JPS61225158A - フエニルカルバメート類 - Google Patents
フエニルカルバメート類Info
- Publication number
- JPS61225158A JPS61225158A JP61048183A JP4818386A JPS61225158A JP S61225158 A JPS61225158 A JP S61225158A JP 61048183 A JP61048183 A JP 61048183A JP 4818386 A JP4818386 A JP 4818386A JP S61225158 A JPS61225158 A JP S61225158A
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound according
- ethyl
- hydrogen
- acceptable salt
- 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
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 title claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 75
- 239000003814 drug Substances 0.000 claims description 38
- 229940079593 drug Drugs 0.000 claims description 36
- 230000000694 effects Effects 0.000 claims description 36
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 150000003839 salts Chemical class 0.000 claims description 19
- 239000000544 cholinesterase inhibitor Substances 0.000 claims description 17
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 15
- 150000002431 hydrogen Chemical class 0.000 claims description 15
- 210000003169 central nervous system Anatomy 0.000 claims description 11
- 125000000217 alkyl group Chemical group 0.000 claims description 10
- 208000024827 Alzheimer disease Diseases 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 6
- 238000011282 treatment Methods 0.000 claims description 6
- 201000010374 Down Syndrome Diseases 0.000 claims description 5
- 208000023105 Huntington disease Diseases 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
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- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 3
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 3
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
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- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims 2
- 208000035475 disorder Diseases 0.000 claims 1
- LBKPGNUOUPTQKA-UHFFFAOYSA-N ethyl n-phenylcarbamate Chemical compound CCOC(=O)NC1=CC=CC=C1 LBKPGNUOUPTQKA-UHFFFAOYSA-N 0.000 claims 1
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 31
- 229960001697 physostigmine Drugs 0.000 description 31
- PIJVFDBKTWXHHD-HIFRSBDPSA-N physostigmine Chemical compound C12=CC(OC(=O)NC)=CC=C2N(C)[C@@H]2[C@@]1(C)CCN2C PIJVFDBKTWXHHD-HIFRSBDPSA-N 0.000 description 31
- 210000004556 brain Anatomy 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
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- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 description 8
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- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 5
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- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 4
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
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- LULNWZDBKTWDGK-UHFFFAOYSA-M neostigmine bromide Chemical compound [Br-].CN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1 LULNWZDBKTWDGK-UHFFFAOYSA-M 0.000 description 3
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- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
- VWLHWLSRQJQWRG-UHFFFAOYSA-O Edrophonum Chemical compound CC[N+](C)(C)C1=CC=CC(O)=C1 VWLHWLSRQJQWRG-UHFFFAOYSA-O 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
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- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
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- HOBWAPHTEJGALG-JKCMADFCSA-N [(1r,5s)-8-methyl-8-azoniabicyclo[3.2.1]octan-3-yl] 3-hydroxy-2-phenylpropanoate;sulfate Chemical compound [O-]S([O-])(=O)=O.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1.C([C@H]1CC[C@@H](C2)[NH+]1C)C2OC(=O)C(CO)C1=CC=CC=C1 HOBWAPHTEJGALG-JKCMADFCSA-N 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- IOUVKUPGCMBWBT-QNDFHXLGSA-N phlorizin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 IOUVKUPGCMBWBT-QNDFHXLGSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/21—Esters, e.g. nitroglycerine, selenocyanates
- A61K31/27—Esters, e.g. nitroglycerine, selenocyanates of carbamic or thiocarbamic acids, meprobamate, carbachol, neostigmine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/26—Psychostimulants, e.g. nicotine, cocaine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/14—Dithiocarbamic acids; Derivatives thereof
- C07C333/30—Dithiocarbamic acids; Derivatives thereof having sulfur atoms of dithiocarbamic groups bound to other sulfur atoms
- C07C333/32—Thiuramsulfides; Thiurampolysulfides
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Biomedical Technology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Psychiatry (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IL74497A IL74497A (en) | 1985-03-05 | 1985-03-05 | Pharmaceutical compositions containing phenyl carbamate derivatives and certain phenyl carbamate derivatives |
| IL74497 | 1985-03-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS61225158A true JPS61225158A (ja) | 1986-10-06 |
| JPH0255416B2 JPH0255416B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1990-11-27 |
Family
ID=11055728
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61048183A Granted JPS61225158A (ja) | 1985-03-05 | 1986-03-04 | フエニルカルバメート類 |
