JPH0255416B2 - - Google Patents
Info
- Publication number
- JPH0255416B2 JPH0255416B2 JP61048183A JP4818386A JPH0255416B2 JP H0255416 B2 JPH0255416 B2 JP H0255416B2 JP 61048183 A JP61048183 A JP 61048183A JP 4818386 A JP4818386 A JP 4818386A JP H0255416 B2 JPH0255416 B2 JP H0255416B2
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- compound
- formula
- ethyl
- hydrogen
- 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.)
- Expired - Lifetime
Links
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical class NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 claims abstract description 16
- 150000001875 compounds Chemical class 0.000 claims description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 37
- 230000000694 effects Effects 0.000 claims description 34
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 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 17
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 210000003169 central nervous system Anatomy 0.000 claims description 10
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- -1 carbamoyl halide Chemical class 0.000 claims description 9
- 150000002431 hydrogen Chemical class 0.000 claims description 9
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 6
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 4
- 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 description 4
- 239000012458 free base Substances 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 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 4
- 239000012948 isocyanate Substances 0.000 claims description 3
- 150000002513 isocyanates Chemical class 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 238000007911 parenteral administration Methods 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims 1
- 239000008024 pharmaceutical diluent Substances 0.000 claims 1
- 239000003814 drug Substances 0.000 abstract description 35
- PIJVFDBKTWXHHD-UHFFFAOYSA-N Physostigmine Natural products C12=CC(OC(=O)NC)=CC=C2N(C)C2C1(C)CCN2C PIJVFDBKTWXHHD-UHFFFAOYSA-N 0.000 description 31
- 229940079593 drug Drugs 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
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- 102100033639 Acetylcholinesterase Human genes 0.000 description 14
- 108010022752 Acetylcholinesterase Proteins 0.000 description 14
- 210000004556 brain Anatomy 0.000 description 14
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 229940022698 acetylcholinesterase Drugs 0.000 description 12
- 102000004190 Enzymes Human genes 0.000 description 9
- 108090000790 Enzymes Proteins 0.000 description 9
- 229940088598 enzyme Drugs 0.000 description 9
- OIPILFWXSMYKGL-UHFFFAOYSA-N acetylcholine Chemical compound CC(=O)OCC[N+](C)(C)C OIPILFWXSMYKGL-UHFFFAOYSA-N 0.000 description 8
- 229960004373 acetylcholine Drugs 0.000 description 8
- 230000005764 inhibitory process Effects 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 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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- 230000002829 reductive effect Effects 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000001727 in vivo Methods 0.000 description 6
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- 238000011282 treatment Methods 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- GQZXRLWUYONVCP-UHFFFAOYSA-N 3-[1-(dimethylamino)ethyl]phenol Chemical compound CN(C)C(C)C1=CC=CC(O)=C1 GQZXRLWUYONVCP-UHFFFAOYSA-N 0.000 description 4
- 229930003347 Atropine Natural products 0.000 description 4
- 208000012661 Dyskinesia Diseases 0.000 description 4
- RKUNBYITZUJHSG-UHFFFAOYSA-N Hyosciamin-hydrochlorid Natural products CN1C(C2)CCC1CC2OC(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-UHFFFAOYSA-N 0.000 description 4
- 231100000111 LD50 Toxicity 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- 229960000396 atropine Drugs 0.000 description 4
- RKUNBYITZUJHSG-SPUOUPEWSA-N atropine Chemical compound O([C@H]1C[C@H]2CC[C@@H](C1)N2C)C(=O)C(CO)C1=CC=CC=C1 RKUNBYITZUJHSG-SPUOUPEWSA-N 0.000 description 4
- 230000001713 cholinergic effect Effects 0.000 description 4
