RU2356887C2 - 2-арилуксусные кислоты, их производные и содержащие их фармацевтические композиции - Google Patents
2-арилуксусные кислоты, их производные и содержащие их фармацевтические композиции Download PDFInfo
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- RU2356887C2 RU2356887C2 RU2005127777/04A RU2005127777A RU2356887C2 RU 2356887 C2 RU2356887 C2 RU 2356887C2 RU 2005127777/04 A RU2005127777/04 A RU 2005127777/04A RU 2005127777 A RU2005127777 A RU 2005127777A RU 2356887 C2 RU2356887 C2 RU 2356887C2
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- Prior art keywords
- methyl
- group
- acetic acid
- alkyl
- pyrrol
- Prior art date
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- 239000008194 pharmaceutical composition Substances 0.000 title claims description 8
- 239000002253 acid Substances 0.000 title abstract description 14
- 150000007513 acids Chemical class 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 108090001007 Interleukin-8 Proteins 0.000 claims abstract description 37
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 29
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 28
- 230000035605 chemotaxis Effects 0.000 claims abstract description 24
- 239000001257 hydrogen Substances 0.000 claims abstract description 23
- 239000003112 inhibitor Substances 0.000 claims abstract description 23
- 125000004429 atom Chemical group 0.000 claims abstract description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 20
- 102100036166 C-X-C chemokine receptor type 1 Human genes 0.000 claims abstract description 19
- 101000947174 Homo sapiens C-X-C chemokine receptor type 1 Proteins 0.000 claims abstract description 18
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 14
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000001301 oxygen Substances 0.000 claims abstract description 13
- 102000016950 Chemokine CXCL1 Human genes 0.000 claims abstract description 11
- 239000000460 chlorine Substances 0.000 claims abstract description 11
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 11
- 101001027327 Bos taurus Growth-regulated protein homolog alpha Proteins 0.000 claims abstract description 10
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 9
- 125000001165 hydrophobic group Chemical group 0.000 claims abstract description 8
- 150000003839 salts Chemical class 0.000 claims abstract description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims abstract description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000001408 amides Chemical class 0.000 claims abstract description 7
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims abstract description 7
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 7
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 7
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 102000004890 Interleukin-8 Human genes 0.000 claims description 36
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 14
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 10
- 125000001424 substituent group Chemical group 0.000 claims description 10
- 208000006545 Chronic Obstructive Pulmonary Disease Diseases 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 8
- 201000004681 Psoriasis Diseases 0.000 claims description 7
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 7
- 239000003814 drug Substances 0.000 claims description 7
- BXVGCNQIUDNXRC-UHFFFAOYSA-N 2-[2-methyl-4-(2-methylpropyl)phenyl]acetic acid Chemical compound CC(C)CC1=CC=C(CC(O)=O)C(C)=C1 BXVGCNQIUDNXRC-UHFFFAOYSA-N 0.000 claims description 6
- 230000010410 reperfusion Effects 0.000 claims description 6
