AR072900A1 - Agentes terapeuticos derivados de pirazolo[3,4-d]pirimidina - Google Patents
Agentes terapeuticos derivados de pirazolo[3,4-d]pirimidinaInfo
- Publication number
- AR072900A1 AR072900A1 ARP090102973A ARP090102973A AR072900A1 AR 072900 A1 AR072900 A1 AR 072900A1 AR P090102973 A ARP090102973 A AR P090102973A AR P090102973 A ARP090102973 A AR P090102973A AR 072900 A1 AR072900 A1 AR 072900A1
- Authority
- AR
- Argentina
- Prior art keywords
- alkyl
- pyridyl
- ring
- pyrazolo
- pyrimidin
- Prior art date
Links
- 239000003814 drug Substances 0.000 title abstract 2
- 229940124597 therapeutic agent Drugs 0.000 title abstract 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title 1
- -1 cyano, carboxy Chemical group 0.000 abstract 31
- 125000000217 alkyl group Chemical group 0.000 abstract 12
- 229910052757 nitrogen Inorganic materials 0.000 abstract 12
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 11
- 125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 abstract 10
- 229910052760 oxygen Inorganic materials 0.000 abstract 6
- 229910052717 sulfur Inorganic materials 0.000 abstract 6
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 5
- 125000005842 heteroatom Chemical group 0.000 abstract 5
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 5
- 125000004103 aminoalkyl group Chemical group 0.000 abstract 4
- 125000003118 aryl group Chemical group 0.000 abstract 4
- 125000000623 heterocyclic group Chemical group 0.000 abstract 4
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 4
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 abstract 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract 3
- 125000001072 heteroaryl group Chemical group 0.000 abstract 3
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 abstract 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 2
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 2
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 abstract 2
- 125000002853 C1-C4 hydroxyalkyl group Chemical group 0.000 abstract 2
- 125000005947 C1-C6 alkylsulfonyloxy group Chemical group 0.000 abstract 2
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 abstract 2
- 125000005843 halogen group Chemical group 0.000 abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 2
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 abstract 1
- 125000004845 (C1-C6) alkylsulfonylamino group Chemical group 0.000 abstract 1
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 abstract 1
- QUKPALAWEPMWOS-UHFFFAOYSA-N 1h-pyrazolo[3,4-d]pyrimidine Chemical compound C1=NC=C2C=NNC2=N1 QUKPALAWEPMWOS-UHFFFAOYSA-N 0.000 abstract 1
- 101100134927 Gallus gallus COR8 gene Proteins 0.000 abstract 1
- 102000030595 Glucokinase Human genes 0.000 abstract 1
- 108010021582 Glucokinase Proteins 0.000 abstract 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 abstract 1
- 208000008589 Obesity Diseases 0.000 abstract 1
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract 1
- 125000005115 alkyl carbamoyl group Chemical group 0.000 abstract 1
- HONIICLYMWZJFZ-UHFFFAOYSA-N azetidine Chemical compound C1CNC1 HONIICLYMWZJFZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 abstract 1
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 201000010099 disease Diseases 0.000 abstract 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 239000008103 glucose Substances 0.000 abstract 1
- 230000003914 insulin secretion Effects 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 125000005647 linker group Chemical group 0.000 abstract 1
- 230000001404 mediated effect Effects 0.000 abstract 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract 1
