Piperidine derivatives and hypotensives containing the same

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.sub.2).sub.n, which may be substituted, in which n is 0 or an integer of 1 to 10, --CH.dbd.CH--, --C.dbd.C--, --O--, --S--, --NH--, --N(COCH.sub.3)--, --N(COOC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO--, or --SO.sub.2 --; Y is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --O--, --S--, --NH--, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, --CH(OH)CH.sub.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.sub.2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH.dbd.CH--, --C.dbd.C--, --O--, --S-- , --NH--, --N(COCH.sub.3), --N(COC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3), --CO--, --SO-- or --SO.sub.2 --, and wherein one or more of the --(CH.sub.2)-groups in X and Q may be substituted by --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.5 -- thereby forming a ring structure.

Description

BACKGROUND OF THE INVENTION

FIELD OF THE INVENTION

The present invention relates to a piperidine derivative and hypotensives containing the same.

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.sub.2).sub.n, which may be substituted, in which n is 0 or an integer of 1 to 10, --CH.dbd.CH--, --C.dbd.C--, --O--, --S--, --NH--, --N(COCH.sub.3)--, --N(COOC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO--, or --SO.sub.2 --; Y is --CH.dbd.CH--, --CH.sub.2 CH.sub.2 --, --CH.sub.2 CO--, --O--, --S--, --NH--, --OCH.sub.2 --, --SCH.sub.2 --, --NHCH.sub.2 --, --CH(OH)CH.sub.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.sub.2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by --CH.dbd.CH--, -- C.dbd.C--, --O--, --S--, --NH--, --N (COCH.sub.3), --N(COC.sub.2 H.sub.5)--, --N(CHO)--, --N(CH.sub.3)--, --CO--, --SO-- or --SO.sub.2 --, and wherein one or more of the --(CH.sub.2)-groups in X and Q may be substituted by --(CH.sub.2).sub.4 -- or --(CH.sub.2).sub.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(CH2)n, wherein n is 1 to 10, C.sub.1 (CH.sub.2).sub.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.sub.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.degree. 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 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, 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)piperidine 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]cyctohepten-5-ylidene)-1-piperidinyl)-1-phenylheptane hydrochloride

Amount yielded 267 mg Yield 55% TLC Rf=0.56 MS 447 (M+) NMR 1.1-1 (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-Dibenzo[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-ethoxycarbonylbenzenesulfon6yl)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 35

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-5ylidene)-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)-2-phenylhexanenitrile 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-.alpha.-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-.alpha.-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-(.alpha.-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-(.alpha.-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-phenylvaleronitrile 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'-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'-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'-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 431 (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'-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-(3,4,5-trimethoxyphenyl)valeronitrile hydrochloride

