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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| 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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| 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 |
| SG176313A1 (en) * | 2001-10-01 | 2011-12-29 | Univ Virginia Patent Found | 2-propynyl adenosine analogs having a2a agonist activity and compositions thereof |
| GB0129270D0 (en) * | 2001-12-06 | 2002-01-23 | Pfizer Ltd | Pharmaceutical combination |
| 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 |
| 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 |
| US7423144B2 (en) * | 2004-05-26 | 2008-09-09 | Inotek Pharmaceuticals Corporation | Purine Derivatives as adenosine A1 receptor agonists and methods of use thereof |
| WO2006023272A1 (en) * | 2004-08-02 | 2006-03-02 | University Of Virginia Patent Foundation | 2-polycyclic propynyl adenosine analogs having a2a agonist activity |
| 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 |
| CA2576826C (en) * | 2004-08-02 | 2014-09-30 | University Of Virginia Patent Foundation | 2-propynyl adenosine analogs with modified 5'-ribose groups having a2a agonist activity |
| JP5011112B2 (ja) * | 2004-09-20 | 2012-08-29 | イノテック ファーマシューティカルズ コーポレイション | プリン誘導体を含有する炎症性疾患の治療用医薬 |
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| GB0510390D0 (en) | 2005-05-20 | 2005-06-29 | Novartis Ag | Organic compounds |
| RU2421464C2 (ru) | 2005-10-21 | 2011-06-20 | Новартис Аг | Человеческие антитела к il-13 и их терапевтическое применение |
| EP1962597A4 (en) * | 2005-11-30 | 2008-12-17 | Inotek Pharmaceuticals Corp | PURINE DERIVATIVES AND METHOD OF USE |
| GB0601951D0 (en) | 2006-01-31 | 2006-03-15 | Novartis Ag | Organic compounds |
| US20080027022A1 (en) * | 2006-02-08 | 2008-01-31 | Linden Joel M | Method to treat gastric lesions |
| WO2007120972A2 (en) | 2006-02-10 | 2007-10-25 | University Of Virginia Patent Foundation | Method to treat sickle cell disease |
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| GB0607950D0 (en) | 2006-04-21 | 2006-05-31 | Novartis Ag | Organic compounds |
| NZ571429A (en) | 2006-04-21 | 2011-09-30 | Novartis Ag | Purine derivatives for use as adenosine A2A receptor agonists |
| US8188063B2 (en) * | 2006-06-19 | 2012-05-29 | University Of Virginia Patent Foundation | Use of adenosine A2A modulators to treat spinal cord injury |
| EP1889846A1 (en) | 2006-07-13 | 2008-02-20 | Novartis AG | Purine derivatives as A2a agonists |
| EP1903044A1 (en) | 2006-09-14 | 2008-03-26 | Novartis AG | Adenosine Derivatives as A2A Receptor Agonists |
| RU2009115954A (ru) | 2006-09-29 | 2010-11-10 | Новартис АГ (CH) | Пиразолопиримидины в качестве ингибиторов липидной киназы р13к |
| WO2008052734A1 (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 |
| JP5584138B2 (ja) | 2008-01-11 | 2014-09-03 | ノバルティス アーゲー | キナーゼ阻害剤としてのピリミジン類 |
| UA104010C2 (xx) * | 2008-12-18 | 2013-12-25 | Эли Лилли Энд Компани | Сполуки пурину$соединения пурина |
| SI2391366T1 (sl) | 2009-01-29 | 2013-01-31 | Novartis Ag | Substituirani benzimidazoli za zdravljenje astrocitomov |
| US8389526B2 (en) | 2009-08-07 | 2013-03-05 | Novartis Ag | 3-heteroarylmethyl-imidazo[1,2-b]pyridazin-6-yl derivatives |
| AU2010283806A1 (en) | 2009-08-12 | 2012-03-01 | Novartis Ag | Heterocyclic hydrazone compounds and their uses to treat cancer and inflammation |
| GEP201706639B (en) | 2009-08-17 | 2017-03-27 | Intellikine Llc | Heterocyclic compounds and uses thereof |
| BR112012008061A2 (pt) | 2009-08-20 | 2016-03-01 | Novartis Ag | compostos de oxima heterocíclica |
| ME02608B (me) | 2010-01-11 | 2017-06-20 | Inotek Pharmaceuticals Corp | Kombinacija, komplet i postupak snižavanja intraokularnog pritiska |
| JP2013523739A (ja) | 2010-03-26 | 2013-06-17 | イノテック ファーマシューティカルズ コーポレイション | Ｎ６−シクロペンチルアデノシン（ｃｐａ）、ｃｐａ誘導体またはそれらのプロドラッグを用いてヒトにおける眼内圧を低下させる方法 |
| WO2012034095A1 (en) | 2010-09-09 | 2012-03-15 | Irm Llc | Compounds and compositions as trk inhibitors |
| UY33597A (es) | 2010-09-09 | 2012-04-30 | Irm Llc | Compuestos y composiciones como inhibidores de la trk |
| 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 |
| AU2012220572A1 (en) | 2011-02-25 | 2013-08-29 | Irm Llc | Compounds and compositions as trk inhibitors |
| US9062045B2 (en) | 2011-09-15 | 2015-06-23 | Novartis Ag | Triazolopyridine compounds |
| JP6130391B2 (ja) | 2011-11-23 | 2017-05-17 | インテリカイン， エルエルシー | Ｍｔｏｒ阻害剤を使用する強化された治療レジメン |
| RS56150B1 (sr) | 2012-01-26 | 2017-11-30 | Inotek Pharmaceuticals Corp | Anhidrovani polimorfi (2r,3s,4r,5r)-5-(6-(ciklopentilamino)-9h-purin-9-yl)-3,4-dihidroksitetrahidrofuran-2-yl)} metil-nitrata i postupak njegove pripreme |
| CN110507654A (zh) | 2012-04-03 | 2019-11-29 | 诺华有限公司 | 有酪氨酸激酶抑制剂的组合产品和其应用 |
| JP2016513706A (ja) | 2013-03-15 | 2016-05-16 | イノテック ファーマシューティカルズ コーポレイション | 点眼用製剤 |
| EP2968340A4 (en) | 2013-03-15 | 2016-08-10 | Intellikine Llc | COMBINING KINASE INHIBITORS AND USES THEREOF |
| 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 |
| EP3174545A1 (de) | 2014-07-28 | 2017-06-07 | Technische Universität Dresden | Effiziente hemmung von hsp27 |
| CA2954862A1 (en) | 2014-07-31 | 2016-02-04 | Novartis Ag | Combination therapy |
| TWI693594B (zh) * | 2015-03-13 | 2020-05-11 | 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 |
| ATE331726T1 (de) * | 1998-10-16 | 2006-07-15 | Pfizer | Adenine-derivate |
| 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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