JP2010520251A5 - - Google Patents
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- Publication number
- JP2010520251A5 JP2010520251A5 JP2009552166A JP2009552166A JP2010520251A5 JP 2010520251 A5 JP2010520251 A5 JP 2010520251A5 JP 2009552166 A JP2009552166 A JP 2009552166A JP 2009552166 A JP2009552166 A JP 2009552166A JP 2010520251 A5 JP2010520251 A5 JP 2010520251A5
- Authority
- JP
- Japan
- Prior art keywords
- formula
- compound
- alkyl
- halogen
- substituted
- 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 15
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 6
- 229910052736 halogen Inorganic materials 0.000 claims 6
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000005843 halogen group Chemical group 0.000 claims 3
- 238000004519 manufacturing process Methods 0.000 claims 3
- 238000000034 method Methods 0.000 claims 3
- LMDZBCPBFSXMTL-UHFFFAOYSA-N 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide Substances CCN=C=NCCCN(C)C LMDZBCPBFSXMTL-UHFFFAOYSA-N 0.000 claims 2
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 claims 2
- -1 HBTU Chemical compound 0.000 claims 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims 2
- 239000012317 TBTU Substances 0.000 claims 2
- CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 claims 2
- FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 claims 2
- 229910000024 caesium carbonate Inorganic materials 0.000 claims 2
- 230000008878 coupling Effects 0.000 claims 2
- 239000007822 coupling agent Substances 0.000 claims 2
- 238000010168 coupling process Methods 0.000 claims 2
- 238000005859 coupling reaction Methods 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 claims 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000006164 6-membered heteroaryl group Chemical group 0.000 claims 1
- 150000002367 halogens Chemical class 0.000 claims 1
- 125000004433 nitrogen atom Chemical group N* 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- YUUGYIUSCYNSQR-LBPRGKRZSA-N C[C@@H](C(F)(F)F)Oc(c(C(N(CC1)CCN1c1ncc(C(F)(F)F)cc1F)=O)c1)ccc1S(C)(=O)=O Chemical compound C[C@@H](C(F)(F)F)Oc(c(C(N(CC1)CCN1c1ncc(C(F)(F)F)cc1F)=O)c1)ccc1S(C)(=O)=O YUUGYIUSCYNSQR-LBPRGKRZSA-N 0.000 description 1
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP07103485 | 2007-03-05 | ||
| EP07103485.4 | 2007-03-05 | ||
| PCT/EP2008/052244 WO2008107334A2 (en) | 2007-03-05 | 2008-02-25 | Process for the synthesis of glyt-1 inhibitors |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2010520251A JP2010520251A (ja) | 2010-06-10 |
| JP2010520251A5 true JP2010520251A5 (https=) | 2010-12-09 |
| JP4745446B2 JP4745446B2 (ja) | 2011-08-10 |
Family
ID=39469606
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2009552166A Active JP4745446B2 (ja) | 2007-03-05 | 2008-02-25 | Ｇｌｙｔ−１阻害剤の合成 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US7812161B2 (https=) |
| EP (1) | EP2131843B1 (https=) |
| JP (1) | JP4745446B2 (https=) |
| KR (1) | KR101143073B1 (https=) |
| CN (1) | CN101622000B (https=) |
| AT (1) | ATE532516T1 (https=) |
| AU (1) | AU2008223915B2 (https=) |
| BR (1) | BRPI0808570B8 (https=) |
| CA (1) | CA2678630C (https=) |
| ES (1) | ES2375585T3 (https=) |
| IL (1) | IL200323A (https=) |
| MX (1) | MX2009009065A (https=) |
| WO (1) | WO2008107334A2 (https=) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5656474B2 (ja) | 2010-06-28 | 2015-01-21 | 関東化学株式会社 | 脂肪族光学活性フルオロアルコールの製造方法 |
