HK1087702B

HK1087702B - Arylmethylamine derivatives for use as tryptase inhibitors

Info

Publication number: HK1087702B
Application number: HK06107891.9A
Authority: HK
Inventors: P．C．阿瑟尔斯; P．R．伊斯特伍德; O．霍伊尔; J．利威尔; H．鲍尔斯; M．泽卡; 梁谷岩; 勇宫; J．普里比什; K．诺恩施万德
Original assignee: Aventisub Llc
Priority date: 2000-05-22
Filing date: 2006-07-14
Publication date: 2010-09-17

Description

Arylmethylamine derivatives useful as tryptase inhibitors

The invention is a divisional application of Chinese patent application 01811952.2 filed on 4, 27/2001, entitled "arylmethylamine derivatives as tryptase inhibitors".

Technical Field

The present invention relates to substituted arylmethylamines, their preparation, pharmaceutical compositions containing these compounds and their use in the treatment of disease states which can be modulated by the inhibition of tryptase.

Background

Tryptase is stored in mast cell secretory granules and is the major secretory protease of human mast cells. Tryptase has been implicated in a variety of biological processes, including the degradation of vasodilatory and bronchorelaxant neuropeptides (Caughey et al, J.Pharmacol. Bxp. Ther. (J.Pharmacol. Bxp. Ther.) (J.Pharmacol. J.Experimental therapeutics), 1988, 244, p.133-137; Franconi et al, J.Pharmacol. exp. Ther. (J.Pharmacol. experimental therapeutics), 1988, 248, p.947-951; Tam et al, am.J.Respir.cell mol. biol. (J.USA. respiring. molecular biol., 1990, 3, p.27-32) and the regulation of bronchial responsiveness to histamine (Sekizawa et al, J.Clin. invest. (J.clinical examination), 1989, 83, p.175-179). As a result, tryptase can be used as an anti-inflammatory agent (K Rice, P.A. Sprengler, Current Opinion in drug discovery and Development, 1999, 2(5), p.463-474), in particular in the treatment of chronic asthma (M.Q.Zhang, H.Timmerman, Mediators Inflamm. (inflammatory Mediators), 1997, 112, p.311-317), and also in the treatment or prevention of allergic rhinitis (S.J.Wilson et al, Clin.p.Allergy (clinical and experimental allergies), 1998, 28, p.220-227), inflammatory bowel disease (S.C. Bischoff et al, Histopathology (pathological histology), 1996, 28, p.1-13), psoriasis (A.Naukkarren et al, Arch.Dermatology allergy.341, Jatology 341, Johnson.51-13), psoriasis (A.J.Patch.A. J.285, atopic dermatitis, Ab.40. J.J.19834, Able., dermatological disease, Able et al, Abort, 1997, 136, p.871-877), rheumatoid arthritis (L.C.Tetlow et al, Ann.Rheum.Dis. (annual reference for rheumatoid disease), 1998, 54, p.549-555), osteoarthritis (M.G.Buckley et al, J.Pathol. (J.Pathol., 1998, 186, p.67-74), gouty arthritis, rheumatoid spondylitis and articular cartilage destructive diseases.

In addition, tryptase has been shown to be a potent mitogen for fibroblasts, suggesting that it is involved in pulmonary fibrosis in asthma and interstitial lung diseases (Ruoss et al, j.clin.invest. (journal of clinical examination), 1991, 88, p.493-499). Thus, tryptase inhibitors may be used for the treatment or prevention of fibrotic disorders (j.a. cairns and a.f. walls, j.clin.invest. (journal of clinical examination), 1997, 99, p.1313-1321), such as fibrosis, scleroderma, pulmonary fibrosis, cirrhosis, cardiac fibrosis, neurofibromas and hypertrophic scarring.

In addition, tryptase inhibitors may be useful in the treatment or prevention of myocardial infarction, stroke, angina and other consequences of atherosclerotic plaque rupture (m. jeziorska et al, j. pathol. (journal of pathology), 1997, 182, p.115-122). It has also been found that tryptase activates pro-stromelysin, which in turn activates collagenase, thereby triggering the destruction of cartilage and periodontal connective tissue, respectively. Therefore, tryptase inhibitors can be used for the treatment or prevention of arthritis, periodontal disease, diabetic retinopathy and tumor growth (w.j.beil et al, exp.hematol. (experimental hematology), (1998)26, p.158-169). Further, tryptase inhibitors may also be used in the treatment of allergy (l.b. schwarz et al, j.clin.invest. (journal of clinical examination), 1995, 96, p.2702-2710), multiple sclerosis (m.steinhoff et al, nat.med. (natural medicine) (n.y.), 2000, 6(2), p.151-158), peptic ulcers and syncytial virus infections.

Mast cell mediated inflammatory conditions, particularly asthma, are increasingly attracting public health concerns. Asthma is often characterized by the progressive development of airway and bronchial hyperreactivity to immunospecific allergens and general chemical or physical stimuli, which causes the onset of chronic inflammation. Leukocytes containing IgE receptors, especially mast cells and basophils, are present in the epithelium, underlying bronchial smooth muscle tissue. These leukocytes initially become activated by the binding of inhaled specific antigens to IgE receptors and then release large amounts of chemical mediators. For example, degranulation of mast cells causes the release of proteoglycans, peroxidases, arylsulfatase B, tryptase and chymase, which results in the constriction of bronchioles.

Therefore, what is needed is a new and useful group of compounds that have valuable pharmaceutical properties, particularly the ability to inhibit tryptase. Such compounds are readily of utility in the treatment of patients whose conditions can be ameliorated by the administration of tryptase inhibitors, for example mast cell mediated inflammatory conditions, inflammation and diseases or disorders associated with the degradation of vasodilatory and bronchorelaxing neuropeptides. Specific examples of such disorders are described below.

Citation of any reference herein shall not be construed as an admission that such reference is available as prior art to the present application.

Disclosure of Invention

In general terms, the invention extends to compounds of formula (I):

such that Ar is an aryl or heteroaryl group,with radicals on aryl radicalsThe position beta to the group is,

wherein:

is a single or double bond;

R¹and R²Each independently is hydrogen or lower alkyl;

R³is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl, heteroarylalkenyl, heterocycloalkenyl, heterocycloalkyl attached to carbon, or alkyl optionally substituted with one or more groups selected from hydroxy, alkoxy, alkoxycarboamido, cycloalkyl, heterocycloalkyl, R⁶、-OR⁶、-S(O)_mR⁶or-C (═ O) -R⁶；

R⁴Is hydrogen, acyl, alkoxy, alkoxycarbonyl, carboxyl, cyano, halo, hydroxy, -C (═ O) -NY¹Y²Or optionally alkoxy, alkylcarbonamido, alkylsulfonylamino, hydroxy, -S (O)_m-alkyl or-NY¹Y²A substituted alkyl group;

R⁵is hydrogen, acyl, alkoxy, alkoxycarbonyl, aryl, carboxyl, cyano, halo, heteroaryl, heteroaryloxy, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylalkoxy, heteroarylalkoxy, hydroxyl, trifluoromethyl, -C (═ O) -NY¹Y²、-NY¹Y²、-Z¹-C_2-6alkylene-R⁷Or optionally alkoxy, alkylcarbonamido, alkylsulfonylamino, aryl, heteroaryl, heterocycloalkyl, hydroxy, ureido, -C (═ O) -NY¹Y²、-SO₂-NY¹Y²、-S(O)_m-alkyl or-NY¹Y²A substituted alkyl group;

R⁶is aryl or heteroaryl;

R⁷is hydroxy, alkoxy, ureido, -C (═ O) -NY¹Y²、-SO₂-NY¹Y²、-S(O)_m-alkyl or-NY¹Y²；

R⁸Is hydrogen or lower alkyl;

Y¹and Y²Independently is hydrogen, alkenyl, alkyl, aryl, arylalkyl, cycloalkyl, heteroaryl, heteroarylalkyl, or heterocycloalkyl; or a radical-NY¹Y²Amines which may be cyclic;

Z¹is O, S (O) m or NR⁸；

m is 0 or an integer from 1 to 2;

n is 0 or an integer from 1 to 4;

an N-oxide of the compound, a prodrug of the compound, a pharmaceutically acceptable salt of the compound, a solvate of the compound, and a hydrate of the compound.

Furthermore, the invention extends to a compound of formula (Ia):

wherein:

is a single or double bond;

R¹and R²Each independently is hydrogen or lower alkyl;

R³is aryl, arylalkenyl, cycloalkenyl, cycloalkyl, heteroaryl, heteroarylalkenyl, heterocycloalkenyl, bonded to carbonOr alkyl optionally substituted by one or more groups selected from hydroxy, alkoxy, alkoxycarbonylamino, cycloalkyl, heterocycloalkyl, R⁶、-OR⁶、-S(O)_mR⁶or-C (═ O) -R⁶；

R⁶is aryl or heteroaryl;

R⁸Is hydrogen or lower alkyl;

Z¹is O,S (O) m or NR⁸；

m is 0 or an integer from 1 to 2;

n is 0 or an integer from 1 to 4;

and the corresponding N-oxides and their prodrugs; pharmaceutically acceptable salts and solvates (e.g. hydrates) of such compounds and their N-oxides and prodrugs.

In another embodiment, the invention extends to a compound of formula (Ib):

wherein:

R⁴Is hydrogen, acyl, alkoxy, alkoxycarbonyl, carboxyl, cyano, halogen, hydroxy, -C (═ O) -NY¹Y²Or optionally alkoxy, alkylcarbonamido, alkylsulfonylamino, hydroxy, -S (O)_m-alkyl or-NY¹Y²A substituted alkyl group;

R⁵is hydrogen, acyl, alkoxy, alkoxycarbonyl, aryl, carboxyl, cyano, halogen, heteroaryl, heteroaryloxy, heterocycloalkyl, heterocycloalkoxy, heterocycloalkylalkoxy, heteroarylalkoxy, hydroxyl, trifluoromethyl, -C (═ O) -NY¹Y²、-NY¹Y²、-Z¹-C_2-6alkylene-R⁷Or optionally alkoxy, alkylcarbonamido, alkylSulfonamido, aryl, heteroaryl, heterocycloalkyl, hydroxy, ureido, -C (═ O) -NY¹Y²、-SO₂-NY¹Y²、-S(O)_m-alkyl or-NY¹Y²A substituted alkyl group;

and the corresponding N-oxides, prodrugs, pharmaceutically acceptable salts, solvates, N-oxides and prodrugs of said compounds.

Specific examples of such compounds are described below.

Furthermore, the invention extends to a pharmaceutical composition comprising a compound of the invention as described above and a pharmaceutically acceptable carrier therefor. Examples of a number of drug carriers that can be used in the present invention are described below.

In addition, the invention extends to a method for treating a subject suffering from a condition ameliorated by the administration of an inhibitor of tryptase, which method comprises administering an effective amount of a compound of the invention. Examples of conditions that can be treated with the compounds of the present invention include, but certainly are not limited to, inflammatory diseases such as joint inflammation, arthritis, rheumatoid spondylitis, gouty arthritis, traumatic arthritis, rubella arthritis, psoriatic arthritis and other chronic inflammatory joint diseases. Examples of other conditions that can be treated by the methods of the invention include articular cartilage destructive diseases, ocular conjunctivitis, vernal conjunctivitis, inflammatory bowel disease, asthma, allergic rhinitis, interstitial lung disease, fibrosis, scleroderma, pulmonary fibrosis, cirrhosis, cardiac fibrosis, neurofibromatosis, hypertrophic scarring, various dermatological conditions such as atopic dermatitis and psoriasis, consequences of myocardial infarction, stroke, angina and other atherosclerotic plaque rupture, as well as periodontal disease, diabetic retinopathy, tumor growth, allergy, multiple sclerosis, peptic ulcer and syncytial virus infection, among others.

In a specific embodiment, the invention extends to a method of treating an asthmatic patient, comprising administering to the patient an effective amount of a compound of the invention.

In another embodiment, the invention extends to a method of treating a subject having joint inflammation comprising administering to the subject an effective amount of a compound of the invention.

In addition, the invention extends to a medicament comprising a compound of the invention and a second compound selected from the group consisting of a beta adrenergic agonist, an anticholinergic agent, an anti-inflammatory corticosteroid and an anti-inflammatory agent, and a pharmaceutically acceptable carrier. Specific inflammatory diseases that can be treated with such pharmaceutical compositions include, but are not limited to, asthma.

In addition, the invention relates toA method for treating a patient having an inflammatory disease comprising administering to the patient a compound of the invention and a second compound selected from the group consisting of a beta adrenergic agonist, an anticholinergic agent, an anti-inflammatory corticosteroid, and an anti-inflammatory agent.

In such a method of the invention, a compound of the invention may be administered to the patient before a second compound, a second compound may be administered to the patient before a compound of the invention, or a compound of the invention and a second compound may be administered concurrently. Specific examples of adrenergic agonists, anticholinergics, anti-inflammatory corticosteroids, and anti-inflammatory agents that can be used in the methods of the invention are described below.

Accordingly, it is a primary object to provide compounds having anti-tryptase activity. Such compounds can be readily used to treat conditions that can be ameliorated by the administration of tryptase inhibitors.

It is another object of the present invention to provide pharmaceutical compositions for treating conditions that can be ameliorated by the administration of an inhibitor of tryptase.

It is also an object of the present invention to provide pharmaceutical compositions comprising the compounds of the present invention.

These and other aspects of the invention will be better appreciated with reference to the following detailed description.

Detailed Description

The following terms, as used above and throughout the specification and claims, shall be understood to have the following meanings, unless otherwise specified:

the term "compounds of the invention" and equivalent expressions as used herein are meant to encompass compounds of formula (I), (Ia) or (Ib) as hereinbefore described, including prodrugs, pharmaceutically acceptable salts and solvates, for example hydrates, if the context allows so. Similarly, references to intermediates, whether claimed themselves or not, are meant to encompass their salts and solvates if the context so permits. Certain circumstances are sometimes indicated herein where the context permits, for clarity, but these are merely illustrative and are not intended to exclude other circumstances where the context permits.

The term "treatment" as used herein includes prophylactic treatment as well as treatment of a given condition.

"patient" includes humans and other mammals.

By "effective amount" is meant an amount describing that the compound of the present invention is effective to inhibit tryptase, thereby producing the desired therapeutic effect.

"acyl" means H-CO-or alkyl-CO-, wherein alkyl is as described herein.

"acylamino" is acyl-NH-wherein acyl is as described herein.

"alkenyl" means an aliphatic hydrocarbon group containing a carbon-carbon double bond, which may be straight or branched, having from about 2 to about 15 carbon atoms in the chain. Preferred alkenyl groups have 2 to about 12 carbon atoms in the chain; more preferably from about 2 to about 4 carbon atoms in the chain. As used herein and throughout "branched" means that one or more lower alkyl groups, such as methyl, ethyl or propyl, are attached to a straight chain, here a straight chain, of alkenyl groups. "lower alkenyl" means about 2 to about 4 carbon atoms in the chain, which may be straight or branched. Exemplary alkenyl groups include ethenyl, propenyl, n-butenyl, isobutenyl, 3-methylbut-2-enyl, n-pentenyl, heptenyl, octenyl and decenyl.

"alkoxy" means alkyl-O-wherein alkyl is as described herein. Exemplary alkoxy groups include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, and heptoxy.

"alkoxycarbonyl" means alkyl-O-C (═ O) -, where alkyl is as described herein. Exemplary alkoxycarbonyl groups include methoxycarbonyl and ethoxycarbonyl.

"alkyl" means, unless otherwise specified, an aliphatic hydrocarbon group, which may be straight or branched, having from about 1 to about 15 carbon atoms in the chain, optionally substituted with alkoxy groups or one or more halogen atoms. Specific alkyl groups have from 1 to about 6 carbon atoms. "lower alkyl" as a group or part of lower alkoxy, lower alkylthio, lower alkylsulfinyl or lower alkylsulfonyl, unless otherwise specified, refers to an aliphatic hydrocarbon group, which may be straight or branched, having from about 1 to about 4 carbon atoms in the chain. Exemplary alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, tert-butyl, n-pentyl, 3-pentyl, heptyl, octyl, nonyl, decyl, and dodecyl.

"alkylcarbonamido" means an alkyl-C (═ O) -NH-where the alkyl group is as described herein. Exemplary alkylcarbonamido groups include acetylamino and propionylamino.

"alkylene" means an aliphatic divalent radical derived from a straight or branched chain alkyl group, wherein the alkyl group is as described herein. Exemplary alkylene radicals include methylene, ethylene, and propylene.

"Alkylenedioxy" means-O-alkyl-O-wherein alkyl is as defined above. Exemplary alkylenedioxy groups include methylenedioxy and ethylenedioxy.

"Alkylsulfinyl" means alkyl-SO-wherein alkyl is as previously described. Preferred alkylsulfinyl radicals are those in which alkyl is C_1-4Those of alkyl groups.

"alkylsulfonyl" means alkyl-SO₂-, wherein alkyl is as previously described. Preferred alkylsulfonyl groups are those wherein alkyl is C_1-4Those of alkyl groups.

"Alkylsulfonamido" refers to alkyl-SO₂-NH-, wherein alkyl is as described herein. Exemplary alkylsulfonylamino groups include methylsulfonylamino and ethylsulfonylamino.

"alkylthio" means an alkyl-S-group in which the alkyl group is as previously described. Exemplary alkylthio groups include methylthio, ethylthio, isopropylthio and heptylthio.

"alkynyl" means an aliphatic hydrocarbon group containing a carbon-carbon triple bond, which may be straight or branched chain, having from about 2 to about 15 carbon atoms in the chain. Preferred alkynyl groups have 2 to about 12 carbon atoms in the chain; more preferably from about 2 to about 4 carbon atoms in the chain. Exemplary alkynyl groups include ethynyl, propynyl, n-butynyl, 2-butynyl, 3-methylbut-2-ynyl and n-pentynyl.

"aroyl" means aryl-CO-wherein aryl is as described herein. Exemplary aroyl groups include benzoyl and 1-and 2-naphthoyl.

An "aroylamino" group is an aroyl-NH-group wherein aroyl is as previously defined.

"aryl" as a group or part of a group means: (i) an optionally substituted monocyclic or polycyclic aromatic carbon ring portion of about 6 to about 14 carbon atoms, such as phenyl or naphthyl; or (ii) an optionally substituted partially saturated polycyclic aromatic carbon ring moiety wherein the aryl and cycloalkyl or cycloalkenyl are fused together to form a cyclic structure, e.g., tetrahydronaphthyl, indenyl or indanylAnd (4) a ring. The aryl group may be substituted with one or more aryl substituents which may be the same or different, where "aryl substituent" includes, for example, acyl, acylamino, alkoxy, alkoxycarbonyl, alkylenedioxy, alkylsulfinyl, alkylsulfonyl, alkylthio, aroyl, aryl, arylalkenyl, arylalkynyl, arylalkoxy, arylalkoxycarbonyl, arylalkylthio, aryloxy, aryloxyalkyl, aryloxycarbonyl, arylsulfinyl, arylsulfonyl, arylthio, carboxyl, cyano, halo, heteroarylacyl, heteroaryl, heteroarylalkenyl, heteroarylalkynyl, heteroarylalkoxy, heteroarylamido, heteroaryloxy, heteroaryloxyalkyl, hydroxyl, nitro, trifluoromethyl, -NY¹Y²、-CONY¹Y²、-SO₂NY¹Y²、-Z²-C_2-6alkylene-NY¹Y²(wherein Z is²Is O, NR⁸Or S (O)_m)、-NY¹-C (═ O) alkyl, -NY¹-SO₂Alkyl or optionally alkoxy, aroyl, aryl, aryloxy, heteroaryl, hydroxy or-NY¹Y²A substituted alkyl group.

"arylalkenyl" refers to aryl-alkenyl-wherein aryl and alkenyl are as previously described. Preferred arylalkenyl groups contain a lower alkenyl moiety. Exemplary arylalkenyl groups include styryl and phenylallyl.

"arylalkyl" means aryl-alkyl-wherein the aryl and alkyl portions are as previously described. Preferred arylalkyl radicals contain C_1-4An alkyl moiety. Exemplary arylalkyl groups include benzyl, 2-phenylethyl and naphthylmethyl.

"arylalkoxy" means arylalkyl-O-wherein arylalkyl is as previously described. Exemplary arylalkoxy groups include benzyloxy and 1-or 2-naphthylmethoxy.

"arylalkoxycarbonyl" means arylalkyl-O-CO-, wherein arylalkyl is as previously described. An exemplary arylalkoxycarbonyl group is benzyloxycarbonyl.

"Arylalkylthio" means an arylalkyl-S-group in which the arylalkyl group is as previously described. An exemplary arylalkylthio group is benzylthio.

"arylalkynyl" means aryl-alkynyl-wherein aryl and alkynyl are as previously described. Exemplary arylalkynyl groups include phenylethynyl and 3-phenylbut-2-ynyl.

"aryloxy" means aryl-O-wherein aryl is as previously described. Exemplary aryloxy groups include optionally substituted phenoxy and naphthoxy.

"aryloxyalkyl" means aryl-O-alkyl-wherein aryl and alkyl are as previously described. Exemplary aryloxyalkyl groups include phenoxymethyl and 1-or 2-naphthyloxymethyl.

"aryloxycarbonyl" refers to aryl-O-C (═ O) -, where aryl is as previously described. Exemplary aryloxycarbonyl groups include phenoxycarbonyl and naphthyloxycarbonyl.

"Arylsulfinyl" means aryl-SO-wherein aryl is as previously described.

"arylsulfonyl" means aryl-SO₂-, wherein aryl is as previously described.

"arylthio" means aryl-S-wherein aryl is as previously described. Exemplary arylthio groups include phenylthio and naphthylthio.

"azaaryl" means an aromatic carbocyclic moiety of about 5 to about 10 ring members, wherein one of the ring members is nitrogen and the other ring members are selected from carbon, oxygen, sulfur, or nitrogen. Examples of azaaryls include benzimidazolyl, imidazolyl, isoquinolyl, isoxazolyl, pyrazolopyrimidinyl, pyridyl, pyrimidinyl, quinolinyl, quinazolinyl, and thiazolyl.

"Cyclic amine" means a 3 to 8 membered monocyclic cycloalkyl ring system in which one of the ring carbon atoms is replaced by nitrogen, and which (i) may optionally contain an additional heteroatom selected from O, S or NY³(wherein Y is³Is hydrogen, alkyl, arylalkyl and aryl), (ii) may be fused with additional aryl or heteroaryl rings to form bicyclic ring systems. Exemplary cyclic amines include pyrrolidine, piperidine, morpholine, piperazine, indoline and dihydropyrrolo [1, 2-alpha ]]Pyridine (pyridine).

"cycloalkenyl" means a cycloalkyl group containing at least one carbon-carbon double bond. Exemplary monocyclic cycloalkenyl rings include cyclopentenyl, cyclohexenyl, or cycloheptenyl.

"cycloalkyl" means a saturated monocyclic or bicyclic ring system of about 3 to about 10 carbon atoms, optionally substituted by oxo, alkyl, aryl or-C (═ O) -NY¹Y²And (4) substitution. Exemplary monocyclic cycloalkyl rings include C_3-8Cycloalkyl rings, such as cyclopropyl, cyclopentyl, cyclohexyl, and cycloheptyl.

"cycloalkylalkyl" means cycloalkyl-alkyl-wherein the cycloalkyl and alkyl portions are as previously described. Exemplary monocyclic cycloalkylalkyl groups include cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, and cycloheptylmethyl.

"halo" or "halogen" means fluoro, chloro, bromo, or iodo. Preferably fluorine or chlorine.

"heteroaroyl" means heteroaryl-C (═ O) -, where heteroaryl is as described herein. Exemplary groups include pyridylcarbonyl.

"Heteroaroylamino" means a heteroaroyl-NH-group in which the heteroaryl moiety is as previously described.

"heteroaryl" as a group or part of a group means: (i) an optionally substituted aromatic monocyclic or polycyclic organic moiety of about 5 to about 10 ring members, wherein one or more of the ring members is an element other than carbon, such as nitrogen, oxygen, or sulfur (examples of such groups include benzimidazolyl, benzothiazolyl, benzothienyl, furanyl, imidazolyl, indolyl, indolizinyl, isoxazolyl, isoquinolinyl, isothiazolyl, oxadiazolyl, pyrazinyl, pyridazinyl, pyrazolyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, 1, 3, 4-thiadiazolyl, thiazolyl, thienyl, and triazolyl, optionally substituted with one or more aryl substituents as defined above); (ii) an optionally substituted partially saturated polycyclic heterocarbocyclic moiety in which the heteroaryl and cycloalkyl or cycloalkenyl groups are fused together to form a cyclic structure (examples of such groups include pyrroloindanyl). Optional substituents include one or more "aryl substituents" as defined above.

"arylene" means an optionally substituted divalent radical derived from an aryl group as defined herein. Exemplary arylene groups include optionally substituted phenylene, naphthylene, and dihydroindenyl groups. Suitable substituents include one or more "aryl substituents" as defined above, in particular halogen, methyl or methoxy.

"heteroarylene" means a divalent radical derived from a heteroaryl group as defined below.

"heteroarylalkenyl" means heteroaryl-alkenyl-wherein the heteroaryl and alkenyl moieties are as previously described. Preferred heteroarylalkenyls contain a lower alkenyl moiety. Exemplary heteroarylalkenyl groups include pyridylvinyl and pyridylallyl.

"heteroarylalkyl" means heteroaryl-alkyl-wherein the heteroaryl and alkyl portions are as previously described. Preferred heteroarylalkyl radicals contain C_1-4An alkyl moiety. Exemplary heteroarylalkyl groups include pyridylmethyl.

"heteroarylalkoxy" means heteroarylalkyl-O-wherein heteroarylalkyl is as previously described. Exemplary heteroarylalkoxy groups include optionally substituted pyridinylmethoxy.

"Heteroarylalkynyl" means heteroaryl-alkynyl-wherein the heteroaryl and alkynyl moieties are as previously described. Exemplary heteroarylalkynyls include pyridylethynyl and 3-pyridylbut-2-ynyl.

"Heteroaryloxy" means heteroaryl-O-wherein heteroaryl is as previously described. Exemplary heteroaryloxy groups include optionally substituted pyridyloxy.

"Heteroaryloxyalkyl" means heteroaryl-O-alkyl-wherein heteroaryl and alkyl are as previously described. Exemplary heteroaryloxyalkyl groups include pyridyloxymethyl and 2-, 3-, or 4-quinolinyloxymethyl.

"Heterocycloalkenyl" means a cycloalkenyl group of about 3 to 7 ring members containing one or more heteroatoms selected from O, S or NY⁴(wherein Y is⁴Is hydrogen, alkyl, aryl, arylalkyl and alkoxycarbonyl). Exemplary heterocycloalkenyl groups include 1, 2, 3, 6-tetrahydropyridine.

"heterocycloalkyl" means: (i) cycloalkyl of about 3 to 7 ring members containing one or more heteroatoms selected from O, S or NY⁴(wherein Y is⁴Is hydrogen, alkyl, aryl, arylalkyl and alkoxycarbonyl) and may optionally be substituted by oxo (examples of such groups include piperidinyl, pyrrolidinyl, morpholinyl, tetrahydropyranyl and tetrahydrothienyl); (ii) an optionally substituted partially saturated polycyclic heterocarbocyclic moiety wherein one or more aryl (or heteroaryl) rings and about 3 to 7 ring members of a cycloalkyl group (which contains one or more heteroatoms selected from O, S or NY)⁴And may optionally be oxo substituted) to form a cyclic structure (examples of such groups include chromanyl, dihydrobenzofuranyl, indolinyl and dihydropyrrolo [1, 2-a ]]Pyridyl).

"Heterocycloalkylalkyl" means heterocycloalkyl-alkyl-wherein the heterocycloalkyl and alkyl moieties are as previously described.

"Heterocycloalkylalkoxy" means heterocycloalkyl-alkyl-O-in which the heterocycloalkyl and alkyl moieties are as previously described.

"Heterocycloalkyloxy" means heterocycloalkyl-O-in which heterocycloalkyl is as previously described.

By "prodrug" is meant a compound that is suitable for administration to a patient without undue toxicity, irritation, allergic response, and the like, and that can be metabolized (e.g., hydrolyzed) in vivo to a compound of the invention, including its N-oxide. For a thorough discussion see t.higuchi and v.stella, Pro-drugs as Novel Delivery Systems, volume 14 of a.c.s.symposium Series; roche ed Bioreversible Cariers in Drug Design, American Pharmaceutical Association and Pergamon Press, 1987, both incorporated herein by reference. For example, esters of the compounds of the invention containing a hydroxy group may be converted to the parent molecule by hydrolysis in vivo. Alternatively, esters of the compounds of the invention containing a carboxyl group may be converted to the parent molecule by hydrolysis in vivo.

Suitable esters of the compounds of the invention containing a hydroxyl group are, for example, acetates, citrates, lactates, tartrates, malonates, oxalates, salicylates, propionates, succinates, fumarates, maleates, methylene-bis- β -hydroxynaphthoates, glycocholates, isethionates, di-p-toluoyltartrate, methanesulfonates, ethanesulfonates, benzenesulfonates, p-toluenesulfonates, cyclohexylsulfamates and quinic acid esters.

A particularly useful class of esters of compounds of the invention containing a hydroxyl group may be formed from an acid moiety selected from those described in Bundgaard et al, j.med.chem. (journal of medicinal chemistry), 1989, 32, p.2503-2507, including substituted (aminomethyl) -benzoates, e.g. dialkylamino-methylbenzoates, in which the two alkyl groups may be linked together and/or interrupted by an oxygen atom or an optionally substituted nitrogen atom, e.g. an alkylated nitrogen atom, more particularly (morpholino-methyl) benzoates, e.g. 3-or 4- (morpholinomethyl) -benzoates, and (4-alkylpiperazin-1-yl) benzoates, e.g. 3-or 4- (4-alkylpiperazin-1-yl) benzoates.

Suitable esters of the compounds of the invention containing a carboxyl group are described, for example, in f.j.leinweber, drug metab.res (studies on drug metabolism), 1987, 18, p.379.

The compounds of the invention are basic and such compounds may be used in the form of their free bases or in the form of pharmaceutically acceptable acid addition salts.

The acid addition salt is more convenient to use; in practice, the use of the salt form is intended to correspond to the use of the free base form. Acids which can be used to prepare acid addition salts preferably include those which, upon combination with the free base, form a pharmaceutically acceptable salt, i.e., a salt whose anion is non-toxic to the patient at a pharmaceutical dosage of the salt, so that the beneficial inhibitory effect inherent in the free base is not vitiated by side effects attributable to the anion. Although pharmaceutically acceptable salts of the basic compounds are preferred, all acid addition salts can be used as sources of the free base form, even if the particular salt itself is only required as an intermediate product, for example when the salt is formed for the sole purpose of purification and identification, or when used as an intermediate in the preparation of a pharmaceutically acceptable salt by ion exchange procedures. Pharmaceutically acceptable salts within the scope of the present invention include those derived from inorganic and organic acids, including hydrohalic salts (e.g., hydrochloride and hydrobromide), sulfates, phosphates, nitrates, sulfamates, acetates, citrates, lactates, tartrates, malonates, oxalates, salicylates, propionates, succinates, fumarates, maleates, methylene-bis- β -hydroxynaphthoates, gentisates, isethionates, di-p-toluoyltartrate, methanesulfonates, ethanesulfonates, benzenesulfonates, p-toluenesulfonates, cyclohexylsulfamates, and quinic acid salts.

In addition to being useful as active compounds per se, salts of the compounds of the invention may also be used for the purpose of purification of the compounds, for example by techniques well known to those skilled in the art, exploiting the differences in solubility between the salts and the parent compound, by-products and/or starting materials.

With reference to formula (Ia) above, the following are specific and preferred groups:

R¹may particularly represent hydrogen.

R²May particularly represent hydrogen.

R³May particularly represent aryl, such as optionally substituted phenyl or optionally substituted naphthyl, especially substituted phenyl. Exemplary optional substituents include one or more halogen atoms or alkyl substituted with aryl, alkyl substituted with aryloxy, alkyl substituted with aroyl, alkyl substituted with heteroaryl, arylalkynyl, heteroarylalkynyl, aryl, heteroaryl, arylalkenyl, or arylalkoxy, wherein the aryl or heteroaryl group may be further substituted with one or more aryl substituents.

R³It may also particularly represent a heteroaryl group, such as an optionally substituted pyridyl group, an optionally substituted quinolyl group, an optionally substituted thienyl group, an optionally substituted furyl group or an optionally substituted indolyl group, especially a substituted thienyl group, a substituted pyridyl group or an indolyl group. Exemplary optional substituents include alkyl substituted with aryl, alkyl substituted with aryloxy, alkyl substituted with aroyl, alkyl substituted with heteroaryl, arylalkynyl, heteroarylalkynyl, heteroaryl, arylalkenyl, or arylalkoxy, wherein aryl or heteroaryl may be further substituted with one or more aryl substituents.

R⁴May particularly represent hydrogen.

R⁴And may also particularly represent cyano, especially when attached to a tertiary ring carbon atom.

R⁵May particularly represent hydrogen.

R⁵And may also specifically represent a lower alkyl group (e.g., methyl) or a halogen atom (e.g., fluorine).

May specifically represent a single bond.

n may specifically represent 2.

It is to be understood that the invention covers all suitable combinations of the specific and preferred groups referred to herein.

A particular group of compounds of the invention are compounds of formula (Ib):

wherein R is³、R⁴And R⁵Is as defined above in that respect,

and the corresponding N-oxides and their prodrugs; and pharmaceutically acceptable salts and solvates (e.g., hydrates) of such compounds and their N-oxides and prodrugs.

Preference is given to compounds of the formula (Ib) in which R³Represents aryl, for example optionally substituted phenyl or optionally substituted naphthyl, especially substituted phenyl. Preferred optional substituents include one or more halogen atoms or alkyl substituted with aryl or alkyl substituted with heteroaryl, wherein the aryl or heteroaryl may be further substituted with one or more aryl substituents. R³In particular dichlorophenyl (e.g. 3, 4-dichlorophenyl), phenyl C_1-3Alkylphenyl radicals (e.g. phenylethyl), hydroxyphenyl radicals C_1-3Alkylphenyl (e.g. 4-hydroxyphenylethylphenyl) and aminopyridyl C_1-3Alkylphenyl (e.g. (4-amino-pyridin-3-yl) ethylphenyl).

Preference is given to compounds of the formula (Ib) in which R³Represents a heteroaryl group, such as an optionally substituted pyridyl group, an optionally substituted quinolyl group, an optionally substituted thienyl group, an optionally substituted furyl group or an optionally substituted indolyl group, especially a substituted thienyl group, a substituted pyridyl group or an indolyl group. Preferred optional substitutionsGroups include alkyl substituted with aryl or alkyl substituted with heteroaryl, where aryl or heteroaryl may be further substituted with one or more aryl substituents. R³In particular represents phenyl C_1-3Alkylpyridyl (e.g. 5-phenethyl-pyridin-3-yl), phenyl C_1-3Alkylthiophenyl (e.g., 5-phenethyl-thiophen-2-yl) and indolyl (e.g., indol-6-yl).

Preference is given to compounds of the formula (Ib) in which R⁴Represents hydrogen.

Preference is also given to compounds of the formula (Ib) in which R is⁴Represents cyano. R⁴Preferably at the 4-position of the piperidine ring.

Preference is given to compounds of the formula (Ib) in which R⁵Represents hydrogen.

Preference is also given to compounds of the formula (Ib) in which R is⁵Represents lower alkyl (e.g. methyl) or halo (e.g. fluoro). R⁵preferably-CH attached to a phenyl ring₂NH₂And (4) contraposition.

A preferred group of compounds of the invention are compounds of formula (Ib) wherein: r³Is substituted phenyl (especially 3, 4-dichlorophenyl, phenethyl, 4-hydroxyphenylethylphenyl and (4-aminopyridin-3-yl) ethylphenyl) or optionally substituted heteroaryl (especially 5-phenethyl-pyridin-3-yl, 5-phenethyl-thiophen-2-yl or indol-6-yl); r⁴Is hydrogen or cyano attached at the 4-position of the piperidine ring; r⁵Is hydrogen or-CH attached to a phenyl ring₂NH₂Lower alkyl (e.g., methyl) or halo (e.g., fluoro) para to (a); and the corresponding N-oxides and their prodrugs; and pharmaceutically acceptable salts and solvates (e.g., hydrates) of such compounds and their N-oxides and prodrugs.

Specific compounds of the invention are selected from the compounds produced by linking the carbon atom (C) of one of the fragments (a1 to a10) shown in table 1 to the carbon atom (C) of one of the fragments (B1 to B12) shown in table 2, and further linking the nitrogen atom (N) of one of the fragments (B1 to B12) shown in table 2 to the carbon atom (C) of one of the acidic fragments (C1 to C103) shown in table 3.

TABLE 1

TABLE 2

TABLE 3

Examples of particularly preferred fragments "A", "B" and "C" are set forth in Table 4 below:

TABLE 4

A1-B1-C1 A1-B1-C2 A1-B1-C3 A1-B1-C4 A1-B1-C5 A1-B1-C6

A1-B1-C7 A1-B1-C8 A1-B1-C9 A1-B1-C10 A1-B1-C11 A1-B1-C12

A1-B1-C13 A1-B1-C14 A1-B1-C15 A1-B1-C16 A1-B1-C17 A1-B1-C18

A1-B1-C19 A1-B1-C20 A1-B1-C21 A1-B1-C22 A1-B1-C23 A1-B1-C24

A1-B1-C25 A1-B1-C26 A1-B1-C27 A1-B1-C28 A1-B1-C29 A1-B1-C30

A1-B1-C31 A1-B1-C32 A1-B1-C33 A1-B1-C34 A1-B1-C35 A1-B1-C36

A1-B1-C37 A1-B1-C38 A1-B1-C39 A1-B1-C40 A1-B1-C41 A1-B1-C42

A1-B1-C43 A1-B1-C44 A1-B1-C45 A1-B1-C46 A1-B1-C47 A1-B1-C48

A1-B1-C49 A1-B1-C50 A1-B1-C51 A1-B1-C52 A1-B1-C53 A1-B1-C54

A1-B1-C55 A1-B1-C56 A1-B1-C57 A1-B1-C58 A1-B1-C59 A1-B1-C60

A1-B1-C61 A1-B1-C62 A1-B1-C63 A1-B1-C64 A1-B1-C65 A1-B1-B66

A1-B1-C67 A1-B1-C68 A1-B1-C69 A1-B1-C70 A1-B1-C71 A1-B1-C72

A1-B1-C73 A1-B1-C74 A1-B1-C75 A1-B1-C76 A1-B1-C77 A1-B1-C78

A1-B1-C79 A1-B1-C80 A1-B1-C81 A1-B1-C82 A1-B1-C83 A1-B1-C84

A1-B1-C85 A1-B1-C86 A1-B1-C87 A1-B1-C88 A1-B1-C89 A1-B1-C90

A1-B1-C91 A1-B1-C92 A1-B1-C93 A1-B1-C94 A1-B1-C95 A1-B1-C96

A1-B1-C97 A1-B1-C98 A1-B1-C99 A1-B1-C100 A1-B1-C101 A1-B1-c102

A1-B1-C103 A1-B1-C104 A1-B1-C105 A1-B1-C106 A1-B1-C107 A1-B1-C108

A1-B1-C109 A1-B1-C110 A1-B1-C111 A1-B1-C112 A1-B1-C113 A1-B1-C114

A1-B1-C115 A1-B1-C116 A1-B1-C117 A1-B1-C118 A1-B1-C119 A1-B1-C120

A1-B1-C121 A1-B1-C122 A1-B1-C123 A1-B1-C124 A1-B1-C125 A1-B1-C126

A1-B1-C127 A1-B1-C128 A1-B1-C129 A1-B1-C130 A1-B1-C131 A1-B1-C132

A1-B1-C133 A1-B1-C134 A1-B1-C135 A1-B1-C136 A1-B1-C137 A1-B1-C138

A1-B1-C139 A1-B1-C140 BLANK BLANK BLANK BLANK

A1-B2-C1 A1-B2-C2 A1-B2-C3 A1-B2-C4 A1-B2-C5 A1-B2-C6

A1-B2-C7 A1-B2-C8 A1-B2-C9 A1-B2-C10 A1-B2-C11 A1-B2-C12

A1-B2-C13 A1-B2-C14 A1-B2-C15 A1-B2-C16 A1-B2-C17 A1-B2-C18

A1-B2-C19 A1-B2-C20 A1-B2-C21 A1-B2-C22 A1-B2-C23 A1-B2-C24

A1-B2-C25 A1-B2-C26 A1-B2-C27 A1-B2-C28 A1-B2-C29 A1-B2-C30

A1-B2-C31 A1-B2-C32 A1-B2-C33 A1-B2-C34 A1-B2-C35 A1-B2-C36

A1-B2-C37 A1-B2-C38 A1-B2-C39 A1-B2-C40 A1-B2-C41 A1-B2-C42

A1-B2-C43 A1-B2-C44 A1-B2-C45 A1-B2-C46 A1-B2-C47 A1-B2-C48

A1-B2-C49 A1-B2-C50 A1-B2-C51 A1-B2-C52 A1-B2-C53 A1-B2-C54

A1-B2-C55 A1-B2-C56 A1-B2-C57 A1-B2-C58 A1-B2-C59 A1-B2-C60

A1-B2-C61 A1-B2-C62 A1-B2-C63 A1-B2-C64 A1-B2-C65 A1-B2-C66

A1-B2-C67 A1-B2-C68 A1-B2-C69 A1-B2-C70 A1-B2-C71 A1-B2-C72

A1-B2-C73 A1-B2-C74 A1-B2-C75 A1-B2-C76 A1-B2-C77 A1-B2-C78

A1-B2-C79 A1-B2-C80 A1-B2-C81 A1-B2-C82 A1-B2-C83 A1-B2-C84

A1-B2-C85 A1-B2-C86 A1-B2-C87 A1-B2-C88 A1-B2-C89 A1-B2-C90

A1-B2-C91 A1-B2-C92 A1-B2-C93 A1-B2-C94 A1-B2-C95 A1-B2-C96

A1-B2-C97 A1-B2-C98 A1-B2-C99 A1-B2-C100 A1-B2-C101 A1-B2-C102

A1-B2-C103 A1-B2-C104 A1-B2-C105 A1-B2-C106 A1-B2-C107 A1-B2-C108

A1-B2-C109 A1-B2-C110 A1-B2-C111 A1-B2-C112 A1-B2-C113 A1-B2-C114

A1-B2-C115 A1-B2-C116 A1-B2-C117 A1-B2-C118 A1-B2-C119 A1-B2-C120

A1-B2-C121 A1-B2-C122 A1-B2-C123 A1-B2-C124 A1-B2-C125 A1-B2-C126

A1-B2-C127 A1-B2-C128 A1-B2-C129 A1-B2-C130 A1-B2-C131 A1-B2-C132

A1-B2-C133 A1-B2-C134 A1-B2-C135 A1-B2-C136 A1-B2-C137 A1-B2-C138

A1-B2-C139 A1-B2-C140 BLANK BLANK BLANK BLANK

A1-B3-C1 A1-B3-C2 A1-B3-C3 A1-B3-C4 A1-B3-C5 A1-B3-C6

A1-B3-C7 A1-B3-C8 A1-B3-C9 A1-B3-C10 A1-B3-C11 A1-B3-C12

A1-B3-C13 A1-B3-C14 A1-B3-C15 A1-B3-C16 A1-B3-C17 A1-B3-C18

A1-B3-C19 A1-B3-C20 A1-B3-C21 A1-B3-C22 A1-B3-C23 A1-B3-C24

A1-B3-C25 A1-B3-C26 A1-B3-C27 A1-B3-C28 A1-B3-C29 A1-B3-C30

A1-B3-C31 A1-B3-C32 A1-B3-C33 A1-B3-C34 A1-B3-C35 A1-B3-C36

A1-B3-C37 A1-B3-C38 A1-B3-C39 A1-B3-C40 A1-B3-C41 A1-B3-C42

A1-B3-C43 A1-B3-C44 A1-B3-C45 A1-B3-C46 A1-B3-C47 A1-B3-C48

A1-B3-C49 A1-B3-C50 A1-B3-C51 A1-B3-C52 A1-B3-C53 A1-B3-C54

A1-B3-C55 A1-B3-C56 A1-B3-C57 A1-B3-C58 A1-B3-C59 A1-B3-C60

A1-B3-C61 A1-B3-C62 A1-B3-C63 A1-B3-C64 A1-B3-C65 A1-B3-C66

A1-B3-C67 A1-B3-C68 A1-B3-C69 A1-B3-C70 A1-B3-C71 A1-B3-C72

A1-B3-C73 A1-B3-C74 A1-B3-C75 A1-B3-C76 A1-B3-C77 A1-B3-C78

A1-B3-C79 A1-B3-C80 A1-B3-C81 A1-B3-C82 A1-B3-C83 A1-B3-C84

A1-B3-C85 A1-B3-C86 A1-B3-C87 A1-B3-C88 A1-B3-C89 A1-B3-C90

A1-B3-C91 A1-B3-C92 A1-B3-C93 A1-B3-C94 A1-B3-C95 A1-B3-C96

A1-B3-C97 A1-B3-C98 A1-B3-C99 A1-B3-C100 A1-B3-C101 A1-B3-C102

A1-B3-C103 A1-B3-C104 A1-B3-C105 A1-B3-C106 A1-B3-C107 A1-B3-C108

A1-B3-C109 A1-B3-C110 A1-B3-C111 A1-B3-C112 A1-B3-C113 A1-B3-C114

A1-B3-C115 A1-B3-C116 A1-B3-C117 A1-B3-C118 A1-B3-C119 A1-B3-C120

A1-B3-C121 A1-B3-C122 A1-B3-C123 A1-B3-C124 A1-B3-C125 A1-B3-C126

A1-B3-C127 A1-B3-C128 A1-B3-C129 A1-B3-C130 A1-B3-C131 A1-B3-C132

A1-B3-C133 A1-B3-C134 A1-B3-C135 A1-B3-C136 A1-B3-C137 A1-B3-C138

A1-B3-C139 A1-B3-C140 BLANK BLANK BLANK BLANK

A1-B4-C1 A1-B4-C2 A1-B4-C3 A1-B4-C4 A1-B4-C5 A1-B4-C6

A1-B4-C7 A1-B4-C8 A1-B4-C9 A1-B4-C10 A1-B4-C11 A1-B4-C12

A1-B4-C13 A1-B4-C14 A1-B4-C15 A1-B4-C16 A1-B4-C17 A1-B4-C18

A1-B4-C19 A1-B4-C20 A1-B4-C21 A1-B4-C22 A1-B4-C23 A1-B4-C24

A1-B4-C25 A1-B4-C26 A1-B4-C27 A1-B4-C28 A1-B4-C29 A1-B4-C30

A1-B4-C31 A1-B4-C32 A1-B4-C33 A1-B4-C34 A1-B4-C35 A1-B4-C36

A1-B4-C37 A1-B4-C38 A1-B4-C39 A1-B4-C40 A1-B4-C41 A1-B4-C42

A1-B4-C43 A1-B4-C44 A1-B4-C45 A1-B4-C46 A1-B4-C47 A1-B4-C48

A1-B4-C49 A1-B4-C50 A1-B4-C51 A1-B4-C52 A1-B4-C53 A1-B4-C54

A1-B4-C55 A1-B4-C56 A1-B4-C57 A1-B4-C58 A1-B4-C59 A1-B4-C60

A1-B4-C61 A1-B4-C62 A1-B4-C63 A1-B4-C64 A1-B4-C65 A1-B4-C66

A1-B4-C67 A1-B4-C68 A1-B4-C69 A1-B4-C70 A1-B4-C71 A1-B4-C72

A1-B4-C73 A1-B4-C74 A1-B4-C75 A1-B4-C76 A1-B4-C77 A1-B4-C78

A1-B4-C79 A1-B4-C80 A1-B4-C81 A1-B4-C82 A1-B4-C83 A1-B4-C84

A1-B4-C85 A1-B4-C86 A1-B4-C87 A1-B4-C88 A1-B4-C89 A1-B4-C90

A1-B4-C91 A1-B4-C92 A1-B4-C93 A1-B4-C94 A1-B4-C95 A1-B4-C96

A1-B4-C97 A1-B4-C98 A1-B4-C99 A1-B4-C100 A1-B4-C101 A1-B4-C102

A1-B4-C103 A1-B4-C104 A1-B4-C105 A1-B4-C106 A1-B4-C107 A1-B4-C108

A1-B4-C109 A1-B4-C110 A1-B4-C111 A1-B4-C112 A1-B4-C113 A1-B4-C114

A1-B4-C115 A1-B4-C116 A1-B4-C117 A1-B4-C118 A1-B4-C119 A1-B4-C120

A1-B4-C121 A1-B4-C122 A1-B4-C123 A1-B4-C124 A1-B4-C125 A1-B4-C126

A1-B4-C127 A1-B4-C128 A1-B4-C129 A1-B4-C130 A1-B4-C131 A1-B4-C132

A1-B4-C133 A1-B4-C134 A1-B4-C135 A1-B4-C136 A1-B4-C137 A1-B4-C138

A1-B4-C139 A1-B4-C140 BLANK BLANK BLANK BLANK

A1-B5-C1 A1-B5-C2 A1-B5-C3 A1-B5-C4 A1-B5-C5 A1-B5-C6

A1-B5-C7 A1-B5-C8 A1-B5-C9 A1-B5-C10 A1-B5-C11 A1-B5-C12

A1-B5-C13 A1-B5-C14 A1-B5-C15 A1-B5-C16 A1-B5-C17 A1-B5-C18

A1-B5-C19 A1-B5-C20 A1-B5-C21 A1-B5-C22 A1-B5-C23 A1-B5-C24

A1-B5-C25 A1-B5-C26 A1-B5-C27 A1-B5-C28 A1-B5-C29 A1-B5-C30

A1-B5-C31 A1-B5-C32 A1-B5-C33 A1-B5-C34 A1-B5-C35 A1-B5-C36

A1-B5-C37 A1-B5-C38 A1-B5-C39 A1-B5-C40 A1-B5-C41 A1-B5-C42

A1-B5-C43 A1-B5-C44 A1-B5-C45 A1-B5-C46 A1-B5-C47 A1-B5-C48

A1-B5-C49 A1-B5-C50 A1-B5-C51 A1-B5-C52 A1-B5-C53 A1-B5-C54

A1-B5-C55 A1-B5-C56 A1-B5-C57 A1-B5-C58 A1-B5-C59 A1-B5-C60

A1-B5-C61 A1-B5-C62 A1-B5-C63 A1-B5-C64 A1-B5-C65 A1-B5-C66

A1-B5-C67 A1-B5-C68 A1-B5-C69 A1-B5-C70 A1-B5-C71 A1-B5-C72

A1-B5-C73 A1-B5-C74 A1-B5-C75 A1-B5-C76 A1-B5-C77 A1-B5-C78

A1-B5-C79 A1-B5-C80 A1-B5-C81 A1-B5-C82 A1-B5-C83 A1-B5-C84

A1-B5-C85 A1-B5-C86 A1-B5-C87 A1-B5-C88 A1-B5-C89 A1-B5-C90

A1-B5-C91 A1-B5-C92 A1-B5-C93 A1-B5-C94 A1-B5-C95 A1-B5-C96

A1-B5-C97 A1-B5-C98 A1-B5-C99 A1-B5-B100 A1-B5-C101 A1-B5-C102

A1-B5-C103 A1-B5-C104 A1-B5-C105 A1-B5-C106 A1-B5-C107 A1-B5-C108

A1-B5-C109 A1-B5-C110 A1-B5-C111 A1-B5-C112 A1-B5-C113 A1-B5-C114

A1-B5-C115 A1-B5-C116 A1-B5-C117 A1-B5-C118 A1-B5-C119 A1-B5-C120

A1-B5-C121 A1-B5-C122 A1-B5-C123 A1-B5-C124 A1-B5-C125 A1-B5-C126

A1-B5-C127 A1-B5-C128 A1-B5-C129 A1-B5-C130 A1-B5-C131 A1-B5-C132

A1-B5-C133 A1-B5-C134 A1-B5-C135 A1-B5-C136 A1-B5-C137 A1-B5-C138

A1-B5-C139 A1-B5-C140 BLANK BLANK BLANK BLANK

A1-B6-C1 A1-B6-C2 A1-B6-C3 A1-B6-C4 A1-B6-C5 A1-B6-C6

A1-B6-C7 A1-B6-C8 A1-B6-C9 A1-B6-C10 A1-B6-C11 A1-B6-C12

A1-B6-C13 A1-B6-C14 A1-B6-C15 A1-B6-C16 A1-B6-C17 A1-B6-C18

A1-B6-C19 A1-B6-C20 A1-B6-C21 A1-B6-C22 A1-B6-C23 A1-B6-C24

A1-B6-C25 A1-B6-C26 A1-B6-C27 A1-B6-C28 A1-B6-C29 A1-B6-C30

A1-B6-C31 A1-B6-C32 A1-B6-C33 A1-B6-C34 A1-B6-C35 A1-B6-C36

A1-B6-C37 A1-B6-C38 A1-B6-C39 A1-B6-C40 A1-B6-C41 A1-B6-C42

A1-B6-C43 A1-B6-C44 A1-B6-C45 A1-B6-C46 A1-B6-C47 A1-B6-C48

A1-B6-C49 A1-B6-C50 A1-B6-C51 A1-B6-C52 A1-B6-C53 A1-B6-C54

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A1-B13-C133 A1-B13-C134 A1-B13-C135 A1-B13-C136 A1-B13-C137 A1-B13-C138

A1-B13-C139 A1-B13-C140 BLANK BLANK BLANK BLANK

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A2-B1-C133 A2-B1-C134 A2-B1-C135 A2-B1-C136 A2-B1-C137 A2-B1-C138

A2-B1-C139 A2-B1-C140 BLANK BLANK BLANK BLANK

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A2-B3-C127 A2-B3-C128 A2-B3-C129 A2-B3-C130 A2-B3-C131 A2-B3-C132

A2-B3-C133 A2-B3-C134 A2-B3-C135 A2-B3-C136 A2-B3-C137 A2-B3-C138

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A2-B4-C127 A2-B4-C128 A2-B4-C129 A2-B4-C130 A2-B4-C131 A2-B4-C132

A2-B4-C133 A2-B4-C134 A2-B4-C135 A2-B4-C136 A2-B4-C137 A2-B4-C138

A2-B4-C139 A2-B4-C140 BLANK BLANK BLANK BLANK

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A2-B5-C127 A2-B5-C128 A2-B5-C129 A2-B5-C130 A2-B5-C131 A2-B5-C132

