CA2605760A1 - New thiazolidinones without basic nitrogen, their production and use as pharmaceutical agents - Google Patents
New thiazolidinones without basic nitrogen, their production and use as pharmaceutical agents Download PDFInfo
- Publication number
- CA2605760A1 CA2605760A1 CA002605760A CA2605760A CA2605760A1 CA 2605760 A1 CA2605760 A1 CA 2605760A1 CA 002605760 A CA002605760 A CA 002605760A CA 2605760 A CA2605760 A CA 2605760A CA 2605760 A1 CA2605760 A1 CA 2605760A1
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- CA
- Canada
- Prior art keywords
- optionally
- ring
- nr3r4
- heterocycloalkyl
- alkyl
- 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.)
- Abandoned
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- 238000004519 manufacturing process Methods 0.000 title claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 title claims description 74
- 229910052757 nitrogen Inorganic materials 0.000 title claims description 38
- 239000008177 pharmaceutical agent Substances 0.000 title claims description 13
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 15
- 239000003112 inhibitor Substances 0.000 claims abstract description 8
- 101000582926 Dictyostelium discoideum Probable serine/threonine-protein kinase PLK Proteins 0.000 claims abstract description 7
- -1 C3-cycloalkyl Chemical group 0.000 claims description 67
- 229910052736 halogen Inorganic materials 0.000 claims description 64
- 150000002367 halogens Chemical class 0.000 claims description 64
- 150000001875 compounds Chemical class 0.000 claims description 47
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 45
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 229910052760 oxygen Inorganic materials 0.000 claims description 35
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 34
- 239000001301 oxygen Substances 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 33
- 125000003118 aryl group Chemical group 0.000 claims description 32
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 29
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000004434 sulfur atom Chemical group 0.000 claims description 22
- 206010028980 Neoplasm Diseases 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 239000001257 hydrogen Substances 0.000 claims description 20
- 125000006577 C1-C6 hydroxyalkyl group Chemical group 0.000 claims description 19
- 238000000034 method Methods 0.000 claims description 16
- 150000003839 salts Chemical class 0.000 claims description 14
- 201000011510 cancer Diseases 0.000 claims description 13
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
- 229910052717 sulfur Inorganic materials 0.000 claims description 12
- 239000011593 sulfur Substances 0.000 claims description 12
- 108091000080 Phosphotransferase Proteins 0.000 claims description 11
- 230000004770 neurodegeneration Effects 0.000 claims description 11
- 208000015122 neurodegenerative disease Diseases 0.000 claims description 11
- 102000020233 phosphotransferase Human genes 0.000 claims description 11
- 150000004677 hydrates Chemical class 0.000 claims description 10
- 239000012453 solvate Substances 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
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- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
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- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 7
- 201000004384 Alopecia Diseases 0.000 claims description 6
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- 239000000203 mixture Substances 0.000 claims description 6
- 125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 230000001154 acute effect Effects 0.000 claims description 5
- 230000001684 chronic effect Effects 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
