USRE38257E1 - Piperdine derivatives and hypotensives containing the same - Google Patents

Piperdine derivatives and hypotensives containing the same Download PDF

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USRE38257E1
USRE38257E1 US09/248,236 US24823699A USRE38257E US RE38257 E1 USRE38257 E1 US RE38257E1 US 24823699 A US24823699 A US 24823699A US RE38257 E USRE38257 E US RE38257E
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dibenzo
ylidene
cyclohepten
piperidinyl
hydrochloride
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US09/248,236
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Masataka Shoji
Kozo Toyota
Chikahiko Eguchi
Ryota Yoshimoto
Yoshikatsu Koyama
Hideki Domoto
Akira Kamimura
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Ajinomoto Co Inc
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Ajinomoto Co Inc
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Priority claimed from US07/354,880 external-priority patent/US5231105A/en
Priority claimed from US07/655,775 external-priority patent/US5250681A/en
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
    • C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D295/145—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with the ring nitrogen atoms and the carbon atoms with three bonds to hetero atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
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    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/01—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms
    • C07C255/32—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring
    • C07C255/42—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms
    • C07C255/43—Carboxylic acid nitriles having cyano groups bound to acyclic carbon atoms having cyano groups bound to acyclic carbon atoms of a carbon skeleton containing at least one six-membered aromatic ring the carbon skeleton being further substituted by singly-bound nitrogen atoms, not being further bound to other hetero atoms the carbon skeleton being further substituted by singly-bound oxygen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
    • C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
    • C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
    • C07D211/32—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
    • C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D211/40—Oxygen atoms
    • C07D211/44—Oxygen atoms attached in position 4
    • C07D211/52—Oxygen atoms attached in position 4 having an aryl radical as the second substituent in position 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
    • C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D211/68—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
    • C07D211/70—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
    • C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
    • C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/02—Ortho- or ortho- and peri-condensed systems
    • C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
    • C07C2603/30—Ortho- or ortho- and peri-condensed systems containing three rings containing seven-membered rings
    • C07C2603/32—Dibenzocycloheptenes; Hydrogenated dibenzocycloheptenes

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Hydrogenated Pyridines (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

A piperidine compound of the formula (I):
Figure USRE038257-20030923-C00001
wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH2)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(COCH3)—, —N(COOC2H5)—, —N(CHO)—, —N(CH3)—, —CO—, —SO—, or —SO2—; Y is —CH≡CH—, —CH2CH2—, —CH2CO—, —O—, —S—, —NH—, —OCH2—, —SCH2—, —NHCH2—, —CH(OH)CH2— 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 —(CH2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by —CH≡CH—, —C≡C—, —O—, —S—, —NH—, —N(COCH3), —N(COC2H5)—, —N(CHO)—, —N(CH3), —CO—, —SO— or —SO2—, and wherein one or more of the —(CH2)-groups in X and Q may be substituted by —(CH2)4— or —(CH2)5— thereby forming a ring structure.

Description

This application is a reissue application of application Ser. No. 08/269,628, filed Jul. 1, 1994, now U.S. Pat. No. 5,393,890 which in turn is a continuation of application Ser. No. 08/072,458, filed Jun. 7, 1993, now abandoned, which is a continuation of application Ser. No. 07/655,775, filed Feb. 15, 1991, now U.S. Pat. No. 5,250,681, which is a continuation of application Ser. No. 07/443,438, filed Nov. 30, 1989, now abandoned, which is a continuation of application Ser. No. 07/354,880, filed May 22, 1989, now U.S. Pat. No. 5,231,105, which is a continuation of application Ser. No. 07/201,911, filed Jun. 2, 1988, now abandoned.
