CA2384111C - Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist - Google Patents
Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist Download PDFInfo
- Publication number
- CA2384111C CA2384111C CA002384111A CA2384111A CA2384111C CA 2384111 C CA2384111 C CA 2384111C CA 002384111 A CA002384111 A CA 002384111A CA 2384111 A CA2384111 A CA 2384111A CA 2384111 C CA2384111 C CA 2384111C
- Authority
- CA
- Canada
- Prior art keywords
- group
- adenosine
- alkyl
- active ingredient
- meca
- 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.)
- Expired - Lifetime
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 29
- 239000003379 purinergic P1 receptor agonist Substances 0.000 title abstract description 9
- 239000000296 purinergic P1 receptor antagonist Substances 0.000 title description 9
- 229940121359 adenosine receptor antagonist Drugs 0.000 title description 6
- 229940122614 Adenosine receptor agonist Drugs 0.000 title description 2
- 230000000694 effects Effects 0.000 claims abstract description 66
- 238000011282 treatment Methods 0.000 claims abstract description 33
- 239000003814 drug Substances 0.000 claims abstract description 32
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- 230000002159 abnormal effect Effects 0.000 claims abstract description 21
- 231100000331 toxic Toxicity 0.000 claims abstract description 19
- 230000002588 toxic effect Effects 0.000 claims abstract description 19
- 239000004480 active ingredient Substances 0.000 claims description 82
- 210000004027 cell Anatomy 0.000 claims description 58
- 229960005305 adenosine Drugs 0.000 claims description 53
- IPSYPUKKXMNCNQ-PFHKOEEOSA-N (2s,3s,4r,5r)-5-[2-chloro-6-[(3-iodophenyl)methylamino]purin-9-yl]-3,4-dihydroxy-n-methyloxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NC)O[C@H]1N1C2=NC(Cl)=NC(NCC=3C=C(I)C=CC=3)=C2N=C1 IPSYPUKKXMNCNQ-PFHKOEEOSA-N 0.000 claims description 52
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 52
- 125000000217 alkyl group Chemical group 0.000 claims description 49
- 230000035755 proliferation Effects 0.000 claims description 48
- HUJXGQILHAUCCV-MOROJQBDSA-N 3-iodobenzyl-5'-N-methylcarboxamidoadenosine Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NC)O[C@H]1N1C2=NC=NC(NCC=3C=C(I)C=CC=3)=C2N=C1 HUJXGQILHAUCCV-MOROJQBDSA-N 0.000 claims description 43
- 229910052739 hydrogen Inorganic materials 0.000 claims description 42
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- -1 nitro, hydroxyl Chemical group 0.000 claims description 25
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
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- MWEQTWJABOLLOS-UHFFFAOYSA-L disodium;[[[5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-oxidophosphoryl] hydrogen phosphate;trihydrate Chemical compound O.O.O.[Na+].[Na+].C1=NC=2C(N)=NC=NC=2N1C1OC(COP(O)(=O)OP([O-])(=O)OP(O)([O-])=O)C(O)C1O MWEQTWJABOLLOS-UHFFFAOYSA-L 0.000 claims description 4
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 3
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- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7052—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides
- A61K31/706—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom
- A61K31/7064—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines
- A61K31/7076—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid
- A61K31/708—Compounds having saccharide radicals and heterocyclic rings having nitrogen as a ring hetero atom, e.g. nucleosides, nucleotides containing six-membered rings with nitrogen as a ring hetero atom containing condensed or non-condensed pyrimidines containing purines, e.g. adenosine, adenylic acid having oxo groups directly attached to the purine ring system, e.g. guanosine, guanylic acid
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- A61P35/02—Antineoplastic agents specific for leukemia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P39/00—General protective or antinoxious agents
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- 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
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- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Molecular Biology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Toxicology (AREA)
- Immunology (AREA)
- Oncology (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
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| IL13186499A IL131864A0 (en) | 1999-09-10 | 1999-09-10 | Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist |
| IL131864 | 1999-09-10 | ||
| IL133680 | 1999-12-23 | ||
| IL13368099A IL133680A0 (en) | 1999-09-10 | 1999-12-23 | Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist |
| PCT/IL2000/000550 WO2001019360A2 (en) | 1999-09-10 | 2000-09-08 | Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist |
Publications (2)
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| CA2384111A1 CA2384111A1 (en) | 2001-03-22 |
| CA2384111C true CA2384111C (en) | 2008-05-27 |
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| CA002384111A Expired - Lifetime CA2384111C (en) | 1999-09-10 | 2000-09-08 | Pharmaceutical compositions comprising an adenosine receptor agonist or antagonist |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| IL121272A (en) * | 1997-07-10 | 2000-06-01 | Can Fite Technologies Ltd | Pharmaceutical compositions comprising adenosine and their use for treating or preventing leukopenia |
| CN1234358C (zh) | 2000-06-21 | 2006-01-04 | 弗·哈夫曼-拉罗切有限公司 | 苯并噻唑衍生物 |
| EP1365776B1 (en) * | 2001-01-16 | 2005-04-13 | Can-Fite Biopharma Ltd. | Use of an adenosine a3 receptor agonist for inhibition of viral replication |
| US20020115635A1 (en) * | 2001-02-21 | 2002-08-22 | Pnina Fishman | Modulation of GSK-3beta activity and its different uses |
| US20040204481A1 (en) * | 2001-04-12 | 2004-10-14 | Pnina Fishman | Activation of natural killer cells by adenosine A3 receptor agonists |
| US7049303B2 (en) * | 2001-11-07 | 2006-05-23 | Medical Research Council | Inhibition of viruses |
| US7414036B2 (en) | 2002-01-25 | 2008-08-19 | Muscagen Limited | Compounds useful as A3 adenosine receptor agonists |
| ATE371191T1 (de) * | 2002-10-22 | 2007-09-15 | Can Fite Biopharma Ltd | Die verwendung von dem a3 adenosin rezeptor als marker eines krankheitszustandes |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
| EP1753760B1 (en) | 2004-05-24 | 2008-01-02 | F.Hoffmann-La Roche Ag | 4-hydroxy-4-methyl-piperidine-1-carboxylic acid (4-methoxy-7-morpholin-4-yl-benzothiazol-2-yl)-amide |
| DE602005020286D1 (de) | 2004-05-26 | 2010-05-12 | Inotek Pharmaceuticals Corp | Purinderivate als adenosin a 1 rezeptoragonisten und anwendungsverfahren dafür |
