AR032175A1 - Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados - Google Patents
Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivadosInfo
- Publication number
- AR032175A1 AR032175A1 ARP010104047A ARP010104047A AR032175A1 AR 032175 A1 AR032175 A1 AR 032175A1 AR P010104047 A ARP010104047 A AR P010104047A AR P010104047 A ARP010104047 A AR P010104047A AR 032175 A1 AR032175 A1 AR 032175A1
- Authority
- AR
- Argentina
- Prior art keywords
- group
- aryl
- alkyl
- hydrogen
- metal cation
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract 3
- 150000007513 acids Chemical class 0.000 title abstract 3
- 238000000034 method Methods 0.000 title abstract 3
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000004432 carbon atom Chemical group C* 0.000 abstract 7
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 7
- 125000003118 aryl group Chemical group 0.000 abstract 6
- -1 cation hydride Chemical class 0.000 abstract 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 5
- 150000001875 compounds Chemical class 0.000 abstract 5
- 125000000623 heterocyclic group Chemical group 0.000 abstract 5
- 229910052799 carbon Inorganic materials 0.000 abstract 4
- 229910052751 metal Inorganic materials 0.000 abstract 4
- 239000002184 metal Substances 0.000 abstract 4
- 125000004429 atom Chemical group 0.000 abstract 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract 3
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 3
- NEAQRZUHTPSBBM-UHFFFAOYSA-N 2-hydroxy-3,3-dimethyl-7-nitro-4h-isoquinolin-1-one Chemical class C1=C([N+]([O-])=O)C=C2C(=O)N(O)C(C)(C)CC2=C1 NEAQRZUHTPSBBM-UHFFFAOYSA-N 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 2
- 150000001768 cations Chemical group 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000005842 heteroatom Chemical group 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
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- ZFFBIQMNKOJDJE-UHFFFAOYSA-N 2-bromo-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(Br)C(=O)C1=CC=CC=C1 ZFFBIQMNKOJDJE-UHFFFAOYSA-N 0.000 abstract 1
- CSDQQAQKBAQLLE-UHFFFAOYSA-N 4-(4-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine Chemical compound C1=CC(Cl)=CC=C1C1C(C=CS2)=C2CCN1 CSDQQAQKBAQLLE-UHFFFAOYSA-N 0.000 abstract 1
- RVDLHGSZWAELAU-UHFFFAOYSA-N 5-tert-butylthiophene-2-carbonyl chloride Chemical compound CC(C)(C)C1=CC=C(C(Cl)=O)S1 RVDLHGSZWAELAU-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 108091000080 Phosphotransferase Proteins 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- KCNKJCHARANTIP-SNAWJCMRSA-N allyl-{4-[3-(4-bromo-phenyl)-benzofuran-6-yloxy]-but-2-enyl}-methyl-amine Chemical compound C=1OC2=CC(OC/C=C/CN(CC=C)C)=CC=C2C=1C1=CC=C(Br)C=C1 KCNKJCHARANTIP-SNAWJCMRSA-N 0.000 abstract 1
- 229940121363 anti-inflammatory agent Drugs 0.000 abstract 1
- 239000002260 anti-inflammatory agent Substances 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
- 201000011510 cancer Diseases 0.000 abstract 1
- SYGWYBOJXOGMRU-UHFFFAOYSA-N chembl233051 Chemical compound C1=CC=C2C3=CC(C(N(CCN(C)C)C4=O)=O)=C5C4=CC=CC5=C3SC2=C1 SYGWYBOJXOGMRU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical group FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 125000001188 haloalkyl group Chemical group 0.000 abstract 1
