CA2560547A1 - Formamide derivatives useful as adrenoceptor - Google Patents

Formamide derivatives useful as adrenoceptor Download PDF

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Publication number
CA2560547A1
CA2560547A1 CA002560547A CA2560547A CA2560547A1 CA 2560547 A1 CA2560547 A1 CA 2560547A1 CA 002560547 A CA002560547 A CA 002560547A CA 2560547 A CA2560547 A CA 2560547A CA 2560547 A1 CA2560547 A1 CA 2560547A1
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Prior art keywords
hydroxyphenyl
formylamino
hydroxyethylamino
methylpropyl
phenyl
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CA002560547A
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French (fr)
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CA2560547C (en
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Alan Daniel Brown
Mark Edward Bunnage
Paul Alan Glossop
Kim James
Charlotte Alice Louise Lane
Russell Andrew Lewthwaite
David Anthony Price
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Pfizer Inc
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Pfizer Inc.
Alan Daniel Brown
Mark Edward Bunnage
Paul Alan Glossop
Kim James
Charlotte Alice Louise Lane
Russell Andrew Lewthwaite
David Anthony Price
Pfizer Limited
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Application filed by Pfizer Inc., Alan Daniel Brown, Mark Edward Bunnage, Paul Alan Glossop, Kim James, Charlotte Alice Louise Lane, Russell Andrew Lewthwaite, David Anthony Price, Pfizer Limited filed Critical Pfizer Inc.
Priority claimed from PCT/IB2005/000619 external-priority patent/WO2005092840A1/en
Publication of CA2560547A1 publication Critical patent/CA2560547A1/en
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Publication of CA2560547C publication Critical patent/CA2560547C/en
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    • C07C217/56—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups bound to carbon atoms of at least one six-membered aromatic ring and amino groups bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings of the same carbon skeleton with amino groups linked to the six-membered aromatic ring, or to the condensed ring system containing that ring, by carbon chains not further substituted by singly-bound oxygen atoms
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    • C07C233/43—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by amino groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by a carbon atom of a six-membered aromatic ring having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of a saturated carbon skeleton
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    • C07C311/45—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound nitrogen atoms, not being part of nitro or nitroso groups at least one of the singly-bound nitrogen atoms being part of any of the groups, X being a hetero atom, Y being any atom, e.g. N-acylaminosulfonamides
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Abstract

The invention relates to compounds of formula (1) and to processes for the preparation of, intermediates used in the preparation of, compositions containing and the uses of, such derivatives. The compounds according to the present invention are useful in numerous diseases, disorders and conditions, in particular inflammatory, allergic and respiratory diseases, disorders and conditions.

Claims (24)

