IL253726B2 - Preparations for the treatment of inflammatory diseases related to uric acid - Google Patents
Preparations for the treatment of inflammatory diseases related to uric acidInfo
- Publication number
- IL253726B2 IL253726B2 IL253726A IL25372617A IL253726B2 IL 253726 B2 IL253726 B2 IL 253726B2 IL 253726 A IL253726 A IL 253726A IL 25372617 A IL25372617 A IL 25372617A IL 253726 B2 IL253726 B2 IL 253726B2
- Authority
- IL
- Israel
- Prior art keywords
- purine
- dione
- dihydro
- chloro
- compound
- Prior art date
Links
- LEHOTFFKMJEONL-UHFFFAOYSA-N Uric Acid Chemical compound N1C(=O)NC(=O)C2=C1NC(=O)N2 LEHOTFFKMJEONL-UHFFFAOYSA-N 0.000 title claims description 75
- TVWHNULVHGKJHS-UHFFFAOYSA-N Uric acid Natural products N1C(=O)NC(=O)C2NC(=O)NC21 TVWHNULVHGKJHS-UHFFFAOYSA-N 0.000 title claims description 61
- 229940116269 uric acid Drugs 0.000 title claims description 61
- 201000005569 Gout Diseases 0.000 title claims description 54
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title claims description 36
- 230000002265 prevention Effects 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 48
- 239000012453 solvate Substances 0.000 claims description 48
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 36
- 229910052736 halogen Inorganic materials 0.000 claims description 35
- 150000002367 halogens Chemical class 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 33
- 239000008194 pharmaceutical composition Substances 0.000 claims description 33
- 201000001431 Hyperuricemia Diseases 0.000 claims description 25
- 206010046337 Urate nephropathy Diseases 0.000 claims description 24
- 230000004054 inflammatory process Effects 0.000 claims description 24
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 23
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 23
- 206010061218 Inflammation Diseases 0.000 claims description 23
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 22
- 208000002193 Pain Diseases 0.000 claims description 18
- 230000001154 acute effect Effects 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 239000001257 hydrogen Substances 0.000 claims description 15
- CGAMDQCXAAOFSR-UHFFFAOYSA-N 8-chloro-3-pentyl-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCCCC)C2=C1NC(Cl)=N2 CGAMDQCXAAOFSR-UHFFFAOYSA-N 0.000 claims description 14
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- IXKIATZUIFUKIE-UHFFFAOYSA-N 3-butyl-8-chloro-1-methyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CCCC)C2=C1NC(Cl)=N2 IXKIATZUIFUKIE-UHFFFAOYSA-N 0.000 claims description 11
- IWPBNHSYRXVLEI-UHFFFAOYSA-N 3-butyl-8-chloro-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCCC)C2=C1NC(Cl)=N2 IWPBNHSYRXVLEI-UHFFFAOYSA-N 0.000 claims description 11
- IQAOHTRPZVQICW-UHFFFAOYSA-N 8-chloro-1-methyl-3-(3-methylbutyl)-7H-purine-2,6-dione Chemical compound ClC1=NC=2N(C(N(C(C=2N1)=O)C)=O)CCC(C)C IQAOHTRPZVQICW-UHFFFAOYSA-N 0.000 claims description 11
- IRKQPAMTLHYJDE-UHFFFAOYSA-N 8-chloro-1-methyl-3-pentyl-7h-purine-2,6-dione Chemical compound O=C1N(C)C(=O)N(CCCCC)C2=C1NC(Cl)=N2 IRKQPAMTLHYJDE-UHFFFAOYSA-N 0.000 claims description 11
- GCRUYCXLSLIMAO-UHFFFAOYSA-N 8-chloro-3-(2-methylpropyl)-7H-purine-2,6-dione Chemical compound ClC1=NC=2N(C(NC(C=2N1)=O)=O)CC(C)C GCRUYCXLSLIMAO-UHFFFAOYSA-N 0.000 claims description 11
- NCLSUDNPUAQNGG-UHFFFAOYSA-N 8-chloro-3-(3-methylbutyl)-7h-purine-2,6-dione Chemical compound O=C1NC(=O)N(CCC(C)C)C2=C1NC(Cl)=N2 NCLSUDNPUAQNGG-UHFFFAOYSA-N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 230000001684 chronic effect Effects 0.000 claims description 9
- 206010003246 arthritis Diseases 0.000 claims description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 206010018634 Gouty Arthritis Diseases 0.000 claims description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 229910052731 fluorine Inorganic materials 0.000 claims description 5
- 239000011737 fluorine Substances 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Chemical group 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 125000001153 fluoro group Chemical group F* 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 4
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- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 9
- 238000004519 manufacturing process Methods 0.000 description 9
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- ONTLUOOEMRVJCI-UHFFFAOYSA-N 8-chloro-3-(2-cyclopropylethyl)-1-methyl-7H-purine-2,6-dione Chemical compound ClC1=NC=2N(C(N(C(C=2N1)=O)C)=O)CCC1CC1 ONTLUOOEMRVJCI-UHFFFAOYSA-N 0.000 description 8
- QQXWQTCMAPWGJA-UHFFFAOYSA-N 8-chloro-3-(2-cyclopropylethyl)-7h-purine-2,6-dione Chemical compound O=C1NC(=O)C=2NC(Cl)=NC=2N1CCC1CC1 QQXWQTCMAPWGJA-UHFFFAOYSA-N 0.000 description 8
- MRYQDAPYAMJCFC-UHFFFAOYSA-N 8-chloro-3-(cyclopropylmethyl)-7h-purine-2,6-dione Chemical compound O=C1NC(=O)C=2NC(Cl)=NC=2N1CC1CC1 MRYQDAPYAMJCFC-UHFFFAOYSA-N 0.000 description 8
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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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4188—1,3-Diazoles condensed with other heterocyclic ring systems, e.g. biotin, sorbinil