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):
Figure USRE038257-20030923-C00002
wherein A is a fused aromatic ring; R is hydrogen, chloro or methoxy; X is (CH2)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(COCH3)—, —N(COOC2H5)—, —N(CHO)—, —N(CH3)—, —CO—, —SO—, or —SO2—; Y is —CH≡CH—, —CH2CH2—, —CH2CO—, —O—, —S—, —NH—, —OCH2—, —SCH2—, —NHCH2—, —CH(OH)CH2—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 —(CH2)-groups of the hexyl, carboxypropyl, ethoxycarbonylpropyl and cyanopropyl groups may be replaced by —CH≡CH—, —C≡C—, —O—, —S—, —NH—, —N (COCH3), —N(COC2H5)—, —N(CHO)—, —N(CH3)—, —CO—, —SO— or —SO2—, and wherein one or more of the —(CH2)-groups in X and Q may be substituted by —(CH2)4— or —(CH2)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, C1(CH2)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 CDCl3 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 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)amino ethyl)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-dimethoxy phenyl)-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-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-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
exp compound (M+) (Rf) solvent
127 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl-1-(4-fluorophenyl)ethane hydrochloride 395 0.55 B
128 1-(2-Chlorobenzyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 397 0.68 B
129 1-(3-Chlorobenzyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 397 0.58 B
130 1-(4-Chlorobenzyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 397 0.58 B
131 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methylbenyl)piperidine hydrochloride 377 0.74 B
132 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methylbenyl)piperidine hydrochloride 377 0.71 B
133 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methylbenyl)piperidine hydrochloride 377 0.65 B
134 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-heptylpiperidine hydrochloride 371 0.70 B
135 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-nondecylpiperidine hydrochloride 399 0.75 B
136 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-undecylpiperidine hydrochloride 427 0.75 B
137 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-tridecylpiperidine hydrochloride 455 0.78 B
138 1-(2-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine dihydrochloride 392 0.38 B
139 1-(3-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine dihydrochloride 392 0.23 B
140 1-(4-Aminobenzy)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine dihydrochloride 392 0.26 B
141 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrobenzyl)piperidine hydrochloride 422 0.85 B
142 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-nitrobenzyl)piperidine hydrochloride 422 0.82 B
143 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrobenzyl)piperidine hydrochloride 422 0.83 B
144 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3-fluorophenyl)-2-isopropylvaleronitrile 500 0.71 B
hydrochloride
145 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3-methoxyphenyl)valeronitrile 512 0.64 B
hydrochloride
146 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(3-methylphenyl)valeronitrile 496 0.68 B
hydrochloride
147 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(2- 549 0.78 B
trifluoromethylphenyl)valeronitrile hydrochloride
148 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-isopropyl-2-(4- 540 0.77 B
trifluoromethylphenyl)valeronitrile hydrochloride
149 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-2-(3- 526 0.77 B
trifluoromethylphenyl)valeronitrile hydrochloride
150 2-Butyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(3- 554 0.80 B
trifluoromethylphenyl)valeronitrile hydrochloride
151 5-(4-(5H-Dibenzo[ac]cyclohepten-5-ylidene)-1-piperidinyl)-2-hexyl-2-(3- 582 0.80 B
trifluoromethylphenyl)valeronitrile hydrochloride
152 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-phenyl-1-butene hydrochloride 403 0.51 B
153 1-Benzyloxy-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethane hydrochloride 407 0.58 B
154 1-Cyclohexyl-6-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)hexane hydrochloride 439 0.62 B
155 1-Cyclohexyl-7-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)heptane hydrochloride 453 0.65 B
156 1-Cyclohexyl-8-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)octane hydrochloride 467 0.68 B
157 1-(4-Cyclohexylbutanoyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine 425 0.75 B
158 1-(2-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 388 0.83 B
159 1-(3-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 388 0.85 B
160 1-(4-Cyanobenzyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 388 0.70 B
161 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-Picolyl)piperidine dihydrochloride 364 0.58 B
162 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-Picolyl)piperidine dihydrochloride 364 0.53 B
