JP2008534495A5 - - Google Patents
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- Publication number
- JP2008534495A5 JP2008534495A5 JP2008502938A JP2008502938A JP2008534495A5 JP 2008534495 A5 JP2008534495 A5 JP 2008534495A5 JP 2008502938 A JP2008502938 A JP 2008502938A JP 2008502938 A JP2008502938 A JP 2008502938A JP 2008534495 A5 JP2008534495 A5 JP 2008534495A5
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- hydroxyl group
- compound
- general formula
- formula
- 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.)
- Granted
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- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 30
- 229910052739 hydrogen Inorganic materials 0.000 claims 30
- 239000001257 hydrogen Substances 0.000 claims 30
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 18
- 150000001875 compounds Chemical class 0.000 claims 17
- -1 3-phenylpropionyl tyramine Chemical compound 0.000 claims 13
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 8
- 238000000034 method Methods 0.000 claims 8
- 150000003839 salts Chemical class 0.000 claims 7
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 125000003277 amino group Chemical group 0.000 claims 6
- 229940035676 analgesics Drugs 0.000 claims 5
- 239000000730 antalgic agent Substances 0.000 claims 5
- 150000001412 amines Chemical class 0.000 claims 4
- 230000000202 analgesic effect Effects 0.000 claims 4
- 230000001430 anti-depressive effect Effects 0.000 claims 4
- 230000000141 anti-hypoxic effect Effects 0.000 claims 4
- 230000003110 anti-inflammatory effect Effects 0.000 claims 4
- 230000002921 anti-spasmodic effect Effects 0.000 claims 4
- 239000000935 antidepressant agent Substances 0.000 claims 4
- 229940005513 antidepressants Drugs 0.000 claims 4
- 239000000812 cholinergic antagonist Substances 0.000 claims 4
- 239000003814 drug Substances 0.000 claims 4
- 230000000694 effects Effects 0.000 claims 4
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- 208000018737 Parkinson disease Diseases 0.000 claims 3
- DZGWFCGJZKJUFP-UHFFFAOYSA-N Tyramine Natural products NCCC1=CC=C(O)C=C1 DZGWFCGJZKJUFP-UHFFFAOYSA-N 0.000 claims 3
- 230000000648 anti-parkinson Effects 0.000 claims 3
- 239000000939 antiparkinson agent Substances 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 claims 3
- KJACRUBFUHSJLG-HNNXBMFYSA-N (2s)-3-(4-hydroxyphenyl)-2-[(2-phenylacetyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CC=1C=CC=CC=1)C1=CC=C(O)C=C1 KJACRUBFUHSJLG-HNNXBMFYSA-N 0.000 claims 2
- XQXPVVBIMDBYFF-UHFFFAOYSA-N 4-hydroxyphenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C=C1 XQXPVVBIMDBYFF-UHFFFAOYSA-N 0.000 claims 2
- 206010010904 Convulsion Diseases 0.000 claims 2
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 claims 2
- 206010021143 Hypoxia Diseases 0.000 claims 2
- OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 claims 2