1. A compound of general formula (1), wherein the (CH2)n-C(=O)Q1 group is in the meta or para position, - R1 and R2 are independently selected from H and C1-C4 alkyl;
- n is 0, 1 or 2;
- Q1 is a group selected from, wherein p is 1 or 2 and q is 1 or 2, said group being optionally bridged by one carbon atom, and a group *-NR8-Q2-A wherein Q2 is a C1-C4 alkylene, R8 is H or C1-C4 alkyl and A is pyridyl, C3-C10 cycloalkyl, said cycloalkyl being optionally bridged by one or more carbon atoms, tetrahydropyranyl, piperidinyl, tetrahydrothiopyranyl.
or a group - R3, R4, R5, R6 and R7 are the same or different and are selected from H, C1-alkyl, OR9, SR9, SOR9, SO2R9, halo, CO2R9, CF3, CN, OCF3, SO2NR9R10, CONR9R10, NR9R10, NHCOR10 and phenyl optionally substituted with 1 to 3 groups selected from OR9, halo and C1-C4 alkyl;
- R9 and R10 are the same or different and are selected from H or C1-C4 alkyl and the * represent the attachment point to the carbonyl group;
or, if appropriate, their pharmaceutically acceptable salts and/or isomers, tautomers, solvates or isotopic variations thereof.
2. A compound according to claim 1 wherein Q1 is a group *-NH-Q2-A, wherein A is cyclohexyl or adamantyl.
3. A compound according to claim 1 wherein Q1 is a group *-NH-Q2-A, wherein A is a group wherein R3, R4, R5, R6 and R7 are the same or different and are selected from H, C1-C4 alkyl, OR9, SR9, SOR9, SO2R9, halo, CN, CO2R9, CF3, OCF3, SO2NR9R10, CONR9R10, NR9R10, NHCOR10 and phenyl optionally substituted with 1 to 3 groups selected from OR9, halo and C1-C4 alkyl provided at least 2.
of R3 to R7 are equal to H;
wherein R9 and R10 are the same or different and are selected from H or C1-C4 alkyl.
4. A compound according to claim 3 wherein Q1 is a group *-NH-Q2-A, wherein A is a group wherein R3, R4, R5, R6 and R7 are the same or different and are selected from H, OH, CH3, OCH3, OCF3, OCH2-CH3, SCH3, N(CH3)2, N(C=O)CH3, C(=O)NH2, COOCH3, SO2CH3, SO2NH2, CN, halo, CF3, and phenyl optionally substituted with OH.
5. A compound according to claim 1 wherein A is a group wherein one of R3 to R7 is OH or phenyl substituted with OH.
6. A compound according to claim 1 wherein A is naphthyl optionally susbstituted with OH.
7. A compound according to any one of claims 1 to 6 wherein Q2 is -CH2-, -(CH2)2-, -(CH2)3-, -CH2-C(CH3)2- or -C(CH3)2-.
8. A compound according to claim 7 wherein Q2 is -CH2-.
9. A compound according to claim 1 wherein Q1 is wherein R3, R4, R5 and R6 are H.
10. A compound according to any one of claims 1 to 9 wherein R1 is H or C1-C4 alkyl and R2 is C1-C4 alkyl.
11. A compound according to claim 10 wherein R1 is H or CH3 and R2 is H or CH3.
12. A compound according to claim 1 to 11 wherein n is 0 or 1.
13. The (R,R)-stereoisomer of a compound according to any one of claims 1 to 12.
14. A compound according to any one of claim 1 to 13 wherein the (CH2)n-C(=O)Q1 group is in the meta position.
15. A compound according to claim 1 selected from the group consisting of N-Benzyl-2-(3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)acetamide;
N-(3,4-Dimethylbenzyl)-2-(3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)acetamide;
N-[2-(4-Chlorophenyl)ethyl]-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
N-[2-(2-Chlorophenyl)ethyl]-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(2-naphthalen-1-ylethyl)benzamide;

3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino)-2-methylpropyl}-N-[2-(4-methylphenyl)ethyl]benzamide;
N-[2-(2,6-Dimethylphenyl)ethyl]-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
N-[2-(2,3-Dimethylphenyl)ethyl]-3-(2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropylbenzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl)-N-[2-(4-hydroxy-2,3-dimethylphenyl)ethyl]benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-[2-(4-methoxyphenyl)ethyl]benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-phenethyl-benzamide;
N-Cyclohexylmethyl-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
N-[5-((1R)-2-{1,1-Dimethyl-2-[3-(piperidine-1-carbonyl)phenyl]ethylamino}-1-hydroxyethyl)-2-hydroxyphenyl]formamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-[2-(3-trifluoromethylphenyl)ethyl]benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(3-phenylpropyl)benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-indan-2-ylbenzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino}-2-methylpropyl}-N-(2-pyridin-2-ylethyl)benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-[2-(4-sulfamoylphenyl)ethyl]benzamide;
N-(4-Dimethylaminobenzyl)-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide;
N-[5-(2-{(1R)-2-[3-(3,4-Dihydro-1H-isoquinoline-2-carbonyl)-phenyl]-1,1-dimethyl-ethylamino}-1-hydroxyethyl)-2-hydroxyphenyl]formamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(4'-hydroxybiphenyl-3-ylmethyl)benzamide 3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-[2-(4-hydroxy-2,5-dimethylphenyl)ethyl]benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-[2-(4-hydroxy-3-methylphenyl)ethyl]benzamide;
N-(4-Acetylaminobenzyl)-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide;
4-{[2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetylamino]methyl}benzamide;
N-AdamantaN-1-yl-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(2-hydroxy-naphthaleN-1-ylmethyl)benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(4-hydroxy-3,5-dimethylbenzyl)benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(6-hydroxy-naphthaleN-2-ylmethyl)benzamide;
N-(3,6-Dichloro-2-hydroxybenzyl)-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
N-(3,4-Dimethylbenzyl)-2-(3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]ethyl}phenyl)acetamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-[2-(4-hydroxyphenyl)-2-methylpropyl]benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-N-(4'-hydroxybiphenyl-4-ylmethyl)benzamide;
N-Adamantan-1-yl-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide;
N-[5-(2-{2-[3-(10-Aza-tricyclo[6.3.1.0*2,7*]dodeca-2(7),3,5-triene-10-carbonyl)phenyl]-1,1-dimethylethylamino}-1-hydroxyethyl)-2-hydroxyphenyl]-formamide;
2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(4'-hydroxybiphenyl-3-ylmethyl)acetamide;