163 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-Picolyl)piperidine dihydrochloride 364 0.44 B
164 1-Decanolyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine 427 0.75 B
165 1-Cyano-3-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane hydrochloride 340 0.58 B
166 1-Cyano-4-[4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane hydrochloride 354 0.52 B
167 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxyacetophenone hydrochloride 451 0.85 B
168 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxypropiophenone hydrochloride 465 0.61 B
169 5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxyvalerophenone hydrochloride 193 0.64 B
170 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′,5′-trimethoxybutyrophenone 509 0.82 B
hydrochloride
171 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2′,3′,4′-trimethoxybutyrophenone 509 0.86 B
hydrochloride
172 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4′-trimethoxybutyrophenone 449 0.61 B
hydrochloride
173 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,3-dimethoxybenzyl)piperidine hydrochloride 423 0.63 B
174 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimethoxybenzyl)piperidine hydrochloride 423 0.73 B
175 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dimethoxybenzyl)piperidine 437 0.58 B
176 1-Cyclohexyl-3,(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propylketone hydrochloride 425 0.51 B
177 2-Cyclohexyl-5,(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)valeronitrile hydrochloride 436 0.60 B
178 1-(4-(3-Chloro-5H-dibenzo[a,d]cyclohepten-5-ylidene-1-piperidinyl)-4-cyclohexylbutane hydrochloride 445 0.62 B
179 1-Cyclohexyl-(4-(3-methoxy-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane hydrochloride 441 0.59 B
180 4,9-Dihydro-4-(1-(4-cyclohexylbutyl)-4-piperidinylidene-10H-benzo[4,5]cyclohepta[1,2-b]thiophen-10-one 433 0.45 B
hydrochloride
181 1-(4-Cyclohexylbutyl-4-(9-xantylidene)piperidine hydrochloride 401 0.64 B
182 1-(4-Cyclohexylbutyl-4-(9-thioxantylidene)piperidine hydrochloride 417 0.65 B
183 6,11-Dihydro-11-(1-(4-cyclohexylbutyl)-4-piperidinylidene-5H-dibenzop[5,6]cycloheptal[1,2-b]pyridine 414 0.41 B
dihydrochloride
184 4-(10,11-dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxybenzyl)piperidine hydrochloride 395 0.73 B
185 1-Decyl-4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 415 0.52 B
186 1-Cyclohexyl-4-(10,11-Dihydro-5H-dibenzo[a,d]cycloheptan-5-ylidene)-1-piperidinyl)butane 413 0.67 B
hydrochloride
187 4-(4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxy- 481 0.66 B
butyrophenone hydrochloride
188 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxybenzyl)piperidine 453 0.69 B
189 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxybenzoyl)piperidine 467 0.71 B
190 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methylbenzoyl)piperidine 391 0.73 B
191 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-(4-fluorophenyl)acetyl)piperidine 409 0.76 B
192 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-dimethoxycinnamoyl)piperidine 463 0.73 B
193 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-dimethoxycinnamyl)piperidine hydrochloride 449 0.46 B
194 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-diethoxybutyrophenone hydrochloride 501 0.49 B
195 1-(4-(4-Aminophenyl)butyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)piperidine dihydrochloride 420 0.34 B
196 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(4-nitrophenyl)butyl)piperidine hydrochloride 450 0.50 B
197 1-(4-(4-Acetylaminophenyl)butyl-4-(5H-dibenzo[a,d]cyclohepten-5-ylidine)piperidine dihydrochloride 462 0.48 B
198 4-(4-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethylbutyrophenone hydrochloride 447 0.53 B
199 Ethyl 4-(4-(5H-dibanzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyrate hydrochloride 387 0.51 B
200 4-((4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyric acid 359 0.15 B
201 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(-3-(3′,4′-dimethoxyphenyl)propyl)piperidine hydrochloride 451 0.60 B
202 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(3′,4′-dimethoxyphenyl)propanoyl)piperidine 465 0.78 B
203 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)piperidine hydrochloride 426 0.60 B
204 N-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-1,2,3,4-tetrahydroisoquinoline 474 0.42 B
hydrochloride
205 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4-dimethoxy)phenyl-1-hydroxybutane 481 0.38 B
hydrochloride
206 1-Acetoxy-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-(3,4-dimethoxy)phenylButane 523 0.49 B
hydroxybutane hydrochloride
207 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 hydrochloride
208 1-(4-Methoxyxyxlohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane 441 0.55 B
hydroxybutane hydrochloride
209 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)piperidine 412 0.03 B
dihydroxybutane hydrochloride
210 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-N-imidazolylmethyl)cinnamyl)piperidine 469 0.44 B
