JP2005527588A5 - - Google Patents
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- Publication number
- JP2005527588A5 JP2005527588A5 JP2003584059A JP2003584059A JP2005527588A5 JP 2005527588 A5 JP2005527588 A5 JP 2005527588A5 JP 2003584059 A JP2003584059 A JP 2003584059A JP 2003584059 A JP2003584059 A JP 2003584059A JP 2005527588 A5 JP2005527588 A5 JP 2005527588A5
- Authority
- JP
- Japan
- Prior art keywords
- furo
- azabicyclo
- spiro
- octane
- pyridine
- 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.)
- Granted
Links
- 150000001875 compounds Chemical class 0.000 claims 11
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims 8
- 208000035475 disorder Diseases 0.000 claims 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims 4
- 229910052736 halogen Inorganic materials 0.000 claims 4
- 150000002367 halogens Chemical class 0.000 claims 4
- 229910052739 hydrogen Inorganic materials 0.000 claims 4
- 239000001257 hydrogen Substances 0.000 claims 4
- 239000008194 pharmaceutical composition Substances 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 102000019315 Nicotinic acetylcholine receptors Human genes 0.000 claims 3
- 108050006807 Nicotinic acetylcholine receptors Proteins 0.000 claims 3
- 239000003814 drug Substances 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 230000002265 prevention Effects 0.000 claims 3
- 150000003839 salts Chemical class 0.000 claims 3
- SNICXCGAKADSCV-JTQLQIEISA-N (-)-Nicotine Chemical compound CN1CCC[C@H]1C1=CC=CN=C1 SNICXCGAKADSCV-JTQLQIEISA-N 0.000 claims 2
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 claims 2
- 208000024827 Alzheimer disease Diseases 0.000 claims 2
- 208000000044 Amnesia Diseases 0.000 claims 2
- 208000019901 Anxiety disease Diseases 0.000 claims 2
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims 2
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims 2
- 208000020925 Bipolar disease Diseases 0.000 claims 2
- 208000019888 Circadian rhythm sleep disease Diseases 0.000 claims 2
- 206010009900 Colitis ulcerative Diseases 0.000 claims 2
- 208000023105 Huntington disease Diseases 0.000 claims 2
- 208000001456 Jet Lag Syndrome Diseases 0.000 claims 2
- 206010026749 Mania Diseases 0.000 claims 2
- 208000026139 Memory disease Diseases 0.000 claims 2
- 206010057852 Nicotine dependence Diseases 0.000 claims 2
- 208000018737 Parkinson disease Diseases 0.000 claims 2
- 208000028017 Psychotic disease Diseases 0.000 claims 2
- 208000025569 Tobacco Use disease Diseases 0.000 claims 2
- 208000000323 Tourette Syndrome Diseases 0.000 claims 2
- 208000016620 Tourette disease Diseases 0.000 claims 2
- 201000006704 Ulcerative Colitis Diseases 0.000 claims 2
- 230000004913 activation Effects 0.000 claims 2
- 150000001350 alkyl halides Chemical class 0.000 claims 2
- 230000036506 anxiety Effects 0.000 claims 2
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims 2
- 230000009286 beneficial effect Effects 0.000 claims 2
- 208000028683 bipolar I disease Diseases 0.000 claims 2
- 230000001713 cholinergic effect Effects 0.000 claims 2
- 208000010877 cognitive disease Diseases 0.000 claims 2
- 235000019788 craving Nutrition 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 201000010099 disease Diseases 0.000 claims 2
- 208000033915 jet lag type circadian rhythm sleep disease Diseases 0.000 claims 2
- 201000003723 learning disability Diseases 0.000 claims 2
- 230000006984 memory degeneration Effects 0.000 claims 2
- 208000023060 memory loss Diseases 0.000 claims 2
- 208000015122 neurodegenerative disease Diseases 0.000 claims 2
- 229960002715 nicotine Drugs 0.000 claims 2
- SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims 2
- 201000000980 schizophrenia Diseases 0.000 claims 2
- 230000005586 smoking cessation Effects 0.000 claims 2
