ES2657676T3 - Proceso para la preparación de derivados de l-alanina protegidos - Google Patents
Proceso para la preparación de derivados de l-alanina protegidos Download PDFInfo
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- ES2657676T3 ES2657676T3 ES09752026.6T ES09752026T ES2657676T3 ES 2657676 T3 ES2657676 T3 ES 2657676T3 ES 09752026 T ES09752026 T ES 09752026T ES 2657676 T3 ES2657676 T3 ES 2657676T3
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- pharmaceutically acceptable
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- 238000000034 method Methods 0.000 title abstract description 4
- QNAYBMKLOCPYGJ-REOHCLBHSA-N L-alanine Chemical class C[C@H](N)C(O)=O QNAYBMKLOCPYGJ-REOHCLBHSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract description 19
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract description 10
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 abstract description 8
- 239000003960 organic solvent Substances 0.000 abstract description 8
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 7
- 239000011701 zinc Substances 0.000 abstract description 6
- 229910052725 zinc Inorganic materials 0.000 abstract description 6
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract description 5
- 229910052740 iodine Inorganic materials 0.000 abstract description 5
- 239000011630 iodine Substances 0.000 abstract description 5
- 239000003054 catalyst Substances 0.000 abstract description 4
- 229910052763 palladium Inorganic materials 0.000 abstract description 4
- 229910000073 phosphorus hydride Inorganic materials 0.000 abstract description 4
- -1 formylamino Chemical group 0.000 abstract description 3
- 239000003446 ligand Substances 0.000 abstract description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 3
- 125000001246 bromo group Chemical group Br* 0.000 abstract description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 4
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 125000003118 aryl group Chemical group 0.000 abstract 3
- 125000005196 alkyl carbonyloxy group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 abstract 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 abstract 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000006517 heterocyclyl carbonyl group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- CYPYTURSJDMMMP-WVCUSYJESA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].[Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 CYPYTURSJDMMMP-WVCUSYJESA-N 0.000 description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/14—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof
- C07C227/16—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton from compounds containing already amino and carboxyl groups or derivatives thereof by reactions not involving the amino or carboxyl groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/06—Preparation of carboxylic acid amides from nitriles by transformation of cyano groups into carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/12—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of acyclic carbon skeletons
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/14—Preparation of carboxylic acid amides by formation of carboxamide groups together with reactions not involving the carboxamide groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/64—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings
- C07C233/65—Carboxylic acid amides having carbon atoms of carboxamide groups bound to carbon atoms of six-membered aromatic rings having the nitrogen atoms of the carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C237/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups
- C07C237/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton
- C07C237/42—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by amino groups having the carbon atom of at least one of the carboxamide groups bound to a carbon atom of a non-condensed six-membered aromatic ring of the carbon skeleton having nitrogen atoms of amino groups bound to the carbon skeleton of the acid part, further acylated
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/16—Preparation of carboxylic acid nitriles by reaction of cyanides with lactones or compounds containing hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C269/00—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C269/06—Preparation of derivatives of carbamic acid, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups by reactions not involving the formation of carbamate groups
-
- 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
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/10—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/22—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to carbon atoms of hydrocarbon radicals substituted by carboxyl groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C303/00—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides
- C07C303/26—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids
- C07C303/28—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of esters of sulfonic acids by reaction of hydroxy compounds with sulfonic acids or derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/06—Zinc compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Toxicology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Catalysts (AREA)