- 125000001072 heteroaryl group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- AFRJJFRNGGLMDW-UHFFFAOYSA-N lithium amide Chemical compound [Li+].[NH2-] AFRJJFRNGGLMDW-UHFFFAOYSA-N 0.000 abstract 1
- SIAPCJWMELPYOE-UHFFFAOYSA-N lithium hydride Chemical compound [LiH] SIAPCJWMELPYOE-UHFFFAOYSA-N 0.000 abstract 1
- 229910000103 lithium hydride Inorganic materials 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 239000008177 pharmaceutical agent Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 102000020233 phosphotransferase Human genes 0.000 abstract 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 abstract 1
- 229910000105 potassium hydride Inorganic materials 0.000 abstract 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 abstract 1
- 230000002062 proliferating effect Effects 0.000 abstract 1
- 208000037803 restenosis Diseases 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 abstract 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C259/00—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups
- C07C259/04—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids
- C07C259/10—Compounds containing carboxyl groups, an oxygen atom of a carboxyl group being replaced by a nitrogen atom, this nitrogen atom being further bound to an oxygen atom and not being part of nitro or nitroso groups without replacement of the other oxygen atom of the carboxyl group, e.g. hydroxamic acids having carbon atoms of hydroxamic groups bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C213/00—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton
- C07C213/08—Preparation of compounds containing amino and hydroxy, amino and etherified hydroxy or amino and esterified hydroxy groups bound to the same carbon skeleton by reactions not involving the formation of amino groups, hydroxy groups or etherified or esterified hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C221/00—Preparation of compounds containing amino groups and doubly-bound oxygen atoms bound to the same carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C227/04—Formation of amino groups in compounds containing carboxyl groups
- C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid
- C07C227/08—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid by reaction of ammonia or amines with acids containing functional groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C253/00—Preparation of carboxylic acid nitriles
- C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
-
- 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
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
-
- 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
- C07D209/44—Iso-indoles; Hydrogenated iso-indoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/08—One of the condensed rings being a six-membered aromatic ring the other ring being five-membered, e.g. indane
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic 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)
- Pyridine Compounds (AREA)
- Indole Compounds (AREA)
Abstract
