CA2648810A1 - Organic compounds - Google Patents
Organic compounds Download PDFInfo
- Publication number
- CA2648810A1 CA2648810A1 CA002648810A CA2648810A CA2648810A1 CA 2648810 A1 CA2648810 A1 CA 2648810A1 CA 002648810 A CA002648810 A CA 002648810A CA 2648810 A CA2648810 A CA 2648810A CA 2648810 A1 CA2648810 A1 CA 2648810A1
- Authority
- CA
- Canada
- Prior art keywords
- purin
- mmol
- compound
- ethylamino
- acid
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000002894 organic compounds Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 91
- 239000003814 drug Substances 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims description 19
- 150000003839 salts Chemical group 0.000 claims description 18
- 230000002757 inflammatory effect Effects 0.000 claims description 17
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 208000027771 Obstructive airways disease Diseases 0.000 claims description 9
- 208000027866 inflammatory disease Diseases 0.000 claims description 9
- 230000003110 anti-inflammatory effect Effects 0.000 claims description 8
- 230000003182 bronchodilatating effect Effects 0.000 claims description 8
- 230000004913 activation Effects 0.000 claims description 7
- 102000007471 Adenosine A2A receptor Human genes 0.000 claims description 6
- 108010085277 Adenosine A2A receptor Proteins 0.000 claims description 6
- 229940124623 antihistamine drug Drugs 0.000 claims description 6
- 239000000739 antihistaminic agent Substances 0.000 claims description 6
- 239000008194 pharmaceutical composition Substances 0.000 claims description 6
- GUGOEEXESWIERI-UHFFFAOYSA-N Terfenadine Chemical compound C1=CC(C(C)(C)C)=CC=C1C(O)CCCN1CCC(C(O)(C=2C=CC=CC=2)C=2C=CC=CC=2)CC1 GUGOEEXESWIERI-UHFFFAOYSA-N 0.000 claims description 5
- 230000001387 anti-histamine Effects 0.000 claims description 5
- 239000003434 antitussive agent Substances 0.000 claims description 5
- 229940124584 antitussives Drugs 0.000 claims description 5
- 229940088679 drug related substance Drugs 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 239000008186 active pharmaceutical agent Substances 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 4
- 230000001404 mediated effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 71
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical group ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 54
- 239000000543 intermediate Substances 0.000 description 35
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 34
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- 239000000243 solution Substances 0.000 description 32
- 239000000203 mixture Substances 0.000 description 28
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 25
- 239000011541 reaction mixture Substances 0.000 description 25
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 23
- 208000006673 asthma Diseases 0.000 description 20
- 239000003795 chemical substances by application Substances 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 238000006243 chemical reaction Methods 0.000 description 18
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 16
- 238000004440 column chromatography Methods 0.000 description 16
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 16
- 229940080818 propionamide Drugs 0.000 description 16
- 230000002441 reversible effect Effects 0.000 description 16
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
- -1 aliphatic monocarboxylic acids Chemical class 0.000 description 15
- 238000000746 purification Methods 0.000 description 15
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 13
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 12
- 239000000047 product Substances 0.000 description 12
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 description 10
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 229910052786 argon Inorganic materials 0.000 description 8
- 239000012298 atmosphere Substances 0.000 description 8
- 201000010099 disease Diseases 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 7
- 239000005557 antagonist Substances 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 6
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 6
- 235000019341 magnesium sulphate Nutrition 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
- 239000012267 brine Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 210000003979 eosinophil Anatomy 0.000 description 5