| US7825102B2 (en) | 2004-07-28 | 2010-11-02 | Can-Fite Biopharma Ltd. | Treatment of dry eye conditions |
| BRPI0515506A (pt) | 2004-09-20 | 2008-07-29 | Inotek Pharmaceuticals Corp | derivados de purina e métodos de uso dos mesmos |
| US20060159627A1 (en) * | 2004-10-15 | 2006-07-20 | Dewan Zeng | Method of preventing and treating airway remodeling and pulmonary inflammation using A2B adenosine receptor antagonists |
| CN101056857B (zh) | 2004-11-05 | 2010-12-01 | 弗·哈夫曼-拉罗切有限公司 | 异烟酸衍生物的制备方法 |
| MX2007005525A (es) * | 2004-11-08 | 2007-07-05 | Can Fite Biopharma Ltd | Tratamiento terapeutico de resorcion ose acelerada. |
| CA2586420A1 (en) * | 2004-11-22 | 2007-04-12 | King Pharmaceuticals Research & Development, Inc. | Enhancing treatment of cancer and hif-1 mediated disoders with adenosine a3 receptor antagonists |
| KR100973609B1 (ko) | 2005-03-23 | 2010-08-03 | 에프. 호프만-라 로슈 아게 | ｍＧｌｕＲ2 길항제로서 아세틸렌일-피라졸로-피리미딘유도체 |
| CA2623721C (en) | 2005-09-27 | 2014-05-13 | F. Hoffmann-La Roche Ag | Oxadiazolyl pyrazolo-pyrimidines as mglur2 antagonists |
| AU2006320578B2 (en) | 2005-11-30 | 2013-01-31 | Inotek Pharmaceuticals Corporation | Purine derivatives and methods of use thereof |
| KR101037095B1 (ko) * | 2006-01-27 | 2011-05-26 | 캔-파이트 바이오파마 리미티드 | 건성안 장애의 치료를 위한 아데노신 ａ3 수용체 아고니스트 |
| WO2008023362A2 (en) * | 2006-08-21 | 2008-02-28 | Can-Fite Biopharma Ltd. | Use of a combination of methotrexate and an a3ar agonist for the treatment of cancer |
| WO2008045330A2 (en) * | 2006-10-06 | 2008-04-17 | The Trustees Of The University Of Pennsylvania | Effective delivery of cross-species a3 adenosine-receptor antagonists to reduce intraocular pressure |
| GB0625100D0 (en) * | 2006-12-15 | 2007-01-24 | Univ Murcia | Epigallocatechin-3-gallate compositions for cancer therapy and chemoprotection |
| US20090088403A1 (en) * | 2007-05-07 | 2009-04-02 | Randy Blakely | A3 adenosine receptors as targets for the modulation of central serotonergic signaling |
| CA2694983A1 (en) * | 2007-07-17 | 2009-01-22 | Combinatorx, Incorporated | Treatments of b-cell proliferative disorders |
| TW200914048A (en) * | 2007-07-17 | 2009-04-01 | Combinatorx Inc | Combinations for the treatment of B-cell proliferative disorders |
| WO2009151569A2 (en) * | 2008-06-09 | 2009-12-17 | Combinatorx, Incorporated | Beta adrenergic receptor agonists for the treatment of b-cell proliferative disorders |
| WO2010027935A1 (en) * | 2008-09-08 | 2010-03-11 | Merck Sharp & Dohme Corp. | Ahcy hydrolase inhibitors for treatment of hyper homocysteinemia |
| AU2010250759B2 (en) | 2009-05-17 | 2013-03-14 | Can-Fite Biopharma Ltd. | A3 adenosine receptor agonists for the reduction of intraocular pressure |
| EP2456419B1 (en) | 2009-07-21 | 2016-11-23 | Oradin Pharmaceutical Ltd. | A3 adenosine receptor ligands for modulation of pigmentation |
| WO2011074903A2 (ko) * | 2009-12-17 | 2011-06-23 | 이화여자대학교 산학협력단 | Ａ3 아데노신 수용체 효능제를 포함하는 약제학적 조성물 |
| EA025415B1 (ru) | 2010-01-11 | 2016-12-30 | Инотек Фармасьютикалз Корпорейшн | Комбинация, набор и способ снижения внутриглазного давления |
| KR20130072189A (ko) | 2010-03-03 | 2013-07-01 | 더 가번먼트 오브 더 유나이티드 스테이츠 오브 아메리카, 레프리젠티드 바이 더 세크러터리, 디파트먼트 오브 헬쓰 앤드 휴먼 서비스즈 | 포도막염의 치료를 위한 ａ3ａｒ 작동약 |
| EP2569325A4 (en) | 2010-03-26 | 2013-10-09 | Inotek Pharmaceuticals Corp | METHOD FOR REDUCING INNER EYE PRESSURE IN HUMANS USING N6-CYCLOPENTYLADENOSINE (CPA), CPA DERIVATIVES OR PRODRUGS THEREOF |
