AR071632A1 - Proceso catalitico para hidrogenacion asimetrica en la sintesis de inhibidores de la dopamina-beta-hidroxilasa" - Google Patents
Proceso catalitico para hidrogenacion asimetrica en la sintesis de inhibidores de la dopamina-beta-hidroxilasa"Info
- Publication number
- AR071632A1 AR071632A1 ARP090101613A ARP090101613A AR071632A1 AR 071632 A1 AR071632 A1 AR 071632A1 AR P090101613 A ARP090101613 A AR P090101613A AR P090101613 A ARP090101613 A AR P090101613A AR 071632 A1 AR071632 A1 AR 071632A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- enantiomer
- group
- alkyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 6
- 238000009876 asymmetric hydrogenation reaction Methods 0.000 title abstract 2
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 108010015720 Dopamine beta-Hydroxylase Proteins 0.000 title 1
- 102100033156 Dopamine beta-hydroxylase Human genes 0.000 title 1
- 230000003197 catalytic effect Effects 0.000 title 1
- 239000003112 inhibitor Substances 0.000 title 1
- 238000003786 synthesis reaction Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 abstract 12
- 125000000217 alkyl group Chemical group 0.000 abstract 9
- 229910052736 halogen Inorganic materials 0.000 abstract 9
- 150000002367 halogens Chemical class 0.000 abstract 9
- 125000003545 alkoxy group Chemical group 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 5
- 125000003282 alkyl amino group Chemical group 0.000 abstract 3
- 125000003806 alkyl carbonyl amino group Chemical group 0.000 abstract 3
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 229910052717 sulfur Inorganic materials 0.000 abstract 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical class [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 2
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052731 fluorine Inorganic materials 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- -1 hydroxycarbonyl groups Chemical group 0.000 abstract 2
- 238000004519 manufacturing process Methods 0.000 abstract 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 239000011593 sulfur Substances 0.000 abstract 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 238000010511 deprotection reaction Methods 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 229910052740 iodine Inorganic materials 0.000 abstract 1
- 239000011630 iodine Substances 0.000 abstract 1
- 239000003446 ligand Substances 0.000 abstract 1
- 150000007524 organic acids Chemical class 0.000 abstract 1
- 125000005544 phthalimido group Chemical group 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000006239 protecting group Chemical group 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 150000003567 thiocyanates Chemical class 0.000 abstract 1
Classifications
-
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
-
- 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
- A61P9/10—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/84—Sulfur atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pyrane Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Un proceso para preparar el enantiomero S o R de un compuesto de la formula (1), comprendiendo el proceso someter un compuesto de la formula (2) a hidrogenacion asimétrica en presencia de un catalizador quiral y una fuente de hidrogeno, en donde: X es CH2, oxígeno o azufre; R1, R2 y R3 son los mismos o diferentes y denotan hidrogenos, halogenos, un grupo alquilo, alquiloxi, hidroxi, nitro, alquilcarbonilamino, alquilamino o dialquilamino; y R4 es alquilo o arilo, en donde el término alquilo denota cadenas hidrocarburo, rectas o ramificadas, que contienen de uno a seis átomos de carbono, opcionalmente sustituidas con grupos arilo, alcoxi, halogeno, alcoxicarbonilo o hidroxicarbonilo; el término arilo denota un grupo fenilo o naftilo, opcionalmente sustituido con un grupo alquiloxi, halogeno o nitro; y el término halogeno denota fluor, cloro, bromo o yodo donde el catalizador quiral comprende un ligando el cual es el enantiomero S o R de TolBINAP y la reaccion se lleva a cabo a una temperatura desde por encima de 70sC hasta 100sC y en presencia de un ácido a una concentracion de 0,05 a 0,2%. Reivindicacion 40: Un proceso para preparar el enantiomero R o S de un compuesto de la formula (3), en donde X es CH2, oxígeno o azufre; R1, R2 y R3 son los mismos o diferentes y denotan hidrogenos, halogenos, un grupo alquilo, alquiloxi, hidroxi, nitro, alquilcarbonilamino, alquilamino o dialquilamino; R4 es alquilo o arilo, en donde el término alquilo denota cadenas hidrocarburo, rectas o ramificadas, que contienen de uno a seis átomos