A2-B5-C133 A2-B5-C134 A2-B5-C135 A2-B5-C136 A2-B5-C137 A2-B5-C138

A2-B5-C139 A2-B5-C140 BLANK BLANK BLANK BLANK

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A2-B6-C121 A2-B6-C122 A2-B6-C123 A2-B6-C124 A2-B6-C125 A2-B6-C126

A2-B6-C127 A2-B6-C128 A2-B6-C129 A2-B6-C130 A2-B6-C131 A2-B6-C132

A2-B6-C133 A2-B6-C134 A2-B6-C135 A2-B6-C136 A2-B6-C137 A2-B6-C138

A2-B6-C139 A2-B6-C140 BLANK BLANK BLANK BLANK

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A3-B1-C1 A3-B1-C2 A3-B1-C3 A3-B1-C4 A3-B1-C5 A3-B1-C6

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A3-B1-C43 A3-B1-C44 A3-B1-C45 A3-B1-C46 A3-B1-C47 A3-B1-C48

A3-B1-C49 A3-B1-C50 A3-B1-C51 A3-B1-C52 A3-B1-C53 A3-B1-C54

A3-B1-C55 A3-B1-C56 A3-B1-C57 A3-B1-C58 A3-B1-C59 A3-B1-C60

A3-B1-C61 A3-B1-C62 A3-B1-C63 A3-B1-C64 A3-B1-C65 A3-B1-C66

A3-B1-C67 A3-B1-C68 A3-B1-C69 A3-B1-C70 A3-B1-C71 A3-B1-C72

A3-B1-C73 A3-B1-C74 A3-B1-C75 A3-B1-C76 A3-B1-C77 A3-B1-C78

A3-B1-C79 A3-B1-C80 A3-B1-C81 A3-B1-C82 A3-B1-C83 A3-B1-C84

A3-B1-C85 A3-B1-C86 A3-B1-C87 A3-B1-C88 A3-B1-C89 A3-B1-C90

A3-B1-C91 A3-B1-C92 A3-B1-C93 A3-B1-C94 A3-B1-C95 A3-B1-C96

A3-B1-C97 A3-B1-C98 A3-B1-C99 A3-B1-C100 A3-B1-C101 A3-B1-C102

A3-B1-C103 A3-B1-C104 A3-B1-C105 A3-B1-C106 A3-B1-C107 A3-B1-C108

A3-B1-C109 A3-B1-C110 A3-B1-C111 A3-B1-C112 A3-B1-C113 A3-B1-C114

A3-B1-C115 A3-B1-C116 A3-B1-C117 A3-B1-C118 A3-B1-C119 A3-B1-C120

A3-B1-C121 A3-B1-C122 A3-B1-C123 A3-B1-C124 A3-B1-C125 A3-B1-C126

A3-B1-C127 A3-B1-C128 A3-B1-C129 A3-B1-C130 A3-B1-C131 A3-B1-C132

A3-B1-C133 A3-B1-C134 A3-B1-C135 A3-B1-C136 A3-B1-C137 A3-B1-C138

A3-B1-C139 A3-B1-C140 BLANK BLANK BLANK BLANK

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A3-B2-C49 A3-B2-C50 A3-B2-C51 A3-B2-C52 A3-B2-C53 A3-B2-C54

A3-B2-C55 A3-B2-C56 A3-B2-C57 A3-B2-C58 A3-B2-C59 A3-B2-C60

A3-B2-C61 A3-B2-C62 A3-B2-C63 A3-B2-C64 A3-B2-C65 A3-B2-C66

A3-B2-C67 A3-B2-C68 A3-B2-C69 A3-B2-C70 A3-B2-C71 A3-B2-C72

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A3-B2-C97 A3-B2-C98 A3-B2-C99 A3-B2-C100 A3-B2-C101 A3-B2-C102

A3-B2-C103 A3-B2-C104 A3-B2-C105 A3-B2-C106 A3-B2-C107 A3-B2-C108

A3-B2-C109 A3-B2-C110 A3-B2-C111 A3-B2-C112 A3-B2-C113 A3-B2-C114

A3-B2-C115 A3-B2-C116 A3-B2-C117 A3-B2-C118 A3-B2-C119 A3-B2-C120

A3-B2-C121 A3-B2-C122 A3-B2-C123 A3-B2-C124 A3-B2-C125 A3-B2-C126

A3-B2-C127 A3-B2-C128 A3-B2-C129 A3-B2-C130 A3-B2-C131 A3-B2-C132

A3-B2-C133 A3-B2-C134 A3-B2-C135 A3-B2-C136 A3-B2-C137 A3-B2-C138

A3-B2-C139 A3-B2-C140 BLANK BLANK BLANK BLANK

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A3-B3-C49 A3-B3-C50 A3-B3-C51 A3-B3-C52 A3-B3-C53 A3-B3-C54

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A3-B3-C103 A3-B3-C104 A3-B3-C105 A3-B3-C106 A3-B3-C107 A3-B3-C108

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A3-B3-C127 A3-B3-C128 A3-B3-C129 A3-B3-C130 A3-B3-C131 A3-B3-C132

A3-B3-C133 A3-B3-C134 A3-B3-C135 A3-B3-C136 A3-B3-C137 A3-B3-C138

A3-B3-C139 A3-B3-C140 BLANK BLANK BLANK BLANK

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A3-B4-C43 A3-B4-C44 A3-B4-C45 A3-B4-C46 A3-B4-C47 A3-B4-C48

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A3-B4-C127 A3-B4-C128 A3-B4-C129 A3-B4-C130 A3-B4-C131 A3-B4-C132

A3-B4-C133 A3-B4-C134 A3-B4-C135 A3-B4-C136 A3-B4-C137 A3-B4-C138

A3-B4-C139 A3-B4-C140 BLANK BLANK BLANK BLANK

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A3-B5-C43 A3-B5-C44 A3-B5-C45 A3-B5-C46 A3-B5-C47 A3-B5-C48

A3-B5-C49 A3-B5-C50 A3-B5-C51 A3-B5-C52 A3-B5-C53 A3-B5-C54

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A3-B5-C97 A3-B5-C98 A3-B5-C99 A3-B5-C100 A3-B5-C101 A3-B5-C102

A3-B5-C103 A3-B5-C104 A3-B5-C105 A3-B5-C106 A3-B5-C107 A3-B5-C108

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A3-B5-C121 A3-B5-C122 A3-B5-C123 A3-B5-C124 A3-B5-C125 A3-B5-C126

A3-B5-C127 A3-B5-C128 A3-B5-C129 A3-B5-C130 A3-B5-C131 A3-B5-C132

A3-B5-C133 A3-B5-C134 A3-B5-C135 A3-B5-C136 A3-B5-C137 A3-B5-C138

A3-B5-C139 A3-B5-C140 BLANK BLANK BLANK BLANK

A3-B6-C1 A3-B6-C2 A3-B6-C3 A3-B6-C4 A3-B6-C5 A3-B6-C6

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A3-B6-C121 A3-B6-C122 A3-B6-C123 A3-B6-C124 A3-B6-C125 A3-B6-C126

A3-B6-C127 A3-B6-C128 A3-B6-C129 A3-B6-C130 A3-B6-C131 A3-B6-C132

A3-B6-C133 A3-B6-C134 A3-B6-C135 A3-B6-C136 A3-B6-C137 A3-B6-C138

A3-B6-C139 A3-B6-C140 BLANK BLANK BLANK BLANK

A3-B7-C1 A3-B7-C2 A3-B7-C3 A3-B7-C4 A3-B7-C5 A3-B7-C6

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A3-B7-C49 A3-B7-C50 A3-B7-C51 A3-B7-C52 A3-B7-C53 A3-B7-C54

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A3-B7-C97 A3-B7-C98 A3-B7-C99 A3-B7-C100 A3-B7-C101 A3-B7-C102

A3-B7-C103 A3-B7-C104 A3-B7-C105 A3-B7-C106 A3-B7-C107 A3-B7-C108

A3-B7-C109 A3-B7-C110 A3-B7-C111 A3-B7-C112 A3-B7-C113 A3-B7-C114

A3-B7-C115 A3-B7-C116 A3-B7-C117 A3-B7-C118 A3-B7-C119 A3-B7-C120

A3-B7-C121 A3-B7-C122 A3-B7-C123 A3-B7-C124 A3-B7-C125 A3-B7-C126

A3-B7-C127 A3-B7-C128 A3-B7-C129 A3-B7-C130 A3-B7-C131 A3-B7-C132

A3-B7-C133 A3-B7-C134 A3-B7-C135 A3-B7-C136 A3-B7-C137 A3-B7-C138

A3-B7-C139 A3-B7-C140 BLANK BLANK BLANK BLANK

A3-B8-C1 A3-B8-C2 A3-B8-C3 A3-B8-C4 A3-B8-C5 A3-B8-C6

A3-B8-C7 A3-B8-C8 A3-B8-C9 A3-B8-C10 A3-B8-C11 A3-B8-C12

A3-B8-C13 A3-B8-C14 A3-B8-C15 A3-B8-C16 A3-B8-C17 A3-B8-C18

A3-B8-C19 A3-B8-C20 A3-B8-C21 A3-B8-C22 A3-B8-C23 A3-B8-C24

A3-B8-C25 A3-B8-C26 A3-B8-C27 A3-B8-C28 A3-B8-C29 A3-B8-C30

A3-B8-C31 A3-B8-C32 A3-B8-C33 A3-B8-C34 A3-B8-C35 A3-B8-C36

A3-B8-C37 A3-B8-C38 A3-B8-C39 A3-B8-C40 A3-B8-C41 A3-B8-C42

A3-B8-C43 A3-B8-C44 A3-B8-C45 A3-B8-C46 A3-B8-C47 A3-B8-C48

A3-B8-C49 A3-B8-C50 A3-B8-C51 A3-B8-C52 A3-B8-C53 A3-B8-C54

A3-B8-C55 A3-B8-C56 A3-B8-C57 A3-B8-C58 A3-B8-C59 A3-B8-C60

A3-B8-C61 A3-B8-C62 A3-B8-C63 A3-B8-C64 A3-B8-C65 A3-B8-C66

A3-B8-C67 A3-B8-C68 A3-B8-C69 A3-B8-C70 A3-B8-C71 A3-B8-C72

A3-B8-C73 A3-B8-C74 A3-B8-C75 A3-B8-C76 A3-B8-C77 A3-B8-C78

A3-B8-C79 A3-B8-C80 A3-B8-C81 A3-B8-C82 A3-B8-C83 A3-B8-C84

A3-B8-C85 A3-B8-C86 A3-B8-C87 A3-B8-C88 A3-B8-C89 A3-B8-C90

A3-B8-C91 A3-B8-C92 A3-B8-C93 A3-B8-C94 A3-B8-C95 A3-B8-C96

A3-B8-C97 A3-B8-C98 A3-B8-C99 A3-B8-C100 A3-B8-C101 A3-B8-C102

A3-B8-C103 A3-B8-C104 A3-B8-C105 A3-B8-C106 A3-B8-C107 A3-B8-C108

A3-B8-C109 A3-B8-C110 A3-B8-C111 A3-B8-C112 A3-B8-C113 A3-B8-C114

A3-B8-C115 A3-B8-C116 A3-B8-C117 A3-B8-C118 A3-B8-C119 A3-B8-C120

A3-B8-C121 A3-B8-C122 A3-B8-C123 A3-B8-C124 A3-B8-C125 A3-B8-C126

A3-B8-C127 A3-B8-C128 A3-B8-C129 A3-B8-C130 A3-B8-C131 A3-B8-C132

A3-B8-C133 A3-B8-C134 A3-B8-C135 A3-B8-C136 A3-B8-C137 A3-B8-C138

A3-B8-C139 A3-B8-C140 BLANK BLANK BLANK BLANK

A3-B9-C1 A3-B9-C2 A3-B9-C3 A3-B9-C4 A3-B9-C5 A3-B9-C6

A3-B9-C7 A3-B9-C8 A3-B9-C9 A3-B9-C10 A3-B9-C11 A3-B9-C12

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A3-B9-C25 A3-B9-C26 A3-B9-C27 A3-B9-C28 A3-B9-C29 A3-B9-C30

A3-B9-C31 A3-B9-C32 A3-B9-C33 A3-B9-C34 A3-B9-C35 A3-B9-C36

A3-B9-C37 A3-B9-C38 A3-B9-B39 A3-B9-C40 A3-B9-C41 A3-B9-C42

A3-B9-C43 A3-B9-C44 A3-B9-C45 A3-B9-C46 A3-B9-C47 A3-B9-C48

A3-B9-C49 A3-B9-C50 A3-B9-C51 A3-B9-C52 B3-B9-C53 A3-B9-C54

A3-B9-C55 A3-B9-C56 A3-B9-C57 A3-B9-C58 A3-B9-C59 A3-B9-C60

A3-B9-C61 A3-B9-C62 A3-B9-C63 A3-B9-C64 A3-B9-C65 A3-B9-C66

A3-B9-C67 A3-B9-C68 A3-B9-C69 A3-B9-C70 A3-B9-C71 A3-B9-C72

A3-B9-C73 A3-B9-C74 A3-B9-C75 A3-B9-C76 A3-B9-C77 A3-B9-C78

A3-B9-C79 A3-B9-C80 A3-B9-C81 A3-B9-C82 A3-B9-C83 A3-B9-C84

A3-B9-C85 A3-B9-C86 A3-B9-C87 A3-B9-C88 A3-B9-C89 A3-B9-C90

A3-B9-C91 A3-B9-C92 A3-B9-C93 A3-B9-C94 A3-B9-C95 A3-B9-C96

A3-B9-C97 A3-B9-C98 A3-B9-C99 A3-B9-C100 A3-B9-C101 A3-B9-C102

A3-B9-C103 A3-B9-C104 A3-B9-C105 A3-B9-C106 A3-B9-C107 A3-B9-C108

A3-B9-C109 A3-B9-C110 A3-B9-C111 A3-B9-C112 A3-B9-C113 A3-B9-C114

A3-B9-C115 A3-B9-C116 A3-B9-C117 A3-B9-C118 A3-B9-C119 A3-B9-C120

A3-B9-C121 A3-B9-C122 A3-B9-C123 A3-B9-C124 A3-B9-C125 A3-B9-C126

A3-B9-C127 A3-B9-C128 A3-B9-C129 A3-B9-C130 A3-B9-C131 A3-B9-C132

A3-B9-C133 A3-B9-C134 A3-B9-C135 A3-B9-C136 A3-B9-C137 A3-B9-C138

A3-B9-C139 A3-B9-C140 BLANK BLANK BLANK BLANK

A3-B10-C1 A3-B10-C2 A3-B10-C3 A3-B10-C4 A3-B10-C5 A3-10-C6

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A3-B10-C43 A3-B10-C44 A3-B10-C45 A3-B10-C46 A3-B10-C47 A3-B10-C48

A3-B10-C49 A3-B10-C50 A3-B10-C51 A3-B10-C52 A3-B10-C53 A3-B10-C54

A3-B10-C55 A3-B10-C56 A3-B10-C57 A3-B10-C58 A3-B10-C59 A3-B10-C60

A3-B10-C61 A3-B10-C62 A3-B10-C63 A3-B10-C64 A3-B10-C65 A3-B10-C66

A3-B10-C67 A3-B10-C68 A3-B10-C69 A3-B10-C70 A3-B10-C71 A3-B10-C72

A3-B10-C73 A3-B10-C74 A3-B10-C75 A3-B10-C76 A3-B10-C77 A3-B10-C78

A3-B10-C79 A3-B10-C80 A3-B10-C81 A3-B10-C82 A3-B10-C83 A3-B10-C84

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A3-B10-C97 A3-B10-C98 A3-B10-C99 A3-B10-C100 A3-B10-C101 A3-B10-C102

A3-B10-C103 A3-B10-C104 A3-B10-C105 A3-B10-C106 A3-B10-C107 A3-B10-C108

A3-B10-C109 A3-B10-C110 A3-B10-C111 A3-B10-C112 A3-B10-C113 A3-B10-C114

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A3-B10-C127 A3-B10-C128 A3-B10-C129 A3-B10-C130 A3-B10-C131 A3-B10-C132

A3-B10-C133 A3-B10-C134 A3-B10-C135 A3-B10-C136 A3-B10-C137 A3-B10-C138

A3-B10-C139 A3-B10-C140 BLANK BLANK BLANK BLANK

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A3-B11-C49 A3-B11-C50 A3-B11-C51 A3-B11-C52 A3-B11-C53 A3-B11-C54

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A3-B11-C127 A3-B11-C128 A3-B11-C129 A3-B11-C130 A3-B11-C131 A3-B11-C132

A3-B11-C133 A3-B11-C134 A3-B11-C135 A3-B11-C136 A3-B11-C137 A3-B11-C138

A3-B11-C139 A3-B11-C140 BLANK BLANK BLANK BLANK

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A3-B12-C43 A3-B12-C44 A3-B12-C45 A3-B12-C46 A3-B12-C47 A3-B12-C48

A3-B12-C49 A3-B12-C50 A3-B12-C51 A3-B12-C52 A3-B12-C53 A3-B12-C54

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A3-B12-C127 A3-B12-C128 A3-B12-C129 A3-B12-C130 A3-B12-C131 A3-B12-C132

A3-B12-C133 A3-B12-C134 A3-B12-C135 A3-B12-C136 A3-B12-C137 A3-B12-C138

A3-B12-C139 A3-B12-C140 BLANK BLANK BLANK BLANK

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A3-B13-C127 A3-B13-C128 A3-B13-C129 A3-B13-C130 A3-B13-C131 A3-B13-C132

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A3-B13-C139 A3-B13-C140 BLANK BLANK BLANK BLANK

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A4-B1-C97 A4-B1-C98 A4-B1-C99 A4-B1-C100 A4-B1-C101 A4-B1-C102

A4-B1-C103 A4-B1-C104 A4-B1-C105 A4-B1-C106 A4-B1-C107 A4-B1-C108

A4-B1-C109 A4-B1-C110 A4-B1-C111 A4-B1-C112 A4-B1-C113 A4-B1-C114

A4-B1-C115 A4-B1-C116 A4-B1-C117 A4-B1-C118 A4-B1-C119 A4-B1-C120

A4-B1-C121 A4-B1-C122 A4-B1-C123 A4-B1-C124 A4-B1-C125 A4-B1-C126

A4-B1-C127 A4-B1-C128 A4-B1-C129 A4-B1-C130 A4-B1-C131 A4-B1-C132

A4-B1-C133 A4-B1-C134 A4-B1-C135 A4-B1-C136 A4-B1-C137 A4-B1-C138

A4-B1-C139 A4-B1-C140 BLANK BLANK BLANK BLANK

A4-B2-C1 A4-B2-C2 A4-B2-C3 A4-B2-C4A 4-B2-C5 A4-B2-C6

A4-B2-C7 A4-B2-C8 A4-B2-C9 A4-B2-C10 A4-B2-C11 A4-B2-C12

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A4-B2-C19 A4-B2-C20 A4-B2-C21 A4-B2-C22 A4-B2-C23 A4-B2-C24

A4-B2-C25 A4-B2-C26 A4-B2-C27 A4-B2-C28 A4-B2-C29 A4-B2-C30

A4-B2-C31 A4-B2-C32 A4-B2-C33 A4-B2-C34 A4-B2-C35 A4-B2-C36

A4-B2-C37 A4-B2-C38 A4-B2-C39 A4-B2-C40 A4-B2-C41 A4-B2-C42

A4-B2-C43 A4-B2-C44 A4-B2-C45 A4-B2-C46 A4-B2-C47 A4-B2-C48

A4-B2-C49 A4-B2-C50 A4-B2-C51 A4-B2-C52 A4-B2-C53 A4-B2-C54

A4-B2-C55 A4-B2-C56 A4-B2-C57 A4-B2-C58 A4-B2-C59 A4-B2-C60

A4-B2-C61 A4-B2-C62 A4-B2-C63 A4-B2-C64 A4-B2-C65 A4-B2-C66

A4-B2-C67 A4-B2-C68 A4-B2-C69 A4-B2-C70 A4-B2-C71 A4-B2-C72

A4-B2-C73 A4-B2-C74 A4-B2-C75 A4-B2-C76 A4-B2-C77 A4-B2-C78

A4-B2-C79 A4-B2-C80 A4-B2-C81 A4-B2-C82 A4-B2-C83 A4-B2-C84

A4-B2-C85 A4-B2-C86 A4-B2-C87 A4-B2-C88 A4-B2-C89 A4-B2-C90

A4-B2-C91 A4-B2-C92 A4-B2-C93 A4-B2-C94 A4-B2-C95 A4-B2-C96

A4-B2-C97 A4-B2-C98 A4-B2-C99 A4-B2-C100 A4-B2-C101 A4-B2-C102

A4-B2-C103 A4-B2-C104 A4-B2-C105 A4-B2-C106 A4-B2-C107 A4-B2-C108

A4-B2-C109 A4-B2-C110 A4-B2-C111 A4-B2-C112 A4-B2-C113 A4-B2-C114

A4-B2-C115 A4-B2-C116 A4-B2-C117 A4-B2-C118 A4-B2-C119 A4-B2-C120

A4-B2-C121 A4-B2-C122 A4-B2-C123 A4-B2-C124 A4-B2-C125 A4-B2-C126

A4-B2-C127 A4-B2-C128 A4-B2-C129 A4-B2-C130 A4-B2-C131 A4-B2-C132

A4-B2-C133 A4-B2-C134 A4-B2-C135 A4-B2-C136 A4-B2-C137 A4-B2-C138

A4-B2-C139 A4-B2-C140 BLANK BLANK BLANK BLANK

A4-B3-C1 A4-B3-C2 A4-B3-C3 A4-B3-C4 A4-B3-C5 A4-B3-C6

A4-B3-C7 A4-B3-C8 A4-B3-C9 A4-B3-C10 A4-B3-C11 A4-B3-C12

A4-B3-C13 A4-B3-C14 A4-B3-C15 A4-B3-C16 A4-B3-C17 A4-B3-C18

A4-B3-C19 A4-B3-C20 A4-B3-C21 A4-B3-C22 A4-B3-C23 A4-B3-C24

A4-B3-C25 A4-B3-C26 A4-B3-C27 A4-B3-C28 A4-B3-C29 A4-B3-C30

A4-B3-C31 A4-B3-C32 A4-B3-C33 A4-B3-C34 A4-B3-C35 A4-B3-C36

A4-B3-C37 A4-B3-C38 A4-B3-C39 A4-B3-C40 A4-B3-C41 A4-B3-C42

A4-B3-C43 A4-B3-C44 A4-B3-C45 A4-B3-C46 A4-B3-C47 A4-B3-C48

A4-B3-C49 A4-B3-C50 A4-B3-C51 A4-B3-C52 A4-B3-C53 A4-B3-C54

A4-B3-C55 A4-B3-C56 A4-B3-C57 A4-B3-C58 A4-B3-C59 A4-B3-C60

A4-B3-C61 A4-B3-C62 A4-B3-C63 A4-B3-C64 A4-B3-C65 A4-B3-C66

A4-B3-C67 A4-B3-C68 A4-B3-C69 A4-B3-C70 A4-B3-C71 A4-B3-C72

A4-B3-C73 A4-B3-C74 A4-B3-C75 A4-B3-C76 A4-B3-C77 A4-B3-C78

A4-B3-C79 A4-B3-C80 A4-B3-C81 A4-B3-C82 A4-B3-C83 A4-B3-C84

A4-B3-C85 A4-B3-C86 A4-B3-C87 A4-B3-C88 A4-B3-C89 A4-B3-C90

A4-B3-C91 A4-B3-C92 A4-B3-C93 A4-B3-C94 A4-B3-C95 A4-B3-C96

A4-B3-C97 A4-B3-C98 A4-B3-C99 A4-B3-C100 A4-B3-C101 A4-B3-C102

A4-B3-C103 A4-B3-C104 A4-B3-C105 A4-B3-C106 A4-B3-C107 A4-B3-C108

A4-B3-C109 A4-B3-C110 A4-B3-C111 A4-B3-C112 A4-B3-C113 A4-B3-C114

A4-B3-C115 A4-B3-C116 A4-B3-C117 A4-B3-C118 A4-B3-C119 A4-B3-C120

A4-B3-C121 A4-B3-C122 A4-B3-C123 A4-B3-C124 A4-B3-C125 A4-B3-C126

A4-B3-C127 A4-B3-C128 A4-B3-C129 A4-B3-C130 A4-B3-C131 A4-B3-C132

A4-B3-C133 A4-B3-C134 A4-B3-C135 A4-B3-C136 A4-B3-C137 A4-B3-C138

A4-B3-C139 A4-B3-C140 BLANK BLANK BLANK BLANK

A4-B4-C1 A4-B4-C2 A4-B4-C3 A4-B4-C4 A4-B4-C5 A4-B4-C6

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A4-B4-C37 A4-B4-C38 A4-B4-C39 A4-B4-C40 A4-B4-C41 A4-B4-C42

A4-B4-C43 A4-B4-C44 A4-B4-C45 A4-B4-C46 A4-B4-C47 A4-B4-C48

A4-B4-C49 A4-B4-C50 A4-B4-C51 A4-B4-C52 A4-B4-C53 A4-B4-C54

A4-B4-C55 A4-B4-C56 A4-B4-C57 A4-B4-C58 A4-B4-C59 A4-B4-C60

A4-B4-C61 A4-B4-C62 A4-B4-C63 A4-B4-C64 A4-B4-C65 A4-B4-C66

A4-B4-C67 A4-B4-C68 A4-B4-C69 A4-B4-C70 A4-B4-C71 A4-B4-C72

A4-B4-C73 A4-B4-C74 A4-B4-C75 A4-B4-C76 A4-B4-C77 A4-B4-C78

A4-B4-C79 A4-B4-C80 A4-B4-C81 A4-B4-C82 A4-B4-C83 A4-B4-C84

A4-B4-C85 A4-B4-C86 A4-B4-C87 A4-B4-C88 A4-B4-C89 A4-B4-C90

A4-B4-C91 A4-B4-C92 A4-B4-C93 A4-B4-C94 A4-B4-C95 A4-B4-C96

A4-B4-C97 A4-B4-C98 A4-B4-C99 A4-B4-C100 A4-B4-C101 A4-B4-C102

A4-B4-C103 A4-B4-C104 A4-B4-C105 A4-B4-C106 A4-B4-C107 A4-B4-C108

A4-B4-C109 A4-B4-C110 A4-B4-C111 A4-B4-C112 A4-B4-C113 A4-B4-C114

A4-B4-C115 A4-B4-C116 A4-B4-C117 A4-B4-C118 A4-B4-C119 A4-B4-C120

A4-B4-C121 A4-B4-C122 A4-B4-C123 A4-B4-C124 A4-B4-C125 A4-B4-C126

A4-B4-C127 A4-B4-C128 A4-B4-C129 A4-B4-C130 A4-B4-C131 A4-B4-C132

A4-B4-C133 A4-B4-C134 A4-B4-C135 A4-B4-C136 A4-B4-C137 A4-B4-C138

A4-B4-C139 A4-B4-C140 BLANK BLANK BLANK BLANK

A4-B5-C1 A4-B5-C2 A4-B5-C3 A4-B5-C4 A4-B5-C5 A4-B5-C6

A4-B5-C7 A4-B5-C8 A4-B5-C9 A4-B5-C10 A4-B5-C11 A4-B5-C12

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A4-B5-C31 A4-B5-C32 A4-B5-C33 A4-B5-C34 A4-B5-C35 A4-B5-C36

A4-B5-C37 A4-B5-C38 A4-B5-C39 A4-B5-C40 A4-B5-C41 A4-B5-C42

A4-B5-C43 A4-B5-C44 A4-B5-C45 A4-B5-C46 A4-B5-C47 A4-B5-C48

A4-B5-C49 A4-B5-C50 A4-B5-C51 A4-B5-C52 A4-B5-C53 A4-B5-C54

A4-B5-C55 A4-B5-C56 A4-B5-C57 A4-B5-C58 A4-B5-C59 A4-B5-C60

A4-B5-C61 A4-B5-C62 A4-B5-C63 A4-B5-C64 A4-B5-C65 A4-B5-C66

A4-B5-C67 A4-B5-C68 A4-B5-C69 A4-B5-C70 A4-B5-C71 A4-B5-C72

A4-B5-C73 A4-B5-C74 A4-B5-C75 A4-B5-C76 A4-B5-C77 A4-B5-C78

A4-B5-C79 A4-B5-C80 A4-B5-C81 A4-B5-C82 A4-B5-C83 A4-B5-C84

A4-B5-C85 A4-B5-C86 A4-B5-C87 A4-B5-C88 A4-B5-C89 A4-B5-C90

A4-B5-C91 A4-B5-C92 A4-B5-C93 A4-B5-C94 A4-B5-C95 A4-B5-C96

A4-B5-C97 A4-B5-C98 A4-B5-C99 A4-B5-C100 A4-B5-C101 A4-B5-C102

A4-B5-C103 A4-B5-C104 A4-B5-C105 A4-B5-C106 A4-B5-C107 A4-B5-C108

A4-B5-C109 A4-B5-C110 A4-B5-C111 A4-B5-C112 A4-B5-C113 A4-B5-C114

A4-B5-C115 A4-B5-C116 A4-B5-C117 A4-B5-C118 A4-B5-C119 A4-B5-C120

A4-B5-C121 A4-B5-C122 A4-B5-C123 A4-B5-C124 A4-B5-C125 A4-B5-C126

A4-B5-C127 A4-B5-C128 A4-B5-C129 A4-B5-C130 A4-B5-C131 A4-B5-C132

A4-B5-C133 A4-B5-C134 A4-B5-C135 A4-B5-C136 A4-B5-C137 A4-B5-C138

A4-B5-C139 A4-B5-C140 BLANK BLANK BLANK BLANK

A4-B6-C1 A4-B6-C2 A4-B6-C3 A4-B6-C4 A4-B6-C5A A4-B6-C6

A4-B6-C7 A4-B6-C8 A4-B6-C9 A4-B6-C10 A4-B6-C11 A4-B6-C12

A4-b6-C13 A4-B6-C14 A4-B6-C15 A4-B6-C16 A4-B6-C17 A4-B6-C18

A4-B6-C19 A4-B6-C20 A4-B6-C21 A4-B6-C22 A4-B6-C23 A4-B6-C24

A4-B6-C25 A4-B6-C26 A4-B6-C27 A4-B6-C28 A4-B6-C29 A4-B6-C30

A4-B6-C31 A4-B6-C32 A4-B6-C33 A4-B6-C34 A4-B6-C35 A4-B6-C36

A4-B6-C37 A4-B6-C38 A4-B6-C39 A4-B6-C40 A4-B6-C41 A4-B6-C42

A4-B6-C43 A4-B6-C44 A4-B6-C45 A4-B6-C46 A4-B6-C47 A4-B6-C48

A4-B6-C49 A4-B6-C50 A4-B6-C51 A4-B6-C52 A4-B6-C53 A4-B6-C54

A4-B6-C55 A4-B6-C56 A4-B6-C57 A4-B6-C58 A4-B6-C59 A4-B6-C60

A4-B6-C61 A4-B6-C62 A4-B6-C63 A4-B6-C64 A4-B6-C65 A4-B6-C66

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A4-B6-C91 A4-B6-C92 A4-B6-C93 A4-B6-C94 A4-B6-C95 A4-B6-C96

A4-B6-C97 A4-B6-C98 A4-B6-C99 A4-B6-C100 A4-B6-C101 A4-B6-C102

A4-B6-C103 A4-B6-C104 A4-B6-C105 A4-B6-C106 A4-B6-C107 A4-B6-C108

A4-B6-C109 A4-B6-C110 A4-B6-C111 A4-B6-C112 A4-B6-C113 A4-B6-C114

A4-B6-C115 A4-B6-C116 A4-B6-C117 A4-B6-C118 A4-B6-C119 A4-B6-C120

A4-B6-C121 A4-B6-C122 A4-B6-C123 A4-B6-C124 A4-B6-C125 A4-B6-C126

A4-B6-C127 A4-B6-C128 A4-B6-C129 A4-B6-C130 A4-B6-C131 A4-B6-C132

A4-B6-C133 A4-B6-C134 A4-B6-C135 A4-B6-C136 A4-B6-C137 A4-B6-C138

A4-B6-C139 A4-B6-C140 BLANK BLANK BLANK BLANK

A4-B7-C1 A4-B7-C2 A4-B7-C3 A4-B7-C4 A4-B7-C5 A4-B7-C6

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A4-B7-C19 A4-B7-C20 A4-B7-C21 A4-B7-C22 A4-B7-C23 A4-B7-C24

A4-B7-C25 A4-B7-C26 A4-B7-C27 A4-B7-C28 A4-B7-C29 A4-B7-C30

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A4-B7-C37 A4-B7-C38 A4-B7-C39 A4-B7-C40 A4-B7-C41 A4-B7-C42

A4-B7-C43 A4-B7-C44 A4-B7-C45 A4-B7-C46 A4-B7-C47 A4-B7-C48

A4-B7-C49 A4-B7-C50 A4-B7-C51 A4-B7-C52 A4-B7-C53 A4-B7-C54

A4-B7-C55 A4-B7-C56 A4-B7-C57 A4-B7-C58 A4-B7-C59 A4-B7-C60

A4-B7-C61 A4-B7-C62 A4-B7-C63 A4-B7-C64 A4-B7-C65 A4-B7-C66

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A4-B7-C97 A4-B7-C98 A4-B7-C99 A4-B7-C100 A4-B7-C101 A4-B7-C102

A4-B7-C103 A4-B7-C104 A4-B7-C105 A4-B7-C106 A4-B7-C107 A4-B7-C108

A4-B7-C109 A4-B7-C110 A4-B7-C111 A4-B7-C112 A4-B7-C113 A4-B7-C114

A4-B7-C115 A4-B7-C116 A4-B7-C117 A4-B7-C118 A4-B7-C119 A4-B7-C120

A4-B7-C121 A4-B7-C122 A4-B7-C123 A4-B7-C124 A4-B7-C125 A4-B7-C126

A4-B7-C127 A4-B7-C128 A4-B7-C129 A4-B7-C130 A4-B7-C131 A4-B7-C132

A4-B7-C133 A4-B7-C134 A4-B7-C135 A4-B7-C136 A4-B7-C137 A4-B7-C138

A4-B7-C139 A4-B7-C140 BLANK BLANK BLANK BLANK

A4-B8-C1 A4-B8-C2 A4-B8-C3 A4-B8-C4 A4-B8-C5 A4-B8-C6

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A4-B8-C19 A4-B8-C20 A4-B8-C21 A4-B8-C22 A4-B8-C23 A4-B8-C24

A4-B8-C25 A4-B8-C26 A4-B8-C27 A4-B8-C28 A4-B8-C29 A4-B8-C30

A4-B8-C31 A4-B8-C32 A4-B8-C33 A4-B8-C34 A4-B8-C35 A4-B8-C36

A4-B8-C37 A4-B8-C38 A4-B8-C39 A4-B8-C40 A4-B8-C41 A4-B8-C42

A4-B8-C43 A4-B8-C44 A4-B8-C45 A4-B8-C46 A4-B8-C47 A4-B8-C48

A4-B8-C49 A4-B8-C50 A4-B8-C51 A4-B8-C52 A4-B8-C53 A4-B8-C54

A4-B8-C55 A4-B8-C56 A4-B8-C57 A4-B8-C58 A4-B8-C59 A4-B8-C60

A4-B8-C61 A4-B8-C62 A4-B8-C63 A4-B8-C64 A4-B8-C65 A4-B8-C66

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A4-B8-C73 A4-B8-C74 A4-B8-C75 A4-B8-C76 A4-B8-C77 A4-B8-C78

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A4-B8-C85 A4-B8-C86 A4-B8-C87 A4-B8-C88 A4-B8-C89 A4-B8-C90

A4-B8-C91 A4-B8-C92 A4-B8-C93 A4-B8-C94 A4-B8-C95 A4-B8-C96

A4-B8-C97 A4-B8-C98 A4-B8-C99 A4-B8-C100 A4-B8-C101 A4-B8-C102

A4-B8-C103 A4-B8-C104 A4-B8-C105 A4-B8-C106 A4-B8-C107 A4-B8-C108

A4-B8-C109 A4-B8-C110 A4-B8-C111 A4-B8-C112 A4-B8-C113 A4-B8-C114

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A4-B8-C121 A4-B8-C122 A4-B8-C123 A4-B8-C124 A4-B8-C125 A4-B8-C126

A4-B8-C127 A4-B8-C128 A4-B8-C129 A4-B8-C130 A4-B8-C131 A4-B8-C132

A4-B8-C133 A4-B8-C134 A4-B8-C135 A4-B8-C136 A4-B8-C137 A4-B8-C138

A4-B8-C139 A4-B8-C140 BLANK BLANK BLANK BLANK

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A4-B9-C31 A4-B9-C32 A4-B9-C33 A4-B9-C34 A4-B9-C35 A4-B9-C36

A4-B9-C37 A4-B9-C38 A4-B9-C39 A4-B9-C40 A4-B9-C41 A4-B9-C42

A4-B9-C43 A4-B9-C44 A4-B9-C45 A4-B9-C46 A4-B9-C47 A4-B9-C48

A4-B9-C49 A4-B9-C50 A4-B9-C51 A4-B9-C52 A4-B9-C53 A4-B9-C54

A4-B9-C55 A4-B9-C56 A4-B9-C57 A4-B9-C58 A4-B9-C59 A4-B9-C60

A4-B9-C61 A4-B9-C62 A4-B9-C63 A4-B9-C64 A4-B9-C65 A4-B9-C66

A4-B9-C67 A4-B9-C68 A4-B9-C69 A4-B9-C70 A4-B9-C71 A4-B9-C72

A4-B9-C73 A4-B9-C74 A4-B9-C75 A4-B9-C76 A4-B9-C77 A4-B9-C78

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A4-B9-C85 A4-B9-C86 A4-B9-C87 A4-B9-C88 A4-B9-C89 A4-B9-C90

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A4-B9-C103 A4-B9-C104 A4-B9-C105 A4-B9-C106 A4-B9-C107 A4-B9-C108

A4-B9-C109 A4-B9-C110 A4-B9-C111 A4-B9-C112 A4-B9-C113 A4-B9-C114

A4-B9-C115 A4-B9-C116 A4-B9-C117 A4-B9-C118 A4-B9-C119 A4-B9-C120

A4-B9-C121 A4-B9-C122 A4-B9-C123 A4-B9-C124 A4-B9-C125 A4-B9-C126

A4-B9-C127 A4-B9-C128 A4-B9-C129 A4-B9-C130 A4-B9-C131 A4-B9-C132

A4-B9-C133 A4-B9-C134 A4-B9-C135 A4-B9-C136 A4-B9-C137 A4-B9-C138

A4-B9-C139 A4-B9-C140 BLANK BLANK BLANK BLANK

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A4-B10-C25 A4-B10-C26 A4-B10-C27 A4-B10-C28 A4-B10-C29 A4-B10-C30

A4-B10-C31 A4-B10-C32 A4-B10-C33 A4-B10-C34 A4-B10-C35 A4-B10-C36

A4-B10-C37 A4-B10-C38 A4-B10-C39 A4-B10-C40 A4-10-C41 A4-B10-C42

A4-B10-C43 A4-B10-C44 A4-B10-C45 A4-B10-C46 A4-B10-C47 A4-B10-C48

A4-B10-C49 A4-B10-C50 A4-B10-C51 A4-B10-C52 A4-B10-C53 A4-B10-C54

A4-B10-C55 A4-B10-C56 A4-B10-C57 A4-B10-C58 A4-B10-C59 A4-B10-C60

A4-B10-C61 A4-B10-C62 A4-B10-C63 A4-B10-C64 A4-B10-C65 A4-B10-C66

A4-B10-C67 A4-B10-C68 A4-B10-C69 A4-B10-C70 A4-B10-C71 A4-B10-C72

A4-B10-C73 A4-B10-C74 A4-B10-C75 A4-B10-C76 A4-B10-C77 A4-B10-C78

A4-B10-C79 A4-B10-C80 A4-B10-C81 A4-B10-C82 A4-B10-C83 A4-B10-C84

A4-B10-C85 A4-B10-C86 A4-B10-C87 A4-B10-C88 A4-B10-C89 A4-B10-C90

A4-B10-C91 A4-B10-C92 A4-B10-C93 A4-B10-C94 A4-B10-C95 A4-B10-C96

A4-B10-C97 A4-B10-C98 A4-B10-C99 A4-B10-C100 A4-B10-C101 A4-B10-C102

A4-B10-C103 A4-B10-C104 A4-B10-C105 A4-B10-C106 A4-B10-C107 A4-B10-C108

A4-B10-C109 A4-B10-C110 A4-B10-C111 A4-B10-C112 A4-B10-C113 A4-B10-C114

A4-B10-C115 A4-B10-C116 A4-B10-C117 A4-B10-C118 A4-B10-C119 A4-B10-C120

A4-B10-C121 A4-B10-C122 A4-B10-C123 A4-B10-C124 A4-B10-C125 A4-B10-C126

A4-B10-C127 A4-B10-C128 A4-B10-C129 A4-B10-C130 A4-B10-C131 A4-B10-C132

A4-B10-C133 A4-B10-C134 A4-B10-C135 A4-B10-C136 A4-B10-C137 A4-B10-C138

A4-B10-C139 A4-B10-C140 BLANK BLANK BLANK BLANK

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A4-B11-C43 A4-B11-C44 A4-B11-C45 A4-B11-C46 A4-B11-C47 A4-B11-C48

A4-B11-C49 A4-B11-C50 A4-B11-C51 A4-B11-C52 A4-B11-C53 A4-B11-C54

A4-B11-C55 A4-B11-C56 A4-B11-C57 A4-B11-C58 A4-B11-C59 A4-B11-C60

A4-B11-C61 A4-B11-C62 A4-B11-C63 A4-B11-C64 A4-B11-C65 A4-B11-C66

A4-B11-C67 A4-B11-C68 A4-B11-C69 A4-B11-C70 A4-B11-C71 A4-B11-C72

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A4-B11-C103 A4-B11-C104 A4-B11-C105 A4-B11-C106 A4-B11-C107 A4-B11-C108

A4-B11-C109 A4-B11-C110 A4-B11-C111 A4-B11-C112 A4-B11-C113 A4-B11-C114

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A4-B11-C127 A4-B11-C128 A4-B11-C129 A4-B11-C130 A4-B11-C131 A4-B11-C132

A4-B11-C133 A4-B11-C134 A4-B11-C135 A4-B11-C136 A4-B11-C137 A4-B11-C138

A4-B11-C139 A4-B11-C140 BLANK BLANK BLANK BLANK

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A4-B12-C43 A4-B12-C44 A4-B12-C45 A4-B12-C46 A4-B12-C47 A4-B12-C48

A4-B12-C49 A4-B12-C50 A4-B12-C51 A4-B12-C52 A4-B12-C53 A4-B12-C54

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A5-B2-C139 A5-B2-C140 BLANK BLANK BLANK BLANK

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A5-B3-C133 A5-B3-C134 A5-B3-C135 A5-B3-C136 A5-B3-C137 A5-B3-C138

A5-B3-C139 A5-B3-C140 BLANK BLANK BLANK BLANK

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A5-B4-C127 A5-B4-C128 A5-B4-C129 A5-B4-C130 A5-B4-C131 A5-B4-C132

A5-B4-C133 A5-B4-C134 A5-B4-C135 A5-B4-C136 A5-B4-C137 A5-B4-C138

A5-B4-C139 A5-B4-C140 BLANK BLANK BLANK BLANK

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A5-B5-C133 A5-B5-C134 A5-B5-C135 A5-B5-C136 A5-B5-C137 A5-B5-C138

A5-B5-C139 A5-B5-C140 BLANK BLANK BLANK BLANK

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A5-B6-C139 A5-B6-C140 BLANK BLANK BLANK BLANK

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A5-B8-C133 A5-B8-C134 A5-B8-C135 A5-B8-C136 A5-B8-C137 A5-B8-C138

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A5-B9-C37 A5-B9-C38 A5-B9-C39 A5-B9-C40 A5-B9-C41 A5-B9-C42

A5-B9-C43 A5-B9-C44 A5-B9-C45 A5-B9-C46 A5-B9-C47 A5-B9-C48

A5-B9-C49 A5-B9-C50 A5-B9-C51 A5-B9-C52 A5-B9-C53 A5-B9-C54

A5-B9-C55 A5-B9-C56 A5-B9-C57 A5-B9-C58 A5-B9-C59 A5-B9-C60

A5-B9-C61 A5-B9-C62 A5-B9-C63 A5-B9-C64 A5-B9-C65 A5-B9-C66

A5-B9-C67 A5-B9-C68 A5-B9-C69 A5-B9-C70 A5-B9-C71 A5-B9-C72

A5-B9-C73 A5-B9-C74 A5-B9-C75 A5-B9-C76 A5-B9-C77 A5-B9-C78

A5-B9-C79 A5-B9-C80 A5-B9-C81 A5-B9-C82 A5-B9-C83 A5-B9-C84

A5-B9-C85 A5-B9-C86 A5-B9-C87 A5-B9-C88 A5-B9-C89 A5-B9-C90

A5-B9-C91 A5-B9-C92 A5-B9-C93 A5-B9-C94 A5-B9-C95 A5-B9-C96

A5-B9-C97 A5-B9-C98 A5-B9-C99 A5-B9-C100 A5-B9-C101 A5-B9-C102

A5-B9-C103 A5-B9-C104 A5-B9-C105 A5-B9-C106 A5-B9-C107 A5-B9-C108

A5-B9-C109 A5-B9-C110 A5-B9-C111 A5-B9-C112 A5-B9-C113 A5-B9-C114

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A5-B9-C121 A5-B9-C122 A5-B9-C123 A5-B9-C124 A5-B9-C125 A5-B9-C126

A5-B9-C127 A5-B9-C128 A5-B9-C129 A5-B9-C130 A5-B9-C131 A5-B9-C132

A5-B9-C133 A5-B9-C134 A5-B9-C135 A5-B9-C136 A5-B9-C137 A5-B9-C138

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A5-B10-C43 A5-B10-C44 A5-B10-C45 A5-B10-C46 A5-B10-C47 A5-B10-C48

A5-B10-C49 A5-B10-C50 A5-B10-C51 A5-B10-C52 A5-B10-C53 A5-B10-C54

A5-B10-C55 A5-B10-C56 A5-B10-C57 A5-B10-C58 A5-B10-C59 A5-B10-C60

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A5-B10-C97 A5-B10-C98 A5-B10-C99 A5-B10-C100 A5-B10-C101 A5-B10-C102

A5-B10-C103 A5-B10-C104 A5-B10-C105 A5-B10-C106 A5-B10-C107 A5-B10-C108

A5-B10-C109 A5-B10-C110 A5-B10-C111 A5-B10-C112 A5-B10-C113 A5-B10-C114

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A5-B10-C127 A5-B10-C128 A5-B10-C129 A5-B10-C130 A5-B10-C131 A5-B10-C132

A5-B10-C133 A5-B10-C134 A5-B10-C135 A5-B10-C136 A5-B10-C137 A5-B10-C138

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A5-B11-C43 A5-B11-C44 A5-B11-C45 A5-B11-C46 A5-B11-C47 A5-B11-C48

A5-B11-C49 A5-B11-C50 A5-B11-C51 A5-B11-C52 A5-B11-C53 A5-B11-C54

A5-B11-C55 A5-B11-C56 A5-B11-C57 A5-B11-C58 A5-B11-C59 A5-B11-C60

A5-B11-C61 A5-B11-C62 A5-B11-C63 A5-B11-C64 A5-B11-C65 A5-B11-C66

A5-B11-C67 A5-B11-C68 A5-B11-C69 A5-B11-C70 A5-B11-C71 A5-B11-C72

A5-B11-C73 A5-B11-C74 A5-B11-C75 A5-B11-C76 A5-B11-C77 A5-B11-C78

A5-B11-C79 A5-B11-C80 A5-B11-C81 A5-B11-C82 A5-B11-C83 A5-B11-C84

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A5-B11-C91 A5-B11-C92 A5-B11-C93 A5-B11-C94 A5-B11-C95 A5-B11-C96

A5-B11-C97 A5-B11-C98 A5-B11-C99 A5-B11-C100 A5-B11-C101 A5-B11-C102

A5-B11-C103 A5-B11-C104 A5-B11-C105 A5-B11-C106 A5-B11-C107 A5-B11-C108

A5-B11-C109 A5-B11-C110 A5-B11-C111 A5-B11-C112 A5-B11-C113 A5-B11-C114

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A5-B11-C127 A5-B11-C128 A5-B11-C129 A5-B11-C130 A5-B11-C131 A5-B11-C132

A5-B11-C133 A5-B11-C134 A5-B11-C135 A5-B11-C136 A5-B11-C137 A5-B11-C138

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A5-B12-C133 A5-B12-C134 A5-B12-C135 A5-B12-C136 A5-B12-C137 A5-B12-C138

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A5-B13-C127 A5-B13-C128 A5-B13-C129 A5-B13-C130 A5-B13-C131 A5-B13-C132

A5-B13-C133 A5-B13-C134 A5-B13-C135 A5-B13-C136 A5-B13-C137 A5-B13-C138

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A6-B2-C127 A6-B2-C128 A6-B2-C129 A6-B2-C130 A6-B2-C131 A6-B2-C132

A6-B2-C133 A6-B2-C134 A6-B2-C135 A6-B2-C136 A6-B2-C137 A6-B2-C138

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A6-B3-C19 A6-B3-C20 A6-B3-C21 A6-B3-C22 A6-B3-C23 A6-B3-C24

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A6-B3-C31 A6-B3-C32 A6-B3-C33 A6-B3-C34 A6-B3-C35 A6-B3-C36

A6-B3-C37 A6-B3-C38 A6-B3-C39 A6-B3-C40 A6-B3-C41 A6-B3-C42

A6-B3-C43 A6-B3-C44 A6-B3-C45 A6-B3-C46 A6-B3-C47 A6-B3-C48

A6-B3-C49 A6-B3-C50 A6-B3-C51 A6-B3-C52 A6-B3-C53 A6-B3-C54

A6-B3-C55 A6-B3-C56 A6-B3-C57 A6-B3-C58 A6-B3-C59 A6-B3-C60

A6-B3-C61 A6-B3-C62 A6-B3-C63 A6-B3-C64 A6-B3-C65 A6-B3-C66

A6-B3-C67 A6-B3-C68 A6-B3-C69 A6-B3-C70 A6-B3-C71 A6-B3-C72

A6-B3-C73 A6-B3-C74 A6-B3-C75 A6-B3-C76 A6-B3-C77 A6-B3-C78

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A6-B3-C85 A6-B3-C86 A6-B3-C87 A6-B3-C88 A6-B3-C89 A6-B3-C90

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A6-B3-C103 A6-B3-C104 A6-B3-C105 A6-B3-C106 A6-B3-C107 A6-B3-C108

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A6-B3-C115 A6-B3-C116 A6-B3-C117 A6-B3-C118 A6-B3-C119 A6-B3-C120

A6-B3-C121 A6-B3-C122 A6-B3-C123 A6-B3-C124 A6-B3-C125 A6-B3-C126

A6-B3-C127 A6-B3-C128 A6-B3-C129 A6-B3-C130 A6-B3-C131 A6-B3-C132

A6-B3-C133 A6-B3-C134 A6-B3-C135 A-3-C136 A6-B3-C137 A6-B3-C138

A6-B3-C139 A6-B3-C140 BLANK BLANK BLANK BLANK

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A6-B4-C37 A6-B4-C38 A6-B4-C39 A6-B4-C40 A6-B4-C41 A6-B4-C42

A6-B4-C43 A6-B4-C44 A6-B4-C45 A6-B4-C46 A6-B4-C47 A6-B4-C48

A6-B4-C49 A6-B4-C50 A6-B4-C51 A6-B4-C52 A6-B4-C53 A6-B4-C54

A6-B4-C55 A6-B4-C56 A6-B4-C57 A6-B4-C58 A6-B4-C59 A6-B4-C60

A6-B4-C61 A6-B4-C62 A6-B4-C63 A6-B4-C64 A6-B4-C65 A6-B4-C66

A6-B4-C67 A6-B4-C68 A6-B4-C69 A6-B4-C70 A6-B4-C71 A6-B4-C72

A6-B4-C73 A6-B4-C74 A6-B4-C75 A6-B4-C76 A6-B4-C77 A6-B4-C78

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A6-B4-C85 A6-B4-C86 A6-B4-C87 A6-B4-C88 A6-B4-C89 A6-B4-C90

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A6-B4-C97 A6-B4-C98 A6-B4-C99 A6-B4-C100 A6-B4-C101 A6-B4-C102

A6-B4-C103 A6-B4-C104 A6-B4-C105 A6-B4-C106 A6-B4-C107 A6-B4-C108

A6-B4-C109 A6-B4-C110 A6-B4-C111 A6-B4-C112 A6-B4-C113 A6-B4-C114

A6-B4-C115 A6-B4-C116 A6-B4-C117 A6-B4-C118 A6-B4-C119 A6-B4-C120

A6-B4-C121 A6-B4-C122 A6-B4-C123 A6-B4-C124 A6-B4-C125 A6-B4-C126

A6-B4-C127 A6-B4-C128 A6-B4-C129 A6-B4-C130 A6-B4-C131 A6-B4-C132

A6-B4-C133 A6-B4-C134 A6-B4-C135 A6-B4-C136 A6-B4-C137 A6-B4-C138

A6-B4-C139 A6-B4-C140 BLANK BLANK BLANK BLANK

A6-B5-C1 A6-B5-C2 A6-B5-C3 A6-B5-C4 A6-B5-C5 A6-B5-C6

A6-B5-C7 A6-B5-C8 A6-B5-C9 A6-B5-C10 A6-B5-C11 A6-B5-C12

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A6-B5-C25 A6-B5-C26 A6-B5-C27 A6-B5-C28 A6-B5-C29 A6-B5-C30

A6-B5-C31 A6-B5-C32 A6-B5-C33 A6-B5-C34 A6-B5-C35 A6-B5-C36

A6-B5-C37 A6-B5-C38 A6-B5-C39 A6-B5-C40 A6-B5-C41 A6-B5-C42

A6-B5-C43 A6-B5-C44 A6-B5-C45 A6-B5-C46 A6-B5-C47 A6-B5-C48

A6-B5-C49 A6-B5-C50 A6-B5-C51 A6-B5-C52 A6-B5-C53 A6-B5-C54

A6-B5-C55 A6-B5-C56 A6-B5-C57 A6-B5-C58 A6-B5-C59 A6-B5-C60

A6-B5-C61 A6-B5-C62 A6-B5-C63 A6-B5-C64 A6-B5-C65 A6-B5-C66

A6-B5-C67 A6-B5-C68 A6-B5-C69 A6-B5-C70 A6-B5-C71 A6-B5-C72

A6-B5-C73 A6-B5-C74 A6-B5-C75 A6-B5-C76 A6-B5-C77 A6-B5-C78

A6-B5-C79 A6-B5-C80 A6-B5-C81 A6-B5-C82 A6-B5-C83 A6-B5-C84

A6-B5-C85 A6-B5-C86 A6-B5-C87 A6-B5-C88 A6-B5-C89 A6-B5-C90

A6-B5-C91 A6-B5-C92 A6-B5-C93 A6-B5-C94 A6-B5-C95 A6-B5-C96

A6-B5-C97 A6-B5-C98 A6-B5-C99 A6-B5-C100 A6-B5-C101 A6-B5-C102

A6-B5-C103 A6-B5-C104 A6-B5-C105 A6-B5-C106 A6-B5-C107 A6-B5-C108

A6-B5-C109 A6-B5-C110 A6-B5-C111 A6-B5-C112 A6-B5-C113 A6-B5-C114

A6-B5-C115 A6-B5-C116 A6-B5-C117 A6-B5-C118 A6-B5-C119 A6-B5-C120

A6-B5-C121 A6-B5-C122 A6-B5-C123 A6-B5-C124 A6-B5-C125 A6-B5-C126

A6-B5-C127 A6-B5-C128 A6-B5-C129 A6-B5-C130 A6-B5-C131 A6-B5-C132

A6-B5-C133 A6-B5-C134 A6-B5-C135 A6-B5-C136 A6-B5-C137 A6-B5-C138

A6-B5-C139 A6-B5-C140 BLANK BLANK BLANK BLANK

A6-B6-C1 A6-B6-C2 A6-B6-C3 A6-B6-C4 A6-B6-C5 A6-B6-C6

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A6-B6-C43 A6-B6-C44 A6-B6-C45 A6-B6-C46 A6-B6-C47 A6-B6-C48

A6-B6-C49 A6-B6-C50 A6-B6-C51 A6-B6-C52 A6-B6-C53 A6-B6-C54

A6-B6-C55 A6-B6-C56 A6-B6-C57 A6-B6-C58 A6-B6-C59 A6-B6-C60

A6-B6-C61 A6-B6-C62 A6-B6-C63 A6-B6-C64 A6-B6-C65 A6-B6-C66

A6-B6-C67 A6-B6-C68 A6-B6-C69 A6-B6-C70 A6-B6-C71 A6-B6-C72

A6-B6-C73 A6-B6-C74 A6-B6-C75 A6-B6-C76 A6-B6-C77 A6-B6-C78

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A6-B6-C103 A6-B6-C104 A6-B6-C105 A6-B6-C106 A6-B6-C107 A6-B6-C108

A6-B6-C109 A6-B6-C110 A6-B6-C111 A6-B6-C112 A6-B6-C113 A6-B6-C114

A6-B6-C115 A6-B6-C116 A6-B6-C117 A6-B6-C118 A6-B6-C119 A6-B6-C120

A6-B6-C121 A6-B6-C122 A6-B6-C123 A6-B6-C124 A6-B6-C125 A6-B6-C126

A6-B6-C127 A6-B6-C128 A6-B6-C129 A6-B6-C130 A6-B6-C131 A6-B6-C132

A6-B6-C133 A6-B6-C134 A6-B6-C135 A6-B6-C136 A6-B6-C137 A6-B6-C138

A6-B6-C139 A6-B6-C140 BLANK BLANK BLANK BLANK

A6-B7-C1 A6-B7-C2 A6-B7-C3 A6-B7-C4 A6-B7-C5 A6-B7-C6

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A6-B7-C43 A6-B7-C44 A6-B7-C45 A6-B7-C46 A6-B7-C47 A6-B7-C48

A6-B7-C49 A6-B7-C50 A6-B7-C51 A6-B7-C52 A6-B7-C53 A6-B7-C54

A6-B7-C55 A6-B7-C56 A6-B7-C57 A6-B7-C58 A6-B7-C59 A6-B7-C60

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A6-B7-C103 A6-B7-C104 A6-B7-C105 A6-B7-C106 A6-B7-C107 A6-B7-C108

A6-B7-C109 A6-B7-C110 A6-B7-C111 A6-B7-C112 A6-B7-C113 A6-B7-C114

A6-B7-C115 A6-B7-C116 A6-B7-C117 A6-B7-C118 A6-B7-C119 A6-B7-C120

A6-B7-C121 A6-B7-C122 A6-B7-C123 A6-B7-C124 A6-B7-C125 A6-B7-C126

A6-B7-C127 A6-B7-C128 A6-B7-C129 A6-B7-C130 A6-B7-C131 A6-B7-C132

A6-B7-C133 A6-B7-C134 A6-B7-C135 A6-B7-C136 A6-B7-C137 A6-B7-C138

A6-B7-C139 A6-B7-C140 BLANK BLANK BLANK BLANK

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A6-B8-C43 A6-B8-C44 A6-B8-C45 A6-B8-C46 A6-B8-C47 A6-B8-C48

A6-B8-C49 A6-B8-C50 A6-B8-C51 A6-B8-C52 A6-B8-C53 A6-B8-C54

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A6-B8-C103 A6-B8-C104 A6-B8-C105 A6-B8-C106 A6-B8-C107 A6-B8-C108

A6-B8-C109 A6-B8-C110 A6-B8-C111 A6-B8-C112 A6-B8-C113 A6-B8-C114

A6-B8-C115 A6-B8-C116 A6-B8-C117 A6-B8-C118 A6-B8-C119 A6-B8-C120

A6-B8-C121 A6-B8-C122 A6-B8-C123 A6B-8-C124 A6-B8-C125 A6-B8-C126

A6-B8-C127 A6-B8-C128 A6-B8-C129 A6-B8-C130 A6-B8-C131 A6-B8-C132

A6-B8-C133 A6-B8-C134 A6-B8-C135 A6-B8-C136 A6-B8-C137 A6-B8-C138

A6-B8-C139 A6-B8-C140 BLANK BLANK BLANK BLANK

A6-B9-C1 A6-B9-C2 A6-B9-C3 A6-B9-C4 A6-B9-C5 A6-B9-C6

A6-B9-C7 A6-B9-C8 A6-B9-C9 A6-B9-C10 A6-B9-C11 A6-B9-C12

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A6-B9-C43 A6-B9-C44 A6-B9-C45 A6-B9-C46 A6-B9-C47 A6-B9-C48

A6-B9-C49 A6-B9-C50 A6-B9-C51 A6-B9-C52 A6-B9-C53 A6-B9-C54

A6-B9-C55 A6-B9-C56 A6-B9-C57 A6-B9-C58 A6-B9-C59 A6-B9-C60

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A6-B9-C97 A6-B9-C98 A6-B9-C99 A6-B9-C100 A6-B9-C101 A6-B9-C102

A6-B9-C103 A6-B9-C104 A6-B9-C105 A6-B9-C106 A6-B9-C107 A6-B9-C108

A6-B9-C109 A6-B9-C110 A6-B9-C111 A6-B9-C112 A6-B9-C113 A6-B9-C114

A6-B9-C115 A6-B9-C116 A6-B9-C117 A6-B9-C118 A6-B9-C119 A6-B9-C120

A6-B9-C121 A6-B9-C122 A6-B9-C123 A6-B9-C124 A6-B9-C125 A6-B9-C126

A6-B9-C127 A6-B9-C128 A6-B9-C129 A6-B9-C130 A6-B9-C131 A6-B9-C132

A6-B9-C133 A6-B9-C134 A6-B9-C135 A6-B9-C136 A6-B9-C137 A6-B9-C138

A6-B9-C139 A6-B9-C140 BLANK BLANK BLANK BLANK

A6-B10-C1 A6-10-C2 A6-B10-C3 A6-B10-C4 A6-B10-C5 A6-B10-C6

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A7-B4-C139 A7-B4-C140 BLANK BLANK BLANK BLANK

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A7-B5-C139 A7-B5-C140 BLANK BLANK BLANK BLANK

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A7-B9-C139 A7-B9-C140 BLANK BLANK BLANK BLANK

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A7-B11-C139 A7-B11-C140 BLANK BLANK BLANK BLANK

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A7-B12-C139 A7-B12-C140 BLANK BLANK BLANK BLANK

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A7-B13-C139 A7-B13-C140 BLANK BLANK BLANK BLANK

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A8-B4-C139 A8-B4-C140 BLANK BLANK BLANK BLANK

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A8-B5-C127 A8-B5-C128 A8-B5-C129 A8-B5-C130 A8-B5-C131 A8-B5-C132

A8-B5-C133 A8-B5-C134 A8-B5-C135 A8-B5-C136 A8-B5-C137 A8-B5-C138

A8-B5-C139 A8-B5-C140 BLANK BLANK BLANK BLANK

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A8-B6-C127 A8-B6-C128 A8-B6-C129 A8-B6-C130 A8-B6-C131 A8-B6-C132

A8-B6-C133 A8-B6-C134 A8-B6-C135 A8-B6-C136 A8-B6-C137 A8-B6-C138

A8-B6-C139 A8-B6-C140 BLANK BLANK BLANK BLANK

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A8-B7-C127 A8-B7-C128 A8-B7-C129 A8-B7-C130 A8-B7-C131 A8-B7-C132

A8-B7-C133 A8-B7-C134 A8-B7-C135 A8-B7-C136 A8-B7-C137 A8-B7-C138

A8-B7-C139 A8-B7-C140 BLANK BLANK BLANK BLANK

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A8-B8-C139 A8-B8-C140 BLANK BLANK BLANK BLANK

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A8-B9-C139 A8-B9-C140 BLANK BLANK BLANK BLANK

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A8-B10-C139 A8-B10-C140 BLANK BLANK BLANK BLANK

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A8-B11-C139 A8-B11-C140 BLANK BLANK BLANK BLANK

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A8-B12-C133 A8-B12-C134 A8-B12-C135 A8-B12-C136 A8-B12-C137 A8-B12-C138

A8-B12-C139 A8-B12-C140 BLANK BLANK BLANK BLANK

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A8-B13-C109 A8-B13-C110 A8-B13-C111 A8-B13-C112 A8-B13-C113 A8-B13-C114

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A8-B13-C127 A8-B13-C128 A8-B13-C129 A8-B13-C130 A8-B13-C131 A8-B13-C132

A8-B13-C133 A8-B13-C134 A8-B13-C135 A8-B13-C136 A8-B13-C137 A8-B13-C138

A8-B13-C139 A8-B13-C140 BLANK BLANK BLANK BLANK

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A9-B1-C139 A9-B1-C140 BLANK BLANK BLANK BLANK

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A9-B2-C139 A9-B2-C140 BLANK BLANK BLANK BLANK

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A9-B3-C139 A9-B3-C140 BLANK BLANK BLANK BLANK

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A9-B4-C139 A9-B4-C140 BLANK BLANK BLANK BLANK

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A9-B5-C133 A9-B5-C134 A9-B5-C135 A9-B5-C136 A9-B5-C137 A9-B5-C138

A9-B5-C139 A9-B5-C140 BLANK BLANK BLANK BLANK

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A9-B6-C55 A9-B6-C56 A9-B6-C57 A9-B6-C58 A9-B6-C59 A9-B6-C60

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A9-B6-C127 A9-B6-C128 A9-B6-C129 A9-B6-C130 A9-B6-C131 A9-B6-C132

A9-B6-C133 A9-B6-C134 A9-B6-C135 A9-B6-C136 A9-B6-C137 A9-B6-C138

A9-B6-C139 A9-B6-C140 BLANK BLANK BLANK BLANK

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A9-B7-C49 A9-B7-C50 A9-B7-C51 A9-B7-C52 A9-B7-C53 A9-B7-C54

A9-B7-C55 A9-B7-C56 A9-B7-C57 A9-B7-C58 A9-B7-C59 A9-B7-C60

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A9-B7-C103 A9-B7-C104 A9-B7-C105 A9-B7-C106 A9-B7-C107 A9-B7-C108

A9-B7-C109 A9-B7-C110 A9-B7-C111 A9-B7-C112 A9-B7-C113 A9-B7-C114

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A9-B7-C127 A9-B7-C128 A9-B7-C129 A9-B7-C130 A9-B7-C131 A9-B7-C132

A9-B7-C133 A9-B7-C134 A9-B7-C135 A9-B7-C136 A9-B7-C137 A9-B7-C138

A9-B7-C139 A9-B7-C140 BLANK BLANK BLANK BLANK

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A9-B8-C49 A9-B8-C50 A9-B8-C51 A9-B8-C52 A9-B8-C53 A9-B8-C54

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A9-B8-C127 A9-B8-C128 A9-B8-C129 A9-B8-C130 A9-B8-C131 A9-B8-C132

A9-B8-C133 A9-B8-C134 A9-B8-C135 A9-B8-C136 A9-B8-C137 A9-B8-C138

A9-B8-C139 A9-B8-C140 BLANK BLANK BLANK BLANK

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A9-B9-C139 A9-B9-C140 BLANK BLANK BLANK BLANK

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A9-B10-C139 A9-B10-C140 BLANK BLANK BLANK BLANK

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A9-B11-C139 A9-B11-C140 BLANK BLANK BLANK BLANK

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A10-B6-C31 A10-B6-C32 A10-B6-C33 A10-B6-C34 A10-B6-C35 A10-B6-C36

A10-B6-C37 A10-B6-C38 A10-B6-C39 A10-B6-C40 A10-B6-C41 A10-B6-C42

A10-B6-C43 A10-B6-C44 A10-B6-C45 A10-B6-C46 A10-B6-C47 A10-B6-C48

A10-B6-C49 A10-B6-C50 A10-B6-C51 A10-B6-C52 A10-B6-C53 A10-B6-C54

A10-B6-C55 A10-B6-C56 A10-B6-C57 A10-B6-C58 A10-B6-C59 A10-B6-C60

A10-B6-C61 A10-B6-C62 A10-B6-C63 A10-B6-C64 A10-B6-C65 A10-B6-C66

A10-B6-C67 A10-B6-C68 A10-B6-C69 A10-B6-C70 A10-B6-C71 A10-B6-C72

A10-B6-C73 A10-B6-C74 A10-B6-C75 A10-B6-C76 A10-B6-C77 A10-B6-C78

A10-B6-C79 A10-B6-C80 A10-B6-C81 A10-B6-C82 A10-B6-C83 A10-B6-C84

A10-B6-C85 A10-B6-C86 A10-B6-C87 A10-B6-C88 A10-B6-C89 A10-B6-C90

A10-B6-C91 A10-B6-C92 A10-B6-C93 A10-B6-C94 A10-B6-C95 A10-B6-C96

A10-B6-C97 A10-B6-C98 A10-B6-C99 A10-B6-C100 A10-B6-C101 A10-B6-C102

A10-B6-C103 A10-B6-C104 A10-B6-C105 A10-B6-C106 A10-B6-C107 A10-B6-C108

A10-B6-C109 A10-B6-C110 A10-B6-C111 A10-B6-C112 A10-B6-C113 A10-B6-C114

A10-B6-C115 A10-B6-C116 A10-B6-C117 A10-B6-C118 A10-B6-C119 A10-B6-C120

A10-B6-C121 A10-B6-C122 A10-B6-C123 A10-B6-C124 A10-B6-C125 A10-B6-C126

A10-B5-C127 A10-B6-C128 A10-B6-C129 A10-B6-C130 A10-B6-C131 A10-B6-C132

A10-B6-C133 A10-B6-C134 A10-B6-C135 A10-B6-C136 A10-B6-C137 A10-B6-C138

A10-B6-C139 A10-B6-C140 BLANK BLANK BLANK BLANK

A10-B7-C1 A10-B7-C2 A10-B7-C3 A10-B7-C4 A10-B7-C5 A10-B7-C6

A10-B7-C7 A10-B7-C8 A10-B7-C9 A10-B7-C10 A10-B7-C11 A10-B7-C12

A10-B7-C13 A10-B7-C14 A10-B7-C15 A10-B7-C16 A10-B7-C17 A10-B7-C18

A10-B7-C19 A10-B7-C20 A10-B7-C21 A10-B7-C22 A10-B7-C23 A10-B7-C24

A10-B7-C25 A10-B7-C26 A10-B7-C27 A10-B7-C28 A10-B7-C29 A10-B7-C30

A10-B7-C31 A10-B7-C32 A10-B7-C33 A10-B7-C34 A10-B7-C35 A10-B7-C36

A10-B7-C37 A10-B7-C38 A10-B7-C39 A10-B7-C40 A10-B7-C41 A10-B7-C42

A10-B7-C43 A10-B7-C44 A10-B7-C45 A10-B7-C46 A10-B7-C47 A10-B7-C48

A10-B7-C49 A10-B7-C50 A10-B7-C51 A10-B7-C52 A10-B7-C53 A10-B7-C54

A10-B7-C55 A10-B7-C56 A10-B7-C57 A10-B7-C58 A10-B7-C59 A10-B7-C60

A10-B7-C61 A10-B7-C62 A10-B7-C63 A10-B7-C64 A10-B7-C65 A10-B7-C66

A10-B7-C67 A10-B7-C68 A10-B7-C69 A10-B7-C70 A10-B7-C71 A10-B7-C72

A10-B7-C73 A10-B7-C74 A10-B7-C75 A10-B7-C76 A10-B7-C77 A10-B7-C78

A10-B7-C79 A10-B7-C80 A10-B7-C81 A10-B7-C82 A10-B7-C83 A10-B7-C84

A10-B7-C85 A10-B7-C86 A10-B7-C87 A10-B7-C88 A10-B7-C89 A10-B7-C90

A10-B7-C91 A10-B7-C92 A10-B7-C93 A10-B7-C94 A10-B7-C95 A10-B7-C96

A10-B7-C97 A10-B7-C98 A10-B7-C99 A10-B7-C100 A10-B7-C101 A10-B7-C102

A10-B7-C103 A10-B7-C104 A10-B7-C105 A10-B7-C106 A10-B7-C107 A10-B7-C108

A10-B7-C109 A10-B7-C110 A10-B7-C111 A10-B7-C112 A10-B7-C113 A10-B7-C114

A10-B7-C115 A10-B7-C116 A10-B7-C117 A10-B7-C118 A10-B7-C119 A10-B7-C120

A10-B7-C121 A10-B7-C122 A10-B7-C123 A10-B7-C124 A10-B7-C125 A10-B7-C126

A10-B7-C127 A10-B7-C128 A10-B7-C129 A10-B7-C130 A10-B7-C131 A10-B7-C132

A10-B7-C133 A10-B7-C134 A10-B7-C135 A10-B7-C136 A10-B7-C137 A10-B7-C138

A10-B7-C139 A10-B7-C140 BLANK BLANK BLANK BLANK

A10-B8-C1 A10-B8-C2 A10-B8-C3 A10-B8-C4 A10-B8-C5 A10-B8-C6

A10-B8-C7 A10-B8-C8 A10-B8-C9 A10-B8-C10 A10-B8-C11 A10-B8-C12

A10-B8-C13 A10-B8-C14 A10-B8-C15 A10-B8-C16 A10-B8-C17 A10-B8-C18

A10-B8-C19 A10-B8-C20 A10-B8-C21 A10-B8-C22 A10-B8-C23 A10-B8-C24

A10-B8-C25 A10-B8-C26 A10-B8-C27 A10-B8-C28 A10-B8-C29 A10-B8-C30

A10-B8-C31 A10-B8-C32 A10-B8-C33 A10-B8-C34 A10-B8-C35 A10-B8-C36

A10-B8-C37 A10-B8-C38 A10-B8-C39 A10-B8-C40 A10-B8-C41 A10-B8-C42

A10-B8-C43 A10-B8-C44 A10-B8-C45 A10-B8-C46 A10-B8-C47 A10-B8-C48

A10-B8-C49 A10-B8-C50 A10-B8-C51 A10-B8-C52 A10-B8-C53 A10-B8-C54

A10-B8-C55 A10-B8-C56 A10-B8-C57 A10-B8-C58 A10-B8-C59 A10-B8-C60

A10-B8-C61 A10-B8-C62 A10-B8-C63 A10-B8-C64 A10-B8-C65 A10-B8-C66

A10-B8-C67 A10-B8-C68 A10-B8-C69 A10-B8-C70 A10-B8-C71 A10-B8-C72

A10-B8-C73 A10-B8-C74 A10-B8-C75 A10-B8-C76 A10-B8-C77 A10-B8-C78

A10-B8-C79 A10-B8-C80 A10-B8-C81 A10-B8-C82 A10-B8-C83 A10-B8-C84

A10-B8-C85 A10-B8-C86 A10-B8-C87 A10-B8-C88 A10-B8-C89 A10-B8-C90

A10-B8-C91 A10-B8-C92 A10-B8-C93 A10-B8-C94 A10-B8-C95 A10-B8-C96

A10-B8-C97 A10-B8-C98 A10-B8-C99 A10-B8-C100 A10-B8-C101 A10-B8-C102

A10-B8-C103 A10-B8-C104 A10-B8-C105 A10-B8-C106 A10-B8-C107 A10-B8-C108

A10-B8-C109 A10-B8-C110 A10-B8-C111 A10-B8-C112 A10-B8-C113 A10-B8-C114

A10-B8-C115 A10-B8-C116 A10-B8-C117 A10-B8-C118 A10-B8-C119 A10-B8-C120

A10-B8-C121 A10-B8-C122 A10-B8-C123 A10-B8-C124 A10-B8-C125 A10-B8-C126

A10-B8-C127 A10-B8-C128 A10-B8-C129 A10-B8-C130 A10-B8-C131 A10-B8-C132

A10-B8-C133 A10-B8-C134 A10-B8-C135 A10-B8-C136 A10-B8-C137 A10-B8-C138

A10-B8-C139 A10-B8-C140 BLANK BLANK BLANK BLANK

A10-B9-C1 A10-B9-C2 A10-B9-C3 A10-B9-C4 A10-B9-C5 A10-B9-C6

A10-B9-C7 A10-B9-C8 A10-B9-C9 A10-B9-C10 A10-B9-C11 A10-B9-C12

A10-B9-C13 A10-B9-C14 A10-B9-C15 A10-B9-C16 A10-B9-C17 A10-B9-C18

A10-B9-C19 A10-B9-C20 A10-B9-C21 A10-B9-C22 A10-B9-C23 A10-B9-C24

A10-B9-C25 A10-B9-C26 A10-B9-C27 A10-B9-C28 A10-B9-C29 A10-B9-C30

A10-B9-C31 A10-B9-C32 A10-B9-C33 A10-B9-C34 A10-B9-C35 A10-B9-C36

A10-B9-C37 A10-B9-C38 A10-B9-C39 A10-B9-C40 A10-B9-C41 A10-B9-C42

A10-B9-C43 A10-B9-C44 A10-B9-C45 A10-B9-C46 A10-B9-C47 A10-B9-C48

A10-B9-C49 A10-B9-C50 A10-B9-C51 A10-B9-C52 A10-B9-C53 A10-B9-C54

A10-B9-C55 A10-B9-C56 A10-B9-C57 A10-B9-C58 A10-B9-C59 A10-B9-C60

A10-B9-C61 A10-B9-C62 A10-B9-C63 A10-B9-C64 A10-B9-C65 A10-B9-C66

A10-B9-C67 A10-B9-C68 A10-B9-C69 A10-B9-C70 A10-B9-C71 A10-B9-C72

A10-B9-C73 A10-B9-C74 A10-B9-C75 A10-B9-C76 A10-B9-C77 A10-B9-C78

A10-B9-C79 A10-B9-C80 A10-B9-C81 A10-B9-C82 A10-B9-C83 A10-B9-C84

A10-B9-C85 A10-B9-C86 A10-B9-C87 A10-B9-C88 A10-B9-C89 A10-B9-C90

A10-B9-C91 A10-B9-C92 A10-B9-C93 A10-B9-C94 A10-B9-C95 A10-B9-C96

A10-B9-C97 A10-B9-C98 A10-B9-C99 A10-B9-C100 A10-B9-C101 A10-B9-C102

A10-B9-C103 A10-B9-C104 A10-B9-C105 A10-B9-C106 A10-B9-C107 A10-B9-C108

A10-B9-C109 A10-B9-C110 A10-B9-C111 A10-B9-C112 A10-B9-C113 A10-B9-C114

A10-B9-C115 A10-B9-C116 A10-B9-C117 A10-B9-C118 A10-B9-C119 A10-B9-C120

A10-B9-C121 A10-B9-C122 A10-B9-C123 A10-B9-C124 A10-B9-C125 A10-B9-C126

A10-B9-C127 A10-B9-C128 A10-B9-C129 A10-B9-C130 A10-B9-C131 A10-B9-C132

A10-B9-C133 A10-B9-C134 A10-B9-C135 A10-B9-C136 A10-B9-C137 A10-B9-C138

A10-B9-C139 A10-B9-C140 BLANK BLANK BLANK BLANK

A10-B10-C1 A10-B10-C2 A10-B10-C3 A10-B10-C4 A10-B10-C5 A10-B10-C6

A10-B10-C7 A10-B10-C8 A10-B10-C9 A10-B10-C10 A10-B10-C11 A10-B10-C12

A10-B10-C13 A10-B10-C14 A10-B10-C15 A10-B10-C16 A10-B10-C17 A10-B10-C18

A10-B10-C19 A10-B10-C20 A10-B10-C21 A10-B10-C22 A10-B10-C23 A10-B10-C24

A10-B10-C25 A10-B10-C26 A10-B10-C27 A10-B10-C28 A10-B10-C29 A10-B10-C30

A10-B10-C31 A10-B10-C32 A10-B10-C33 A10-B10-C34 A10-B10-C35 A10-B10-C36

A10-B10-C37 A10-B10-C38 A10-B10-C39 A10-B10-C40 A10-B10-C41 A10-B10-C42

A10-B10-C43 A10-B10-C44 A10-B10-C45 A10-B10-C46 A10-B10-C47 A10-B10-C48

A10-B10-C49 A10-B10-C50 A10-B10-C51 A10-B10-C52 A10-B10-C53 A10-B10-C54

A10-B10-C55 A10-B10-C56 A10-B10-C57 A10-B10-C58 A10-B10-C59 A10-B10-C60

A10-B10-C61 A10-B10-C62 A10-B10-C63 A10-B10-C64 A10-B10-C65 A10-B10-C66

A10-B10-C67 A10-B10-C68 A10-B10-C69 A10-B10-C70 A10-B10-C71 A10-B10-C72

A10-B10-C73 A10-B10-C74 A10-B10-C75 A10-B10-C76 A10-B10-C77 A10-B10-C78

A10-B10-C79 A10-B10-C80 A10-B10-C81 A10-B10-C82 A10-B10-C83 A10-B10-C84

A10-B10-C85 A10-B10-C86 A10-B10-C87 A10-B10-C88 A10-B10-C89 A10-B10-C90

A10-B10-C91 A10-B10-C92 A10-B10-C93 A10-B10-C94 A10-B10-C95 A10-B10-C96

A10-B10-C97 A10-B10-C98 A10-B10-C99 A10-B10-C100 A10-B10-C101 A10-B10-C102

A10-B10-C103 A10-B10-C104 A10-B10-C105 A10-B10-C106 A10-B10-C107 A10-B10-C108

A10-B10-C109 A10-B10-C110 A10-B10-C111 A10-B10-C112 A10-B10-C113 A10-B10-C114

A10-B10-C115 A10-B10-C116 A10-B10-C117 A10-B10-C118 A10-B10-C119 A10-B10-C120

A10-B10-C121 A10-B10-C122 A10-B10-C123 A10-B10-C124 A10-B10-C125 A10-B10-C126

A10-B10-C127 A10-B10-C128 A10-B10-C129 A10-B10-C130 A10-B10-C131 A10-B10-C132

A10-B10-C133 A10-B10-C134 A10-B10-C135 A10-B10-C136 A10-B10-C137 A10-B10-C138

A10-B10-C139 A10-B10-C140 BLANK BLANK BLANK BLANK

A10-B11-C1 A10-B11-C2 A10-B11-C3 A10-B11-C4 A10-B11-C5 A10-B11-C6

A10-B11-C7 A10-B11-C8 A10-B11-C9 A10-B11-C10 A10-B11-C11 A10-B11-C12

A10-B11-C13 A10-B11-C14 A10-B11-C15 A10-B11-C16 A10-B11-C17 A10-B11-C18

A10-B11-C19 A10-B11-C20 A10-B11-C21 A10-B11-C22 A10-B11-C23 A10-B11-C24

A10-B11-C25 A10-B11-C26 A10-B11-C27 A10-B11-C28 A10-B11-C29 A10-B11-C30

A10-B11-C31 A10-B11-C32 A10-B11-C33 A10-B11-C34 A10-B11-C35 A10-B11-C36

A10-B11-C37 A10-B11-C38 A10-B11-C39 A10-B11-C40 A10-B11-C41 A10-B11-C42

A10-B11-C43 A10-B11-C44 A10-B11-C45 A10-B11-C46 A10-B11-C47 A10-B11-C48

A10-B11-C49 A10-B11-C50 A10-B11-C51 A10-B11-C52 A10-B11-C53 A10-B11-C54

A10-B11-C55 A10-B11-C56 A10-B11-C57 A10-B11-C58 A10-B11-C59 A10-B11-C60

A10-B11-C61 A10-B11-C62 A10-B11-C63 A10-B11-C64 A10-B11-C65 A10-B11-C66

A10-B11-C67 A10-B11-C68 A10-B11-C69 A10-B11-C70 A10-B11-C71 A10-B11-C72

A10-B11-C73 A10-B11-C74 A10-B11-C75 A10-B11-C76 A10-B11-C77 A10-B11-C78

A10-B11-C79 A10-B11-C80 A10-B11-C81 A10-B11-C82 A10-B11-C83 A10-B11-C84

A10-B11-C85 A10-B11-C86 A10-B11-C87 A10-B11-C88 A10-B11-C89 A10-B11-C90

A10-B11-C91 A10-B11-C92 A10-B11-C93 A10-B11-C94 A10-B11-C95 A10-B11-C96

A10-B11-C97 A10-B11-C98 A10-B11-C99 A10-B11-C100 A10-B11-C101 A10-B11-C102

A10-B11-C103 A10-B11-C104 A10-B11-C105 A10-B11-C106 A10-B11-C107 A10-B11-C108

A10-B11-C109 A10-B11-C110 A10-B11-C111 A10-B11-C112 A10-B11-C113 A10-B11-C114

A10-B11-C115 A10-B11-C116 A10-B11-C117 A10-B11-C118 A10-B11-C119 A10-B11-C120

A10-B11-C121 A10-B11-C122 A10-B11-C123 A10-B11-C124 A10-B11-C125 A10-B11-C126

A10-B11-C127 A10-B11-C128 A10-B11-C129 A10-B11-C130 A10-B11-C131 A10-B11-C132

A10-B11-C133 A10-B11-C134 A10-B11-C135 A10-B11-C136 A10-B11-C137 A10-B11-C138

A10-B11-C139 A10-B11-C140 BLANK BLANK BLANK BLANK

A10-B12-C1 A10-B12-C2 A10-B12-C3 A10-B12-C4 A10-B12-C5 A10-B12-C6

A10-B12-C7 A10-B12-C8 A10-B12-C9 A10-B12-C10 A10-B12-C11 A10-B12-C12

A10-B12-C13 A10-B12-C14 A10-B12-C15 A10-B12-C16 A10-B12-C17 A10-B12-C18

A10-B12-C19 A10-B12-C20 A10-B12-C21 A10-B12-C22 A10-B12-C23 A10-B12-C24

A10-B12-C25 A10-B12-C26 A10-B12-C27 A10-B12-C28 A10-B12-C29 A10-B12-C30

A10-B12-C31 A10-B12-C32 A10-B12-C33 A10-B12-C34 A10-B12-C35 A10-B12-C36

A10-B12-C37 A10-B12-C38 A10-B12-C39 A10-B12-C40 A10-B12-C41 A10-B12-C42

A10-B12-C43 A10-B12-C44 A10-B12-C45 A10-B12-C46 A10-B12-C47 A10-B12-C48

A10-B12-C49 A10-B12-C50 A10-B12-C51 A10-B12-C52 A10-B12-C53 A10-B12-C54

A10-B12-C55 A10-B12-C56 A10-B12-C57 A10-B12-C58 A10-B12-C59 A10-B12-C60

A10-B12-C61 A10-B12-C62 A10-B12-C63 A10-B12-C64 A10-B12-C65 A10-B12-C66

A10-B12-C67 A10-B12-C68 A10-B12-C69 A10-B12-C70 A10-B12-C71 A10-B12-C72

A10-B12-C73 A10-B12-C74 A10-B12-C75 A10-B12-C76 A10-B12-C77 A10-B12-C78

A10-B12-C79 A10-B12-C80 A10-B12-C81 A10-B12-C82 A10-B12-C83 A10-B12-C84

A10-B12-C85 A10-B12-C86 A10-B12-C87 A10-B12-C88 A10-B12-C89 A10-B12-C90

A10-B12-C91 A10-B12-C92 A10-B12-C93 A10-B12-C94 A10-B12-C95 A10-B12-C96

A10-B12-C97 A10-Bl2-C98 A10-B12-C99 A10-B12-C100 A10-B12-C101 A10-B12-C102

A10-B12-C103 A10-B12-C104 A10-B12-C105 A10-B12-C106 A10-B12-C107 A10-B12-C108

A10-B12-C109 A10-B12-C110 A10-B12-C111 A10-B12-C112 A10-B12-C113 A10-B12-C114

A10-B12-C115 A10-B12-C116 A10-B12-C117 A10-B12-C118 A10-B12-C119 A10-B12-C120

A10-B12-C121 A10-B12-C122 A10-B12-C123 A10-B12-C124 A10-B12-C125 A10-B12-C126

A10-B12-C127 A10-B12-C128 A10-B12-C129 A10-B12-C130 A10-B12-C131 A10-B12-C132

A10-B12-C133 A10-B12-C134 A10-B12-C135 A10-B12-C136 A10-B12-C137 A10-B12-C138

A10-B12-C139 A10-B12-C140 BLANK BLANK BLANK BLANK

A10-B13-C1 A10-B13-C2 A10-B13-C3 A10-B13-C4 A10-B13-C5 A10-B13-C6

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A11-B13-C115 A11-B13-C116 A11-B13-C117 A11-B13-C118 A11-B13-C119 A11-B13-C120