TLC Rf=0.66 MS 562 (M+) __________________________________________________________________________ MD TLC sol-exp compound (M+) (Rf) vent__________________________________________________________________________127 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl-1-(4-fluoroph enyl)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-methylbenyl)piperidine hydrochloride 377 0.74 B132 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methylbenyl)piperidine hydrochloride 377 0.71 B133 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methylbenyl)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-nondecylpiperidine 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-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine dihydrochloride 392 0.38 B139 1-(3-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine dihydrochloride 392 0.23 B140 1-(4-Aminobenzy)-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-fluor ophenyl)-2-isopropylvaleronitrile 500 0.71 B hydrochloride145 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl- 2-(3-methoxyphenyl)valeronitrile 512 0.64 B hydrochloride146 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl- 2-(3-methylphenyl)valeronitrile 496 0.68 B hydrochloride147 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl- 2-(2- 549 0.78 B trifluoromethylphenyl)valeronitrile hydrochloride148 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl- 2-(4- 540 0.77 B trifluoromethylphenyl)valeronitrile hydrochloride149 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-2-(3 - 526 0.77 B trifluoromethylphenyl)valeronitrile hydrochloride150 2-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3 - 554 0.80 B trifluoromethylphenyl)valeronitrile hydrochloride151 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-hexyl-2-(3 - 582 0.80 B trifluoromethylphenyl)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-Cyclohexyl-6-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl) hexane hydrochloride 439 0.62 B155 1-Cyclohexyl-7-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl) heptane hydrochloride 453 0.65 B156 1-Cyclohexyl-8-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl) octane hydrochloride 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-Decanolyl-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)propa ne hydrochloride 354 0.52 B167 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4'-dimeth oxyacetophenone hydrochloride 451 0.85 B168 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4'-dimeth oxyptopiophenone hydrochloride 465 0.61 B169 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4'-dimeth oxyvalerophenone hydrochloride 193 0.64 B170 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4','5'-tr imethoxybutryrophenone 509 0.82 B hydrochloride171 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2',3',4'-tri methoxybutyrophenone 509 0.86 B hydrochloride172 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4'-methoxybu tyrophenone 449 0.61 B hydrochloride173 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-dimethoxybenzyl)piperid ine 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-cy clohexylbutane hydrochloride 445 0.62 B179 1-Cyclohexyl-(4-(3-methoxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-pipe ridinyl)butane hydrochloride 441 0.59 B180 4,9-Dihydro-4-(1-(4-cyclohexylbutyl)-4-piperidinylidene-10H-benzo[4,5]c yclohepta[1,2-b]thiophen-10-one 433 0.45 B hydrochloride181 1-(4-Cyclohexylbutyl-4-(9-xantylidene)piperidine hydrochloride 401 0.64 B182 1-(4-Cyclohexylbutyl-4-(9-thioxantylidene)piperidine 417rochloride 0.65 B183 6,11-Dihydro-11-(1-(4-cyclohexylbutyl)-4-piperidinylidene-5H-dibenzo[5, 6]cycloheptal[1,2-b]pyridine 414 0.41 B dihydrochloride184 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxybenz yl)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 B186 1-Cyclohexyl-4-(4-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptan-5-ylidene)- 1-piperidinyl)butane 413 0.67 B hydrochloride187 4-(4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl )-3',4'-dimethoxy- 481 0.66 B butyrophenone hydrochloride188 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxybenzyl)pipe ridine 453 0.69 B189 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxybenzoyl)pip eridine 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-(2-dimethoxycinnamoyl)piperi dine 463 0.73 B193 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-dimethoxycinnamyl)piperid ine hydrochloride 449 0.46 B194 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4'-dietho xybutyrophenone hydrochloride 501 0.49 B195 1-(4-(4-Aminophenyl)butyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)pipe ridine dihydrochloride 420 0.34 B196 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(4-nitrophenyl)buytl)pipe ridine hydrochloride 450 0.50 B197 1-(4-(4-Acetylaminophenyl)butyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidine )piperidine dihydrochloride 462 0.48 B198 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4'-dimeth ylbutyrophenone hydrochloride 447 0.53 B199 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 acid 359 0.15 B201 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(-3-(3',4'-dimethoxyphenyl)p ropyl)piperidine hydrochloride 451 0.60 B202 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(3',4'-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 hydroxybutane 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 hydroxybutane hydrochloride208 1-(4-Methoxyxyxlohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-p iperidinyl)butane 441 0.55 B hydroxybutane hydrochloride209 1-(4-(4-(5H-Dibenzo[ a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)pi peridine 412 0.03 B dihydroxybutane hydrochloride210 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(N-imidazolylmethyl)cinna myl)piperidine 469 0.44 B dihydroxybutane hydrochloride211 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphthoyl)piperidine 427 0.88 B212 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphthylmethyl)piperidine