- 235000020824 obesity Nutrition 0.000 abstract 1
- 230000002265 prevention Effects 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920006395 saturated elastomer Polymers 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 abstract 1
- 125000004434 sulfur atom Chemical group 0.000 abstract 1
- 208000001072 type 2 diabetes mellitus Diseases 0.000 abstract 1
Classifications
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/519—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/04—Anorexiants; Antiobesity agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Diabetes (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Obesity (AREA)
- Hematology (AREA)
- Endocrinology (AREA)
- Emergency Medicine (AREA)
- Child & Adolescent Psychology (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Agentes terapéuticos derivados de pirazolo[3,4-d]pirimidina util en el tratamiento o prevencion de una enfermedad o afeccion médica mediada por glucoquinasa (GLK o GK), que conduce a una reduccion del umbral de glucosa para la secrecion de insulina, diabetes tipo 2 y obesidad. Reivindicacion 1: Un compuesto de formula (1) o una sal farmacéuticamente aceptable del mismo en donde A y B son cada uno N o CR6, siempre que al menos uno de A y B sea CR6; X es C o N; Y es CH o N; Z es C o N; en donde X, Y y Z se seleccionan de forma tal que al menos dos de X, Y y Z son N, el anillo que los contiene es aromático y ningun átomo de N del anillo está cuaternizado; R1 es alquilo C1-6, arilo, arilalquilo C1-6, o HET-1, en donde el arilo, arilalquilo C1-6 y HET-1 están opcionalmente sustituidos por uno, dos, o tres grupos que se seleccionan independientemente de halo, alquilo C1-4, alcoxi C1-4, trifluorometilo, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, ciano, carboxi, alcoxi C1-6carbonilo, carbamoilo, N-alquil C1-4carbamoilo, N,N-dialquil C1-4carbamoilo, aminosulfonilo, alquil C1-6aminosulfonilo, dialquil C1-6aminosulfonilo, alcanoil C1-4amino, hidroxialquilo C1-4, alcoxi C1-4-alquilo C1-4, alquil C1-4S(O)p-alquilo C1-4, aminoalquilo C1-4, alquil C1-4-aminoalquilo C1-4, dialquil C1-4-aminoalquilo C1-4, alcoxi C1-6-carbonilalquilo C1-4, alquil C1-6-sulfoniloxi, cicloalquil C3-6-sulfonilo, alquil C1-6-sulfonilamino, azetidinilcarbonilo, pirrolidinilcarbonilo y HET-3A; en donde HET-1 es un anillo heteroarilo unido a C de 5 o 6 miembros, o un sistema de anillos bicíclico fusionado de formula -D-E, en donde el anillo D está unido a Z y es un anillo arilo o heteroarilo de 6 miembros y un anillo E es un anillo heteroarilo, heterociclilo o cicloalquilo de 5 o 6 miembros que está fusionado al anillo D en cualquier posicion disponible; R2 es alquilo C1-6 opcionalmente sustituido por uno o dos hidroxi o por uno de los siguientes: carboxi, carbamoilo, N,N-dialquil C1-4carbamoilo, alcoxi C1-6carbonilo, un grupo -N(R7)COR8 o un grupo NR9R10; o R2 es un grupo -(CHR4)n-P-Q en donde n es 1, 2, 3 o 4; P es un enlazante que se selecciona de O, SO2, CONH y NHCO; Q se selecciona de alquilo C1-6, cicloalquilo C3-6 y un heterociclilo de 4, 5 o 6 miembros (en donde dicho anillo heterociclilo contiene 1, 2 o 3 heteroátomos que se seleccionan independientemente de O, N y S, siempre que no haya enlaces O-O, S-S ni O-S en donde un átomo de C disponible en el anillo puede oxidarse para convertirse en un grupo carbonilo, un átomo de S disponible en el anillo puede oxidarse para convertirse en un grupo SO o SO2 y en donde opcionalmente hay un enlace doble en el anillo) y Q está opcionalmente sustituido en un átomo de C disponible por hidroxi o alcoxi C1-4; R3 es HET-2 en donde