HRP20161145T1 - Postupak za pripravu l-argininske soli perindoprila - Google Patents
Postupak za pripravu l-argininske soli perindoprila Download PDFInfo
- Publication number
- HRP20161145T1 HRP20161145T1 HRP20161145TT HRP20161145T HRP20161145T1 HR P20161145 T1 HRP20161145 T1 HR P20161145T1 HR P20161145T T HRP20161145T T HR P20161145TT HR P20161145 T HRP20161145 T HR P20161145T HR P20161145 T1 HRP20161145 T1 HR P20161145T1
- Authority
- HR
- Croatia
- Prior art keywords
- perindopril
- preparation
- arginine salt
- arginine
- formula
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 9
- 238000002360 preparation method Methods 0.000 title claims 7
- IPVQLZZIHOAWMC-QXKUPLGCSA-N perindopril Chemical compound C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 IPVQLZZIHOAWMC-QXKUPLGCSA-N 0.000 title claims 6
- 229960002582 perindopril Drugs 0.000 title claims 6
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical class OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 title claims 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 6
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical group C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims 6
- RYCSJJXKEWBUTI-YDYAIEMNSA-N perindopril arginine Chemical compound OC(=O)[C@@H](N)CCCNC(N)=N.C1CCC[C@H]2C[C@@H](C(O)=O)N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H]21 RYCSJJXKEWBUTI-YDYAIEMNSA-N 0.000 claims 6
- AUVAVXHAOCLQBF-UHFFFAOYSA-N 2-[(1-ethoxy-1-oxopentan-2-yl)azaniumyl]propanoate Chemical compound OC(=O)C(C)NC(CCC)C(=O)OCC AUVAVXHAOCLQBF-UHFFFAOYSA-N 0.000 claims 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims 3
- 229930064664 L-arginine Natural products 0.000 claims 3
- 235000014852 L-arginine Nutrition 0.000 claims 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims 3
- 230000003213 activating effect Effects 0.000 claims 3
- 238000006243 chemical reaction Methods 0.000 claims 3
- 239000003795 chemical substances by application Substances 0.000 claims 3
- 239000000203 mixture Substances 0.000 claims 3
- CQYBNXGHMBNGCG-FXQIFTODSA-N (2s,3as,7as)-2,3,3a,4,5,6,7,7a-octahydro-1h-indol-1-ium-2-carboxylate Chemical compound C1CCC[C@@H]2[NH2+][C@H](C(=O)[O-])C[C@@H]21 CQYBNXGHMBNGCG-FXQIFTODSA-N 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- 150000008535 L-arginines Chemical class 0.000 claims 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- YHNUDLCUIKMNSN-UHFFFAOYSA-N bis(1,2,4-triazol-1-yl)methanone Chemical compound C1=NC=NN1C(=O)N1C=NC=N1 YHNUDLCUIKMNSN-UHFFFAOYSA-N 0.000 claims 1
- PFYXSUNOLOJMDX-UHFFFAOYSA-N bis(2,5-dioxopyrrolidin-1-yl) carbonate Chemical compound O=C1CCC(=O)N1OC(=O)ON1C(=O)CCC1=O PFYXSUNOLOJMDX-UHFFFAOYSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 claims 1
- 238000010612 desalination reaction Methods 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- IYNMDWMQHSMDDE-MHXJNQAMSA-N perindopril erbumine Chemical compound CC(C)(C)N.C1CCC[C@@H]2N(C(=O)[C@H](C)N[C@@H](CCC)C(=O)OCC)[C@H](C(O)=O)C[C@@H]21 IYNMDWMQHSMDDE-MHXJNQAMSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- UCPYLLCMEDAXFR-UHFFFAOYSA-N triphosgene Chemical compound ClC(Cl)(Cl)OC(=O)OC(Cl)(Cl)Cl UCPYLLCMEDAXFR-UHFFFAOYSA-N 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/42—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- 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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
- A61K31/403—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil condensed with carbocyclic rings, e.g. carbazole
- A61K31/404—Indoles, e.g. pindolol
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/04—Inotropic agents, i.e. stimulants of cardiac contraction; Drugs for heart failure
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C277/00—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups
- C07C277/08—Preparation of guanidine or its derivatives, i.e. compounds containing the group, the singly-bound nitrogen atoms not being part of nitro or nitroso groups of substituted guanidines
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Vascular Medicine (AREA)
- Urology & Nephrology (AREA)
- Hospice & Palliative Care (AREA)
- Epidemiology (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Indole Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Claims (6)
1. Postupak za pripravu perindopril L-argininske soli formule (I):
[image]
naznačen time, da se sastoji od reakcije između perindoprila i L-arginina u sustavu otapala koji je odabran od:
binarne mješavine acetonitrila i dimetil sulfoksida,
binarne mješavine etil acetata i dimetil sulfoksida,
trodjelne mješavine acetonitrila, dimetil sulfoksida i toluena,
pri temperaturi od 10 do 100°C,
nakon čega slijedi izolazija putem filtracije tako dobivene L-argininske soli.
2. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 1, naznačen time, da je perindopril dobiven reakcijom N-[1-(S)-etoksikarbonil-butil]-(S)-alanina formule (II):
[image]
sa sredstvom za aktiviranje formule X2C=O pri čemu X predstavlja odlazeću skupinu, u organskom otapalu ili sustavu organskih otapala, pri temperaturi od -20 do 80°C,
uz reakciju tako dobivenog intermedijernog spoja formule (III):
[image]
sa (2S, 3aS, 7aS)-2-karboksiperhidroindolom pri temperaturi od 0 do 80°C, a potom tako dobiveni perindopril reagira s L-argininom iz postupka prema patentnom zahtjevu 1.
3. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 2, naznačen time, da je sredstvo za aktiviranje N,N’-karbonildiimidazol, fosgen, trifosgen, (1,1’-karbonildi(1,2,4-triazol) ili di(N-sukcinimidil) karbonat.
4. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 3, naznačen time, da je sredstvo za aktivaciju N,N’-karbonildiimidazol, a količina N,N’-karbonildiimidazola je između 0.8 i 1.2 mola, uključeno, po molu od N-[1-(S)-etoksikarbonil-butil]-(S)-alanina.
5. Postupak za pripravu perindopril L-argininske soli prema bilo kojem od patentnih zahtjeva 2 do 4, naznačen time, da je količina (2S, 3aS, 7aS)-2-karboksiperhidroindola između 0.8 i 1.2 mola, uključujući, po molu od N-[1- (S)-etoksikarbonil-butil]-(S)-alanina.
6. Postupak za pripravu perindopril L-argininske soli prema patentnom zahtjevu 1, naznačen time, da je perindopril dobiven desalinizacijom perindopril terc-butilamina djelovanjem kiseline, a potom tako dobiveni perindopril reagira L-argininom prema postupku iz patentnog zahtjeva 1.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR1200034A FR2985512B1 (fr) | 2012-01-05 | 2012-01-05 | Procede de preparation du sel de l-arginine du perindopril |
| EP13150305.4A EP2612851B1 (fr) | 2012-01-05 | 2013-01-04 | Procédé de préparation du sel de l-arginine du périndopril |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20161145T1 true HRP20161145T1 (hr) | 2016-11-18 |
Family
ID=47427278
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20161145TT HRP20161145T1 (hr) | 2012-01-05 | 2016-09-06 | Postupak za pripravu l-argininske soli perindoprila |
Country Status (46)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016178591A2 (en) | 2015-05-05 | 2016-11-10 | Gene Predit, Sa | Genetic markers and treatment of male obesity |
| TWI544987B (zh) | 2015-10-27 | 2016-08-11 | 財團法人工業技術研究院 | 輕便型動力工具 |
| WO2019071209A1 (en) | 2017-10-06 | 2019-04-11 | Rad Steve | SYSTEM AND KIT OF INCREASED REALITY |
| US10430658B2 (en) | 2017-10-06 | 2019-10-01 | Steve Rad | Augmented reality system and kit |
| CN110283104B (zh) * | 2018-08-22 | 2022-06-14 | 南京济群医药科技股份有限公司 | 一种精氨酸培哚普利的制备方法 |
| CN112047999B (zh) * | 2020-09-18 | 2022-12-02 | 天津力生制药股份有限公司 | 一种γ晶型的精氨酸培哚普利盐的制备方法 |
| CN114149357B (zh) * | 2021-12-29 | 2024-06-25 | 江苏嘉逸医药有限公司 | 一种γ晶型培哚普利精氨酸盐的制备方法 |
| CN114894940A (zh) * | 2022-06-02 | 2022-08-12 | 江苏嘉逸医药有限公司 | 一种高效液相色谱法测定精氨酸培哚普利中杂质的方法 |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2503155A2 (fr) * | 1980-10-02 | 1982-10-08 | Science Union & Cie | Nouveaux imino diacides substitues, leurs procedes de preparation et leur emploi comme inhibiteur d'enzyme |
| FR2620709B1 (fr) * | 1987-09-17 | 1990-09-07 | Adir | Procede de synthese industrielle du perindopril et de ses principaux intermediaires de synthese |
| AR036187A1 (es) * | 2001-07-24 | 2004-08-18 | Adir | Un proceso para la preparacion de perindopril, compuestos analogos y sus sales, compuesto intermediario 2,5-dioxo-oxazolidina y proceso para preparar un intermediario |
