ZA200206526B - Purine derivatives. - Google Patents
Purine derivatives. Download PDFInfo
- Publication number
- ZA200206526B ZA200206526B ZA200206526A ZA200206526A ZA200206526B ZA 200206526 B ZA200206526 B ZA 200206526B ZA 200206526 A ZA200206526 A ZA 200206526A ZA 200206526 A ZA200206526 A ZA 200206526A ZA 200206526 B ZA200206526 B ZA 200206526B
- Authority
- ZA
- South Africa
- Prior art keywords
- compound
- formula
- alkyl
- amino
- purine
- Prior art date
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- 229940083251 peripheral vasodilators purine derivative Drugs 0.000 title description 4
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 title 1
- 229910052799 carbon Inorganic materials 0.000 claims description 92
- 150000001875 compounds Chemical class 0.000 claims description 88
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- -1 fluorenyi Chemical group 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 36
- 238000000034 method Methods 0.000 claims description 30
- 230000008569 process Effects 0.000 claims description 30
- 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 23
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000003386 piperidinyl group Chemical group 0.000 claims description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 125000001624 naphthyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 13
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 11
- 125000006239 protecting group Chemical group 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 10
- 125000005843 halogen group Chemical group 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000000203 mixture Substances 0.000 claims description 9
- 125000003282 alkyl amino group Chemical group 0.000 claims description 8
- 201000010099 disease Diseases 0.000 claims description 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 125000001589 carboacyl group Chemical group 0.000 claims description 7
- 206010001052 Acute respiratory distress syndrome Diseases 0.000 claims description 6
- 208000007882 Gastritis Diseases 0.000 claims description 6
- 208000013616 Respiratory Distress Syndrome Diseases 0.000 claims description 6
- 208000011341 adult acute respiratory distress syndrome Diseases 0.000 claims description 6
- 201000000028 adult respiratory distress syndrome Diseases 0.000 claims description 6
- 208000010668 atopic eczema Diseases 0.000 claims description 6
- 206010006451 bronchitis Diseases 0.000 claims description 6
- 150000002431 hydrogen Chemical group 0.000 claims description 6
- 125000004193 piperazinyl group Chemical group 0.000 claims description 6
- 208000006673 asthma Diseases 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
- 125000004076 pyridyl group Chemical group 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 230000006378 damage Effects 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000002883 imidazolyl group Chemical group 0.000 claims description 4
- 125000002757 morpholinyl group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 4
- 101150051188 Adora2a gene Proteins 0.000 claims description 3
- 206010006458 Bronchitis chronic Diseases 0.000 claims description 3
- 206010008120 Cerebral ischaemia Diseases 0.000 claims description 3
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 3
- 206010009137 Chronic sinusitis Diseases 0.000 claims description 3
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 3
- 208000011231 Crohn disease Diseases 0.000 claims description 3
- 201000003883 Cystic fibrosis Diseases 0.000 claims description 3
- 201000004624 Dermatitis Diseases 0.000 claims description 3
- 206010012434 Dermatitis allergic Diseases 0.000 claims description 3
- 206010014561 Emphysema Diseases 0.000 claims description 3
- 208000010228 Erectile Dysfunction Diseases 0.000 claims description 3
- 206010020772 Hypertension Diseases 0.000 claims description 3
- 208000022559 Inflammatory bowel disease Diseases 0.000 claims description 3
- 208000018262 Peripheral vascular disease Diseases 0.000 claims description 3
- 201000004681 Psoriasis Diseases 0.000 claims description 3
- 208000028017 Psychotic disease Diseases 0.000 claims description 3
- 206010063837 Reperfusion injury Diseases 0.000 claims description 3
