WO1999034804A1 - A2a adenosine receptor agonists - Google Patents
A2a adenosine receptor agonists Download PDFInfo
- Publication number
- WO1999034804A1 WO1999034804A1 PCT/US1999/000366 US9900366W WO9934804A1 WO 1999034804 A1 WO1999034804 A1 WO 1999034804A1 US 9900366 W US9900366 W US 9900366W WO 9934804 A1 WO9934804 A1 WO 9934804A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- rolipram
- alkyl
- groups
- adenosine receptor
- type
- Prior art date
Links
- 0 *[C@@]([C@@]([C@]1O)O)O[C@]1[n]1c(NC(*)N=C2N)c2nc1 Chemical compound *[C@@]([C@@]([C@]1O)O)O[C@]1[n]1c(NC(*)N=C2N)c2nc1 0.000 description 1
Classifications
-
- 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
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- 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
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Definitions
- Figure 3 illustrates the synergistic effect of WRC-0474[SHA 211] and rolipram in inhibiting TNF ⁇ -stimulated adherent PMN superoxide release;
- each of R 5 and R 6 independently may be hydrogen, C 3.7 -cycloalkyl, or any of the meanings of R 1 , provided that R 5 and R 6 are not both hydrogen;
- R 18 and R 19 each are alike or different and are hydrocarbon radicals having up to 18 carbon atoms with at least one being other than methyl, a heterocychc ring, or alkyl of 1-5 carbon atoms which is substituted by one or more of halogen atoms, hydroxy, carboxy, alkoxy, alkoxycarbonyl or an amino group or amino.
- alkyl groups examples include hydroxy groups, e.g., 2-hydroxyethyl or 3-hydroxypropyl; carboxy groups, e.g., carboxymethyl or carboxyethyl; alkoxy groups, wherein each alkoxy group contains 1-5 carbon atoms, e.g., ethoxymethyl, isopropoxymethyl, 2- methoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2-isobutyoxyethyl, and 3- pentoxypropyl.
- alkoxycarbonyl of 1-5 carbon atoms in the alkoxy group are alkoxycarbonyl of 1-5 carbon atoms in the alkoxy group.
- the compound of formula (I) may be administered in the form of a pharmaceutically acceptable salt.
- salts include acid addition salts.
- Preferred pharmaceutically acceptable addition salts include salts of mineral acids, for example, hydrochloric acid, sulfuric acid, nitric acid, and the like; salts of monobasic carboxylic acids, such as, for example, acetic acid, propionic acid, and the like; salts of dibasic carboxylic acids, such as maleic acid, fumaric acid, oxalic acid, and the like; and salts of tribasic carboxylic acids, such as carboxysuccinic acid, citric acid, and the like.
- the amount of active agent per oral dosage unit usually is 0.1-20 mg, preferably 0.5-10 mg.
- the daily dosage is usually 0.1- 50 mg, preferably 1-30 mg p.o.
- the amount of active agent per dosage unit is usually 0.005-10 mg, preferably 0.01-5 mg.
- the daily dosage is usually 0.01-20 mg, preferably 0.02-5 mg i.v. or i.m.
- dosage levels and their related procedures would be consistent with those known in the art, such as those dosage levels and procedures described in U.S. Patent No. 5,565,462 to Eitan et al., which is incorporated herein by reference.
- the dosage of the A 2A adenosine receptor agonist may be reduced by a factor of 5 to 10 from the dosage used when no Type IV phosphodiesterase inhibitor is administered. This reduces the possibility of side effects.
- the present invention will now be described in more detail in the context of the coadministration of WRC-0470, WRC-0474[SHA 211], WRC-0090 or WRC-0018 and rolipram. However, it is to be understood that the present invention may be practiced with other compounds of formula (I) and other Type IV phosphodiesterase inhibitors of formula (V).
- Adenoviral- mediated gene transfer affords several advantages over other techniques.
- gene expression is only transient, and has been observed for 7-14 days with diminution or loss of expression by 28 days. Lack of persistence may result form host immune cytolytic responses directed against infected cells.
- the inflammatory response generated by the present generation of adenovims results in neointimal lesion formation and may thus offset the benefit of a therapeutic gene.