| FR2838648B1 (fr) * | 2002-04-18 | 2004-05-21 | Servier Lab | Nouveau sel de perindopril et les compositions pharmaceutiques qui le contiennent |
| WO2005026845A1 (en) | 2003-09-18 | 2005-03-24 | Research Laboratories Of Australia Pty Ltd | Marking liquid method of preparation and product produced thereby |
| US7291745B2 (en) * | 2005-03-21 | 2007-11-06 | Glenmark Pharmaceuticals Limited | Process for the preparation of perindopril |
| FR2897865B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline beta du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| FR2897866B1 (fr) * | 2006-02-28 | 2008-04-18 | Servier Lab | Forme cristalline alpha du sel d'arginine du perindopril, son procede de preparation, et les compositions pharmaceutiques qui la contiennent |
| EP1864973A1 (en) * | 2006-06-09 | 2007-12-12 | Sochinaz SA | Process for the preparation of perindopril and salts thereof |
| DK2318365T3 (en) * | 2008-06-24 | 2015-11-23 | Mylan Lab Ltd | NOVEL polymorphic forms of perindopril (L) -arginine AND PROCESS FOR PREPARATION THEREOF |
| AU2009212902A1 (en) | 2008-09-03 | 2010-03-18 | Apotex Pharmachem Inc. | Amorphous form of an L-arginine salt of perindopril and processes of preparation thereof |
| SI23001A (sl) * | 2009-03-20 | 2010-09-30 | Diagen@d@o@o | Nove soli perindoprila nov postopek za njihovo pripravo in njihova uporaba za zdravljenje kardiovaskularnih bolezni |
-
2012
- 2012-01-05 FR FR1200034A patent/FR2985512B1/fr not_active Expired - Fee Related
- 2012-12-18 PH PH12012000392A patent/PH12012000392B1/en unknown
- 2012-12-19 JO JOP/2012/0384A patent/JO3196B1/ar active
- 2012-12-19 SG SG2012093589A patent/SG192337A1/en unknown
- 2012-12-19 CR CR20120654A patent/CR20120654A/es unknown
- 2012-12-20 AU AU2012268816A patent/AU2012268816B2/en active Active
- 2012-12-20 IL IL223753A patent/IL223753A/en active IP Right Grant
- 2012-12-20 PE PE2012002463A patent/PE20131098A1/es not_active Application Discontinuation
- 2012-12-25 TN TNP2012000620A patent/TN2012000620A1/fr unknown
- 2012-12-26 CO CO12232909A patent/CO6700138A1/es unknown
- 2012-12-27 NI NI201200195A patent/NI201200195A/es unknown
- 2012-12-27 TW TW101150662A patent/TWI449693B/zh active
- 2012-12-27 MY MYPI2012701295A patent/MY160902A/en unknown
- 2012-12-27 UY UY0001034553A patent/UY34553A/es unknown
- 2012-12-28 MD MDA20120129A patent/MD4415C1/ro active IP Right Grant
- 2012-12-28 EA EA201201667A patent/EA022573B1/ru unknown
-
2013
- 2013-01-02 MA MA35525A patent/MA35001B1/fr unknown
- 2013-01-02 AP AP2013006655A patent/AP2013006655A0/xx unknown
- 2013-01-02 SA SA113340172A patent/SA113340172B1/ar unknown
- 2013-01-03 US US13/733,353 patent/US8865915B2/en active Active
- 2013-01-03 UA UAA201300118A patent/UA111333C2/uk unknown
- 2013-01-03 CL CL2013000022A patent/CL2013000022A1/es unknown
- 2013-01-03 CA CA 2801089 patent/CA2801089C/fr active Active
- 2013-01-03 AR ARP130100016A patent/AR089632A1/es not_active Application Discontinuation
- 2013-01-04 CU CUP2013000003A patent/CU24293B1/xx unknown
- 2013-01-04 GE GEAP201312951A patent/GEP20146183B/en unknown
- 2013-01-04 KR KR1020130001012A patent/KR101502946B1/ko active IP Right Grant
- 2013-01-04 PT PT131503054T patent/PT2612851T/pt unknown
- 2013-01-04 HU HUE13150305A patent/HUE030042T2/en unknown
- 2013-01-04 DK DK13150305.4T patent/DK2612851T3/en active
- 2013-01-04 LT LTEP13150305.4T patent/LT2612851T/lt unknown
- 2013-01-04 ES ES13150305.4T patent/ES2595236T3/es active Active
- 2013-01-04 BR BR102013000256-9A patent/BR102013000256B1/pt active IP Right Grant
