HRP20010927A2 - Purine derivatives - Google Patents
Purine derivatives Download PDFInfo
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- HRP20010927A2 HRP20010927A2 HR20010927A HRP20010927A HRP20010927A2 HR P20010927 A2 HRP20010927 A2 HR P20010927A2 HR 20010927 A HR20010927 A HR 20010927A HR P20010927 A HRP20010927 A HR P20010927A HR P20010927 A2 HRP20010927 A2 HR P20010927A2
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- Prior art keywords
- compound
- alkyl
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- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 3
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 211
- 239000000203 mixture Substances 0.000 claims description 88
- 238000002360 preparation method Methods 0.000 claims description 88
- -1 -CONR4R4 Chemical group 0.000 claims description 76
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 57
- 150000003839 salts Chemical class 0.000 claims description 43
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 41
- 238000000034 method Methods 0.000 claims description 39
- 125000006239 protecting group Chemical group 0.000 claims description 34
- 238000011282 treatment Methods 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 29
- 239000012453 solvate Substances 0.000 claims description 29
- 125000005843 halogen group Chemical group 0.000 claims description 25
- 125000002947 alkylene group Chemical group 0.000 claims description 24
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 22
- 125000001624 naphthyl group Chemical group 0.000 claims description 20
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 19
- 241000124008 Mammalia Species 0.000 claims description 16
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 15
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 15
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims description 14
- 229910002091 carbon monoxide Inorganic materials 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001153 fluoro group Chemical group F* 0.000 claims description 13
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 13
- 125000001589 carboacyl group Chemical group 0.000 claims description 12
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 11
- 230000006378 damage Effects 0.000 claims description 11
- 239000003814 drug Substances 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
- 125000000579 2,2-diphenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(C1=C([H])C([H])=C([H])C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 10
- 208000007882 Gastritis Diseases 0.000 claims description 10
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 10
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 10
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 10
- 208000010668 atopic eczema Diseases 0.000 claims description 10
- 206010006451 bronchitis Diseases 0.000 claims description 10
- 239000003054 catalyst Substances 0.000 claims description 10
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 10
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 9
- 201000004624 Dermatitis Diseases 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 8
- 150000002148 esters Chemical class 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 101150051188 Adora2a gene Proteins 0.000 claims description 7
- 208000006673 asthma Diseases 0.000 claims description 7
- 125000002393 azetidinyl group Chemical group 0.000 claims description 7
- 125000000623 heterocyclic group Chemical group 0.000 claims description 7
- 125000002757 morpholinyl group Chemical group 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- 125000006528 (C2-C6) alkyl group Chemical group 0.000 claims description 6
- 229940044601 receptor agonist Drugs 0.000 claims description 6
- 239000000018 receptor agonist Substances 0.000 claims description 6
- ZNUJAZSDJXSBIG-YVIFWTNJSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-n-(2-piperidin-1-ylethyl)purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(C(=O)NCCN3CCCCC3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 ZNUJAZSDJXSBIG-YVIFWTNJSA-N 0.000 claims description 5
- 201000006474 Brain Ischemia Diseases 0.000 claims description 5
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 5
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 5
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 5
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 208000011231 Crohn disease Diseases 0.000 claims description 5
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 5
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 5
