BRPI0710514A2 - compostos orgánicos, seus usos e processos de preparação, e composições farmacêuticas compreendendo os mesmos - Google Patents
compostos orgánicos, seus usos e processos de preparação, e composições farmacêuticas compreendendo os mesmos Download PDFInfo
- Publication number
- BRPI0710514A2 BRPI0710514A2 BRPI0710514-2A BRPI0710514A BRPI0710514A2 BR PI0710514 A2 BRPI0710514 A2 BR PI0710514A2 BR PI0710514 A BRPI0710514 A BR PI0710514A BR PI0710514 A2 BRPI0710514 A2 BR PI0710514A2
- Authority
- BR
- Brazil
- Prior art keywords
- alkyl
- formula
- optionally
- alkoxy
- halo
- Prior art date
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- 238000002360 preparation method Methods 0.000 title claims abstract description 17
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 6
- 238000000034 method Methods 0.000 title claims description 21
- 230000008569 process Effects 0.000 title claims description 3
- 150000002894 organic compounds Chemical class 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 67
- 239000000825 pharmaceutical preparation Substances 0.000 claims abstract 2
- 229940127557 pharmaceutical product Drugs 0.000 claims abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
- 229910052757 nitrogen Inorganic materials 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 32
- -1 C1-C8-alkoxy Chemical group 0.000 claims description 31
- 125000005843 halogen group Chemical group 0.000 claims description 28
- 229910052717 sulfur Chemical group 0.000 claims description 28
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 27
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 27
- 239000001301 oxygen Substances 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 27
- 239000011593 sulfur Chemical group 0.000 claims description 27
- 125000005842 heteroatom Chemical group 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 17
- 125000002619 bicyclic group Chemical group 0.000 claims description 16
- 125000000623 heterocyclic group Chemical group 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical group 0.000 claims description 9
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- 238000011282 treatment Methods 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 125000004414 alkyl thio group Chemical group 0.000 claims description 6
- 229910052799 carbon Inorganic materials 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 108010060261 Adenosine A3 Receptor Proteins 0.000 claims description 5
- 102000008161 Adenosine A3 Receptor Human genes 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 5
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 230000004913 activation Effects 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000004043 oxo group Chemical group O=* 0.000 claims description 4
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 230000001404 mediated effect Effects 0.000 claims description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 2
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 2
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims 1
- 125000000000 cycloalkoxy group Chemical group 0.000 claims 1
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims 1
- 125000005167 cycloalkylaminocarbonyl group Chemical group 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 57
- 230000002829 reductive effect Effects 0.000 description 29
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 28
- 239000000047 product Substances 0.000 description 26
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- 239000011541 reaction mixture Substances 0.000 description 23
- 238000003818 flash chromatography Methods 0.000 description 20
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000000203 mixture Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 18
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- 238000002425 crystallisation Methods 0.000 description 17
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- 238000003556 assay Methods 0.000 description 16
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- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 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 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- KCXVZYZYPLLWCC-UHFFFAOYSA-N EDTA Chemical compound OC(=O)CN(CC(O)=O)CCN(CC(O)=O)CC(O)=O KCXVZYZYPLLWCC-UHFFFAOYSA-N 0.000 description 12
- 239000007995 HEPES buffer Substances 0.000 description 12
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 12
- 239000012131 assay buffer Substances 0.000 description 12
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- 208000021386 Sjogren Syndrome Diseases 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 9
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 9
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 9
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- ZKBQDFAWXLTYKS-UHFFFAOYSA-N 6-Chloro-1H-purine Chemical group ClC1=NC=NC2=C1NC=N2 ZKBQDFAWXLTYKS-UHFFFAOYSA-N 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 210000004027 cell Anatomy 0.000 description 7
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 7
- 125000006239 protecting group Chemical group 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
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- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 4
