# US 2010/0168103 A1 · Diaryl piperidine compounds as calcium channel blockers

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- Number: US 2010/0168103 A1
- Document ID: US20100168103A1
- Status: Published application
- Kind: A1
- Application number: 12/441,364
- Filed: 2007-09-14
- Published: 2010-07-01
- Earliest claimed: 2006-09-14
- Assignees: Neuromed Pharmaceuticals Ltd.
- Inventors: Hassan Pajouhesh; Yanbing Ding; Hossein Pajouhesh; Richard Holland; Gabriel Hum
- Web page: https://patentgrep.com/patent/US20100168103A1

## CPC

- A61K 31/4545: containing a six-membered ring with nitrogen as a ring hetero atom, e.g. pipamperone, anabasine
- A61K 31/496: Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
- A61P 3/00: Drugs for disorders of the metabolism (of the blood or the extracellular fluid A61P7/00)
- A61P 9/00: Drugs for disorders of the cardiovascular system
- A61P 15/16: Masculine contraceptives
- A61P 25/00: Drugs for disorders of the nervous system
- A61P 25/16: Anti-Parkinson drugs
- A61P 25/18: Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- C07D 211/26: with hydrocarbon radicals, substituted by nitrogen atoms
- C07D 401/06: linked by a carbon chain containing only aliphatic carbon atoms
- A61K: PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES (devices or methods specially adapted for bringing pharmaceutical products into particular physical or administering forms A61J3/00; chemical aspects of, or use of materials for deodorisation of air, for disinfection or sterilisation, or for bandages, dressings, absorbent pads or surgical articles A61L; soap compositions C11D)
- A61P: SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

Methods and compounds effective in ameliorating conditions characterized by unwanted calcium channel activity, particularly unwanted N-type calcium channel activity are disclosed. Specifically, a series of diaryl piperidine compounds are disclosed of the general formula (I) where X is a linker and Y may be C, O, S or N.

## Claims

### Claim at position 1

-35. (canceled)

### Claim 36

A method to treat a condition modulated by calcium ion channel activity, which method comprises administering to a subject in need of such treatment an amount of the compound of formula (1) effective to ameliorate said condition, wherein said compound is of the formula:
or a pharmaceutically acceptable salt or conjugate thereof, wherein
X is an optionally substituted alkylene (1-6C), alkenylene (2-6C), alkynylene (2-6C), heteroalkylene (2-6C), heteroalkenylene (2-6C), or heteroalkynylene (2-6C);
Y is CR′2, O, S(O)q or NR′ wherein q is 0-2 and each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
each Ar is independently an optionally substituted aromatic or heteroaromatic ring and wherein the two Ar groups may be linked together to form an optionally substituted fluorenyl;
each R1, R2 and R3 is independently ═O, ═NOR′, halo, CN, OR′, SR′, SOR′, SO2R′, NR′2, NR′(CO)R′, or NR′SO2R′, wherein each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
or each R1, R2 and R3 may independently be an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C), heteroalkenyl (2-6C), heteroalkynyl (2-6C), aryl (6-10C), heteroaryl (5-12C), O-aryl (6-10C), O-heteroaryl (5-12C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
a is 0-5, b is 0-1 and c is 0-4; and
wherein the optional substituents on each Ar, X, R′, R1, R2 and R3 are independently selected from halo, CN, NO2, CF3, OCF3, COOR″, CONR″2, OR″, SR″, SOR″, SO2R″, NR″2, NR″(CO)R″, and NR″SO2R″, wherein each R″ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl; or the optional substituent may be an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C), heteroalkenyl (2-6C), heteroalkynyl (2-6C), aryl (6-10C), heteroaryl (5-12C), O-aryl (6-10C), O-heteroaryl (5-12C) and C6-C12-aryl-C1-C6-alkyl; and wherein the optional substituent on X may further be selected from ═O and ═NOR″.

### Claim 37 (depends on 36)

The method of claim 36 wherein said condition is modulated by N-type calcium channel activity.

### Claim 38 (depends on 36)

The method of claim 36, wherein said condition is chronic or acute pain, a mood disorder, a neurodegenerative disorder, a gastrointestinal disorder, a genitorurinary disorder, neuroprotection, a metabolic disorder, cardiovascular disease, epilepsy, diabetes, prostate cancer, a sleep disorder, Parkinson's disease, schizophrenia or male birth control.