- OKKJLVBELUTLKV-VMNATFBRSA-N methanol-d1 Chemical compound [2H]OC OKKJLVBELUTLKV-VMNATFBRSA-N 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 230000009466 transformation Effects 0.000 description 5
- 238000000844 transformation Methods 0.000 description 5
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 4
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 4
- 206010027654 Allergic conditions Diseases 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
- 150000001408 amides Chemical class 0.000 description 4
- 230000001363 autoimmune Effects 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
- 230000001684 chronic effect Effects 0.000 description 4
- 208000035475 disorder Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 125000000524 functional group Chemical group 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 230000008569 process Effects 0.000 description 4
- 230000005855 radiation Effects 0.000 description 4
- 230000002829 reductive effect Effects 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- 235000009518 sodium iodide Nutrition 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- OKRROXQXGNEUSS-UHFFFAOYSA-N 1h-imidazol-1-ium-1-carboxylate Chemical compound OC(=O)N1C=CN=C1 OKRROXQXGNEUSS-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 102100035875 C-C chemokine receptor type 5 Human genes 0.000 description 3
- 101710149870 C-C chemokine receptor type 5 Proteins 0.000 description 3
- 102100027047 Cell division control protein 6 homolog Human genes 0.000 description 3
- 206010014950 Eosinophilia Diseases 0.000 description 3
- 101000914465 Homo sapiens Cell division control protein 6 homolog Proteins 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 206010063837 Reperfusion injury Diseases 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000001154 acute effect Effects 0.000 description 3
- 239000000443 aerosol Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 206010006451 bronchitis Diseases 0.000 description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000012043 crude product Substances 0.000 description 3
- 206010012601 diabetes mellitus Diseases 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 235000019439 ethyl acetate Nutrition 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 229960004592 isopropanol Drugs 0.000 description 3
- GTGCBQSIGWTVFC-UHFFFAOYSA-N n-(1-pyridin-2-ylpiperidin-4-yl)imidazole-1-carboxamide Chemical compound C1=CN=CN1C(=O)NC(CC1)CCN1C1=CC=CC=N1 GTGCBQSIGWTVFC-UHFFFAOYSA-N 0.000 description 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
- RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 3
- 230000000069 prophylactic effect Effects 0.000 description 3
- 239000012453 solvate Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 125000001424 substituent group Chemical group 0.000 description 3
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- 238000002560 therapeutic procedure Methods 0.000 description 3
- NGXSWUFDCSEIOO-SCSAIBSYSA-N (3r)-pyrrolidin-3-amine Chemical compound N[C@@H]1CCNC1 NGXSWUFDCSEIOO-SCSAIBSYSA-N 0.000 description 2
- DKCWQRKXTQSULZ-UHFFFAOYSA-N 1h-imidazole;urea Chemical compound NC(N)=O.C1=CNC=N1 DKCWQRKXTQSULZ-UHFFFAOYSA-N 0.000 description 2
- RXMTUVIKZRXSSM-UHFFFAOYSA-N 2,2-diphenylethanamine Chemical compound C=1C=CC=CC=1C(CN)C1=CC=CC=C1 RXMTUVIKZRXSSM-UHFFFAOYSA-N 0.000 description 2
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 description 2
- FJKROLUGYXJWQN-UHFFFAOYSA-N 4-hydroxybenzoic acid Chemical compound OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 2
- IHOXNOQMRZISPV-YJYMSZOUSA-N 5-[(1r)-1-hydroxy-2-[[(2r)-1-(4-methoxyphenyl)propan-2-yl]azaniumyl]ethyl]-2-oxo-1h-quinolin-8-olate Chemical compound C1=CC(OC)=CC=C1C[C@@H](C)NC[C@H](O)C1=CC=C(O)C2=C1C=CC(=O)N2 IHOXNOQMRZISPV-YJYMSZOUSA-N 0.000 description 2
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 2
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 description 2
- 239000005711 Benzoic acid Substances 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- JZUFKLXOESDKRF-UHFFFAOYSA-N Chlorothiazide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC2=C1NCNS2(=O)=O JZUFKLXOESDKRF-UHFFFAOYSA-N 0.000 description 2
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 description 2
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- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 208000009319 Keratoconjunctivitis Sicca Diseases 0.000 description 2
