AR080149A1 - Procedimiento para la preparacion del nevibolol - Google Patents
Procedimiento para la preparacion del nevibololInfo
- Publication number
- AR080149A1 AR080149A1 ARP110100405A ARP110100405A AR080149A1 AR 080149 A1 AR080149 A1 AR 080149A1 AR P110100405 A ARP110100405 A AR P110100405A AR P110100405 A ARP110100405 A AR P110100405A AR 080149 A1 AR080149 A1 AR 080149A1
- Authority
- AR
- Argentina
- Prior art keywords
- methyl
- mixture
- butanol
- bis
- mixed
- Prior art date
Links
- 238000000034 method Methods 0.000 title abstract 2
- 238000002360 preparation method Methods 0.000 title abstract 2
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 abstract 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 5
- 239000000203 mixture Substances 0.000 abstract 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 4
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 abstract 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229960000619 nebivolol Drugs 0.000 abstract 3
- 239000002904 solvent Substances 0.000 abstract 3
- KOHIRBRYDXPAMZ-YHBROIRLSA-N (S,R,R,R)-nebivolol Chemical compound C1CC2=CC(F)=CC=C2O[C@H]1[C@H](O)CNC[C@@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 KOHIRBRYDXPAMZ-YHBROIRLSA-N 0.000 abstract 2
- WFRBDWRZVBPBDO-UHFFFAOYSA-N 2-methyl-2-pentanol Chemical compound CCCC(C)(C)O WFRBDWRZVBPBDO-UHFFFAOYSA-N 0.000 abstract 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 abstract 2
- -1 Nebivolol compound Chemical class 0.000 abstract 2
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 150000002118 epoxides Chemical class 0.000 abstract 2
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 abstract 2
- 125000006239 protecting group Chemical group 0.000 abstract 2
- JWEXHQAEWHKGCW-BIISKSHESA-N (R,S,S,S)-nebivolol hydrochloride Chemical compound Cl.C1CC2=CC(F)=CC=C2O[C@H]1[C@@H](O)CNC[C@H](O)[C@H]1OC2=CC=C(F)C=C2CC1 JWEXHQAEWHKGCW-BIISKSHESA-N 0.000 abstract 1
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-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
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 abstract 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 abstract 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 125000003118 aryl group Chemical group 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
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000001033 ether group Chemical group 0.000 abstract 1
- 239000012467 final product Substances 0.000 abstract 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract 1
- 238000001640 fractional crystallisation Methods 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 abstract 1
- 229940011051 isopropyl acetate Drugs 0.000 abstract 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- 229940068174 nebivolol hydrochloride Drugs 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000012454 non-polar solvent Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
- C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
- C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
-
- 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
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
-
- 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
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C07D311/60—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4 with aryl radicals attached in position 2
