Classifications

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Definitions

• the present invention relates to substituted phenoxyacetic acids as useful pharmaceutical compounds for treating respiratory disorders, pharmaceutical compositions containing them, and processes for their preparation.
• EPA 1 170 594 discloses methods for the identification of compounds useful for the treatment of disease states mediated by prostaglandin D2, a ligand for orphan receptor CRTH2.
• GB 1356834 discloses a series of compounds said to possess anti-inflammatory, analgesic and antipyretic activity. It has been found that certain phenoxyacetic acids are active at the CRTH2 receptor, and as a consequence are expected to be potentially useful for the treatment of various respiratory diseases, including asthma and COPD.
• the invention therefore provides a compound of formula (I) or a pharmaceutically acceptable salt or solvate thereof:
• X is halogen, cyano, nitro, S(O) Q R or C 1 . 4 al yl which is substituted by one or more halogen atoms;
• Y is selected from hydrogen, halogen, CN, nitro, SO 2 R 3 , OR 4 , SR 4 , SOR 3 , S0 2 NR 4 R 5 , CONR 4 R 5 , NR 4 R 5 , NR 6 S0 2 R 3 , NR 6 CO 2 R 6 , NR 6 COR 3 , C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl or C ⁇ alkyl, the latter four groups being optionally substituted by one or more substituents independently selected from halogen, OR 6 and NR 6 R 7 , S(0) n R 6 where n is 0, 1 or 2;
• Z is aryl or a ring A, where A is a six membered heterocyclic aromatic ring containing one or more nitrogen atoms or may be a 6,6 or 6,5 fused bicycle containing one or more O, N, S atoms, the aryl or A rings all being optionally substituted by one or more substituents independently selected from from hydrogen, halogen, CN, OH, SH, nitro, COR 9 , CO 2 R 6 , SO 2 R 9 , OR 9 , SR 9 , SOR 9 ,SO 2 NR 10 R n , CONR 10 R ⁇ , NR 10 R n , NHS0 2 R 9 , NR 9 S0 2 R 9 , NR 6 CO 2 R 6 , NHCOR 9 , NR 9 COR 9 , NR 6 CONR 4 R 5 , NR 6 SO 2 NR 4 R 5 , aryl, heteroaryl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl,
• R 1 and R 2 independently represent a hydrogen atom, halogen, C -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl or a C ⁇ . 6 alkyl group, the latter four groups being optionally substituted by one or more substituents independently selected from halogen, C 3 -C cycloalkyl, NR 6 R 7 , OR 6 , S(0) n R 6 (where n is 0, 1 or 2);
• R and R together can form a 3-8 membered ring optionally containing one or more atoms selected from O, S, NR 6 and itself optionally substituted by one or more C ⁇ -C 3 alkyl or halogen;
• R 6 and R 7 independently represents a hydrogen atom or C ⁇ -C 6 alkyl
• R 8 is hydrogen, C 4 alkyl, -COd-d alkyl, C0 2 d-C 4 aikyl or CONR 6 C ⁇ -C alkyl;
• aryl examples include phenyl and naphthyl.
• Heteroaryl is defined as a 5-7 member aromatic ring or can be 6,6- or 6,5-fused bicyclic ring optionally containing one or more heteroatoms selected from N, S and O.
• the bicyclic ring may be linked through carbon or nitrogen and may be attached through the 5 or 6 membered ring and can be fully or partially saturated.
• Examples include pyridine, pyrirnidine, thiazole, oxazole, pyrazole, imidazole, furan, isoxazole, pyrrole, isothiazole and azulene, naphthyl, indene, quinoline, isoquinoline, indole, indolizine, benzo[b]furan, benzo[b]thiophene, IH-indazole, benzimidazole, benzthiazole, benzoxazole, purine, 4H-quinolizine, cinnoline, phthalazine, quinazoline, quinoxaline, 1,8-naphthyridine, pteridine, quinolone and 1,2-methylenedioxy benzene.
• Aryl or heteroaryl groups can be optionally substituted by one or more substituents independently selected from hydrogen, halogen, CN, OH, SH, nitro, CO 2 R 6 , SO 2 R 9 , OR 9 , SR 9 , SOR 9 , SO 2 NR 10 R ⁇ , CONR 10 R ⁇ , NR 10 R ⁇ , NHSO 2 R 9 , NR 9 SO 2 R 9 , NR 6 CO 2 R 6 , NHCOR 9 , NR 9 COR 9 , aryl, heteroaryl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 7 cycloalkyl or Ci- ⁇ alkyl, the latter four groups being optionally substituted by one or more substituents independently selected from halogen, C 3 -C 7 cycloalkyl, OR 6 , NR 6 R 7 , S(O) n R 6 (where n is 0, 1 or 2), CONR 6 R 7 ,
• Substituents can be present at any suitable position, including appropriate substituents on nitrogen atoms.
• the group A is a six membered heterocyclic ring containing one or more nitrogen atoms or may be a 6,6 or 6,5 fused bicycle containing one or more O, N, S atoms.
• suitable rings include pyridine, pyrimidine, pyrazine, pyridazine, indole, quinoline, isoquinoline, benzimidazole, benzthiazole, benzofuran, benzoxazole, benzthiophene, phthalazine and quinazoline.
• an alkyl or alkenyl group or an alkyl or alkenyl moiety in a substituent group may be linear or branched.
• Heterocyclic rings as defined for R 4 , R 5 and R 10 and R 11 means saturated heterocycles, examples include morpholine, azetidine, pyrrolidine, piperidine and piperazine. Substitents can be present on carbon and appropriate nitrogen atoms of said rings.
• X is trifluoromethyl, nitro, cyano or halogen. More preferably X is trifluoromethyl, nitro, cyano, chloro or fluoro, even more preferably X is trifluoromethyl, chloro or fluoro. Most preferably X is trifluoromethyl or chloro.