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- 238000002731 protein assay Methods 0.000 description 1
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- 239000012264 purified product Substances 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005258 radioactive decay Effects 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 230000000306 recurrent effect Effects 0.000 description 1
- 239000012088 reference solution Substances 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 229930187593 rose bengal Natural products 0.000 description 1
- 229940081623 rose bengal Drugs 0.000 description 1
- STRXNPAVPKGJQR-UHFFFAOYSA-N rose bengal A Natural products O1C(=O)C(C(=CC=C2Cl)Cl)=C2C21C1=CC(I)=C(O)C(I)=C1OC1=C(I)C(O)=C(I)C=C21 STRXNPAVPKGJQR-UHFFFAOYSA-N 0.000 description 1
- 210000003296 saliva Anatomy 0.000 description 1
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- 230000035939 shock Effects 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
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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 1
- JJOIPZNUMCWSCX-LCLWPZTBSA-N tert-butyl n-[(1s,2r,3s,4r)-4-[2-chloro-6-[(3-iodophenyl)methylamino]purin-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(NCC=3C=C(I)C=CC=3)=C2N=C1 JJOIPZNUMCWSCX-LCLWPZTBSA-N 0.000 description 1
- 150000003536 tetrazoles Chemical class 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
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- ZTWIEIFKPFJRLV-UHFFFAOYSA-K trichlororuthenium;trihydrate Chemical compound O.O.O.Cl[Ru](Cl)Cl ZTWIEIFKPFJRLV-UHFFFAOYSA-K 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
- 239000011534 wash buffer Substances 0.000 description 1
- 230000029663 wound healing Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/08—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing alicyclic rings
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
- C07D473/40—Heterocyclic compounds containing purine ring systems with halogen atoms or perhalogeno-alkyl radicals directly attached in position 2 or 6
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
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| GBGB0607944.6A GB0607944D0 (en) | 2006-04-21 | 2006-04-21 | Organic compounds |
| GB0607944.6 | 2006-04-21 | ||
| PCT/EP2007/053847 WO2007147659A1 (en) | 2006-04-21 | 2007-04-19 | Adenosine a3 receptor agonists |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BRPI0710514A2 true BRPI0710514A2 (pt) | 2011-08-16 |
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| BRPI0710514-2A BRPI0710514A2 (pt) | 2006-04-21 | 2007-04-19 | compostos orgánicos, seus usos e processos de preparação, e composições farmacêuticas compreendendo os mesmos |
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| US (1) | US20090281126A1 (enExample) |
| EP (1) | EP2013199A1 (enExample) |
| JP (1) | JP2009534358A (enExample) |
| KR (1) | KR20080110845A (enExample) |
| CN (1) | CN101426785A (enExample) |
| AU (1) | AU2007263237B2 (enExample) |
| BR (1) | BRPI0710514A2 (enExample) |
| CA (1) | CA2649648A1 (enExample) |
| GB (1) | GB0607944D0 (enExample) |
| MX (1) | MX2008013520A (enExample) |
| RU (1) | RU2008145708A (enExample) |
| WO (1) | WO2007147659A1 (enExample) |
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| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0607948D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| WO2007121920A2 (en) | 2006-04-21 | 2007-11-01 | Novartis Ag | Purine derivatives for use as adenosin a2a receptor agonists |
| GB0607953D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607945D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607950D0 (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 |
| US20100041918A1 (en) * | 2006-11-10 | 2010-02-18 | Novartis Ag | Cyclopentene diol monoacetate derivatives |
| CN101827847A (zh) * | 2007-10-17 | 2010-09-08 | 诺瓦提斯公司 | 用作腺苷a1受体配体的嘌呤衍生物 |
| WO2009123881A1 (en) | 2008-03-31 | 2009-10-08 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Purine derivatives as a3 receptor- selective agonists |
| US8916570B2 (en) | 2008-03-31 | 2014-12-23 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor agonists and antagonists |
| US8796291B2 (en) | 2008-08-01 | 2014-08-05 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor antagonists and partial agonists |
| US9181253B2 (en) | 2008-08-01 | 2015-11-10 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Adenosine receptor agonists, partial agonists, and antagonists |
Family Cites Families (39)
| Publication number | Priority date | Publication date | Assignee | Title |
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| GB1528382A (en) * | 1974-12-26 | 1978-10-11 | Teijin Ltd | Cyclopentene diols and acyl esters thereof and processes for their preparation |
| US4738954A (en) * | 1985-11-06 | 1988-04-19 | Warner-Lambert Company | Novel N6 -substituted-5'-oxidized adenosine analogs |
| US4954504A (en) * | 1986-11-14 | 1990-09-04 | Ciba-Geigy Corporation | N9 -cyclopentyl-substituted adenine derivatives having adenosine-2 receptor stimulating activity |
| US5688774A (en) * | 1993-07-13 | 1997-11-18 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| BR9612341A (pt) * | 1996-01-02 | 1999-12-28 | Rhone Poulenc Rorer Pharma | Processo para preparar 2,4-diidróxipiridina. |