- HIUONFHURKCCKW-UHFFFAOYSA-N N-phenethylhydrocinnamide Natural products C=1C=CC=CC=1CCNC(=O)CCC1=CC=CC=C1 HIUONFHURKCCKW-UHFFFAOYSA-N 0.000 claims 2
- 208000002193 Pain Diseases 0.000 claims 2
- 102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 claims 2
- 108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 claims 2
- 230000036461 convulsion Effects 0.000 claims 2
- MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 230000007954 hypoxia Effects 0.000 claims 2
- 230000002757 inflammatory effect Effects 0.000 claims 2
- 230000002401 inhibitory effect Effects 0.000 claims 2
- LRKMKJMUWJYINS-UHFFFAOYSA-N n-[2-(4-hydroxyphenyl)ethyl]-2-phenylacetamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)CC1=CC=CC=C1 LRKMKJMUWJYINS-UHFFFAOYSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 239000008194 pharmaceutical composition Substances 0.000 claims 2
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 claims 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 claims 2
- 208000011580 syndromic disease Diseases 0.000 claims 2
- 229960003732 tyramine Drugs 0.000 claims 2
- JQPTWLBWTVDKNO-INIZCTEOSA-N (2s)-2-[3-(4-hydroxyphenyl)propanoylamino]-3-phenylpropanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CCC=1C=CC(O)=CC=1)C1=CC=CC=C1 JQPTWLBWTVDKNO-INIZCTEOSA-N 0.000 claims 1
- LASNYAREGNBWNQ-SFHVURJKSA-N (2s)-2-acetamido-3-(4-hydroxyphenyl)-n-(2-phenylethyl)propanamide Chemical compound C([C@H](NC(=O)C)C(=O)NCCC=1C=CC=CC=1)C1=CC=C(O)C=C1 LASNYAREGNBWNQ-SFHVURJKSA-N 0.000 claims 1
- QNJQWNPLJLOTKX-AWEZNQCLSA-N (2s)-3-(4,4-dihydroxycyclohexa-1,5-dien-1-yl)-2-[(2-phenylacetyl)amino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CC=1C=CC=CC=1)C1=CCC(O)(O)C=C1 QNJQWNPLJLOTKX-AWEZNQCLSA-N 0.000 claims 1
- MCWLXSHTRCIDDZ-INIZCTEOSA-N (2s)-3-(4-hydroxyphenyl)-2-(3-phenylpropanoylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CCC=1C=CC=CC=1)C1=CC=C(O)C=C1 MCWLXSHTRCIDDZ-INIZCTEOSA-N 0.000 claims 1
- COMSBNSFYYEQOJ-INIZCTEOSA-N (2s)-3-(4-hydroxyphenyl)-2-[3-(4-hydroxyphenyl)propanoylamino]propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CCC=1C=CC(O)=CC=1)C1=CC=C(O)C=C1 COMSBNSFYYEQOJ-INIZCTEOSA-N 0.000 claims 1
- PKOVGZQJPDDEJO-INIZCTEOSA-N (2s)-3-phenyl-2-(3-phenylpropanoylamino)propanoic acid Chemical compound C([C@@H](C(=O)O)NC(=O)CCC=1C=CC=CC=1)C1=CC=CC=C1 PKOVGZQJPDDEJO-INIZCTEOSA-N 0.000 claims 1
- PPKXEPBICJTCRU-XMZRARIVSA-N (R,R)-tramadol hydrochloride Chemical compound Cl.COC1=CC=CC([C@]2(O)[C@H](CCCC2)CN(C)C)=C1 PPKXEPBICJTCRU-XMZRARIVSA-N 0.000 claims 1
- SERBNUYNEAQHNJ-UHFFFAOYSA-N 2-phenyl-n-(2-phenylethyl)acetamide Chemical compound C=1C=CC=CC=1CCNC(=O)CC1=CC=CC=C1 SERBNUYNEAQHNJ-UHFFFAOYSA-N 0.000 claims 1
- GYXQXOGMDKYDFU-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-n-(2-phenylethyl)propanamide Chemical compound C1=CC(O)=CC=C1CCC(=O)NCCC1=CC=CC=C1 GYXQXOGMDKYDFU-UHFFFAOYSA-N 0.000 claims 1
- XJOMECIQGMSDHB-UHFFFAOYSA-N 3-(4-hydroxyphenyl)-n-[2-(4-hydroxyphenyl)ethyl]propanamide Chemical compound C1=CC(O)=CC=C1CCNC(=O)CCC1=CC=C(O)C=C1 XJOMECIQGMSDHB-UHFFFAOYSA-N 0.000 claims 1
