CA2450202A1 - Macrocycles useful in the treatment of alzheimer's disease - Google Patents
Macrocycles useful in the treatment of alzheimer's disease Download PDFInfo
- Publication number
- CA2450202A1 CA2450202A1 CA002450202A CA2450202A CA2450202A1 CA 2450202 A1 CA2450202 A1 CA 2450202A1 CA 002450202 A CA002450202 A CA 002450202A CA 2450202 A CA2450202 A CA 2450202A CA 2450202 A1 CA2450202 A1 CA 2450202A1
- Authority
- CA
- Canada
- Prior art keywords
- ethyl
- alkyl
- fluoro
- optionally substituted
- oxa
- 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
Links
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- 125000001042 pteridinyl group Chemical group N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000003226 pyrazolyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
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- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 229960001404 quinidine Drugs 0.000 description 1
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- 125000004620 quinolinyl-N-oxide group Chemical group 0.000 description 1
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- 238000012552 review Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- NCDNCNXCDXHOMX-XGKFQTDJSA-N ritonavir Chemical compound N([C@@H](C(C)C)C(=O)N[C@H](C[C@H](O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1SC=NC=1)CC=1C=CC=CC=1)C(=O)N(C)CC1=CSC(C(C)C)=N1 NCDNCNXCDXHOMX-XGKFQTDJSA-N 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
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- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- 238000009738 saturating Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
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- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- QFJCIRLUMZQUOT-HPLJOQBZSA-N sirolimus Chemical compound C1C[C@@H](O)[C@H](OC)C[C@@H]1C[C@@H](C)[C@H]1OC(=O)[C@@H]2CCCCN2C(=O)C(=O)[C@](O)(O2)[C@H](C)CC[C@H]2C[C@H](OC)/C(C)=C/C=C/C=C/[C@@H](C)C[C@@H](C)C(=O)[C@H](OC)[C@H](O)/C(C)=C/[C@@H](C)C(=O)C1 QFJCIRLUMZQUOT-HPLJOQBZSA-N 0.000 description 1
- 229960002930 sirolimus Drugs 0.000 description 1
- WBHQBSYUUJJSRZ-UHFFFAOYSA-M sodium bisulfate Chemical compound [Na+].OS([O-])(=O)=O WBHQBSYUUJJSRZ-UHFFFAOYSA-M 0.000 description 1
- 229910000342 sodium bisulfate Inorganic materials 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
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- 229960001603 tamoxifen Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- QJPROAFAUVCYBP-UHFFFAOYSA-N tert-butyl n-[(3-ethylphenyl)methyl]-n-[4-(3-fluoro-5-phenylmethoxyphenyl)-2-hydroxy-3-[[2-(phenylmethoxycarbonylamino)acetyl]amino]butyl]carbamate Chemical compound CCC1=CC=CC(CN(CC(O)C(CC=2C=C(OCC=3C=CC=CC=3)C=C(F)C=2)NC(=O)CNC(=O)OCC=2C=CC=CC=2)C(=O)OC(C)(C)C)=C1 QJPROAFAUVCYBP-UHFFFAOYSA-N 0.000 description 1
- GMJZDMOCYCKGJF-UHFFFAOYSA-N tert-butyl n-[3-[(2-aminoacetyl)amino]-4-(3-fluoro-5-hydroxyphenyl)-2-hydroxybutyl]-n-[(3-ethylphenyl)methyl]carbamate Chemical compound CCC1=CC=CC(CN(CC(O)C(CC=2C=C(F)C=C(O)C=2)NC(=O)CN)C(=O)OC(C)(C)C)=C1 GMJZDMOCYCKGJF-UHFFFAOYSA-N 0.000 description 1
- ILMRJRBKQSSXGY-UHFFFAOYSA-N tert-butyl(dimethyl)silicon Chemical group C[Si](C)C(C)(C)C ILMRJRBKQSSXGY-UHFFFAOYSA-N 0.000 description 1
- 125000003718 tetrahydrofuranyl group Chemical group 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
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- 125000000147 tetrahydroquinolinyl group Chemical group N1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