-
- 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
-
- 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
- C07D473/08—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 with methyl radicals in positions 1 and 3, e.g. theophylline
-
- 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
- A61K31/522—Purines, e.g. adenine having oxo groups directly attached to the heterocyclic ring, e.g. hypoxanthine, guanine, acyclovir
-
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/04—Drugs for disorders of the urinary system for urolithiasis
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P13/00—Drugs for disorders of the urinary system
- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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- 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
- A61P19/00—Drugs for skeletal disorders
- A61P19/06—Antigout agents, e.g. antihyperuricemic or uricosuric agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
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- 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]
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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
- C07D473/04—Heterocyclic compounds containing purine ring systems with oxygen, sulphur, or nitrogen atoms directly attached in positions 2 and 6 two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2300/00—Mixtures or combinations of active ingredients, wherein at least one active ingredient is fully defined in groups A61K31/00 - A61K41/00
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- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Urology & Nephrology (AREA)
- Physical Education & Sports Medicine (AREA)
- Neurosurgery (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
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| CN201510048096 | 2015-01-30 | ||
| CN201510079809 | 2015-02-13 | ||
| CN201510080714 | 2015-02-13 | ||
| CN201510216089 | 2015-04-30 | ||
| PCT/CN2016/000061 WO2016119570A1 (zh) | 2015-01-30 | 2016-01-28 | 尿酸性或痛风性疾病的预防或治疗 |
Publications (3)
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| IL253726A0 IL253726A0 (en) | 2017-09-28 |
| IL253726B1 IL253726B1 (en) | 2023-03-01 |
| IL253726B2 true IL253726B2 (en) | 2023-07-01 |
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| IL253726A IL253726B2 (en) | 2015-01-30 | 2017-07-30 | Preparations for the treatment of inflammatory diseases related to uric acid |
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| US12566174B2 (en) | 2017-05-11 | 2026-03-03 | The Research Foundation For The State University Of New York | Method and kit for determining the presence of monosodium urate crystals in joint synovial fluid |
| US20260035370A1 (en) | 2023-02-27 | 2026-02-05 | Shanton Pharma Pte. Ltd. | Crystal form of 8-chloro-3-pentyl-3,7-dihydro-1h-purin-2,6-dione compound and preparation method therefor |
| CN116650490B (zh) * | 2023-06-07 | 2025-05-20 | 中国人民解放军海军军医大学 | 化合物mt-1207在降低尿酸方面的应用 |
| EP4497439A1 (en) * | 2023-07-28 | 2025-01-29 | Universitat de les Illes Balears | Compounds for the treatment or prevention of gout |
| TWI902254B (zh) * | 2024-05-16 | 2025-10-21 | 新加坡商珊頓醫藥科技新加坡公司 | 化合物8-氯-3-戊基-3,7-二氫-1h-嘌呤-2,6-二酮的晶型及其製備方法 |
Citations (3)
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| WO1993016699A1 (en) * | 1992-02-21 | 1993-09-02 | Smithkline Beecham Corporation | Tnf inhibitors |
| WO2005077950A2 (en) * | 2004-02-14 | 2005-08-25 | Smithkline Beecham Corporation | Medicaments with hm74a receptor activity |
| US20110136835A1 (en) * | 2009-09-14 | 2011-06-09 | Nuon Therapeutics, Inc. | Combination formulations of tranilast and allopurinol and methods related thereto |
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| GB8906792D0 (en) | 1989-03-23 | 1989-05-10 | Beecham Wuelfing Gmbh & Co Kg | Treatment and compounds |
| AR015966A1 (es) | 1997-10-17 | 2001-05-30 | Smithkline Beecham Corp | Uso de un compuesto inhibidor de pde4 para la preparacion de un medicamento util para el tratamiento de prurito |
| CN101479273B (zh) * | 2006-06-23 | 2011-11-30 | 英赛特股份有限公司 | 作为hm74a激动剂的嘌呤酮衍生物 |
| KR20090025262A (ko) * | 2006-06-23 | 2009-03-10 | 인사이트 코포레이션 | Ｈｍ７４ａ 아고니스트로서 푸리논 유도체 |
| WO2010071865A1 (en) | 2008-12-19 | 2010-06-24 | Nuon Therapeutics, Inc. | Pharmaceutical compositions and methods for treating hyperuricemia and related disorders |
| WO2011057110A1 (en) | 2009-11-06 | 2011-05-12 | Ruprecht-Karls-Universitat-Heidelberg | Gpr109a agonists for the treatment of cerebral ischemia |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993016699A1 (en) * | 1992-02-21 | 1993-09-02 | Smithkline Beecham Corporation | Tnf inhibitors |
| WO2005077950A2 (en) * | 2004-02-14 | 2005-08-25 | Smithkline Beecham Corporation | Medicaments with hm74a receptor activity |
| US20110136835A1 (en) * | 2009-09-14 | 2011-06-09 | Nuon Therapeutics, Inc. | Combination formulations of tranilast and allopurinol and methods related thereto |
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