RU2391339C2 - 5-[3-(4-бензилоксифенилтио)-фур-2-ил]-имидазолидин-2,4-дион и аналоги в качестве ингибиторов эластазы макрофагов - Google Patents
5-[3-(4-бензилоксифенилтио)-фур-2-ил]-имидазолидин-2,4-дион и аналоги в качестве ингибиторов эластазы макрофагов Download PDFInfo
- Publication number
- RU2391339C2 RU2391339C2 RU2007105822/04A RU2007105822A RU2391339C2 RU 2391339 C2 RU2391339 C2 RU 2391339C2 RU 2007105822/04 A RU2007105822/04 A RU 2007105822/04A RU 2007105822 A RU2007105822 A RU 2007105822A RU 2391339 C2 RU2391339 C2 RU 2391339C2
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- Prior art keywords
- mmp
- methoxyphenyl
- chlorophenyl
- methylphenyl
- fur
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- ZUOUZWHAINARGI-UHFFFAOYSA-N 5-[3-(4-phenylmethoxyphenyl)sulfanylfuran-2-yl]imidazolidine-2,4-dione Chemical compound O=C1NC(=O)NC1C1=C(SC=2C=CC(OCC=3C=CC=CC=3)=CC=2)C=CO1 ZUOUZWHAINARGI-UHFFFAOYSA-N 0.000 title 1
- 239000003602 elastase inhibitor Substances 0.000 title 1
- -1 4-benzyloxyphenyl Chemical group 0.000 claims abstract description 31
- 150000001875 compounds Chemical class 0.000 claims abstract description 23
- 238000000034 method Methods 0.000 claims abstract description 9
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims abstract 7
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 claims abstract 4
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 claims abstract 4
- 125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 claims abstract 4
- 239000004305 biphenyl Substances 0.000 claims abstract 4
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims abstract 4
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 claims abstract 4
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims abstract 4
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims abstract 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract 4
- 150000003839 salts Chemical class 0.000 claims abstract 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 16
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 14
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- 102000004190 Enzymes Human genes 0.000 description 5
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- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
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- VKUYLANQOAKALN-UHFFFAOYSA-N 2-[benzyl-(4-methoxyphenyl)sulfonylamino]-n-hydroxy-4-methylpentanamide Chemical compound C1=CC(OC)=CC=C1S(=O)(=O)N(C(CC(C)C)C(=O)NO)CC1=CC=CC=C1 VKUYLANQOAKALN-UHFFFAOYSA-N 0.000 description 2
- KSAVZSUPQGDMRC-UHFFFAOYSA-N 3-bromofuran-2-carbaldehyde Chemical compound BrC=1C=COC=1C=O KSAVZSUPQGDMRC-UHFFFAOYSA-N 0.000 description 2
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- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
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- BFPSDSIWYFKGBC-UHFFFAOYSA-N chlorotrianisene Chemical compound C1=CC(OC)=CC=C1C(Cl)=C(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 BFPSDSIWYFKGBC-UHFFFAOYSA-N 0.000 description 2
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- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
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- 125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 description 1
- IEQAICDLOKRSRL-UHFFFAOYSA-N 2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-[2-(2-dodecoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethanol Chemical compound CCCCCCCCCCCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCOCCO IEQAICDLOKRSRL-UHFFFAOYSA-N 0.000 description 1
- JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
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- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/4164—1,3-Diazoles
- A61K31/4178—1,3-Diazoles not condensed 1,3-diazoles and containing further heterocyclic rings, e.g. pilocarpine, nitrofurantoin
