ZA200600156B - Tacrine derivatives as inhibitors of acetylcholinesterase - Google Patents
Tacrine derivatives as inhibitors of acetylcholinesterase Download PDFInfo
- Publication number
- ZA200600156B ZA200600156B ZA200600156A ZA200600156A ZA200600156B ZA 200600156 B ZA200600156 B ZA 200600156B ZA 200600156 A ZA200600156 A ZA 200600156A ZA 200600156 A ZA200600156 A ZA 200600156A ZA 200600156 B ZA200600156 B ZA 200600156B
- Authority
- ZA
- South Africa
- Prior art keywords
- ylamino
- chloro
- tetrahydro
- acridin
- substituted
- Prior art date
Links
- 108010022752 Acetylcholinesterase Proteins 0.000 title claims abstract description 32
- 229940022698 acetylcholinesterase Drugs 0.000 title abstract description 26
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- 239000003112 inhibitor Substances 0.000 title description 8
- 102000012440 Acetylcholinesterase Human genes 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 99
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- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 30
- 201000010099 disease Diseases 0.000 claims abstract description 26
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- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 20
- 230000001404 mediated effect Effects 0.000 claims abstract 3
- -1 6-Chloro-1,2,3,4-tetrahydro-acridin-9-ylamino Chemical group 0.000 claims description 33
- 150000003839 salts Chemical class 0.000 claims description 25
- 238000000034 method Methods 0.000 claims description 24
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- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 125000003545 alkoxy group Chemical group 0.000 claims description 14
- 229910052736 halogen Inorganic materials 0.000 claims description 14
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- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 210000000478 neocortex Anatomy 0.000 description 1
- 230000003988 neural development Effects 0.000 description 1
- 230000001537 neural effect Effects 0.000 description 1
- 230000004770 neurodegeneration Effects 0.000 description 1
- 208000015122 neurodegenerative disease Diseases 0.000 description 1
- 210000002682 neurofibrillary tangle Anatomy 0.000 description 1
- 230000014511 neuron projection development Effects 0.000 description 1
- 230000004031 neuronal differentiation Effects 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 239000012457 nonaqueous media Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000007170 pathology Effects 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003053 piperidines Chemical class 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000004237 preparative chromatography Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 210000001176 projection neuron Anatomy 0.000 description 1
- XJMOSONTPMZWPB-UHFFFAOYSA-M propidium iodide Chemical compound [I-].[I-].C12=CC(N)=CC=C2C2=CC=C(N)C=C2[N+](CCC[N+](C)(CC)CC)=C1C1=CC=CC=C1 XJMOSONTPMZWPB-UHFFFAOYSA-M 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Chemical group 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000002278 tabletting lubricant Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 102000013498 tau Proteins Human genes 0.000 description 1
- 108010026424 tau Proteins Proteins 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
- RXBYRTSOWREATF-UHFFFAOYSA-N tetrahydroacridine Natural products C1=CC=C2C=C(CCCC3)C3=NC2=C1 RXBYRTSOWREATF-UHFFFAOYSA-N 0.000 description 1
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 238000011200 topical administration Methods 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- HLXQFVXURMXRPU-UHFFFAOYSA-L trimethyl-[10-(trimethylazaniumyl)decyl]azanium;dibromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C HLXQFVXURMXRPU-UHFFFAOYSA-L 0.000 description 1
- 229910052722 tritium Inorganic materials 0.000 description 1
- 238000005550 wet granulation Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000002424 x-ray crystallography Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom 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
- A61P21/00—Drugs for disorders of the muscular or neuromuscular 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Psychology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Measuring Or Testing Involving Enzymes Or Micro-Organisms (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0316094.2A GB0316094D0 (en) | 2003-07-09 | 2003-07-09 | Acetylcholinesterase dual inhibitors |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ZA200600156B true ZA200600156B (en) | 2007-04-25 |
Family
ID=27741882
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ZA200600156A ZA200600156B (en) | 2003-07-09 | 2006-01-06 | Tacrine derivatives as inhibitors of acetylcholinesterase |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US7910739B2 (ru) |
| EP (1) | EP1646622B1 (ru) |