| US6376472B1 (en) * | 1996-07-08 | 2002-04-23 | Aventis Pharmaceuticals, Inc. | Compounds having antihypertensive, cardioprotective, anti-ischemic and antilipolytic properties |
| GB9813554D0 (en) * | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
| KR20010089751A (ko) * | 1998-12-31 | 2001-10-08 | 오흘러 로스 제이. | Ｎ6-치환된 데아자-아데노신 유도체의 제조방법 |
| US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| US6403567B1 (en) * | 1999-06-22 | 2002-06-11 | Cv Therapeutics, Inc. | N-pyrazole A2A adenosine receptor agonists |
| US6586413B2 (en) * | 1999-11-05 | 2003-07-01 | The United States Of America As Represented By The Department Of Health And Human Services | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
| BR0206492A (pt) * | 2001-01-16 | 2004-02-10 | Can Fite Biopharma Ltd | Composição farmacêutica para inibir a replicação de um vìrus dentro de células, uso de pelo menos um agonista receptor de adenosina a3, e, métodos para inibir a replicação de um vìrus em células |
| US20040162422A1 (en) * | 2001-03-20 | 2004-08-19 | Adrian Hall | Chemical compounds |
| EP1258247A1 (en) * | 2001-05-14 | 2002-11-20 | Aventis Pharma Deutschland GmbH | Adenosine analogues for the treatment of insulin resistance syndrome and diabetes |
| US7414036B2 (en) * | 2002-01-25 | 2008-08-19 | Muscagen Limited | Compounds useful as A3 adenosine receptor agonists |
| PL1699459T3 (pl) * | 2003-12-29 | 2007-12-31 | Can Fite Biopharma Ltd | Sposób leczenia stwardnienia rozsianego |
| US7825102B2 (en) * | 2004-07-28 | 2010-11-02 | Can-Fite Biopharma Ltd. | Treatment of dry eye conditions |
| EP1778239B1 (en) * | 2004-07-28 | 2013-08-21 | Can-Fite Biopharma Ltd. | Adenosine a3 receptor agonists for the treatment of dry eye disorders including sjogren's syndrome |
| CN101056879B (zh) * | 2004-09-09 | 2011-10-05 | 美国政府卫生与公共服务部 | 作为a3和a1腺苷受体激动剂的嘌呤衍生物 |
| GT200500281A (es) * | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| US7176172B2 (en) * | 2004-10-25 | 2007-02-13 | Unilever Home & Personal Care Usa, Division Of Conopco, Inc. | Quaternary ammonium polyol salts as anti-aging actives in personal care compositions |
| US20080051364A1 (en) * | 2004-11-08 | 2008-02-28 | Pninna Fishman | Therapeutic Treatment of Accelerated Bone Resorption |
| GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| EP1848718B1 (en) * | 2005-02-04 | 2012-08-01 | Millennium Pharmaceuticals, Inc. | Inhibitors of e1 activating enzymes |
| CA2622879C (en) * | 2005-11-30 | 2011-07-05 | Can-Fite Biopharma Ltd. | Use of a3 adenosine receptor agonist in osteoarthritis treatment |
| DK1983990T3 (da) * | 2006-01-26 | 2011-07-11 | Us Gov Health & Human Serv | Allosteriske A3-adenosin-receptormodulatorer |
| CN106008512B (zh) * | 2006-02-02 | 2019-03-12 | 千禧药品公司 | E1活化酶抑制剂 |
| WO2007121920A2 (en) * | 2006-04-21 | 2007-11-01 | Novartis Ag | Purine derivatives for use as adenosin a2a receptor agonists |
| GB0607950D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| GB0607954D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
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| GB0607951D0 (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 |
| US8008307B2 (en) * | 2006-08-08 | 2011-08-30 | Millennium Pharmaceuticals, Inc. | Heteroaryl compounds useful as inhibitors of E1 activating enzymes |
| EP1903044A1 (en) * | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| US20100041918A1 (en) * | 2006-11-10 | 2010-02-18 | Novartis Ag | Cyclopentene diol monoacetate derivatives |
| US20090181934A1 (en) * | 2007-10-17 | 2009-07-16 | Novartis Ag | Organic Compounds |
| CN101827847A (zh) * | 2007-10-17 | 2010-09-08 | 诺瓦提斯公司 | 用作腺苷a1受体配体的嘌呤衍生物 |
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2006
- 2006-04-21 GB GBGB0607944.6A patent/GB0607944D0/en not_active Ceased
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2007
- 2007-04-19 US US12/296,714 patent/US20090281126A1/en not_active Abandoned
- 2007-04-19 CA CA002649648A patent/CA2649648A1/en not_active Abandoned
- 2007-04-19 AU AU2007263237A patent/AU2007263237B2/en not_active Ceased
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- 2007-04-19 MX MX2008013520A patent/MX2008013520A/es not_active Application Discontinuation
- 2007-04-19 EP EP07845239A patent/EP2013199A1/en not_active Withdrawn
- 2007-04-19 CN CNA2007800142903A patent/CN101426785A/zh active Pending
- 2007-04-19 BR BRPI0710514-2A patent/BRPI0710514A2/pt not_active IP Right Cessation
- 2007-04-19 JP JP2009505894A patent/JP2009534358A/ja active Pending
- 2007-04-19 RU RU2008145708/04A patent/RU2008145708A/ru not_active Application Discontinuation
- 2007-04-19 KR KR1020087025605A patent/KR20080110845A/ko not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| AU2007263237A1 (en) | 2007-12-27 |
| EP2013199A1 (en) | 2009-01-14 |
| GB0607944D0 (en) | 2006-05-31 |
| CA2649648A1 (en) | 2007-12-27 |
| MX2008013520A (es) | 2008-10-29 |
| WO2007147659A1 (en) | 2007-12-27 |
| AU2007263237B2 (en) | 2010-09-30 |
| JP2009534358A (ja) | 2009-09-24 |
| RU2008145708A (ru) | 2010-05-27 |
| US20090281126A1 (en) | 2009-11-12 |
| KR20080110845A (ko) | 2008-12-19 |
| CN101426785A (zh) | 2009-05-06 |
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Free format text: ANULADA A PUBLICACAO CODIGO 8.12 NA RPI NO 2259 DE 22/04/2014 POR TER SIDO INDEVIDA. |
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