CA2940536A1 - 6-substituted estradiol derivatives for the treatment of alzheimer's disease - Google Patents
6-substituted estradiol derivatives for the treatment of alzheimer's disease Download PDFInfo
- Publication number
- CA2940536A1 CA2940536A1 CA2940536A CA2940536A CA2940536A1 CA 2940536 A1 CA2940536 A1 CA 2940536A1 CA 2940536 A CA2940536 A CA 2940536A CA 2940536 A CA2940536 A CA 2940536A CA 2940536 A1 CA2940536 A1 CA 2940536A1
- Authority
- CA
- Canada
- Prior art keywords
- methyl
- cyclopenta
- decahydro
- phenanthrene
- diol
- 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
- 208000024827 Alzheimer disease Diseases 0.000 title claims description 26
- 150000002159 estradiols Chemical class 0.000 title claims description 16
- 238000011282 treatment Methods 0.000 title description 15
- 150000001875 compounds Chemical class 0.000 claims description 89
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 64
- 229910052739 hydrogen Inorganic materials 0.000 claims description 58
- 238000000034 method Methods 0.000 claims description 45
- -1 (methoxymethyl)amino Chemical group 0.000 claims description 34
- 108010013563 Lipoprotein Lipase Proteins 0.000 claims description 27
- 150000003839 salts Chemical class 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 16
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 14
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 12
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 10
- 125000001475 halogen functional group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 230000003827 upregulation Effects 0.000 claims description 7
- 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 6
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- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 claims description 6
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- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
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- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- ACVYVLVWPXVTIT-UHFFFAOYSA-M phosphinate Chemical group [O-][PH2]=O ACVYVLVWPXVTIT-UHFFFAOYSA-M 0.000 claims description 4
- 239000012453 solvate Substances 0.000 claims description 4
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 3
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 3
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- 125000000468 ketone group Chemical group 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
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- GBAGOJGTNKBYMI-OCJHARCKSA-N (6r,8r,9s,10r,13s,14s)-6-(methoxymethyl)-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound C([C@@]12C)CC(O)CC1[C@H](COC)C[C@@H]1[C@@H]2CC[C@]2(C)C(O)CC[C@H]21 GBAGOJGTNKBYMI-OCJHARCKSA-N 0.000 claims 4
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- 125000003837 (C1-C20) alkyl group Chemical group 0.000 claims 2
- NMPCUPPFFBXPKH-LOPRSAABSA-N (6r,8s,9s,14s,17s)-6-(methoxymethyl)-7,8,9,11,12,13,14,15,16,17-decahydro-6h-cyclopenta[a]phenanthrene-3,17-diol Chemical compound C12=CC=C(O)C=C2[C@H](COC)C[C@@H]2[C@@H]1CCC1[C@@H](O)CC[C@H]12 NMPCUPPFFBXPKH-LOPRSAABSA-N 0.000 claims 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/565—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids not substituted in position 17 beta by a carbon atom, e.g. estrane, estradiol
-
- 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
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
Landscapes
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Steroid Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461955578P | 2014-03-19 | 2014-03-19 | |
| US61/955,578 | 2014-03-19 | ||
| PCT/US2015/021538 WO2015143201A2 (en) | 2014-03-19 | 2015-03-19 | 6-substituted estradiol derivatives for the treatment of alzheimer's disease |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2940536A1 true CA2940536A1 (en) | 2015-09-24 |
Family
ID=54141046
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2940536A Abandoned CA2940536A1 (en) | 2014-03-19 | 2015-03-19 | 6-substituted estradiol derivatives for the treatment of alzheimer's disease |
Country Status (11)
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102719543B1 (ko) * | 2019-06-03 | 2024-10-17 | 아이홀 코포레이션 | 히알루로난 접합체 및 이의 용도 |
| US20210024568A1 (en) * | 2019-07-23 | 2021-01-28 | Endece Llc | Methods for modulation of lipoprotein lipase and apolipoprotein c2 expression and/or activity in the treatment of peripheral and central nervous system tissue disease states |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10174070B2 (en) * | 2005-09-30 | 2019-01-08 | Endece Llc | 6-substituted estradiol derivatives and methods of use |
| WO2008100560A2 (en) * | 2007-02-14 | 2008-08-21 | University Of Southern California | Estrogen receptor modulators, associated pharmaceutical compositions and methods of use |
| WO2012129324A2 (en) * | 2011-03-21 | 2012-09-27 | Endece Llc | 6-substituted estradiol derivatives for use in remyelination of nerve axons |
-
2015
- 2015-03-19 JP JP2016556841A patent/JP2017512769A/ja active Pending
- 2015-03-19 AU AU2015231172A patent/AU2015231172A1/en not_active Abandoned
- 2015-03-19 EP EP15765290.0A patent/EP3119402A4/en not_active Withdrawn
- 2015-03-19 SG SG11201607693WA patent/SG11201607693WA/en unknown
- 2015-03-19 CN CN201580014623.7A patent/CN106255501A/zh active Pending
- 2015-03-19 US US14/663,043 patent/US20150265630A1/en not_active Abandoned
- 2015-03-19 KR KR1020167028986A patent/KR20160136363A/ko not_active Withdrawn
- 2015-03-19 MX MX2016012045A patent/MX2016012045A/es unknown
- 2015-03-19 BR BR112016021408A patent/BR112016021408A2/pt not_active IP Right Cessation
- 2015-03-19 CA CA2940536A patent/CA2940536A1/en not_active Abandoned
- 2015-03-19 WO PCT/US2015/021538 patent/WO2015143201A2/en not_active Ceased
-
2018
- 2018-02-12 AU AU2018201003A patent/AU2018201003A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| BR112016021408A2 (pt) | 2017-12-19 |
| AU2015231172A1 (en) | 2016-09-08 |
| EP3119402A4 (en) | 2017-11-01 |
| KR20160136363A (ko) | 2016-11-29 |
| AU2018201003A1 (en) | 2018-03-01 |
| JP2017512769A (ja) | 2017-05-25 |
| SG11201607693WA (en) | 2016-10-28 |
| CN106255501A (zh) | 2016-12-21 |
| US20150265630A1 (en) | 2015-09-24 |
| EP3119402A2 (en) | 2017-01-25 |
| MX2016012045A (es) | 2017-01-19 |
| WO2015143201A2 (en) | 2015-09-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |
Effective date: 20160822 |
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| FZDE | Dead |
Effective date: 20200106 |