DE69811070T2 - 9-azabicyclo(3.3.1)non-2-ene und nonanderivate als liganden der nicotinergen rezeptoren - Google Patents
9-azabicyclo(3.3.1)non-2-ene und nonanderivate als liganden der nicotinergen rezeptorenInfo
- Publication number
- DE69811070T2 DE69811070T2 DE69811070T DE69811070T DE69811070T2 DE 69811070 T2 DE69811070 T2 DE 69811070T2 DE 69811070 T DE69811070 T DE 69811070T DE 69811070 T DE69811070 T DE 69811070T DE 69811070 T2 DE69811070 T2 DE 69811070T2
- Authority
- DE
- Germany
- Prior art keywords
- azabicyclo
- ene
- pyridyl
- methyl
- disease
- 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
- ODYAYVUDAZHKHK-UHFFFAOYSA-N 9-azabicyclo[3.3.1]non-3-ene Chemical compound C1C=CC2CCCC1N2 ODYAYVUDAZHKHK-UHFFFAOYSA-N 0.000 title claims description 10
- 239000003446 ligand Substances 0.000 title abstract description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 74
- -1 thiocycloalkoxy Chemical group 0.000 claims abstract description 65
- 239000000203 mixture Substances 0.000 claims abstract description 57
- 150000003839 salts Chemical class 0.000 claims abstract description 21
- 108010009685 Cholinergic Receptors Proteins 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 10
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 9
- 150000002367 halogens Chemical class 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 9
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 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 abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims abstract description 5
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
- 102000034337 acetylcholine receptors Human genes 0.000 claims abstract 2
- 238000000034 method Methods 0.000 claims description 38
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 35
- 201000010099 disease Diseases 0.000 claims description 24
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims description 23
- 229960002715 nicotine Drugs 0.000 claims description 23
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 20
- 239000000126 substance Substances 0.000 claims description 17
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 15
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- 238000006243 chemical reaction Methods 0.000 claims description 8
- 125000004076 pyridyl group Chemical group 0.000 claims description 6
- 230000000391 smoking effect Effects 0.000 claims description 6
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 5
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- 125000001624 naphthyl group Chemical group 0.000 claims description 5
- 230000008569 process Effects 0.000 claims description 5
- SDTHNELQRNSYSO-UHFFFAOYSA-N 3-(1-benzothiophen-2-yl)-9-methyl-9-azabicyclo[3.3.1]non-3-ene Chemical compound C1=CC=C2SC(C3=CC4CCCC(C3)N4C)=CC2=C1 SDTHNELQRNSYSO-UHFFFAOYSA-N 0.000 claims description 4
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 4
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- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
- 125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
- 125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
- 230000008602 contraction Effects 0.000 claims description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
