RU2455281C2 - Способ получения 1-формамидо-3,5-диметиладамантана - Google Patents
Способ получения 1-формамидо-3,5-диметиладамантана Download PDFInfo
- Publication number
- RU2455281C2 RU2455281C2 RU2008138891/04A RU2008138891A RU2455281C2 RU 2455281 C2 RU2455281 C2 RU 2455281C2 RU 2008138891/04 A RU2008138891/04 A RU 2008138891/04A RU 2008138891 A RU2008138891 A RU 2008138891A RU 2455281 C2 RU2455281 C2 RU 2455281C2
- Authority
- RU
- Russia
- Prior art keywords
- dimethyladamantane
- formamido
- acid
- formamide
- producing
- Prior art date
Links
- NYQWYYMEIBHRSB-UHFFFAOYSA-N n-(3,5-dimethyl-1-adamantyl)formamide Chemical compound C1C(C2)CC3(C)CC1(C)CC2(NC=O)C3 NYQWYYMEIBHRSB-UHFFFAOYSA-N 0.000 title claims abstract description 16
- 238000000034 method Methods 0.000 title claims abstract description 15
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 14
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims abstract description 12
- CWNOIUTVJRWADX-UHFFFAOYSA-N 1,3-dimethyladamantane Chemical compound C1C(C2)CC3CC1(C)CC2(C)C3 CWNOIUTVJRWADX-UHFFFAOYSA-N 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000002253 acid Substances 0.000 claims abstract description 10
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000007513 acids Chemical class 0.000 claims abstract description 9
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 9
- 230000007062 hydrolysis Effects 0.000 claims abstract description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims abstract description 4
- 230000003993 interaction Effects 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 2
- 239000001117 sulphuric acid Substances 0.000 abstract 2
- 235000011149 sulphuric acid Nutrition 0.000 abstract 2
- 230000015572 biosynthetic process Effects 0.000 description 4
- 229960004640 memantine Drugs 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000006227 byproduct Substances 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 2
- HXGDTGSAIMULJN-UHFFFAOYSA-N acenaphthylene Chemical compound C1=CC(C=C2)=C3C2=CC=CC3=C1 HXGDTGSAIMULJN-UHFFFAOYSA-N 0.000 description 2
- 230000026030 halogenation Effects 0.000 description 2
- 238000005658 halogenation reaction Methods 0.000 description 2
- 239000012535 impurity Substances 0.000 description 2
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 2
- IYQYZZHQSZMZIG-UHFFFAOYSA-N tricyclo[5.2.1.0(2.6)]deca-3,8-diene, 4.9-dimethyl Chemical compound C1C2C3C=C(C)CC3C1C=C2C IYQYZZHQSZMZIG-UHFFFAOYSA-N 0.000 description 2
- RTPQXHZLCUUIJP-UHFFFAOYSA-N 1,2-dimethyladamantane Chemical compound C1C(C2)CC3CC1C(C)C2(C)C3 RTPQXHZLCUUIJP-UHFFFAOYSA-N 0.000 description 1
- KEQGZUUPPQEDPF-UHFFFAOYSA-N 1,3-dichloro-5,5-dimethylimidazolidine-2,4-dione Chemical compound CC1(C)N(Cl)C(=O)N(Cl)C1=O KEQGZUUPPQEDPF-UHFFFAOYSA-N 0.000 description 1
- -1 1,3-disubstituted adamantane Chemical class 0.000 description 1
- QUCXLVDIVQWYJR-UHFFFAOYSA-N 1-bromo-3,5-dimethyladamantane Chemical compound C1C(C2)CC3(C)CC1(C)CC2(Br)C3 QUCXLVDIVQWYJR-UHFFFAOYSA-N 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- LBWCITVBZLTEKW-UHFFFAOYSA-N 3,5-dimethyladamantan-1-ol Chemical compound C1C(C2)CC3(C)CC1(C)CC2(O)C3 LBWCITVBZLTEKW-UHFFFAOYSA-N 0.000 description 1
- 208000024827 Alzheimer disease Diseases 0.000 description 1
