Literature cited
S. K. Dickerman and H. G. Lindwall, J. Org. Chem.,14, 530–536 (1949).
R. Tomita, J. Pharm. Soc. Jpn.,71, 1053–1059 (1951).
K. Tomita, Pharmazie,7, 497–498 (1952).
K. Hohenlohe-Oehringer, Monatsh.,94, 1222–1224 (1963).
I. N. Nazarov, S. G. Matsoyan, and V. A. Rudenko, Izv. Akad. Nauk SSSR Otd. Khim. Nauk, 1069–1074 (1952).
B. Gutkowska, Acta Pol. Pharm.,31, 735–738 (1974).
H. Piotowska, W. Sas, and J. Winiazski, Rocz. Chem.,51, 2417–2420 (1977).
H. G. Wechen, R. I. Russev, and P. Held, J. Prakt. Chem.,321, 865–869 (1979).
H. G. Werchen, R. I. Rusev, P. Held, et al., Z. Chem.,20, 56–57 (1980).
N. F. Kucherova, L. A. Aksenova, L. M. Sharkova, et al., Khim. Geterotsikl. Soedin., 1469–1472 (1971).
C. Harris, Ann.,417, 107–146 (1918).
P. Brookes, R. J. Terry, and J. Walker, J. Chem. Soc, 3165–3172 (1957).
Fr. Pat. No. 1434489 (1966); Chem. Abstr.,66, 26875 (1967).
Fr. Pat. No. 1542649 (1968); Chem. Abstr.,71, 124400 (1969).
Ger. Pat. No. 2731299 (1978): Chem. Abstr.,88, 136657 (1978).
Jpn. Pat. No. 7802475 (1978); Chem. Abstr.,89, 43120 (1978).
N. I. Harper and C. F. Chignall, J. Med. Chem.,7, 729–732 (1964).
L. Zhelyazkov, N. Bikova, L. Krcheteva, et al., Sb. Tr. NIKhFI (Sofia),7, 55–67 (1972).
B. Emmert and W. Dorn, Chem. Ber.,48, 687–692 (1915).
E. Koenigs and L. Neumann, Chem. Ber.,48, 956–963 (1915).
L. Orthnier, Ann.,456, 225–252 (1927).
J. N. Walker, M. A. Moore, and B. N. Beaver, J. Org. Chem.,26, 2740–2747 (1961).
J. N. Walker and M. A. Moore, J. Org. Chem.,26, 432–439 (1961).
L. N. Yakhontov, S. V. Yachenko, and M. V. Rubtsov, Zh. Obshch. Khim.,28, 3115–3119 (1958).
E. Cerkovnikov and V. Prelog, Chem. Ber.,74, 1648–1658 (1941).
V. Hahn, E. Cerkovnikov, and V. Prelog, Helv. Chim. Acta,26, 1132–1142 (1943).
V. Hahn, E. Cerkovnikov, and V. Prelog, Chem. Ber.,74, 1658–1660 (1941).
N. S. Prostakov, N. N. Mikheeva, and D. Pkhal'gumani, Khim. Geterotsikl. Soedin.,4, 671–673 (1967).
S. Afr. Pat. No. 6701679 (1968); Chem. Abstr.,70, 106395 (1969).
R. C. Fuson, W. E. Parham, and L. J. Reed, J. Am. Chem. Soc,68, 1239–1240 (1946).
R. H. Reitsema and J. H. Hunter, J. Am. Chem. Soc,70, 4009–4011 (1948).
J. Colonge, G. Descotes, and G. Fresnay, Compt. Rend.,256, 2638–2639 (1963).
J. Colonge, G. Descotes, and G. Fresnay, Bull. Soc. Chim. Fr., 2264–2270 (1963).
Br. Pat. No. 1122110 (1968); Chem. Abstr.,69, 106572 (1968).
Fr. Pat. No. 1344366 (1963); Chem. Abstr.,61, 3076 (1963).
Fr. M. Pat. No. 2430 (1964); Chem. Abstr.,62, 14634 (1964).
Fr. Pat. No. 1434489 (1966); Chem. Abstr.,66, 28675 (1967).
Fr. Pat. No. 1517670 (1968); Chem. Abstr.,71, 13026 (1969).