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- 125000000714 pyrimidinyl group Chemical group 0.000 claims description 4
- 125000000168 pyrrolyl group Chemical group 0.000 claims description 4
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 3
- GUGWVENEJVJHBG-UHFFFAOYSA-N 3-(1-benzofuran-2-yl)-9-methyl-9-azabicyclo[3.3.1]non-3-ene Chemical compound C1=CC=C2OC(C3=CC4CCCC(C3)N4C)=CC2=C1 GUGWVENEJVJHBG-UHFFFAOYSA-N 0.000 claims description 3
- QACPLNQNDLMTLC-UHFFFAOYSA-N 5-(9-methyl-9-azabicyclo[3.3.1]non-3-en-3-yl)quinoline Chemical compound C1=CC=C2C(C3=CC4CCCC(C3)N4C)=CC=CC2=N1 QACPLNQNDLMTLC-UHFFFAOYSA-N 0.000 claims description 3
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- PAEJVIJIKOQBHV-UHFFFAOYSA-N 1-(9-methyl-9-azabicyclo[3.3.1]non-3-en-3-yl)ethanone Chemical compound C1CCC2C=C(C(C)=O)CC1N2C PAEJVIJIKOQBHV-UHFFFAOYSA-N 0.000 claims description 2
- VIPNLMWWYPARBJ-UHFFFAOYSA-N 2-(9-methyl-9-azabicyclo[3.3.1]non-3-en-3-yl)-1,3-benzothiazole Chemical compound C1=CC=C2SC(C3=CC4CCCC(C3)N4C)=NC2=C1 VIPNLMWWYPARBJ-UHFFFAOYSA-N 0.000 claims description 2
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
- YTTBKUHBSPVOSJ-UHFFFAOYSA-N 3-(9-methyl-9-azabicyclo[3.3.1]non-3-en-3-yl)quinoline Chemical compound C1=CC=CC2=CC(C3=CC4CCCC(C3)N4C)=CN=C21 YTTBKUHBSPVOSJ-UHFFFAOYSA-N 0.000 claims description 2
- CYVHLASJYAQLDM-UHFFFAOYSA-N 3-(furan-3-yl)-9-methyl-9-azabicyclo[3.3.1]non-3-ene Chemical compound CN1C(C2)CCCC1C=C2C=1C=COC=1 CYVHLASJYAQLDM-UHFFFAOYSA-N 0.000 claims description 2
- YRFUDMMKRFROIT-UHFFFAOYSA-N 9-benzyl-3-pyridin-3-yl-9-azabicyclo[3.3.1]non-3-ene Chemical compound C=1C=CC=CC=1CN1C(C2)CCCC1C=C2C1=CC=CN=C1 YRFUDMMKRFROIT-UHFFFAOYSA-N 0.000 claims description 2
- AAPSAWLYCJKYPS-UHFFFAOYSA-N 9-ethyl-3-pyridin-3-yl-9-azabicyclo[3.3.1]non-3-ene Chemical compound CCN1C(C2)CCCC1C=C2C1=CC=CN=C1 AAPSAWLYCJKYPS-UHFFFAOYSA-N 0.000 claims description 2
- IAXKSWAPCAZPNA-UHFFFAOYSA-N 9-methyl-3-naphthalen-2-yl-9-azabicyclo[3.3.1]non-3-ene Chemical compound C1=CC=CC2=CC(C3=CC4CCCC(C3)N4C)=CC=C21 IAXKSWAPCAZPNA-UHFFFAOYSA-N 0.000 claims description 2
- APTUPAXCDMGCCK-UHFFFAOYSA-N 9-methyl-3-pyridin-3-yl-9-azabicyclo[3.3.1]non-3-ene Chemical compound CN1C(C2)CCCC1C=C2C1=CC=CN=C1 APTUPAXCDMGCCK-UHFFFAOYSA-N 0.000 claims description 2
- IXCBWNBUDGHRFJ-UHFFFAOYSA-N 9-methyl-3-pyrimidin-5-yl-9-azabicyclo[3.3.1]non-3-ene Chemical compound CN1C(C2)CCCC1C=C2C1=CN=CN=C1 IXCBWNBUDGHRFJ-UHFFFAOYSA-N 0.000 claims description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical group OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003814 drug Substances 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 12
- 125000002950 monocyclic group Chemical group 0.000 abstract description 10
- 125000003118 aryl group Chemical group 0.000 abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 abstract description 9
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 abstract description 6
- 125000000304 alkynyl group Chemical group 0.000 abstract description 6
- 125000004104 aryloxy group Chemical group 0.000 abstract description 6
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract description 4
- 125000001072 heteroaryl group Chemical group 0.000 abstract description 4