4-{[2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)-acetylamino]methyl}benzoic acid methyl ester;
2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)-N-(4-trifluoromethoxy-benzyl)acetamide;
N-(2-Chloro-4-hydroxybenzyl)-N-ethyl-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)-cetamide;
N-(2-Chloro-4-hydroxybenzyl)-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-phenyl)acetamide;
2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(4-hydroxy-3,5-dimethylbenzyl)acetamide;
2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(2-hydroxynaphthalen-1-ylmethyl)acetamide;
N-(5-Chloro-2-hydroxybenzyl)-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide;
N-(3,5-Dichloro-2-hydroxybenzyl)-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide;
2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(6-hydroxynaphthalen-2-ylmethyl)acetamide;
2-(3-{(2R)-2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(4'-hydroxybiphenyl-4-ylmethyl)acetamide;
N-(4-Cyano-benzyl)-2-(3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-phenyl)-acetamide;
2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-phenyl)-N-(4-methanesulfonyl-benzyl)-acetamide;
2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-phenyl)-N-(4-methylsulfanyl-benzyl)-acetamide;
2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-phenyl)-N-(4-trifluoromethyl-benzyl)-acetamide;
2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)-N-(4'-hydroxy-biphenyl-4-ylmethyl)acetamide;

N-[2-(5-Chloro-2-hydroxyphenyl)-ethyl]-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}-benzamide;
2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)-N-(4'-hydroxybiphenyl-3-ylmethyl)-acetamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-propyl}-N-[2-(4-hydroxyphenyl)-2-methylpropyl]-benzamide;
N-(2-Chloro-4-hydroxybenzyl)-2-(3-{(2R)-2-[(2R)-(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide;
N-[2-(5-Chloro-2-hydroxyphenyl)-ethyl]-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide;
3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-propyl}-N-[2-(4-hydroxyphenyl)-2-methylpropyl]-benzamide;
2-(3-{2-[(2R)-2-(3-Formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)-N-(tetrahydro-thiopyran-4-yl)acetamide;
N-(5-Chloro-2-hydroxybenzyl)-2-(3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}phenyl)acetamide; and, N-{5-[(1R)-2-((1R)-2-{3-[3-(3,4-Dihydro-1H-isoquinolin-2-yl)-3-oxopropyl]phenyl}-1-methylethylamino)-1-hydroxyethyl]-2-hydroxyphenyl}formamide.
16. A pharmaceutical composition comprising at least an effective amount of a compound of the formula (1) as described in any one of claims 1 to 15 or a pharmaceutically acceptable salt or derived form thereof.
17. A compound of the formula (1) as described in any one of claims 1 to 15 or a .pharmaceutically acceptable salt, derived form or composition thereof, for use as a medicament.
18. The use of a compound of the formula (1) as described in any one of claims 1 to 15 or of a pharmaceutically acceptable salt, derived form or composition thereof, for the manufacture of a drug for the treatment of diseases, disorders, and conditions selected from the group consisting of:

.cndot. asthma of whatever type, etiology, or pathogenesis, in particular asthma.
that is a member selected from the group consisting of atopic asthma, non-atopic asthma, allergic asthma, atopic bronchial IgE-mediated asthma, bronchial asthma, essential asthma, true asthma, intrinsic asthma caused by pathophysiologic disturbances, extrinsic asthma caused by environmental factors, essential asthma of unknown or inapparent cause, non-atopic asthma, bronchitic asthma, emphysematous asthma, exercise-induced asthma, allergen induced asthma, cold air induced asthma, occupational asthma, infective asthma caused by bacterial, fungal, protozoal, or viral infection, non-allergic asthma, incipient asthma, wheezy infant syndrome and bronchiolytis, .cndot. chronic or acute bronchoconstriction, chronic bronchitis, small airways obstruction, and emphysema, .cndot. obstructive or inflammatory airways diseases of whatever type, etiology, or pathogenesis, in particular an obstructive or inflammatory airways disease that is a member selected from the group consisting of chronic eosinophilic pneumonia, chronic obstructive pulmonary disease (COPD), COPD that includes chronic bronchitis, pulmonary emphysema or dyspnea associated or not associated with COPD, COPD that is characterized by irreversible, progressive airways obstruction, adult respiratory distress syndrome (ARDS), exacerbation of airways hyper-reactivity consequent to other drug therapy and airways disease that is associated with pulmonary hypertension, .cndot. bronchitis of whatever type, etiology, or pathogenesis, in particular bronchitis that is a member selected from the group consisting of acute bronchitis, acute laryngotracheal bronchitis, arachidic bronchitis, catarrhal bronchitis, croupus bronchitis, dry bronchitis, infectious asthmatic bronchitis, productive bronchitis, staphylococcus or streptococcal bronchitis and vesicular bronchitis, .cndot. acute lung injury, .cndot. bronchiectasis of whatever type, etiology, or pathogenesis, in particular bronchiectasis that is a member selected from the group consisting of cylindric bronchiectasis, sacculated bronchiectasis, fusiform bronchiectasis, capillary bronchiectasis, cystic bronchiectasis, dry bronchiectasis and follicular bronchiectasis.
19. Combination of a compound according to any one of claims 1 to 15 with other therapeutic agent(s) selected from:
(a) 5-Lipoxygenase (5-LO) inhibitors or 5-lipoxygenase activating protein (FLAP) antagonists, (b) Leukotriene antagonists (LTRAs) including antagonists of LTB4, LTC4, LTD4, and LTE4, (c) Histamine receptor antagonists including H1 and H3 antagonists, (d) .alpha.1- and .alpha.2-adrenoceptor agonist vasoconstrictor sympathomimetic agents for decongestant use, (e) muscarinic M3 receptor antagonists or anticholinergic agents, (f) PDE inhibitors, e.g. PDE3, PDE4 and PDE5 inhibitors, (g) Theophylline, (h) Sodium cromoglycate, (i) COX inhibitors both non-selective and selective COX-1 or COX-2 inhibitors (NSAIDs), (j) Oral and inhaled glucocorticosteroids, (k) Monoclonal antibodies active against endogenous inflammatory entities, (l) Anti tumor necrosis factor (anti-TNF-.alpha.) agents, (m)Adhesion molecule inhibitors including VLA-4 antagonists, (n) Kinin-B1 - and B2 -receptor antagonists, (o) Immunosuppressive agents, (p) Inhibitors of matrix metalloproteases (MMPs), (q) Tachykinin NK1, NK2 and NK3 receptor antagonists, (r) Elastase inhibitors, (s) Adenosine A2a receptor agonists, (t) Inhibitors of urokinase, (u) Compounds that act on dopamine receptors, e.g. D2 agonists, (v) Modulators of the NF .kappa..beta. pathway, e.g. IKK inhibitors, (w) modulators of cytokine signalling pathyways such as p38 MAP kinase or syk kinase, (x) Agents that can be classed as mucolytics or anti-tussive, (y) Antibiotics, (z) HDAC inhibitors, and, (aa) P13 kinase inhibitors.
20. The compound N-(5-chloro-2-hydroxybenzyl)-2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)acetamide, or a pharmaceutically acceptable salt or solvate thereof.
21. The compound 2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(4-hydroxy-3,5-dimethylbenzyl)acetamide, or a pharmaceutically acceptable salt or solvate thereof.
22. The compound 2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(6-hydroxynaphthalen-2-ylmethyl)acetamide, or a pharmaceutically acceptable salt or solvate thereof.
23. The compound 2-(3-{(2R)-2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]propyl}phenyl)-N-(4'-hydroxybiphenyl-4-ylmethyl)acetamide, or a pharmaceutically acceptable salt or solvate thereof.
24. The compound N-[2-(4-chlorophenyl)ethyl]-3-{2-[(2R)-2-(3-formylamino-4-hydroxyphenyl)-2-hydroxyethylamino]-2-methylpropyl}benzamide, or a pharmaceutically acceptable salt or solvate thereof.
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