TWI655179B - 胺基羰基胺基甲酸酯化合物 - Google Patents
胺基羰基胺基甲酸酯化合物 Download PDFInfo
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- TWI655179B TWI655179B TW104106005A TW104106005A TWI655179B TW I655179 B TWI655179 B TW I655179B TW 104106005 A TW104106005 A TW 104106005A TW 104106005 A TW104106005 A TW 104106005A TW I655179 B TWI655179 B TW I655179B
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- TW
- Taiwan
- Prior art keywords
- aminocarbonyl
- amino
- propyl
- carbamate
- compound
- Prior art date
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- -1 Aminocarbonyl carbamate compound Chemical class 0.000 title claims description 200
- 150000001875 compounds Chemical class 0.000 claims abstract description 102
- 150000003839 salts Chemical class 0.000 claims abstract description 54
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 19
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 18
- 150000002367 halogens Chemical class 0.000 claims abstract description 18
- 125000003118 aryl group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 8
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- GTCAXTIRRLKXRU-UHFFFAOYSA-N carbamic acid methyl ester Natural products COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 claims description 73
- VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 59
- 229960003638 dopamine Drugs 0.000 claims description 29
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 21
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 239000002253 acid Substances 0.000 claims description 17
- 201000010099 disease Diseases 0.000 claims description 15
- 208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 13
- 208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 11
- 208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 11
- 239000000203 mixture Substances 0.000 claims description 11
- 150000002148 esters Chemical class 0.000 claims description 10
- 239000008194 pharmaceutical composition Substances 0.000 claims description 10
- 238000011282 treatment Methods 0.000 claims description 9
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical group N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims description 5
- LGINNYTYYKXJBZ-SNVBAGLBSA-N [(2R)-2-amino-3-phenylpropyl] N-(2-amino-2-oxoethyl)carbamate Chemical compound NC(=O)CNC(OC[C@@H](CC1=CC=CC=C1)N)=O LGINNYTYYKXJBZ-SNVBAGLBSA-N 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 claims description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N benzene Substances C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 4
- 238000009472 formulation Methods 0.000 claims description 4
- 241000124008 Mammalia Species 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 2
- PYLWMHQQBFSUBP-UHFFFAOYSA-N monofluorobenzene Chemical group FC1=CC=CC=C1 PYLWMHQQBFSUBP-UHFFFAOYSA-N 0.000 claims 1
- 238000000034 method Methods 0.000 abstract description 36
- 229940094659 Dopamine reuptake inhibitor Drugs 0.000 abstract description 3
- 239000000221 dopamine uptake inhibitor Substances 0.000 abstract description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 60
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 34
- 238000005160 1H NMR spectroscopy Methods 0.000 description 29
- 239000000376 reactant Substances 0.000 description 24
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
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- 238000012360 testing method Methods 0.000 description 8
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
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- 108010044266 Dopamine Plasma Membrane Transport Proteins Proteins 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
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- 239000007858 starting material Substances 0.000 description 6
- DUGOZIWVEXMGBE-UHFFFAOYSA-N Methylphenidate Chemical compound C=1C=CC=CC=1C(C(=O)OC)C1CCCCN1 DUGOZIWVEXMGBE-UHFFFAOYSA-N 0.000 description 5
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 5