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- 239000000203 mixture Substances 0.000 description 4
- 229960005181 morphine Drugs 0.000 description 4
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- 239000002244 precipitate Substances 0.000 description 4
- 208000003870 Drug Overdose Diseases 0.000 description 3
- 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
- 208000024412 Friedreich ataxia Diseases 0.000 description 3
- 206010021079 Hypopnoea Diseases 0.000 description 3
- 241000699670 Mus sp. Species 0.000 description 3
- 206010028293 Muscle contractions involuntary Diseases 0.000 description 3
- 206010033296 Overdoses Diseases 0.000 description 3
- RVOLLAQWKVFTGE-UHFFFAOYSA-N Pyridostigmine Chemical compound CN(C)C(=O)OC1=CC=C[N+](C)=C1 RVOLLAQWKVFTGE-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000009471 action Effects 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 229930013930 alkaloid Natural products 0.000 description 3
- 229940035676 analgesics Drugs 0.000 description 3
- 239000000730 antalgic agent Substances 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 235000006708 antioxidants Nutrition 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 3
- 229940048961 cholinesterase Drugs 0.000 description 3
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- 239000003193 general anesthetic agent Substances 0.000 description 3
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- 230000007062 hydrolysis Effects 0.000 description 3
- 238000006460 hydrolysis reaction Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229960002362 neostigmine Drugs 0.000 description 3
- 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
- 239000008188 pellet Substances 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
- 241000167854 Bourreria succulenta Species 0.000 description 2
- 229920002261 Corn starch Polymers 0.000 description 2
- 206010012289 Dementia Diseases 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
- 208000001308 Fasciculation Diseases 0.000 description 2
- 238000012404 In vitro experiment Methods 0.000 description 2
- 241000124008 Mammalia Species 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- 241000699666 Mus <mouse, genus> Species 0.000 description 2
- 102000014415 Muscarinic acetylcholine receptor Human genes 0.000 description 2
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- 241000283973 Oryctolagus cuniculus Species 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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- 229940065524 anticholinergics inhalants for obstructive airway diseases Drugs 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 229940049706 benzodiazepine Drugs 0.000 description 2
- 125000003310 benzodiazepinyl group Chemical class N1N=C(C=CC2=C1C=CC=C2)* 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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- 230000000670 limiting effect Effects 0.000 description 1
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 1
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- 239000007788 liquid Substances 0.000 description 1
- 238000011866 long-term treatment Methods 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- 210000005171 mammalian brain Anatomy 0.000 description 1
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- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical class COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 1
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- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
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- OFCCYDUUBNUJIB-UHFFFAOYSA-N n,n-diethylcarbamoyl chloride Chemical compound CCN(CC)C(Cl)=O OFCCYDUUBNUJIB-UHFFFAOYSA-N 0.000 description 1
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- GVEAYVLWDAFXET-XGHATYIMSA-N pancuronium Chemical compound C[N+]1([C@@H]2[C@@H](OC(C)=O)C[C@@H]3CC[C@H]4[C@@H]5C[C@@H]([C@@H]([C@]5(CC[C@@H]4[C@@]3(C)C2)C)OC(=O)C)[N+]2(C)CCCCC2)CCCCC1 GVEAYVLWDAFXET-XGHATYIMSA-N 0.000 description 1
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- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
