JP4216072B2 - ドーパミンd2受容体及びセロトニン再取り込み部位に対する高い親和性を有する8−{4−[3−(5−フルオロー1h−インドール−3−イル)−プロピル]−ピペラジン−1−イル}−2−メチル−4h−ベンゾ[1,4]オキサジン−3−オンメシラート - Google Patents
ドーパミンd2受容体及びセロトニン再取り込み部位に対する高い親和性を有する8−{4−[3−(5−フルオロー1h−インドール−3−イル)−プロピル]−ピペラジン−1−イル}−2−メチル−4h−ベンゾ[1,4]オキサジン−3−オンメシラート Download PDFInfo
- Publication number
- JP4216072B2 JP4216072B2 JP2002565987A JP2002565987A JP4216072B2 JP 4216072 B2 JP4216072 B2 JP 4216072B2 JP 2002565987 A JP2002565987 A JP 2002565987A JP 2002565987 A JP2002565987 A JP 2002565987A JP 4216072 B2 JP4216072 B2 JP 4216072B2
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- Prior art keywords
- mesylate
- dopamine
- receptor
- serotonin reuptake
- oxazin
- 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 - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- 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
- A61P25/22—Anxiolytics
-
- 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
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- 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)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Engineering & Computer Science (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Neurology (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Psychiatry (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
Description
【0001】
本発明は式(I):
【0002】
【化1】
【0003】
の新規なフェニルピペラジン誘導体に関する。
【背景技術】
【0004】
特許出願明細書(特許文献1(WO01/14330)参照。)は、一群の新規なフェニルピペラジンに関する。この群の化合物は、ドーパミンD2受容体及びセロトニン再取り込み部位の両方に対する高い親和性を示す。この組み合わせは、全ての病徴(例えば、陽性症状及び陰性症状)のいっそう完全な処置を可能する統合失調症(schizophrenia)及び他の精神病性障害の処置に有用である。
【0005】
これらの化合物は、マウスにおいてアポモルフィンで誘発されるクライミング行動を潜在的に中和するので、ドーパミンD2受容体でのアンタゴニストとしての活性を示す。これらの化合物はまた、マウスにおいて5−HTPで誘発される行動を増強するので、セロトニン再取り込みのインヒビターとしての活性も示す。
【0006】
これらの化合物は、臨床的に関連する抗精神病薬(antipsychotics)(例えば、条件回避反応(conditioned avoidance response);(非特許文献1参照。)及び抗うつ薬もしくは抗不安薬(例えば、ストレスで誘発される発声の抑制(stress-induced vocalization);(非特許文献2参照。)に感受性の治療モデルにおいて有効である。
【0007】
臨床的に関連するドーパミンD2受容体アンタゴニストと異なり、記述する化合物は、げっ歯類においてカタレプシー(catalepsy)を誘発する傾向が低く、そしてそのようなものとして従来の抗精神病薬より少ない錐体外路副作用を誘発すると思われる。
【0008】
これらの化合物に固有のセロトニン再取り込みの阻害活性は、抗うつ薬もしくは抗不安薬のいずれかに感受性の行動モデルにおいて認められる治療効果を引き起こすことができる。
【0009】
これらの化合物は、ドーパミン作動性(dopaminergic)もしくはセロトニン作動性(serotonergic)の系のいずれかにおける障害により引き起こされる中枢神経系の障害もしくは疾患、例えば:攻撃、不安障害、自閉症、めまい、うつ病、認知もしくは記憶の障害、パーキンソン病、並びに特に統合失調症及び他の精神病性障害の処置に用いることができる。
【特許文献1】
特許出願第PCT/EP00/08190号明細書
【非特許文献1】
Van der Heyden & Bradford,Behav.Brain.Res.,1988,31:61−67
【非特許文献2】
van der Poel et al.,Psychopharmacology,1989,97:147−148
【発明の開示】
【0010】
今回、上記の式のメシラートが、遊離塩基(すなわち、WO01/14330の化合物番号89)と比較して特に好ましい性質を有することが見出された。
【0011】
このメシラート化合物は、遊離塩基よりはるかによく水に可溶性であり、優れた生物学的利用能をもたらす。
【0012】
該化合物はキラリティーの中心を有し;ラセミ混合物及び個々の鏡像異性体の両方とも本発明に帰属する。
【0013】
該化合物は、液体及び固体担体物質のような補助物質を用いて適当な方法によって投与に適当な形態にすることができる。
【0014】
化合物の遊離塩基は、WO01/14330に記述されているように製造することができる。
【0015】
遊離塩基は、塩形成のためのそれ自体既知である方法に従ってメシラートに転化することができる。
【0016】
本発明を以下の実施例によって例示する。
【実施例】
【0017】