| CN104628679B (zh) * | 2013-11-08 | 2018-02-09 | 江苏恩华药业股份有限公司 | Bitopertin的合成方法及其中间体 |
| CN106397312B (zh) * | 2015-07-31 | 2020-03-24 | 广东东阳光药业有限公司 | 一种制备glyt-1抑制剂的方法 |
| KR20220125326A (ko) | 2020-01-09 | 2022-09-14 | 디스크 메디슨, 인크. | 적혈구형성 프로토포르피린증, x-연계된 프로토포르피린증, 또는 선천성 적혈구 조혈포르피린증을 글리신 운반 억제제로 치료하는 방법 |
| CA3195702A1 (en) | 2020-10-13 | 2022-04-21 | Boehringer Ingelheim International Gmbh | Process of reworking |
| WO2024042043A1 (en) | 2022-08-24 | 2024-02-29 | Boehringer Ingelheim International Gmbh | A scalable process for the preparation of a glyt-1 inhibitor |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3992441A (en) * | 1972-12-26 | 1976-11-16 | Pfizer Inc. | Sulfamylbenzoic acids |
| US4480102A (en) * | 1982-07-23 | 1984-10-30 | The Dow Chemical Company | 2,3-Difluoro-5-(trifluoromethyl)pyridine and methods of making and using the same |
| DE68912282T2 (de) * | 1988-11-24 | 1994-04-28 | Akzo Nv | 1-[Mono- oder bis(trifluormethyl)-2-pyridinyl]piperazine enthaltende pharmazeutische Zusammensetzungen. |
| DE4235155A1 (de) * | 1992-10-19 | 1994-04-21 | Basf Ag | Verfahren zur Herstellung von Methylsulfonylbenzoesäuren |
| US6384080B1 (en) * | 1998-04-20 | 2002-05-07 | Fujisawa Pharmaceutical Co., Ltd. | Anthranilic acid derivatives as inhibitors of the cGMP-phosphodiesterase |
| DE10112040A1 (de) * | 2001-03-14 | 2002-10-02 | Aventis Pharma Gmbh | Verbessertes Verfahren zur Herstellung von Sulfonylcarboxamidderivaten |
| GB0227240D0 (en) * | 2002-11-21 | 2002-12-31 | Glaxo Group Ltd | Compounds |
| RS53252B (sr) * | 2003-08-11 | 2014-08-29 | F.Hoffmann-La Roche Ag. | Piperazin sa or-supstituisanom fenil grupom i njihova upotreba kao inhibitora glyt1 |
| HRP20090264T1 (hr) * | 2004-12-09 | 2009-06-30 | F. Hoffmann - La Roche Ag | Derivati fenil-piperazin metanona |
| CA2593453A1 (en) * | 2005-01-06 | 2006-07-13 | F. Hoffmann-La Roche Ag | Sulfanyl substituted phenyl methanones as glycine transporter 1 (glyt-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| AU2005324024B2 (en) * | 2005-01-07 | 2011-02-17 | F. Hoffmann-La Roche Ag | [4-(Heteroaryl) piperazin-1-yl]-(2,5-substituted -phenyl)methanone derivatives as glycine transporter 1 (GlyT-1) inhibitors for the treatment of neurological and neuropsychiatric disorders |
| CN101218350B (zh) * | 2005-07-08 | 2011-08-31 | 弗·哈夫曼-拉罗切有限公司 | 1,1,1-三氟丙酮的不对称还原反应 |
-
2008
- 2008-02-25 WO PCT/EP2008/052244 patent/WO2008107334A2/en not_active Ceased
- 2008-02-25 AU AU2008223915A patent/AU2008223915B2/en active Active
- 2008-02-25 JP JP2009552166A patent/JP4745446B2/ja active Active
- 2008-02-25 MX MX2009009065A patent/MX2009009065A/es active IP Right Grant
- 2008-02-25 CA CA2678630A patent/CA2678630C/en active Active
- 2008-02-25 ES ES08709206T patent/ES2375585T3/es active Active
- 2008-02-25 BR BRPI0808570A patent/BRPI0808570B8/pt active IP Right Grant
- 2008-02-25 CN CN200880006900XA patent/CN101622000B/zh active Active
- 2008-02-25 AT AT08709206T patent/ATE532516T1/de active
- 2008-02-25 EP EP08709206A patent/EP2131843B1/en active Active
- 2008-02-25 KR KR1020097018418A patent/KR101143073B1/ko active Active
- 2008-02-27 US US12/038,006 patent/US7812161B2/en active Active
-
2009
- 2009-08-10 IL IL200323A patent/IL200323A/en active IP Right Grant
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