HET-2 es un anillo heteroarilo monocíclico unido a C de 5 o 6 miembros, que contiene un átomo de N en la posicion 2 y opcionalmente 1 o 2 heteroátomos del anillo adicionales que se seleccionan independientemente de O, N y S; o HET-2 es un anillo heteroarilo bicíclico unido a C de 8, 9 o 10 miembros que contiene un átomo de N en la posicion 2 con hasta cinco heteroátomos del anillo adicionales que se seleccionan independientemente de O, N y S; en donde HET-2 está opcionalmente sustituido en un átomo de C disponible, o en un átomo de N del anillo siempre que no quede de este modo cuaternizado, con 1 o 2 sustituyentes que se seleccionan independientemente de R11; cada R4 se selecciona independientemente de H, hidroxi, metilo y etilo; siempre que cuando n es > 1, entonces no más de dos grupos R4 son hidroxi; R5 es H, alcoxi C1-4 o alquilo C1-4; R6 es H, alcoxi C1-4 o alquilo C1-4; R7 es H, o alquilo C1-4; R8 es alquilo C1-4; R9 es H o alquilo C1-4 opcionalmente sustituido por hidroxi o metoxi; R10 es H o alquilo C1-4; o -NR9R10 forma una azetidina opcionalmente sustituida por hidroxi; R11 se selecciona independientemente de halo, alquilo C1-4, alcoxi C1-4, trifluorometilo, alquil C1-6tio, alquil C1-6sulfinilo, alquil C1-6sulfonilo, ciano, carboxi, alcoxi C1-6carbonilo, carbamoilo, N-alquil C1-4carbamoilo, N,N-dialquil C1-4carbamoilo, aminosulfonilo, alquil C1-6aminosulfonilo, dialquil C1-6aminosulfonilo, alcanoil C1-4amino, hidroxialquilo C1-4, alcoxi C1-4-alquilo C1-4, alquil C1-4S(O)p-alquilo C1-4 (en donde p es 0, 1 o 2), aminoalquilo C1-4, alquil C1-4-aminoalquilo C1-4, dialquil C1-4-aminoalquilo C1-4, alcoxi C1-6-carbonilalquilo C1-4, alquil C1-6-sulfoniloxi, cicloalquil C3-6-sulfonilo, alquil C1-6-sulfonilamino, azetidinilcarbonilo, pirrolidinilcarbonilo y HET-3; HET-3 y HET-3A son cada uno independientemente un anillo heteroarilo insustituido unido a C o N de 5 o 6 miembros que contiene 1, 2 o 3 heteroátomos del anillo que se seleccionan independientemente de O, N y S, o un anillo heterociclilo saturado insustituido unido a C o N de 4, 5 o 6 miembros que contiene un heteroátomo del anillo que se selecciona de O, N y S; L es S, O o NR12; y R12 es H o alquilo C1-4; pero excluyendo N-(5-cloro-2-piridinil)-2-[(1-fenil-1H-pirazolo[3,4-d]pirimidin-4-il)tio]propanamida; N-[1-(1-metiletil)-1H-pirazol-5-il]-2-[(1-fenil-1H-pirazolo[3,4-d]pirimidin-4-il)tio]propanamida; N-(5-(metil)isoxazol-3-il)-2-[[1-(4-fluorofenil)-1H-pirazolo[3,4-d]pirimidin-4-il]tio]butanamida; N-(5-(metil)isoxazol-3-il)-2-[[1-(4-fluorofenil)-1H-pirazolo[3,4-d]pirimidin-4-il]tio]propanamida; (2R)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-5-hidroxi-N-(5-metil-2-piridil)pentanamida; (2R)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-5-hidroxi-pentanamida; (2S)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-ciano-2-piridil)-3-[(1S)-2-hidroxi-1-metil-etoxi]propanamida; (2R)-2-[1-(2-clorofenil)pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-ciano-2-piridil)-3-(2-hidroxietoxi)propanamida; (2S)-N-(5-ciano-2-piridil)-2-[1-(2,5-dimetilfenil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-(2-hidroxietoxi)-propanamida; (2S)-3-(2-hidroxietoxi)-N-(5-metil-2-piridil)-2-(9-fenilpurin-6-il)oxi-propanamida; (2R)-2-[1-(2-clorofenil)pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-fluoro-2-piridil)-3-(2-hidroxietoxi)propanamida; (2S)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-[(2R)-2-hidroxipropoxi]propanamida; (2R)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-[(2R)-2-hidroxipropoxi]propanamida; (2S)-2-[1-(3-cloro-2-piridil)-pirazolo[4,5-e]pirimidin-4-il]oxi-N-(5-ciano-2-piridil)-3-(3-hidroxiciclobutoxi)propanamida; y (2S)-N-(5-cloro-2-piridil)-2-[1-(3-cloro-2-piridil)pirazolo[4,5-e]pirimidin-4-il]oxi-3-(3-hidroxiciclobutoxi)propanamida.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US8591908P | 2008-08-04 | 2008-08-04 | |