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU21082/99A AU2108299A (en) | 1998-01-08 | 1999-01-07 | A2A adenosine receptor agonists |
EP99901368A EP1044004A1 (de) | 1998-01-08 | 1999-01-07 | A2a adenosin rezeptor agonisten in kombination mit typ iv phosphodiesterase inhibitoren |
JP2000527253A JP2002500188A (ja) | 1998-01-08 | 1999-01-07 | A2aアデノシンレセプター作動因子 |
CA002317093A CA2317093A1 (en) | 1998-01-08 | 1999-01-07 | A2a adenosine receptor agonists |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US393098A | 1998-01-08 | 1998-01-08 | |
US09/003,930 | 1998-01-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1999034804A1 true WO1999034804A1 (en) | 1999-07-15 |
Family
ID=21708282
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1999/000366 WO1999034804A1 (en) | 1998-01-08 | 1999-01-07 | A2a adenosine receptor agonists |
Country Status (5)
Country | Link |
---|---|
EP (1) | EP1044004A1 (de) |
JP (1) | JP2002500188A (de) |
AU (1) | AU2108299A (de) |
CA (1) | CA2317093A1 (de) |
WO (1) | WO1999034804A1 (de) |
Cited By (33)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2000072799A2 (en) * | 1999-05-27 | 2000-12-07 | The University Of Virginia Patent Foundation | Method and compositions for treating the inflammatory response |
WO2001081346A2 (en) * | 2000-04-25 | 2001-11-01 | Icos Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
US6326359B1 (en) * | 1998-10-16 | 2001-12-04 | Pfizer Inc | Adenosine A2A receptor agonists as antiinflammatory agents |
WO2001093909A2 (en) * | 2000-06-06 | 2001-12-13 | Glaxo Group Limited | Cancer treatment composition containing an anti-neoplastic agent and a pde4 inhibitor |
WO2002000676A1 (en) * | 2000-06-27 | 2002-01-03 | Pfizer Limited | Purine derivatives |
US6339072B2 (en) | 1997-06-18 | 2002-01-15 | Discovery Therapeutics Inc. | Compositions and methods for preventing restenosis following revascularization procedures |
US6514949B1 (en) | 1994-07-11 | 2003-02-04 | University Of Virginia Patent Foundation | Method compositions for treating the inflammatory response |
US6624158B2 (en) | 2000-09-15 | 2003-09-23 | Pfizer Inc | Purine derivatives |
WO2003086408A1 (en) * | 2002-04-10 | 2003-10-23 | University Of Virginia Patent Foundation | Use of a2a adenosine receptor agonists for the treatment of inflammatory diseases |
US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
WO2004078184A1 (en) * | 2003-03-07 | 2004-09-16 | Cambridge Biotechnology Ltd | Use of adenosine receptor agonists in therapy |
US6921753B2 (en) | 2000-06-27 | 2005-07-26 | Pfizer Inc | Purine derivatives |
US7214665B2 (en) | 2001-10-01 | 2007-05-08 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having A2A agonist activity and compositions thereof |
US7226913B2 (en) | 1999-02-01 | 2007-06-05 | University Of Virginia Patent Foundation | Pharmaceutical compositions having A2A adenosine receptor agonist activity |
EP1802316A2 (de) * | 2004-09-20 | 2007-07-04 | Inotek Pharmaceuticals Corporation | Purin-derivate und anwendungsverfahren |
US7378400B2 (en) | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
US7442687B2 (en) | 2004-08-02 | 2008-10-28 | The University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
US7576069B2 (en) | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
US7605143B2 (en) | 2004-08-02 | 2009-10-20 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5′-ribose groups having A2A agonist activity |
EP2178370A1 (de) * | 2007-07-17 | 2010-04-28 | Combinatorx, Incorporated | Kombinationen für die behandlung von proliferativen b-zellen-erkrankungen |
US7759321B2 (en) | 2003-03-07 | 2010-07-20 | Cambridge Biotechnology Ltd | Compounds for the treatment of pain |
US7932260B2 (en) | 2004-05-13 | 2011-04-26 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US8252766B2 (en) | 2002-12-09 | 2012-08-28 | Cbt Development Limited | Use of spongosine for the treatment of pain |