A. F. Casy, M. M. A. Hassan, A. B. Simmonds, et al., J. Pharm. Pharmacol.,21, 434–440 (1969).
Swiss Pat. No. 535767 (1973); Chem. Abstr.,79, 42359 (1973).
E. S. Nikitskaya, G. S. Arutyunyan, M. D. Mashkovskii, et al., Khim.-farm. Zh., No. 2, 16–21 (1974).
I. Van Wiingarden and Sindgin, Life Sci.,7, 1239–1244 (1968).
U.S. Pat. No. 3655675 (1972); Chem. Abstr.,77, 34349 (1972).
U.S. Pat. No. 3763168 (1973); Chem. Abstr.,80, 47860 (1974).
Swiss Pat. No. 528507 (1972); Chem. Abstr.,78, 58251 (1973).
S. Grobmann, U. Moser, and E. Mutschler, Arch. Pharm.,311, 1010–1015 (1978).
Hung. Pat. No. 157325 (1970); Chem. Abstr.,73, 25305 (1970).
U.S. Pat. No. 2683714 (1954); Chem. Abstr.,49, 10383 (1955).
Br. Pat. No. 700097 (1953); Chem. Abstr.,49, 6318 (1955).
U. S. Pat. No. 3691176 (1972); Chem. Abstr.,77, 151984 (1972).
U. S. Pat. No. 3686187 (1972); Chem. Abstr.,77, 139829 (1972).
I. I. Nazarov and V. A. Rudenko, Zh. Obshch. Khim.,22, 623–632 (1952).
P. Brookes, R. J. Terry, and J. Walker, J. Chem. Soc, 3165–3172 (1957).
U. S. Pat. No. 2496955 (1950); Chem. Abstr.,44, 5397 (1950).
U. S. Pat. No. 2496956 (1950); Chem. Abstr.,44, 5397 (1950).
U. S. Pat. No. 2496957 (1950); Chem. Abstr.,44, 5397 (1950).
U. S. Pat. No. 2496958 (1950); Chem. Abstr.,44, 5398 (1950).
U. S. Pat. No. 2476914 (1949); Chem. Abstr.,44, 4043 (1950).
U. S. Pat. No. 2476913 (1949); Chem. Abstr.,44, 1143 (1950).
U. S. Pat. No. 2476912 (1949); Chem. Abstr.,44, 1143 (1950).
U. S. Pat. No. 3480635 (1969); Chem. Abstr.,72, 3163 (1970).
I. N. Nazarov and E. T. Golovin, Zh. Obshch. Khim.,26, 1496–1507 (1956).
J. L. Hughes and J. K. Sayler, J. Med. Chem.,14, 894–895 (1971).
U. S. Pat. No. 718124 (1941); Chem. Abstr.,44, 4045 (1950).
U. S. Pat. No. 2485162 (1949); Chem. Abstr.,44, 4045 (1950).
Jpn. Pat. No. 7797978, 199 (1977); Chem. Abstr.,88, 89666 (1978).
Pol. Pat. No. 69950 (1974); Chem. Abstr.,81, 91368 (1974).
B. Gutkowska, Acta. Pol. Pharm.,34, 241–244 (1977).
Ger. Pat. No. 2302717 (1973); Chem. Abstr.,79, 136989 (1973).
Jpn. Pat. No. 7787176 (1977); Chem. Abstr.,88, 37793 (1978).
Ger. Pat. No. 891547 (1953); Chem. Abstr.,52, 13805 (1958).
U. S. Pat. No. 2757175 (1956); Chem. Abstr.,51, 2055 (1957).
Br. Pat. No. 717227 (1954); Chem. Abstr.,50, 2864 (1956).
Pol. Pat. No. 65775 (1972); Chem. Abstr.,77, 151949 (1972).
M. N. Aboul-Enein, M. Khalifa, and A. A. El-Azonny, Pharm. Acta Helv.,48, 151–156 (1973).
B. Gutkowska, Rocz. Chem.,48, 1081–1082 (1974).
Swiss Pat. No. 602705 (1978); Chem. Abstr.,89, 215223 (1978).
N. S. Prostakov, N. N. Mikheeva, and S. Ya. Govor, Khim. Geterotsikl. Soedin., 945–947 (1969).
Br. Pat. No. 1530931 (1978); Chem. Abstr.,90, 186803 (1979).
