JP2821233B2 - 脳乏血の予防ならびに治療におけるアダマンタン誘導体 - Google Patents
脳乏血の予防ならびに治療におけるアダマンタン誘導体Info
- Publication number
- JP2821233B2 JP2821233B2 JP2099117A JP9911790A JP2821233B2 JP 2821233 B2 JP2821233 B2 JP 2821233B2 JP 2099117 A JP2099117 A JP 2099117A JP 9911790 A JP9911790 A JP 9911790A JP 2821233 B2 JP2821233 B2 JP 2821233B2
- Authority
- JP
- Japan
- Prior art keywords
- hydrogen
- pharmaceutical composition
- amino
- composition according
- carbon atoms
- 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.)
- Expired - Lifetime
Links
- ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical class C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 title claims abstract description 26
- 206010008120 Cerebral ischaemia Diseases 0.000 title claims abstract description 16
- 238000011282 treatment Methods 0.000 title claims abstract description 10
- 230000002265 prevention Effects 0.000 title claims abstract description 7
- 201000006474 Brain Ischemia Diseases 0.000 title claims description 15
- 206010008118 cerebral infarction Diseases 0.000 title claims description 15
- 229940052761 dopaminergic adamantane derivative Drugs 0.000 title abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 13
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
- 239000008194 pharmaceutical composition Substances 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000004480 active ingredient Substances 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 210000002569 neuron Anatomy 0.000 claims description 5
- 208000028867 ischemia Diseases 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims description 3
- 208000024827 Alzheimer disease Diseases 0.000 claims description 2
- 230000007850 degeneration Effects 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 1
- 230000003449 preventive effect Effects 0.000 claims 1
- 230000001225 therapeutic effect Effects 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 43
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 28
- 239000000243 solution Substances 0.000 description 25
- 238000012360 testing method Methods 0.000 description 25
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- 238000002360 preparation method Methods 0.000 description 24
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- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- 238000001816 cooling Methods 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 12
- 235000019341 magnesium sulphate Nutrition 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 11
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- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
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- 229910052794 bromium Inorganic materials 0.000 description 8
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- 239000005457 ice water Substances 0.000 description 6
- LPIWUJAIURURAQ-UHFFFAOYSA-N 1-(2-bromoethyl)-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2(CCBr)C3 LPIWUJAIURURAQ-UHFFFAOYSA-N 0.000 description 5
- HOKKHZGPKSLGJE-GSVOUGTGSA-N N-Methyl-D-aspartic acid Chemical compound CN[C@@H](C(O)=O)CC(O)=O HOKKHZGPKSLGJE-GSVOUGTGSA-N 0.000 description 5
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical compound C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 5
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- ISDSLPMQFWIUPU-UHFFFAOYSA-N 1-propan-2-yladamantane Chemical compound C1C(C2)CC3CC2CC1(C(C)C)C3 ISDSLPMQFWIUPU-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
- 241001465754 Metazoa Species 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 241000700159 Rattus Species 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
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- QLTXKCWMEZIHBJ-PJGJYSAQSA-N dizocilpine maleate Chemical compound OC(=O)\C=C/C(O)=O.C12=CC=CC=C2[C@]2(C)C3=CC=CC=C3C[C@H]1N2 QLTXKCWMEZIHBJ-PJGJYSAQSA-N 0.000 description 4
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