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- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 4
- CFFZDZCDUFSOFZ-UHFFFAOYSA-N 3,4-Dihydroxy-phenylacetic acid Chemical compound OC(=O)CC1=CC=C(O)C(O)=C1 CFFZDZCDUFSOFZ-UHFFFAOYSA-N 0.000 description 4
- RGHNJXZEOKUKBD-SQOUGZDYSA-N D-gluconic acid Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C(O)=O RGHNJXZEOKUKBD-SQOUGZDYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
- 241000699670 Mus sp. Species 0.000 description 4
- PJLCNWPOTRZGFK-UHFFFAOYSA-N NC(=O)NC(OCC(CC1=CC=CC=C1)N)=O Chemical compound NC(=O)NC(OCC(CC1=CC=CC=C1)N)=O PJLCNWPOTRZGFK-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
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- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- GTOVBVXKJLFDMR-SNVBAGLBSA-N [(2r)-2-amino-3-phenylpropyl] n-methylcarbamate Chemical compound CNC(=O)OC[C@H](N)CC1=CC=CC=C1 GTOVBVXKJLFDMR-SNVBAGLBSA-N 0.000 description 4
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 4
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 4
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- 235000011090 malic acid Nutrition 0.000 description 4
- 238000011160 research Methods 0.000 description 4
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- 230000008925 spontaneous activity Effects 0.000 description 4
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
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- 210000003169 central nervous system Anatomy 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 229940079593 drug Drugs 0.000 description 3
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- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229940093915 gynecological organic acid Drugs 0.000 description 3
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 3
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- 150000002513 isocyanates Chemical class 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
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- UCTRAOBQFUDCSR-UHFFFAOYSA-N (2-amino-3-phenylpropyl) carbamate Chemical compound NC(=O)OCC(N)CC1=CC=CC=C1 UCTRAOBQFUDCSR-UHFFFAOYSA-N 0.000 description 2
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- QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 2
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- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002287 radioligand Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 229940099204 ritalin Drugs 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000035807 sensation Effects 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000002603 single-photon emission computed tomography Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 230000000946 synaptic effect Effects 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229940126585 therapeutic drug Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 125000000165 tricyclic carbocycle group Chemical group 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-M urea-1-carboxylate Chemical compound NC(=O)NC([O-])=O AVWRKZWQTYIKIY-UHFFFAOYSA-M 0.000 description 1
- AVWRKZWQTYIKIY-UHFFFAOYSA-N urea-1-carboxylic acid Chemical class NC(=O)NC(O)=O AVWRKZWQTYIKIY-UHFFFAOYSA-N 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- NAUWTFJOPJWYOT-UHFFFAOYSA-N vanoxerine Chemical compound C1=CC(F)=CC=C1C(C=1C=CC(F)=CC=1)OCCN1CCN(CCCC=2C=CC=CC=2)CC1 NAUWTFJOPJWYOT-UHFFFAOYSA-N 0.000 description 1
- 229940013007 vyvanse Drugs 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- 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
- A61K31/325—Carbamic acids; Thiocarbamic acids; Anhydrides or salts thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/0053—Mouth and digestive tract, i.e. intraoral and peroral administration
-
- 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
-
- 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
- C07C275/00—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C275/46—Derivatives of urea, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups containing any of the groups, X being a hetero atom, Y being any atom, e.g. acylureas
