AR061964A1 - Una sintesis enantioselectiva de pirrolidinas sustituidas con flavonas, y procesos de preparacion de sus intermediarios de obtencion - Google Patents
Una sintesis enantioselectiva de pirrolidinas sustituidas con flavonas, y procesos de preparacion de sus intermediarios de obtencionInfo
- Publication number
- AR061964A1 AR061964A1 ARP070103023A ARP070103023A AR061964A1 AR 061964 A1 AR061964 A1 AR 061964A1 AR P070103023 A ARP070103023 A AR P070103023A AR P070103023 A ARP070103023 A AR P070103023A AR 061964 A1 AR061964 A1 AR 061964A1
- Authority
- AR
- Argentina
- Prior art keywords
- compound
- formula
- represented
- trans
- referred
- Prior art date
Links
- 229930003944 flavone Natural products 0.000 title abstract 3
- 235000011949 flavones Nutrition 0.000 title abstract 3
- 238000002360 preparation method Methods 0.000 title abstract 3
- 230000015572 biosynthetic process Effects 0.000 title abstract 2
- 150000002213 flavones Chemical group 0.000 title abstract 2
- 238000003786 synthesis reaction Methods 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 16
- 239000002904 solvent Substances 0.000 abstract 6
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 abstract 4
- 238000000034 method Methods 0.000 abstract 4
- 239000000203 mixture Substances 0.000 abstract 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 abstract 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 abstract 3
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 abstract 3
- 239000002585 base Substances 0.000 abstract 3
- 239000003054 catalyst Substances 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 abstract 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 abstract 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000003638 chemical reducing agent Substances 0.000 abstract 2
- 229940126214 compound 3 Drugs 0.000 abstract 2
- 229940125898 compound 5 Drugs 0.000 abstract 2
- 238000010438 heat treatment Methods 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
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 abstract 2
- AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 abstract 2
- 150000003235 pyrrolidines Chemical group 0.000 abstract 2
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Natural products C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 abstract 2
- YHGHAFKDRXNDMC-LKFCYVNXSA-N (2r,3s)-1-methyl-5-oxo-3-(2,4,6-trimethoxyphenyl)pyrrolidine-2-carboxylic acid Chemical compound COC1=CC(OC)=CC(OC)=C1[C@H]1[C@H](C(O)=O)N(C)C(=O)C1 YHGHAFKDRXNDMC-LKFCYVNXSA-N 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 abstract 1
- VKVJIWVUYNTBEZ-UHFFFAOYSA-N 1,3-bis(3,5-dichlorophenyl)urea Chemical group ClC1=CC(Cl)=CC(NC(=O)NC=2C=C(Cl)C=C(Cl)C=2)=C1 VKVJIWVUYNTBEZ-UHFFFAOYSA-N 0.000 abstract 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 abstract 1
- JJSDPGSJXCYILH-MNOVXSKESA-N 1-[2-hydroxy-3-[(2r,3s)-2-(hydroxymethyl)-1-methylpyrrolidin-3-yl]-4,6-dimethoxyphenyl]ethanone Chemical compound COC1=CC(OC)=C(C(C)=O)C(O)=C1[C@H]1[C@H](CO)N(C)CC1 JJSDPGSJXCYILH-MNOVXSKESA-N 0.000 abstract 1
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 abstract 1
- 229910015900 BF3 Inorganic materials 0.000 abstract 1
- 108091007914 CDKs Proteins 0.000 abstract 1
- 102000003903 Cyclin-dependent kinases Human genes 0.000 abstract 1
- 108090000266 Cyclin-dependent kinases Proteins 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000002841 Lewis acid Substances 0.000 abstract 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- GAMYVSCDDLXAQW-AOIWZFSPSA-N Thermopsosid Natural products O(C)c1c(O)ccc(C=2Oc3c(c(O)cc(O[C@H]4[C@H](O)[C@@H](O)[C@H](O)[C@H](CO)O4)c3)C(=O)C=2)c1 GAMYVSCDDLXAQW-AOIWZFSPSA-N 0.000 abstract 1
- UYQMRAQWCFNNAV-NEPJUHHUSA-N [(2r,3s)-1-methyl-3-(2,4,6-trimethoxyphenyl)pyrrolidin-2-yl]methanol Chemical compound COC1=CC(OC)=CC(OC)=C1[C@H]1[C@H](CO)N(C)CC1 UYQMRAQWCFNNAV-NEPJUHHUSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000003513 alkali Substances 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 abstract 1
- 150000008041 alkali metal carbonates Chemical class 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000002947 alkylene group Chemical group 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 239000007864 aqueous solution Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 239000011230 binding agent Substances 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 1
- 229940125782 compound 2 Drugs 0.000 abstract 1
- 150000004696 coordination complex Chemical class 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 239000012649 demethylating agent Substances 0.000 abstract 1
- 230000017858 demethylation Effects 0.000 abstract 1
- 238000010520 demethylation reaction Methods 0.000 abstract 1
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 abstract 1
- -1 dimethoxy compound Chemical class 0.000 abstract 1
- FRXQVOYXWZGMLI-UHFFFAOYSA-N dimethyl 5-oxo-3-(2,4,6-trimethoxyphenyl)pyrrolidine-2,4-dicarboxylate Chemical compound COC(=O)C1NC(=O)C(C(=O)OC)C1C1=C(OC)C=C(OC)C=C1OC FRXQVOYXWZGMLI-UHFFFAOYSA-N 0.000 abstract 1
- BEPAFCGSDWSTEL-UHFFFAOYSA-N dimethyl malonate Chemical compound COC(=O)CC(=O)OC BEPAFCGSDWSTEL-UHFFFAOYSA-N 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000002212 flavone derivatives Chemical class 0.000 abstract 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 150000007517 lewis acids Chemical class 0.000 abstract 1
- 229910052744 lithium Inorganic materials 0.000 abstract 1
- YZPQGUSGVWCEFZ-JXMROGBWSA-N methyl (e)-2-nitro-3-(2,4,6-trimethoxyphenyl)prop-2-enoate Chemical compound COC(=O)C(\[N+]([O-])=O)=C/C1=C(OC)C=C(OC)C=C1OC YZPQGUSGVWCEFZ-JXMROGBWSA-N 0.000 abstract 1
- LNUMNTDMTRECOT-UHFFFAOYSA-N methyl 5-oxo-3-(2,4,6-trimethoxyphenyl)pyrrolidine-2-carboxylate Chemical compound COC(=O)C1NC(=O)CC1C1=C(OC)C=C(OC)C=C1OC LNUMNTDMTRECOT-UHFFFAOYSA-N 0.000 abstract 1
- 239000012022 methylating agents Substances 0.000 abstract 1
- 239000002808 molecular sieve Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 239000012299 nitrogen atmosphere Substances 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229920000137 polyphosphoric acid Polymers 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
- 239000011541 reaction mixture Substances 0.000 abstract 1
- 238000007363 ring formation reaction Methods 0.000 abstract 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 abstract 1
- 239000011780 sodium chloride Substances 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 230000000707 stereoselective effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- KFGFAPZWUZEIPL-UHFFFAOYSA-N trimethyl 3-nitro-2-(2,4,6-trimethoxyphenyl)propane-1,1,3-tricarboxylate Chemical compound COC(=O)C(C(=O)OC)C(C(C(=O)OC)[N+]([O-])=O)C1=C(OC)C=C(OC)C=C1OC KFGFAPZWUZEIPL-UHFFFAOYSA-N 0.000 abstract 1
- VHBFFQKBGNRLFZ-UHFFFAOYSA-N vitamin p Natural products O1C2=CC=CC=C2C(=O)C=C1C1=CC=CC=C1 VHBFFQKBGNRLFZ-UHFFFAOYSA-N 0.000 abstract 1
- 239000011592 zinc chloride Substances 0.000 abstract 1
- 235000005074 zinc chloride Nutrition 0.000 abstract 1
Classifications
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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