A11-B13-C121 A11-B13-C122 A11-B13-C123 A11-B13-C124 A11-B13-C125 A11-B13-C126

A11-B13-C127 A11-B13-C128 A11-B13-C129 A11-B13-C130 A11-B13-C131 A11-B13-C132

A11-B13-C133 A11-B13-C134 A11-B13-C135 A11-B13-C136 A11-B13-C137 A11-B13-C138

A11-B13-C139 A11-B13-C140 BLANK BLANK BLANK BLANK

A12-B1-C1 A12-B1-C2 A12-B1-C3 A12-B1-C4 A12-B1-C5 A12-B1-C6

A12-B1-C7 A12-B1-C8 A12-B1-C9 A12-B1-C10 A12-B1-C11 A12-B1-C12

A12-B1-C13 A12-B1-C14 A12-B1-C15 A12-B1-C16 A12-B1-C17 A12-B1-C18

A12-B1-C19 A12-B1-C20 A1-B1-C21 A12-B1-C22 A12-B1-C23 A12-B1-C24

A12-B1-C25 A12-B1-C26 A12-B1-C27 A12-B1-C28 A12-B1-C29 A12-B1-C30

A12-B1-C31 A12-B1-C32 A12-B1-C33 A12-B1-C34 A12-B1-C35 A12-B1-C36

A12-B1-C37 A12-B1-C38 A12-B1-C39 A12-B1-C40 A12-B1-C41 A12-B1-C42

A12-B1-C43 A12-B1-C44 A1-B1-C45 A12-B1-C46 A12-B1-C47 A12-B1-C48

A12-B1-C49 A12-B1-C50 A12-B1-C51 A12-B1-C52 A12-B1-C53 A12-B1-C54

A12-B1-C55 A12-B1-C56 A12-B1-C57 A12-B1-C58 A12-B1-C59 A12-B1-C60

A12-B1-C61 A12-B1-C62 A12-B1-C63 A12-B1-C64 A12-B1-C65 A12-B1-C66

A12-B1-C67 A12-B1-C68 A12-B1-C69 A12-B1-C70 A12-B1-C71 A12-B1-C72

A12-B1-C73 A12-B1-C74 A12-B1-C75 A12-B1-C76 A12-B1-C77 A12-B1-C78

A12-B1-C79 A12-B1-C80 A12-B1-C81 A12-B1-C82 A12-B1-C83 A12-B1-C84

A12-B1-C85 A12-B1-C86 A12-B1-C87 A12-B1-C88 A12-B1-C89 A12-B1-C90

A12-B1-C91 A12-B1-C92 A12-B1-C93 A12-B1-C94 A12-B1-C95 A12-B1-C96

A12-B1-C97 A12-B1-C98 A12-B1-C99 A12-B1-C100 A12-B1-C101 A12-B1-C102

A12-B1-C103 A12-B1-C104 A12-B1-C105 A12-B1-C106 A12-B1-C107 A12-B1-C108

A12-B1-C109 A12-B1-C110 A12-B1-C111 A12-B1-C112 A12-B1-C113 A12-B1-C114

A12-B1-C115 A12-B1-C116 A12-B1-C117 A12-B1-C118 A12-B1-C119 A12-B1-C120

A12-B1-C121 A12-B1-C122 A12-B1-C123 A12-B1-C124 A12-B1-C125 A12-B1-C126

A12-B1-C127 A12-B1-C128 A12-B1-C129 A12-B1-C130 A12-B1-C131 A12-B1-C132

A12-B1-C133 A12-B1-C134 A12-B1-C135 A12-B1-C136 A12-B1-C137 A12-B1-C138

A12-B1-C139 A12-B1-C140B LANK BLANK BLANK BLANK

A12-B2-C1 A12-B2-C2 A12-B2-C3 A12-B2-C4 A12-B2-C5 A12-B2-C6

A12-B2-C7 A12-B2-C8 A12-B2-C9 A12-B2-C10 A12-B2-C11 A12-B2-C12

A12-B2-C13 A12-B2-C14 A12-B2-C15 A12-B2-C16 A12-B2-C17 A12-B2-C18

A12-B2-C19 A12-B2-C20 A12-B2-C21 A12-B2-C22 A12-B2-C23 A12-B2-C24

A12-B2-C25 A12-B2-C26 A12-B2-C27 A12-B2-C28 A12-B2-C29 A12-B2-C30

A12-B2-C31 A12-B2-C32 A12-B2-C33 A12-B2-C34 A12-B2-C35 A12-B2-C36

A12-B2-C37 A12-B2-C38 A12-B2-C39 A12-B2-C40 A12-B2-C41 A12-B2-C42

A12-B2-C43 A12-B2-C44 A12-B2-C45 A12-B2-C46 A12-B2-C47 A12-B2-C48

A12-B2-C49 A12-B2-C50 A12-B2-C51 A12-B2-C52 A12-B2-C53 A12-B2-C54

A12-B2-C55 A12-B2-C56 A12-B2-C57 A12-B2-C58 A12-B2-C59 A12-B2-C60

A12-B2-C61 A12-B2-C62 A12-B2-C63 A12-B2-C64 A12-B2-C65 A12-B2-C66

A12-B2-C67 A12-B2-C68 A12-B2-C69 A12-B2-C70 A12-B2-C71 A12-B2-C72

A12-B2-C73 A12-B2-C74 A12-B2-C75 A12-B2-C76 A12-B2-C77 A12-B2-C78

A12-B2-C79 A12-B2-C80 A12-B2-C81 A12-B2-C82 A12-B2-C83 A12-B2-C84

A12-B2-C85 A12-B2-C86 A12-B2-C87 A12-B2-C88 A12-B2-C89 A12-B2-C90

A12-B2-C91 A12-B2-C92 A12-B2-C93 A12-B2-C94 A12-B2-C95 A12-B2-C96

A12-B2-C97 A12-B2-C98 A12-B2-C99 A12-B2-C100 A12-B2-C101 A12-B2-C102

A12-B2-C103 A12-B2-C104 A12-B2-C105 A12-B2-C106 A12-B2-C107 A12-B2-C108

A12-B2-C109 A12-B2-C110 A12-B2-C111 A12-B2-C112 A12-B2-C113 A12-B2-C114

A12-B2-C115 A12-B2-C116 A12-B2-C117 A12-B2-C118 A12-B2-C119 A12-B2-C120

A12-B2-C121 A12-B2-C122 A12-B2-C123 A12-B2-C124 A12-B2-C125 A12-B2-C126

A12-B2-C127 A12-B2-C128 A12-B2-C129 A12-B-C130 A12-B2-C131 A12-B2-C132

A12-B2-C133 A12-B2-C134 A12-B2-C135 A12-B2-C136 A12-B2-C137 A12-B2-C138

A12-B2-C139A 12-B2-C140 BLANK BLANK BLANK BLANK

A12-B3-C1 A12-B3-C2 A12-B3-C3 A12-B3-C4 A12-B3-C5 A12-B3-C6

A12-B3-C7 A12-B3-C8 A12-B3-C9 A12-B3-C10 A12-B3-C11 A12-B3-C12

A12-B3-C13 A12-B3-C14 A12-B3-C15 A12-B3-C16 A12-B3-C17 A12-B3-C18

A12-B3-C19 A12-B3-C20 A12-B3-C21 A12-B3-C22 A12-B3-C23 A12-B3-C24

A12-B3-C25 A12-B3-C26 A12-B3-C27 A12-B3-C28 A12-B3-C29 A12-B3-C30

A12-B3-C31 A12-B3-C32 A12-B3-C33 A12-B3-C34 A12-B3-C35 A12-B3-C36

A12-B3-C37 A12-B3-C38 A12-B3-C39 A12-B3-C40 A12-B3-C41 A12-B3-C42

A12-B3-C43 A12-B3-C44 A12-B3-C45 A12-B3-C46 A12-B3-C47 A12-B3-C48

A12-B3-C49 A12-B3-C50 A12-B3-C51 A12-B3-C52 A12-B3-C53 A12-B3-C54

A12-B3-C55 A12-B3-C56 A12-B3-C57 A12-B3-C58 A12-B3-C59 A12-B3-C60

A12-B3-C61 A12-B3-C62 A12-B3-C63 A12-B3-C64 A12-B3-C65 A12-B3-C66

A12-B3-C67 A12-B3-C68 A12-B3-C69 A12-B3-C70 A12-B3-C71 A12-B3-C72

A12-B3-C73 A12-B3-C74 A12-B3-C75 A12-B3-C76 A12-B3-C77 A12-B3-C78

A12-B3-C79 A12-B3-C80 A12-B3-C81 A12-B3-C82 A12-B3-C83 A12-B3-C84

A12-B3-C85 A12-B3-C86 A12-B3-C87 A12-B3-C88 A12-B3-C89 A12-B3-C90

A12-B3-C91 A12-B3-C92 A12-B3-C93 A12-B3-C94 A12-B3-C95 A12-B3-C96

A12-B3-C97 A12-B3-C98 A12-B3-C99 A12-B3-C100 A12-B3-C101 A12-B3-C102

A12-B3-C103 A12-B3-C104 A12-B3-C105 A12-B3-C106 A12-B3-C107 A12-B3-C108

A12-B3-C109 A12-B3-C110 A12-B3-C111 A12-B3-C112 A12-B3-C113 A12-B3-C114

A12-B3-C115 A12-B3-C116 A12-B3-C117 A12-B3-C118 A12-B3-C119 A12-B3-C120

A12-B3-C121 A12-B3-C122 A12-B3-C123 A12-B3-C124 A12-B3-C125 A12-B3-C126

A12-B3-C127 A12-B3-C128 A12-B3-C129 A12-B3-C130 A12-B3-C131 A12-B3-C132

A12-B3-C133 A12-B3-C134 A12-B3-C135 A12-B3-C136 A12-B3-C137 A12-B3-C138

A12-B3-C139 A12-B3-C140 BLANK BLANK BLANK BLANK

A12-B4-C1 A12-B4-C2 A12-B4-C3 A12-B4-C4 A12-B4-C5 A12-B4-C6

A12-B4-C7 A12-B4-C8 A12-B4-C9 A12-B4-C10 A12-B4-C11 A12-B4-C12

A12-B4-C13 A12-B4-C14 A12-B4-C15 A12-B4-C16 A12-B4-C17 A12-B4-C18

A12-B4-C19 A12-B4-C20 A12-B4-C21 A12-B4-C22 A12-B4-C23 A12-B4-C24

A12-B4-C25 A12-B4-C26 A12-B4-C27 A12-B4-C28 A12-B4-C29 A12-B4-C30

A12-B4-C31 A12-B4-C32 A12-B4-C33 A12-B4-C34 A12-B4-C35 A12-B4-C36

A12-B4-C37 A12-B4-C38 A12-B4-C39 A12-B4-C40 A12-B4-C41 A12-B4-C42

A12-B4-C43 A12-B4-C44 A12-B4-C45 A12-B4-C46 A12-B4-C47 A12-B4-C48

A12-B4-C49 A12-B4-C50 A12-B4-C51 A12-B4-C52 A12-B4-C53 A12-B4-C54

A12-B4C55 A12-B4-C56 A12-B4C57 A12-B4-C58 A12-B4-C59 A12-B4-C60

A12-B4-C61 A12-B4-C62 A12-B4-C63 A12-B4-C64 A12-B4-C65 A12-B4-C66

A12-B4-C67 A12-B4-C68 A12-B4-C69 A12-B4-C70 A12-B4-C71 A12-B4-C72

A12-B4-C73 A12-B4-C74 A12-B4-C75 A12-B4-C76 A12-B4-C77 A12-B4-C78

A12-B4-C79 A12-B4-C80 A12-B4-C81 A12-B4-C82 A12-B4-C83 A12-B4-C84

A12-B4-C85 A12-B4-C86 A12-B4-C87 A12-B4-C88 A12-B4-C89 A12-B4-C90

A12-B4-C91 A12-B4-C92 A12-B4-C93 A12-B4-C94 A12-B4-C95 A12-B4-C96

A12-B4-C97 A12-B4C98 A12-B4-C99 A12-B4-C100 A12-B4-C101 A12-B4-C102

A12-B4-C103 A12-B4-C104 A12-B4-C105 A12-B4-C106 A12-B4-C107 A12-B4-C108

A12-B4-C109 A12-B4-C110 A12-B4-C111 A12-B4-C112 A12-B4-C113 A12-B4-C114

A12-B4-C115 A12-B4-C116 A12-B4-C117 A12-B4-C118 A12-B4-C119 A12-B4-C120

A12-B4-C121 A12-B4-C122 A12-B4-C123 A12-B4-C124 A12-B4-C125 A12-B4-C126

A12-B4-C127 A12-B4-C128 A12-B4-C129 A12-B4-C130 A12-B4-C131 A12-B4-C132

A12-B4-C133 A12-B4-C134 A12-B4-C135 A12-B4-C136 A12-B4-C137 A12-B4-C138

A12-B4-C139 A12-B4-C140 BLANK BLANK BLANK BLANK

A12-B5-C1 A12-B5-C2 A12-B5-C3 A12-B5-C4 A12-B5-C5 A12-B5-C6

A12-B5-C7 A12-B5-C8 A12-B5-C9 A12-B5-C10 A12-B5-C11 A12-B5-C12

A12-B5-C13 A12-B5-C14 A12-B5-C15 A12-B5-C16 A12-B5-C17 A12-B5-C18

A12-B5-C19 A12-B5-C20 A12-B5-C21 A12-B5-C22 A12-B5-C23 A12-B5-C24

A12-B5-C25 A12-B5-C26 A12-B5-C27 A12-B5-C28 A12-B5-C29 A12-B5-C30

A12-B5-C31 A12-B5-C32 A12-B5-C33 A12-B5-C34 A12-B5-C35 A12-B5-C36

A12-B5-C37 A12-B5-C38 A12-B5-C39 A12-B5-C40 A12-B5-C41 A12-B5-C42

A12-B5-C43 A12-B5-C44 A12-B5-C45 A12-B5-C46 A12-B5-C47 A12-B5-C48

A12-B5-C49 A12-B5-C50 A12-B5-C51 A12-B5-C52 A12-B5-C53 A12-B5-C54

A12-B5-C55 A12-B5-C56 A12-B5-C57 A12-B5-C58 A12-B5-C59 A12-B5-C60

A12-B5-C61 A12-B5-C62 A12-B5-C63 A12-B5-C64 A12-B5-C65 A12-B5-C66

A12-B5-C67 A12-B5-C68 A12-B5-C69 A12-B5-C70 A12-B5-C71 A12-B5-C72

A12-B5-C73 A12-B5-C74 A12-B5-C75 A12-B5-C76 A12-B5-C77 A12-B5-C78

A12-B5-C79 A12-B5-C80 A12-B5-C81 A12-B5-C82 A12-B5-C83 A12-B5-C84

A12-B5-C85 A12-B5-C86 A12-B5-C87 A12-B5-C88 A12-B5-C89 A12-B5-C90

A12-B5-C91 A12-B5-C92 A12-B5-C93 A12-B5-C94 A12-B5-C95 A12-B5-C96

A12-B5-C97 A12-B5-C98 A12-B5-C99 A12-B5-C100 A12-B5-C101 A12-B5-C102

A12-B5-C103 A12-B5-C104 A12-B5-C105 A12-B5-C106 A12-B5-C107 A12-B5-C108

A12-B5-C109 A12-B5-C110 A12-B5-C111 A12-B5-C112 A12-B5-C113 A12-B5-C114

A12-B5-C115 A12-B5-C116 A12-B5-C117 A12-B5-C118 A12-B5-C119 A12-B5-C120

A12-B5-C121 A12-B5-C122 A12-B5-C123 A12-B5-C124 A12-B5-C125 A12-B5-C126

A12-B5-C127 A12-B5-C128 A12-B5-C129 A12-B5-C130 A12-B5-C131 A12-B5-C132

A12-B5-C133 A12-B5-C134 A12-B5-C135 A12-B5-C136 A12-B5-C137 A12-B5-C138

A12-B5-C139 A12-B5-C140 BLANK BLANK BLANK BLANK

A12-B6-C1 A12-B6-C2 A12-B6-C3 A12-B6-C4 A12-B6-C5 A12-B6-C6

A12-B6-C7 A12-B6-C8 A12-B6-C9 A12-B6-C10 A12-B6-C11 A12-B6-C12

A12-B6-C13 A12-B6-C14 A12-B6-C15 A12-B6-C16 A12-B6-C17 A12-B6-C18

A12-B6-C19 A12-B6-C20 A12-B6-C21 A12-B6-C22 A12-B6-C23 A12-B6-C24

A12-B6-C25 A12-B6-C26 A12-B6-C27 A12-B6-C28 A12-B6-C29 A12-B6-C30

A12-B6-C31 A12-B6-C32 A12-B6-C33 A12-B6-C34 A12-B6-C35 A12-B6-C36

A12-B6-C37 A12-B6-C38 A12-B6-C39 A12-B6-C40 A12-B6-C41 A12-B6-C42

A12-B6-C43 A12-B6-C44 A12-B6-C45 A12-B6-C46 A12-B6-C47 A12-B6-C48

A12-B6-C49 A12-B6-C50 A12-B6-C51 A12-B6-C52 A12-B6-C53 A12-B6-C54

A12-B6-C55 A12-B6-C56 A12-B6-C57 A12-B6-C58 A12-B6-C59 A12-B6-C60

A12-B6-C61 A12-B6-C62 A12-B6-C63 A12-B6-C64 A12-B6-C65 A12-B6-C66

A12-B6-C67 A12-B6-C68 A12-B6-C69 A12-B6-C70 A12-B6-C71 A12-B6-C72

A12-B6-C73 A12-B6-C74 A12-B6-C75 A12-B6-C76 A12-B6-C77 A12-B6-C78

A12-B6-C79 A12-B6-C80 A12-B6-C81 A12-B6-C82 A12-B6-C83 A12-B6-C84

A12-B6-C85 A12-B6-C86 A12-B6-C87 A12-B6-C88 A12-B6-C89 A12-B6-C90

A12-B6-C91 A12-B6-C92 A12-B6-C93 A12-B6-C94 A12-B6-C95 A12-B6-C96

A12-B6-C97 A12-B6-C98 A12-B6-C99 A12-B6-C100 A12-B6-C101 A12-B6-C102

A12-B6-C103 A12-B6-C104 A12-B6-C105 A12-B6-C106 A12-B6-C107 A12-B6-C108

A12-B6-C109 A12-B6-C110 A12-B6-C111 A12-B6-C112 A12-B6-C113 A12-B6-C114

A12-B6-C115 A12-B6-C116 A12-B6-C117 A12-B6-C118 A12-B6-C119 A12-B6-C120

A12-B6-C121 A12-B6-C122 A12-B6-C123 A12-B6-C124 A12-B6-C125 A12-B6-C126

A12-B6-C127 A12-B6-C128 A12-B6-C129 A12-B6-C130 A12-B6-C131 A1-B6-C132

A12-B6-C133 A12-B6-C134 A12-B6-C135 A12-B6-C136 A12-B6-C137 A12-B6-C138

A12-B6-C139 A12-B6-C140 BLANK BLANK BLANK BLANK

A12-B7-C1 A12-B7-C2 A12-B7-C3 A12-B7-C4 A12-B7-C5 A12-B7-C6

A12-B7-C7 A12-B7-C8 A12-B7-C9 A12-B7-C10 A12-B7-C11 A12-B7-C12

A12-B7-C13 A12-B7-C14 A12-B7-C15 A12-B7-C16 A12-B7-C17 A12-B7-C18

A12-B7-C19 A12-B7-C20 A12-B7-C21 A12-B7-C22 A12-B7-C23 A12-B7-C24

A12-B7-C25 A12-B7-C26 A12-B7-C27 A12-B7-C28 A12-B7-C29 A12-B7-C30

A12-B7-C31 A12-B7-C32 A12-B7-C33 A12-B7-C34 A12-B7-C35 A12-B7-C36

A12-B7-C37 A12-B7-C38 A12-B7-C39 A12-B7-C40 A12-B7-C41 A12-B7-C42

A12-B7-C43 A12-B7-C44 A12-B7-C45 A12-B7-C46 A12-B7-C47 A12-B7-C48

A12-B7-C49 A12-B7-C50 A12-B7-C51A 12-B7-C52 A12-B7-C53 A12-B7-C54

A12-B7-C55 A12-B7-C56 A12-B7-C57 A12-B7-C58 A12-B7-C59 A12-B7-C60

A12-B7-C61 A12-B7-C62 A12-B7-C63 A12-B7-C64 A12-B7-C65 A12-B7-C66

A12-B7-C67 A12-B7-C68 A12-B7-C69 A12-B7-C70 A12-B7-C71 A12-B7-C72

A12-B7-C73 A12-B7-C74 A12-B7-C75 A12-B7-C76 A12-B7-C77 A12-B7-C78

A12-B7-C79 A12-B7-C80 A12-B7-C81 A12-B7-C82 A12-B7-C83 A12-B7-C84

A12-B7-C85 A12-B7-C86 A12-B7-C87 A12-B7-C88 A12-B7-C89 A12-B7-C90

A12-B7-C91 A12-B7-C92 A12-B7-C93 A12-B7-C94 A12-B7-C95 A12-B7-C96

A12-B7-C97 A12-B7-C98 A12-B7-C99 A12-B7-C100 A12-B7-C101 A12-B7-C102

A12-B7-C103 A12-B7-C104 A12-B7-C105 A12-B7-C106 A12-B7-C107 A12-B7-C108

A12-B7-C109 A12-B7-C110 A12-B7-C111 A12-B7-C112 A12-B7-C113 A12-B7-C114

A12-B7-C115 A12-B7-C116 A12-B7-C117 A12-B7-C118 A12-B7-C119 A12-B7-C120

A12-B7-C121 A12-B7-C122 A12-B7-C123 A12-B7-C124 A12-B7-C125 A12-B7-C126

A12-B7-C127 A12-B7-C128 A12-B7-C129 A12-B7-C130 A12-B7-C131 A12-B7-C132

A12-B7-C133 A12-B7-C134 A12-B7-C135 A12-B7-C136 A12-B7-C137 A12-B7-C138

A12-B7-C139 A12-B7-C140 BLANK BLANK BLANK BLANK

A12-B8-C1 A12-B8-C2 A12-B8-C3 A12-B8-C4 A12-B8-C5 A12-B8-C6

A12-B8-C7 A12-B8-C8 A12-B8-C9 A12-B8-C10 A12-B8-C11 A12-B8-C12

A12-B8-C13 A12-B8-C14 A12-B8-C15 A12-B8-C16 A12-B8-C17 A12-B8-C18

A12-B8-C19 A12-B8-C20 A12-B8-C21 A12-B8-C22 A12-B8-C23 A12-B8-C24

A12-B8-C25 A12-B8-C26 A12-B8-C27 A12-B8-C28 A12-B8-C29 A12-B8-C30

A12-B8-C31 A12-B8-C32 A12-B8-C33 A12-B8-C34 A12-B8-C35 A12-B8-C36

A12-B8-C37 A12-B8-C38 A12-B8-C39 A12-B8-C40 A12-B8-C41 A12-B8-C42

A12-B8-C43 A12-B8-C44 A12-B8-C45 A12-B8-C46 A12-B8-C47 A12-B8-C48

A12-B8-C49 A12-B8-C50 A12-B8-C51 A12-B8-C52 A12-B8-C53 A12-B8-C54

A12-B8-C55 A12-B8-C56 A12-B8-C57 A12-B8-C58 A12-B8-C59 A12-B8-C60

A12-B8-C61 A12-B8-C62 A12-B8-C63 A12-B8-C64 A12-B8-C65 A12-B8-C66

A12-B8-C67 A12-B8-C68 A12-B8-C69 A12-B8-C70 A12-B8-C71 A12-B8-C72

A12-B8-C73 A12-B8-C74 A12-B8-C75 A12-B8-C76 A12-B8-C77 A12-B8-C78

A12-B8-C79 A12-B8-C80 A12-B8-C81 A12-B8-C82 A12-B8-C83 A12-B8-C84

A12-B8-C85 A12-B8-C86 A12-B8-C87 A12-B8-C88 A12-B8-C89 A12-B8-C90

A12-B8-C91 A12-B8-C92 A12-B8-C93 A12-B8-C94 A12-B8-C95 A12-B8-C96

A12-B8-C97 A12-B8-C98 A12-B8-C99 A12-B8-C100 A12-B8-C101 A12-B8-C102

A12-B8-C103 A12-B8-C104 A12-B8-C105 A12-B8-C106 A12-B8-C107 A12-B8-C108

A12-B8-C109 A12-B8-C110 A12-B8-C111 A12-B8-C112 A12-B8-C113 A12-B8-C114

A12-B8-C115 A12-B8-C116 A12-B8-C117 A12-B8-C118 A12-B8-C119 A12-B8-C120

A12-B8-C121 A12-B8-C122 A12-B8-C123 A12-B8-C124 A12-B8-C125 A12-B8-C126

A12-B8-C127 A12-B8-C128 A12-B8-C129 A12-B8-C130 A12-B8-C131 A12-B8-C132

A12-B8-C133 A12-B8-C134 A12-B8-C135 A12-B8-C136 A12-B8-C137 A12-B8-C138

A12-B8-C139 A12-B8-C140 BLANK BLANK BLANK BLANK

A12-B9-C1 A12-B9-C2 A12-B9-C3 A12-B9-C4 A12-B9-C5 A12-B9-C6

A12-B9-C7 A12-B9-C8 A12-B9-C9 A12-B9-C10 A12-B9-C11 A12-B9-C12

A12-B9-C13 A12-B9-C14 A12-B9-C15 A12-B9-C16 A12-B9-C17 A12-B9-C18

A12-B9-C19 A12-B9-C20 A12-B9-C21 A12-B9-C22 A12-B9-C23 A12-B9-C24

A12-B9-C25 A12-B9-C26 A12-B9-C27 A12-B9-C28 A12-B9-C29 A12-B9-C30

A12-B9-C31 A12-B9-C32 A12-B9-C33 A12-B9-C34 A12-B9-C35 A12-B9-C36

A12-B9-C37 A12-B9-C38 A12-B9-C39 A12-B9-C40 A12-B9-C41 A12-B9-C42

A12-B9-C43 A12-B9-C44 A12-B9-C45 A12-B9-C46 A12-B9-C47 A12-B9-C48

A12-B9-C49 A12-B9-C50 A12-B9-C51 A12-B9-C52 A12-B9-C53 A12-B9-C54

A12-B9-C55 A12-B9-C56 A12-B9-C57 A12-B9-C58 A12-B9-C59 A12-B9-C60

A12-B9-C61 A12-B9-C62 A12-B9-C63 A12-B9-C64 A12-B9-C65 A12-B9-C66

A12-B9-C67 A12-B9-C68 A12-B9-C69 A12-B9-C70 A12-B9-C71 A12-B9-C72

A12-B9-C73 A12-B9-C74 A12-B9-C75 A12-B9-C76 A12-B9-C77 A12-B9-C78

A12-B9-C79 A12-B9-C80 A12-B9-C81 A12-B9-C82 A12-B9-C83 A12-B9-C84

A12-B9-C85 A12-B9-C86 A12-B9-C87 A12-B9-C88 A12-B9-C89 A12-B9-C90

A12-B9-C91 A12-B9-C92 A12-B9-C93 A12-B9-C94 A12-B9-C95 A12-B9-C96

A12-B9-C97 A12-B9-C98 A12-B9-C99 A12-B9-C100 A12-B9-C101 A12-B9-C102

A12-B9-C103 A12-B9-C104 A12-B9-C105 A12-B9-C106 A12-B9-C107 A12-B9-C108

A12-B9-C109 A12-B9-C110 A12-B9-C111 A12-B9-C112 A12-B9-C113 A12-B9-C114

A12-B9-C115 A12-B9-C116 A12-B9-C117 A12-B9-C118 A12-B9-C119 A12-B9-C120

A12-B9-C121 A12-B9-C122 A12-B9-C123 A12-B9-C124 A12-B9-C125 A12-B9-C126

A12-B9-C127 A12-B9-C128 A12-B9-C129 A12-B9-C130 A12-B9-C131 A12-B9-C132

A12-B9-C133 A12-B9-C134 A12-B9-C135 A12-B9-C136 A12-B9-C137 A12-B9-C138

A12-B9-C139 A12-B9-C140 BLANK BLANK BLANK BLANK

A12-B10-C1 A12-B10-C2 A12-B10-C3 A12-B10-C4 A12-B10-C5 A12-B10-C6

A12-B10-C7 A12-B10-C8 A12-B10-C9 A12-B10-C10 A12-B10-C11 A12-B10-C12

A12-B10-C13 A12-B10-C14 A12-B10-C15 A12-B10-C16 A12-B10-C17 A12-B10-C18

A12-B10-C19 A12-B10-C20 A12-B10-C21 A12-B10-C22 A12-B10-C23 A12-B10-C24

A12-B10-C25 A12-B10-C26 A12-B10-C27 A12-B10-C28 A12-B10-C29 A12-B10-C30

A12-B10-C31 A12-B10-C32 A12-B10-C33 A12-B10-C34 A12-B10-C35 A12-B10-C36

A12-B10-C37 A12-B10-C38 A12-B10-C39 A12-B10-C40 A12-B10-C41 A12-B10-C42

A12-B10-C43 A12-B10-C44 A12-B10-C45 A12-B10-C46 A12-B10-C47 A12-B10-C48

A12-B10-C49 A12-B10-C50 A12-B10-C51 A12-B10-C52 A12-B10-C53 A12-B10-C54

A12-B10-C55 A12-B10-C56 A12-B10-C57 A12-B10-C58 A12-B10-C59 A12-B10-C60

A12-B10-C61 A12-B10-C62 A12-B10-C63 A12-B10-C64 A12-B10-C65 A12-B10-C66

A12-B10-C67 A12-B10-C68 A12-B10-C69 A12-B10-C70 A12-B10-C71 A12-B10-C72

A12-B10-C73 A12-B10-C74 A12-B10-C75 A12-B10-C76 A12-B10-C77 A12-B10-C78

A12-B10-C79 A12-B10-C80 A12-B10-C81 A12-B10-C82 A12-B10-C83 A12-B10-C84

A12-B10-C85 A12-B10-C86 A12-B10-C87 A12-B10-C88 A12-B10-C89 A12-B10-C90

A12-B10-C91 A12-B10-C92 A12-B10-C93 A12-B10-C94 A12-B10-C95 A12-B10-C96

A12-B10-C97 A12-B10-C98 A12-B10-C99 A12-B10-C100 A12-B10-C101 A12-B10-C102

A12-B10-C103 A12-B10-C104 A12-B10-C105 A12-B10-C106 A12-B10-C107 A12-B10-C108

A12-B10-C109 A12-B10-C110 A12-B10-C111 A12-B10-C112 A12-B10-C113 A12-B10-C114

A12-B10-C115 A12-B10-C116 A12-B10-C117 A12-B10-C118 A12-B10-C119 A12-B10-C120

A12-B10-C121 A12-B10-C122 A12-B10-C123 A12-B10-C124 A12-B10-C125 A12-B10-C126

A12-B10-C127 A12-B10-C128 A12-B10-C129 A12-B10-C130 A12-B10-C131 A12-B10-C132

A12-B10-C133 A12-B10-C134 A12-B10-C135 A12-B10-C136 A12-B10-C137 A12-B10-C138

A12-B10-C139 A12-B10-C140 BLANK BLANK BLANK BLANK

A12-B11-C1 A12-B11-C2 A12-B11-C3 A12-B11-C4 A12-B11-C5 A12-B11-C6

A12-B11-C7 A12-B11-C8 A12-B11-C9 A12-B11-C10 A12-B11-C11 A12-B11-C12

A12-B11-C13 A12-B11-C14 A12-B11-C15 A12-B11-C16 A12-B11-C17 A12-B11-C18

A12-B11-C19 A12-B11-C20 A12-B11-C21 A12-B11-C22 A12-B11-C23 A12-B11-C24

A12-B11-C25 A12-B11-C26 A12-B11-C27 A12-B11-C28 A12-B11-C29 A12-B11-C30

A12-B11-C31 A12-B11-C32 A12-B11-C33 A12-B11-C34 A12-B11-C35 A12-B11-C36

A12-B11-C37 A12-B11-C38 A12-B11-C39 A12-B11-C40 A12-B11-C41 A12-B11-C42

A12-B11-C43 A12-B11-C44 A12-B11-C45 A12-B11-C46 A12-B11-C47 A12-B11-C48

A12-B11-C49 A12-B11-C50 A12-B11-C51 A12-B11-C52 A12-B11-C53 A12-B11-C54

A12-B11-C55 A12-B11-C56 A12-B11-C57 A12-B11-C58 A12-B11-C59 A12-B11-C60

A12-B11-C61 A12-B11-C62 A12-B11-C63 A12-B11-C64 A12-B11-C65 A12-B11-C66

A12-B11-C67 A12-B11-C68 A12-B11-C69 A12-B11-C70 A12-B11-C71 A12-B11-C72

A12-B11-C73 A12-B11-C74 A12-B11-C75 A12-B11-C76 A12-B11-C77 A12-B11-C78

A12-B11-C79 A12-B11-C80 A12-B11-C81 A12-B11-C82 A12-B11-C83 A12-B11-C84

A12-B11-C85 A12-B11-C86 A12-B11-C87 A12-B11-C88 A12-B11-C89 A12-B11-C90

A12-B11-C91 A12-B11-C92 A12-B11-C93 A12-B11-C94 A12-B11-C95 A12-B11-C96

A12-B11-C97 A12-B11-C98 A12-B11-C99 A12-B11-C100 A12-B11-C101 A12-B11-C102

A12-B11-C103 A12-B11-C104 A12-B11-C105 A12-B11-C106 A12-B11-C107 A12-B11-C108

A12-B11-C109 A12-B11-C110 A12-B11-C111 A12-B11-C112 A12-B11-C113 A12-B11-C114

A12-B11-C115 A12-B11-C116 A12-B11-C117 A12-B11-C118 A12-B11-C119 A12-B11-C120

A12-B11-C121 A12-B11-C122 A12-B11-C123 A12-B11-C124 A12-B11-C125 A12-B11-C126

A12-B11-C127 A12-B11-C128 A12-B11-C129 A12-B11-C130 A12-B11-C131 A12-B11-C132

A12-B11-C133 A12-B11-C134 A12-B11-C135 A12-B11-C136 A12-B11-C137 A12-B11-C138

A12-B11-C139 A12-B11-C140 BLANK BLANK BLANK BLANK

A12-B12-C1 A12-B12-C2 A12-B12-C3 A12-B12-C4 A12-B12-C5 A12-B12-C6

A12-B12-C7 A12-B12-C8 A12-B12-C9 A12-B12-C10 A12-B12-C11 A12-B12-C12

A12-B12-C13 A12-B12-C14 A12-B12-C15 A12-B12-C16 A12-B12-C17 A12-B12-C18

A12-B12-C19 A12-B12-C20 A12-B12-C21 A12-B12-C22 A12-B12-C23 A12-B12-C24

A12-B12-C25 A12-B12-C26 A12-B12-C27 A12-B12-C28 A12-B12-C29 A12-B12-C30

A12-B12-C31 A12-B12-C32 A12-B12-C33 A12-B12-C34 A12-B12-C35 A12-B12-C36

A12-B12-C37 A12-B12-C38 A12-B12-C39 A12-B12-C40 A12-B12-C41 A12-B12-C42

A12-B12-C43 A12-B12-C44 A12-B12-C45 A12-B12-C46 A12-B12-C47 A12-B12-C48

A12-B12-C49 A12-B12-C50 A12-B12-C51 A12-B12-C52 A12-B12-C53 A12-B12-C54

A12-B12-C55 A12-B12-C56 A12-B12-C57 A12-B12-C58 A12-B12-C59 A12-B12-C60

A12-B12-C61 A12-B12-C62 A12-B12-C63 A12-B12-C64 A12-B12-C65 A12-B12-C66

A12-B12-C67 A12-B12-C68 A12-B12-C69 A12-B12-C70 A12-B12-C71 A12-B12-C72

A12-B12-C73 A12-B12-C74 A12-B12-C75 A12-B12-C76 A12-B12-C77 A12-B12-C78

A12-B12-C79 A12-B12-C80 A12-B12-C81 A12-B12-C82 A12-B12-C83 A12-B12-C84

A12-B12-C85 A12-B12-C86 A12-B12-C87 A12-B12-C88 A12-B12-C89 A12-B12-C90

A12-B12-C91 A12-B12-C92 A12-B12-C93 A12-B12-C94 A12-B12-C95 A12-B12-C96

A12-B12-C97 A12-B12-C98 A12-B12-C99 A12-B12-C100 A12-B12-C101 A12-B12-C102

A12-B12-C103 A12-B12-C104 A12-B12-C105 A12-B12-C106 A12-B12-C107 A12-B12-C108

A12-B12-C109 A12-B12-C110 A12-B12-C111 A12-B12-C112 A12-B12-C113 A12-B12-C114

A12-B12-C115 A12-B12-C116 A12-B12-C117 A12-B12-C118 A12-B12-C119 A12-B12-C120

A12-B12-C121 A12-B12-C122 A12-B12-C123 A12-B12-C124 A12-B12-C125 A12-B12-C126

A12-B12-C127 A12-B12-C128 A12-B12-C129 A12-B12-C130 A12-B12-C131 A12-B12-C132

A12-B12-C133 A12-B12-C134 A12-B12-C135 A12-B12-C136 A12-B12-C137 A12-B12-C138

A12-B12-C139 A12-B12-C140 BLANK BLANK BLANK BLANK

A12-B13-C1 A12-B13-C2 A12-B13-C3 A12-B13-C4 A12-B13-C5 A12-B13-C6

A12-B13-C7 A12-B13-C8 A12-B13-C9 A12-B13-C10 A12-B13-C11 A12-B13-C12

A12-B13-C13 A12-B13-C14 A12-B13-C15 A12-B13-C16 A12-B13-C17 A12-B13-C18

A12-B13-C19 A12-B13-C20 A12-B13-C21 A12-B13-C22 A12-B13-C23 A12-B13-C24

A12-B13-C25 A12-B13-C26 A12-B13-C27 A12-B13-C28 A12-B13-C29 A12-B13-C30

A12-B13-C31 A12-B13-C32 A12-B13-C33 A12-B13-C34 A12-B13-C35 A12-B13-C36

A12-B13-C37 A12-B13-C38 A12-B13-C39 A12-B13-C40 A12-B13-C41 A12-B13-C42

A12-B13-C43 A12-B13-C44 A12-B13-C45 A12-B13-C46 A12-B13-C47 A12-B13-C48

A12-B13-C49 A12-B13-C50 A12-B13-C51 A12-B13-C52 A12-B13-C53 A12-B13-C54

A12-B13-C55 A12-B13-C56 A12-B13-C57 A12-B13-C58 A12-B13-C59 A12-B13-C60

A12-B13-C61 A12-B13-C62 A12-B13-C63 A12-B13-C64 A12-B13-C65 A12-B13-C66

A12-B13-C67 A12-B13-C68 A12-B13-C69 A12-B13-C70 A12-B13-C71 A12-B13-C72

A12-B13-C73 A12-B13-C74 A12-B13-C75 A12-B13-C76 A12-B13-C77 A12-B13-C78

A12-B13-C79 A12-B13-C80 A12-B13-C81 A12-B13-C82 A12-B13-C83 A12-B13-C84

A12-B13-C85 A12-B13-C86 A12-B13-C87 A12-B13-C88 A12-B13-C89 A12-B13-C90

A12-B13-C91 A12-B13-C92 A12-B13-C93 A12-B13-C94 A12-B13-C95 A12-B13-C96

A12-B13-C97 A12-B13-C98 A12-B13-C99 A12-B13-C100 A12-B13-C101 A12-B13-C102

A12-B13-C103 A12-B13-C104 A12-B13-C105 A12-B13-C106 A12-B13-C107 A12-B13-C108

A12-B13-C109 A12-B13-C110 A12-B13-C111 A12-B13-C112 A12-B13-C113 A12-B13-C114

A12-B13-C115 A12-B13-C116 A12-B13-C117 A12-B13-C118 A12-B13-C119 A12-B13-C120

A12-B13-C121 A12-B13-C122 A12-B13-C123 A12-B13-C124 A12-B13-C125 A12-B13-C126

A12-B13-C127 A12-B13-C128 A12-B13-C129 A12-B13-C130 A12-B13-C131 A12-B13-C132

A12-B13-C133 A12-B13-C134 A12-B13-C135 A12-B13-C136 A12-B13-C137 A12-B13-C138

A12-B13-C139 A12-B13-C140 BLANK BLANK BLANK.

"BLANK" is BLANK

Thus, for example, in the above list, the compounds represented by A1-B1-C1 are the products of the combination of A1 in Table 1 with B1 in Table 2 with C1 in Table 3, i.e.

Preferred compounds of the invention are selected from:

3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine;

3- [1- (3-phenethyl-benzoyl) -piperidin-4-yl ] -benzylamine;

3- {1- [3- (4-hydroxyphenyl) ethyl-benzoyl ] -piperidin-4-yl } -benzylamine;

3- {1- [3- (6-amino-pyridin-3-yl) ethyl-benzoyl ] -piperidin-4-yl } -benzylamine;

3- [1- (5-phenethyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine;

4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine;

4-methyl-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine;

3- [1- (indole-6-carbonyl) -piperidin-4-yl ] -benzylamine;

4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-4-carbonitrile;

[4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (3, 4-dichlorophenyl) methanone;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-methylsulfanyl-6, 7-carboxylic acid

dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-methylsulfanyl-6, 7-dihydro-benzo [ c ] thiophen-1-yl) -methanone trifluoroacetate salt;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-ethylsulfanyl-6, 6-dimethyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-propylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-isopropylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1-benzo [ b ] thiophen-2-yl-methanone trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone bistrifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1-methyl-1H-indol-3-yl) -methanone trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (2-fluoro-phenylethynyl) -phenyl ] -methanone trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (2-fluoro-phenyl) -ethyl ] -phenyl } -methanone trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (6-amino-pyridin-3-yl) -ethyl ] -phenyl } -methanone trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (6-chloro-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt;

(3R, 4S) and (3S, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride;

3- [1- (5-phenylethynyl-furan-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate;

4- (3-aminomethyl-phenyl) -piperidine-1-carboxylic acid (3, 4-dichlorophenyl) -amide trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (2, 3-dihydro-benzofuran-5-yl) -methanone;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5, 6-dihydro-pyridin-3-yl) -methanone;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-bromo-4-fluoro-phenyl) -methanone;

(E) -1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3- (2-nitro-phenyl) -propenone;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-bromo-5-iodo-phenyl) -methanone;

(E) -1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3-phenyl-propenone;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3-cyclohexyl-propan-1-one; and the corresponding N-oxides and their prodrugs; and pharmaceutically acceptable salts and solvates (e.g., hydrates) of such compounds and their N-oxides and prodrugs.

Pharmaceutical composition

As explained above, the compounds of the present invention exhibit useful pharmacological activity and are therefore incorporated into pharmaceutical compositions for the treatment of patients suffering from certain medical disorders. Thus according to a further aspect, the present invention provides a compound of the invention and a pharmaceutical composition comprising a compound of the invention for use in therapy, wherein the pharmaceutical composition of the invention comprises a compound of the invention and a pharmaceutically acceptable carrier therefor. The term "pharmaceutically acceptable" as used herein preferably means approved by a governmental, particularly regulatory agency of the federal or a state government or listed in the U.S. pharmacopeia or another generally recognized pharmacopeia for use in animals, and more particularly in humans. Suitable Pharmaceutical carriers are described in Remington's Pharmaceutical Science (Remington's Pharmaceutical Science) of e.w. martin.

The pharmaceutical compositions according to the invention can be prepared in a conventional manner using one or more pharmaceutically acceptable auxiliaries or excipients. Adjuvants include, inter alia, diluents, sterile aqueous media and various non-toxic organic solvents. The compositions may be in the form of tablets, pills, granules, powders, aqueous solutions or suspensions, injectable solutions, elixirs or syrups, and may contain one or more agents selected from the group consisting of sweetening agents, flavouring agents, colouring agents or stabilising agents, in order to obtain a pharmaceutically acceptable formulation. The choice of carrier and the amount of active substance in the carrier will generally be determined according to the solubility and chemical nature of the active compound, the particular mode of administration and the items observed in pharmaceutical practice. For example, to prepare tablets, excipients such as lactose, sodium citrate, calcium carbonate, dicalcium phosphate, and disintegrating agents such as starch, alginic acid and certain complex silicates, as well as lubricating agents such as magnesium stearate, sodium lauryl sulfate and talc may be used. For the preparation of capsules, lactose and high molecular weight polyethylene glycols are advantageously used. When aqueous suspensions are used, they may contain emulsifying agents or agents which facilitate suspension. Diluents such as sucrose, ethanol, polyethylene glycol, propylene glycol, glycerol and chloroform or mixtures thereof may also be used. Such pharmaceutically acceptable carriers can also be sterile water and oils, including petroleum, animal, vegetable or synthetic derived oils, such as coconut oil, soybean oil, mineral oil, sesame oil and the like. Water is a preferred carrier when the pharmaceutical composition is administered intravenously. Saline solutions and aqueous dextrose and glycerol solutions may also be employed as liquid carriers, particularly for injectable solutions. Suitable pharmaceutical excipients include mannitol, Human Serum Albumin (HSA), starch, glucose, lactose, sucrose, gelatin, malt, rice, flour, chalk, silica gel, magnesium carbonate, magnesium stearate, sodium stearate, glycerol monostearate, talc, sodium chloride, anhydrous skim milk, glycerol, propylene glycol, water, ethanol and the like. These compositions may take the form of solutions, suspensions, tablets, pills, capsules, powders, sustained release formulations and the like.

Naturally, the pharmaceutical compositions of the invention will contain a diagnostically or therapeutically effective amount of the active compound, together with an appropriate amount of carrier, to provide a dosage form suitable for administration to a patient. Intravenous injection is a very effective mode of administration, although other modes of administration may be employed, such as injection or oral, nasal or parenteral, as discussed below.

Method of treatment

Compounds within the scope of the present invention have tryptase inhibitory activity according to the tests described in the literature and the in vitro procedures described below, and these test results are believed to correlate with pharmacological activity in humans and other animals. Thus, in a further embodiment, the invention provides a compound of the invention and compositions containing a compound of the invention for use in treating a subject suffering from, or susceptible to, a condition which can be ameliorated by the administration of an inhibitor of tryptase. For example, the compounds of the invention may be useful in the treatment of inflammatory diseases, such as arthritis, rheumatoid arthritis and other joint conditions, including arthritis, rheumatoid arthritis and other joint disorders, such as rheumatoid spondylitis, gouty arthritis, traumatic arthritis, rubella arthritis, psoriatic arthritis, osteoarthritis and other chronic inflammatory joint diseases, or articular cartilage destructive diseases, ocular conjunctivitis, vernal conjunctivitis, inflammatory bowel diseases, asthma, allergic rhinitis, interstitial lung disease, fibrosis, scleroderma, pulmonary fibrosis, cirrhosis, myocardial fibrosis, neurofibromas, hypertrophic scars, various dermatological conditions, such as atopic dermatitis and psoriasis, myocardial infarction, stroke, angina and other consequences of atherosclerotic plaque rupture, as well as periodontal disease, diabetic retinopathy, tumor growth, allergy, multiple sclerosis, and other joint disorders, Peptic ulcer and syncytial virus infection.

A particular embodiment of the therapeutic method of the present invention is the treatment of asthma.

Another particular embodiment of the therapeutic method of the present invention is the treatment of joint inflammation.

Another particular embodiment of the therapeutic method of the present invention is the treatment of inflammatory bowel disease.

According to a further feature of the invention there is provided a method of treatment of a human or animal subject suffering from, or susceptible to, a condition which can be ameliorated by the administration of an inhibitor of tryptase, for example a condition described hereinbefore, which method comprises administering to the subject an effective amount of a compound of the invention or a composition comprising a compound of the invention. By "effective amount" is meant an amount describing that the compound of the present invention is effective to inhibit tryptase, thereby producing the desired therapeutic effect.

Combination therapy

As explained above, other pharmaceutically active agents may be employed in combination with the compounds of the present invention, depending on the disease to be treated. For example, in the treatment of asthma, β -adrenergic agonists such as salbutamol, terbutaline, formoterol, fenoterol or pramipeline (prenaline) may be included, anticholinergic agents such as ipratropium bromide, anti-inflammatory corticosteroids such as beclomethasone dipropionate, triamcinolone acetonide, flunisolide or dexamethasone, and anti-inflammatory agents such as cromolyn sodium and nedocromil sodium may also be included. Accordingly, the invention extends to a pharmaceutical composition comprising a compound of the invention and a second compound selected from a β -adrenergic agonist, an anticholinergic agent, an anti-inflammatory corticosteroid, and an anti-inflammatory agent; and a pharmaceutically acceptable carrier thereof. Specific pharmaceutical carriers that can be used in the pharmaceutical composition are as described herein.

Furthermore, the invention extends to a method of treating a patient suffering from asthma, comprising administering to the patient a compound of the invention and a second compound selected from a beta-adrenergic agonist, an anticholinergic agent, an anti-inflammatory corticosteroid, and an anti-inflammatory agent. In such a combination method, the compound of the invention may be administered prior to the administration of the second compound, the compound of the invention may be administered after the administration of the second compound, or the compound of the invention and the second compound may be administered concurrently.

Mode of release

According to the present invention, a compound of the present invention or a pharmaceutical composition of the present invention may be introduced to a patient parenterally, transmucosally (e.g., orally, nasally, pulmonarily, or rectally), or transdermally.

Oral delivery

The use contemplated herein is an oral solid dosage form generally described in Remington's pharmaceutical Science, 18 th edition, 1990(Mack Publishing co. easton PA 18042) chapter 89, incorporated herein by reference. Solid dosage forms include tablets, capsules, pills, troches or lozenges, cachets or pellets. Furthermore, the compositions of the present invention may be formulated using liposome or protein-like encapsulation processes (e.g., protein-like microspheres as reported in U.S. Pat. No.4,925,673). Liposome encapsulation processes can be utilized and liposomes can be derived from a variety of polymers (e.g., U.S. Pat. No.5,013,556). A description of solid dosage forms that may be used for therapeutic agents is given in Marshall, k., Modern pharmaceuticals, edited by g.s.banker and c.t.rhodes, chapter 10, 1979, incorporated herein by reference. In general, the formulations will include a compound of the invention and an inert ingredient which protects from the gastric environment and releases the biologically active material, i.e., the compound of the invention, in the intestine.

Also specifically contemplated are oral dosage forms of the compounds of the invention. Such a compound may be chemically modified for more effective oral delivery. Typically, the chemical modification is the attachment of at least one moiety to the component molecule itself, wherein the moiety can (a) inhibit proteolysis; and (b) uptake into the blood stream from the stomach or intestine. There is also a need to increase the overall stability of the compounds of the invention, increasing circulation time in vivo. Examples of such moieties include: polyethylene glycol, copolymers of ethylene glycol and propylene glycol, carboxymethyl cellulose, dextran, polyvinyl alcohol, polyvinylpyrrolidone, and polyproline. Abuchowski and Davis, 1981, "Soluble Polymer-enzyme Adducts" (Soluble Polymer-enzyme adducts), Enzymes as Drugs, Hocenberg and Roberts eds., Wiley-Interscience, New York, NY, pp.367-383; newmark et al, 1982, j.appl.biochem (journal of applied biochemistry), 4: 185-189. Other polymers that may be used are poly-1, 3-dioxolane and poly-1, 3, 6-tioxocane. Preferred for such pharmaceutical use are polyethylene glycol moieties.

With respect to the compounds of the present invention, the site of release may be the stomach, small intestine (duodenum, jejunum or ileum) or large intestine. One skilled in the art can utilize formulations that will not dissolve in the stomach, but release the material elsewhere in the duodenum or intestine. Preferably, the release will avoid the harmful effects of the gastric environment, either by protecting the compounds of the invention, or releasing the compounds outside the gastric environment, e.g. the intestine.

To ensure complete gastric tolerance, a coating impermeable to at least pH 5.0 is necessary. Examples of inert ingredients more commonly used as enteric coatings are Cellulose Acetate Trimellitate (CAT), hydroxypropylmethylcellulose phthalate (HPMCP), HPMCP 50, HPMCP 55, polyvinyl acetate phthalate (PVAP), Eudragit L30D, Aquateric, Cellulose Acetate Phthalate (CAP), Eudragit L, Eudragit S and shellac. These coatings can be used as mixed films.

Coatings or coating mixtures may also be used on tablets, which are not intended to protect against the stomach. They may include sugar coatings or coatings that allow the tablets to be swallowed. Capsules may consist of a hard shell (e.g., gelatin) for the release of dry therapeutic agents, i.e., powders; for liquid dosage forms, a soft gelatin shell may be used. The outer shell material of the cachets can be thick starch or other edible paper. For pills, lozenges, molded tablets or troches, wet-mass techniques can be utilized.

The therapeutic agent multiparticulates in the form of granules or pellets having a particle size of about 1mm may be included in the formulation. The materials used to formulate capsules can also be powders, lightly compressed fillers or even tablets. The therapeutic agent may be prepared by compression.

Both coloring and flavoring agents may be included. For example, the compounds of the present invention may be formulated (e.g., encapsulated by liposomes or microspheres) and then further included in edible products, such as frozen beverages containing colorants and flavoring agents.

The volume of the therapeutic agent may be diluted or increased with an inert material. These diluents may include carbohydrates, especially mannitol, alpha-lactose, anhydrous lactose, cellulose, sucrose, modified dextrans and starch. Certain inorganic salts may also be used as fillers, including calcium triphosphate, magnesium carbonate and sodium chloride. Some commercially available diluents are Fast-Flo, Emdex, STA-Rx 1500, Emcompress and Avicell.

The therapeutic agent may be formulated to include a disintegrant and be in a solid dosage form. Materials used as disintegrants include, but are not limited to, starch, including the commercial disintegrant based on starch, Explotab. Sodium starch glycolate, Amberlite, sodium carboxymethylcellulose, ultramylopectin, sodium alginate, gelatin, orange peel, acid carboxymethyl cellulose, natural sponge and bentonite may all be used. Another form of disintegrant is an insoluble cation exchange resin. Powdered gums may be used as disintegrants and binders and they may include powdered gums such as agar, karaya or tragacanth. Alginic acid and its sodium salt may also be used as a disintegrant.

Binders may be used to hold the therapeutic agents together to form a hard tablet, including materials from natural products such as acacia, tragacanth, starch and gelatin. Others include Methyl Cellulose (MC), Ethyl Cellulose (EC) and carboxymethyl cellulose (CMC). Both polyvinylpyrrolidone (PVP) and Hydroxypropylmethylcellulose (HPMC) may be used in an alcoholic solution to granulate the therapeutic agent.

An anti-friction agent may be included in the formulation of the therapeutic agent to prevent sticking during the formulation process. A layer of lubricant may be used between the therapeutic agent and the die wall, including but not limited to: stearic acid, including its magnesium and calcium salts, Polytetrafluoroethylene (PTFE), liquid paraffin, vegetable oils and waxes. Soluble lubricants such as sodium lauryl sulfate, magnesium lauryl sulfate, polyethylene glycols of various molecular weights, Carbowax 4000 and 6000 may also be used.

Glidants may be added to improve the flow properties of the drug during formulation and to aid rearrangement during compression. Glidants may include starch, talc, fumed silica and hydrated aluminosilicates.

To aid in the dissolution of the therapeutic agent in an aqueous environment, a surfactant may be added as a wetting agent. The surfactant may include anionic detergents such as sodium lauryl sulfate, sodium dioctyl sulfosuccinate and sodium dioctyl sulfonate. Cationic detergents may be used, including benzalkonium chloride or benzethonium chloride. A list of nonionic detergents that may be included in the formulation as surfactants are lauromaprogol 400, polyoxyl 40 stearate, polyoxyethylene hydrogenated castor oil 10, 50 and 60, glyceryl monostearate, polysorbate 40, 60, 65 and 80, sucrose fatty acid esters, methyl cellulose and carboxymethyl cellulose. These surfactants may be present in the formulations of the compounds of the present invention either individually or as mixtures in varying proportions.

Possible additives that enhance the uptake of the compounds of the invention are fatty acids, such as oleic acid, linoleic acid and linolenic acid.

Controlled release oral formulations may be desirable. The drug may be incorporated into an inert matrix, such as a gum, for release by a diffusion or leaching mechanism. Slowly denaturing matrices may also be incorporated into the formulation. Some enteric coatings also have a delayed release effect.

Another controlled release form of this therapeutic agent is a method based on the Oros therapeutic system (Alza Corp.), that is, the drug is encapsulated in a semipermeable membrane which, due to osmotic action, allows water to enter and push the drug out through a single small orifice.

Other coatings may be used in the formulation. They include a variety of sugars that can be used in coating pans. The therapeutic agent may also be in the form of film-coated tablets, in which case the materials used are divided into 2 groups. The first group is non-enteric materials including methylcellulose, ethylcellulose, hydroxyethylcellulose, methylhydroxyethylcellulose, hydroxypropylcellulose, hydroxypropylmethylcellulose, sodium carboxymethylcellulose, povidone, and polyethylene glycol. The second group consists of enteric materials, which are commonly used phthalates.

Mixtures of materials may be used to provide an optimal film coating. Film coating can be carried out in a coating pan or in a fluidized bed, or by compression coating.

Pulmonary delivery

Also encompassed herein are pulmonary releases of the compounds of the invention, either alone or in pharmaceutical compositions. The compound is released into the lungs of the mammal simultaneously with inhalation, passing through the lung intraepithelial layer into the bloodstream. Other reports on this include Adjei et al, 1990, Pharmaceutical Research, 7: 565-569; adjei et al, 1990, International journal of pharmacy, 63: 135-144 (leuproloidetate); braquet et al, 1989, Journal of cardiovascular pharmacology, 13 (supplement 5): 143-146 (endothelin-1); hubbard et al, 1989, Annals of Internal Medicine, Vol.III, pp.206-212(a 1-antitrypsin); smith et al, 1989, j.clin.invest. (journal of clinical examination), 84: 1145-1146 (a-1-protease); oswein et al, 1990, "Aerosolization of Proteins", proceedings of Symposium on Respiratory Drug Delivery II, Keystone, Colorado, March (recombinant human growth hormone); debs et al, 1988, j. immunol. (journal of immunology), 140: 3482-3488 (interferon-. gamma.and tumor necrosis factor-. alpha.); platz et al, U.S. Pat. No.5,284,656 (granulocyte colony stimulating factor). Methods and compositions for pulmonary delivery of systemically acting drugs are described in Wong et al, U.S. patent No.5,451,569, published 9/19 in 1995.

A wide range of mechanical devices designed for pulmonary delivery of therapeutic products are contemplated in the practice of the present invention, including but not limited to nebulizers, metered dose inhalers, and powder inhalers, all of which are familiar to those skilled in the art.

Some specific examples of commercially available devices suitable for practicing the present invention are the Ultravent nebulizer, manufactured by Mallinckrodt, inc., st.louis, Missouri; acorn II nebulizer, manufactured by Marquest Medical Products, Englewood, Colorado; a Ventolin metered dose inhaler manufactured by Glaxo inc, research flare Park, North Carolina; spinhaler powder inhalers, manufactured by Fisons Corp., Bedford, Massachusetts, and others. All such devices require the use of a formulation suitable for dispensing the compounds of the present invention. Generally, each formulation is specific to the type of device employed, and may involve the use of suitable propellant materials in addition to diluents, adjuvants and/or carriers ordinarily employed in therapy. Also, the use of liposomes, microcapsules or microspheres, including complexes or other types of carriers, is contemplated. The chemically modified compounds of the invention may also be formulated in different formulations depending on the type of chemical modification or the type of device employed.

Formulations suitable for use in a jet or ultrasonic nebulizer will generally comprise the compound of the invention dissolved in water at a concentration of about 0.1 to 25mg of compound per ml of solution. The formulation may also include buffers and monosaccharides (e.g., for stabilization and adjustment of osmotic pressure). The nebulizer formulation may also contain a surfactant to reduce or prevent surface-induced compound aggregation caused by nebulization of the solution when forming an aerosol.

Formulations suitable for metered dose inhalation devices will generally comprise a finely divided powder comprising a compound of the invention suspended in a propellant by means of a surfactant. The propellant may be any material conventionally used for this purpose, such as chlorofluorocarbons, hydrofluorocarbons or hydrocarbons, including trichlorofluoromethane, dichlorodifluoromethane, dichlorotetrafluoroethanol and 1, 1, 2, 2-tetrafluoroethane or combinations thereof. Suitable surfactants include sorbitan trioleate and soy lecithin. Oleic acid may also be used as a surfactant.

Formulations for dispersion from a powder inhalation device will comprise a finely divided dry powder containing a compound of the invention and may also include a bulking agent such as lactose, sorbitol, sucrose or mannitol in an amount which facilitates dispersion of the powder from the device, for example 50 to 90% by weight of the formulation. The compounds of the invention should most advantageously be formulated in particulate form with an average particle size of less than 10mm (or microns), most preferably 0.5 to 5mm, for most effective delivery to the distal lung.

Nasal delivery

Nasal release of the compounds of the invention is also contemplated. Nasal release allows the compound to pass directly into the bloodstream after the therapeutic product is administered to the nose, without the product being deposited in the lungs. Nasal release formulations include those utilizing dextran or cyclodextrin.

Transdermal delivery

Various and numerous methods are known in the art for transdermal delivery of drugs, such as via a transdermal patch, and may be used in the present invention. Transdermal patches are described, for example, in U.S. Pat. No.5,407,713 to Rolando et al, published 4,8, 1995; fallon et al U.S. Pat. No.5,352,456 issued on 10/4/1994; U.S. Pat. No.5,332,213 to D' Angelo et al, published 8,9, 1994; U.S. Pat. No.5,336,168 to Sibalis et al, published 1994, 8, 9; farhadie et al, U.S. Pat. No.5,290,561, published 3, 1, 1994; U.S. Pat. No.5,254,346 to Tucker et al, published 1993 at 10/19; berger et al, U.S. Pat. No.5,164,189, issued 11, 17, 1992; U.S. Pat. No.5,163,899 to Sibalis et al, published 11/17/1992; U.S. patent nos.5,088,977 and 5,087,240 to Sibalis et al, published on 18.2.1992; benecke et al, U.S. Pat. No.5,008,110, published 4, 16, 1991; U.S. patent No.4,921,475 to Sibalis, published 5/1/1990, each incorporated herein by reference in its entirety.

It will be readily appreciated that transdermal routes of administration may be enhanced by the use of skin permeation enhancers, such as described in U.S. Pat. No.5,164,189 (supra), U.S. Pat. No.5,008,110 (supra), and U.S. Pat. No.4,879,119 to Aruga et al, published 11/7 1989, each of which is incorporated herein by reference in its entirety.

Topical administration of drugs

For topical administration, gels (aqueous or alcoholic), creams or ointments containing the compounds of the invention may be used. The compounds of the present invention may also be incorporated into a patch gel or matrix to allow for controlled release of the compound across a transdermal barrier.

Rectal administration

Solid compositions for rectal administration include suppositories, formulated according to known methods, containing at least one compound of the invention.

The percentage of active ingredient in the composition of the invention may vary and it is necessary that it should constitute a proportion such that a suitable dosage form should be obtained. Obviously, several unit dosage forms may be administered at about the same time. The dosage employed will be determined by a physician and will depend upon the desired therapeutic effect, the route of administration and the duration of the treatment and the condition of the patient. For adults, the inhaled dose is generally from about 0.001 to about 50, preferably from about 0.001 to about 5mg/kg body weight per day, the orally administered dose is generally from about 0.01 to about 100, preferably from 0.1 to 70, especially from 0.5 to 10mg/kg body weight per day, and the intravenously administered dose is generally from about 0.001 to about 10, preferably from 0.01 to 1mg/kg body weight per day. In each particular case, the dosage will be determined based on subject-specific factors such as age, weight, general health, and other characteristics that can affect the efficacy of the pharmaceutical product.

Furthermore, the compounds according to the invention may be administered as frequently as necessary in order to obtain the desired therapeutic effect. Some patients may respond rapidly to higher or lower doses, and weaker maintenance doses may be found to be appropriate. With respect to other patients, long-term treatment may be required, with administration 1 to 4 times per day, depending on the physiological needs of each particular patient. In general, the active product may be administered orally from 1 to 4 times per day. Of course, for some patients, it will be necessary not to exceed one or two times per day.

Naturally, the patient to whom the compound of the invention is administered is preferably a human, but may be any animal. Thus, as one of ordinary skill in the art can readily appreciate, the methods and pharmaceutical compositions of the present invention are particularly suited for administration to any animal, particularly mammals, including, but in no way limited to, pets, such as cats or dogs, livestock, such as, but not limited to, cattle, horses, goats, sheep and pigs, wild animals (whether wild or in zoos), research animals, such as mice, rats, rabbits, goats, sheep, pigs, dogs, cats, and the like, birds, such as chickens, turkeys, birds, and the like, i.e., veterinary uses.

Preparation of the Compounds of the invention

The compounds of the invention can be prepared by using or adapting known methods, which means methods used hitherto or described in the literature, such as those described in R.C. Larock, comprehensive organic Transformations, VCH, 1989.

In the reactions described below, it may be necessary to protect reactive functional groups, such as hydroxyl, amino, imino, thio or carboxyl groups (which are required in the end product) to avoid their unwanted participation in the reaction. Conventional protecting Groups may be used in accordance with standard practice, see, for example, T.W.Greene and P.G.M.Wuts, "Protective Groups in organic chemistry", John Wiley and Sons, 1991.

Compounds of formula (Ia) represented by formula (IX) can be prepared as shown in scheme 1, wherein R³、R⁴、R⁵And n is as defined above, R¹And R²Are all hydrogen and are in the form of hydrogen,is a single bond.

Scheme 1

For example, the compound of formula (IX) may be prepared by:

(i) in an inert solvent, such as tetrahydrofuran, at a temperature of about-78 deg.C⁴And n is as defined above, P¹A compound of formula (II) which is a suitable protecting group, e.g. benzyloxycarbonyl, is treated with a suitable base, e.g. hexamethyldisilazane lithium, and then reacted with N-phenyltrifluoromethanesulfonimide to give a compound of formula (III) wherein R is⁴、P¹And n is as defined above, Tf is-SO₂CF₃；

(ii) Reacting a triflate of formula (III) with an arylboronic acid of formula (X) in the presence of an aqueous base, such as sodium bicarbonate, and a palladium catalyst, such as tetrakis (triphenylphosphine) palladium, at a temperature of from about 80 to about 100 ℃:

to give a compound of the formula (IV) in which R⁴、R⁵、P¹And n is as defined above;

(iii) reduction of the compound of formula (IV) with sodium borohydride in ethanol to give the compound of formula (V), wherein R⁴、R⁵、P¹And n is as defined above;

(iv) the conversion of the hydroxymethyl group in the compound of formula (V) to a suitably protected aminomethyl group is advantageous as described further belowE.g. reaction of a compound of formula (V) with phosphorus tribromide in pyridine, followed by treatment of the resulting bromomethyl intermediate with di-tert-butyliminodicarboxylate to give a compound of formula (VI), wherein R⁴、R⁵、P¹And n is as defined above, P²And P³Each being tert-butyloxycarbonyl (a suitable protecting group, followed by removal of the protecting group P¹Is stable under the conditions of (a);

(v) removing the protecting group P from the compound of formula (VI)¹For example if P¹Is benzyloxycarbonyl, P²And P³All are t-butyloxycarbonyl, deprotection can suitably be carried out by hydrogenation in the presence of a suitable metal catalyst, such as platinum or palladium, optionally supported on an inert support, such as carbon, preferably in a solvent, such as methanol or ethanol, to give a compound of formula (VII) wherein R is⁴、R⁵And n is as defined above, P²And P³As just defined;

(vi) the compound of formula (VII) is reacted with a compound of formula (XI) using standard coupling reactions:

wherein R is³Is as defined above, X¹Is hydroxy or halogen, preferably chlorine [ e.g. if X¹Is a hydroxyl group, the reaction can be carried out using standard peptide coupling procedures, for example in tetrahydrofuran (or dimethylformamide) in the presence of O- (7-azabenzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium hexafluorophosphate and triethylamine (or diisopropylethylamine); if X1 is a halogen atom, the acylation may be carried out with the aid of a base (e.g. pyridine), preferably in a solvent (e.g. tetrahydrofuran), at a temperature of about room temperature]To give a compound of the formula (VIII) in which R³、R⁴、R⁵、n、P²And P³Is as defined above;

(vii) removal of the protecting group P from the compound (VIII)²And P³For example if P²And P³All are t-butyloxycarbonyl, the reaction can be conveniently carried out in the presence of an acid (e.g., trifluoroacetic acid), in an inert solvent (e.g., dichloromethane), or in methanol with hydrogen chloride.

Compounds of formula (Ia) represented by formula (XVI) can be prepared as shown in scheme 2, wherein R¹、R²、R³、R⁴、R⁵And n is as defined above, and n is,is a single bond.

Scheme 2

For example, a compound of formula (XVI) can be prepared by:

(i) in the presence of potassium carbonate and a palladium catalyst, the latter being, for example, [1, 1' -bis- (diphenylphosphino) ferrocenyl]-dichloropalladium (II) -dichloromethane complex, in an inert solvent, for example dimethyl sulfoxide, at a temperature of about 80 ℃, in which R⁴And n is as defined above, P¹A compound of formula (II) which is a suitable protecting group (e.g. benzyloxycarbonyl) is reacted with an arylboronic ester of formula (XVII):

to give a compound of the formula (XII) in which R¹、R²、R⁴、R⁵、n、P¹、P²And P³Is as defined above; alternatively, compounds of formula (XII) may be prepared in the presence of potassium acetate, (diphenylphosphino) ferrocene and [1, 1' -bis- (diphenylphosphino) ferrocenyl]-reacting a compound of formula (II) with bis (pinacolato) boron in the presence of dichloropalladium (II) in an inert solvent (e.g. dioxane) at a temperature of about 80 ℃, followed by the presence of potassium carbonate and a palladium catalyst, the latter e.g. [1, 1' -bis- (diphenylphosphino) ferrocenyl]-dichloropalladium (II) -dichloromethane complex, reacting the intermediate boronate of formula (XIII) with the compound of formula (XVIII) in an inert solvent (for example dimethyl sulfoxide) at a temperature of about 80 ℃:

wherein R is¹、R²、P¹And P²Is as defined above.

(ii) Removing the protecting group P from the compound of formula (XII)¹For example if P¹Is benzyloxycarbonyl, P²And P³Are both t-butyloxycarbonyl, deprotection can be carried out by hydrogenation as described above to give compounds of formula (XIV) wherein R is¹、R²、R⁴、R⁵、n、P²And P³As just defined;

(iii) using standard coupling conditions (such as those described above), the compound of formula (XIV) is reacted with a compound of formula (XI), wherein R is¹Is as defined above, X¹Is a hydroxyl group or a halogen atom, preferably chlorine, to give a compound of the formula (XV) wherein R¹、R²、R³、R⁴、R⁵、n、P²And P³Is as defined above;

(iv) removal of the protecting group P in Compound (XV) Using standard coupling conditions (e.g.those described above)²And P³。

Compounds of formula (Ia) represented by formula (XVI) can also be prepared using resin techniques as shown in scheme 3, wherein R¹、R²、R³、R⁴、R⁵And n is as defined above:

scheme 3

For example, a compound of formula (XVI) can be prepared by:

(i) according to the process described in J.M.Salvino et al, International patent application publication No. WO 99/67228, whereinCoupling of a resin representing the polymeric core (containing polystyrene cross-linked with 1% to 2% divinylbenzene) (XIX, aminomethylated styrene/divinylbenzene copolymer) with 4-hydroxy-2, 3,5, 6-tetrafluorobenzoic acid gives TFP resins, in whichIs as defined above;

(ii) the TFP resin is treated with an acid of formula (XI) wherein R is an acid of formula (XI) in the presence of diisopropylcarbodiimide and dimethylaminopyridine in an inert solvent, such as dimethylformamide, at a temperature of about room temperature³Is as defined above, X¹Is hydroxy, to give resin 1, wherein R³Andis as defined above;

(iii) resin 1 is treated with a compound of formula (XIV) wherein R is¹、R²、R⁴、R⁵、n、P¹And P²Is as just defined to give a compound of formula (XV);

(iv) removing the protecting group from the compound of formula (XV), e.g. if P²And P³All are tert-butyloxycarbonyl, the reaction can be conveniently carried out in the presence of an acid, such as trifluoroacetic acid, in an inert solvent, such as dichloromethane, or in methanol with hydrogen chloride.

Compounds of formula (Ib) represented by formula (XX), wherein R is as shown in scheme 4, can be prepared³And R⁵Is as defined above, R⁴Is cyano attached at the 4-position of the piperidine ring:

scheme 4

For example, a compound of formula (XX) may be prepared:

(i) in the presence of a phase transfer catalyst, such as tetrabutylammonium bromide, in a mixture of water and an inert solvent, such as dichloromethane, at a temperature of about room temperature, wherein R⁵Is the reaction of benzyl bromide of formula (XXI) as defined above with sodium cyanide to give a compound of formula (XXII) wherein R is⁵Is as defined above;

(ii) treatment of benzyl cyanide of formula (XXII) with an appropriately protected bis- (2-haloethyl) amine of formula (XXVIII) in the presence of sodium hydride in an inert solvent, such as dimethylformamide, at a temperature of about room temperature:

wherein X is halo, preferably chloro, P¹Is a suitable protecting group, e.g. tert-butyloxycarbonyl, to give a compound of formula (XXIII) wherein R is⁵And P¹Is as defined above;

(iii) hydrogenating the compound of formula (XXIII) in ethanol in the presence of hydrochloric acid under pressure to obtain a compound of formula (XXIV), wherein R is⁵And P¹Is as defined above;

(iv) the amino group in the compound of formula (XXIV) is protected with a suitable protecting group, such as benzyloxycarbonyl, to give a compound of formula (XXV) wherein R is⁵、P¹And P²Is as defined above;

(v) removing the protecting group P from the compound of formula (XXV)¹To give a compound of the formula (XXVI) in which R⁵And P²Is as defined above;

(vi) using standard coupling conditions (such as those described above), a compound of formula (XXVI) is reacted with a compound of formula (XI), wherein R is¹Is as defined above, X¹Is hydroxy or a halogen atom, preferably chlorine, to give a compound of the formula (XXVII) in which R is⁵And P²Is as defined above;

(vii) the protecting group P in the compound of formula (XXVII) is removed using standard coupling conditions (such as those described above)²。

Compounds of formula (Ia) represented by formula (IX) wherein R is³、R⁴、R⁵And n is as defined above, R¹And R²Are all hydrogen and are in the form of hydrogen,is a double bond: removing P from the compound of formula (VI)¹Protecting group, then acylating with a compound of formula (XI), followed by removal of P²And P³A protecting group.