WO01/14330(化合物番号89)に記述されているようにして得ることができる2.0g(4.7mmol)の遊離塩基を40mlのメタノールに懸濁する。懸濁液を60℃に温め、そして10mlのメタノール中0.45g(4.7mmol)のメタンスルホン酸の溶液を約2分の間に加える。清澄な溶液が得られる。60℃で5分間攪拌した後、結晶化が始まる。溶液を60分の間に20℃にゆっくりと冷却し、そしてその温度で30分間攪拌する。60分の間に0℃にさらに冷却し、そして90分間攪拌を実施する。濾過によって固体物質を単離し、5mlのメタノールで洗浄し、そして減圧下で50℃で一晩の間乾燥させる。収量2.17g(88%)の白色に着色したメシラート。
Claims (1)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01200610 | 2001-02-21 | ||
PCT/EP2002/001795 WO2002066473A1 (en) | 2001-02-21 | 2002-02-19 | 8’4-’3-(5-fluoro-1h-indol-3yl) propyl!-1-piperazynyl!-2-methyl-2h-1,4-benzoxazin -3 (4h)- one methanesulfonate with high affinity for the dopamine d 2 receptor and the serotonin reuptake site |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2004518747A JP2004518747A (ja) | 2004-06-24 |
JP2004518747A5 JP2004518747A5 (ja) | 2005-12-22 |
JP4216072B2 true JP4216072B2 (ja) | 2009-01-28 |
Family
ID=8179909
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2002565987A Expired - Fee Related JP4216072B2 (ja) | 2001-02-21 | 2002-02-19 | ドーパミンd2受容体及びセロトニン再取り込み部位に対する高い親和性を有する8−{4−[3−(5−フルオロー1h−インドール−3−イル)−プロピル]−ピペラジン−1−イル}−2−メチル−4h−ベンゾ[1,4]オキサジン−3−オンメシラート |
Country Status (25)
Country | Link |
---|---|
US (2) | US6958396B2 (ja) |
EP (1) | EP1366044B1 (ja) |
JP (1) | JP4216072B2 (ja) |
KR (1) | KR100859107B1 (ja) |
CN (1) | CN1284780C (ja) |
AR (1) | AR032712A1 (ja) |
AT (1) | ATE472545T1 (ja) |
AU (1) | AU2002250983B2 (ja) |
BR (1) | BR0206162A (ja) |
CA (1) | CA2430707C (ja) |
CZ (1) | CZ20032171A3 (ja) |
DE (1) | DE60236848D1 (ja) |
DZ (1) | DZ3490A1 (ja) |
ES (1) | ES2347321T3 (ja) |
HK (1) | HK1078569A1 (ja) |
HU (1) | HUP0303330A3 (ja) |
IL (1) | IL155720A0 (ja) |
MX (1) | MXPA03007430A (ja) |
NO (1) | NO325298B1 (ja) |
NZ (1) | NZ526018A (ja) |
PL (1) | PL201176B1 (ja) |
RU (1) | RU2281945C2 (ja) |
SK (1) | SK10412003A3 (ja) |
WO (1) | WO2002066473A1 (ja) |
ZA (1) | ZA200304267B (ja) |
Families Citing this family (9)
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IL148218A0 (en) * | 1999-08-23 | 2002-09-12 | Solvay Pharm Bv | New phenylpiperazines |
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US7371769B2 (en) | 2004-12-07 | 2008-05-13 | Solvay Pharmaceuticals B.V. | Tetrahydropyridin-4-yl indoles with a combination of affinity for dopamine-D2 receptors and serotonin reuptake sites |
JP2008523026A (ja) * | 2004-12-07 | 2008-07-03 | ソルベイ・フアーマシユーチカルズ・ベー・ブイ | ドーパミン−d2受容体に関する親和力およびセロトニン再吸収部位の組み合わせを有するフェニルピペラジン類 |
US20060122247A1 (en) | 2004-12-08 | 2006-06-08 | Solvay Pharmaceuticals B.V. | Aryloxyethylamine and phenylpiperazine derivatives with a combination of partial dopamine-D2 receptor agonism and serotonin reuptake inhibition |
GT200600416A (es) * | 2005-09-12 | 2007-09-20 | Sales salicilato y gentisato de un compuesto de piperazina | |
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PE20070523A1 (es) * | 2005-09-12 | 2007-06-28 | Wyeth Corp | Formulacion de liberacion sostenida del glucuronato de (8-{4-[3-(5-fluoro-1h-indol-3-il)-propil]-piperazin-1-il}-2-metil-4h-benzo[1,4]oxazin-3-ona |
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