Literature cited
S. A. Stone, H. C. Wenger, C. T. Ludden, et al., J. Pharmacol. Exp. Ther.,131, 73–84 (1961).
B. V. Clineschmidt, H. M. Hanson, J. C. McGuffin, et al., Arch. Int. Pharmacodyn.,223, 283–300 (1976).
U. S. Patent No. 1014911 (1969); Chem. Abstr.,56, 10112 (1962).
E. D. Engelhardt, H. C. Zell, W. S. Saari, et al., J. Med. Chem.,8, 829–835 (1965).
A. Ebnother, E. Jucker, and A. Stoll, Helv. Chim. Acta,48, 1237–1249 (1965).
West German Patent No. 1920070 (1969); Chem. Abstr.,72, 43297 (1970).
U. S. Patent No. 4022902 (1977), Chem. Abstr.,88, 74299 (1978).
U. S. Patent No. 4132796 (1979), Chem. Abstr.,90, 137685 (1979).
West German Patent No. 2813255 (1978); Chem. Abstr.,90, 22830 (1979).
U. S. Patent No. 4031222 (1977); Chem. Abstr.,87, 102184 (1977).
U. S. Patent No. 4031223 (1977); Chem. Abstr.,87, 102185 (1977).
U. S. Patent No. 4220651 (1980); Chem. Abstr.,94, 3935 (1981).
European Patent Application No. 12988 (1980); Chem. Abstr.,94, 65476 (1981).
West German Patent No. 2550395 (1976); Chem. Abstr.,85, 46416 (1976).
Spanish Patent No. 391955 (1973); Chem. Abstr.,80, 82704 (1974).
Spanish Patent No. 407655 (1975); Chem. Abstr.,84, 180062 (1976).
Spanish Patent No. 363078 (1969); Chem. Abstr.,74, 141557 (1971).
Japanese Patent No. 7305744 (1973); Chem. Abstr.,78, 97494 (1971).
West German Patent No. 1921934 (1969); Chem. Abstr.,72, 31625 (1970).
Spanish Patent No. 370028 (1969); Chem. Abstr.,72, 100536 (1970).
Spanish Patent No. 370029 (1969); Chem. Abstr.,72, 100537 (1970).
Spanish Patent No. 391813 (1973); Chem. Abstr.,82, 171074 (1975).
Spanish Patent No. 350757 (1969); Chem. Abstr.,72, 12587 (1970).
Spanish Patent No. 443127 (1977); Chem. Abstr.,88, 94816 (1978).
Spanish Patent No. 416684 (1976); Chem. Abstr.,86, 47288 (1977).
Spanish Patent No. 364151 (1971); Chem. Abstr.,75, 121423 (1971).
Spanish Patent No. 373803 (1972); Chem. Abstr.,78, 43285 (1973).
Spanish Patent No. 385005 (1973); Chem. Abstr.,79, 96986 (1973).
Spanish Patent No. 418804 (1976); Chem. Abstr.,85, 198165 (1976).
Spanish Patent No. 404946 (1975); Chem. Abstr.,84, 65271 (1976).
B. Birknes, Acta Crystallogr.,33B, 687–691 (1977).
H. Y. Aboul-Enein and A. A. Al-Badr, Anal. Profiles Drug Subst.,9, 155–179 (1980); Chem. Abstr.,95, 12599 (1981).
U. S. Patent No. 3352869 (1967); Chem. Abstr.,68, 104986 (1968).
Br. Patent No. 1111733 (1968); Chem. Abstr.,69, 67224 (1968).
French Patent No. 2197526 (1974); Chem. Abstr.,81, 134881 (1974).
R. D. Wilkerson, J. Med. Chem.,23, 1255–1258 (1980).
U. S. Patent No. 3475438 (1969); Chem. Abstr.,72, 3382 (1970).
German Patent No. 2102196 (1971); Chem. Abstr.,76, 14350 (1972).
