AR056919A1 - SíNTESIS EXO- Y DIASTEREO- SELECTIVAS DE ANÁLOGOS DE HIMBACINA - Google Patents
SíNTESIS EXO- Y DIASTEREO- SELECTIVAS DE ANÁLOGOS DE HIMBACINAInfo
- Publication number
- AR056919A1 AR056919A1 ARP060100127A ARP060100127A AR056919A1 AR 056919 A1 AR056919 A1 AR 056919A1 AR P060100127 A ARP060100127 A AR P060100127A AR P060100127 A ARP060100127 A AR P060100127A AR 056919 A1 AR056919 A1 AR 056919A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- mixture
- produce
- nitro
- isomer
- Prior art date
Links
- FMPNFDSPHNUFOS-LPJDIUFZSA-N himbacine Chemical class C(/[C@@H]1[C@H]2CCCC[C@@H]2C[C@@H]2C(=O)O[C@H]([C@H]12)C)=C\[C@H]1CCC[C@H](C)N1C FMPNFDSPHNUFOS-LPJDIUFZSA-N 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 2
- 150000000644 6-membered heterocyclic compounds Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 229940125898 compound 5 Drugs 0.000 abstract 1
- 230000001351 cycling effect Effects 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 238000006345 epimerization reaction Methods 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 abstract 1
- 239000003856 thrombin receptor antagonist Substances 0.000 abstract 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
- C07D263/54—Benzoxazoles; Hydrogenated benzoxazoles
- C07D263/56—Benzoxazoles; Hydrogenated benzoxazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
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- 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
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/10—Preparation of nitro compounds by substitution of functional groups by nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C201/00—Preparation of esters of nitric or nitrous acid or of compounds containing nitro or nitroso groups bound to a carbon skeleton
- C07C201/06—Preparation of nitro compounds
- C07C201/12—Preparation of nitro compounds by reactions not involving the formation of nitro groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/44—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by —CHO groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/55—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups or carboxyl groups bound to carbon atoms of rings other than six-membered aromatic rings of the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/10—Preparation of carboxylic acid amides from compounds not provided for in groups C07C231/02 - C07C231/08
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C235/00—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms
- C07C235/02—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C235/28—Carboxylic acid amides, the carbon skeleton of the acid part being further substituted by oxygen atoms having carbon atoms of carboxamide groups bound to acyclic carbon atoms and singly-bound oxygen atoms bound to the same carbon skeleton the carbon skeleton being acyclic and unsaturated
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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
- C07C303/32—Preparation of esters or amides of sulfuric acids; Preparation of sulfonic acids or of their esters, halides, anhydrides or amides of salts of sulfonic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/07—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton
- C07C309/08—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing oxygen atoms bound to the carbon skeleton containing hydroxy groups bound to the carbon skeleton
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/52—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom
- C07C69/606—Esters of acyclic unsaturated carboxylic acids having the esterified carboxyl group bound to an acyclic carbon atom having only or additionally carbon-to-carbon triple bonds as unsaturation in the carboxylic acid moiety
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
- C07C69/66—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
- C07C69/73—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids
- C07C69/732—Esters of carboxylic acids having esterified carboxylic groups bound to acyclic carbon atoms and having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety of unsaturated acids of unsaturated hydroxy carboxylic acids