de carbono, opcionalmente sustituidas con grupos arilo, alcoxi, halogeno, alcoxicarbonilo o hidroxicarbonilo; el término arilo denota un grupo fenilo o naftilo, opcionalmente sustituido con un grupo alquiloxi, halogeno o nitro; y el término halogeno denota fluor, cloro, bromo o yodo, que comprende la formacion del enantiomero R o S de un compuesto de la formula (1) a través de un proceso de acuerdo con cualquier reivindicacion precedente, seguida por la conversion del enantiomero R o S del compuesto de formula (1) al respectivo enantiomero R o S de un compuesto de la formula (3). Reivindicacion 46: Un proceso para formar el enantiomero R o S de un compuesto de la formula (4) o una sal del mismo, R1, R2 y R3 son los mismos o diferentes y denotan hidrogenos, halogenos, un grupo alquilo, alquiloxi, hidroxi, nitro, alquilcarbonilamino, alquilamino o dialquilamino; X significa O, S o CH2; n significa 1, 2 o 3; y R12 significa un grupo hidrogeno, alquilo o alquilarilo, que comprende formar el enantiomero R o S de un compuesto de la formula (3) de acuerdo con el proceso de cualquiera de las reivindicaciones 40 a 45, y convertir el enantiomero R o S del compuesto de la formula (3) al enantiomero R o S del compuesto de la formula (4). Reivindicacion 49: Un proceso de acuerdo con la reivindicacion 47 o 48, que comprende hacer reaccionar el enantiomero R o S del compuesto de la formula (3) con un compuesto de la formula (5) donde n significa 1, 2 o 3; cuando n es 1 o 2, R12 significa un grupo hidrogeno, alquilo o alquilarilo; R11, significa un grupo protector hidroxilo y R13 significa un grupo protector amino; cuando n significa 3, R11 significa un grupo protector hidroxilo pero R12 y R13 tomados conjuntamente representan un grupo ftalimido; y con una sal tiocianato soluble en agua en presencia de un ácido orgánico en un solvente sustancialmente inerte, seguido por la posterior desproteccion de los productos intermediarios de formulas (6) a (9).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5075408P | 2008-05-06 | 2008-05-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR071632A1 true AR071632A1 (es) | 2010-06-30 |
Family
ID=40933790
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090101613A AR071632A1 (es) | 2008-05-06 | 2009-05-05 | Proceso catalitico para hidrogenacion asimetrica en la sintesis de inhibidores de la dopamina-beta-hidroxilasa" |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US8710239B2 (es) |
| EP (1) | EP2303855B1 (es) |
| JP (1) | JP2011519919A (es) |
| AR (1) | AR071632A1 (es) |
| CA (1) | CA2723411A1 (es) |
| ES (1) | ES2531458T3 (es) |
| PT (1) | PT2303855E (es) |
| WO (1) | WO2009136803A2 (es) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR071632A1 (es) | 2008-05-06 | 2010-06-30 | Bial Portela & Ca Sa | Proceso catalitico para hidrogenacion asimetrica en la sintesis de inhibidores de la dopamina-beta-hidroxilasa" |
| BR112015010969B1 (pt) | 2012-11-14 | 2020-05-26 | Bial - Portela & C.A., S.A. | Uso de um composto (r)-5-(2-(benzilamino)etil)-1-(6,8-difluorcroman-3-il)-1h-imidazol-2(3h)-tiona |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7125904B2 (en) | 2002-10-11 | 2006-10-24 | Portela & C.A., S.A. | Peripherally-selective inhibitors of dopamine-β-hydroxylase and method of their preparation |
| CA2671830C (en) * | 2006-12-12 | 2019-03-19 | Bial - Portela & C.A., S.A. | Catalytic process for asymmetric hydrogenation |
| AR071632A1 (es) | 2008-05-06 | 2010-06-30 | Bial Portela & Ca Sa | Proceso catalitico para hidrogenacion asimetrica en la sintesis de inhibidores de la dopamina-beta-hidroxilasa" |
-
2009
- 2009-05-05 AR ARP090101613A patent/AR071632A1/es unknown
- 2009-05-06 JP JP2011508434A patent/JP2011519919A/ja active Pending
- 2009-05-06 WO PCT/PT2009/000025 patent/WO2009136803A2/en not_active Ceased
- 2009-05-06 PT PT09742906T patent/PT2303855E/pt unknown
- 2009-05-06 US US12/990,918 patent/US8710239B2/en active Active
- 2009-05-06 EP EP09742906.2A patent/EP2303855B1/en not_active Not-in-force
- 2009-05-06 CA CA2723411A patent/CA2723411A1/en not_active Abandoned
- 2009-05-06 ES ES09742906.2T patent/ES2531458T3/es active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US20110237803A1 (en) | 2011-09-29 |
| PT2303855E (pt) | 2015-03-11 |
| EP2303855A2 (en) | 2011-04-06 |
| WO2009136803A2 (en) | 2009-11-12 |
| WO2009136803A3 (en) | 2010-07-22 |
| EP2303855B1 (en) | 2014-12-31 |
| JP2011519919A (ja) | 2011-07-14 |
| CA2723411A1 (en) | 2009-11-12 |
| US8710239B2 (en) | 2014-04-29 |
| ES2531458T3 (es) | 2015-03-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |