in der Schmidt-Reaktion. Helv. chim. Acta 39, 607–618 (1956).
Schulemann, W., Friebel, H.: Chemische und pharmakologische Untersuchungen über einen neuen Antihistaminkörper. Dtsch. med. Wschr. 78, 540–549 (1953).
Schuler, W.A., Klebe, H.: Synthesen von 4-Aza-phenothiazinen. I. 4-Aza-phenothiazine und deren 10-Aminoalkyl-Derivate. Ann. Chem. 653, 172–180 (1962).
Schwartz, E., Reicher, J.: A clinical evaluation of neohetramine in allergic disease. Ann. Allergy 7, 320–324 (1949).
Shafi’ee, A., Hite, G.: The absolute configurations of the pheniramines, methyl phenidates and pipradols. J. med. Chem. 12, 266–270 (1969).
Sigal, B., Herblot, M.: Action antiprurigineuse du dimaleate d’azatadine dans certaines affections dermatologiques. Gaz. méd. Fr. 77, 364–365 (1970).
Sperber, N., Papa, D., Schwenk, E.: 3-Pyridylpropylamine antihistaminic substances. U.S. 2,676,964 27 April 1954. Chem. Abstr. 49, 6316f.
Sperber, N., Papa, D., Schwenk, E., Sherlock, M.: Pyridylsubstituted alkamine ethers as antihistaminic agents. J. Amer. chem. Soc. 71, 887–890 (1949).
Sperber, N., Papa, D., Schwenk, E., Sherlock, M., Fricano, R.: Histamine antagonists. γ,γ-Disubstituted N,N-dialkylpropylamines. J. Amer. chem. Soc. 73, 5752–5559 (1951).
Staub, A.M.: Recherches sur quelques bases synthétiques antagonistes de l’histamine. Ann. Inst. Pasteur. 63, 400–436 (1939a).
Staub, A.M.: Recherches sur quelques bases synthétiques antagonistes de l’histamine. Ann. Inst. Pasteur 63, 485–524 (1939b).
Stoll, A., Bourquin, J.P.: Piperidine derivatives. U.S. Patent 2,757,175 (1956). Chem. Abstr. 51, 2055 (1957).
Stoll, W.G., Frey, Ch., Morel, Ch.J.: Antihistaminica III. Über α-(Aminoalkyl)stilbene. Helv. chim. Acta 33, 1208–1217 (1950b).
Stoll, W.G., Morel, Ch.J., Frey, Ch.: Antihistaminica II. Über die Synthese von 1, 2-disubstituierten 4-Amino-Δ 2-butenen. Helv. chim. Acta 33, 1194–1207 (1950a).
Stone, C.A., Wenger, H.C., Ludden, C.T., Stavorski, J.M., Ross, C.A.: Antiserotonin-antihistaminic properties of cyproheptadine. J. Pharmacol, exp. Ther. 131, 73–84 (1961).
Thomas, J.W., Kelley, F.R.: Clinical evaluation of ambodryl hydrochloride; report of 100 cases. Ann. Allergy 9, 481–486 (1951).
Tilford, C.H., Shelton, R.S., van Campen, M.G.: Histamine antagonists. Basically substituted pyridine derivatives. J. Amer. chem. Soc. 70, 4001–4009 (1948).
Toldy, L., Vargha, L., Toth, I., Borsy, J.: Promethazine I. Acta Chim. Acad. Sci. Hungary 19, 273–275 (1959).
Tozzi, S.: Pulmonary and antiallergy agents. A. R. med. Chem. 7, 89–98 (1972).
Treibs, W., Klinkhammer, H.J.: Über das 1.2;4.5-Dibenz-suberon-(3). Chem. Ber. 83, 367–371 (1950).
Treibs, W., Klinkhammer, H.J.: Über das 2.3;6.7-Dibenz-suberon-(1). II. Mitt. Synthese des 2.3;6.7-Dibenz-suberen-(4)-ons-(1) und des 2.3;6.7-Dibenz-suberens-(4). Chem. Ber. 84, 671–677 (1951).
Trottier, R.W., Malone, M.H.: Comparative in vitro evaluation of cryogenine, cyproheptadine, and diphenhydramine as antagonists of furtrethonium, histamine and serotonin. J. pharm. Sci. 58, 1250–1253 (1969).
Ungar, G., Parrot, J.-L., Bovet, D.: Inhibition of the effects of histamine on isolated guinea-pig intestine by various sympathicomimetic and sympathicolytic substances. C. R. Soc. Biol. (Paris) 124, 445–446 (1937).
Van der Brook, M.J., Olson, K.J., Richmond, M.T., Kuizenga, M.H.: Pharmacology of a new antihistamine, 10-[β-(1-pyrrolidine)ethyl] phenothiazine monohydrochloride (pyrrolazote). J. Pharmacol, exp. Ther. 94, 197–208 (1948).
Van der Stelt, C., Harms, A.F., Nauta, W.Th.: The effect of alkyl-substitution in drugs. V. Synthesis and chemical properties of some dibenzo[a,d]1,4-cycloheptadienyl ethers. J. med. Pharm. Chem. 4, 335–349 (1961).
Van der Vlies, C.: Binding of a diphenhydramine analogue to BSA. An NMR investigation. Biochem. Pharmacol. 19, 859–864 (1970).
