ZA200404161B - Adenosine A2a receptor antagonists. - Google Patents
Adenosine A2a receptor antagonists. Download PDFInfo
- Publication number
- ZA200404161B ZA200404161B ZA200404161A ZA200404161A ZA200404161B ZA 200404161 B ZA200404161 B ZA 200404161B ZA 200404161 A ZA200404161 A ZA 200404161A ZA 200404161 A ZA200404161 A ZA 200404161A ZA 200404161 B ZA200404161 B ZA 200404161B
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- South Africa
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- 229940123702 Adenosine A2a receptor antagonist Drugs 0.000 title 1
- 239000002467 adenosine A2a receptor antagonist Substances 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 46
- 208000018737 Parkinson disease Diseases 0.000 claims description 24
- 125000000217 alkyl group Chemical group 0.000 claims description 21
- 239000000203 mixture Substances 0.000 claims description 18
- 125000003118 aryl group Chemical group 0.000 claims description 16
- 239000003795 chemical substances by application Substances 0.000 claims description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 239000008194 pharmaceutical composition Substances 0.000 claims description 14
- -1 alkylsulfonamino Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 11
- 229910052736 halogen Inorganic materials 0.000 claims description 11
- 150000002367 halogens Chemical class 0.000 claims description 11
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 208000015114 central nervous system disease Diseases 0.000 claims description 8
- 125000001072 heteroaryl group Chemical group 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 6
- 239000003937 drug carrier Substances 0.000 claims description 6
- 239000003112 inhibitor Substances 0.000 claims description 6
- 208000024827 Alzheimer disease Diseases 0.000 claims description 5
- 102000010909 Monoamine Oxidase Human genes 0.000 claims description 5
- 108010062431 Monoamine oxidase Proteins 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 206010039966 Senile dementia Diseases 0.000 claims description 4
- 125000004442 acylamino group Chemical group 0.000 claims description 4
- 125000004423 acyloxy group Chemical group 0.000 claims description 4
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 125000004471 alkyl aminosulfonyl group Chemical group 0.000 claims description 4
- 125000004472 dialkylaminosulfonyl group Chemical group 0.000 claims description 4
- 239000000534 dopa decarboxylase inhibitor Substances 0.000 claims description 4
- 229940052760 dopamine agonists Drugs 0.000 claims description 4
- 239000003136 dopamine receptor stimulating agent Substances 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 230000004770 neurodegeneration Effects 0.000 claims description 4
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 4
- 125000003386 piperidinyl group Chemical group 0.000 claims description 4
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 206010039987 Senile psychosis Diseases 0.000 claims description 3
- 125000003725 azepanyl group Chemical group 0.000 claims description 3
- 208000010877 cognitive disease Diseases 0.000 claims description 3
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 2
- 125000005422 alkyl sulfonamido group Chemical group 0.000 claims description 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 2
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 239000012453 solvate Substances 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 14
- WTDRDQBEARUVNC-LURJTMIESA-N L-DOPA Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-LURJTMIESA-N 0.000 claims 3
- WTDRDQBEARUVNC-UHFFFAOYSA-N L-Dopa Natural products OC(=O)C(N)CC1=CC=C(O)C(O)=C1 WTDRDQBEARUVNC-UHFFFAOYSA-N 0.000 claims 3
- 239000003543 catechol methyltransferase inhibitor Substances 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- SQVRNKJHWKZAKO-PFQGKNLYSA-N N-acetyl-beta-neuraminic acid Chemical compound CC(=O)N[C@@H]1[C@@H](O)C[C@@](O)(C(O)=O)O[C@H]1[C@H](O)[C@H](O)CO SQVRNKJHWKZAKO-PFQGKNLYSA-N 0.000 claims 2
- 239000007789 gas Substances 0.000 claims 1
- 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 22
- 239000002126 C01EB10 - Adenosine Substances 0.000 description 11
- 229960005305 adenosine Drugs 0.000 description 11
- LRFVTYWOQMYALW-UHFFFAOYSA-N 9H-xanthine Chemical compound O=C1NC(=O)NC2=C1NC=N2 LRFVTYWOQMYALW-UHFFFAOYSA-N 0.000 description 5
- 239000005557 antagonist Substances 0.000 description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000004122 cyclic group Chemical group 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000002464 receptor antagonist Substances 0.000 description 3
- 229940044551 receptor antagonist Drugs 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 102000006378 Catechol O-methyltransferase Human genes 0.000 description 2
- 108020002739 Catechol O-methyltransferase Proteins 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 125000001246 bromo group Chemical group Br* 0.000 description 2
- 210000003169 central nervous system Anatomy 0.000 description 2
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000000144 pharmacologic effect Effects 0.000 description 2
- 229940075420 xanthine Drugs 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 206010006482 Bronchospasm Diseases 0.000 description 1
- 229940081615 DOPA decarboxylase inhibitor Drugs 0.000 description 1
- 229940123736 Decarboxylase inhibitor Drugs 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- 108091006027 G proteins Proteins 0.000 description 1
- 102000030782 GTP binding Human genes 0.000 description 1
- 108091000058 GTP-Binding Proteins 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 208000028017 Psychotic disease Diseases 0.000 description 1
- 206010047139 Vasoconstriction Diseases 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 description 1
- 102000030621 adenylate cyclase Human genes 0.000 description 1
- 108060000200 adenylate cyclase Proteins 0.000 description 1
- 210000001789 adipocyte Anatomy 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 125000005213 alkyl heteroaryl group Chemical group 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 230000002744 anti-aggregatory effect Effects 0.000 description 1
- 230000001430 anti-depressive effect Effects 0.000 description 1
- 230000003556 anti-epileptic effect Effects 0.000 description 1
- 239000003146 anticoagulant agent Substances 0.000 description 1
- 239000000935 antidepressant agent Substances 0.000 description 1
- 229940005513 antidepressants Drugs 0.000 description 1
- 229940125688 antiparkinson agent Drugs 0.000 description 1
- 239000002249 anxiolytic agent Substances 0.000 description 1
- 230000000949 anxiolytic effect Effects 0.000 description 1
- 125000003435 aroyl group Chemical group 0.000 description 1
- 125000004659 aryl alkyl thio group Chemical group 0.000 description 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 description 1
- 125000005135 aryl sulfinyl group Chemical group 0.000 description 1
- 125000004391 aryl sulfonyl group Chemical group 0.000 description 1
- 125000005110 aryl thio group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 210000004227 basal ganglia Anatomy 0.000 description 1
- 230000002051 biphasic effect Effects 0.000 description 1
- 230000007885 bronchoconstriction Effects 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000000747 cardiac effect Effects 0.000 description 1
- 210000000748 cardiovascular system Anatomy 0.000 description 1
- 230000003920 cognitive function Effects 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
- 239000003954 decarboxylase inhibitor Substances 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 229960003638 dopamine Drugs 0.000 description 1
- 239000002552 dosage form Substances 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004475 heteroaralkyl group Chemical group 0.000 description 1
- 125000005150 heteroarylsulfinyl group Chemical group 0.000 description 1
- 125000005143 heteroarylsulfonyl group Chemical group 0.000 description 1
- 125000005368 heteroarylthio group Chemical group 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 230000004130 lipolysis Effects 0.000 description 1
- 230000001404 mediated effect Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000006574 non-aromatic ring group Chemical group 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 230000035790 physiological processes and functions Effects 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 210000002345 respiratory system Anatomy 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 239000000932 sedative agent Substances 0.000 description 1
- 230000001624 sedative effect Effects 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 230000024883 vasodilation Effects 0.000 description 1
- 229940124549 vasodilator Drugs 0.000 description 1
- 239000003071 vasodilator agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
- C07D487/14—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US33434201P | 2001-11-30 | 2001-11-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200404161B true ZA200404161B (en) | 2005-11-30 |
Family
ID=23306779
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200404161A ZA200404161B (en) | 2001-11-30 | 2004-05-27 | Adenosine A2a receptor antagonists. |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US6916811B2 (https=) |
| EP (1) | EP1448565B1 (https=) |
| JP (2) | JP4284182B2 (https=) |
| KR (1) | KR20050044593A (https=) |
| CN (1) | CN1692116A (https=) |
| AR (1) | AR037680A1 (https=) |
| AT (1) | ATE453647T1 (https=) |
| AU (1) | AU2002346503A1 (https=) |
| CA (1) | CA2468649C (https=) |
| DE (1) | DE60234951D1 (https=) |
| ES (1) | ES2336435T3 (https=) |
| HU (1) | HUP0402018A3 (https=) |
| IL (1) | IL161716A0 (https=) |
| MX (1) | MXPA04005209A (https=) |
| PE (1) | PE20030665A1 (https=) |
| TW (1) | TW200306837A (https=) |
| WO (1) | WO2003048165A1 (https=) |
| ZA (1) | ZA200404161B (https=) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE60110219T2 (de) * | 2000-05-26 | 2006-03-09 | Schering Corp. | Adenosin a2a rezeptor antagonisten |
| US6964288B2 (en) * | 2001-07-06 | 2005-11-15 | Ksaria Corporation | Apparatus and method for automated preparation of an optical fiber |
| KR100687954B1 (ko) | 2001-10-15 | 2007-02-27 | 쉐링 코포레이션 | 아데노신 Ａ2ａ 수용체 길항제로서의이미다조（4,3-ｅ）-1,2,4-트리아졸로（1,5-ｃ） 피리미딘 |
| AU2003245380A1 (en) * | 2002-05-30 | 2003-12-19 | King Pharmaceuticals Research & Development, Inc. | Pharmaceutically active compounds having a tricyclic pyrazolotriazolopyrimidine ring structure and methods of use |
| TWI331036B (en) | 2002-12-19 | 2010-10-01 | Schering Corp | Adenosine a2a receptor antagonists for the treatment of extra-pyramidal syndrome and other movement disorders |
| WO2005039506A2 (en) * | 2003-10-24 | 2005-05-06 | Exelixis, Inc. | P70s6 kinase modulators and method of use |
| ES2278353T3 (es) * | 2003-10-28 | 2007-08-01 | Schering Corporation | Procedimiento para preparar 5-amino-pirazolo-(4,3-e)-1,2,4-triazolo(1,5-c)pirimidinas sustituidas. |
| CA2550071A1 (en) * | 2003-12-19 | 2005-07-07 | Schering Corporation | Pharmaceutical compositions |
| EP2258372B8 (en) * | 2005-06-07 | 2012-12-19 | Kyowa Hakko Kirin Co., Ltd. | A2A antagonists for use in the treatment of motor disorders |
| ES2273599B1 (es) | 2005-10-14 | 2008-06-01 | Universidad De Barcelona | Compuestos para el tratamiento de la fibrilacion auricular. |
| PE20080145A1 (es) * | 2006-03-21 | 2008-02-11 | Janssen Pharmaceutica Nv | Tetrahidro-pirimidoazepinas como moduladores de trpv1 |
| US7723343B2 (en) * | 2007-03-30 | 2010-05-25 | King Pharmaceuticals Research And Development, Inc. | Adenosine A2A receptor antagonists |
| WO2009078999A1 (en) | 2007-12-17 | 2009-06-25 | Janssen Pharmaceutica N.V. | Imidazolo-, oxazolo-, and thiazolopyrimidine modulators of trpv1 |
| US12246013B2 (en) | 2008-08-01 | 2025-03-11 | Eye Therapies Llc | Vasoconstriction compositions and methods of use |
| US8952011B2 (en) | 2008-08-01 | 2015-02-10 | Eye Therapies Llc | Compositions and methods for the treatment of nasal conditions |
| US20100203165A1 (en) | 2008-08-01 | 2010-08-12 | Gerald Horn | Compositions and methods for treatment of disorders or conditions of the eye |
| HRP20141047T1 (hr) | 2008-08-01 | 2015-01-02 | Eye Therapies Llc | Pripravci za sužavanje krvnih žila i metode njihove uporabe |
| US8273754B2 (en) | 2008-12-30 | 2012-09-25 | Arqule, Inc. | Substituted 1H-pyrazolo[3,4-D]pyrimidine-6-amine compounds |
| US8343961B2 (en) | 2009-03-31 | 2013-01-01 | Arqule, Inc. | Substituted heterocyclic compounds |
| US8987270B2 (en) | 2009-07-27 | 2015-03-24 | Eye Therapies Llc | Formulations of selective alpha-2 agonists and methods of use thereof |
| US20110152271A1 (en) * | 2009-12-17 | 2011-06-23 | Gerald Horn | Compositions and methods for ophthalmic delivery of nasal decongestants |
| US8445526B2 (en) | 2011-02-03 | 2013-05-21 | Glaucoma & Nasal Therapies Llc | Compositions and methods for treatment of glaucoma |
| US8999938B2 (en) | 2013-06-21 | 2015-04-07 | Gnt Llc | Ophthalmic lipophilic drug delivery vehicle formulations |
| CN110742893B (zh) * | 2018-07-23 | 2024-04-05 | 百济神州(北京)生物科技有限公司 | A2a受体拮抗剂治疗癌症的方法 |
| US12414952B2 (en) | 2018-11-20 | 2025-09-16 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2019383948A1 (en) | 2018-11-20 | 2021-05-20 | Merck Sharp & Dohme Llc | Substituted amino triazolopyrimidine and amino triazolopyrazine adenosine receptor antagonists, pharmaceutical compositions and their use |
| WO2020112700A1 (en) | 2018-11-30 | 2020-06-04 | Merck Sharp & Dohme Corp. | 9-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| AU2019388872A1 (en) | 2018-11-30 | 2021-05-27 | Merck Sharp & Dohme Llc | 7-, 8-, and 10-substituted amino triazolo quinazoline derivatives as adenosine receptor antagonists, pharmaceutical compositions and their use |
| DE102019116986A1 (de) | 2019-06-24 | 2020-12-24 | Helmholtz-Zentrum Dresden-Rossendorf E. V. | Deuterierte 7-(3-(4-(2-([18F]Fluor)ethoxy)phenyl)propyl)-2-(furan-2-yl)-7H-pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidin-5-amin-Derivate |
| JP2022540583A (ja) * | 2019-07-17 | 2022-09-16 | テオン セラピューティクス，インク． | アデノシンａ２ａ受容体アンタゴニスト及びその使用 |
| CN112592354B (zh) | 2019-07-30 | 2022-05-27 | 厦门宝太生物科技股份有限公司 | 一种异噁唑并嘧啶类杂环化合物的制备方法 |
| CN112028891B (zh) | 2019-07-30 | 2022-07-05 | 厦门宝太生物科技股份有限公司 | 腺苷受体拮抗剂 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT1264901B1 (it) | 1993-06-29 | 1996-10-17 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(15-c)pirimidine ad attivita' antagonista per il recettore a2 dell'adenosina |
| WO1995003806A1 (en) * | 1993-07-27 | 1995-02-09 | Kyowa Hakko Kogyo Co., Ltd. | Remedy for parkinson's disease |
| IT1277392B1 (it) * | 1995-07-28 | 1997-11-10 | Schering Plough S P A | Analoghi eterociclici di 1,2,4-triazolo(1,5-c]pirimidine ad attivita' antagonista per il recettore a2a dell'adenosina |
| IT1291372B1 (it) | 1997-05-21 | 1999-01-07 | Schering Plough S P A | Uso di analoghi eterociclici di 1,2,4-triazolo (1,5-c) pirimidine per la preparazione di medicamenti utili per il trattamento delle malattie |
| US6921825B2 (en) * | 1998-09-16 | 2005-07-26 | King Pharmaceuticuals Research & Development, Inc. | Adenosine A3 receptor modulators |
| US6448253B1 (en) * | 1998-09-16 | 2002-09-10 | King Pharmaceuticals Research And Development, Inc. | Adenosine A3 receptor modulators |
| DE60110219T2 (de) * | 2000-05-26 | 2006-03-09 | Schering Corp. | Adenosin a2a rezeptor antagonisten |
| AU2003245380A1 (en) * | 2002-05-30 | 2003-12-19 | King Pharmaceuticals Research & Development, Inc. | Pharmaceutically active compounds having a tricyclic pyrazolotriazolopyrimidine ring structure and methods of use |
| EP1622912B1 (en) * | 2003-04-23 | 2009-05-27 | Schering Corporation | 2-alkynyl-and 2-alkenyl-pyrazolo- [4,3-e ] -1,2,4-triazolo- [1,5-c] -pyrimidine adenosine a2a receptor antagonists |
-
2002
- 2002-11-26 IL IL16171602A patent/IL161716A0/xx unknown
- 2002-11-26 EP EP02784568A patent/EP1448565B1/en not_active Expired - Lifetime
- 2002-11-26 KR KR1020047007876A patent/KR20050044593A/ko not_active Withdrawn
- 2002-11-26 WO PCT/US2002/037710 patent/WO2003048165A1/en not_active Ceased
- 2002-11-26 AU AU2002346503A patent/AU2002346503A1/en not_active Abandoned
- 2002-11-26 HU HU0402018A patent/HUP0402018A3/hu unknown
- 2002-11-26 MX MXPA04005209A patent/MXPA04005209A/es active IP Right Grant
- 2002-11-26 DE DE60234951T patent/DE60234951D1/de not_active Expired - Lifetime
- 2002-11-26 JP JP2003549355A patent/JP4284182B2/ja not_active Expired - Fee Related
- 2002-11-26 US US10/304,931 patent/US6916811B2/en not_active Expired - Lifetime
- 2002-11-26 AT AT02784568T patent/ATE453647T1/de not_active IP Right Cessation
- 2002-11-26 CN CNA02823782XA patent/CN1692116A/zh active Pending
- 2002-11-26 ES ES02784568T patent/ES2336435T3/es not_active Expired - Lifetime
- 2002-11-26 CA CA002468649A patent/CA2468649C/en not_active Expired - Fee Related
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- 2002-11-27 PE PE2002001143A patent/PE20030665A1/es not_active Application Discontinuation
- 2002-11-27 TW TW091134471A patent/TW200306837A/zh unknown
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2004
- 2004-05-27 ZA ZA200404161A patent/ZA200404161B/en unknown
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| ATE453647T1 (de) | 2010-01-15 |
| IL161716A0 (en) | 2004-09-27 |
| HUP0402018A3 (en) | 2008-06-30 |
| CA2468649C (en) | 2009-03-10 |
| WO2003048165A1 (en) | 2003-06-12 |
| JP2005511699A (ja) | 2005-04-28 |
| MXPA04005209A (es) | 2004-08-19 |
| CN1692116A (zh) | 2005-11-02 |
| JP2008260776A (ja) | 2008-10-30 |
| DE60234951D1 (de) | 2010-02-11 |
| US6916811B2 (en) | 2005-07-12 |
| JP4284182B2 (ja) | 2009-06-24 |
| AU2002346503A1 (en) | 2003-06-17 |
| HK1063780A1 (en) | 2005-01-14 |
| KR20050044593A (ko) | 2005-05-12 |
| HUP0402018A2 (hu) | 2005-02-28 |
| AR037680A1 (es) | 2004-12-01 |
| CA2468649A1 (en) | 2003-06-12 |
| PE20030665A1 (es) | 2003-08-08 |
| EP1448565B1 (en) | 2009-12-30 |
| US20030212059A1 (en) | 2003-11-13 |
| EP1448565A1 (en) | 2004-08-25 |
| ES2336435T3 (es) | 2010-04-13 |
| TW200306837A (en) | 2003-12-01 |
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