hydrochloride 413 0.94 B213 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphthoyl)piperidine 427 0.59 B214 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphthylmethyl)piperidine hydrochloride 413 0.83 B215 2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)cycl ohexanone hydrochloride 426 0.50 B (H+)216 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)- 4-hydroxypiperidine hydrochloride 442 0.58 B217 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)- 4-ethoxyxarbonpiperidine 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 0.55 B hydrochloride (H+)220 Ethyl 2-cyclohexyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperi dinyl)valerate hydrochloride 483 0.65 B221 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(3',4'-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 hydrochloride 456 0.38 B (H+)224 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphth oyl)piperidine 431 0.90 B225 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphth ylmethyl)piperidine 417 0.55 B226 N-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanoyl) cyclohexylamine hydrochloride 426 0.64 B227 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl cyclohexanecarboxylate hydrochloride 427 0.71 B228 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-cyclohexylbutane hydrochloride 431 0.74 B229 4-(4-(5H-Dibenzo[a,d]thiepin-5-ylidene)-1-piperidinyl)-3+,4+-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 hydrochloride 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-t etrahydropyranyl)ether 415 0.55 B hydrochloride236 Cyclohexyl 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)pr opionate hydrochloride 427 0.71 B237 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)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 ',6'-dimethoxyindan hydrochloride 477 0.41 B241 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',4'-d imethoxybenzamide hydrochloride 480 0.44 G243 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl cyclohexanecarboxamide hydrochloride 426 0.75 B244 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl isonicotinamide hydrochloride 421 0.20 B245 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)m orpholine hydrochloride 428 0.31 C246 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)t hiomorpholine hydrochloride 444 0.43 C247 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-notroph enyl)propane hydrochloride 436 0.34 H248 1-(4-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid inyl)propane dihydrochloride 406 0.33 B249 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 dihydrochloride 406 0.52 B252 1-(2-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-p iperidinyl)propane 448 0.51 B dihydrochloride253 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylpheny lsulphoxide hydrochloride 425 0.20 H254 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl phenylsulphone hydrochloride 455 0.71 B255 4-(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 hydrochloride 430 0.17 J (H+)257 Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1 -propylsulphoxide hydrochloride 445 0.51 B258 Cyclohexyl-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1 -propylsulphone hydrochloride 462 0.28 H (H+)259 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-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5',6 '-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)ethylsulfone hydrochloride 461 0.94 B264 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidi nyl)-1-ethylsulfoxide 441 0.48 B hydrochloride (H+)265 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidi nyl)-1-ethylsulfide hydrochloride 429 0.85 B266 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-ethoxycarbonylcyclohexane 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',4'-dimeth oxybutyrophenone N-oxide 477 0.45 B (M-18)272 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-ylidene)-1-piperi dinyl)-1-butyl)cyclohexane 483 0.86 B hydrochloride274 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyl-3', 4'-dimethoxybutyrophenone 493 0.22 B hydrochloride275 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-propyl) -3',4'-dimethoxybutyrophenone 521 0.28 H hydrochloride276 2-Allyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3',4 'dimethoxybutyrophenone 519 0.30 H hydrochloride277 4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-propyl) -3',4'-dimethoxybutyrophenone 521 0.38 H hydrochloride278 4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-3',4 '-dimethoxybutyrophenone 507 0.33 H hydrochloride279 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidi nyl)-2-ethyl)ether hydrochloride 413 0.73 B280 1-(n-Acetyl-3-piperidinyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)- 1-piperidinyl)propane hydrochloride 440 0.75 B281 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)-1-(3-piperii dinyl)propane dihydrochloride 398 0.16 A282 1-(3-Acetylamino-4-methoxyphenyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-yl idine)-1-piperidinyl)butane 492 0.58 B hydrochloride283 4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)-1-butyl)c yclohexane hydrochloride 425 0.63 B284 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)-1-(2-pyridyl )-1-propene hdiydrochloride 390 0.66 H285 2,6-Dimethyl-4-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)-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-ylidine)-1-piperidinyl)-1-(2,3-dimet hoxyphenyl)propane hydrochloride 451 0.68 H287 2-(4-(5H-Dibenzo[ a,d]cyclohepten-5-ylidine)-1-piperidinyl)methyl-5',6 '-dimethoxyindan hydrochloride 463 0.59 H288 2,6-Dimethyl-4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidin yl)-1-butyl)-5-methylpyrydine- 527 0.68 B 3,5-dicarboxylate dihydrochloride289 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)-1-(4-pyridyl )propane dihydrochloride 392 0.37 B290 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)ethyl-3-nitro benzamide hydrochloride 466 0.48 D (H+)291 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)ethyl-2-nitro