JP2013505902A5 - - Google Patents
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- Publication number
- JP2013505902A5 JP2013505902A5 JP2012530174A JP2012530174A JP2013505902A5 JP 2013505902 A5 JP2013505902 A5 JP 2013505902A5 JP 2012530174 A JP2012530174 A JP 2012530174A JP 2012530174 A JP2012530174 A JP 2012530174A JP 2013505902 A5 JP2013505902 A5 JP 2013505902A5
- Authority
- JP
- Japan
- Prior art keywords
- pentamethylcyclohexane
- cyanide
- acid
- iii
- hydrogen cyanide
- 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.)
- Ceased
Links
- LELOWRISYMNNSU-UHFFFAOYSA-N hydrogen cyanide Chemical compound N#C LELOWRISYMNNSU-UHFFFAOYSA-N 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 14
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 claims description 8
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical group N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- BMRINMQQUFUCHR-UHFFFAOYSA-N 1,3,3,5,5-pentamethylcyclohexan-1-ol Chemical compound CC1(C)CC(C)(C)CC(C)(O)C1 BMRINMQQUFUCHR-UHFFFAOYSA-N 0.000 claims description 6
- OGZQTTHDGQBLBT-UHFFFAOYSA-N neramexane Chemical compound CC1(C)CC(C)(C)CC(C)(N)C1 OGZQTTHDGQBLBT-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims 17
- 239000002253 acid Substances 0.000 claims 9
- 150000001875 compounds Chemical class 0.000 claims 5
- 239000000203 mixture Substances 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- -1 Salt ammonium cyanide Chemical class 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 230000003301 hydrolyzing effect Effects 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical group C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 claims 2
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 238000005580 one pot reaction Methods 0.000 claims 1
- 238000000746 purification Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 150000003377 silicon compounds Chemical class 0.000 claims 1
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 3
- ICAIHGOJRDCMHE-UHFFFAOYSA-O ammonium cyanide Chemical compound [NH4+].N#[C-] ICAIHGOJRDCMHE-UHFFFAOYSA-O 0.000 description 2
- GEZWVPAURSSPEA-UHFFFAOYSA-N 1,1,2,2,3-pentamethylcyclohexane Chemical compound CC1CCCC(C)(C)C1(C)C GEZWVPAURSSPEA-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 229940125898 compound 5 Drugs 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 229950004543 neramexane Drugs 0.000 description 1
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US27769109P | 2009-09-28 | 2009-09-28 | |
| EP09012283.9 | 2009-09-28 | ||
| US61/277,691 | 2009-09-28 | ||
| EP09012283 | 2009-09-28 | ||
| PCT/EP2010/005864 WO2011035924A1 (en) | 2009-09-28 | 2010-09-24 | Method of preparing neramexane or a salt thereof |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015106988A Division JP2015166383A (ja) | 2009-09-28 | 2015-05-27 | ネラメキサン又はその塩を調製する方法 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JP2013505902A JP2013505902A (ja) | 2013-02-21 |
| JP2013505902A5 true JP2013505902A5 (https=) | 2015-02-05 |
Family
ID=41786478
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2012530174A Ceased JP2013505902A (ja) | 2009-09-28 | 2010-09-24 | ネラメキサン又はその塩を調製する方法 |
| JP2015106988A Pending JP2015166383A (ja) | 2009-09-28 | 2015-05-27 | ネラメキサン又はその塩を調製する方法 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2015106988A Pending JP2015166383A (ja) | 2009-09-28 | 2015-05-27 | ネラメキサン又はその塩を調製する方法 |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US8692021B2 (https=) |
| EP (1) | EP2483234A1 (https=) |
| JP (2) | JP2013505902A (https=) |
| WO (1) | WO2011035924A1 (https=) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2483234A1 (en) * | 2009-09-28 | 2012-08-08 | Merz Pharma GmbH & Co. KGaA | Method of preparing neramexane or a salt thereof |
| WO2021110859A1 (en) * | 2019-12-05 | 2021-06-10 | Syngenta Crop Protection Ag | One step process for the preparation of phenyl ethyl amine derivatives |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| UA61962C2 (uk) * | 1997-06-30 | 2003-12-15 | Мерц Фарма Гмбх Унд Ко. Кгаа | Сполука 1-аміноалкілциклогексану, фармацевтична композиція на її основі та спосіб лікування |
| TW388752B (en) * | 1997-07-07 | 2000-05-01 | Rohm & Haas | Tertiary-alkyl primary amines and process for preparing the same |
| WO2005062724A2 (en) * | 2003-12-31 | 2005-07-14 | Sun Pharmaceutical Industries Limited | Novel process for the preparation of aminoadamantane derivatives |
| EP2483234A1 (en) * | 2009-09-28 | 2012-08-08 | Merz Pharma GmbH & Co. KGaA | Method of preparing neramexane or a salt thereof |
-
2010
- 2010-09-24 EP EP10762600A patent/EP2483234A1/en not_active Withdrawn
- 2010-09-24 JP JP2012530174A patent/JP2013505902A/ja not_active Ceased
- 2010-09-24 US US13/498,432 patent/US8692021B2/en not_active Expired - Fee Related
- 2010-09-24 WO PCT/EP2010/005864 patent/WO2011035924A1/en not_active Ceased
-
2015
- 2015-05-27 JP JP2015106988A patent/JP2015166383A/ja active Pending
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