Se propone un proceso para la preparacion de ácidos N-aril-antranílicos, que son agentes farmacéuticos utiles, por ejemplo, como agentes antiinflamatorios. Dichos ácidos pueden servir como intermedios en la preparacion de amidas N-aril antranílicas, ácidos hidroxámicos N-aril-antranílicos y ésteres de ácidos hidroxámicos N-aril-antranílicos. Dichos compuestos inhiben ciertas enzimas quinasa de especificidad doble involucradas en enfermedades proliferativas tales como cáncer y restenosis. Un proceso para sintetizar un compuesto de formula (1), o una sal farmacéuticamente aceptable de él, en donde R1 es hidrogeno, alquilo, alcoxi, o arilo; R2, R3, R4, R5, R6, R7, R8, R9 y R10 se seleccionan cada uno independientemente de: hidrogeno, halo, alquilo, arilo, un grupo heterocíclico, haloalquilo, alcoxi, nitro, CN, -(=)m-(CH2) n-R11, en donde m, n, y R11 son lo definido abajo, o dos sustituyentes cualquiera de R2, R3, R4, R5, R6, R7, R8, R9 y R10 que están unidos a átomos de carbono de anillos contiguos, se pueden tomar junto con los átomos de carbono de los anillos contiguos, para formar un grupo arilo, heteroarilo, heterocíclico, o cicloalquilo de 4 a 7 átomos totales en el anillo, o R1 y R6 se pueden tomar junto con el átomo de nitrogeno, al cual está unido R1, el átomo de carbono al cual está unido R6 y el átomo de carbono contiguo a dicho átomo de carbono al cual está unido R6 para formar un anillo aromático o dihidroaromático de 5 o 6 miembros que tiene átomos de carbono en 1 o 2 átomos de nitrogeno; R11 es hidrogeno, hidroxi,, -CO2H, o N(R12)R13, R12 y R13 son cada uno independientemente hidrogeno, alquilo o R12 y R13 se toman junto con el átomo de nitrogeno al cual están unidos para formar un grupo heterocíclico de 3 a 10 miembros que tiene átomos de carbono y uno, dos o tres heteroátomos seleccionados de O, S, y NR14, en donde R14 es hidrogeno o alquilo; m es un numero entero de 0 a 1; n es un numero entero seleccionado de 0, 1, 2, 3, 4; y -Z es COOH, COOM, COOR15, -C(O)R15, -C(O)N(R16)R17, -C(O)N(R18)OR19, NO2, o CN, en donde M es un cation de metal del GrupoI metal o un hemication de metal del Grupo II, R15 es alquilo, alquenilo, arilo o un grupo heterocíclico, y R16, R17, R18 y R19 se seleccionan cada uno independientemente de hidrogeno, alquilo, alquenilo, fenilo, y bencilo, o R16 y R17 se toman junto con el átomo de nitrogeno al cual están unidos para formar un grupo heterocíclico de 3 a 10 miembros que tiene átomos de carbono y uno, dos o tres heteroátomos seleccionados de O, S, y NR14, en donde R14 es hidrogeno o alquilo; que comprende hacer reaccionar un compuesto de formula (2), en donde R1, R6, R7, R8, R9, y R10 son lo definido anteriormente, con un compuesto de la formula (3), en donde Z, R2, R3, R4 y R5 son lo definido anteriormente, y X es halo o O-LG, en donde LG es SO2R20 o P(=O) (OR20)2, donde R20 es alquilo o arilo, optativamente en un solvente, y en la presencia de 1 equivalente en moles a 10 equivalentes en moles de una base, en donde la base se selecciona de: un hidruro de cation de metal del Grupo I o un hidruro de cation de metal del Grupo II, que incluyen hidruro de litio, hidruro de sodio, hidruro de potasio, e hidruro de calcio, una dialquilamida de cation de metal del Grupo II, que incluyen diisopropilamida de litio, una amida de cation de metal del Grupo I o una amida de cation de metal del Grupo II, que incluyen amida de litio, amida de sodio, amida de potasio, y un alcoxido de cation de metal del Grupo I o un alcoxido de cation de metal del Grupo II, que incluyen etoxido de sodio, ter-butoxido de potasio, y etoxido de magnesio, durante un tiempo, y a una temperatura suficiente para dar un compuesto de la formula (1).