| US16804809P | 2009-04-09 | 2009-04-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR072900A1 true AR072900A1 (es) | 2010-09-29 |
Family
ID=41563374
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP090102973A AR072900A1 (es) | 2008-08-04 | 2009-08-03 | Agentes terapeuticos derivados de pirazolo[3,4-d]pirimidina |
Country Status (23)
| Country | Link |
|---|---|
| US (1) | US8143263B2 (es) |
| EP (1) | EP2324028A2 (es) |
| JP (1) | JP2011529955A (es) |
| KR (1) | KR20110052676A (es) |
| CN (1) | CN102171213A (es) |
| AR (1) | AR072900A1 (es) |
| AU (1) | AU2009278929B2 (es) |
| BR (1) | BRPI0917589A2 (es) |
| CA (1) | CA2732165A1 (es) |
| CL (1) | CL2011000249A1 (es) |
| CO (1) | CO6351730A2 (es) |
| CR (1) | CR20110065A (es) |
| DO (1) | DOP2011000047A (es) |
| EA (1) | EA201100097A1 (es) |
| EC (1) | ECSP11010809A (es) |
| IL (1) | IL210778A0 (es) |
| MX (1) | MX2011001333A (es) |
| PE (1) | PE20110568A1 (es) |
| SV (1) | SV2011003829A (es) |
| TW (1) | TW201011026A (es) |
| UY (1) | UY32032A (es) |
| WO (1) | WO2010015849A2 (es) |
| ZA (1) | ZA201101663B (es) |
Families Citing this family (24)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| TW200600086A (en) * | 2004-06-05 | 2006-01-01 | Astrazeneca Ab | Chemical compound |
| TW200714597A (en) * | 2005-05-27 | 2007-04-16 | Astrazeneca Ab | Chemical compounds |
| CL2007003061A1 (es) * | 2006-10-26 | 2008-08-01 | Astrazeneca Ab | Compuestos derivados de 3,5-dioxi-benzamida; proceso de preparacion; composicion farmaceutica que comprende a dichos compuestos; y su uso para tratar una enfermedad mediada a traves de glk, tal como la diabetes tipo 2. |
| GB0902434D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Chemical process |
| GB0902406D0 (en) * | 2009-02-13 | 2009-04-01 | Astrazeneca Ab | Crystalline polymorphic form |
| AR076221A1 (es) * | 2009-04-09 | 2011-05-26 | Astrazeneca Ab | Derivado de pirazol [4,5-e] pirimidina y su uso para tratar diabetes y obesidad |
| WO2010116177A1 (en) * | 2009-04-09 | 2010-10-14 | Astrazeneca Ab | A pyrazolo [4,5-e] pyrimidine derivative and its use to treat diabetes and obesity |
| US8530413B2 (en) | 2010-06-21 | 2013-09-10 | Sanofi | Heterocyclically substituted methoxyphenyl derivatives with an oxo group, processes for preparation thereof and use thereof as medicaments |
| TW201215387A (en) | 2010-07-05 | 2012-04-16 | Sanofi Aventis | Spirocyclically substituted 1,3-propane dioxide derivatives, processes for preparation thereof and use thereof as a medicament |
| TW201215388A (en) | 2010-07-05 | 2012-04-16 | Sanofi Sa | (2-aryloxyacetylamino)phenylpropionic acid derivatives, processes for preparation thereof and use thereof as medicaments |
| TW201221505A (en) | 2010-07-05 | 2012-06-01 | Sanofi Sa | Aryloxyalkylene-substituted hydroxyphenylhexynoic acids, process for preparation thereof and use thereof as a medicament |
| WO2013037390A1 (en) | 2011-09-12 | 2013-03-21 | Sanofi | 6-(4-hydroxy-phenyl)-3-styryl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| WO2013045413A1 (en) | 2011-09-27 | 2013-04-04 | Sanofi | 6-(4-hydroxy-phenyl)-3-alkyl-1h-pyrazolo[3,4-b]pyridine-4-carboxylic acid amide derivatives as kinase inhibitors |
| CN103450124B (zh) * | 2013-08-30 | 2016-03-09 | 江苏九九久科技股份有限公司 | 决奈达隆合成方法 |
| US10538522B2 (en) | 2015-05-14 | 2020-01-21 | The Regents Of The University Of California | Brassinosteroid mimetics |