US8440677B2 (en) | 2009-03-24 | 2013-05-14 | Gilead Calistoga Llc | Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use |
US8691829B2 (en) | 2009-07-21 | 2014-04-08 | Gilead Calistoga Llc | Treatment of liver disorders with PI3K inhibitors |
US8865730B2 (en) | 2012-03-05 | 2014-10-21 | Gilead Calistoga Llc | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US9238070B2 (en) | 2008-11-13 | 2016-01-19 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US9505796B2 (en) | 2006-03-21 | 2016-11-29 | Crozet Medical Gmbh | Phosphorylated A2A receptor agonists |
US9567337B2 (en) | 2013-12-20 | 2017-02-14 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
US9708327B2 (en) | 2013-12-20 | 2017-07-18 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US11021467B2 (en) | 2014-06-13 | 2021-06-01 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
-
1999
- 1999-01-07 AU AU21082/99A patent/AU2108299A/en not_active Abandoned
- 1999-01-07 EP EP99901368A patent/EP1044004A1/de not_active Withdrawn
- 1999-01-07 WO PCT/US1999/000366 patent/WO1999034804A1/en not_active Application Discontinuation
- 1999-01-07 CA CA002317093A patent/CA2317093A1/en not_active Abandoned
- 1999-01-07 JP JP2000527253A patent/JP2002500188A/ja active Pending
Non-Patent Citations (3)
Title |
---|
BUSTER B(A) ET AL: "The effect of adenosine receptor agonists on neutrophil pleocytosis and blood-brain barrier pathophysiology in experimental bacterial meningitis.", ABSTRACTS OF THE INTERSCIENCE CONFERENCE ON ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, 1997, 37TH INTERSCIENCE CONFERENCE ON ANTIMICROBIAL AGENTS AND CHEMOTHERAPY, vol. 37, pages 39, XP002104913 * |
SULLIVAN GW ET AL: "The specific type IV phosphodiesterase inhibitor rolipram combined with adenosine reduces tumor necrosis factor-alpha-primed neutrophil oxidative activity.", INT J IMMUNOPHARMACOL;17(10):793-803 1995, XP002104914 * |
WALKER BA ET AL: "Adenosine A2a receptor activation delays apoptosis in human neutrophils.", J IMMUNOL, MAR 15 1997, 158 (6) P2926-31, UNITED STATES, XP002104915 * |
Cited By (73)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US6514949B1 (en) | 1994-07-11 | 2003-02-04 | University Of Virginia Patent Foundation | Method compositions for treating the inflammatory response |
US6339072B2 (en) | 1997-06-18 | 2002-01-15 | Discovery Therapeutics Inc. | Compositions and methods for preventing restenosis following revascularization procedures |
US6372723B1 (en) | 1997-06-18 | 2002-04-16 | Discovery Therapeutics, Inc. | Compositions and methods for preventing restenosis following revascularization procedures |
US6326359B1 (en) * | 1998-10-16 | 2001-12-04 | Pfizer Inc | Adenosine A2A receptor agonists as antiinflammatory agents |
US7378400B2 (en) | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
US7226913B2 (en) | 1999-02-01 | 2007-06-05 | University Of Virginia Patent Foundation | Pharmaceutical compositions having A2A adenosine receptor agonist activity |
US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
WO2000072799A3 (en) * | 1999-05-27 | 2001-07-12 | Univ Virginia | Method and compositions for treating the inflammatory response |
WO2000072799A2 (en) * | 1999-05-27 | 2000-12-07 | The University Of Virginia Patent Foundation | Method and compositions for treating the inflammatory response |
US8637533B2 (en) | 2000-04-25 | 2014-01-28 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US6800620B2 (en) | 2000-04-25 | 2004-10-05 | Icos | Inhibitors of human phosphatidylinositol 3-kinase delta |
US6518277B1 (en) | 2000-04-25 | 2003-02-11 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US10695349B2 (en) | 2000-04-25 | 2020-06-30 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US8653077B2 (en) | 2000-04-25 | 2014-02-18 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US6667300B2 (en) | 2000-04-25 | 2003-12-23 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US9487772B2 (en) | 2000-04-25 | 2016-11-08 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