benzamide hydrochloride 466 D (H+)292 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)ethyl-3,4-dim ethoxybenzamide hydrochloride 481 0.31 D (H+)293 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)-1-(2-pyrolle )-1-butane hydrochloride 409 B (H+)294 1-(N-Acetyl-2-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)- 1-piperidinyl)propane hydrochloride 440 0.30 B295 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidine)-1-piperidinyl)-1-(N-methyl- 3-piperidinyl)butane dihydrochloride 426 0.07 B296 1-(1-(4-Hydroxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidine) -1-piperidinyl)butane hydrochloride 427 0.45 B297 1-(1-(4-Cyano)cyclohexyl)-4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1 -piperidinyl)butane hydrochloride 436 0.55 F298 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-methoxy phenyl)propane hydrochloride 421 0.81 B299 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 yclohexanoe 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 hydrochloride 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)t etrahydropyran 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 A308 1-(N-Acetyl-4-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)- 1-piperidinyl)propane hydrochloride 440 0.23 H309 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-piperid inyl)propane dihydrochloride 398 0.03 B310 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)i ndane hydrochloride 417 0.59 B311 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-dihydropyridine-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 hydrochloride 994 0.48 B317 3-(4-(5H-Dibenzol[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4,5-tr imethoxyphenyl)propane 481 0.65 B dihydrochloride318 2-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)- 5,6-dimethoxy- 491 0.21 H 1,2,3,4-tetrahydronaphthalene 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- 1000 0.30 B 1,4-dihydropyridine-3,5-dicarboxylate hydrochloride323 2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)- 3,4,5,6-tetramethylpyridine- 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 (5H-Dibenzo[b,e]thiepiz-5-ylidene)-1-(4-nitrocinnamyl)piperidine hydrochloride 454 0.89 B326 1-(4-Aminocinnamyl)-4-(5H-Dibenzo[b,e]thiepiz-5-ylidene)piperidine dihydrochloride 424 0.65 B327 1-(4-Acetylaminominocinnamyl)-4-(5H-Dibenzo[b,e]thiepiz-5-ylidene)piper idine hydrochloride 466 0.58 B328 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2,4-dimet hoxyphenyl)propane dihydrochloride 451 0.64 B329 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-4'-nit roindan hydrochloride 448 0.49 I330 4'-Amino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)meth ylindan hydrochloride 418 0.38 H331 4'Acetylamino-2(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-Piperidinyl) methylindan hydrochloride 460 0.33 B332 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-5'-nit roindan hydrochloride 448 0.50 I333 5'-Amino2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methy lindan hydrochloride 418 0.34 B334 5'-Acetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidiny l)methyllindan 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 lisonicotinamide hydrochloride 455 B338 1-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethy lisonicotinamide hydrochloride 455 B339 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethynicotinam ide hydrochloride 421 0.42 B340 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethnicotinami de N-oxide hydrochloride 437 0.27 D (H+)341 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonicot inamide N-oxide hydrochloride 437 0.30 D (H+)342 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 dihydrochloride 406 0.64 B352 1-(4-Acetylaminocinnamyl)-4-(10.11 dihydro-5H-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'-nitroindan hydrochloride 462 0.34 H355 4'-Amino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-pioperidinyl) -1-ethyl)indan hydrochloride 432 0.53 B356 4'-Acetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidiny l)-1-ethyl)indan hydrochloride 474 0.24 B357 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)- 5'-nitroindan hydrochloride 462 0.31 H358 5'-Amino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)- 1-ethyl)indan dihydrochloride 432 0.23 H359 5'-Acetylamino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperid inyl)-1-ethyl)indan dihydrochloride 474 0.05 H360 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)- 5'-methanesulfonylaminoindan 510 0.11 H hydrochloride361 1-(Cyclohexyl-4-(4-(10.11-dihydroxy-5H-Dibenzo[a,d]cyclohepten-5-yliden e)-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)piperdine hydrochloride 406 0.55 B (H+)364 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-methoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene )piperidine hydrochloride 477 0.83 B367 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-hydroxycinnamyl)piperidin e 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-ethoxycarbonylaminocinnam yl)piperidine hydrochloride 476 0.20 H372 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methanesulfonylaminocinna myl)piperidine hydrochloride 482 0.44 B373 1-(N,N-Bis(methanesulfonyl)aminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten -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)pi peridine hydrochloride 464 0.30 H378 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylaminocinna myl)piperidine hydrochloride 462 0.53 B379 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-ethoxycarbonylcinnamyl)pi peridine 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 0.35 B (H+)385 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 0.48 B (H+)387 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 dose 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 -11108 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 -129 -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 -20308 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.