- C07D405/04—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/08—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon radicals, substituted by hetero atoms, attached to ring carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyrrole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Abstract
Síntesis enantioselectiva de (+)-trans enantiómero de pirrolidinas sustituido con flavonas, representado por la fórmula (1) o sales de las mismas, que son inhibidores de las quinasas ciclino dependientes y pueden ser utilizados para el tratamiento de desórdenes proliferativos tales como el cáncer. Reivindicación 1: Un proceso para la preparación del (+)-trans enantiómero de pirrolidina sustituida con una flavona, representado por la fórmula (1); o una sal farmacéuticamente aceptable del mismo; en donde Ar es fenilo, que es no sustituido o sustituido por 1, 2 ó 3 sustituyentes idénticos o diferentes seleccionados de: halógeno, nitro, ciano, alquilo C₁₋₄, fluorometil, difluorometil, trifluorometil, hidroxil, alcoxi C₁₋₄, carboxi, alcoxi C₁₋₄carbonil, alquileno C₁₋₄hidroxil, CONH₂, CONR¹R³, SO₂NR¹R², cicloalquil, NR¹R² y SR³; en donde R¹ y R² son cada uno independientemente seleccionados de hidrógeno, alquilo C₁₋₄, alquil C₁₋₄carbonil y aril, o R¹ y R² junto con el átomo de nitrógeno a los que se encuentran enlazados, forman un anillo de 5 ó 6 miembros, que puede contener opcionalmente por lo menos un heteroátomo adicional; y R³ es seleccionado de hidrógeno, alquilo C₁₋₄, arilo y SR⁴, en donde R⁴ es alquilo C₁₋₄ o arilo; comprendiendo los pasos de: (a) tratar un compuesto representado por la fórmula (2) (referido a continuación como compuesto 2) con anhídrido ascético en la presencia de un catalizador seleccionado de: ácido polifosfórico y un ácido Lewis seleccionado de: cloruro de zinc, cloruro de aluminio, trifluoruro de boro y tribromuro de boro, para obtener (-)-trans-ácido ascético 3-(3-acetil-2-hidroxi-4,6-dimetoxi-fenil)-1-metil-pirrolidin-2-il metil éster representado por la fórmula (3) (referido a continuación como compuesto 3); (b) tratar el compuesto 3 con una solución acuosa de un álcali seleccionado de: hidróxido de sodio e hidróxido de potasio, y elevar la temperatura de la mezcla de reacción a alrededor de 50°C para obtener (-)-trans-1-[2-hidroxi-3-(2hidroximetil-1-metil-pirrolidin-3-il)-4,6-dimetoxi-fenil]-etanona representado por la fórmula (4) (referido a continuación como compuesto 4); (c) hacer reaccionar el compuesto 4 con un éster de Fórmula ArCOOCH₃ (en donde Ar es tal como se ha definido en Fórmula (1)) en la presencia de un base seleccionada de: hidruro de sodio, n-butil litio, litio hexametildisilacida y litio diisopropilamida y un solvente seleccionado de: tetrahidrofurano, N,N-dimetilformamida y dioxano bajo la atmósfera de nitrógeno, seguido de ciclización catalizada ácida para producir el compuesto dimetoxi representado por la fórmula (5) (referido a continuación como compuesto 5); (d) someter el compuesto 5 a desmetilación calentándolo con un agente desmetilante seleccionado de: hidrocloruro de piridina, tribromuro de boro, eterato de trifluoruro de boro y tricloruro de aluminio a una temperatura en el rango de 120°C a 180°C; y (e) opcionalmente, convertir el compuesto resultante de la fórmula (1) en una sal farmacéuticamente aceptable. Reivindicación 3: Un proceso para la preparación del compuesto (-)-trans-(1-metil-3-(2,4,6-trimetoxifenil)pirrolidin-2-il)-metanol representado por la fórmula (2); tal como se ha mencionado en el paso (a) del procedimiento tal como se ha reivindicado en la