RU2239455C2 - Фармацевтические композиции, содержащие агонист или антагонист аденозинового рецептора - Google Patents
Фармацевтические композиции, содержащие агонист или антагонист аденозинового рецептора Download PDFInfo
- Publication number
- RU2239455C2 RU2239455C2 RU2002109228/15A RU2002109228A RU2239455C2 RU 2239455 C2 RU2239455 C2 RU 2239455C2 RU 2002109228/15 A RU2002109228/15 A RU 2002109228/15A RU 2002109228 A RU2002109228 A RU 2002109228A RU 2239455 C2 RU2239455 C2 RU 2239455C2
- Authority
- RU
- Russia
- Prior art keywords
- group
- adenosine
- active ingredient
- iodobenzyl
- alkyl
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 28
- 239000000556 agonist Substances 0.000 title abstract description 14
- 108050000203 Adenosine receptors Proteins 0.000 title abstract description 10
- 102000009346 Adenosine receptors Human genes 0.000 title abstract description 10
- 239000005557 antagonist Substances 0.000 title description 9
- 230000000694 effects Effects 0.000 claims abstract description 65
- 230000035755 proliferation Effects 0.000 claims abstract description 54
- 108010017080 Granulocyte Colony-Stimulating Factor Proteins 0.000 claims abstract description 44
- 102000004269 Granulocyte Colony-Stimulating Factor Human genes 0.000 claims abstract description 44
- 239000003814 drug Substances 0.000 claims abstract description 37
- 229940079593 drug Drugs 0.000 claims abstract description 34
- 201000002364 leukopenia Diseases 0.000 claims abstract description 32
- 231100001022 leukopenia Toxicity 0.000 claims abstract description 32
- 238000011282 treatment Methods 0.000 claims abstract description 31
- 239000000203 mixture Substances 0.000 claims abstract description 20
- 231100000331 toxic Toxicity 0.000 claims abstract description 18
- 230000002588 toxic effect Effects 0.000 claims abstract description 18
- 230000028327 secretion Effects 0.000 claims abstract description 13
- 230000012010 growth Effects 0.000 claims abstract description 8
- 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 claims description 102
- 239000004480 active ingredient Substances 0.000 claims description 93
- 210000004027 cell Anatomy 0.000 claims description 61
- 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
- 229960005305 adenosine Drugs 0.000 claims description 51
- 239000002126 C01EB10 - Adenosine Substances 0.000 claims description 49
- 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 47
- -1 nitro, hydroxyl Chemical group 0.000 claims description 42
- 210000002798 bone marrow cell Anatomy 0.000 claims description 41
- 210000000265 leukocyte Anatomy 0.000 claims description 39
- 229910052739 hydrogen Inorganic materials 0.000 claims description 33
- 239000001257 hydrogen Substances 0.000 claims description 33
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 206010028980 Neoplasm Diseases 0.000 claims description 30
- 125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 29
- 239000002246 antineoplastic agent Substances 0.000 claims description 28
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- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000001875 compounds Chemical class 0.000 claims description 22
- 150000002367 halogens Chemical class 0.000 claims description 22
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 22
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 20
- 238000004519 manufacturing process Methods 0.000 claims description 20
- 150000002431 hydrogen Chemical class 0.000 claims description 18