U. S. Patent No. 3903286 (1975); Chem. Abstr.,83, 193104 (1975).
U. S. Patent No. 3960872 (1976); Chem. Abstr.,85, 142991 (1976).
U. S. Patent No. 3968115 (1976); Chem. Abstr.,86, 16544 (1977).
U. S. Patent No. 3981876 (1976); Chem. Abstr.,86, 29643 (1977).
U. S. Patent No. 3988342 (1976); Chem. Abstr.,86, 106395 (1977).
U. S. Patent No. 3894032 (1975); Chem. Abstr.,83, 193093 (1975).
U. S. Patent No. 3974285 (1976); Chem. Abstr.,85, 192575 (1976).
D. C. Remy, A. W. Raab, K. E. Rittle, et al., J. Med. Chem.,20, 836–838 (1977).
U. S. Patent No. 3981877 (1976); Chem. Abstr.,86, 29640 (1977).
European Patent Application No. 16349 (1980); Chem. Abstr.,94, 103181 (1981).
U. S. Patent No. 4212871 (1980); Chem. Abstr.,93, 220603 (1980).
D. C. Remy, K. E. Rittle, G. A. Hunt, et al., J. Med. Chem.,20, 1013–1019 (1977).
D. C. Remy, K. E. Rittle, G. A. Hunt, et al., J. Med. Chem.,20, 1681–1687 (1977).
W. C. Randell, P. S. Anderson, E. L. Caesson, et al., J. Med. Chem.,22, 1222–1230 (1979).
S. E. Robinson, V. J. Lotti, and F. Sulser, J. Pharm. Pharmacol.,29, 564–565 (1977).
U. S. Patent No. 2985660 (1961); Chem. Abstr.,65, 12150 (1966).
J. Metysova, J. Metys, and M. Protiva, Arzneim.-Forsch.,13, 1039–1043 (1963).
E. Adlerova, V. Seidlova, and M. Protiva, Cs1. Farm.,12, 122–126 (1963).
F. Gadient, E. Jucker, A. Lindenmann, et al., Helv. Chim. Acta,45, 1860–1870 (1962).
Br. Patent No. 1006822 (1965); Chem. Abstr.,64, 718 (1966).
Swiss Patent No. 384589 (1965); Chem. Abstr.,63, 1776 (1965).
French Patent No. 1332145 (1963); Chem. Abstr.,60, 2917 (1964).
Czechoslovak Patent No. 107632 (1963); Chem. Abstr.,60, 1718 (1964).
Belgian Patent No. 618591 (1962); Chem. Abstr.,58, 9036 (1963).
Belgian Patent No. 626301 (1963); Chem. Abstr.,60, 10658 (1964).
A. E. Drukker, C. I. Judd, J. M. Spoerl, et al., J. Heterocycl. Chem.,2, 276–282 (1965).
French M. Patent No. 3348 (1965); Chem. Abstr.,63, 14831 (1965).
French Patent No. 1391767 (1965); Chem. Abstr.,63, 18055 (1965).
U. S. Patent No. 3692906 (1972); Chem. Abstr.,78, 16070 (1973).
West German Patent No. 1470379 (1970); Chem. Abstr.,73, 45376 (1970).
Br. Patent No. 1207116 (1970); Chem. Abstr.,74, 13023 (1971).
Br. Patent No. 1128374 (1968); Chem. Abstr.,70, 37665 (1979).
C. Kaiser, P. J. Fowler, D. H. Tedeschi, et al., J. Med. Chem.,17, 57–62 (1974).
U. S. Patent No. 4148903 (1979); Chem. Abstr.,91, 20349 (1979).
Jpn. Patent No. 7927597 (1979); Chem. Abstr.,91, 56825 (1979).
U. S. Patent No. 4195091 (1980); Chem. Abstr.,93, 71581 (1980).
T. Yanagida, H. Yizuka, A. Shimada, et al., Zenzinsho Kaukyuho,1, 79–89 (1975); Chem. Abstr.,84, 38611 (1976).
S. Tozzi, F. E. Roth, and I. I. A. Tabachnik, Agents Action,4, 264–270 (1970).
Belgian Patent No. 647043 (1964); Chem. Abstr.,63, 14829 (1965).
