CA2070714A1 - ¬(arylalkylpiperidin-4-yl)methyl|-2a,3,4,5-tetrahydro-1(2h) -acenaphthylen-1-ones and related compounds (case hoe 91/s 013/hr-1223) - Google Patents
¬(arylalkylpiperidin-4-yl)methyl|-2a,3,4,5-tetrahydro-1(2h) -acenaphthylen-1-ones and related compounds (case hoe 91/s 013/hr-1223)Info
- Publication number
- CA2070714A1 CA2070714A1 CA002070714A CA2070714A CA2070714A1 CA 2070714 A1 CA2070714 A1 CA 2070714A1 CA 002070714 A CA002070714 A CA 002070714A CA 2070714 A CA2070714 A CA 2070714A CA 2070714 A1 CA2070714 A1 CA 2070714A1
- Authority
- CA
- Canada
- Prior art keywords
- compound
- methyl
- hydrogen
- acenaphthylen
- tetrahydro
- 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
- 150000001875 compounds Chemical class 0.000 title claims abstract description 57
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 title claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 230000007074 memory dysfunction Effects 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 3
- 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 8
- 230000000694 effects Effects 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- 239000003814 drug Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- DTBYMCHMSLOFIJ-UHFFFAOYSA-N 2-[(1-benzylpiperidin-4-yl)methyl]-1,2,3,3a,4,5-hexahydroacenaphthylen-1-ol Chemical compound C=12C3CCCC2=CC=CC=1C(O)C3CC(CC1)CCN1CC1=CC=CC=C1 DTBYMCHMSLOFIJ-UHFFFAOYSA-N 0.000 claims description 3
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- 229910052799 carbon Inorganic materials 0.000 description 16
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 13
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- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 description 1
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- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
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- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
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- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
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- 239000003826 tablet Substances 0.000 description 1
- YLJREFDVOIBQDA-UHFFFAOYSA-N tacrine Chemical compound C1=CC=C2C(N)=C(CCCC3)C3=NC2=C1 YLJREFDVOIBQDA-UHFFFAOYSA-N 0.000 description 1
- 229960001685 tacrine Drugs 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/26—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/20—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms
- C07D211/22—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by singly bound oxygen or sulphur atoms by oxygen atoms
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/30—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by doubly bound oxygen or sulfur atoms or by two oxygen or sulfur atoms singly bound to the same carbon atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Hospice & Palliative Care (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Hydrogenated Pyridines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Lubricants (AREA)
- Pyridine Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US713,249 | 1991-06-07 | ||
| US07/713,249 US5106856A (en) | 1991-06-07 | 1991-06-07 | [(Arylalkylpiperidin-4-yl)methyl]-2a,3,4,5-tetrahydro-1(2H)-acenaphthylen-1-ones and related compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2070714A1 true CA2070714A1 (en) | 1992-12-08 |
Family
ID=24865395
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002070714A Abandoned CA2070714A1 (en) | 1991-06-07 | 1992-06-08 | ¬(arylalkylpiperidin-4-yl)methyl|-2a,3,4,5-tetrahydro-1(2h) -acenaphthylen-1-ones and related compounds (case hoe 91/s 013/hr-1223) |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US5106856A (enExample) |
| EP (1) | EP0517221B1 (enExample) |
| JP (1) | JP2961013B2 (enExample) |
| KR (1) | KR100234445B1 (enExample) |
| AT (1) | ATE131814T1 (enExample) |
| AU (1) | AU646784B2 (enExample) |
| CA (1) | CA2070714A1 (enExample) |
| CZ (1) | CZ284591B6 (enExample) |
| DE (1) | DE69206889T2 (enExample) |
| DK (1) | DK0517221T3 (enExample) |
| ES (1) | ES2081517T3 (enExample) |
| FI (1) | FI101297B1 (enExample) |
| GR (1) | GR3018558T3 (enExample) |
| HU (1) | HU217967B (enExample) |
| IE (1) | IE72199B1 (enExample) |
| IL (1) | IL102118A (enExample) |
| MX (1) | MX9202736A (enExample) |