dihydroxybutane hydrochloride
211 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphthoyl)piperidine 427 0.88 B
212 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-naphthylmethyl)piperidine hydrochloride 413 0.94 B
213 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphthoyl)piperidine 427 0.59 B
214 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1-naphthylmethyl)piperidine hydrochloride 413 0.83 B
215 2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)cyclohexanone 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 B
217 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)-4-ethoxyxarbonpiperidine 499 0.26 B
hydrochloride
218 Cyclohexyl 3-(4-(5H-Dibenzo[a,d]cyclohpetan-5-ylidene)-1-piperidinyl)propylether hydrochloride 413 0.48 B
219 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-butyl)-1-methoxycarbonylcyclohexane 470 0.55 B
hydrochloride (H+)
220 Ethyl 2-cyclohexyl-5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)valerate hydrochloride 483 0.65 B
221 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(3′,4′-dimethoxyphenyl)butyl)piperidine hydrochloride 465 0.66 B
222 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 hydrochloride
223 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-naphthoyl)piperidine 431 0.90 B
225 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(1,2,3,4-tetrahydro-2-naphthylmethyl)piperidine 417 0.55 B
226 N-(3,(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propanoyl)cyclohexylamine hydrochloride 426 0.64 B
227 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl cyclohexanecarboxylate hydrochloride 427 0.71 B
228 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-cyclohexylbutane hydrochloride 431 0.74 B
229 4-(4-(5H-Dibenzo[a,d]thiepin-5-ylidene)-1-piperidinyl)-3+,4+-dimethoxybutyrophenone hydrochloride 499 0.46 B
230 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrocinnamyl)piperidine hydrochloride 434 0.70 B
231 1-(4-Aminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 404 0.36 B
232 1-(4-Acetylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)piperidine dihydrochloride 446 0.27 B
233 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-furyl)-1-butanone hydrochloride 409 B
234 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-thienyl)-1-butanone hydrochloride 425 B
235 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl(2-tetrahydropyranyl)ether 415 0.55 B
hydrochloride
236 Cyclohexyl 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propionate hydrochloride 427 0.71 B
237 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-4-nitrobenzamide hydrochloride 465 0.49 H
238 2-Cyclohexyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyric acid 455 0.26 B
239 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl phenylsulphoxide hydrochloride 409 0.29 H
240 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl-5′,6′-dimethoxyindan hydrochloride 477 0.41 B
241 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl phenylsulphone hydrochloride 441 0.36 B
242 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3′,4′-dimethoxybenzamide hydrochloride 480 0.44 G
243 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl cyclohexanecarboxamide hydrochloride 426 0.75 B
244 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl isonicotinamide hydrochloride 421 0.20 B
245 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)morpholine hydrochloride 428 0.31 C
246 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butanoyl)thiomorpholine hydrochloride 444 0.43 C
247 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-notrophenyl)propane hydrochloride 436 0.34 H
248 1-(4-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane dihydrochloride 406 0.13 B
249 1-(4-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane 448 0.43 B
dihydrochloride
250 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-nitrophenyl)propane hydrochloride 436 0.53 H
251 1-(2-Aminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane dihydrochloride 406 0.52 B
252 1-(2-Acetylaminophenyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane 448 0.51 B
dihydrochloride
253 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylphenylsulphoxide hydrochloride 425 0.20 H
254 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl phenylsulphone hydrochloride 455 0.71 B
255 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-nitrophenyl)butane hydrochloride 450 0.49 H
256 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 B
258 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
hydrochloride
260 1-(4-acetylamino-1-cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane 468 0.43 B
hydrochloride
261 2-(2-4-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5′,6′-dimethoxy-1-indanone 477 0.41 B
hydrochloride
262 Ethyl 2-(2-cyclohexylethyl-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propionate 483 0.74 B
hydrochloride
263 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylsulfone hydrochloride 461 0.94 B
