TWI224598B - Glyco derivatives of xanthines, process for their preparation and pharmaceutical composition containing them - Google Patents
Glyco derivatives of xanthines, process for their preparation and pharmaceutical composition containing them Download PDFInfo
- Publication number
- TWI224598B TWI224598B TW088113815A TW88113815A TWI224598B TW I224598 B TWI224598 B TW I224598B TW 088113815 A TW088113815 A TW 088113815A TW 88113815 A TW88113815 A TW 88113815A TW I224598 B TWI224598 B TW I224598B
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- Taiwan
- Prior art keywords
- dioxo
- tetrahydro
- methyl ether
- cyclohexylmethyl
- glycol methyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title abstract description 4
- 238000000034 method Methods 0.000 title abstract description 3
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical class O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 33
- 239000003814 drug Substances 0.000 abstract description 5
- 208000026278 immune system disease Diseases 0.000 abstract description 4
- 238000011282 treatment Methods 0.000 abstract description 4
- 230000004968 inflammatory condition Effects 0.000 abstract description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- 208000018522 Gastrointestinal disease Diseases 0.000 abstract 1
- 206010064147 Gastrointestinal inflammation Diseases 0.000 abstract 1
- 206010040070 Septic Shock Diseases 0.000 abstract 1
- 208000035475 disorder Diseases 0.000 abstract 1
- 238000011321 prophylaxis Methods 0.000 abstract 1
- 230000036303 septic shock Effects 0.000 abstract 1
- 229920000847 nonoxynol Polymers 0.000 description 75
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 72
- WGKYSFRFMQHMOF-UHFFFAOYSA-N 3-bromo-5-methylpyridine-2-carbonitrile Chemical compound CC1=CN=C(C#N)C(Br)=C1 WGKYSFRFMQHMOF-UHFFFAOYSA-N 0.000 description 69
- 229940114081 cinnamate Drugs 0.000 description 68
- -1 phenylfluorenyl Chemical group 0.000 description 65
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 65
- 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 description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 13
- 125000000217 alkyl group Chemical group 0.000 description 11
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 9
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 6
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 208000028169 periodontal disease Diseases 0.000 description 5
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 4
- 102100035353 Cyclin-dependent kinase 2-associated protein 1 Human genes 0.000 description 4
- 229930016911 cinnamic acid Natural products 0.000 description 4
- 235000013985 cinnamic acid Nutrition 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 4
- 201000004624 Dermatitis Diseases 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004544 purin-8-yl group Chemical group N1=CN=C2N=C(NC2=C1)* 0.000 description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 description 3
- AGWKUHGLWHMYTG-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound COCCOCCOCCOCCOCCOCCOCCO AGWKUHGLWHMYTG-UHFFFAOYSA-N 0.000 description 2
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 2
- 125000006284 3-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(F)=C1[H])C([H])([H])* 0.000 description 2
- KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 description 2
- CYSPWCARDHRYJX-UHFFFAOYSA-N 9h-fluoren-1-amine Chemical compound C12=CC=CC=C2CC2=C1C=CC=C2N CYSPWCARDHRYJX-UHFFFAOYSA-N 0.000 description 2
- 244000223760 Cinnamomum zeylanicum Species 0.000 description 2
- 206010009900 Colitis ulcerative Diseases 0.000 description 2
- 201000003883 Cystic fibrosis Diseases 0.000 description 2
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 2
- 206010061216 Infarction Diseases 0.000 description 2
- 206010035664 Pneumonia Diseases 0.000 description 2
- 206010036774 Proctitis Diseases 0.000 description 2
- 201000004681 Psoriasis Diseases 0.000 description 2
- 201000006704 Ulcerative Colitis Diseases 0.000 description 2
- 230000003187 abdominal effect Effects 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 208000006673 asthma Diseases 0.000 description 2
- ZMCUBGBEPHLPAI-UHFFFAOYSA-N azane;methoxymethane Chemical compound N.COC ZMCUBGBEPHLPAI-UHFFFAOYSA-N 0.000 description 2
- NQONXKLCMOMECA-UHFFFAOYSA-N benzoic acid methoxymethane Chemical compound COC.OC(=O)c1ccccc1 NQONXKLCMOMECA-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 206010006451 bronchitis Diseases 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000002512 chemotherapy Methods 0.000 description 2