- 125000003003 spiro group Chemical group 0.000 claims 2
- 210000000225 synapse Anatomy 0.000 claims 2
- 229930192474 thiophene Natural products 0.000 claims 2
- RGRFTIUNUVXJFV-NRFANRHFSA-N (3r)-5'-(1-benzothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1=CC=C2SC(C=3C=C4C[C@]5(C6CCN(CC6)C5)OC4=NC=3)=CC2=C1 RGRFTIUNUVXJFV-NRFANRHFSA-N 0.000 claims 1
- MKMCCVGYQLOGJN-NRFANRHFSA-N (3r)-5'-(1-benzothiophen-3-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C1=CC=C2C(C=3C=C4C[C@]5(C6CCN(CC6)C5)OC4=NC=3)=CSC2=C1 MKMCCVGYQLOGJN-NRFANRHFSA-N 0.000 claims 1
- XMYKXOCVJKLGSH-SFHVURJKSA-N (3r)-5'-(4-methylthiophen-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound CC1=CSC(C=2C=C3C[C@@]4(OC3=NC=2)C2CCN(CC2)C4)=C1 XMYKXOCVJKLGSH-SFHVURJKSA-N 0.000 claims 1
- CABQJIZQLLQXQI-KRWDZBQOSA-N (3r)-5'-(5-bromothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(Br)=CC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 CABQJIZQLLQXQI-KRWDZBQOSA-N 0.000 claims 1
- DBGIZTGPWQNSSJ-KRWDZBQOSA-N (3r)-5'-(5-bromothiophen-3-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(Br)=CC(C=2C=C3C[C@@]4(OC3=NC=2)C2CCN(CC2)C4)=C1 DBGIZTGPWQNSSJ-KRWDZBQOSA-N 0.000 claims 1
- CJYZUXDETNGQMM-KRWDZBQOSA-N (3r)-5'-(5-chlorothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(Cl)=CC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 CJYZUXDETNGQMM-KRWDZBQOSA-N 0.000 claims 1
- RQFPIXLGXRQAPI-KRWDZBQOSA-N (3r)-5'-(5-chlorothiophen-3-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(Cl)=CC(C=2C=C3C[C@@]4(OC3=NC=2)C2CCN(CC2)C4)=C1 RQFPIXLGXRQAPI-KRWDZBQOSA-N 0.000 claims 1
- OMSGRSKTHWPJNV-KRWDZBQOSA-N (3r)-5'-(5-fluorothiophen-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(F)=CC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 OMSGRSKTHWPJNV-KRWDZBQOSA-N 0.000 claims 1
- DYLBIMKJVBZUNA-KRWDZBQOSA-N (3r)-5'-(5-fluorothiophen-3-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(F)=CC(C=2C=C3C[C@@]4(OC3=NC=2)C2CCN(CC2)C4)=C1 DYLBIMKJVBZUNA-KRWDZBQOSA-N 0.000 claims 1
- PVCRUOGAHDRKGZ-SFHVURJKSA-N (3r)-5'-(5-methylthiophen-2-yl)spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound S1C(C)=CC=C1C1=CN=C(O[C@]2(C3)C4CCN(CC4)C2)C3=C1 PVCRUOGAHDRKGZ-SFHVURJKSA-N 0.000 claims 1
- AHRUHWJGGHPBCA-KRWDZBQOSA-N (3r)-5'-thiophen-2-ylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C1=CC=CS1 AHRUHWJGGHPBCA-KRWDZBQOSA-N 0.000 claims 1
- PKEIGGSVAYHOQK-KRWDZBQOSA-N (3r)-5'-thiophen-3-ylspiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine] Chemical compound C([C@]1(C2CCN(CC2)C1)OC1=NC=2)C1=CC=2C=1C=CSC=1 PKEIGGSVAYHOQK-KRWDZBQOSA-N 0.000 claims 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 1
- LYTMVABTDYMBQK-UHFFFAOYSA-N 2-benzothiophene Chemical compound C1=CC=CC2=CSC=C21 LYTMVABTDYMBQK-UHFFFAOYSA-N 0.000 claims 1
- 208000028698 Cognitive impairment Diseases 0.000 claims 1
- 201000004311 Gilles de la Tourette syndrome Diseases 0.000 claims 1
- LELOWRISYMNNSU-UHFFFAOYSA-N Hydrocyanic acid Natural products N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- 208000020358 Learning disease Diseases 0.000 claims 1
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical group [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims 1
- 230000008484 agonism Effects 0.000 claims 1
- 230000001270 agonistic effect Effects 0.000 claims 1
- 125000003342 alkenyl group Chemical group 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- 125000000304 alkynyl group Chemical group 0.000 claims 1
- 230000003042 antagnostic effect Effects 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 230000006735 deficit Effects 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 230000002285 radioactive effect Effects 0.000 claims 1
- 208000024891 symptom Diseases 0.000 claims 1
- ACJGOCAFNPOHJE-AHJYMZSGSA-N trimethyl-[(3r)-spiro[1-azabicyclo[2.2.2]octane-3,2'-3h-furo[2,3-b]pyridine]-5'-yl]stannane Chemical compound C1N(CC2)CCC2[C@@]11OC2=NC=C([Sn](C)(C)C)C=C2C1 ACJGOCAFNPOHJE-AHJYMZSGSA-N 0.000 claims 1
- 229910052722 tritium Inorganic materials 0.000 claims 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SE0201187A SE0201187D0 (sv) | 2002-04-18 | 2002-04-18 | Thienyl compounds |
| SE0203608A SE0203608D0 (sv) | 2002-12-04 | 2002-12-04 | Thienyl compounds |
| PCT/SE2003/000614 WO2003087103A1 (en) | 2002-04-18 | 2003-04-15 | Thienyl compounds |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2005527588A JP2005527588A (ja) | 2005-09-15 |
| JP2005527588A5 true JP2005527588A5 (https=) | 2006-06-01 |
| JP4511196B2 JP4511196B2 (ja) | 2010-07-28 |
Family
ID=29253789
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2003584059A Expired - Fee Related JP4511196B2 (ja) | 2002-04-18 | 2003-04-15 | チエニル化合物 |
Country Status (16)
| Country | Link |
|---|---|
| US (3) | US7186836B2 (https=) |
| EP (1) | EP1499615B1 (https=) |
| JP (1) | JP4511196B2 (https=) |
| KR (1) | KR20040099448A (https=) |
| CN (1) | CN1325499C (https=) |
| AT (1) | ATE477256T1 (https=) |
| AU (1) | AU2003224545B2 (https=) |
| BR (1) | BR0309342A (https=) |
| CA (1) | CA2482312A1 (https=) |
| DE (1) | DE60333746D1 (https=) |
| ES (1) | ES2348282T3 (https=) |
| IL (1) | IL164613A0 (https=) |
| MX (1) | MXPA04010193A (https=) |
| NO (1) | NO20044997L (https=) |
| NZ (1) | NZ535978A (https=) |
| WO (1) | WO2003087103A1 (https=) |
Families Citing this family (29)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR036040A1 (es) | 2001-06-12 | 2004-08-04 | Upjohn Co | Compuestos de heteroarilo multiciclicos sustituidos con quinuclidinas y composiciones farmaceuticas que los contienen |
| CA2462453C (en) | 2001-10-02 | 2009-07-28 | Pharmacia & Upjohn Company | Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease |
| DE10164139A1 (de) | 2001-12-27 | 2003-07-10 | Bayer Ag | 2-Heteroarylcarbonsäureamide |
| US7417049B2 (en) * | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Furyl compounds |
| ES2348282T3 (es) * | 2002-04-18 | 2010-12-02 | Astrazeneca Ab | Compuestos de tienilo. |
| BRPI0415546A (pt) * | 2003-10-21 | 2006-12-26 | Astrazeneca Ab | composto, composição farmacêutica, uso de um composto, e, métodos de tratamento ou profilaxia de doenças ou condições humanas, e de distúrbios |
| US7045530B2 (en) | 2003-12-22 | 2006-05-16 | Abbott Laboratories | Spirocyclic quinuclidinic ether derivatives |
| TW200813067A (en) | 2006-05-17 | 2008-03-16 | Astrazeneca Ab | Nicotinic acetylcholine receptor ligands |
| 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 |
| CN102131791B (zh) | 2008-06-20 | 2014-12-24 | 阿斯利康(瑞典)有限公司 | 二苯并硫杂氮杂*衍生物及其用途 |
| 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 |
| PE20170923A1 (es) | 2010-05-17 | 2017-07-12 | Forum Pharmaceuticals Inc | Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin-3-il)benzo[b]tiofeno-2-carboxamida monohidratado |
| GB201111705D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Compounds and their use |
| GB201111704D0 (en) | 2011-07-07 | 2011-08-24 | Takeda Pharmaceutical | Novel compounds |
| JO3115B1 (ar) | 2011-08-22 | 2017-09-20 | Takeda Pharmaceuticals Co | مركبات بيريدازينون واستخدامها كمثبطات daao |
| EP3461481A1 (en) | 2012-05-08 | 2019-04-03 | Forum Pharmaceuticals Inc. | Methods of maintaining, treating or improving cognitive function |
| GB201209587D0 (en) | 2012-05-30 | 2012-07-11 | Takeda Pharmaceutical | Therapeutic compounds |
| JP6478923B2 (ja) | 2013-02-07 | 2019-03-06 | ヘプタレス セラピューティクス リミテッドＨｅｐｔａｒｅｓ Ｔｈｅｒａｐｅｕｔｉｃｓ Ｌｉｍｉｔｅｄ | ムスカリンｍ４受容体アゴニストとしてのピペリジン−１−イル及びアゼピン−１−イルカルボキシレート |
