SK110399A3 - Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6- dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders - Google Patents

Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6- dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders Download PDF

Info

Publication number: SK110399A3
Authority: SK; Slovakia
Prior art keywords: phenyl; cyclohexylmethyl; bis; purin; tetrahydro
Prior art date: 1997-02-14

Application number

SK1103-99A

Other languages

English (en)

Slovak (sk)

Inventor

Susan Mary Daluge

Douglas Alan Livingston

Gerald Wolberg

Original Assignee

Glaxo Group Ltd

Priority date (The priority date 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 date listed.)

1997-02-14

Filing date

1998-02-12

Publication date

2000-06-12

1998-02-12 Application filed by Glaxo Group Ltd filed Critical Glaxo Group Ltd

2000-06-12 Publication of SK110399A3 publication Critical patent/SK110399A3/sk

Links

238000011282 treatment Methods 0.000 title claims abstract description 17
230000004968 inflammatory condition Effects 0.000 title claims abstract description 12
208000026278 immune system disease Diseases 0.000 title claims abstract description 10
-1 (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6- dioxo-9h-purin-8-yl)phenyl Chemical class 0.000 title claims description 73
238000002360 preparation method Methods 0.000 title claims description 69
150000001875 compounds Chemical class 0.000 claims abstract description 115
239000012453 solvate Substances 0.000 claims abstract description 22
150000002148 esters Chemical class 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
239000001257 hydrogen Substances 0.000 claims abstract description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 61
125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 55
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 35
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XWSKURWERJWSKI-UHFFFAOYSA-N COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C(C=CC1=CC=CC=C1)(=O)O Chemical compound COCCOCCOCCOCCOCCOCCOCCOCCOCCO.C(C=CC1=CC=CC=C1)(=O)O XWSKURWERJWSKI-UHFFFAOYSA-N 0.000 claims description 3
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125000001424 substituent group Chemical group 0.000 claims description 2
GZWUQOCKCAKYIS-UHFFFAOYSA-N 1,3-bis(cyclohexylmethyl)-7h-purine-2,6-dione Chemical compound C1=2N=CNC=2C(=O)N(CC2CCCCC2)C(=O)N1CC1CCCCC1 GZWUQOCKCAKYIS-UHFFFAOYSA-N 0.000 claims 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
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238000002560 therapeutic procedure Methods 0.000 claims 1
150000001408 amides Chemical class 0.000 abstract description 4
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239000005457 ice water Substances 0.000 description 1
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238000007689 inspection Methods 0.000 description 1
230000003993 interaction Effects 0.000 description 1
210000000936 intestine Anatomy 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
201000004614 iritis Diseases 0.000 description 1
KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
229940039717 lanolin Drugs 0.000 description 1
235000019388 lanolin Nutrition 0.000 description 1
210000002429 large intestine Anatomy 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000594 mannitol Substances 0.000 description 1
235000010355 mannitol Nutrition 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
210000004379 membrane Anatomy 0.000 description 1
239000012528 membrane Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229940071648 metered dose inhaler Drugs 0.000 description 1
AGZPHKMSWBPKLR-UHFFFAOYSA-N methyl 3-[4-(dimethoxymethyl)phenyl]prop-2-enoate Chemical compound COC(OC)C1=CC=C(C=CC(=O)OC)C=C1 AGZPHKMSWBPKLR-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
210000002850 nasal mucosa Anatomy 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
230000017074 necrotic cell death Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000002674 ointment Substances 0.000 description 1
ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
201000008482 osteoarthritis Diseases 0.000 description 1
238000010979 pH adjustment Methods 0.000 description 1
230000020477 pH reduction Effects 0.000 description 1
239000006072 paste Substances 0.000 description 1
235000011007 phosphoric acid Nutrition 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
239000002504 physiological saline solution Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000004033 plastic Substances 0.000 description 1
210000004224 pleura Anatomy 0.000 description 1
208000008423 pleurisy Diseases 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229940068917 polyethylene glycols Drugs 0.000 description 1
229910000343 potassium bisulfate Inorganic materials 0.000 description 1
CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002265 prevention Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
238000011552 rat model Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
206010039073 rheumatoid arthritis Diseases 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
210000003491 skin Anatomy 0.000 description 1
208000017520 skin disease Diseases 0.000 description 1
150000003384 small molecules Chemical class 0.000 description 1
210000002460 smooth muscle Anatomy 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
208000010110 spontaneous platelet aggregation Diseases 0.000 description 1
239000007921 spray Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
230000004083 survival effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
239000001069 triethyl citrate Substances 0.000 description 1
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
235000013769 triethyl citrate Nutrition 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
229940099259 vaseline Drugs 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000000341 volatile oil Substances 0.000 description 1
238000010792 warming Methods 0.000 description 1
239000008215 water for injection Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- 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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
- C07D473/06—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms with radicals containing only hydrogen and carbon atoms, attached in position 1 or 3
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/08—Bronchodilators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
- A61P17/06—Antipsoriatics
- 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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- 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
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/02—Immunomodulators
- A61P37/06—Immunosuppressants, e.g. drugs for graft rejection
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Public Health (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Immunology (AREA)
Rheumatology (AREA)
Pulmonology (AREA)
Pain & Pain Management (AREA)
Ophthalmology & Optometry (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Transplantation (AREA)
Urology & Nephrology (AREA)
Dermatology (AREA)
Vascular Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

SK1103-99A 1997-02-14 1998-02-12 Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6- dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders SK110399A3 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GBGB9703044.9A GB9703044D0 (en)	1997-02-14	1997-02-14	Phenyl xanthine esters and amides
PCT/EP1998/000784 WO1998035966A1 (en)	1997-02-14	1998-02-12	Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders

Publications (1)

Publication Number	Publication Date
SK110399A3 true SK110399A3 (en)	2000-06-12

Family

ID=10807635

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1103-99A SK110399A3 (en)	1997-02-14	1998-02-12	Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6- dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders

Country Status (37)

Country	Link
US (3)	US6355646B1 (pl)
EP (1)	EP0970081B1 (pl)
JP (1)	JP2001511792A (pl)
KR (1)	KR100522639B1 (pl)
CN (1)	CN1140527C (pl)
AP (1)	AP1000A (pl)
AR (1)	AR011441A1 (pl)
AT (1)	ATE304542T1 (pl)
AU (1)	AU754456B2 (pl)
BG (1)	BG103722A (pl)
BR (1)	BR9807682B1 (pl)
CA (1)	CA2280730C (pl)
CO (1)	CO4940444A1 (pl)
CZ (1)	CZ298764B6 (pl)
DE (1)	DE69831559T2 (pl)
DK (1)	DK0970081T3 (pl)
EA (1)	EA199900648A1 (pl)
EE (1)	EE9900348A (pl)
ES (1)	ES2249822T3 (pl)
GB (1)	GB9703044D0 (pl)
HR (1)	HRP980077A2 (pl)
HU (1)	HU225962B1 (pl)
ID (1)	ID22770A (pl)
IL (1)	IL131179A (pl)
IS (1)	IS5144A (pl)
MY (1)	MY118545A (pl)
NO (1)	NO325685B1 (pl)
NZ (1)	NZ336923A (pl)
PE (1)	PE58899A1 (pl)
PL (1)	PL188018B1 (pl)
SK (1)	SK110399A3 (pl)
TR (1)	TR199901942T2 (pl)
TW (1)	TW520371B (pl)
UA (1)	UA57767C2 (pl)
WO (1)	WO1998035966A1 (pl)
YU (1)	YU38399A (pl)
ZA (1)	ZA981175B (pl)

