CA2515940C - Substituted heterocycles - Google Patents
Substituted heterocycles Download PDFInfo
- Publication number
- CA2515940C CA2515940C CA2515940A CA2515940A CA2515940C CA 2515940 C CA2515940 C CA 2515940C CA 2515940 A CA2515940 A CA 2515940A CA 2515940 A CA2515940 A CA 2515940A CA 2515940 C CA2515940 C CA 2515940C
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- CA
- Canada
- Prior art keywords
- compound
- hydroxy
- formula
- methyl
- salt
- 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.)
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 27
- 150000003839 salts Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 14
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- QEOQCQQSHXAFLY-UHFFFAOYSA-N s-cyclohexyl 2-[cyclohex-2-en-1-yl(hydroxy)methyl]-4-hexyl-3-hydroxy-3-methyl-5-oxopyrrolidine-2-carbothioate Chemical compound CC1(O)C(CCCCCC)C(=O)NC1(C(=O)SC1CCCCC1)C(O)C1C=CCCC1 QEOQCQQSHXAFLY-UHFFFAOYSA-N 0.000 description 1
- 239000000523 sample Substances 0.000 description 1
- 239000012723 sample buffer Substances 0.000 description 1
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- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 241000380967 soil bacterium S31M1 Species 0.000 description 1
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- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000011975 tartaric acid Chemical class 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- WROMPOXWARCANT-UHFFFAOYSA-N tfa trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.OC(=O)C(F)(F)F WROMPOXWARCANT-UHFFFAOYSA-N 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000000341 threoninyl group Chemical group [H]OC([H])(C([H])([H])[H])C([H])(N([H])[H])C(*)=O 0.000 description 1
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- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
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- 239000003643 water by type Substances 0.000 description 1
- 238000001262 western blot Methods 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 238000012982 x-ray structure analysis Methods 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
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- 229910052725 zinc Inorganic materials 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member 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
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones 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 other ring carbon atoms
- C07D207/277—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- General Health & Medical Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Microbiology (AREA)
- General Engineering & Computer Science (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Virology (AREA)
- Pulmonology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyrrole Compounds (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP03003495 | 2003-02-14 | ||
| EP03003495.3 | 2003-02-14 | ||
| EP03007594.9 | 2003-04-02 | ||
| EP03007594 | 2003-04-02 | ||
| PCT/EP2004/001097 WO2004071382A2 (en) | 2003-02-14 | 2004-02-06 | Substituted heterocycles |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2515940A1 CA2515940A1 (en) | 2004-08-26 |
| CA2515940C true CA2515940C (en) | 2011-12-06 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2515940A Expired - Fee Related CA2515940C (en) | 2003-02-14 | 2004-02-06 | Substituted heterocycles |
Country Status (15)
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| Publication number | Priority date | Publication date | Assignee | Title |
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| AU4322802A (en) | 2000-11-16 | 2002-06-24 | Univ California | Marine actinomycete taxon for drug and fermentation product dicovery |
| US7176232B2 (en) | 2002-06-24 | 2007-02-13 | The Regents Of The University Of California | Salinosporamides and methods for use thereof |
| NZ544858A (en) * | 2003-06-20 | 2009-07-31 | Univ California | Salinosporamides and methods for use thereof |
| CA2532066C (en) * | 2003-06-20 | 2015-07-28 | Nereus Pharmaceuticals, Inc. | Methods of using [3.2.0] heterocyclic compounds and analogs thereof |
| WO2005099687A2 (en) * | 2004-04-09 | 2005-10-27 | President And Fellows Of Harvard College | Analogs of salinosporamide a |
| EP2266988A1 (en) * | 2004-04-30 | 2010-12-29 | Nereus Pharmaceuticals, Inc. | [3.2.0] Heterocyclic compounds and methods of using the same |
| US7579371B2 (en) | 2004-04-30 | 2009-08-25 | Nereus Pharmaceuticals, Inc. | Methods of using [3.2.0] heterocyclic compounds and analogs thereof |
| JP2008505956A (ja) * | 2004-07-12 | 2008-02-28 | バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト | 真菌駆除剤および昆虫駆除剤としての置換されている２−ピロリドン誘導体 |
| BRPI0517134A2 (pt) * | 2004-12-03 | 2011-10-11 | Nereus Pharmaceuticals Inc | métodos de uso de compostos heterocìclicos [ 3.2.0 ] e seus análogos |
| PL1830838T3 (pl) * | 2004-12-03 | 2013-07-31 | Dana Farber Cancer Inst Inc | Kompozycje i sposoby leczenia chorób neoplastycznych |
| WO2006118973A2 (en) * | 2005-04-29 | 2006-11-09 | Nereus Pharmaceuticals, Inc. | Methods of using heterobyclic compounds for treatment of rectal cancer |
