CN107311988B - A kind of drug for treating Alzheimer disease - Google Patents
A kind of drug for treating Alzheimer disease Download PDFInfo
- Publication number
- CN107311988B CN107311988B CN201710578019.8A CN201710578019A CN107311988B CN 107311988 B CN107311988 B CN 107311988B CN 201710578019 A CN201710578019 A CN 201710578019A CN 107311988 B CN107311988 B CN 107311988B
- Authority
- CN
- China
- Prior art keywords
- formula
- alzheimer disease
- drug
- treating alzheimer
- bis
- 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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- 208000024827 Alzheimer disease Diseases 0.000 title claims abstract description 20
- 239000003814 drug Substances 0.000 title abstract description 16
- 229940079593 drug Drugs 0.000 title abstract description 14
- 239000000126 substance Substances 0.000 claims abstract description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 10
- 238000003786 synthesis reaction Methods 0.000 claims description 10
- 239000000843 powder Substances 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 7
- 239000002775 capsule Substances 0.000 claims description 3
- 238000002347 injection Methods 0.000 claims description 3
- 239000007924 injection Substances 0.000 claims description 3
- 239000003826 tablet Substances 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 2
- 239000008187 granular material Substances 0.000 claims description 2
- 239000006187 pill Substances 0.000 claims description 2
- 150000003839 salts Chemical class 0.000 claims description 2
- 238000010189 synthetic method Methods 0.000 claims 1
- 102000013455 Amyloid beta-Peptides Human genes 0.000 abstract description 11
- 108010090849 Amyloid beta-Peptides Proteins 0.000 abstract description 11
- 230000004083 survival effect Effects 0.000 abstract description 9
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- 238000011282 treatment Methods 0.000 abstract description 3
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 5
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
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- 150000002240 furans Chemical class 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 238000001291 vacuum drying Methods 0.000 description 3
- CJGKNWNOOUZIDB-UHFFFAOYSA-N 2-fluoroquinazoline Chemical class C1=CC=CC2=NC(F)=NC=C21 CJGKNWNOOUZIDB-UHFFFAOYSA-N 0.000 description 2
- 125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
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- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 125000004432 carbon atom Chemical group C* 0.000 description 2
- 125000004802 cyanophenyl group Chemical group 0.000 description 2
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- 150000004508 retinoic acid derivatives Chemical class 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- GNUFQJQCEBFWDQ-UHFFFAOYSA-N (3,5-difluorophenoxy)boronic acid Chemical class OB(O)OC1=CC(F)=CC(F)=C1 GNUFQJQCEBFWDQ-UHFFFAOYSA-N 0.000 description 1
- CCQCRVHVJHAXJB-UHFFFAOYSA-N (4-propan-2-ylphenoxy)boronic acid Chemical compound CC(C)C1=CC=C(OB(O)O)C=C1 CCQCRVHVJHAXJB-UHFFFAOYSA-N 0.000 description 1
- 102100027831 14-3-3 protein theta Human genes 0.000 description 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 1
- YEUFXMPHEYKKGP-UHFFFAOYSA-N 3-bromopyrazine-2-carbaldehyde Chemical compound BrC1=NC=CN=C1C=O YEUFXMPHEYKKGP-UHFFFAOYSA-N 0.000 description 1
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 1
- 239000006144 Dulbecco’s modified Eagle's medium Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001503 Glucan Polymers 0.000 description 1
- 206010029350 Neurotoxicity Diseases 0.000 description 1
- BELBBZDIHDAJOR-UHFFFAOYSA-N Phenolsulfonephthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2S(=O)(=O)O1 BELBBZDIHDAJOR-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 206010044221 Toxic encephalopathy Diseases 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
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- 238000004220 aggregation Methods 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- JYTVKRNTTALBBZ-UHFFFAOYSA-N bis demethoxycurcumin Natural products C1=CC(O)=CC=C1C=CC(=O)CC(=O)C=CC1=CC=CC(O)=C1 JYTVKRNTTALBBZ-UHFFFAOYSA-N 0.000 description 1
- PREBVFJICNPEKM-YDWXAUTNSA-N bisdemethoxycurcumin Chemical compound C1=CC(O)=CC=C1\C=C\C(=O)CC(=O)\C=C\C1=CC=C(O)C=C1 PREBVFJICNPEKM-YDWXAUTNSA-N 0.000 description 1
- 210000005013 brain tissue Anatomy 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000004113 cell culture Methods 0.000 description 1
- 230000024245 cell differentiation Effects 0.000 description 1
- 230000009087 cell motility Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 230000019771 cognition Effects 0.000 description 1
- 230000003930 cognitive ability Effects 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- ZXZBMGGWHWRHPS-UHFFFAOYSA-N cyanato(phenyl)borinic acid Chemical compound N#COB(O)C1=CC=CC=C1 ZXZBMGGWHWRHPS-UHFFFAOYSA-N 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- YXAKCQIIROBKOP-UHFFFAOYSA-N di-p-hydroxycinnamoylmethane Natural products C=1C=C(O)C=CC=1C=CC(=O)C=C(O)C=CC1=CC=C(O)C=C1 YXAKCQIIROBKOP-UHFFFAOYSA-N 0.000 description 1
- 238000003745 diagnosis Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 239000000890 drug combination Substances 0.000 description 1
- 230000004064 dysfunction Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 210000004709 eyebrow Anatomy 0.000 description 1
- 210000000720 eyelash Anatomy 0.000 description 1
- 239000012894 fetal calf serum Substances 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
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- 230000003340 mental effect Effects 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 239000004090 neuroprotective agent Substances 0.000 description 1
- 230000007135 neurotoxicity Effects 0.000 description 1
- 231100000228 neurotoxicity Toxicity 0.000 description 1
- 239000002858 neurotransmitter agent Substances 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000036285 pathological change Effects 0.000 description 1
- 231100000915 pathological change Toxicity 0.000 description 1
- 230000001575 pathological effect Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 229960003531 phenolsulfonphthalein Drugs 0.000 description 1
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
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- 238000010992 reflux Methods 0.000 description 1
- 230000002000 scavenging effect Effects 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- 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
- C07D405/14—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 three or more hetero rings
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L33/00—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof
- A23L33/10—Modifying nutritive qualities of foods; Dietetic products; Preparation or treatment thereof using additives
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Mycology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
Description
Group | Cell survival rate |
Blank control group | 100 |
Model group | 21 |
Positive controls | 74 |
Ⅰa | 99 |
Ⅰb | 76 |
Ⅰc | 88 |
Ⅰd | 99 |
Claims (5)
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710578019.8A CN107311988B (en) | 2017-07-15 | 2017-07-15 | A kind of drug for treating Alzheimer disease |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN201710578019.8A CN107311988B (en) | 2017-07-15 | 2017-07-15 | A kind of drug for treating Alzheimer disease |
Publications (2)
Publication Number | Publication Date |
---|---|
CN107311988A CN107311988A (en) | 2017-11-03 |
CN107311988B true CN107311988B (en) | 2018-08-21 |
Family
ID=60177918
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN201710578019.8A Active CN107311988B (en) | 2017-07-15 | 2017-07-15 | A kind of drug for treating Alzheimer disease |
Country Status (1)
Country | Link |
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CN (1) | CN107311988B (en) |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101218206A (en) * | 2005-07-04 | 2008-07-09 | 诺沃-诺迪斯克有限公司 | Histamine H3 receptor antagonists |
WO2008099210A2 (en) * | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
WO2009037247A1 (en) * | 2007-09-17 | 2009-03-26 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
CN103328468A (en) * | 2010-10-27 | 2013-09-25 | 普罗克斯马根有限公司 | Alpha-7 nicotinic receptor modulators for the treatment of pain, a psychotic disorder, cognitive impairment or alzheimer's disease |
WO2014165263A1 (en) * | 2013-03-12 | 2014-10-09 | The Regents Of The University Of California, A California Corporation | Gamma-secretase modulators |
CN105189494A (en) * | 2013-03-13 | 2015-12-23 | 普罗克西梅根有限公司 | Imidazo[4,5-c]pyridine and pyrrolo[2,3-c]pyridine derivatives as SSAO inhibitors |
-
2017
- 2017-07-15 CN CN201710578019.8A patent/CN107311988B/en active Active
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101218206A (en) * | 2005-07-04 | 2008-07-09 | 诺沃-诺迪斯克有限公司 | Histamine H3 receptor antagonists |
WO2008099210A2 (en) * | 2007-02-12 | 2008-08-21 | Merck & Co., Inc. | Piperazine derivatives for treatment of ad and related conditions |
WO2009037247A1 (en) * | 2007-09-17 | 2009-03-26 | Neurosearch A/S | Pyrazine derivatives and their use as potassium channel modulators |
CN103328468A (en) * | 2010-10-27 | 2013-09-25 | 普罗克斯马根有限公司 | Alpha-7 nicotinic receptor modulators for the treatment of pain, a psychotic disorder, cognitive impairment or alzheimer's disease |
WO2014165263A1 (en) * | 2013-03-12 | 2014-10-09 | The Regents Of The University Of California, A California Corporation | Gamma-secretase modulators |
CN105189494A (en) * | 2013-03-13 | 2015-12-23 | 普罗克西梅根有限公司 | Imidazo[4,5-c]pyridine and pyrrolo[2,3-c]pyridine derivatives as SSAO inhibitors |
Also Published As
Publication number | Publication date |
---|---|
CN107311988A (en) | 2017-11-03 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination | ||
TA01 | Transfer of patent application right | ||
TA01 | Transfer of patent application right |
Effective date of registration: 20180706 Address after: No. 200, companion Kun Road, Minhang District, Shanghai Applicant after: Shanghai Pukang Pharmaceutical Co.,Ltd. Address before: 262600 Wolong Town, Linqu County, Weifang, Shandong Applicant before: Ju De Feng |
|
GR01 | Patent grant | ||
GR01 | Patent grant | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right | ||
PE01 | Entry into force of the registration of the contract for pledge of patent right |
Denomination of invention: A drug for treating Alzheimer's disease Effective date of registration: 20230627 Granted publication date: 20180821 Pledgee: Bank of Hangzhou Limited by Share Ltd. Shanghai branch Pledgor: Shanghai Pukang Pharmaceutical Co.,Ltd. Registration number: Y2023310000315 |
|
PC01 | Cancellation of the registration of the contract for pledge of patent right | ||
PC01 | Cancellation of the registration of the contract for pledge of patent right |
Granted publication date: 20180821 Pledgee: Bank of Hangzhou Limited by Share Ltd. Shanghai branch Pledgor: Shanghai Pukang Pharmaceutical Co.,Ltd. Registration number: Y2023310000315 |