- C07C275/58—Y being a hetero atom
- C07C275/60—Y being an oxygen atom, e.g. allophanic acids
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Organic Chemistry (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Physiology (AREA)
- Nutrition Science (AREA)
- Biomedical Technology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201461946142P | 2014-02-28 | 2014-02-28 | |
| US61/946,142 | 2014-02-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| TW201623224A TW201623224A (zh) | 2016-07-01 |
| TWI655179B true TWI655179B (zh) | 2019-04-01 |
Family
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| Application Number | Title | Priority Date | Filing Date |
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| TW104106005A TWI655179B (zh) | 2014-02-28 | 2015-02-25 | 胺基羰基胺基甲酸酯化合物 |
| TW108106172A TWI698415B (zh) | 2014-02-28 | 2015-02-25 | 胺基羰基胺基甲酸酯化合物 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW108106172A TWI698415B (zh) | 2014-02-28 | 2015-02-25 | 胺基羰基胺基甲酸酯化合物 |
Country Status (15)
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| US (4) | US9403761B2 (OSRAM) |
| EP (2) | EP3110792B1 (OSRAM) |
| JP (2) | JP6452731B2 (OSRAM) |
| KR (2) | KR102309903B1 (OSRAM) |
| CN (2) | CN109627186B (OSRAM) |
| AR (1) | AR099581A1 (OSRAM) |
| AU (2) | AU2015223579B2 (OSRAM) |
| CA (1) | CA2939835C (OSRAM) |
| CL (1) | CL2016002165A1 (OSRAM) |
| ES (2) | ES2968840T3 (OSRAM) |
| MX (2) | MX387796B (OSRAM) |
| PL (1) | PL3110792T3 (OSRAM) |
| RU (1) | RU2688673C2 (OSRAM) |
| TW (2) | TWI655179B (OSRAM) |
| WO (1) | WO2015130121A1 (OSRAM) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US10888542B2 (en) * | 2014-02-28 | 2021-01-12 | Sk Biopharmaceuticals Co., Ltd. | Aminocarbonylcarbamate compounds |
| TWI655179B (zh) * | 2014-02-28 | 2019-04-01 | 南韓商愛思開生物製藥股份有限公司 | 胺基羰基胺基甲酸酯化合物 |
| US10195151B2 (en) | 2016-09-06 | 2019-02-05 | Jazz Pharmaceuticals International Iii Limited | Formulations of (R)-2-amino-3-phenylpropyl carbamate |
| JP7219213B2 (ja) | 2016-09-06 | 2023-02-07 | ジャズ ファーマスティカルズ アイルランド リミテッド | （ｒ）－２－アミノ－３－フェニルプロピルカルバメートの溶媒和物フォーム |
| SG11201903076QA (en) * | 2016-10-06 | 2019-05-30 | Jazz Pharmaceuticals International Iii Ltd | Carbamoyl phenylalaninol compounds and uses therof |
| KR20240162165A (ko) | 2017-06-02 | 2024-11-14 | 재즈 파마슈티칼즈 아일랜드 리미티드 | 과다 졸림증을 치료하기 위한 방법 및 조성물 |
| CN111153863A (zh) * | 2019-12-13 | 2020-05-15 | 浙江工业大学 | 一种合成动物用抗球虫药物妥曲珠利的方法 |
| US10940133B1 (en) | 2020-03-19 | 2021-03-09 | Jazz Pharmaceuticals Ireland Limited | Methods of providing solriamfetol therapy to subjects with impaired renal function |
| KR102390194B1 (ko) | 2020-08-03 | 2022-04-25 | 셀라이온바이오메드 주식회사 | 페닐알킬 카바메이트 화합물을 포함하는 Kca3.1채널 매개질환 치료용 조성물 |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430201A2 (en) * | 1989-11-30 | 1991-06-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Aminocarbonylcarbamates related to physostigmine, a process for their preparation and their use as medicaments |
| CN102762201A (zh) * | 2009-11-06 | 2012-10-31 | 爱思开生物制药株式会社 | 注意力缺陷/多动症的治疗方法 |
Family Cites Families (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0665226A1 (en) * | 1992-10-28 | 1995-08-02 | Toyama Chemical Co., Ltd. | Novel 1,2-benzisoxazole derivative or salt thereof, and brain protective agent comprising the same |
| KR100197892B1 (ko) | 1994-09-09 | 1999-06-15 | 남창우 | 신규한 페닐알킬아미노 카바메이트 화합물과 그의 제조방법 |
| KR0173862B1 (ko) * | 1995-02-11 | 1999-04-01 | 조규향 | O-카바모일-(d)-페닐알라닌올 화합물과 그의 약제학적으로 유용한 염 및 이들의 제조방법 |
| US5756817C1 (en) | 1995-02-11 | 2001-04-17 | Sk Corp | O-carbamoyl-phenylananinol compounds their pharmaceutically useful salts and process for preparing the same |
| KR0173863B1 (ko) | 1995-04-10 | 1999-04-01 | 조규향 | 페닐에 치환체가 있는 o-카바모일-페닐알라닌올 화합물과 그의 약제학적으로 유용한 염 및 이들의 제조방법 |
| EP1636188A1 (en) * | 2003-06-12 | 2006-03-22 | Novo Nordisk A/S | Para-substituted phenyl carbamates as inhibitors of hormone sensitive lipase |
