JP2010527371A5 - - Google Patents
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- Publication number
- JP2010527371A5 JP2010527371A5 JP2010508552A JP2010508552A JP2010527371A5 JP 2010527371 A5 JP2010527371 A5 JP 2010527371A5 JP 2010508552 A JP2010508552 A JP 2010508552A JP 2010508552 A JP2010508552 A JP 2010508552A JP 2010527371 A5 JP2010527371 A5 JP 2010527371A5
- Authority
- JP
- Japan
- Prior art keywords
- methylpiperidin
- methylpropyloxy
- fluorophenylmethyl
- phenylmethyl
- carbamide
- 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
- 238000000034 method Methods 0.000 claims 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 16
- 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims 9
- -1 4-fluorophenylmethyl Chemical group 0.000 claims 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 9
- 235000013877 carbamide Nutrition 0.000 claims 8
- 239000004202 carbamide Substances 0.000 claims 8
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 5
- 229940095064 tartrate Drugs 0.000 claims 5
- 239000007795 chemical reaction product Substances 0.000 claims 4
- 239000013078 crystal Substances 0.000 claims 4
- 239000012535 impurity Substances 0.000 claims 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- JBVKKHDTYSDPHA-UHFFFAOYSA-N [4-(2-methylpropoxy)phenyl]methanamine Chemical compound CC(C)COC1=CC=C(CN)C=C1 JBVKKHDTYSDPHA-UHFFFAOYSA-N 0.000 claims 3
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 claims 3
- PWASYRSZCSTUIW-UHFFFAOYSA-N 4-(2-methylpropoxy)benzaldehyde Chemical compound CC(C)COC1=CC=C(C=O)C=C1 PWASYRSZCSTUIW-UHFFFAOYSA-N 0.000 claims 2
- RGHHSNMVTDWUBI-UHFFFAOYSA-N 4-hydroxybenzaldehyde Chemical compound OC1=CC=C(C=O)C=C1 RGHHSNMVTDWUBI-UHFFFAOYSA-N 0.000 claims 2
- VPEGFBXWSGBVDN-UHFFFAOYSA-N acetic acid;[4-(2-methylpropoxy)phenyl]methanamine Chemical compound CC(O)=O.CC(C)COC1=CC=C(CN)C=C1 VPEGFBXWSGBVDN-UHFFFAOYSA-N 0.000 claims 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 2
- BPILZXNFTZZYJJ-UHFFFAOYSA-N 1-(isocyanatomethyl)-4-(2-methylpropoxy)benzene Chemical compound CC(C)COC1=CC=C(CN=C=O)C=C1 BPILZXNFTZZYJJ-UHFFFAOYSA-N 0.000 claims 1
- HLVFKOKELQSXIQ-UHFFFAOYSA-N 1-bromo-2-methylpropane Chemical compound CC(C)CBr HLVFKOKELQSXIQ-UHFFFAOYSA-N 0.000 claims 1
- YLEVZJKJJKYRKJ-UHFFFAOYSA-N 2,3-dihydroxybutanedioic acid;hydrobromide Chemical compound Br.OC(=O)C(O)C(O)C(O)=O YLEVZJKJJKYRKJ-UHFFFAOYSA-N 0.000 claims 1
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 claims 1
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 claims 1
- PLYWEOOWONUOBN-UHFFFAOYSA-N n-[(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine Chemical compound C1CN(C)CCC1NCC1=CC=C(F)C=C1 PLYWEOOWONUOBN-UHFFFAOYSA-N 0.000 claims 1
- 229910000027 potassium carbonate Inorganic materials 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 150000003892 tartrate salts Chemical class 0.000 claims 1
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11/749,115 US7790899B2 (en) | 2004-09-27 | 2007-05-15 | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
| PCT/US2008/063555 WO2008144326A2 (en) | 2007-05-15 | 2008-05-13 | Synthesis of n-(4-fluorobenzyl)-n-(l-methylpiperidin-4-yl)-n'-(4- (2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2010527371A JP2010527371A (ja) | 2010-08-12 |
| JP2010527371A5 true JP2010527371A5 (https=) | 2011-06-30 |
Family