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GB9703044D0 (en) *	1997-02-14	1997-04-02	Glaxo Group Ltd	Phenyl xanthine esters and amides
GB9817623D0 (en) *	1998-08-13	1998-10-07	Glaxo Group Ltd	Pharmaceutical compounds
US6545002B1 (en) *	1999-06-01	2003-04-08	University Of Virginia Patent Foundation	Substituted 8-phenylxanthines useful as antagonists of A2B adenosine receptors
FR2804958B1 (fr) *	2000-02-15	2005-07-08	Hoechst Marion Roussel Inc	Derives de xanthine, leur procede de preparation et les intermediaires de ce procede, leur application comme medicament et les compositions pharmaceutiques les renfermant
JP2004523559A (ja) *	2001-02-28	2004-08-05	スミスクラインビーチャムコーポレーション	過敏性腸症候群および機能性胃腸症の治療方法
US7125993B2 (en) *	2001-11-09	2006-10-24	Cv Therapeutics, Inc.	A2B adenosine receptor antagonists
US20080318983A1 (en) *	2001-11-09	2008-12-25	Rao Kalla	A2b adenosine receptor antagonists
US20040072848A1 (en) *	2002-02-26	2004-04-15	Huber Brian E	Methods of treating irritable bowel syndrome and functional dyspepsia
AU2012227249B2 (en) *	2003-12-16	2014-10-02	Nektar Therapeutics	Chemically modified small molecules
HRP20140361T1 (hr) *	2003-12-16	2014-05-23	Nektar Therapeutics	Monodisperzne smjese pegiliranog naloksola
US20060182692A1 (en)	2003-12-16	2006-08-17	Fishburn C S	Chemically modified small molecules
WO2005102976A1 (en) *	2004-04-21	2005-11-03	Smithkline Beecham Corporation	Process for preparing nonaethylene glycol monomethyl ether
SI1789053T1 (sl) *	2004-09-01	2012-09-28	Gilead Sciences Inc	Postopek celjenja rane z uporabo antagonistov A2B adenozinskih receptorjev
US20070059740A1 (en) *	2005-08-26	2007-03-15	Linden Joel M	Method of targeting a2b adenosine receptor antagonist therapy
US8193200B2 (en) *	2007-01-04	2012-06-05	University Of Virginia Patent Foundation	Antagonists of A2B adenosine receptors for treatment of inflammatory bowel disease

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GB8510758D0 (en)	1985-04-27	1985-06-05	Wellcome Found	Compounds
US4968672A (en)	1987-01-02	1990-11-06	The United States Of America As Represented By The Department Of Health And Human Services	Adenosine receptor prodrugs
US5015647A (en)	1987-04-24	1991-05-14	Burroughs Wellcome Co.	Method for treating viral infections
GB8826595D0 (en)	1988-11-14	1988-12-21	Beecham Wuelfing Gmbh & Co Kg	Active compounds
GB8906792D0 (en)	1989-03-23	1989-05-10	Beecham Wuelfing Gmbh & Co Kg	Treatment and compounds
NZ240644A (en)	1990-11-21	1994-08-26	Smithkline Beecham Corp	Use of xanthine derivatives to inhibit the production of tumour necrosis factor (tnf)
GB9210839D0 (en) *	1992-05-21	1992-07-08	Smithkline Beecham Plc	Novel compounds
TW252044B (pl) *	1992-08-10	1995-07-21	Boehringer Ingelheim Kg
JP2613355B2 (ja)	1992-09-28	1997-05-28	協和醗酵工業株式会社	パーキンソン氏病治療剤
GB9415529D0 (en) *	1994-08-01	1994-09-21	Wellcome Found	Phenyl xanthine derivatives
DE19535504A1 (de)	1995-09-25	1997-03-27	Bayer Ag	Substituierte Xanthine
ATE226583T1 (de) *	1996-06-07	2002-11-15	Hoechst Ag	Verwendung von theophyllinderivaten zur behandlung und propylaxe von schockzuständen, neue xanthinverbindungen und verfahren zu deren herstellung
GB9703044D0 (en) *	1997-02-14	1997-04-02	Glaxo Group Ltd	Phenyl xanthine esters and amides
US6117878A (en)	1998-02-24	2000-09-12	University Of Virginia	8-phenyl- or 8-cycloalkyl xanthine antagonists of A2B human adenosine receptors
WO1999043673A1 (en)	1998-02-26	1999-09-02	Zenyaku Kogyo Kabushiki Kaisha	1-azaindolizine derivatives
GB9817623D0 (en) *	1998-08-13	1998-10-07	Glaxo Group Ltd	Pharmaceutical compounds
US6649629B2 (en)	1999-12-23	2003-11-18	Nitromed, Inc.	Nitrosated and nitrosylated cyclooxygenase-2 inhibitors, compositions and methods of use
US6751206B1 (en) *	2000-06-29	2004-06-15	Qualcomm Incorporated	Method and apparatus for beam switching in a wireless communication system