Claims

1. A piperidine compound of the formula (I) ##STR3## wherein: A is pyridine;

R is --H, --Cl or --OCH.sub.3 ;

X is --(CH.sub.2).sub.n --, --CO--(CH.sub.2).sub.3, --CONH--(CH.sub.2).sub.2, --NHCO--(CH.sub.2).sub.2, or --CH.dbd.CH--(CH.sub.2).sub.2 --; and

n is an integer of from 3 to 5;

Y is --CH.dbd.CH--, --(CH.sub.2).sub.2, --OCH.sub.2 --, --SCH.sub.2 --, or --O--; and

Q is --CN, substituted or unsubstituted cyclohexyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted piperazinyl, substituted or unsubstituted phenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted morpholinyl, or substituted or unsubstituted thiomorpholinyl, wherein when Q is substituted, the substituent(s) is/are selected from the group consisting of H--CH.sub.2).sub.n wherein n is an integer of 1 to 10, Cl--CH.sub.2).sub.3, allyl, formyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, ethoxycarboxyl, 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, and wherein when X and/or Q contain --CH.sub.2 -- groups, one or more of the --CH.sub.2 -- groups in X and/or Q may be substituted by --CH.sub.2).sub.4 or --CH.sub.2).sub.5, thereby forming a ring structure.

2. The piperidine compound of claim 1, wherein the hydrogen atoms of one or more of the --CH.sub.2 -- groups in X and Q are substituted by --CH.sub.2).sub.4 or --CH.sub.2).sub.5, thereby forming a ring structure.

3. The piperidine compound of claim 1, wherein Q is substituted by at least one substituent selected from the group consisting of H--CH.sub.2).sub.n wherein n is an integer of 1 to 10, Cl--CH.sub.2).sub.3, allyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, ethoxycarboxyl, 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.

4. The piperidine compound of claim 1, wherein X is --CONH--(CH.sub.2).sub.2.

5. The piperidine compound of claim 1, wherein Y is --CH.dbd.CH--.

6. The piperidine compound of claim 1, wherein Y is --(CH.sub.2).sub.2 --.

7. The piperidine compound of claim 1, wherein Q is substituted or unsubstituted piperidinyl.

8. The piperidine compound of claim 1, wherein X is --CONH--(CH.sub.2).sub.2, and Q is substituted or unsubstituted piperidinyl.