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
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- 206010038923 Retinopathy Diseases 0.000 description 2
- 206010039085 Rhinitis allergic Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 206010047924 Wheezing Diseases 0.000 description 2
- YEEZWCHGZNKEEK-UHFFFAOYSA-N Zafirlukast Chemical compound COC1=CC(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C)=CC=C1CC(C1=C2)=CN(C)C1=CC=C2NC(=O)OC1CCCC1 YEEZWCHGZNKEEK-UHFFFAOYSA-N 0.000 description 2
- JAHYUTXINRZWIP-JGVFFNPUSA-N [(1s,4r)-4-(2,6-dichloropurin-9-yl)cyclopent-2-en-1-yl] ethyl carbonate Chemical compound C1=C[C@@H](OC(=O)OCC)C[C@H]1N1C2=NC(Cl)=NC(Cl)=C2N=C1 JAHYUTXINRZWIP-JGVFFNPUSA-N 0.000 description 2
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
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- 239000000556 agonist Substances 0.000 description 2
- NDAUXUAQIAJITI-UHFFFAOYSA-N albuterol Chemical compound CC(C)(C)NCC(O)C1=CC=C(O)C(CO)=C1 NDAUXUAQIAJITI-UHFFFAOYSA-N 0.000 description 2
- 230000029936 alkylation Effects 0.000 description 2
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- CFBUZOUXXHZCFB-OYOVHJISSA-N chembl511115 Chemical compound COC1=CC=C([C@@]2(CC[C@H](CC2)C(O)=O)C#N)C=C1OC1CCCC1 CFBUZOUXXHZCFB-OYOVHJISSA-N 0.000 description 2
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- 239000008101 lactose Substances 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
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- UVLGOYYWYHFWSY-XPZSDMQCSA-N n-[(1s,2r,3s,4r)-4-[6-(2,2-diphenylethylamino)-2-[2-(1-propan-2-ylimidazol-4-yl)ethylamino]purin-9-yl]-2,3-dihydroxycyclopentyl]-2,2-dimethylpropanamide Chemical compound CC(C)N1C=NC(CCNC=2N=C3N([C@H]4[C@@H]([C@H](O)[C@@H](NC(=O)C(C)(C)C)C4)O)C=NC3=C(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)N=2)=C1 UVLGOYYWYHFWSY-XPZSDMQCSA-N 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 230000001737 promoting effect Effects 0.000 description 2
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- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 150000003431 steroids Chemical class 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
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- DGCUKMKXWAJAAE-RSLMWUCJSA-N tert-butyl n-[(1s,2r,3s,4r)-4-(2,6-dichloropurin-9-yl)-2,3-dihydroxycyclopentyl]-n-[(2-methylpropan-2-yl)oxycarbonyl]carbamate Chemical compound O[C@@H]1[C@H](O)[C@@H](N(C(=O)OC(C)(C)C)C(=O)OC(C)(C)C)C[C@H]1N1C2=NC(Cl)=NC(Cl)=C2N=C1 DGCUKMKXWAJAAE-RSLMWUCJSA-N 0.000 description 2
- 229940124597 therapeutic agent Drugs 0.000 description 2
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- XWTYSIMOBUGWOL-UHFFFAOYSA-N (+-)-Terbutaline Chemical compound CC(C)(C)NCC(O)C1=CC(O)=CC(O)=C1 XWTYSIMOBUGWOL-UHFFFAOYSA-N 0.000 description 1
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- MWYHLEQJTQJHSS-UHFFFAOYSA-N tomelukast Chemical compound C1=CC(C(C)=O)=C(O)C(CCC)=C1OCCCCC1=NNN=N1 MWYHLEQJTQJHSS-UHFFFAOYSA-N 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 230000037317 transdermal delivery Effects 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 201000005539 vernal conjunctivitis Diseases 0.000 description 1
- 208000018464 vernal keratoconjunctivitis Diseases 0.000 description 1
- 229960004764 zafirlukast Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/02—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6
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- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
- A61K31/52—Purines, e.g. adenine
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-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
- C07D473/32—Nitrogen atom
- C07D473/34—Nitrogen atom attached in position 6, e.g. adenine
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pulmonology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Hematology (AREA)
- Physical Education & Sports Medicine (AREA)
- Rheumatology (AREA)
- Ophthalmology & Optometry (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Emergency Medicine (AREA)
- Otolaryngology (AREA)
- Anesthesiology (AREA)
- Pain & Pain Management (AREA)
- Endocrinology (AREA)
- Obesity (AREA)
- Psychiatry (AREA)
- Immunology (AREA)
- Vascular Medicine (AREA)
- Hospice & Palliative Care (AREA)
- Gastroenterology & Hepatology (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0607945.3 | 2006-04-21 | ||
| GBGB0607945.3A GB0607945D0 (en) | 2006-04-21 | 2006-04-21 | Organic compounds |
