RU96113126A - CARBAMATES OF PHENYLALKYLAMINOSPIRTS AND METHODS FOR THEIR PRODUCTION - Google Patents
CARBAMATES OF PHENYLALKYLAMINOSPIRTS AND METHODS FOR THEIR PRODUCTIONInfo
- Publication number
- RU96113126A RU96113126A RU96113126/04A RU96113126A RU96113126A RU 96113126 A RU96113126 A RU 96113126A RU 96113126/04 A RU96113126/04 A RU 96113126/04A RU 96113126 A RU96113126 A RU 96113126A RU 96113126 A RU96113126 A RU 96113126A
- Authority
- RU
- Russia
- Prior art keywords
- structural formula
- phenylalaninol
- carbamoyl
- formation
- benzyloxycarbonyl
- Prior art date
Links
- 150000004657 carbamic acid derivatives Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 9
- 230000015572 biosynthetic process Effects 0.000 claims 7
- 238000005755 formation reaction Methods 0.000 claims 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 6
- 230000001681 protective Effects 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 239000011780 sodium chloride Substances 0.000 claims 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N HCl Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 5
- 239000007864 aqueous solution Substances 0.000 claims 5
- UCTRAOBQFUDCSR-SECBINFHSA-N [(2R)-2-amino-3-phenylpropyl] carbamate Chemical compound NC(=O)OC[C@H](N)CC1=CC=CC=C1 UCTRAOBQFUDCSR-SECBINFHSA-N 0.000 claims 4
- 239000000243 solution Substances 0.000 claims 4
- HSDAJNMJOMSNEV-UHFFFAOYSA-N Benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 claims 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims 3
- 239000000908 ammonium hydroxide Substances 0.000 claims 3
- 238000007327 hydrogenolysis reaction Methods 0.000 claims 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 3
- UCTRAOBQFUDCSR-VIFPVBQESA-N [(2S)-2-amino-3-phenylpropyl] carbamate Chemical compound NC(=O)OC[C@@H](N)CC1=CC=CC=C1 UCTRAOBQFUDCSR-VIFPVBQESA-N 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- STVVMTBJNDTZBF-SECBINFHSA-N (2R)-2-amino-3-phenylpropan-1-ol Chemical compound OC[C@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-SECBINFHSA-N 0.000 claims 1
- STVVMTBJNDTZBF-VIFPVBQESA-N L-Phenylalaninol Chemical compound OC[C@@H](N)CC1=CC=CC=C1 STVVMTBJNDTZBF-VIFPVBQESA-N 0.000 claims 1
- KAOVAAHCFNYXNJ-FVGYRXGTSA-N [(2S)-2-amino-3-phenylpropyl] carbamate;hydrochloride Chemical compound Cl.NC(=O)OC[C@@H](N)CC1=CC=CC=C1 KAOVAAHCFNYXNJ-FVGYRXGTSA-N 0.000 claims 1
- JVCZEXMSWYJTJB-MRXNPFEDSA-N benzyl N-[(2R)-1-carbamoyloxy-3-phenylpropan-2-yl]carbamate Chemical compound C([C@H](COC(=O)N)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 JVCZEXMSWYJTJB-MRXNPFEDSA-N 0.000 claims 1
- WPOFMMJJCPZPAO-MRXNPFEDSA-N benzyl N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate Chemical compound C([C@H](CO)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 WPOFMMJJCPZPAO-MRXNPFEDSA-N 0.000 claims 1
- JVCZEXMSWYJTJB-INIZCTEOSA-N benzyl N-[(2S)-1-carbamoyloxy-3-phenylpropan-2-yl]carbamate Chemical compound C([C@@H](COC(=O)N)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 JVCZEXMSWYJTJB-INIZCTEOSA-N 0.000 claims 1
- WPOFMMJJCPZPAO-INIZCTEOSA-N benzyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate Chemical compound C([C@@H](CO)NC(=O)OCC=1C=CC=CC=1)C1=CC=CC=C1 WPOFMMJJCPZPAO-INIZCTEOSA-N 0.000 claims 1
- UCTRAOBQFUDCSR-UHFFFAOYSA-N NC(Cc1ccccc1)COC(N)=O Chemical compound NC(Cc1ccccc1)COC(N)=O UCTRAOBQFUDCSR-UHFFFAOYSA-N 0.000 description 2
- ILOGFJAZRYULRV-SNVBAGLBSA-N N[C@H](Cc1ccccc1)COCO Chemical compound N[C@H](Cc1ccccc1)COCO ILOGFJAZRYULRV-SNVBAGLBSA-N 0.000 description 1
Claims (9)
и его фармацевтически приемлемые соли.1. O-car6amoyl- (D / L) -phenylalaninol of structural formula I
and its pharmaceutically acceptable salts.