• Y is hydrogen, halogen or C ⁇ . 3 alkyl. More preferably Y is hydrogen, flouoro or methyl. Most preferably Y is hydrogen.
• Z is phenyl, pyridinyl, pyrimidyl, naphthyl, quinolyl, benzo[b]thienyl or benzofuranyl each optionally substituted as defined above, more preferably phenyl optionally substituted as defined above.
• Preferred substituents for all Z groups include those substituents exemplified herein, in particular halogen, C ⁇ _ 3 alkyl, cyano, S0 2 R 9 , OR 9 , SR 9 , CO 2 R 6 , NHSO 2 R 9 , NR 9 SO 2 R 9 and SO 2 NR 10 R 1 * .
• Z is phenyl it is optionally substituted by one to three, preferably one or two, substituents selected from SEt, S0 2 Me, S0 2 Et, chloro, fluoro, cyano, methoxy, propoxy, C0 2 H, methyl, ethyl, propyl, butyl, amino, hydroxyl, NHCONHEt, NHCONHMe, NHCONHPr, NHCONH-cyclopropyl, CONH 2 , SO 2 NH 2 , OCF 3 , COMe, CO 2 Me, nitro, phenyl, SCF 3 , 1-pyrrolidinylsulphonyl, dimethylaminosulphonyl, ((phenylmethy)lamino)sulphonyl, [(2,2,2-trifluoroethyl)]amino]sulphonyl, [(5-methyl-2- thiazolyl)amino]sulphonyl, (phenylarrhn
• Z is pyridyl it is optionally substituted by one or two groups selected from S0 NH 2, methyl, amino, chloro and NMeS0 2 Me,. More preferably when Z is pyrimidine it is optionally substituted by one or two groups selected from amino, methyl, morpholinyl, dimethylamino, methylamino, benzylamino, piperidine, NMeSO 2 Me i (methylsulphonul)(benzyl)arnino, (ethylsulphonul)(benzyl)amino, acetyl(phenylmethyl)amino, 5-methyl-l,l-dioxido-l,2,5-thiadiazohdin-2-yl, l,l-dioxido-2- isothiazolidinyl, 3-hydroxy-l-azetidinyl, 4-methyl-l -piperazinyl, 1-pyrrolidinyl and NHS0 2 NMe 2 .
• Z is naphthyl it is preferably substituted with methoxy.
• R 1 and R 2 are independently hydrogen or C ⁇ alkyl. More preferably both R 1 aanndd RR 22 aarree hhyyddrrooggeenn oorr oonnee iiss hhyyddrrooggeenn aanndd ttlhe other is methyl or ethyl or both are methyl. Most preferably both R 1 and R 2 are hydrogen.
• Preferred compounds of the invention include those exemplified herein both in free base form as well as pharmaceutically acceptable salts and solvates thereof.
• Certain compounds of formula (I) are capable of existing in stereoisomeric forms. It will be understood that the invention encompasses all geometric and optical isomers of the compounds of formula (I) and mixtures thereof including racemates. Tautomers and mixtures thereof also form an aspect of the present invention.
• the compound of formula (I) above may be converted to a pharmaceutically acceptable salt or solvate thereof, preferably a basic addition salt such as sodium, potassium, calcium, aluminium, lithium, magnesium, zinc, benzathine, chloroprocaine, choline, diethanolamine, ethanolamine, ethyldiamine, meglumine, tromethamine or procaine, or an acid addition salt such as a hydrochloride, hydrobromide, phosphate, acetate, fumarate, maleate, tartrate, citrate, oxalate, methanesulphonate orp-toluenesulphonate.
• a basic addition salt such as sodium, potassium, calcium, aluminium, lithium, magnesium, zinc, benzathine, chloroprocaine, choline, diethanolamine, ethanolamine, ethyldiamine, meglumine, tromethamine or procaine
• an acid addition salt such as a hydrochloride, hydrobromide, phosphate
• R 19 is H or C Cio alkyl group and L is a leaving group, and optionally thereafter in any order:
• the reaction can be carried out in a suitable solvent such as DMF using a base such as potassium carbonate or the like.
• Suitable groups R 12 include -6 alkyl groups such as methyl, ethyl or tert-butyl.
• Suitable L is a leaving group such as halo, in particular chlorine or bromine. L may also be hydroxy so that a Mitsunobu reaction may be performed with compound (H) using for example triphenylphosphine and diethyl azodicarboxylate.
• Hydrolysis of the ester group R 12 can be carried out using routine procedures, for example treatment of methyl and ethyl esters with aqueous sodium hydroxide, and treatment of tert-butyl esters with acids such as trifluoroacetic acid.
• R 13 is H or a suitable protecting group, for example benzyl
• L 1 is iodide, bromide, chloride or triflate
• R 14 and R 15 are H or C ⁇ -C 6 alkyl groups or R 14 and R 15 together can form a 5 or 6 membered ring optionally substituted by one or more Ci-C 3 alkyl.
• the reaction can be carried out in a suitable solvent such as dioxane using a palladium catalyst such as [l,l-bis(diphenylphosphino)ferrocene]dichloropalladium and a base such as cesium fluoride, preferably at elevated temperatures.
• a palladium catalyst such as [l,l-bis(diphenylphosphino)ferrocene]dichloropalladium and a base such as cesium fluoride, preferably at elevated temperatures.
• Compounds of formula (IV) may also be prepared by a palladium catalysed coupling of compounds of formula (VLU) with a suitable boronic ester, for example (IX) or (X).
• a compound of formula (XHI) may be formed by reaction of a compound of formula (XIV) with a compound of formula (XV).
• X, Y and R 13 are as defined above and R 16 is as defined as a substituent on Z as defined in formula (I) or are protected derivatives thereof.
