Abstract:
A piperidine compound of the formula (I): ##STR1## wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH 2 ) n , which may be substituted, in which n is 0 or an integer of 1 to 10, --CH═CH--, --C═C--, --O--, --S--, --NH--, --N(COCH 3 )--, --N(COOC 2  H 5 )--, --N(CHO)--, --N(CH 3 )--, --CO--, --SO--, or --SO 2  --; Y is --CH═CH--, --CH 2  CH 2  --, --CH 2  CO--, --O--, --S--, --NH--, --OCH 2  --, --SCH 2  --, --NHCH 2  --, --CH(OH)CH 2  -- or --CH(OH)CH(OH)--; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the --(CH 2 )-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH═CH--, --C═C--, --O--, --S--, --NH--, --N(COCH 3 ), --N(COC 2  H 5 )--, --N(CHO)--, --N(CH 3 )--, --CO--, --SO-- or --SO 2  --, and wherein one or more of the --(CH 2 )-groups in X and Q may be substituted by --(CH 2 ) 4  -- or --(CH 2 ) 5  -- thereby forming a ring structure.

Description:
CROSS REFERENCE TO RELATED APPLICATIONS 
     This application is a continuation-in-part of application Ser. No. 07/443,438 filed Nov. 30, 1989, now abandoned, which is a continuation-in-part of application Ser. No. 07/354,880 filed May 22, 1989 which is a continuation-in-part of abandoned application Ser. No. 07/201,911 filed Jun. 2, 1988, now abandoned. 
    
    
     BACKGROUND OF THE INVENTION 
     1. Field of the Invention 
     The present invention relates to a piperidine derivative and hypotensives containing the same. 
     2. Description of the Background 
     It is said that there are about 13,000,000 patients with hypertension in Japan and its frequency of occurrence in individuals becomes greater with advancing age. Further, as the age of a given population increases, increased attention is directed to hypertension which becomes more and more of a dangerous factor in severe heart and cerebral diseases represented by cardiac infarction and cerebral apoplexy. In recent years, calcium antagonists or angiotensin convertase inhibitors have been widely used as excellent primary selection drugs for treatment of hypertension. But the pharmaceutical effects or safety of these hypotensives have recently come into question. 
     A need therefore continues to exist for new hypotensive agents which exhibit excellent pharmaceutical effects and safety which can be industrially prepared at low cost and in a simple manner. 
     SUMMARY OF THE INVENTION 
     Accordingly, one object of the present invention is to provide an effective hypotensive agent which is relatively simple to prepare at low cost. 
     Briefly, this object and other objects of the present invention as hereinafter will become more readily apparent can be attained by a piperidine derivative of formula (I): ##STR2## wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH 2 ) n , whch may be substituted, in which n is 0 or an integer of 1 to 10, --CH═CH--, --C═C--, --O--, --S--, --NH--, --N(COCH 3 )--, --N(COOC 2  H 5 )--, --N(CHO)--, --N(CH 3 )--, --CO--, --SO-- or --SO 2  --; Y is --CH═CH--, --CH 2  CH 2  --, --CH 2  CO--, --O--, --S--, --NH--, --OCH 2  --, --SCH 2  --, --NHCH 2  --, --CH(OH)CH 2  -- or --CH(OH)CH(OH)--; and Q is substituted or unsubstituted n-hexyl, carboxypropyl, ethoxycarbonylpropyl, cyanopropyl, cyclohexyl, phenyl, indanyl, naphthyl, tetrahydronaphthyl, benzocycloheptyl, piperidinyl, tetrahydroisoquinolinyl, indolyl, pyrolyl, furyl, thienyl, thiazolyl, oxazolyl or N-methylpyrolyl, wherein any one or more of the --(CH 2 )-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH═CH--, --C═C--, --O--, --S--, --NH--, --N(COCH 3 ), --N(COC 2  H 5 )--, --N(CHO)--, --N(CH 3 )--, --CO--, --SO-- or --SO 2  --, and wherein one or more of the --(CH 2 )-groups in X and Q may be substituted by --(CH 2 ) 4  -- or --(CH 2 ) 5  -- thereby forming a ring structure. 
    
    
     DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS 
     It has now been discovered that piperidine derivatives of the formula (I) above are effective as hypotensive agents. The present piperidine derivative exhibits excellent hypotensive action, its method of synthesis is simple and its derivatives can be easily prepared. 
     In formula (I), the fused aromatic ring (A) is a fused benzene, thiophene, pyridine or the like ring. Further, in formula (I) above, substituents X and Q may be substituted by at least one substituent selected from the group consisting of H(CH 2 ) n , wherein n is 1 to 10, Cl(CH 2 ) 3 , allyl phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, ethoxycarboxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, cyano, imidazolylmethyl, trifluoromethyl, benzoyl, 2-hydroxybenzyl, nitro, amino, acetylamino, propanoylamino, butanoylamino, pivaloylamino, trifluoromethylamino, methoxycarbonylamino, ethoxycarbonylamino, cinnamoylamino, methanesulfonylamino, N,N-bis(methanesulfonyl)amino, aminocarbonyl, aminosulfonyl, hydroxymethyl and acetoxymethyl. 
     The method of administration of the present piperidine derivative when used as a hypotensive, include oral and parenteral routes. Dose is determined depending upon age, body weight and condition of the patient and route of administration. Daily dose is generally 0.01 to 2000 mg/kg for oral administration. In the case of parenteral administration, the daily dose is 0.01 to 1000 mg/kg. The present piperidine derivative may be prepared in the form of ordinary preparations such as for example, tablets, powders, capsules, solutions, sugar-coated tablets or depots, which may be prepared in a conventional manner using conventional preparation aids. For example, tablets can be obtained by mixing the piperidine derivative of the present invention diluents (e.g., lactose, calcium carbonate or calcium phosphate), binders (e.g., gum arabic, corn starch or gelatin), swelling agents (e.g., alginic acid, corn starch or pregelinated starch), sweeteners (e.g., sucrose or saccharin), flavors (e.g., peppermint, Gaultheria adenothrix oil or cherry), lubricating and wetting agents (e.g., magnesium stearate, talc or carboxymethyl cellulose). 
     Having now generally described this invention, a further understanding can be obtained by reference to certain specific examples which are provided herein for purposes of illustration only and are not intended to be limited unless otherwise specified. 
     Unless otherwise indicated, the developing conditions for silica gel TLC procedures were under chloroform/methanol=9/1. Mass spectra (MS) were performed in the FD mode (m/z) and nuclear magnetic resonance spectra (NMR) were measured using tetramethylsilane as the internal standard and CDCl 3  as the solvent. 
     EXAMPLE 1 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-hexylpiperidine hydrochloride 
     A solution of 273 mg (1 mmol) of 4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-hexylpiperidine, 165 mg (1 mmol) of 1-bromohexane, 745 mg (5 mmols) of sodium iodide and 414 mg (3 mmols) of potassium carbonate in 20 ml of methyl isobutyl ketone was stirred and refluxed at 120° C. overnight on an oil bath. After the reaction, the mixture was washed by adding 20 ml of water thereto. Then the organic phase was separated and the solvent was distilled off under reduced pressure. After purifying by silica gel column chromatography (eluent: methanol/chloroform, 1/100-1/50), the product was converted into the hydrochloride with an equimolar hydrogen chloride/dioxane solution. 
     Amount yielded 180 mg 
     Yield 46% 
     TLC Rf=0.68 
     MS 357 (M+) 
     NMR 0.83 (3H, t), 1.2-1.4 (6H, m), 1.7-1.9 (2H, m), 2.31 (2H, dd), 2.53 (2H, d), 2.7-2.8 (2H, m), 3.14 (2H, dd), 3.38 (2H, dd), 3.38 (2H, d), 6.92 (2H, s), 7.2-7.4 (8H, m) 
     Hereafter procedures were carried out in a manner similar to Example 1. 