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/64—Benzothiazoles with only hydrocarbon or substituted hydrocarbon radicals attached in position 2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/92—Naphthofurans; Hydrogenated naphthofurans
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/54—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the hetero ring
- C07D333/56—Radicals substituted by oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
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- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
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- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/576—Six-membered rings
- C07F9/58—Pyridine rings
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Public Health (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Cardiology (AREA)
- Urology & Nephrology (AREA)
- Heart & Thoracic Surgery (AREA)
- Pain & Pain Management (AREA)
- Rheumatology (AREA)
- Diabetes (AREA)
- Hematology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Furan Compounds (AREA)
- Peptides Or Proteins (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
Esta solicitud describe un proceso para la preparacion de análogos de himbacina utiles como antagonistas de los receptores de trombina. El proceso se basa en parte en el uso de una epimerizacion dinámica promovida por base de un centro nitro quiral. La química descrita en la presente invencion puede ser ejemplificada mediante grupo de formulas (1). REIVINDICACIoN 1.- Un proceso para preparar el compuesto (1) comprendiendo dicho proceso las etapas de (a) ciclar el compuesto (2) en un primer solvente a una temperatura elevada donde R5 y R6 son cada uno independientemente seleccionados del grupo formado por H, alquilo, alquenilo, alquinilo, alcoxi, cicloalquilo, arilo, alquilarilo, arilalquilo, grupos heterocíclicos y heteroarilo, o R5 y R6, junto con el nitrogeno al cual están unidos, forman un compuesto heterocíclico de 3 a 6 miembros que contiene 1-4 heteroátomos, para producir una primera mezcla de exo isomeros (3) teniendo dichos isomeros una union de anillo trans-[5,6]; y endo- isomeros: (4); (b) epimerizar dicha union de anillo trans-[5,6] en el compuesto (3) tratando dicha primera mezcla con una primera base para producir una segunda mezcla que comprende union de anillo cis-[5,6]- nitro-isomero alfa y union de anillo cis- [5,6]-nitro-isomero beta del compuesto (5) y, (c) tratar dicha segunda mezcla con un segundo solvente, haciendo que dicho isomero alfa del compuesto 5 precipite para producir el compuesto 1.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US64446405P | 2005-01-14 | 2005-01-14 |
Publications (1)
Publication Number | Publication Date |
---|---|
AR056919A1 true AR056919A1 (es) | 2007-11-07 |
Family
ID=36168544
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ARP060100127A AR056919A1 (es) | 2005-01-14 | 2006-01-12 | SíNTESIS EXO- Y DIASTEREO- SELECTIVAS DE ANÁLOGOS DE HIMBACINA |
Country Status (22)
Country | Link |
---|---|
US (4) | US7605275B2 (es) |
EP (4) | EP2196454B1 (es) |
JP (3) | JP4681616B2 (es) |
CN (2) | CN102757423B (es) |
AR (1) | AR056919A1 (es) |
AT (2) | ATE530516T1 (es) |
CA (2) | CA2875768C (es) |
CY (2) | CY1109896T1 (es) |
DE (1) | DE602006012450D1 (es) |
DK (2) | DK1848705T3 (es) |
ES (3) | ES2374379T3 (es) |
HK (1) | HK1108893A1 (es) |
HR (2) | HRP20100218T1 (es) |
ME (1) | ME01967B (es) |
MX (1) | MX2007008665A (es) |
PL (2) | PL2206697T3 (es) |
PT (2) | PT2206697E (es) |
RS (2) | RS51315B (es) |
SG (2) | SG192505A1 (es) |
SI (2) | SI1848705T1 (es) |
WO (1) | WO2006076415A2 (es) |
ZA (1) | ZA200706711B (es) |
Families Citing this family (23)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7488742B2 (en) * | 2000-06-15 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
US7772276B2 (en) | 2005-01-14 | 2010-08-10 | Schering Corporation | Exo-selective synthesis of himbacine analogs |
CA2594741A1 (en) * | 2005-01-14 | 2006-07-20 | Schering Corporation | Synthesis of himbacine analogs |
EP2196454B1 (en) | 2005-01-14 | 2014-08-27 | Merck Sharp & Dohme Corp. | Exo-and diastereo-selective syntheses of himbacine analogs |
EP1971336A2 (en) * | 2005-12-22 | 2008-09-24 | Shering Corporation | Thrombin receptor antagonists as phophylaxis to complications from cardiopulmonary surgery |