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- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 description 4
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 4
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- XACJBFHSZJWBBP-UHFFFAOYSA-N 1-phenyladamantane Chemical compound C1C(C2)CC(C3)CC1CC23C1=CC=CC=C1 XACJBFHSZJWBBP-UHFFFAOYSA-N 0.000 description 3
- OVQNSGBYKOJYBK-UHFFFAOYSA-N 3-ethyladamantan-1-amine Chemical compound C1C(C2)CC3CC2(N)CC1(CC)C3 OVQNSGBYKOJYBK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
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- IOPVEZQBHDNEEW-UHFFFAOYSA-N 1-bromo-3-propan-2-yladamantane Chemical compound C1C(C2)CC3CC2(Br)CC1(C(C)C)C3 IOPVEZQBHDNEEW-UHFFFAOYSA-N 0.000 description 2
- CQGHTYOKYHAPCM-UHFFFAOYSA-N 1-cyclohexyladamantane Chemical compound C1CCCCC1C1(C2)CC(C3)CC2CC3C1 CQGHTYOKYHAPCM-UHFFFAOYSA-N 0.000 description 2
- FTNPDAKMYKMVKB-UHFFFAOYSA-N 1-ethyl-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC2(C)CC1(CC)C3 FTNPDAKMYKMVKB-UHFFFAOYSA-N 0.000 description 2
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- 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
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- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/33—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings
- C07C211/34—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton
- C07C211/38—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of rings other than six-membered aromatic rings of a saturated carbon skeleton containing condensed ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
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- Life Sciences & Earth Sciences (AREA)
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- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
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- General Chemical & Material Sciences (AREA)
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- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Cardiology (AREA)
- Psychiatry (AREA)
- Heart & Thoracic Surgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
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- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP89106657A EP0392059B1 (de) | 1989-04-14 | 1989-04-14 | Verwendung von Adamantan-Derivaten zur Prävention und Behandlung der cerebralen Ischämie |
| EP89106657.3 | 1989-04-14 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH02292214A JPH02292214A (ja) | 1990-12-03 |
| JP2821233B2 true JP2821233B2 (ja) | 1998-11-05 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2099117A Expired - Lifetime JP2821233B2 (ja) | 1989-04-14 | 1990-04-13 | 脳乏血の予防ならびに治療におけるアダマンタン誘導体 |
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| EP (1) | EP0392059B1 (enExample) |
| JP (1) | JP2821233B2 (enExample) |
| AT (1) | ATE94384T1 (enExample) |
| CA (1) | CA2014453C (enExample) |
| CH (1) | CH679208A5 (enExample) |
| DD (1) | DD293493A5 (enExample) |
| DE (2) | DE58905637D1 (enExample) |
| DK (1) | DK173356B1 (enExample) |
| ES (1) | ES2059602T3 (enExample) |
| HU (1) | HU215592B (enExample) |
| IE (1) | IE63467B1 (enExample) |
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| NL (1) | NL300107I1 (enExample) |
| PT (1) | PT93763B (enExample) |
| SE (1) | SE9001329L (enExample) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008010481A1 (en) | 2006-07-18 | 2008-01-24 | Astellas Pharma Inc. | Aminoindan derivative or salt thereof |
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| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US11505555B2 (en) | 2016-12-19 | 2022-11-22 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US10369187B2 (en) | 2017-02-09 | 2019-08-06 | Vanderbilt University | Peptide regulators of JNK family kinases |
| WO2019018185A1 (en) | 2017-07-15 | 2019-01-24 | Arisan Therapeutics Inc. | ENANTIOMERICALLY PURE ADAMATANE DERIVATIVES FOR THE TREATMENT OF FILOVIRUS INFECTIONS |