The compound of formula (Ia) represented by formula (XVI) can be prepared wherein R¹、R²、R³、R⁴、R⁵And n is as defined above, and n is,is a double bond: removing P from the compound of formula (XII)¹Protecting group, then acylating with a compound of formula (XI), followed by removal of P²And P³A protecting group.

According to a further feature of the present invention, the compounds of the present invention may be prepared by interconversion of other compounds of the present invention.

As an example of an interconversion process, where R¹、R²、R⁴、R⁵And n is as defined above, R³Compounds of formula (Ia) containing an optionally substituted alkylene linkage may be prepared by hydrogenating the corresponding compound of formula (Ia), wherein R is³Containing corresponding optionally substituted alkenylene or alkynylene linkages. The hydrogenation may be carried out using hydrogen (optionally under pressure) in the presence of a suitable metal catalyst, such as platinum or palladium, optionally supported on an inert support, such as carbon, preferably in a solvent, such as methanol or ethanol, at a temperature of about room temperature.

As another example of an interconversion process, compounds of the present invention containing heterocyclic groups in which the heteroatom is a nitrogen atom may be oxidized to their corresponding N-oxides. The oxidation may suitably be carried out by reaction with a mixture of hydrogen peroxide and an organic acid, such as acetic acid, preferably at room temperature or above, for example at a temperature of about 60-90 ℃. Alternatively, the oxidation may be carried out by reacting with a peracid, such as peracetic acid or m-chloroperbenzoic acid, in an inert solvent, such as chloroform or dichloromethane, at a temperature from about room temperature to reflux, preferably at elevated temperature. The oxidation may also be carried out by reacting with hydrogen peroxide in the presence of sodium tungstate at a temperature between room temperature and about 60 ℃.

As another example of the interconversion process, the compound of formula (Ia) containing a sulfone bond may be prepared by oxidation of the corresponding compound containing an-S-or sulfoxide bond. For example, the oxidation may suitably be carried out by reaction with a peracid, such as 3-chloroperbenzoic acid, preferably in an inert solvent such as dichloromethane, preferably at or near room temperature.

It will be appreciated that the compounds of the invention may contain asymmetric centers. These asymmetric centers may independently be in the R or S configuration. It will be apparent to those skilled in the art that certain compounds of the invention may also exhibit geometric isomerism. It is to be understood that the present invention includes individual geometric isomers and stereoisomers of the compounds of the invention and mixtures thereof, including racemic mixtures. Such isomers may be isolated from their mixtures using or adapting known methods, such as chromatographic techniques and recrystallization techniques, or they may be prepared separately from the appropriate isomers of their intermediates.

According to a further feature of the present invention, acid addition salts of the compounds of the present invention may be prepared by reaction of the free base with the appropriate acid, using or adapting known procedures. For example, acid addition salts of the compounds of the invention may be prepared by dissolving the free base in water or aqueous alcohol or other suitable solvent with the appropriate acid, isolating the salt by evaporating the solution, or reacting the free base with the acid in an organic solvent, in which case the salt is isolated directly or may be obtained by concentrating the solution.

Acid addition salts of the compounds of the present invention may be regenerated from the salts using or modifying known methods. For example, the parent compounds of the invention may be regenerated from their acid addition salts by treatment with a base, such as aqueous sodium bicarbonate or aqueous ammonia.

The starting materials and intermediates can be prepared by, or in a manner adjusted to, known methods, e.g. the methods described in the reference examples or their obvious chemical equivalents.

Wherein R is¹、R²、P²And P³Arylboronic esters of formula (XVII) as defined above may be prepared in the presence of potassium acetate and [1, 1' -bis- (diphenylphosphino) ferrocenyl group]-palladium (II) dichloride in an inert solvent, such as dioxane, at a temperature of about 80 ℃, wherein R¹、R²、P²And P³Is the reaction of a compound of formula (XVIII) as defined above with bis (pinacolato) boron.

Wherein R is¹And R²Is as defined above, P²And P³Compounds of formula (XVIII), both tert-butyloxycarbonyl, can be prepared by reacting a compound of formula (XXIX) in an inert solvent, such as tetrahydrofuran, at a temperature of about room temperature:

with sodium hydride and di-tert-butyliminodicarboxylate.

The intermediates of formula (VIII) and (XV) are novel compounds and therefore they and the processes described herein for their preparation constitute further features of the invention.

The following illustrative examples and reference examples further illustrate but do not limit the invention.

In nuclear magnetic resonance spectroscopy (NMR), the chemical drift is expressed in ppm relative to tetramethylsilane. The abbreviations have the following meanings: br is broad, dd is bimodal, s is unimodal, m is multiplet.

For determining the retention time (R)_T) The conditions for high performance liquid chromatography/mass spectrometry (LC-MS) of (1) were as follows: a 3 micron Luna C18(2) HPLC column (30mmx4.6mm) eluting with: (i) a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (1: 19, v/v), eluted for 2 minutes, (ii) a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (ii) (ii)(ii) a gradient of from 1: 19 to 19: 1, v/v) eluting over 10 minutes, (iii) a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (19: 1, v/v) eluting for 2 minutes, (iv) a gradient of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (1: 19 to 19: 1, v/v) eluting over 2 minutes; the flow rate was 2 ml/min, approximately 200. mu.l/min giving to the mass spectrum; the injection volume is 10-40 μ l; linear diode array (220-450nm), linear Evaporative Light Scattering (ELS) detection ELS-temperature 50 ℃, collection 8-1.8 ml/min; the heat source temperature was 150 ℃.

Detailed Description

The invention may be better understood by reference to the following non-limiting examples, which are intended to be exemplary of the invention. The following examples are provided to more fully illustrate specific embodiments of the invention. They should in no way be construed as limiting the broad invention.

In the nuclear magnetic resonance spectrum (NMR) reported below, the chemical drift is expressed in ppm relative to tetramethylsilane. The abbreviations have the following meanings: br is broad, dd is bimodal, s is unimodal, m is multiplet. "parallel object" means partial masking.

Also in the examples, for determining the retention time (R)_T) The conditions for high performance liquid chromatography/mass spectrometry (LC-MS) of (1) were as follows: a 3 micron Luna C18(2) HPLC column (30mmx4.6mm) eluting with: (i) elution is carried out for 2 minutes with a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (1: 19, v/v), (ii) a gradient of a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (1: 19 to 19: 1, v/v) over 10 minutes, (iii) a gradient of a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (19: 1, v/v) over 2 minutes, (iv) a gradient of a mixture of acetonitrile containing 0.05% trifluoroacetic acid and water containing 0.05% trifluoroacetic acid (1: 19 to 1: 19, v/v) over 2 minutes; the flow rate was 2 ml/min, approximately 200. mu.l/min giving to the mass spectrum; the injection volume is 10-40 μ l; linear diodeArray (220) and 450nm), linear Evaporative Light Scattering (ELS) detection ELS-temperature 50 ℃, gain 8-1.8 ml/min; the heat source temperature was 150 ℃. "ion spray" means ion spray.

Example 1

3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (5-phenylethynyl-pyridin-3-yl) -methanone) dihydrochloride)

B- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -pinacolato-boron

A solution of 3-bromobenzyl bromide (7.5g, 30mmol) and di-tert-butyliminodicarboxylate (6.5g, 30mmol) in dry tetrahydrofuran (80ml) was treated portionwise with sodium hydride (1.2g, 60% dispersion in mineral oil). After stirring at ambient temperature for 7 hours, the reaction mixture was partitioned between saturated aqueous ammonium chloride (90ml) and ethyl acetate (250ml 2 parts). The organic layers were combined, washed with brine (75ml), then dried over magnesium sulfate and then concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a mixture of pentane and dichloromethane (2: 1, v/v) to give 3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]Bromobenzene as a pale yellow oil (9.52 g). A sample of this material (2.0g, 5.2mmol) was dissolved in anhydrous dimethyl sulfoxide (30ml) and the solution was treated with potassium acetate (1.52g, 15.5mmol), bis (pinacolato) diboron (1.45g, 5.7mmol) and [1, 1' -bis- (diphenylphosphino) ferrocenyl]dichloro-Palladium (II) -Dichloromethane Complex (0.13g, 0.16 mmol). The mixture was stirred at 80 ℃ under nitrogen for 5 hours, then cooled and then partitioned between water (100ml) and diethyl ether (75ml 4 parts). The organic layers were combined, washed twice with brine (75ml), then dried over magnesium sulfate and then concentrated under vacuum. The residue is chromatographed on silica, eluting with a mixture of pentane and dichloromethane (2: 1, v/v) to give B- [ N-bis- (tert-butoxycarbonyl) -aminomethyl]-phenyl } -pinacolato-boron as a colourless oil (1.08 g).¹H NMR(CDCl₃，500MHz)：δ7.78(s，1H)，7.70(m，1H)，7.39(m，1H)，7.30(m，1H)，4.79(s，2H)，127(s，18H)，1.35(s，12H).MS(EI)：434(M⁺+H).

4- {3- [ N, N-bis- (tert-Butoxycarbonyl) aminomethyl ] -phenyl } -piperidine

To a solution of lithium diisopropylamide (54mmol) in anhydrous tetrahydrofuran (50ml) was added dropwise a solution of benzyl 4-oxo-1-piperidinecarboxylate (11.4g, 49mmol) in anhydrous tetrahydrofuran (50ml) at-78 ℃. The mixture was stirred at-78 ℃ for 20 minutes and then treated with a solution of N-phenyltrifluoromethanesulfonimide (19.26g, 54mmol) in dry tetrahydrofuran (55 ml). The resulting orange suspension was warmed to 0 ℃, then stirred at 0 ℃ for 2 hours, then concentrated under vacuum. The residue was chromatographed on silica gel eluting with dichloromethane to give benzyl 1, 2, 3, 6-tetrahydro-4- (trifluoromethanesulfonyloxy) pyridine-1-carboxylate as a yellow oil (11.34 g). A portion of this material (0.84g, 2.3mmol) was dissolved in anhydrous dimethylformamide (20ml), and the solution was taken up with B- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]-phenyl-pinacolato-boron (1.0g, 2.3mmol), potassium carbonate (0.96g, 6.7mmol) and [1, 1' -bis- (diphenylphosphino) ferrocenyl]Palladium (II) dichloride-dichloromethane complex (0.1g, 0.14 mmol). The mixture was heated at 80 ℃ under nitrogen for 18 hours, then cooled, and then concentrated under vacuum. The residue was partitioned between ethyl acetate (100ml 2 parts) and water (100ml) containing concentrated ammonium hydroxide (6 ml). The organic extracts were combined, dried over magnesium sulfate and then concentrated in vacuo. The oil was chromatographed on silica gel eluting with a mixture of ethyl acetate and pentane (1: 4, v/v) to give a yellow oil (0.9 g). This material was dissolved in ethanol (20ml), and the solution was treated with 10% palladium on carbon (20mg), followed by stirring at ambient temperature under a hydrogen atmosphere for 5 hours. The reaction mixture was filtered through a short hyflo pad and the filtrate was concentrated under vacuum to give 4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]Phenyl } -piperidine, as a colourless oil (0.54 g).¹H NMR(CDCl₃，500MHz)：δ7.10(m，4H)，4.80(s，2H)，4.45(br m，1H)，3.20(br m，1H)，2.98(br m，1H)，2.75(br m，1H)，1.90(m，1H)，1.75-1.60(m，3H)，1.42(s，18H).MS(EI)：391(M⁺+H).

C.N, N-bis- (tert-butyloxycarbonyl) -3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (0.25g, 1.1mmol) in dry dimethylformamide (5ml) was treated with O- (7-azabenzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium hexafluorophosphate (0.42g, 1.1mmol) and diisopropylethylamine (0.5ml, 3mmol). The mixture was stirred at ambient temperature for 15 minutes and then treated with 4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]-phenyl } -piperidine (0.39g, 1.0mmol) in dimethylformamide (5 ml). After stirring at ambient temperature for 18 hours, the reaction mixture was concentrated under vacuum. The residue was partitioned between ethyl acetate (50ml) and saturated aqueous sodium bicarbonate (15 ml). The organic layer was dried over magnesium sulfate and then concentrated under vacuum. The residue was chromatographed on silica gel, eluting with a mixture of dichloromethane and methanol (49: 1, v/v) to give N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl]Benzylamine as a yellow oil (0.25 g).¹H NMR[(CD₃)₂SO，500MHz]：δ8.82(s，1H)，8.62(s，1H)，8.02(s，1H)，7.61(m，2H)，7.45(m，3H)，7.30(m，1H)，7.20(m，1H)，7.15(m，1H)，7.04(m，1H)，4.68(s，2H)，4.62(br m，1H)，3.60(br m，1H)，3.23(brm，1H)，2.85(m，2H)，1.83(br m，1H)，1.65(m，3H)，1.39(s，18H).MS(EI)：596(M⁺+H).

3- [1- (5-Phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride

Reacting 3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl]A solution of benzonitrile (0.15g, 0.25mmol) in ethyl acetate (20ml) was cooled to 0 ℃ and then saturated with hydrogen chloride gas. The reaction mixture was stirred at ambient temperature for 4 hours and then concentrated to dryness under vacuum. The residue was treated with ethyl acetate (10ml) and the solvent was removed in vacuo. This procedure was repeated twice to give 3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl]Benzylamine dihydrochloride as a white solid (0.11 g).¹H NMR[(CD₃)₂SO，500MHz]：δ8.83(s，1H)，8.63(s，1H)，8.08(s，1H)，7.61(m，2H)，7.45(m，3H)，7.44(s，1H)，7.37(m，3H)，4.64(br m，1H)，4.00(m，2H)，3.62(br m，1H)，3.25(brm，1H)，2.90(br m，2H)，1.88(br m，1H)，1.70(m，3H).MS(EI)：396(M⁺+H).

Example 2

3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride)

A.5-phenethyl-pyridine-3-carboxylic acid

A solution of 5-phenylethynyl-pyridine-3-carboxylic acid (2g, 8.9mmol) in tetrahydrofuran (50ml) was treated with 10% palladium on carbon (200mg) and stirred at ambient temperature under a hydrogen atmosphere for 5 hours. The reaction mixture was filtered through a short hyflo pad and the filtrate was concentrated in vacuo to give 5-phenethyl-pyridine-3-carboxylic acid as a white solid (2 g).¹H NMR[(CD₃)₂SO，500MHz]：δ8.90(m，1H)，8.60(m，1H)，8.12(m，1H)，7.21(m，5H)，3.38(br s，1H)，2.95(m，4H).

N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine

Preparation of N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] by proceeding in a similar manner to the procedure described in example 1C but using 5-phenethyl-pyridine-3-carboxylic acid instead of 5-phenylethynyl-pyridine-3-carboxylic acid]-benzylamine as white amorphous solid.¹H NMR[(CD₃)₂SO，500MHz]：δ8.50(s，1H)，8.41(s，1H)，7.61(m，1H)，7.30-7.05(m，9H)，4.68(s，2H)，4.62(br m，1H)，3.48(br m，1H)，3.35(s，4H)，3.18(brm，1H)，2.85(m，2H)，1.82(br m，1H)，1.65(br m，1H)，1.58(br m，2H)，1.39(s，18H).MS(EI)：600(M⁺+H).

C.3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride

The procedure was carried out in a similar manner to the procedure described in example 1D, but using N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl]-benzylamine instead of N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl]Benzylamine, preparation of 3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl]Benzylamine dihydrochloride, as a white solid.¹H NMR[(CD₃)₂SO，500MHz]：δ8.90(m，2H)，8.42(s，1H)，7.58(m，1H)，7.38-7.20(m，8H)，4.62(br m，1H)，4.00(m，2H)，3.45(br m，1H)，3.20(br m，1H)，3.17(m，2H)，3.00(m，2H)，2.90(br m，2H)，1.88(br m，1H)，1.70(br m，3H).MS(EI)：400(M⁺+H).

Example 3

3- [1- (1-oxo-5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (1-oxo-5-phenethyl-pyridin-3-yl) -methanone hydrochloride)

Reacting N, N-bis- (tert-butyloxycarbonyl) -3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl]A solution of benzylamine (100mg, 0.17mmol, example 2B) in dichloromethane (10ml) was treated with m-chloroperbenzoic acid (80%, 80mg, 0.37 mmol). After stirring at ambient temperature for 18 h, the reaction mixture was diluted with dichloromethane (40ml) and then washed three times with saturated aqueous sodium bicarbonate solution (20 ml). The organic phase is dried over magnesium sulfate and then concentrated under vacuum. The residue was chromatographed on silica gel eluting with a mixture of dichloromethane and methanol (98: 2, v/v) to give N, N-bis- (tert-butoxycarbonyl) -3- [1- (1-oxo-5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl]Benzylamine, colorless oil (70 mg). This material was dissolved in ethyl acetate (10ml), and the mixture was evaporatedThe solution was cooled to 0 ℃, then saturated with hydrogen chloride gas, then stirred at ambient temperature for 4 hours, then concentrated to dryness under vacuum. The residue was treated with ethyl acetate (10ml) and the solvent was removed in vacuo. This procedure was repeated twice to give the title compound as a white solid (45 mg).¹H NMR[(CD₃)₂SO，500MHz]：δ8.39(s，1H)，8.30(s，1H)，7.45(s，1H)，7.40(s，1H)，7.38-7.18(m，8H)，4.59(br m，1H)，4.00(m，2H)，3.50(br m，1H)，3.20(br m，1H)，2.98(s，4H)，2.85(br m，2H)，1.84(br m，1H)，1.68(br m，3H).MS(EI)：416(M⁺+H).

Example 4

3- [1- (quinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -quinolin-3-yl-methanone dihydrochloride)

The title compound was prepared as a white amorphous solid by proceeding in a similar manner to the method described in example 1, but using quinoline-3-carboxylic acid instead of 5-phenylethynyl-pyridine-3-carboxylic acid.

¹H NMR[(CD₃)₂SO，500MHz]：δ9.10(s，1H)，8.78(s，1H)，8.20(m，2H)，7.98(m，1H)，7.80(m，1H)，7.50(s，1H)，7.35(m，3H)，4.72(br m，1H)，4.00(m，2H)，3.80(br m，1H)，3.30(br m，1H)，2.90(br m，2H)，1.90(brm，1H)，1.75(br m，3H).MS(EI)：346(M⁺+H).

Example 5

3- [1- (3-phenylethynyl-benzoyl) -piperidin-4-yl ] -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (3-phenylethynyl-phenyl) -methanone hydrochloride)

N, N-bis- (tert-butyloxycarbonyl) -3- [1- (3-ethynyl-benzoyl) -piperidin-4-yl ] -benzylamine

In a similar manner to the procedure described in example 1C, but using 3-ethynylbenzoic acid (prepared according to the procedures described in c.eabom et al, j.chem.soc. (british chemical society) C, 1967, (15), p.1364-1366) instead of 5-phenylethynyl-pyridine-3-carboxylic acid, N-bis- (tert-butoxycarbonyl) -3- [1- (3-ethynyl-benzoyl) -piperidin-4-yl ] -benzylamine was prepared as a white amorphous solid.

¹H NMR(CDCl₃，500MHz)：δ7.76(m，2H)，7.40(m，2H)，7.25(m，2H)，7.10(m，4H)，4.95(br m，1H)，4.79(s，2H)，3.80(br m，1H)，3.10(br m，1H)，2.84(br m，1H)，2.78(brm，1H)，1.90(m，1H)，1.75(m，3H)，1.42(s，18H).MS(EI)：541(M⁺+Na).

N, N-bis- (tert-butyloxycarbonyl) -3- [1- (3-phenylethynyl-benzoyl) -piperidin-4-yl ] -benzylamine

A mixture of N, N-bis- (tert-butoxycarbonyl) -3- [1- (3-ethynyl-benzoyl) -piperidin-4-yl ] -benzylamine (0.24g, 0.46mmol), iodobenzene (95mg, 0.46mmol), dichlorobis (triphenylphosphine) palladium (II) (35mg, 0.05mmol), copper (I) iodide (26mg, 0.14mmol), triethylamine (0.57ml, 4.1mmol) and anhydrous dimethylformamide (8ml) was stirred at ambient temperature under nitrogen for 18 h. The solvent was removed under vacuum and the residue partitioned between ethyl acetate (50ml 3 parts) and water (20 ml). The organic layers were combined, washed with brine (50ml), then dried over magnesium sulfate and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of cyclohexane and ethyl acetate (3: 2, v/v) to give N, N-bis- (tert-butoxycarbonyl) -3- [1- (3-phenylethynyl-benzoyl) -piperidin-4-yl ] -benzylamine as a yellow oil (0.23 g).

¹H NMR(CDCl₃，500MHz)：δ7.58(m，4H)，7.40(m，5H)，7.25(m，1H)，7.10(m，3H)，4.90(br m，1H)，4.79(s，2H)，3.80(br m，1H)，3.15(br m，1H)，2.84(br m，1H)，2.78(br m，1H)，1.95(m，1H)，1.80(m，3H)，1.42(s，18H).MS(EI)：617(M⁺+Na).

C.3- [1- (3-Phenylethynyl-benzoyl) -piperidin-4-yl ] -benzylamine hydrochloride

Cooling to 0 deg.C N, N-bis- (tert-butoxycarbonyl) -3- [1- (3-phenylethynyl-benzoyl) -piperidin-4-yl]A solution of-benzylamine (100mg, 0.17mmol) in methanol (10ml) was saturated with hydrogen chloride gas. The mixture was stirred at ambient temperature for 4 hours and then concentrated to dryness under vacuum. The residue was triturated with a mixture of dichloromethane and diethyl ether to give 3- [1- (3-phenylethynyl-benzoyl) -piperidin-4-yl]Benzylamine hydrochloride as a white amorphous solid (46 mg).¹H NMR[(CD₃)₂SO，500MHz]：δ7.61-7.30(m，13H)，4.62(br m，1H)，4.00(s，2H)，3.62(brm，1H)，3.25(br m，1H)，2.85(br m，2H)，1.88(br m，1H)，1.70(br m，3H).MS(EI)：395(M⁺+H).

Example 6

2- {3- [4- (3-aminomethyl-phenyl) -piperidine-1-carbonyl ] -phenyl } -1- (4-hydroxyphenyl) -ethanone (a.k.a.2- {3- [4- (3-aminomethyl-phenyl) -piperidine-1-carbonyl ] -phenyl } -1- (4-hydroxy-phenyl) -ethanone hydrochloride)

N, N-bis- (tert-butyloxycarbonyl) -3- {1- [3- (4-hydroxyphenyl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine

Prepared in a similar manner to the method described in example 5B, but using 4-iodophenol instead of iodobenzene, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (4-hydroxyphenyl) ethynyl-benzoyl]-piperidin-4-yl } -benzylamine as a yellow amorphous solid.¹H NMR(CDCl₃，500MHz)：δ7.58(m，2H)，7.40(m，4H)，7.25(m，1H)，7.15(m，3H)，6.80(m，2H)，4.90(brm，1H)，4.79(s，2H)，3.90(br m，1H)，3.15(br m，1H)，2.84(br m，1H)，2.78(br m，1H)，1.98(m，1H)，1.80(m，3H)，1.42(s，18H).MS(EI)：633(M⁺+Na).

B.2- {3- [4- (3-aminomethyl-phenyl) -piperidine-1-carbonyl ] -phenyl } -1- (4-hydroxyphenyl) -ethanone hydrochloride

By proceeding in a similar manner to the method described in example 5C, but using N, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (4-hydroxyphenyl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine, 2- {3- [4- (3-aminomethyl-phenyl) -piperidine-1-carbonyl ] -phenyl } -1- (4-hydroxyphenyl) -ethanone hydrochloride was prepared as a white amorphous solid.

¹H NMR[(CD₃)₂SO，500MHz]：δ7.92(m，2H)，7.40-7.28(m，8H)，6.82(m，2H)，4.60(br m，1H)，438(s，2H)，4.00(s，2H)，3.62(br m，1H)，3.18(brm，1H),2.80(br m，2H)，1.88(br m，1H)，1.70-1.60(br m，3H)，MS(EI)：429(M⁺+H).

Example 7

3- {1- [3- (6-amino-pyridin-3-yl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [3- (6-amino-pyridin-3-ylethynyl) -phenyl ] methanone hydrochloride)

A.3-iodo-6- (tert-butoxycarbonylamino) pyridine

To a stirred solution of 6-amino-3-iodopyridine (0.44g, 2.0mmol) in anhydrous tetrahydrofuran (7ml) under nitrogen was added dropwise a solution of sodium bis (trimethylsilyl) amide (1M, 4.4ml, 4.4 mmol). After further stirring for 15 minutes, the mixture was treated with a solution of di-tert-butyl dicarboxylate (440mg, 2mmol) in anhydrous tetrahydrofuran (3 ml). The resulting concentrated slurry was stirred at ambient temperature for 18 hours and then partitioned between ethyl acetate (50ml 3 parts) and water (50 ml). The organics were combined, dried over sodium sulfate, and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of cyclohexane and ethyl acetate (9: 1, v/v) to give 3-iodo-6- (tert-butoxycarbonylamino) pyridine as a white solid (0.56 g).

¹H NMR(CDCl₃，500MHz)δ8.50(s，1H)，7.92(m，1H)，7.85(m，1H)，1.58(s，9H).MS(EI)：319(M⁺-H).

N, N-bis- (tert-butyloxycarbonyl) -3- {1- [3- (6-tert-butyloxycarbonylamino-pyridin-3-yl) ethynylbenzoyl ] -piperidin-4-yl } -benzylamine

By proceeding in a similar manner to the method described in example 5B, but using 3-iodo-6- (tert-butoxycarbonylamino) pyridine instead of iodobenzene, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (6-tert-butoxycarbonylamino-pyridin-3-yl) ethynyl-benzoyl ] -piperidin-4-yl } benzylamine was prepared as a yellow amorphous solid.

¹H NMR(CDCl₃，500MHz)：δ8.41(s，1H)，7.99(m，1H),7.80(m，1H)，7.61(s，1H)，7.59(m，2H)，7.40(m，2H)，7.23(m，1H)，7.12(m，3H)，4.90(br m，1H)，4.79(s，2H)，3.84(br m，1H)，3.15(br m，1H)，2.84(br m，1H)，2.78(br m，1H)，1.95(m，1H)，1.80(m，3H)，1.55(s，9H)，1.42(s，18H).MS(E)：710(M⁺).

3- {1- [3- (6-amino-pyridin-3-yl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride

By proceeding in a similar manner to the method described in example 5C, but using N, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (6-tert-butoxycarbonylamino-pyridin-3-yl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine, 3- {1- [3- (6-amino-pyridin-3-yl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride was prepared as a white amorphous solid.

¹H NMR[(CD₃)₂SO，500MHz]：δ8.22(s，1H)， 8.15(br s，2H)，7.90(m，1H)，7.60-7.41(m，5H)，7.30(m，3H)，6.93(m，1H)，4.60(br m，1H)，4.00(m，2H)，3.62(br m，1H)，3.25(br m，1H)，2.85(br m，2H)，1.84(br m，1H)，1.60(br m，3H).MS(EI)：411(M⁺+H).

Example 8

3- {1- [3- (4-hydroxymethylphenyl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [3- (4-hydroxymethyl-phenylethynyl) -phenyl ] -methanone hydrochloride)

The procedure was carried out in a similar manner to that described in example 5, butThe title compound was prepared as a white amorphous solid using 4-iodobenzyl alcohol (prepared according to the procedures described in d.s.tan et al, j.am.chem.soc. (american chemical society), 1998, 120(33), p.8565-8566) instead of iodobenzene.¹H NMR[(CD₃)₂SO，500MHz]：δ7.61-7.25(m，12H)，5.33(m，1H)，4.62(br m，1H)，4.58(m，2H)，4.00(s，2H)，3.62(brm，1H)，3.20(br m，1H)，2.83(br m，2H)，1.84(br m，1H)，1.72-1.62(br m，3H).MS(EI)：425(M⁺+H).

Example 9

3- [1- (3-phenethyl-benzoyl) -piperidin-4-yl ] -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (3-phenethyl-phenyl) -methanone hydrochloride)

A solution of N, N-bis- (tert-butoxycarbonyl) -3- [1- (3-phenylethynyl-benzoyl) -piperidin-4-yl ] -benzylamine (110mg, 0.18mmol, example 5B) in ethanol (10ml) was treated with 10% palladium on carbon (20mg) and then stirred at ambient temperature under a hydrogen atmosphere for 8 hours. The reaction mixture was filtered through a short hyflo pad and then concentrated under vacuum to give a white amorphous solid (0.54 g). This material was treated with a solution of hydrogen chloride in methanol according to the procedure described for example 5C to give the title compound as a white amorphous solid (25 mg).

¹H NMR[(CD₃)₂SO，500MHz]：δ7.40-7.15(m，13H)，4.62(br m，1H)，4.00(s，2H)，3.60(br m，1H)，3.10(br m，1H)，2.80(br m，2H)，1.85(br m，1H)，1.60(br m，3H)，MS(EI)：399(M⁺+H).

Example 10

3- {1- [3- (4-hydroxyphenyl) ethyl-benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - {3- [2- (4-hydroxy-phenyl) -ethyl ] -phenyl } -methanone hydrochloride)

The procedure was carried out in a similar manner to the procedure described in example 9, but using N, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (4-hydroxyphenyl) ethyl esterAlkynyl-benzoyl]-piperidin-4-yl } -benzylamine (example 6A) the title compound was prepared as a white amorphous solid.¹H NMR[(CD₃)₂SO，500MHz]：δ9.18(br s，1H)，7.41(s，1H)，7.35(m，5H)，7.20(m，2H)，6.98(m，2H)，6.60(m，2H)，4.82(br m，1H)，4.00(m，2H)，3.80(br m，1H)，3.10(br m，1H)，2.80(m，6H)，1.82(br m，1H)，1.70(br m，1H)，1.60(br m，2H).MS(EI)：415(M⁺+H).

Example 11

3- {1- [3- (6-amino-pyridin-3-yl) ethyl-benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - {3- [2- (6-amino-pyridin-3-yl) -ethyl ] -phenyl } -methanone hydrochloride)

In a similar manner to the process described in example 9, but using N, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (6-tert-butoxycarbonylamino-pyridin-3-yl) ethynyl-benzoyl]-piperidin-4-yl } benzylamine (example 7B) the title compound was prepared as a white amorphous solid.¹HNMR[(CD₃)₂SO，500MHz]：δ7.90(br s，2H)，7.85(m，1H)，7.76(s，1H)，7.43(s，1H)，7.40-730(m，5H)，7.24(m，2H)，6.93(m，1H)，4.61(br m，1H)，4.00(m，2H)，3.60(br m，1H)，3.15(br m，1H)，2.92(brm，6H)，1.90(br m，1H)，1.70(br m，1H)，1.60(br m，2H).MS(EI)：415(M⁺+H).

Example 12

3- [1- (4-phenethyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (4-phenethyl-thiophen-2-yl) -methanone hydrochloride)

The title compound was prepared in a similar manner to the method described in example 1, but using 4-phenethylthiophene-2-carboxylic acid (prepared according to the procedure described in S.Gronowitz et al, Heterocycles, 1981, 15(2), p.947-959) instead of 5-phenylethynyl-pyridine-3-carboxylic acid.¹H NMR[(CD₃)₂SO，500MHz]：δ7.41-7.18(m，11H)，4.37(br m，1H)，4.00(m，2H)，3.05(br m，2H)，2.98(s，4H)，2.85(br m，2H)，1.90(br m，2H)，1.60(br m，2H)，MS(EI)：405(M⁺+H).

Example 13

3- [1- (5-phenethyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (5-phenethyl-thiophen-2-yl) -methanone hydrochloride)

The title compound was prepared in a similar manner to the method described in example 2, but using 5-phenylethynyl-thiophene-2-carboxylic acid instead of 5-phenylethynyl-pyridine-3-carboxylic acid.¹H NMR[(CD₃)₂SO，500MHz]：δ7.41(s，1H)，7.38-7.20(m，9H)，6.83(s，1H)，4.40(br m，1H)，4.00(br s，2H)，3.12(m，2H)，3.08(brm，2H)，2.98(m，2H)，2.85(br m，2H)，1.82(br m，2H)，1.60(br m，2H)，MS(EI)：405(M⁺+H).

Example 14

3- {1- [3- (benzoxazol-2-yl) -benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (3-benzoxazol-2-yl-phenyl) -methanone hydrochloride)

The title compound was prepared in a similar manner to the method described in example 1, but using 3- (benzoxazol-2-yl) -benzoic acid (prepared according to the procedure described in v.f.bystrov et al, zh.obshch.khim. (journal of common chemistry), 1968, 38(5), p.1001-1005) instead of 5-phenylethynyl-pyridine-3-carboxylic acid.

¹H NMR[(CD₃)₂SO，500MHz]：δ8.28(m，1H)， 8.19(s，1H)，7.81(m，2H)，7.50(m，2H)，7.43(m，3H)，7.30(m，3H)，4.66(br m，1H)，4.00(m，2H)，3.70(br m，1H)，3.25(br m，1H)，2.92(br m，1H)，2.82(br m，1H)，1.90(br m，1H)，1.70(br m，3H)，MS(EI)：412(M⁺+H).

Example 15

3- [1- (3-phenoxymethyl-benzoyl) -piperidin-4-yl ] -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (3-phenoxymethyl-phenyl) -methanone hydrochloride)

The title compound was prepared in a similar manner to the method described in example 1, but using 3-phenoxymethyl-benzoic acid (prepared according to the procedure described in h.oelschlaeger et al, arch.pharm. (pharmaceutical literature) (Weinheim, Ger.), 1978, 311(2), p.81-97) instead of 5-phenylethynyl-pyridine-3-carboxylic acid.¹H NMR[(CD₃)₂SO，500MHz]：δ7.58-7.25(m，10H)，7.00(m，2H)，6.96(m，1H)，5.18(s，2H)，4.62(br m，1H)，4.00(m，2H)，3.62(br m，1H)，3.18(br m，1H)，2.82(br m，2H)，1.88(br m，1H)，1.65(br m，3H)，MS(EI)：401(M⁺+H).

Example 16

3- {1- [3- (2-E-phenylvinyl) -benzoyl ] -piperidin-4-yl } -benzylamine hydrochloride (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [3- ((E) -styryl) -phenyl ] -methanone hydrochloride)

The title compound was prepared in a similar manner to the procedure described in example 1, but using 3- (2-E-phenylvinyl) -benzoic acid (prepared according to the procedure described in n.a. bumagin et al, zh.org.khim. (journal of organic chemistry), 1995, 31(4), p.481-487) instead of 5-phenylethynyl-pyridine-3-carboxylic acid as a white amorphous solid.

¹H NMR[(CD₃)₂SO，500MHz]：δ7.71(m，1H)，7.63(m，3H)，7.50(m，2H)，7.40-7.25(m，9H)，4.63(br m，1H)，4.00(s，2H)，3.71(br m，1H)，3.10(br m，1H)，2.84(br m，2H)，1.88(br m，1H)，1.70(br m，3H)，MS(EI)：397(M⁺+H).

Example 17

4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (a.k.a. [4- (5-aminomethyl-2-fluoro-phenyl) -piperidin-1-yl ] - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride)

4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine trifluoroacetate salt

To a solution of lithium diisopropylamide (59mmol) in anhydrous tetrahydrofuran (50ml) was added dropwise a solution of tert-butyl 4-oxo-1-piperidinecarboxylate (10.7g, 54mmol) in anhydrous tetrahydrofuran (70ml) at-78 ℃. After further stirring at-78 ℃ for 20 minutes, the reaction mixture was treated with a solution of N-phenyltrifluoromethanesulfonimide (21.2g, 59mmol) in dry tetrahydrofuran (90 ml). The resulting orange suspension was warmed to 0 ℃, then stirred at 0 ℃ for 3 hours, then concentrated under vacuum. The residue was chromatographed on silica gel eluting with a mixture of pentane and dichloromethane (1: 1, v/v) and then on alumina eluting with a mixture of pentane and ethyl acetate (9: 1, v/v) to give 1, 2, 3, 6-tetrahydro-4- (trifluoromethanesulfonyloxy) -pyridine-1-carboxylic acid tert-butyl ester as a yellow oil (15 g). A portion of this material (1.72g, 5.2mmol) was dissolved in anhydrous dioxane (30ml) and the solution was treated with bis (pinacolato) diboron (1.46g, 5.75mmol), potassium acetate (1.54g, 15.7mmol), (diphenylphosphino) -ferrocene (86mg, 0.16mmol) and [1, 1' -bis- (diphenylphosphino) ferrocenyl ] -dichloropalladium (II) (114mg, 0.16 mmol). The reaction mixture was heated at 80 ℃ under nitrogen for 18 hours, then cooled, and then concentrated under vacuum. The residue was partitioned between ethyl acetate (100ml 2 parts) and water (100 ml). The organic extracts were combined, dried over magnesium sulfate and then concentrated in vacuo. The oil was chromatographed on silica gel eluting with a mixture of ethyl acetate and pentane (1: 8, v/v) to give a yellow oil (1.4 g). A solution of the material in dichloromethane (10ml) cooled to 0 ℃ was treated with trifluoroacetic acid (3.9 ml). The mixture was stirred at ambient temperature for 2 hours and then concentrated in vacuo to give 4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine trifluoroacetate as a brown oil.

¹H NMR[(CD₃)₂SO，500MHz]：δ8.76(br s，2H)，6.39(br s，1H)，3.61(br m，2H)，3.11(br m，2H)，2.23(br m，2H)，1.20(s 12H).MS(EI)：210(M⁺+H).

1- (5-phenethyl-pyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine

A solution of 5-phenethyl-pyridine-3-carboxylic acid (0.46g, 2.0mmol, example 2A) in anhydrous dimethylformamide (9ml) was treated with O- (7-azabenzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium hexafluorophosphate (0.87g, 2.2mmol) and diisopropylethylamine (1.7ml, 10 mmol). The mixture was stirred at ambient temperature for 10 minutes and then treated with a solution of 4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine trifluoroacetate (0.81g, 2.5mmol) in dimethylformamide (9 ml). The reaction mixture was stirred at ambient temperature for 18 hours and then concentrated in vacuo. The residue was partitioned between dichloromethane (50ml 2 parts) and saturated aqueous sodium bicarbonate (15 ml). The organic layers were combined, dried over magnesium sulfate, and then concentrated in vacuo. The residue was chromatographed on silica gel eluting with ethyl acetate to give 1- (5-phenethyl-pyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine as a brown amorphous solid (0.73 g).¹H NMR[(CD₃)₂SO，500MHz]：δ8.49(s，1H)，8.40(s，1H)，7.61(s，1H)，7.20(m，5H)，6.48(br s，1H)，4.18(br m，1H)，3.83(br m，1H)，3.62(br m，1H)，3.23(br m，1H)，2.98(m，4H)，2.17(br m，2H)，1.20(s，12H).MS(EI)：441(M⁺+Na).

C.N- (tert-Butoxycarbonyl) -3-bromo-4-fluoro-benzylamine

A mixture of 3-bromo-4-fluoro-benzylamine hydrochloride (2.41g, 10mmol), triethylamine (2.8ml, 20mmol) and di-tert-butoxycarbonate (1.8g, 10.3mmol) in dichloromethane (20ml) was stirred at ambient temperature for 18 h and then washed with water (20 ml). The organic phase is dried over magnesium sulfate and then concentrated under vacuum. Subjecting the residue to silica gel chromatography with cyclohexaneA mixture of alkane and ethyl acetate (3: 1, v/v) was eluted to give N- (tert-butoxycarbonyl) -3-bromo-4-fluoro-benzylamine as a white solid (1.4 g).¹H NMR(CDCl₃，500MHz)：δ7.45(m，1H) 7.20(m，1H)，7.08(m，1H)，4.85(br s，1H)，4.21(m，2H)，1.42(s，9H).

D.N- (tert-Butoxycarbonyl) -4-fluoro-3-1- (5-phenethyl-pyridine-3-carbonyl) -1, 2, 3, 6-tetrahydropyridin-4-yl ] -benzylamine

N- (tert-Butoxycarbonyl) -3-bromo-4-fluoro-benzylamine (0.28g, 0.92mmol), anhydrous dimethylformamide (10ml), 1- (5-phenethyl-pyridine-3-carbonyl) -4- (pinacolato-boronyl) -1, 2, 3, 6-tetrahydro-pyridine (0.37g, 0.88mmol), potassium carbonate (0.36g, 2.6mmol) and [1, 1' -bis (diphenylphosphino) ferrocenyl]A mixture of dichloropalladium (II) -dichloromethane complex (43mg, 0.05mmol) was heated at 80 ℃ under nitrogen for 18 h. The reaction mixture was cooled to room temperature and then concentrated under vacuum. The residue was partitioned between ethyl acetate (50ml 2 parts) and water (10 ml). The organic extracts were combined, dried over magnesium sulfate and then concentrated in vacuo. Subjecting the resulting oil to silica gel chromatography, eluting with ethyl acetate, to give N- (tert-butoxycarbonyl) -4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -1, 2, 3, 6-tetrahydro-pyridin-4-yl]Benzylamine as a pale yellow oil (0.18 g).¹HNMR(CDCl₃，500MHz)：δ8.58(s，1H)，8.50(s，1H)，7.51(s，1H)，7.25(m，2H)，7.18(m，5H)，7.00(m，1H)，6.01(br s，1H)，4.83(br s，1H)，4.38(br m，1H)，4.27(m，2H)，3.98(br m，2H)，3.50(br m，1H)，2.99(m，4H)，2.60(br m，1H)，2.50(br m，1H).MS(EI)：538(M⁺+Na).

E.4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride

A solution of N- (tert-butoxycarbonyl) -4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -1, 2, 3, 6-tetrahydro-pyridin-4-yl ] -benzylamine in ethanol (12ml) was treated with 10% palladium on carbon (75mg), and the mixture was stirred at ambient temperature under a hydrogen atmosphere for 72 hours. The reaction mixture was filtered through a short hyflo pad and the filtrate was concentrated in vacuo to give N- (tert-butoxycarbonyl-4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine as a colourless oil (85 mg). this material was dissolved in methanol (10ml), the solution was cooled to 0c, the mixture was then saturated with hydrogen chloride gas, stirred at ambient temperature for 4 hours and then concentrated to dryness in vacuo the residue was triturated with a mixture of dichloromethane and diethyl ether to give 4-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride as a white amorphous solid (50 mg).

¹H NMR[(CD₃)₂SO，500MHz]：δ8.60(s，1H)，8.58(s，1H)，7.83(s，1H)，7.60(m，1H)，738(m，1H)，7.20(m，6H)，4.61(br m，1H)，4.00(m，2H)，3.50(br m，1H)，3.20(br m，2H)，2.99(m，2H)，2.95(m，2H)，2.90(br m，1H)，1.82(br m，1H)，1.65(br m，3H).MS(EI)：418(M⁺+H).

Example 18

4-methyl-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (a.k.a. [4- (5-aminomethyl-2-methyl-phenyl) -piperidin-1-yl ] - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride)

A.4- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -2-bromo-toluene

To a solution of 4-methyl-3-bromobenzyl bromide (1.63g, 6.2mmol, prepared according to the procedure described in International patent application No. WO 00/09475) and di-tert-butyliminodicarboxylate (1.48g, 6.8mmol) in dry tetrahydrofuran (15ml) was added dropwise sodium hydride (0.27g of a 60% dispersion in mineral oil, 6.8 mmol). The mixture was stirred at ambient temperature for 18 hours and then partitioned between saturated aqueous ammonium chloride (20ml) and ethyl acetate (80ml 3 parts). The organic layers were combined, washed with brine (80ml), then dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel, eluting with a mixture of cyclohexane and diethyl ether (9: 1, v/v) to give 4- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]-2-bromo-toluene as a pale yellow oil (2.4 g).¹H NMR(CDCl₃，500MHz)：δ7.45(s，1H)，7.18(m，2H)，4.71(s，2H)，2.38(s，3H)，1.43(s，18H).

B.4-methyl-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride

The procedure was carried out in a similar manner to the procedure described in example 17, but using 4- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]Preparation of 4-methyl-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzyl-amine by substituting N- (tert-butoxycarbonyl) -3-bromo-4-fluoro-benzylamine with (2-bromo-toluene]Benzylamine dihydrochloride, as a white amorphous solid.¹H NMR[(CD₃)₂SO，500MHz]：δ8.60(m，2H)，7.83(s，1H)，7.41(s，1H)，7.20(m，7H)，4.62(br m，1H)，3.98(m，2H)，3.45(br m，1H)，3.20(br m，1H)，3.07(m，2H)，3.00(m，2H)，2.95(m，2H)，2.32(s，3H)，1.80(br m，1H)，1.70(br m，3H).MS(EI)：414(M⁺+H).

Example 19

3- {1- [3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -phenylcarbonyl ] -piperidin-4-yl } -benzylamine hydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -phenyl ] methanone hydrochloride)

3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -benzoic acid

A mixture of methyl isophthalate (1.8g, 10mmol), benzoyl hydrazine (1.4g, 10mmol) and phosphorus oxychloride (20ml) was heated at 120 ℃ for 18 hours under nitrogen, then cooled to room temperature and poured into ice water (500 ml). The mixture was treated with solid sodium carbonate until the aqueous layer was basic (pH 8-9) and the resulting pink solid was filtered. The material was treated with 100ml of methanol and the suspension treated with sodium hydroxide solution (30ml, 1M). The reaction mixture was heated at reflux for 4 hours, then cooled, and then concentrated to dryness. The residue was dissolved in water (100ml) and the solution acidified to pH 3 by addition of concentrated HCl. The resulting precipitate was filtered, then dried and then chromatographed on silica gel, eluting with a mixture of dichloromethane and methanol (98: 2, v/v) to give 3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -benzoic acid as a white solid (600 mg).

¹H NMR[(CD₃)₂SO，500MHz]：δ8.80(s，1H)，8.38(m，1H)，8.18(m，3H)，7.78(m，1H)，7.62(m，3H).MS(EI)：265(M⁺-H).

B.3- {1- [3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -phenylcarbonyl ] -piperidin-4-yl } -benzylamine hydrochloride

Prepared in a similar manner to the method described in example 1, but using 3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -benzoic acid in place of 5-phenylethynyl-pyridine-3-carboxylic acid 3- {1- [3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -phenylcarbonyl]-piperidin-4-yl } -benzylamine hydrochloride as a light yellow amorphous solid.¹H NMR[(CD₃)₂SO，500MHz]：δ8.21(m，1H)，8.20(m，3H)，7.75(m，2H)，7.68(m，3H)，7.50(s，1H)，7.37(m，3H)，4.70(br m，1H)，4.00(m，2H)，3.70(br m，1H)，3.25(br m，1H)，2.90(br m，1H)，2.85(br m，1H)，1.88(br m，1H)，1.70(m，3H)，MS(EI)：439(M⁺+H).

Example 20

3- [1- (indole-6-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (1H-indol-6-yl) -methanone trifluoroacetate)

In a glass vial, a solution of diisopropylamine in dimethylformamide (1ml, 180. mu.M) was treated with a solution of O- (7-azabenzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium hexafluorophosphate in dimethylformamide (1ml, 60. mu.M) and then with a solution of indole-6-carboxylic acid in dimethylformamide (1ml, 60. mu.M). After 15 minutes at ambient temperature, the mixture was treated with a solution of 4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidine in dimethylformamide (1ml, 60. mu.M, example 1B). The reaction mixture was left at ambient temperature for 18 hours and then evaporated. The residue was treated with chloroform (5ml) and aqueous sodium carbonate (5%). The mixture was shaken gently for 30 minutes, poured into a sintered polypropylene tube, and the organic layer that penetrated the glass frit was collected in a glass vial. Chloroform was evaporated under vacuum and the residue was treated with trifluoroacetic acid, a mixture of dichloromethane and water (4ml, 55/40/5, v/v/v). The mixture was shaken gently for 2 hours and then evaporated to give the title compound as a yellow oil.

LC-MS：R_T3.43 min (> 96% by ELSD); MS (ES)⁺)334(MH⁺).

Example 21

3- [1- (coumarin-3-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A.3- [4- (3-aminomethyl-phenyl) -piperidine-1-carbonyl ] -1-benzopyran-2-one trifluoroacetate)

The title compound was prepared in a yellow oil by proceeding in a similar manner to the method described in example 20, but using coumarin-3-carboxylic acid instead of indole-6-carboxylic acid.

LC-MS：R_T3.15 minutes; (> 86% by ELSD); MS (ES)⁺)，363(MH⁺).

Example 22

3- [1- (naphthyl-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -naphthalen-2-yl-methanone trifluoroacetate)

The title compound was prepared in a yellow oil by proceeding in a similar manner to the method described in example 20, but using 2-naphthoic acid instead of indole-6-carboxylic acid.

LC-MS：R_T3.66 minutes; (100% by ELSD); MS (ES)⁺)，345(MH⁺).

Example 23

3- {1- [3- (2-Naphthalylthio) propionyl ] -piperidin-4-yl } -benzylamine trifluoroacetate (A.K.A.1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3- (naphthalen-2-ylsulfanyl) -propan-1-one trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using 3- (2-naphthylthio) propionic acid instead of indole-6-carboxylic acid as yellow oil.

LC-MS：R_T4.00 min (> 95% by ELSD); MS (ES)⁺)，405(MH⁺).

Example 24

3- {1- [4- (indol-3-yl) butyryl ] -piperidin-4-yl } -benzylamine trifluoroacetate (A.K.A.1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -4- (1H-indol-3-yl) -butan-1-one trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using 4- (indol-3-yl) butyric acid instead of indole-6-carboxylic acid as a yellow oil.

LC-MS：R_T3.64 min (> 90% by ELSD); MS (ES)⁺)，376(MH⁺).

Example 25

3- {1- [4- (4-biphenyl) -4-ketobutyryl ] -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -biphenyl-4-yl-methanone trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using 4- (4-biphenyl) -4-ketobutyric acid instead of indole-6-carboxylic acid as a yellow oil.

LC-MS：R_T4.00 min; (100% by ELSD); MS (ES)⁺)，427(MH⁺).

Example 26

3- [1- (3-benzyloxybenzoyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (3-benzyloxy-phenyl) -methanone trifluoroacetate)

The title compound was prepared in a yellow oil by proceeding in a similar manner to the method described in example 23, but using 3-benzyloxybenzoic acid instead of indole-6-carboxylic acid.

LC-MS：R_T3.87 min (100% by ELSD); MS (ES)⁺)，401(MH⁺).

Example 27

3- [1- (5-phenylethynyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (5-phenylethynyl-thiophen-2-yl) -methanone trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using 5-phenylethynyl-thiophene-2-carboxylic acid instead of indole-6-carboxylic acid.

LC-MS：R_T4.09 min (> 97% by ELSD); MS (ES)⁺)，410(MH⁺).

Example 28

3- [1- (4-phenylethynyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (4-phenylethynyl-thiophen-2-yl) -methanone trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using 4-phenylethynyl-thiophene-2-carboxylic acid instead of indole-6-carboxylic acid.

LC-MS：R_T4.08 min; (> 96% by ELSD); MS (ES)⁺)，401(MH⁺).

Example 29

3- (1-benzoyl-piperidin-4-yl) -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -phenyl-methanone trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using benzoic acid instead of indole-6-carboxylic acid as a yellow oil.

R_T3.39 min (> 95% by ELSD); MS (ES)⁺)295(MH⁺).

Example 30

3- [1- (4-N, N-dimethylaminobenzoyl) -piperidin-4-yl ] -benzylamine trifluoroacetate (A.K.A. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (4-dimethylamino-phenyl) -methanone trifluoroacetate)

The title compound was prepared in a similar manner to the method described in example 20, but using 4-N, N-dimethylaminobenzoic acid instead of indole-6-carboxylic acid as a yellow oil.

LC-MS：R_T3.32 minutes (100% by ELSD); MS (ES)⁺)338(MH⁺).

Example 31

6-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (A.K.A. [4- (3-aminomethyl-4-fluoro-phenyl) -piperidin-1-yl ] - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride)

The title compound was prepared as a pale yellow oil by proceeding in a similar manner to the method described in example 17, but using 3-bromo-6-fluoro-benzylamine instead of 3-bromo-4-fluoro-benzylamine.

¹H NMR[(CD₃)₂SO，500MHz]：δ8.44(m，2H)，7.61(s，1H)，7.40(m，1H)，7.20(m，6H)，7.05(m，1H)，4.62(br m，1H)，3.98(m，2H)，3.45(br m，1H)，3.20(br m，1H)，3.07(m，2H)，3.00(m，2H)，2.95(m，2H)1.80(br m，1H)，1.70(br m，3H).MS(EI)：418(M⁺+H).

Example 32

1- {3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -phenyl) ethylamine dihydrochloride (A.K.A. {4- [3- (1-amino-ethyl) -phenyl ] -piperidin-1-yl } - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride)

The title compound was prepared in a similar manner to the method described in example 17, but using 1- (3-bromophenyl) ethylamine (prepared according to the procedure described in c.p. chen et al, Tetrahedron Letters, 199, 32(49), p.7175-7178) instead of 3-bromo-4-fluoro-benzylamine.

¹H NMR[(CD₃)₂SO，500MHz]：δ8.62(m，2H)，7.95(s，1H)，7.50(s，1H)，7.20(m，8H)，4.62(br m，1H)，4.38(t，J＝6Hz，1H)，3.50(m，1H)，3.45(br m，1H)，3.20(br m，1H)，3.07(m，2H)，3.00(m，2H)，2.95(m，2H)，1.87(br m，1H)，1.65(br m，3H)，1.50(d，J＝6Hz，3H).MS(EI)：414(M⁺+H).

Example 33

3- [1- (4-hydroxy-quinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (4-hydroxy-quinolin-3-yl) -methanone)

The title compound was prepared in a similar manner to the method described in example 1, but using 4-hydroxyquinoline-3-carboxylic acid (prepared according to the procedures described in k.j.shah and e.a.coats, j.med.chem. (journal of medicinal chemistry), 1977, 20(8), p.1001-1006) instead of 5-phenylethynyl-pyridine-3-carboxylic acid.