- 206010014561 Emphysema Diseases 0.000 claims description 5
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 5
- 206010020772 Hypertension Diseases 0.000 claims description 5
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 5
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 5
- 201000004681 Psoriasis Diseases 0.000 claims description 5
- 206010063837 Reperfusion injury Diseases 0.000 claims description 5
- 206010040070 Septic Shock Diseases 0.000 claims description 5
- 208000006011 Stroke Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 208000027418 Wounds and injury Diseases 0.000 claims description 5
- 229940124599 anti-inflammatory drug Drugs 0.000 claims description 5
- 201000008937 atopic dermatitis Diseases 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 201000009267 bronchiectasis Diseases 0.000 claims description 5
- 206010008118 cerebral infarction Diseases 0.000 claims description 5
- 208000007451 chronic bronchitis Diseases 0.000 claims description 5
- 201000009151 chronic rhinitis Diseases 0.000 claims description 5
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 5
- 206010012601 diabetes mellitus Diseases 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 206010015037 epilepsy Diseases 0.000 claims description 5
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 5
- 201000001881 impotence Diseases 0.000 claims description 5
- 208000014674 injury Diseases 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 201000006417 multiple sclerosis Diseases 0.000 claims description 5
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 5
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 5
- 125000004193 piperazinyl group Chemical group 0.000 claims description 5
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- 208000023504 respiratory system disease Diseases 0.000 claims description 5
- 206010039083 rhinitis Diseases 0.000 claims description 5
- 230000036303 septic shock Effects 0.000 claims description 5
- 230000003637 steroidlike Effects 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000004434 sulfur atom Chemical group 0.000 claims description 5
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000002346 iodo group Chemical group I* 0.000 claims description 4
- 125000002950 monocyclic group Chemical group 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
- HHQYBAUCNJBTQH-IXXGIDSLSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-n-(2-phenylethyl)purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(C(=O)NCCC=3C=CC=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 HHQYBAUCNJBTQH-IXXGIDSLSA-N 0.000 claims description 3
- FPNQDMRKZOZDRH-YVIFWTNJSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-n-(2-pyridin-2-ylethyl)purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(C(=O)NCCC=3N=CC=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 FPNQDMRKZOZDRH-YVIFWTNJSA-N 0.000 claims description 3
- AJDRQAFLYHVTOO-YVIFWTNJSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-n-(3-pyrrolidin-1-ylpropyl)purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(C(=O)NCCCN3CCCC3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 AJDRQAFLYHVTOO-YVIFWTNJSA-N 0.000 claims description 3
- INTKDKBGAKNHPG-KTLRCIACSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-n-[2-(4-propan-2-ylpiperidin-1-yl)ethyl]purine-2-carboxamide Chemical compound C1CC(C(C)C)CCN1CCNC(=O)C1=NC(NCC(C=2C=CC=CC=2)C=2C=CC=CC=2)=C(N=CN2[C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=N1 INTKDKBGAKNHPG-KTLRCIACSA-N 0.000 claims description 3
- OYCQUNYSOYGYSI-LQLFOZJWSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-n-[2-(dimethylamino)ethyl]-6-(2,2-diphenylethylamino)purine-2-carboxamide Chemical compound C=12N=CN([C@H]3[C@@H]([C@H](O)[C@@H](CO)O3)O)C2=NC(C(=O)NCCN(C)C)=NC=1NCC(C=1C=CC=CC=1)C1=CC=CC=C1 OYCQUNYSOYGYSI-LQLFOZJWSA-N 0.000 claims description 3
- 238000005910 aminocarbonylation reaction Methods 0.000 claims description 3
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 125000002883 imidazolyl group Chemical group 0.000 claims description 3
- 125000001041 indolyl group Chemical group 0.000 claims description 3
- 125000000904 isoindolyl group Chemical group C=1(NC=C2C=CC=CC12)* 0.000 claims description 3
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 3
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 3
- 125000002971 oxazolyl group Chemical group 0.000 claims description 3
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 3
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 3
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 3