- 235000017803 cinnamon Nutrition 0.000 description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 description 2
- 125000006622 cycloheptylmethyl group Chemical group 0.000 description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 description 2
- 230000002496 gastric effect Effects 0.000 description 2
- 125000005842 heteroatom Chemical group 0.000 description 2
- 230000007574 infarction Effects 0.000 description 2
- 230000008595 infiltration Effects 0.000 description 2
- 238000001764 infiltration Methods 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 2
- 230000000241 respiratory effect Effects 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 239000012453 solvate Substances 0.000 description 2
- 230000009278 visceral effect Effects 0.000 description 2
- WXUAQHNMJWJLTG-VKHMYHEASA-N (S)-methylsuccinic acid Chemical compound OC(=O)[C@@H](C)CC(O)=O WXUAQHNMJWJLTG-VKHMYHEASA-N 0.000 description 1
- NTVYNLYQURIAKG-UHFFFAOYSA-N 1-benzyl-9h-fluorene Chemical compound C=1C=CC=2C3=CC=CC=C3CC=2C=1CC1=CC=CC=C1 NTVYNLYQURIAKG-UHFFFAOYSA-N 0.000 description 1
- WZJLGICGNMAUFC-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-fluorene Chemical compound C12=CC=CC=C2CC2=C1CCCC2 WZJLGICGNMAUFC-UHFFFAOYSA-N 0.000 description 1
- SLNYBUIEAMRFSZ-UHFFFAOYSA-N 2-(2-{2-[2-(2-methoxy-ethoxy)-ethoxy]-ethoxy}-ethoxy)-ethanol Chemical compound COCCOCCOCCOCCOCCO SLNYBUIEAMRFSZ-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- DANLZOIRUUHIIX-UHFFFAOYSA-N 4-[1-[2-chloro-6-(trifluoromethyl)benzoyl]indazol-3-yl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C(C1=CC=CC=C11)=NN1C(=O)C1=C(Cl)C=CC=C1C(F)(F)F DANLZOIRUUHIIX-UHFFFAOYSA-N 0.000 description 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 description 1
- 125000002373 5 membered heterocyclic group Chemical group 0.000 description 1
- 125000004070 6 membered heterocyclic group Chemical group 0.000 description 1
- 208000030507 AIDS Diseases 0.000 description 1
- 206010002091 Anaesthesia Diseases 0.000 description 1
- 235000000509 Chenopodium ambrosioides Nutrition 0.000 description 1
- 244000098897 Chenopodium botrys Species 0.000 description 1
- 235000005490 Chenopodium botrys Nutrition 0.000 description 1
- 206010010741 Conjunctivitis Diseases 0.000 description 1
- 208000011231 Crohn disease Diseases 0.000 description 1
- 206010012735 Diarrhoea Diseases 0.000 description 1
- 206010012742 Diarrhoea infectious Diseases 0.000 description 1
- 206010061218 Inflammation Diseases 0.000 description 1
- 206010030216 Oesophagitis Diseases 0.000 description 1
- 208000025747 Rheumatic disease Diseases 0.000 description 1
- 201000002661 Spondylitis Diseases 0.000 description 1
- 210000001015 abdomen Anatomy 0.000 description 1
- 150000001335 aliphatic alkanes Chemical group 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 230000037005 anaesthesia Effects 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- 208000010668 atopic eczema Diseases 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 210000004351 coronary vessel Anatomy 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- DTPCFIHYWYONMD-UHFFFAOYSA-N decaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO DTPCFIHYWYONMD-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 208000001848 dysentery Diseases 0.000 description 1
- 208000006881 esophagitis Diseases 0.000 description 1
- DOMLXBPXLNDFAB-UHFFFAOYSA-N ethoxyethane;methyl prop-2-enoate Chemical compound CCOCC.COC(=O)C=C DOMLXBPXLNDFAB-UHFFFAOYSA-N 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- IIRDTKBZINWQAW-UHFFFAOYSA-N hexaethylene glycol Chemical compound OCCOCCOCCOCCOCCOCCO IIRDTKBZINWQAW-UHFFFAOYSA-N 0.000 description 1
- 125000005597 hydrazone group Chemical group 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002458 infectious effect Effects 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000000265 leukocyte Anatomy 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- DNMZJIGSDQVGSA-UHFFFAOYSA-N methoxymethane;hydrochloride Chemical compound Cl.COC DNMZJIGSDQVGSA-UHFFFAOYSA-N 0.000 description 1
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical group COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 210000003097 mucus Anatomy 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 201000008482 osteoarthritis Diseases 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 230000000552 rheumatic effect Effects 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000035922 thirst Effects 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 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