reivindicación 1; que comprende tratar el compuesto (-)-trans-1-metil-5-oxo-3-(2,4,6-trimetoxifenil) pirrolidina-2-ácido carboxílico de la fórmula (6) (referido a continuación como el compuesto 6), con un agente reductor en un solvente. Reivindicación 4: Un procedimiento de acuerdo con la reivindicación 3, en donde el compuesto 6 es preparado por las etapas de: (a) llevar a cabo una adición éstereoespecífica Michael de dimetil malonato a (E)-metil-2-nitro-3-(2,4,6-trimetoxifenil)acrilato en un solvente en la presencia de un complejo catalizador, una base y tamices moleculares, en donde el complejo catalizador comprende un ligante quiral bis(oxazolina) y un complejo de metal, para obtener (+)-trimetil-3-nitro-2-(2,4,6-trimetoxifenil)-propano-1,1,3-tricarboxilato representado por la fórmula (7) (referido a continuación como compuesto 7); (b) tratar el compuesto 7 tal como se ha obtenido en el paso (a) con un agente reductor en un solvente para obtener (+)-dimetil-5-oxo-3-(2,4,6-trimetoxifenil)-pirrolidina-2,4-dicarboxilato representado por la fórmula (8) (referido a continuación como compuesto 8); (c) tratar el compuesto 8 con cloruro de sodio en un solvente y calentar la mezcla resultante de la reacción a una temperatura en el rango de 120°C a 170°C para obtener (+)-metil-5-oxo-3-(2,4,6-trimetoxifenil)-pirrolidina-2-carboxilato como una mezcla de isómeros cis y trans, representado por la fórmula (9) (referido a continuación como compuesto 9); (d) reaccionar el compuesto 9 con un agente metilador en un solvente y una base seleccionado de: un hidrato metálico alcalino y un carbonato metálico alcalino, seguido de someter la mezcla resultante de compuestos cis y trans a hidrólisis alcalino con un hidróxido de metal alcalino en un alcohol, y calentar la mezcla resultante de la reacción a una temperatura en el rango de 50°C a 100°C para obtener el compuesto 6 como único isómero trans.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/IB2006/052294 WO2008007169A1 (en) | 2006-07-07 | 2006-07-07 | An enantioselective synthesis of pyrrolidine-substituted flavones |
Publications (1)
Publication Number | Publication Date |
---|---|
AR061964A1 true AR061964A1 (es) | 2008-08-10 |
Family
ID=37546592
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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ARP070103023A AR061964A1 (es) | 2006-07-07 | 2007-07-06 | Una sintesis enantioselectiva de pirrolidinas sustituidas con flavonas, y procesos de preparacion de sus intermediarios de obtencion |
Country Status (18)
Country | Link |
---|---|
US (1) | US7951961B2 (es) |
EP (1) | EP2041121B1 (es) |
JP (1) | JP5006396B2 (es) |
KR (1) | KR101285957B1 (es) |
CN (1) | CN101484445B (es) |
AR (1) | AR061964A1 (es) |
AT (1) | ATE517892T1 (es) |
AU (1) | AU2006346193C1 (es) |
BR (1) | BRPI0621851A2 (es) |
CA (1) | CA2658215C (es) |
DK (1) | DK2041121T3 (es) |
HK (1) | HK1126762A1 (es) |
IL (1) | IL196298A0 (es) |
MX (1) | MX2009000109A (es) |
NZ (1) | NZ573841A (es) |
PT (1) | PT2041121E (es) |
TW (1) | TWI391388B (es) |
WO (1) | WO2008007169A1 (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7884127B2 (en) | 2002-07-08 | 2011-02-08 | Pirimal Life Sciences Ltd. | Inhibitors of cyclin dependent kinases and their use |
LV14179B (lv) * | 2008-12-03 | 2010-08-20 | Ivars Kalvins | 2,2'-ciklopropilidēn-bis-oksazolīnu reģenerēšana |
TWI461194B (zh) | 2009-05-05 | 2014-11-21 | Piramal Entpr Ltd | 吡咯啶取代黃酮作為輻射致敏劑 |
WO2012069972A1 (en) | 2010-11-19 | 2012-05-31 | Piramal Life Sciences Limited | A pharmaceutical combination for the treatment of breast cancer |