U. S. Patent No. 3357986 (1967); Chem. Abstr.,69, 27262 (1968).
U. S. Patent No. 3366635 (1968); Chem. Abstr.,69, 10372 (1968).
U. S. Patent No. 4282233 (1981); Chem. Abstr.,95, 203761 (1981).
U. S. Patent No. 3301863 (1967); Chem. Abstr.,67, 21833 (1967).
Belgian Patent No. 636717 (1964); Chem. Abstr.,61, 14643 (1964).
J. M. Bastian, A. Ebnother, E. Jucker, et al., Helv. Chim. Acta,49, 214–233 (1966).
Netherlands Patent Application No. 6414548 (1965); Chem. Abstr.,64, 715 (1966).
West German Patent No. 2605980 (1976); Chem. Abstr.,85, 192580 (1976).
Swiss Patent No. 587845 (1977); Chem. Abstr.,87, 84830 (1977).
West German Patent No. 2626583 (1977); Chem. Abstr.,86, 139876 (1977).
West German Patent No. 2441591 (1975); Chem. Abstr.,83, 79084 (1975).
South African Patent No. 7501548 (1976); Chem. Abstr.,87, 201319 (1977).
Austrian Patent No. 340419 (1977); Chem. Abstr.,88, 105163 (1978).
USSR Patent No. 597169 (1978); Chem. Abstr.,89, 43119 (1978).
Israeli Patent No. 46784 (1979); Chem. Abstr.,92, 18102 (1980).
U. S. Patent No. 4223035 (1980); Chem. Abstr.,94, 83933 (1981).
West German Patent No. 2423721 (1974); Chem. Abstr.,83, 144155 (1975).
West German Patent No. 2004743 (1970); Chem. Abstr.,73, 98789 (1970).
French Addn. Patent No. 91084 (1968); Chem. Abstr.,72, 43474 (1970).
T. M. Speight and G. S. Avery, Drugs,3, 159–203 (1972).
A. K. Dixon, R. C. Hill, D. Rocmer, et al., Arzneim.-Forsch.,27, 1968–1979 (1977).
J. M. Bastian, A. Ebnother, E. Jucker, et al., Helv. Chim. Acta,54, 277–282 (1971).
U. S. Patent No. 3458522 (1969); Chem. Abstr.,71, 91466 (1969).
E. Waldvogel, G. Schwarb, J. M. Bastian, et al., Helv. Chim. Acta,59, 866–877 (1976).
West German Patent No. 2302944 (1973); Chem. Abstr.,79, 105088 (1973).
West German Patent No. 2302970 (1973); Chem. Abstr.,79, 105090 (1973).
Swiss Patent No. 544113 (1973); Chem. Abstr.,70, 82635 (1974).
West German Patent No. 2657769 (1977); Chem. Abstr.,87, 152032 (1977).
Austrian Patent No. 328445 (1976); Chem. Abstr.,85, 142973 (1976).
Swiss Patent No. 579077 (1976); Chem. Abstr.,85, 192578 (1976).
Polish Patent No. 106551 (1979); Chem. Abstr.,94, 3934 (1981).
West German Patent No. 2144490 (1972); Chem. Abstr.,77, 34296 (1972).
West German Patent No. 2605980 (1976); Chem. Abstr.,85, 192580 (1976).
U. Martin and D. Roemer, Monogr. Allergy,12, 145–149 (1977).
B. Wietrich, P. Radielovic, and M. Debelie, Int. J. Clin. Pharmacol.,16, 424–429 (1978).
K. V. Andersson and K. Hedman, Svensk. Farm. T.,82, 568–570 (1978).
M. Alhadeff, Med. Actual.,14, 367–373 (1978).
U. M. Ney, U. Bretz, U. Martin, et al., Res. Clin. Forums,4, 9–16 (1982).
U. Martin and D. Roemer, Triangle,17, 141–147 (1978).
E. L. Engelhardt, H. C. Zell, W. S. Saari, et al., J. Med. Chem.,8, 829–835 (1965).
Br. Patent No. 942877 (1963); Chem. Abstr.,60, 15839 (1964).