264 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylsulfoxide 441 0.48 B
hydrochloride (H+)
265 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethylsulfide hydrochloride 429 0.85 B
266 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-4-amino-6,7-dimethoxyquinazoline 476 0.34 B
dihydrochloride
267 N-Acetyl-N-(3-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propylcyclohexylamine 454 0.35 B
hydrochloride
268 N-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-2-piperidone hydrochloride 426 0.39 B
269 1-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-1-ethoxycarbonxylcyclohexane 483 0.82 B
hydrochloride
270 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-pyridyl)propane dihydrochloride 392 0.44 B
271 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′-dimethoxybutyrophenone 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
hydrochloride
273 1-Acetoxymethyl-1-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)cyclohexane 483 0.86 B
hydrochloride
274 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-methyl-3′,4′-dimethoxybutyrophenone 493 0.22 B
hydrochloride
275 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(2-propyl)-3′,4′-dimethoxybutyrophenone 521 0.28 H
hydrochloride
276 2-Allyl-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-3′,4′dimethoxybutyrophenone 519 0.30 H
hydrochloride
277 4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-(1-propyl)-3′,4′-dimethoxybutyrophenone 521 0.38 H
hydrochloride
278 4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl-3′,4′-dimethoxybutyrophenone 507 0.33 H
hydrochloride
279 Cyclohexylmethyl-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-2-ethyl)ether hydrochloride 413 0.73 B
280 1-(n-Acetyl-3-piperidinyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane hydrochloride 440 0.75 B
281 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-piperidinyl)propane dihydrochloride 398 0.16 A
282 1-(3-Acetylamino-4-methoxyphenyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane 492 0.58 B
hydrochloride
283 4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)cyclohexane hydrochloride 425 0.63 B
284 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-pyridyl)-1-propane hydrochloride 390 0.66 H
285 2,6-Dimethyl-4-(4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butyl)-5-methyl-1,4- 528 0.30 F
dihydropyrydine-3,5-dicarboxylate hydrochloride
286 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2,3-dimethoxyphenyl)propane hydrochloride 451 0.68 H
287 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-5′,6′-dimethoxyindan hydrochloride 463 0.59 H
288 2,6-Dimethyl-4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-5-methylpyrydine- 527 0.68 B
3,5-dicarboxylate dihydrochloride
289 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(4-pyridyl)propane dihydrochloride 392 0.37 B
290 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-3-nitrobenzamide hydrochloride 466 0.48 D
(H+)
291 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-2-nitrobenzamide hydrochloride 466 D
(H+)
292 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethyl-2,4-dimethoxybenzamide hydrochloride 481 0.31 D
(H+)
293 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-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-ylidene)-1-piperidinyl)propane hydrochloride 440 0.30 B
295 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(N-methyl-3-piperidinyl)butane dihydrochloride 426 0.07 B
296 1-(1-(4-Hydroxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane hydrochloride 427 0.45 B
297 1-(1-(4-Cyano)cyclohexyl)-4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane hydrochloride 436 0.55 F
298 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-methoxyphenyl)propane hydrochloride 421 0.81 B
299 1-(1-(3-Methoxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane 441 0.71 B
hydrochloride
300 1-(1-(3-Hydroxyoxy)cyclohexyl)-4-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane 427 0.47 B
hydrochloride
301 3-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)cyclohexanoe hydrochloride 425 0.70 B
302 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-nitrocinnamyl)piperidinyl hydrochloride 434 0.91 B
303 1-(2-Aminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride 404 0.62 B
304 1-(2-Acetylaminocinnamyl)-4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride 446 0.55 B
305 4-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)tetrahydropyran hydrochloride 413 0.69 B
306 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-nitrocinnamyl)piperidine hydrochloride 984 0.90 B
307 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2-piperidinyl)propane dihydrochloride 398 0.07 A
308 1-(N-acetyl-4-piperidinyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane hydrochloride 440 0.23 H
309 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane dihydrochloride 398 0.03 B
310 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indane hydrochloride 417 0.59 B