| US20130109645A1 (en) | 2010-03-31 | 2013-05-02 | The united States of America,as represented by Secretary,Dept.,of Health and Human Services | Adenosine receptor agonists for the treatment and prevention of vascular or joint capsule calcification disorders |
| AU2012358803C1 (en) | 2011-12-22 | 2019-12-19 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| HK1202053A1 (en) * | 2012-01-23 | 2015-09-18 | Can-Fite Biopharma Ltd. | Treatment of liver conditions |
| 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 |
| US9441007B2 (en) | 2012-03-21 | 2016-09-13 | Alios Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| USRE48171E1 (en) | 2012-03-21 | 2020-08-25 | Janssen Biopharma, Inc. | Substituted nucleosides, nucleotides and analogs thereof |
| US8822460B2 (en) | 2012-04-06 | 2014-09-02 | Janssen Pharmaceutica Nv | Fused cyclopentyl antagonists of CCR2 |
| ES2627010T3 (es) | 2012-07-19 | 2017-07-26 | Janssen Pharmaceutica, N.V. | Antagonistas de octahidro-ciclopentapirrolilo de CCR2 |
| BR112015002697A8 (pt) | 2012-08-09 | 2018-01-16 | Can Fite Biopharma Ltd | uso de ligante de receptor de adenosina a3 (a3ar), ligante de a3ar, e, composição farmacêutica para tratar disfunção sexual em um indivíduo |
| CA2903114A1 (en) | 2013-03-15 | 2014-09-25 | Inotek Pharmaceuticals Corporation | Ophthalmic formulations |
| IL242723B (en) | 2015-11-23 | 2019-12-31 | Can Fite Biopharma Ltd | A3 adenosine receptor ligand for the treatment of ectopic fat accumulation |
| KR102445887B1 (ko) | 2016-04-21 | 2022-09-21 | 아스트로사이트 파마슈티컬스, 인코포레이티드 | 신경계 및 심혈관계 병태 치료를 위한 화합물 및 방법 |
| IL254535A0 (en) * | 2017-09-17 | 2017-11-30 | Can Fite Biopharma Ltd | Adenosine a3 receptor ligand for use in the management of cytokine release syndrome |
| EP3749322A4 (en) | 2018-02-09 | 2021-11-17 | Astrocyte Pharmaceuticals, Inc. | COMPOUNDS AND METHODS FOR THE TREATMENT OF ADDICTION AND RELATED DISORDERS |
| EP3856741A4 (en) | 2018-09-26 | 2022-06-22 | Astrocyte Pharmaceuticals, Inc. | POLYMORPHOUS COMPOUNDS AND USES THEREOF |
| IL264112A (en) | 2019-01-06 | 2020-07-30 | Fishman Pnina | Adenosine a3 receptor ligand for use in lowering adipocyte levels |
| IT202300014340A1 (it) | 2023-07-10 | 2025-01-10 | Consiglio Nazionale Ricerche | Trattamento di malattie associate alla disfunzione del gene ocrl. |
Family Cites Families (16)
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| US5443836A (en) * | 1993-03-15 | 1995-08-22 | Gensia, Inc. | Methods for protecting tissues and organs from ischemic damage |
| DE69428536T2 (de) * | 1993-07-13 | 2002-06-06 | The United States Of America, As Represented By The Secretary Of The Department Of Health And Human Services | A3 -adenosin -rezeptor agonisten |
| US5688774A (en) * | 1993-07-13 | 1997-11-18 | The United States Of America As Represented By The Department Of Health And Human Services | A3 adenosine receptor agonists |
| GB2289218A (en) * | 1994-05-06 | 1995-11-15 | Merck & Co Inc | Inhibition of TNFalpha production with agonists of the A2b subtype of the adenosine receptor |
| RU2071770C1 (ru) * | 1994-12-14 | 1997-01-20 | Владислав Алексеевич Шматко | Способ лечения рака шейки матки и яичников |
| RU2071771C1 (ru) * | 1995-01-11 | 1997-01-20 | Владислав Алексеевич Шматко | Способ лечения рака молочной железы |