EP2223922A3 (de) * | 2000-04-25 | 2011-04-27 | ICOS Corporation | Hemmer der menschlichen Phosphatidyl-inositol-3-kinase delta |
US10010550B2 (en) | 2000-04-25 | 2018-07-03 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US10398695B2 (en) | 2000-04-25 | 2019-09-03 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
US6949535B2 (en) | 2000-04-25 | 2005-09-27 | Icos Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
EA008241B1 (ru) * | 2000-04-25 | 2007-04-27 | Айкос Корпорейшн | Ингибиторы фосфатидилинозитол-3-киназы дельта человека |
WO2001081346A3 (en) * | 2000-04-25 | 2002-03-21 | Icos Corp | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
US8138195B2 (en) | 2000-04-25 | 2012-03-20 | Icos Corporation | Inhibitors of human phosphatidylinositol 3-kinase delta |
WO2001081346A2 (en) * | 2000-04-25 | 2001-11-01 | Icos Corporation | Inhibitors of human phosphatidyl-inositol 3-kinase delta |
WO2001093909A3 (en) * | 2000-06-06 | 2002-12-05 | Glaxo Group Ltd | Cancer treatment composition containing an anti-neoplastic agent and a pde4 inhibitor |
WO2001093909A2 (en) * | 2000-06-06 | 2001-12-13 | Glaxo Group Limited | Cancer treatment composition containing an anti-neoplastic agent and a pde4 inhibitor |
US7238676B2 (en) | 2000-06-27 | 2007-07-03 | Pfizer Inc. | Purine derivatives |
US6921753B2 (en) | 2000-06-27 | 2005-07-26 | Pfizer Inc | Purine derivatives |
AP1372A (en) * | 2000-06-27 | 2005-02-21 | Pfizer | Purine derivatives. |
WO2002000676A1 (en) * | 2000-06-27 | 2002-01-03 | Pfizer Limited | Purine derivatives |
US6624158B2 (en) | 2000-09-15 | 2003-09-23 | Pfizer Inc | Purine derivatives |
US7214665B2 (en) | 2001-10-01 | 2007-05-08 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having A2A agonist activity and compositions thereof |
WO2003086408A1 (en) * | 2002-04-10 | 2003-10-23 | University Of Virginia Patent Foundation | Use of a2a adenosine receptor agonists for the treatment of inflammatory diseases |
US8252766B2 (en) | 2002-12-09 | 2012-08-28 | Cbt Development Limited | Use of spongosine for the treatment of pain |
WO2004078184A1 (en) * | 2003-03-07 | 2004-09-16 | Cambridge Biotechnology Ltd | Use of adenosine receptor agonists in therapy |
US7759321B2 (en) | 2003-03-07 | 2010-07-20 | Cambridge Biotechnology Ltd | Compounds for the treatment of pain |
US7790698B2 (en) | 2003-03-07 | 2010-09-07 | Cambridge Biotechnology Ltd | Use of adenosine receptor agonists in therapy |
US7932260B2 (en) | 2004-05-13 | 2011-04-26 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US8980901B2 (en) | 2004-05-13 | 2015-03-17 | Icos Corporation | 5-fluoro-3-phenyl-2[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US10336756B2 (en) | 2004-05-13 | 2019-07-02 | Icos Corporation | (S)-2-(1-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one precursor of a quinazolinone as inhibitor of human phosphatidylinositol 3-kinase delta |
US9149477B2 (en) | 2004-05-13 | 2015-10-06 | Icos Corporation | 5-fluoro-3-phenyl-2-[1-(9h-purin-6-ylamino)propyl]-3h-quinazolin-4-one as an inhibitor of human phosphatidylinositol 3-kinase delta |
US8207153B2 (en) | 2004-05-13 | 2012-06-26 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US8993583B2 (en) | 2004-05-13 | 2015-03-31 | Icos Corporation | 5-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)propyl]-3H-quinazolin-4-one and 6-fluoro-3-phenyl-2-[1-(9H-purin-6-ylamino)ethyl]-3H-quinazolin-4-one as inhibitors of human phosphatidylinositol 3-kinase delta |
US10906907B2 (en) | 2004-05-13 | 2021-02-02 | Icos Corporation | Tert-butyl (s)-(1-(5-fluoro-4-oxo-3-phenyl-3,4-dihydroquinazolin-2-yl)propyl)carbamate precursor of a quinazolinone inhibitor of human phosphatidylinositol 3-kinase delta and a process for preparing thereof |
USRE44599E1 (en) | 2004-05-13 | 2013-11-12 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