Br. Pat. No, 1486104 (1977); Chem. Abstr.,88, 22653 (1978).
Br. Pat. No. 1470357 (1970); Chem. Abstr.,74, 111918 (1971).
Ger. Pat. No. 2705949 (1977); Chem. Abstr.,88, 6727 (1978).
Belg. Pat. No. 860139 (1978); Chem. Abstr.,89, 109105 (1978).
Br. Pat. No. 1514151 (1978); Chem. Abstr.,89, 215230 (1978).
Ger. Pat. No. 2247960 (1978); Chem. Abstr.,89, 109112 (1978).
Ger. Pat. No. 2751181 (1978); Chem. Abstr.,89, 109117 (1978).
Ger. Pat. No. 2751138 (1978); Chem. Abstr.,89, 109118 (1978).
Ger. Pat. No. 2751139 (1978); Chem. Abstr.,89, 109119 (1978).
Br. Pat. No. 1507463 (1978); Chem. Abstr.,90, 22817 (1979).
Span. Pat. No. 470772 (1979); Chem. Abstr.,91, 74482 (1979).
A. Jonczyk, M. Jawdosiuk, M. Makosza, et al., Przem. Chem.,57, 131–134 (1978).
A. Jonczyk, M. Jawdosiuk, and M. Makosza, Przem. Chem.,57, 180–182 (1978).
Ger. Pat. No. 1938512 (1971); Chem. Abstr.,74, 87840 (1971).
U. S. Pat. No. 3647805 (1972); Chem. Abstr.,76, 140556 (1972).
U. S. Pat. No. 3531487 (1970); Chem. abstr.,74, 53547 (1971).
Swiss Pat. No. 602706 (1978); Chem. Abstr.,89, 215222 (1978).
Ger. Pat. No. 2710714 (1977); Chem. Abstr.,88, 6729 (1978).
Br. Pat. No. 1537867 (1979); Chem. Abstr.,91, 74474 (1979).
Ger. Pat. No. 2718405 (1977); Chem. Abstr.,90, 87285 (1979).
Ger. Pat. No. 2341229 (1974); Chem. Abstr.,80, 133438 (1974).
Jpn. Pat. No. 7785174 (1977); Chem. Abstr.,88, 22640 (1978).
N. S. Prostakov, N. A. Mikheeva, and S. K. Banerdzhi, Khim. Geterotsikl. Soedin., 273–274 (1968).
P. Stern, Arch. Exp. Path. Pharmakol.,199, 251–264 (1942).
A. Krauchaar, Arzneim.-Forsch.,1, 157–160 (1950).
A. Kraushaar, Dtsch. Med. Wschr.,75, 1148–1149 (1950).
H. John, Arzneim.-Forsch.,2, 250–251 (1952).
E. Rothlin and A. Cerletti, Ann. Allergy,13, 80–89 (1955).
Ger. Pat. No. 955541 (1957); Chem. Abstr.,53, 18399 (1959).
S. L. Agarwal and R. B. Arora, Ind. J. Med. Res.,48, 451–456 (1960).
F. Gregoire, M. Comean, and L. Roy, Un. Med. Can.,89, 173–181 (1960).
H. Calvin, Toxicol. Appl. Pharmacol.,3, 393–401 (1961).
C. M. Smith and P. D. Luna, J. Med. Chem.,14, 894–895 (1971).
Fr. Pat. No. 2121423 (1973); Chem. Abstr.,78, 136–315 (1973),
Jpn. Pat. No. 7029823 (1970); Chem. Abstr.,74, 22709 (1971).
Swiss Pat. No. 535767 (1973); Chem. Abstr.,79, 42359 (1973).
Br. Pat. No. 1000686 (1965); Chem. Abstr.,63, 13279 (1965).
Br. Pat. No. 1278166 (1972); Chem. Abstr.,77, 101–395 (1972).
Jpn. Pat. No. 7211231 (1972); Chem. Abstr.,77, 34356 (1972).
Jpn. Pat. No. 7342876 (1973); Chem. Abstr.,81, 63499 (1974).
Jpn. Pat. No. 7343746 (1973); Chem. Abstr.,81, 13527 (1974).