     EXAMPLE 2 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-octylpiperidine hydrochloride 
     Amount yielded 300 mg 
     Yield 72% 
     TLC Rf=0.71 
     MS 385 (M+) 
     NMR 0.85 (3H, t), 1.2-1.4 (10H, m), 1.7-2.0 (2H, m), 2.30 (2H, dd), 2.53 (2H, d), 2.7-2.9 (2H, m), 3.13 (2H, dd), 3.38 (2H, d), 6.90 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 3 
     1-Decyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 
     Amount yielded 300 mg 
     Yield 67% 
     TLC Rf=0.75 
     MS 413 (M+) 
     NMR 0.85 (3H, t), 1.2-1.4 (14H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.54 (2H, d), 2.7-2.8 (2H, m), 3.15 (2H, dd), 3.39 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 4 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-dodecylpiperidine hydrochloride 
     Amount yielded 1.10 g 
     Yield 92% 
     TLC Rf=0.78 
     MS 441 (M+) 
     NMR 0.85 (3H, t), 1.1-1.5 (18H, m), 1.7-1.9 (2H, m), 2.32 (2H, dd), 2.54 (2H, d), 2.7-2.8 (2H, m), 3.12 (2H, dd), 3.36 (2H, d), 6.93 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 5 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-tetradecylpiperidine hydrochloride 
     Amount yielded 1.20 g 
     Yield 95% 
     TLC Rf=0.78 
     MS 469 (M+) 
     NMR 0.82 (3H, t), 1.1-1.5 (22H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.55 (2H, d), 2.7-2.8 (2H, m), 3.15 (2H, dd), 3.40 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 6 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-hexadecylpiperidine hydrochloride 
     Amount yielded 1.18 g 
     Yield 88% 
     TLC Rf=0.80 
     MS 497 (M+) 
     NMR 0.80 (3H, t), 1.1-1.6 (26H, m), 1.7-1.9 (2H, m), 2.33 (2H, dd), 2.58 (2H, d), 2.7-2.8 (2H, m), 3.20 (2H, dd), 3.40 (2H, d), 6.88 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 7 
     1-Cyclohexylmethyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 
     Amount yielded 520 mg 
     Yield 51% 
     TLC Rf=0.75 
     MS 369 (M+) 
     NMR 0.8-2.1 (11H, m), 2.42 (2H, dd), 2.65 (2H, d), 2.78 (2H, d), 3.20 (2H, dd), 3.42 (2H, d), 6.91 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 8 
     1-Cyclohexyl-2-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethane hydrochloride 
     Amount yielded 780 mg 
     Yield 74% 
     TLC Rf=0.75 
     MS 383 (M+) 
     NMR 0.8-2.1 (13H, m), 2.45 (2H, dd), 2.67 (2H, d), 2.7-2.9 (2H, m), 3.0 (2H, dd), 3.48 (2H, d), 6.94 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 9 
     1-Cyclohexyl-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane hydrochloride 
     Amount yielded 1.02 g 
     Yield 94% 
     TLC Rf=0.77 
     MS 397 (M+) 
     NMR 0.8-2.1 (15H, m), 2.47 (2H, dd), 2.68 (2H, d), 2.7-2.9 (2H, m), 3.0 (2H, dd), 3.49 (2H, d), 6.94 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 10 
     1-Cyclohexyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane hydrochloride 
     Amount yielded 815 mg 
     Yield 72% 
     TLC Rf=0.78 
     MS 411 (M+) 
     NMR 0.8-2.1 (17H, m), 2.28 (2H, dd), 2.52 (2H, d), 2.7-2.9 (2H, m), 3.08 (2H, dd), 3.35 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 11 
     1-Cyclohexyl-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)pentane hydrochloride 
     Amount yielded 750 mg 
     Yield 65% 
     TLC RF=0.80 
     MS 411 (M+) 
     NMR 0.8-2.1 (19H, m), 2.25 (2H, dd), 2.68 (2H, d), 2.7-2.9 (2H, m), 3.12 (2H, dd), 3.38 (2H, d), 6.92 (2H, s), 7.1-7.4 (8H, m) 
     EXAMPLE 12 
     1-Benzyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidien hydrochloride 
     Amount yielded 320 mg 
     Yield 80% 
     TLC Rf=0.42 
     MS 363 (M+) 
     NMR 2.28 (2H, dd), 2.52 (2H, d), 3.14 (2H, dd), 3.31 (2H, d), 4.01 (2H, d), 6.90 (2H, s), 7.1-7.6 (13H, m) 
     EXAMPLE 13 
     2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylethane hydrochloride 
     Amount yielded 310 mg 
     Yield 75% 
     TLC Rf=0.45 
     MS 377 (M+) 
     NMR 2.28 (2H, dd), 2.51 (2H, d), 3.0-3.3 (6H, m), 3.47 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 14 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylpropane hydrochloride 
     Amount yielded 330 mg 
     Yield 77% 
     TLC Rf=0.50 
     MS 391 (M+) 
     NMR 2.1-2.4 (4H, m), 2.51 (2H, d), 2.65 (2H, t), 2.7-2.9 (2H, m), 3.12 (2H, dd), 3.38 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 15 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylbutane hydrochloride 
     Amount yielded 180 mg 
     Yield 41% 
     TLC Rf=0.50 
     MS 405 (M+) 
     NMR 1.4-1.9 (4H, m), 2.28 (2H, dd), 2.52 (2H, d), 2.61 (2H,t), 2.7-2.8 (2H, m), 3.12 (2H, dd), 3.35 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 16 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylpentane hydrochloride 
     Amount yielded 110 mg 
     Yield 24% 
     TLC Rf=0.55 
     MS 419 (M+) 
     NMR 1.2-1.9 (6H, m), 2.25 (2H, dd), 2.52 (2H, d), 2.60 (2H, t), 2.7-2.8 (2H, m), 3.08 (2H, dd), 3.35 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 17 
     6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylhexane hydrochloride 
     Amount yielded 315 mg 
     Yield 67% 
     TLC Rf=0.56 
     MS 433 (M+) 
     NMR 1.1-1.9 (8H, m), 2.26 (2H, dd), 2.56 (2H, d), 2.61 (2H, t), 2.7-2.8 (2H, m), 3.10 (2H, dd), 3.35 (2H, d), 6.91 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 18 
     7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylheptane hydrochloride 
     Amount yielded 267 mg 
     Yield 55% 
     TLC Rf=0.56 
     MS 447 (M+) 
     NMR 1.1-1.9 (10H, m), 2.25 (2H, dd), 2.55 (2H, d), 2.65 (2H, t), 2.7-2.8 (2H, m), 3.07 (2H, dd), 3.32 (2H, d), 6.90 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 19 
     2-(4-(5H-Oibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenoxyethane hydrochloride 
     Amount yielded 1.95 g 
     Yield 55% 
     TLC Rf=0.56 
     MS 393 (M+) 
     NMR (fee base) 2.1-2.5 (2H, m), 2.58 (2H, t), 2.6-2.7 (2H, m), 4.05 (2H, t), 6.89 (2H, d), 6.92 (2H, s), 7.1-7.4 (11H, m) 
     EXAMPLE 20 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenoxypropane hydrochloride 
     Amount yielded 2.15 g 
     Yield 48% 
     TLC Rf=0.58 
     MS 407 (M+) 
     NMR (free base) 1.97 (2H, tt), 2.1-2.5 (6H, m), 2.54 (2H, t), 2.6-2.7 (2H, m), 3.97 (2H, dd), 6.86 (2H, d), 6.90 (2H, s), 7.1-7.4 (11H, m) 
     EXAMPLE 21 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenoxybutane hydrochloride 
     Amount yielded 1.18 g 
     Yield 86% 
     TLC Rf=0.61 
     MS 421 (M+) 
     NMR (free base) 1.8-2.7 (14H, m), 3.96 (2H, t), 6.87 (2H, d), 6.90 (2H, s), 7.1-7.4 (11H, m) 
     EXAMPLE 22 
     2-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylthioethane hydrochloride 
     Amount yielded 0.97 g 
     Yield 87% 
     TLC Rf=0.55 
     MS 409 (M+) 
     NMR (free base) 2.0-2.6 (10H, m), 2.78 (2H, t), 6.86 (2H, s), 7.1-7.4 (11H, m) 
     EXAMPLE 23 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylthiopropane hydrochloride 
     Amount yielded 0.85 g 
     Yield 74% 
     TLC Rf=0.62 
     MS 423 (M+) 
     NMR (free base) 1.73 (2H, tt), 2.0-2.6 (10H, m), 2.80 (2H, t), 6.88 (2H, d), 7.1-7.4 (11H, m) 
     EXAMPLE 24 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenylthiobutane hydrochloride 
     Amount yielded 0.85 g 
     Yield 72% 
     TLC Rf=0.62 
     MS 437 (M+) 
     NMR (free base) 1.6-2.6 (14H, m), 2.80 (2H, t), 6.88 (2H, d), 7.1-7.4 (11H, m) 
     EXAMPLE 25 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(2-nitrobenzenesulfonyl)aminoethyl)piperidine hydrochloride 
     TLC Rf=0.72 
     MS 502 (M+) 
     EXAMPLE 26 
     1-(2-(2-Aminobenzenesulfonyl)aminoethyl)-4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine hydrochloride 
     TLC Rf=0.51 
     MS 472 (M+) 
     EXAMPLE 27 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(2-ethoxycarbon-ylbenzenesulfon6yl)aminoethyl)piperidine hydrochloride 
     TLC Rf=0.68 
     MS 544 (M+) 
     EXAMPLE 28 
     3-(2-((4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-ethyl)-2,4(1H,3H)quinazolinedione hydrochloride 
     TLC Rf=0.85 
     MS 462 (M+) 
     EXAMPLE 29 
     5,6-Benzo-2,4-diazo(2-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl)tetrahydrothiopyrane hydrochloride 
     TLC Rf=0.91 
     MS 498 (M+) 
     EXAMPLE 30 
     2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4-dimethoxyphenyl)ethane hydrochloride 
     TLC Rf=0.78 
     MS 450 (M+) 
     EXAMPLE 31 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride 
     TLC Rf=0.92 
     MS 532 (M+) 
     NMR 0.77 (3H, d), 1.18 (3H, d), 1.6-3.3 (15H, m), 3.86 (3H, s), 3.92 (3H, s), 6.8-7.4 (11H, m) 
     EXAMPLE 32 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-propyl-4-fluorophenylsulfoxide hydrochloride 
     TLC Rf=0.78 
     MS 457 (M+) 
     EXAMPLE 33 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-propyl-4-fluorophenylsulfone hydrochloride 
     TLC Rf=0.62 
     MS 473 (M+) 
     EXAMPLE 34 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(2-aminophenylthio)-1-propyl)piperidine hydrochloride 
     TLC Rf=0.84 
     MS 439 (M+) 
     EXAMPLE 25 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-(2-benzoylamino)ethyl)piperidine hydrochloride 
     TLC Rf=0.84 
     MS 420 (M+) 
     EXAMPLE 36 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-(2-N-phenylcarbamoylamino)ethyl)piperidine hydrochloride 
     TLC Rf=0.55 
     MS 435 (M+) 
     EXAMPLE 37 
     1-(3-(2-Cinnamoylaminophenylthio)-1-propyl)-4-(5H-dibenzo[a,d]-cyclohepten-5-ylidene)piperidine hydrochloride 
     TLC Rf=0.66 
     MS 568 (M+) 
     NMR (free base) 1.74 (2H, tt), 2.0-2.6 (8H, m), 2.80 (2H, t), 6.59 (1H, d), 6.88 (2H, s), 7.0-7.6 (16H, m), 7.75 (1H, d), 8.5 (1H, d), 8.68 (1H, bs) 
     EXAMPLE 38 
     1-Cinnamyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 
     TLC Rf=0.84 
     MS 389 (M+) 
     NMR (free base) 2.1-2.7 (8H, m), 3.15 (2H, d), 6.25 (1H, td), 6.47 (1H, d), 6.90 (2H, s), 7.1-7.4 (13H, m) 
     EXAMPLE 39 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4,5-trimethoxyphenyl)-2-isopropylvaleronitrile hydrochloride 
     TLC Rf=0.80 
     MS 563 (M+) 
     EXAMPLE 40 
     2-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-2-phenyl-1,3-dithiane-1,1,3,3-tetroxide hydrochloride 
     TLC Rf=0.48 
     MS 573 (M+) 
     EXAMPLE 41 
     2-(3,4-Dimethoxyphenyl)-2-(3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-1,3-dithiane-1,1,3,3-tetroxide hydrochloride 
     TLC Rf=0.48 
     MS 573 (M+) 
     EXAMPLE 42 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dichlorophenyl)-2-isopropylvaleronitrile hydrochloride 
     TLC Rf=0.94 
     MS 540 (M+) 
     EXAMPLE 43 
     2-(3-Benzoylphenyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methylvaleronitrile hydrochloride 
     TLC Rf=0.88 
     MS 548 (M+) 
     EXAMPLE 44 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2,2-diphenylvaleronitrile hydrochloride 
     TLC Rf=0.74 
     MS 506 (M+) 
     EXAMPLE 45 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3,4-dimethoxybutyrophenone hydrochloride 
     TLC Rf=0.61 
     MS 479 (M+) 
     EXAMPLE 46 
     6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2phenylhexanenitrile hydrochloride 
     TLC Rf=0.86 
     MS 430 (M+) 
     EXAMPLE 47 
     6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenylhexanenitrile hydrochloride 
     TLC Rf=0.88 
     MS 472 (M+) 
     EXAMPLE 48 
     6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropylhexanenitrile hydrochloride 
     TLC Rf=0.81 
     MS 546 (M+) 
     EXAMPLE 49 
     7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylheptanenitrile hydrochloride 
     TLC Rf=0.84 
     MS 444 (M+) 
     EXAMPLE 50 
     7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenylheptanenitrile hydrochloride 
     TLC Rf=0.84 
     MS 486 (M+) 
     EXAMPLE 51 
     7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropylheptanenitrile hydrochloride 
     TLC Rf=0.86 
     MS 560 (M+) 
     EXAMPLE 52 
     2-(3-Chloropropyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrile hydrochloride 
     TLC Rf=0.92 
     MS 506 (M+) 
     EXAMPLE 53 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenyl-2-phenylthiovaleronitrile hydrochloride 
     TLC Rf=0.81 
     MS 538 (M+) 
     EXAMPLE 54 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-phenylthiovaleronitrile hydrochloride 
     TLC Rf=0.91 
     MS 598 (M+) 
     EXAMPLE 55 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-naphthyl)valeronitrile hydrochloride 
     TLC Rf=0.85 
     MS 580 (M+) 