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/02—Stomatological preparations, e.g. drugs for caries, aphtae, periodontitis
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
- 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
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- 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
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Immunology (AREA)
- Communicable Diseases (AREA)
- Pulmonology (AREA)
- Oncology (AREA)
- Dermatology (AREA)
- Rheumatology (AREA)
- Pain & Pain Management (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (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)
Description
8 8 8 8 A BCD 1224598 申請專利範圍 員雜環基，其視情況地含選自0，N或S之其他雜原子； R4與R5獨立地表示 -C3-8環坑基 -直鍵或分支Ci_6坑基 -氫 -苯基或經CN12烷基、氫或-CN取代之苯基； -口比呢基， R6與R7獨立地表示0或S ; 其條件為在 -y與y’均表示1， -k表示 1， -p1表示0， -R2表示Η或Me， -R3表示Η， -X表示0或ΝΗ，及 -Ζ表示苯基時 R4與R5不均表示環己基； 或其醫藥上可接受之鹽。 2. 一種式（la)化合物
-2- 59705-940205.doc 本紙張尺度適用中國國家標準(CNS) A4規格(210χ 297公釐）
A B c D 1224598 六、申請專利範圍 其中 Z表7JT表基、苯硫基或卩比卩定基； R1表示氫； R2表示氫，（:丨心烷基，苯基或c丨·12苯烷基； k表示〇或1 η表示8至15之整數； X 表 π -0-，-N(H)-，-N(Ci_6 烷基）·， 烷基，苯基或（^_12苯烷基）]-，-Cll2〇·或_CH2NH_ ; πι表不〇 - 6 Q 表示（-CH2)p，（-CH=CH-)p，或（、CH2(〇)pi)p，其中 p 與 P1獨立地表示0或1之整數； y與yf獨立地表示0至4之整數； R3表示氫，直鏈或分支Cl_s烷基（其視情況地以苯基， -C0-苯基，CN，-CCKCw)烷基，-C〇2(Ci 3)烷基取代， 或在烷鏈含一至三個〇原子）；cl 0直鏈或分支烯基，Cw 直鏈或分支炔基或-c^烷基-NR8R9基 其中R8與R9獨立地為Η，C!_3烷基或一起形成5或6 員雜環基，其視情況地含選自〇，N或S之其他雜原子； R4與R5獨立地表示 -C 3 - 8環燒基 -直鏈或分支CN6烷基 -氫 -苯基或C i i 2苯垸基； -吡啶基； 59705-940205.doc _ Ο ^ 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐)
8 8 8 8 A B c D 1224598 六、申請專利範圍 R6與R7獨立地表示0或S ; 其條件為在 -y與y1均表示1， -k表示 1， _pi表示0， -R3表示Η， -X表示0或ΝΗ，及 -Ζ表TF冬基時 R4與R5不均表示環己基； 或其醫藥上可接受之鹽 3. 根據申請專利範圍第1或2項之化合物，其中R3表示 Cu 烷基 NR8R9。 4. 根據申請專利範圍第1或2項之化合物，其中
在對位置連接至苯環。 5. 根據申請專利範圍第1或2項之化合物，其中R2為甲基 或乙基。 6. 根據申請專利範圍第1或2項之化合物，其中k為1。 7. 根據申請專利範圍第1或2項之化合物，其中X為-0-， -N(H)-，或-N(CH3)-。 8. 根據申請專利範圍第1或2項之化合物，其中Q為 59705-940205.doc ~ 4 ~ 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐） 2
('CH-CH-)p 〇 9·根據申請專利範圍第8項之化合物，其中p為1。 1〇·根據申請專利範圍第1或2項之化合物，其中R3為甲基。 U·根據申請專利範圍第1或2項之化合物，其中y與y，為 相同的。 12 4 •根據申請專利範圍第11項之化合物，其中y與y，為i。 13.根據申請專利範圍第1或2項之化合物，其中R4與R5 獨立地選自包括Cl 6烷基，c3 8環烷基與芳基。 14·根據申請專利範圍第1 3項之化合物，其中R4與R5獨立 地選自環丁基’環戊基，環己基，丙基，丁基，異丙基， 異丁基與苯基。 15·根據申請專利範圍第14項之化合物，其中R4與R5為相 同的。 16·根據申請專利範圍第i或2項之化合物，其中R6與r7 為相同的。 17·根據申請專利範圍第16項之化合物，其中R6與R7為〇。 队根據申請專利範圍第1或2項之化合物，其中χ為 且R1為Η。 19·根據申請專利範圍第1或2項之化合物，其係選自下列 之任一化合物： (E)-4-(l，3-貳（苄基）-ΐ，2,3,6-四氫-2,6-二氧-9Η-嗓呤- 8- 基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（環戊基甲基）-1，2,3,6_四氫-2,6_二氧_91^嘌 呤-8·基）桂皮酸九乙二醇甲醚酯； 59705-940205.doc _ ^ _ 本紙張尺度適用中國國家標準(CNS) Α4規格(210 X 297公釐）
8 8 8 8 A B c D 1224598 六、申請專利範圍 斤）-4-(1，3-貳（丙基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（環丙基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-3-((l -丙基-3-苄基）-1，2,3,6-四氫-2,6-二氧-9H-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（環庚基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； 口）-4-(1，3-貳（環己基乙基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（苯基）-1，2,3,6-四氫-2,6-二氧-9H-嘌呤-8- 基）桂皮酸九乙二醇甲醚酯； (£)-4-(1，3-貳（2-甲基-丙基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-((l -丙基-3-環己基甲基）-1，2,3,6·四氫-2,6-二氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（雙環（2.2.1)庚-2-基甲基）-1，2,3,6-四氬-2,6-二氧-9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 巧）-4-(1-環己基甲基-3-丁基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤-8·基）桂皮酸九乙二醇甲醚酯； (E)-4-((l-環己基甲基-3-丙基）-1，2,3,6-四氫-2,6-二氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（芊基）-1，2,3,6-四氫-2-硫氧-6-氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 59705-940205.doc - 6 ~ 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐) 1224598 - C8 • D8 六、申請專利範圍 (E)-4-(l -甲基-3-(3 -氣基卞基））-l，2,3,6 -四氯-2,6 -二氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（3-氟苄基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； (幻-4-(1，3-貳（2-氟苄基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； (Ε)·4-((1，3·二苯乙基）-1，2,3,6-四氫-2,6-二氧-9H-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； (£)-4-((1-緣己基甲基-3-甲基）-1，2,3,6-四氯-2,6-二氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (£)-4-((1-13-(2-甲基-丙基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（4-氟苄基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(153-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-9^嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (丑）-4-(1，3-貳（環丁基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l-甲基-3-環己基甲基）-l，2,3,6-四氫-2,6-二氧-9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l-甲基-3-異丁基）-1，2,3,6-四氫-2,6-二氧-9H-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（環己基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 59705-940205.doc ~ 7 ~ 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐）.
(Ε)-Μ!，3-貳（環戊基甲基Μ，2,3,6·四氫+氧I硫氧 票呤-8_基）桂皮酸九乙二醇甲醚醯胺； (^)-4-(1,3-貳（2-甲基-丙基 四氫 _2,6_ 二氧 _9Η_ 鳴呤-8-基）桂皮酸九乙二醇甲醚醯胺； (^)-4-(1-環己基甲基-3-丙基3,6_四氫_2,6_二氧_9Η_ 嗓呤-8-基）桂皮酸九乙二醇甲醚醯胺； 4-(1，3-貳（環己基甲基）-1，2,3,6-四氫_2,6-二氧-91嘌呤 、8 -基）苯甲酸九乙二醇甲_醯胺； 4-(1，3-貳（環己基甲基）-1，2,3,6_四氫-2,6_二氧_91^嘌呤 8·基）丰甲酸-Ν-甲基-九乙二醇甲醚醯胺； (£)-4-(1，3-貳（環己基甲基）_2,3,6,7-四氫_2,6_二氧-7_爷 基-1Η-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（環己基甲基）_2,3,6,7-四氫-2,6-二氧-7-(2-氧苯乙基）-1Η-嘌呤_8_基）桂皮酸九乙二醇 (办4-(1，3-武（環己基甲基）-2,3从四氫仏二氧^甲 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (幻-心（1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6_二氧-7-(2-内块基）-1Η-嘌呤-8-基）桂皮酸九乙二醇甲_酷； (£)-心（1，3-貳（環己基甲基）-2,3,6,7-四氫—2,6_二氧_7_(2-氧甲基乙基）-1H_嗓呤_8_基）桂皮酸九乙二醇甲醚醋； (E)-4-(l，3-貳（環己基甲基）_2,3,6,7-四氫·2,6-二氧-7-(3- 嗎啉基丙基）-1Η-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)·•心（1，3-貳（環己基甲基）_2,3,6,7-四氫·2,6•二氧_7-乙 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯；
59705-940205.doc Q
A BCD 1224598 六、申請專利範圍 (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧_7-(2. 乙氧基-2-氧乙基）-lH-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧 _7-(2_ 甲基-2-丙烯基）-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (5)-4-(1，3-武（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-(氰 基甲基）-1Η -嗓吟-8-基）桂皮酸九乙二醇甲醚酿； 4-(1，3-貳（環己基甲基）-2,3,6,7-四氫_2,6_二氧-7-芊基 -1H-嘌呤-8·基）苯甲酸九乙二醇甲醚酯； 4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7_甲基 -1H-嘌呤-8-基）苯甲酸九乙二醇甲醚酯； 4-[(1,3-武（$衣己基甲基）-2,3,6,7-四氫-2,6-二氧_7-甲基 -1H-嘌呤-8_基）苯基]丙酸九乙二醇甲醚酿； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7_甲 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚醯胺； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6_ 二氧 _7·芊 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚醯胺； 4-(1，3 -武（環己基甲基）-2,3,6,7·四氫-2,6-二氧-7-爷基 -1H-嘌呤-8-基）苯甲酸九乙二醇甲醚醯胺； 4-(1，3-武（環己基甲基）-2,3,6,7-四氫_2,6-二氧_7-甲基 -1H-嘌呤-8-基）苯甲酸九乙二醇甲醚醯胺； 1，3-貳（環己基甲基）-8-[4-(2,5,8，11，14，17,20,23,26,29-十 ，三十-1-基）苯基]-3,7-二氫-1H-嘌呤_2,6_二§同； (E)-3-[5-[l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6_ 二氧 -1H-嘌呤-8-基]-2塞基]-2 -丙烯酸九乙二醇甲醚酯； 59705-940205.doc - Θ - 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐） " -----
A B c D 1224598 六、申請專利範圍 6-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-9H-嘌呤 -8-基）菸蠄酸九乙二醇甲醚醯胺； 斤）-3-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸N-環丙基甲基九乙二醇甲醚醯胺； (E)-4-(l，3-貳（環己基甲基）-1,2,3,6-四氫-2,6-二氧-9H-嘌 呤-8-基）桂皮酸六乙二醇芊醚醯胺； (E)-4-[(3-環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-甲基 -1H-嘌呤-8-基]桂皮酸七乙二醇甲醚酯； (E)-4-[(3-環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-甲基 -1H-嘌呤-8-基]桂皮酸九乙二醇甲醚酯； (E)-4-[(3-環己基甲基）-2,3,6,7-四氫-2,6-二氧-1，7-二甲 基-1H-嘌呤-8-基]桂皮酸九乙二醇甲醚酯； 4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）芊胺七乙二醇甲醚； 4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）苄胺N-七乙二醇甲醚氫氯酸鹽； 4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）芊胺N-九乙二醇甲醚； 1，3-貳（環己基甲基）-8-[3-(2,5,8，11，14，17,20,23,26,29-十 哼三十-1-基）苯基]-3,7-二氫-1H-嘌呤-2,6-二酮； 斤）-4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-甲 基-1H-嘌呤-8-基）桂皮酸七乙二醇甲醚酯； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-甲 基-1H-嘌呤-8-基）桂皮酸五乙二醇甲醚酯； 59705-940205.doc ~ 1 0 ~ 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐）