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- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 229940081974 saccharin Drugs 0.000 description 1
- 235000019204 saccharin Nutrition 0.000 description 1
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
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- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 230000006403 short-term memory Effects 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940124547 specific antidotes Drugs 0.000 description 1
- 238000002798 spectrophotometry method Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
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- 230000009885 systemic effect Effects 0.000 description 1
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- 231100001274 therapeutic index Toxicity 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
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- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
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- 239000003029 tricyclic antidepressant agent Substances 0.000 description 1
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Classifications
-
- 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
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- 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)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Psychiatry (AREA)
- Epidemiology (AREA)
- Hospice & Palliative Care (AREA)
- Emergency Medicine (AREA)
- Pain & Pain Management (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 JPS61225158A (ja) | 1986-10-06 |
| JPH0255416B2 true 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)
Families Citing this family (81)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH667001A5 (de) * | 1985-09-03 | 1988-09-15 | Hugo Degen | Untermatratze. |
| HU201906B (en) * | 1987-03-04 | 1991-01-28 | Sandoz Ag | Process for producing phenyl-carbamate derivative and acid additional salts and pharmaceutical compositions containing them |
| 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 |
| ES2241064T3 (es) | 1996-12-18 | 2005-10-16 | Teva Pharmaceutical Industries, Ltd. | Derivados de aminoindano. |
| US6251938B1 (en) | 1996-12-18 | 2001-06-26 | Teva Pharmaceutical Industries, Ltd., | Phenylethylamine derivatives |
| PT951284E (pt) * | 1996-12-18 | 2003-12-31 | Yissum Res Dev Co | Derivados de feniletilamina |
| WO1998031356A1 (en) * | 1997-01-17 | 1998-07-23 | Takeda Chemical Industries, Ltd. | Idebenone containing combination agent for treating alzheimer's disease |
| US5962535A (en) * | 1997-01-17 | 1999-10-05 | Takeda Chemical Industries, Ltd. | Composition for alzheimer's disease |
| GB9716879D0 (en) * | 1997-08-08 | 1997-10-15 | Shire Int Licensing Bv | Treatment of attention deficit disorders |
| US6316023B1 (en) * | 1998-01-12 | 2001-11-13 | Novartis Ag | TTS containing an antioxidant |
| US7939522B1 (en) * | 1998-11-23 | 2011-05-10 | Bonnie M Davis | Dosage formulations for acetylcholinesterase inhibitors |
| GB9923045D0 (en) * | 1999-09-29 | 1999-12-01 | Novartis Ag | New oral formulations |
| US6534541B1 (en) * | 1999-10-19 | 2003-03-18 | Novartis Ag | Treatment of ocular disorders |
| MXPA02007321A (es) | 2000-01-28 | 2003-01-28 | Omegatech Inc | Produccion mejorada de lipidos que contienen acidos grasos polienoicos por cultivos de alta densidad de microbios eucarioticos en fermentadores. |
| DK1311272T3 (da) * | 2000-03-03 | 2007-02-26 | Eisai R&D Man Co Ltd | Hidtil ukendte fremgangsmåder hvor der anvendes cholinesteraseinhibitorer |
| US20030153598A1 (en) * | 2000-07-25 | 2003-08-14 | Raymond Pratt | Methods for treating Parkinson's disease with cholinesterase inhibitors |
| JP2003530437A (ja) * | 2000-04-13 | 2003-10-14 | マヨ ファウンデーション フォー メディカル エデュケーション アンド リサーチ | Ａβ４２低下物質 |
| GB0126378D0 (en) * | 2001-11-02 | 2002-01-02 | Oxford Biomedica Ltd | Antigen |
| US20040010038A1 (en) * | 2002-02-27 | 2004-01-15 | Eran Blaugrund | Propargylamino indan derivatives and propargylamino tetralin derivatives as brain-selective MAO inhibitors |
| WO2003101917A2 (en) * | 2002-05-31 | 2003-12-11 | Sun Pharmaceutical Industries Limited | A process for the preparation of phenylcarbamates |
