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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- mmp
- methoxyphenyl
- chlorophenyl
- methylphenyl
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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
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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
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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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- 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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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P13/12—Drugs for disorders of the urinary system of the kidneys
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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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- A61P19/02—Drugs for skeletal disorders for joint disorders, e.g. arthritis, arthrosis
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- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
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- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
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- Immunology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Rheumatology (AREA)
- Physical Education & Sports Medicine (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
ID=35968136
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 (https=) |
| EP (1) | EP1789036B1 (https=) |
| JP (1) | JP5042833B2 (https=) |
| KR (1) | KR101197325B1 (https=) |
| CN (1) | CN101014338B (https=) |
| AT (1) | ATE508744T1 (https=) |
| AU (1) | AU2005277432B2 (https=) |
| BR (1) | BRPI0514470B8 (https=) |
| CA (1) | CA2577430C (https=) |
| DK (1) | DK1789036T3 (https=) |
| ES (1) | ES2364068T3 (https=) |
| MX (1) | MX2007001940A (https=) |
| NZ (1) | NZ553258A (https=) |
| RU (1) | RU2391339C2 (https=) |
| SI (1) | SI1789036T1 (https=) |
| WO (1) | WO2006023562A2 (https=) |
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 |
|---|---|---|---|---|
| WO2007084485A2 (en) * | 2006-01-13 | 2007-07-26 | Battelle Memorial Institute | Markers for assessing copd-related 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 |
| MX387820B (es) * | 2016-08-19 | 2025-03-18 | Foresee Pharmaceuticals Co Ltd | Composición farmacéutica y métodos de usos. |
| US10532102B2 (en) * | 2016-08-19 | 2020-01-14 | Foresee Pharmaceuticals Co., Ltd. | Pharmaceutical composition and methods of uses |
| SI3793995T1 (sl) | 2018-05-15 | 2024-05-31 | Foresee Pharmaceuticals Usa, Inc. | Zaviralci matrične metaloproteinaze (mmp)in načini njihove uporabe |
| CA3158234A1 (en) * | 2019-11-14 | 2021-05-20 | Foresee Pharmaceuticals Co., Ltd. | Matrix metalloproteinase (mmp) inhibitors and methods of use thereof |
| EP4351566A4 (en) * | 2021-06-08 | 2025-04-23 | 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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| Publication number | Priority date | Publication date | Assignee | Title |
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| EP1150975A1 (en) | 1998-12-31 | 2001-11-07 | 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 |
| US6890915B2 (en) | 2001-05-25 | 2005-05-10 | Bristol-Myers Squibb Pharma Company | Hydantoins and related heterocycles as inhibitors of matrix metalloproteinases and/or TNF-α converting enzyme (TACE) |
| 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 |
| SE0202539D0 (sv) * | 2002-08-27 | 2002-08-27 | Astrazeneca Ab | Compounds |
| GB0219896D0 (en) | 2002-08-27 | 2002-10-02 | Bayer Ag | Dihydropyridine derivatives |
-
2005
- 2005-08-17 JP JP2007527975A patent/JP5042833B2/ja not_active Expired - Fee Related
- 2005-08-17 CA CA2577430A patent/CA2577430C/en not_active Expired - Fee Related
- 2005-08-17 NZ NZ553258A patent/NZ553258A/en not_active IP Right Cessation
- 2005-08-17 ES ES05786673T patent/ES2364068T3/es not_active Expired - Lifetime
- 2005-08-17 SI SI200531283T patent/SI1789036T1/sl unknown
- 2005-08-17 CN CN2005800285556A patent/CN101014338B/zh not_active Expired - Fee Related
- 2005-08-17 DK DK05786673.3T patent/DK1789036T3/da active
- 2005-08-17 AU AU2005277432A patent/AU2005277432B2/en not_active Ceased
- 2005-08-17 AT AT05786673T patent/ATE508744T1/de not_active IP Right Cessation
- 2005-08-17 WO PCT/US2005/029259 patent/WO2006023562A2/en not_active Ceased
- 2005-08-17 EP EP05786673A patent/EP1789036B1/en not_active Expired - Lifetime
- 2005-08-17 US US11/205,954 patent/US7179831B2/en not_active Expired - Lifetime
- 2005-08-17 MX MX2007001940A patent/MX2007001940A/es active IP Right Grant
- 2005-08-17 RU RU2007105822/04A patent/RU2391339C2/ru not_active IP Right Cessation
- 2005-08-17 KR KR1020077006294A patent/KR101197325B1/ko not_active Expired - Fee Related
- 2005-08-17 BR BRPI0514470A patent/BRPI0514470B8/pt not_active IP Right Cessation
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 |
|---|---|
| EP1789036A2 (en) | 2007-05-30 |
| ES2364068T3 (es) | 2011-08-24 |
| SI1789036T1 (sl) | 2011-09-30 |
| KR20070045330A (ko) | 2007-05-02 |
| DK1789036T3 (da) | 2011-06-27 |
| RU2007105822A (ru) | 2008-09-27 |
| CN101014338B (zh) | 2010-06-16 |
| WO2006023562A2 (en) | 2006-03-02 |
| WO2006023562A3 (en) | 2006-04-20 |
| WO2006023562B1 (en) | 2006-06-22 |
| US7179831B2 (en) | 2007-02-20 |
| AU2005277432A1 (en) | 2006-03-02 |
| AU2005277432B2 (en) | 2011-11-24 |
| NZ553258A (en) | 2011-02-25 |
| EP1789036B1 (en) | 2011-05-11 |
| US20060041000A1 (en) | 2006-02-23 |
| HK1107774A1 (en) | 2008-04-18 |
| MX2007001940A (es) | 2007-07-24 |
| KR101197325B1 (ko) | 2012-11-05 |
| EP1789036A4 (en) | 2008-08-27 |
| JP5042833B2 (ja) | 2012-10-03 |
| BRPI0514470A (pt) | 2008-06-10 |
| BRPI0514470B8 (pt) | 2021-07-20 |
| CA2577430A1 (en) | 2006-03-02 |
| JP2008510701A (ja) | 2008-04-10 |
| CA2577430C (en) | 2010-12-07 |
| CN101014338A (zh) | 2007-08-08 |
| ATE508744T1 (de) | 2011-05-15 |
| BRPI0514470B1 (pt) | 2021-01-05 |
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