• the reaction can be carried out in a solvent such as ethanol under reflux, and a base such as sodium ethoxide can be used if compound of formula (XV) is a salt
• R > 16 is a group S-alkyl
• this may be further elaborated by oxidation to the sulfoxide or sulphone using an oxidizing agent such as mcpba in DCM at RT. This may then be displaced with an appropriate nucleophile as defined for Z in formula 1.
• a compound of formula (XVI) may be formed by the reaction of a compound of formula (XVII) with a compound of formula (XII) using a Suzuki coupling.
• Compounds of formula (I) may also be prepared by reaction of a compound of formula (XVm) in which in which X, Y, R 1 , R 2 , R 12 ,R 14 and R 15 are as defined above with a compound of formula (V) using Suzuki coupling method as defined above.
• a compound of formula (XVILT) may be prepared by method A or B
• the acid was first converted to the acid chloride, using for example oxalylchloride in DCM at RT, then reacted with 3-methyl-3-oxetanemethanol in the presence of a base such as triethylamine to give the ester.
• a base such as triethylamine
• the oxetane ester is the rearranged to the OBO ester using boron trifluoride diethyletherate in DCM at -78°C to RT.
• Deprotonation with a base such as sec -butyl lithium at low temperature followed by quenching with trimethylborate gave the protected diacid which was then deprotected using HCI then sodium hydroxide Method B
• the benzyl group may be removed by hydrogenation at RT using palladium on carbon as catalyst then alkylated with a compound of formula (LTJ) using a base or mitsunobu conditions. Treatment with acid such as HCI or trifluoroacetic acid then removes the protecting groups.
• the present invention provides the use of a compound of formula (I), a prodrug, pharmaceutically acceptable salt or solvate thereof for use in therapy.
• the compounds of formula (I) have activity as pharmaceuticals, in particular as modulators of CRTh2 receptor activity, and may be used in the treatment (therapeutic or prophylactic) of conditions/diseases in human and non-human animals which are exacerbated or caused by excessive or unregulated production of PGD 2 and its metabolites.
• conditions/diseases include:
• obstructive airways diseases including: asthma (such as bronchial, allergic, intrinsic, extrinsic and dust asthma particularly chronic or inveterate asthma (e.g. late asthma and airways hyper-responsiveness)); chronic obstructive pulmonary disease (COPD)(such as irreversible COPD); bronchitis (including eosinophilic bronchitis); acute, allergic, atrophic rhinitis or chronic rhinitis (such as rhinitis caseosa, hypertrophic rhinitis, rhinitis purulenta, rhinitis sicca), rhinitis occidentalamentosa, membranous rhinitis (including croupous, fibrinous and pseudomembranous rhinitis), scrofoulous rhinitis., perennial allergic rhinitis, easonal rhinitis (including rhinitis nervosa
• hay fever and vasomotor rhinitis nasal polyposis; sarcoidosis; farmer's lung and related diseases; fibroid lung; idiopathic interstitial pneumonia; cystic fibrosis; antitussive activity; treatment of chronic cough associated with inflammation or iatrogenic induced ;
• arthrides including rheumatic, infectious, autoimmune, seronegative, spondyloarthropathies (such as ankylosing spondylitis, psoriatic arthritis and Reiter's disease), Behcet's disease, Sjogren's syndrome and systemic sclerosis;
• Neurodegenerative diseases and dementia disorders such as Alzheimer's disease, amyotrophic lateral sclerosis and other motor neuron diseases, Creutzfeldt-Jacob's disease and other prion diseases, HIV encephalopathy (AIDS dementia complex), Huntington's disease, frontotemporal dementia, Lewy body dementia and vascular dementia), polyneuropathies (such as Guillain-Barre syndrome, chronic inflammatory demyelinating polyradiculoneuropathy, multifocal motor neuropathy), plexopathies, CNS demyelination (such as multiple sclerosis, acute ⁇ sseminatedhaemorrhagic encephalomyelitis, and subacute sclerosing panencephalitis), neuromuscular disorders (such as myasthenia gravis and Lambert-Eaton syndrome), spinal diorders (such as tropical spastic paraparesis, and stiff-man syndrome), paraneoplastic syndromes (such as cerebellar degeneration and encephalo
• AIDS Immunodeficiency Syndrome
• lupus erythematosus lupus erythematosus
• systemic lupus erythematosus
• Hashimoto's thyroiditis type I diabetes, nephrotic syndrome, eosinophilia fascitis, hyper IgE syndrome, lepromatous leprosy, idiopathic thrombocytopenia pupura
• obstructive diseases of the airways including: asthma, including bronchial, allergic, intrinsic, extrinsic, exercise-induced, drug-induced (including aspirin and NS ATD-induced) and dust-induced asthma, both intermittent and persistent and of all severities, and other causes of airway hyper-responsiveness ; chronic obstructive pulmonary disease (COPD) ; bronchitis , including infectious and eosinophilic bronchitis; emphysema; bronchiectasis; cystic fibrosis; sarcoidosis; farmer's lung and related diseases; hypersensitivity pneumonitis; lung fibrosis, including cryptogenic fibrosing alveolitis, idiopathic interstitial pneumonias, fibrosis complicating anti-neoplastic therapy and chronic infection, including tuberculosis and aspergillosis and other fungal infections
• osteoarthritides associated with or including osteoarthritis/osteoarthrosis, both primary and secondary to e.g. congenital hip dysplasia; cervical and lumbar spondylitis, and low back and neck pain; rheumatoid arthritis and Still's disease; seronegative spondyloarthropathies including ankylosing spondylitis, psoriatic arthritis, reactive arthritis and undifferentiated spondarthropathy; septic arthritis and other infection-related arthopathies and bone disorders such as tuberculosis, including Potts' disease and Poncet's syndrome; acute and chronic crystal-induced synovitis including urate gout, calcium pyrophosphate deposition disease, and calcium apatite related tendon, bursal and synovial inflammation; Behcet's disease; primary and secondary Sjogren's syndrome; systemic sclerosis and limited scleroderma; systemic lupus erythematosus, mixed
• hepatitis including autoimmune, alcoholic and viral; fibrosis and cirrhosis of the liver; cholecystitis; pancreatitis, both acute and chronic.