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 3
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 3
- 125000000335 thiazolyl group Chemical group 0.000 claims description 3
- 125000001544 thienyl group Chemical group 0.000 claims description 3
- 125000001425 triazolyl group Chemical group 0.000 claims description 3
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 claims description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims description 2
- JCILWHMBYGQAQY-RAYZIOHUSA-N 9-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-(2,2-diphenylethylamino)-n-(2-morpholin-4-ylethyl)purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1N1C2=NC(C(=O)NCCN3CCOCC3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 JCILWHMBYGQAQY-RAYZIOHUSA-N 0.000 claims description 2
- 125000002619 bicyclic group Chemical group 0.000 claims description 2
- 239000011230 binding agent Substances 0.000 claims description 2
- 125000001246 bromo group Chemical group Br* 0.000 claims description 2
- 230000008878 coupling Effects 0.000 claims description 2
- 238000010168 coupling process Methods 0.000 claims description 2
- 238000005859 coupling reaction Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
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- 208000027866 inflammatory disease Diseases 0.000 claims description 2
- 239000008194 pharmaceutical composition Substances 0.000 claims description 2
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- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 2
- 125000004185 ester group Chemical group 0.000 claims 2
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 claims 1
- 201000003068 rheumatic fever Diseases 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 159
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 111
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 96
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- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 58
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 56
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 48
- 239000007787 solid Substances 0.000 description 46
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 43
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Classifications
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- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
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- C07D473/26—Heterocyclic compounds containing purine ring systems with an oxygen, sulphur, or nitrogen atom directly attached in position 2 or 6, but not in both
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
-
- 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
-
- 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
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- A61P9/14—Vasoprotectives; Antihaemorrhoidals; Drugs for varicose therapy; Capillary stabilisers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- C07H19/167—Purine radicals with ribosyl as the saccharide radical
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pulmonology (AREA)
- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Dermatology (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Biomedical Technology (AREA)
- Endocrinology (AREA)
- Communicable Diseases (AREA)
- Reproductive Health (AREA)
- Gynecology & Obstetrics (AREA)
- Otolaryngology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Urology & Nephrology (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9913932.1A GB9913932D0 (en) | 1999-06-15 | 1999-06-15 | Purine derivatives |
PCT/IB2000/000789 WO2000077018A2 (en) | 1999-06-15 | 2000-06-13 | Purine derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
HRP20010927A2 true HRP20010927A2 (en) | 2003-04-30 |
Family
ID=10855403
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
HR20010927A HRP20010927A2 (en) | 1999-06-15 | 2001-12-13 | Purine derivatives |
Country Status (39)
Country | Link |
---|---|
US (2) | US6900309B1 (zh) |
EP (1) | EP1185542A2 (zh) |
JP (1) | JP2003502339A (zh) |
KR (1) | KR20020010707A (zh) |
CN (1) | CN1179970C (zh) |
AP (1) | AP2001002361A0 (zh) |
AR (1) | AR024345A1 (zh) |
AU (1) | AU764106B2 (zh) |
BG (1) | BG106289A (zh) |
BR (1) | BR0011705A (zh) |
CA (1) | CA2379786C (zh) |
CZ (1) | CZ20014397A3 (zh) |
DZ (1) | DZ3168A1 (zh) |
EA (1) | EA004861B1 (zh) |
EC (1) | ECSP003531A (zh) |
EE (1) | EE200100681A (zh) |
GB (1) | GB9913932D0 (zh) |
GT (1) | GT200000096A (zh) |
HK (1) | HK1047111A1 (zh) |
HN (1) | HN2000000097A (zh) |