- 230000002401 inhibitory effect Effects 0.000 claims description 18
- 102000005962 receptors Human genes 0.000 claims description 17
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- 125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 14
- 230000002265 prevention Effects 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
- 230000010261 cell growth Effects 0.000 claims description 13
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 11
- 230000002159 abnormal effect Effects 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
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- 150000003833 nucleoside derivatives Chemical group 0.000 claims description 9
- 229910052760 oxygen Inorganic materials 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000001188 haloalkyl group Chemical group 0.000 claims description 8
- 230000004069 differentiation Effects 0.000 claims description 7
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- 239000002593 adenosine A3 receptor agonist Substances 0.000 claims description 6
- 150000003931 anilides Chemical group 0.000 claims description 6
- 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 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 5
- 230000009471 action Effects 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- 229940122216 Adenosine A3 receptor agonist Drugs 0.000 claims description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 claims description 4
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 4
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000304 alkynyl group Chemical group 0.000 claims description 3
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- 125000000101 thioether group Chemical group 0.000 claims description 3
- XTPOZVLRZZIEBW-SCFUHWHPSA-N (2r,3r,4s,5r)-2-[6-[2-(4-aminophenyl)ethylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol Chemical compound C1=CC(N)=CC=C1CCNC1=NC=NC2=C1N=CN2[C@H]1[C@H](O)[C@H](O)[C@@H](CO)O1 XTPOZVLRZZIEBW-SCFUHWHPSA-N 0.000 claims description 2
- 125000006832 (C1-C10) alkylene group Chemical group 0.000 claims description 2
- 125000003853 4-amino-3-iodobenzyl group Chemical group [H]N([H])C1=C(I)C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
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- 208000008784 apnea Diseases 0.000 claims description 2
- 125000002648 azanetriyl group Chemical group *N(*)* 0.000 claims description 2
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 claims description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005030 pyridylthio group Chemical group N1=C(C=CC=C1)S* 0.000 claims description 2
- 125000005309 thioalkoxy group Chemical group 0.000 claims description 2
- FDEACFAXFCKCHZ-MOROJQBDSA-N (2s,3s,4r,5r)-5-(6-amino-2-hex-1-ynylpurin-9-yl)-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound C12=NC(C#CCCCC)=NC(N)=C2N=CN1[C@@H]1O[C@H](C(=O)NCC)[C@@H](O)[C@H]1O FDEACFAXFCKCHZ-MOROJQBDSA-N 0.000 claims 15
- 238000009472 formulation Methods 0.000 claims 5
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 4
- 229930024421 Adenine Natural products 0.000 claims 2
- GFFGJBXGBJISGV-UHFFFAOYSA-N Adenine Chemical compound NC1=NC=NC2=C1N=CN2 GFFGJBXGBJISGV-UHFFFAOYSA-N 0.000 claims 2
- 229960000643 adenine Drugs 0.000 claims 2
- WHYVKEGFJPLEJZ-UHFFFAOYSA-N n-[(3-iodophenyl)methyl]-7h-purin-6-amine Chemical compound IC1=CC=CC(CNC=2C=3NC=NC=3N=CN=2)=C1 WHYVKEGFJPLEJZ-UHFFFAOYSA-N 0.000 claims 2