     EXAMPLE 56 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-naphthyl)-2-isopropylvaleronitrile hydrochloride 
     TLC Rf=0.90 
     MS 522 (M+) 
     EXAMPLE 57 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-naphthyl)valeronitrile hydrochloride 
     TLC Rf=0.85 
     MS 480 (M+) 
     EXAMPLE 58 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-naphthyl)-2-isopropylvaleronitrile hydrochloride 
     TLC Rf=0.87 
     MS 522 (M+) 
     EXAMPLE 59 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-trifluoromethylphenyl)valeronitrile hydrochloride 
     TLC Rf=0.72 
     MS 498 (M+) 
     EXAMPLE 60 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3-trifluoromethylphenyl)valeronitrile hydrochloride 
     TLC Rf=0.75 
     MS 540 (M+) 
     EXAMPLE 61 
     8-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenyloctanenitrile hydrochloride 
     TLC Rf=0.84 
     MS 472 (M+) 
     EXAMPLE 62 
     8-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenyloctanenitrile hydrochloride 
     TLC Rf=0.88 
     MS 514 (M+) 
     EXAMPLE 63 
     8-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-isopropyloctanenitrile hydrochloride 
     TLC Rf=0.82 
     MS 574 (M+) 
     EXAMPLE 64 
     1-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-1-indanenitrile hydrochloride 
     TLC Rf=0.90 
     MS 456 (M+) 
     EXAMPLE 65 
     1-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-5,6-dimethoxy-1-indanenitrile hydrochloride 
     TLC Rf=0.85 
     MS 516 (M+) 
     EXAMPLE 66 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-methylpyrrol-2-yl)valeronitrile hydrochloride 
     TLC Rf=0.61 
     MS 433 (M+) 
     EXAMPLE 67 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(1-methylpyrrol-2-yl)valeronitrile hydrochloride 
     TLC Rf=0.71 
     MS 475 (M+) 
     EXAMPLE 68 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(pyrrol-2-yl)valeronitrile hydrochloride 
     TLC Rf=0.55 
     MS 461 (M+) 
     EXAMPLE 69 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-α-hydroxybenzyl)phenyl)-2-methylvaleronitrile hydrochloride 
     TLC Rf=0.51 
     MS 550 (M+) 
     EXAMPLE 70 
     2-(3-Benzoylphenyl)-6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methylhexanenitrile hydrochloride 
     TLC Rf=0.88 
     MS 562 (M+) 
     EXAMPLE 71 
     6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-(α-hydroxybenzyl)phenyl-2-methylhexanenitrile hydrochloride 
     TLC Rf=0.52 
     MS 564 (M+) 
     EXAMPLE 72 
     2-(3-Benzoylphenyl)-7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methylheptanenitrile hydrochloride 
     TLC Rf=0.91 
     MS 576 (M+) 
     EXAMPLE 73 
     7-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-(α-hydroxybenzyl)phenyl-2-methylheptanenitrile hydrochloride 
     TLC Rf=0.52 
     MS 578 (M+) 
     EXAMPLE 74 
     2-(3-Benzoylphenyl)-8-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyloctanenitrile hydrochloride 
     TLC Rf=0.90 
     MS 590 (M+) 
     EXAMPLE 75 
     8-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-(α-hydroxybenzyl)phenyl-2-methyloctanenitrile hydrochloride 
     TLC Rf=0.61 
     MS 592 (M+) 
     EXAMPLE 76 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyl-2-phenylvaleronitrile hydrochloride 
     TLC Rf=0.91 
     MS 544 (M+) 
     EXAMPLE 77 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-methylvaleronitrile hydrochloride 
     TLC Rf=0.85 
     MS 504 (M+) 
     EXAMPLE 78 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-2-phenylvaleronitrile hydrochloride 
     TLC Rf=0.92 
     MS 458 (M+) 
     EXAMPLE 79 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-ethylvaleronitrile hydrochloride 
     TLC Rf=0.90 
     MS 518 (M+) 
     EXAMPLE 80 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-propyl-2-phenylvaleronitrile hydrochloride 
     TLC Rf=0.93 
     MS 472 (M+) 
     EXAMPLE 81 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-propylvaleronitrile hydrochloride 
     TLC Rf=0.91 
     MS 532 (M+) 
     EXAMPLE 82 
     2-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrile hydrochloride 
     TLC Rf=0.95 
     MS 486 (M+) 
     EXAMPLE 83 
     2-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)valeronitrile hydrochloride: 
     TLC Rf=0.90 
     MS 546 (M+) 
     EXAMPLE 84 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-pentyl-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.95 
     MS 500 (M+) 
     EXAMPLE 85 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-pentylvaleronitrile hydrochloride: 
     TLC Rf=0.92 
     MS 560 (M+) 
     EXAMPLE 86 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-hexyl-2-=henylvaleronitrile hydrochloride: 
     TLC Rf=0.95 
     MS 514 (M+) 
     EXAMPLE 87 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-hexylvaleronitrile hydrochloride: 
     TLC Rf=0.92 
     MS 574 (M+) 
     EXAMPLE 88 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)2-heptyl-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.95 
     MS 528 (M+) 
     EXAMPLE 89 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-heptylvaleronitrile hydrochloride: 
     TLC Rf=0.91 
     MS 588 (M+) 
     EXAMPLE 90 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-octyl-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.94 
     MS 542 (M+) 
     EXAMPLE 91 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-octylvaleronitrile hydrochloride: 
     TLC Rf=0.94 
     MS 602 (M+) 
     EXAMPLE 92 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-nonyl-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.95 
     MS 556 (M+) 
     EXAMPLE 93 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)-2-nonylvaleronitrile hydrochloride: 
     TLC Rf=0.93 
     MS 616 (M+) 
     EXAMPLE 94 
     2-Decyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.95 
     MS 570 (M+) 
     EXAMPLE 95 
     2-Decyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)valeronitrile hydrochloride: 
     TLC Rf=0.94 
     MS 630 (M+) 
     EXAMPLE 96 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-acetophenone hydrochloride: 
     TLC Rf=0.71 
     MS 391 (M+) 
     EXAMPLE 97 
     2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylethane hydrochloride: 
     TLC Rf=0.36 
     MS 393 (M+) 
     EXAMPLE 98 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-propiophenone hydrochloride: 
     TLC Rf=0.74 
     MS 405 (M+) 
     EXAMPLE 99 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)1-hydroxy-1-phenylpropane hydrochloride: 
     TLC Rf=0.35 
     MS 407 (M+) 
     EXAMPLE 100 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-butyrophenone hydrochloride: 
     TLC Rf=0.75 
     MS 419 (M+) 
     EXAMPLE 101 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylbutane hydrochloride: 
     TLC Rf=0.39 
     MS 421 (M+) 
     EXAMPLE 102 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-valerophenone hydrochloride: 
     TLC Rf=0.76 
     MS 433 (M+) 
     EXAMPLE 103 
     5-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-phenylpentane hydrochloride: 
     TLC Rf=0.78 
     MS 447 (M+) 
     EXAMPLE 104 
     2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4&#39;-fluoroacetophenone hydrochloride: 
     TLC Rf=0.80 
     MS 409 (M+) 
     EXAMPLE 105 
     2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)1-hydroxy-1-(4-fluorophenyl)ethane hydrochloride: 
     TLC Rf=0.44 
     MS 411 (M+) 
     EXAMPLE 106 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)4&#39;-fluoropropiophenone hydrochloride: 
     TLC Rf=0.80 
     MS 423 (M+) 
     EXAMPLE 107 
     3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)propane hydrochloride: 
     TLC Rf=0.44 
     MS 425 (M+) 
     EXAMPLE 108 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)butane hydrochloride: 
     TLC Rf=0.45 
     MS 439 (M+) 
     EXAMPLE 109 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4&#39;-fluorovalerophenone hydrochloride: 
     TLC Rf=0.84 
     MS 451 (M+) 
     EXAMPLE 110 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-hydroxy-1-(4-fluorophenyl)pentane hydrochloride: 
     TLC Rf=0.51 
     MS 453 (M+) 
     EXAMPLE 111 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-fluorobenzyl)-piperidine hydrochloride: 
     TLC Rf=0.75 
     MS 381(M+) 
     EXAMPLE 112 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-fluorobenzyl)piperidine hydrochloride: 
     TLC Rf=0.79 
     MS 381 (M+) 
     EXAMPLE 113 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-fluorobenzyl)piperidine hydrochloride: 
     TLC Rf=0.61 
     MS 381 (M+) 
     EXAMPLE 114 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-trifluoromethylbenzyl)piperidine hydrochloride: 
     TLC Rf=0.83 
     MS 43I (M+) 
     EXAMPLE 115 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-trifluoromethylbenzyl)piperidine hydrochloride: 
     TLC Rf=0.82 
     MS 431 (M+) 
     EXAMPLE 116 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride: 
     TLC Rf=0.79 
     MS 431 (M+) 
     EXAMPLE 117 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxybenzyl)piperidine hydrochloride: 
     TLC Rf=0.61 
     MS 393 (M+) 
     EXAMPLE 118 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxybenzyl)piperidine hydrochloride: 
     TLC Rf=0.61 
     MS 393 (M+) 
     EXAMPLE 119 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxybenzyl)piperidine hydrochloride: 
     TLC Rf=0.52 
     MS 393 (M+) 
     EXAMPLE 120 
     4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-pentafluorobenzylpiperidine hydrochloride: 
     TLC Rf=0.80 
     MS 453 (M+) 
     EXAMPLE 121 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.86 
     MS 440 (M+) 
     EXAMPLE 122 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-phenylvaleronitrile hydrochloride: 
     TLC Rf=0.82 
     MS 488 (M+) 
     EXAMPLE 123 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3,4-dimethoxyphenyl)valeronitrile hydrochloride: 
     TLC Rf=0.75 
     MS 500 (M+) 
     EXAMPLE 124 
     2-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl-2-(4-fluorophenyl)-1,3-dioxolane hydrochloride: 
     TLC Rf=0.68 
     MS 481 (M+) 
     EXAMPLE 125 
     4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4&#39;-fluorobutyrophenone hydrochloride: 
     TLC Rf=0.82 
     MS 437 (M+) 
     EXAMPLE 126 
     5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2 isopropyl-2-(3,4,5trimethoxyphenyl)valeronitrile hydrochloride: 
     TLC Rf=0.66 
     MS 562 (M+) 
     
         __________________________________________________________________________                                                   TLCexp   compound                                       MS(M+)                                                   (Rf)                                                      solvent__________________________________________________________________________127   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-fluorop   henyl)ethane hydrochloride                     395   0.55                                                      B128   1-(2-Chlorobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  397   0.68                                                      B129   1-(3-Chlorobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  397   0.58                                                      B130   1-(4-Chlorobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  397   0.58                                                      B131   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methylbenzyl)piperidine   hydrochloride                                  377   0.74                                                      B132   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methylbenzyl)piperidine   hydrochloride                                  377   0.71                                                      B133   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methylbenzyl)piperidine   hydrochloride                                  377   0.65                                                      B134   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-heptylpiperidine   hydrochloride                                  371   0.70                                                      B135   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-nonylpiperidine   hydrochloride                                  399   0.75                                                      B136   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-undecylpiperidine   