HR (1) | HRP20010927A2 (zh) |
HU (1) | HUP0203419A3 (zh) |
IL (1) | IL147098A0 (zh) |
IS (1) | IS6196A (zh) |
MA (1) | MA26799A1 (zh) |
MX (1) | MXPA01013094A (zh) |
NO (1) | NO20016109L (zh) |
NZ (1) | NZ516094A (zh) |
OA (1) | OA11968A (zh) |
PA (1) | PA8497001A1 (zh) |
PE (1) | PE20010430A1 (zh) |
PL (1) | PL354367A1 (zh) |
SK (1) | SK18192001A3 (zh) |
SV (1) | SV2001000100A (zh) |
TN (1) | TNSN00133A1 (zh) |
TR (1) | TR200103607T2 (zh) |
UY (1) | UY26204A1 (zh) |
WO (1) | WO2000077018A2 (zh) |
ZA (1) | ZA200110208B (zh) |
Families Citing this family (48)
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EP1121372B1 (en) * | 1998-10-16 | 2006-06-28 | Pfizer Limited | Adenine derivatives |
GB9913932D0 (en) * | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
GB9924361D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Ltd | Purine derivatives |
GB0003960D0 (en) | 2000-02-18 | 2000-04-12 | Pfizer Ltd | Purine derivatives |
US6753322B2 (en) * | 2000-06-06 | 2004-06-22 | Pfizer Inc | 2-aminocarbonyl-9H-purine derivatives |
TWI227240B (en) * | 2000-06-06 | 2005-02-01 | Pfizer | 2-aminocarbonyl-9H-purine derivatives |
US6921753B2 (en) | 2000-06-27 | 2005-07-26 | Pfizer Inc | Purine derivatives |
GB0015727D0 (en) * | 2000-06-27 | 2000-08-16 | Pfizer Ltd | Purine derivatives |
GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
GB0104555D0 (en) * | 2001-02-23 | 2001-04-11 | Glaxo Group Ltd | New Therapeutic method |
AU2002238748A1 (en) * | 2001-03-12 | 2002-09-24 | Glaxo Group Limited | Pharmaceutical aerosol formulation |
GB0129273D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Crystalline drug form |
GB0129397D0 (en) * | 2001-12-07 | 2002-01-30 | Pfizer Ltd | Pharmaceutical combination |
GB0228723D0 (en) | 2002-12-09 | 2003-01-15 | Cambridge Biotechnology Ltd | Treatment of pain |
TW200519106A (en) | 2003-05-02 | 2005-06-16 | Novartis Ag | Organic compounds |
JPWO2005019238A1 (ja) * | 2003-08-22 | 2006-10-19 | 明治製菓株式会社 | 新規アザライド及びアザラクタム誘導体とその製造法 |
JP2005132767A (ja) * | 2003-10-30 | 2005-05-26 | Sumitomo Chemical Co Ltd | プリン化合物の製造方法 |
GB0401334D0 (en) | 2004-01-21 | 2004-02-25 | Novartis Ag | Organic compounds |
TWI346109B (en) * | 2004-04-30 | 2011-08-01 | Otsuka Pharma Co Ltd | 4-amino-5-cyanopyrimidine derivatives |
GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
GB0426164D0 (en) | 2004-11-29 | 2004-12-29 | Novartis Ag | Organic compounds |
GB0500785D0 (en) * | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
WO2007045477A2 (en) | 2005-10-21 | 2007-04-26 | Novartis Ag | Human antibodies against il-13 and therapeutic uses |
GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
EP2581381A3 (en) * | 2006-02-03 | 2013-10-30 | Gilead Sciences, Inc. | Process for preparing an A2A-adenosine receptor agonist and its polymorphs |
AU2007302263A1 (en) | 2006-09-29 | 2008-04-03 | Novartis Ag | Pyrazolopyrimidines as P13K lipid kinase inhibitors |
WO2008052734A1 (en) | 2006-10-30 | 2008-05-08 | Novartis Ag | Heterocyclic compounds as antiinflammatory agents |
PT2231642E (pt) | 2008-01-11 | 2014-03-12 | Novartis Ag | Pirimidinas como inibidores de quinase |
WO2010088335A1 (en) | 2009-01-29 | 2010-08-05 | Novartis Ag | Substituted benzimidazoles for the treatment of astrocytomas |
US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
BR112012003262A8 (pt) | 2009-08-12 | 2016-05-17 | Novartis Ag | compostos de hidrazona heterocíclica e seus usos para tratar câncer e inflamação |
CN105078978A (zh) | 2009-08-17 | 2015-11-25 | 因特利凯公司 | 杂环化合物及其用途 |
WO2011020861A1 (en) | 2009-08-20 | 2011-02-24 | Novartis Ag | Heterocyclic oxime compounds |
UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
US20130324526A1 (en) | 2011-02-10 | 2013-12-05 | Novartis Ag | [1,2,4] triazolo [4,3-b] pyridazine compounds as inhibitors of the c-met tyrosine kinase |
JP5808826B2 (ja) | 2011-02-23 | 2015-11-10 | インテリカイン, エルエルシー | 複素環化合物およびその使用 |
CA2828219A1 (en) | 2011-02-25 | 2012-08-30 | Irm Llc | Pyrazolo [1,5-a] pyridines as trk inhibitors |
CA2848809A1 (en) | 2011-09-15 | 2013-03-21 | Novartis Ag | 6-substituted 3-(quinolin-6-ylthio)-[1,2,4]triazolo[4,3-a]pyradines as c-met tyrosine kinase |
EP2793893A4 (en) | 2011-11-23 | 2015-07-08 | Intellikine Llc | IMPROVED TREATMENT REGIMES USING MTOR INHIBITORS |
WO2013149581A1 (en) | 2012-04-03 | 2013-10-10 | Novartis Ag | Combination products with tyrosine kinase inhibitors and their use |
CN105246482A (zh) | 2013-03-15 | 2016-01-13 | 因特利凯有限责任公司 | 激酶抑制剂的组合及其用途 |
WO2015084804A1 (en) | 2013-12-03 | 2015-06-11 | Novartis Ag | Combination of mdm2 inhibitor and braf inhibitor and their use |
WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
WO2016016822A1 (en) | 2014-07-31 | 2016-02-04 | Novartis Ag | Combination therapy |
TW202140550A (zh) | 2020-01-29 | 2021-11-01 | 瑞士商諾華公司 | 使用抗tslp抗體治療炎性或阻塞性氣道疾病之方法 |
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JPS55153798A (en) * | 1979-05-18 | 1980-11-29 | Kikkoman Corp | Novel 2-substituted-adenosine 3',5'-cyclic phosphate and its preparation |
JPH0313934A (ja) * | 1989-06-12 | 1991-01-22 | Konica Corp | ハロゲン化銀写真感光材料 |
KR0166088B1 (ko) | 1990-01-23 | 1999-01-15 | . | 수용해도가 증가된 시클로덱스트린 유도체 및 이의 용도 |
US5376645A (en) | 1990-01-23 | 1994-12-27 | University Of Kansas | Derivatives of cyclodextrins exhibiting enhanced aqueous solubility and the use thereof |
EP0601322A3 (en) | 1992-10-27 | 1994-10-12 | Nippon Zoki Pharmaceutical Co | Adenosine deaminase inhibitor. |
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NZ306280A (en) * | 1995-04-14 | 1999-07-29 | Glaxo Wellcome Inc | Metered dose inhaler for salmeterol |
GB9711643D0 (en) | 1997-06-05 | 1997-07-30 | Janssen Pharmaceutica Nv | Glass thermoplastic systems |
ZA9810490B (en) | 1997-12-03 | 1999-05-20 | Dainippon Pharmaceutical Co | 2-Aryl-8-oxodihydropurine derivative process for the preparation thereof pharmaceutical composition containing the same and intermediate therefor |
US6232297B1 (en) | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
RU2258071C2 (ru) | 1999-05-24 | 2005-08-10 | Юниверсити Оф Вирджиния Пэйтент Фаундейшн | Производные 2-алкиниладенозина для борьбы с воспалительной реакцией |
GB9913932D0 (en) * | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
GB0003960D0 (en) * | 2000-02-18 | 2000-04-12 | Pfizer Ltd | Purine derivatives |
-
1999
- 1999-06-15 GB GBGB9913932.1A patent/GB9913932D0/en not_active Ceased
-
2000
- 2000-06-08 US US09/590,585 patent/US6900309B1/en not_active Expired - Fee Related
- 2000-06-13 HN HN2000000097A patent/HN2000000097A/es unknown
- 2000-06-13 DZ DZ003168A patent/DZ3168A1/xx active
- 2000-06-13 AP APAP/P/2001/002361A patent/AP2001002361A0/en unknown
- 2000-06-13 PE PE2000000582A patent/PE20010430A1/es not_active Application Discontinuation
- 2000-06-13 EP EP00931495A patent/EP1185542A2/en not_active Withdrawn
- 2000-06-13 CA CA002379786A patent/CA2379786C/en not_active Expired - Fee Related
- 2000-06-13 MX MXPA01013094A patent/MXPA01013094A/es active IP Right Grant
- 2000-06-13 SK SK1819-2001A patent/SK18192001A3/sk unknown
- 2000-06-13 NZ NZ516094A patent/NZ516094A/en unknown
- 2000-06-13 JP JP2001503875A patent/JP2003502339A/ja not_active Ceased
- 2000-06-13 HU HU0203419A patent/HUP0203419A3/hu unknown
- 2000-06-13 CN CNB008130647A patent/CN1179970C/zh not_active Expired - Fee Related
- 2000-06-13 EE EEP200100681A patent/EE200100681A/xx unknown
- 2000-06-13 CZ CZ20014397A patent/CZ20014397A3/cs unknown
- 2000-06-13 AU AU49443/00A patent/AU764106B2/en not_active Ceased
- 2000-06-13 OA OA1200100332A patent/OA11968A/en unknown
- 2000-06-13 AR ARP000102905A patent/AR024345A1/es unknown
- 2000-06-13 KR KR1020017016127A patent/KR20020010707A/ko not_active Application Discontinuation
- 2000-06-13 UY UY26204A patent/UY26204A1/es not_active Application Discontinuation
- 2000-06-13 EA EA200101203A patent/EA004861B1/ru not_active IP Right Cessation
- 2000-06-13 BR BR0011705-6A patent/BR0011705A/pt not_active IP Right Cessation
- 2000-06-13 PL PL00354367A patent/PL354367A1/xx not_active Application Discontinuation
- 2000-06-13 WO PCT/IB2000/000789 patent/WO2000077018A2/en active Application Filing
- 2000-06-13 TR TR2001/03607T patent/TR200103607T2/xx unknown
- 2000-06-13 IL IL14709800A patent/IL147098A0/xx unknown
- 2000-06-14 TN TNTNSN00133A patent/TNSN00133A1/fr unknown
- 2000-06-14 EC EC2000003531A patent/ECSP003531A/es unknown
- 2000-06-14 GT GT200000096A patent/GT200000096A/es unknown
- 2000-06-14 PA PA20008497001A patent/PA8497001A1/es unknown
- 2000-06-14 SV SV2000000100A patent/SV2001000100A/es unknown
-
2001
- 2001-12-11 IS IS6196A patent/IS6196A/is unknown
- 2001-12-12 MA MA26440A patent/MA26799A1/fr unknown
- 2001-12-12 ZA ZA200110208A patent/ZA200110208B/xx unknown
- 2001-12-13 HR HR20010927A patent/HRP20010927A2/hr not_active Application Discontinuation
- 2001-12-14 NO NO20016109A patent/NO20016109L/no not_active Application Discontinuation
-
2002
- 2002-01-08 BG BG06289A patent/BG106289A/xx unknown
- 2002-11-29 HK HK02108621A patent/HK1047111A1/xx not_active IP Right Cessation
-
2005
- 2005-01-24 US US11/042,582 patent/US20050124574A1/en not_active Abandoned
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