и его фармацевтически приемлемые соли.2. O-carbamoyl- (D) -phenylalaninol of structural formula II
and its pharmaceutically acceptable salts.
и его фармацевтически приемлемые соли.3. O-carbamoyl- (L) -phenylalaninol of structural formula III
and its pharmaceutically acceptable salts.
бензилхлорформиатом в основном водном растворе с образованием N-бензилоксикарбонил-(D/L)-фенилаланинола структурной формулы V
осуществления взаимодействия соединения структурной формулы V с фосгеном и затем обработки избытком концентрированного раствора гидроокиси аммония с получением о-карбамоил-N-бензилоксикарбонил(D/L)-фенилаланинола структурной формулы VI
удаления защитной группы Y соединения структурной формулы VI путем гидрогенолиза с образованием О-карбамоил-(D/L)-фенилаланинола структурной формулы I.4. The method of obtaining O-carbamoyl- (D / L) -phenylalaninol of structural formula I
benzyl chloroformate in the main aqueous solution with the formation of N-benzyloxycarbonyl- (D / L) -phenylalaninol of structural formula V
reacting a compound of structural formula V with phosgene and then treating with an excess of a concentrated solution of ammonium hydroxide to obtain o-carbamoyl-N-benzyloxycarbonyl (D / L) -phenylalaninol of structural formula VI
removing the protective group Y of a compound of structural formula VI by hydrogenolysis to form O-carbamoyl- (D / L) -phenylalaninol of structural formula I.
являющейся фармацевтически приемлемой солью.5. The method according to p. 4, characterized in that the compounds of structural formula I are treated with anhydrous hydrogen chloride in a solution of simple ether, followed by a stage of removal of the protective group with the formation of hydrochloric acid salt of o-carbamate (D / L) -phenylalanol of structural formula VII
being a pharmaceutically acceptable salt.
включающий стадии: обработки (D)-фенилаланинола структурной формулы IV'
бензилхлорформиатом в основном водном растворе с образованием N-бензилоксикарбонил-(D)-фенилаланинола структурной формулы V'
осуществления реакции соединения структурной формулы V с фосгеном и затем обработки избытком концентрированного водного раствора гидроокиси аммония с получением O-карбамоил-N-бензилоксикарбонил-(D)-фенилаланинола структурной формулы VI'
удаления защитной группы Y соединения структурной формулы VI' путем гидрогенолиза с получением O-карбамоил-(D)-фенилаланинола структурной формулы II.6. The method of obtaining O-carbamoyl- (D) -phenylalaninol of structural formula II
comprising the steps of: treating (D) -phenylalaninol of structural formula IV '
benzyl chloroformate in the main aqueous solution with the formation of N-benzyloxycarbonyl- (D) -phenylalaninol of structural formula V '
the reaction of the compound of structural formula V with phosgene and then treatment with an excess of a concentrated aqueous solution of ammonium hydroxide with obtaining O-carbamoyl-N-benzyloxycarbonyl- (D) -phenylalaninol of structural formula VI '
removing the protective group Y of the compound of structural formula VI 'by hydrogenolysis to obtain O-carbamoyl- (D) -phenylalaninol of structural formula II.