311 4-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ehtyl)-2,4,5,6-tetramethyl- 524 0.68 B
1,4-dihydropyridino-3,5-dicarboxylate hydrochloride
312 4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(N-ethoxycarbonyl-3-piperidinyl)butane 484 0.64 B
hydrochloride
313 1-(5-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-pentyl)-1-methoxycarbonylcyclohexane 483 0.72 B
hydrochloride
314 1-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-propyl)-1-methoxycarbonylcyclohexane 455 0.75 B
hydrochloride
315 1-(3-Aminophenyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane dihydrochloride 993 0.62 B
316 1-(3-Acetylaminophenyl)-3-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane hydrochloride 994 0.48 B
317 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3,4,5-trimethoxyphenyl)propane 481 0.65 B
dihydrochloride
318 2-(3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5,6-dimethoxy- 491 0.21 H
1,2,34-tetrahydronaphthalene hydrochloride
319 6-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-2,3-dimethoxybenzocycloheptene 491 0.56 H
hydrochloride
320 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4,5-trimethoxycinnamyl)piperdine hydrochloride 479 0.69 B
321 1-(N-Acetyl-4-piperidinyl)-5-(4-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-pentene 466 0.33 B
dihydrochloride
322 2-(4-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-butyl)-3,4,5,6-tetrmethyl- 1000  0.30 B
1,4-dihydropyridine-3,5-dicarboxylate hydrochloride
323 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 hydrochloride
324 1-(1-(4-Methoxy)cyclohecyl)-3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)propane 427 0.48 B
hydrochloride
325 (5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrocinnamyl)piperidine hydrochloride 454 0.89 B
326 1-(4-Aminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine dihydrochloride 424 0.65 B
327 1-(4-Acetylaminominocinnamyl)-4-(5H-Dibenzo[a,d]thiepiz-5-ylidene)-1-piperidine hydrochloride 466 0.58 B
328 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(2,4-dimethoxyphenyl)propane dihydrochloride 451 0.64 B
329 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-4′-nitroindan hydrochloride 448 0.49 I
330 4′-Amino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methylindan hydrochloride 418 0.38 H
331 4′Acetylamino-2(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-Piperidinyl)methylindan hydrochloride 460 0.33 B
332 2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methyl-5′-nitroindan hydrochloride 448 0.51 I
333 5′-Amino2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methylindan hydrochloride 418 0.34 B
334 5′-acetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)methylindan hydrochloride 460 0.29 H
335 4-Amino-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylbenzamide hydrochloride 435 B
336 3-Amino-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylbenzamide hydrochloride 435 B
337 1-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonipecotinamide hydrochloride 455 B
338 1-Formyl-N-(2-(5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonicotinamide hydrochloride 455 B
339 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylnicotinamide hydrochloride 421 0.42 B
340 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethnicotinamide N-oxide hydrochloride 437 0.27 D
(H+)
341 N-(2-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)ethylisonicotinamide N-oxide hydrochloride 437 0.30 D
(H+)
342 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,4-dimethoxycinnamyl)piperidine hydrochloride 449 0.73 B
343 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,5-dimethoxycinnamyl)piperidine hydrochloride 449 0.73 B
344 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2,3-dimethoxycinnamyl)piperidine hydrochloride 449 0.90 B
345 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,5-dimethoxycinnamyl)piperidine hydrochloride 449 0.74 B
346 1-(4-Cyanocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride 414 0.70 B
347 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxycinnamyl)piperidine hydrochloride 419 0.87 B
348 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxycinnamyl)piperidine hydrochloride 419 0.89 B
349 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride 419 0.85 B
350 4-(10,11-Dihydro-5H-dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-nitrocinnamyl)piperidine hydrochloride 436 0.93 B
351 1-(4-Aminocinnamyl)-4-(10,11-dihydro-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine dihydrochloride 406 0.64 B
352 1-(4-Acetylaminocinnamyl)-4-(10,11 dihydro-5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine 448 0.54 B
dihydrochloride
353 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-4-fluorocinnamyl)piperidine hydrochloride 407 0.88 B
354 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-4′-nitroindan hydrochloride 462 0.34 H
355 4′-Amino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indan hydrochloride 432 0.53 B