hydrochloride                                  427   0.75                                                      B137   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-tridecylpiperidine   hydrochloride                                  455   0.78                                                      B138   1-(2-Aminobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   dihydrochloride                                392   0.38                                                      B139   1-(3-Aminobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   dihydrochloride                                392   0.23                                                      B140   1-(4-Aminobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   dihydrochloride                                392   0.26                                                      B141   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrobenzyl)piperidine   hydrochloride                                  422   0.85                                                      B142   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-nitrobenzyl)piperidine   hydrochloride                                  422   0.82                                                      B143   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrobenzyl)piperidine   hydrochloride                                  422   0.83                                                      B144   5-(4-(5H-Dibenzo[ a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-fluoro   phenyl)-2-isopropylvaleronitrile               500   0.71                                                      B   hydrochloride145   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-   2-                                             512   0.64                                                      B   (3-methoxyhenyl)valeronitrile hydrochloride146   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-   2-                                             496   0.68                                                      B   (3-methylphenyl)valeronitrile hydrochloride147   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-   2-(2-trifluoromethylphenyl)                    549   0.78                                                      B   valeronitrile hydrochloride148   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-   2-(4-trifluoromethylphenyl)                    540   0.77                                                      B   valeronitrile hydrochloride149   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-2-(3   -trifluoromethylphenyl)                        526   0.77                                                      B   valeronitrile hydrochloride150   2-Butyl-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3   -trifluoromethylphenyl)                        554   0.80                                                      B   valeronitrile hydrochloride151   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-hexyl-2-(3   -trifluoromethylphenyl)                        582   0.80                                                      B   valeronitrile hydrochloride152   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-phenyl-1-b   utene hydrochloride                            403   0.51                                                      B153   1-Benzyloxy-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)e   thane hydrochloride                            407   0.58                                                      B154   1-Cylcohexyl-6-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)   hexane hydorchloride                           439   0.62                                                      B155   1-Cylcohexyl-7-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)   heptane hydorchloride                          453   0.65                                                      B156   1-Cylcohexyl-8-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)   octane hydorchloride                           467   0.68                                                      B157   1-(4-Cyclohexylbutanoyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperi   dine                                           425   0.75                                                      B158   1-(2-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  388   0.83                                                      B159   1-(3-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  388   0.85                                                      B160   1-(4-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  388   0.70                                                      B161   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-Picolyl)piperidine   dihydrochloride                                364   0.58                                                      B162   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-Picolyl)piperidine   dihydrochloride                                364   0.53                                                      B163   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-Picolyl)piperidine   dihydrochloride                                364   0.44                                                      B164   1-Decanoyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine                                             427   0.75                                                      B165   1-Cyano-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propa   ne hydrochloride                               340   0.58                                                      B166   1-Cyano-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butan   e hydrochloride                                354   0.52                                                      B167   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;-dimeto   xyacetophenone hydrochloride                   451   0.85                                                      B168   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;-dimeto   xypropiophenone                                465   0.61                                                      B   hydrochloride169   5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;-dimeto   xyvalerophenone                                493   0.64                                                      B   hydrochloride170   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;,5&#39;-tri   metoxybutyrophenone                            509   0.82                                                      B   hydrochloride171   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2&#39;,3&#39;,4&#39;-tri   metoxybutyrophenone                            509   0.85                                                      B   hydrochloride172   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4&#39;-metoxybut   yrophenone hydrochloride                       449   0.61                                                      B173   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,3-dimethoxybenzyl)piperid   ine hydrochloride                              423   0.63                                                      B174   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimethoxybenzyl)piperid   ine hydrochloride                              423   0.73                                                      B175   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimethoxybenzoyl)piperi   dine                                           437   0.58                                                      B176   1-Cyclohexyl-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)   propylketone hydrochloride                     425   0.51                                                      B177   2-Cyclohexyl-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)   valeronitrile hydrochloride                    436   0.60                                                      B178   1-(4-(3-Chloro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4-c   yclohexylbutane                                445   0.62                                                      B   hydrochloride179   1-Cyclohexyl-(4-(3-metoxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piper   idinyl)butane hydrochloride                    441   0.59                                                      B180   4,9-Dihydro-4-(1-(4-cyclohexylbutyl)-4-piperidinylidene)-10H-benzo[4,5]   cyclohepta[1,2-b]biophen-10-                   433   0.45                                                      B   one hydrochloride181   1-(4-Cyclohexylbutyl)-4-(9-xantylidene)piperidine hydrochloride                                             401   0.64                                                      B182   1-(4-Cyclohexylbutyl)-4-(9-tioxantylidene)piperidine                                             417rochloride                                                   0.65                                                      B183   6,11-Dihydro-11-(1-(4-cyclohexylbutyl)-4-piperidinylidene)-5H-benzo[5,6   ]cyclohepta[1,2-b]pyridine                     414   0.41                                                      B   dihydrochloride184   4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene]-1-(3-metoxybenzy   l)piperidine hydrochloride                     395   0.73                                                      B185   1-Decyl-4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidin   e hydrochloride                                415   0.52                                                      H186   1-Cyclohexyl-4-(4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-   1-piperidinyl)butane                           413   0.67                                                      H   hydrochloride187   4-(4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl   )-3&#39;,4&#39;-                                       481   0.66                                                      B   dimetoxybutyrophenone hydrochloride188   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimetoxybenzyl)piper   idine                                          453   0.69                                                      B189   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimetoxybenzoyl)pipe   ridine                                         467   0.71                                                      B190   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methylbenzoyl)piperidine                                             391   0.73                                                      B191   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(4-fluorophenyl)acetyl)pi   peridine                                       409   0.76                                                      B192   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimetoxycinnamoyl)piper   idine                                          463   0.73                                                      B193   4-(5H-Dibenzo[a,d] cyclohepten-5-ylidend)-1-(3,4-dimetoxycinnamyl)piper   idine hydrochloride                            449   0.46                                                      B194   4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;-dietho   xybutyrophenone hydrochloride                  501   0.49                                                      B195   1-(4-(4-Aminophenyl)butyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)pipe   ridine dihydrochloride                         420   0.34                                                      B196   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(4-nitrophenyl)butyl)pipe   ridine hydrochloride                           450   0.50                                                      B197   1-(4-(4-Acetylaminophenyl)butyl)-4-(5H-dibenzo[a,d]cyclohepten-5-yliden   e)piperidine dihydrochloride                   462   0.48                                                      B198   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;-dimeth   ylbutyrophenone                                447   0.53                                                      B   hydrochloride199   Ethyl 4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyrat   e hydrochloride                                387   0.51                                                      B200   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyric                                             359d  0.15                                                      