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Heart & Thoracic Surgery (AREA)
- Cardiology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Urology & Nephrology (AREA)
- Vascular Medicine (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrane Compounds (AREA)
- Epoxy Compounds (AREA)
- Steroid Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Peptides Or Proteins (AREA)
- Saccharide Compounds (AREA)
- Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
- Treatment Of Liquids With Adsorbents In General (AREA)
- Treating Waste Gases (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
REIVINDICACION 1: 1. Procedimiento para la preparacion del compuesto Nebivolol en forma de mezcla racémica de dos enantiomeros [2S[2R[R[R]]]] a, a'-[imino--bis (metileno)] bis[6-fluoro- croman-2---metanol] y [2R[2S[S[S]]]] a,a'-[imino-bis (metileno)] bis[6-fluoro-croman-2-metanol], con las siguientes formulas FJ''OF F'3'GF Nebivolol (SRRR + RSSS)caracterizado porque comprende las siguientes fases: a. se pone a reaccionar una mezcla de cuatro isomeros SR, RS, PR e SS del epoxido de formula (1)(SR+RS+ RR+SS) con una amina R-NH2 donde: - R es un grupo protector seleccionado entre metil, alil, tbutil, bencil, difenilmetil, trifenilmet.il, fluorenil, 9,10- dihidroantracen-9-il, dibencil, donde los anillos aromáticos presentes en los grupos pueden ser eventualmente mono o di sustituidos con un grupo seleccionado entre: halogeno, nitro, una cadena alquílica Cl-C4, CF3, CHF2, un grupo 0R2, donde R2 es un hidrogeno, un alquilo Cl-C4, en un solvente conveniente representado por un alcohol estéricamente obstruido seleccionado entre iPrOH (isopropanol), sec-BuOH, tert-BuOH, isoamílico, 2-metil-2-butanol, 2-metil--2-pentanol, solo o en mezcla con un solvente apolar seleccionado dentro del grupo éter de petroleo, pentano, hexano, ciclohexano, metilciclohexano, heptano, benceno, tolueno, para obtener una mezcla de los cuatro compuestos 2, 3, 4 y 5, donde el par 2/3 está separado del par 4/5; figuras 2, 3, 4 y 5 b. se ponen a reaccionar las aminas 2 y 3, mezcladas, con el par de epoxidos 4 y 5, mezclados, para obtener una mezcla de cuatro compuestos (6, 7, 8 y 9) figuras 6, 7 8 y 9 c. se separan los compuestos 6 y 8 (RSSS + SRRR), mezclados, de 7 y 9 por cristalizacion fraccionada de un primer solvente seleccionado entre etanol, isopropanol, butanol, tert-butanol, 2-metil--2-butanol, y sucesivamente de una mezcla de un solvente polar aprotico seleccionado entre metil acetato, etil acetato, isopropil acetato, acetona, metil etil cetona, acetonitrilo, isopropil éter, con un solvente apolar seleccionado entre pentano, hexano, ciclohexano, metilciclohexano, heptano, benceno, tolueno. d. se elimina el grupo protector R, y opcionalmente se forma sucesivamente la sal hidrocloruro, para obtener el producto final Nebivolol o Nebivolol hidrocloruro.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ITRM2010A000053A IT1397962B1 (it) | 2010-02-11 | 2010-02-11 | Processo per la preparazione del nebivololo. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR080149A1 true AR080149A1 (es) | 2012-03-14 |
Family
ID=42289104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP110100405A AR080149A1 (es) | 2010-02-11 | 2011-02-09 | Procedimiento para la preparacion del nevibolol |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US8487122B2 (es) |