申請專利範圍 1224598 (Ε)-4·(1，3-貳（環己基甲基）-2,3,6,夂四氫·2,6_二氧刀-丙 基_1Η·嘌呤-8-基）桂皮酸九乙二醇甲醚酯。 20.根據申請專利範圍第19項之化合物，其係選自下列之任 一化合物： ' (£)-4-(1，3_貳（苄基）-1，2,3,6-四氳-2,6-二氧_9只-嘌呤"·8-基）桂皮酸九乙二醇甲酸酯； ^、‘（^•貳^袤戊基甲基卜^^四氫-^心二氧^^^嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（丙基）-1，2,3,6-四氫-2,6-二氧-9Η-嘌呤-8- 基）桂皮酸九乙二醇甲醚酯； (Ε)-4-(1，3-貳（環庚基甲基）-1，2,3,6-四氫_2,6_二氧_91嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（環己基乙基）-1，2,3,6-四氫 _2,6·二氧 _9^1_嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）_4-(1，3-武（苯基）-1，2,3,6-四氫-2,6_二氧_911_票吟-8- 基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（2-甲基-丙基）-l，2,3,6-四氫·2,6-二氧 _9Η_ 嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (£)-4-((1-丙基-3-環己基甲基）_1，2,3,6-四氫_2,6_二氧 -9Η-嘌呤-8-基）桂皮酸九乙二醇甲醚酿； (Ε)-4-(1，3·貳（雙環（2.2.1)庚-2-基甲基四氫·2,6· 二氧- 9Η-ρ票呤-8-基）桂皮酸九乙二醇甲酸酉旨； (Ε)-4-(1-環己基甲基-3-丁基 l·1，253,6_四氫_2,6_二氧_9H_ 嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 59705-940205.doc - 1 1 - 本紙張尺度適用中國國家標準(CNS) Α4規格(210 X 297公釐）
8 8 8 8 A B c D 1224598 六、申請專利範圍 (E)-4-((l-環己基甲基-3 -丙基）-1，2,3,6-四氫-2,6-二氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (£)-4-(1，3-貳（3-氟苄基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（2-氟苄基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； (£)-4-((1，3_貳苯乙基）-1，2,3,6-四氫-2,6-二氧-91嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； (五）-4-((1-11-3-(2-甲基-丙基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (丑）-4-(1，3-貳（4-氟芊基）-1,2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸六乙二醇甲醚酯； 斤）-4-(1，3-貳（環丁基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l-甲基-3-異丁基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）桂皮酸九乙二醇甲醚酯； (£)_4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-91^嘌 呤-8-基）桂皮酸-N-甲基九乙二醇甲醚醯胺； 斤）-4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚醯胺； 4-(1，3-貳（環己基曱基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基）苯甲酸九乙二醇甲醚醯胺； 59705-940205.doc - 1 2 ~ 本紙張尺度適用中國國家標準(CNS) A4規格(210X 297公釐）
A B c D 1224598 *------- -六、申請專利範圍 (E)-4-(l，3-貳（環己基曱基）-2,3,6,7-四氫-2,6-二氧 _7-爷 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲酸酯； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧- 7-(2- 氧-2-苯乙基）-1Η-嘌呤-8-基）桂皮酸九乙二醇甲酸酿； (£)-4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧_7-甲 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； ^)-4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧_7-(2- 丙块:基）-1Η-ρ票呤-8-基）桂皮酸九乙二醇甲齡酿·， (£)-4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6_二氧_7-(2- 氧-2-甲基乙基）-iH-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3 -貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧- 7-(3- 嗎4基丙基）-1Η-嘌呤-8-基）桂皮酸九乙二醇甲酸醋； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧 _7_ 乙 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-(2- 乙氧基-2-氧乙基）-1Η-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6、二氧_7-(2- 甲基-2-丙烯基）-1Η-嘌呤-8-基）桂皮酸九乙二醇甲酸醋； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-(氰 基甲基）-1Η-ρ票呤-8-基）桂皮酸九乙二醇甲_酉旨； 4-(1，3 -武（3幕己基甲基）-2,3,6,7 -四氫-2,6 -二氧-7—爷基 -1H -嘌呤-8-基）苯甲酸九乙二醇甲醚酯； 4-(1,3 -武（％己基甲基）-2,3,6,7 -四氮-2,6·二氧_7-甲基 -1Η-嘌呤-8-基）苯甲酸九乙二醇甲醚酯； 59705-940205.doc - 1 3 ** 本紙張尺度適用中國國家標準(CNS) Α4規格(210X297公釐）— 〜----