¹H NMR[(CD₃)₂SO，500MHz]：δ8.10(m，2H)，7.68(m，1H)，7.59(m，1H)，7.36(m，3H),7.22(m，2H),4.65(br m，1H),4.00(m，2H)，3.80(br m，1H)，3.35(br m，1H)，3.10(br m，1H)，3.00(brm，1H)，1.90-1.75(br m，4H).MS(EI)：362(M⁺+H).

Example 34

3- [1- (6-phenyl-quinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride (a.k.a. [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - (6-phenyl-quinolin-3-yl) -methanone dihydrochloride)

The title compound was prepared in a similar manner to the method described in example 1, but using 6-phenylquinoline-3-carboxylic acid (prepared according to the procedure described in j.biwersi et al, am.j.physiol. (journal of physiology in usa), 1992, 262(1, pt.1), C243-C250) instead of 5-phenylethynyl-pyridine-3-carboxylic acid.

¹H NMR[(CD₃)₂SO，500MHz]：δ9.00(s，1H)，8.59(s，1H)，8.41(s，1H)，8.10(m，2H)，7.85(m，2H)，7.58(m，2H)，7.45(m，2H)，7.34(m，3H)，4.75(br m，1H)，4.00(m，2H)，3.80(br m，1H)，3.35(br m，1H)，3.00(br m，1H)，2.90(br m，1H)，1.90-1.75(br m，4H).MS(EI)：422(M⁺+H).

Example 35

4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-4-carbonitrile

A.3-cyanobenzylnitriles

To a 50ml aqueous solution of 9.8g (200mmol) sodium cyanide and 1.61g (5mmol) tetrabutylammonium bromide was added a solution of 19.61g (100mmol) α -bromo-m-tolunitrile in 150ml dichloromethane. The mixture was stirred at room temperature for 24 hours. To this mixture was added 6.2ml (100mmol) of methyl iodide. The mixture was stirred at room temperature for 3 hours. The layers were separated and the organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue triturated with petroleum ether and the insolubles collected to give 14.5g of a white solid, mp-66-9 ℃ in 100% yield:¹H-NMR(300MHz，CDCl₃)δ(TMS)3.80-3.90(s，2H)，7.49-7.72(m，4H).

N-Boc-bis (2-chloroethyl) amine

A mixture of 17.85g (100mmol) of bis (2-chloroethyl) amine hydrochloride and 24.0g (110mmol) of di-tert-butyldicarbonate in 100ml of dichloromethane is added dropwise over the course of 30 minutes to a solution of 15.3ml (110mmol) of triethylamine in 50ml of dichloromethane. The mixture was stirred at room temperature for 24 hours and poured into water. The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated to give 24g of oil in 100% yield:

¹H-NMR(300MHz，CDCL₃)δ(TMS)1.37-1.56(m，9H)，3.50-3.62(m，8H)；MS(ESI)m/e 242(M+H)⁺.

c.4- (3-cyanophenyl) -1-tert-butoxycarbonyl-piperidine-4-carbonitrile

To a solution of 2.8g (19.7mmol) of 3-cyanobenzonitrile and 4.77g (19.7mmol) of N-tert-butylcarbonyl-bis (2-chloroethyl) amine in 100ml of anhydrous DMF was added 2.36g (59.1mmol) of 60% sodium hydride portionwise over a period of 10 minutes. The mixture was stirred at room temperature for 3 days, poured into water and extracted with ether. The ether layer was dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue was purified by flash chromatography, eluting with 4: 1 hexane: ethyl acetate to give the product as a white solid:¹H-NMR(300MHz，CDCl₃)δ(TMS)1.45(s，9H)，1.85-2.0(m，2H)，2.0-2.28(m，2H)，3.05-3.30(m，2H)，4.12-4.4(m，2H)，7.53-7.80(m，4H).

4- (3-aminomethyl-phenyl) -1-tert-butoxycarbonyl-piperidine-4-carbonitrile

To a mixture of 0.31g (1mmol)4- (3-cyanophenyl) -1-tert-butoxycarbonyl-piperidine-4-carbonitrile in 30ml absolute ethanol was added 0.08ml (1mmol) concentrated hydrochloric acid followed by 30mg 5% Pd/C. The mixture was stirred in a Parr shaker for 3 hours in the presence of 30lbs of hydrogen. The mixture was filtered through celite and the filtrate was evaporated. The residue was treated with ether, stirred for 30 min and filtered. The filter cake was treated with aqueous sodium carbonate and extracted with dichloromethane to give 0.2g of product:¹H-NMR(300MHz，CDCl₃)δ(TMS)1.38-1.60(m，9H)，1.88-2.18(m，4H)，3.05-3.30(m，4H)，3.79-4.0(m，2H)，7.22-7.85(m，4H)；MS(ESI)m/e 316(M+H)⁺.

e.4- (3-benzyloxycarbonylaminomethyl-phenyl) -1-tert-butoxycarbonyl-piperidine-4-carbonitrile

To a solution of 0.2g 4- (3-aminomethyl-phenyl) -1-tert-butoxycarbonyl-piperidine-4-carbonitrile in 15ml dichloromethane were added a few drops of triethylamine followed by a few drops of benzyl chloroformate. The mixture was stirred at room temperature for 1 hourPoured into an aqueous solution of sodium carbonate and extracted with dichloromethane. The organic layer was dried over magnesium sulfate and filtered. The filtrate was evaporated and the residue was used directly in the next step without further purification:¹H-NMR(300MHz，CDCL₃)δ(TMS)1.39-1.52(m，9H)，1.80-2.16(m，4H，3.08-3.42(m，4H)，4.19-4.50(m，2H)，5.08-5.13(d，2H)，7.28-7.79(m，9H)；MS(ESI)m/e450(M+H)⁺.

f.4- (3-benzyloxycarbonylaminomethyl-phenyl) -piperidine-4-carbonitrile

The residue obtained above was dissolved in dichloromethane containing 1ml of trifluoroacetic acid, and the solution was stirred at room temperature for 45 minutes. The solution was poured into aqueous sodium carbonate and extracted with dichloromethane. The organic layer was dried, evaporated and the residue purified by flash chromatography eluting with 7: 3 hexane: ethyl acetate to give the product:

¹H-NMR (300MHz，CDCL₃)δ(TMS)1.80-2.18(m，4H)，3.07-3.35(m，4H)，4.28-4.50(m，2H)，5.09-5.13(d，H)，7.10-7.77(m，9H)；MS(ESI)m/e 349(M+H)⁺.

g.4- (3-benzyloxycarbonylaminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-4-carbonitrile

To a solution of 0.15g (0.33mmol)4- (3-benzyloxycarbonylaminomethyl-phenyl) -piperidine-4-carbonitrile in 20ml acetonitrile was added 0.038g (0.33mmol) N-ethylmorpholine and then 0.11g (0.33mmol) TBTU. To this solution was added 0.075g (0.33mmol) of 5-phenethylpyridine-3-carboxylic acid in portions over 10 minutes. The mixture was stirred for 2 hours. The solution was concentrated and the residue was purified by flash chromatography, eluting with 95: 5 dichloromethane: methanol, to give 0.2g of product:

¹H-NMR(300MHz，CDCL₃)δ(TMS)1.79-2.20(m，4H)，2.70-2.82(m，4H)，2.90-3.07(m，2H)，3.15-3.70(m，2H)，4.35-4.40(d，2H)，5.07-5.25(d，2H)，7.10-7.50(m，15H)，8.42-8.58(m，2H)；MS(ESI)m/e 559(M+H)⁺.

h.4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-4-carbonitrile

To 0.15g of 4- (3-benzyloxycarbonylaminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-4-carbonitrile in 5ml of glacial acetic acid was added 1ml of 30% HBr in glacial acetic acid. The solution was stirred at room temperature for 2 hours. The solution was poured into saturated sodium carbonate solution and extracted with dichloromethane. The organic layer was dried over magnesium sulfate, filtered and evaporated. The residue was purified by rainin hplc eluting with 10-100% (acetonitrile-0.1% aqueous TFA) to give 16mg of the product as the trifluoroacetate salt:

¹H-NMR(300MHz，DMSO-d⁶)δ(TMS)；1.95-2.30(m，4H)，2.45-2.62(m，2H)，2.88-3.12(m，4H)，3.70-4.20(m，2H)，7.12-7.38(m，4H)，7.45-7.82(m，6H)，8.50-8.65(m，2H)；MS(ESI)m/e 425(M+H)⁺.

example 36

[4- (3-Aminomethylphenyl) piperidin-1-yl ] - (3, 4-dichlorophenyl) methanone trifluoroacetate salt

TFP resin (125mg of 1.25mmol/g resin, acid loading 100%, 156mmol, prepared according to the procedure described in International patent application publication No. WO 99/67228, J.M. Salvino et al) was swollen in dichloromethane (2.5ml) for 15 minutes and then treated with a solution of 4- (3-aminomethylphenyl) piperidine (40mg, 100mmol) in dichloromethane (2.5 ml). The mixture was sealed in the reaction vessel and then shaken for 8 hours. The resin was filtered and then washed with dichloromethane (2ml) (TLC (5% MeOH/EtOAc) showed a single product spot (no baseline amine)) then treated with trifluoroacetic acid (0.5 ml). After shaking for 2 hours, TLC showed no residual intermediate and the reaction mixture was evaporated. The residue (HPLC purity 97%: R)_T7.32 minutes; 10 micron C₁₈Reverse phase column (4.6mmx10cm) eluted with 10-100% acetonitrile and water containing 0.1% trifluoroacetic acid was dissolved in water (50ml) and the solution was freeze dried to give the title compound as an amorphous solid.

¹H NMR[(CD₃)₂SO]：δ8.15(br s，3H)，7.72-7.69(m，2H)，7.40(dd，1H)，7.36-7.25(m，4H)，4.66-4.51(m，1H)，4.05-3.96(m，2H)，3.69-3.48(m，1H)，3.303.11(m，1H)，2.91-2.73(m，2H)，1.90-1.54(m，4H).MS(Ion spray)：363 and365(M⁺+1).

Example 37

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (2-phenoxy-phenyl) -methanone trifluoroacetate salt

The title compound was prepared as a white amorphous solid by proceeding in a similar manner to the method described in example 36, but using a 2-phenoxybenzoic acid-derivatized TFP resin instead of a 3, 4-dichlorobenzoic acid TFP resin.¹H NMR[(CD₃)₂SO]：δ8.11(br s，3H，NH3+)；7.43-7.04(m，10H)；7.02-6.85(m，3H)；4.65-4.52(m，H)；4.05-3.90(m，2H)；3.62-3.49(m，H)；3.21-3.05(m，H)；2.86-2.66(m，2H)；1.87-1.30(m，4H).MS(Ion spray)：587(M⁺+1).

Example 38

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-methylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt

2- (1H-benzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium tetrafluoroborate (TBTU) (120mg, 0.38mmol) was added to a room temperature solution of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carboxylic acid (88mg, 0.36mmol) and diisopropylethylamine (140mg, 1.08mmol) in dimethylformamide (2ml) under nitrogen. The reaction mixture was stirred at room temperature for 10 minutes, then a solution of 4- [3- (N, N-di-tert-butoxycarbonylaminomethyl) phenyl ] piperidine (140mg, 0.36mmol) and diisopropylethylamine (140mg, 1.08mmol) in dimethylformamide (2mL) was added. The reaction mixture was stirred at room temperature for 16H, concentrated to dryness in vacuo and subjected to flash column chromatography on anhydrous silica, eluting with 50: 50 dichloromethane: ethyl acetate, to isolate 1- {1- [4- (3- (N, N-di-tert-butoxycarbonylaminomethyl) phenyl) -piperidin-1-yl ] -formyl } -3-methylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one as a colorless oil (177 mg). The intermediate was dissolved in dichloromethane (20ml), cooled at 0 ℃ and treated with trifluoroacetic acid (2 ml). The reaction mixture was stirred at room temperature under nitrogen for 2 hours and concentrated to dryness in vacuo. The residue was dissolved in 20% acetonitrile/water (containing 0.1% trifluoroacetic acid) (9ml) and purified by preparative reverse phase HPLC (C-18, 10 micron reverse phase column) eluting with 10% to 100% acetonitrile/water (containing 0.1% trifluoroacetic acid). The product fractions were combined and acetonitrile was removed in vacuo. The aqueous residue was lyophilized to give the title compound as an amorphous white solid (122mg, 64%).

¹H NMR[(CD₃)₂SO]：δ8.16(br s，3H，NH₃ ⁺)；7.41-7.24(m，4H)；4.21(br d，2H)；4.03(q，2H)；3.18-3.02(m，2H)；2.91-2.72(m，3H)；2.59(s，3H)；2.53-2.41(m，2H)；1.98-1.90(m，2H)；1.90-1.79(m，2H)；1.68-1.50(m，2H).MS(Ion spray)：415(M⁺+1).

Example 39

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (6-chloro-benzo [ b ] thiophen-2-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 6-chlorobenzo [ b ] thiophene-2-carboxylic acid (prepared according to the procedure described in international patent application No. wo 01/07436) instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylic acid.

¹H NMR[(CD₃)₂SO]：δ8.17(d，H)；8.14(br s，3H，NH₃ ⁺)；7.91(d，H)；7.73(s，H)；7.45(dd，H)；7.37(s，H)；7.35-7.24(m，3H)；4.42(br s，2H)；4.00(q，2H)；3.12(br s，2H)；2.93-2.79(m，H)；1.89-1.77(m，2H)；1.70-1.55(m，2H).MS(Ion spray)：385387(M⁺+1).

Example 40

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-1H-indol-2-yl) -methanone trifluoroacetate salt

The procedure was carried out in a similar manner to the procedure described in example 38, but using 5-chloro-1H-indole-2-carboxylic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹H NMR[(CD₃)₂SO]：δ11.78(s，H)；8.14(br s，3H，NH₃ ⁺)；7.63(s，H)；7.43-7.22(m，5H)；7.16(dd，H)；6.76(s，H)；4.55(br d，2H)；4.00(q，2H)；3.14(br s，2H)；2.94-2.80(m，H)；1.90-1.79(m，2H)；1.73-1.54(m，2H)；MS(Ion spray)：368370(M⁺+1).

EXAMPLE 41

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (8-chloro-4H-1, 5-dithia-cyclopenta [ a ] naphthalen-2-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 8-chloro-4H-1, 5-dithiacyclopenta [ a ] naphthalene-2-carboxylic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylic acid.

¹H NMR[(CD₃)₂SO]：δ8.14(br s，3H，NH₃ ⁺)；7.52(d，H)；7.44-7.23(m，7H)；4.45(s，2H)；4.43(br d，2H)；4.00(q，2H)；3.12(br s，2H)；2.95-2.80(m，H)；1.90-1.78(m，2H)；1.72-1.56(m，2H).MS(Ion spray)：453455(M⁺+1).

Example 42

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (2 ', 4' -difluoro-4-hydroxy-biphenyl-3-yl) -methanone trifluoroacetate salt

The procedure was carried out in a similar manner to the procedure described in example 38, but using diflunisal instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹H NMR[(CD₃)₂SO]：δ10.15(s，H，OH)；8.15(br s，3H，NH₃ ⁺；7.56-7.46(m，H)；7.407.22(m，7H)；7.13(td，H)；6.97(d，H)；4.64(br s，H)；3.98(q，2H)；3.51(br s，H)；3.10(br s，H)；2.88-2.71(m，H)；1.90-1.46(m，4H).MS(Ion spray)：423424(M⁺+1).

Example 43

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-methylsulfanyl-6, 7-dihydro-benzo [ c ] thiophen-1-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 3-methylsulfanyl-6, 7-dihydro-benzo [ c ] thiophene-1-carboxylic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylic acid.

¹H NMR[CDCl₃]：δ8.13(br s，3H，NH₃ ⁺)；738-730(m，H)；7.27-7.18(m，3H)；6.68(d，H) 6.11-6.04(m，H)；4.52-4.25(br m，2H)；4.01-3.93(br m，2H)；3.40-3.38(m，H)；3.12-2.97(m，H)；2.90-2.75(m，H)；2.75(t，2H)；2.43(s，3H)；2.37-2.28(m，2H)；1.97-1.81(m，2H)；1.89-1.60(m，2H).MS(Ion spray)：400(M⁺+1).

Example 44

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -6, 6-dimethyl-3-methylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt

Carried out in a similar manner to the method described in example 38, but using 6, 6-dimethyl-3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹H NMR[(CD₃)₂SO]：δ8.16(br s，3H，NH₃ ⁺；7.40-7.34(m，2H)；7.32-7.26(m，2H)；4.20(br d，2H)；4.01(br s，2H)；3.20-3.06(m，2H)；2.93-2.80(m，H)；2.67(s，2H)；2.60(s，3H)；2.38(3，2H)；1.89-1.78(m，2H)；1.67-150(m，2H)；0.98(s，H).MS(Ion spray)：444(M⁺+1).

Example 45

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (6-bromo-pyridin-3-yl) -methanone bistrifluoroacetate

A.6-Bromonicotinic acid hydrochloride

N-butyllithium (8.0ml of a 2.5M hexane solution, 20mmol) was added dropwise to a stirred solution of 2, 5-dibromopyridine (4.74g, 20mmol) in THF (100ml) at-100 ℃ under nitrogen. The reaction mixture was allowed to stand at this temperature for 30 minutes and then anhydrous carbon dioxide gas was bubbled through the reaction mixture (for 20 minutes) and warmed to-20 ℃. The reaction was quenched with 1N HCl (20ml) and brine (20ml), extracted with ethyl acetate, dried over magnesium sulfate and concentrated to dryness. 6-Bromonicotinic acid hydrochloride was isolated as a pale yellow powder (3.8g, 16 mmol).

¹H NMR[CDCl₃+CD₃OD]：δ8.86(d，1H)，8.07(dd，1H)，7.52(d，1H).MS(Ionspray)：202204(M⁺+1).

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -I- (6-bromo-pyridin-3-yl) -methanone bistrifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using 6-bromonicotinic acid hydrochloride instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylic acid.

¹H NMR[CD₃OD]：δ8.48(d，H)；7.89(dd，H)；7.82(d，H)；7.48-7.30(m，4H)；4.90-4.81(m，H)；4.15(s，2H)；3.84(br d，H)；3.46-3.36(m，H)；3.11-2.91(m，2H)；2.13-1.68(m，4H).MS(Ionspray)：374376(M⁺+1).

Example 46

6- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -2, 3-dihydro-thiazolo [3, 2-a ] pyrimidin-5-one

The title compound was prepared in a similar manner to the method described in example 38, but using 5-oxo-2, 3-dihydro-5H-thiazolo [3, 2-a ] pyrimidine-6-carboxylic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylic acid.

¹H NMR[CD₃OD]：δ7.97(s，H)；7.44-7.29(m，4H)；4.76(br d，H)；4.59-4.51(m，2H)；4.07(s，2H)；3.83(br d，H)；3.69-3.57(m，2H)；3.41-3.21(m，H)；3.02-2.85(m，2H)；2.05-1.67(m，4H).MS(Ion spray)：371(M⁺+1).

Example 47

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-chloro-phenyl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 3-chlorobenzoic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylic acid.

¹HNMR[(CD₃)₂SO]：δ8.14(br s，3H，NH₃ ⁺)；7.57-7.43(m，3H)；7.40-7.22(m，5H)；4.70-4.56(m，H)；4.01(q，2H)；3.64-3.56(m，H)；3.23-3.10(m，H)；2.91-2.79(m，2H)；1.92-1.52(m，4H).MS(Ion spray)：329and331(M⁺+1).

Example 48

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (4-chloro-phenyl) -methanone trifluoroacetate salt

The procedure was carried out in a similar manner to the process described in example 38, but using 4-chlorobenzoic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹H NMR[(CD₃)₂SO]：δ8.15(br s，3H，NH₃ ⁺)；7.53(d，2H)；7.44(d，2H)；7.40-7.23(m，4H)；4.64-4.56(m，H)；4.02(q，2H)；3.72-3.58(m，H)；3.24-3.10(m，H)；2.95-2.89(m，2H)；1.90-1.50(m，4H).MS(Ionspray)：329331(M⁺+1).

Example 49

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [5- (2-chloro-phenyl) - [1, 3, 4] oxadiazol-2-yl ] -phenyl } -methanone trifluoroacetate

3- [5- (2-chlorophenyl) - [1, 3, 4] oxadiazol-2-yl ] -benzoic acid methyl ester

At room temperature, methyl 3- (2H-tetrazol-5-yl) -benzoate (204mg, 1mmol) (according to Tanaka et al, J.Med.chem. (journal of medicinal chemistry), 1998, 41 (13)) 2406) was combined with 2-chlorobenzoyl chloride (175mg, 1mmol) in anisole (10ml), and a solution of 2,4, 6-collidine (121mg, 1mmol) in anisole (1ml) was added. The reaction mixture was heated at 100 ℃ for 1 hour and then at 120 ℃ for 15 minutes, with the evolution of gas being monitored with a balloon (the volume of gas evolved was measured by active displacement of water, total 22 ml). The reaction mixture was cooled to room temperature and concentrated to dryness in vacuo. The residue was subjected to flash column chromatography on silica eluting with a gradient of 5% to 40% ethyl acetate in heptane to isolate 3- [5- (2-chlorophenyl) - [1, 3, 4]]Oxadiazol-2-yl]-methyl benzoate as colorless powder (229mg, 73%).¹HNMR[CDCl₃]：δ8.79(s，H)；8.36(d，H)；8.25(d，H)；8.14(d，H)；7.72-7.57(m，2H)；7.57-7.41(m，2H)；4.00(s，3H).MS(Ion spray)：315317(M⁺+1).

To 3- [5- (2-chlorophenyl) - [1, 3, 4]]Oxadiazol-2-yl]Methyl benzoate (113mg, 0.36mmol) in methanol (5ml) and THF (2ml) 1N sodium hydroxide (2ml, 2mmol) was added and the reaction mixture was stirred at room temperature for 2 hours and then neutralized to pH 7 with 1N hydrochloric acid. The solution was evaporated to dryness in vacuo and left under high vacuum overnight. The crude material was used as is without purification. (MS (ion spray): 301, 303 (M)⁺+ 1); LC/MS purity > 95%, the only major impurity being sodium chloride). 2- (1H-benzotriazol-1-yl) -1, 1, 3, 3-tetramethyluronium tetrafluoroborate (TBTU) (116mg, 0.36mmol) was added to crude 3- [5- (2-chlorophenyl) - [1, 3, 4] at room temperature under nitrogen]Oxadiazol-2-yl]Benzoic acid and diisopropylethylamine (150mg, 1.14mmol) in dimethylformamide (2ml) solution/suspension. The reaction mixture was stirred at room temperature for 10 minutes, and then 4- [3- (N, N-di-tert-butoxycarbonylaminomethyl) phenyl ] was added]Piperidine (78mg, 0.2 mmol)) With diisopropylethylamine (150mg, 1.14mmol) in dimethylformamide (2 ml). The reaction mixture was stirred at room temperature for 16 h, concentrated to dryness in vacuo, subjected to flash column chromatography on anhydrous silica, eluting with 50: 50 dichloromethane: ethyl acetate, and 1- {4- [3- (N, N-di-tert-butoxycarbonylaminomethyl) phenyl ] was isolated]-piperidin-1-yl } -1- {3- [5- (2-chloro-phenyl) - [1, 3, 4]Oxadiazol-2-yl]-phenyl } -methanone, a colourless oil, which was dissolved in dichloromethane (10ml), cooled at 0 ℃ and treated with trifluoroacetic acid (1 ml). The reaction mixture was stirred at room temperature under nitrogen for 2 hours and concentrated to dryness in vacuo. The residue was dissolved in 20% acetonitrile/water (containing 0.1% trifluoroacetic acid) (9ml) and purified by preparative reverse phase HPLC (C-18, 10 micron reverse phase column) eluting with 20% to 60% acetonitrile/water (containing 0.1% trifluoroacetic acid). The product fractions were combined and concentrated to dryness in vacuo. The title compound was isolated as an amorphous white glassy solid (98mg, 83%).

¹H NMR[(CD₃)₂SO]：δ8.16(br s，3H，NH₃ ⁺)：8.22-8.16(m，2H)8.13(s，H)；7.79-7.72(m，3H)；7.69(td，H)；7.62(td，H)；7.41(s，H)；7.39-7.27(m，3H)；4.64(br d，H)；4.03(q，2H)；3.79-3.63(m，H)；3.28-3.20(m，H)；3.03-2.80(m，2H)；1.96-1.57(m，4H).MS(Ionspray)：473475(M⁺+1).

Example 50

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (5-pyridin-3-yl- [1, 3, 4] oxadiazol-2-yl) -phenyl ] methanone bistrifluoroacetate

3- (5-pyridin-3-yl- [1, 3, 4] oxadiazol-2-yl) -benzoic acid methyl ester

Prepared in a similar manner to that described in example 49A, but using nicotinoyl chloride hydrochloride instead of 2-chlorobenzoyl chloride, and 2mmol of 2,4, 6-collidine, and heating at 110 ℃ instead of 100 ℃. The residue was subjected to silica flash column chromatography, eluting with ethyl acetate and 5% methanol/ethyl acetate, to isolate 3- (5-pyridin-3-yl- [1, 3, 4] oxadiazol-2-yl) -benzoic acid methyl ester as a colourless powder (84mg, 30%).

¹H NMR[CDCl₃]：δ9.40(s，H)；8.84-8.80(m，H)；8.80-8.78(m，H)；8.47(dt，H)；8.38(dt，H)；8.26(dt，H)；7.67(t，H)；7.52(dd，H)；4.00(s，3H).MS(Ion spray)：282(M⁺+1).

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (5-pyridin-3-yl- [1, 3, 4] oxadiazol-2-yl) -phenyl ] -methanone bistrifluoroacetate

In a similar manner to the process described in example 49B, but using 3- (5-pyridin-3-yl- [1, 3, 4)]Oxadiazole-2-yl) -benzoic acid methyl ester instead of 3- [5- (2-chlorophenyl) [1, 3, 4]]Oxadiazol-2-yl]-methyl benzoate, preparing the title compound as an amorphous white glassy solid.¹HNMR[(CD₃)₂SO]：δ9.37(br s，H)；8.86(br s，H)；8.55(d，H)；8.28-8.23(m，H)；8.20(s，H)；8.16(br s，3H，NH3+)；7.79-7.65(m，3H)；7.41(s，H)；7.39-7.26(m，3H)；4.63(br d，H)；4.09-4.00(m，2H)；3.80-3.62(m，H)；3.37-3.16(m，H)；3.02-2.80(m，2H)；1.98-1.55(m，4H).MS(Ion spray)：441(M⁺+1).

Example 51

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl-formyl } -3-ethylsulfanyl-6, 6-dimethyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt

Following a procedure similar to that described in example 49BBy the method of (1), but using 3-ethylthio-6, 6-dimethyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid methyl ester instead of 3- [5- (2-chlorophenyl) - [1, 3, 4]]Oxadiazol-2-yl]-methyl benzoate, preparing the title compound as an amorphous white glassy solid.¹H NMR[(CD₃)₂SO]：δ8.16(br s，3H，NH₃ ⁺)；7.40-7.33(m，2H)；7.32-7.26(m，2H)；4.30-4.00(m，4H)；3.21-3.10(m，2H)；3.06(q，2H)；2.92-2.80(m，H)；2.66(s，2H)；2.38(s，2H)；1.90-1.78(m，2H)；1.68-1.50(m，2H)；0.98(s，6H).MS(Ion spray)：458(M⁺+1).

Example 52

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-propylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt

Carried out in a similar manner to the method described in example 49B, but using 4-oxo-3-propylsulfanyl-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid ethyl ester instead of 3- [5- (2-chlorophenyl) - [1, 3, 4]]Oxadiazol-2-yl]-methyl benzoate, preparing the title compound as an amorphous white glassy solid.¹H NMR[(CD₃)₂SO]：δ8.14(br s，3H，NH₃ ⁺)；7.41-7.23(m，4H)；4.21(br d，2H)；4.08-3.99(m，2H)；3.39-2.99(m，4H)；2.94-2.71(m，3H)；2.54-2.49(m，2H)；2.02-1.90(m，2H)；1.90-1.70(m，4H)；1.70-1.51(m，2H)；1.03(t，3H).MS(Ion spray)：443(M⁺+1).

Example 53

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-isopropylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt

Carried out in a similar manner to the method described in example 49B, but using 3-isopropylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid ethyl ester instead of 3- [5- (2-chlorophenyl) - [1, 3, 4]]Oxadiazol-2-yl]-benzoic acid methyl ester, preparation of the title compoundThe product was an amorphous white glassy solid.¹HNMR[(CD₃)₂SO]：δ8.14(br s，3H，NH₃ ⁺)；7.43-7.23(m，4H)；4.30-4.16(m，2H)；4.09-3.98(m，2H)；3.53(septet，H)；3.22-3.03(m，2H)；2.93-2.72(m，3H)；2.54-2.47(m，2H)；2.02-1.86(m，4H)；1.70-1.51(m，2H)；1.42(d，6H).MS(Ion spray)：443(M⁺+1).

Example 54

3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carbonitrile trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 49B, but using ethyl 3-cyano-6, 6-dimethyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ] thiophene-1-carboxylate instead of methyl 3- [5- (2-chlorophenyl) - [1, 3, 4] oxadiazol-2-yl ] -benzoate.

¹H NMR[(CD₃)₂SO]：δ8.14(br s，3H，NH₃ ⁺)；7.41-7.33(m，2H)；7.32-7.26(m，2H)；4.30-3.90(br m，2H)；4.04-3.98(m，2H)；3.30-3.01(m，2H)；2.93-2.80(m，H)；2.71(s，2H)；2.54(s，2H)；1.89-1.76(m，2H)；1.73-1.51(m，2H)；1.01(s，6H).MS(Ion spray)：423(M⁺+1).

Example 55

3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carboxylic acid trifluoroacetate salt

The title compound was isolated as a by-product in example 54 from the reaction carried out to synthesize 3- {1- [4- (3 aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carbonitrile trifluoroacetate.

¹H NMR[(CD₃)₂SO]：δ9.70(s，H，OH)；8.11(br s，3H，NH₃ ⁺)；7.42-7.26(m，4H)；4.28-3.96(br m，2H)；4.03-3.99(m，2H)；3.27-3.06(m，2H)；2.96-2.85(m，H)；2.70(s，2H)；2.63(s，2H)；1.93-1.72(m，2H)；1.69-1.52(m，2H)；1.01(s，6H).MS(Ion spray)：442(M⁺+1).

Example 56

3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carboxylic acid methyl ester trifluoroacetate salt

¹H NMR[(CD₃)₂SO]：δ8.16(brs，3H，NH₃ ⁺)；7.41-7.34(m，2H)；7.33-7.27(m，2H)；4.30-3.95(br m，2H)；4.06-4.00(m，2H)；3.84(s，3H)；3.25-3.04(m，2H)；2.94-2.80(m，H)；2.71(s，2H)；2.51(s，2H)；1.90-1.78(m，2H)；1.71-1.51(m，2H)；1.00(s，6H).MS(Ion spray)：456(M⁺+1).

Example 57

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl-formyl } -3-methoxy-6, 6-dimethyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one

Carried out in a similar manner to the procedure described in example 38, but using 3-methoxy-6, 6-dimethyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹HNMR[(CD₃)₂SO]：δ8.22(br s，3H，NH₃ ⁺)，7.54-7.27(m，4H)，4.29-4.22(m，2H)，4.14(s，3H)，4.13-4.02(m，2H)，3.26-3.08(m，2H)，3.04-2.86(m，1H)，2.71(s，2H)，2.37(s，2H)，2.02-1.84(m，2H)，1.79-1.54(m，2H)，1.04(s，6H).MS(Ion spray)：427.3(M⁺+1).

Example 58

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (4-pyrrol-1-yl-phenyl) -methanone-trifluoroacetate salt

The procedure was carried out in a similar manner to the process described in example 38, but using 4- (1H-pyrrol-1-yl) benzoic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹HNMR[(CD₃OD]：δ7.62-7.51(m，4H)，7.41-7.22(m，6H)，6.32-6.28(m，2H)，4.85-4.66(m，2H)，4.08(s，2H)，4.03-3.88(m，1H)，3.15-2.86(m，2H)，2.11-1.62(m，4H).MS(Ion spray)：360(M⁺+1).

Example 59

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1-benzo [ b ] thiophen-2-yl-methanone-trifluoroacetate salt

Carried out in a similar manner to the method described in example 38, but using benzo (b) thiophene-2-carboxylic acid instead of 3-methylsulfanyl-4-oxo-4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-carboxylic acid the title compound was prepared as an amorphous white solid.¹HNMR[(CD₃OD]：δ7.98-7.81(m，2H)，7.62(s，1H)，7.45-7.32(m，5H)，7.31-722(m，1H)，4.80-4.40(m，2H)，4.10(s，2H)，3.28-3.05(m，1H)，3.02-2.90(m，2H)，2.02-1.88(m，2H)，1.86-1.65(m，2H).MS(Ion spray)：351(M⁺+1).

Example 60

(E) -1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3- (3-methoxy-phenyl) -propenone-trifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using 3-methoxycinnamic acid, as an amorphous white solid.

¹HNMR[(CD₃OD]：δ7.56(d，1H)，7.45-7.25(m，5H)，7.23-7.13(m，3H)，6.98-6.90(m，1H)，4.85-4.70(m，1H)，4.50-4.35(m，1H)，4.08(s，2H)，3.83(s，3H)，3.40-3.32(m，1H)，3.01-2.75(m，2H)，2.08-1.83(m，2H)，1.81-1.61(m，2H).MS(Ion spray)：351(M⁺+1).

Example 61

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-ethoxy-thiophen-2-yl) -methanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 3-ethoxythiophene-2-carboxylic acid as an amorphous white solid.¹H NMR[(CD₃OD]：δ7.53(d，1H)，7.46-7.22(m，4H)，6.94(d，1H)，4.60-4.21(br.m.，2H)，4.19(q，2H)，4.08(s，2H)，3.18-2.98(m，1H)，2.96-2.85(m，2H)，2.0-1.86(m，2H)，1.84-1.65(m，2H)，1.37(t，3H).MS(Ion spray)：345(M⁺+1).

Example 62

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -2-indan-2-yl-ethanone-trifluoroacetate

The title compound was prepared in a similar manner to the procedure described for example 38 but using 2-indanyl acetic acid as amorphous white solid.¹HNMR[(CD₃OD]：δ7.45-7.25(m，4H)，7.18-7.15(m，2H)，7.147.04(m，2H)，4.78-4.65(m，1H)，4.18-4.11(m，1H)，4.08(s，2H)，3.28-3.08(m，2H)，2.95-2.76(m，2H)，2.74-2.58(m，6H) 2.01-1.85(m，2H)，1.75-1.51(m，2H).MS(Ion spray)：349(M⁺+1).

Example 63

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (3-chloro-phenyl) -pyridin-3-yl ] -methanone-bistrifluoroacetate

A.5- (3-chlorophenyl) -nicotinic acid

A three-necked flask was charged with 5-bromonicotinic acid (2g, 9.90mmol), 3-chlorophenylboronic acid (1.55g, 9.90mmol), 0.4M aqueous sodium carbonate (37ml, 14.8mmol), and acetonitrile (37 ml). The solution was degassed under vacuum, tetrakis (triphenylphosphine) palladium (0) (0.57g, 0.495mmol) was added and the reaction refluxed under nitrogen overnight. The reaction was cooled to room temperature and filtered through a pad of celite. The filtrate was partially evaporated under reduced pressure and the remaining solution was acidified with 1H HCl to pH 2. The resulting solid was collected by filtration and dried under vacuum.¹HNMR[(CD₃)₂SO]：δ9.15-9.05(m，2H)，8.45(s，1H)，7.85(s，1H)，7.80-7.65(m，1H) 7.60-7.42(m，2H).

The title compound was prepared in a similar manner to the method described in example 38, but using 5- (3-chlorophenyl) -nicotinic acid as an amorphous white solid.¹HNMR[(CD₃)₂SO]：_δ8.99(s，1H)，8.65(s，1H)，8.18(s，1H)，8.13(br.s.，3H，NH₃ ⁺)，7.88(s，1H)，7.76(d，1H)，7.58-7.45(m，2H)，7.40-7.20(m，4H)，4.80-4.58(m，1H) 3.98(q，H)，3.78-3.55(m，1H)，3.33-3.18(m，1H)，2.98-2.71(m，2H)，1.95-1.52(m，4H).MS(Ion spray)：406(M⁺+1).

Example 64

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-benzo [ b ] thiophen-2-yl) -methanone trifluoroacetate salt

In a similar manner to the procedure described in example 38, but using, for example, WO015-chlorobenzo (b) thiophene-2-carboxylic acid prepared at 07436 to prepare the title compound as an amorphous white solid.¹H NMR[(CD₃)₂SO]：_δ8.08(br s.，3H，NH₃ ⁺)，8.05(d，1H)，8.01(s，1H)，7.68(s，1H)，7.47(d，1H)，7.40-7.21(m，4H)，4.41(br.s.，2H)，3.99，(q，2H)，3.30-3.15(m，2H)，2.95-2.78(m，1H)，1.90-1.75(m，2H)，1.73-1.52(m，2H).MS(Ion spray)：385(M⁺+1).

Example 65

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -2- (3, 4-dichloro-phenyl) -ethanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 3, 4-dichlorophenyl acetic acid as an amorphous white solid.¹HNMR[(CD₃)₂SO]：_δ8.08(br.s.，3H，NH₃ ⁺)，7.56(d，1H)，7.48(s，1H)，7.38-7.15(m，5H)，4.58-4.45(m，1H)，4.15-3.92(m，3H)，3.85-3.65(m，2H)，3.18-3.03(m，1H)，2.85-2.55(m，2H)，1.80-1.65(m，2H)，1.55-1.32(m，2H).MS(Ion spray)：376(M⁺+1).

Example 66

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -2- (5-chloro-pyridin-3-yloxy) -ethanone-bistrifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using (5-chloropyridin-3-yloxy) -acetic acid as prepared in WO01/07436 as an amorphous white solid.¹HNMR[(CD₃)₂SO]：δ8.28-8.21(m，2H)，8.15(br.s.，3H，NH₃ ⁺)，7.58(s，1H)，7.40-7.20(M，4H)，5.01(s，2H)，4.52-4.38(m，1H)，3.98(q，2H)，3.93-3.80(m，1H)，3.22-3.05(m，1H)，2.88-2.58(m，2H)，1.88-1.35(m，4H).MS(Ion spray)：360(M⁺+1).

Example 67

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -2- (6-chloro-pyridin-2-yloxy) -ethanone-bistrifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using (6-chloropyridin-2-yloxy) -acetic acid as prepared in WO01/07436 as an amorphous white solid.¹HNMR[(CD₃)₂SO]：_δ8.10(br.s.，3H，NH₃ ⁺)，7.81-7.71(m，1H)，7.41-7.18(m，4H)，7.08(d，1H)，6.88(d，1H)，5.15-4.92(m，2H)，4.50-4.31(m，1H)，4.08-3.81(m，3H)，3.27-3.08(m，1H)，2.92-2.76(m，1H)，2.75-2.60(m，1H)，1.90-1.58(m，2H)，1.57-135(m，2H).MS(Ionspray)：360(M⁺+1).

Example 68

(E) -1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3- (5-chloro-thiophen-2-yl) -propenone-trifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using 3- (5-chloro-thiophen-2-yl) -acrylic acid as prepared in WO01/07436 as an amorphous white solid.¹H NMR[(CD₃)₂SO]：_δ8.08(br.s.，3H，NH₃ ⁺)，7.56(d，1H)，7.40-7.28(m，3H)，7.26-7.18(m，2H)，7.12(d，1H)，6.92(d，1H)，4.70-4.50(m，1H)，4.41-4.21-(m，1H)，3.98(q，2H)，3.28-3.05(m，1H)，2.90-2.63(m，2H)，1.91-1.72(m，2H)，1.65-1.35(m，2H).).MS(Ion spray)：361(M++1).

Example 69

(E) -1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -3- (4-chloro-thiophen-2-yl) -propenone-trifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using 3- (4-chloro-thiophen-2-yl) -acrylic acid as prepared in WO01/07436 as an amorphous white solid.

¹H NMR[(CD₃)₂SO]：_δ8.06(br.s.，3H，NH₃ ⁺)，7.65(s，1H)，7.60-7.48(m，2H)，7.40-7.20(m，4H)，7.08(d，1H)，4.70-4.51(m，1H)，4.42-4.25(m，1H)，4.05-3.93(m，2H)，328-3.08(m，1H)，2.90-2.63(m，2H)，1.90-1.65(m，2H)，1.63-1.40(m，2H).MS(Ion spray)：361(M⁺+1).

Example 70

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (4, 5,6, 7-tetrahydro-benzo [ c ] thiophen-1-yl) methanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 4, 5,6, 7-tetrahydro-benzo (c) thiophene-1-carboxylic acid as prepared in JOC V62#61997p.1599 as an amorphous white solid.¹H NMR[(CD₃)₂SO]：_δ8.13(br.s.，3H，NH₃ ⁺)，7.40-7.33(m，2H)，731-7.25(m，2H)，7.20(s，1H)，4.35-4.15(m，2H)，4.03(q，2H)，3.17-2.98(m，2H)，2.95-2.78(m，1H)，2.73-2.58(m，4H)，1.90-1.78(m，2H)，1.75-1.63(m，4H)，1.61-1.42(m，2H).MS(Ion spray)：355(M⁺+1).

Example 71

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-4-methoxy-thiophen-3-yl) -methanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 2-chloro-3-methoxy-thiophene-4-carboxylic acid as an amorphous white solid.¹H NMR[(CD₃)₂SO]：δ8.13(br.s.，3H，NH₃ ⁺)，7.57(s，1H)，7.40-7.22(m，4H)，4.70-4.58(m，1H)，4.05(q，2H)，3.85(s，3H)，3.75-3.60(m，1H)，3.25(m，1H)，2.95-2.78(m，2H)，1.93-1.70(m，2H)，1.68-1.45(m，2H).MS(Ion spray)：365(M⁺+1).

Example 72

(3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1H-indol-3-yl) -methanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using indole-3 carboxylic acid as an amorphous white solid.¹HNMR[(CD₃)₂SO]：δ8.13(br.s.，3H，NH₃ ⁺)，7.78-7.63(m，2H)，7.52-7.20(m，6H)，7.20-7.03(m，2H)，4.57-4.38(m，2H)，4.03(q，2H)，3.17-3.02(m，2H)，2.95-2.75(m，1H)，1.90-1.78(m，2H)，1.75-1.57(m，2H).MS(Ion spray)：334(M⁺+1).

Example 73

1- [4- (3-aminomethyl-phenyl) -4-hydroxy-piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone-bistrifluoroacetate

A.4- (3-cyano-phenyl) -4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

A solution of 3-bromobenzonitrile (0.48g, 2.64mmol) in THF (20ml) was stirred under nitrogen at-78 ℃. A solution of 2.0M n-BuLi in hexane (1.38ml, 2.72mmol) was added dropwise thereto. The solution was allowed to warm to-15 ℃ over 1.5 hours. The solution was cooled to-78 ℃ again, and a solution of N-Boc-4-piperidone (0.53g, 2.64mmol) in THF (5ml) was added dropwise. The reaction mixture was allowed to warm to-10 ℃ and stirred at this temperature for 3 hours. The reaction was quenched with 1/2 saturated ammonium chloride solution (30ml) and stirred for 15 minutes. THF was removed by evaporation and the residue was extracted with dichloromethane (3 × 50 ml). The combined organic extracts were dried over sodium sulfate and evaporated to give an orange oil which was purified by flash chromatography eluting with 3: 5: 2 dichloromethane: heptane: ethyl acetate to give the title compound (0.30g) as a clear oil.

¹H NMR[(CDCl₃]：_δ7.82(s，1H)，7.72(d，1H)，7.58(d，1H)，7.55-7.42(m，1H)，4.20-3.95(m，2H)，3.35-3.10(m，2H)，2.08-1.83(m，2H)，1.80-1.66(m，2H)，1.51(s，9H).

4- [3- (benzyloxycarbonylamino-methyl) -phenyl ] -4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester

A solution of 4- (3-cyano-phenyl) -4-hydroxy-piperidine-1-carboxylic acid-tert-butyl ester (0.30g, 0.99mmol) in 7N ammonia/methanol (25ml) and 5% aluminum rhodium (0.15g) on a Parr apparatus (45psi) was hydrogenated overnight. The reaction was filtered through celite, evaporated and azeotroped with MeOH: toluene 1: 1 (2X 30ml) to give 4- (3-aminomethyl-phenyl) -4-hydroxy-piperidine-1-carboxylic acid-tert-butyl ester as a foam. This compound was used directly in the next step.

To a stirred mixture of tert-butyl 4- (3-aminomethyl-phenyl) -4-hydroxy-piperidine-1-carboxylate (0.30g, 0.99mmol), dichloromethane (10ml) and water (10ml) was added potassium carbonate (0.28g, 2.02mmol) followed by benzyl chloroformate (0.34g, 2.02 mmol). The reaction was stirred at room temperature overnight. The reaction was extracted with dichloromethane (3 × 30 ml). The combined organic extracts were dried over sodium sulfate and evaporated to give a yellow-brown oil. Purification by flash chromatography with 40% ethyl acetate: heptane elution gave 4- [3- (benzyloxycarbonylamino-methyl) -phenyl ] -4-hydroxy-piperidine-1-carboxylic acid-tert-butyl ester (0.40 g).

¹H NMR[(CDCl₃]：δ7.45-7.18(m，9H)，5.15(s，2H)，5.08(br.s.，1H，NH)，4.40(d，2H)，4.15-3.93(m，2H)，335-3.15(m，2H)，2.08-1.90(m，2H)，1.75-1.62(m，2H)，1.50(s，9H).

1- [4- (3-aminomethyl-phenyl) -4-hydroxy-piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone bistrifluoroacetate

To a stirred solution of 4- [3- (benzyloxycarbonylamino-methyl) -phenyl ] -4-hydroxy-piperidine-1-carboxylic acid-tert-butyl ester (0.38g, 0.86mmol) and dichloromethane (15ml) was added trifluoroacetic acid (5ml) at 0 ℃. The reaction was allowed to warm to room temperature, stirred for 1 hour and evaporated to dryness to give [3- (4- (hydroxy-piperidin-4-yl) -benzyl ] -carbamic acid benzyl ester, which was used directly in the next step.

To a stirred solution of 5-phenethyl-pyridine-3-carboxylic acid (0.027g, 0.1mmol) and DMF (10ml) was added diisopropylethylamine (0.014g, 0.11mmol) followed by TBTU (0.0353g, 0.11 mmol). This was stirred for 5 minutes then a solution of [3- (4- (hydroxy-piperidin-4-yl) -benzyl ] -carbamic acid benzyl ester (0.045g, 0.1mmol), DMF (2ml) and diisopropylethylamine (0.039g, 0.3mmol) was added the reaction stirred at room temperature overnight the solvent was evaporated off and the remaining residue partitioned between ethyl acetate (50ml) and saturated sodium bicarbonate (10ml) the organic phase was separated, washed again with saturated sodium bicarbonate (10ml), dried over magnesium sulphate evaporated and then purified by flash chromatography (100% ethyl acetate) to give (3- { 4-hydroxy-1- [1- (5-phenethyl-pyridin-3-yl) -formyl ] -piperidin-4-yl } -benzyl) -carbamic acid benzyl ester (0.030g), the oil was clear oil. Hydrogenation with methanol (10ml), acetic acid (1ml) and a catalytic amount of 10% palladium on carbon overnight, followed by filtration through celite afforded the crude product, which was purified by HPLC as in example 38 to afford the title compound as an amorphous solid (9.1 mg).

¹H NMR[(CD₃)₂SO]：_δ8.58-8.42(m，2H)，8.15(br.s.，3H，NH₃ ⁺)，7.73(s，1H)，7.63-7.51(m，2H)，7.40(t，1H)，7.38-7.25(m，1H)，7.23-7.10(m，5H)，4.58-4.38(m，1H)，4.03(q，2H)，3.60-3.10(m，3H)，3.05-2.86(m，4H)，2.06-1.80(m，2H)，1.78-1.63(m，1H)，1.62-1.42(m，1H).MS(Ion spray)：416(M⁺+1).

Example 74

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1-methyl-1H-indol-3-yl) -methanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 1-methyl-1H-indole-3-carboxylic acid as an amorphous white solid.¹HNMR[CDCl₃]：δ8.63(br.s.，3H，NH₃ ⁺)，7.60(d，1H)，7.51(s，1H)，7.41-7.18(m，5H)，7.15-7.05(m，2H)，4.55-4.35(m，2H)，4.01(br.s.，2H)，3.78(s，3H)，3.18-2.95(m，2H)，2.80-2.61(m，1H)，1.85-1.45(m，4H).MS(Ion spray)：348(M⁺+1).

Example 75

1- (3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -indol-1-yl) -ethanone-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 1-acetyl-1H-indole-3-carboxylic acid as an amorphous white solid.¹HNMR[(CD₃)₂SO]：_δ8.39(d，1H)，8.21(br.s.，3H，NH₃ ⁺)，8.13(s，1H)，7.70(d，1H)，7.68-7.25(m，6H)，4.40(br.s.，2H)，4.15-4.02(m，2H)，3.15-3.03(m，2H)，2.99-2.80(m，1H)，2.71(s，3H)，1.95-1.76(m，2H)，1.74-1.55(m，2H).MS(Ion spray)：376(M⁺+1).

Example 76

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-methoxy-1-methyl-1H-indol-3-yl) -methanone-trifluoroacetate salt

The title compound is prepared in a similar manner to the method described in example 38, but using 5-methoxy-1-methyl-1H-indole-3-carboxylic acid as prepared in WO95/22524 as an amorphous white solid.¹H NMR[(CD₃)₂SO]：_δ8.13(br.s.，3H，NH₃ ⁺)，7.71(s，1H)，7.51-7.23(m，5H)，7.20(s，1H)，6.83(dd，1H)，4.53-4.40(m，2H)，4.13-3.95(m，2H)，3.80(s，3H)，3.76(s，3H)，3.18-3.01(m，2H)，2.95-2.75(m，1H)1.95-1.76(m，2H)，1.75-1.52(m，2H).MS(Ion spray)：378(M⁺+1).

Example 77

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (2-trifluoromethyl-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

4- {3- [ N, N-bis- (tert-Butoxycarbonyl) aminomethyl ] -phenyl } -piperidine

As an alternative route, the title compound was prepared using a single pot cross-coupling method. Reacting 3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]A solution of-bromobenzene (example 1A) (7.7g, 20mmol) in anhydrous DMF (60ml) was treated with potassium acetate (5.9g, 60mmol), bis (pinacolato) diboron (5g, 20mmol) and [1, 1' -bis- (diphenylphosphino) ferrocenyl]Palladium (II) dichloride-dichloromethane complex (0.49g, 0.60 mmol). The mixture was stirred at 80 ℃ under nitrogen for 4 hours, then benzyl 1, 2, 3, 6-tetrahydro-4- (trifluoromethanesulfonyloxy) -pyridine-1-carboxylate (example 1B) (9.2g, crude, < 25mmol) was added followed by aqueous Na₂CO₃(2M, 60 ml). The mixture was heated at 80 ℃ under nitrogen for an additional 2 hours and then concentrated. After purification (as described in example 1B) the cross-coupled product (2.2g) was obtained. Further reduction (as described in example 1B) gave the title compound.

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (2-trifluoromethyl-phenylethynyl) -phenyl ] -methanone trifluoroacetate

The title compound was prepared in a similar manner to the coupling procedure described in example 5B, but using 2-iodotrifluorotoluene and further deprotected as described in example 38, as an amorphous, incompletely white solid.¹H NMR[CD₃OD]：δ7.80-7.30(m，12H)，4.81(br，1H)，4.10(s，2H)，3.87(br 1H)，3.30(br，1H)，2.97(m，2H)，2.05-1.60(br，4H).MS(Ion spray)：463(M+1).

Example 78

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (2-methyl-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the coupling procedure described in example 5b, but using 2-iodotoluene and further deprotected as described in example 38, as an amorphous, incompletely white solid.¹H NMR[CD₃OD]：δ7.66-7.16(m，12H)，4.81(br，1H)，4.11(s，2H)，3.87(br 1H)，3.30(br，1H)，2.97(m，H)，2.51(s，3H)，2.055-1.60(br，4H).MS(Ionspray)：409(M+1).

Example 79

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (4-chloro-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the coupling procedure described in example 5b, but using 1-chloro-4-iodobenzene and then deprotected as described in example 38, as an amorphous, incompletely white solid.¹HNMR[CD₃OD]：δ7.68-7.28(m，12H)，4.82(br，1H)，4.11(s，2H)，3.87(br 1H)，3.30(br，1H)，2.97(m，2H)，2.05-1.60(br，4H).MS(Ion spray)：429431(M+1).

Example 80

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1-3- (2-chloro-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the coupling procedure described in example 5b, but using 1-chloro-2-iodobenzene and then deprotected as described in example 38, as an amorphous, incompletely white solid.¹H NMR[CD₃OD]：δ7.69-7.28(m，12H)，4.82(br，1H)，4.11(s，2H)，3.87(br 1H)，3.30(br，1H)，2.97(m，2H)，2.05-1.60(br，4H).MS(Ion spray)：429431(M+1).

Example 81

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (2-fluoro-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

The procedure is carried out in a similar manner to the coupling procedure described in example 5b, but using 1-fluoro-2-iodobenzene, as in example 38The title compound was prepared as an amorphous, incompletely white solid by the deprotection.¹H NMR[CD₃OD]：δ7.69-7.16(m，12H)，4.80(br，1H)，4.10(s，2H)，3.84(br 1H)，3.30(br，1H)，2.96(m，2H)，2.05-1.60(br，4H).MS(Ion spray)：413(M+1).

Example 82

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (3-fluoro-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the coupling procedure described in example 5b, but using 1-fluoro-3-iodobenzene and then deprotected as described in example 38, as an amorphous, incompletely white solid.¹HNMR[CD₃OD]：δ7.67-7.10(m，12H)，4.80(br，1H)，4.10(s，2H)，3.85(br 1H)，3.30(br，1H)，2.95(m，2H)，2.05-1.60(br，4H).MS(Ion spray)：413(M+1).

Example 83

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (4-fluoro-phenylethynyl) -phenyl ] -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the coupling procedure described in example 5b, but using 1-fluoro-4-iodobenzene and then deprotected as described in example 38, as an amorphous, incompletely white solid.¹H NMR[CD₃OD]：δ7.64-7.10(m，12H)，4.80(br，1H)，4.10(s，2H)，3.85(br 1H)，3.30(br，1H)，2.97(m，2H)，2.05-1.60(br，4H).MS(Ion spray)：413(M+1).