| US7465720B2 (en) | 2005-09-12 | 2008-12-16 | President And Fellows Of Harvard College | Proteasome inhibiting β-lactam compounds |
| JP2009532484A (ja) | 2006-04-06 | 2009-09-10 | ネレアス ファーマシューティカルズ インコーポレイテッド | サリノスポラミドａ及びその類縁体の全合成 |
| US7824698B2 (en) * | 2007-02-02 | 2010-11-02 | Nereus Pharmaceuticals, Inc. | Lyophilized formulations of Salinosporamide A |
| WO2008137780A2 (en) * | 2007-05-04 | 2008-11-13 | Nereus Pharmaceuticals, Inc. | Use of [3.2.0] heterocyclic compounds and analogs thereof for treating infectious diseases |
| US8394816B2 (en) | 2007-12-07 | 2013-03-12 | Irene Ghobrial | Methods of using [3.2.0] heterocyclic compounds and analogs thereof in treating Waldenstrom's Macroglobulinemia |
| EP2088205A1 (en) | 2008-02-11 | 2009-08-12 | Institut National De La Sante Et De La Recherche Medicale (Inserm) | PSMB10: A diagnosis marker and therapeutic target of chronic rejection. |
| MX2010009860A (es) | 2008-03-07 | 2010-09-30 | Nereus Pharmaceuticals Inc | Sintesis total de salinosporamida a y sus analogos. |
| KR20110011645A (ko) | 2008-05-12 | 2011-02-08 | 니리어스 파마슈티컬즈, 인코퍼레이션 | 프로테아좀 저해제로서의 살리노스포라마이드 유도체 |
| EP2399129B1 (en) | 2009-02-20 | 2015-11-25 | Michael P. Lisanti | A method of diagnosis or prognosis of a neoplasm comprising determining the level of expression of a protein in stromal cells adjacent to the neoplasm |
| US9126997B1 (en) | 2010-09-07 | 2015-09-08 | Northwestern University | Synergistic effect of glucocorticoid receptor agonists in combination with proteosome inhibitors for treating leukemia and myeloma |
| ES2776144T3 (es) | 2011-10-28 | 2020-07-29 | Millennium Pharm Inc | Biomarcadores de respuesta a inhibidores de NAE |
| US20150184246A1 (en) | 2011-11-11 | 2015-07-02 | Millennium Pharmaceuticals, Inc. | Biomarkers of response to proteasome inhibitors |
| WO2013112601A1 (en) | 2012-01-24 | 2013-08-01 | Millennium Pharmaceuticals, Inc. | Methods of treatment of cancer |
| WO2013112881A1 (en) | 2012-01-27 | 2013-08-01 | Thomas Jefferson University | Mct protein inhibitor-related prognostic and therapeutic methods |
| CN104822844B (zh) | 2012-10-01 | 2019-05-07 | 米伦纽姆医药公司 | 预测对抑制剂的反应的生物标记物和方法以及其用途 |
| EP2986290A4 (en) | 2013-04-19 | 2017-01-04 | Thomas Jefferson University | Caveolin-1 related methods for treating glioblastoma with temozolomide |
| EP3339291A1 (en) | 2016-12-22 | 2018-06-27 | Vita Api | Proteasome inhibiting ss-lactam prodrugs useful for the treatment of cancer and neurodegenerative disorders |
Family Cites Families (2)
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| US6335358B1 (en) * | 1995-04-12 | 2002-01-01 | President And Fellows Of Harvard College | Lactacystin analogs |
| AU4322802A (en) * | 2000-11-16 | 2002-06-24 | Univ California | Marine actinomycete taxon for drug and fermentation product dicovery |
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2004
- 2004-02-06 ES ES04708731T patent/ES2336562T3/es not_active Expired - Lifetime
- 2004-02-06 CN CN2004800093759A patent/CN1845925B/zh not_active Expired - Fee Related
- 2004-02-06 KR KR1020057014935A patent/KR20050098928A/ko not_active Abandoned
- 2004-02-06 JP JP2006501755A patent/JP4795931B2/ja not_active Expired - Fee Related
- 2004-02-06 MX MXPA05008478 patent/MX272108B/es active IP Right Grant
- 2004-02-06 WO PCT/EP2004/001097 patent/WO2004071382A2/en active Application Filing
- 2004-02-06 EP EP04708731A patent/EP1597262B1/en not_active Expired - Lifetime
- 2004-02-06 CA CA2515940A patent/CA2515940C/en not_active Expired - Fee Related
- 2004-02-06 AT AT04708731T patent/ATE448232T1/de not_active IP Right Cessation
- 2004-02-06 AU AU2004212296A patent/AU2004212296B2/en not_active Ceased
- 2004-02-06 IN IN3350DE2005 patent/IN228043B/en unknown
- 2004-02-06 US US10/545,449 patent/US20060229353A1/en not_active Abandoned
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- 2004-02-06 BR BR0407234-0A patent/BRPI0407234A/pt not_active IP Right Cessation
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2005
- 2005-07-26 IL IL169897A patent/IL169897A0/en unknown
-
2009
- 2009-01-08 US US12/350,696 patent/US20110015248A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| US20110015248A1 (en) | 2011-01-20 |
| IL169897A0 (en) | 2007-07-04 |
| JP4795931B2 (ja) | 2011-10-19 |
| BRPI0407234A (pt) | 2006-01-31 |
| IN228043B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2009-02-13 |
| EP1597262B1 (en) | 2009-11-11 |
| AU2004212296B2 (en) | 2010-06-17 |
| WO2004071382A2 (en) | 2004-08-26 |
| WO2004071382A3 (en) | 2005-01-06 |
| HK1096392A1 (en) | 2007-06-01 |
| IN2005DE03350A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 2007-06-01 |
| MX272108B (es) | 2009-11-25 |
| US20060229353A1 (en) | 2006-10-12 |
| ES2336562T3 (es) | 2010-04-14 |
| MXPA05008478A (es) | 2005-10-18 |
| CA2515940A1 (en) | 2004-08-26 |
| JP2006517934A (ja) | 2006-08-03 |
| DE602004024037D1 (de) | 2009-12-24 |
| AU2004212296A1 (en) | 2004-08-26 |
| CN1845925B (zh) | 2010-11-03 |
| CN1845925A (zh) | 2006-10-11 |
| KR20050098928A (ko) | 2005-10-12 |
| EP1597262A2 (en) | 2005-11-23 |
| ATE448232T1 (de) | 2009-11-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20130206 |