CA2518675A1 - Novel diazabicyclic aryl derivatives - Google Patents
Novel diazabicyclic aryl derivatives Download PDFInfo
- Publication number
- CA2518675A1 CA2518675A1 CA002518675A CA2518675A CA2518675A1 CA 2518675 A1 CA2518675 A1 CA 2518675A1 CA 002518675 A CA002518675 A CA 002518675A CA 2518675 A CA2518675 A CA 2518675A CA 2518675 A1 CA2518675 A1 CA 2518675A1
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- alkyl
- diaza
- bicyclo
- furan
- 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
- 125000003118 aryl group Chemical group 0.000 title claims abstract description 121
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 85
- 201000010099 disease Diseases 0.000 claims abstract description 43
- 208000035475 disorder Diseases 0.000 claims abstract description 41
- 238000011282 treatment Methods 0.000 claims abstract description 26
- 208000002193 Pain Diseases 0.000 claims abstract description 12
- 239000000126 substance Substances 0.000 claims abstract description 11
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- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 claims abstract description 6
- 230000004770 neurodegeneration Effects 0.000 claims abstract description 5
- 230000016160 smooth muscle contraction Effects 0.000 claims abstract description 5
- -1 cyano, amino Chemical group 0.000 claims description 172
- 125000000217 alkyl group Chemical group 0.000 claims description 103
- 229910052739 hydrogen Inorganic materials 0.000 claims description 79
- 239000001257 hydrogen Substances 0.000 claims description 79
- 238000000034 method Methods 0.000 claims description 75
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 73
- 239000000203 mixture Substances 0.000 claims description 68
- 125000001188 haloalkyl group Chemical group 0.000 claims description 59
- 125000001072 heteroaryl group Chemical group 0.000 claims description 56
- 125000003545 alkoxy group Chemical group 0.000 claims description 55
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 54
- 150000003839 salts Chemical class 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 45
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 38
- 125000005553 heteroaryloxy group Chemical group 0.000 claims description 37
- 125000004104 aryloxy group Chemical group 0.000 claims description 34
- 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 description 31
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 31
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 31
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 30
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 30
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 21
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims description 14
- BJLUNDZICFZBJD-UHFFFAOYSA-N [5-(4-aminophenyl)furan-2-yl]-(1,4-diazabicyclo[3.2.2]nonan-4-yl)methanone Chemical compound C1=CC(N)=CC=C1C1=CC=C(C(=O)N2C3CCN(CC3)CC2)O1 BJLUNDZICFZBJD-UHFFFAOYSA-N 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
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- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 10
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- 125000004076 pyridyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 125000002541 furyl group Chemical group 0.000 claims description 7
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- 229910052717 sulfur Inorganic materials 0.000 claims description 7
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- 125000004521 1,3,4-thiadiazol-2-yl group Chemical group S1C(=NN=C1)* 0.000 claims description 6
- ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 claims description 6
- 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 claims description 6
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- 241001465754 Metazoa Species 0.000 claims description 6
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- 125000000842 isoxazolyl group Chemical group 0.000 claims description 6
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- 125000002883 imidazolyl group Chemical group 0.000 claims description 5