- IQCYKHUXUJYEQT-UHFFFAOYSA-N 2-(2-methyl-3-propan-2-ylphenyl)acetic acid Chemical compound CC(C)C1=CC=CC(CC(O)=O)=C1C IQCYKHUXUJYEQT-UHFFFAOYSA-N 0.000 claims description 5
- 206010009900 Colitis ulcerative Diseases 0.000 claims description 5
- 201000006704 Ulcerative Colitis Diseases 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 5
- YGTZOCNQAGVWON-UHFFFAOYSA-N n-[2-methyl-4-(2-methylpropyl)phenyl]acetamide Chemical compound CC(C)CC1=CC=C(NC(C)=O)C(C)=C1 YGTZOCNQAGVWON-UHFFFAOYSA-N 0.000 claims description 5
- QTPAUDWUWBSRLX-UHFFFAOYSA-N 2-(5-acetyl-1-methylpyrrol-2-yl)acetic acid Chemical compound CC(=O)C1=CC=C(CC(O)=O)N1C QTPAUDWUWBSRLX-UHFFFAOYSA-N 0.000 claims description 4
- FPVHGWJOLPNFOE-UHFFFAOYSA-N 2-[1-methyl-5-(2-methylpropanoyl)pyrrol-2-yl]acetic acid Chemical compound CC(C)C(=O)C1=CC=C(CC(O)=O)N1C FPVHGWJOLPNFOE-UHFFFAOYSA-N 0.000 claims description 4
- 206010016654 Fibrosis Diseases 0.000 claims description 4
- 206010018364 Glomerulonephritis Diseases 0.000 claims description 4
- 206010034277 Pemphigoid Diseases 0.000 claims description 4
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 4
- 230000004761 fibrosis Effects 0.000 claims description 4
- 201000001441 melanoma Diseases 0.000 claims description 4
- LRJZKWXVWFQBMV-UHFFFAOYSA-N n-(5-acetyl-1-methylpyrrol-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C(C(C)=O)N1C LRJZKWXVWFQBMV-UHFFFAOYSA-N 0.000 claims description 4
- 230000002265 prevention Effects 0.000 claims description 4
- 206010039073 rheumatoid arthritis Diseases 0.000 claims description 4
- DZGOOVJENNOITA-UHFFFAOYSA-N 2-[2-methyl-4-(trifluoromethylsulfonylamino)phenyl]acetic acid Chemical compound CC1=CC(NS(=O)(=O)C(F)(F)F)=CC=C1CC(O)=O DZGOOVJENNOITA-UHFFFAOYSA-N 0.000 claims description 3
- KCLNYLPISWGIHL-UHFFFAOYSA-N N-[2-methyl-4-(trifluoromethylsulfonylamino)phenyl]-2-oxopropane-1-sulfonamide Chemical compound C(C)(=O)CS(=O)(=O)NC1=C(C=C(C=C1)NS(=O)(=O)C(F)(F)F)C KCLNYLPISWGIHL-UHFFFAOYSA-N 0.000 claims description 3
- 208000000594 bullous pemphigoid Diseases 0.000 claims description 3
- 239000000969 carrier Substances 0.000 claims description 3
- GNFVGZYSNLZISU-UHFFFAOYSA-N n-[1-methyl-5-(2-methylpropanoyl)pyrrol-2-yl]acetamide Chemical compound CC(C)C(=O)C1=CC=C(NC(C)=O)N1C GNFVGZYSNLZISU-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 0.000 claims description 3
- 150000003456 sulfonamides Chemical class 0.000 claims description 3
- MLZOYRSGVAWKCO-UHFFFAOYSA-N N-(5-acetyl-1-methylpyrrol-2-yl)-N-methylsulfonylacetamide Chemical compound CC(=O)N(c1ccc(C(C)=O)n1C)S(C)(=O)=O MLZOYRSGVAWKCO-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- XPKXFUZKROWVQH-UHFFFAOYSA-N n-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]-2-oxopropane-1-sulfonamide Chemical compound CN1C(NS(=O)(=O)CC(=O)C)=CC=C1C(=O)C1=CC=C(C)C=C1 XPKXFUZKROWVQH-UHFFFAOYSA-N 0.000 claims description 2
- IZTCNMANEXXNBG-UHFFFAOYSA-N n-[2-methyl-4-(2-methylpropyl)phenyl]-n-methylsulfonylacetamide Chemical compound CC(C)CC1=CC=C(N(C(C)=O)S(C)(=O)=O)C(C)=C1 IZTCNMANEXXNBG-UHFFFAOYSA-N 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 208000035475 disorder Diseases 0.000 claims 2
- 239000002671 adjuvant Substances 0.000 claims 1
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- 230000005764 inhibitory process Effects 0.000 abstract description 8
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- 125000006527 (C1-C5) alkyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 55
- -1 benzenesulfonyloxy Chemical group 0.000 description 50
- XKTZWUACRZHVAN-VADRZIEHSA-N interleukin-8 Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@H](CC=1C2=CC=CC=C2NC=1)NC(=O)[C@@H](NC(C)=O)CCSC)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(O)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CC(N)=O)C(=O)N[C@@H](CC=1C=CC=CC=1)C(=O)N[C@@H]([C@@H](C)O)C(=O)NCC(=O)N[C@@H](CCSC)C(=O)N1[C@H](CCC1)C(=O)N1[C@H](CCC1)C(=O)N[C@@H](C)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CCC(O)=O)C(=O)N[C@H](CC(O)=O)C(=O)N[C@H](CC=1C=CC(O)=CC=1)C(=O)N[C@H](CO)C(=O)N1[C@H](CCC1)C(N)=O)C1=CC=CC=C1 XKTZWUACRZHVAN-VADRZIEHSA-N 0.000 description 34
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- 238000000034 method Methods 0.000 description 26
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- 235000011054 acetic acid Nutrition 0.000 description 16
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- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 12
- 238000002474 experimental method Methods 0.000 description 12
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 11
- CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- 125000001931 aliphatic group Chemical group 0.000 description 11
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- 230000002829 reductive effect Effects 0.000 description 10
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- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
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- WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 description 5
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- HJIAMFHSAAEUKR-UHFFFAOYSA-N (2-hydroxyphenyl)-phenylmethanone Chemical compound OC1=CC=CC=C1C(=O)C1=CC=CC=C1 HJIAMFHSAAEUKR-UHFFFAOYSA-N 0.000 description 4
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- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 4
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- VIQXGZVEOFNYAI-UHFFFAOYSA-N N-[2-methyl-4-(2-methylpropyl)phenyl]-2-oxopropane-1-sulfonamide Chemical compound C(C)(=O)CS(=O)(=O)NC1=C(C=C(C=C1)CC(C)C)C VIQXGZVEOFNYAI-UHFFFAOYSA-N 0.000 description 4
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- MDSMFFNGDIUDOF-UHFFFAOYSA-N 2-(1-benzoyl-2-chloropyrrol-3-yl)acetic acid Chemical compound ClC1=C(CC(=O)O)C=CN1C(=O)C1=CC=CC=C1 MDSMFFNGDIUDOF-UHFFFAOYSA-N 0.000 description 3
- AZCOEIZFVQEQCU-UHFFFAOYSA-N 2-(1-benzoyl-2-methylindol-3-yl)acetic acid Chemical compound CC1=C(CC(O)=O)C2=CC=CC=C2N1C(=O)C1=CC=CC=C1 AZCOEIZFVQEQCU-UHFFFAOYSA-N 0.000 description 3
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Rheumatology (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Dermatology (AREA)
- Urology & Nephrology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Vascular Medicine (AREA)
- Immunology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrrole Compounds (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03002716 | 2003-02-06 | ||
| EP03002716.3 | 2003-02-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2005127777A RU2005127777A (ru) | 2006-05-27 |
| RU2356887C2 true RU2356887C2 (ru) | 2009-05-27 |
Family
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| RU2005127777/04A RU2356887C2 (ru) | 2003-02-06 | 2004-02-04 | 2-арилуксусные кислоты, их производные и содержащие их фармацевтические композиции |
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| EP (1) | EP1590314B1 (enExample) |
| JP (1) | JP5208411B2 (enExample) |
| CN (1) | CN100562511C (enExample) |
| AU (2) | AU2004210082B2 (enExample) |
| CA (1) | CA2511582C (enExample) |
| DK (1) | DK1590314T3 (enExample) |
| ES (1) | ES2551929T3 (enExample) |
| HU (1) | HUE026285T2 (enExample) |