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- 238000001890 transfection Methods 0.000 description 1
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- 125000001425 triazolyl group Chemical group 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229950010938 valspodar Drugs 0.000 description 1
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- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960001722 verapamil Drugs 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
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- 235000019165 vitamin E Nutrition 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
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- IHOVFYSQUDPMCN-QKUIIBHLSA-N zosuquidar Chemical compound C([C@H](COC=1C2=CC=CN=C2C=CC=1)O)N(CC1)CCN1C1C2=CC=CC=C2C2C(F)(F)C2C2=CC=CC=C12 IHOVFYSQUDPMCN-QKUIIBHLSA-N 0.000 description 1
- 125000004933 β-carbolinyl group Chemical group C1(=NC=CC=2C3=CC=CC=C3NC12)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D273/00—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00
- C07D273/02—Heterocyclic compounds containing rings having nitrogen and oxygen atoms as the only ring hetero atoms, not provided for by groups C07D261/00 - C07D271/00 having two nitrogen atoms and only one oxygen atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Neurosurgery (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Hospice & Palliative Care (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Psychiatry (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US29754601P | 2001-06-12 | 2001-06-12 | |
| US60/297,546 | 2001-06-12 | ||
| US33308301P | 2001-11-19 | 2001-11-19 | |
| US60/333,083 | 2001-11-19 | ||
| PCT/US2002/019076 WO2002100856A1 (en) | 2001-06-12 | 2002-06-12 | Macrocycles useful in the treatment of alzheimer's disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2450202A1 true CA2450202A1 (en) | 2002-12-19 |
Family
ID=26970209
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002450202A Abandoned CA2450202A1 (en) | 2001-06-12 | 2002-06-12 | Macrocycles useful in the treatment of alzheimer's disease |
Country Status (10)
| Country | Link |
|---|---|
| US (2) | US6969709B2 (enExample) |
| EP (1) | EP1404671B1 (enExample) |
| JP (1) | JP2004534064A (enExample) |
| AT (1) | ATE323084T1 (enExample) |
| BR (1) | BR0210392A (enExample) |
| CA (1) | CA2450202A1 (enExample) |
| DE (1) | DE60210614T2 (enExample) |
| ES (1) | ES2261699T3 (enExample) |
| MX (1) | MXPA03011466A (enExample) |
| WO (1) | WO2002100856A1 (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008116302A1 (en) * | 2007-03-26 | 2008-10-02 | Merck Frosst Canada Ltd. | Cathepsin cysteine protease inhibitors |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MXPA04005428A (es) | 2001-12-06 | 2004-12-06 | Elan Pharm Inc | Hidroxietilaminas substituidas. |
| CA2512111A1 (en) | 2003-01-07 | 2004-07-29 | Merck And Co., Inc. | Macrocyclic beta-secretase inhibitors for treatment of alzheimer's disease |
| US7521481B2 (en) | 2003-02-27 | 2009-04-21 | Mclaurin Joanne | Methods of preventing, treating and diagnosing disorders of protein aggregation |
| DE602004025569D1 (de) | 2003-06-18 | 2010-04-01 | Tranzyme Pharma Inc | Makrozyklische motilin rezeptorantagonisten |
| GB0325830D0 (en) * | 2003-11-05 | 2003-12-10 | Novartis Ag | Organic compounds |
| ATE396990T1 (de) * | 2004-07-28 | 2008-06-15 | Schering Corp | Makrocyclische inhibitoren der beta-sekretase |