KR101264012B1 (ko) * | 2010-12-31 | 2013-05-13 | 주식회사 코리아나화장품 | 플라바논 화합물 및 그 제조방법, 이로부터 제조된 화장료 조성물 |
WO2012123889A1 (en) | 2011-03-14 | 2012-09-20 | Piramal Healthcare Limited | A synergistic pharmaceutical combination for the treatment of pancreatic cancer |
CA2840017A1 (en) | 2011-06-24 | 2012-12-27 | Piramal Enterprises Limited | Compounds for the treatment of cancers associated with human papillomavirus |
IN2014MN01546A (es) | 2012-01-13 | 2015-05-08 | Piramal Entpr Ltd | |
EP2877461B1 (en) * | 2012-07-27 | 2018-05-09 | Emory University | Heterocyclic flavone derivatives, compositions, and methods related thereto |
JP5988305B2 (ja) * | 2013-03-29 | 2016-09-07 | 国立大学法人山口大学 | 光学活性α−ブロモベンゾイル酢酸エステル類の製造方法 |
DK3019166T3 (da) | 2013-07-12 | 2019-07-29 | Piramal Entpr Ltd | A Pharmaceutical Combination for the Treatment of Melanoma |
CN104725279B (zh) * | 2015-02-12 | 2018-03-02 | 威海迪素制药有限公司 | 一种N‑Boc‑联苯丙氨酸衍生物的制备方法 |
CN113402394B (zh) * | 2015-05-12 | 2024-04-26 | Fmc公司 | 作为除草剂的芳基取代的双环化合物 |
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US5849733A (en) * | 1996-05-10 | 1998-12-15 | Bristol-Myers Squibb Co. | 2-thio or 2-oxo flavopiridol analogs |
AU2001255090A1 (en) * | 2000-05-03 | 2001-11-12 | Lg Live Sciences Ltd. | Cdk inhibitors having 3-hydroxychromen-4-one structure |
US6784167B2 (en) * | 2000-09-29 | 2004-08-31 | Bayer Pharmaceuticals Corporation | 17-beta-hydroxysteroid dehydrogenase-II inhibitors |
TWI331034B (en) * | 2002-07-08 | 2010-10-01 | Piramal Life Sciences Ltd | Inhibitors of cyclin-dependent kinases and their use |
NZ574266A (en) | 2006-06-21 | 2011-10-28 | Piramal Life Sciences Ltd | Enantiomerically pure flavone derivatives for the treatment of poliferative disorders and processes for their preparation |
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2006
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- 2006-07-07 WO PCT/IB2006/052294 patent/WO2008007169A1/en active Application Filing
- 2006-07-07 CN CN200680055257.0A patent/CN101484445B/zh not_active Expired - Fee Related
- 2006-07-07 AU AU2006346193A patent/AU2006346193C1/en not_active Ceased
- 2006-07-07 AT AT06766035T patent/ATE517892T1/de active
- 2006-07-07 PT PT06766035T patent/PT2041121E/pt unknown
- 2006-07-07 KR KR1020097002349A patent/KR101285957B1/ko not_active IP Right Cessation
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- 2006-07-07 CA CA2658215A patent/CA2658215C/en active Active
- 2006-07-07 EP EP06766035A patent/EP2041121B1/en not_active Not-in-force
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Publication number | Publication date |
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ATE517892T1 (de) | 2011-08-15 |
AU2006346193A2 (en) | 2009-02-12 |
PT2041121E (pt) | 2011-09-12 |
EP2041121A1 (en) | 2009-04-01 |
TWI391388B (zh) | 2013-04-01 |
US7951961B2 (en) | 2011-05-31 |
CN101484445A (zh) | 2009-07-15 |
EP2041121B1 (en) | 2011-07-27 |
US20100113803A1 (en) | 2010-05-06 |
KR101285957B1 (ko) | 2013-07-12 |
HK1126762A1 (en) | 2009-09-11 |
AU2006346193B2 (en) | 2012-11-15 |
IL196298A0 (en) | 2009-09-22 |
BRPI0621851A2 (pt) | 2013-01-29 |
KR20090033465A (ko) | 2009-04-03 |
CA2658215C (en) | 2013-08-27 |
JP5006396B2 (ja) | 2012-08-22 |
AU2006346193C1 (en) | 2014-02-20 |
CA2658215A1 (en) | 2008-01-17 |
MX2009000109A (es) | 2009-03-16 |
TW200815413A (en) | 2008-04-01 |
AU2006346193A1 (en) | 2008-01-17 |
CN101484445B (zh) | 2012-09-05 |
WO2008007169A1 (en) | 2008-01-17 |
NZ573841A (en) | 2011-11-25 |
JP2009542796A (ja) | 2009-12-03 |
DK2041121T3 (da) | 2011-11-14 |
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