| NO (1) | NO334149B1 (enExample) |
| PT (1) | PT1590314E (enExample) |
| RU (1) | RU2356887C2 (enExample) |
| SI (1) | SI1590314T1 (enExample) |
| WO (1) | WO2004069782A2 (enExample) |
Families Citing this family (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2477604A1 (en) | 2002-03-13 | 2003-09-25 | Signum Biosciences, Inc. | Modulation of protein methylation and phosphoprotein phosphate |
| CN1934077B (zh) * | 2004-03-23 | 2010-09-29 | 冬姆佩制药股份公司 | 2-苯基丙酸衍生物及含有它们的药物组合物 |
| US7923041B2 (en) | 2005-02-03 | 2011-04-12 | Signum Biosciences, Inc. | Compositions and methods for enhancing cognitive function |
| EP1843734A4 (en) | 2005-02-03 | 2008-09-10 | Signum Biosciences Inc | COMPOSITIONS AND METHOD FOR INTENSIFYING COGNITIVE FUNCTIONS |
| GB0525144D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| GB0525143D0 (en) * | 2005-12-09 | 2006-01-18 | Novartis Ag | Organic compounds |
| CN102014897B (zh) | 2008-04-21 | 2015-08-05 | 西格纳姆生物科学公司 | 化合物、组合物和其制备方法 |
| CN103159674A (zh) * | 2013-04-03 | 2013-06-19 | 苏州安诺生物医药技术有限公司 | 2-苯烷酰胺类化合物及其制备方法、药物组合物和用途 |
| CN107398233B (zh) * | 2016-05-20 | 2019-07-05 | 中国石油天然气股份有限公司 | 一种酰胺基苯磺酸盐表面活性剂及其制备方法和应用 |
| MA53188A1 (fr) * | 2018-10-11 | 2021-12-31 | Basf As | Composés aromatiques et leurs utilisations pharmaceutiques |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1574570A (enExample) * | 1967-07-26 | 1969-07-11 |
Family Cites Families (15)
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| GB119562A (en) * | 1917-10-22 | 1918-10-10 | William Davidson | Improvements in Implements for Cultivating or Pulverising the Soil. |
| US2425821A (en) * | 1944-04-19 | 1947-08-19 | Paul A Peters | Method and apparatus for determining the eye color reflex sensation |
| US2425721A (en) | 1945-08-06 | 1947-08-19 | Univ Michigan | Thiophene compounds and methods of obtaining the same |
| GB1148908A (en) * | 1965-04-19 | 1969-04-16 | Sumitomo Chemical Co | Indole derivatives and processes for making them |
| FR8113M (enExample) * | 1967-07-26 | 1970-08-03 | ||
| US3752826A (en) * | 1970-01-26 | 1973-08-14 | Mcneilab Inc | Aroyl substituted pyrroles |
| US3833608A (en) * | 1970-11-23 | 1974-09-03 | Merck Sharp & Dohme | Indole-3-methanesulfonamides |
| US3883541A (en) | 1971-02-22 | 1975-05-13 | Dow Chemical Co | 4-Amino-3,5,6-trichloro-2-(functionally substituted methyl) pyridine compounds |
| WO2000010610A2 (en) * | 1998-08-19 | 2000-03-02 | Theramark Limited | Drug targeting |
| WO2001036415A1 (en) | 1999-11-18 | 2001-05-25 | Novartis Ag | Pesticidal aminoheterocyclamide compounds |
| IT1317826B1 (it) | 2000-02-11 | 2003-07-15 | Dompe Spa | Ammidi, utili nell'inibizione della chemiotassi dei neutrofiliindotta da il-8. |
| US7135495B2 (en) * | 2000-03-09 | 2006-11-14 | Ono Pharmaceutical Co., Ltd. | Indole derivatives |
| ITMI20010395A1 (it) | 2001-02-27 | 2002-08-27 | Dompe Spa | Omega-amminoalchilammidi di acidi r-2-aril-propionici come inibitori della chemiotassi di cellule polimorfonucleate e mononucleate |
| WO2003013526A1 (en) | 2001-08-08 | 2003-02-20 | Merck & Co. Inc. | Anticoagulant compounds |
| KR20040044856A (ko) * | 2001-09-07 | 2004-05-31 | 오노 야꾸힝 고교 가부시키가이샤 | 인돌 유도체 화합물 |
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2004
- 2004-02-04 PT PT47079264T patent/PT1590314E/pt unknown
- 2004-02-04 RU RU2005127777/04A patent/RU2356887C2/ru not_active IP Right Cessation
- 2004-02-04 HU HUE04707926A patent/HUE026285T2/en unknown
- 2004-02-04 SI SI200432275T patent/SI1590314T1/sl unknown
- 2004-02-04 CN CNB2004800087419A patent/CN100562511C/zh not_active Expired - Fee Related