8 8 8 8 A B c D 1224598 六、申請專利範圍 巧）_4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-甲 基-1H-嘌呤-8-基）桂皮酸九乙二醇甲醚醯胺； (E)-4-(l，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-爷 基-111-嗓吟-8 -基）桂皮酸九乙二醇甲醚酸胺； 4-(1，3-武（5幕己基甲基）-2,3,6,7-四氯-2,6-二氧-7-卞基 -1H-嘌呤-8-基）苯甲酸九乙二醇甲醚醯胺； 1，3-貳（環己基甲基）-8-[4-(2,5,8，11，14，17,20,23,26,29-十 口号三十-卜基）苯基]-3,7-二氫-1H-嘌呤-2,6-二酮； (Ε)·3-[5-[1，3-貳（環己基甲基）-2,3,6,7-四氫-2,6-二氧 -1H-嘌呤-8-基]-2-嘧基]-2-丙晞酸九乙二醇甲醚酯； 6-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-9H-嘌呤 -8-基）菸礆酸九乙二醇甲醚醯胺； 斤）-3_(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸N-環丙基甲基九乙二醇甲醚醯胺； 斤）-4-[(3-(環己基甲基）-2,3,6,7-四氫-2,6-二氧-7-甲基 -1H-嘌呤-8-基]桂皮酸七乙二醇曱醚酯； 4-[1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌呤 -8-基]芊胺N-七乙二醇甲醚氫氯酸鹽； 1，3-貳（環己基甲基）-8-[3-(2,5,8，11，14，17,20,23,26,29-十 嘮三十-1-基）苯基]-3,7-二氫-1H-嘌呤-2,6-二酮； (E)-4-(l，3-貳（環己基甲基）-1，2,3,6-四氫-6-氧-2-硫氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯； 斤）-4-(1，3-貳（環己基甲基）-2,3,6,7-四氫-6-二氧-7-丙基 -1Η -嘌呤-8 -基）桂皮酸九乙二醇甲醚酯。 59705-940205.doc ~ 14 ~ 本紙張尺度適用中國國家標準(CNS) Α4規格(210X 297公釐） 1224598 ^、申請專利範圍 21·-種用於治療與白血球對發炎組織滲透有 “'、、 或免疫失調之醫藥组人铷 晷火病況 酋条、、且口物，其包含根據申請 1或2項任一項之化合物與醫 軛圍弟 22.根據申請專利範圍第 ^ 钟或載體。 病m 列所組成之群：哮喘、成人呼吸 肺炎支氣管炎、囊腫性纖維化、類風濕性 茴瞪少^, 月關即炎、蹋風關節炎、葡 : 發炎性内臟病況、克羅恩氏病、潰瘍 性結腸炎、末稍直腸炎、令搭^ 化學療法-誘發枯液、tD_誘發腸胃破壞、 柏履Ams相關腹渴、傳染性腹滴、牛 皮癬、濕殄、皮膚炎及冠狀動脈梗塞破壞。 仏：據申請專利範圍第…項之化合物，其係用於治療 =白止球«炎組織滲透有關之發炎病況或免疫失調之 治療之醫藥劑製造。 24·根據申請專利範圍第23項之化合物，其係用於製造用 =治療選自下列所組成之群之發炎病況或免疫失調之醫 樂劑：哮喘、成人呼吸病痛症候群、肺炎支氣管炎、囊 ^生纖維化、類風濕性關節炎、類風濕性脊椎炎、骨關 節炎、，風關節炎、葡葡膜炎、結膜炎、纟炎性内臟病 況、克維恩氏病、潰瘍性結腸炎、末稍直腸炎、食道炎、 NS^ID-誘發腸胃破壞、化學療法j秀發粘液、AIDS相關 腹4、傳染性腹瀉、牛皮癬、濕疹、皮膚炎及冠狀動脈 梗塞破壞。 25.根據申請專利範圍第}或2項之化合物，其係製造用於 15· 59705-940205.doc 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐)
申請專利範 牙周疾病之治療之醫藥劑。 26. —種用於治療牙周疾病之醫藥彳且人 專利範園第】或2項之化人^其包含根據 載體。 U員H與醫藥可接受之稀釋刻成 種祕治療牙周疾病之醫藥、组合物，其包含式⑽化舍
Q 為（-CH2-)p，（·〇Η=(：Η-)ρ， 之整數； (-CsC-)p，其中ρ為〇至4 R1為氫或甲基； R2與R3獨立地表示〇或s。 η為1至50之整數；及 R為氫或甲基； 及醫藥可接受稀釋劑或載體。 28·根據申請專利範圍第27項之醫藥組合物，其中式（Ib)化 合物為： 呤-8 -基）桂皮酸十 乙二醇甲醚酉旨；及 -16- 59705-940205.doc 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐)
8 8 8 8 A B c D 1224598 申請專利範圍 (£)-4-(1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； (E)-3-(l，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-9H-嘌 呤-8-基）桂皮酸九乙二醇甲醚酯； 口）-4-[1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基]桂皮酸九乙二醇甲醚醯胺；或 (£)-4-[1，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧-911-嘌 呤-8-基]苯甲酸九乙二醇甲醚酯， 其係用於治療牙周疾病。 29. 根據申請專利範圍第27項之醫藥組合物，其中式（lb)化 合物係（E)-4-(l，3-貳（環己基甲基）-1，2,3,6-四氫-2,6-二氧 -9H-嘌呤-8-基）桂皮酸九乙二醇甲醚酯，其係用於治療牙 周疾病。 30. —種製備（I)或（la)化合物，或其溶劑合物之方法，其包 含反應式（II)化合物
RJCH2)y.、N 0人N. /)- 2'
•N 、(Qh -OH (II) (ch2)v r5/ 或其活化衍生物與式（ΙΠ)化合物
2 ⑽ 17 59705-940205.doc 本紙張尺度適用中國國家標準(CNS) A4規格(210 X 297公釐）
8 8 8 8 A B c D 1224598 六、申請專利範圍 其中 Q，X，R1，R2，R4，R5，R6，y，y’與 η 如申請專 利範圍第1項所定義； 及視情況地將如此形成之式（I)化合物轉化成不同之式（I) 化合物或對應之溶劑合物。 59705-940205.doc - 1 8 本紙張尺度適用中國國家標準(CNS) A4規格(210X297公釐）
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB9817623.3A GB9817623D0 (en) | 1998-08-13 | 1998-08-13 | Pharmaceutical compounds |
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| Publication Number | Publication Date |
|---|---|