- 201000006474 Brain Ischemia Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- DKNWSYNQZKUICI-UHFFFAOYSA-N amantadine Chemical class C1C(C2)CC3CC2CC1(N)C3 DKNWSYNQZKUICI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 206010008118 cerebral infarction Diseases 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- XTHPWXDJESJLNJ-UHFFFAOYSA-N chlorosulfonic acid Substances OS(Cl)(=O)=O XTHPWXDJESJLNJ-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000002290 gas chromatography-mass spectrometry Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- WVIRSYCDAYUOMJ-UHFFFAOYSA-N n-(3,5-dimethyl-1-adamantyl)acetamide Chemical compound C1C(C2)CC3(C)CC2(C)CC1(NC(=O)C)C3 WVIRSYCDAYUOMJ-UHFFFAOYSA-N 0.000 description 1
- 229940033872 namenda Drugs 0.000 description 1
- 238000005580 one pot reaction Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/08—Preparation of carboxylic acid amides from amides by reaction at nitrogen atoms of carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2603/00—Systems containing at least three condensed rings
- C07C2603/56—Ring systems containing bridged rings
- C07C2603/58—Ring systems containing bridged rings containing three rings
- C07C2603/70—Ring systems containing bridged rings containing three rings containing only six-membered rings
- C07C2603/74—Adamantanes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006009279A DE102006009279A1 (de) | 2006-03-01 | 2006-03-01 | Verfahren zur Herstellung von 1-Formamido-3,5-dimethyladamantan |
| DE102006009279.1 | 2006-03-01 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2008138891A RU2008138891A (ru) | 2010-04-10 |
| RU2455281C2 true RU2455281C2 (ru) | 2012-07-10 |
Family
ID=38197988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2008138891/04A RU2455281C2 (ru) | 2006-03-01 | 2007-02-20 | Способ получения 1-формамидо-3,5-диметиладамантана |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8138375B2 (OSRAM) |
| EP (1) | EP1989175B1 (OSRAM) |
| JP (1) | JP5345403B2 (OSRAM) |
| DE (1) | DE102006009279A1 (OSRAM) |
| ES (1) | ES2392550T3 (OSRAM) |
| RU (1) | RU2455281C2 (OSRAM) |
| WO (1) | WO2007101536A1 (OSRAM) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2549901C1 (ru) * | 2013-12-30 | 2015-05-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный университет" (ФГБОУ ВПО "КубГУ") | Способ получения n-адамантилированных амидов |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2103597A1 (en) * | 2008-03-20 | 2009-09-23 | Merz Pharma GmbH & Co.KGaA | Process for the manufacture of memantine and intermediate product |
| EP2274276B1 (en) * | 2008-03-20 | 2014-07-09 | Merz Pharma GmbH & Co. KGaA | Process for the manufacture of memantine and intermediate product |
| ES2409692T3 (es) | 2008-12-17 | 2013-06-27 | Merz Pharma Gmbh & Co. Kgaa | Método para la producción de memantina |
| US20110282100A1 (en) * | 2009-01-21 | 2011-11-17 | Merz Pharma Gmbh & Co. Kgaa | Process for preparing memantine |
| US8581262B2 (en) | 2009-08-04 | 2013-11-12 | Merck Patent Gmbh | Electronic devices comprising multi cyclic hydrocarbons |
| JP2013180983A (ja) * | 2012-03-01 | 2013-09-12 | Tokyo Univ Of Agriculture & Technology | Ｎ置換アミド化合物の製造方法 |
| EP4005565A1 (en) | 2020-11-30 | 2022-06-01 | Merz Pharmaceuticals GmbH | Novel uses of adamantane derivatives |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1643528A1 (ru) * | 1988-10-03 | 1991-04-23 | Научно-производственное объединение "Комплекс" | Способ получени 1-ацетаминоадамантана |
| RU2002135270A (ru) * | 2002-12-25 | 2004-07-10 | ООО "Циклан" | Способ получения гидрохлорида 1-амино-3,5,-диметиладамантана |
| CN1566075A (zh) * | 2003-07-01 | 2005-01-19 | 北京德众万全药物技术开发有限公司 | 一种取代的金刚烷胺类化合物或其盐的制备方法 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2318461A1 (de) | 1973-04-12 | 1974-10-31 | Merz & Co | Verfahren zur herstellung von 1,3,5trisubstituierten adamanta-verbindungen |
| JPS63159330A (ja) * | 1986-12-23 | 1988-07-02 | Kawasaki Steel Corp | １，３−ジメチルアダマンタンの製造方法 |
| JPS63295519A (ja) * | 1987-05-27 | 1988-12-01 | Kawasaki Steel Corp | １，３−ジメチルアダマンタンの製造方法 |
| ES2059602T3 (es) | 1989-04-14 | 1994-11-16 | Merz & Co Gmbh & Co | Uso de derivados de adamantano para la prevencion y tratamiento de isquemia cerebral. |
| US5117056A (en) * | 1990-12-21 | 1992-05-26 | Air Products And Chemicals, Inc. | Preparation of N-(1-alkoxyalkyl)formamide and bis formamides |
| RU2246482C2 (ru) * | 2002-12-25 | 2005-02-20 | ООО "Циклан" | Способ получения гидрохлорида 1-амино-3,5-диметиладамантана |
| EP1789380A1 (de) * | 2004-07-23 | 2007-05-30 | Justus-Liebig-Universität Giessen | Aminoadamantan-derivate, verfahren zu ihrer herstellung und ihre verwendung |
-
2006
- 2006-03-01 DE DE102006009279A patent/DE102006009279A1/de not_active Ceased
-
2007
- 2007-02-20 ES ES07722859T patent/ES2392550T3/es active Active
- 2007-02-20 WO PCT/EP2007/001433 patent/WO2007101536A1/de not_active Ceased
- 2007-02-20 EP EP07722859A patent/EP1989175B1/de active Active
- 2007-02-20 US US12/224,575 patent/US8138375B2/en active Active
- 2007-02-20 JP JP2008556686A patent/JP5345403B2/ja active Active
- 2007-02-20 RU RU2008138891/04A patent/RU2455281C2/ru active
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU1643528A1 (ru) * | 1988-10-03 | 1991-04-23 | Научно-производственное объединение "Комплекс" | Способ получени 1-ацетаминоадамантана |
| RU2002135270A (ru) * | 2002-12-25 | 2004-07-10 | ООО "Циклан" | Способ получения гидрохлорида 1-амино-3,5,-диметиладамантана |
| CN1566075A (zh) * | 2003-07-01 | 2005-01-19 | 北京德众万全药物技术开发有限公司 | 一种取代的金刚烷胺类化合物或其盐的制备方法 |
Non-Patent Citations (1)
| Title |
|---|
| Климочкин Ю.Н. и др. Синтез алкоксикарбониламино- и ацетиламинопроизводных адамантанового ряда в среде азотной кислоты. - М.: Наука, Известия Академии Наук СССР, №4, апрель 1988 г. * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2549901C1 (ru) * | 2013-12-30 | 2015-05-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Кубанский государственный университет" (ФГБОУ ВПО "КубГУ") | Способ получения n-адамантилированных амидов |
Also Published As
| Publication number | Publication date |
|---|---|
| ES2392550T3 (es) | 2012-12-11 |
| JP2009528309A (ja) | 2009-08-06 |
| EP1989175B1 (de) | 2012-09-19 |
| WO2007101536A1 (de) | 2007-09-13 |
| DE102006009279A1 (de) | 2007-09-06 |
| US8138375B2 (en) | 2012-03-20 |
| US20090299097A1 (en) | 2009-12-03 |
| EP1989175A1 (de) | 2008-11-12 |
| JP5345403B2 (ja) | 2013-11-20 |
| RU2008138891A (ru) | 2010-04-10 |
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