- 125000005309 thioalkoxy group Chemical group 0.000 abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 abstract description 3
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract description 3
- 125000000266 alpha-aminoacyl group Chemical group 0.000 abstract description 2
- 125000002619 bicyclic group Chemical group 0.000 abstract description 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
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- C07D451/14—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing 9-azabicyclo [3.3.1] nonane ring systems, e.g. granatane, 2-aza-adamantane; Cyclic acetals thereof
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- A61P13/00—Drugs for disorders of the urinary system
- A61P13/06—Anti-spasmodics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- 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
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- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Addiction (AREA)
- Psychiatry (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Psychology (AREA)
- Pulmonology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DK62897 | 1997-05-30 | ||
| PCT/DK1998/000224 WO1998054182A1 (en) | 1997-05-30 | 1998-05-29 | 9-AZABICYCLO(3.3.1)NON-2-ENE AND NONANE DERIVATIVES AS CHOLINERGIC LIGANDS AT NICOTINIC ACh RECEPTORS |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69811070D1 DE69811070D1 (de) | 2003-03-06 |
| DE69811070T2 true DE69811070T2 (de) | 2003-10-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69811070T Expired - Lifetime DE69811070T2 (de) | 1997-05-30 | 1998-05-29 | 9-azabicyclo(3.3.1)non-2-ene und nonanderivate als liganden der nicotinergen rezeptoren |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6392045B1 (enExample) |
| EP (1) | EP0984966B1 (enExample) |
| JP (1) | JP2002502383A (enExample) |
| CN (1) | CN1205210C (enExample) |
| AT (1) | ATE231861T1 (enExample) |
| AU (1) | AU736798B2 (enExample) |
| CA (1) | CA2289570C (enExample) |
| DE (1) | DE69811070T2 (enExample) |
| DK (1) | DK0984966T3 (enExample) |
| NZ (1) | NZ500645A (enExample) |
| WO (1) | WO1998054182A1 (enExample) |
| ZA (1) | ZA984640B (enExample) |
Families Citing this family (34)
| Publication number | Priority date | Publication date | Assignee | Title |
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| DE60007841T2 (de) | 1999-01-28 | 2004-07-08 | Neurosearch A/S | Neue azabicyclo derivate und ihre verwendung |
| US7265115B2 (en) | 1999-01-29 | 2007-09-04 | Abbott Laboratories | Diazabicyclic CNS active agents |
| PT1147112E (pt) * | 1999-01-29 | 2004-03-31 | Abbott Lab | Derivados diazabiciclicos como liganos nicotinicos do receptor de acetilcolina |
| ATE261448T1 (de) * | 1999-05-04 | 2004-03-15 | Neurosearch As | Heteroaryl diazabicycloalkene, deren herstellung und verwendung |
| WO2001044243A2 (en) * | 1999-12-14 | 2001-06-21 | Neurosearch A/S | Novel heteroaryl-diazabicycloalkanes |
| MY145722A (en) * | 2000-04-27 | 2012-03-30 | Abbott Lab | Diazabicyclic central nervous system active agents |
| US6852721B2 (en) | 2000-05-25 | 2005-02-08 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| US6521288B2 (en) * | 2000-05-31 | 2003-02-18 | Board Of Control Of Michigan Technological University | Compositions and methods for wood preservation |