B201   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(3&#39;,4&#39;-dimethoxyphenyl)pr   opyl)piperidine                                451   0.60                                                      B   hydrochloride202   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(3&#39;,4&#39;-dimethoxyphenyl)pr   opanoyl)piperidine                             465   0.78                                                      B203   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)p   iperidine hydrochloride                        426   0.60                                                      B204   N-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-   1,2,3,4-tetrahydroisoquinoline                 474   0.42                                                      B   hydrochloride205   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4-dimet   hoxy)phenyl-1-hydroxybutane                    481   0.38                                                      B   hydrochloride206   1-Acetoxy-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-   (3,4-dimethoxy)phenylbutane                    523   0.49                                                      B   hydrochloride207   1-Butyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3   ,4-dimethoxy)phenyl-1-                         537   0.45                                                      B   hydroxybutane hydrochloride208   1-(4-Metoxycyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-pi   peridinyl)butane                               441   0.55                                                      B   hydrochloride209   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)pipe   ridine dihydrochloride                         412   0.03                                                      B210   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(N-imidazolylmethyl)cinna   myl)piperidine                                 469   0.44                                                      B   dihydrochloride211   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphtoyl)piperidine                                             427   0.88                                                      B212   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphtylmethyl)piperidine   hydrochloride                                  413   0.94                                                      B213   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphtoyl)piperidine                                             427   0.59                                                      B214   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphtylmethyl)piperidine   hydrochloride                                  413   0.83                                                      B215   2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)cycl   ohexanone hydrochloride                        426(H+)                                                   0.50                                                      B216   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-   4-hydroxypiperidine                            442   0.58                                                      B   hydrochloride217   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-   4-ethoxycarbonylpiperazine                     499   0.26                                                      B   hydrochloride218   Cyclohexyl 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)pr   opylether hydrochloride                        413   0.48                                                      B219   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-   1-methoxycarbonylcyclohexane                   470(H+)                                                   0.55                                                      B   hydrochloride220   Ethyl 2-cyclohexyl-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperi   dinyl)valerate hydrochloride                   483   0.65                                                      B221   3-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(3&#39;,4&#39;-dimethoxyphenyl)bu   tyl)piperidine hydrochloride                   465   0.66                                                      B222   2-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl-   2-(3,4-dimethoxyphenyl)-                       523   0.54                                                      B   1,3-dioxolane hydrochloride223   1-Carboxyl-1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl   )butylcyclohexane                              456(H+)                                                   0.38                                                      B   hydrochloride224   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphto   y)piperidine                                   431   0.90                                                      B225   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphty   lmethyl)piperidine                             417   0.55                                                      B226   N-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanoyl)   cyclohexylamine                                426   0.64                                                      B   hydrochloride227   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl   cyclohexanecarboxylate                         427   0.71                                                      B   hydrochloride228   4-(4-(5H-Dibenzo[b,e]thiepin-5-ylidene)-1-piperidinyl)-1-cyclohexylbuta   ne hydrochloride                               431   0.74                                                      B229   4-(4-(5H-Dibenzo[b,e]thiepin-5-ylidene)-1-piperidinyl)-3&#39;-4&#39;-dimethoxyb   utyrophenone hydrochloride                     499   0.46                                                      B230   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrocinnamyl)piperidine   hydrochloride                                  434   0.70                                                      B231   1-(4-Aminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   dihydrochloride                                404   0.36                                                      B232   1-(4-Acetylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piper   idine dihydrochloride                          446   0.27                                                      B233   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-furyl)-   1-butanone hydrochloride                       409      B234   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-thienyl   )-1-butanone hydrochloride                     425      B235   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl   (2-tetrahydropyranyl)                          415   0.55                                                      B   ether hydrochloride236   Cyclohexyl 3-(4-(5H-Dibenzo[a,d]cycloheptea-5-ylidene)-1-piperidinyl)pr   opionate hydrochloride                         427   0.71                                                      B237   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidiayl)ethyl-4-nitro   benzamide hydrochloride                        465   0.49                                                      H238   2-Cyclohexyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)   butyric acid                                   455   0.26                                                      B239   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl   phenylsulphoxide hydrochloride                 409   0.29                                                      H240   2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   5&#39;,6&#39;-dimethoxyindan                           477   0.41                                                      B   hydrochloride241   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl   phenylsulphone hydrochloride                   441   0.36                                                      B242   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3&#39;,4&#39;-d   imethoxybenzamide                              480   0.44                                                      G   hydrochloride243   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl   cyclohexanecarboxamide                         426   0.75                                                      B   hydrochloride244   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl   isonicotinamide dihydrochloride                421   0.20                                                      B245   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)m   orphine hydrochloride                          428   0.31                                                      C246   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)t   hiomorphorine hydrochloride                    444   0.43                                                      C247   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-nitroph   enyl)propane hydrochloride                     436   0.34                                                      H248   1-(4-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid   inyl)propane                                   406   0.33                                                      B   dihydrochloride249   1-(4-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-p   iperidinyl)propane                             448   0.43                                                      B   dihydrochloride250   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-nitroph   enyl)propane hydrochloride                     436   0.53                                                      H251   1-(2-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid   inyl)propane                                   406   0.52                                                      B   dihydrochloride252   1-(2-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-p   iperidinyl)propane                             448   0.51                                                      B   hydrochloride253   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl   phenylsulphoxide hydrochloride                 425   0.20                                                      H254   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl   phenylsulphone hydrochloride                   455   0.71                                                      B255   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-nitroph   enyl)butane hydrochloride                      450   0.49                                                      H256   Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1   -propylsulphide                                430(H+)                                                   0.17                                                      J   hydrochloride257   Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1   -propylsulphoxide                              445   0.51                                                      B   hydrochloride258   Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1   -propylsulphone                                462(H+)                                                   0.28                                                      H   hydrochloride259   Ethyl 2-cyclohexylmethyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-   piperidinyl)butyrate                           483   0.70                                                      B   hydrochloride260   1-(4-Acetylamino-1-cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylide   ne)-1-piperidinyl)butane                       468   0.43                                                      B   hydrochloride261   2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   5&#39;,6&#39;-dimethoxy-1-indanone                     477   0.41                                                      B   hydrochloride262   Ethyl 2-(2-cyclohexylethyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)   -1-piperidinyl)propionate                      483   0.74                                                      B   hydrochloride263   Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidi   nyl)-1-ethylsulfone                            461   0.94                                                      B   hydrochloride264   Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidi   nyl)-1-ethylsulfoxide                          441(H+)                                                   0.48                                                      