| GB0500683D0 (en) | 2005-01-13 | 2005-02-23 | Novartis Ag | Organic compounds |
| BRPI0606636A2 (pt) * | 2005-01-13 | 2009-07-07 | Novartis Ag | compostos macrocìclicos úteis como inibidores de bace |
| AU2006235344B2 (en) | 2005-04-08 | 2012-07-26 | Comentis, Inc. | Compounds which inhibit beta-secretase activity and methods of use thereof |
| US7338974B2 (en) | 2005-08-12 | 2008-03-04 | Bristol-Myers Squibb Company | Macrocyclic diaminopropanes as beta-secretase inhibitors |
| GB0526614D0 (en) * | 2005-12-30 | 2006-02-08 | Novartis Ag | Organic compounds |
| CN101490018A (zh) * | 2006-07-20 | 2009-07-22 | 诺瓦提斯公司 | 用作bace抑制剂的大环化合物 |
| CA2656869A1 (en) * | 2006-07-20 | 2008-01-24 | Novartis Ag | Macrocyclic lactams |
| US7678784B2 (en) | 2006-11-20 | 2010-03-16 | Bristol-Myers Squibb Company | Oxime-containing macrocyclic acyl guanidines as β-secretase inhibitors |
| US7772221B2 (en) | 2007-02-09 | 2010-08-10 | Bristol-Meyers Squibb Company | Diaminopropane derived macrocycles as inhibitors of β amyloid production |
| US7732434B2 (en) | 2007-04-20 | 2010-06-08 | Bristol-Myers Squibb Company | Macrocyclic acyl guanidines as beta-secretase inhibitors |
| US20160022649A1 (en) * | 2013-03-15 | 2016-01-28 | The Board Of Regents Of The University Of Texas System | Use of inhibitors of mtor to improve vascular functions in apoe4 carriers |
| CA2933908C (en) | 2013-12-31 | 2024-01-30 | Rapamycin Holdings, Llc | Oral rapamycin nanoparticle preparations and use |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AUPM982594A0 (en) | 1994-12-02 | 1995-01-05 | University Of Queensland, The | HIV protease inhibitors |
| CA2376420A1 (en) * | 1999-06-15 | 2000-12-21 | Elan Pharmaceuticals, Inc. | Statine-derived tetrapeptide inhibitors of beta-secretase |
-
2002
- 2002-06-12 MX MXPA03011466A patent/MXPA03011466A/es active IP Right Grant
- 2002-06-12 CA CA002450202A patent/CA2450202A1/en not_active Abandoned
- 2002-06-12 JP JP2003503623A patent/JP2004534064A/ja active Pending
- 2002-06-12 US US10/171,182 patent/US6969709B2/en not_active Expired - Fee Related
- 2002-06-12 BR BR0210392-3A patent/BR0210392A/pt not_active IP Right Cessation
- 2002-06-12 AT AT02752056T patent/ATE323084T1/de not_active IP Right Cessation
- 2002-06-12 EP EP02752056A patent/EP1404671B1/en not_active Expired - Lifetime
- 2002-06-12 WO PCT/US2002/019076 patent/WO2002100856A1/en not_active Ceased
- 2002-06-12 DE DE60210614T patent/DE60210614T2/de not_active Expired - Fee Related
- 2002-06-12 ES ES02752056T patent/ES2261699T3/es not_active Expired - Lifetime
-
2005
- 2005-09-02 US US11/218,879 patent/US7442691B2/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008116302A1 (en) * | 2007-03-26 | 2008-10-02 | Merck Frosst Canada Ltd. | Cathepsin cysteine protease inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| MXPA03011466A (es) | 2004-07-01 |
| DE60210614T2 (de) | 2007-03-01 |
| US20060040910A1 (en) | 2006-02-23 |
| JP2004534064A (ja) | 2004-11-11 |
| US20030236199A1 (en) | 2003-12-25 |
| WO2002100856A1 (en) | 2002-12-19 |
| BR0210392A (pt) | 2004-10-13 |
| EP1404671B1 (en) | 2006-04-12 |
| ATE323084T1 (de) | 2006-04-15 |
| DE60210614D1 (de) | 2006-05-24 |
| US7442691B2 (en) | 2008-10-28 |
| ES2261699T3 (es) | 2006-11-16 |
| EP1404671A1 (en) | 2004-04-07 |
| US6969709B2 (en) | 2005-11-29 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| FZDE | Discontinued | ||
| FZDE | Discontinued |
Effective date: 20100614 |