| JP4675103B2 (ja) | 2002-06-14 | 2011-04-20 | 富山化学工業株式会社 | 脳機能を改善する医薬組成物および脳機能を改善するための方法 |
| UA80841C2 (en) | 2002-10-07 | 2007-11-12 | Univ California | Fatty acid amide hydrolase inhibitors, pharmaceutical composition (variants) and method to treat appetite disorders, glaucoma, pain, and related neurological disorders (variants) |
| CZ293014B6 (cs) * | 2002-10-24 | 2004-01-14 | Léčiva, A.S. | Způsob výroby (-)-(S)-3-[1-(dimethylamino)ethyl]fenyl-N-ethyl-N-methylkarbamátu |
| DE10301851A1 (de) * | 2003-01-17 | 2004-07-29 | Lts Lohmann Therapie-Systeme Ag | Verfahren zur medikamentösen Prophylaxe gegen Vergiftungen durch Cholinesterase-Hemmer, sowie hierfür geeignete Wirkstoffe und Arzneimittel |
| EP1603548A4 (en) * | 2003-02-05 | 2007-10-10 | Myriad Genetics Inc | METHOD AND COMPOSITION FOR THE TREATMENT OF NEURODEEGENERATIVE DISEASES |
| US7521481B2 (en) | 2003-02-27 | 2009-04-21 | Mclaurin Joanne | Methods of preventing, treating and diagnosing disorders of protein aggregation |
| KR20060040676A (ko) * | 2003-07-11 | 2006-05-10 | 미리어드 제네틱스, 인크. | 알츠하이머병을 치료하기 위한 약제학적 방법, 투약 방법및 제형 |
| AU2004285893B2 (en) * | 2003-10-21 | 2011-12-15 | Colucid Pharmaceuticals, Inc. | Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents |
| JP4864719B2 (ja) | 2003-11-26 | 2012-02-01 | ファイザー・プロダクツ・インク | Ｇｓｋ−３インヒビターとしてのアミノピラゾール誘導体 |
| GB0329284D0 (en) * | 2003-12-18 | 2004-01-21 | Avecia Ltd | Process |
| GB2409453A (en) * | 2003-12-24 | 2005-06-29 | Generics | Process for the preparation of aminoalkyl phenylcarbamates |
| US20050222123A1 (en) | 2004-01-27 | 2005-10-06 | North Shore-Long Island Jewish Research Institute | Cholinesterase inhibitors for treating inflammation |
| KR20060127136A (ko) * | 2004-02-19 | 2006-12-11 | 노파르티스 아게 | 콜린에스테라아제 억제제의 혈관성 우울증을 치료하기 위한용도 |
| WO2006001877A2 (en) * | 2004-04-13 | 2006-01-05 | Myriad Genetics, Inc. | Combination treatment for neurodegenerative disorders comprising r-flurbiprofen |
| BRPI0514303A (pt) * | 2004-08-11 | 2008-06-10 | Myriad Genetics Inc | composição farmacêutica e método para tratar distúrbios neurodegenerativos |
| WO2006020852A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| WO2006020850A2 (en) * | 2004-08-11 | 2006-02-23 | Myriad Genetics, Inc. | Pharmaceutical composition and method for treating neurodegenerative disorders |
| CA2589102C (en) * | 2004-11-02 | 2013-08-13 | Northwestern University | Pyridazine compounds and methods for using the compounds to treat inflammatory diseases |
| RU2393148C2 (ru) * | 2004-11-08 | 2010-06-27 | Эмкюр Фармасьютикалз Лимитед | Способ получения (s)-3-[(1-диметиламино)этил]-фенил-n-этил-n-метил-карбамата |
| EP1819681B1 (en) * | 2004-11-23 | 2009-08-12 | Warner-Lambert Company LLC | 7-(2h-pyrazol-3-yl)-3,5-dihydroxy-heptanoic acid derivatives as hmg co-a reductase inhibitors for the treatment of lipidemia |
| US7619007B2 (en) | 2004-11-23 | 2009-11-17 | Adamas Pharmaceuticals, Inc. | Method and composition for administering an NMDA receptor antagonist to a subject |
| DK1874282T3 (da) * | 2005-04-06 | 2010-10-25 | Adamas Pharmaceuticals Inc | Fremgangsmåder og præparater til behandling af CNS lidelser |
| US20070015832A1 (en) * | 2005-07-14 | 2007-01-18 | Myriad Genetics, Incorporated | Methods of treating overactive bladder and urinary incontinence |
| ES2267399B1 (es) | 2005-08-04 | 2008-02-01 | Ragactives, S.L. | Procedimiento para la obtencion de carbamatos de fenilo. |
| CN101325871B (zh) * | 2005-12-09 | 2013-04-10 | 耶路撒冷希伯来大学伊森姆研究发展公司 | 低剂量Ladostigil用于神经保护的用途 |
| TW200744576A (en) * | 2006-02-24 | 2007-12-16 | Teva Pharma | Propargylated aminoindans, processes for preparation, and uses thereof |
| US7767843B2 (en) * | 2006-03-02 | 2010-08-03 | Apotex Pharmachem Inc. | Process for the preparation of phenylcarbamates |
| EP2015750A2 (en) * | 2006-04-28 | 2009-01-21 | Northwestern University | Compositions and treatments using pyridazine compounds and cholinesterase inhibitors |
| EP2046119A2 (en) * | 2006-07-07 | 2009-04-15 | Myriad Genetics, Inc. | Treatment of psychiatric disorders |
| ATE472523T1 (de) * | 2006-08-17 | 2010-07-15 | Alembic Ltd | Verbessertes verfahren zur herstellung von rivastigmin |