являющейся фармацевтически приемлемой солью.7. The method according to p. 6, characterized in that the compounds of structural formula II are treated with anhydrous hydrogen chloride in a solution of simple ether, followed by removal of the protective group with the formation of hydrochloric acid salt of O-carbamoyl- (D) -phenylalaninol of structural formula VII '
being a pharmaceutically acceptable salt.
включающий стадии обработки (L) - фенилаланинола структурной формулы IV"
бензилхлорформиатом в основном водном растворе с образованием N-бензилоксикарбонил-(L)-фенилаланинола структурной формулы V"
осуществления реакции соединения структурной формулы V" с фосгеном и затем обработки избытком концентрированного водного раствора гидроокиси аммония с образованием О-карбамоил-N-бензилоксикарбонил-(L)-фенилаланинола структурной формулы VI"
удаления защитной группы Y соединения структурной формулы VI" путем гидрогенолиза с образованием O-кapбaмоил-(L)-фeнилaланинола структурной формулы III.8. The method of obtaining O-carbamoyl- (L) -phenylalaninol of structural formula III
including the processing steps of (L) - phenylalaninol of structural formula IV "
benzyl chloroformate in the main aqueous solution with the formation of N-benzyloxycarbonyl- (L) -phenylalaninol of structural formula V "
the implementation of the reaction of compounds of structural formula V "with phosgene and then processing an excess of a concentrated aqueous solution of ammonium hydroxide with the formation of O-carbamoyl-N-benzyloxycarbonyl- (L) -phenylalaninol of structural formula VI"
removing the protective group Y of a compound of structural formula VI "by hydrogenolysis to form O-carbamate- (L) -phenyl-alaninol of structural formula III.
являющейся фармацевтически приемлемой солью.9. The method according to p. 8, characterized in that the compounds of structural formula III are treated with anhydrous hydrogen chloride in an ether solution followed by removal of the protective group with the formation of O-carbamoyl- (L) -phenylalaninol hydrochloride salt of the structural formula VII "
being a pharmaceutically acceptable salt.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1019940022798A KR100197892B1 (en) | 1994-09-09 | 1994-09-09 | Novel phenylalkylaminoalcohol carbamates and process for preparing the same |
| KR1994/22798 | 1994-09-09 | ||
| PCT/KR1995/000114 WO1996007637A1 (en) | 1994-09-09 | 1995-09-06 | Novel phenylalkylaminoalcohol carbamates and process for preparing the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU96113126A true RU96113126A (en) | 1998-01-10 |
| RU2104266C1 RU2104266C1 (en) | 1998-02-10 |
Family
ID=19392447
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU96113126/04A RU2104266C1 (en) | 1994-09-09 | 1995-09-06 | Phenylalkylamino alcohols and methods of preparing thereof |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US5955499A (en) |
| EP (1) | EP0728129B1 (en) |
| JP (1) | JP2680478B2 (en) |
| KR (1) | KR100197892B1 (en) |
| CN (1) | CN1069635C (en) |
| AU (1) | AU700544B2 (en) |
| CA (1) | CA2176012C (en) |
| DE (1) | DE69513140T2 (en) |
| ES (1) | ES2140703T3 (en) |
| RU (1) | RU2104266C1 (en) |
| WO (1) | WO1996007637A1 (en) |