| US11173132B2 (en) | 2017-12-20 | 2021-11-16 | Corium, Inc. | Transdermal adhesive composition comprising a volatile liquid therapeutic agent having low melting point |
| BR112020026062B1 (pt) | 2018-06-19 | 2023-04-04 | Agenebio, Inc | Compostos derivados de benzodiazepina ou um sal farmaceuticamente aceitavel, isômero ou combinação dos mesmos, composição farmacêutica compreendendo os mesmos e usos dos mesmos para o tratamento de comprometimento cognitivo, câncer cerebral e psicose da doença de parkinson |
| CA3119036A1 (en) | 2018-12-05 | 2020-06-11 | The Regents Of The University Of California | Anti-cancer activity of adamantane derivatives |
| WO2020240505A1 (en) | 2019-05-31 | 2020-12-03 | TECNIMEDE - Sociedade Técnico-medicinal, SA | Immediate release fixed-dose combination of memantine and donepezil |
| EP4005565A1 (en) | 2020-11-30 | 2022-06-01 | Merz Pharmaceuticals GmbH | Novel uses of adamantane derivatives |
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Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3450761A (en) * | 1967-03-30 | 1969-06-17 | Sun Oil Co | 1-aminoethyldimethyladamantane |
| US4748154A (en) * | 1985-12-24 | 1988-05-31 | Takeda Chemical Industries, Ltd. | Peptide derivatives, their production and use |
| IT1205042B (it) * | 1987-05-28 | 1989-03-10 | Crinos Industria Farmaco | Composizione farmaceutica ad attivita' terapeutica per il trattamento della demenza senile di tipo alzheimer |
-
1989
- 1989-04-14 ES ES89106657T patent/ES2059602T3/es not_active Expired - Lifetime
- 1989-04-14 EP EP89106657A patent/EP0392059B1/de not_active Expired - Lifetime
- 1989-04-14 AT AT89106657T patent/ATE94384T1/de active
- 1989-04-14 DE DE89106657T patent/DE58905637D1/de not_active Expired - Lifetime
- 1989-04-14 DE DE2002199048 patent/DE10299048I2/de active Active
-
1990
- 1990-03-16 IE IE99690A patent/IE63467B1/en not_active IP Right Cessation
- 1990-04-10 CH CH1539/90A patent/CH679208A5/de not_active IP Right Cessation
- 1990-04-11 CA CA002014453A patent/CA2014453C/en not_active Expired - Lifetime
- 1990-04-11 DK DK199000916A patent/DK173356B1/da not_active IP Right Cessation
- 1990-04-11 US US07/508,109 patent/US5061703A/en not_active Expired - Lifetime
- 1990-04-11 SE SE9001329A patent/SE9001329L/xx not_active Application Discontinuation
- 1990-04-12 DD DD90339741A patent/DD293493A5/de not_active IP Right Cessation
- 1990-04-12 PT PT93763A patent/PT93763B/pt not_active IP Right Cessation
- 1990-04-13 JP JP2099117A patent/JP2821233B2/ja not_active Expired - Lifetime
- 1990-04-13 HU HU902434A patent/HU215592B/hu unknown
-
2002
- 2002-11-13 LU LU90988C patent/LU90988I2/fr unknown
- 2002-11-14 NL NL300107C patent/NL300107I1/nl unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008010481A1 (en) | 2006-07-18 | 2008-01-24 | Astellas Pharma Inc. | Aminoindan derivative or salt thereof |
| US8013018B2 (en) | 2006-07-18 | 2011-09-06 | Astellas Pharma Inc. | Aminoindane derivative or salt thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| DE10299048I1 (de) | 2003-03-27 |
| DE10299048I2 (de) | 2006-07-13 |
| PT93763B (pt) | 1996-04-30 |
| NL300107I2 (nl) | 2003-02-03 |
| IE63467B1 (en) | 1995-04-19 |
| ES2059602T3 (es) | 1994-11-16 |
| NL300107I1 (nl) | 2003-02-03 |
| IE900996L (en) | 1990-10-14 |
| ATE94384T1 (de) | 1993-10-15 |
| JPH02292214A (ja) | 1990-12-03 |
| PT93763A (pt) | 1990-11-20 |
| DK173356B1 (da) | 2000-08-07 |
| DK91690D0 (da) | 1990-04-11 |
| DK91690A (da) | 1990-10-15 |
| HUT58200A (en) | 1992-02-28 |
| DD293493A5 (de) | 1991-09-05 |
| EP0392059B1 (de) | 1993-09-15 |
| CA2014453A1 (en) | 1990-10-14 |
| HU215592B (hu) | 1999-01-28 |
| HU902434D0 (en) | 1990-08-28 |
| SE9001329L (sv) | 1990-10-15 |
| CH679208A5 (enExample) | 1992-01-15 |
| CA2014453C (en) | 2000-03-28 |
| EP0392059A1 (de) | 1990-10-17 |
| US5061703A (en) | 1991-10-29 |
| SE9001329D0 (sv) | 1990-04-11 |
| LU90988I2 (fr) | 2003-01-13 |
| DE58905637D1 (de) | 1993-10-21 |
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