1997
- 1997-02-14 GB GBGB9703044.9A patent/GB9703044D0/en active Pending
1998
- 1998-02-11 MY MYPI98000546A patent/MY118545A/en unknown
- 1998-02-11 PE PE1998000099A patent/PE58899A1/es not_active Application Discontinuation
- 1998-02-11 CO CO98007044A patent/CO4940444A1/es unknown
- 1998-02-12 CN CNB988039419A patent/CN1140527C/zh not_active Expired - Fee Related
- 1998-02-12 TR TR1999/01942T patent/TR199901942T2/xx unknown
- 1998-02-12 DK DK98908090T patent/DK0970081T3/da active
- 1998-02-12 JP JP53534098A patent/JP2001511792A/ja not_active Ceased
- 1998-02-12 WO PCT/EP1998/000784 patent/WO1998035966A1/en not_active Ceased
- 1998-02-12 SK SK1103-99A patent/SK110399A3/sk unknown
- 1998-02-12 IL IL13117998A patent/IL131179A/en not_active IP Right Cessation
- 1998-02-12 DE DE69831559T patent/DE69831559T2/de not_active Expired - Lifetime
- 1998-02-12 KR KR10-1999-7007276A patent/KR100522639B1/ko not_active Expired - Fee Related
- 1998-02-12 ID IDW990879A patent/ID22770A/id unknown
- 1998-02-12 YU YU38399A patent/YU38399A/sh unknown
- 1998-02-12 CA CA002280730A patent/CA2280730C/en not_active Expired - Fee Related
- 1998-02-12 AT AT98908090T patent/ATE304542T1/de active
- 1998-02-12 ZA ZA9801175A patent/ZA981175B/xx unknown
- 1998-02-12 AU AU66221/98A patent/AU754456B2/en not_active Ceased
- 1998-02-12 ES ES98908090T patent/ES2249822T3/es not_active Expired - Lifetime
- 1998-02-12 HU HU0000894A patent/HU225962B1/hu not_active IP Right Cessation
- 1998-02-12 US US09/367,313 patent/US6355646B1/en not_active Expired - Lifetime
- 1998-02-12 PL PL98335135A patent/PL188018B1/pl unknown
- 1998-02-12 EA EA199900648A patent/EA199900648A1/ru unknown
- 1998-02-12 AP APAP/P/1999/001622A patent/AP1000A/en active
- 1998-02-12 EP EP98908090A patent/EP0970081B1/en not_active Expired - Lifetime
- 1998-02-12 BR BRPI9807682-5A patent/BR9807682B1/pt not_active IP Right Cessation
- 1998-02-12 CZ CZ0288799A patent/CZ298764B6/cs not_active IP Right Cessation
- 1998-02-12 EE EEP199900348A patent/EE9900348A/xx unknown
- 1998-02-12 NZ NZ336923A patent/NZ336923A/en unknown
- 1998-02-13 AR ARP980100664A patent/AR011441A1/es active IP Right Grant
- 1998-02-13 HR HR9703044.9A patent/HRP980077A2/hr not_active Application Discontinuation
- 1998-02-24 TW TW087102632A patent/TW520371B/zh not_active IP Right Cessation
- 1998-12-02 UA UA99084601A patent/UA57767C2/uk unknown
1999
- 1999-07-30 IS IS5144A patent/IS5144A/is unknown
- 1999-08-13 NO NO19993915A patent/NO325685B1/no not_active IP Right Cessation
- 1999-09-09 BG BG103722A patent/BG103722A/xx unknown
2001
- 2001-06-01 US US09/872,546 patent/US6437124B1/en not_active Expired - Fee Related
2002
- 2002-06-17 US US10/174,414 patent/US7002012B2/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
AU6622198A (en)	1998-09-08
PE58899A1 (es)	1999-06-17
CA2280730C (en)	2006-10-10
TW520371B (en)	2003-02-11
CA2280730A1 (en)	1998-08-20
NO993915D0 (no)	1999-08-13
CN1252071A (zh)	2000-05-03
EP0970081A1 (en)	2000-01-12
CZ288799A3 (cs)	2000-04-12
KR20000071010A (ko)	2000-11-25
AP9901622A0 (en)	1999-09-30
ATE304542T1 (de)	2005-09-15
AR011441A1 (es)	2000-08-16
YU38399A (sh)	2002-06-19
ES2249822T3 (es)	2006-04-01
PL188018B1 (pl)	2004-11-30
BG103722A (en)	2000-06-30
ZA981175B (en)	1999-08-12
HUP0000894A2 (hu)	2001-05-28
HK1022907A1 (en)	2000-08-25
IL131179A0 (en)	2001-01-28
HRP980077A2 (en)	1998-12-31
CZ298764B6 (cs)	2008-01-23
EA199900648A1 (ru)	2000-04-24
NZ336923A (en)	2001-02-23
US20030181471A1 (en)	2003-09-25
AP1000A (en)	2001-08-11
IL131179A (en)	2004-05-12
NO993915L (no)	1999-10-13
WO1998035966A1 (en)	1998-08-20
EE9900348A (et)	2000-02-15
ID22770A (id)	1999-12-09
MY118545A (en)	2004-12-31
KR100522639B1 (ko)	2005-10-19
DE69831559D1 (de)	2005-10-20
TR199901942T2 (xx)	1999-12-21
BR9807682A (pt)	2000-02-15
DE69831559T2 (de)	2006-06-14
US6437124B1 (en)	2002-08-20
CN1140527C (zh)	2004-03-03
IS5144A (is)	1999-07-30
UA57767C2 (uk)	2003-07-15
US7002012B2 (en)	2006-02-21
GB9703044D0 (en)	1997-04-02
US6355646B1 (en)	2002-03-12
PL335135A1 (en)	2000-04-10
HU225962B1 (en)	2008-01-28
JP2001511792A (ja)	2001-08-14
CO4940444A1 (es)	2000-07-24
DK0970081T3 (da)	2006-02-06
EP0970081B1 (en)	2005-09-14
HUP0000894A3 (en)	2002-04-29
BR9807682B1 (pt)	2009-01-13
NO325685B1 (no)	2008-07-07
AU754456B2 (en)	2002-11-14