| PCT/EP2007/003432 WO2007121917A2 (en) | 2006-04-21 | 2007-04-19 | Purine derivatives as adenosine receptor activator |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2648810A1 true CA2648810A1 (en) | 2007-11-01 |
Family
ID=36581042
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002648810A Abandoned CA2648810A1 (en) | 2006-04-21 | 2007-04-19 | Organic compounds |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US20090281127A1 (enExample) |
| EP (1) | EP2018382A2 (enExample) |
| JP (1) | JP2009534335A (enExample) |
| KR (1) | KR20080110837A (enExample) |
| CN (1) | CN101421271A (enExample) |
| AU (1) | AU2007241340A1 (enExample) |
| BR (1) | BRPI0710484A2 (enExample) |
| CA (1) | CA2648810A1 (enExample) |
| GB (1) | GB0607945D0 (enExample) |
| MX (1) | MX2008013522A (enExample) |
| RU (1) | RU2008145714A (enExample) |
| WO (1) | WO2007121917A2 (enExample) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0607950D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| AR060607A1 (es) | 2006-04-21 | 2008-07-02 | Novartis Ag | Derivados de purina,composiciones farmaceuticas que los contienen, metodo de preparacion y usos en enfermedades obstructivas o inflamatorias de las vias respiratorias. |
| GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) * | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| KR20090087054A (ko) * | 2006-11-10 | 2009-08-14 | 노파르티스 아게 | 시클로펜텐 디올 모노아세테이트 유도체 |
| US20100197914A1 (en) * | 2007-10-17 | 2010-08-05 | Robin Alec Fairhurst | Purine Derivatives as Adenosine Al Receptor Ligands |
| US20090181934A1 (en) * | 2007-10-17 | 2009-07-16 | Novartis Ag | Organic Compounds |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2264826T3 (es) * | 1998-10-16 | 2007-01-16 | Pfizer Inc. | Derivados de adenina. |
| US20040162422A1 (en) * | 2001-03-20 | 2004-08-19 | Adrian Hall | Chemical compounds |
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| DK1848718T3 (da) * | 2005-02-04 | 2012-08-27 | Millennium Pharm Inc | E1 aktiveringsenzymhæmmere |
| PT1989206E (pt) * | 2006-02-02 | 2012-10-15 | Millennium Pharm Inc | Inibidores da enzima de ativação e1 |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607944D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| US8008307B2 (en) * | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| US20090181934A1 (en) * | 2007-10-17 | 2009-07-16 | Novartis Ag | Organic Compounds |
-
2006
- 2006-04-21 GB GBGB0607945.3A patent/GB0607945D0/en not_active Ceased
-
2007
- 2007-04-19 US US12/297,007 patent/US20090281127A1/en not_active Abandoned
- 2007-04-19 MX MX2008013522A patent/MX2008013522A/es not_active Application Discontinuation
- 2007-04-19 KR KR1020087025546A patent/KR20080110837A/ko not_active Withdrawn
- 2007-04-19 EP EP07724369A patent/EP2018382A2/en not_active Withdrawn
- 2007-04-19 JP JP2009505776A patent/JP2009534335A/ja active Pending
- 2007-04-19 BR BRPI0710484-7A patent/BRPI0710484A2/pt not_active IP Right Cessation
- 2007-04-19 WO PCT/EP2007/003432 patent/WO2007121917A2/en not_active Ceased
- 2007-04-19 CN CNA2007800136743A patent/CN101421271A/zh active Pending
- 2007-04-19 RU RU2008145714/04A patent/RU2008145714A/ru not_active Application Discontinuation
- 2007-04-19 CA CA002648810A patent/CA2648810A1/en not_active Abandoned
- 2007-04-19 AU AU2007241340A patent/AU2007241340A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP2018382A2 (en) | 2009-01-28 |
| KR20080110837A (ko) | 2008-12-19 |
| CN101421271A (zh) | 2009-04-29 |
| WO2007121917A2 (en) | 2007-11-01 |
| GB0607945D0 (en) | 2006-05-31 |
| RU2008145714A (ru) | 2010-05-27 |
| BRPI0710484A2 (pt) | 2011-08-16 |
| MX2008013522A (es) | 2008-10-29 |
| WO2007121917A3 (en) | 2007-12-06 |
| US20090281127A1 (en) | 2009-11-12 |
| AU2007241340A1 (en) | 2007-11-01 |
| JP2009534335A (ja) | 2009-09-24 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2322525B1 (en) | Purine derivatives for use as adenosin A2A receptor agonists | |
| EP2066669B1 (en) | Adenosine derivatives as a2a receptor agonists | |
| US20090099214A1 (en) | Organic Compounds | |
| CA2648810A1 (en) | Organic compounds | |
| US20090105476A1 (en) | Organic Compounds | |
| WO2008006563A1 (en) | Purine derivatives as a2a agonists | |
| AU2005298878B2 (en) | Purine derivatives for use as adenosin A-2A receptor agonists | |
| HK1131392B (en) | Adenosine derivatives as a2a receptor agonists |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |