KR20050097971A - Ａ₁아데노신 수용체의 부분 및 전 작용제 - Google Patents
Ａ₁아데노신 수용체의 부분 및 전 작용제 Download PDFInfo
- Publication number
- KR20050097971A KR20050097971A KR1020057014259A KR20057014259A KR20050097971A KR 20050097971 A KR20050097971 A KR 20050097971A KR 1020057014259 A KR1020057014259 A KR 1020057014259A KR 20057014259 A KR20057014259 A KR 20057014259A KR 20050097971 A KR20050097971 A KR 20050097971A
- Authority
- KR
- South Korea
- Prior art keywords
- amino
- hydroxymethyl
- oxolan
- purin
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Ceased
Links
- 230000036961 partial effect Effects 0.000 title claims abstract description 12
- 239000000556 agonist Substances 0.000 title description 6
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- 150000001875 compounds Chemical class 0.000 claims abstract description 133
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 20
- 201000010099 disease Diseases 0.000 claims abstract description 17
- 239000003379 purinergic P1 receptor agonist Substances 0.000 claims abstract description 16
- 206010003662 Atrial flutter Diseases 0.000 claims abstract description 3
- 208000010125 myocardial infarction Diseases 0.000 claims abstract description 3
- -1 (3R) -3-({9-[(5S, 2R, 3R) -3-hydroxy-5- (hydroxymethyl) oxolan-2-yl] purin-6-yl} amino) pyrrolidinyl 4 -(Trifluoromethyl) phenyl Chemical group 0.000 claims description 107
- 125000000217 alkyl group Chemical group 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 51
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 29
- 125000000623 heterocyclic group Chemical group 0.000 claims description 28
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 25
- 150000002367 halogens Chemical class 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 24
- 229910052739 hydrogen Inorganic materials 0.000 claims description 24
- 238000000034 method Methods 0.000 claims description 24
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 22
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 18
- 125000004545 purin-9-yl group Chemical group N1=CN=C2N(C=NC2=C1)* 0.000 claims description 15
- 125000003107 substituted aryl group Chemical group 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 125000002252 acyl group Chemical group 0.000 claims description 13
- 150000002431 hydrogen Chemical class 0.000 claims description 11
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 11
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 9
- 241000124008 Mammalia Species 0.000 claims description 7
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 206010003658 Atrial Fibrillation Diseases 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- MFXDELGNEJDVLX-SSRZYRBLSA-N (2r,3r,5s)-2-[6-[[(1r)-2-hydroxycyclohexyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3C(CCCC3)O)=C2N=C1 MFXDELGNEJDVLX-SSRZYRBLSA-N 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- BKTHVDXBRSAQQK-DXEZIKHYSA-N (3-fluorophenyl)-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical class O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=C(F)C=CC=3)=C2N=C1 BKTHVDXBRSAQQK-DXEZIKHYSA-N 0.000 claims description 4
- 206010015037 epilepsy Diseases 0.000 claims description 4
- FZCFGTYSKJLRRR-UHFFFAOYSA-N heptan-1-one Chemical compound CCCCCC[C]=O FZCFGTYSKJLRRR-UHFFFAOYSA-N 0.000 claims description 4
- 206010047302 ventricular tachycardia Diseases 0.000 claims description 4
- SDFGTAJVYBDLPM-VTLCSEFTSA-N (2r,3r,5s)-2-[6-[[(1s,2s)-2-hydroxycyclopentyl]amino]purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@@H]3[C@H](CCC3)O)=C2N=C1 SDFGTAJVYBDLPM-VTLCSEFTSA-N 0.000 claims description 3
- CYHHDZBHMDFNRX-FKEXNYPISA-N (2r,3r,5s)-2-[6-[[(3r)-1-(benzenesulfonyl)pyrrolidin-3-yl]amino]purin-9-yl]-5-(hydroxymethyl)oxolan-3-ol Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)S(=O)(=O)C=3C=CC=CC=3)=C2N=C1 CYHHDZBHMDFNRX-FKEXNYPISA-N 0.000 claims description 3
- UBHMODPMTPUDCA-DXEZIKHYSA-N (4-fluorophenyl)-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical class O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=CC(F)=CC=3)=C2N=C1 UBHMODPMTPUDCA-DXEZIKHYSA-N 0.000 claims description 3
- KFGXJHQSLQFNQM-AZKPJATDSA-N 1-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1NC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)C[C@@H](CO)O1 KFGXJHQSLQFNQM-AZKPJATDSA-N 0.000 claims description 3
- JWILUNHPKQXCHA-MPWIWIEXSA-N 4-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidine-1-carbonyl]benzonitrile Chemical compound O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=CC(=CC=3)C#N)=C2N=C1 JWILUNHPKQXCHA-MPWIWIEXSA-N 0.000 claims description 3
- 206010007559 Cardiac failure congestive Diseases 0.000 claims description 3
- 206010019280 Heart failures Diseases 0.000 claims description 3
- 208000008589 Obesity Diseases 0.000 claims description 3
- DOFPFDWPFNKNSO-PUXBEBEGSA-N [(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]-(4-methoxyphenyl)methanone Chemical compound C1=CC(OC)=CC=C1C(=O)N1C[C@H](NC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H](C[C@@H](CO)O2)O)CC1 DOFPFDWPFNKNSO-PUXBEBEGSA-N 0.000 claims description 3
- VACCDLQQNSXQLB-XZWCOCNFSA-N [(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]-naphthalen-2-ylmethanone Chemical class O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=C4C=CC=CC4=CC=3)=C2N=C1 VACCDLQQNSXQLB-XZWCOCNFSA-N 0.000 claims description 3
- 206010012601 diabetes mellitus Diseases 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 235000020824 obesity Nutrition 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- AFUIROHXZUNVTG-KXUBAAQCSA-N (2-fluorophenyl)-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical class O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C(=CC=CC=3)F)=C2N=C1 AFUIROHXZUNVTG-KXUBAAQCSA-N 0.000 claims description 2
- CZPJWGPCAGWPDF-OIMFZILRSA-N (4-ethylphenyl)-[(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]methanone Chemical compound C1=CC(CC)=CC=C1C(=O)N1C[C@H](NC=2C=3N=CN(C=3N=CN=2)[C@H]2[C@@H](C[C@@H](CO)O2)O)CC1 CZPJWGPCAGWPDF-OIMFZILRSA-N 0.000 claims description 2
- SHSCEZIUPOISRQ-JNIYBQFBSA-N 1-[(3r)-3-[[2-chloro-9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]ethanone Chemical compound C1N(C(=O)C)CC[C@H]1NC1=NC(Cl)=NC2=C1N=CN2[C@H]1[C@H](O)C[C@@H](CO)O1 SHSCEZIUPOISRQ-JNIYBQFBSA-N 0.000 claims description 2
- HIWFRXMELCYHOX-IGMJJTELSA-N 1-[(3r)-3-[[2-chloro-9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]heptan-1-one Chemical compound C1N(C(=O)CCCCCC)CC[C@H]1NC1=NC(Cl)=NC2=C1N=CN2[C@H]1[C@H](O)C[C@@H](CO)O1 HIWFRXMELCYHOX-IGMJJTELSA-N 0.000 claims description 2
- 206010002388 Angina unstable Diseases 0.000 claims description 2
- 208000007718 Stable Angina Diseases 0.000 claims description 2
- 208000007814 Unstable Angina Diseases 0.000 claims description 2
- JHANUSIJHKGOQS-DXEZIKHYSA-N [(3r)-3-[[9-[(2r,3r,5s)-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]amino]pyrrolidin-1-yl]-phenylmethanone Chemical class O1[C@H](CO)C[C@@H](O)[C@@H]1N1C2=NC=NC(N[C@H]3CN(CC3)C(=O)C=3C=CC=CC=3)=C2N=C1 JHANUSIJHKGOQS-DXEZIKHYSA-N 0.000 claims description 2
- 201000004332 intermediate coronary syndrome Diseases 0.000 claims description 2
- 229940122614 Adenosine receptor agonist Drugs 0.000 claims 1
- 208000031226 Hyperlipidaemia Diseases 0.000 claims 1
- 208000006011 Stroke Diseases 0.000 claims 1
- 208000028867 ischemia Diseases 0.000 claims 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 1
- 150000002790 naphthalenes Chemical class 0.000 claims 1
- 125000005475 oxolanyl group Chemical group 0.000 claims 1
- 208000001871 Tachycardia Diseases 0.000 abstract description 2
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- 206010002383 Angina Pectoris Diseases 0.000 abstract 1
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- 125000003118 aryl group Chemical group 0.000 description 43
- 239000004480 active ingredient Substances 0.000 description 29
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 28
- 125000003545 alkoxy group Chemical group 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- 239000004615 ingredient Substances 0.000 description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 23
- 125000004181 carboxyalkyl group Chemical group 0.000 description 23
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 22
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- 125000003342 alkenyl group Chemical group 0.000 description 19
- 150000001412 amines Chemical class 0.000 description 19
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- 125000000392 cycloalkenyl group Chemical group 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 16
- 125000000304 alkynyl group Chemical group 0.000 description 15
- 210000004027 cell Anatomy 0.000 description 15
- 239000003795 chemical substances by application Substances 0.000 description 15
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 15
- 102000009346 Adenosine receptors Human genes 0.000 description 14
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 14
- 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 14
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 14
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 14
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Classifications
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- 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
-
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/06—Antiarrhythmics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cardiology (AREA)
- Diabetes (AREA)
- Heart & Thoracic Surgery (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Vascular Medicine (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Child & Adolescent Psychology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pain & Pain Management (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44452603P | 2003-02-03 | 2003-02-03 | |
| US60/444,526 | 2003-02-03 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR20050097971A true KR20050097971A (ko) | 2005-10-10 |
Family
ID=32850877
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1020057014259A Ceased KR20050097971A (ko) | 2003-02-03 | 2004-02-02 | Ａ₁아데노신 수용체의 부분 및 전 작용제 |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US7163928B2 (https=) |
| EP (1) | EP1590359A2 (https=) |
| JP (1) | JP2006516641A (https=) |
| KR (1) | KR20050097971A (https=) |
| AU (1) | AU2004209986C1 (https=) |
| CA (1) | CA2515068A1 (https=) |
| NZ (1) | NZ541651A (https=) |
| WO (1) | WO2004069185A2 (https=) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR050630A1 (es) * | 2004-09-09 | 2006-11-08 | Solvay Pharm Bv | DERIVADOS DE 6- TRIFLUOROMETIL PURINA 2- SUSTITUIDA CON ACTIVIDAD ANTAGONISTA DE ADENOSINA-A3. PROCESOS DE OBTENCIoN Y COMPOSICIONES FARMACÉUTICAS. |
| US7338964B2 (en) | 2004-09-09 | 2008-03-04 | Solvay Pharmaceuticals, B.V. | 2-substituted-1-deaza purine derivatives with adenosine receptor modulating activity |
| US7371737B2 (en) | 2004-09-09 | 2008-05-13 | Solvay Pharmaceuticals, B.V. | 2-substituted-6-trifluoromethyl purine derivatives with adenosine-A3 antagonistic activity |
| WO2007047401A2 (en) * | 2005-10-13 | 2007-04-26 | Cv Therapeutics, Inc. | A1 adenosine receptor agonists |
| EA015683B1 (ru) * | 2005-11-30 | 2011-10-31 | Инотек Фармасьютикалз Корпорейшн | Производные пурина и способы их применения |
| CN101903372B (zh) | 2007-12-21 | 2014-06-18 | 弗·哈夫曼-拉罗切有限公司 | 作为食欲肽受体拮抗剂的杂芳基衍生物 |
| ES2375919T3 (es) | 2008-01-11 | 2012-03-07 | F. Hoffmann-La Roche Ag | Moduladores de beta-amiloide. |
| MX2010008700A (es) | 2008-02-22 | 2010-08-30 | Hoffmann La Roche | Moduladores de beta-amiloide. |
| ES2429517T3 (es) | 2008-10-09 | 2013-11-15 | F. Hoffmann-La Roche Ag | Moduladores para la beta amiloide |
| CN102209537A (zh) | 2008-11-10 | 2011-10-05 | 弗·哈夫曼-拉罗切有限公司 | 杂环γ分泌酶调节剂 |
| EA201270102A1 (ru) | 2009-06-30 | 2012-08-30 | Форест Лэборетериз Холдингз Лимитед | Соединения алкокси-карбонил-амино-алкинил-аденозина и их производные в качестве агонистов ar |
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| US3346560A (en) * | 1965-01-29 | 1967-10-10 | Merck & Co Inc | Purine 3-deoxynucleosides |
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| JPS55160796A (en) * | 1979-06-01 | 1980-12-13 | Yamasa Shoyu Co Ltd | Preparation of n6-alkyl cordycepin |
| AU575438B2 (en) | 1984-10-26 | 1988-07-28 | Warner-Lambert Company | N6 - substituted deoxyribose analogues of adenosines |
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| WO1998001459A1 (en) | 1996-07-05 | 1998-01-15 | Novo Nordisk A/S | Novel n-alkoxyadenine derivatives acting as cytokine inhibitors |
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| AU750322B2 (en) * | 1997-05-09 | 2002-07-18 | Trustees Of The University Of Pennsylvania, The | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
| WO1999020284A1 (en) * | 1997-10-23 | 1999-04-29 | Trustees Of The University Of Pennsylvania | Methods for reducing ischemic injury of the heart via the sequential administration of monophosphoryl lipid a and adenosine receptor agents |
| GB9723589D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723566D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| GB9723590D0 (en) | 1997-11-08 | 1998-01-07 | Glaxo Group Ltd | Chemical compounds |
| EP1069903A1 (en) * | 1998-03-11 | 2001-01-24 | Lipitek International, Inc. | Novel nucleoside analogs and uses in treating disease |
| GB9813554D0 (en) | 1998-06-23 | 1998-08-19 | Glaxo Group Ltd | Chemical compounds |
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| US6946449B2 (en) | 2001-07-13 | 2005-09-20 | Cv Therapeutics, Inc. | Partial and full agonists of A1 adenosine receptors |
| CA2508479A1 (en) * | 2002-12-03 | 2004-06-17 | Baylor University | Compounds resistant to metabolic deactivation and methods of use |
-
2004
- 2004-02-02 KR KR1020057014259A patent/KR20050097971A/ko not_active Ceased
- 2004-02-02 WO PCT/US2004/002868 patent/WO2004069185A2/en not_active Ceased
- 2004-02-02 JP JP2006503239A patent/JP2006516641A/ja active Pending
- 2004-02-02 EP EP04707373A patent/EP1590359A2/en not_active Withdrawn
- 2004-02-02 US US10/770,542 patent/US7163928B2/en not_active Expired - Lifetime
- 2004-02-02 AU AU2004209986A patent/AU2004209986C1/en not_active Ceased
- 2004-02-02 CA CA002515068A patent/CA2515068A1/en not_active Abandoned
- 2004-02-02 NZ NZ541651A patent/NZ541651A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| EP1590359A2 (en) | 2005-11-02 |
| AU2004209986A1 (en) | 2004-08-19 |
| AU2004209986B2 (en) | 2009-01-22 |
| WO2004069185A3 (en) | 2004-09-23 |
| AU2004209986C1 (en) | 2009-08-13 |
| US20040198691A1 (en) | 2004-10-07 |
| US7163928B2 (en) | 2007-01-16 |
| WO2004069185A2 (en) | 2004-08-19 |
| JP2006516641A (ja) | 2006-07-06 |
| CA2515068A1 (en) | 2004-08-19 |
| NZ541651A (en) | 2009-01-31 |
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