Example 84

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (2-fluoro-phenyl) -ethyl ] -phenyl ] -methanone trifluoroacetate salt

The title compound was prepared as an amorphous, incompletely white solid by performing in a similar manner to the reduction procedure described in example 9 and then deprotecting as described in example 38.

¹H NMR[CD₃OD]：δ7.43-6.96(m，12H)，4.78(br，1H)，4.11(s，2H)，3.72(br 1H)，3.18(br，1H)，3.02-2.86(m，6H)，2.05-1.50(br，4H).MS(Ion spray)：417(M+1).

Example 85

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (3-fluoro-phenyl) -ethyl) -phenyl } -methanone trifluoroacetate salt

¹H NMR[CD₃OD]：δ7.43-6.80(m，12H)，4.78(br，1H)，4.11(s，2H)，3.70(br 1H)，3.18(br，1H)，3.02-2.85(m，6H)，2.05-1.50(br，4H).MS(Ion spray)：417(M+1).

Example 86

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (4-fluoro-phenyl) -ethyl ] -phenyl } -methanone trifluoroacetate salt

¹H NMR[CD₃OD]：δ7.43-6.88(m，12H)，4.78(br，1H)，4.10(s，2H)，3.69(br 1H)：3.18(br，1H)，3.00-2.85(m，6H)，2.05-1.50(br，4H).MS(Ion spray)：417(M+1).

Example 87

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (6-amino-pyridin-3-yl) ethynyl ] -phenyl } -methanone tris-trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using (6-tert-butoxycarbonylamino-pyridin-3-yl) ethynyl-pyridine-3-carboxylic acid (prepared according to the method described in example 7) as an amorphous incompletely white solid.

¹HNMR[CD₃OD]：δ8.82(s，1H)，8,66(s，1H)，8.17(s，1H)，8.07(s，1H)，8.02(d，1H)，7.43-7.27(m，4H)，7.05(d，1H)，4.81(br，1H)，4.10(s，2H)，3.79(br 1H)，3.37(br，1H)，2.97(m，2H)，2.05-1.70(br，4H).MS(Ion spray)：412(M+1).

Example 88

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (6-amino-pyridin-3-yl) -ethyl ] -phenyl } -methanone tris-trifluoroacetate salt

¹H NMR[CD₃OD]：δ8.60(m，2H)，7.94(s，1H)，7.89(d，1H)，7.61(s，1H)，7.45-7.28(m，4H)，6.97(d，1H)，4.80(br，1H)，4.11(s，2H)，3.76(br 1H)，3.10-2.90(m，7H)，2.05-1.60(br，4H).MS(Ion spray)：416(M+1).

Example 89

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (6-chloro-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 6-chlorothieno [3, 2-b ] thiophene-2-carboxylic acid, as an amorphous, incompletely white solid.

¹HNMR[CD₃OD]：δ7.60(s，1H)，7.47(s，1H)，7.33-7.18(m，4H)，4.50(br，2H)，3.98(s，2H)，3.12(br，2H)，2.86(m，1H)，1.85(b，2H)，1.67(m，2H).MS(Ion spray)：391393(M+1).

Example 90

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-fluoro-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 5-fluorothieno [3, 2-b ] thiophene-2-carboxylic acid as an amorphous, incompletely white solid.

¹HNMR[CD₃OD]：δ7.65(s，1H)，7.44-7.17(m，4H)，7.03(s，1H)，4.60(br，2H)，4.12(s，2H)，3.22(br，2H)，2.97(m，1H)，1.97(b，2H)，1.78(m，2H).MS(Ion spray)：375(M+1).

Example 91

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-methyl-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 5-methylthieno [3, 2-b ] thiophene-2-carboxylic acid as an amorphous, incompletely white solid.

¹HNMR[CD₃OD]：δ7.60(s，1H)，7.42-730(m，4H)，7.07(s，1H)，4.63(br，2H)，4.11(s，2H)，3.21(br，2H)，2.97(m，1H) 2.60(s，3H)，1.96(b，2H)，1.78(m，2H).MS(Ion spray)：371(M+1).

Example 92

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt

The title compound was prepared in a similar manner to the method described in example 38, but using 5-chlorothieno [3, 2-b ] thiophene-2-carboxylic acid, as an amorphous, incompletely white solid.

¹H NMR[CD₃OD]：δ7.63(s，1H)，7.42-7.29(m，5H)，4.60(br，2H)，4.11(s，2H)，3.12(br，2H)，2.97(m，1H)，1.97(b，2H)，1.78(m，2H).MS(Ion spray)：391

The following compounds were prepared in a similar manner to the above procedure:

example 93

1- {4- [3- (1-aminoethyl) phenyl ] -piperidin-1-yl } -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride

[1- (3-bromophenyl) ethyl ] -carbamic acid tert-butyl ester

3-Bromobenzophenone oxime (23.4mmol) was stirred in glacial acetic acid (150ml) at room temperature under nitrogen, and zinc powder (94mmol) was added in portions. The reaction mixture was stirred at room temperature for 24 hours, the solid was filtered off and the filtrate was concentrated to dryness. The residue was diluted with water, acidified to pH 5 with 1N HCl and washed with ethyl acetate. The aqueous phase was basified with sodium bicarbonate, extracted with ethyl acetate, dried over magnesium sulfate and concentrated to dryness. The residue was dissolved in dimethylformamide (30ml), and triethylamine (36.9mmol) was added. To the solution was added dropwise a solution of di-tert-butyldicarbonate (32.4mmol) in DMF (10 ml). The reaction mixture was stirred at room temperature for 6 hours, left to stand for 24 hours, and then concentrated to dryness. The residue was partitioned between water and ethyl acetate and the aqueous phase was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over magnesium sulfate and concentrated to dryness. The residue was purified by column chromatography on silica gel using dichloromethane as eluent to give [1- (3-bromophenyl) ethyl ] ethyl]Tert-butyl carbamate, a pale yellow oil, crystallized on standing. Ms (ei): 300 and 302 (M)⁺+H).

By following a similar procedure to the one described in example 17D, but using [1- (3-bromophenyl) ethyl ]]-carbamic acid tert-butyl ester instead of N- (tert-butoxycarbonyl) -3-bromo-4-fluorobenzylPreparation of [1- (3- {1- [1- (3-phenethyl-phenyl) -formyl ] amine]-1, 2, 3, 6-tetrahydro-pyridin-4-yl]-phenyl) -ethyl]-carbamic acid tert-butyl ester. This material was subjected to the same conditions as described in example 2A, but using [1- (3- {1- [1- (3-phenethyl-phenyl) -formyl group]-1, 2, 3, 6-tetrahydro-pyridin-4-yl } -phenyl) -ethyl]-carbamic acid tert-butyl ester instead of 5-phenylethynylpyridine-3-carboxylic acid. The crude reaction product was purified by silica gel column chromatography and then subjected to the same conditions as those described in example 1D, except that [1- (3- {1- [1- (3-phenethylphenyl) -formyl group was used]-piperidin-4-yl } phenyl) ethyl]Replacement of 3- [1- (5-Phenylethynylpyridine-3-carbonyl) piperidin-4-yl with tert-butyl carbamate]A benzonitrile. Isolation of 1- {4- [3- (1-aminoethyl) phenyl]-piperidin-1-yl]-1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride as a light yellow solid. Ms (ei): 414 (M)⁺+H).

Example 94

1- [4- (5-aminomethyl-3-hydroxyphenyl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride

A.3-bromo-N, N- (bis-tert-butoxycarbonyl) -5- (tert-butyldimethylsilyloxy) benzylamine

(3-bromo-5-methyl-phenoxy) -tert-butyldimethylsilane (3.32mmol) (prepared according to J.E.Baldwin et al, Tetrahedron, 1991, 47(29), 5603), N-bromosuccinimide (3.65mmol) and benzoyl peroxide (0.332mmol) were dissolved in dichloromethane (10ml) and the reaction mixture was irradiated for 4 hours. Dilute with dichloromethane, wash with water, dry over magnesium sulfate, and concentrate to dryness. The crude material was purified by column chromatography on silica gel eluting with 10% ethyl acetate/cyclohexane to give (3-bromo-5-bromomethyl-phenoxy) -tert-butyldimethylsilane as a colorless oil. This material was subjected to the conditions described in the first part of example 1A, but using (3-bromo-5-bromomethyl-phenoxy) -tert-butyldimethylsilyl instead of 3-bromobenzyl bromide, to give 3-bromo-N, N- (bis-tert-butoxycarbonyl) -5- (tert-butyldimethylsilyloxy) benzylamine as a colorless oil. MS (EI)516 and 518 (M)⁺+H).

1- (5-Phenylethynylpyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydropyridine

By proceeding in a similar manner to the method described in example 17B, but using 5-phenylethynylpyridine-3-carboxylic acid instead of 5-phenethylpyridine-3-carboxylic acid, 1- (5-phenylethynylpyridine-3-carbonyl) -4- (pinacolatoboronyl) -1, 2, 3, 6-tetrahydropyridine was prepared as a light yellow solid. MS (EI)415 (M)⁺+H).

1- {4- [3- (N, N-bis-tert-Butoxycarbonyl) aminomethyl-5-hydroxyphenyl ] -3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenylethynylpyridin-3-yl) methanone

In a similar manner to the process described in example 17D, but using 3-bromo-N, N- (bis-tert-butoxycarbonyl) -5- (tert-butyldimethylsilyloxy) benzylamine instead of N- (tert-butoxycarbonyl) -3-bromo-4-fluorobenzylamine, and 1- (5-phenylethynylpyridine-3-carbonyl) -4- (pinacolboronyl) -1, 2, 3, 6-tetrahydropyridine was used instead of 1- (5-phenylethynylpyridine-3-carbonyl) -4- (pinacolboronyl) -1, 2, 3, 6-tetrahydropyridine to prepare 1- {4- [3- (N, N-bis-tert-butoxycarbonyl) aminomethyl-5-hydroxyphenyl.]-3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenylethynylpyridin-3-yl) methanone as a light brown solid. MS (EI)610 (M)⁺+ H). The tert-butyldimethylsilyl moiety has been unexpectedly removed during the process.

In a similar manner to the process described in example 2A, but using 1- {4- [3- (N, N-bis-tert-butoxycarbonyl) aminomethyl-5-hydroxyphenyl]Preparation of 1- {4- [3- (N, N-bis-tert-butoxycarbonyl) aminomethyl-5-hydroxy-phenyl-methanone instead of 5-phenylethynyl pyridine-3-carboxylic acid-3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenylethynyl-pyridin-3-yl) methanone]Piperidin-1-yl } -1- (5-phenethylpyridin-3-yl) methanone. The crude reaction product was purified by column chromatography on silica gel and then subjected to the same conditions as described in example 1D, except that 1- {4- [3- (N, N-bis-tert-butoxycarbonyl) carbamic acid methyl ester was usedRadical-5-hydroxyphenyl]Piperidin-1-yl } -1- (5-phenethylpyridin-3-yl) methanone instead of 3- [1- (5-phenylethynylpyridine-3-carbonyl) piperidin-4-yl]A benzonitrile. Isolation of 1- [4- (5-aminomethyl-3-hydroxyphenyl) -piperidin-1-yl]-1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride as a light yellow solid. Ms (ei): 416 (M)⁺+H).

Example 95

1- [4- (5-aminomethyl-2-hydroxyphenyl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride

A.4-benzyloxy-3-bromobenzylcarbamic acid tert-butyl ester

3-bromo-4-fluorobenzonitrile (3.00g, 15mmol), benzyl alcohol (1.71ml, 16.5mmol) and THF (40ml) were combined and treated with 60% sodium hydride in oil (0.66g, 16.5 mmol). The reaction mixture was heated to reflux under nitrogen for 3 hours. By aqueous workup and chromatography (cyclohexane: dichloromethane 3: 1), 4-benzyloxy-3-bromobenzylnitrile is obtained as a white solid (3.88g, 13.5 mmol). A portion of this material (2.64g, 9.16mmol) in THF (25ml) was treated with 1M borane in THF (18.3ml, 18.3 mmol). After the exotherm subsided, the reaction was refluxed under nitrogen for two to three days. Addition of methanol destroyed excess borane and 4-benzyloxy-3-bromobenzylamine precipitated as the hydrochloride salt (1.58g, 4.8 mmol). This material was suspended in dichloromethane (30ml) and treated successively with triethylamine (1.68ml, 12.02mmol) and di-tert-butyl dicarbonate (1.26g, 5.77 mmol). The reaction mixture was stirred under nitrogen for 4 hours; by aqueous workup and chromatographic purification (ethyl acetate: cyclohexane 3: 7), the title compound is obtained as a white solid (1.69g, 4.3 mmol.) MS (EI): 394 (M)⁺)

4-benzyloxy-3- {1- [1- (5-phenethylpyridin-3-yl) formyl ] -1, 2, 3, 6-tetrahydropyridin-4-yl } benzylcarbamic acid tert-butyl ester

1- (5-Phenethylpyridine-3-carbonyl) -4- (pinacolatoboronyl) -1, 2, 3, 6-tetrahydropyridine prepared as in example 17B (0.628g, 1.5mmol), tert-butyl 4-benzyloxy-3-bromobenzylcarbamate (0.62g, 1.58mmol), dichlorobis (triphenylphosphine) palladium (II) (0.074g, 0.08mmol), potassium carbonate (0.622g, 4.5mmol) and DMF (15ml) were heated to 80 ℃ under nitrogen for 3 h. DMF was removed in vacuo, the residue was worked up with water and the organic residue was purified by chromatography to give a grey foam (0.45g, 0.75 mmol).

3-hydroxy-2- {1- [1- (5-phenethylpyridin-3-yl) formyl ] -piperidin-4-yl } -benzylcarbamic acid tert-butyl ester

4-benzyloxy-3- {1- [1- (5-phenethylpyridin-3-yl) formyl group]-1, 2, 3, 6-tetrahydropyridin-4-yl } -benzylcarbamic acid tert-butyl ester (0.34g, 0.56mmol) was hydrogenated with hydrogen and 10% P/C to give the title compound as a white foam (0.27g, 0.52 mmol). Ms (ei): 515 (M)⁺)

3-hydroxy-2- {1- [1- (5-phenethylpyridin-3-yl) formyl following the procedure described in example 5C]-piperidin-4-yl } -benzylcarbamic acid tert-butyl ester (0.09g, 0.175mmol) was converted to the title compound (0.053g, 0.11 mmol). Ms (ei): 416 (M)⁺+H).

Example 96

1- [4- (5-aminomethyl-2-benzyloxyphenyl) -3, 6-dihydro-2H-pyridin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride

4-benzyloxy-3- {1- [1- (5-phenethylpyridin-3-yl) formyl according to the procedure described in example 5C]-1, 2, 3, 6-tetrahydropyridin-4-yl } -benzylcarbamic acid tert-butyl ester (0.11g, 0.184mmol) was converted to the title compound (0.080g, 0.15 mmol). Ms (ei): 504 (M)⁺+H).

Example 97

1- [4- (3-Aminomethylphenyl) -piperidin-1-yl ] -1- (4-phenethyl-phenyl) -methanone hydrochloride

A.4-Phenylethynylbenzoic acid

To silver oxide (0.56g, 2.43 mmo)l) was suspended in water (15ml) 4-phenylacetylbenzaldehyde (1.01g, 4.85mmol) and sodium hydroxide (0.97g, 24.3mmol) were added. The reaction mixture was heated to 90 ℃ for 1.5 hours, cooled and acidified. The aqueous mixture was extracted with ethyl acetate and the organic layer was concentrated. The resulting solid was partitioned between ether and 0.1M sodium hydroxide solution. The aqueous layer was acidified and the precipitated title compound (0.55g, 2.5mmol) was collected. M.P.224-225 ℃; ms (ei): 222 (M)⁺)

By proceeding in a similar manner to the method described in example 1C, but using 4-phenylacetylbenzoic acid, N-bis- (tert-butoxycarbonyl) -3- [1- (4-phenylethynyl-benzoyl) -piperidin-4-yl]-benzylamine. The title compound was then prepared using the method described in example 9. Ms (ei): 399 (M)⁺+H).

Example 98

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [2- (2-hydroxy-phenyl) -ethyl ] -phenyl } -methanone hydrochloride

Proceeding in a similar manner to the method described in example 10, but using N, N-bis- (tert-butoxycarbonyl) -3- {1- [3- (2-hydroxyphenyl) ethynyl-benzoyl ] -piperidin-4-yl } -benzylamine prepared in a similar manner to the method described in example 6a (but using 2-iodophenol), the title compound was prepared as a white amorphous solid. Ms (ei): 415(M + H).

Example 99

1- [4- (5-aminomethyl-2-hydroxymethylphenyl) -3, 6-dihydro-2H-pyridin-1-yl ] -1- (5-phenethylpyridin-3-yl) -methanone

A. Acetic acid 4- (N, N-bis-tert-butoxycarbonyl) aminomethyl-2-bromobenzyl ester

2-bromo-4- (bromomethyl) benzyl bromide (2.91mmol) (prepared according to Bridger et al, J.Med.Chem. (J.Med. chem.) 1995, 38(2), 366 process) and di-tert-butyliminodicarboxylate (2.91 mmo)l) was dissolved in tetrahydrofuran (10ml) and sodium hydride (60% in mineral oil, 2.91mmol) was added at room temperature under argon. The reaction mixture was stirred at room temperature for 4 days, quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate, washed with brine, dried over magnesium sulfate, and concentrated to dryness. The crude residue was purified by column chromatography on silica eluting with cyclohexane/ethyl acetate 9: 1. 3-bromo-4-bromomethyl- (N, N-bis-tert-butoxycarbonyl) benzylamine was isolated as a white solid. A portion of 3-bromo-4-bromomethyl- (N, N-bis-tert-butoxycarbonyl) benzylamine (1.88mmol) was dissolved in acetonitrile (15ml), to which was added potassium acetate (3.7mmol) and 18-crown-6 (0.095 mmol). The reaction mixture was stirred at room temperature for 16 h, concentrated to dryness, extracted with ethyl acetate, washed with brine, dried over magnesium sulfate and concentrated to dryness. Purification by column chromatography on silica eluting with diethyl ether and cyclohexane 1: 1. Acetic acid 4- (N, N-bis-tert-butoxycarbonyl) aminomethyl-2-bromobenzyl ester was isolated as a colorless solid. MS (EI)458 and 460 (M)⁺+H).

1- {4- [5- (N, N-bis-tert-butoxycarbonyl) aminomethyl-2-acetoxymethylphenyl ] -3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenethylpyridin-3-yl) methanone

1- {4- [5- (N, N-bis-tert-Butoxycarbonyl) aminomethyl-2-acetoxymethylphenylphenyl prepared in a similar manner to the procedure described in example 17D but using 4- (N, N-bis-tert-butoxycarbonyl) aminomethyl-2-bromobenzyl acetate in place of N- (tert-butoxycarbonyl) -3-bromo-4-fluorobenzylamine]-3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenethylpyridin-3-yl) methanone. MS (EI)670 (M)⁺+H).

1- [4- (5-aminomethyl-2-hydroxymethylphenyl) -3, 6-dihydro-2H-pyridin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone

1- {4- [5- (N, N-bis-tert-butoxycarbonyl) aminomethyl-2-acetoxymethylphenyl]-3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenethylpyridin-3-yl) methanone (0.3mmol) was dissolved in methanol (10ml) and cooled at 0 ℃ while adding potassium carbonate (0.1 mmol). After 16 h at room temperature, it was concentrated to dryness and the crude residue was used directly in the next step. According to the combination of the ingredientsThe procedure described in example 1D is carried out in a similar manner, but using 1- {4- [5- (N, N-bis-tert-butoxycarbonyl) aminomethyl-2-hydroxymethylphenyl]Preparation of 1- [4- (5-aminomethyl-2-hydroxymethylphenyl) -3, 6-dihydro-2H-pyridin-1-yl ] methanone instead of 3- [1- (5-phenylethynylpyridine-3-carbonyl) piperidin-4-ylbenzonitrile (3, 6-dihydro-2H-pyridin-1-yl } -1- (5-phenethylpyridin-3-yl) methanone]-1- (5-phenethyl-pyridin-3-yl) -methanone as a light yellow solid. Ms (ei): 428 (M)⁺+H).

Example 100

1- [4- (5-aminomethyl-thiophen-2-yl) -piperidin-1-yl ] - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride

A.2- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -4-bromo-thiophene

The title compound was prepared in a similar manner to the method described in example 1A, but using 4-bromo-2-bromomethyl-thiophene, prepared from the reduction of 4-bromo-thiophene-2-carbaldehyde and subsequent bromination of the alcohol.

The title compound was prepared in a similar manner to the method described for example 93, but using 2- [ N, N-bis (tert-butoxycarbonyl) aminomethyl ] -4-bromo-thiophene as a white amorphous solid. Ms (ei): 406(M + H).

Example 101

[4- (5-aminomethyl-pyridin-3-yl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone trihydrochloride

A.3-bromo-5- (N, N-bis-tert-butoxycarbonyl) aminomethylpyridine

3-bromo-5-hydroxymethylpyridine (16.1mmol) (prepared according to Ashimori et al, chem.pharm.Bull. (chemical and pharmaceutical bulletin) 1990, 38(9), 2446 mmol) and pyridine (32.3mmol) were dissolved in acetonitrile (32ml) and cooled to 0 ℃. Dibromotriphenylphosphorane (20.9mmol) was added and the reaction mixture was calcined in a sealThe internal temperature of the flask was allowed to warm to room temperature for 4 hours. The crude reaction mixture was directly purified by column chromatography on silica eluting with diethyl ether and cyclohexane 1: 3. The 3-bromo-5-bromomethylpyridine was isolated as a light brown solid. 3-bromo-5-bromomethylpyridine (7.7mmol) and di-tert-butyliminodicarboxylate (10mmol) were dissolved in tetrahydrofuran (20ml) and sodium hydride (60% in mineral oil, 10mmol) was added at room temperature under argon. The reaction mixture was stirred at room temperature for 16 hours, quenched with saturated aqueous ammonium chloride, extracted with ethyl acetate, washed with brine, dried over nitrile magnesium sulfate and concentrated to dryness. The crude residue was purified by column chromatography on silica eluting with cyclohexane/diethyl ether 2: 1. The 3-bromo-5- (N, N-bis-tert-butoxycarbonyl) aminomethylpyridine was isolated as a pale yellow solid. MS (EI)387 and 389 (M)⁺+H).

By proceeding in a similar manner to the method described in example 17D, but using 3-bromo-5- (N, N-bis-tert-butoxycarbonyl) aminomethylpyridine instead of N- (tert-butoxycarbonyl) -3-bromo-4-fluorobenzylamine, 1- (5-phenylethynylpyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydropyridine instead of 1- (5-phenylethynylpyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydropyridine, 1- [5- (N, N-bis-tert-butoxycarbonyl) aminomethyl-3 ', 6 ' -dihydro-2 ' H- [3, 4']Bipyridyl-1' -yl]-1- (5-phenylethynylpyridin-3-yl) methanone. This material was subjected to the same conditions as described in example 2A, but using 1- [5- (N, N-bis-tert-butoxycarbonyl) aminomethyl-3 ', 6' -dihydro-2 'H- [3, 4']Bipyridyl-1' -yl]-1- (5-phenylethynylpyridin-3-yl) methanone instead of 5-phenylethynylpyridine-3-carboxylic acid. The crude reaction product was purified by column chromatography on silica gel and then subjected to the same conditions as described in example 1D, except that {4- [5- (N, N-bis-tert-butoxycarbonyl) aminomethylpyridin-3-yl ] was used]-piperidin-1-yl } -1- (5-phenethyl-pyridin-3-yl) -methanone instead of 3- [1- (5-phenylethynylpyridine-3-carbonyl) piperidin-4-yl]A benzonitrile. Isolation of [4- (5-aminomethyl-pyridin-3-yl) -piperidin-1-yl]-1- (5-phenethyl-pyridin-3-yl) -methanone tri-saltAcid salt as light yellow solid. Ms (ei): 401 (M)⁺+H).

Example 102

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1-ethyl-1H-indol-3-yl) -methanone-trifluoroacetate salt

A.1-Ethyl-1H-indole-3-carboxylic acid methyl ester

A flask was charged with a solution of methyl 1H-indole-3-carboxylate (2g, 11.41mmol) and ethyl iodide (4.4g, 28.5mmol) in anhydrous THF (25 ml). The mixture was stirred in a water bath and 60% sodium hydride (0.68g, 17.12mmol) in mineral oil dispersion was added portionwise over 5 minutes. The reaction was stirred for 48 hours and quenched by careful addition of water. The mixture was extracted with dichloromethane (2 × 100ml), dried over sodium sulfate and evaporated under reduced pressure. The crude product was purified by flash chromatography on silica (10% ethyl acetate in heptane) to give methyl 1-ethyl-1H-3-carboxylate (1.8 g).¹HNMR[CDCl₃]：_δ8.22-8.15(m，1H)，7.87(s，1H)，7.42-7.33(m，1H)，7.31-7.25(m，2H)，4.22(q，2H)，3.92(s，3H)，1.52(t，3H).

B.1-Ethyl-1H-indole-3-carboxylic acid

A solution of methyl 1-ethyl-1H-indole-3-carboxylate (1.8g, 8.8mmol) in a 1: 1 mixture of THF: MeOH (40ml) was stirred and 2N NaOH (20ml) was added to it. The reaction was heated to reflux for 4 hours. The reaction mixture was partially evaporated, THF, MeOH removed, and the residue diluted with water (20ml) and acidified to pH 2 with 1N HCl. The mixture was extracted with dichloromethane (100ml), dried over sodium sulphate and evaporated under reduced pressure to give the title compound as a white solid which was used directly in the next step.

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1-ethyl-1H-indol-3-yl) -methanone trifluoroacetate

The title compound was prepared in a similar manner to the method described in example 38, but using 1-ethyl-1H-indole-3-carboxylic acid as an amorphous white solid.¹HNMR[CD₃OD]：δ7.75-7.63(m，2H)，7.52(d，1H)，7.43-7.36(m，3H)，7.35-7.15(m，3H)，4.63-4.51(m，2H)，4.30(q，2H)，4.11(s，2H)，3.30-3.13(m，2H)，3.03-2.85(m，1H)，2.00-1.86(m，2H)，1.85-1.68(m，2H)，1.49(t，3H).MS(ion spray)：362(M⁺+1).

Example 103

(3S, 4S) and (3R, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride

A.4-hydroxy-5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

To a solution of 4-piperidone-3-carboxylic acid ethyl ester hydrochloride (5g, 24.05mmol) in THF (70ml) and water (35ml) at 0 deg.C was added triethylamine (8.7ml, 62.5mmol) followed by N- (benzyloxycarbonyloxy) succinimide (7.79g, 31.27 mmol). The reaction mixture was stirred and allowed to warm to room temperature. After 3 hours, the reaction mixture was diluted with water (50ml) and ethyl acetate (100ml) was added. The aqueous phase was extracted with ethyl acetate (2 × 100 ml). The combined organic phases were washed with brine (50ml) and dried (MgSO)₄) The solvent was removed in vacuo. The crude product was purified by column chromatography on silica gel (eluent ethyl acetate: pentane 1: 5) to give 4-hydroxy-5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester as a colourless oil (7.26g, 94%). MS (EI)305 (M)⁺).

B.4-Trifluoromethanesulfonyloxy-5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

1-benzyl 3-ethyl 4-hydroxy-5, 6-dihydro-2H-pyridine-1, 3-dicarboxylate (15.94g, 52.5mmol) was dissolved in THF (150ml) under nitrogen and cooled at-78 deg.C while adding sodium bis (trimethylsilyl) amide (1M in THF; 68ml, 68mmol) via cannula. After stirring at this temperature for 30 minutes, a solution of N-phenyltrifluoromethanesulfonimide (22.42g, 62.8mmol) in THF (230ml) was added via cannula. The reaction mixture was stirred at this temperature for 10 minutes, then warmed to 0 ℃ and stirred for 2 hours. After 48 hours, the reaction mixture is chargedWater was added to quench the reaction, extracted with DCM and dried (MgSO)₄) And concentrated in vacuo. The crude product was purified by flash column chromatography on silica gel (eluent ethyl acetate: pentane 4: 1) to give 4-trifluoromethanesulfonyloxy-5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester as a colorless oil (18.59g, 81%). The material decomposed to a dark red color after standing and was therefore stored under nitrogen and in the dark at 0 ℃. MS (EI)437 (M)⁺).

C.4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

4-Trifluoromethanesulfonyloxy-5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (200mg, 0.458mmol) was dissolved in anhydrous dioxane (6ml) and added dropwise to potassium acetate (135mg, 1.374mmol), 1 '-bis (diphenylphosphino) ferrocene (8mg, 0.014mmol), [1, 1' -bis (diphenylphosphino) ferrocenyl ] under nitrogen via a cannula]Dichloropalladium-dichloromethane complex (10mg, 0.014mmol) and bis-pinacoldiborane (116mg, 0.458 mmol). The mixture was heated at 80 ℃ overnight, cooled to room temperature, and partitioned between DCM and water. The aqueous phase was extracted with DCM, the organic phases were combined and dried (MgSO)₄). The crude product was purified by flash column chromatography on silica gel (eluent pentane: ethyl acetate 5: 1) to give 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester as a colorless oil (94mg, 50%). MS (EI)415 (M)⁺).

4- {3- [ (N, N-bis-tert-butoxycarbonyl) aminomethyl ] phenyl } -5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester

Reacting 3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl under nitrogen]Bromobenzene (3.51g, 9.1mmol) (prepared as in example 1A) and 4- (4, 4, 5, 5-tetramethyl-1, 3, 2-dioxaborolan-2-yl) -5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (3.6g, 8.67mmol) in DMF (120ml) were added via cannula to a solution of [1, 1' -bis (diphenylphosphino) ferrocenyl group]Dichloro palladium-diMethyl chloride complex (425mg, 0.52mmol) and potassium carbonate (3.59g, 26 mmol). The reaction mixture was heated at 80 ℃ overnight, concentrated to dryness in vacuo, and the residue partitioned between DCM and water. The aqueous phase was extracted with DCM, the organic phases were combined, washed with brine and dried (MgSO)₄). The crude material was purified by column chromatography on silica gel (eluent pentane: ethyl acetate 6: 1) to give 4- {3- [ (N, N-bis-tert-butoxycarbonyl) aminomethyl]Phenyl } -5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester as a colorless oil (2.27g, 44%). MS (EI)594 (M)⁺).

(3S, 4S) and (3R, 4R) -4- {3- [ (N, N-bis-tert-butoxycarbonyl) aminomethyl ] phenyl } -piperidine-3-carboxylic acid ethyl ester

Solid carbon dioxide (1g) was added to 4- {3- [ (N, N-bis-tert-butoxycarbonyl) aminomethyl]Phenyl } -5, 6-dihydro-2H-pyridine-1, 3-dicarboxylic acid 1-benzyl ester 3-ethyl ester (2.07g, 3.48mmol) in IMS (20 ml). 10% Palladium on carbon (200mg) was added to the solution, and the reaction mixture was stirred at room temperature under a hydrogen atmosphere for 4 hours. The palladium on carbon was filtered off through celite to give (3S, 4S) and (3R, 4R) -4- {3- [ (N, N-bis-tert-butoxycarbonyl) aminomethyl]A1: 1 mixture of ethyl phenyl } -piperidine-3-carboxylate as a pale grey/brown oil (1.35g, 84%) was sufficiently pure for the subsequent reaction. MS (EI)462 (M)⁺).

(3S, 4S) and ethyl (3R, 4R) -4- {3- [ (bis-tert-butoxycarbonyl) aminomethyl ] phenyl } -1- (5-phenethylpyridine-3-carbonyl) piperidine-3-carboxylate

Carried out in a similar manner to the procedure described in example 2B, 2B but using (3S, 4S) and (3R, 4R) -4- {3- [ (N, N-bis-tert-butoxycarbonyl) aminomethyl]1: 1 mixture of ethyl phenyl } -piperidine-3-carboxylate instead of 4- {3- [ N, N-bis (tert-butoxycarbonyl) aminomethyl]Phenyl } piperidine, preparation of (3S, 4S) and (3R, 4R) -4- {3- [ (bis-tert-butoxycarbonyl) aminomethyl]A1: 1 mixture of ethyl phenyl } -1- (5-phenethylpyridine-3-carbonyl) piperidine-3-carboxylate as a colorless glassy solid (414mg, 0.62 mmol). MS (EI)671 (M)⁺).

G. (3S, 4S) and (3R, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride

The procedure was carried out in a similar manner to the procedure described in example 1D, but using (3S, 4S) and (3R, 4R) -4- {3- [ (bis-tert-butoxycarbonyl) aminomethyl]1: 1 mixture of ethyl phenyl } -1- (5-phenethylpyridine-3-carbonyl) piperidine-3-carboxylate instead of N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenylethynylpyridine-3-carbonyl) piperidin-4-yl]Benzylamine, a 1: 1 mixture of (3S, 4S) and (3R, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride was prepared as a white solid. MS (EI)471 (M)⁺).

Example 104

(3R, 4S) and (3S, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride

A. (3R, 4S) and ethyl (3S, 4R) -4- {3- [ (tert-butoxycarbonyl) aminomethyl ] phenyl } -1- (5-phenethylpyridine-3-carbonyl) -piperidine-3-carboxylate

Sodium hydride (10mg, 60% mineral oil, 0.25mmol) was added to ethanol (10ml), and after the effervescence subsided, (3S, 4S) and (3R, 4R) -4- {3- [ (bis-tert-butoxycarbonyl) aminomethyl were added at room temperature]A1: 1 mixture of ethyl phenyl } -1- (5-phenethylpyridine-3-carbonyl) piperidine-3-carboxylate (100 mg). After 1 hour, the solvent was removed in vacuo and the residue partitioned between DCM and water. The aqueous phase was extracted with DCM, the organic phases were combined, washed with brine and dried (MgSO)₄). The crude material was purified by column chromatography on silica gel (eluent DCM: MeOH 10: 1) to give (3R, 4S) and (3S, 4R) -4- {3- [ (tert-butoxycarbonyl) aminomethyl]A1: 1 mixture of phenyl } -1- (5-phenethylpyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester was a light yellow glassy solid (43mg, 51%). MS (EI)571 (M)⁺).

Dihydrochloride of (3R, 4S) and (3S, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester

The procedure was carried out in a similar manner to the procedure described in example 1D, but using (3R, 4S) and (3S, 4R) -4- {3- [ (tert-butoxycarbonyl) aminomethyl]1: 1 mixture of phenyl } -1- (5-phenethylpyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester instead of N, N-bis- (tert-butoxycarbonyl) -3- [1- (5-phenylethynylpyridine-3-carbonyl) piperidin-4-yl]Benzylamine, a 1: 1 mixture of (3R, 4S) and (3S, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride was prepared as a white solid. MS (EI)471 (M)⁺).

Example 105

[4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-2-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride

A.5-Boc-amino-nicotinic acid

To a solution of diethyl 3, 5-pyridinedicarboxylate (prepared according to J.C. Speelman and R.M. Kellogg, J.org.chem., 1990, 55(2), p.647-653 procedures; 64.19g, 0.248mol) in ethanol (650ml) was added KOH particles (14.56g, 0.260 mol). The reaction mixture was stirred at room temperature overnight. The solvent was evaporated to give a white solid, which was washed with dichloromethane and then dissolved in water. The aqueous solution was extracted with ether and then acidified to pH 3. The resulting white precipitate was collected by filtration and dried to give monomethyl pyridine-3, 5-dicarboxylate (33.70 g). A portion of this material (10.00g, 51.3mmol) was dissolved in dry tert-butanol (300ml) followed by triethylamine (7.85ml, 56.4mmol) and diphenylphosphoryl azide (11.5ml, 53.4 mmol). The mixture was refluxed for 90 minutes and then stirred at ambient temperature overnight. The solvent was removed under reduced pressure and the residue partitioned between water and dichloromethane. The layers were separated and the aqueous phase was extracted twice with dichloromethane. The combined organic phases were dried and concentrated. Chromatography on silica gel eluting with a mixture of pentane and ethyl acetate (3: 1, v/v) gave ethyl 5-tert-butoxycarbonylamino-nicotinate (4.79 g). The ester was dissolved in methanol (45ml) and treated with 1N NaOH (54ml, 54 mmol). After stirring for 2 hours, the volatiles were evaporated under reduced pressure and the residue was treated with 1N HCl until the resulting slurry reached pH 3. For treatingThe precipitate was collected by filtration, washed with water, and dried to give 5-tert-butoxycarbonylamino-nicotinic acid (4.21 g).¹HNMR(300Mz，DMSO-d₆)δ13.39(br s，1H)，9.82(s，1H)，8.78(d，J＝2.5Hz，1H)，8.69(d，J＝1.9Hz，1H)，8.45-8.50(m，1H)，1.50(s，9H)；¹³C NMR(75MHz，DMSO-d₆)δ166.2，152.7，143.4，143.2，136.2，126.3，124.9，80.0，27.9；MS(ESI)m/z 239(M+H).

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) formyl ] -pyridin-3-yl } carbamic acid tert-butyl ester

To a solution of 4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidine (0.1545g, 0.3956mmol, example 1B), 5-tert-butoxycarbonylamino-nicotinic acid (0.0966g, 0.4055mmol), 1-hydroxy-7-azabenzotriazole (0.0290g, 0.2131mmol) and 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (0.1500g, 0.7824mmol) in dimethylformamide (5.0ml) at 0 deg.C was added pyridine (0.065ml, 0.8037 mmol). The reaction mixture was stirred at 0 ℃ for 30 minutes and then warmed to room temperature under an inert atmosphere. After 16 h at ambient temperature, the reaction solution was diluted with ethyl acetate (30ml) and washed with saturated ammonium chloride (2 × 15ml), saturated sodium bicarbonate (15ml) and brine (15 ml). The organic phase is dried over magnesium sulfate, filtered and evaporated to dryness. The residue was chromatographed on silica gel eluting with a mixture of ethyl acetate and dichloromethane (1: 1, v/v) to give {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) formyl ] -pyridin-3-yl } carbamic acid tert-butyl ester as a colorless oil (0.1812 g): TLC, 50: 50-dichloromethane: ethyl acetate,

R_f＝0.20.¹HNMR(300MHz，CDCl₃)δ8.67(d，J＝2.6Hz，1H)，8.34(d，J＝1.4Hz，1H)，8.09(s，1H)，7.93(s，1H)，7.21-7.35(m，1H)，7.08-7.18(m，3H)，4.81-4.93(m，1H)，4.78(s，2H)，3.81-3.93(br m，1H)，3.11-3.28(br m，1H)，2.70-2.96(m，2H)，1.51(s，9H)，1.45(s，18H)，1.40-2.02(m partiallyobscmed，4H)；¹³C NMR(75MHz，CDCl₃)δ167.5，152.6，152.5，144.8，141.3，141.0，138.9，135.7，131.8，128.5，125.6，125.3，125.2，124.1，82.4，81.0，77.2，49.3，42.5，28.1，27.8；MS(CI)m/z 611(M+H).

(4-bromo-2-fluoro-benzyl) - {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl ] -piperidin-1-yl) -formyl ] -pyridin-3-yl } -carbamic acid dimethyl-ethyl ester

To {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl [)]-phenyl } -piperidin-1-yl) formyl]A solution of tert-butyl-pyridin-3-yl } carbamate (0.0745g, 0.1220mmol) in dimethylformamide (2.0ml) was added sodium hydride (61% dispersion in mineral oil, 0.0216g, 0.5499 mmol). Deprotonation was allowed for 3 minutes while stirring under an inert atmosphere. To the anionic solution was added 4-bromo-2-fluorobenzyl bromide (0.1559g, 0.5819 mmol). The mixture was stirred for another 10 minutes, then the reaction was quenched with water (5.0 ml). The reaction solution was extracted with ethyl acetate (15ml), the organic phase was washed with brine (2 × 10ml), dried over magnesium sulfate, filtered and evaporated to dryness. The residue was purified on silica gel eluting with ethyl acetate/dichloromethane/hexane (1: 2, v/v/v) followed by ethyl acetate and dichloromethane (1: 1, v/v) to give (4-bromo-2-fluoro-benzyl) - {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl-]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl } -carbamic acid dimethyl-ethyl ester as a colourless oil (0.0917 g): TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.59

¹H NMR(300MHz，CDCl₃)δ8.47-8.51(m，2H)，7.61(br s，1H)，7.07-7.32(m，7H)，4.89(s，2H)，4.78(s，2H)，4.77-4.92(m partially obscured，1H)，3.68-3.83(br m，1H)，3.09-3.24(br m，1H)，2.70-2.97(m，2H)，1.45(s，18H)，1.44(s，9H)，1.30-2.04(m partially obscured，4H)；¹³CNMR(75MHz，CDCl₃)δ167.0，160.4(d，250.8)，154.0，152.7，148.5，144.9，139.0，138.7，132.2，131.9，130.7，129.7，127.9(d，3.4)，125.8，125.7，1253，123.8(d，14.5)，121.8(d，9.7)，119.3(d，24.8)，82.5，82.2，49.5，46.9，42.6，32.8(br)，28.4，28.2，28.0；¹⁹F NMR(282MHz，CDCl₃)δ-114.9；MS(CI)m/z797(M+H).

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-2-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride

(4-bromo-2-fluoro-benzyl) - {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } piperidin-1-yl) -formyl ] -pyridin-3-yl } -carbamic acid dimethyl-ethyl ester (0.0806g, 0.1010mmol) was treated with 4M HCl in 1, 4-dioxane (2.0ml, 8.0mmol) and stirred at ambient temperature. After 25 minutes, the reaction mixture was diluted with isopropanol (0.5ml) and stirring was continued for another 2.5 hours. The reaction solution was immersed in diethyl ether (40ml) and vigorously stirred to give a white precipitate, which was collected by filtration, washed with fresh diethyl ether (3.0ml) and dried to give 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-2-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride (0.0563 g):

¹H NMR(300MHz，DMSO-d₆)δ8.39(br s，2H)，8.16(d，J＝2.7Hz，1H)，8.08(s，1H)，7.16-7.70(m，8H)，4.49-4.64(br m，1H)，4.46(s，2H)，4.05-4.30(m，1H)，4.00(AB q，J＝5.7Hz，2H)，3.01-3.25(m，1H)，2.77-2.95(m，2H)，1.75-1.92(m，1H)，1.45-1.75(br m，3H)；¹⁹F NMR(282MHz，DMSO-d₆)δ-114.1；MS(ESI) m/z 497(M+H).

example 106

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-benzylamino-pyridin-3-yl) -methanone trihydrochloride

A. Benzyl- {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } -carbamic acid dimethyl-ethyl ester

Preparation of benzyl- (5- [1- (4- {3- [ N, N-bis-benzyl) bromide by analogy with the procedure described in example 105C, but using benzyl bromide instead of 4-bromo-2-fluorobenzyl bromide- (tert-butyloxycarbonyl) aminomethyl]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl } -carbamic acid dimethyl-ethyl ester as a yellow oil. TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.48.¹HNMR(300MHz，CDCl₃)δ8.52(d，J＝2.2Hz，1H)，8.46(d，J＝1.2Hz，1H)，7.56(s，1H)，7.04-7.38(m，9H)，4.89(s，2H)，4.78(s，2H)，4.75-4.90(m partially obscured，1H)，3.63-3.88(br m，1H)，3.00-3.19(br m，1H)，2.68-2.90(m，2H)，1.45(s，18H)，1.44(s，9H)，1.37-2.04(m，4H)；¹³C NMR(75MHz，CDCl₃)δ167.0，154.1，152.6，148.4，144.8，144.5，138.9，137.5，132.0，131.5，128.6，128.5，127.5，127.2，125.7，125.5，125.2，82.4，81.6，53.4，49.4，42.5，33.8，28.1，28.1，27.9；MS(CI) m/z 701 (M+H).

In a similar manner to the process described in example 105D, but using benzyl- {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl } -carbamic acid dimethyl-ethyl ester preparation of 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ester]-1- (5-benzylamino-pyridin-3-yl) -methanone trihydrochloride as a white solid.¹H NMR(300MHz，DMSO-d₆)δ8.45(br s，2H)，8.13(d，J＝2.5Hz，1H)，8.08(d，J＝1.0Hz，1H)，7.54(s，1H)，7.47(s，1H)，7.18-7.45(m，8H)，4.50-4.63(br m，1H)，4.45(s，2H)，4.02-4.12(m，1H)，3.99(AB q，J＝5.5Hz，2H)，3.05-3.25(m，1H)，2.70-2.95(m，2H)，1.75-1.90(br m，1H)，1.50-1.70(br m，3H)；MS(ESI)m/z 401(M+H).

Example 107

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (naphthalen-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone trihydrochloride

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) -formyl } -pyridin-3-yl } -naphthalen-2-ylmethyl-carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using 2- (bromomethyl) naphthalene instead of 4-bromo-2-fluorobenzyl bromide, {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] is prepared]-phenyl } -piperidin-1-yl) -formyl } -pyridin-3-yl } -naphthalen-2-ylmethyl-carbamic acid dimethyl-ethyl ester as a colorless oil. TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.42.¹H NMR(300MHz，CDCl₃)δ8.55(d，J＝1.8Hz，1H)，8.13(d，J＝187.5Hz，1H)，7.68-7.83(m，3H)，7.60(s，1H)，7.54(br s，1H)，7.35-7.49(m，3H)，7.21-7.29(mpartially obscured，1H)，7.16(d，J＝7.7Hz，1H)，7.08(s，1H)，7.01(d，J＝7.7Hz，1H)，5.00-5.08(m，2H)，4.77(s，2H)，3.48-3.62(br m，1H)，2.59-3.03(m，3H)，1.45(s，27H)，1.27-1.95(m，4H)；¹³CNMR(75MHz，CDCl₃)δ166.9，154.3，152.6，148.6，144.8，144.7，138.9，138.8，134.9，133.3，132.8，132.2，131.6，128.6，127.7，126.3，126.2，126.0，125.8，125.5，125.3，125.2，82.4，81.8，53.6，49.4，42.5，33.2，28.4，28.2，28.0；MS(CI) m/z 752(M+H).

In a similar manner to the method described in example 105D, but using {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) -formyl } -pyridin-3-yl } -naphthalen-2-ylmethyl-carbamic acid dimethyl-ethyl ester, 1- [4- (3-aminomethylphenyl) -piperidin-1-yl ] -1- {5- [ (naphthalen-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone trihydrochloride was prepared as a white solid.

¹H NMR(300MHz，DMSO-d₆)δ8.34(br s，2H)，8.17(s，1H)，8.03(s，1H)，7.75-7.97(m，4H)，5.58-7.77(m，1H)，7.25-7.57(m，6H)，7.22(d，J＝7.2Hz，1H)，4.61(s，2H)，4.50-4.68(m partially obscured，1H)，4.10-4.35(m，1H)，4.00(AB q，J＝5.7Hz，2H)，2.91-3.12(m，1H)，2.66-2.90(m，2H)，1.70-1.89(m，1H)，136-1.69(m，3H)；MS(ESI)m/z 451(M+H).

Example 108

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride

(4-bromobenzyl) - {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } -carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using 4-bromobenzyl bromide instead of 4-bromo-2-fluorobenzyl bromide, preparation of (4-bromobenzyl) - {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-bromide]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl]Dimethyl-ethyl carbamate, as a colorless oil. TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.41.

¹H NMR(300MHz，CDCl₃)δ8.45-8.51(m，2H)，7.56(br s，1H)，7.43(d，J＝8.4Hz，2H)，7.24-7.30(m partially obscured，1H)，7.11(d，J＝8.4Hz，2H)，6.96-7.17(mpartially obscured，3H)，4.83(s，2H)，4.77(s，2H)，4.75-4.87(m partially obscured，1H)，3.65-3.80(brm，1H)，3.05-3.23(br m，1H)，2.69-2.91(m，2H)，1.45(s，18H)，1.43(s，9H)，1.30-2.00(m，4H)；¹³CNMR(75MHz，CDCl₃)δ166.8，154.0，152.5，148.4，144.7，138.9，138.7，136.5，132.1，131.8，131.7，131.5，129.0，128.6，125.7，125.5，125.2，121.4，82.4，81.9，52.8，49.3，42.5，33.5，28.3，28.1，27.9；MS(CI) m/z 781(M+H).

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-benzylamino) -pyridin-3-yl ] methanone trihydrochloride

In a similar manner to the method described in example 105D, but using (4-bromobenzyl) - {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } -carbamic acid dimethyl-ethyl ester, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride was prepared as a cream-colored solid.

¹H NMR(300MHz，DMSO-d₆)δ8.34(br s，2H)，8.11(d，J＝2.5Hz，1H)，8.04(s，1H)，7.52(d，J＝8.5Hz，2H)，7.34(d，J＝8.5Hz，2H)，7.15-7.67(m，5H)，4.49-4.64(br m，1H)，4.42(s，2H)，4.05-4.15(m，1H)，4.01(AB q，J＝5.7Hz，2H)，3.00-3.20(m，H)，2.70-2.90(m，2H)，1.72-1.88(m，1H)，1.45-1.70(m，3H)；MS(ESI) m/z 479(M+H).

Example 109

3- [ (5- {1- [4- (3-aminomethyl-phenyl) piperidin-1-yl ] -formyl } -pyridin-3-ylamino) -methyl ] -benzonitrile trihydrochloride salt

{5- [1- (4- {3-N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } - (3-cyano-benzyl) -carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using α -bromo-m-tolunitrile instead of 4-bromo-2-fluorobenzyl bromide, {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-bromide is prepared]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl } - (3-cyano-benzyl) -carbamic acid dimethyl-ethyl ester as a yellow oil. TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.44.

¹H NMR(300MHz，CDCl₃)δ8.46-8.52(m，2H)，7.51-7.65(m，3H)，7.36-7.50(m，2H)，7.24-7.31(m partially obscured，1H)，7.03-7.18(m，3H)，4.92(s，2H)，4.79-4.92(m partially obscured，1H)，4.78(s，2H)，3.70-3.85(br m，1H)，3.10-3.28(br m，1H)，2.71-2.99(m，2H)，1.45(s，18H)，1.44(s，9H)，1.30-2.05(m partially obscured，4H)；¹³C NMR(75MHz CDCl₃)δ166.7，153.8，152.5，148.1，145.2，144.7，139.2，138.9，138.7，132.1，131.9，131.5，131.2，130.6，129.6，128.6，125.6，125.5，125.2，118.3，112.9，82.4，80.6，52.8，49.3，42.4，33.5，28.3，28.0，27.9；MS(CI) m/z 727(M+H).

3- [ (5- {1- [4- (3-aminomethyl-phenyl) piperidin-1-yl ] -formyl } -pyridin-3-ylamino) -methyl) -benzonitrile trihydrochloride

In a similar manner to the method described in example 105D, but using {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } - (3-cyano-benzyl) -carbamic acid dimethyl-ethyl ester, 3- [ (5- {1- [4- (3-aminomethylphenyl) piperidin-1-yl ] -formyl } -pyridin-3-ylamino) -methyl ] -benzonitrile trihydrochloride was prepared as a white solid.

¹H NMR(300MHz，DMSO-d₆)δ8.33(br s，2H)，8.13(d，J＝2.5Hz，1H)，8.02(s，1H)，7.80-7.91(m，1H)，7.63-7.75(m，2H)，7.42-7.58(m，H)，7.20-7.7.41(m，4H)，4.51(s，2H)，4.40-4.62(m partially obscured，1H)，4.10-4.25(m，1H)，4.00(AB q，J＝5.7Hz，2H)，2.90-3.20(m，1H)，2.72-2.93(m，2H)，1.75-1.90(br m，1H)，1.45-1.70(br m，3H)；MS(ESI) m/z 426(M+H).

Example 110

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (2-chloro-4-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } - (2-chloro-4-fluoro-benzyl) -carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using 2-chloro-4-fluorobenzyl bromide instead of 4-bromo-2-fluorobenzyl bromide, {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] is prepared]-phenyl } -piperidin-1-yl) -Formyl radical]-pyridin-3-yl } - (2-chloro-4-fluoro-benzyl) -carbamic acid dimethyl-ethyl ester as a colorless oil. TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.48.

¹H NMR(300MHz，CDCl₃)δ8.51(d，J＝2.2Hz，1H)，8.46(d，J＝1.8Hz，1H)，7.62(s，1H)，7.24-7.34(m，2H)，7.04-7.19(m，4H)，6.97(td，J＝8.2，2Hz，1H)，4.96(s，2H)，4.77(s，2H)，4.75-4.90(m partially obscured，1H)，3.70-3.85(br m，1H)，3.05-3.25(br m，1H)，2.70-2.90(m，J＝21.45，s Hz，18H)，1.44(s，9H)，1.30-2.05(m，4H)；¹³CNMR(75MHz，CDCl₃)δ166.9，161.8(d，250.1)，153.8，152.6，148.1，144.7，144.6，138.9，138.6，133.6(d，9.7)，131.8，131.7，130.8(d，3.4)，129.8(d，7.6)，128.6，125.7，125.6，125.2，117.0(d，24.9)，114.3(d，21.4)，82.4，82.1，50.3，49.4，42.5，33.8，28.3，28.1，27.9；¹⁹F NMR(282MHz，CDCl₃)δ-112.0；MS(CI) m/z 754(M+H).

In a similar manner to the method described in example 105D, but using {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } - (2-chloro-4-fluoro-benzyl) -carbamic acid dimethyl-ethyl ester, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (2-chloro-4-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride was prepared as a white solid.

¹H NMR(300MHz，DMSO-d₆)δ8.34(br s，2H)，8.15(d，J＝2.5Hz，1H)，8.07(s，1H)，7.12-7.55(m，8H)，4.50-4.65(br m，1H)，4.46(s，2H)，4.12-4.24(br m，1H)，4.00(AB q，J＝5.8Hz，2H)，3.05-3.20(br m，1H)，2.70-2.90(m，2H)，1.72-1.90(br m，1H)，1.48-1.73(br m，3H)；¹⁹F NMR(282MHz，DMSO-d₆)δ-112.6；MS(ESI)m/z 453(M+H).

Example 111

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-trifluoromethoxy-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } - (4-trifluoromethoxy-benzyl) -carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using 4- (trifluoromethoxy) benzyl bromide instead of 4-bromo-2-fluorobenzyl bromide, preparation of {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl } - (4-trifluoromethoxy-benzyl) -carbamic acid dimethyl-ethyl ester as a colorless oil. TLC, 50: 50-dichloromethane: ethyl acetate, R_f＝0.48.