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US22820600P | 2000-08-25 | 2000-08-25 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR032175A1 true AR032175A1 (es) | 2003-10-29 |
Family
ID=22856235
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP010104047A AR032175A1 (es) | 2000-08-25 | 2001-08-24 | Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados |
Country Status (31)
| Country | Link |
|---|---|
| EP (1) | EP1313694A1 (es) |
| JP (1) | JP2004507518A (es) |
| KR (1) | KR20030059115A (es) |
| CN (1) | CN1458921A (es) |
| AP (1) | AP2001002249A0 (es) |
| AR (1) | AR032175A1 (es) |
| AU (1) | AU2001277044A1 (es) |
| BG (1) | BG107635A (es) |
| BR (1) | BR0113520A (es) |
| CA (1) | CA2420003A1 (es) |
| CZ (1) | CZ2003477A3 (es) |
| DO (1) | DOP2001000238A (es) |
| EA (1) | EA200300187A1 (es) |
| GT (1) | GT200100174A (es) |
| HN (1) | HN2001000216A (es) |
| HU (1) | HUP0300828A2 (es) |
| IL (1) | IL154507A0 (es) |
| IS (1) | IS6724A (es) |
| MA (1) | MA26949A1 (es) |
| MX (1) | MXPA03001654A (es) |
| NO (1) | NO20030844L (es) |
| PA (1) | PA8526501A1 (es) |
| PE (1) | PE20020393A1 (es) |
| PL (1) | PL360699A1 (es) |
| SK (1) | SK2072003A3 (es) |
| SV (1) | SV2002000601A (es) |
| TN (1) | TNSN01127A1 (es) |
| UY (1) | UY26908A1 (es) |
| WO (1) | WO2002018319A1 (es) |
| YU (1) | YU14303A (es) |
| ZA (1) | ZA200301182B (es) |
Families Citing this family (38)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US7235537B2 (en) | 2002-03-13 | 2007-06-26 | Array Biopharma, Inc. | N3 alkylated benzimidazole derivatives as MEK inhibitors |
| PA8569301A1 (es) | 2002-03-13 | 2004-10-08 | Array Biopharma Inc | "derivados de bencimidazol n3 alquilado como inhibidores de mek" "n3 alkylated benzimidazole derivatives as mek inhibitors" |
| US7144907B2 (en) | 2003-09-03 | 2006-12-05 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| US7538120B2 (en) | 2003-09-03 | 2009-05-26 | Array Biopharma Inc. | Method of treating inflammatory diseases |
| RU2352558C2 (ru) | 2003-10-21 | 2009-04-20 | Уорнер-Ламберт Компани Ллс | Полиморфная форма n-[(r)-2,3-дигидроксипропокси]-3,4-дифтор-2-(2-фтор-4 йодфениламино)бензамида |
| US7732616B2 (en) | 2003-11-19 | 2010-06-08 | Array Biopharma Inc. | Dihydropyridine and dihydropyridazine derivatives as inhibitors of MEK and methods of use thereof |
| US7517994B2 (en) | 2003-11-19 | 2009-04-14 | Array Biopharma Inc. | Heterocyclic inhibitors of MEK and methods of use thereof |
| BRPI0416692A (pt) | 2003-11-19 | 2007-01-30 | Array Biopharma Inc | inibidores heterocìclicos de mek e métodos de emprego destes |
| US20050130954A1 (en) | 2003-11-21 | 2005-06-16 | Mitchell Ian S. | AKT protein kinase inhibitors |
| UA89035C2 (ru) * | 2003-12-03 | 2009-12-25 | Лео Фарма А/С | Эфиры гидроксамовых кислот и их фармацевтическое применение |
| PT1877379E (pt) | 2005-04-13 | 2013-04-17 | Astex Therapeutics Ltd | Derivados de hidroxibenzamida e seu uso como inibidores de hsp90 |