• nephritis including interstitial and glomerulonephritis; nephrotic syndrome; cystitis including acute and chronic (interstitial) cystitis and Hunner's ulcer; acute and chronic urethritis, prostatitis, epididymitis, oophoritis and salpingitis; vulvo-vaginitis; Peyronie's disease; erectile dysfunction (both male and female).
• the present invention provides a compound of formula (I), or a pharmaceutically- acceptable salt or solvate thereof, as hereinbefore defined for use in therapy.
• the compounds of the invention are used to treat diseases in which the chemokine receptor belongs to the CRTh2 receptor subfamily.
• Particular conditions which can be treated with the compounds of the invention are asthma, rhinitis and other diseases in which raised levels of PGD 2 or its metabolites. It is preferred that the compounds of the invention are used to treat asthma.
• the present invention provides the use of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof, as hereinbefore defined in the manufacture of a medicament for use in therapy.
• the present invention provides the use of a compound or formula (I), or a pharmaceutically acceptable salt or solvate thereof, as hereinbefore defined in the manufacture of a medicament for use in therapy in combination with drags used to treat asthma and rhinitis (such as inhaled and oral steroids, inhaled ⁇ 2-receptor agonists and oral leukotriene receptor antagonists).
• the invention further relates to combination therapies wherein a compound of formula (1) or a pharmaceutically acceptable salt, solvate or in vivo hydrolysable ester thereof, or a pharmaceutical composition or formulation comprising a compound of formula (1) is administered concurrently or sequentially or as a combined preparation with another therapeutic agent or agents, for the treatment of one or more of the conditions listed .
• tumour necrosis factor alpha (TNF- ⁇ ) inhibitors such as anti-TNF monoclonal antibodies (for example Remicade, CDP-870 and adalimumab) and TNF receptor immunoglobulin molecules (such as Enbrel); non-selective cyclo-oxygenase (COX)-l / COX-2 inhibitors whether applied topically or systemically (such as piroxicam, diclofenac, propionic acids such as naproxen, flubiprofen, fenoprofen, ketoprofen and ibuprofen, fenamates such as mefenamic acid, indomethacin, sulindac, azapropazone, pyrazolones such as phenylbutazone,
• TNF- ⁇ tumour necrosis factor alpha
• COX non-selective cyclo-oxygenase
• the present invention still further relates to the combination of a compound of the invention together with a leukotriene biosynthesis inhibitor, 5-lipoxygenase (5-LO) inhibitor or 5-lipoxygenase activating protein (FLAP) antagonist such as; zileuton; ABT- 761; fenleuton; tepoxalin; Abbott-79175; Abbott-85761; N-(5-substituted)-thiophene-2- alkylsulfonamides; 2,6-di-tert-butylphenol hydrazones; methoxytetrahydropyrans such as Zeneca ZD-2138; the compound SB-210661; pyridinyl-substituted 2-cyanona ⁇ hthalene compounds such as L-739,010; 2-cyanoquinoline compounds such as L-746,530; indole and quinoline compounds such as MK-591, MK-886, and BAY x 1005.
• the present invention still further relates to the combination of a compound of the invention together with a receptor antagonist for leukotrienes( LT)B4, LTC4, LTD4, and LTE4.
• a receptor antagonist for leukotrienes( LT)B4, LTC4, LTD4, and LTE4 selected from the group consisting of the phenothiazin-3-ls such as L-651,392; amidino compounds such as CGS-25019c; benzoxalamines such as ontazolast; benzenecarboximidamides such as BHL 284/260; and compounds such as zafirlukast, ablukast, montelukast, pranlukast, verlukast (MK-679), RG-12525, Ro-245913, iralukast (CGP 45715A), and BAY x 7195.
• a receptor antagonist for leukotrienes( LT)B4, LTC4, LTD4, and LTE4.
• the present invention still further relates to the combination of a compound of the invention together with a phosphodiesterase (PDE) inhibitor such as the methylxanthanines including theophylline and aminophylline; and selective PDE isoenzyme inhibitors including PDE4 inhibitors and inhibitors of the isoform PDE4D, and inhibitors of PDE5.
• PDE phosphodiesterase
• the present invention still further relates to the combination of a compound of the invention together with histamine type 1 receptor antagonists such as cetirizine, loratadine, desloratadine, fexofenadine, acrivastine, terfenadine, aste izole, azelastine, levocabastine, chlo heniramine, promethazine, cyclizine, and mizolastine applied orally, topically or parenterally.
• histamine type 1 receptor antagonists such as cetirizine, loratadine, desloratadine, fexofenadine, acrivastine, terfenadine, aste izole, azelastine, levocabastine, chlo heniramine, promethazine, cyclizine, and mizolastine applied orally, topically or parenterally.
• the present invention still further relates to the combination of a compound of the invention together with a gastroprotective histamine type 2 receptor antagonist.
• the present invention still further relates to the combination of a compound of the invention with antagonists of the histamine type 4 receptor.
• the present invention still further relates to the combination of a compound of the invention together with an alpha- l/al ⁇ ha-2 adrenoceptor agonist vasoconstrictor sympathomimetic agent, such as propylhexedrine, phenylephrine, phenylpropanolamine, ephedrine, pseudoephedrine, naphazoline hydrochloride, oxymetazoline hydrochloride, tetrahydrozoline hydrochloride, xylometazoline hydrochloride, tramazoline hydrochloride, and ethylnorepinephrine hydrochloride.