- 2004-02-04 ES ES04707926.4T patent/ES2551929T3/es not_active Expired - Lifetime
- 2004-02-04 CA CA2511582A patent/CA2511582C/en not_active Expired - Fee Related
- 2004-02-04 US US10/541,429 patent/US7776909B2/en not_active Expired - Fee Related
- 2004-02-04 EP EP04707926.4A patent/EP1590314B1/en not_active Expired - Lifetime
- 2004-02-04 WO PCT/EP2004/001021 patent/WO2004069782A2/en not_active Ceased
- 2004-02-04 AU AU2004210082A patent/AU2004210082B2/en not_active Ceased
- 2004-02-04 DK DK04707926.4T patent/DK1590314T3/en active
- 2004-02-04 JP JP2006501731A patent/JP5208411B2/ja not_active Expired - Fee Related
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2005
- 2005-08-30 NO NO20054017A patent/NO334149B1/no not_active IP Right Cessation
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2010
- 2010-06-30 US US12/828,181 patent/US8871784B2/en not_active Expired - Fee Related
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2011
- 2011-03-22 AU AU2011201305A patent/AU2011201305B2/en not_active Ceased
- 2011-04-22 US US13/092,571 patent/US8648110B2/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1574570A (enExample) * | 1967-07-26 | 1969-07-11 |
Non-Patent Citations (1)
| Title |
|---|
| Walsh D.A. et al. «Antiinflammatory Agents. 2. Syntheses and Antiinflammatory Activity of Substituted 2-Aminophenylacetic Acid Derivatives», J. Med. Chem., 1982, 25, p.446-451. Большая медицинская энциклопедия, под ред. Б.В. Петровского, т.21. - М.: Советская энциклопедия, с.371-375, т.11. - М.: Советская энциклопедия, с.116-125, т.15. - М.: Советская энциклопедия, с.1-3, т.28. - М.: Советская энциклопедия, с.156-161, т.21. - М.: Советская энциклопедия, с.382-383, т.22. - М.: Советская энциклопедия, с.91, т.6. - М.: Советская энциклопедия, с.145. Идиопатический ретроперитонеальный фиброз. Найдено в Интернете, on-line, http://pochemutak.ru/md/mod/tex/views/73726/. Системные васкулиты. Найдено в Интернете, on-line, http://www.rheumo.ru. Поражение тонкого кишечника при ишемии-реперфузии. Найдено в Интернете, on-line, http://www.volgmed.ru/depts/patph/s/intestine_ischemia.doc. * |
Also Published As
| Publication number | Publication date |
|---|---|
| US20110195967A1 (en) | 2011-08-11 |
| US20100267726A1 (en) | 2010-10-21 |
| RU2005127777A (ru) | 2006-05-27 |
| CN100562511C (zh) | 2009-11-25 |
| WO2004069782A3 (en) | 2004-09-16 |
| HK1090356A1 (zh) | 2006-12-22 |
| PT1590314E (pt) | 2015-11-19 |
| NO20054017L (no) | 2005-08-30 |
| AU2004210082B2 (en) | 2011-03-17 |
| HUE026285T2 (en) | 2016-05-30 |
| ES2551929T3 (es) | 2015-11-24 |
| US8871784B2 (en) | 2014-10-28 |
| DK1590314T3 (en) | 2015-11-02 |
| CN1768026A (zh) | 2006-05-03 |
| JP2006516592A (ja) | 2006-07-06 |
| AU2011201305B2 (en) | 2013-01-31 |
| EP1590314B1 (en) | 2015-08-05 |
| CA2511582A1 (en) | 2004-08-19 |
| US7776909B2 (en) | 2010-08-17 |
| US20060223842A1 (en) | 2006-10-05 |
| CA2511582C (en) | 2012-01-24 |
| US8648110B2 (en) | 2014-02-11 |
| SI1590314T1 (sl) | 2015-12-31 |
| JP5208411B2 (ja) | 2013-06-12 |
| EP1590314A2 (en) | 2005-11-02 |
| WO2004069782A2 (en) | 2004-08-19 |
| AU2004210082A1 (en) | 2004-08-19 |
| NO334149B1 (no) | 2013-12-16 |
| AU2011201305A1 (en) | 2011-04-07 |
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| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
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| PC43 | Official registration of the transfer of the exclusive right without contract for inventions |
Effective date: 20151027 |
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| MM4A | The patent is invalid due to non-payment of fees |
Effective date: 20190205 |