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- XQFRJNBWHJMXHO-RRKCRQDMSA-N IDUR Chemical compound C1[C@H](O)[C@@H](CO)O[C@H]1N1C(=O)NC(=O)C(I)=C1 XQFRJNBWHJMXHO-RRKCRQDMSA-N 0.000 claims description 3
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
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- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 38
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 24
- 125000006728 (C1-C6) alkynyl group Chemical group 0.000 claims 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 6
- 125000006727 (C1-C6) alkenyl group Chemical group 0.000 claims 4
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 2
- QDQOWPROXUVFAH-NHERBMIYSA-N (2z)-2-[(5z)-5-[(4-bromophenyl)methylidene]-3-ethyl-4-oxo-1,3-thiazolidin-2-ylidene]-2-cyano-n-ethylacetamide Chemical compound O=C1N(CC)C(=C(\C#N)C(=O)NCC)/S\C1=C/C1=CC=C(Br)C=C1 QDQOWPROXUVFAH-NHERBMIYSA-N 0.000 claims 1
- WCUPYUNZBJILQE-ZLHHJAJDSA-N (2z)-2-cyano-2-[(5z)-3-ethyl-4-oxo-5-[(4-pyrrolidin-1-ylphenyl)methylidene]-1,3-thiazolidin-2-ylidene]-n-prop-2-ynylacetamide Chemical compound S1\C(=C(\C#N)C(=O)NCC#C)N(CC)C(=O)\C1=C\C1=CC=C(N2CCCC2)C=C1 WCUPYUNZBJILQE-ZLHHJAJDSA-N 0.000 claims 1
- FMQOESLCPZJIDB-SOUBVSJWSA-N (2z)-2-cyano-2-[(5z)-3-ethyl-5-[(3-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-n-(1-hydroxy-2-methylpropan-2-yl)acetamide Chemical compound S1\C(=C(\C#N)C(=O)NC(C)(C)CO)N(CC)C(=O)\C1=C\C1=CC=CC(O)=C1 FMQOESLCPZJIDB-SOUBVSJWSA-N 0.000 claims 1
- RXMFMJABFPXKJA-SOUBVSJWSA-N (2z)-2-cyano-2-[(5z)-3-ethyl-5-[(3-nitrophenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-n-(1-hydroxy-2-methylpropan-2-yl)acetamide Chemical compound S1\C(=C(\C#N)C(=O)NC(C)(C)CO)N(CC)C(=O)\C1=C\C1=CC=CC([N+]([O-])=O)=C1 RXMFMJABFPXKJA-SOUBVSJWSA-N 0.000 claims 1
- YEXAZUTZGUZIDV-GQIGLLADSA-N (2z)-2-cyano-2-[(5z)-3-ethyl-5-[(4-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]-n-prop-2-ynylacetamide Chemical compound S1\C(=C(\C#N)C(=O)NCC#C)N(CC)C(=O)\C1=C\C1=CC=C(O)C=C1 YEXAZUTZGUZIDV-GQIGLLADSA-N 0.000 claims 1
- XBZYCRQHURWCLE-NHERBMIYSA-N (2z)-2-cyano-n-ethyl-2-[(5z)-3-ethyl-5-[(3-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]acetamide Chemical compound O=C1N(CC)C(=C(\C#N)C(=O)NCC)/S\C1=C/C1=CC=CC(O)=C1 XBZYCRQHURWCLE-NHERBMIYSA-N 0.000 claims 1
- ZXFMKMUIRXXIIH-NHERBMIYSA-N (2z)-2-cyano-n-ethyl-2-[(5z)-3-ethyl-5-[(4-hydroxyphenyl)methylidene]-4-oxo-1,3-thiazolidin-2-ylidene]acetamide Chemical compound O=C1N(CC)C(=C(\C#N)C(=O)NCC)/S\C1=C/C1=CC=C(O)C=C1 ZXFMKMUIRXXIIH-NHERBMIYSA-N 0.000 claims 1
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- 108010056274 polo-like kinase 1 Proteins 0.000 claims 1
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 66
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
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- 125000004432 carbon atom Chemical group C* 0.000 description 13
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 10
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- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
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- A—HUMAN NECESSITIES
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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
- A61K31/425—Thiazoles
- A61K31/426—1,3-Thiazoles
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/34—Oxygen atoms
-
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing aromatic rings
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
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- Life Sciences & Earth Sciences (AREA)
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- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
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- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Orthopedic Medicine & Surgery (AREA)