- 206010040070 Septic Shock Diseases 0.000 claims description 3
- 208000006011 Stroke Diseases 0.000 claims description 3
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 3
- 150000001412 amines Chemical class 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 201000008937 atopic dermatitis Diseases 0.000 claims description 3
- 125000004567 azetidin-3-yl group Chemical group N1CC(C1)* 0.000 claims description 3
- 238000006243 chemical reaction Methods 0.000 claims description 3
- 208000007451 chronic bronchitis Diseases 0.000 claims description 3
- 201000009151 chronic rhinitis Diseases 0.000 claims description 3
- 208000027157 chronic rhinosinusitis Diseases 0.000 claims description 3
- 238000010511 deprotection reaction Methods 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 206010015037 epilepsy Diseases 0.000 claims description 3
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000002541 furyl group Chemical group 0.000 claims description 3
- 210000001035 gastrointestinal tract Anatomy 0.000 claims description 3
- 201000001881 impotence Diseases 0.000 claims description 3
- 201000006417 multiple sclerosis Diseases 0.000 claims description 3
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 3
- 208000023504 respiratory system disease Diseases 0.000 claims description 3
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 3
- 206010039083 rhinitis Diseases 0.000 claims description 3
- 230000036303 septic shock Effects 0.000 claims description 3
- SIOVKLKJSOKLIF-HJWRWDBZSA-N trimethylsilyl (1z)-n-trimethylsilylethanimidate Chemical compound C[Si](C)(C)OC(/C)=N\[Si](C)(C)C SIOVKLKJSOKLIF-HJWRWDBZSA-N 0.000 claims description 3
- 230000029663 wound healing Effects 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 2
- 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004195 4-methylpiperazin-1-yl group Chemical group [H]C([H])([H])N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 238000006136 alcoholysis reaction Methods 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 125000002393 azetidinyl group Chemical group 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002618 bicyclic heterocycle group Chemical group 0.000 claims description 2
- 201000009267 bronchiectasis Diseases 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002140 imidazol-4-yl group Chemical group [H]N1C([H])=NC([*])=C1[H] 0.000 claims description 2
- 125000002911 monocyclic heterocycle group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
- 125000002971 oxazolyl group Chemical group 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 125000004592 phthalazinyl group Chemical group C1(=NN=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 2
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
- 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 2
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 2
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 claims description 2
- 125000001113 thiadiazolyl group Chemical group 0.000 claims description 2
- 125000000335 thiazolyl group Chemical group 0.000 claims description 2
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000001425 triazolyl group Chemical group 0.000 claims description 2
- FTVLMFQEYACZNP-UHFFFAOYSA-N trimethylsilyl trifluoromethanesulfonate Chemical compound C[Si](C)(C)OS(=O)(=O)C(F)(F)F FTVLMFQEYACZNP-UHFFFAOYSA-N 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 27
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 27
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 27
- 241000124008 Mammalia Species 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 4
- RMFWVOLULURGJI-UHFFFAOYSA-N 2,6-dichloro-7h-purine Chemical compound ClC1=NC(Cl)=C2NC=NC2=N1 RMFWVOLULURGJI-UHFFFAOYSA-N 0.000 claims 2
- 208000028257 Joubert syndrome with oculorenal defect Diseases 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
- 239000000018 receptor agonist Substances 0.000 claims 2
- 229940044601 receptor agonist Drugs 0.000 claims 2
- 230000003637 steroidlike Effects 0.000 claims 2
- WNWVKZTYMQWFHE-UHFFFAOYSA-N 4-ethylmorpholine Chemical group [CH2]CN1CCOCC1 WNWVKZTYMQWFHE-UHFFFAOYSA-N 0.000 claims 1