- 206010002556 Ankylosing Spondylitis Diseases 0.000 claims 1
- 208000036487 Arthropathies Diseases 0.000 claims 1
- YNQAXBDGNBPSCC-DEOSSOPVSA-N C1=CC=C(C=C1)CCCN[C@@H](CC2=CC=C(C=C2)O)C(=O)OCC3=CC=CC=C3 Chemical compound C1=CC=C(C=C1)CCCN[C@@H](CC2=CC=C(C=C2)O)C(=O)OCC3=CC=CC=C3 YNQAXBDGNBPSCC-DEOSSOPVSA-N 0.000 claims 1
- 206010061218 Inflammation Diseases 0.000 claims 1
- 208000012659 Joint disease Diseases 0.000 claims 1
- 125000003047 N-acetyl group Chemical group 0.000 claims 1
- LIIPHJDKZNTNII-HNNXBMFYSA-N N-phenylacetylphenylalanine Chemical compound C([C@@H](C(=O)O)NC(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 LIIPHJDKZNTNII-HNNXBMFYSA-N 0.000 claims 1
- 206010028980 Neoplasm Diseases 0.000 claims 1
- 206010034010 Parkinsonism Diseases 0.000 claims 1
- 206010065016 Post-traumatic pain Diseases 0.000 claims 1
- 208000004550 Postoperative Pain Diseases 0.000 claims 1
- 206010047249 Venous thrombosis Diseases 0.000 claims 1
- 230000003213 activating effect Effects 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 239000013543 active substance Substances 0.000 claims 1
- 230000004075 alteration Effects 0.000 claims 1
- 229940035678 anti-parkinson drug Drugs 0.000 claims 1
- 206010003246 arthritis Diseases 0.000 claims 1
- CBYGLQVAMOUFIE-QFIPXVFZSA-N benzyl (2s)-3-(4-hydroxyphenyl)-2-[(2-phenylacetyl)amino]propanoate Chemical compound C1=CC(O)=CC=C1C[C@@H](C(=O)OCC=1C=CC=CC=1)NC(=O)CC1=CC=CC=C1 CBYGLQVAMOUFIE-QFIPXVFZSA-N 0.000 claims 1
- 230000000035 biogenic effect Effects 0.000 claims 1
- 201000011510 cancer Diseases 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003795 chemical substances by application Substances 0.000 claims 1
- 210000002808 connective tissue Anatomy 0.000 claims 1
- 229940079593 drug Drugs 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000002996 emotional effect Effects 0.000 claims 1
- 230000002708 enhancing effect Effects 0.000 claims 1
- 230000004054 inflammatory process Effects 0.000 claims 1
- DJGAAPFSPWAYTJ-UHFFFAOYSA-M metamizole sodium Chemical compound [Na+].O=C1C(N(CS([O-])(=O)=O)C)=C(C)N(C)N1C1=CC=CC=C1 DJGAAPFSPWAYTJ-UHFFFAOYSA-M 0.000 claims 1
- VKSRNHXARKOPHJ-KRWDZBQOSA-N methyl (2s)-2-[3-(4-hydroxyphenyl)propanoylamino]-3-phenylpropanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)CCC=1C=CC(O)=CC=1)C1=CC=CC=C1 VKSRNHXARKOPHJ-KRWDZBQOSA-N 0.000 claims 1
- VNVRBDDZSYIUJK-INIZCTEOSA-N methyl (2s)-3-(4-hydroxyphenyl)-2-[(2-phenylacetyl)amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)CC=1C=CC=CC=1)C1=CC=C(O)C=C1 VNVRBDDZSYIUJK-INIZCTEOSA-N 0.000 claims 1
- ITMGOEJLSLAEDI-KRWDZBQOSA-N methyl (2s)-3-phenyl-2-(3-phenylpropanoylamino)propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)CCC=1C=CC=CC=1)C1=CC=CC=C1 ITMGOEJLSLAEDI-KRWDZBQOSA-N 0.000 claims 1
- OCGCFGFKKQLWOK-INIZCTEOSA-N methyl (2s)-3-phenyl-2-[(2-phenylacetyl)amino]propanoate Chemical compound C([C@@H](C(=O)OC)NC(=O)CC=1C=CC=CC=1)C1=CC=CC=C1 OCGCFGFKKQLWOK-INIZCTEOSA-N 0.000 claims 1