356 4′-Caetylamino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indan hydrochloride 474 0.24 B
357 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5′-nitroindan hydrochloride 462 0.31 H
358 5′-Amino-2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indan dihydrochloride 432 0.23 H
359 5′-Acetylamino-2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)indan dihydrochloride 474 0.05 H
360 2-(2-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-ethyl)-5′-methanesulfonylaminoindan 510 0.11 H
hydrochloride
361 1-(Cyclohexyl-4-(4-(10,11-dihydroxy-5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)butane 445 0.84 B
362 3-(4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidinyl)-1-(3-pyridyl)-1-propene dihydrochloride 390 0.44 B
363 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-hydroxycinnamyl)piperidine hydrochloride 406 0.55 B
(H+)
364 1-(4-Acetoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 447 0.87 B
365 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-hydroxy-3-methoxycinnamyl)piperidine hydrochloridine 435 0.63 B
366 1-(4-Acetoxy-3-methoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-piperidine hydrochloride 477 0.83 B
367 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-hydroxycinnamyl)piperidine hydrochloride 405 0.45 B
368 1-(3-Acetoxycinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 447 0.80 B
369 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-(2-methoxyacetoxy)cinnamyl)piperidine hydrochloride 477 0.65 B
370 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-propanoylaminocinnamyl)piperidine hydrochloride 460 0.21 H
371 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-ethoxycarbonylaminocinnamyl)piperidine hydrochloride 476 0.20 H
372 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methanesulfonylaminocinnamyl)piperidine hydrochloride 482 0.44 B
373 1-(N,N-Bis(methanesulfonyl)amminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine 560 0.88 B
hydrochloride
374 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-methoxycarbonylcinnamyl)piperidine hydrochloride 447 0.55 B
375 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxycarbonylcinnamyl)piperidine hydrochloride 447 0.48 H
376 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylcinnamyl)piperidine hydrochloride 447 0.50 B
377 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-3-methoxy-2-nitrocinnamyl)piperidine hydrochloride 464 0.30 H
378 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-methoxycarbonylaminocinnamyl)piperidine hydrochloride 462 0.53 B
379 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-pivaloy)aminocinnamyl)piperidine hydrochloride 488 0.51 B
380 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-trifluoroacetylaminocinnamyl)piperidine hydrochloride 500 0.44 B
381 1-(4-Butanoylaminocinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 474 0.50 B
382 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-ethoxycarbonylcinnamyl)piperidine hydrochloride 477 0.85 B
383 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(4-(2-methoxyacetoxy)cinnamyl)piperidine hydrochloride 477 0.45 B
384 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3,4-dihydroxycinnamyl)piperidine hydrochloride 422 0.35 B
(H+)
385 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(2-indolylmethyl)piperidine hydrochloride 402 0.67 H
386 1-(4-Aminosulfonylcinnamyl)-4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)piperidine hydrochloride 468 0.48 B
(H+)
387 4-(5H-Dibenzo[a,d]cyclohepten-5-ylidene)-1-(3-methoxy-4-nitrocinnamyl)piperidine 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 pressure
Dose (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 −48
100 10 −35 −5
101 10 −89 −14
107 10 −88 −11
108 10 −126 −50
111 10 −98 −13
112 10 −16 0
113 1 −151 −81
115 10 −53 −19
116 10 −36 −12
117 10 −143 −25
118 10 −129 −24
119 10 −34 −5
120 3 −17 −12
121 10 −42 −19
122 10 −120 −62
123 10 −55 −7
124 10 −90 −20
125 10 −93 −14
126 10 −87 −19
128 10 −129 −8
129 10 −17 −1
130 10 −42 9
131 10 −116 2
132 10 −106 −5
133 3 −146 −84
134 10 −115 −30
135 10 −132 −50
136 10 −100 −40
138 10 −129 −33
139 10 −139 −89
140 3 −113 −101
142 10 −43 0
149 10 −116 −32
150 10 −110 −47
151 10 −81 −43
154 10 −131 −105
155 10 −131 −105
156 10 −110 −42
157 10 −32 −13
158 10 −8 7
159 10 −27 −12
160 10 −3 −10
161 10 −64 −12
162 10 −62 −3
163 10 −1 4
164 10 −91 −22
165 10 −22 12
166 10 −45 6
168 10 −108 0
169 10 −130 −4
171 10 −122 −8
172 10 −115 −25
173 10 −98 −25
174 10 −8 −16
175 10 −87 −1
176 10 −105 −10
180 10 −25 −24
181 10 −56 −27
182 10 −11 −6
184 10 −16 −4
185 10 −66 −10
186 10 −95 −12
187 10 −47 −9
188 10 −94 −12
189 10 −72 −15
190 10 −11 −15
191 10 −29 −20
192 10 −25 −36
193 10 −124 −59
194 10 −59 −17
195 10 −100 −51
196 10 −145 −81
197 10 −51 −26
198 10 −124 −25
199 10 −15 −24
200 10 −10 −24
201 10 −118 −21
202 10 −54 −16
203 3 −123 −58
204 10 −141 −84
205 10 −22 −4
206 10 −61 −27
207 10 −98 −43
208 10 −131 −19
209 10 −49 −13
210 1 −78 −69
212 10 −155