ID=39595699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2010508552A Abandoned JP2010527371A (ja) | 2007-05-15 | 2008-05-13 | Ｎ−（４−フルオロベンジル）−ｎ−（１−メチルピペリジン−４−イル）−ｎ’−（４−（２−メチルプロピルオキシ）フェニルメチル）カルバミドならびにその酒石酸塩および各種の結晶形の合成 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US7790899B2 (https=) |
| EP (1) | EP2146960A2 (https=) |
| JP (1) | JP2010527371A (https=) |
| CN (1) | CN101778821A (https=) |
| AU (1) | AU2008254238A1 (https=) |
| CA (1) | CA2692001A1 (https=) |
| WO (1) | WO2008144326A2 (https=) |
Families Citing this family (40)
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| DK2009000T3 (da) | 2003-01-16 | 2011-09-05 | Acadia Pharm Inc | Selektive serotonin 2A/2C-receptor invers-agonister som terapeutika for neurodegenerative sygdomme |
| US7790899B2 (en) * | 2004-09-27 | 2010-09-07 | Acadia Pharmaceuticals, Inc. | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
| CA2580129A1 (en) * | 2004-09-27 | 2006-04-06 | Acadia Pharmaceuticals Inc. | Salts of n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and their preparation |
| WO2014085362A1 (en) | 2012-11-27 | 2014-06-05 | Acadia Pharmaceuticals Inc. | Methods for the treatment of parkinson's disease psychosis using pimavanserin |
| CN105418460B (zh) * | 2014-08-11 | 2017-04-12 | 苏州鹏旭医药科技有限公司 | 匹莫范色林及其类似化合物中间体，其制备方法和制备匹莫范色林及其类似化合物的方法 |
| CN104961671B (zh) * | 2014-09-05 | 2018-01-02 | 苏州晶云药物科技有限公司 | N‑(4‑氟苄基)‑n‑(1‑甲基哌啶‑4‑基)‑n’‑(4‑(2‑甲基丙氧基)‑苯基甲基)脲半酒石酸盐的晶型及其制备方法 |
| WO2016141003A1 (en) | 2015-03-02 | 2016-09-09 | Teva Pharmaceutical Industries Ltd. | Processes and intermediates for the preparation of pimavanserin |
| CN104961672B (zh) * | 2015-05-20 | 2017-10-20 | 沈阳药科大学 | 一种n‑(4‑氟苄基)‑n‑(1‑甲基哌啶‑4‑基)‑n’‑(4‑异丁氧基苄基)脲的酒石酸盐的合成方法 |
| ES2890492T3 (es) * | 2015-07-20 | 2022-01-20 | Acadia Pharm Inc | Métodos para preparar N-(4-fluorobencil)-N-(1-metilpiperidin-4-il)-N'-(4-(2-metilpropiloxi)fenilmetil)carbamida y su sal de tartrato y forma polimórfica C |
| CN105111135A (zh) * | 2015-09-09 | 2015-12-02 | 安徽省逸欣铭医药科技有限公司 | 取代的尿素衍生物制备方法 |
| CN105153016B (zh) * | 2015-10-12 | 2017-10-03 | 北京诺康达医药科技有限公司 | 一种匹莫范色林的制备方法 |
| CN106588753B (zh) * | 2015-10-19 | 2021-07-09 | 重庆医药工业研究院有限责任公司 | 一种制备匹马色林的方法 |
| CN105481757A (zh) * | 2015-12-25 | 2016-04-13 | 北京康立生医药技术开发有限公司 | 一种哌马色林的制备方法 |
| CN105523993A (zh) * | 2015-12-28 | 2016-04-27 | 重庆两江药物研发中心有限公司 | N-(4-氟苄基)-n-(1-甲基哌啶-4-基)-n’-(4-(2-甲基丙氧基)苯基甲基)脲酒石酸盐晶型c及制备应用 |
| US10953000B2 (en) | 2016-03-25 | 2021-03-23 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome P450 modulators |
| WO2017165635A1 (en) | 2016-03-25 | 2017-09-28 | Acadia Pharmaceuticals Inc. | Combination of pimavanserin and cytochrome p450 modulators |
| CN105820110B (zh) * | 2016-05-09 | 2018-07-24 | 杭州科巢生物科技有限公司 | 匹莫范色林合成方法 |
| CN109563036A (zh) * | 2016-05-19 | 2019-04-02 | 上海诚妙医药科技有限公司 | 匹莫范色林酒石酸盐的新晶型及其制备方法和用途 |
| CN105859608B (zh) * | 2016-05-27 | 2018-12-28 | 成都百裕制药股份有限公司 | 一种制备哌马色林半酒石酸盐晶型b的方法 |
| CN106008323B (zh) * | 2016-05-30 | 2018-11-23 | 成都百裕制药股份有限公司 | 一种制备哌马色林半酒石酸盐晶型c的方法 |
| HU231097B1 (hu) * | 2016-07-08 | 2020-08-28 | Egis Gyógyszergyár Zrt. | Gyógyászati készítmény előállítására alkalmazható pimavanserin sók |
| EP3558311A1 (en) | 2016-12-20 | 2019-10-30 | Acadia Pharmaceuticals Inc. | Pimavanserin alone or in combination for use in the treatment of alzheimer's disease psychosis |
| CN106916098A (zh) * | 2017-03-07 | 2017-07-04 | 江苏艾立康药业股份有限公司 | 一种哌马色林单酒石酸盐半水合物及制备方法 |