- LJHIBXVWVCGOJI-UHFFFAOYSA-N n-[2-(4,4-dihydroxycyclohexa-1,5-dien-1-yl)ethyl]-2-phenylacetamide Chemical compound C1=CC(O)(O)CC=C1CCNC(=O)CC1=CC=CC=C1 LJHIBXVWVCGOJI-UHFFFAOYSA-N 0.000 claims 1
- 210000005036 nerve Anatomy 0.000 claims 1
- 201000008482 osteoarthritis Diseases 0.000 claims 1
- 229960003424 phenylacetic acid Drugs 0.000 claims 1
- 239000003279 phenylacetic acid Substances 0.000 claims 1
- 201000003068 rheumatic fever Diseases 0.000 claims 1
- 206010039073 rheumatoid arthritis Diseases 0.000 claims 1
- 201000005671 spondyloarthropathy Diseases 0.000 claims 1
- 150000003668 tyrosines Chemical class 0.000 claims 1
- 125000001493 tyrosinyl group Chemical group [H]OC1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])(N([H])[H])C(*)=O 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| RU2005108492/04A RU2309144C2 (ru) | 2005-03-25 | 2005-03-25 | Фенилсодержащие n-ацильные производные аминов, способ их получения, фармацевтическая композиция и их применение в качестве противовоспалительных и анальгетических средств |
| RU2005108492 | 2005-03-25 | ||
| PCT/RU2006/000139 WO2006101422A1 (fr) | 2005-03-25 | 2006-03-24 | Derives n-acyles d'amines et d'acides amines amines contenant des phenyles, procede de fabrication, composition pharmaceutique et son utilisation |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2008534495A JP2008534495A (ja) | 2008-08-28 |
| JP2008534495A5 true JP2008534495A5 (https=) | 2009-05-14 |
| JP5384096B2 JP5384096B2 (ja) | 2014-01-08 |
Family
ID=37024023
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2008502938A Expired - Fee Related JP5384096B2 (ja) | 2005-03-25 | 2006-03-24 | アミン及びアミノ酸のフェニル−ｎ−アシル誘導体、それらの調製法、それらの製薬組成物及び使用 |
Country Status (18)
| Country | Link |
|---|---|
| US (2) | US8309766B2 (https=) |
| EP (1) | EP1876169B1 (https=) |
| JP (1) | JP5384096B2 (https=) |
| KR (1) | KR101383580B1 (https=) |
| CN (1) | CN101180267B (https=) |
| CA (1) | CA2602545C (https=) |
| CY (1) | CY1117449T1 (https=) |
| DK (1) | DK1876169T3 (https=) |
| EA (1) | EA013644B1 (https=) |
| ES (1) | ES2564238T3 (https=) |
| HU (1) | HUE027009T2 (https=) |
| MX (1) | MX2007011852A (https=) |
| PL (1) | PL1876169T3 (https=) |
| PT (1) | PT1876169E (https=) |
| RU (1) | RU2309144C2 (https=) |
| SI (1) | SI1876169T1 (https=) |
| UA (1) | UA88688C2 (https=) |
| WO (1) | WO2006101422A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1546088B1 (en) | 2002-10-03 | 2014-12-17 | Novaremed Ltd. | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| JP4939396B2 (ja) | 2004-03-26 | 2012-05-23 | ノヴァレメッド リミテッド | Ａｉｄｓ及び他のウイルス性疾患及びｈｉｖ関連感染症の改善又はその治療用化合物及びそのような化合物を含む組成物、そのような疾患及び感染症の治療方法及びそのような化合物及び組成物の製造方法 |
| GB0804213D0 (en) | 2008-03-06 | 2008-04-16 | New Era Biotech Ltd | A method of printing or preventing pain |
| CA2722087C (en) * | 2008-04-29 | 2013-07-09 | F. Hoffmann-La Roche Ag | 4-dimethylaminobutyric acid derivatives |