| EP1967516B1 (en) | 2005-05-18 | 2009-11-04 | Array Biopharma, Inc. | 4-(phenylamino)-6-oxo-1,6-dihydropyridazine-3-carboxamide derivatives as MEK inhibitors for the treatment of hyperproliferative diseases |
| US7754725B2 (en) | 2006-03-01 | 2010-07-13 | Astex Therapeutics Ltd. | Dihydroxyphenyl isoindolymethanones |
| JP5231411B2 (ja) | 2006-07-06 | 2013-07-10 | アレイ バイオファーマ、インコーポレイテッド | Ａｋｔプロテインキナーゼ阻害剤としてのジヒドロチエノピリミジン |
| DE602007011628D1 (de) | 2006-07-06 | 2011-02-10 | Array Biopharma Inc | Dihydrofuropyrimidine als akt-proteinkinaseinhibitoren |
| US8063050B2 (en) | 2006-07-06 | 2011-11-22 | Array Biopharma Inc. | Hydroxylated and methoxylated pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| MX2008016203A (es) | 2006-07-06 | 2009-01-27 | Array Biopharma Inc | Ciclopenta [d] pirimidinas como inhibidores de la proteina cinasa akt. |
| EP2073802A1 (en) | 2006-10-12 | 2009-07-01 | Astex Therapeutics Limited | Pharmaceutical combinations |
| JP5410285B2 (ja) | 2006-10-12 | 2014-02-05 | アステックス、セラピューティックス、リミテッド | 医薬化合物 |
| US8883790B2 (en) | 2006-10-12 | 2014-11-11 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US9730912B2 (en) | 2006-10-12 | 2017-08-15 | Astex Therapeutics Limited | Pharmaceutical compounds |
| GB0620259D0 (en) | 2006-10-12 | 2006-11-22 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| US8916552B2 (en) | 2006-10-12 | 2014-12-23 | Astex Therapeutics Limited | Pharmaceutical combinations |
| US9409886B2 (en) | 2007-07-05 | 2016-08-09 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as AKT protein kinase inhibitors |
| KR101624361B1 (ko) | 2007-07-05 | 2016-05-25 | 어레이 바이오파마 인크. | Ａｋｔ 단백질 키나제 억제제로서의 피리미딜 시클로펜탄 |
| US8846683B2 (en) | 2007-07-05 | 2014-09-30 | Array Biopharma, Inc. | Pyrimidyl cyclopentanes as Akt protein kinase inhibitors |
| CA2692502C (en) | 2007-07-05 | 2016-03-01 | Array Biopharma Inc. | Pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| EP2247578B1 (en) | 2008-01-09 | 2013-05-22 | Array Biopharma, Inc. | Hydroxylated pyrimidyl cyclopentanes as akt protein kinase inhibitors |
| NZ586720A (en) | 2008-01-09 | 2012-11-30 | Array Biopharma Inc | Hydroxylated pyrimidyl cyclopentane as akt protein kinase inhibitor |
| GB0806527D0 (en) | 2008-04-11 | 2008-05-14 | Astex Therapeutics Ltd | Pharmaceutical compounds |
| CN101985428B (zh) * | 2009-07-29 | 2014-02-12 | 杭州民生药业有限公司 | 邻苯胺基苯甲酸衍生物或其药学上可接受的盐、其制备方法及其用途 |
| US20120316337A1 (en) * | 2010-02-19 | 2012-12-13 | Universite Du Maine | Method for preparing chemical compounds of interest by nucleophilic aromatic substitution of aromatic carboxylic acid derivatives supporting at least one electro-attractive group |
| JP2013519715A (ja) * | 2010-02-19 | 2013-05-30 | センター ナショナル デ ラ リシェルシェ サイエンティフィック | 少なくとも１つの電子求引性基を有する芳香族カルボン酸誘導体の芳香族求核置換による目的の化学化合物の調製方法 |
| MY179607A (en) | 2011-04-01 | 2020-11-11 | Genentech Inc | Combinations of akt inhibitor compounds and abiraterone, and methods of use |
| BR112013025397A2 (pt) | 2011-04-01 | 2019-09-24 | Deepak Sampath | combinação de um composto, composto de fórmula i ou um sal farmaceuticamente aceitável do mesmo, uso, kit, produto, método para tratamento de um distúrbio hiperproliferativo e método para tratamento de uma doença ou afecção modulada por quinase akt em um mamífero |
| CN104837826B (zh) * | 2012-10-12 | 2018-07-27 | 埃克塞里艾克西斯公司 | 制备用于治疗癌症的化合物的新型方法 |