| CN107011137B (zh) * | 2017-04-10 | 2020-09-11 | 杭州科耀医药科技有限公司 | 一种匹莫范色林中间体的合成方法 |
| EP3615028A1 (en) | 2017-04-28 | 2020-03-04 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating impulse control disorder |
| CN107216271B (zh) * | 2017-06-02 | 2018-11-13 | 沈阳药科大学 | 酒石酸匹莫范色林杂质及其制备方法 |
| EP3672960A2 (en) | 2017-08-21 | 2020-07-01 | Acadia Pharmaceuticals Inc. | Compounds, salts thereof and their use for the treatment of diseases |
| MX2020001757A (es) * | 2017-08-21 | 2020-09-07 | Acadia Pharm Inc | Compuestos, sales de los mismos y metodos para el tratamiento de enfermedades. |
| EP3675827A1 (en) | 2017-08-30 | 2020-07-08 | Acadia Pharmaceuticals Inc. | Formulations of pimavanserin |
| CA3079142A1 (en) * | 2017-11-06 | 2019-05-09 | Olon S.P.A. | Amorphous form of pimavanserin hemitartrate |
| IT201800003736A1 (it) | 2018-03-19 | 2019-09-19 | Lundbeck Pharmaceuticals Italy S P A | Processo per la produzione di Pimavanserin |
| CN108947891B (zh) | 2018-07-26 | 2021-02-09 | 丽珠集团新北江制药股份有限公司 | 利用三光气安全制备匹莫范色林及其酒石酸盐的方法 |
| IT201800009690A1 (it) * | 2018-10-23 | 2020-04-23 | Lundbeck Pharmaceuticals Italy Spa | Processo per la produzione di pimavanserina |
| US20220016101A1 (en) | 2018-10-30 | 2022-01-20 | Acadia Pharmaceuticals Inc. | Methods of treating depression, anxiety and sexual dysfunction using the compound pimavanserin |
| CN109734652A (zh) * | 2019-03-07 | 2019-05-10 | 夸克侠医药科技(辽宁)有限公司 | 一种高纯度匹莫范色林的制备方法 |
| ES2908812T3 (es) | 2019-04-17 | 2022-05-04 | Zakl Farmaceutyczne Polpharma S A | Proceso para la preparación de un agente farmacéutico |
| ES2906868T3 (es) | 2019-05-22 | 2022-04-20 | Zakl Farmaceutyczne Polpharma S A | Intermedio farmacéutico para preparar pimavanserina |
| WO2021016369A1 (en) | 2019-07-22 | 2021-01-28 | Acadia Pharmaceuticals Inc. | Pimavanserin for trating schizophrenia or for treating psychosis secondary to neurodegenerative disorders or depressive disorder |
| US20220323429A1 (en) | 2019-08-15 | 2022-10-13 | Acadia Pharmaceuticals Inc. | Pimavanserin for treating neurodegenerative diseases |
| WO2022094230A1 (en) | 2020-11-02 | 2022-05-05 | Acadia Pharmaceuticals Inc. | Compounds for treating psychosis or depression |
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| US7790899B2 (en) * | 2004-09-27 | 2010-09-07 | Acadia Pharmaceuticals, Inc. | Synthesis of N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N′-(4-(2-methylpropyloxy)phenylmethyl)carbamide and its tartrate salt and crystalline forms |
| CA2580129A1 (en) | 2004-09-27 | 2006-04-06 | Acadia Pharmaceuticals Inc. | Salts of n-(4-fluorobenzyl)-n-(1-methylpiperidin-4-yl)-n'-(4-(2-methylpropyloxy)phenylmethyl)carbamide and their preparation |
| WO2007133802A2 (en) * | 2006-05-15 | 2007-11-22 | Acadia Pharmaceuticals Inc. | Pharmaceutical formulations of pimavanserin |
-
2007
- 2007-05-15 US US11/749,115 patent/US7790899B2/en active Active
-
2008
- 2008-05-13 AU AU2008254238A patent/AU2008254238A1/en not_active Abandoned
- 2008-05-13 CN CN200880021061A patent/CN101778821A/zh active Pending
- 2008-05-13 JP JP2010508552A patent/JP2010527371A/ja not_active Abandoned
- 2008-05-13 WO PCT/US2008/063555 patent/WO2008144326A2/en not_active Ceased
- 2008-05-13 CA CA002692001A patent/CA2692001A1/en not_active Abandoned
- 2008-05-13 EP EP08755415A patent/EP2146960A2/en not_active Withdrawn
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