• an alpha- l/al ⁇ ha-2 adrenoceptor agonist vasoconstrictor sympathomimetic agent such as propylhexedrine, phenylephrine, phenylpropanolamine, ephedrine, pseudoephedrine, naphazoline hydrochloride, oxymetazo
• the present invention still further relates to the combination of a compound of the invention together with anticholinergic agents including muscarinic receptor (Ml, M2, and M3) antagonists such as atropine, hyoscine, glycpyrrrolate, ipratropium bromide; tiotropium bromide; oxitropium bromide; pirenzepine; and telenzepine.
• Ml, M2, and M3 antagonists such as atropine, hyoscine, glycpyrrrolate, ipratropium bromide; tiotropium bromide; oxitropium bromide; pirenzepine; and telenzepine.
• the present invention still further relates to the combination of a compound of the invention together with a beta-adrenoceptor agonist (including beta receptor subtypes 1-4) such as isoprenaline, salbutamol, formoterol, salmeterol, terbutaline, orciprenaline, bitolterol mesylate, and pirbuterol .
• a beta-adrenoceptor agonist including beta receptor subtypes 1-4
• beta receptor subtypes 1-4 such as isoprenaline, salbutamol, formoterol, salmeterol, terbutaline, orciprenaline, bitolterol mesylate, and pirbuterol .
• the present invention still further relates to the combination of a compound of the invention together with a chromone, including sodium cromoglycate and nedocromil sodium.
• the present invention still further relates to the combination of a compound of the invention together with an insulin-like growth factor type I (IGF-1) mimetic.
• IGF-1 insulin-like growth factor type I
• the present invention still further relates to the combination of a compound of the invention together with an inhaled glucocorticoid, such as flunisolide, triamcinolone acetonide, beclomethasone dipropionate, budesonide, fluticasone propionate, ciclesonide, and mometasone furoate.
• an inhaled glucocorticoid such as flunisolide, triamcinolone acetonide, beclomethasone dipropionate, budesonide, fluticasone propionate, ciclesonide, and mometasone furoate.
• the present invention still further relates to the combination of a compound of the invention together with an inhibitor of matrix m ⁇ talloproteases (MMPs), i.e., the stromelysins, the coUagenases, and the gelatinases, as well as aggrecanase; especially collagenase-1 (MMP-1), collagenase-2 (MMP-8), collagenase-3 (MMP-13), stromelysin-1 (MMP-3), stromelysin-2 (MMP-10), and stromelysin-3 (MMP-11) and MMP-9 and MMP-12.
• MMPs matrix m ⁇ talloproteases
• the present invention still further relates to the combination of a compound of the invention together with modulators of chemokine receptor function such as antagonists of CCR1, CCR2, CCR2A, CCR2B, CCR3, CCR4, CCR5, CCR6, CCR7, CCR8, CCR9, CCR10 and CCR11 (for the C-C family); CXCR1, CXCR2, CXCR3, CXCR4 and CXCR5 (for the C-X-C family) and CX 3 CR1 for the C-X 3 -C family.
• modulators of chemokine receptor function such as antagonists of CCR1, CCR2, CCR2A, CCR2B, CCR3, CCR4, CCR5, CCR6, CCR7, CCR8, CCR9, CCR10 and CCR11 (for the C-C family); CXCR1, CXCR2, CXCR3, CXCR4 and CXCR5 (for the C-X-C family) and CX 3 CR1 for the C-X 3 -C family
• the present invention still further relates to the combination of a compound of the invention together with a cytokine or modulator of cytokine function, including alpha-, beta-, and gamma-interferon; interleukins (IL) including LL1 to 15, and interleukin antagonists or inhibitors, including agents which act on cytokine signalling pathways.
• a cytokine or modulator of cytokine function including alpha-, beta-, and gamma-interferon
• interleukins (IL) including LL1 to 15
• interleukin antagonists or inhibitors including agents which act on cytokine signalling pathways.
• the present invention still further relates to the combination of a compound of the invention together with an immunoglobulin (Ig) or Ig preparation or an antagonist or antibody modulating Ig function such as anti-IgE (omalizumab).
• Ig immunoglobulin
• Ig preparation or an antagonist or antibody modulating Ig function such as anti-IgE (omalizumab).
• the present invention still further relates to the combination of a compound of the invention together with other systemic or topically-applied anti-inflammatory agents including thalidomide and derivatives, retinoids, dithranol, and calcipotriol.
• the present invention still further relates to the combination of a compound of the invention together with an antibacterial agent including penicillin derivatives, tetracyclines, macrohdes, beta-lactams, flouroquinolones, and inhaled aminoglycosides; and antiviral agents including acyclovir, famciclovir, valaciclovir, ganciclovir, cidofovir; amantadine, rimantadine; ribavirin; zanamavir and oseltamavir; protease inhibitors such as indinavir, nelfinavir, ritonavir, and saquinavir; nucleoside reverse transcriptase inhibitors such as didanosine, lamivudine, stavudine, zalcitabine, zidovudine; non-nucleoside reverse transcriptase inhibitors such as nevirapine, efavirenz.
• an antibacterial agent including penicillin derivative
• the present invention still further relates to the combination of a compound of the invention together with cardiovascular agents such as calcium channel blockers, beta- adrenoceptor blockers, angiotensin-con verting enzyme (ACE) inhibitors, angiotensin-2 receptor antagonists; lipid lowering agents such as statins, and fibrates; modulators of blood cell morphology such as pentoxyfyUine; thrombolytics, and anticoagulants including platelet aggregation inhibitors.