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- XNMFNLRNMZWUIA-UHFFFAOYSA-N n-[4-[5-(1,4-diazabicyclo[3.2.2]nonane-4-carbonyl)furan-2-yl]phenyl]prop-2-enamide Chemical compound C1=CC(NC(=O)C=C)=CC=C1C1=CC=C(C(=O)N2C3CCN(CC3)CC2)O1 XNMFNLRNMZWUIA-UHFFFAOYSA-N 0.000 claims description 5
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- KZTBGMWRHBBBPK-UHFFFAOYSA-N 1,4-diazabicyclo[3.2.2]nonan-4-yl-[5-(2-phenylethynyl)furan-2-yl]methanone Chemical compound C1CN(CC2)CCC2N1C(=O)C(O1)=CC=C1C#CC1=CC=CC=C1 KZTBGMWRHBBBPK-UHFFFAOYSA-N 0.000 claims description 3
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Classifications
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Landscapes
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Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US44987103P | 2003-02-27 | 2003-02-27 | |
| DKPA200300310 | 2003-02-27 | ||
| US60/449,871 | 2003-02-27 | ||
| DKPA200300310 | 2003-02-27 | ||
| DKPA200300940 | 2003-06-24 | ||
| DKPA200300940 | 2003-06-24 | ||
| US48202203P | 2003-06-25 | 2003-06-25 | |
| US60/482,022 | 2003-06-25 | ||
| PCT/EP2004/050079 WO2004076453A1 (en) | 2003-02-27 | 2004-02-04 | Novel diazabicyclic aryl derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2518675A1 true CA2518675A1 (en) | 2004-09-10 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002518675A Abandoned CA2518675A1 (en) | 2003-02-27 | 2004-02-04 | Novel diazabicyclic aryl derivatives |
Country Status (11)
| Country | Link |
|---|---|
| US (2) | US7678788B2 (enExample) |
| EP (1) | EP1599476B1 (enExample) |
| JP (1) | JP2006519208A (enExample) |
| AT (1) | ATE445618T1 (enExample) |
| AU (1) | AU2004215658B2 (enExample) |
| BR (1) | BRPI0407216A (enExample) |
| CA (1) | CA2518675A1 (enExample) |
| DE (1) | DE602004023586D1 (enExample) |
| MX (1) | MXPA05006861A (enExample) |
| NZ (1) | NZ540998A (enExample) |
| WO (1) | WO2004076453A1 (enExample) |
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| SE0202430D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New Compounds |
| US7094572B2 (en) | 2003-03-14 | 2006-08-22 | Bristol-Myers Squibb | Polynucleotide encoding a novel human G-protein coupled receptor variant of HM74, HGPRBMY74 |
| TW200529860A (en) * | 2003-12-22 | 2005-09-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| AU2005210039B2 (en) * | 2004-02-04 | 2010-09-02 | Neurosearch A/S | Diazabicyclic aryl derivatives as nicotinic acetylcholine receptor ligands |
| ATE437880T1 (de) * | 2004-02-04 | 2009-08-15 | Neurosearch As | Dimere azacyclische verbindungen und deren verwendung |
| RU2386633C2 (ru) | 2004-05-07 | 2010-04-20 | Мемори Фармасьютиклз Корпорейшн | 1h-индазолы, бензотиазолы, 1, 2-бензоизоксазолы, 1, 2-бензоизотиазолы и хромоны и их получение и применения |
| US7514450B2 (en) | 2004-05-19 | 2009-04-07 | Neurosearch A/S | Azabicyclic aryl derivatives |
| TWI405763B (zh) | 2006-11-02 | 2013-08-21 | Targacept Inc | 菸鹼乙醯膽鹼受體亞型選擇性之二氮雜雙環烷類醯胺 |
| SA08290475B1 (ar) | 2007-08-02 | 2013-06-22 | Targacept Inc | (2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه |
| GB0723814D0 (en) * | 2007-12-05 | 2008-01-16 | Glaxo Group Ltd | Compounds |
| DE102008015033A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte (Pyrazolyl-carbonyl)imidazolidinone und ihre Verwendung |
| DE102008015032A1 (de) | 2008-03-17 | 2009-09-24 | Aicuris Gmbh & Co. Kg | Substituierte Pyrazolamide und ihre Verwendung |
| DE102008062878A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte Furancarboxamide und ihre Verwendung |
| DE102008062863A1 (de) | 2008-12-17 | 2010-06-24 | Aicuris Gmbh & Co. Kg | Substituierte (Thiophenyl-carbonyl)imidazolidinone und ihre Verwendung |
| TW201031664A (en) | 2009-01-26 | 2010-09-01 | Targacept Inc | Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide |
| TWI558398B (zh) | 2009-09-22 | 2016-11-21 | 諾華公司 | 菸鹼乙醯膽鹼受體α７活化劑之用途 |
| WO2012087833A1 (en) | 2010-12-22 | 2012-06-28 | Abbott Laboratories | Hepatitis c inhibitors and uses thereof |