Jpn. Pat. No. 7342877 (1973); Chem. Abstr.,81, 49576 (1974).
Br. Pat. No. 991509 (1965); Chem. Abstr.,63, 16313 (1965).
Ger. Pat. No. 2403786 (1974); Chem. Abstr.,82, 72791 (1974).
Ger. Pat. No. 2901336 (1980); Chem. Abstr,93, 204468 (1980).
Ger. Pat. No. 2922159 (1980); Chem. Abstr.,94, 156971 (1981).
Jpn. Pat. No. 7686476 (1976); Chem. Abstr.,86, 72466 (1977).
Jpn. Pat. No. 8040656 (1980); Chem. Abstr.,93, 239259 (1977).
Jpn. Pat. No. 76105096 (1976); Chem. Abstr.,86, 189992 (1977).
Jpn. Pat. No. 6465(65) (1962); Chem. Abstr.,63, 1772 (1965).
U. S. Pat. No. 3883539 (1975); Chem. Abstr.,83, 131472 (1975).
U. S. Pat. No. 3147268 (1968); Chem. Abstr.,61, 13287 (1964).
Fr. Pat. No. 2157692 (1973); Chem. Abstr.,79, 146414 (1973).
Br. Pat. No. 1530931 (1978); Chem. Abstr.,90, 186803 (1979).
U. S. Pat. No. 3879401 (1975); Chem, Abstr.,83, 79085 (1975).
U. S. Pat. No. 3910932 (1975); Chem. Abstr.,84, 4823 (1976).
Br. Pat. No. 1507463 (1978); Chem. Abstr.,90, 22817 (1979).
U. S. Pat. No. 4105771 (1978); Chem. Abstr.,90, 54835 (1979).
U. S. Pat. No. 4105666 (1978); Chem. Abstr.,90, 38799 (1979).
Br. Pat. No. 1532671 (1978); Chem. Abstr.,90, 203877 (1979).
U. S. Pat. No. 3879401 (1975); Chem. Abstr.,83, 79085 (1975).
Br. Pat. No. 1538542 (1979); Chem. Abstr.,91, 91507 (1979).
Ger. Pat. No. 2831447 (1980); Chem. Abstr.,93, 8035 (1980).
Ger. Pat. No. 2919194 (1980); Chem. Abstr.,94, 3940 (1981).
Ger. Pat. No. 2910195 (1980); Chem. Abstr.,94, 15595 (1981).
Br, Pat. No. 1413708 (1975); Chem. Abstr.,84, 89997 (1976).
Br. Pat. No. 1532671 (1978); Chem. Abstr.,90, 203877 (1979).
U. S. Pat. No. 3910932 (1975); Chem. Abstr.,84, 4823 (1976).
Ger. Pat. No. 2513136 (1976); Chem. Abstr.,84, 30108 (1976).
Br. Pat. No. 1423591 (1976); Chem. Abstr.,84, 180063 (1976).
U. S. Pat. No. 3910931 (1975); Chem. Abstr.,84, 43866 (1976).
Ger. Pat. No. 2423897 (1975); Chem. Abstr.,86, 59225 (1976).
Ger. Pat. No. 2831431 (1980); Chem. Abstr.,93, 8034 (1980).
U. S. Pat. No. 3462242 (1969); Chem. Abstr.,71, 91343 (1969).
U. S. Pat. No. 3452030 (1969); Chem. Abstr.,71, 81202 (1969).
U. S. Pat. No. 3869463 (1975); Chem. Abstr.,83, 58661 (1975).
Br. Pat. No. 1410783 (1975); Chem. Abstr.,84, 43873 (1976).
Br. Pat. No. 1411782 (1975); Chem. Abstr.,84, 43875 (1976).
Br. Pat. No. 1411783 (1975); Chem. Abstr.,84, 43876 (1976).
U. S. Pat. No. 3907813 (1975); Chem. Abstr.,84, 48–21 (1976).
U. S. Pat. No. 3907811 (1975); Chem. Abstr.,84, 4822 (1976).
Z. Shen-Hus and W. Wan-kung, J. Chin. Chem. Soc. (Taipei),27, 147–149 (1980); Chem. Abstr.,94, 174821 (1981).
E. Carmeliet, P. A. Janssen, R. Marsboom, et al., Arch. Int. Pharmacodynam.,231, 104–130 (1978).
U. Klotz, P. Mueller-Scidlitz, and P. Heinburg, Clin. Pharmacodyn.,3, 407–418 (1978).
Ger. Pat. No. 2642856 (1977); Chem. Abstr.,87, 53094 (1977).