| EP2475361B1 (en) * | 2009-09-09 | 2019-11-06 | Novaremed Ltd. | N-substituted benzenepropanamides for use in the treatment of pain and inflammation |
| US8802734B2 (en) | 2009-09-09 | 2014-08-12 | Novaremed Limited | Method of treating or preventing pain |
| SG187666A1 (en) * | 2010-08-27 | 2013-03-28 | Neopharm Co Ltd | Novel compound accelerating secretion of human-derived anti-microbial peptide, method for preparing same, and composition having same as active ingredient |
| GB201116335D0 (en) * | 2011-09-21 | 2011-11-02 | Novaremed Ltd | A method of treating or preventing affective disorders |
| ES2578377B1 (es) | 2014-12-22 | 2017-05-04 | Consejo Superior De Investigaciones Científicas (Csic) | Compuestos moduladores del sensor neuronal de calcio dream y sus usos terapéuticos. |
| RU2690188C2 (ru) * | 2017-05-26 | 2019-05-31 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Новый мультитаргетный препарат для лечения заболеваний у млекопитающих |
| EP3672934A4 (en) * | 2017-08-21 | 2021-05-05 | Plex Pharmaceuticals, Inc. | DOUBLE ACTING FKBP12 AND FKBP52 INHIBITORS |
| RU2678563C1 (ru) * | 2017-10-27 | 2019-01-30 | Михаил Владимирович Овчинников | Водорастворимые производные тирозина, обладающие анальгетическим, противовоспалительным и противоотечным действием |
| RU2697414C1 (ru) * | 2018-05-11 | 2019-08-14 | Общество с ограниченной ответственностью "АЙ БИ ДИ Терапевтикс" | Новый антагонист тахикининовых рецепторов и его применение |
| RU2727703C2 (ru) * | 2018-10-29 | 2020-07-23 | Общество С Ограниченной Ответственностью "Фарминтерпрайсез" | Новый способ получения (S)-2-(2-(4-гидроксифенил)ацетамидо)-3-фенилпропановой кислоты |
| RU2716258C1 (ru) * | 2019-07-30 | 2020-03-11 | Автономная некоммерческая образовательная организация высшего образования Сколковский институт науки и технологий | Пептидный антагонист нмда-рецептора |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2711656A1 (de) * | 1977-03-17 | 1978-09-21 | Basf Ag | Neue pyridin-3-ole |
| DE2861593D1 (en) * | 1977-06-29 | 1982-03-11 | Beecham Group Plc | Peptides, pharmaceutical compositions containing the peptides and a process for the preparation of the peptides |
| JPS57145891A (en) * | 1981-03-05 | 1982-09-09 | Sagami Chem Res Center | Optically active diphosphine ligand |
| JPS57193437A (en) | 1981-05-21 | 1982-11-27 | Ajinomoto Co Inc | Amino acid derivative |
| ES8607214A1 (es) * | 1985-10-16 | 1986-06-01 | Gema Sa | Procedimiento enzimatico de resolucion de n-fenilacetil-ami-nocompuestos y purificacion de sus isomeros opticamente ac- tivos |
| USRE37160E1 (en) * | 1990-06-12 | 2001-05-01 | Rutgers, The State University | Synthesis of tyrosine derived diphenol monomers |
| US5403851A (en) * | 1994-04-05 | 1995-04-04 | Interneuron Pharmaceuticals, Inc. | Substituted tryptamines, phenalkylamines and related compounds |
| AU1463997A (en) * | 1995-12-22 | 1997-07-17 | Acea Pharmaceuticals, Inc. | Subtype-selective nmda receptor ligands and the use thereof |