| EP (1) | EP2534142B1 (es) |
| JP (1) | JP5698266B2 (es) |
| KR (1) | KR101726468B1 (es) |
| CN (1) | CN102858759B (es) |
| AR (1) | AR080149A1 (es) |
| AU (1) | AU2011214396B2 (es) |
| BR (1) | BR112012020252B8 (es) |
| CA (1) | CA2786833C (es) |
| EA (1) | EA019691B1 (es) |
| ES (1) | ES2445543T3 (es) |
| HR (1) | HRP20140155T1 (es) |
| IL (1) | IL220846A (es) |
| IT (1) | IT1397962B1 (es) |
| MX (1) | MX2012009386A (es) |
| PL (1) | PL2534142T3 (es) |
| PT (1) | PT2534142E (es) |
| RS (1) | RS53134B (es) |
| SG (1) | SG183266A1 (es) |
| WO (1) | WO2011098474A1 (es) |
| ZA (1) | ZA201206221B (es) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US8785664B2 (en) * | 2010-02-11 | 2014-07-22 | Menarini International Operations Luxembourg S.A. | Process for the preparation of nebivolol |
| ITRM20110418A1 (it) | 2011-08-02 | 2013-02-03 | Menarini Int Operations Lu Sa | Processo per la preparazione di epossidi quali intermedi per la sintesi del nebivololo. |
| CN104650022B (zh) * | 2013-11-20 | 2018-09-25 | 浙江奥翔药业股份有限公司 | 奈必洛尔的合成方法及其中间体化合物 |
| MX354930B (es) * | 2014-10-23 | 2018-03-20 | Consorcio Comex S A De C V | Composicion para aerosol usada para marcar o delimitar en cualquier tipo de superficie con una duracion temporal. |
| JP6921913B2 (ja) * | 2015-05-19 | 2021-08-18 | チョーチアン オウスン ファーマシューティカル カンパニー リミテッド | ネビボロールの合成方法及びその中間化合物 |
| WO2016183809A1 (zh) * | 2015-05-19 | 2016-11-24 | 浙江奥翔药业股份有限公司 | 奈必洛尔的合成方法及其中间体化合物 |
| CN105085499B (zh) * | 2015-08-07 | 2018-09-25 | 上海现代制药海门有限公司 | 盐酸奈必洛尔中间体混合物的结晶分离方法 |
| ITUB20160227A1 (it) * | 2016-01-21 | 2017-07-21 | Menarini Int Operations Luxembourg Sa | Processo per la sintesi di intermedi di Nebivololo |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2475298A1 (fr) * | 1980-02-01 | 1981-08-07 | Thomson Csf | Cellule photovoltaique et pile solaire utilisant une telle cellule |
| US4654362A (en) * | 1983-12-05 | 1987-03-31 | Janssen Pharmaceutica, N.V. | Derivatives of 2,2'-iminobisethanol |
| CA1337429C (en) | 1983-12-05 | 1995-10-24 | Guy Rosalia Eugene Van Lommen | Derivatives of 2,2'-iminobisethanol |
| CA1337432C (en) * | 1988-03-23 | 1995-10-24 | Raymond M. Xhonneux | Method of lowering the blood pressure |
| US6545040B1 (en) | 1988-03-23 | 2003-04-08 | Janssen Pharmaceutica N.V. | Method of lowering the blood pressure |
| DE3809857A1 (de) | 1988-03-24 | 1989-10-05 | Philips Patentverwaltung | Blasformmaschine zum blasformen von hohlkoerpern mit polsterregelung |
| TW355683B (en) | 1994-02-17 | 1999-04-11 | Janssen Pharmaceutica Nv | Composition containing micronized nebivolol |
| HU227236B1 (en) * | 2002-11-06 | 2010-12-28 | Egis Gyogyszergyar Nyilvanosan Muekoedoe Reszvenytarsasag | New process for the production of racemic and the pure [2s[2r*[r[r*]]]]-and [2r[2s*[s[s*]]]]-enantiomers of nebivolol |
| US8604222B2 (en) | 2004-07-30 | 2013-12-10 | Forest Laboratories Holdings Limited | Nebivolol and its pharmaceutically acceptable salts, process for preparation and pharmaceutical compositions of nebivolol |
| KR20070046877A (ko) | 2004-08-13 | 2007-05-03 | 하두르 메카니즘 프로덕션 엘티디 | 다중 트랙 프로파일 랩핑기용 시스템 및 방법 |
| AT502220A1 (de) * | 2005-07-19 | 2007-02-15 | Pharmacon Forschung & Beratung | Verfahren zur herstellung von nebivolol |
| WO2007041805A1 (en) | 2005-10-13 | 2007-04-19 | Burns Bay Investments Pty Ltd | Elongate lighting means |