Abstract
Un procedimiento para la preparación de un compuesto de fórmula (I) **(Ver fórmula)** donde PG1 es un grupo protector de nitrógeno; R0 se selecciona del grupo que consiste en hidrógeno, alquilo C1-4 y bencilo; R6 se selecciona del grupo que consiste en hidrógeno y alquilo C1-6; R4 es arilo; en el que el arilo está opcionalmente sustituido con uno a cinco sustituyentes seleccionados independientemente del grupo que consiste en alquilo C1-6, alcoxi C1-6, ariloC1-6alkoxy, ariloC1-6alquilcarboniloxi, heteroariloC1-6alquilcarboniloxi, heteroarilo, hidroxi, halógeno, aminosulfonilo, formilamino, aminocarbonilo, C1- 6alquilaminocarbonilo, di(alquilo C1-6)aminocarbonilo, heterociclilcarbonilo, carboxi y ciano; en el que el alquilo C1- 6 está opcionalmente sustituido con amino, alquilamino C1-6, o 2amino (alquilo C1-6); y en el que la porción de arilo de ariloC1-6alquilcarboniloxi está opcionalmente sustituido con uno a cuatro sustituyentes seleccionados independientemente entre el grupo que consiste en alquilo C1-6, alcoxi C1-6, halógeno, ciano, amino e hidroxi; y enantiómeros farmacéuticamente aceptables, diastereómeros farmacéuticamente aceptables, racematos farmacéuticamente aceptables y sal farmacéuticamente aceptable de los mismos; comprendiendo **(Ver fórmula)** reaccionar un compuesto de fórmula (X), en el que PG1 es un grupo protector de nitrógeno, con el zinc; en presencia de una fuente de yodo; en un primer disolvente orgánico, o una mezcla de disolventes orgánicos en el que el primer disolvente orgánico es no reactivo para el yodo fuente; para producir el compuesto correspondiente de fórmula (XI); **(Ver fórmula)** hacer reaccionar el compuesto de fórmula (XI) con un compuesto de fórmula (XII), en donde LG1 es un grupo bromo; en presencia de un catalizador de paladio y el sistema de ligando de fosfina; en un segundo disolvente orgánico o una mezcla de disolventes orgánicos; para producir el compuesto correspondiente de fórmula (I).
Description
10
Esquema 1
[0053] Por consiguiente, un compuesto adecuadamente sustituido de fórmula (X), un compuesto conocido o un compuesto preparado por métodos conocidos, en el que PG1 es un grupo protector de nitrógeno adecuadamente 15 seleccionado tal como Boc, Cbz, y similares, preferiblemente Boc; se hace reaccionar con zinc, preferentemente polvo de zinc; en el que el zinc está presente preferiblemente en una cantidad en el intervalo de 0,5 a 3,0 equivalentes molares, más preferiblemente presente en una cantidad en el intervalo de 0,5 a 1,5 equivalentes molares, más preferiblemente aproximadamente 1,1 equivalentes molares; en presencia de una fuente de yodo, preferiblemente yodo; en el que la fuente de yodo está presente preferiblemente en una cantidad en el intervalo de 20 0,1 a 1,0 equivalentes molares, más preferiblemente en una cantidad en el intervalo de 0,1 a 0,5 equivalentes molares, más preferiblemente aproximadamente 0,3 equivalentes molares, más preferiblemente en una cantidad catalítica suficiente para activar el zinc; en un primer disolvente orgánico o mezcla de los mismos, en el que el primer disolvente orgánico es no reactivo para el yodo fuente, tal como, DMAc, una mezcla de DMAc y 2-metilo-THF, THF, tolueno, y DMF, más preferiblemente DMAc; preferiblemente a una temperatura en el intervalo de -20°C a 10°C, más
25 preferiblemente a una temperatura de menos de aproximadamente 10°C, más preferiblemente a aproximadamente -8°C; para producir el compuesto correspondiente de fórmula (XI). Preferiblemente, no se aísla el compuesto de fórmula (XI). Preferentemente, el zinc y la fuente de yodo se mezclan antes de la adición al compuesto de fórmula (X), para activar el zinc.
30 [0054] El compuesto de fórmula (XI) se hace reaccionar con un compuesto adecuadamente sustituido de fórmula (XII), en donde LG1 es Br; en el que el compuesto de fórmula (XII) está presente preferiblemente en una cantidad en el intervalo de 0,1 a 3,0 equivalentes molares, más preferiblemente en una cantidad en el intervalo de 0,25 a 1,0 equivalentes molares, más preferiblemente en una cantidad en el intervalo de de 0,5 a 1,1 equivalentes molares; en presencia de un sistema catalizador de paladio y el ligando de fosfina tal como Pd2(dba)3 en combinación con P(o
35 tol)3, cloruro de paladio en combinación con PPh3, Pd(PPh3)2Cl2, Pd(PPh3)4, y similares, más preferiblemente Pd2(dba)3 en combinación con P(o-tol)3, en el que el catalizador de paladio y el sistema de ligando de fosfina está presente preferiblemente en una cantidad catalítica; en un segundo disolvente orgánico o mezcla de los mismos tales como, DMAc, una mezcla de DMAc y 2-metilo-THF, THF, DMF, y tolueno, más preferiblemente DMAc; preferiblemente en el mismo disolvente que se utiliza en el paso anterior; preferiblemente a una temperatura en el
40 intervalo de 50°C a 100°C, más preferiblemente a aproximadamente 80°C; para producir el compuesto correspondiente de fórmula (I). Preferiblemente, se añade el compuesto de fórmula (XI) a una mezcla del compuesto de fórmula (XII), el catalizador de paladio y el agente de fosfina.
