ES2392550T3 - Procedimiento para la producción de 1-formamido-3,5-dimetiladamantano - Google Patents
Procedimiento para la producción de 1-formamido-3,5-dimetiladamantano Download PDFInfo
- Publication number
- ES2392550T3 ES2392550T3 ES07722859T ES07722859T ES2392550T3 ES 2392550 T3 ES2392550 T3 ES 2392550T3 ES 07722859 T ES07722859 T ES 07722859T ES 07722859 T ES07722859 T ES 07722859T ES 2392550 T3 ES2392550 T3 ES 2392550T3
- Authority
- ES
- Spain
- Prior art keywords
- dimethylamantane
- formamido
- production
- acid
- procedure
- 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.)
- Active
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 9
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims abstract description 7
- 150000007513 acids Chemical class 0.000 claims abstract description 7
- 229910017604 nitric acid Inorganic materials 0.000 claims abstract description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- BUGYDGFZZOZRHP-UHFFFAOYSA-N memantine Chemical compound C1C(C2)CC3(C)CC1(C)CC2(N)C3 BUGYDGFZZOZRHP-UHFFFAOYSA-N 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 3
- 238000006460 hydrolysis reaction Methods 0.000 claims description 3
- 238000011065 in-situ storage Methods 0.000 claims description 3
- 239000002243 precursor Substances 0.000 claims description 3
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- 125000002091 cationic group Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 230000017105 transposition Effects 0.000 claims description 2
- 239000012141 concentrate Substances 0.000 claims 1
- 229960004640 memantine Drugs 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-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
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 2
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 2
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 239000005642 Oleic acid Substances 0.000 description 2
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-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
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002825 nitriles Chemical class 0.000 description 2
- 239000012038 nucleophile Substances 0.000 description 2
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000007858 starting material Substances 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 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
- 206010008120 Cerebral ischaemia Diseases 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 238000005903 acid hydrolysis reaction Methods 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 230000001476 alcoholic effect Effects 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
- 239000006227 byproduct Substances 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
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052681 coesite Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052906 cristobalite Inorganic materials 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 231100001231 less toxic Toxicity 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- LDDHMLJTFXJGPI-UHFFFAOYSA-N memantine hydrochloride Chemical compound Cl.C1C(C2)CC3(C)CC1(C)CC2(N)C3 LDDHMLJTFXJGPI-UHFFFAOYSA-N 0.000 description 1
- 229940033872 namenda Drugs 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229910052682 stishovite Inorganic materials 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 229910052905 tridymite Inorganic materials 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 (3)
| 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 | 2006-03-01 | ||
| PCT/EP2007/001433 WO2007101536A1 (de) | 2006-03-01 | 2007-02-20 | Verfahren zur herstellung von 1-formamido-3,5-dimethyladamantan |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2392550T3 true ES2392550T3 (es) | 2012-12-11 |
Family
ID=38197988
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES07722859T Active ES2392550T3 (es) | 2006-03-01 | 2007-02-20 | Procedimiento para la producción de 1-formamido-3,5-dimetiladamantano |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US8138375B2 (enExample) |
| EP (1) | EP1989175B1 (enExample) |
| JP (1) | JP5345403B2 (enExample) |
| DE (1) | DE102006009279A1 (enExample) |
| ES (1) | ES2392550T3 (enExample) |
| RU (1) | RU2455281C2 (enExample) |
| WO (1) | WO2007101536A1 (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ES2507085T3 (es) * | 2008-03-20 | 2014-10-14 | Merz Pharma Gmbh & Co. Kgaa | Proceso para la fabricación de Memantina y producto intermedio |
| EP2103597A1 (en) * | 2008-03-20 | 2009-09-23 | Merz Pharma GmbH & Co.KGaA | Process for the manufacture of memantine and intermediate product |
| EP2373612B1 (en) | 2008-12-17 | 2013-04-17 | Merz Pharma GmbH & Co. KGaA | Method for producing memantine |
| JP5548702B2 (ja) * | 2009-01-21 | 2014-07-16 | メルツ・ファルマ・ゲゼルシヤフト・ミト・ベシュレンクテル・ハフツング・ウント・コンパニー・コマンデイトゲゼルシヤフト・アウフ・アクティーン | メマンチンの製造方法 |
| JP5778148B2 (ja) | 2009-08-04 | 2015-09-16 | メルク パテント ゲーエムベーハー | 多環式炭水化物を含む電子デバイス |
| 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 |
| 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 |
| EP4005565A1 (en) | 2020-11-30 | 2022-06-01 | Merz Pharmaceuticals GmbH | Novel uses of adamantane derivatives |
Family Cites Families (9)
| 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 |
| SU1643528A1 (ru) * | 1988-10-03 | 1991-04-23 | Научно-производственное объединение "Комплекс" | Способ получени 1-ацетаминоадамантана |
| DE10299048I2 (de) | 1989-04-14 | 2006-07-13 | Merz Pharma Gmbh & Co Kgaa | Verwendung von Adamantan-Derivaten zur Pr{vention und Behandlung der cerebralen Isch{mie |
| 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 |
| CN100345819C (zh) | 2003-07-01 | 2007-10-31 | 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 |
| US20080275112A1 (en) | 2004-07-23 | 2008-11-06 | Schreiner Peter R | Invention Concerning Aminoadamantane Compounds |
-
2006
- 2006-03-01 DE DE102006009279A patent/DE102006009279A1/de not_active Ceased
-
2007
- 2007-02-20 JP JP2008556686A patent/JP5345403B2/ja active Active
- 2007-02-20 RU RU2008138891/04A patent/RU2455281C2/ru active
- 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 ES ES07722859T patent/ES2392550T3/es active Active
- 2007-02-20 WO PCT/EP2007/001433 patent/WO2007101536A1/de not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| JP5345403B2 (ja) | 2013-11-20 |
| DE102006009279A1 (de) | 2007-09-06 |
| US8138375B2 (en) | 2012-03-20 |
| US20090299097A1 (en) | 2009-12-03 |
| JP2009528309A (ja) | 2009-08-06 |
| RU2455281C2 (ru) | 2012-07-10 |
| WO2007101536A1 (de) | 2007-09-13 |
| EP1989175B1 (de) | 2012-09-19 |
| RU2008138891A (ru) | 2010-04-10 |
| EP1989175A1 (de) | 2008-11-12 |
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