ES2446644T3 - Inhibidor de recaptación de serotonina y norepinefrina - Google Patents
Inhibidor de recaptación de serotonina y norepinefrina Download PDFInfo
- Publication number
- ES2446644T3 ES2446644T3 ES10713753.1T ES10713753T ES2446644T3 ES 2446644 T3 ES2446644 T3 ES 2446644T3 ES 10713753 T ES10713753 T ES 10713753T ES 2446644 T3 ES2446644 T3 ES 2446644T3
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- pyrrolidine
- mmol
- pyridyloxy
- butyl
- Prior art date
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- 229940121991 Serotonin and norepinephrine reuptake inhibitor Drugs 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 135
- 150000003839 salts Chemical class 0.000 claims abstract description 48
- -1 chloro, bromo, methyl Chemical group 0.000 claims abstract description 43
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 24
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims abstract description 21
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 12
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract description 11
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 10
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 27
- 208000002193 Pain Diseases 0.000 claims description 25
- 241000282414 Homo sapiens Species 0.000 claims description 7
- SNNRWIBSGBMYRF-ZFWWWQNUSA-N 6-methoxy-2-methyl-3-[(1s)-3-methyl-1-[(3s)-pyrrolidin-3-yl]butoxy]pyridine Chemical compound CC1=NC(OC)=CC=C1O[C@@H](CC(C)C)[C@@H]1CNCC1 SNNRWIBSGBMYRF-ZFWWWQNUSA-N 0.000 claims description 6
- 208000000094 Chronic Pain Diseases 0.000 claims description 6
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- 239000003937 drug carrier Substances 0.000 claims description 4
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 238000002560 therapeutic procedure Methods 0.000 claims description 2
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- SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 13
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- SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 13
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- 229910052794 bromium Inorganic materials 0.000 description 12
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- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
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- GBQSPYSYTXCLEV-VUWPPUDQSA-N tert-butyl (3s)-3-(1-hydroxybutyl)pyrrolidine-1-carboxylate Chemical compound CCCC(O)[C@H]1CCN(C(=O)OC(C)(C)C)C1 GBQSPYSYTXCLEV-VUWPPUDQSA-N 0.000 description 1
- PIMHNEBWYKVGLC-JTQLQIEISA-N tert-butyl (3s)-3-(2-oxobut-3-enyl)pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@@H](CC(=O)C=C)C1 PIMHNEBWYKVGLC-JTQLQIEISA-N 0.000 description 1
- BSMMBVNMUXWHAI-NSHDSACASA-N tert-butyl (3s)-3-(cyclobutanecarbonyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1C(=O)C1CCC1 BSMMBVNMUXWHAI-NSHDSACASA-N 0.000 description 1
- DBAGVNHLDFJPAM-JTQLQIEISA-N tert-butyl (3s)-3-(cyclopropanecarbonyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1C(=O)C1CC1 DBAGVNHLDFJPAM-JTQLQIEISA-N 0.000 description 1
- SKONKHNFBLVNME-PXYINDEMSA-N tert-butyl (3s)-3-[cyclobutyl(hydroxy)methyl]pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CC[C@@H]1C(O)C1CCC1 SKONKHNFBLVNME-PXYINDEMSA-N 0.000 description 1