M. Alhadeff, Med. Actual.,13, 401–506 (1977); Chem. Abstr.,88, 114939 (1978).
U. S. Patent No. 3055903 (1962); Chem. Abstr.,58, 4527 (1963).
U. S. Patent No. 4021561 (1977); Chem. Abstr.,87, 84825 (1977).
Swiss Patent No. 433300 (1967); Chem. Abstr.,68, 95691 (1968).
French Patent No. 2290202 (1976); Chem. Abstr.,86, 121184 (1977).
Belgian Patent No. 617251 (1962); Chem. Abstr.,58, 12518 (1963).
Br. Patent No. 1153977 (1969); Chem. Abstr.,72, 3379 (1970).
European Patent Application No. 2902 (1980); Chem. Abstr.,92, 110854 (1980).
West German Patent No. 2629420 (1978); Chem. Abstr.,88, 105150 (1978).
U. S. Patent No. 4076714 (1978); Chem. Abstr.,89, 6234 (1978).
Br. Patent No. 1495890 (1977); Chem. Abstr.,89, 43116 (1978).
French Patent No. 2357251 (1978); Chem. Abstr.,89, 163419 (1978).
European Patent Application No. 5607 (1979); Chem. Abstr.,93, 8082 (1980).
French M. Patent No. 4424 (1966); Chem. Abstr.,68, 2814 (1968).
West German Patent No. 2256392 (1973); Chem. Abstr.,79, 66177 (1973).
French Patent No. 1392046 (1965); Chem. Abstr.,63, 1788 (1965).
French Patent No. 1499847 (1967); Chem. Abstr.,69, 1968 (1969).
Netherlands Patent Application No. 6411476 (1965); Chem. Abstr.,63, 13265 (1965).
Netherlands Patent Application No. 6512881 (1966); Chem. Abstr.,65, 8916 (1966).
French Patent No. 1441426 (1966); Chem. Abstr.,66, 95016 (1967).
U. S. Patent No. 4073912 (1978); Chem. Abstr.,89, 24156 (1978).
F. J. Villani, T. A. Mann, E. A. Wefer, et al., J. Med. Chem.,18, 1–8 (1975).
P. Nautka-Namirski, J. Piechaczek, and J. Wrotak, Acta Pol. Pharm.,34, 1–7 (1977).
West German Patent No. 2156235 (1972); Chem. Abstr.,77, 75203 (1972).
L. Diamond, G. K. Adams, B. Bleidt, et al., J. Pharmacol. Exp. Ther.,193, 256–263 (1975).
U. S. Patent No. 3966944 (1976); Chem. Abstr.,85, 87546 (1976).
French M. Patent No. 6265 (1968); Chem. Abstr.,74, 99722 (1971).