Ger. Pat. No. 2551235 (1976); Chem. Abstr.,85, 44240 (1976).
Ger. Pat. No. 2545501 (1976); Chem. Abstr.,85, 32864 (1976).
Ger. Pat. No. 2505500 (1975); Chem. Abstr.,85, 43855 (1976).
Aust. Pat. No. 500990 (1979); Chem. Abstr.,91, 211272 (1979).
Eur. Pat. No. 2886 (1979); Chem. Abstr.,92, 94237 (1980).
Ger. Pat. No. 2423897 (1975); Chem. Abstr.,84, 59225 (1976).
Ger. Pat. No. 2718405 (1977); Chem. Abstr.,90, 87285 (1979).
Jpn. Pat. No. 7249064 (1972); Chem. Abstr.,78, 111138 (1973).
Swiss Pat. No. 350650 (1956); Chem. Abstr.,56, 1435 (1962).
Swiss Pat. No. 347525 (1956); Chem. Abstr.,55, 16572 (1961).
A. Ednother, E. Jucker, A. Lindemann, et al., Helv. Chim. Acta,42, 533–563 (1953).
U. S. Pat. No. 2959593 (1960); Chem. Abstr.,55, 9430 (1961).
J. E. Robertson. J. H. Biel, and F. Diliero, J. Med. Chem.,6, 381–384 (1963).
Belg. Pat. No. 642315 (1965); Chem. Abstr.,63, 6979 (1965).
U. S. Pat. No. 3793333 (1974); Chem. Abstr.,80, 120792 (1974).
A. Ebnother, E. Jicker, E. Rissi, et al., Helv. Chim. Acta,42, 2013–2035 (1959).
U. S. Pat. No. 2865922 (1958); Chem. Abstr.,53, 8168 (1959).
U. S. Pat. No. 2955112 (1960); Chem. Abstr.,57, 2199 (1962).
A. Ebnother, E. Jucker, E. Rissi, et al., Helv. Chim. Acta,42, 918–955 (1959).
Swiss Pat. No. 367177 (1963); Chem. Abstr.,60, 529 (1964).
Br. Pat. No, 889033 (1962); Chem. Abstr.,57, 3451 (1962).
Swiss Pat. No. 346885 (1960); Chem. Abstr.,58, 5965 (1963).
U. S. Pat. No. 2903460 (1960); Chem. Abstr.,54, 11053 (1960).
Neth. Pat. No. 6409687 (1965); Chem. Abstr.,63, 11569 (1963).
Er. M. Pat. No. 1698 (1963); Chem. Abstr.,59, 11503 (1963).
U. S. Pat. No. 3041343 (1962); Chem. Abstr.,57, 13764 (1962).
Ger. Pat. No. 1116674 (1961); Chem. Abstr.,56, 12907 (1961).
U. S. Pat. No. 3041342 (1962); Chem. Abstr.,57, 13766 (1962).
Br. Pat. No. 858792 (1961); Chem. Abstr.,55, 14491 (1961).
Swiss Pat. No. 441310 (1968); Chem. Abstr.,69, 35964 (1968).
Swiss Pat. No. 357720 (1961); Chem. Abstr.,57, 11172 (1962).
Br. Pat. No. 1005723 (1965); Chem. Abstr.,64, 714 (1965).
U. S. Pat. No. 3745163 (1973); Chem. Abstr.,79, 78621 (1973).
Ger. Pat. No. 2135170 (1972); Chem. Abstr.,77, 5455 (1972).
Belg. Pat. No. 626307 (1963); Chem. Abstr.,60, 10689 (1964).
Er. Pat. No. 1344366 (1963); Chem. Abstr.,61, 1871 (1964).
U. S. Pat. No. 3161645 (1964); Chem. Abstr.,63, 2980 (1965).
U. S. Pat. No. 3225052 (1965); Chem. Abstr.,64, 8194 (1966).
Belg. Pat. No. 663433 (1965); Chem. Abstr.,65, 722 (1966).