| WO2014202999A1 (en) | 2013-06-21 | 2014-12-24 | Takeda Cambridge Limited | 1-sulfonyl piperidine derivatives as modulators of prokineticin receptors |
| GB201314286D0 (en) | 2013-08-08 | 2013-09-25 | Takeda Pharmaceutical | Therapeutic Compounds |
| GB201318222D0 (en) | 2013-10-15 | 2013-11-27 | Takeda Pharmaceutical | Novel compounds |
| GB201320905D0 (en) | 2013-11-27 | 2014-01-08 | Takeda Pharmaceutical | Therapeutic compounds |
| TW201613864A (en) | 2014-02-20 | 2016-04-16 | Takeda Pharmaceutical | Novel compounds |
| GB201616839D0 (en) | 2016-10-04 | 2016-11-16 | Takeda Pharmaceutical Company Limited | Therapeutic compounds |
| GB201619514D0 (en) | 2016-11-18 | 2017-01-04 | Takeda Pharmaceuticals Co | Novel compounds |
| JP2021138648A (ja) | 2020-03-04 | 2021-09-16 | 武田薬品工業株式会社 | 経口固形製剤 |
| CN112898312B (zh) * | 2021-01-29 | 2021-11-12 | 湖南南新制药股份有限公司 | 一种稠合多环吡啶酮衍生物及其用途 |
| GB202414197D0 (en) | 2024-09-27 | 2024-11-13 | Addex Pharmaceuticals Sa | Novel compounds |
| GB202414193D0 (en) | 2024-09-27 | 2024-11-13 | Addex Pharmaceuticals Sa | Novel compounds |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR013184A1 (es) * | 1997-07-18 | 2000-12-13 | Astrazeneca Ab | Aminas heterociclicas espiroazobiciclicas, composicion farmaceutica, uso de dichas aminas para preparar medicamentos y metodo de tratamiento o profilaxis |
| SE9900100D0 (sv) * | 1999-01-15 | 1999-01-15 | Astra Ab | New compounds |
| FR2788982B1 (fr) * | 1999-02-02 | 2002-08-02 | Synthelabo | Compositions pharmaceutiques contenant de la nicotine et leur application dans le sevrage tabagique |
| US20010016677A1 (en) * | 1999-02-16 | 2001-08-23 | Dan Russell Poole | Incubator with thermoelectric cooler |
| US6569865B2 (en) * | 2001-06-01 | 2003-05-27 | Astrazeneca Ab | Spiro 1-azabicyclo[2.2.2]octane-3,2′(3′h)-furo[2,3-b]pyridine |
| BR0210075A (pt) * | 2001-06-01 | 2004-08-17 | Astrazeneca Ab | Composto, composição farmacêutica, uso de um composto, e, métodos de tratamento ou profilaxia de doenças ou condições humanas, de distúrbios psicóticos ou distúrbios da debilitação intelectual e de fadiga de vÈo, cessamento de fumar, dependência de nicotina, dores, e para a colite ulcerativa |
| ES2348282T3 (es) * | 2002-04-18 | 2010-12-02 | Astrazeneca Ab | Compuestos de tienilo. |
| US7417049B2 (en) * | 2002-04-18 | 2008-08-26 | Astrazeneca Ab | Furyl compounds |
-
2003
- 2003-04-15 ES ES03721208T patent/ES2348282T3/es not_active Expired - Lifetime
- 2003-04-15 BR BR0309342-5A patent/BR0309342A/pt not_active IP Right Cessation
- 2003-04-15 CN CNB038137828A patent/CN1325499C/zh not_active Expired - Fee Related
- 2003-04-15 KR KR10-2004-7016548A patent/KR20040099448A/ko not_active Ceased
- 2003-04-15 WO PCT/SE2003/000614 patent/WO2003087103A1/en not_active Ceased
- 2003-04-15 CA CA002482312A patent/CA2482312A1/en not_active Abandoned
- 2003-04-15 AU AU2003224545A patent/AU2003224545B2/en not_active Expired - Fee Related
- 2003-04-15 MX MXPA04010193A patent/MXPA04010193A/es active IP Right Grant
- 2003-04-15 JP JP2003584059A patent/JP4511196B2/ja not_active Expired - Fee Related
- 2003-04-15 US US10/511,522 patent/US7186836B2/en not_active Expired - Fee Related
- 2003-04-15 DE DE60333746T patent/DE60333746D1/de not_active Expired - Lifetime
- 2003-04-15 NZ NZ535978A patent/NZ535978A/en unknown
- 2003-04-15 EP EP03721208A patent/EP1499615B1/en not_active Expired - Lifetime
- 2003-04-15 AT AT03721208T patent/ATE477256T1/de not_active IP Right Cessation
-
2004
- 2004-10-14 IL IL16461304A patent/IL164613A0/xx unknown
- 2004-11-17 NO NO20044997A patent/NO20044997L/no not_active Application Discontinuation
-
2007
- 2007-01-29 US US11/668,099 patent/US20070142419A1/en not_active Abandoned
-
2010
- 2010-10-27 US US12/912,840 patent/US20110124672A1/en not_active Abandoned
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