### Claim 39 (depends on 38)

The method of claim 38, wherein said condition is chronic or acute pain.

### Claim 40 (depends on 36)

The method of claim 36, wherein X is an optionally substituted alkylene (1-6C) or an optionally substituted heteroalkylene (1-6C).

### Claim 41 (depends on 40)

The method of claim 40, wherein X is X′Y′ wherein X′ is an optionally substituted alkylene (1-5C) or an optionally substituted heteroalkylene (1-5C) and Y′ is CR′2, O, S, SO, SO2 or NR′ wherein each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl.

### Claim 42 (depends on 41)

The method of claim 41, wherein X is CO(CH2)pY′ wherein p is 0-4.

### Claim 43 (depends on 42)

The method of claim 42, wherein Y′ is CH2, O, S, SO, SO2, NH or NCH3.

### Claim 44 (depends on 36)

The method of claim 36, wherein both Ar are independently optionally substituted phenyl.

### Claim 45 (depends on 36)

The method of claim 36, wherein Y is CH2, O, NH, N(CH3) or N(t-butyl).

### Claim 46 (depends on 36)

The method of claim 36, wherein a is 0-2.

### Claim 47 (depends on 46)

The method of claim 46, wherein R1 is ═O, alkyl(1-6C), heteroalkyl(1-6C), aryl(6-10C) or heteroaryl(5-12C).

### Claim 48 (depends on 36)

The method of claim 36, wherein R2 is ═O, alkyl(1-6C), heteroalkyl(1-6C), aryl(6-10C) or heteroaryl(5-12C).

### Claim 49 (depends on 36)

The method of claims 36, wherein c is 0-2.

### Claim 50 (depends on 36)

The method of claim 36, wherein R3 is ═O, alkyl(1-6C), heteroalkyl(1-6C), aryl(6-10C) or heteroaryl(5-12C).

### Claim 51 (depends on 36)

The method of claim 36, wherein the compound is:
2-(benzhydrylamino)-1-(4-(morpholino(phenyl)methyl)piperidin-1-yl)ethanone;
1-(4-(morpholino(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
N-benzhydryl-4-(morpholino(phenyl)methyl)piperidine-1-carboxamide;
2-(benzhydryloxy)-1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylthio)-1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylamino)-1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-diphenylpropanon-1-one;
N-benzhydryl-4-((4-methylpiperazine-1-yl)methyl)piperidine-1-carboxamide;
1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
N-benzhydryl-4-(4-methylpiperazine-1-carbonyl)piperidine-1-carboxamide;
1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-(piperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydryloxy)-1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylamino)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydrylthio)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
N-benzhydryl-4-(3,5-dimethylpiperazine-1-carbonyl)piperidine-1-carboxamide;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylamino)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidine-1-carboxamide;
2-(benzhydrylamino)-1-(4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)ethanone;
2-(benzhydrylamino)-1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidine-1-carboxamide;
1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
3,3-diphenyl-1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)propan-1-one;
N-benzhydryl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylamino)-1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylamino)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
3,3-diphenyl-1-(4-(phenyl(piperidin-1-yl)methyl)piperidin-1-yl)propan-1-one;
1-(4-(phenyl(piperidin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydryloxy)-1-(4-(phenyl(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
N-benzhydryl-4-(phenyl(piperidin-1-yl)methyl)piperidine-1-carboxamide;
1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-benzhydryl-4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-benzhydryl-4-phenyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-phenyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-((4-tert-butylpiperazin-1-yl)methyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
3,3-bis(4-fluorophenyl)-1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)propan-1-one;
3,3-bis(4-fluorophenyl)-N-(2-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-2-oxoethyl)propanamide;
2-(benzhydryloxy)-1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-6,6-diphenylhexan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-6,6-bis(4-fluorophenyl)hexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-6,6-bis(4-fluorophenyl)hexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-6,6-diphenylhexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-(4-tert-butylpiperazin-1-carbonyl)piperidine-1-carboxamide;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-bis(4-fluorophenyl)propan-1-one;
2-(bis(4-fluorophenyl)methoxy)-1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
1-(4-((2,3-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
2-(benzhydryloxy)-1-(4-((2,3-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
2-(bis(4-fluorophenyl)methoxy)-1-(4-((2,3-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
N-(bis(4-fluorophenyl)methyl)-4-(4-tert-butylpiperazine-1-carbonyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-(4-tert-butylpiperazine-1-carbonyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-((4-tert-butylpiperazin-1-yl)methyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-((4-tert-butylpiperazin-1-yl)methyl)piperidine-1-carboxamide;
2-(bis(4-fluorophenyl)methoxy)-1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
2-(9H-fluoren-9-yl)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
2-(bis(4-fluorophenyl)methoxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
N-benzhydryl-4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
2-(benzhydryloxy)-1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
or a pharmaceutically acceptable salt of one of these.