- UMMMZHIKPLYIHG-LPWJYYESSA-N (1s,2r,3s,4r)-4-(6-amino-2-chloropurin-9-yl)cyclopentane-1,2,3-triol Chemical compound C1=NC=2C(N)=NC(Cl)=NC=2N1[C@@H]1C[C@H](O)[C@@H](O)[C@H]1O UMMMZHIKPLYIHG-LPWJYYESSA-N 0.000 claims 1
- OZCCPYHYSIPRDM-PAPYEOQZSA-N (1s,2r,3s,4r)-4-[6-amino-2-(2-phenylethylamino)purin-9-yl]cyclopentane-1,2,3-triol Chemical compound N=1C=2N([C@H]3[C@@H]([C@H](O)[C@@H](O)C3)O)C=NC=2C(N)=NC=1NCCC1=CC=CC=C1 OZCCPYHYSIPRDM-PAPYEOQZSA-N 0.000 claims 1
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims 1
- 125000006681 (C2-C10) alkylene group Chemical group 0.000 claims 1
- NFHVNDANLVCJHE-UHFFFAOYSA-N 2-chloro-n-[(3-iodophenyl)methyl]-9-(oxolan-2-yl)purin-6-amine Chemical compound C=12N=CN(C3OCCC3)C2=NC(Cl)=NC=1NCC1=CC=CC(I)=C1 NFHVNDANLVCJHE-UHFFFAOYSA-N 0.000 claims 1
- ATOXAERIKXFYQV-UHFFFAOYSA-N 2-chloro-n-[(3-iodophenyl)methyl]-9-methylpurin-6-amine Chemical compound N1=C(Cl)N=C2N(C)C=NC2=C1NCC1=CC=CC(I)=C1 ATOXAERIKXFYQV-UHFFFAOYSA-N 0.000 claims 1
- OJUZWXZBQQALOH-UHFFFAOYSA-N 2-n-hexyl-6-n-[(3-iodophenyl)methyl]-9-methylpurine-2,6-diamine Chemical compound C=12N=CN(C)C2=NC(NCCCCCC)=NC=1NCC1=CC=CC(I)=C1 OJUZWXZBQQALOH-UHFFFAOYSA-N 0.000 claims 1
- APXSDGLADFOEDD-UHFFFAOYSA-N 4-[6-[(3-iodophenyl)methylamino]purin-9-yl]butanenitrile Chemical compound IC1=CC=CC(CNC=2C=3N=CN(CCCC#N)C=3N=CN=2)=C1 APXSDGLADFOEDD-UHFFFAOYSA-N 0.000 claims 1
- XBNTWQABLLKTFL-UHFFFAOYSA-N 6-n-[(3-iodophenyl)methyl]-2-n,2-n,9-trimethylpurine-2,6-diamine Chemical compound C=12N=CN(C)C2=NC(N(C)C)=NC=1NCC1=CC=CC(I)=C1 XBNTWQABLLKTFL-UHFFFAOYSA-N 0.000 claims 1
- IKLSILSIWVEUSQ-UHFFFAOYSA-N 6-n-[(3-iodophenyl)methyl]-2-n,9-dimethylpurine-2,6-diamine Chemical compound C=12N=CN(C)C2=NC(NC)=NC=1NCC1=CC=CC(I)=C1 IKLSILSIWVEUSQ-UHFFFAOYSA-N 0.000 claims 1
- AZPDSYNWGWXMJJ-UHFFFAOYSA-N 6-n-[(3-iodophenyl)methyl]-9-methyl-2-n-propylpurine-2,6-diamine Chemical compound C=12N=CN(C)C2=NC(NCCC)=NC=1NCC1=CC=CC(I)=C1 AZPDSYNWGWXMJJ-UHFFFAOYSA-N 0.000 claims 1
- CRCODYWJYJOVSH-UHFFFAOYSA-N 6-n-[(3-iodophenyl)methyl]-9-methylpurine-2,6-diamine Chemical compound N1=C(N)N=C2N(C)C=NC2=C1NCC1=CC=CC(I)=C1 CRCODYWJYJOVSH-UHFFFAOYSA-N 0.000 claims 1
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- ISRXYCXDEAVHOY-UHFFFAOYSA-N n-[(3-iodophenyl)methyl]-2-methoxy-9-methylpurin-6-amine Chemical compound C=12N=CN(C)C2=NC(OC)=NC=1NCC1=CC=CC(I)=C1 ISRXYCXDEAVHOY-UHFFFAOYSA-N 0.000 claims 1
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| RU2391103C2 (ru) * | 2004-10-15 | 2010-06-10 | Си Ви Терапьютикс, Инк. | Способ предупреждения и лечения ремоделирования дыхательных путей и воспаления легких с применением антагонистов аденозиновых рецепторов a2b |
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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 |
| RU2251419C2 (ru) | 2000-06-21 | 2005-05-10 | Ф. Хоффманн-Ля Рош Аг | Производные бензотиазола |
| CA2434906C (en) | 2001-01-16 | 2008-08-19 | 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 |
| US20040137477A1 (en) * | 2002-10-22 | 2004-07-15 | Can-Fite Biopharma, Ltd. | A3AR as a marker for a diseased state |
| US7087761B2 (en) | 2003-01-07 | 2006-08-08 | Hoffmann-La Roche Inc. | Cyclization process for substituted benzothiazole derivatives |
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| ME01072B (me) | 2004-05-26 | 2012-10-20 | Inotek Pharmaceuticals Corp | Derivati purina kao agonisti receptora adenozina a1 i postupci za njihovu upotrebu |
| US7825102B2 (en) | 2004-07-28 | 2010-11-02 | Can-Fite Biopharma Ltd. | Treatment of dry eye conditions |