| US6319492B1 (en) * | 1996-11-27 | 2001-11-20 | Rutgers, The State University | Copolymers of tyrosine-based polyarylates and poly(alkylene oxides) |
| US5912225A (en) * | 1997-04-14 | 1999-06-15 | Johns Hopkins Univ. School Of Medicine | Biodegradable poly (phosphoester-co-desaminotyrosyl L-tyrosine ester) compounds, compositions, articles and methods for making and using the same |
| JPH11127894A (ja) * | 1997-10-30 | 1999-05-18 | Ono Pharmaceut Co Ltd | カルボキシペプチダーゼａ活性測定方法および測定用キット |
| RU2123041C1 (ru) * | 1998-04-02 | 1998-12-10 | Пипия Гулади Эрастович | Бальзам "саратовский" |
| EP1073688B1 (en) * | 1998-04-13 | 2015-03-04 | Rutgers, The State University | The construction of copolymer libraries |
| EP1073434A1 (en) * | 1998-04-27 | 2001-02-07 | Smithkline Beecham Corporation | Ccr-3 receptor antagonists |
| US6414173B1 (en) * | 1998-07-02 | 2002-07-02 | University Of Maryland | Hypervalent silane and siloxane derivatives and the use thereof |
| US6852856B2 (en) * | 2000-03-09 | 2005-02-08 | Tokuyama Corporation | Method for preserving quaternary ammonium salt |
| RU2246501C2 (ru) * | 2000-09-27 | 2005-02-20 | Дзе Проктер Энд Гэмбл Компани | Лиганды меланокортиновых рецепторов |
| EP1546088B1 (en) * | 2002-10-03 | 2014-12-17 | Novaremed Ltd. | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| RU2233289C2 (ru) | 2002-11-04 | 2004-07-27 | Институт органического синтеза Уральского отделения РАН | Способ получения дипептидов |
-
2005
- 2005-03-25 RU RU2005108492/04A patent/RU2309144C2/ru active
-
2006
- 2006-03-24 PL PL06733250T patent/PL1876169T3/pl unknown
- 2006-03-24 EA EA200702072A patent/EA013644B1/ru not_active IP Right Cessation
- 2006-03-24 HU HUE06733250A patent/HUE027009T2/en unknown
- 2006-03-24 ES ES06733250.2T patent/ES2564238T3/es not_active Expired - Lifetime
- 2006-03-24 CN CN200680017304.2A patent/CN101180267B/zh not_active Expired - Fee Related
- 2006-03-24 KR KR1020077024641A patent/KR101383580B1/ko not_active Expired - Fee Related
- 2006-03-24 JP JP2008502938A patent/JP5384096B2/ja not_active Expired - Fee Related
- 2006-03-24 SI SI200632027A patent/SI1876169T1/sl unknown
- 2006-03-24 CA CA2602545A patent/CA2602545C/en not_active Expired - Fee Related
- 2006-03-24 EP EP06733250.2A patent/EP1876169B1/en not_active Expired - Lifetime
- 2006-03-24 PT PT67332502T patent/PT1876169E/pt unknown
- 2006-03-24 MX MX2007011852A patent/MX2007011852A/es active IP Right Grant
- 2006-03-24 US US11/886,965 patent/US8309766B2/en not_active Expired - Fee Related
- 2006-03-24 UA UAA200711752A patent/UA88688C2/ru unknown
- 2006-03-24 DK DK06733250.2T patent/DK1876169T3/en active
- 2006-03-24 WO PCT/RU2006/000139 patent/WO2006101422A1/ru not_active Ceased
-
2012
- 2012-11-12 US US13/674,339 patent/US8546612B2/en not_active Expired - Fee Related
-
2016
- 2016-03-10 CY CY20161100208T patent/CY1117449T1/el unknown
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