Vaughan, J.R., Anderson, G.W., Clapp, R.C., Clark, J.H., English, J.P., Howard, K.L., Marson, L.H., Sutherland, L.H., Denton, J.J.: Antihistamine agents. IV. Halogenated N,N-dimethyl-N′-benzyl-N′-2-pyridylethylenediamines. J. org. Chem. 14, 228–234 (1949).
Veidis, M.V., Palenik, G.J., Schaffrin, R., Trotter, J.: Crystal structure of histamine diphosphate monohydrate. J. chem. Soc. A. 2659–2666 (1969).
Viaud, P.: Les amines derivées de la phenothiazine. J. Pharm. Pharmacol. 6, 361–389 (1954).
Villani, F.J., Daniels, P.J.L., Ellis, C.A., Mann, T.A., Wang, K.-C.: Derivatives of 10, 11-dihydro-5H-dibenzo[a, d]cycloheptene and related compounds. III. Azaketones. J. Het. Chem. 8, 73–81 (1971).
Villani, F.J., Daniels, P.J.L., Ellis, C.A., Mann, T.A., Wang, K.-C., Wefer, E.A.: Derivatives of 10,11-dihydro-5H-dibenzo[a, d]cycloheptene and related compounds. 6. Aminoalkyl derivatives of the aza isosteres. J. med. Chem. 15, 750–754 (1972).
Votava, Z., Metysová, J., Horáková, Z.: Pharmacological studies of compounds with an expected neuroplegic effect. 1. Derivatives of homophenothiazine and homocridane. Cs. Farm. 7, 125–129 (1958).
Wahner, H.W., Peters, C.A.: An evaluation of some newer antihistaminic drugs against pollinosis. Proc. Mayo Clin. 35, 161–169 (1960).
Waringa, C.G.: 1,1-Diaryl-3-aminopropenes and some related compounds: synthesis and biological activities. Academisch Proefschrift, Free University of Amsterdam 1974.
Weiss, R.: Benzalphthalide. Org. Syn. Coll. 2, 61–63 (1943).
Weisz, I., Dudás, A.: The stereochemistry of methyl α-(2-piperidyl)phenylacetate. Acta Pharm. Hung. 31/B, Suppl. 116–117 (1961).
Werle, E., Kopp, K., Leysath, G.: Die Antihistaminwirkung von 2,7-Diazaphenothiazin und einige seiner Derivate. Arzneimittel-Forsch. 12, 443–444 (1962).
Weston, A.W.: N,N-Dimethyl-N′-2-pyridyl-N′-2-thenylethylene diamine, an antihistaminic agent. J. Amer. chem. Soc. 69, 980–981 (1947).
White, A.C., Green, A.F., Hudson, A.: Some pharmacological properties of 3,3-diphenylpro-panolamines,-allylamines and -propylamines. Brit. J. Pharmacol. 6, 560–571 (1951).
Wilken-Jensen, K.: Experimental and clinical study of new antihistaminic paradryl (quaternary ammonium compound). Ugeskr. Loeg. 112, 679–681 (1950).
Winder, C.V., Kaiser, M.E., Anderson, M.M., Glassco, E.M.: Myotropic, spasmolytic, histaminolytic, and atropine-like actions of some derivatives of dimethylaminoethyl benzhydryl ether hydrochloride (benadryl). J. Pharmacol, exp. Ther. 87, 121–131 (1946).
Witiak, D.T.: Antiallergenic agents in medicinal chemistry. In: Burger, A. (Ed.): Medicinal Chemistry, 3rd Ed., pp. 1643–1668. New York: Wiley-Interscience 1970.
Witiak, D.T., Hsu, S.Y., Ollmann, J.E., Griffith, R.K., Seth, S.K., Gerald, M.C.: D-(R)- and L-(S)-3-Alkylamino-pyrrolidino-substituted dihydrodibenzo[b,f]-and-[b,e]thiepins, xanthenes, and diphenylmethanes. J. med. Chem. 17, 690–696 (1974).
Witiak, D.T., Muhi-Eldeen, Z., Mahishi, N., Sethi, O.P., Gerald, M.C.: L(S)- and D(R)-3-Amino-1-phenylpyrrolidines. Selective antagonists for histamine and acetylcholine receptors in vitro. J. med. Chem. 14, 24–30 (1971).
Yale, H.L., Sowinski, F.: Novel polycyclic heterocycles. II. Derivatives of 5,11-Dihydrodibenz[b,e][1,4]oxazepine. J. med. Chem. 7, 609–614 (1964).
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 1978 Springer-Verlag Berlin Heidelberg
About this chapter
Cite this chapter
Casy, A.F. (1978). Chemistry of Anti-H1 Histamine Antagonists. In: Rocha e Silva, M. (eds) Histamine II and Anti-Histaminics. Handbuch der experimentellen Pharmakologie / Handbook of Experimental Pharmacology, vol 18 / 2. Springer, Berlin, Heidelberg. https://doi.org/10.1007/978-3-642-66445-8_4
Download citation
DOI: https://doi.org/10.1007/978-3-642-66445-8_4
Publisher Name: Springer, Berlin, Heidelberg
Print ISBN: 978-3-642-66447-2
Online ISBN: 978-3-642-66445-8
eBook Packages: Springer Book Archive