| NO (1) | NO178889C (enExample) |
| NZ (1) | NZ243013A (enExample) |
| PL (1) | PL169423B1 (enExample) |
| RU (1) | RU2043989C1 (enExample) |
| TW (1) | TW206214B (enExample) |
| ZA (1) | ZA924109B (enExample) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW248556B (enExample) * | 1993-01-18 | 1995-06-01 | Takeda Pharm Industry Co | |
| US6939879B2 (en) * | 1998-08-28 | 2005-09-06 | Aventis Pharmaceuticals Inc. | Use of R (+)-α-(2,3-dimethoxyphenyl)-1-[2-(4-fluorophenyl)ethyl]-4-piperidinemethanol for the treatment of substance induced insomnia |
| HUP0104493A3 (en) | 1998-09-30 | 2002-12-28 | Takeda Pharmaceutical | Drugs for improving vesical excretory strength |
| EP2533645B1 (en) | 2010-02-09 | 2016-07-27 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| AU2011328993B2 (en) | 2010-11-15 | 2017-03-02 | Agenebio, Inc. | Pyridazine derivatives, compositions and methods for treating cognitive impairment |
| US10154988B2 (en) | 2012-11-14 | 2018-12-18 | The Johns Hopkins University | Methods and compositions for treating schizophrenia |
| CA2904767C (en) | 2013-03-15 | 2022-06-21 | Agenebio, Inc. | Methods and compositions for improving cognitive function |
| US10806717B2 (en) | 2013-03-15 | 2020-10-20 | The Johns Hopkins University | Methods and compositions for improving cognitive function |
| EP4032889B1 (en) | 2013-12-20 | 2026-05-06 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| EA034167B8 (ru) | 2015-05-22 | 2021-04-27 | Эйджинбайо, Инк. | Фармацевтические композиции леветирацетама пролонгированного высвобождения |
| EP3310785B1 (en) | 2015-06-19 | 2024-11-20 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| US20180170941A1 (en) | 2016-12-19 | 2018-06-21 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| AU2019288382B2 (en) | 2018-06-19 | 2024-07-25 | Agenebio, Inc. | Benzodiazepine derivatives, compositions, and methods for treating cognitive impairment |
| EP4572852A1 (en) | 2022-08-19 | 2025-06-25 | Agenebio, Inc. | Benzazepine derivatives, compositions, and methods for treating cognitive impairment |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2589934A (en) * | 1950-08-24 | 1952-03-18 | Abbott Lab | 2-aminomethyl-tetrahydroacenapthones-1 and their preparation |
| US3391178A (en) * | 1964-12-30 | 1968-07-02 | Ernest E. Campaigne | Dialkylaminoalkyl 1-oxo-2alpha, 3, 4, 5-tetrahydroacenaphthen-2alpha-carboxylates |
| FI95572C (fi) * | 1987-06-22 | 1996-02-26 | Eisai Co Ltd | Menetelmä lääkeaineena käyttökelpoisen piperidiinijohdannaisten tai sen farmaseuttisen suolan valmistamiseksi |
| JP2969359B2 (ja) * | 1989-01-13 | 1999-11-02 | 武田薬品工業株式会社 | 環状アミン化合物 |
-
1991
- 1991-06-07 US US07/713,249 patent/US5106856A/en not_active Expired - Fee Related
-
1992
- 1992-05-23 TW TW081104034A patent/TW206214B/zh active
- 1992-06-04 EP EP92109467A patent/EP0517221B1/en not_active Expired - Lifetime
- 1992-06-04 DK DK92109467.8T patent/DK0517221T3/da active
- 1992-06-04 NZ NZ243013A patent/NZ243013A/en unknown
- 1992-06-04 FI FI922592A patent/FI101297B1/fi not_active IP Right Cessation
- 1992-06-04 ES ES92109467T patent/ES2081517T3/es not_active Expired - Lifetime
- 1992-06-04 DE DE69206889T patent/DE69206889T2/de not_active Expired - Fee Related
- 1992-06-04 AT AT92109467T patent/ATE131814T1/de not_active IP Right Cessation
- 1992-06-05 AU AU18015/92A patent/AU646784B2/en not_active Ceased
- 1992-06-05 JP JP4144694A patent/JP2961013B2/ja not_active Expired - Fee Related
- 1992-06-05 NO NO922223A patent/NO178889C/no not_active IP Right Cessation
- 1992-06-05 CZ CS921713A patent/CZ284591B6/cs not_active IP Right Cessation
- 1992-06-05 IL IL10211892A patent/IL102118A/en not_active IP Right Cessation
- 1992-06-05 KR KR1019920009765A patent/KR100234445B1/ko not_active Expired - Fee Related
- 1992-06-05 PL PL92294803A patent/PL169423B1/pl unknown
- 1992-06-05 ZA ZA924109A patent/ZA924109B/xx unknown
- 1992-06-05 HU HU9201887A patent/HU217967B/hu not_active IP Right Cessation
- 1992-06-06 RU SU925052251A patent/RU2043989C1/ru active
- 1992-06-08 CA CA002070714A patent/CA2070714A1/en not_active Abandoned
- 1992-06-08 MX MX9202736A patent/MX9202736A/es not_active IP Right Cessation
- 1992-07-01 IE IE921840A patent/IE72199B1/en not_active IP Right Cessation
-
1995
- 1995-12-28 GR GR950403690T patent/GR3018558T3/el unknown
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