- JYZISXDTPDDOTM-LQHHRKQYSA-N 6-(1,3-diphenylpropan-2-ylamino)-9-[(2r,3r,4s,5s)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-n-(2-piperidin-1-ylethyl)purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(C(=O)NCCN3CCCCC3)=NC(NC(CC=3C=CC=CC=3)CC=3C=CC=CC=3)=C2N=C1 JYZISXDTPDDOTM-LQHHRKQYSA-N 0.000 claims 1
- NZLDCINKSRAJSR-LQHHRKQYSA-N 6-(2,2-diphenylethylamino)-9-[(2r,3r,4s,5s)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-n-[3-(pyridin-2-ylamino)propyl]purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(C(=O)NCCCNC=3N=CC=CC=3)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 NZLDCINKSRAJSR-LQHHRKQYSA-N 0.000 claims 1
- CSWKLOGHYJISOL-ZVJSOJQNSA-N 6-(2,2-diphenylethylamino)-9-[(2r,3r,4s,5s)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]-n-[3-[methyl(methylsulfonyl)amino]propyl]purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(C(=O)NCCCN(C)S(C)(=O)=O)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 CSWKLOGHYJISOL-ZVJSOJQNSA-N 0.000 claims 1
- BMHHQPYFORGXQA-UHFFFAOYSA-N 7h-purine-2-carboxamide Chemical compound NC(=O)C1=NC=C2N=CNC2=N1 BMHHQPYFORGXQA-UHFFFAOYSA-N 0.000 claims 1
- 102100022749 Aminopeptidase N Human genes 0.000 claims 1
- 101710099461 Aminopeptidase N Proteins 0.000 claims 1
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000005910 aminocarbonylation reaction Methods 0.000 claims 1
- 229910002091 carbon monoxide Inorganic materials 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 208000027866 inflammatory disease Diseases 0.000 claims 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims 1
- GOBHYUHHXFEITR-ZVJSOJQNSA-N n-[3-(dimethylamino)propyl]-6-(2,2-diphenylethylamino)-9-[(2r,3r,4s,5s)-5-(ethylcarbamoyl)-3,4-dihydroxyoxolan-2-yl]purine-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(C(=O)NCCCN(C)C)=NC(NCC(C=3C=CC=CC=3)C=3C=CC=CC=3)=C2N=C1 GOBHYUHHXFEITR-ZVJSOJQNSA-N 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
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- 125000006308 propyl amino group Chemical group 0.000 claims 1
- 210000000440 neutrophil Anatomy 0.000 description 7
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine Chemical compound C1=NC=2C(N)=NC=NC=2N1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 description 6
- 101000851058 Homo sapiens Neutrophil elastase Proteins 0.000 description 4
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- 102000052502 human ELANE Human genes 0.000 description 4
- 108020003175 receptors Proteins 0.000 description 4
- 102000005962 receptors Human genes 0.000 description 4
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 3
- 230000004913 activation Effects 0.000 description 3
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- 230000004044 response Effects 0.000 description 3
- 101150007969 ADORA1 gene Proteins 0.000 description 2
- 230000002757 inflammatory effect Effects 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 210000004072 lung Anatomy 0.000 description 2
- 150000003212 purines Chemical class 0.000 description 2
- 210000002345 respiratory system Anatomy 0.000 description 2
- 210000001519 tissue Anatomy 0.000 description 2
- JWZZKOKVBUJMES-UHFFFAOYSA-N (+-)-Isoprenaline Chemical compound CC(C)NCC(O)C1=CC=C(O)C(O)=C1 JWZZKOKVBUJMES-UHFFFAOYSA-N 0.000 description 1
- ZEYSHALLPAKUHG-UHFFFAOYSA-N 4-methoxypiperidine Chemical compound COC1CCNCC1 ZEYSHALLPAKUHG-UHFFFAOYSA-N 0.000 description 1
- 108010041368 Adenosine A2 Receptors Proteins 0.000 description 1
- 102000000506 Adenosine A2 Receptors Human genes 0.000 description 1
- 102000007471 Adenosine A2A receptor Human genes 0.000 description 1
- 108010085277 Adenosine A2A receptor Proteins 0.000 description 1
- 102000007470 Adenosine A2B Receptor Human genes 0.000 description 1
- 108010085273 Adenosine A2B receptor Proteins 0.000 description 1
- 229940122086 Adenosine A2a receptor agonist Drugs 0.000 description 1
- 108050000203 Adenosine receptors Proteins 0.000 description 1
- 102000009346 Adenosine receptors Human genes 0.000 description 1
- YZXBAPSDXZZRGB-DOFZRALJSA-M Arachidonate Chemical compound CCCCC\C=C/C\C=C/C\C=C/C\C=C/CCCC([O-])=O YZXBAPSDXZZRGB-DOFZRALJSA-M 0.000 description 1
- 102000010834 Extracellular Matrix Proteins Human genes 0.000 description 1