B   hydrochloride265   Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidi   nyl)-1-ethylsulfide                            429   0.85                                                      B   hydrochloride266   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4-amino-6,7-   dimethoxyquinazoline                           476   0.34                                                      B   dihydrochloride267   N-Acetyl-N-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-   1-propyl)cyclohexylamine                       454   0.35                                                      B   hydrochloride268   N-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-   2-piperidone hydrochloride                     426   0.39                                                      B269   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-   1-ethoxycarboxylcyclohexane                    483   0.82                                                      B   hydrochloride270   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-pyridyl   )propane dihydrochloride                       392   0.44                                                      B271   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4&#39;-dimeth   oxybutyrophenone N-oxide                       477(M-18)                                                   0.45                                                      B272   1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-   1-hydroxymethylcyclohexane                     441   0.55                                                      B   hydrochloride273   1-Acetoxymethyl-1-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylideae)-1-piperi   dinyl)-1-butyl)cyclohexane                     483   0.86                                                      B   hydrochloride274   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-metyl-3&#39;,4   &#39;-dimethoxybutyrophenone                       493   0.22                                                      B   hydrochloride275   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-propyl)   -3&#39;,4&#39;-dimethoxybutyrophenone                  521   0.28                                                      H   hydrochloride276   2-Allyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3&#39;,4   &#39;-dimethoxybutyrophenone                       519   0.30                                                      H   hydrochloride277   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-propyl)   -3&#39;,4&#39;-dimethoxybutyrophenone                  521   0.38                                                      H   hydrochloride278   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-3&#39;,4   &#39;-dimethoxybutyrophenone                       507   0.33                                                      H   hydrochloride279   Cyclohexylmethyl-2-(4-(5H-Dibeazo[a,d]cyclohepten-5-ylidene)-1-piperidi   nyl)-2-ethyl)ether                             413   0.73                                                      B   hydrochloride280   1-(N-Acetyl-3-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-   1-piperidinyl)propane                          440   0.75                                                      B   hydrochloride281   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-piperid   inyl)propane dihydrochloride                   398   0.16                                                      A282   1-(3-Acetylamino-4-methoxyphenyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-yl   idene)-1-piperidinyl)butane                    492   0.58                                                      B   hydrochloride283   4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)c   yclohexanone hydrochloride                     425   0.63                                                      B284   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-pyridyl   )-1-propene dihydrochloride                    390   0.66                                                      H285   2,6-Dimethyl-4-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidin   yl)butyl)-5-methyl-1,4-                        528   0.30                                                      F   dihydropyrydine-3,5-dicarboxylate hydrochloride286   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2,3-dimet   hoxyphenyl)propane                             451   0.68                                                      H   hydrochloride287   2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-5&#39;,6&#39;-   dimethoxyindan hydrochloride                   463   0.59                                                      H288   2,6-Dimethyl-4-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidin   yl)-1-butyl)-5-methylpyrydine-                 527   0.68                                                      B   3,5-dicarboxylate dihydrochloride289   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-pyridyl   )propane dihydrochloride                       392   0.37                                                      B290   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3-nitro   benzamide hydrochloride                        466(H+)                                                   0.48                                                      D291   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-2-nitro   benzamide hydrochloride                        466(H+)  D292   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3,4-dim   ethoxybenzamide                                481(H+)                                                   0.31                                                      D   hydrochloride293   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-pyrolle   )-1-butanone hydrochloride                     409(H+)  B294   1-(N-Acetyl-2-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-   1-piperidinyl)propane                          440   0.30                                                      B   hydrochloride295   4-(4-(5H-Dibenzo[a,d]cycloheptea-5-ylidene)-1-piperidinyl)-1-(N-methyl-   3-piperidinyl)butane                           426   0.07                                                      B   dihydrochloride296   1-(1-(4-Hydroxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)   -1-piperidinyl)butane                          427   0.45                                                      B   hydrochloride297   1-(1-(4-Cyano)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cycloheptea-5-ylidene)-1   -piperidinyl)butane                            436   0.55                                                      F   hydrochloride298   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-methoxy   phenyl)propane                                 421   0.81                                                      B   hydrochloride299   1-(1-(3-Methoxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)   -1-piperidinyl)butane                          441   0.71                                                      B   hydrochloride300   1-(1-(3-Hydroxyoxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylide   ne)-1-piperidinyl)butane                       427   0.47                                                      B   hydrochloride301   3-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)c   yclohexanone hydrochloride                     425   0.70                                                      B302   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrocinnamyl)piperidine   hydrochloride                                  434   0.91                                                      B303   1-(2-Aminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   dihydrochloride                                404   0.62                                                      B304   1-(2-Acetylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piper   idine hydrochloride                            446   0.55                                                      B305   4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)   tetrahydropyran hydrochloride                  413   0.69                                                      B306   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-nitrocinnamyl)piperidine   hydrochloride                                  984   0.90                                                      B307   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-piperid   inyl)propane dihydrochloride                   398   0.07                                                      B308   1-(N-Acetyl-4-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-   1-piperidinyl)propane                          440   0.23                                                      B   hydrochloride309   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-piperid   inyl)propane dihydrochloride                   398   0.03                                                      A310   2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)i   ndane hydrochloride                            417   0.59                                                      H311   4-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   2,4,5,6-tetramethyl-                           524   0.68                                                      B   1,4-dihydropyrydine-3,5-dicarboxylate hydrochloride312   4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(N-ethoxyc   arbonyl-3-piperidinyl)butane                   484   0.64                                                      B   hydrochloride313   1-(5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-pentyl)   -1-methoxycarbonylcyclohexane                  483   0.72                                                      B   hydrochloride314   1-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)   -1-methoxycarbonylcyclohexane                  455   0.75                                                      B   hydrochloride315   1-(3-Aminophenyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid   inyl)propane dihydrochloride                   993   0.62                                                      B316   1-(3-Acetylaminophenyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-p   iperidinyl)propane                             994   0.48                                                      B   hydrochloride317   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid   0.4inyl)-1-(3,4,5-trimetoxyphenyl)propane      481   0.65                                                      B   dihydrochloride318   2-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   5,6-dimethoxy-1,2,3,4-                         491   0.21                                                      H   tetrahydronaphtalene hydrochloride319   6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-2,3-di   methoxybenzocycloheptene                       491   0.56                                                      H   hydrochloride320   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxycinnamyl)pi   peridine hydrochloride                         479   0.69                                                      B321   1-(N-Acetyl-4-piperidinyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-   1-piperidinyl)-1-pentene                       466   0.33                                                      B   dihydrochloride322   2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-   3,4,5,6-tetramethyl-1,4-                       1000  0.30                                                      B   dihydropyrydine-3,5-dicarboxylate hydrochloride323   2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-   3,4,5,6-tetramethylpyrydine-                   550   0.43                                                      B   3,5-dicarboxylate hydrochloride324   1-(1-(4-Methoxy)cyclohexyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)   -1-piperidinyl)propane                         427   0.48                                                      B   hydrochloride325   4-(5H-Dibenzo[b,e]thiepin-5-ylidene)-1-(4-nitrocinnamyl)piperidine   hydrochloride                                  454   0.89                                                      B326   1-(4-Aminocinnamyl)-4-(5H-dibeazo[b,e]thiepin-5-ylideae)piperidine   dihydrochloride                                424   0.65                                                      B327   1-(4-Acetylaminominocinnamyl)-4-(5H-Dibenzo[b,e]thiepin-5-ylideae)piper   idine hydrochloride                            