| US20050080268A1 (en) | 2003-10-08 | 2005-04-14 | Yong-Moon Choi | Process of preparing O-carbamoyl compounds in the presence of active amine group |
| US7897639B2 (en) * | 2003-10-21 | 2011-03-01 | Colucid Pharmaceuticals, Inc. | Carbamoyl esters that inhibit cholinesterase and release pharmacologically active agents |
| WO2006050037A1 (en) | 2004-10-28 | 2006-05-11 | Sk Corporation | Adjunctive therapy for depression |
| US7598279B2 (en) * | 2005-04-22 | 2009-10-06 | Sk Holdings Co., Ltd. | Neurotherapeutic azole compounds |
| PL1890684T3 (pl) | 2005-06-08 | 2014-05-30 | Sk Biopharmaceuticals Co Ltd | Leczenie zaburzeń snu i czuwania |
| ATE459393T1 (de) | 2005-06-22 | 2010-03-15 | Sk Holdings Co Ltd | Behandlung der sexuellen dysfunktion |
| TW200820963A (en) * | 2006-07-28 | 2008-05-16 | Xenoport Inc | Acyloxyalkyl carbamate prodrugs of α-amino acids, methods of synthesis and use |
| CN101631770A (zh) * | 2007-02-02 | 2010-01-20 | 科露西德医药品公司 | 抑制胆碱酯酶的化合物 |
| WO2011005473A2 (en) | 2009-06-22 | 2011-01-13 | Shionogi Pharma, Inc. | Methods for treating or preventing fatigue |
| US8232315B2 (en) | 2009-06-26 | 2012-07-31 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating drug addiction and improving addiction-related behavior |
| RU2557533C2 (ru) | 2009-11-06 | 2015-07-20 | Ск Биофармасъютиклс Ко., Лтд. | Способы лечения синдрома фибромиалгии |
| US8623913B2 (en) | 2010-06-30 | 2014-01-07 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating restless legs syndrome |
| US9610274B2 (en) | 2010-06-30 | 2017-04-04 | Sk Biopharmaceuticals Co., Ltd. | Methods for treating bipolar disorder |
| CN105873576B (zh) * | 2013-07-18 | 2019-07-19 | 爵士制药国际Iii有限公司 | 治疗肥胖 |
| TWI655179B (zh) * | 2014-02-28 | 2019-04-01 | 南韓商愛思開生物製藥股份有限公司 | 胺基羰基胺基甲酸酯化合物 |
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2015
- 2015-02-25 TW TW104106005A patent/TWI655179B/zh active
- 2015-02-25 TW TW108106172A patent/TWI698415B/zh active
- 2015-02-26 AR ARP150100575A patent/AR099581A1/es active IP Right Grant
- 2015-02-27 CA CA2939835A patent/CA2939835C/en active Active
- 2015-02-27 CN CN201811495363.1A patent/CN109627186B/zh active Active
- 2015-02-27 EP EP15754658.1A patent/EP3110792B1/en active Active
- 2015-02-27 CN CN201580010772.6A patent/CN106458866B/zh active Active
- 2015-02-27 RU RU2016136193A patent/RU2688673C2/ru active
- 2015-02-27 ES ES19188405T patent/ES2968840T3/es active Active
- 2015-02-27 KR KR1020167022646A patent/KR102309903B1/ko active Active
- 2015-02-27 MX MX2020003020A patent/MX387796B/es unknown
- 2015-02-27 MX MX2016010973A patent/MX2016010973A/es active IP Right Grant
- 2015-02-27 ES ES15754658T patent/ES2759312T3/es active Active
- 2015-02-27 AU AU2015223579A patent/AU2015223579B2/en active Active
- 2015-02-27 PL PL15754658T patent/PL3110792T3/pl unknown
- 2015-02-27 WO PCT/KR2015/001915 patent/WO2015130121A1/en not_active Ceased
- 2015-02-27 US US14/633,388 patent/US9403761B2/en active Active
- 2015-02-27 JP JP2016572221A patent/JP6452731B2/ja active Active
- 2015-02-27 EP EP19188405.5A patent/EP3587394B1/en active Active
- 2015-02-27 KR KR1020217031464A patent/KR102487051B1/ko active Active
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2016
- 2016-06-28 US US15/195,326 patent/US9833432B2/en active Active
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- 2017-11-07 US US15/805,293 patent/US10314808B2/en active Active
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- 2018-12-11 JP JP2018231320A patent/JP6595078B2/ja active Active
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- 2019-04-26 US US16/395,422 patent/US10485781B2/en active Active
- 2019-09-25 AU AU2019236666A patent/AU2019236666B2/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0430201A2 (en) * | 1989-11-30 | 1991-06-05 | Hoechst-Roussel Pharmaceuticals Incorporated | Aminocarbonylcarbamates related to physostigmine, a process for their preparation and their use as medicaments |
| CN102762201A (zh) * | 2009-11-06 | 2012-10-31 | 爱思开生物制药株式会社 | 注意力缺陷/多动症的治疗方法 |
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