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 (enExample) | 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 (enExample) |
| EP (1) | EP1876169B1 (enExample) |
| JP (1) | JP5384096B2 (enExample) |
| KR (1) | KR101383580B1 (enExample) |
| CN (1) | CN101180267B (enExample) |
| CA (1) | CA2602545C (enExample) |
| CY (1) | CY1117449T1 (enExample) |
| DK (1) | DK1876169T3 (enExample) |
| EA (1) | EA013644B1 (enExample) |
| ES (1) | ES2564238T3 (enExample) |
| HU (1) | HUE027009T2 (enExample) |
| MX (1) | MX2007011852A (enExample) |
| PL (1) | PL1876169T3 (enExample) |
| PT (1) | PT1876169E (enExample) |
| RU (1) | RU2309144C2 (enExample) |
| SI (1) | SI1876169T1 (enExample) |
| UA (1) | UA88688C2 (enExample) |
| WO (1) | WO2006101422A1 (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7642290B2 (en) | 2002-10-03 | 2010-01-05 | Novaremed Limited | Compounds for use in the treatment of autoimmune diseases, immuno-allergical diseases and organ or tissue transplantation rejection |
| US7674829B2 (en) | 2004-03-26 | 2010-03-09 | Novaremed Limited | Compounds for the treatment of AIDS and other viral diseases |
| GB0804213D0 (en) | 2008-03-06 | 2008-04-16 | New Era Biotech Ltd | A method of printing or preventing pain |
| WO2009132978A1 (en) * | 2008-04-29 | 2009-11-05 | F. Hoffmann-La Roche Ag | 4-dimethylaminobutyric acid derivatives |
| WO2011030205A1 (en) * | 2009-09-09 | 2011-03-17 | Novaremed Ltd. | N-substituted benzenepropanamide or benzenepropenamide 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 |
| CN103221383B (zh) * | 2010-08-27 | 2016-04-20 | 株式会社新药 | 促进人源性抗菌肽分泌的新化合物、其制备方法以及含有其作为活性成分的组合物 |
| 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 |
| JP2021509398A (ja) * | 2017-08-21 | 2021-03-25 | プレックス ファーマスーティカルズ，インク | 二重作用ｆｋｂｐ１２およびｆｋｂｐ５２阻害剤 |
| 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 |
| CN117886714A (zh) * | 2024-01-16 | 2024-04-16 | 中国药科大学 | 丙氨酸衍生物、其制备方法及医药用途 |
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" |
| AU761458B2 (en) * | 1998-04-13 | 2003-06-05 | Rutgers, The State University | The construction of copolymer libraries |
| WO1999055330A1 (en) * | 1998-04-27 | 1999-11-04 | 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 |
| DE60116200T2 (de) * | 2000-03-09 | 2006-08-17 | Tokuyama Corp., Shunan | Verfahren zur lagerung quaternärer ammonium-salze |
| HUP0303085A2 (hu) * | 2000-09-27 | 2003-12-29 | The Procter & Gamble Co. | Melanokortin receptor ligandumok és ezeket tartalmazó gyógyszerkészítmények |
| US7642290B2 (en) * | 2002-10-03 | 2010-01-05 | Novaremed Limited | 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 MX MX2007011852A patent/MX2007011852A/es active IP Right Grant
- 2006-03-24 KR KR1020077024641A patent/KR101383580B1/ko not_active Expired - Fee Related
- 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 PT PT67332502T patent/PT1876169E/pt unknown
- 2006-03-24 EA EA200702072A patent/EA013644B1/ru not_active IP Right Cessation
- 2006-03-24 US US11/886,965 patent/US8309766B2/en not_active Expired - Fee Related
- 2006-03-24 HU HUE06733250A patent/HUE027009T2/en unknown
- 2006-03-24 SI SI200632027A patent/SI1876169T1/sl unknown
- 2006-03-24 JP JP2008502938A patent/JP5384096B2/ja not_active Expired - Fee Related
- 2006-03-24 WO PCT/RU2006/000139 patent/WO2006101422A1/ru not_active Ceased
- 2006-03-24 UA UAA200711752A patent/UA88688C2/ru unknown
- 2006-03-24 CA CA2602545A patent/CA2602545C/en not_active Expired - Fee Related
- 2006-03-24 DK DK06733250.2T patent/DK1876169T3/en active
- 2006-03-24 EP EP06733250.2A patent/EP1876169B1/en not_active Expired - Lifetime
- 2006-03-24 PL PL06733250T patent/PL1876169T3/pl unknown
-
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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