9. A piperidine compound of the formula ##STR4## wherein: R is --H, --Cl or --OCH.sub.3 ;

X is --(CH.sub.2).sub.n --, --CO--(CH.sub.2).sub.4, --CONH--(CH.sub.2).sub.2, --NHCO--(CH.sub.2).sub.2, or --CH.dbd.CH--(CH.sub.2).sub.2 --; and

n is an integer of from 3 to 5;

Y is --CH.dbd.CH--, --(CH.sub.2).sub.2 --, --OCH.sub.2 --, --SCH.sub.2 --; and

Q is --CN, substituted or unsubstituted piperidinyl, substituted or unsubstituted piperazinyl, substituted or unsubstituted thienyl, substituted or unsubstituted morpholinyl, or substituted or unsubstituted thiomorpholinyl, wherein when Q is substituted, the substituent(s) is/are selected from the group consisting of H--CH.sub.2).sub.3 wherein n is an integer of 1 to 10, Cl--CH.sub.2).sub.3, allyl, formyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, carboxyl, methoxycarbonyl, ethoxycarbonyl, cyano, imidazolylmethyl, trifluoromethyl, benzoyl, 2-hdyroxybenzyl, nitro, amino, acetylamino, propanoylamino, butanoylamino, pivaloylamino, trifluoromethylamino, methoxycarbonylamino, ethoxycarbonylamino, cinnamoylamino, methanesulfonylamino, N,N-bis(methanesulfonyl)amino, aminocarbonyl, aminosulfonyl, hydroxymethyl and acetoxymethyl, and wherein when X and/or Q contain --CH.sub.2 -- groups, one or more of the --CH.sub.2 -- groups in X and/or Q may be substituted by --CH.sub.2).sub.4 or --CH.sub.2).sub.5, thereby forming a ring structure.

10. The piperidine compound of claim 9, wherein X is --CONH--(CH.sub.2).sub.2, Y is --CH.dbd.CH--, and Q is N-formylpiperidinyl.

11. A piperidine compound of the formula ##STR5## wherein: R is --H, --Cl or --OCH.sub.3 ;

X is --CO--(CH.sub.2).sub.3, --CONH--(CH.sub.2).sub.2, --NHCO--(CH.sub.2).sub.2, or --CH.dbd.CH-- (CH.sub.2).sub.2 --; and

Q is --CN, substituted or unsubstituted cyclohexyl, substituted or unsubstituted piperidinyl, substituted or unsubstituted piperazinyl, substituted or unsubstituted phenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, substituted or unsubstituted morpholinyl, or substituted or unsubstituted thiomorpholinyl, wherein when Q is substituted, the substituent(s) is/are selected from the group consisting of H--CH.sub.2).sub.n wherein n is an integer of 1 to 10, Cl--CH.sub.2).sub.3, allyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, ethoxycarboxyl, 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, and wherein when X and/or Q contain --CH.sub.2 -- groups, one or more of the --CH.sub.2 -- groups in X and/or Q may be substituted by --CH.sub.2).sub.4 or --CH.sub.2).sub.5 thereby forming a ring structure.

12. A piperidine compound of the formula ##STR6## wherein: R is --H, --Cl or --OCH.sub.3 ;

X is --(CH.sub.2).sub.n --;

n is an integer of from 3 to 5; and

Q is --CN, substituted or unsubstituted phenyl, substituted or unsubstituted furyl, substituted or unsubstituted thienyl, substituted or unsubstituted pyrrolyl, substituted or unsubstituted pyridyl, wherein when Q is substituted, the substituent(s) is/are selected from the group consisting of H--CH.sub.2).sub.n wherein n is an integer of 1 to 10, Cl--CH.sub.2).sub.3, allyl, phenyl, isopropyl, hydroxy, methoxy, ethoxy, fluoro, chloro, acetoxy, 2-methoxyacetoxy, ethoxycarboxyl, 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, and wherein one or more of the --CH.sub.2 -- groups in X may be substituted by --CH.sub.2).sub.4 or --CH.sub.2).sub.5 thereby forming a ring structure.