| EP1803716B1 (en) | 2005-12-28 | 2012-07-25 | Acino Pharma AG | A process for preparation of racemic nebivolol |
| US7560575B2 (en) * | 2005-12-28 | 2009-07-14 | Acino Pharma Ag | Process for preparation of racemic Nebivolol |
| WO2007083318A1 (en) | 2006-01-18 | 2007-07-26 | Hetero Drugs Limited | Process for isolation of desired isomers of nebivolol intermediates |
| CN101541791B (zh) | 2006-11-27 | 2014-01-29 | Zach系统股份公司 | 制备奈必洛尔的方法 |
| ES2346371T3 (es) | 2006-11-27 | 2010-10-14 | Zach System S.P.A. | Proceso para la preparacion de nebivolol. |
| CN101235024A (zh) * | 2008-02-01 | 2008-08-06 | 中国科学院上海有机化学研究所 | 一类苯并二氢吡喃类化合物、合成方法和用途 |
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2010
- 2010-02-11 IT ITRM2010A000053A patent/IT1397962B1/it active
-
2011
- 2011-02-09 MX MX2012009386A patent/MX2012009386A/es active IP Right Grant
- 2011-02-09 AR ARP110100405A patent/AR080149A1/es active IP Right Grant
- 2011-02-09 BR BR112012020252A patent/BR112012020252B8/pt active IP Right Grant
- 2011-02-09 HR HRP20140155AT patent/HRP20140155T1/hr unknown
- 2011-02-09 EA EA201201127A patent/EA019691B1/ru not_active IP Right Cessation
- 2011-02-09 JP JP2012552378A patent/JP5698266B2/ja active Active
- 2011-02-09 RS RS20140025A patent/RS53134B/sr unknown
- 2011-02-09 CA CA2786833A patent/CA2786833C/en active Active
- 2011-02-09 PT PT117022632T patent/PT2534142E/pt unknown
- 2011-02-09 WO PCT/EP2011/051876 patent/WO2011098474A1/en not_active Ceased
- 2011-02-09 KR KR1020127023672A patent/KR101726468B1/ko active Active
- 2011-02-09 AU AU2011214396A patent/AU2011214396B2/en active Active
- 2011-02-09 CN CN201180008074.4A patent/CN102858759B/zh active Active
- 2011-02-09 PL PL11702263T patent/PL2534142T3/pl unknown
- 2011-02-09 US US13/578,018 patent/US8487122B2/en active Active
- 2011-02-09 SG SG2012059366A patent/SG183266A1/en unknown
- 2011-02-09 EP EP11702263.2A patent/EP2534142B1/en active Active
- 2011-02-09 ES ES11702263.2T patent/ES2445543T3/es active Active
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- 2012-08-17 ZA ZA2012/06221A patent/ZA201206221B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| PL2534142T3 (pl) | 2014-05-30 |
| HK1179626A1 (en) | 2013-10-04 |
| EA019691B1 (ru) | 2014-05-30 |
| EP2534142A1 (en) | 2012-12-19 |
| ZA201206221B (en) | 2014-01-29 |
| US20120316351A1 (en) | 2012-12-13 |
| HRP20140155T1 (hr) | 2014-03-14 |
| US8487122B2 (en) | 2013-07-16 |
| CN102858759A (zh) | 2013-01-02 |
| BR112012020252A2 (pt) | 2016-08-09 |
| SG183266A1 (en) | 2012-09-27 |
| AU2011214396A1 (en) | 2012-10-04 |
| CA2786833A1 (en) | 2011-08-18 |
| AU2011214396B2 (en) | 2014-06-05 |
| KR101726468B1 (ko) | 2017-04-12 |
| WO2011098474A1 (en) | 2011-08-18 |
| ITRM20100053A1 (it) | 2011-08-12 |
| BR112012020252B1 (pt) | 2021-05-04 |
| BR112012020252B8 (pt) | 2021-05-25 |
| IL220846A0 (en) | 2012-08-30 |
| KR20120129952A (ko) | 2012-11-28 |
| RS53134B (sr) | 2014-06-30 |
| EA201201127A1 (ru) | 2013-01-30 |
| MX2012009386A (es) | 2012-09-12 |
| JP5698266B2 (ja) | 2015-04-08 |
| IL220846A (en) | 2014-12-31 |
| ES2445543T3 (es) | 2014-03-03 |
| PT2534142E (pt) | 2014-02-24 |
| IT1397962B1 (it) | 2013-02-04 |
| CN102858759B (zh) | 2015-12-16 |
| JP2013519647A (ja) | 2013-05-30 |
| EP2534142B1 (en) | 2013-11-27 |
| CA2786833C (en) | 2017-03-07 |
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