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Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102005020105 | 2005-04-25 | ||
| DE102005020105A DE102005020105A1 (de) | 2005-04-25 | 2005-04-25 | Neue Thiazolidinone ohne basischen Stickstoff, deren Herstellung und Verwendung als Arzneimittel |
| PCT/EP2006/004226 WO2006114334A1 (en) | 2005-04-25 | 2006-04-24 | New thiazolidinones without basic nitrogen, their production and use as pharmaceutical agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2605760A1 true CA2605760A1 (en) | 2006-11-02 |
Family
ID=36693046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002605760A Abandoned CA2605760A1 (en) | 2005-04-25 | 2006-04-24 | New thiazolidinones without basic nitrogen, their production and use as pharmaceutical agents |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP1874744A1 (zh) |
| JP (1) | JP2008538756A (zh) |
| KR (1) | KR20080005971A (zh) |
| CN (1) | CN101208317A (zh) |
| AU (1) | AU2006239444A1 (zh) |
| BR (1) | BRPI0610832A2 (zh) |
| CA (1) | CA2605760A1 (zh) |
| DE (1) | DE102005020105A1 (zh) |
| IL (1) | IL186747A0 (zh) |
| MX (1) | MX2007013306A (zh) |
| NO (1) | NO20076038L (zh) |
| RU (1) | RU2007143513A (zh) |
| WO (1) | WO2006114334A1 (zh) |
| ZA (1) | ZA200710147B (zh) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2014069434A1 (ja) * | 2012-10-30 | 2014-05-08 | カルナバイオサイエンス株式会社 | 新規チアゾリジノン誘導体 |
| JP6480629B1 (ja) * | 2018-08-07 | 2019-03-13 | キッコーマン株式会社 | グルコースデヒドロゲナーゼの組換え製造方法 |
| CN113533723B (zh) * | 2021-07-28 | 2023-06-20 | 中国医科大学附属第一医院 | 一种被hiv和/或siv感染的细胞的标志物及其应用 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DD147241A1 (de) * | 1979-11-21 | 1981-03-25 | Klaus Peseke | Verfahren zur herstellung von furanderivaten |
| DD267492A1 (de) * | 1987-12-01 | 1989-05-03 | Univ Rostock | Verfahren zur herstellung von thiazolidinderivaten |
| JP2005538048A (ja) * | 2002-05-03 | 2005-12-15 | シエーリング アクチエンゲゼルシャフト | チアゾリジノン類、それらの生成及び医薬剤としての使用 |
| US20040092561A1 (en) * | 2002-11-07 | 2004-05-13 | Thomas Ruckle | Azolidinone-vinyl fused -benzene derivatives |
-
2005
- 2005-04-25 DE DE102005020105A patent/DE102005020105A1/de not_active Ceased
-
2006
- 2006-04-24 MX MX2007013306A patent/MX2007013306A/es not_active Application Discontinuation
- 2006-04-24 CN CNA2006800228878A patent/CN101208317A/zh active Pending
- 2006-04-24 CA CA002605760A patent/CA2605760A1/en not_active Abandoned
- 2006-04-24 EP EP06742815A patent/EP1874744A1/en not_active Withdrawn
- 2006-04-24 BR BRPI0610832-6A patent/BRPI0610832A2/pt not_active Application Discontinuation
- 2006-04-24 AU AU2006239444A patent/AU2006239444A1/en not_active Abandoned
- 2006-04-24 RU RU2007143513/04A patent/RU2007143513A/ru unknown
- 2006-04-24 WO PCT/EP2006/004226 patent/WO2006114334A1/en active Application Filing
- 2006-04-24 JP JP2008507025A patent/JP2008538756A/ja active Pending
- 2006-04-24 KR KR1020077027261A patent/KR20080005971A/ko not_active Application Discontinuation
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2007
- 2007-10-18 IL IL186747A patent/IL186747A0/en unknown
- 2007-11-23 NO NO20076038A patent/NO20076038L/no not_active Application Discontinuation
- 2007-11-26 ZA ZA200710147A patent/ZA200710147B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU2006239444A1 (en) | 2006-11-02 |
| RU2007143513A (ru) | 2009-06-10 |
| WO2006114334A1 (en) | 2006-11-02 |
| KR20080005971A (ko) | 2008-01-15 |
| IL186747A0 (en) | 2008-02-09 |
| NO20076038L (no) | 2008-01-16 |
| BRPI0610832A2 (pt) | 2010-07-27 |
| JP2008538756A (ja) | 2008-11-06 |
| DE102005020105A1 (de) | 2006-10-26 |
| CN101208317A (zh) | 2008-06-25 |
| EP1874744A1 (en) | 2008-01-09 |
| ZA200710147B (en) | 2009-08-26 |
| MX2007013306A (es) | 2007-12-13 |
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| Date | Code | Title | Description |
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| FZDE | Discontinued |