• cardiovascular agents such as calcium channel blockers, beta- adrenoceptor blockers, angiotensin-con verting enzyme (ACE) inhibitors, angiotensin-2 receptor antagonists; lipid lowering agents such as statins, and fibrates; modulators of blood cell morphology such as pentoxyfyUine; thrombolytics, and anticoagulants including platelet aggregation inhibitors.
• the present invention still further relates to the combination of a compound of the invention together with CNS agents such as antidepressants (such as sertraline), anti-
• Parkinsonian drugs such as deprenyl, L-dopa, Requip, Mirapex, MAOB inhibitors such as selegine and rasagiline, comP inhibitors such as Tasmar, A-2 inhibitors, dopamine reuptake inhibitors, NMDA antagonists, nicotine agonists, dopamine agonists and inhibitors of neuronal nitric oxide synthase), and anti- Alzheimer's drugs such as donepezil, tacrine, COX-2 inhibitors, propentofylline or metrifonate.
• comP inhibitors such as Tasmar, A-2 inhibitors, dopamine reuptake inhibitors, NMDA antagonists, nicotine agonists, dopamine agonists and inhibitors of neuronal nitric oxide synthase
• anti- Alzheimer's drugs such as donepezil, tacrine, COX-2 inhibitors, propentofylline or metrifonate.
• the present invention still further relates to the combination of a compound of the invention together with agents for the treatment of acute and chronic pain, including centrally and peripherally-acting analgesics such as opioid analogues and derivatives, carbamazepine, phenytoin, sodium valproate, amitryptiline and other antidepressant agents, and non-steroidal anti-inflammatory agents.
• agents for the treatment of acute and chronic pain including centrally and peripherally-acting analgesics such as opioid analogues and derivatives, carbamazepine, phenytoin, sodium valproate, amitryptiline and other antidepressant agents, and non-steroidal anti-inflammatory agents.
• the present invention still further relates to the combination of a compound of the invention together with parenterally or topically-applied local anaesthetic agents such as lignocaine.
• the present invention still further relates to the combination of a compound of the invention together with (i) tryptase inhibitors; (ii) platelet activating factor (PAF) antagonists; (iii) interleukin converting enzyme (ICE) inhibitors; (iv) IMPDH inhibitors; (v) adhesion molecule inhibitors including VLA-4 antagonists; (vi) cathepsins; (vii) MAP kinase inhibitors; (viii) glucose-6 phosphate dehydrogenase inhibitors; (ix) kinin-B.subl. - and B.sub2.
• -receptor antagonists include anti-gout agents, e.g., colchicine; (xi) xanthine oxidase inhibitors, e.g., allopurinol; (xii) uricosuric agents, e.g., probenecid, sulfinpyrazone, and benzbromarone; (xiii) growth hormone secretagogues; (xiv) transforming growth factor (TGF ⁇ ); (xv) platelet-derived growth factor (PDGF); (xvi) fibroblast growth factor, e.g., basic fibroblast growth factor (bFGF); (xvii) granulocyte macrophage colony stimulating factor (GM-CSF); (xviii) capsaicin cream; (xix) Tachykinin NK.subl.
• anti-gout agents e.g., colchicine
• xi xanthine oxidase inhibitors, e.g., allopurinol
• NKP-608C selected from the group consisting of NKP-608C; SB-233412 (talnetant); and D-4418;
• elastase inhibitors selected from the group consisting of UT-77 and ZD-0892;
• elastase inhibitors selected from the group consisting of UT-77 and ZD-0892;
• iNOS induced nitric oxide synthase inhibitors
• chemoattractant receptor-homologous molecule expressed on TH2 cells CRTH2 antagonists
• the compounds of the present invention may also, be used in combination with anti- osteoporosis agents including hormonal agents such as raloxifene, and biphosphonates such as alendronate.
• NS AIDs standard non-steroidal anti-inflammatory agents
• piroxicam diclofenac
• propionic acids such as naproxen, flubiprofen, fenoprofen, ketoprofen and ibuprofen
• fenamates such as mefenamic acid, indomethacin, sulindac, apazone, pyrazolones such as phenylbutazone
• salicylates such as aspirin
• COX-2 inhibitors such as celecoxib, valdecoxib, rofecoxib and etoricoxib
• intra- articular therapies such as corticosteroids and hyaluronic acid derivatives, and nutritional supplements such as glucosamine.
• agents to be used in combination include: (i) antiproliferative/antineoplastic drugs and combinations thereof, as used in medical oncology, such as alkylating agents (for example cis-platin, carboplatin, cyclophosphamide, nitrogen mustard, melphalan, chlorambucil, busulphan and nitrosoureas); antimetabolites (for example antifolates such as fluoropyrimidines like 5-fluorouracil and tegafur, raltitrexed, methotrexate, cytosine arabinoside, hydroxyurea, gemcitabine and paclitaxel; antitumour antibiotics (for example anthracyclines like adriamycin, bleomycin, doxorubicin, daunomycin, epirubicin, idarubicin, mitomycin-C, dactinomycin and mithra
• alkylating agents for example cis-platin, carboplatin,
• Agents which inhibit cancer cell invasion for example metalloproteinase inhibitors like marimastat and inhibitors of urokinase plasminogen activator receptor function);
• inhibitors of growth factor function include growth factor antibodies, growth factor receptor antibodies (for example the anti-erbb2 antibody trastuzumab and the anti-erbbl antibody cetuximab [C225]) , farnesyl transferase inhibitors, tyrosine kinase inhibitors and serine/threonine kinase inhibitors, for example inhibitors of the epidermal growth factor family (for example EGFR family tyrosine kinase inhibitors such as N-(3-chloro-4-fluorophenyl)-7-methoxy-6-(3- morpholinopropoxy)quinazolin-4-amine (gefitinib, AZD1839), N-(3-ethynylphenyl)-6
• gene therapy approaches including for example approaches to replace aberrant genes such as aberrant p53 or aberrant BRCA1 or BRCA2, GDEPT (gene-directed enzyme pro-drug therapy) approaches such as those using cytosine deaminase, thymidine kinase or a bacterial nitroreductase enzyme and approaches to increase patient tolerance to chemotherapy or radiotherapy such as multi-drug resistance gene therapy; and
• GDEPT gene-directed enzyme pro-drug therapy
• immunotherapy approaches including for example ex- vivo and in-vivo approaches to increase the immunogenicity of patient tumour cells, such as transfection with cytokines such as interleukin 2, interleukin 4 or granulocyte-macrophage colony stimulating factor, approaches to decrease T-cell anergy, approaches using transfected immune cells such as cytokine-transfected dendritic cells, approaches using cytokine-transfected tumour cell lines and approaches using anti-idiotypic antibodies.