### Claim 52 (depends on 36)

The method of claim 36, wherein the compound is:
1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
2-(benzhydryloxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylsulfinyl)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(phenyl(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-6,6-diphenylhexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
or a pharmaceutically acceptable salt of one of these.

### Claim 53

A compound of the formula:
or a pharmaceutically acceptable salt or conjugate thereof, wherein
X is an optionally substituted alkylene (1-6C), alkenylene (2-6C), alkynylene (2-6C), heteroalkylene (2-6C), heteroalkenylene (2-6C), or heteroalkynylene (2-6C);
Y is CR′2, O, S(O)q or NR′ wherein q is 0-2 and each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
each Ar is independently an optionally substituted aromatic or heteroaromatic ring and wherein the two Ar groups may be linked together to form an optionally substituted fluorenyl;
each R1, R2 and R3 is independently ═O, ═NOR′, halo, CN, OR′, SR′, SOR′, SO2R′, NR′2, NR′(CO)R′, or NR′SO2R′, wherein each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
or each R1, R2 and R3 may independently be an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C), heteroalkenyl (2-6C), heteroalkynyl (2-6C), aryl (6-10C), heteroaryl (5-12C), O-aryl (6-10C), O-heteroaryl (5-12C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
a is 0-5, b is 0-1 and c is 0-4; and
wherein the optional substituents on each Ar, X, R′, R1, R2 and R3 are independently selected from halo, CN, NO2, CF3, OCF3, COOR″, CONR″2, OR″, SR″, SOR″, SO2R″, NR″2, NR″(CO)R″, and NR″SO2R″, wherein each R″ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl; or the optional substituent may be an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C), heteroalkenyl (2-6C), heteroalkynyl (2-6C), aryl (6-10C), heteroaryl (5-12C), O-aryl (6-10C), O-heteroaryl (5-12C) and C6-C12-aryl-C1-C6-alkyl; and wherein the optional substituent on X may further be selected from ═O and ═NOR″;
with the proviso that if X is (CH2)2-4O, then at least one Ar is unsubstituted.

### Claim 54 (depends on 53)

The compound of claim 53, wherein X is an optionally substituted alkylene (1-6C) or an optionally substituted heteroalkylene (1-6C).

### Claim 55 (depends on 53)

The compound of claim 53, wherein X is X′Y′ wherein X′ is an optionally substituted alkylene (1-5C) or an optionally substituted heteroalkylene (1-5C) and Y′ is CR′2, O, S, SO, SO2 or NR′ wherein R′ is H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), and aryl (6-10C).

### Claim 56 (depends on 55)

The compound of claim 55, wherein X is CO(CH2)pY′ wherein p is 0-4.

### Claim 57 (depends on 56)

The compound of claim 56, wherein Y′ is CH2, O, S, SO, SO2, NH or NCH3.

### Claim 58 (depends on 53)

The compound of claim 53, wherein both Ar are independently optionally substituted phenyl.

### Claim 59 (depends on 53)

The compound of claim 53, wherein Y is CH2, O, NH, N(CH3) or N(t-butyl).

### Claim 60 (depends on 53)

The compound of claim 53, wherein a is 0-2.

### Claim 61 (depends on 53)

The compound of claim 53, wherein R1 is ═O, alkyl(1-6C), heteroalkyl(1-6C), aryl(6-10C) or heteroaryl(5-12C).

### Claim 62 (depends on 53)

The compound of claim 53, wherein R2 is ═O, alkyl(1-6C), heteroalkyl(1-6C), aryl(6-10C) or heteroaryl(5-12C).