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- 241001465754 Metazoa Species 0.000 description 1
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- 239000002465 adenosine A2a receptor agonist Substances 0.000 description 1
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- 230000002411 adverse Effects 0.000 description 1
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- 239000002975 chemoattractant Substances 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
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- 210000003979 eosinophil Anatomy 0.000 description 1
- 210000002744 extracellular matrix Anatomy 0.000 description 1
- 230000023266 generation of precursor metabolites and energy Effects 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 210000003630 histaminocyte Anatomy 0.000 description 1
- 102000055905 human ADORA2A Human genes 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 229960001317 isoprenaline Drugs 0.000 description 1
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- VNYSSYRCGWBHLG-AMOLWHMGSA-N leukotriene B4 Chemical compound CCCCC\C=C/C[C@@H](O)\C=C\C=C\C=C/[C@@H](O)CCCC(O)=O VNYSSYRCGWBHLG-AMOLWHMGSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D473/00—Heterocyclic compounds containing purine ring systems
-
- 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
-
- 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
-
- 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
- A61P11/02—Nasal agents, e.g. decongestants
-
- 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
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
-
- 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
-
- A—HUMAN NECESSITIES
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- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
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- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
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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
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
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Applications Claiming Priority (1)
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| GBGB0003960.2A GB0003960D0 (en) | 2000-02-18 | 2000-02-18 | Purine derivatives |
Publications (1)
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| ZA200206526B true ZA200206526B (en) | 2003-10-16 |
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| KR (1) | KR20030036138A (de) |
| CN (1) | CN1400975A (de) |
| AP (1) | AP2002002598A0 (de) |
| AR (1) | AR027437A1 (de) |
| AT (1) | ATE325807T1 (de) |
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| BR (1) | BR0108408A (de) |
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| CR (1) | CR6722A (de) |
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| GB (1) | GB0003960D0 (de) |
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| US7378400B2 (en) * | 1999-02-01 | 2008-05-27 | University Of Virginia Patent Foundation | Method to reduce an inflammatory response from arthritis |
| US7427606B2 (en) * | 1999-02-01 | 2008-09-23 | University Of Virginia Patent Foundation | Method to reduce inflammatory response in transplanted tissue |
| US6232297B1 (en) * | 1999-02-01 | 2001-05-15 | University Of Virginia Patent Foundation | Methods and compositions for treating inflammatory response |
| GB9913932D0 (en) * | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
| US6753322B2 (en) * | 2000-06-06 | 2004-06-22 | Pfizer Inc | 2-aminocarbonyl-9H-purine derivatives |
| US6921753B2 (en) | 2000-06-27 | 2005-07-26 | Pfizer Inc | Purine derivatives |
| GB0022695D0 (en) | 2000-09-15 | 2000-11-01 | Pfizer Ltd | Purine Derivatives |
| WO2003029264A2 (en) * | 2001-10-01 | 2003-04-10 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
| GB0129273D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Crystalline drug form |
| GB0129270D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Pharmaceutical combination |
| GB0129397D0 (en) * | 2001-12-07 | 2002-01-30 | Pfizer Ltd | Pharmaceutical combination |
| US7414036B2 (en) | 2002-01-25 | 2008-08-19 | Muscagen Limited | Compounds useful as A3 adenosine receptor agonists |