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Medicinal Chemistry (AREA)
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- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Enzymes And Modification Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US60273604P | 2004-08-19 | 2004-08-19 | |
| US60/602?736 | 2004-08-19 | ||
| US60/602,736 | 2004-08-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2007105822A RU2007105822A (ru) | 2008-09-27 |
| RU2391339C2 true RU2391339C2 (ru) | 2010-06-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2007105822/04A RU2391339C2 (ru) | 2004-08-19 | 2005-08-17 | 5-[3-(4-бензилоксифенилтио)-фур-2-ил]-имидазолидин-2,4-дион и аналоги в качестве ингибиторов эластазы макрофагов |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US7179831B2 (enExample) |
| EP (1) | EP1789036B1 (enExample) |
| JP (1) | JP5042833B2 (enExample) |
| KR (1) | KR101197325B1 (enExample) |
| CN (1) | CN101014338B (enExample) |
| AT (1) | ATE508744T1 (enExample) |
| AU (1) | AU2005277432B2 (enExample) |
| BR (1) | BRPI0514470B8 (enExample) |
| CA (1) | CA2577430C (enExample) |
| DK (1) | DK1789036T3 (enExample) |
| ES (1) | ES2364068T3 (enExample) |
| MX (1) | MX2007001940A (enExample) |
| NZ (1) | NZ553258A (enExample) |
| RU (1) | RU2391339C2 (enExample) |
| SI (1) | SI1789036T1 (enExample) |
| WO (1) | WO2006023562A2 (enExample) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2735600C2 (ru) * | 2016-09-23 | 2020-11-05 | Какен Фармасьютикал Ко., Лтд. | Способ получения (r)-5-(3,4-дифторфенил)-5-[(3-метил-2-оксопиридин-1(2h)-ил)метил]имидазолидин-2,4-диона и промежуточное соединение для его получения |
| RU2766551C1 (ru) * | 2021-07-19 | 2022-03-15 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | 5-(4-хлорфенил)-3-((4-хлорфенил)амино)-5-(фенилтио)фуран-2(5н)-он, обладающий противомикробной активностью |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008051260A1 (en) * | 2006-01-13 | 2008-05-02 | Battelle Memorial Institute | Methods for assessing copd-retlated diseases |
| EP2907512A1 (en) | 2014-02-14 | 2015-08-19 | Commissariat A L'energie Atomique Et Aux Energies Alternatives | Inhibitors of MMP-12 as antiviral Agents |
| US10532102B2 (en) * | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
| ES2910833T3 (es) * | 2016-08-19 | 2022-05-13 | Foresee Pharmaceuticals Co Ltd | Composición farmacéutica y procedimientos de usos |
| FI3793992T3 (fi) | 2018-05-15 | 2024-04-17 | Foresee Pharmaceuticals Usa Inc | Matriksin metalloproteinaasin (mmp) estäjiä ja niiden käyttömenetelmiä |
| DK4058437T3 (da) * | 2019-11-14 | 2025-01-20 | Foresee Pharmaceuticals Usa Inc | Matrix-metalloproteinase-(MMP)-inhibitorer og fremgangsmåder til anvendelse heraf |
| AU2022290589A1 (en) * | 2021-06-08 | 2023-11-23 | Foresee Pharmaceuticals Usa, Inc. | Safe administration of mmp-12 inhibitor |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2150469C1 (ru) * | 1999-06-01 | 2000-06-10 | Уфимский государственный нефтяной технический университет | Способ получения 2-(фурил-2)-1,3-имидазолидинов |
| US20040067996A1 (en) * | 2002-10-04 | 2004-04-08 | James Sheppeck | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE) |
| WO2004108086A2 (en) * | 2003-06-05 | 2004-12-16 | Bristol-Myers Squibb Company | HYDANTOIN DERIVATIVES AS INHIBITORS OF TUMOR NECROSIS FACTOR-α CONVERTING ENZYME (TACE) |
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| WO2000040577A1 (en) | 1998-12-31 | 2000-07-13 | Aventis Pharmaceuticals Inc. | 1-carboxymethyl-2-oxo-azepan derivatives useful as selective inhibitors of mmp-12 |
| US6352976B1 (en) * | 1998-12-31 | 2002-03-05 | Aventis Pharmaceuticals Inc. | Selective inhibitors of MMP-12 |
| EP1288199A4 (en) | 2000-04-28 | 2005-10-12 | Shionogi & Co | INHIBITORS OF MMP-12 |
| SE0100903D0 (sv) | 2001-03-15 | 2001-03-15 | Astrazeneca Ab | Compounds |
| CA2447475A1 (en) | 2001-05-25 | 2002-12-05 | Chu-Biao Xue | Hydantion derivatives as inhibitors of matrix metalloproteinases |