| WO2020163248A1 (en) | 2019-02-04 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| WO2020163541A1 (en) | 2019-02-05 | 2020-08-13 | Skyhawk Therapeutics, Inc. | Methods and compositions for modulating splicing |
| JP7603594B2 (ja) | 2019-02-06 | 2024-12-20 | スカイホーク・セラピューティクス・インコーポレーテッド | スプライシングを調節するための方法および組成物 |
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| US7122339B2 (en) * | 1998-10-09 | 2006-10-17 | Medical Research Council | Method for generating diversity |
| FR2791678B1 (fr) * | 1999-03-30 | 2001-05-04 | Synthelabo | Derives de 1,4-diazabicyclo [3.2.2] nonane-4-carboxylates et -carboxamides, leur preparation et leur application en therapeutique |
| NZ513575A (en) * | 1999-05-04 | 2003-07-25 | Neurosearch As | Heteroaryl diazabicycloalkanes useful for treating or preventing a disease or a disorder responsive to the activity of nAChR modulators |
| FR2804430B1 (fr) | 2000-01-28 | 2002-03-22 | Sanofi Synthelabo | Derives de 4-heteroaryl-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
| FR2809730B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo[3.2.2] nonanebenzoxazole, -benzothiazole et -benzimidazole, leur preparation et leur application therapeutique |
| FR2809731B1 (fr) * | 2000-05-31 | 2002-07-19 | Sanofi Synthelabo | Derives de 1,4-diazabicyclo-[3.2.2] nonane-pheylisoxazole, leur preparation et leur application en therapeutique |
| US20020086871A1 (en) * | 2000-12-29 | 2002-07-04 | O'neill Brian Thomas | Pharmaceutical composition for the treatment of CNS and other disorders |
| DE60216830T2 (de) * | 2001-02-06 | 2007-06-14 | Pfizer Products Inc., Groton | Pharmazeutische Zusammensetzungen zur Behandlung von Störungen des ZNS oder anderen Erkrankungen |
| FR2832712B1 (fr) | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(oxadiazol-3-yl)-1,4-diazabicyclo[3.2.2]nonane, leur preparation et leur application en therapeutique |
| FR2832713B1 (fr) | 2001-11-23 | 2004-02-13 | Sanofi Synthelabo | Derives de 4-(1,3,4-thiadiazol-2-yl)-1,4-diazabicyclo[3.2.2] nonane, leur preparation et leur application en therapeutique |
| AU2002311553A1 (en) | 2002-06-26 | 2004-01-19 | Nokia Corporation | Method and network element for optimisation of radio resource utilisation in a radio access network |
| SE0202430D0 (sv) * | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New Compounds |
| SE0202465D0 (sv) | 2002-08-14 | 2002-08-14 | Astrazeneca Ab | New compounds |
| DE60311853T2 (de) | 2002-09-30 | 2007-06-21 | Neurosearch A/S | Neue 1,4-diazabicycloalkanderivate, deren herstellung und verwendung |
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2004
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- 2004-02-04 BR BR0407216-2A patent/BRPI0407216A/pt not_active Application Discontinuation
- 2004-02-04 AU AU2004215658A patent/AU2004215658B2/en not_active Ceased
- 2004-02-04 AT AT04707948T patent/ATE445618T1/de not_active IP Right Cessation
- 2004-02-04 WO PCT/EP2004/050079 patent/WO2004076453A1/en not_active Ceased
- 2004-02-04 DE DE602004023586T patent/DE602004023586D1/de not_active Expired - Lifetime
- 2004-02-04 NZ NZ540998A patent/NZ540998A/en not_active IP Right Cessation
- 2004-02-04 EP EP04707948A patent/EP1599476B1/en not_active Expired - Lifetime
- 2004-02-04 MX MXPA05006861A patent/MXPA05006861A/es active IP Right Grant
- 2004-02-04 CA CA002518675A patent/CA2518675A1/en not_active Abandoned
- 2004-02-04 US US10/547,157 patent/US7678788B2/en active Active
-
2010
- 2010-01-27 US US12/694,952 patent/US20100130483A1/en not_active Abandoned
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|---|---|
| WO2004076453A1 (en) | 2004-09-10 |
| NZ540998A (en) | 2008-06-30 |
| ATE445618T1 (de) | 2009-10-15 |
| US7678788B2 (en) | 2010-03-16 |
| US20100130483A1 (en) | 2010-05-27 |
| AU2004215658A1 (en) | 2004-09-10 |
| US20060148789A1 (en) | 2006-07-06 |
| AU2004215658B2 (en) | 2010-06-24 |
| EP1599476B1 (en) | 2009-10-14 |
| JP2006519208A (ja) | 2006-08-24 |
| MXPA05006861A (es) | 2005-12-12 |
| DE602004023586D1 (de) | 2009-11-26 |
| EP1599476A1 (en) | 2005-11-30 |
| BRPI0407216A (pt) | 2006-01-24 |
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