• cytokines such as interleukin 2, interleukin 4 or granulocyte-macrophage colony stimulating factor
• the present invention provides the use of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof, as hereinbefore defined in the manufacture of a medicament for the treatment of human diseases or conditions in which modulation of CRTh2 receptor activity is beneficial.
• the term “therapy” also includes “prophylaxis” unless there are specific indications to the contrary.
• the terms “therapeutic” and “therapeuticaUy” should be construed accordingly.
• the invention still further provides a method of treating diseases mediated by PGD2 or its metabolites wherein the prostanoid binds to its receptor (especially CRTh2) receptor, which comprises administering to a patient a therapeuticaUy effective amount of a compound of formula (I), or a pharmaceutically acceptable salt, solvate or prodrug thereof, as hereinbefore defined.
• the invention also provides a method of treating an inflammatory disease, especially psoriasis, in a patient suffering from, or at risk of, said disease, which comprises administering to the patient a therapeuticaUy effective amount of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof, as hereinbefore defined.
• a therapeuticaUy effective amount of a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof as hereinbefore defined.
• the dosage administered will, of course, vary with the compound employed, the mode of administration, the treatment desired and the disorder indicated.
• the dosage administered will, of course, vary with the compound employed, the mode of administration, the treatment desired and the disorder indicated.
• the compound of formula (I), prodrugs and pharmaceutically acceptable salts and solvates thereof may be used on their own but will generally be administered in the form of a pharmaceutical composition in which the formula (I) compound/salt solvate (active ingredient) is in association with a pharmaceutically acceptable adjuvant, diluent or carrier.
• the pharmaceutical composition will preferably comprise from 0.05 to 99 %w (per cent by weight), more preferably from 0.05 to 80 %w, still more preferably from 0.10 to 70 %w, and even more preferably from 0.10 to 50 %w, ... of active ingredient, all percentages by weight being based on total composition.
• the present invention also provides a pharmaceutical composition
• a pharmaceutical composition comprising a compound of formula (I), or a pharmaceutically acceptable salt or solvate thereof, as herein before defined, in association with a pharmaceutically acceptable adjuvant, diluent or carrier.
• compositions may be administered topically (e.g. to the lung and/or airways or to the skin) in the form of solutions, suspensions, heptafluoroalkane aerosols and dry powder formulations; or systemically, e.g. by oral administration in the form of tablets, capsules, syrups, powders or granules, or by parenteral administration in the form of solutions or suspensions, or by subcutaneous administration or by rectal administration in the form of suppositories or transdermally.
• the compound of the invention is administered orally.
• reverse phase HPLC was conducted using a Symmetry, NovaPak or Ex-Terra reverse phase silica column; (v) solvents were dried with MgSO or Na 2 SO 4 (vi) the following abbreviations are used:
• the subtitle compound was prepared by the method of example 1 step (ii) using the product from example 1 step (i) and 4-chlorophenylboronic acid. Yield 0.63g
• Example 17 ⁇ 2-[5-(Aminosulfonyl)pyridin-2-yl]-4-chlorophenoxy ⁇ acetic acid
• the title compound was prepared by the method of example 16. Yield 0.022g
• the subtitle compound was prepared by the method of example 2 step (i) using the product from step (ii).
• the subtitle compound was prepared by the method of example 16 step (iv) and example 1 step (i) using the product from step (iii). Yield 1.04g
• the subtitle compound was prepared by the method of example 1 step (i) using the product from step (v). Yield 0.253g
• the subtitle compound was prepared by the method of example 1 step (ii) using the product from step (ii) and the product from example 16 step (ii). Yield 0.55g
• the title compound was prepared by the method of example 32 using methyl-S-lactate, yield 0.2g.
• Example 36 2-[[4 , -(Ethylsulfonyl)-2'-methyl-5-(trifluoromethyl)[l,l'-biphenyl]-2-yl]oxy]-2- methyl- propanoic acid, sodium salt
• the subtitle compound was prepared by the method of example 1 step (ii) using the product from step (i) and 5-chloro-2-hydroxyphenyl-boronic acid , yield 0.25g.
• Example 40 [2-[2-[Acetyl(phenylmethyl)amino]-5-pyrimidinyl]-4-chlorophenoxy]-acetic acid (i) N-(5-Bromo-2-pyrimidinyl)-N-(phenylmethyl)-acetamide
• the subtitle compound was prepared by the method of example 38 step (i) using benzyl-(5- bromo-pyrimidin-2-yl)-amine and acetylchloride , yield 0.2 lg.
• the aqueous layer was extracted with ethylacetate, the organics combined and evaporated under reduced pressure.
• the residue was dissolved in methanol (500ml) then bondelut- NH 2 resin(180g) added and the mixture swirled for 0.5h then filtered.
• the resin was washed with 10% acetic acid /methanol, the washings then evaporated under reduced pressure and dried under high vacuum.