| EP1394159A1 (fr) * | 2002-08-13 | 2004-03-03 | Warner-Lambert Company LLC | Nouveaux dérivés de thiophène, leur procédé de préparation et les compositions pharmaceutiques qui les contiennent |
| GB0219896D0 (en) | 2002-08-27 | 2002-10-02 | Bayer Ag | Dihydropyridine derivatives |
| SE0202539D0 (sv) | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
-
2005
- 2005-08-17 AT AT05786673T patent/ATE508744T1/de not_active IP Right Cessation
- 2005-08-17 CA CA2577430A patent/CA2577430C/en not_active Expired - Fee Related
- 2005-08-17 WO PCT/US2005/029259 patent/WO2006023562A2/en not_active Ceased
- 2005-08-17 MX MX2007001940A patent/MX2007001940A/es active IP Right Grant
- 2005-08-17 EP EP05786673A patent/EP1789036B1/en not_active Expired - Lifetime
- 2005-08-17 DK DK05786673.3T patent/DK1789036T3/da active
- 2005-08-17 NZ NZ553258A patent/NZ553258A/en not_active IP Right Cessation
- 2005-08-17 JP JP2007527975A patent/JP5042833B2/ja not_active Expired - Fee Related
- 2005-08-17 CN CN2005800285556A patent/CN101014338B/zh not_active Expired - Fee Related
- 2005-08-17 BR BRPI0514470A patent/BRPI0514470B8/pt not_active IP Right Cessation
- 2005-08-17 ES ES05786673T patent/ES2364068T3/es not_active Expired - Lifetime
- 2005-08-17 AU AU2005277432A patent/AU2005277432B2/en not_active Ceased
- 2005-08-17 SI SI200531283T patent/SI1789036T1/sl unknown
- 2005-08-17 RU RU2007105822/04A patent/RU2391339C2/ru not_active IP Right Cessation
- 2005-08-17 US US11/205,954 patent/US7179831B2/en not_active Expired - Lifetime
- 2005-08-17 KR KR1020077006294A patent/KR101197325B1/ko not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2150469C1 (ru) * | 1999-06-01 | 2000-06-10 | Уфимский государственный нефтяной технический университет | Способ получения 2-(фурил-2)-1,3-имидазолидинов |
| US20040067996A1 (en) * | 2002-10-04 | 2004-04-08 | James Sheppeck | Hydantoin derivatives as inhibitors of matrix metalloproteinases and/or TNF-alpha converting enzyme (TACE) |
| WO2004108086A2 (en) * | 2003-06-05 | 2004-12-16 | Bristol-Myers Squibb Company | HYDANTOIN DERIVATIVES AS INHIBITORS OF TUMOR NECROSIS FACTOR-α CONVERTING ENZYME (TACE) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2735600C2 (ru) * | 2016-09-23 | 2020-11-05 | Какен Фармасьютикал Ко., Лтд. | Способ получения (r)-5-(3,4-дифторфенил)-5-[(3-метил-2-оксопиридин-1(2h)-ил)метил]имидазолидин-2,4-диона и промежуточное соединение для его получения |
| RU2766551C1 (ru) * | 2021-07-19 | 2022-03-15 | Федеральное государственное автономное образовательное учреждение высшего образования "Пермский государственный национальный исследовательский университет" (ПГНИУ) | 5-(4-хлорфенил)-3-((4-хлорфенил)амино)-5-(фенилтио)фуран-2(5н)-он, обладающий противомикробной активностью |
Also Published As
| Publication number | Publication date |
|---|---|
| CA2577430A1 (en) | 2006-03-02 |
| SI1789036T1 (sl) | 2011-09-30 |
| WO2006023562B1 (en) | 2006-06-22 |
| HK1107774A1 (en) | 2008-04-18 |
| DK1789036T3 (da) | 2011-06-27 |
| RU2007105822A (ru) | 2008-09-27 |
| CN101014338B (zh) | 2010-06-16 |
| BRPI0514470B1 (pt) | 2021-01-05 |
| JP5042833B2 (ja) | 2012-10-03 |
| KR20070045330A (ko) | 2007-05-02 |
| CN101014338A (zh) | 2007-08-08 |
| NZ553258A (en) | 2011-02-25 |
| EP1789036B1 (en) | 2011-05-11 |
| MX2007001940A (es) | 2007-07-24 |
| BRPI0514470A (pt) | 2008-06-10 |
| KR101197325B1 (ko) | 2012-11-05 |
| ATE508744T1 (de) | 2011-05-15 |
| WO2006023562A3 (en) | 2006-04-20 |
| WO2006023562A2 (en) | 2006-03-02 |
| EP1789036A2 (en) | 2007-05-30 |
| BRPI0514470B8 (pt) | 2021-07-20 |
| AU2005277432B2 (en) | 2011-11-24 |
| US7179831B2 (en) | 2007-02-20 |
| CA2577430C (en) | 2010-12-07 |
| ES2364068T3 (es) | 2011-08-24 |
| JP2008510701A (ja) | 2008-04-10 |
| EP1789036A4 (en) | 2008-08-27 |
| US20060041000A1 (en) | 2006-02-23 |
| AU2005277432A1 (en) | 2006-03-02 |
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