- NPQBRICVBVRTHV-JTQLQIEISA-N tert-butyl (3s)-3-but-3-enoylpyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CC[C@H](C(=O)CC=C)C1 NPQBRICVBVRTHV-JTQLQIEISA-N 0.000 description 1
- GJJYYMXBCYYXPQ-UHFFFAOYSA-N tert-butyl 2-oxopyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1=O GJJYYMXBCYYXPQ-UHFFFAOYSA-N 0.000 description 1
- UIPCANSIESEVFI-UHFFFAOYSA-N tert-butyl 3-(2-cyclobutyl-1-hydroxyethyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C(O)CC1CCC1 UIPCANSIESEVFI-UHFFFAOYSA-N 0.000 description 1
- MMLYPRGGSZIVMJ-UHFFFAOYSA-N tert-butyl 3-(2-cyclobutylideneacetyl)pyrrolidine-1-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCC1C(=O)C=C1CCC1 MMLYPRGGSZIVMJ-UHFFFAOYSA-N 0.000 description 1
- YQPCCBZVSVEPGX-UHFFFAOYSA-N tert-butyl 3-(2-diethoxyphosphorylacetyl)pyrrolidine-1-carboxylate Chemical compound CCOP(=O)(OCC)CC(=O)C1CCN(C(=O)OC(C)(C)C)C1 YQPCCBZVSVEPGX-UHFFFAOYSA-N 0.000 description 1
- LPQZERIRKRYGGM-UHFFFAOYSA-N tert-butyl pyrrolidine-1-carboxylate Chemical compound CC(C)(C)OC(=O)N1CCCC1 LPQZERIRKRYGGM-UHFFFAOYSA-N 0.000 description 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
- 230000000451 tissue damage Effects 0.000 description 1
- 231100000827 tissue damage Toxicity 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 238000010200 validation analysis Methods 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- PNVNVHUZROJLTJ-UHFFFAOYSA-N venlafaxine Chemical compound C1=CC(OC)=CC=C1C(CN(C)C)C1(O)CCCCC1 PNVNVHUZROJLTJ-UHFFFAOYSA-N 0.000 description 1
- 229960004688 venlafaxine Drugs 0.000 description 1
- 210000001835 viscera Anatomy 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4439—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a five-membered ring with nitrogen as a ring hetero atom, e.g. omeprazole
-
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Epidemiology (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US16807909P | 2009-04-09 | 2009-04-09 | |
| US168079P | 2009-04-09 | ||
| PCT/US2010/030038 WO2010117979A2 (en) | 2009-04-09 | 2010-04-06 | Serotonin and norepinephrine reuptake inhibitor |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2446644T3 true ES2446644T3 (es) | 2014-03-10 |
Family
ID=42698378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES10713753.1T Active ES2446644T3 (es) | 2009-04-09 | 2010-04-06 | Inhibidor de recaptación de serotonina y norepinefrina |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US8173821B2 (https=) |
| EP (1) | EP2417124B1 (https=) |
| JP (1) | JP2012523416A (https=) |
| KR (1) | KR101378260B1 (https=) |
| CN (1) | CN102388036A (https=) |
| AR (1) | AR075988A1 (https=) |
| AU (1) | AU2010234610B2 (https=) |
| BR (1) | BRPI1014382A2 (https=) |
| CA (1) | CA2758251C (https=) |
| EA (1) | EA201171230A1 (https=) |
| ES (1) | ES2446644T3 (https=) |
| MX (1) | MX2011010658A (https=) |
| TW (1) | TW201103908A (https=) |
| WO (1) | WO2010117979A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2434250T3 (es) | 2008-07-24 | 2013-12-16 | Theravance, Inc. | Compuestos de 3-(fenoxifenilmetil)pirrolidina |
| JP2012524098A (ja) * | 2009-04-15 | 2012-10-11 | セラヴァンス， インコーポレーテッド | ３−（フェノキシピロリジン−３−イル−メチル）ヘテロアリール、３−（フェニルピロリジン−３−イルメトキシ）ヘテロアリールおよび３−（ヘテロアリールピロリジン−３−イルメトキシ）ヘテロアリール化合物 |
| US7994209B2 (en) | 2009-07-13 | 2011-08-09 | Theravance, Inc. | 3-phenoxymethylpyrrolidine compounds |
| JP5714580B2 (ja) * | 2009-07-21 | 2015-05-07 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | ３−フェノキシメチルピロリジン化合物 |