[0055] La presente invención se dirige además a un procedimiento para la preparación de un compuesto de fórmula 45 (I-A) como se describe en más detalle en el Esquema 2, a continuación, en donde LG1 es un grupo bromo.
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Claims (1)
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imagen1 imagen2 imagen3
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10864908P | 2008-10-27 | 2008-10-27 | |
| US108649P | 2008-10-27 | ||
| PCT/US2009/062191 WO2010062590A2 (en) | 2008-10-27 | 2009-10-27 | Process for the preparation of protected l-alanine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES2657676T3 true ES2657676T3 (es) | 2018-03-06 |
Family
ID=41796530
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES09752026.6T Active ES2657676T3 (es) | 2008-10-27 | 2009-10-27 | Proceso para la preparación de derivados de l-alanina protegidos |
Country Status (25)
| Country | Link |
|---|---|
| US (3) | US8710256B2 (es) |
| EP (1) | EP2362868B1 (es) |
| JP (2) | JP5592893B2 (es) |
| KR (1) | KR101690195B1 (es) |
| CN (2) | CN107382781A (es) |
| AR (1) | AR075291A1 (es) |
| AU (1) | AU2009320156B2 (es) |
| BR (1) | BRPI0920834B1 (es) |
| CA (1) | CA2741790C (es) |
| CL (1) | CL2011000936A1 (es) |
| CO (1) | CO6361989A2 (es) |
| CR (1) | CR20110286A (es) |
| EA (1) | EA018913B1 (es) |
| EC (1) | ECSP11011008A (es) |
| ES (1) | ES2657676T3 (es) |
| HN (1) | HN2011001186A (es) |
| HU (1) | HUE038302T2 (es) |
| IL (1) | IL212464A (es) |
| MX (1) | MX2011004393A (es) |
| NI (1) | NI201100078A (es) |
| NZ (1) | NZ592415A (es) |
| PE (2) | PE20110417A1 (es) |
| TW (1) | TWI468375B (es) |
| UA (1) | UA110600C2 (es) |
| WO (1) | WO2010062590A2 (es) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TWI468375B (zh) * | 2008-10-27 | 2015-01-11 | Janssen Pharmaceutica Nv | 製備經保護之ｌ－丙胺酸衍生物之方法 |
| EP3974563A1 (en) | 2011-12-28 | 2022-03-30 | Chugai Seiyaku Kabushiki Kaisha | Cyclic peptides |
| BR112016017997A2 (pt) | 2014-02-03 | 2017-08-08 | Quadriga Biosciences Inc | Beta aminoácidos beta-substituídos e análogos como agentes quimioterapêuticos |
| WO2015117146A1 (en) | 2014-02-03 | 2015-08-06 | Quadriga Biosciences, Inc. | Beta-substituted gamma-amino acids and analogs as chemotherapeutic agents |
| JP7020910B2 (ja) | 2015-03-13 | 2022-02-16 | 中外製薬株式会社 | 改変アミノアシルｔＲＮＡ合成酵素およびその用途 |
| EP3331851A1 (en) | 2015-08-03 | 2018-06-13 | Quadriga Biosciences, Inc. | Beta-substituted beta-amino acids and analogs as chemotherapeutic agents and uses thereof |
| WO2017043626A1 (ja) * | 2015-09-11 | 2017-03-16 | 株式会社カネカ | 光学活性４－カルバモイル－２，６－ジメチルフェニルアラニン誘導体の製造法 |
| CN105777584B (zh) * | 2016-03-28 | 2018-01-02 | 成都伊诺达博医药科技有限公司 | 丙氨酸衍生物的制备方法 |