Families Citing this family (28)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR0173862B1 (en) * | 1995-02-11 | 1999-04-01 | 조규향 | O-carbamoyl- (D) -phenylalaninol compounds and their pharmaceutically useful salts and methods for their preparation |
| US20030069630A1 (en) * | 2001-03-02 | 2003-04-10 | Robert Burgermeister | Stent with radiopaque markers incorporated thereon |
| AU2005302589B2 (en) * | 2004-10-28 | 2010-09-16 | Sk Biopharmaceuticals Co., Ltd. | Adjunctive therapy for depression |
| PL1890684T3 (en) | 2005-06-08 | 2014-05-30 | Sk Biopharmaceuticals Co Ltd | Treatment of sleep-wake disorders |
| EP1893291B1 (en) * | 2005-06-22 | 2010-03-03 | SK Holdings Co., Ltd. | Treatment of sexual dysfunction |
| KR20090082213A (en) * | 2006-10-13 | 2009-07-29 | 얀센 파마슈티카 엔.브이. | Phenylalkylamino carbamate compositions |
| US8642772B2 (en) | 2008-10-14 | 2014-02-04 | Sk Biopharmaceuticals Co., Ltd. | Piperidine compounds, pharmaceutical composition comprising the same and its use |
| US8741950B2 (en) | 2009-06-22 | 2014-06-03 | Sk Biopharmaceuticals Co., Ltd. | 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 |
| CN102781436B (en) | 2009-11-06 | 2014-01-08 | 爱思开生物制药株式会社 | Methods for treating fibromyalgia syndrome |
| RU2556585C2 (en) * | 2009-11-06 | 2015-07-10 | Ск Биофармасъютиклс Ко., Лтд. | Method of treating attention deficit/hyperactivity syndrome |
| 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 |
| TWI684450B (en) | 2013-03-13 | 2020-02-11 | 南韓商愛思開生物製藥股份有限公司 | Treatment of cataplexy |
| EP3021838B1 (en) | 2013-07-18 | 2020-05-27 | Jazz Pharmaceuticals Ireland Limited | Treatment for obesity |
| TWI655179B (en) | 2014-02-28 | 2019-04-01 | 南韓商愛思開生物製藥股份有限公司 | Aminocarbonyl carbamate compound |
| US10888542B2 (en) | 2014-02-28 | 2021-01-12 | Sk Biopharmaceuticals Co., Ltd. | Aminocarbonylcarbamate compounds |
| DK3509582T3 (en) * | 2016-09-06 | 2024-02-12 | Axsome Malta Ltd | Solvatform af (r)-2-amino-3-phenylpropylcarbamat |
| US10195151B2 (en) * | 2016-09-06 | 2019-02-05 | Jazz Pharmaceuticals International Iii Limited | Formulations of (R)-2-amino-3-phenylpropyl carbamate |
| EP4316592A3 (en) | 2016-10-06 | 2024-05-01 | Axsome Malta Ltd. | Carbamoyl phenylalaninol compounds and uses thereof |
| WO2018133703A1 (en) * | 2017-01-20 | 2018-07-26 | 苏州科睿思制药有限公司 | Crystal form of r228060 hydrochloride and preparation method and use thereof |
| WO2018222954A1 (en) | 2017-06-02 | 2018-12-06 | Jazz Pharmaceuticals International Iii Limited | Methods and compositions for treating excessive sleepiness |
| AU2018312328B2 (en) | 2017-07-31 | 2022-12-15 | Jazz Pharmaceuticals Ireland Limited | Carbamoyl phenylalaninol analogs and uses thereof |
| WO2020035769A1 (en) | 2018-08-14 | 2020-02-20 | Glenmark Pharmaceuticals Limited; Glenmark Life Sciences Limited | Process for the preparation of solriamfetol and salt thereof |
| WO2021001457A1 (en) | 2019-07-04 | 2021-01-07 | Sandoz Ag | Crystalline (r)-2-amino-3-phenylpropylcarbamate acid addition salts |
| US10940133B1 (en) | 2020-03-19 | 2021-03-09 | Jazz Pharmaceuticals Ireland Limited | Methods of providing solriamfetol therapy to subjects with impaired renal function |
| IT202000013855A1 (en) | 2020-06-10 | 2021-12-10 | Flamma Spa | A PROCESS FOR THE PURIFICATION OF (R)-2-AMINO-3-PHENYLPROPYL CARBAMATE |