| CN112745237B (zh) * | 2019-10-29 | 2023-06-20 | 中国科学院上海药物研究所 | 2-芳基胺类化合物及其制备方法和应用 |
| WO2024011559A1 (en) * | 2022-07-15 | 2024-01-18 | Southern University Of Science And Technology | Fused aromatic amine preparing from isocyanide and cyclopropene |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3138636A (en) * | 1960-06-23 | 1964-06-23 | Parke Davis & Co | Anthranilic acid derivatives |
| WO1998037881A1 (en) * | 1997-02-28 | 1998-09-03 | Warner Lambert Company | Method of treating or preventing septic shock by administering a mek inhibitor |
| HUP0003731A3 (en) * | 1997-07-01 | 2002-11-28 | Warner Lambert Co | 4-bromo or 4-iodo phenylamino benzhydroxamic acid derivatives and their use as mek inhibitors |
| EP0993437B1 (en) * | 1997-07-01 | 2006-11-08 | Warner-Lambert Company Llc | 2-(4-bromo or 4-iodo phenylamino) benzoic acid derivatives and their use as mek inhibitors |
| CA2348236A1 (en) * | 1999-01-13 | 2000-07-20 | Stephen Douglas Barrett | 4-arylamino, 4-aryloxy, and 4-arylthio diarylamines and derivatives thereof as selective mek inhibitors |
| HK1045682B (zh) * | 1999-04-21 | 2006-04-07 | 沃尼尔‧朗伯公司 | 制备-2-(n-苯基氨基)苯甲酸衍生物的方法 |
-
2001
- 2001-07-20 EA EA200300187A patent/EA200300187A1/ru unknown
- 2001-07-20 CZ CZ2003477A patent/CZ2003477A3/cs unknown
- 2001-07-20 JP JP2002523437A patent/JP2004507518A/ja active Pending
- 2001-07-20 EP EP01954824A patent/EP1313694A1/en not_active Withdrawn
- 2001-07-20 BR BR0113520-1A patent/BR0113520A/pt not_active Application Discontinuation
- 2001-07-20 WO PCT/US2001/022948 patent/WO2002018319A1/en not_active Ceased
- 2001-07-20 HU HU0300828A patent/HUP0300828A2/hu unknown
- 2001-07-20 SK SK207-2003A patent/SK2072003A3/sk unknown
- 2001-07-20 IL IL15450701A patent/IL154507A0/xx unknown
- 2001-07-20 AP APAP/P/2001/002249A patent/AP2001002249A0/en unknown
- 2001-07-20 YU YU14303A patent/YU14303A/sh unknown
- 2001-07-20 PL PL36069901A patent/PL360699A1/xx unknown
- 2001-07-20 CN CN01815869A patent/CN1458921A/zh active Pending
- 2001-07-20 AU AU2001277044A patent/AU2001277044A1/en not_active Abandoned
- 2001-07-20 MX MXPA03001654A patent/MXPA03001654A/es unknown
- 2001-07-20 CA CA002420003A patent/CA2420003A1/en not_active Abandoned
- 2001-07-20 KR KR10-2003-7002675A patent/KR20030059115A/ko not_active Withdrawn
- 2001-08-15 SV SV2001000601A patent/SV2002000601A/es not_active Application Discontinuation
- 2001-08-22 TN TNTNSN01127A patent/TNSN01127A1/en unknown
- 2001-08-23 PA PA20018526501A patent/PA8526501A1/es unknown
- 2001-08-24 UY UY26908A patent/UY26908A1/es not_active Application Discontinuation
- 2001-08-24 PE PE2001000853A patent/PE20020393A1/es not_active Application Discontinuation
- 2001-08-24 DO DO2001000238A patent/DOP2001000238A/es unknown
- 2001-08-24 GT GT200100174A patent/GT200100174A/es unknown
- 2001-08-24 AR ARP010104047A patent/AR032175A1/es unknown
- 2001-09-26 HN HN2001000216A patent/HN2001000216A/es unknown
-
2003
- 2003-02-12 ZA ZA200301182A patent/ZA200301182B/en unknown
- 2003-02-20 IS IS6724A patent/IS6724A/is unknown
- 2003-02-24 NO NO20030844A patent/NO20030844L/no not_active Application Discontinuation
- 2003-03-13 BG BG107635A patent/BG107635A/bg unknown
- 2003-03-14 MA MA27069A patent/MA26949A1/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CA2420003A1 (en) | 2002-03-07 |