| AR044519A1 (es) | 2003-05-02 | 2005-09-14 | Novartis Ag | Derivados de piridin-tiazol amina y de pirimidin-tiazol amina |
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| GB0411056D0 (en) | 2004-05-18 | 2004-06-23 | Novartis Ag | Organic compounds |
| DK1758596T3 (da) * | 2004-05-26 | 2010-07-26 | Inotek Pharmaceuticals Corp | Purinderivater som adenosin-A1-receptoragonister og fremgangsmåder til anvendelse deraf |
| EP1778712B1 (de) * | 2004-08-02 | 2013-01-30 | University Of Virginia Patent Foundation | 2-propynyl-adenosin-analoga mit modifizierten 5'-ribosegruppen mit a2a-agonistenaktivität |
| WO2006028618A1 (en) * | 2004-08-02 | 2006-03-16 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity |
| WO2006023272A1 (en) * | 2004-08-02 | 2006-03-02 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having a2a agonist activity |
| US7863253B2 (en) * | 2004-09-20 | 2011-01-04 | Inotek Pharmaceuticals Corporation | Purine Derivatives and methods of use thereof |
| GT200500281A (es) | 2004-10-22 | 2006-04-24 | Novartis Ag | Compuestos organicos. |
| GB0424284D0 (en) | 2004-11-02 | 2004-12-01 | Novartis Ag | Organic compounds |
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| GB0500785D0 (en) | 2005-01-14 | 2005-02-23 | Novartis Ag | Organic compounds |
| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| US7910708B2 (en) | 2005-10-21 | 2011-03-22 | Novartis Ag | Anti-IL13 human antibodies |
| CA2627319A1 (en) * | 2005-11-30 | 2007-06-07 | Prakash Jagtap | Purine derivatives and methods of use thereof |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| WO2007092936A2 (en) * | 2006-02-08 | 2007-08-16 | University Of Virginia Patent Foundation | Method to treat gastric lesions |
| US8178509B2 (en) | 2006-02-10 | 2012-05-15 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
| GB0607950D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| KR20080110925A (ko) * | 2006-04-21 | 2008-12-19 | 노파르티스 아게 | 아데노신 ａ２ａ 수용체 효능제로서 사용하기 위한 퓨린 유도체 |
| GB0607951D0 (en) * | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| EP1889846A1 (de) | 2006-07-13 | 2008-02-20 | Novartis AG | Purinderivate als A2a Agonisten |
| EP1903044A1 (de) | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosinderivate als Agonisten des A2A-Rezeptors |
| DE602007013441D1 (de) | 2006-09-29 | 2011-05-05 | Novartis Ag | Pyrazolopyrimidine als pi3k-lipidkinasehemmer |
| CA2667962A1 (en) | 2006-10-30 | 2008-05-08 | Novartis Ag | Heterocyclic compounds as antiinflammatory agents |
| JP2008285478A (ja) * | 2007-04-16 | 2008-11-27 | Santen Pharmaceut Co Ltd | アデノシンａ２ａ受容体アゴニストを有効成分として含有する緑内障治療剤 |
| US8058259B2 (en) * | 2007-12-20 | 2011-11-15 | University Of Virginia Patent Foundation | Substituted 4-{3-[6-amino-9-(3,4-dihydroxy-tetrahydro-furan-2-yl)-9H-purin-2-yl]-prop-2-ynyl}-piperidine-1-carboxylic acid esters as A2AR agonists |
| PL2231642T3 (pl) | 2008-01-11 | 2014-04-30 | Novartis Ag | Pirymidyny jako inhibitory kinazy |
| UA104010C2 (en) * | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Purine compounds |
| PT2391366E (pt) | 2009-01-29 | 2013-02-05 | Novartis Ag | Benzimidazoles substituídos para o tratamento de astrocitomas |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| EP2464649A1 (de) | 2009-08-12 | 2012-06-20 | Novartis AG | Heterocyclische hydrazonverbindungen und ihre verwendung zur behandlung von krebs und entzündung |
| NZ598220A (en) | 2009-08-17 | 2014-02-28 | Intellikine Llc | Heterocyclic compounds and uses thereof |
| CA2771432A1 (en) | 2009-08-20 | 2011-02-24 | Novartis Ag | Heterocyclic oxime compounds |
| SG10201502588UA (en) | 2010-01-11 | 2015-05-28 | Inotek Pharmaceuticals Corp | Combination, kit and method of reducing intraocular pressure |
| MX2012010724A (es) | 2010-03-26 | 2012-11-12 | Inotek Pharmaceuticals Corp | Metodo para reducir la presion intraocular en seres humanos empleando n6-ciclopentiladenosina (cpa), derivados de cpa o profarmacos de los mismos. |
| 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 |
| JP2014505088A (ja) | 2011-02-10 | 2014-02-27 | ノバルティス アーゲー | Ｃ−ＭＥＴチロシンキナーゼ阻害剤としての［１，２，４］トリアゾロ［４，３−ｂ］ピリダジン化合物 |
| 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 |
| US9102671B2 (en) | 2011-02-25 | 2015-08-11 | Novartis Ag | Compounds and compositions as TRK inhibitors |
| UY34329A (es) | 2011-09-15 | 2013-04-30 | Novartis Ag | Compuestos de triazolopiridina |
| US9174994B2 (en) | 2011-11-23 | 2015-11-03 | Intellikine, Llc | Enhanced treatment regimens using mTor inhibitors |
| US9278991B2 (en) | 2012-01-26 | 2016-03-08 | Inotek Pharmaceuticals Corporation | Anhydrous polymorphs of [(2R,3S,4R,5R)-5-(6-(cyclopentylamino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)} methyl nitrate and processes of preparation thereof |
| CN104245701A (zh) | 2012-04-03 | 2014-12-24 | 诺华有限公司 | 有酪氨酸激酶抑制剂的组合产品和其应用 |
| CN105188714A (zh) | 2013-03-15 | 2015-12-23 | 伊诺泰克制药公司 | 眼用配制品 |
| EP2968340A4 (de) | 2013-03-15 | 2016-08-10 | Intellikine Llc | Kombination von kinaseinhibitoren und verwendungen davon |
| TW201605450A (zh) | 2013-12-03 | 2016-02-16 | 諾華公司 | Ｍｄｍ２抑制劑與ＢＲＡＦ抑制劑之組合及其用途 |
| WO2016011658A1 (en) | 2014-07-25 | 2016-01-28 | Novartis Ag | Combination therapy |
| US20170216297A1 (en) | 2014-07-28 | 2017-08-03 | Technische Universitaet Dresden | Efficient inhibition of hsp27 |
| KR20170036037A (ko) | 2014-07-31 | 2017-03-31 | 노파르티스 아게 | 조합 요법 |
| TWI758146B (zh) * | 2015-03-13 | 2022-03-11 | 瑞典商杜比國際公司 | 解碼具有增強頻譜帶複製元資料在至少一填充元素中的音訊位元流 |
| 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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| US5140015A (en) * | 1990-02-20 | 1992-08-18 | Whitby Research, Inc. | 2-aralkoxy and 2-alkoxy adenosine derivatives as coronary vasodilators and antihypertensive agents |
| US5189027A (en) * | 1990-11-30 | 1993-02-23 | Yamasa Shoyu Kabushiki Kaisha | 2-substituted adenosine derivatives and pharmaceutical compositions for circulatory diseases |
| IT1254915B (it) * | 1992-04-24 | 1995-10-11 | Gloria Cristalli | Derivati di adenosina ad attivita' a2 agonista |
| BR9914526A (pt) * | 1998-10-16 | 2001-07-03 | Pfizer | Derivados de adenina |
| GB9913932D0 (en) | 1999-06-15 | 1999-08-18 | Pfizer Ltd | Purine derivatives |
| GB9924361D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Ltd | Purine derivatives |
| GB9924363D0 (en) | 1999-10-14 | 1999-12-15 | Pfizer Central Res | Purine derivatives |
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2000
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2001
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- 2001-02-09 EE EEP200200452A patent/EE200200452A/xx unknown
- 2001-02-09 AP APAP/P/2002/002598A patent/AP2002002598A0/en unknown
- 2001-02-09 HU HU0301055A patent/HUP0301055A2/hu unknown
- 2001-02-09 SK SK1169-2002A patent/SK11692002A3/sk unknown
- 2001-02-09 ES ES01902583T patent/ES2260199T3/es not_active Expired - Lifetime
- 2001-02-09 IL IL15054301A patent/IL150543A0/xx unknown
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- 2001-02-09 AT AT01902583T patent/ATE325807T1/de not_active IP Right Cessation
- 2001-02-09 DE DE60119492T patent/DE60119492T2/de not_active Expired - Fee Related
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- 2001-02-09 MX MXPA02008068A patent/MXPA02008068A/es active IP Right Grant
- 2001-02-09 AU AU2001230440A patent/AU2001230440A1/en not_active Abandoned
- 2001-02-09 CZ CZ20022703A patent/CZ20022703A3/cs unknown
- 2001-02-09 CA CA002400619A patent/CA2400619A1/en not_active Abandoned
- 2001-02-09 WO PCT/IB2001/000167 patent/WO2001060835A1/en active IP Right Grant
- 2001-02-09 BR BR0108408-9A patent/BR0108408A/pt not_active IP Right Cessation
- 2001-02-09 EP EP01902583A patent/EP1255764B8/de not_active Expired - Lifetime
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- 2001-02-12 GT GT200100027A patent/GT200100027A/es unknown
- 2001-02-15 CO CO01012091A patent/CO5271668A1/es not_active Application Discontinuation
- 2001-02-15 AR ARP010100690A patent/AR027437A1/es not_active Application Discontinuation
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- 2001-02-15 HN HN2001000027A patent/HN2001000027A/es unknown
- 2001-02-16 TN TNTNSN01028A patent/TNSN01028A1/fr unknown
- 2001-02-16 PE PE2001000174A patent/PE20011122A1/es not_active Application Discontinuation
- 2001-02-16 SV SV2001000317A patent/SV2002000317A/es not_active Application Discontinuation
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2002
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