| CN105693554B (zh) * | 2016-04-06 | 2017-08-08 | 成都伊诺达博医药科技有限公司 | 丙氨酸衍生物的制备方法 |
| EP3515434A4 (en) | 2016-09-20 | 2020-02-26 | Sun Pharmaceutical Industries Limited | PROCESSES FOR THE PREPARATION OF ELUXADOLINE |
| CN106636241B (zh) * | 2016-12-28 | 2020-04-03 | 尚科生物医药（上海）有限公司 | 一种酶法制备艾沙度林中间体的方法 |
| CN106636246B (zh) * | 2016-12-28 | 2020-03-24 | 尚科生物医药（上海）有限公司 | 生物法制备(s)-1-(5-苯基-1h-咪唑-2-基)乙胺 |
| CN106866463B (zh) * | 2017-01-24 | 2018-08-28 | 富乐马鸿凯（大连）医药有限公司 | 艾沙度林中间体的制备方法 |
| WO2018143145A1 (ja) | 2017-01-31 | 2018-08-09 | 中外製薬株式会社 | 無細胞翻訳系におけるペプチドの合成方法 |
| US11542299B2 (en) | 2017-06-09 | 2023-01-03 | Chugai Seiyaku Kabushiki Kaisha | Method for synthesizing peptide containing N-substituted amino acid |
| JP7411414B2 (ja) | 2017-12-15 | 2024-01-11 | 中外製薬株式会社 | ペプチドの製造方法、及び塩基の処理方法 |
| CN110092735B (zh) * | 2018-01-31 | 2021-05-11 | 尚科生物医药（上海）有限公司 | 一种l-丙氨酸衍生物的制备方法 |
| WO2019197274A1 (en) | 2018-04-09 | 2019-10-17 | Quimica Sintetica, S. A. | Process for the preparation of opioid modulators |
| KR20250119653A (ko) | 2018-11-07 | 2025-08-07 | 추가이 세이야쿠 가부시키가이샤 | O-치환 세린 유도체의 제조 방법 |
| EP3889164A4 (en) | 2018-11-30 | 2022-11-02 | Chugai Seiyaku Kabushiki Kaisha | METHOD FOR DEPROTECTION AND METHOD FOR RESIN REMOVAL IN A SOLID PHASE REACTION OF A PEPTIDE COMPOUND OR AN AMIDE COMPOUND, AND METHOD FOR PRODUCTION OF A PEPTIDE COMPOUND |
| JP7472101B2 (ja) | 2019-03-15 | 2024-04-22 | 中外製薬株式会社 | 芳香族アミノ酸誘導体の製造方法 |
| JP6880352B1 (ja) | 2019-11-07 | 2021-06-02 | 中外製薬株式会社 | Ｋｒａｓ阻害作用を有する環状ペプチド化合物 |
| CN111620876B (zh) * | 2020-05-07 | 2021-09-28 | 普济生物科技（台州）有限公司 | 瑞德西韦关键中间体的合成方法 |
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| JP2780372B2 (ja) | 1989-08-29 | 1998-07-30 | 株式会社日立製作所 | デイスク制御装置のキヤツシユ組込制御方法 |
| JP2881473B2 (ja) * | 1990-03-30 | 1999-04-12 | 日産化学工業株式会社 | α―置換シクロペンテノン誘導体及びその製造法並びに該誘導体を得るための有機亜鉛試剤 |
| US5554753A (en) | 1993-08-25 | 1996-09-10 | Indiana University Foundation | Catalytic enantioselective synthesis of α-amino acid derivatives by phase-transfer catalysis |
| SE9402880D0 (sv) | 1994-08-30 | 1994-08-30 | Astra Ab | New peptide derivatives |
| JP4228587B2 (ja) * | 2002-05-22 | 2009-02-25 | 昭和電工株式会社 | アミノメチル基含有ベンズアミド化合物の製造方法 |
| US7230137B2 (en) * | 2002-12-04 | 2007-06-12 | Ciba Specialty Chemicals Corp. | Process for the synthesis of cycloorganylphosphanes and di(alkyli metal/alkaline earth metal) oligophosphanediides |
| UA86053C2 (ru) * | 2004-03-15 | 2009-03-25 | Янссен Фармацевтика Н.В. | Соединения как модуляторы опиоидных рецепторов |
| BRPI0607792A2 (pt) * | 2005-03-14 | 2009-06-13 | Janssen Pharmaceutica Nv | processo para a preparação de moduladores de opióides |
| TWI468375B (zh) * | 2008-10-27 | 2015-01-11 | Janssen Pharmaceutica Nv | 製備經保護之ｌ－丙胺酸衍生物之方法 |
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