• the residue was dissolved in methanol(50ml), tetrahydrofuran (50ml) and saturated aqueous sodium hydroxide solution (2ml), left for 30min then 2M hydrochloric acid (50ml) added and the organics evaporated under reduced pressure.
• the residual aqueous layer was extracted with ethylacetate, the organics separated, dried and evaporated under reduced pressure, yield 5.05g.
• N-(5-Bromo-4-methyl-2-pyrimidinyl)-NN-dimethyl- sulfamide A mixture of 5-bromo-4-methyl-2-pyrimidinamine (0.75g) and dimethylsulphonyl chloride (0.43ml) in pyridine (20ml) was heated at 80°C for 17h. The solvent was removed under reduced pressure and the residue purified by chromatography on silica eluting with diethylether then ethylacetate. The residue was then purified by RPHPLC, yield 0.12g.
• the subtitle compound was prepared by the method of example 1 step (i) using the product from step (ii). Yield 0.07g. Used in step (iv) without characterisation.
• step (iii) (0.07g) was dissolved in DCM (5ml), triethylamine (0.024ml) added, followed by methyl chloroformate (0.013ml) and stirred for 20h. Further triethylamine (0.024ml) and methyl chloroformate (0.013ml) were added three times over to achieve complete reaction. The solvent was removed by evaporation to give the crude product which was carried forward to step (v) without characterisation.
• the subtitle compound was prepared by the method of example 144 step (ii) using the product from step (iii). Yield 0.95g NMR DMSO-d6: ⁇ 10.72 (s, IH), 8.08 (d, IH), 7.93 (dd, IH), 7.63-7.68 (m, 2H), 7.49
• Example 146 2-[[3'-Cyano-5-(trifluoromethyl)[l,l'-biphenyl]-2-yl]oxy]-(2S)-propanoic acid i) 4,4,5 ,5-Tetramethyl-2- [2-(phenylmethoxy)-5-(txifluoromethyl)phenyl]- 1 ,3 ,2- dioxaborolane Pinacol (1.82g) was added to a solution of the product from example 32 step (ii) (4.54g) in ether (40ml) and stirred at RT for 20h. The reaction was diluted with ether (100ml), washed with brine, dried (MgS0 4 ) and evaporated. Yield 5.7g.
• the title compound was prepared by the method of example 144 step (i) using the product from example 146 step (iv) and 4-bromo-N,N-dimethyl-benzenesulfonamide.
• the subtitle compound was prepared by the method of example 144 step (i) using the product from example 16 step (ii) and the product from example 145 step (ii). Yield 1.08g. NMR DMSO-d6: ⁇ 8.09 (d, IH), 7.94 (dd, IH), 7.67 (d, IH), 7.49 (dd, IH), 7.22-7.34 (m, 7H), 5.14 (s, 2H), 3.35 (s, 3H)
• the title compound was prepared by the method of example 155 using the product from example 151 step (iv) and the product from example 149 step (i).
• the title compound was prepared by the method of example 144 step (i) using the product from example 151 step (iv), l-[(4-bromophenyl)sulfonyl]azetidine and THF as solvent.
• Example 161 2-[(3'-Cyano-5-fluoro[l,l'-biphenyl]-2-yl)oxy]-(25)-propanoic acid, sodium salt i) 2-(2-Bromo-4-fluorophenoxy)-(2S)-propanoic acid, 1,1-dimethylethyl ester
• the subtitle compound was prepared by the method of example 159 step (i) using 2- bromo-4-fluorophenol (2.5g). Yield 3.0g.
• the subtitle compound was prepared by the method of example 146 step (ii) using the product from step (iii) and ethanol as solvent.
• step (v) 4-Fluoro-2-[2-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy]-(2S)- propanoic acid, 1,1-dimethylethyl ester
• the subtitle compound was prepared by the method of example 32 step (v) using the product from step (iv) and tert-butyl R-lactate. Yield 2.6g.
• the crude material was carried forward to step (vi).
• the title compound was prepared by the method of example 155 using the product from example 161 step (ii) and 2-bromo-l-chloro-4-(trifluoromethyl)benzene.
• the product was dissolved in acetonitrile, treated with IM sodium hydroxide and evaporated to give the title compound. Yield 0.07g.
• the subtitle compound was prepared by the method of example 1 step (ii) using the product from step (i) (1.78g) and 4-(ethylthio)phenylboronic acid (1.6g). Yield 2.59g. ⁇ NMR CDC1 3 : ⁇ 8.02 (d, IH), 8.0 (d, 2H), 7.45 (d, 2H), 6.75 (d, IH), 4.65 (s, 2H), 3.76 (s, 3H), 3.2 (q, 2H), 2.25 (s, 3H) 1.36 (t, 3H)
• step (iv) [[4'-(Methylsulfonyl)-2',5-bis(trifluoromethyl)[l,r-bi ⁇ henyl]-2-yl]oxy]acetic acid, 1,1-dimethylethyl ester
• the product from step (iv) (0.564g) was dissolved in 50% aqueous acetone (10ml), sodium bicarbonate (0.94g) added, followed by a solution of oxone (1.5g) in water (ml) and stined for 3h. The reaction was quenched with aqueous sodium metabisulfite, extracted with
• Example 168 2-[4-Chloro-2-[4-methyl-6-[methyl(methylsulfonyl)amino]-3-pyridinyl]phenoxy]-(2S)- propanoic acid i) N-(5-Bromo-4-methyl-2-pyridinyl)methanesulfonamide 5-Bromo-4-methylpyridin-2-amine (1.56g) was dissolved in DCM (40ml), trimethylamine (1.4ml) added, followed by methanesulfonyl chloride (1.9g) and the mixture stirred for 20min. The solution was washed with water, dried (MgSO 4 ) and evaporated.

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