Belg. Pat. No. 666432 (1965); Chem. Abstr.,65, 722 (1966).
U. S. Pat. No. 3318900 (1967); Chem. Abstr.,67, 8661 (1967).
U. S. Pat. No. 3712898 (1973); Chem. Abstr.,78, 97659 (1973).
Jpn. Pat. No. 7300474 (1973); Chem. Abstr.,78, 124586 (1973).
Ger. Pat. No. 2313258 (1973); Chem. Abstr.,79, 146409 (1973).
U. S. Pat. No. 3723441 (1973); Chem. Abstr.,79, 32058 (1973).
Jpn. Pat. No. 7805174 (1978); Chem. Abstr.,88, 109828 (1978).
Jpn. Pat. No. 7991874 (1977); Chem. Abstr.,88, 50658 (1978).
Jpn. Pat. No. 7797978 (1977); Chem, Abstr.,88, 89666 (1978).
Jpn. Pat. No. 7787176 (1977); Chem. Abstr.,88, 37793 (1978).
Jpn. Pat. No. 77131582 (1977); Chem. Abstr.,88, 105339 (1978).
M. Sato, H. Arimoto, K. Ueno, et al., J. Med. Chem.,21, 1116–1120 (1978).
Jpn. Pat. No. 7584579 (1975); Chem. Abstr.,84, 31059 (1976).
Belg. Pat. No. 830171 (1975); Chem. Abstr.,85, 16009 (1976).
Jpn. Pat. No. 76136673 (1976); Chem. Abstr.,86, 189933 (1977).
Jpn. Pat. No. 7823978 (1978); Chem. Abstr.,90, 6394 (1969).
M. Sato, M. Kitagawa, F. Uchimazu, et al., Chem. Pharm. Bull (Tokyo),27, 119–152 (1979).
Ger. Pat. No. 2607300 (1976); Chem. Abstr.,86, 29816 (1977).
Jpn. Pat. No. 7643764 (1976); Chem. Abstr.,86, 5456 (1977).
Jpn. Pat. No. 76136676 (1976); Chem. Abstr.,87, 53289 (1977).
Jpn. Pat. No. 76131879 (1976); Chem. Abstr.,87, 5967 (1977).
U. S. Pat. No. 4083755 (1978); Chem. Abstr.,89, 197539 (1978).
Swiss Pat. No. 603629 (1978); Chem. Abstr.,89, 180003 (1978).
U. S. Pat. No. 3838118 (1974); Chem. Abstr.,83, 79239 (1975).
Ger. Pat. No. 2265094 (1976); Chem. Abstr.,85, 33016 (1976).
Jpn. Pat. No. 7446285 (1974); Chem. Abstr.,83, 10083 (1975).
Ger. Pat. No. 2924064 (1979); Chem. Abstr.,94, 208866 (1981).
Jpn. Pat. No. 80585 (1980); Chem. Abstr.,94, 47325 (1981).
Ger. Pat. No. 2638705 (1977); Chem. Abstr.,87, 102325 (1977).
Ger. Pat. No. 2632870 (1977); Chem. Abstr.,87, 23274 (1977).
Jpn. Pat. No. 7936276 (1979); Chem. Abstr.,91, 39481 (1979).
Eur. Pat. No. 0485 (1979); Chem. Abstr.,92, 41948 (1980).
Ger. Pat. No. 2701794 (1977); Chem. Abstr.,87, 152208 (1977).
Jpn. Pat. No. 8024155 (1980); Chem. Abstr.,93, 186387 (1980).
Jpn. Pat. No. 7431673 (1974); Chem. Abstr.,81, 105507 (1974).
V. Kleim, W. Besk, and E. Mutschler, Arch. Pharm.,307, 360–366 (1974).
Ger. Pat. No. 2533567 (1976); Chem. Abstr.,85, 464–23 (1976).
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Translated from Khimiko-farmatsevticheskii Zhurnal, Vol. 17, No. 5, pp. 540–550, May, 1983.
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Vartanyan, R.S. 4-N-substituted piperidines (review). Pharm Chem J 17, 329–338 (1983). https://doi.org/10.1007/BF00765637
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DOI: https://doi.org/10.1007/BF00765637