USRE44638E1 (en) | 2004-05-13 | 2013-12-10 | Icos Corporation | Quinazolinones as inhibitors of human phosphatidylinositol 3-kinase delta |
US7989431B2 (en) | 2004-08-02 | 2011-08-02 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5′-ribose groups having A2A agonist activity |
US7576069B2 (en) | 2004-08-02 | 2009-08-18 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
US7442687B2 (en) | 2004-08-02 | 2008-10-28 | The University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having A2A agonist activity |
US7605143B2 (en) | 2004-08-02 | 2009-10-20 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5′-ribose groups having A2A agonist activity |
EP1802316A2 (de) * | 2004-09-20 | 2007-07-04 | Inotek Pharmaceuticals Corporation | Purin-derivate und anwendungsverfahren |
US7863253B2 (en) | 2004-09-20 | 2011-01-04 | Inotek Pharmaceuticals Corporation | Purine Derivatives and methods of use thereof |
EP1802316A4 (de) * | 2004-09-20 | 2010-08-25 | Inotek Pharmaceuticals Corp | Purin-derivate und anwendungsverfahren |
US8133880B2 (en) | 2004-09-20 | 2012-03-13 | Inotek Pharmaceuticals Corporation | Purine derivatives and methods of use thereof |
US9505796B2 (en) | 2006-03-21 | 2016-11-29 | Crozet Medical Gmbh | Phosphorylated A2A receptor agonists |
EP2178370A4 (de) * | 2007-07-17 | 2011-01-12 | Zalicus Inc | Kombinationen für die behandlung von proliferativen b-zellen-erkrankungen |
EP2178370A1 (de) * | 2007-07-17 | 2010-04-28 | Combinatorx, Incorporated | Kombinationen für die behandlung von proliferativen b-zellen-erkrankungen |
US9238070B2 (en) | 2008-11-13 | 2016-01-19 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US10154998B2 (en) | 2008-11-13 | 2018-12-18 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US9492449B2 (en) | 2008-11-13 | 2016-11-15 | Gilead Calistoga Llc | Therapies for hematologic malignancies |
US8440677B2 (en) | 2009-03-24 | 2013-05-14 | Gilead Calistoga Llc | Atropisomers of 2-purinyl-3-tolyl-quinazolinone derivatives and methods of use |
US8691829B2 (en) | 2009-07-21 | 2014-04-08 | Gilead Calistoga Llc | Treatment of liver disorders with PI3K inhibitors |
US9469643B2 (en) | 2012-03-05 | 2016-10-18 | Gilead Calistoga, LLC. | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US10730879B2 (en) | 2012-03-05 | 2020-08-04 | Gilead Calistoga Llc | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US8865730B2 (en) | 2012-03-05 | 2014-10-21 | Gilead Calistoga Llc | Polymorphic forms of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US10059677B2 (en) | 2013-12-20 | 2018-08-28 | Gilead Calistoga Llc | Process for preparing phosphatidylinositol 3-kinase inhibitors and intermediates thereof |
US10047060B2 (en) | 2013-12-20 | 2018-08-14 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
US9708327B2 (en) | 2013-12-20 | 2017-07-18 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US10414737B2 (en) | 2013-12-20 | 2019-09-17 | Gilead Sciences, Inc. | Process methods for phosphatidylinositol 3-kinase inhibitors |
US10442805B2 (en) | 2013-12-20 | 2019-10-15 | Gilead Calistoga Llc | Polymorphic forms of a hydrochloride salt of (S)-2-(1-(9H-purin-6-ylamino)propyl)-5-fluoro-3-phenylquinazolin-4(3H)-one |
US9567337B2 (en) | 2013-12-20 | 2017-02-14 | Gilead Calistoga Llc | Process methods for phosphatidylinositol 3-kinase inhibitors |
US10954199B2 (en) | 2013-12-20 | 2021-03-23 | Gilead Sciences, Inc. | Process methods for phosphatidylinositol 3-kinase inhibitors |
US11021467B2 (en) | 2014-06-13 | 2021-06-01 | Gilead Sciences, Inc. | Phosphatidylinositol 3-kinase inhibitors |
Also Published As
Publication number | Publication date |
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EP1044004A1 (de) | 2000-10-18 |
AU2108299A (en) | 1999-07-26 |
JP2002500188A (ja) | 2002-01-08 |
CA2317093A1 (en) | 1999-07-15 |
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