| WO2008037433A1 (en) | 2006-09-29 | 2008-04-03 | Synthon B.V. | Process for making aminoalkylphenyl carbamates and intermediates therefor |
| KR20090087009A (ko) | 2006-10-27 | 2009-08-14 | 메디베이션 뉴롤로지 인코퍼레이티드 | 아이.에이. 다임본 및 도레페질을 사용하여 알츠하이머 병을 치료하기 위한 조합 요법 |
| WO2008097546A2 (en) * | 2007-02-02 | 2008-08-14 | Colucid Pharmaceuticals, Inc. | Compounds that inhibit cholinesterase |
| US8013181B2 (en) | 2007-04-10 | 2011-09-06 | Dr. Reddy's Laboratories Limited | Preparation of rivastigmine and its salts |
| CN101707952B (zh) * | 2007-04-16 | 2012-08-29 | 上海特化医药科技有限公司 | 一种制备利伐斯的明的方法及其中间体 |
| US7884121B2 (en) | 2007-06-11 | 2011-02-08 | Apotex Pharmachem Inc. | Process for the preparation of phenylcarbamates |
| EP2182938A2 (en) * | 2007-07-18 | 2010-05-12 | Colucid Pharmaceuticals, Inc. | Methods for promoting wakefulness |
| US8593728B2 (en) * | 2009-02-19 | 2013-11-26 | Toyota Motor Engineering & Manufacturing North America, Inc. | Multilayer photonic structures |
| WO2010023535A1 (en) | 2008-08-25 | 2010-03-04 | Jubilant Organosys Limited | A process for producing (s)-3-[(1-dimethylamino)ethyl] phenyl-n-ethyl-n-methyl-carbamate via novel intermediates |
| US8247405B2 (en) | 2008-12-10 | 2012-08-21 | Conopco, Inc. | Skin lightening compositions with acetylcholinesterase inhibitors |
| CN101580482B (zh) * | 2009-05-27 | 2014-04-23 | 沈阳药科大学 | 一种重酒石酸盐卡巴拉汀的制备方法和应用 |
| ES2363395B1 (es) * | 2010-01-20 | 2012-02-23 | Farmalider, S.A. | Composición farmacéutica l�?quida de rivastigmina o de una de sus sales de adición de �?cido para la administración por v�?a oral. |
| CN102134206B (zh) * | 2010-01-27 | 2013-11-20 | 上海京新生物医药有限公司 | 一种卡巴拉汀的制备方法 |
| BR112012019923A2 (pt) | 2010-02-09 | 2016-08-09 | Univ Johns Hopkins | métodos e composições para melhorar a função cognitiva |
| WO2011151359A1 (en) | 2010-06-02 | 2011-12-08 | Noscira, S.A. | Combined treatment with a cholinesterase inhibitor and a thiadiazolidinedione derivative |
| WO2011151669A1 (en) | 2010-06-02 | 2011-12-08 | Jubilant Life Sciences Limited | Process for producing enantiomerically enriched isomer of 3-(1-aminoethyl) phenyl derivative and employing the same to produce rivastigmine or its pharmaceutically acceptable salt |
| DK2582799T3 (en) | 2010-06-17 | 2018-02-12 | Codexis Inc | BIOCATALATORS AND PROCEDURES FOR THE SYNTHESIS OF (S) -3- (1-AMINOETHYL) -PHENOL |
| WO2012131699A1 (en) | 2011-03-30 | 2012-10-04 | Neon Laboratories Ltd. | Process for preparation of highly pure 3-dimethylaminophenyl dimethylcarbamate |
| CN102786441B (zh) * | 2011-05-18 | 2013-11-13 | 浙江海正药业股份有限公司 | 利凡斯的明的制备方法、其中间体以及中间体的制备方法 |
| CA2870303A1 (en) | 2012-04-14 | 2013-10-17 | Intra-Cellular Therapies, Inc. | Organic compounds |
| ES2449215B1 (es) * | 2012-09-17 | 2014-07-14 | Galenicum Health S.L. | Solución oral de (S)-3-[1-(dimetilamino)etil]fenil N-etil-N-metilcarbamato |
| HK1215170A1 (zh) | 2012-11-14 | 2016-08-19 | The Johns Hopkins University | 治療精神分裂症的方法和組合物 |
| EP2968237A4 (en) | 2013-03-15 | 2016-08-31 | Univ Johns Hopkins | METHOD AND COMPOSITIONS FOR IMPROVING COGNITIVE FUNCTION |
| CN105142623A (zh) | 2013-03-15 | 2015-12-09 | 艾吉因生物股份有限公司 | 用于改善认知功能的方法和组合物 |
| EP3033082B1 (en) | 2013-08-16 | 2021-06-16 | Universiteit Maastricht | Treatment of cognitive impairment with pde4 inhibitor |
| MX384391B (es) | 2015-05-22 | 2025-03-14 | Agenebio Inc | Composiciones farmacéuticas de levetiracetam de liberación extendida. |
| KR20200035359A (ko) | 2018-09-26 | 2020-04-03 | 캐딜라 파마슈티클즈 리미티드 | 리바스티그민 제조용 중간체의 합성 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1905990A (en) * | 1931-01-02 | 1933-04-25 | Hoffmann La Roche | Disubstituted carbamic acid esters of phenols containing a basic constituent |
| 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 |
| US2362508A (en) * | 1940-12-06 | 1944-11-14 | Merck & Co Inc | Therapeutic substances |
| 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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1985
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1986
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- 1986-03-04 JP JP61048183A patent/JPS61225158A/ja active Granted
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