AR061727A1 (es) * | 2006-06-30 | 2008-09-17 | Schering Corp | Sintesis de dietil [[ 5- ( 3-fluorofenil) -piridin -2il] metil] fosfonato |
WO2008005344A2 (en) * | 2006-06-30 | 2008-01-10 | Schering Corporation | Synthesis of 3-(5-nitrocyclohex-1-enyl) acrylic acid and esters thereof |
WO2008076316A2 (en) * | 2006-12-15 | 2008-06-26 | Schering Corporation | Bisulfite purification of an alpha-keto amide |
AU2008310956B2 (en) | 2007-10-08 | 2014-08-07 | Aurinia Pharmaceuticals Inc. | Ophthalmic compositions comprising calcineurin inhibitors or mTOR inhibitors |
CN101910148B (zh) * | 2007-10-24 | 2014-06-04 | 默沙东公司 | 制备十二氢-萘并-呋喃基-氨基甲酸酯中间体的高纯度合成方法 |
JP5945593B2 (ja) * | 2011-06-21 | 2016-07-05 | ブルースター・シリコーンズ・フランス・エスアエス | ヒドロシリル化反応抑制剤及び安定な硬化性シリコーン組成物を調製するためのその使用 |
CN105330689B (zh) * | 2014-08-08 | 2018-08-17 | 博瑞生物医药(苏州)股份有限公司 | 制备Himbacine类似物中间体的制备方法 |
CN105985303B (zh) * | 2015-02-13 | 2020-08-14 | 上海彩迩文生化科技有限公司 | 抗凝血剂的制备方法、中间体及其制备方法 |
CN105348241B (zh) * | 2015-12-11 | 2017-09-05 | 南京华威医药科技开发有限公司 | 一种硫酸沃拉帕沙中间体的合成方法 |
US11247940B2 (en) | 2016-10-26 | 2022-02-15 | The Regents Of The University Of California | Efficient integration of manufacturing of upcycled concrete product into power plants |
CN106749138B (zh) * | 2016-12-07 | 2019-08-16 | 扬子江药业集团四川海蓉药业有限公司 | 一种硫酸沃拉帕沙中间体醛的制备方法 |
CN106866450B (zh) * | 2017-01-13 | 2019-01-11 | 阜阳欣奕华材料科技有限公司 | 硫酸沃拉帕沙中间体的制备方法 |
CN108658910B (zh) * | 2017-03-29 | 2020-11-03 | 北京新领先医药科技发展有限公司 | 一种沃拉帕沙中间体1-α的制备方法 |
US20190224275A1 (en) | 2017-05-12 | 2019-07-25 | Aurinia Pharmaceuticals Inc. | Protocol for treatment of lupus nephritis |
WO2019006352A1 (en) | 2017-06-30 | 2019-01-03 | The Regents Of The University Of California | CO2 MINERALIZATION IN PRODUTED AND INDUSTRIAL EFFLUENT WATER BY PH CHANGE CARBONATION |
US11339094B2 (en) | 2017-08-14 | 2022-05-24 | The Regents Of The University Of California | Mitigation of alkali-silica reaction in concrete using readily-soluble chemical additives |
WO2019057946A1 (en) | 2017-09-25 | 2019-03-28 | F. Hoffmann-La Roche Ag | MULTI-CYCLIC AROMATIC COMPOUNDS AS D-FACTOR INHIBITORS |
US11384029B2 (en) | 2019-03-18 | 2022-07-12 | The Regents Of The University Of California | Formulations and processing of cementitious components to meet target strength and CO2 uptake criteria |
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ID24726A (id) * | 1997-11-25 | 2000-08-03 | Schering Corp | Antagonis-antagonis reseptor trombin |
US6063847A (en) * | 1997-11-25 | 2000-05-16 | Schering Corporation | Thrombin receptor antagonists |
EP1075480B1 (en) * | 1998-05-05 | 2004-05-19 | Eli Lilly And Company | Purification of carboxaldehyde |
US7488742B2 (en) * | 2000-06-15 | 2009-02-10 | Schering Corporation | Thrombin receptor antagonists |
US20040192753A1 (en) | 2000-06-15 | 2004-09-30 | Samuel Chackalamannil | Methods of use of thrombin receptor antagonists |
PE20020235A1 (es) * | 2000-06-15 | 2002-04-02 | Schering Corp | Derivados de nor-seco himbacina como antagonistas de los receptores de trombina |
US7235567B2 (en) | 2000-06-15 | 2007-06-26 | Schering Corporation | Crystalline polymorph of a bisulfate salt of a thrombin receptor antagonist |
US8124625B2 (en) * | 2001-09-14 | 2012-02-28 | Shionogi & Co., Ltd. | Method of enhancing the expression of apolipoprotein AI using olefin derivatives |
ATE525378T1 (de) * | 2001-10-18 | 2011-10-15 | Schering Corp | Himbacinanaloga als thrombinrezeptorantagonisten |
CA2482858C (en) | 2002-04-16 | 2010-11-30 | Schering Corporation | Tricyclic thrombin receptor antagonists |
CA2567981C (en) * | 2004-05-28 | 2010-08-31 | Schering Corporation | Constrained himbacine analogs as thrombin receptor antagonists |
CA2594741A1 (en) * | 2005-01-14 | 2006-07-20 | Schering Corporation | Synthesis of himbacine analogs |
US7772276B2 (en) * | 2005-01-14 | 2010-08-10 | Schering Corporation | Exo-selective synthesis of himbacine analogs |
US7541471B2 (en) * | 2005-01-14 | 2009-06-02 | Schering Corporation | Synthesis of himbacine analogs |
EP2196454B1 (en) | 2005-01-14 | 2014-08-27 | Merck Sharp & Dohme Corp. | Exo-and diastereo-selective syntheses of himbacine analogs |
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