466   0.58                                                      B328   3-(4-(5H-Dibenzo[a,d]cycloheptea-5-ylidene)-1-piperidinyl)-1-(2,4-dimet   oxyphenyl)propane                              451   0.64                                                      B   dihydrochloride329   2-(4-(5H-Dibenzo[a,d]cycloheptea-5-ylidene)-1-piperidinyl)methyl-4&#39;-nit   roindan hydrochloride                          448   0.49                                                      I330   4&#39;-Amino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)meth   ylindan hydrochloride                          418   0.38                                                      H331   4&#39;-Acetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidiny   l)methylindan hydrochloride                    460   0.33                                                      B332   2-(4-(5H-Dibenzo[a,d] cyclohepten-5-ylidene)-1-piperidinyl)methyl-5-&#39;-n   itroindan hydrochloride                        448   0.50                                                      I333   5&#39;-Amino2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methy   lindan hydrochloride                           418   0.34                                                      B334   5&#39;-Acetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperdinyl   )methylindane hydrochloride                    460   0.29                                                      H335   4-Amino-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl   benzamide hydrochloride                        435      B336   3-Amino-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl   benzamide hydrochloride                        435      B337   1-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethy   isonipecotinamide                              455      B   hydrochloride338   1-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethy   nipecotinamide                                 455      B   hydrochloride339   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethynicotinam   ide dihydrochloride                            421   0.42                                                      B340   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethynicotinam   ide N-oxide hydrochloride                      437(H+)                                                   0.27                                                      D341   N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyisonicoti   namide N-oxide                                 437(H+)                                                   0.30                                                      D   hydrochloride342   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,4-dimethoxycinnamyl)piper   idine hydrochloride                            449   0.73                                                      B343   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,5-dimethoxycinnamyl)piper   idine hydrochloride                            449   0.73                                                      B344   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,3-dimethoxycinnamyl)piper   idine hydrochloride                            449   0.90                                                      B345   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,5-dimethoxycinnamyl)piper   idine hydrochloride                            449   0.74                                                      B346   1-(4-Cyanocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine   hydrochloride                                  414   0.70                                                      B347   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxycinnamyl)piperidin   e hydrochloride                                419   0.87                                                      B348   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxycinnamyl)piperidin   e hydrochloride                                419   0.89                                                      B349   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycinnamyl)piperidin   e hydrochloride                                419   0.85                                                      B350   4-(10.11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrocinnam   yl)piperidine hydrochloride                    436   0.93                                                      B351   1-(4-Aminocinnamyl)-4-(10.11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylide   ne)piperidine                                  406   0.64                                                      B   dihydrochloride352   1-(4-Acetylaminocinnamyl)-4-(10.11-dihydro5H-dibenzo[a,d]cyclohepten-5-   ylidene)piperidine                             448   0.54                                                      B   dihydrochloride353   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-fluorocinnamyl)piperidine    hydrochloride                                 407   0.88                                                      B354   2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   4&#39;-nitroindan hydrochloride                    462   0.34                                                      H355   4&#39;-Amino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-   1-ethyl)indan hydrochloride                    432   0.53                                                      B356   4&#39;-Acetylamino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid   inyl)-1-ethyl)indan                            474   0.24                                                      B   hydrochloride357   2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   5&#39;-nitroindan hydrochloride                    462   0.31                                                      H358   5&#39;-Amino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-   1-ethyl)indan dihydrochloride                  432   0.23                                                      H359   5&#39;-Acetylamino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid   inyl)-1-ethyl)indan                            474   0.05                                                      H   hydrochloride360   2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-   5&#39;-methanesulfonylaminoindan                   510   0.11                                                      H   hydrochloride361   1-Cyclohexyl-4-(4-(10.11-dihydroxy-5H-dibenzo[a,d]cyclohepten-5-ylidene   )-1-piperidinyl)butane                         445   0.84                                                      B362   3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-pyridyl   )-1-propene dihydrochloride                    390   0.44                                                      B363   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-hydroxycinnamyl)piperidin   e hydrochloride                                406(H+)                                                   0.55                                                      B364   1-(4-Acetoxycinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidin   e hydrochloride                                447   0.87                                                      B365   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-hydroxy-3-methoxycinnamyl   )piperidine hydrochloride                      435   0.63                                                      B366   1-(4-Acetoxy-3-metoxycinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)   piperidine hydrochloride                       477   0.83                                                      B367   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidiene)-1-(3-hydroxycinnamyl)piperidi   ne hydrochloride                               405   0.45                                                      B368   1-(3-Acetoxycinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidin   e hydrochloride                                447   0.80                                                      B369   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(2-methoxyacetoxy)cinnamy   l)piperidine hydrochloride                     477   0.65                                                      B370   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-propanoylaminocinnamyl)pi   peridine hydrochloride                         460   0.21                                                      H371   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-ethoxycarbomylaminocinnam   yl)piperidine                                  476   0.20                                                      H   hydrochloride372   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methanesulfonylaminocinna   myl)piperidine                                 482   0.44                                                      B   hydrochloride373   1-(N,N,-Bis(methanesulfonyl)aminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepte   n-5-ylidene)piperidine                         560   0.88                                                      B   hydrochloride374   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxycarbonylcinnamyl)p   iperidine hydrochloride                        447   0.55                                                      B375   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxycarbonylcinnamyl)p   iperidine hydrochloride                        447   0.48                                                      H376   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylcinnamyl)p   iperidine hydrochloride                        447   0.50                                                      B377   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxy-2-nitrocinnamyl)p   iperidine hydrochloride                        464   0.30                                                      H378   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylaminocinna   myl)piperidine                                 462   0.53                                                      B   hydrochloride379   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-pivaloylaminocinnamyl)pip   eridine hydrochloride                          488   0.51                                                      B380   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-trifluoroacetylaminocinna   myl)piperidine hydrochloride                   500   0.44                                                      B381   1-(4-Butanoylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)pip   eridine hydrochloride                          474   0.50                                                      B382   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-ethoxycarboxycinnamyl)pip   eridine hydrochloride                          477   0.85                                                      B383   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(2-methoxyacetoxy)cinnamy   l)piperidine hydrochloride                     477   0.45                                                      B384   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dihydroxycinnamyl)piper   idine hydrochloride                            422(H+)                                                   0.35                                                      B385   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-indolylmethyl)piperidine   hydrochloride                                  402   0.67                                                      H386   1-(4-Aminosulfonylcinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)pip   eridine hydrochloride                          468(H+)                                                   0.48                                                      B387   4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxy-4-nitrocinnamyl)p   iperidine hydrochloride                        464   0.29                                                      H__________________________________________________________________________ solvent: solvent for TLC A: chloroform/methanol = 4/1 B: chloroform/methanol = 9/1 C: chloroform/methanol = 20/1 D: chloroform/methanol = 25/1 E: chloroform/methanol = 50/1 F: ethylacetate/hexane = 5/1 G: ethylacetate/hexane = 3/1 H: ethylacetate/hexane = 1/1 I: ethylacetate/hexane = 1/2 G: ethylacetate/hexane = 1/5 
    
     EXAMPLE 154 
     As test animals, four male spontaneously hypertensive rats (weight 400 to 440 g) that were sufficiently adapted for feeding and in which hypertension was confirmed were used. 
     Physiological saline aqueous solution containing 2.5% Nicolle and 2.5% ethanol of sample was intravenously administered by bolus injection at a does of 1 ml per 1 kg of body weight. Systolic blood pressure after administration was measured by the indirect (tail-cuff) method. 
     The results are shown below. 
     
         ______________________________________        Decrease in systolic blood pressureDose         (mmHg) time after administration (hour)Compound   (mg/kg)  0.5           4______________________________________ 1      10        -67            1 2      10       -125          -34 3       3       -110          -22 4      10        -76            0 5      10        -56          -20 7      10        -57          -15 8      10        -95          -21 9      10        -91          -19 10     10       -129          -21 11     10       -166 12     10        -27            1 13     10        -47            4 14     10       -105          -10 15     10       -130          -136 16     10       -114          -30 17     10        -84          -16 20     10        -37            2 23     10        -34           10 25     10        -8            -7 28     10        -52            4 31     10        -61          -11 37     10        -78          -36 38     10       -140          -76 42     10        -66          -14 45     10       -147          -38 52     10        -23           -9 59     10        -87          -21 60     10       -121          -48100     10        -35           -5101     10        -89          -14107     10        -88          -19108     10       -126          -50111     10        -98          -13112     10        -16            0113      1       -151          -81115     10        -53          -19116     10        -36          -12117     10       -143          -25118     10       -129          -24119     10        -34           -5120      3        -17          -12121     10        -42          -19122     10       -120          -62123     10        -55           -7124     10        -90          -20125     10        -93          -14126     10        -87          -19128     10       -128           -8129     10        -17           - 1130     10        -42           -9131     10       -116            2132     10       -106           -5133      3       -146          -84134     10       -115          -30135     10       -132          -50136     10       -100          -40138     10       -129          -33139     10       -139          -89140      3       -113          -101142     10        -43            0149     10       -116          -32150     10       -110          -47151     10        -81          -43154     10       -131          -105155     10       -131          -105156     10       -110          -42157     10        -32          -13158     10        -8             7159     10        -27          -12160     10        -3           -10161     10        -64          -12162     10        -62           -3163     10        -1             4164     10        -91          -22165     10        -22           12166     10        -45            6168     10       -108            0169     10       -130           -4171     10       -122           -8172     10       -115          -25173     10        -98          -25174     10        -8           -16175     10        -87           -1176     10       -105          -10180     10        -25          -24181     10        -56          -27182     10        -11           -6184     10        -16           -4185     10        -66          -10186     10        -95          -12187     10        -47           -9188     10        -94          -12189     10        -72          -15190     10        -11          -15191     10        -29          -20192     10        -25          -36193     10       -124          -59194     10        -59          -17195     10       -100          -51196     10       -145          -81197     10        -51          -26198     10       -124          -25199     10        -15          -24200     10        -10          -24201     10       -118          -21202     10        -54          -16203      3       - 123         -58204     10       -141          -84205     10        -22           -4206     10        -61          -27207     10        -98          -43208     10       -131          -19209     10        -49          -13210      1        -78          -69212     10       -155213     10        -82            3214     10       -126          -21215     10       -128          -14216      3        -2           -27217     10        -18          -20218     10        -97          -11219     10       -104          -33220     10       -148          -54221     10        -70          -13222     10        -94           -5224     10        -69          -61225     10       -115          -31226     10       -131          -16228      3       -112          -14229      3        -77          -14230      3       -131          -91231      3       -132          -115232      1        -92          -85233     10        -35           -1234     10        -96           -2235     10        -99           -5236     10        -10          -15237     10        -65          -14238     10        -14           -5239     10        -68          -15240      3       -118           -5241     10        -73           -4242     10        -28            7243     10       -111          -31244     10        -19            4245     10        -34          -10246     10        -34           -4247     10       -119          -40248     10       -101          -92249     10       -121          -100250     10       -136          -30251     10       -110          -24252     10        -23           -5253     10        -12            1255     10        -62            2256     10        -60          -11257     10        -70          -13258     10        -74          -10259     10        -46           -5260     10        -51          -10261     10       -123          -11262     10        -16           -3264     10        -38           - 5265     10        -61          -11266     10       -133          -77267     10        -40            0268     10        -29           13269     10       -143          -71270     10        -18            2271     10        -17          -13272     10        -76           -3273     10        -37            5274     10       -102          -21275     10        -66          -20276     10        -24           -1277     10        -27            0278     10        -64            2279      3        -83          -24280     10        -50          -11281     10        -31           -5282     10        -72          -15283     10       -112            4284      3       -151          -40285     10        -62           -7286     10       -134          -40287     10        -83          -16288     10        -92          -14289      3        -20           10290      3        -15           15291      3        -8            15292      3        -31            3293     10       -122            4294      3        -17            7295      3        -36            1296     10       -109          -14297     10       -129          -57298     10       -111          -31299     10       -134          -45300     10        -97          -22301     10       -100          -12302     10        -83          -41303      3        -90          -19304     10        -49           -5305     10        -95           -9306     10       -138          -37307     10        -62          -10308      3        -27           -5310     10        -90          -18311     10        -90          -18312     10       -115          -11313     10       -154          -85314     10        -61          -11315     10        -43           -3316      1       -100            8317     10       -118          -14318     10        -83          -57319     10       -104          -20320     10       -147          -113321     10        -60           -4322     10       -100          -16323     10       -117          -11324     10       -137          -46325     10       -115          -100326      1       -125          -102327      3        -10          -43328     10       -125          -87329     10        -34           -7330     10        -93          -25331     10        -62          -14332     10       -111          -57343      3        -83          -45344      1       -123          -35345      3       -120          -95346      3       -142          -121347      3       -116          -53348      3       -105          -12349      1        -48          -43350     10       -136          -85351      3        -70          -21352      3        -93          -60353     10       -147          -138354      3        -89           -8363      3       -120364      1       -113365      3        -80          -56366      3       -152          -113367     10         -98         -63368      3       -110          -68369     10       -101          -83370     10        -99          -69374      3       -119           11375      1       -126          -70376      3       -106          -77377      1       -151          -73378      1       -106          -90379      1       -118          -59380       0.3    -141381      3       -136382      3       -129          -74383      3       -112          -86384      3       -130          -93385     10       -123          -96386     10        -83          -96387     10       -112          -50______________________________________ 
    
     Effects of the Invention 
     From the foregoing results, it is understood that the piperidine derivatives of the present invention possess hypotensive activity and are usable as hypotensives and therefore, they can be expected to provide an excellent hypotensive effect. Accordingly, the present invention is extremely useful, particularly in the pharmaceutical industry. 
     Having now fully described the invention, it will be apparent to one of ordinary skill in the art that many changes and modifications can be made thereto without departing from the spirit or scope of the invention as set forth herein.