| SV2002000601A (es) | 2002-04-03 |
| MA26949A1 (fr) | 2004-12-20 |
| EP1313694A1 (en) | 2003-05-28 |
| YU14303A (sh) | 2006-08-17 |
| CN1458921A (zh) | 2003-11-26 |
| PL360699A1 (en) | 2004-09-20 |
| MXPA03001654A (es) | 2004-09-10 |
| PA8526501A1 (es) | 2002-07-30 |
| KR20030059115A (ko) | 2003-07-07 |
| SK2072003A3 (en) | 2004-01-08 |
| NO20030844L (no) | 2003-02-25 |
| NO20030844D0 (no) | 2003-02-24 |
| IL154507A0 (en) | 2003-09-17 |
| DOP2001000238A (es) | 2003-01-31 |
| CZ2003477A3 (cs) | 2003-10-15 |
| AU2001277044A1 (en) | 2002-03-13 |
| EA200300187A1 (ru) | 2003-08-28 |
| PE20020393A1 (es) | 2002-05-09 |
| HUP0300828A2 (hu) | 2003-09-29 |
| BG107635A (bg) | 2004-09-30 |
| TNSN01127A1 (en) | 2005-11-10 |
| AP2001002249A0 (en) | 2001-09-30 |
| ZA200301182B (en) | 2004-05-12 |
| JP2004507518A (ja) | 2004-03-11 |
| WO2002018319A1 (en) | 2002-03-07 |
| GT200100174A (es) | 2002-07-18 |
| IS6724A (is) | 2003-02-20 |
| BR0113520A (pt) | 2003-06-24 |
| UY26908A1 (es) | 2001-11-30 |
| HN2001000216A (es) | 2002-05-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| AR032175A1 (es) | Proceso para la fabricacion de acidos n-aril-antranilicos y sus derivados | |
| RU2361870C2 (ru) | Новые кумарины, их карбоксамидные производные, способы получения, композиции и применение | |
| AR038881A1 (es) | Compuestos que modulan la actividad de ppar, composicion farmaceutica que los contiene y un procedimiento para la preparcion de aquellos | |
| BG99495A (bg) | Фармацевтични съединения | |
| AR038883A1 (es) | Compuestos que modulan la actividad de ppar, composicion farmaceutica que los contiene y un metodo para prepararlos | |
| AR035548A1 (es) | Compuestos organicos | |
| RU2010116253A (ru) | Производные n-гидроксилсульфонамида как новые физиологически применимые доноры нитроксила | |
| PE58699A1 (es) | Derivados de acido arilsulfonil hidroxamico | |
| NL960021I2 (nl) | Nieuwe trifenylalkaan en alkeenderivaten den de bereiding en toepassing daarvan. | |
| YU47970B (sh) | Postupak za dobijanje spiro-supstituisanih glutaramidnih jedinjenja | |
| AR038882A1 (es) | Compuestos que modulan la actividad de ppar y composicion farmaceutica que los contiene | |
| RU2011152891A (ru) | Диарилгидантоины | |
| SE9702799D0 (sv) | New compounds | |
| AR025735A1 (es) | Compuestos terapeuticos | |
| ATE52498T1 (de) | Amidderivate. | |
| DK116480A (da) | Fremgangsmaade til fremstilling af substituerede chromoner | |
| TW200510353A (en) | Alpha substituted carboxylic acids as PPAR modulators | |
| HUP9900584A2 (hu) | Új benzoil-guanidin-származékok, eljárás előállításukra és gyógyszerkészítmények előállításában való felhasználásuk | |
| FI954016A0 (fi) | Uudet yhdisteet | |
| BG60338B2 (en) | Thienothiazines | |
| FR2682107B1 (fr) | Quinoleines 2-substituees pour le traitement des leishmanioses. | |
| ES2131549T3 (es) | Derivados macrolidas de 16 eslabones y su procedimiento de preparacion. | |
| BR9606985A (pt) | Processo para preparar um composto | |
| GB1092921A (en) | Anthranilic acid derivatives | |
| AR035982A1 (es) | Derivados de c-furano-2-il-metilamina y c-tiofeno-2-il-metilamina sustituidos y metodo de preparacion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FB | Suspension of granting procedure |