| TWI224598B true TWI224598B (en) | 2004-12-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW088113815A TWI224598B (en) | 1998-08-13 | 1999-08-12 | Glyco derivatives of xanthines, process for their preparation and pharmaceutical composition containing them |
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| Country | Link |
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| US (3) | US6608069B1 (zh) |
| EP (1) | EP1104422B1 (zh) |
| JP (3) | JP3631961B2 (zh) |
| KR (1) | KR20010085369A (zh) |
| CN (2) | CN1251676C (zh) |
| AP (1) | AP1408A (zh) |
| AR (1) | AR020154A1 (zh) |
| AT (1) | ATE259810T1 (zh) |
| AU (1) | AU775819B2 (zh) |
| BR (1) | BR9913020A (zh) |
| CA (1) | CA2340350A1 (zh) |
| CO (1) | CO5130007A1 (zh) |
| DE (1) | DE69914921T2 (zh) |
| DK (1) | DK1104422T3 (zh) |
| EA (1) | EA004139B1 (zh) |
| EE (1) | EE04721B1 (zh) |
| ES (1) | ES2215399T3 (zh) |
| GB (1) | GB9817623D0 (zh) |
| HU (1) | HUP0103637A3 (zh) |
| ID (1) | ID28723A (zh) |
| IL (1) | IL141318A0 (zh) |
| IS (1) | IS5843A (zh) |
| MA (1) | MA26673A1 (zh) |
| MY (1) | MY133393A (zh) |
| NO (1) | NO20010715L (zh) |
| NZ (1) | NZ509778A (zh) |
| PE (1) | PE20000952A1 (zh) |
| PL (1) | PL346055A1 (zh) |
| PT (1) | PT1104422E (zh) |
| SI (1) | SI1104422T1 (zh) |
| SK (1) | SK2222001A3 (zh) |
| TR (1) | TR200100448T2 (zh) |
| TW (1) | TWI224598B (zh) |
| WO (1) | WO2000009507A1 (zh) |
| YU (1) | YU11601A (zh) |
| ZA (1) | ZA200101186B (zh) |
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| EP1372661B1 (en) * | 2001-02-28 | 2006-05-17 | SmithKline Beecham Corporation | Glycol derivatves of xanthines for treating irritable bowel syndrome |
| WO2003017964A1 (en) | 2001-08-24 | 2003-03-06 | Unilever N.V. | Oral composition comprising an alkylhydroxybenzoate |
| US7125993B2 (en) | 2001-11-09 | 2006-10-24 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US6977300B2 (en) | 2001-11-09 | 2005-12-20 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| US7317017B2 (en) | 2002-11-08 | 2008-01-08 | Cv Therapeutics, Inc. | A2B adenosine receptor antagonists |
| JP4350517B2 (ja) | 2001-11-09 | 2009-10-21 | シーブイ・セラピューティクス・インコーポレイテッド | Ａ２ｂアデノシン受容体アンタゴニスト |
| US20040072848A1 (en) * | 2002-02-26 | 2004-04-15 | Huber Brian E | Methods of treating irritable bowel syndrome and functional dyspepsia |
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| CN101851238B (zh) * | 2003-08-25 | 2012-07-18 | 卓维斯医药品有限责任公司 | 取代的8-杂芳基黄嘌呤 |
| GB0324086D0 (en) * | 2003-10-14 | 2003-11-19 | Glaxo Group Ltd | Process for preparing a co-precipitate of a non-crystalline solid drug substance |
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| US7618962B2 (en) * | 2005-02-25 | 2009-11-17 | Pgx Health, Llc | Pyrazolyl substituted xanthines |
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| US7884100B2 (en) * | 2006-06-16 | 2011-02-08 | Pgxhealth, Llc | Substituted 8-[6-amino-3-pyridyl]xanthines |
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| WO2009140517A1 (en) | 2008-05-14 | 2009-11-19 | Hydra Biosciences, Inc. | Compounds and compositions for treating chemical warfare agent-induced injuries |