Country Status (25)
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS63238054A (ja) * | 1987-03-04 | 1988-10-04 | サンド・アクチエンゲゼルシャフト | フェニルカルバメート |
| JP2002530300A (ja) * | 1998-11-23 | 2002-09-17 | デイビス、ボニー | アセチルコリンエステラーゼ阻害剤のための投与製剤 |
| JP2003512324A (ja) * | 1999-10-19 | 2003-04-02 | ノバルティス アクチエンゲゼルシャフト | 眼疾患の処置のためのリバスチグミン |
| JP2006516267A (ja) * | 2003-01-17 | 2006-06-29 | エルテーエス ローマン テラピー−ジステーメ アーゲー | コリンエステラーゼ阻害剤中毒の医薬的予防方法並びにこれに適する活性物質および医薬 |
| JP2007509152A (ja) * | 2003-10-21 | 2007-04-12 | センション，インコーポレイテッド | コリンエステラーゼを阻害し、薬理活性物質を放出するカルバモイルエステル類 |
| US7342043B2 (en) | 2002-06-14 | 2008-03-11 | Toyama Chemical Co., Ltd. | Medicinal compositions improving brain function and method for improving brain function |
| JP2008519023A (ja) * | 2004-11-08 | 2008-06-05 | エムキュア ファーマシューティカルズ リミテッド | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
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| CH667001A5 (de) * | 1985-09-03 | 1988-09-15 | Hugo Degen | Untermatratze. |
| DE3805744C2 (de) * | 1987-03-04 | 1999-09-23 | Novartis Ag | Phenylcarbamate zur Hemmung der Acetylcholinesterase |
| US5091583A (en) * | 1990-05-07 | 1992-02-25 | Air Products And Chemicals, Inc. | Tertiary amine catalysts for polurethanes |
| IT1271679B (it) * | 1994-07-18 | 1997-06-04 | Mediolanum Farmaceutici Srl | Derivati del fenilcarbammato atti all'impiego come anticolinesterasici |
| US20100210590A1 (en) * | 1995-09-27 | 2010-08-19 | Northwestern University | Compositions and treatments for seizure-related disorders |
| AU4078997A (en) * | 1996-08-22 | 1998-03-06 | New York University | Cholinesterase inhibitors for treatment of parkinson's disease |
| PT951284E (pt) * | 1996-12-18 | 2003-12-31 | Yissum Res Dev Co | Derivados de feniletilamina |
| JP4222632B2 (ja) | 1996-12-18 | 2009-02-12 | テバ・ファーマシューティカル・インダストリーズ・リミテッド | アミノインダン誘導体 |
| US6251938B1 (en) | 1996-12-18 | 2001-06-26 | Teva Pharmaceutical Industries, Ltd., | Phenylethylamine derivatives |
| US5962535A (en) * | 1997-01-17 | 1999-10-05 | Takeda Chemical Industries, Ltd. | Composition for alzheimer's disease |
| WO1998031356A1 (en) * | 1997-01-17 | 1998-07-23 | Takeda Chemical Industries, Ltd. | Idebenone containing combination agent for treating alzheimer's disease |
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| US2208485A (en) * | 1937-04-24 | 1940-07-16 | Hoffmann La Roche | Process for the manufacture of disubstituted carbamic acid esters of phenols containing a basic substituent |
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| US2493710A (en) * | 1947-03-21 | 1950-01-03 | Hoffmann La Roche | Carbamic acid esters |
| DE1037753B (de) * | 1956-07-13 | 1958-08-28 | Rohm & Haas | Schaedlingsbekaempfungsmittel |
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- 1986-02-28 PH PH33465A patent/PH23325A/en unknown
- 1986-03-03 GR GR860586A patent/GR860586B/el unknown
- 1986-03-03 PT PT82127A patent/PT82127B/pt unknown
- 1986-03-03 NZ NZ215348A patent/NZ215348A/en unknown
- 1986-03-03 IE IE55886A patent/IE58838B1/en not_active IP Right Cessation
- 1986-03-03 HU HU86870A patent/HU201297B/hu unknown
- 1986-03-04 KR KR1019860001491A patent/KR940010764B1/ko not_active Expired - Lifetime
- 1986-03-04 DK DK198600991A patent/DK172851B1/da not_active IP Right Cessation
- 1986-03-04 AT AT86102812T patent/ATE58130T1/de active
- 1986-03-04 PL PL1986258224A patent/PL146301B1/pl unknown
- 1986-03-04 JP JP61048183A patent/JPS61225158A/ja active Granted
- 1986-03-04 DE DE1998175046 patent/DE19875046I1/de active Pending
- 1986-03-04 ES ES552627A patent/ES8801193A1/es not_active Expired
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS63238054A (ja) * | 1987-03-04 | 1988-10-04 | サンド・アクチエンゲゼルシャフト | フェニルカルバメート |
| JPH09165362A (ja) * | 1987-03-04 | 1997-06-24 | Sandoz Ag | フェニルカルバメート |
| JP2002530300A (ja) * | 1998-11-23 | 2002-09-17 | デイビス、ボニー | アセチルコリンエステラーゼ阻害剤のための投与製剤 |
| JP2003512324A (ja) * | 1999-10-19 | 2003-04-02 | ノバルティス アクチエンゲゼルシャフト | 眼疾患の処置のためのリバスチグミン |
| US7342043B2 (en) | 2002-06-14 | 2008-03-11 | Toyama Chemical Co., Ltd. | Medicinal compositions improving brain function and method for improving brain function |
| US7834053B2 (en) | 2002-06-14 | 2010-11-16 | Toyama Chemical Co., Ltd. | Medicinal compositions improving brain function and method for improving brain function |
| USRE42327E1 (en) | 2002-06-14 | 2011-05-03 | Toyama Chemical Co., Ltd. | Medicinal compositions improving brain function and method for improving brain function |
| EP2389937A1 (en) | 2002-06-14 | 2011-11-30 | Toyama Chemical Co., Ltd. | Medicinal composition for improving brain function |
| JP2006516267A (ja) * | 2003-01-17 | 2006-06-29 | エルテーエス ローマン テラピー−ジステーメ アーゲー | コリンエステラーゼ阻害剤中毒の医薬的予防方法並びにこれに適する活性物質および医薬 |
| JP2007509152A (ja) * | 2003-10-21 | 2007-04-12 | センション，インコーポレイテッド | コリンエステラーゼを阻害し、薬理活性物質を放出するカルバモイルエステル類 |
| JP2008519023A (ja) * | 2004-11-08 | 2008-06-05 | エムキュア ファーマシューティカルズ リミテッド | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
| JP2012072171A (ja) * | 2004-11-08 | 2012-04-12 | Emcure Pharmaceuticals Ltd | （ｓ）−３−［（１−ジメチルアミノ）エチル］−フェニル−ｎ−エチル−ｎ−メチル−カルバミン酸の効率的製造方法 |
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