| CA2581132A1 (en) | 2004-09-20 | 2006-03-30 | Inotek Pharmaceuticals Corporation | Purine 5'-carboxamide derivatives and their use as adenosine receptor agonists |
| EP1812392B1 (en) | 2004-11-05 | 2008-07-09 | F.Hoffmann-La Roche Ag | Process for preparation of isonicotinic acid derivatives |
| BRPI0517639A (pt) * | 2004-11-08 | 2008-10-14 | Can Fite Biopharma Ltd | método para o tratamento de ressorção óssea acelerada, composição farmacêutica, e, uso de um agonista de a3ar |
| 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 |
| PT1863818E (pt) | 2005-03-23 | 2010-04-09 | Hoffmann La Roche | Derivados de acetilenil-pirazolo-pirimidina como antagonistas de mglur2 |
| ATE463495T1 (de) | 2005-09-27 | 2010-04-15 | Hoffmann La Roche | Oxadiazolylpyrazolopyrimidine als mglur2- antagonisten |
| BRPI0619261A2 (pt) | 2005-11-30 | 2011-09-27 | Inotek Pharmaceuticals Corp | derivados de purina e métodos de uso desses |
| AU2006336834B2 (en) * | 2006-01-27 | 2009-12-10 | Can-Fite Biopharma Ltd. | Adenosine A3 receptor agonists for the treatment of dry eye disorders |
| 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 |
| BRPI0715318A2 (pt) * | 2006-10-06 | 2013-07-16 | Univ Pennsylvania | mÉtodo para reduzir a pressço itraocular e mÉtodo para assegurara a liberaÇço de uma composiÇço terapÊutica para reduzir a pressço intraocular |
| 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 |
| WO2009011893A2 (en) * | 2007-07-17 | 2009-01-22 | Combinatorx, Incorporated | Treatments of b-cell proliferative disorders |
| EP2178370A4 (en) * | 2007-07-17 | 2011-01-12 | Zalicus Inc | COMBINATIONS FOR THE TREATMENT OF PROLIFERATIVE B-CELL DISEASES |
| WO2009151569A2 (en) * | 2008-06-09 | 2009-12-17 | Combinatorx, Incorporated | Beta adrenergic receptor agonists for the treatment of b-cell proliferative disorders |
| US8629275B2 (en) | 2008-09-08 | 2014-01-14 | Merck Sharp & Dohme Corp. | AHCY hydrolase inhibitors for treatment of hyper homocysteinemia |
| WO2010134067A1 (en) | 2009-05-17 | 2010-11-25 | Can-Fite Biopharma Ltd. | A3 adenosine receptor agonists for the reduction of intraocular pressure |
| US9199102B2 (en) | 2009-07-21 | 2015-12-01 | 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 |
| JP2013516495A (ja) | 2010-01-11 | 2013-05-13 | 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 | 眼圧を低下させる組合せ、キット、および方法 |
| US20130045943A1 (en) | 2010-03-03 | 2013-02-21 | The Government Of The United States Of America As Represented By The Secretary Of The Department Of | A3ar agonists for the treatment of uveitis |
| 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 |
| WO2011123518A1 (en) * | 2010-03-31 | 2011-10-06 | The United States Of America, As Represented By The Secretary, Department Of Health And Human Services | Adenosine receptor agonists for the treatment and prevention of vascular or joint capsule calcification disorders |
| KR102072041B1 (ko) | 2011-12-22 | 2020-01-31 | 앨리오스 바이오파마 인크. | 치환된 뉴클레오사이드, 뉴클레오타이드 및 그의 유사체 |
| WO2013111132A1 (en) * | 2012-01-23 | 2013-08-01 | Can-Fite Biopharma Ltd. | Treatment of liver conditions |
| SMT201700377T1 (it) | 2012-01-26 | 2017-09-07 | Inotek Pharmaceuticals Corp | Polimorfi anidri di (2r,3s,4r,5r)-5-(6-(ciclopentilammino)-9h-purin-9-il)-3,4- diidrossitetraidrofuran-2-il)}metil nitrato e processi di sua preparazione |
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| MX378538B (es) | 2012-08-09 | 2025-03-10 | Can Fite Biopharma Ltd | Ligandos del receptor de adenosina a3 para su uso en el tratamiento de una disfuncion sexual. |
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| IL242723B (en) | 2015-11-23 | 2019-12-31 | Can Fite Biopharma Ltd | A3 adenosine receptor ligand for the treatment of ectopic fat accumulation |
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| WO1995002604A1 (en) * | 1993-07-13 | 1995-01-26 | The United States Of America, Represented By The Secretary, Department Of Health And Human Services | A3 adenosine receptor agonists |
| 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 |
| WO1999002143A2 (en) * | 1997-07-10 | 1999-01-21 | Can-Fite Technologies Ltd. | Medicament comprising adenosine |
| WO1999006053A1 (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 |
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| US5443836A (en) * | 1993-03-15 | 1995-08-22 | Gensia, Inc. | Methods for protecting tissues and organs from ischemic damage |
| 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 |
| US6048865A (en) * | 1997-07-29 | 2000-04-11 | Medco Research, Inc. | N6 -substituted-adenosine-5'-uronamides as adenosine receptor modulator |
| CA2316994A1 (en) | 1998-06-08 | 1999-12-16 | Epigenesis Pharmaceuticals, Inc. | Composition and method for prevention and treatment of cardiopulmonary and renal failure or damage associated with ischemia, endotoxin release, ards or brought about by administration of certain drugs |
| 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 |
| EE05185B1 (et) * | 1999-02-01 | 2009-06-15 | University Of Virginia Patent Foundation | Kompositsioonid p?letikuliste protsesside ksitlemiseks |
| 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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- 2000-09-08 EP EP00956773A patent/EP1261322B1/en not_active Expired - Lifetime
- 2000-09-08 BR BR0013905-0A patent/BR0013905A/pt not_active Application Discontinuation
- 2000-09-08 WO PCT/IL2000/000550 patent/WO2001019360A2/en not_active Ceased
- 2000-09-08 KR KR1020067006473A patent/KR100674529B1/ko not_active Expired - Lifetime
- 2000-09-08 US US09/700,751 patent/US7064112B1/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 AU AU68634/00A patent/AU782826B2/en not_active Expired
- 2000-09-08 PL PL356469A patent/PL199852B1/pl unknown
- 2000-09-08 CN CNB008148007A patent/CN100358512C/zh not_active Expired - Lifetime
- 2000-09-08 MX MXPA02002546A patent/MXPA02002546A/es active IP Right Grant
- 2000-09-08 HK HK03105018.4A patent/HK1052653B/zh not_active IP Right Cessation
- 2000-09-08 PT PT00956773T patent/PT1261322E/pt unknown
- 2000-09-08 DK DK00956773T patent/DK1261322T3/da active
- 2000-09-08 ES ES00956773T patent/ES2296637T3/es not_active Expired - Lifetime
- 2000-09-08 HU HU0203870A patent/HU226913B1/hu unknown
- 2000-09-08 RU RU2002109228/15A patent/RU2239455C2/ru active
- 2000-09-08 CA CA002384111A patent/CA2384111C/en not_active Expired - Lifetime
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2005
- 2005-11-25 US US11/286,376 patent/US20060084626A1/en not_active Abandoned
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| 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 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2391103C2 (ru) * | 2004-10-15 | 2010-06-10 | Си Ви Терапьютикс, Инк. | Способ предупреждения и лечения ремоделирования дыхательных путей и воспаления легких с применением антагонистов аденозиновых рецепторов a2b |
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