| AU2009251291B2 (en) * | 2008-05-30 | 2013-05-02 | F. Hoffmann-La Roche Ag | Purine PI3K inhibitor compounds and methods of use |
| CN102260260B (zh) * | 2010-05-24 | 2014-08-06 | 中国科学院上海药物研究所 | 8-苯基黄嘌呤类化合物、其制备方法、包含该化合物的药物组合物及其用途 |
| CN102993203B (zh) * | 2011-09-09 | 2015-11-25 | 温州医学院 | 8-苯基黄嘌呤类衍生物的制备及应用 |
| US9502952B2 (en) | 2012-10-12 | 2016-11-22 | Persimmon Technologies, Corp. | Hybrid motor |
| KR20160005364A (ko) * | 2013-05-10 | 2016-01-14 | 님버스 아폴로, 인코포레이티드 | Acc 억제제 및 이의 용도 |
| US10208063B2 (en) | 2013-05-10 | 2019-02-19 | Gilead Apollo, Llc | ACC inhibitors and uses thereof |
| KR20160005365A (ko) | 2013-05-10 | 2016-01-14 | 님버스 아폴로, 인코포레이티드 | Acc 억제제 및 이의 용도 |
| WO2014182943A1 (en) * | 2013-05-10 | 2014-11-13 | Nimbus Apollo, Inc. | Acc inhibitors and uses thereof |
| CN120435477A (zh) | 2022-12-20 | 2025-08-05 | 英威欧斯有限公司 | 被取代的3,7-二氢-1h-嘌呤-2,6-二酮及其用途 |
| EP4389749A1 (en) * | 2022-12-20 | 2024-06-26 | invIOs GmbH | Substituted 3,7-dihydro-1h-purine-2,6-diones and use thereof |
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| 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 |
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| 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 |
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| WO1999043673A1 (en) | 1998-02-26 | 1999-09-02 | Zenyaku Kogyo Kabushiki Kaisha | 1-azaindolizine derivatives |
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| US6751206B1 (en) | 2000-06-29 | 2004-06-15 | Qualcomm Incorporated | Method and apparatus for beam switching in a wireless communication system |
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1998
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1999
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- 1999-08-11 HU HU0103637A patent/HUP0103637A3/hu unknown
- 1999-08-11 US US09/762,559 patent/US6608069B1/en not_active Expired - Fee Related
- 1999-08-11 DK DK99944358T patent/DK1104422T3/da active
- 1999-08-11 AT AT99944358T patent/ATE259810T1/de not_active IP Right Cessation
- 1999-08-11 MY MYPI99003429A patent/MY133393A/en unknown
- 1999-08-11 KR KR1020017001799A patent/KR20010085369A/ko not_active Abandoned
- 1999-08-11 MA MA25728A patent/MA26673A1/fr unknown
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- 1999-08-11 CA CA002340350A patent/CA2340350A1/en not_active Abandoned
- 1999-08-11 YU YU11601A patent/YU11601A/sh unknown
- 1999-08-11 PL PL99346055A patent/PL346055A1/xx not_active Application Discontinuation
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- 1999-08-11 PE PE1999000814A patent/PE20000952A1/es not_active Application Discontinuation
- 1999-08-11 AP APAP/P/2001/002071A patent/AP1408A/en active
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- 1999-08-11 WO PCT/EP1999/005814 patent/WO2000009507A1/en not_active Ceased
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- 1999-08-12 TW TW088113815A patent/TWI224598B/zh not_active IP Right Cessation
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- 2003-06-09 JP JP2003164252A patent/JP2004137251A/ja not_active Withdrawn
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