G. Engelhardt, Arzneim.-Forsch.,25, 1723–1737 (1975).
J. Kaehling, H. Ziegler, and H. Ballhause, Arzneim.-Forsch.,25, 1737–1744 (1975).
J. Maj, L. Baran, H. Sowinska, et al., Arch. Immunol. Ther. Exp.,24, 205–222 (1976).
B. Saletu, J. Grunberger, R. Flener, et al., Curr. Ther. Res.,20, 810–821 (1976).
J. Maj, H. Sowinska, and L. Baran, Arch. Immunol. Ther. Exp.,24, 197–203 (1976).
E. Zandarowska, J. Z. Novak, and B. Bielkievicz, Arch. Immunol. Ther. Exp.,28, 931–934 (1980).
M. Wielosz, E. Przegalinski, and Z. Kleinrok, Agressologie,20D, 253–257 (1979).
A. Clodera, D. Cenajek, and K. Mazurek, Arzneim.-Forsch.,31, 61–63 (1981).
E. Mogilinska and V. Klimek, J. Pharm. Pharmacol.,31, 704–705 (1979).
M. Wielosz, E. Przegalinski, and Z. Kleinrok, Pol. J. Pharmacol. Pharm.,30, 263–268 (1978).
J. Maj, E. Mogilinska, and V. Klimek, Pol. J. Pharmacol. Pharm.,30, 413–420 (1978).
U. S. Patent No. 2403483 (1946); Chem. Abstr.,40, 6505 (1946).
U. S. Patent No. 2404219 (1946); Chem. Abstr.,40, 6505 (1946).
French CAM Patent No. 204 (1968); Chem. Abstr.,72, 3382 (1970).
Netherlands Patent Application No. 6611868 (1967); Chem. Abstr.,68, 21845 (1968).
French M. Patent No. 4889 (1967); Chem. Abstr.,69, 52020 (1968).
French CAM Patent No. 0185 (1968); Chem. Abstr.,77, 5345 (1977).
Br. Patent No. 1134987 (1968); Chem. Abstr.,70, 77811 (1969).
French M. Patent No. 5465 (1967); Chem. Abstr.,71, 81186 (1969).
French M. Patent No. 4576 (1966); Chem. Abstr.,70, 3840 (1969).
French Addn. Patent No. 90605 (1968); Chem. Abstr.,71, 22038 (1969).
Netherlands Patent Application No. 6606860 (1966); Chem. Abstr.,67, 90680 (1967).
J. Fouche, J. C. Blondel, R. Horclois, et al., Bull. Soc. Chim. Fr.,9–10, 2697–2701 (1973).
U. S. Patent No. 3532702 (1970); Chem. Abstr.,74, 3681 (1971).
French Patent No. 1602883 (1971); Chem. Abstr.,79, 18780 (1973).
U. S. Patent No. 4045445 (1975); Chem. Abstr.,88, 6947 (1978).
Belgian Patent No. 632403 (1963); Chem. Abstr.,60, 15838 (1964).
U. S. Patent No. 3125578 (1964); Chem. Abstr.,60, 14483 (1964).
B. Hermans, P. Van Daele, C. Van de Westeringh, et al., J. Med. Chem.,11, 797–800 (1968).
P. A. J. Janssen and C. J. E. Niemegeers, Psychopharmacologia (Berl.),11, 231–254 (1967).
J. Van Wijngaarden, Life Sci.,8, 517–523 (1969).
P. A. J. Janssen, C. J. E. Niemegeers, K. H. L. Schellekens, et al., Arzneim.-Forsch., 1365–1373 (1971).
A. L. Spek, A. F. Peerdeman, J. Van Wijngaarden, et al., Nature,232, 375–376 (1971).
M. H. J. Koch and O. Dideberg, Acta Crystallogr.,29B, 369–371 (1973).
A. L. Spek, Acta Crystallogr.,32B, 870–877 (1976).
J. Van Wijngaarden and W. Soudijn, J. Labelled Comp.,1, 207–213 (1965).
J. Van Wijngaarden, Life Sci.,9, 489–500 (1970).
J. Van Wijngaarden, W. Soudijn, and C. Van der Eychen, Life Sci.,9, 1289–1302 (1970).
West German Patent No. 2053405 (1971); Chem. Abstr.,75, 35757 (1971).
U. S. Patent No. 3855729 (1974); Chem. Abstr.,82, 139966 (1975).
West German Patent No. 2053404 (1971); Chem. Abstr.,75, 35787 (1971).
West German Patent No. 2145320 (1972); Chem. Abstr.,77, 5343 (1972).
West German Patent No. 2303176 (1973); Chem. Abstr.,79, 105078 (1973).
V. J. Bauer, H. P. Dalalian, W. J. Fanshawe, et al., J. Med. Chem.,11, 981–985 (1968).
Jpn. Patent No. 7411710 (1974); Chem. Abstr.,81, 91556 (1974).
West German Patent No. 2408476 (1974); Chem. Abstr.,82, 43186 (1975).