¹H NMR(300MHz，CDCl₃)δ8.45-8.53(m，2H)，7.60(s，1H)，7.20-7.30(m，3H)，7.05-7.20(m，5H)，4.88(s，2H)，4.77(s，2H)，4.75-4.90(m partiallyobscured，1H)，3.70-3.84(br m，1H)，3.08-3.24(br m，1H)，2.70-2.93(m，2H)，1.45(s，18H)，1.44(s，9H)，1.35-2.05(m，4H)；¹³C NMR(75MHz CDCl₃)δ166.9，154.0，152.6，148.3，144.7，144.6，138.9，138.8，136.3，132.2，131.9，128.7，128.6，125.7，125.6，125.2，121.2，120.1(q，262)，82.4，82.0，52.7，49.4，42.5，32.3，28.3，28.1，27.9；¹⁹F NMR(282MHz，CDCl₃)δ-57.4；MS(CI)m/z 786(M+H).

In a similar manner to the method described in example 105D, but using {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } - (4-trifluoromethoxy-benzyl) -carbamic acid dimethyl-ethyl ester, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-trifluoromethoxy-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride was prepared as a white solid.

¹H NMR(300MHz，DMSO-d₆)δ8.35(br s，2H)，8.12(d，J＝2.8Hz，1H)，8.05(s，1H)，7.20-7.75(m，9H)，4.50-4.65(m，1H)，4.48(s，2H)，4.05-4.20(m，1H)，4.00(ABq，J＝5.9Hz，2H)，3.05-3.25(m，1H)，2.70-2.90(m，2H)，1.75-1.90(m，1H)，1.50-1.70(br m，3H)；¹⁹FNMR(282MHz，DMSO-d₆)δ-56.3；MS(ESI)m/z 485(M+H).

Example 112

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-3-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate hydrochloride

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } -pyridin-3-ylmethyl-carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using 3- (chloromethyl) pyridine hydrochloride instead of 4-bromo-2-fluorobenzyl bromide, {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] amide is prepared]-phenyl } -piperidin-1-yl) -formyl]-pyridin-3-yl } -pyridin-3-ylmethyl-carbamic acid dimethyl-ethyl ester as a colorless oil. TLC, 15: 85 isopropanol dichloromethane, R_f＝0.54.¹H NMR(300MHz，CDCl₃)δ8.46-8.56(m，4H)，7.53-7.62(m，2H)，7.22-7.31(m partially obscured，2H)，7.05-7.18(m，3H))，4.90(s，2H)，4.77(s，2H)，4.75-4.99(m partially obscured，1H)，3.69-3.83(br m，1H)，3.05-3.25(br m，1H)，2.70-2.96(m，2H)，1.45(s，18H)，1.44(s，9H)，1.20-2.03(m，4H)；¹³C NMR(75MHz，CDCl₃)δ166.8，154.0，152.6，149.1，149.0，148.6，144.9，144.7，138.9，138.7，135.1，133.1，132.4，131.9，128.7，125.7，125.6，1253，123.6，82.5，82.2，51.2，49.4，42.6，33.9，28.4，28.2，28.0；MS(CI)m/z 702(M+H).

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-3-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrah-ydrochloride

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] pyridin-3-yl } -pyridin-3-ylmethyl-carbamic acid dimethyl-ethyl ester (0.0250g, 0.0356mmol) was treated with a 5-6M HCl in isopropanol (1.0ml, 8.0mmol) and stirred at ambient temperature. After 90 minutes, the reaction mixture was diluted with methanol (0.5ml) and stirring was continued for a further 75 minutes. The reaction solution was immersed in diethyl ether (40ml) and vigorously stirred to give a white precipitate, which was collected by filtration, washed with fresh diethyl ether (3.0ml) and dried to give 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-3-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate hydrochloride (0.0160 g):

¹H NMR(300MHz，DMSO-d₆)δ8.60-8.95(m，2H)，8.39(br s，2H)，8.29(d，J＝8.0Hz，1H)，7.97-8.25(m，2H)，7.65-7.85(m，2H)，7.47(d，J＝8.0Hz，2H)，7.20-7.38(m，3H)，4.63(s，2H)，4.43-4.61(m partially obscured，1H)，4.00(AB q，J＝5.8Hz，2H)，3.05-3.25(m partially obscured，1H)，2.72-2.95(m，2H)，1.80-1.88(m，1H)，1.47-1.77(m，3H)；MS(CI) m/z 402(M+H).

example 113

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate

{5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } -pyridin-2-ylmethyl-carbamic acid dimethyl-ethyl ester

By proceeding in a similar manner to the method described in example 105C, but using 2- (chloromethyl) pyridine hydrochloride instead of 4-bromo-2-fluorobenzyl bromide, {5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] is prepared]-phenyl radical} -piperidin-1-yl) -formyl]-pyridin-3-yl } -pyridin-2-ylmethyl-carbamic acid dimethyl-ethyl ester as a colorless oil. TLC, 50: 50 dichloromethane: ethyl acetate, R_f＝0.09.

¹H NMR(300MHz CDCl₃)δ8.67(d，J＝2.3Hz，1H，8.52(d，J＝4.7Hz，1H)，8.44(d，J＝1.8Hz，1H)，7.81(s，1H)，7.59-7.72(m，1H)，7.22-7.31(m partiallyobscured，2H)，7.00-7.20(m，4H)，4.97(s，2H)，4.77(s，2H)，4.72-4.90(m partially obscured，1H)，3.74-3.89(br m，1H)，3.04-3.25(br m，1H)，2.69-2.94(m，2H)，1.45(s，18H)，1.41(s，9H)，1.23-2.03(m partially obscured，4H)；MS(CI) m/z 702(M+H).

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrah-ydrochloride

In a similar manner to the procedure described in example 112B, but using 5- [1- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidin-1-yl) -formyl ] -pyridin-3-yl } -pyridin-2-ylmethyl-carbamic acid dimethyl-ethyl ester, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate salt was prepared as a white solid. MS (ESI) M/z 402(M + H).

The following compounds were prepared in a similar manner to the methods described in examples 105 and 112:

example 114

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-4-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate hydrochloride

Example 115

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-benzylamino-phenyl) -methanone dihydrochloride

[3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester

By proceeding in a similar manner to the method described in example 105B, but using 3- (Boc amino) benzoic acid instead of 5-tert-butoxycarbonylamino-nicotinic acid, [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-acid ] was prepared]-phenyl } -piperidine-1-carbonyl) -phenyl]-tert-butyl carbamate as white solid.¹H NMR(300MHz CDCl₃)δ7.40-7.50(m，2H)，7.22-7.37(m，2H)，7.04-7.15(m，4H)，4.77-4.90(br m，1H)，4.76(s，2H)，3.81-3.96(br m，1H)，3.05-3.20(br m，1H)，2.68-2.90(m，2H)，1.52(s，9H)，1.45(s，18H)，1.35-1.85(m partially obscured，4H))；MS(CI) m/z610(M+H).

B. Benzyl- [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester

In a similar manner to the procedure described in example 105C, but using benzyl bromide instead of 4-bromo-2-fluorobenzyl bromide and [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-bromide]-phenyl } -piperidine-1-carbonyl) -phenyl]Preparation of benzyl- [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -carbamic acid tert-butyl ester]-phenyl } -piperidine-1-carbonyl) -phenyl]-tert-butyl carbamate as white solid.¹H NMR(300MHz，CDCl₃)δ7.03-7.34(m，13H)，4.84(br s，2H)，4.78-4.90(m partially obscured，1H)，4.77(s，2H)，3.69-3.85(brm，1H)，2.90-3.10(br m，1H)，2.65-2.88(m，2H)，1.45(s，18H)，1.41(s，9H)，1.35-1.95(m partiallyobscured，4H))；MS(CI) m/z 700(M+H).

C.1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-benzylamino-phenyl) -methanone dihydrochloride

By proceeding in a similar manner to the method described in example 105D, but using the benzyl- [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester prepared, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-benzylamino-phenyl) -methanone dihydrochloride is prepared as a white solid. MS (ESI) M/z 400(M + H).

Example 116

1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (naphthalen-2-ylmethyl) -amino ] -phenyl } -methanone dihydrochloride

[3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -naphthalen-2-ylmethyl-carbamic acid tert-butyl ester

By proceeding in a similar manner to the method described in example 105C, but using 2- (bromomethyl) naphthalene instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, we prepare [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -naphthalen-2-ylmethyl-carbamic acid tert-butyl ester as a white solid. MS (ESI) M/z650(M + H).

1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (naphthalen-2-ylmethyl) -amino ] -phenyl } methanone dihydrochloride

By proceeding in a similar manner to the method described in example 105D, but using tert-butyl [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -naphthalen-2-ylmethyl-carbamate, 1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (naphthalen-2-ylmethyl) -amino ] -phenyl ] -methanone dihydrochloride is prepared as a white solid. MS (ESI) M/z 450(M + H).

Example 117

3- [ (3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -phenylamino) -methyl ] -benzonitrile dihydrochloride

[3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] - (3-cyano-benzyl) -carbamic acid tert-butyl ester

In a similar manner to the procedure described in example 105C, but using α -bromo-m-tolunitrile instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, the preparation of [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] - (3-cyano-benzyl) -carbamic acid tert-butyl ester was prepared as a white solid. MS (CI) M/z 725(M + H).

3- [ (3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -phenylamino) -methyl ] benzonitrile dihydrochloride

By proceeding in a similar manner to the method described in example 105D, but using tert-butyl [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] - (3-cyano-benzyl) -carbamate, 3- [ (3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] formyl } -phenylamino) -methyl ] -benzonitrile dihydrochloride is prepared as a white solid. MS (ESI) M/z 425(M + H).

Example 118

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (4-bromo-benzylamino) -phenyl ] -methanone dihydrochloride

(4-bromo-benzyl) - [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester

By proceeding in a similar manner to the method described in example 105C, but using 4-bromobenzyl bromide instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, (4-bromo-benzyl) - [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester was prepared as a clear oil. MS (CI) M/z 778(M + H).

By proceeding in a similar manner to the method described in example 105D, but using (4-bromobenzyl) - [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) phenyl ] -carbamic acid tert-butyl ester, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (4-bromo-benzylamino) -phenyl ] -methanone dihydrochloride is prepared as a white solid. MS (ESI) M/z 480(M + H).

Example 119

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (pyridin-2-ylmethyl) -amino ] -phenyl } -methanone trihydrochloride

[3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -pyridin-2-ylmethyl-carbamic acid tert-butyl ester

By proceeding in a similar manner to the method described in example 105C, but using 2-methylpyridinyl chloride hydrochloride instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, we prepare [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -pyridin-2-ylmethyl-carbamic acid tert-butyl ester as a white solid.

¹H NMR(300MHz，CDCl₃)：δ8.53(d，1H)，7.60-7.70(m，2H)，7.29-7.37(m，4H)，7.08-7.24(m，5H)，4.97(s，2H)，4.70-4.90(m partially obscurd，1H)，4.77(s，2H)，3.75-3.95(br m，1H)，2.65-3.20(br m，3H)，1.40-2.00(m partially obscured，4H)，1.45(s，18H)，1.39(s，9H).MS(ESI)：m/z 701(M+H).

1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (pyridin-2-ylmethyl) -amino ] -phenyl } -methanone trihydrochloride

In a similar manner to the process described in example 105D, but using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-l-methyl- ] -methyl]-phenyl } -piperidine-1-carbonyl) -phenyl]Preparation of 1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -tert-butyl (pyridin-2-ylmethyl) -carbamate]-1- {3- [ (pyridin-2-ylmethyl) -amino]-phenyl } -methanone trihydrochloride as a light yellow solid.¹HNMR[300MHz，(CD₃)₂SO]：δ8.69(d，1H)，8.34(br s，3H)，8.19(tr，1H)，7.73(d，1H)，7.63(tr，1H)，7.25-7.42(m，4H)，7.14(tr，1H)，6.68(d，1H)，6.61(m，2H)，4.40-4.70(br m partially obscured，1H)，4.61(s，2H)，4.01(q，2H)，3.70-3.95(br m partially obscured，1H)，2.90-3.15(br m，1H)，2.65-2.90(brm，2H)，1.35-1.95(br m，4H).MS(ESI)：m/z 401(M+H).

Example 120

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (pyridin-3-ylmethyl) -amino ] -phenyl } -methanone trihydrochloride

[3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -pyridin-3-ylmethyl-carbamic acid tert-butyl ester

In a similar manner to the procedure described in example 105C, but using 3-methylpyridinyl chloride hydrochloride instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl-phenyl ] -carbamic acid tert-butyl ester, was prepared [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -pyridin-3-ylmethyl-carbamic acid tert-butyl ester as a cream-like oil.

¹H NMR(300MHz，CDCl₃)：δ8.49(br s，2H)，7.57(d，1H)，7.33(m，1H)，7.07-7.24(m，8H)，4.70-4.95(m partiallyobscured，1H)，4.85(s，2H)，4.77(s，2H)，3.65-3.90(br m，1H)，2.65-3.15(br m，3H)，1.40-2.00(mpartially obscured，4H)，1.45(s，18H)，1.41(s，9H).MS(ESI)：m/z 701(M+H).

1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (pyridin-3-ylmethyl) -amino ] -phenyl } methanone trihydrochloride

In a similar manner to the process described in example 105D, but using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-l-methyl- ] -methyl]-phenyl } -piperidine-1-carbonyl) -phenyl]-pyridin-3-ylmethyl-carbamic acid tert-butyl esterPreparation of 1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl group]-1- {3- [ (pyridin-3-ylmethyl) -amino]-phenyl } -methanone trihydrochloride as a light yellow solid.¹HNMR[300MHz，(CD₃)₂SO]：δ8.81(s，1H)，8.70(d，1H)，8.34(m，4H)，7.86(tr，1H)，7.25-7.41(m，4H)，7.14(tr，1H)，6.67(d，1H)，6.59(m，2H)，4.40-4.70(br m partially obscured，1H)，4.50(s，2H)，4.01(q，2H)，3.70-3.90(br m partially obscured，1H)，2.90-3.15(br m，1H)，2.65-2.90(br m，2H)，1.35-1.95(br m，4H).MS(ESI)：m/z 401(M+H).

Example 121

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (pyridin-4-ylmethyl) -amino ] -phenyl } -methanone trihydrochloride

[3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -pyridin-4-ylmethyl-carbamic acid tert-butyl ester

In a similar manner to the procedure described in example 105C, but using 4-methylpyridinyl chloride hydrochloride instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, was prepared [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) phenylamino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -pyridin-4-ylmethyl-carbamic acid tert-butyl ester as a cream oil.

¹H NMR(300MHz CDCl₃)：δ8.55(br d，2H)，7.33(q，2H)，7.06-7.26(m，8H)，4.70-4.90(m partially obscured，1H)，4.84(s，2H)，4.77(s，2H)，3.70-3.90(br，1H)，268-3.15(br m，3H)，1.40-2.00(m partiallyobscured，4H)，1.45(s，18H)，1.41(s，9H).MS(ESI)：m/z 701(M+H).

1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {3- [ (pyridin-4-ylmethyl) -amino ] -phenyl } -methanone trihydrochloride

Following a procedure similar to that described in example 105DBy the following formula (I), but using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl- ]]-phenyl } -piperidine-1-carbonyl) -phenyl]Preparation of 1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -carbamic acid tert-butyl ester]-1- {3- [ (pyridin-4-ylmethyl) -amino]-phenyl } -methanone trihydrochloride as a creamy oil.¹HNMR[300Mz，(CD₃)₂SO]：δ8.76(br s，2H)，8.33(br s，3H)，7.87(d，2H)，724-7.41(m，4H)，7.13(tr，1H)，6.65-7.00(br，1H)，6.56-6.64(m，3H)，4.40-4.70(br m partially obscured，1H)，4.61(s，2H)，4.01(q，2H)，3.70-3.90(br m partially obscured，1H)，2.90-3.15(br m，1H)，2.652.90(br m，2H)，1.35-1.95(br m，4H).MS(ESI)：m/z 401(M+H).

Example 122

3- [1- (5-Phenylethynyl-furan-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate

4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethyl ester

A solution of 4-piperidone monohydrate hydrochloride (13.55g, 88mmol), 2-trimethylsilylethyl-p-nitrophenylcarbonate (25.00g, 88mmol) in acetonitrile (300ml) was treated with triethylamine (50ml, 359mmol) and dimethylaminopyridine (10.78g, 88mmol) and heated at reflux for 2 h. The solution was cooled and concentrated to an oil. The residue was dissolved in dichloromethane (300ml), washed twice with 1M hydrochloric acid and twice with 1M sodium hydroxide until all yellow color was faded from the organic layer. The organic layer was then washed with brine, dried over magnesium sulfate and concentrated in vacuo to give 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethyl ester as a colorless oil (19.35 g).¹H NMR(CDCl₃，300MHz)：δ4.24(2H，t)，3.78(4H，t)，2.45(4H，t)，1.05(2H，t)，0.05(9H，s)MS(EI)284(M+CH₃CN).

B.4- (3-cyano-phenyl) -3, 6-dihydro-2H-pyridine-1-carboxylic acid 2-trimethylsilyl-ethyl ester

To a solution of lithium hexamethyldisilazide (60mmol) in anhydrous tetrahydrofuran (150ml) at-78 deg.C was added dropwise a solution of 4-oxo-piperidine-1-carboxylic acid (trimethylsilyl) ethyl ester (13.30g, 55mmol) in anhydrous tetrahydrofuran (50 ml). The addition was carried out over a period of 20 minutes, maintaining the internal temperature at-65 to-70 ℃. The solution was stirred at-78 ℃ for 45 minutes and then treated with a solution of N-phenyltrifluoromethanesulfonimide (19.65g, 55mmol) in dry tetrahydrofuran (75 ml). The solution was warmed to 0 ℃ and then stirred at 0 ℃ for 3 hours, then concentrated in vacuo. The residue was dissolved in dichloromethane, washed with water, dried over magnesium sulfate and concentrated to give 2- (trimethylsilyl) ethyl 1, 2, 3, 6-tetrahydro-4- (trifluoromethanesulfonyloxy) -pyridine-1-carboxylate as a yellow oil (22.1 g). Crude product of this material was used because it was deteriorated by silica gel or alumina column chromatography. A portion of this material (20.65g, 55mmol) was dissolved in acetonitrile (300ml) and the solution treated with 3-cyanoboronic acid (8.90g, 60mmol), 2M sodium carbonate (82.5ml, 165mmol) and lithium chloride (6.98g, 165 mmol). The heterogeneous mixture was stirred vigorously, flushed with nitrogen for 5 minutes, and then tetrakis (triphenylphosphine) palladium (0) (3.10g, 3mmol) was added. The mixture was heated to reflux (90 ℃ oil bath) for 90 minutes, then cooled and filtered. The red filtrate was concentrated and the residue partitioned between dichloromethane (100ml 3 parts) and 2M sodium carbonate (200 ml). The organic extracts were combined, dried over magnesium sulfate and then concentrated in vacuo. The resulting oil was chromatographed on silica gel eluting with a mixture of ethyl acetate, heptane and dichloromethane (1: 5: 1, v/v/v) to give 4- (3-cyano-phenyl) -3, 6-dihydro-2H-pyridine-1-carboxylic acid 2-trimethylsilyl-ethyl ester as a yellow oil (10.46 g).

¹H NMR(CDCl₃，300MHz)：δ7.40-7.65(m，4H)，6.10(m，1H)，4.23(t，2H)，4.15(d，2H)，3.70(t，2H)，2.45(m，2H)，1.12(t，2H)，0.05(s，9H).

C.4- (3-aminomethyl-phenyl) -piperidine-1-carboxylic acid 2-trimethylsilyl-ethyl ester hydrochloride

4- (3-cyanophenyl) -3, 6-dihydro-2H-pyridine-1-carboxylic acid 2-trimethylsilyl-ethyl ester (10.40g, 32mmol) was dissolved in ethanol (250ml) and concentrated hydrochloric acid was added(3ml, 35mmol) and 10% palladium on carbon (50% moisture, 5.0 g). The mixture was hydrogenated at 50psi for 4 hours, then filtered through celite and concentrated. The resulting oily solid was triturated with ether/pentane to give 4- (3-aminomethyl-phenyl) -piperidine-1-carboxylic acid 2-trimethylsilyl-ethyl ester hydrochloride as a white solid (7.10 g).¹H NMR[(CD₃)₂SO，300MHz]：δ8.38(br s，2H)，7.20-7.40(m，4H)，4.10(t，4H)，3.98(s，2H)，2.63-3.00(m，3H)，1.75(m，2H)，1.50(m，2H)，0.94(t，2H)，0.02(s，9H).LC-MS(ES)335(M⁺+H)，93％TIC.

(3-piperidin-4-yl-benzyl) carbamate Wang resin

P-nitrophenylcarbonate Wang resin (11.00g, 15mmol) and anhydrous dimethylformamide (100ml) were placed in a peptide synthesis vessel and the resin was allowed to swell for 15 minutes. It was then treated with 4- (3-aminomethyl-phenyl) -piperidine-1-carboxylic acid 2-trimethylsilyl-ethyl ester hydrochloride (7.50g, 21mmol) in 50ml dimethylformamide, dimethylaminopyridine (0.72g, 6mmol) and diisopropylethylamine. The peptide container was shaken at room temperature for 24 hours, then washed thoroughly with dimethylformamide (x5), methanol (x2), dimethylformamide (x2), methanol (x2), dichloromethane (x3), methanol (x2), dichloromethane (x2), methanol (x3), and dried. The resin was then treated with tetrahydrofuran to swell the resin and then drained. Then anhydrous tetrahydrofuran (100ml) and tetrabutylammonium fluoride (75ml, 1M tetrahydrofuran solution) were added and the resin was shaken for 18 hours. The resin was drained, washed with tetrahydrofuran (x5), methanol (x3), dichloromethane (x3), methanol (x3), dichloromethane (x3), methanol (x3) and dried to give (3-piperidin-4-yl-benzyl) carbamate Wang resin (12.30 g).

E.3- [1- (5-Phenylethynyl-furan-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate

(3-piperidin-4-yl-benzyl) carbamate Wang resin (60mg, 0.075mmol) was suspended in dimethylformamide (3ml), and 5-phenylethynyl-furan-2-carboxylic acid (80mg, 0.38mmol), diisopropylcarbodiimide (48mg, 0.38mmol) and 1-hydroxysuccinimide (Beckman @Phenylbenzotriazole (50mg, 0.38 mmol). The mixture was shaken at room temperature overnight and washed with dimethylformamide (x5), methanol (x5), dichloromethane and methanol again (5 repetitions). The resin was treated with trifluoroacetic acid and dichloromethane (1: 1v/v, 4ml) for 45 minutes and filtered. Concentrating the filtrate to obtain 3- [1- (5-phenylethynyl-furan-2-carbonyl) -piperidin-4-yl]Benzylamine trifluoroacetate as a pale yellow oil (30mg), LC-MS (ES)385 (M)⁺+H)100％TIC.

In a similar manner to the method described in example 112, the following compounds described in table 5 were prepared as the trifluoroacetate salts:

TABLE 5

Following a similar procedure to that described in example 36, but using the appropriate carboxylic acid TFP resin instead of 3, 4-dichlorobenzoic acid TFP resin, the following compounds described in table 6 were prepared as trifluoroacetates:

TABLE 6

Example 344

[4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [1, 1'; 4', 1 "] terphenyl-3-yl-methanone hydrochloride

{4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - (3-bromo-phenyl) -methanone

By proceeding in a similar manner to the method described in example 105B, but using 3-bromobenzoic acid instead of 5-tert-butoxycarbonylamino-nicotinic acid, {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - (3-bromo-phenyl) -methanone was prepared as a colorless oil. MS (CI) M/z 573(M + H).

{4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - [1, 1'; 4', 1 "] terphenyl-3-yl-methanone

In a similar manner to the procedure described in example 17D, but using 4-biphenylboronic acid instead of 1- (5-phenethyl-pyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine, {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - (3-bromo-phenyl) -methanone instead of N- (tert-butoxycarbonyl) -3-bromo-4-fluoro-benzylamine, {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - [1 is prepared, 1'; 4', 1 "] terphenyl-3-yl-methanone, as a yellow oil. MS (CI) M/z 647(M + H).

In a similar manner to the process described in example 105D, but using {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - [1, 1'; 4 ', 1 "] terphenyl-3-yl-methanone, [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [1, 1'; 4', 1 "] terphenyl-3-yl-methanone hydrochloride as a cream colored solid. MS (CI) M/z 447(M + H).

Example 345

3- [1- (6-chloroquinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride

A.6-chloroquinoline-3-carboxylic acid ethyl ester

Ethyl 4, 6-dichloroquinoline-3-carboxylate (prepared as described in C.C.price and R.M.Roberts, J.Amer.chem.Soc. (Proc. chem., USA chem., Sam., USA chem.) 68, 1204 (1964); C.J.Ohnmacht, Jr.J.Med.chem. (J.Med.Chem.) 14, 17 (1971)) (2.0g, 7.4mmol) was added portionwise to a solution of sodium borohydride (1.2g, 31mmol) in 15ml of methoxyethanol at about 0 ℃. The reaction mixture was warmed to room temperature over 3 hours and then diluted with ethyl acetate. Standard aqueous work-up (dilute HCl; saturated NaHCO)₃) After that, the organic layer was dried (Na)₂SO₄) And concentrated to a residue. The residue was air oxidized (about 14 days) and repeatedly extracted with boiling heptane. The heptane was removed in vacuo to give 6-chloroquinoline-3-carboxylic acid ethyl ester as an off-white solid.¹H NMR[(CDCl₃)，300MHz]：δ9.38(bs，1H)，8.68(s，1H)，8.05(d，1H)，7.83(s，2H)，7.69(d，1H)，4.40(q，2H)，139(t，3H).MS(EI)：236(M⁺+H).

B.6-chloroquinoline-3-carboxylic acid

Ethyl 6-chloroquinoline-3-carboxylate (0.19g, 0.81mmol) was treated with dioxane (10ml) and 10% aqueous sodium hydroxide (10ml), refluxed for 3 hours, and saponified. Removing dioxane under vacuum; the remaining aqueous solution was acidified with HCl. The precipitated product was collected, washed with water, and 6-chloroquinoline-3-carboxylic acid was isolated as an incompletely white solid (0.14g, 0.67 mmol).¹H NMR[(CD₃OD)，300MHz]：δ9.35(s，1H)，8.95(s，1H)，8.17(s，1H)，8.1(d，2H)，7.87(d，1H).

C.N, N-bis- (tert-butyloxycarbonyl) -3- [1- (6-chloroquinoline-3-carbonyl) -piperidin-4-yl ] benzylamine

The crude title compound was prepared in a similar manner to the method described in example 1C, but using 6-chloroquinoline-3-carboxylic acid instead of 5-phenylethynyl-pyridine-3-carboxylic acid. The crude product was purified by flash chromatography (25-50% ethyl acetate/heptane) to give the title compound as a white amorphous solid.¹H NMR(CDCl₃)，300MHz]：δ8.98(bs，1H)，8.20(s，1H)，8.05(d，1H)，7.88(s，1H)，7.72(d，1H)，7.08-7.31(m，4H)，4.93(br m，1H)，4.78(s，2H)，3.90(br m，1H)，3.27(br m，1H)，3.95(br m，1H)，2.82(m，1H)，1.62.1(brm，4H)，1.47(s，18H).

3- [1- (6-chloroquinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine

N, N-bis- (tert-butyloxycarbonyl) -3- [1- (6-chloroquinoline-3-carbonyl) -piperidin-4-yl at 0 ℃]Benzylamine (0.055g, 0.095mmol) was treated with 15% trifluoroacetic acid in dichloromethane (5 ml). The reaction was warmed to ambient temperature over 2.5 hours and the solvent was removed under vacuum. The residue was triturated with ether to give the title compound (0.033g, 0.087mmol) as an amorphous solid.¹H NMR[(CD₃)₂SO，500MHz]：δ8.95(s，1H)，8.44(s，1H)，8.20(s，1H)，8.07(d，1H)，7.84(d，2H)，7.23-7.40(m，4H)，4.67(m，1H)，7.34(m，3H)，4.75(br m，1H)，4.05(m，2H)，3.75(br m，1H)，3.30(br m，1H)，2.80-3.00(br m，2H)，1.90(br m，1H) 1.6-1.8(br m，3H).MS(EI)：380(M⁺+H).

Example 346

According to example 105The procedure described in B is carried out in a similar manner but using 3- (Boc amino) benzoic acid instead of 5-tert-butoxycarbonylamino-nicotinic acid to prepare [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-acid]-phenyl } -piperidine-1-carbonyl) -phenyl]-tert-butyl carbamate as white solid.¹H NMR(300MHz，CDCl₃)：δ7.40-7.50(m，2H)，7.22-7.37(m，2H)，7.04-7.15(m，4H)，4.75-4.90(br m，1H)，4.76(s，2H)，3.80-3.96(br m，1H)，3.00-3.25(br m，1H)，2.68-2.95(m，2H)，1.40-2.05(m partially obscured，4H)，1.52(s，9H)，1.45(s，18H).MS(CI)：m/z610(M+H).

B. Benzyl- [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) phenyl ] -carbamic acid tert-butyl ester

In a similar manner to the procedure described in example 105C, but using benzyl bromide instead of 4-bromo-2-fluorobenzyl bromide and [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-bromide]-phenyl } -piperidine-1-carbonyl) -phenyl]Preparation of benzyl- [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -carbamic acid tert-butyl ester]-phenyl } -piperidine-1-carbonyl) -phenyl]-tert-butyl carbamate as white solid.¹H NMR(300MHz，CDCl₃)：δ7.03-7.34(m，13H)，4.75-4.90(m partially obscured，1H)，4.84(br s，2H)，4.77(s，2H)，3.69-3.85(brm，1H)，2.90-3.10(br m，1H)，2.65-2.90(m，2H)，1.40-2.00(m partially obscured，4H)，1.45(s，18H)，1.41(s，9H).MS(CI)：m/z 700(M+H).

By proceeding in a similar manner to the method described in example 105D, but using the benzyl- [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester prepared, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-benzylamino-phenyl) -methanone dihydrochloride is prepared as a white solid.

¹H NMR[300MHz，(CD₃)₂SO]：δ8.26(br s，3H)，7.20-7.55(m，9H)，7.11(tr，1H)，6.66(d，1H)，6.57(m，2H)，4.40-4.70(br m，1H)，430(s，2H)，4.15(m，1H)，4.01(q，2H)，2.90-3.15(br m，1H)，2.65-2.90(br m，2H)，1.35-1.95(brm，4H).MS(ESI)：m/z 400(M+H).

Example 347

By proceeding in a similar manner to the method described in example 105C, but using 2- (bromomethyl) naphthalene instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, we prepare [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -naphthalen-2-ylmethyl-carbamic acid tert-butyl ester as a white solid.

¹H NMR(300MHz，CDCl₃)：δ7.61-7.80(m，4H)，7.38-7.45(m，3H)，6.99-7.34(m，8H)，5.00(br s，2H)，4.70-4.90(m partially obscured，1H)，4.76(s，2H)，3.55-3.75(br m，1H)，2.70-2.95(br m，2H)，2.55-2.70(m，1H)，1.40-1.95(m partially obscured，4H)，1.45(s，18H)，1.42(s，9H).MS(ESI)：m/z 650(M+H).

In a similar manner to the process described in example 105D, but using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-l-methyl- ] -methyl]-phenyl } -piperidine-1-carbonyl) -phenyl]Preparation of 1- {4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -2-ylmethyl-carbamic acid tert-butyl ester]-1- {3- [ (naphthalen-2-ylmethyl) -amino]-phenyl-Methanone dihydrochloride as a white solid.¹HNMR[300MHz，(CD₃)₂SO]：δ8.22(br s，3H)，7.81-7.88(m，4H)，7.11-7.54(m，8H)，6.69(d，1H)，6.59(s，1H)，6.54(d，1H)，4.45-4.65(m partially obscured，1H)，4.47(s，2H)，4.01(q，2H)，3.60-3.80(m partially obscured，1H)，2.85-3.05(br m，1H)，2.65-2.85(bt m，2H)，1.30-1.95(br m，4H).MS(ESI)：m/z 450(M+H).

Example 348

3- [ {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -phenylamino ] -methyl ] -benzonitrile dihydrochloride

The procedure was carried out in a similar manner to the method described in example 105C, but using α -bromo-m-tolunitrile instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-bromide]-phenyl } -piperidine-1-carbonyl) -phenyl]Preparation of [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -carbamic acid tert-butyl ester]-phenyl } -piperidine-1-carbonyl) -phenyl]- (3-cyano-benzyl) -carbamic acid tert-butyl ester as a white solid.¹H NMR(300MHz，CDCl₃)：δ7.06-7.55(m，12H)，4.70-4.90(m partially obscured，1H)，4.86(s，2H)，4.77(s，2H)，3.70-3.90(br m，1H)，2.95-3.20(br m，1H)，2.65-2.95(br m，2H)，1.40-2.00(m partially obscured，4H)，1.45(s，18H)，1.41(s，9H).MS(CI)：m/z 725(M+H).

In a similar manner to the process described in example 105D, but using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl-l-methyl- ] -methyl]-phenyl } -piperidine-1-carbonyl) -phenyl]- (3-cyano-benzyl) -carbamic acid tert-butyl ester preparation of 3- [ (3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl)]-formyl radicals} -phenylamino) -methyl]Benzonitrile dihydrochloride, as a white solid.¹H NMR[300MHz，(CD₃)₂SO]：δ8.18(br s，3H)，7.75(s，1H)，7.65(m，2H)，7.49(tr 1H)，7.21-7.35(m，4H)，7.08(tr，1H)，6.61(d，1H)，6.52(m，2H)，4.40-4.70(br m，1H)，4.33(s，2H)，3.98(q，2H)，3.50-3.70(mpartially obscured，1H)，2.85-3.10(br m，1H)，2.65-2.85(br m，2H)，1.30-1.90(br m，4H).MS(ESI)：m/z 425(M+H).

Example 349

By proceeding in a similar manner to the method described in example 105C, but using 4-bromobenzyl bromide instead of 4-bromo-2-fluorobenzyl bromide and using [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, (4-bromo-benzyl) - [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester was prepared as a clear oil.

¹H NMR(300MHz，CDCl₃)：δ7.41(d，2H)，7.06-7.38(m，8H)，7.10(d，2H)，4.70-4.90(br m，partially obscured，1H)，4.78(s，2H)，4.77(s，2H)，4.25-4.45(br m，1H)，3.70-3.85(br m，1H)，2.90-3.15(br m，1H)，2.65-2.90(br m，2H)，1.40-2.00(m partially obscured，4H)，1.45(s，18H)，1.41(s，9H).MS(CI)：m/z 778(M+H).

By proceeding in a similar manner to the method described in example 105D, but using (4-bromobenzyl) - [3- (4- {3- [ N, N-bis- (tert-butoxycarbonyl) amino-methyl ] -phenyl } -piperidine-1-carbonyl) -phenyl ] -carbamic acid tert-butyl ester, 1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [3- (4-bromo-benzylamino) -phenyl ] -methanone dihydrochloride is prepared as a white solid.

¹H NMR[300MHz，(CD₃)₂SO]：δ8.28(br s，3H)，7.25-7.66(m，8H)，7.11(tr，1H)，6.64(d，1H)，6.55(m，2H)，4.45-4.70(br m，1H)，4.28(s，2H)，4.15(m.1H)，4.01(q，2H)，2.903.15(br m，1H)，2.65-2.90(br m，2H)，1.30-1.95(br m，4H).MS(ESI)：m/z 480(M+H).

Example 350

{4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - (3-bromo-phenyl) methanone

By proceeding in a similar manner to the method described in example 105B, but using 3-bromobenzoic acid instead of 5-tert-butoxycarbonylamino-nicotinic acid, {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl ] -phenyl } -piperidin-1-yl } - (3-bromo-phenyl) -methanone was prepared as a colorless oil.

¹H NMR(300MHz，CDCl₃)：δ7.55(m，2H)，7.24-7.37(m，2H)，7.08-7.16(m，4H)，4.75-4.92(br m，1H)，4.77(s，2H)，3.75-3.90(br m，1H)，3.00-3.25(br m，1H)，2.70-3.00(br m，2H)，1.50-2.00(m partially obscured，4H)1.45(s，18H).MS(CI)：m/z 573(M+H).

In a similar manner to the procedure described in example 17D, but using 4-biphenylboronic acid instead of 1- (5-phenethyl-pyridine-3-carbonyl) -4- (pinacolato boronyl) -1, 2, 3, 6-tetrahydro-pyridine, {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - (3-bromo-phenyl) -methanone instead of N- (tert-butoxycarbonyl) -3-bromo-4-fluoro-benzylamine, {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - [1 is prepared, 1'; 4', 1 "] terphenyl-3-yl-methanone, as a yellow oil.

¹H NMR(300MHz，CDCl₃)：δ7.61-7.71(m，8H)，7.34-7.53(m，6H)，7.14(m，3H)，4.80-5.00(m，1H)，4.77(s，2H)，3.85-4.05(br m，1H)，3.00-3.25(br m，1H)，2.70-3.00(br m，2H)，1.50-2.05(m，4H)，1.44(s，18H).MS(CI)：m/z 647(M+H).

In a similar manner to the process described in example 105D, but using {4- [3-N, N-di- (tert-butoxycarbonyl) aminomethyl) -phenyl ] -piperidin-1-yl } - [1, 1'; 4 ', 1 "] terphenyl-3-yl-methanone, [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] - [1, 1'; 4', 1 "] terphenyl-3-yl-methanone hydrochloride as a cream colored solid.

¹H MR[300MHz，(CD₃)₂SO]：δ8.24(br s，3H)，7.73-7.84(m，8H)，7.29-7.61(m，9H)，4.55-4.80(br m，1H)，4.01(q，2H)，3.65-3.85(br m，1H)，2.75-3.05(br m，2H)，1.50-2.00(br m，4H).MS(CI)：m/z 447(M+H).

Example 351

4- (3-aminomethyl-phenyl) -piperidine-1-carboxylic acid (3, 4-dichloro-phenyl) -amide trifluoroacetate salt

3, 4-dichlorophenyl isocyanate (60mg, 0.319mmol) was added to a stirred solution of 4- [3- (N, N-di-tert-butoxycarbonylaminomethyl) phenyl ] piperidine (100mg, 0.256mmol) in DCM (5ml) at room temperature. After 16 h, the reaction was quenched with water (5ml), separated and the aqueous phase extracted with DCM (5 ml). The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to dryness. The residue was purified by flash column chromatography on dry silica eluting with 50: 50 dichloromethane: ethyl acetate. 4- [3- (N, N-di-tert-butoxycarbonylaminomethyl) phenyl ] -piperidine-1-carboxylic acid (3, 4-dichloro-phenyl) -amide was isolated as a colourless oil, dissolved in dichloromethane (25ml), cooled at 0 ℃ and treated with trifluoroacetic acid (3 ml). The reaction mixture was stirred at room temperature under nitrogen for 2 hours and concentrated to dryness in vacuo. The residue was dissolved in 20% acetonitrile/water (containing 0.1% trifluoroacetic acid) (9ml) and purified by preparative reverse phase HPLC (C-18, 10 micron reverse phase column) eluting with 10% to 100% acetonitrile/water (containing 0.1% trifluoroacetic acid). The product fractions were combined and acetonitrile was removed in vacuo. The aqueous residue was lyophilized to give the title compound as an amorphous white solid (68mg, 53%).

¹HNMR[(CD₃)₂SO]：δ8.82(s，H，NH)；7.88(s，H)；7.84(brs，3H，NH₃ ⁺)；7.46(s，H)；7.37-7.22(m，5H)；4.24(br d，2H)；3.99(s，2H)；2.89(br t，2H)；2.83-2.70(m，H)；1.82-1.71(m，2H)；1.60-1.44(m，2H).MS(Ion spray)：378 and 380(M⁺+1).

Example 352

4- (3-aminomethyl-phenyl) -piperidine-1-carboxylic acid 2, 3-dimethoxybenzylamide-trifluoroacetate salt

(3-piperidin-4-yl-benzyl) carbamate Wang resin (example 122D) (60. mu. mol) was suspended in dichloromethane (2ml), diisopropylethylamine (0.66mmol) was added, followed by phosgene (0.6mmol of 20% in toluene). The reaction mixture was shaken for 5 minutes, then the resin was washed with toluene (x 8). The resin was suspended in DMF (2ml), a solution of 2, 3-dimethoxybenzylamine (0.6mmol) in DMF (1.5ml) was added to it, the reaction mixture was shaken for 5 minutes, and the resin was washed with DMF (x 3). The resin was then suspended in dichloromethane (2ml) and treated with TFA (0.5 ml). The reaction mixture was shaken for 5 minutes, then the resin was filtered off and the filtrate was concentrated to dryness to give the title compound (48 μmol) as a pale yellow solid. MS (EI)383 (M)⁺).

In a manner similar to the methods described in examples 351 and 352, the following compounds described in table 7 were prepared as the trifluoroacetates salts:

TABLE 7

In vitro test procedure

As described in the background section, since all the effects of tryptase are dependent on its catalytic activity, a compound that inhibits its catalytic activity will likely inhibit the effects of tryptase. The inhibition of this catalytic activity can be measured by in vitro enzyme assays and cellular assays.

Tryptase inhibitory activity was confirmed using either ex vivo human pulmonary tryptase or recombinant human β -tryptase expressed in yeast cells. Essentially equivalent results were obtained using either the native enzyme ex vivo or the expressed enzyme. The assay procedure used a 96-well microplate (Costar 3590) using L-pyroglutamyl-L-prolyl-L-arginine-p-nitro-anilide (S2366: Quadratech) as substrate (essentially as described in McEuen et al, Biochem Pharm (biochemistry and pharmacy), 1996, 52, p.331-340). The assay was performed at room temperature using 0.5mM substrate (2 xK)_m) The microplate was read at 405nm on a microplate reader (Beckman Biomek Plate reader). The inhibition constants (Ki) for specific compounds of the invention are listed in table 8. It was determined using the procedure described herein.

Materials and methods for tryptase Primary screening (chromogenic assay)

Assay buffer

50mM Tris (pH 8.2), 100mM NaCl, 0.05% Tween 20, 50. mu.g/ml heparin

Substrate

S2366(2.5mM stock solution)

Enzyme

Purified stock solution of recombinant beta tryptase, 310. mu.g/ml

Protocol (Single point assay)

Add 60. mu.l of diluted substrate to each well (final concentration in assay buffer 500. mu.M)

Compound was added in duplicate at a final concentration of 20. mu.M in a volume of 20. mu.l

Enzyme was added to a final concentration of 50ng/ml in a volume of 20. mu.l

Total volume per well of 100. mu.l

Mixing by simple stirring, and incubating at room temperature and in the dark for 30 minutes

Absorbance reading at 405nm

Each plate had the following controls:

the method comprises the following steps: 60. mu.l substrate, 20. mu.l buffer (containing 0.2% final concentration of DMSO), 20. mu.l enzyme

Non-specificity: 60 μ l substrate, 40 μ l buffer (containing 0.2% DMSO)

The method comprises the following steps: 60. mu.l substrate, 20. mu.l buffer (without DMSO), 20. mu.l enzyme

Non-specificity: 60 μ l substrate, 40 μ l buffer (without DMSO)

Scheme (IC)₅₀And Ki assay

The protocol was essentially the same except that compounds were added in duplicate at the following final concentrations: 0.01, 0.03, 0.1, 0.3, 1, 3, 10 μ M (all dilutions were done manually). With respect to each assay, whether single point or IC₅₀Determination, all using standard compounds to derive IC₅₀For comparison. Slave IC₅₀The values can be calculated Ki using the following formula: ki ═ IC₅₀/(1+ [ substrate)]/Km)。

Using this procedure, Ki values for tryptase for specific compounds of the invention are listed in table 8 below:

TABLE 8

Example #	Name (R)	Tryptase Ki (nM)
Example #	Name (R)	Tryptase Ki (nM)	13	[4- (3-aminomethyl-phenyl) -piperidin-1-yl radical]- (5-phenethyl-thiophen-2-yl) -methanone hydrochloride	50
15	[4- (3-aminomethyl-phenyl) -piperidin-1-yl radical]- (3-phenoxymethyl-phenyl) -methanone hydrochloride	1,070	13		50
15		1,070	18	[4- (5-aminomethyl-2-methyl-phenyl) -piperidin-1-yl]- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride	69

Example #	Name (R)	Tryptase Ki (nM)
Example #	Name (R)	Tryptase Ki (nM)	19	[4- (3-aminomethyl-phenyl) -piperidin-1-yl radical]- [3- (5-phenyl-1, 3, 4-oxadiazol-2-yl) -phenyl]-methanone hydrochloride	180
35	4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-4-carbonitrile	93	19		180
35		93	36	[4- (3-Aminomethylphenyl) piperidin-1-yl group]- (3, 4-dichloro-phenyl) -methanone trifluoroacetate salt	31
48	1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl]-1- (4-chloro-phenyl) -methanone trifluoroacetate salt	390	36		31
48		390	49	1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl]-1- {3- [5- (2-chloro-phenyl) - [1, 3, 4]]Oxadiazol-2-yl]-phenyl } -methanone trifluoroacetate salt	390
70	1-[4-(3-aminomethyl-phenyl) -piperidin-1-yl]-1- (4, 5,6, 7-tetrahydro-benzo [ c ]]Thiophene-1-	290	49		390
70		290		Phenyl) -methanone trifluoroacetate salt
83	1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl]-1- [3- (4-fluoro-phenylethynyl) -phenyl]-Methanone trifluoroacetate salt	870		Phenyl) -methanone trifluoroacetate salt
83		870	92	1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl]-1- (5-chloro-thieno [3, 2-b)]Thien-2-yl) -methanone trifluoroacetate salt	190
97	[4- (3-Aminomethylphenyl) -piperidin-1-yl]- (4-phenethyl-phenyl) -methanone hydrochloride	450	92		190
97		450	98	[4- (3-Aminomethylphenyl) -piperidin-1-yl]- {3- [2- (2-hydroxyphenyl) -ethyl]-phenyl) -methanone hydrochloride	180

Example #	Name (R)	Tryptase Ki (nM)
Example #	Name (R)	Tryptase Ki (nM)	100	[4- (5-aminomethyl-thiophen-2-yl) -piperidin-1-yl]- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride	490

The data clearly show that the compounds of the invention exhibit tryptase inhibitory activity. Thus, the compounds of the present invention readily have application in pharmaceutical compositions for treating a wide range of tryptase-related disorders and methods for treating such disorders in a patient.

The present invention is not to be limited in scope by the specific embodiments described herein. Indeed, various modifications of the invention in addition to those described above will become apparent to those skilled in the art from the foregoing description and accompanying drawings. Such variations are intended to fall within the scope of the claims.

Various publications are cited herein, the disclosures of which are incorporated herein by reference in their entirety.

Claims

1. A compound of formula (Ib):

wherein:

R³is aryl, styryl, phenylallyl, cyclopentenyl, cyclohexenyl, cycloheptenyl, C_3-8Cycloalkyl, benzimidazolyl, benzothiazolyl, benzothienyl, furanyl, imidazolyl,Indolyl, indolizinyl, isoxazolyl, isoquinolyl, isothiazolyl, oxadiazolyl, pyrazinyl, pyridazinyl, pyrazolyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, 1, 3, 4-thiadiazolyl, thiazolyl, thienyl and triazolyl, pyridylvinyl, pyridylallyl, C_3-7Heterocycloalkenyl, heterocycloalkyl attached to carbon, or alkyl optionally substituted with one or more groups selected from hydroxy, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, heptoxy, alkoxycarbonylamino, cycloalkyl, piperidinyl, pyrrolidinyl, morpholinyl, tetrahydropyranyl, tetrahydrothienyl, chromanyl, dihydrobenzofuranyl, indolinyl, dihydropyrrolo [1, 2-alpha ]]Pyridyl radical, R⁶、-OR⁶、-S(O)_mR⁶or-C (═ O) -R⁶Wherein R is⁶Represents an aryl or heteroaryl group selected from benzimidazolyl, benzothiazolyl, benzothienyl, furanyl, imidazolyl, indolyl, indolizinyl, isoxazolyl, isoquinolinyl, isothiazolyl, oxadiazolyl, pyrazinyl, pyridazinyl, pyrazolyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl, quinolinyl, 1, 3, 4-thiadiazolyl, thiazolyl, thienyl and triazolyl;

R⁴is hydrogen or cyano; and is

R⁵Is hydrogen, halogen, methyl, hydroxyl, benzyloxy, ethoxy or hydroxymethyl.

2. The compound of claim 1, wherein R⁴Is hydrogen.

3. The compound of claim 1, wherein R⁵Is hydrogen.

4. The compound of claim 1, wherein R⁵Is fluorine.

5. The compound of claim 4, wherein R⁵Is linked to-CH₂NH₂Para to the group.

6. The compound of claim 1, or a pharmaceutically acceptable salt thereof, selected from:

3- [1- (5-phenylethynyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride;

3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride;

3- [1- (1-oxo-5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine hydrochloride;

3- [1- (quinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride;

3- [1- (4-phenethyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine hydrochloride;

3- [1- (5-phenethyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine hydrochloride;

3- [1- (indole-6-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate;

3- [1- (coumarin-3-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate;

3- [1- (5-phenylethynyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate;

3- [1- (4-phenylethynyl-thiophene-2-carbonyl) -piperidin-4-yl ] -benzylamine trifluoroacetate;

6-fluoro-3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride;

1- {3- [1- (5-phenethyl-pyridine-3-carbonyl) -piperidin-4-yl ] -phenyl } ethanamine dihydrochloride;

3- [1- (4-hydroxy-quinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine;

3- [1- (6-phenyl-quinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-methylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (6-chloro-benzo [ b ] thiophen-2-yl) -methanone trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-1H-indol-2-yl) -methanone trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (8-chloro-4H-1, 5-dithia-cyclopenta [ a ] naphthalen-2-yl) -methanone trifluoroacetate;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -6, 6-dimethyl-3-methylsulfanyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (6-bromo-pyridin-3-yl) -methanone bistrifluoroacetate;

6- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -2, 3-dihydro-thiazolo [3, 2-a ] pyrimidin-5-one;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl-formyl ] -3-ethylsulfanyl-6, 6-dimethyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one trifluoroacetate salt;

3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carbonitrile trifluoroacetate salt;

3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carboxylic acid trifluoroacetate salt;

3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -5, 5-dimethyl-7-oxo-4, 5,6, 7-tetrahydrobenzo [ c ] thiophene-1-carboxylic acid methyl ester trifluoroacetate salt;

1- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -3-methoxy-6, 6-dimethyl-6, 7-dihydro-5H-benzo [ c ] thiophen-4-one;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1-benzo [ b ] thiophen-2-yl-methanone-trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (3-ethoxy-thiophen-2-yl) -methanone-trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (3-chloro-phenyl) -pyridin-3-yl ] -methanone-bistrifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-benzo [ b ] thiophen-2-yl) -methanone trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (4, 5,6, 7-tetrahydro-benzo [ c ] thiophen-1-yl) methanone-trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-4-methoxy-thiophen-3-yl) -methanone-trifluoroacetate salt;

(3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1H-indol-3-yl) -methanone-trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -4-hydroxy-piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone-bistrifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (1-methyl-1H-indol-3-yl) -methanone-trifluoroacetate;

1- (3- {1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -formyl } -indol-1-yl) -ethanone-trifluoroacetate;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-methoxy-1-methyl-1H-indol-3-yl) -methanone-trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-fluoro-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-methyl-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- (5-chloro-thieno [3, 2-b ] thiophen-2-yl) -methanone trifluoroacetate salt;

1- {4- [3- (1-aminoethyl) phenyl ] -piperidin-1-yl } -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride;

1- [4- (5-aminomethyl-3-hydroxyphenyl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride;

1- [4- (5-aminomethyl-2-hydroxyphenyl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride;

1- [4- (5-aminomethyl-2-benzyloxyphenyl) -3, 6-dihydro-2H-pyridin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride;

1- [4- (5-aminomethyl-2-hydroxymethylphenyl) -3, 6-dihydro-2H-pyridin-1-yl ] -1- (5-phenethylpyridin-3-yl) -methanone;

1- [4- (5-aminomethyl-thiophen-2-yl) -piperidin-1-yl ] - (5-phenethyl-pyridin-3-yl) -methanone dihydrochloride;

[4- (5-aminomethyl-pyridin-3-yl) -piperidin-1-yl ] -1- (5-phenethyl-pyridin-3-yl) -methanone trihydrochloride;

(3S, 4S) and (3R, 4R) -4- (3-aminomethyl-phenyl) -1- (5-phenethyl-pyridine-3-carbonyl) -piperidine-3-carboxylic acid ethyl ester dihydrochloride;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-2-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- ([5- (4-bromo-2-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (naphthalen-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone trihydrochloride;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-bromo-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride;

3- [ (5- {1- [4- (3-aminomethyl-phenyl) piperidin-1-yl ] -formyl } -pyridin-3-ylamino) -methyl ] -benzonitrile trihydrochloride salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (2-chloro-4-fluoro-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- [5- (4-trifluoromethoxy-benzylamino) -pyridin-3-yl ] -methanone trihydrochloride;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-3-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-2-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate salt;

1- [4- (3-aminomethyl-phenyl) -piperidin-1-yl ] -1- {5- [ (pyridin-4-ylmethyl) -amino ] -pyridin-3-yl } -methanone tetrahydrate salt; and

3- [1- (6-chloroquinoline-3-carbonyl) -piperidin-4-yl ] -benzylamine dihydrochloride.

7. A pharmaceutical composition comprising a pharmaceutically effective amount of a compound of claim 1, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable carrier.

8. The pharmaceutical composition of claim 7, further comprising a second compound selected from the group consisting of a beta adrenergic agonist, an anticholinergic agent, an anti-inflammatory corticosteroid, and an anti-inflammatory agent.

9. The pharmaceutical composition of claim 8, wherein

The beta adrenergic agonist is selected from the group consisting of salbutamol, terbutaline, formoterol, fenoterol and pramipeline;

the anticholinergic agent is ipratropium bromide;

the antiinflammatory corticosteroid is selected from beclomethasone dipropionate, triamcinolone acetonide, flunisolide and dexamethasone; and is

The anti-inflammatory agent is selected from cromolyn sodium and nedocromil sodium.