| JP (1) | JP2007534616A (ru) |
| KR (1) | KR20060110264A (ru) |
| CN (1) | CN1832937A (ru) |
| AT (1) | ATE486863T1 (ru) |
| AU (1) | AU2004255930B2 (ru) |
| BR (1) | BRPI0411960A (ru) |
| CA (1) | CA2530780A1 (ru) |
| DE (1) | DE602004029892D1 (ru) |
| DK (1) | DK1646622T3 (ru) |
| ES (1) | ES2354979T3 (ru) |
| GB (1) | GB0316094D0 (ru) |
| IL (1) | IL172710A0 (ru) |
| PL (1) | PL1646622T3 (ru) |
| PT (1) | PT1646622E (ru) |
| RU (1) | RU2402545C2 (ru) |
| WO (1) | WO2005005413A1 (ru) |
| ZA (1) | ZA200600156B (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2011101774A1 (en) | 2010-02-16 | 2011-08-25 | Pfizer Inc. | (r)-4-((4-((4-(tetrahydrofuran-3-yloxy)benzo[d]isoxazol-3-yloxy)methyl)piperidin-1-yl)methyl)tetrahydro-2h-pyran-4-ol, a partial agonist of 5-ht4 receptors |
| EP2714658B1 (en) | 2011-06-03 | 2015-04-29 | Uniwersytet Warszawski | Novel hybrid cholinesterase inhibitors |
| CN102936244B (zh) * | 2012-12-04 | 2015-02-04 | 合肥工业大学 | 一种他克林-吩噻嗪异二联体类化合物及其制备方法 |
| CN104817538A (zh) * | 2015-03-13 | 2015-08-05 | 东南大学 | 去铁斯诺-他克林金属离子鳌合剂及其药物用途 |
| CN105111195B (zh) * | 2015-08-28 | 2018-06-19 | 河南大学 | 他克林-联苯双酯杂合物、其制备方法及应用 |
| CZ201615A3 (cs) * | 2016-01-14 | 2017-03-01 | Fakultní nemocnice Hradec Králové | Konjugáty na bázi takrinu a tryptofanu, způsob jejich přípravy a jejich použití |
| CN107814787A (zh) * | 2017-11-13 | 2018-03-20 | 济南大学 | 一种他克林‑吲哚乙酸杂联体化合物及其制备方法和应用 |
| CN108840864B (zh) * | 2018-07-31 | 2021-07-27 | 中国医学科学院生物医学工程研究所 | 一种他克林-杂环轭联物的制备方法及用途 |
| US20210095419A1 (en) * | 2019-09-27 | 2021-04-01 | Frederick Dombrow, JR. | Method of Binding Mineral Particles to Fibers |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4916135A (en) | 1989-05-08 | 1990-04-10 | Hoechst Roussel Pharmaceuticals Inc. | N-heteroaryl-4-quinolinamines |
| FR2651230B1 (fr) | 1989-08-25 | 1992-03-13 | Synthese Rech | Derives de la 5-amino-1,2,3,4 tetrahydro-acridine et applications comme medicaments. |
| HU213107B (en) | 1994-02-23 | 1997-02-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing acetic acid derivatives and pharmaceutical compositions containing them |
| US6194403B1 (en) * | 1999-09-09 | 2001-02-27 | Unitech Pharmaceuticals, Inc. | Tacrine derivatives for treating Alzheimer's disease |
| KR100579813B1 (ko) | 2001-10-16 | 2006-05-12 | 주식회사 에스티씨나라 | 피페리딘 유도체, 이의 제조방법 및 이를 포함하는 치매치료용 약학적 조성물 |
| GB0223494D0 (en) | 2002-10-09 | 2002-11-13 | Neuropharma Sa | Dual binding site acetylcholinesterase inhibitors for the treatment of alzheimer's disease |
-
2003
- 2003-07-09 GB GBGB0316094.2A patent/GB0316094D0/en not_active Ceased
-
2004
- 2004-07-09 EP EP04743319A patent/EP1646622B1/en active Active
- 2004-07-09 AU AU2004255930A patent/AU2004255930B2/en not_active Ceased
- 2004-07-09 PT PT04743319T patent/PT1646622E/pt unknown
- 2004-07-09 CN CNA2004800195841A patent/CN1832937A/zh active Pending
- 2004-07-09 WO PCT/GB2004/002978 patent/WO2005005413A1/en active Application Filing
- 2004-07-09 ES ES04743319T patent/ES2354979T3/es active Active
- 2004-07-09 JP JP2006518364A patent/JP2007534616A/ja active Pending
- 2004-07-09 BR BRPI0411960-6A patent/BRPI0411960A/pt not_active IP Right Cessation
- 2004-07-09 AT AT04743319T patent/ATE486863T1/de active
- 2004-07-09 US US10/887,974 patent/US7910739B2/en not_active Expired - Fee Related
- 2004-07-09 DE DE602004029892T patent/DE602004029892D1/de active Active
- 2004-07-09 DK DK04743319.8T patent/DK1646622T3/da active
- 2004-07-09 KR KR1020067000455A patent/KR20060110264A/ko not_active Application Discontinuation
- 2004-07-09 RU RU2006103790/04A patent/RU2402545C2/ru not_active IP Right Cessation
- 2004-07-09 PL PL04743319T patent/PL1646622T3/pl unknown
- 2004-07-09 CA CA002530780A patent/CA2530780A1/en not_active Abandoned
-
2005
- 2005-12-20 IL IL172710A patent/IL172710A0/en not_active IP Right Cessation
-
2006
- 2006-01-06 ZA ZA200600156A patent/ZA200600156B/en unknown
-
2011
- 2011-02-18 US US13/030,239 patent/US20110144148A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004255930A1 (en) | 2005-01-20 |
| RU2006103790A (ru) | 2006-07-27 |
| US20110144148A1 (en) | 2011-06-16 |
| US7910739B2 (en) | 2011-03-22 |
| KR20060110264A (ko) | 2006-10-24 |
| US20050148621A1 (en) | 2005-07-07 |
| PL1646622T3 (pl) | 2011-04-29 |
| DK1646622T3 (da) | 2011-02-07 |
| ES2354979T3 (es) | 2011-03-21 |
| EP1646622A1 (en) | 2006-04-19 |
| DE602004029892D1 (de) | 2010-12-16 |
| WO2005005413A1 (en) | 2005-01-20 |
| JP2007534616A (ja) | 2007-11-29 |
| GB0316094D0 (en) | 2003-08-13 |
| BRPI0411960A (pt) | 2006-08-29 |
| EP1646622B1 (en) | 2010-11-03 |
| ATE486863T1 (de) | 2010-11-15 |
| CN1832937A (zh) | 2006-09-13 |
| RU2402545C2 (ru) | 2010-10-27 |
| IL172710A0 (en) | 2006-04-10 |
| PT1646622E (pt) | 2011-01-28 |
| AU2004255930B2 (en) | 2009-10-01 |
| CA2530780A1 (en) | 2005-01-20 |
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