West German Patent No. 2423835 (1974); Chem. Abstr.,82, 170693 (1975).
West German Patent No. 2653147 (1977); Chem. Abstr.,87, 84837 (1977).
Swiss Patent No. 592656 (1977); Chem. Abstr.,88, 50662 (1978).
Swiss Patent No. 605924 (1978); Chem. Abstr.,90, 87281 (1979).
Swiss Patent No. 610588 (1979); Chem. Abstr.,91, 211251 (1979).
Swiss Patent No. 611618 (1979); Chem. Abstr.,91, 123635 (1979).
Swiss Patent No. 611617 (1979); Chem. Abstr.,91, 107900 (1979).
Swiss Patent No. 611619 (1979); Chem. Abstr.,91, 107902 (1979).
Swiss Patent No. 605924 (1979); Chem. Abstr.,92, 6428 (1980).
Swiss Patent No. 613450 (1979); Chem. Abstr.,92, 76303 (1980).
Swiss Patent No. 605927 (1978); Chem. Abstr.,90, 72062 (1979).
Swiss Patent No. 605926 (1978); Chem. Abstr.,90, 72063 (1979).
Swiss Patent No. 613452 (1979); Chem. Abstr.,92, 215281 (1980).
West German Patent No. 2537837 (1976); Chem. Abstr.,84, 180070 (1976).
Swiss Patent No. 609978 (1979); Chem. Abstr.,91, 56828 (1979).
Swiss Patent No. 609979 (1979); Chem. Abstr.,91, 39334 (1979).
Swiss Patent No. 609980 (1979); Chem. Abstr.,91, 39335 (1979).
U. S. Patent No. 4259338 (1981); Chem. Abstr.,95, 61971 (1981).
Br. Patent No. 2056435 (1981); Chem. Abstr.,95, 150414 (1981).
West German Patent No. 2738646 (1978); Chem. Abstr.,89, 6229 (1978).
European Patent Application No. 3199 (1979); Chem. Abstr.,92, 94236 (1980).
West German Patent No. 2951912 (1980); Chem. Abstr.,93, 239245 (1980).
West German Patent No. 3026365 (1981); Chem. Abstr.,94, 156767 (1981).
K. Freter, J. Org. Chem.,40, 2525–2529 (1975).
J. Bergman, J. Heterocycl. Chem.,7, 1071–1076 (1970).
European Patent Application No. 4494 (1979); Chem. Abstr.,92, 128936 (1980).
French Patent No. 2457290 (1980); Chem. Abstr.,95, 80984 (1981).
West German Patent No. 2719294 (1972); Chem. Abstr.,88, 62398 (1978).
Belgian Patent No. 854112 (1977); Chem. Abstr.,90, 137836 (1979).
French Patent No. 2391211 (1978); Chem. Abstr.,92, 22511 (1980).
West German Patent No. 2338283 (1974); Chem. Abstr.,80, 120790 (1974).
West German Patent No. 2322470 (1974); Chem. Abstr.,82, 57565 (1975).
Austrian Patent No. 332401 (1976); Chem. Abstr.,86, 89618 (1977).
West German Patent No. 2502326 (1975); Chem. Abstr.,83, 193353 (1975).
West German Patent No. 2503816 (1974); Chem. Abstr.,83, 193099 (1975).
U. S. Patent No. 4267185 (1981); Chem. Abstr.,95, 97600 (1981).
West German Patent No. 2456246 (1975); Chem. Abstr.,83, 163998 (1975).
V. Paragamian and J. F. Gardocki, J. Med. Chem.,11, 1064–1066 (1968).
R. S. Vartanyan, Khim.-farm. Zh., No. 5, 540–550 (1983).
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Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 18, No. 11, pp. 1294–1309, November, 1984.
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Vartanyan, R.S. Synthesis and biological activity of uncondensed cyclic derivatives of piperidine (review). Pharm Chem J 18, 736–749 (1984). https://doi.org/10.1007/BF00779895
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DOI: https://doi.org/10.1007/BF00779895