### Claim 63 (depends on 53)

The compound of claim 53, wherein c is 0-2.

### Claim 64 (depends on 53)

The compound of claim 53, wherein R3 is ═O, alkyl(1-6C), heteroalkyl(1-6C), aryl(6-10C) or heteroaryl(5-12C).

### Claim 65 (depends on 53)

The compound of claim 53, wherein the compound is:
2-(benzhydrylamino)-1-(4-(morpholino(phenyl)methyl)piperidin-1-yl)ethanone;
1-(4-(morpholino(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
N-benzhydryl-4-(morpholino(phenyl)methyl)piperidine-1-carboxamide;
2-(benzhydryloxy)-1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylthio)-1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylamino)-1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-diphenylpropanon-1-one;
N-benzhydryl-4-((4-methylpiperazine-1-yl)methyl)piperidine-1-carboxamide;
1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
N-benzhydryl-4-(4-methylpiperazine-1-carbonyl)piperidine-1-carboxamide;
1-(4-((4-methylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-(piperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydryloxy)-1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydrylamino)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
2-(benzhydrylthio)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
N-benzhydryl-4-(3,5-dimethylpiperazine-1-carbonyl)piperidine-1-carboxamide;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylamino)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidine-1-carboxamide;
2-(benzhydrylamino)-1-(4-((4-methylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)ethanone;
2-(benzhydrylamino)-1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidine-1-carboxamide;
1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
3,3-diphenyl-1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)propan-1-one;
N-benzhydryl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylamino)-1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylamino)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydrylsulfinyl)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
3,3-diphenyl-1-(4-(phenyl(piperidin-1-yl)methyl)piperidin-1-yl)propan-1-one;
1-(4-(phenyl(piperidin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydryloxy)-1-(4-(phenyl(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
N-benzhydryl-4-(phenyl(piperidin-1-yl)methyl)piperidine-1-carboxamide;
1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-benzhydryl-4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-benzhydryl-4-phenyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-phenyl-4-(piperidin-1-ylmethyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-((4-tert-butylpiperazin-1-yl)methyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
3,3-bis(4-fluorophenyl)-1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)propan-1-one;
3,3-bis(4-fluorophenyl)-N-(2-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-2-oxoethyl)propanamide;
2-(benzhydryloxy)-1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-6,6-diphenylhexan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-6,6-bis(4-fluorophenyl)hexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-6,6-bis(4-fluorophenyl)hexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-6,6-diphenylhexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
N-benzhydryl-4-(4-tert-butylpiperazin-1-carbonyl)piperidine-1-carboxamide;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-bis(4-fluorophenyl)propan-1-one;
2-(bis(4-fluorophenyl)methoxy)-1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
1-(4-((2,3-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
2-(benzhydryloxy)-1-(4-((2,3-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
2-(bis(4-fluorophenyl)methoxy)-1-(4-((2,3-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
N-(bis(4-fluorophenyl)methyl)-4-(4-tert-butylpiperazine-1-carbonyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-(4-tert-butylpiperazine-1-carbonyl)piperidine-1-carboxamide;
N-(bis(3-fluorophenyl)methyl)-4-((4-tert-butylpiperazin-1-yl)methyl)piperidine-1-carboxamide;
N-(bis(4-fluorophenyl)methyl)-4-((4-tert-butylpiperazin-1-yl)methyl)piperidine-1-carboxamide;
2-(bis(4-fluorophenyl)methoxy)-1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
2-(9H-fluoren-9-yl)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
2-(bis(4-fluorophenyl)methoxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)ethanone;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-bis(2-methoxyphenyl)propan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-2-(9H-fluoren-9-yl)ethanone;
N-benzhydryl-4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidine-1-carboxamide;
2-(benzhydryloxy)-1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)ethanone;
or a pharmaceutically acceptable salt of one of these.