| KR102390194B1 (en) | 2020-08-03 | 2022-04-25 | 셀라이온바이오메드 주식회사 | A composition for treating Kca3.1 channel mediated diseases comprising phenylalkyl carbamate compounds |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1434826A (en) * | 1973-11-14 | 1976-05-05 | Gallardo Antonio Sa | Esters and carbamates of aminoalkanols |
-
1994
- 1994-09-09 KR KR1019940022798A patent/KR100197892B1/en not_active IP Right Cessation
-
1995
- 1995-09-06 US US08/619,657 patent/US5955499A/en not_active Expired - Lifetime
- 1995-09-06 ES ES95931444T patent/ES2140703T3/en not_active Expired - Lifetime
- 1995-09-06 AU AU34856/95A patent/AU700544B2/en not_active Expired
- 1995-09-06 EP EP95931444A patent/EP0728129B1/en not_active Expired - Lifetime
- 1995-09-06 CN CN95190875A patent/CN1069635C/en not_active Expired - Lifetime
- 1995-09-06 RU RU96113126/04A patent/RU2104266C1/en active
- 1995-09-06 CA CA002176012A patent/CA2176012C/en not_active Expired - Lifetime
- 1995-09-06 JP JP8509386A patent/JP2680478B2/en not_active Expired - Fee Related
- 1995-09-06 WO PCT/KR1995/000114 patent/WO1996007637A1/en active IP Right Grant
- 1995-09-06 DE DE69513140T patent/DE69513140T2/en not_active Expired - Lifetime
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| RU96113126A (en) | CARBAMATES OF PHENYLALKYLAMINOSPIRTS AND METHODS FOR THEIR PRODUCTION | |
| CA2176012A1 (en) | Novel Phenylalkylaminoalcohol Carbamates and Process for Preparing the Same | |
| RU94013439A (en) | HETEROCYCLIC COMPOUNDS, METHOD OF THEIR PRODUCTION, PHARMACEUTICAL COMPOSITION AND METHOD OF TREATMENT | |
| PL353398A1 (en) | Method for the preparation of pure citalopram | |
| CA2378456A1 (en) | Albumin-binding compounds that prevent nonenzymatic glycation and that may be used for treatment of glycation-related pathologies | |
| EP0133170A3 (en) | A compound and a composition for therapeutic or diagnostic use and a method for therapeutic treatment | |
| RU96115166A (en) | ANTI-TRADING SULFAMATS OF PSEVDOFRUCTOPIRANOSE | |
| RU96107890A (en) | INTERMEDIATE PRODUCT AND ITS USE IN SYNTHESIS | |
| DE69233249D1 (en) | Process for the preparation of a 3-cephem-4-carboxylic acid derivative | |
| RU99128028A (en) | CYANOGUANIDINES AS CELL GROWTH INHIBITORS | |
| PT85972A (en) | METHOD FOR PRODUCING A BREAKAGE GRANULATE AND BREWING GRANULATED THEREOF AND USE THEREOF | |
| DE69206607D1 (en) | TREATMENT OF COGNITIVE DISORDERS. | |
| EP1415985A4 (en) | Process for producing optically active azetidine-2-carboxylic acid | |
| ATE168987T1 (en) | IMPROVED PROCESS FOR PRODUCING PROPARGYL AMMONIUM CHLORIDE DERIVATIVES | |
| DE50306068D1 (en) | PROCESS FOR PRODUCING SALTS OF TOLPERISON | |
| EP0759425A3 (en) | Process for the preparation of optically active 1-aryl-alkylamines | |
| EP0214550B1 (en) | Process for the preparation of aspartame and agent for its preparation | |
| EP0985414A3 (en) | Method of treating glaucoma and ischemic retinopathy | |
| RU2000126720A (en) | METHOD FOR PROCESSING ALLOYED METAL PLUTONIUM | |
| IE781561L (en) | Geminally disubstituted indenes. | |
| SU1574605A1 (en) | Aluminium sulphate complexes with derivatives of ethanolamine as tanners of natural skins | |
| RU97104544A (en) | IMPROVED METHOD FOR OBTAINING SULFONYL ISOCYANATES | |
| PL340685A1 (en) | Method of obtaining n2-(1(s)-carboxy-3-phenylpropyl)-l-lysil-l-proline | |
| JPS5721399A (en) | Fortimicin a derivative and its preparation | |
| SU1503250A1 (en) | METHOD OF CLEANING METHYL CHLOROFORM |