213 10 −82 3
214 10 −126 −21
215 10 −128 −14
216 3 −2 −27
217 10 −18 −20
218 10 −97 −11
219 10 −104 −33
220 10 −148 −54
221 10 −70 −13
222 10 −94 −5
224 10 −69 −61
225 10 −115 −31
226 10 −131 −16
228 3 −112 −14
229 3 −77 −14
230 3 −131 −91
231 3 −132 −115
232 1 −92 −85
233 10 −35 −1
234 10 −96 −2
235 10 −99 −5
236 10 −10 −15
237 10 −65 −14
238 10 −14 −5
239 10 −68 −15
240 3 −118 −5
241 10 −73 −4
242 10 −28 7
243 10 −111 −31
244 10 −19 4
245 10 −34 −10
246 10 −34 −4
247 10 −119 −40
248 10 −101 −92
249 10 −121 −100
250 10 −136 −30
251 10 −110 −24
252 10 −23 −5
253 10 −12 1
255 10 −62 2
256 10 −60 −11
257 10 −70 −13
258 10 −74 −10
259 10 −46 −5
260 10 −51 −10
261 10 −123 −11
262 10 −16 −3
264 10 −38 −5
265 10 −61 −11
266 10 −133 −77
267 10 −40 0
268 10 −29 13
269 10 143 −71
270 10 −18 2
271 10 −17 −13
272 10 −76 −3
273 10 −37 5
274 10 −102 −21
275 10 −66 −20
276 10 −24 −1
277 10 −27 0
278 10 −64 2
279 3 −83 −24
280 10 −50 −11
281 10 −31 −5
282 10 −72 −15
283 10 −112 4
284 3 −151 −40
285 10 −62 −7
286 10 −134 −40
287 10 −83 −16
288 10 −92 −14
289 3 −20 10
290 3 −15 15
291 3 −8 15
292 3 −31 3
293 10 −122 4
294 3 −17 7
295 3 −36 1
296 10 −109 −14
297 10 −129 −57
298 10 −111 −31
299 10 −134 −45
300 10 −97 −22
301 10 −100 −12
302 10 −83 −41
303 3 −90 −19
304 10 −49 −5
305 10 −95 −9
306 10 −138 −37
307 10 −62 −20
308 3 −27 −5
310 10 −90 −18
311 10 −90 −18
312 10 −115 −11
313 10 −154 −85
314 10 −61 −11
315 10 −43 −3
316 1 −100 8
317 10 −118 −14
318 10 −83 −57
319 10 −104 −20
320 10 −147 −113
321 10 −60 −4
322 10 −100 −16
323 10 −117 −11
324 10 −137 −46
325 10 −115 −100
326 1 −125 −102
327 3 −10 −43
328 10 −125 −87
329 10 −34 −7
330 10 −93 −25
331 10 −62 −14
332 10 −111 −57
343 3 −83 −45
344 1 −123 −35
345 3 −120 −95
346 3 −142 −121
347 3 −116 −53
348 3 −105 −12
349 1 −48 −43
350 10 −136 −85
351 3 −70 −21
352 3 −93 −60
353 10 −147 −138
354 3 −89 −8
363 3 −120
364 1 −113
365 3 −80 −56
366 3 −152 −113
367 10 −98 −63
368 3 −110 −68
369 10 −101 −83
370 10 −99 −69
374 3 −119 11
375 1 −126 −70
376 3 −106 −77
377 1 −151 −73
378 1 −106 −90
379 1 −118 −59
380 0.3 −141
381 3 −136
382 3 −129 −74
383 3 −112 −86
334 3 −130 −93
385 10 −123 −96
386 10 −83 −96
387 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 (13)

What is claimed as new and is intended to be secured by Letters Patent of the United States is:
1. A piperidine compound of the formula (I)
Figure USRE038257-20030923-C00003
wherein:
A is pyridine;
R is —H, —Cl or —OCH3;
X is —(CH2)n—, —CO—(CH2)3, —CONH—(CH2)2, —NHCO—(CH2)2, or —CH≡CH—(CH2)2—; and
n is an integer of from 3 to 5;
Y is —CH≡CH—, —(CH2)2, —OCH2—, —SCH2—, 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CH2n wherein n is an integer of 1 to 10, ClCH23, 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 CH2 groups, one or more of the CH2 groups in X and/or Q may be substituted by CH24 CH25, thereby forming a ring structure.
2. The piperidine compound of claim 1, wherein the hydrogen atoms of one or more of the —CH2— groups in X and Q are substituted by CH24 or CH25, 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CH2n wherein n is an integer of 1 to 10, ClCH23, 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—(CH2)2.
5. The piperidine compound of claim 1, wherein Y is —CH≡CH—.
6. The piperidine compound of claim 1, wherein Y is —(CH2)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—(CH2)2, and Q is substituted or unsubstituted piperidinyl.
9. A piperidine compound of the formula
Figure USRE038257-20030923-C00004
wherein:
R is —H, —Cl or —OCH3;
X is —(CH2)n—, —CO—(CH2)3, —CONH—(CH2)2, —NHCO—(CH2)2, or —CH≡CH—(CH2)2—; and
n is an integer of from 3 to 5;
Y is —CH≡CH—, —(CH2)2—, —OCH2—, —SCH2—; 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CH2n wherein n is an integer of 1 to 10, ClCH23, 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 CH2groups, one or more of the CH2 groups in X and/or Q may be substituted by CH24 or CH25, thereby forming a ring structure.
10. The piperidine compound of claim 9, wherein X is —CONH—(CH2)2, Y is —CH≡CH—, and Q is N-formylpiperidinyl.
11. A piperidine compound of the formula
Figure USRE038257-20030923-C00005
wherein:
R is —H, —Cl or —OCH3;
X is —CO—(CH2)3, —CONH—(CH2)2, —NHCO—(CH2)2, or —CH≡CH— (CH2)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CH2n wherein n is an integer of 1 to 10, ClCH23, 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 CH2 groups, one or more of the CH2 groups in X and/or Q may be substituted by CH24 or CH25 thereby forming a ring structure.
12. A piperidine compound of the formula
Figure USRE038257-20030923-C00006
wherein:
R is —H, —Cl or —OCH3;
X is —(CH2)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CH2n wherein n is an integer of 1 to 10, ClCH23, 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 CH2 groups in X may be substituted by CH24 or CH25 thereby forming a ring structure.
13. The piperidine compounds of claim 10, wherein R is —H.
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