| CA2410945A1 (en) * | 2000-07-04 | 2002-01-10 | Neurosearch A/S | Aryl and heteroaryl diazabicycloalkanes, their preparation and use |
| US6579878B1 (en) | 2000-07-07 | 2003-06-17 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| US6624167B1 (en) | 2000-08-04 | 2003-09-23 | Targacept, Inc. | Pharmaceutical compositions and methods for use |
| ES2269467T3 (es) * | 2000-10-13 | 2007-04-01 | Neurosearch A/S | Tratamiento de transtornos afectivos por la accion combinada de un agonista del receptor nicotinico y una sustancia monoaminergenica. |
| DE60203007T2 (de) * | 2001-06-01 | 2005-07-07 | Neurosearch A/S | Heteroaryl-diazabicycloalkanderivaten als cns-modulatoren |
| US7238715B2 (en) | 2002-12-06 | 2007-07-03 | The Feinstein Institute For Medical Research | Treatment of pancreatitis using alpha 7 receptor-binding cholinergic agonists |
| US7273872B2 (en) † | 2002-12-06 | 2007-09-25 | The Feinstein Institute For Medical Research | Inhibition of inflammation using α 7 receptor-binding cholinergic agonists |
| AU2005284908B2 (en) | 2004-09-13 | 2011-12-08 | Morningside Venture Investments Limited | Biosynchronous transdermal drug delivery |
| DE602006019561D1 (de) | 2005-02-16 | 2011-02-24 | Neurosearch As | Diazabicyclische arylderivate und ihre verwendung als chinolinergische liganden an nikotin-acetylcholin-rezeptoren |
| US8316104B2 (en) | 2005-11-15 | 2012-11-20 | California Institute Of Technology | Method and apparatus for collaborative system |
| CN101305004B (zh) | 2005-12-06 | 2011-11-16 | 神经研究公司 | 新颖的二氮杂双环芳基衍生物和它们的医药用途 |
| EP1984366B1 (en) | 2006-02-10 | 2010-12-15 | NeuroSearch A/S | 3, 9-diazabicyclo ý3.3. 1¨nonane derivatives and their use as monoamine?neurotransmitter re-uptake inhibitors |
| CN101379063A (zh) | 2006-02-10 | 2009-03-04 | 神经研究公司 | 3,9-二氮杂双环[3.3.1]壬烷衍生物及其作为单胺神经递质再摄取抑制剂的用途 |
| WO2007090888A1 (en) | 2006-02-10 | 2007-08-16 | Neurosearch A/S | 3-heteroaryl- 3,9-diazabicyclo[3.3.1]nonane derivatives as nicotinic acetylcholine receptor agonists |
| US7855208B2 (en) | 2006-02-14 | 2010-12-21 | Neurosearch A/S | 3, 9-diazabicyclo(3.3.1)non-3-yl-aryl methanone derivatives as nicotinic acetylcholine receptor agonists |
| TW200845977A (en) * | 2007-03-30 | 2008-12-01 | Targacept Inc | Sub-type selective azabicycloalkane derivatives |
| ES2521494T3 (es) | 2007-04-02 | 2014-11-12 | Parkinson's Institute | Métodos y composiciones para la reducción de los efectos secundarios de tratamientos terapéuticos |
| US8697722B2 (en) | 2007-11-02 | 2014-04-15 | Sri International | Nicotinic acetylcholine receptor modulators |
| WO2009058120A1 (en) * | 2007-11-02 | 2009-05-07 | Sri International | Nicotinic acetylcholine receptor modulators |
| US20110142758A1 (en) * | 2008-06-10 | 2011-06-16 | Neurosearch A/S | Indolyl-pyridazinyl-diazabicyclononane derivatives in labelled and unlabelled form and their use in diagnostic methods |
| JP5421368B2 (ja) | 2008-08-01 | 2014-02-19 | パーデュー、ファーマ、リミテッド、パートナーシップ | テトラヒドロピリジニルおよびジヒドロピロリル化合物およびそれらの使用 |
| RU2560729C2 (ru) | 2010-01-11 | 2015-08-20 | АСТРАЕА ТЕРАПЕУТИКС, ЭлЭлСи | Модуляторы никотиновых ацетилхолиновых рецепторов |
| WO2016123406A1 (en) | 2015-01-28 | 2016-08-04 | Chrono Therapeutics Inc. | Drug delivery methods and systems |