| JP5873877B2 (ja) | 2010-10-11 | 2016-03-01 | セラヴァンス バイオファーマ アール＆ディー アイピー， エルエルシー | セロトニン再取込みインヒビター |
| WO2012075239A1 (en) | 2010-12-03 | 2012-06-07 | Theravance, Inc. | Serotonin reuptake inhibitors |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL1004346C2 (nl) | 1996-10-23 | 1998-04-24 | Dsm Nv | Werkwijze voor het scheiden van een mengsel van enantiomeren in een geschikt oplosmiddel. |
| DE69717148T2 (de) * | 1996-12-10 | 2003-10-02 | Abbott Laboratories, Abbott Park | 3-pyridylenantiomere und ihre verwendung als analgetika |
| PT1047690E (pt) | 1997-12-19 | 2004-07-30 | Abbott Lab | Compostos eter e tioeter heterociclicos uteis no controlo da transmissao quimica sinaptica |
| MXPA02002115A (es) | 1999-09-14 | 2002-10-31 | Abbott Lab | Compuestos de eter 3-pirrolidiniloxi-3'-piridilico, utiles para controlar la transmision sinaptica quimica. . |
| US20020151712A1 (en) | 1999-09-14 | 2002-10-17 | Nan-Horng Lin | 3-pyrrolidinyloxy-3'-pyridyl ether compounds useful for controlling chemical synaptic transmission |
| JP4185154B2 (ja) | 2004-04-30 | 2008-11-26 | ワーナー−ランバート カンパニー リミテッド ライアビリティー カンパニー | 中枢神経系障害治療用の置換モルホリン化合物 |
| WO2008023258A1 (en) | 2006-08-23 | 2008-02-28 | Pfizer Products Inc. | Piperidine derivatives |
| JP5330260B2 (ja) | 2006-12-06 | 2013-10-30 | スミスクライン ビーチャム コーポレーション | 二環式化合物ならびに抗糖尿病薬としての使用 |
| ES2434250T3 (es) | 2008-07-24 | 2013-12-16 | Theravance, Inc. | Compuestos de 3-(fenoxifenilmetil)pirrolidina |
-
2010
- 2010-03-29 AR ARP100101017A patent/AR075988A1/es unknown
- 2010-04-02 TW TW099110421A patent/TW201103908A/zh unknown
- 2010-04-06 BR BRPI1014382A patent/BRPI1014382A2/pt not_active IP Right Cessation
- 2010-04-06 ES ES10713753.1T patent/ES2446644T3/es active Active
- 2010-04-06 CN CN2010800160763A patent/CN102388036A/zh active Pending
- 2010-04-06 KR KR1020117023570A patent/KR101378260B1/ko not_active Expired - Fee Related
- 2010-04-06 EP EP10713753.1A patent/EP2417124B1/en not_active Not-in-force
- 2010-04-06 EA EA201171230A patent/EA201171230A1/ru unknown
- 2010-04-06 JP JP2012504759A patent/JP2012523416A/ja active Pending
- 2010-04-06 US US12/754,800 patent/US8173821B2/en not_active Expired - Fee Related
- 2010-04-06 WO PCT/US2010/030038 patent/WO2010117979A2/en not_active Ceased
- 2010-04-06 CA CA2758251A patent/CA2758251C/en not_active Expired - Fee Related
- 2010-04-06 AU AU2010234610A patent/AU2010234610B2/en not_active Ceased
- 2010-04-06 MX MX2011010658A patent/MX2011010658A/es active IP Right Grant
Also Published As
| Publication number | Publication date |
|---|---|
| JP2012523416A (ja) | 2012-10-04 |
| CA2758251C (en) | 2013-08-06 |
| AU2010234610A1 (en) | 2011-10-06 |
| MX2011010658A (es) | 2011-10-21 |
| EP2417124B1 (en) | 2013-12-18 |
| KR20110123287A (ko) | 2011-11-14 |
| US8173821B2 (en) | 2012-05-08 |
| KR101378260B1 (ko) | 2014-03-27 |
| CA2758251A1 (en) | 2010-10-14 |
| WO2010117979A3 (en) | 2011-02-17 |
| US20100261762A1 (en) | 2010-10-14 |
| EA201171230A1 (ru) | 2012-03-30 |
| EP2417124A2 (en) | 2012-02-15 |
| TW201103908A (en) | 2011-02-01 |
| CN102388036A (zh) | 2012-03-21 |
| BRPI1014382A2 (pt) | 2016-04-05 |
| WO2010117979A2 (en) | 2010-10-14 |
| AR075988A1 (es) | 2011-05-11 |
| AU2010234610B2 (en) | 2013-04-18 |
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