- 2013-01-04 WO PCT/FR2013/050017 patent/WO2013102740A1/fr active Application Filing
- 2013-01-04 JP JP2013000108A patent/JP5722924B2/ja active Active
- 2013-01-04 SI SI201330308A patent/SI2612851T1/sl unknown
- 2013-01-04 EC ECSP13012366 patent/ECSP13012366A/es unknown
- 2013-01-04 ME MEP-2016-171A patent/ME02493B/me unknown
- 2013-01-04 CN CN201310001282.2A patent/CN103193863B/zh active Active
- 2013-01-04 GT GT201300002A patent/GT201300002A/es unknown
- 2013-01-04 PL PL13150305.4T patent/PL2612851T3/pl unknown
- 2013-01-04 EP EP13150305.4A patent/EP2612851B1/fr active Active
- 2013-01-04 RS RS20160720A patent/RS55096B1/sr unknown
- 2013-01-07 MX MX2013000009A patent/MX2013000009A/es active IP Right Grant
-
2016
- 2016-09-06 HR HRP20161145TT patent/HRP20161145T1/hr unknown
- 2016-10-05 CY CY20161100993T patent/CY1118079T1/el unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| HRP20161145T1 (hr) | Postupak za pripravu l-argininske soli perindoprila | |
| ES2567047T3 (es) | Derivados de pirimidina anti-virales | |
| UA115043C2 (uk) | Амідні похідні n-карбамідзаміщених амінокислот як модулятори формілпептидного рецептора 1 (fprl-1) | |
| WO2013184476A3 (en) | Processes to produce certain 2-(pyridine-3-yl)thiazoles | |
| WO2020016749A3 (en) | Chemical process for preparing phenylpiperidinyl indole derivatives | |
| CL2011000845A1 (es) | Uso de dl-metionil-dl-metionina y sus sales como aditivo para productos alimenticios para animales mantenidos en cultivos marinos; mezcla de alimentos que lo comprende; procedimiento para la preparacion de dl-metionil-dl-metionina; procedimiento para la aislacion de la mezcla de diasteromeros de dd/ll/dl/ld- metionilmetionina y procedimiento para la disociacion de la mezcla de diasteromeros de dd/ll/dl/ld-metionilmetionina. | |
| AR091044A1 (es) | Derivados dipeptidos de lisina-acido glutamico | |
| HRP20210321T1 (hr) | Postupak za pročišćavanje pirazolpiridazina | |
| CN104926796A (zh) | 一种新的ns5a抑制剂药物的制备方法 | |
| WO2019229376A3 (fr) | Procede de purification du sel de lithium de bis(fluorosulfonyl)imide | |
| DE602007013796D1 (de) | Ausstossflüssigkeit und ausstossverfahren | |
| Dusek et al. | Synthesis and antiproliferative activities of novel O-benzyl salicylamide derivatives | |
| WO2013024358A3 (en) | Substituted heterocyclic amine compounds as cholestryl ester-transfer protein (cetp) inhibitors | |
| RU2006125090A (ru) | Противовоспалительное средство для наружного применения | |
| RU2013106503A (ru) | Способ получения контрастных агентов | |
| ES2624961T3 (es) | Síntesis de productos de péptido que contienen imida cíclica | |
| ES2473271T3 (es) | Proceso de preparación de dimiracetam | |
| Rao et al. | A NOVEL SYNTHESIS OF 4-(5-SUBSTITUTED AMINOMETHYL)-1H-TETRAZOL-1-YL) BENZONITRILES | |
| Suyoga Vardhan et al. | Synthesis and urease inhibition studies of ureas and thioureas derived from amino acids conjugated heterocycle | |
| Krasikovs et al. | Iodoacetic acid is an efficient reagent for the synthesis of amino acid derived 2-aminobenzimidazoles | |
| Polygalova et al. | Synthesis of Amino Acid Esters: Derivatives of 1, 2, 3, 4-Tetrahydroisoquinoline. | |
| Risseeuw et al. | Sugar amino acid based peptide epoxyketones as potential proteasome inhibitors | |
| MX2018001548A (es) | Procedimiento para la preparacion del compuesto n-(3,5-dimetilfenil)-n'-(2-trifluorometilfenil) guanidina. | |
| HRP20140839T1 (hr) | Postupak sinteze ivabradina i njegovih adicijskih soli i farmaceutski prihvatljivih kiselina | |
| CN105315178B (zh) | 达芦那韦相关物质及其制备方法 |