Publication	Publication Date	Title
US6608069B1 (en)	2003-08-19	Phenyl xanthine derivatives
CA2094270C (en)	1997-01-21	Xanthine derivatives
JPH03204880A (ja)	1991-09-06	縮合プリン誘導体
US6437124B1 (en)	2002-08-20	Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9h-purin-8-yl) phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders
FI91155C (fi)	1994-05-25	Menetelmä uuden, terapeuttisesti käyttökelpoisen 9-(2-hydroksietoksimetyyli)guaniiniesterin valmistamiseksi
MXPA99007508A (en)	2000-04-24	Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders
HK1022907B (en)	2006-02-03	Substituted (1,3-bis(cyclohexylmethyl)-1,2,3,6-tetrahydro-2,6-dioxo-9h-purin-8-yl)phenyl derivatives, their preparation and their use in the treatment of inflammatory conditions and immune disorders
JPH0576468B2 (pl)	1993-10-22
MXPA01001632A (en)	2001-12-04	Phenyl yanthine derivatives
JPH0616668A (ja)	1994-01-25	キサンチン誘導体
CZ2001552A3 (cs)	2001-07-11	Fenylxanthinové deriváty
HK1035195B (en)	2004-09-10	Phenyl xanthine derivatives
JPWO1992006976A1 (ja)	1992-11-05	キサンチン誘導体