| CA3049529A1 (en) | 2017-01-06 | 2018-07-12 | Chrono Therapeutics Inc. | Transdermal drug delivery devices and methods |
| CA3101966A1 (en) | 2018-05-29 | 2019-12-05 | Morningside Venture Investments Limited | Drug delivery methods and systems |
| US12397141B2 (en) | 2018-11-16 | 2025-08-26 | Morningside Venture Investments Limited | Thermally regulated transdermal drug delivery system |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3133073A (en) * | 1959-12-10 | 1964-05-12 | Sterling Drug Inc | 3-aryl-1, 5-iminocycloalkanes and preparation thereof |
| DE1174793B (de) * | 1962-11-13 | 1964-07-30 | Boehringer & Soehne Gmbh | Verfahren zur Herstellung von 3ª‡-Phenyl-granatanen und ihren Hydrohalogeniden |
| US3509161A (en) * | 1967-07-10 | 1970-04-28 | Boehringer & Soehne Gmbh | 3-phenyl-granatene-(2)-derivatives |
| IL59004A0 (en) | 1978-12-30 | 1980-03-31 | Beecham Group Ltd | Substituted benzamides their preparation and pharmaceutical compositions containing them |
| EP0093488A3 (en) | 1982-03-18 | 1984-05-23 | Beecham Group Plc | Nortropyl benzopyrrolinone compounds, process for their preparation and pharmaceutical compositions containing them |
| EP0588917B1 (en) * | 1991-05-29 | 2000-11-08 | Abbott Laboratories | Isoxazole and isothiazole compounds that enhance cognitive function |
| JPH11512443A (ja) * | 1995-09-22 | 1999-10-26 | ノボ ノルディスク アクティーゼルスカブ | 新規な置換アザ環式またはアザ二環式化合物 |
| WO1998025924A1 (en) * | 1996-11-26 | 1998-06-18 | Zeneca Limited | 8-azabicyclo[3.2.1]octane-, 8-azabicyclo[3.2.1]oct-6-ene-, 9-azabicyclo[3.3.1]nonane-, 9-aza-3-oxabicyclo[3.3.1]nonane- and 9-aza-3-thiabicyclo[3.3.1]nonane derivatives, their preparation and their use as insecticides |
-
1998
- 1998-05-29 AU AU74260/98A patent/AU736798B2/en not_active Ceased
- 1998-05-29 JP JP50012999A patent/JP2002502383A/ja not_active Withdrawn
- 1998-05-29 AT AT98921377T patent/ATE231861T1/de not_active IP Right Cessation
- 1998-05-29 EP EP98921377A patent/EP0984966B1/en not_active Expired - Lifetime
- 1998-05-29 CA CA002289570A patent/CA2289570C/en not_active Expired - Fee Related
- 1998-05-29 ZA ZA984640A patent/ZA984640B/xx unknown
- 1998-05-29 DK DK98921377T patent/DK0984966T3/da active
- 1998-05-29 CN CNB988054159A patent/CN1205210C/zh not_active Expired - Fee Related
- 1998-05-29 DE DE69811070T patent/DE69811070T2/de not_active Expired - Lifetime
- 1998-05-29 WO PCT/DK1998/000224 patent/WO1998054182A1/en not_active Ceased
- 1998-05-29 NZ NZ500645A patent/NZ500645A/en unknown
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1999
- 1999-11-29 US US09/450,635 patent/US6392045B1/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| CA2289570C (en) | 2007-04-03 |
| US6392045B1 (en) | 2002-05-21 |
| AU7426098A (en) | 1998-12-30 |
| ZA984640B (en) | 1998-12-11 |
| CA2289570A1 (en) | 1998-12-03 |
| WO1998054182A1 (en) | 1998-12-03 |
| ATE231861T1 (de) | 2003-02-15 |
| EP0984966A1 (en) | 2000-03-15 |
| NZ500645A (en) | 2001-06-29 |
| EP0984966B1 (en) | 2003-01-29 |
| JP2002502383A (ja) | 2002-01-22 |
| CN1257500A (zh) | 2000-06-21 |
| DK0984966T3 (da) | 2003-05-05 |
| CN1205210C (zh) | 2005-06-08 |
| AU736798B2 (en) | 2001-08-02 |
| DE69811070D1 (de) | 2003-03-06 |
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