### Claim 66 (depends on 53)

The compound of claim 53, wherein the compound is:
1-(4-(4-methylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
2-(benzhydryloxy)-1-(4-(3,5-dimethylpiperazine-1-carbonyl)piperidin-1-yl)ethanone;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-(3,5-dimethylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)methyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-(4-methylpiperazine-1-carbonyl)-4-phenylpiperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
2-(benzhydrylsulfinyl)-1-(4-phenyl-4-(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
2-(benzhydryloxy)-1-(4-(phenyl(piperidin-1-ylmethyl)piperidin-1-yl)ethanone;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-diphenylpropan-1-one;
1-(4-((4-methylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((3,5-dimethylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)methyl)piperidin-1-yl)-6,6-diphenylhexan-1-one;
1-(4-(4-tert-butylpiperazine-1-carbonyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
1-(4-((4-tert-butylpiperazin-1-yl)(phenyl)methyl)piperidin-1-yl)-3,3-di-o-tolylpropan-1-one;
or a pharmaceutically acceptable salt of one of these.

### Claim 67 (depends on 53)

A pharmaceutical composition which comprises the compound of claim 53, in admixture with a pharmaceutically acceptable excipient.

### Claim 68 (depends on 36)

The method of claim 36, wherein the compound is a compound of formula (2):
wherein X′ is (CH2)p or (CH2)p—O—, where p is 0-4;
Y′ represents CHR′ or NR′, wherein R′ is H or optionally substituted alkyl (1-6C);
R1 is H, or an optionally substituted alkyl (1-6C) or phenyl;
R2 represents H, optionally substituted phenyl, or carbonyl (═O); and
and each Ar is independently an optionally substituted phenyl ring;
with the proviso that if X′ is (CH2)2-4O, then at least one Ar is unsubstituted;
or a salt thereof.

### Claim 69 (depends on 53)

The compound of claim 53, which is a compound of formula (2):
wherein X′ is (CH2)p or (CH2)p—O—, where p is 0-4;
Y′ represents CHR′ or NR′, wherein R′ is H or optionally substituted alkyl (1-6C);
R1 is H, or an optionally substituted alkyl (1-6C) or phenyl;
R2 represents H, optionally substituted phenyl, or carbonyl (═O); and
and each Ar is independently an optionally substituted phenyl ring;
with the proviso that if X′ is (CH2)2-4O, then at least one Ar is unsubstituted;
or a salt thereof.

### Claim 70

A library of compounds, which library comprises at least 10 compounds of formula (1):
or a pharmaceutically acceptable salt or conjugate thereof, wherein
X is an optionally substituted alkylene (1-6C), alkenylene (2-6C), alkynylene (2-6C), heteroalkylene (2-6C), heteroalkenylene (2-6C), or heteroalkynylene (2-6C);
Y is CR′2, O, S(O)q or NR′ wherein q is 0-2 and each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
each Ar is independently an optionally substituted aromatic or heteroaromatic ring and wherein the two Ar groups may be linked together to form an optionally substituted fluorenyl;
each R1, R2 and R3 is independently ═O, ═NOR′, halo, CN, OR′, SR′, SOR′, SO2R′, NR′2, NR′(CO)R′, or NR′SO2R′, wherein each R′ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
or each R1, R2 and R3 may independently be an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C), heteroalkenyl (2-6C), heteroalkynyl (2-6C), aryl (6-10C), heteroaryl (5-12C), O-aryl (6-10C), O-heteroaryl (5-12C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl;
a is 0-5, b is 0-1 and c is 0-4; and
wherein the optional substituents on each Ar, X, R′, R1, R2 and R3 are independently selected from halo, CN, NO2, CF3, OCF3, COOR″, CONR″2, OR″, SR″, SOR″, SO2R″, NR″2, NR″(CO)R″, and NR″SO2R″, wherein each R″ is independently H or an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C) heteroalkenyl (2-6), heteroalkynyl (2-6C), heteroaryl (5-12C), aryl (6-10C), C5-C12-heteroaryl-C1-C6-alkyl, and C6-C12-aryl-C1-C6-alkyl; or the optional substituent may be an optionally substituted group selected from alkyl (1-6C), alkenyl (2-6C), alkynyl (2-6C), heteroalkyl (2-6C), heteroalkenyl (2-6C), heteroalkynyl (2-6C), aryl (6-10C), heteroaryl (5-12C), O-aryl (6-10C), O-heteroaryl (5-12C) and C6-C12-aryl-C1-C6-alkyl; and wherein the optional substituent on X may further be selected from ═O and ═NOR″;
with the proviso that if X is (CH2)2-4O, then at least one Ar is unsubstituted.