| PT3395801T (pt) | 2015-12-16 | 2021-05-24 | Nippon Soda Co | Composto de arilazol e agente de controlo de pragas |
| CN106361753A (zh) * | 2016-11-13 | 2017-02-01 | 曹艳 | 一种别嘌醇衍生物及其在制备抗肿瘤药物中的用途 |
| CN106749265A (zh) * | 2016-11-13 | 2017-05-31 | 曹艳 | 一种别嘌醇衍生物及其在制备抗肿瘤药物中的用途 |
| CN106749264A (zh) * | 2016-11-13 | 2017-05-31 | 曹艳 | 一种别嘌醇衍生物及其在制备抗肿瘤药物中的用途 |
| CN106749263A (zh) * | 2016-11-13 | 2017-05-31 | 曹艳 | 一种别嘌醇衍生物及其在制备抗肿瘤药物中的用途 |
| EP3357928B1 (en) | 2017-02-03 | 2021-01-06 | Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V. | Novel dyes with phosphinic acid, phosphinate, phosphonate and phosphonamidate substituents as auxochromic groups and methods for preparing the same |
| CN108033966A (zh) * | 2018-01-05 | 2018-05-15 | 天津药明康德新药开发有限公司 | 7-叔丁基3-乙基8-甲基5,6二氢三唑并吡嗪3,7(8h)二甲酸基酯的合成方法 |
| WO2020254553A1 (en) | 2019-06-19 | 2020-12-24 | Nmd Pharma A/S | Compounds for the treatment of neuromuscular disorders |
| CN113185520A (zh) * | 2021-04-28 | 2021-07-30 | 山东鲁抗医药股份有限公司 | 替格瑞洛杂质b及其制备方法 |
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-
2009
- 2009-08-03 EP EP09785441A patent/EP2324028A2/en not_active Withdrawn
- 2009-08-03 AR ARP090102973A patent/AR072900A1/es unknown
- 2009-08-03 KR KR1020117004895A patent/KR20110052676A/ko not_active Withdrawn
- 2009-08-03 EA EA201100097A patent/EA201100097A1/ru unknown
- 2009-08-03 AU AU2009278929A patent/AU2009278929B2/en not_active Expired - Fee Related
- 2009-08-03 PE PE2011000125A patent/PE20110568A1/es not_active Application Discontinuation
- 2009-08-03 MX MX2011001333A patent/MX2011001333A/es not_active Application Discontinuation
- 2009-08-03 CA CA2732165A patent/CA2732165A1/en not_active Abandoned
- 2009-08-03 CN CN2009801395833A patent/CN102171213A/zh active Pending
- 2009-08-03 WO PCT/GB2009/050970 patent/WO2010015849A2/en not_active Ceased
- 2009-08-03 BR BRPI0917589A patent/BRPI0917589A2/pt not_active IP Right Cessation
- 2009-08-03 JP JP2011521643A patent/JP2011529955A/ja not_active Withdrawn
- 2009-08-04 TW TW098126200A patent/TW201011026A/zh unknown
- 2009-08-04 UY UY0001032032A patent/UY32032A/es not_active Application Discontinuation
- 2009-08-04 US US12/535,293 patent/US8143263B2/en not_active Expired - Fee Related
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2011
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- 2011-02-04 CL CL2011000249A patent/CL2011000249A1/es unknown
- 2011-02-04 EC EC2011010809A patent/ECSP11010809A/es unknown
- 2011-02-04 CR CR20110065A patent/CR20110065A/es unknown
- 2011-03-03 ZA ZA2011/01663A patent/ZA201101663B/en unknown
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| PE20110568A1 (es) | 2011-09-07 |
| TW201011026A (en) | 2010-03-16 |
| US20100093757A1 (en) | 2010-04-15 |
| EA201100097A1 (ru) | 2011-10-31 |
| CR20110065A (es) | 2011-05-10 |
| UY32032A (es) | 2010-03-26 |
| AU2009278929A1 (en) | 2010-02-11 |
| IL210778A0 (en) | 2011-03-31 |
| WO2010015849A3 (en) | 2010-04-01 |
| JP2011529955A (ja) | 2011-12-15 |
| CO6351730A2 (es) | 2011-12-20 |
| CL2011000249A1 (es) | 2011-07-15 |
| WO2010015849A2 (en) | 2010-02-11 |
| SV2011003829A (es) | 2011-07-01 |
| EP2324028A2 (en) | 2011-05-25 |
| CN102171213A (zh) | 2011-08-31 |
| CA2732165A1 (en) | 2010-02-11 |
| KR20110052676A (ko) | 2011-05-18 |
| MX2011001333A (es) | 2011-03-15 |
| ECSP11010809A (es) | 2011-03-31 |
| ZA201101663B (en) | 2011-11-30 |
| AU2009278929A8 (en) | 2011-03-10 |
| DOP2011000047A (es) | 2011-02-28 |
| AU2009278929B2 (en) | 2012-07-05 |
| BRPI0917589A2 (pt) | 2015-11-17 |
| US8143263B2 (en) | 2012-03-27 |
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