| WO1998050047A1 (en) * | 1997-05-09 | 1998-11-12 | Trustees Of The University Of Pennsylvania | Methods and compositions for reducing ischemic injury of the heart by administering adenosine receptor agonists and antagonists |
| IL121272A (en) * | 1997-07-10 | 2000-06-01 | Can Fite Technologies Ltd | Pharmaceutical compositions comprising adenosine and their use for treating or preventing leukopenia |
| US6048865A (en) * | 1997-07-29 | 2000-04-11 | Medco Research, Inc. | N6 -substituted-adenosine-5'-uronamides as adenosine receptor modulator |
| CA2296485A1 (en) * | 1997-07-29 | 1999-02-11 | Medco Research, Inc. | N6-substituted-adenosine-5'-uronamides as adenosine receptor modulators |
| 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 |
| EP1011608A4 (en) * | 1998-06-08 | 2002-05-15 | Epigenesis Pharmaceuticals Inc | COMPOSITION AND METHOD FOR THE PREVENTION AND TREATMENT OF HEART AND NEUTRAL FAILURE OR DAMAGE RELATED TO ISCHEMIA, ENDOTOXIN RELEASE, ARDS OR CALLED BY THE ADDITION OF SPECIFIC MEDICINES |
| US6448253B1 (en) | 1998-09-16 | 2002-09-10 | King Pharmaceuticals Research And Development, Inc. | Adenosine A3 receptor modulators |
| IL127947A0 (en) | 1999-01-07 | 1999-11-30 | Can Fite Technologies Ltd | Pharmaceutical use of adenosine agonists |
| BR0007864A (pt) * | 1999-02-01 | 2001-11-06 | Univ Virginia | Composto, e, uso de um composto |
| IL131096A (en) | 1999-07-26 | 2004-09-27 | Can Fite Technologies Ltd | Method for preparing a composition derived from muscle tissue |
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1999
- 1999-12-23 IL IL13368099A patent/IL133680A0/xx not_active IP Right Cessation
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2000
- 2000-09-08 BR BR0013905-0A patent/BR0013905A/pt not_active Application Discontinuation
- 2000-09-08 HU HU0203870A patent/HU226913B1/hu unknown
- 2000-09-08 WO PCT/IL2000/000550 patent/WO2001019360A2/en not_active Ceased
- 2000-09-08 EP EP00956773A patent/EP1261322B1/en not_active Expired - Lifetime
- 2000-09-08 JP JP2001522994A patent/JP4980530B2/ja not_active Expired - Lifetime
- 2000-09-08 KR KR1020027003164A patent/KR100584797B1/ko not_active Expired - Lifetime
- 2000-09-08 KR KR1020067006473A patent/KR100674529B1/ko not_active Expired - Lifetime
- 2000-09-08 MX MXPA02002546A patent/MXPA02002546A/es active IP Right Grant
- 2000-09-08 RU RU2002109228/15A patent/RU2239455C2/ru active
- 2000-09-08 US US09/700,751 patent/US7064112B1/en not_active Expired - Lifetime
- 2000-09-08 CA CA002384111A patent/CA2384111C/en not_active Expired - Lifetime
- 2000-09-08 HK HK03105018.4A patent/HK1052653B/zh not_active IP Right Cessation
- 2000-09-08 DK DK00956773T patent/DK1261322T3/da active
- 2000-09-08 AU AU68634/00A patent/AU782826B2/en not_active Expired
- 2000-09-08 ES ES00956773T patent/ES2296637T3/es not_active Expired - Lifetime
- 2000-09-08 PL PL356469A patent/PL199852B1/pl unknown
- 2000-09-08 DE DE60037277T patent/DE60037277T2/de not_active Expired - Lifetime
- 2000-09-08 PT PT00956773T patent/PT1261322E/pt unknown
- 2000-09-08 CN CNB008148007A patent/CN100358512C/zh not_active Expired - Lifetime
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2005
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2007
- 2007-05-14 JP JP2007128137A patent/JP2007204496A/ja active Pending
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