AR120291A2 - Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-triazol-2-il]n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato - Google Patents
Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-triazol-2-il]n-metil-2-[4-(2-piridinil)fenil]acetamida monohidratoInfo
- Publication number
- AR120291A2 AR120291A2 ARP200102938A ARP200102938A AR120291A2 AR 120291 A2 AR120291 A2 AR 120291A2 AR P200102938 A ARP200102938 A AR P200102938A AR P200102938 A ARP200102938 A AR P200102938A AR 120291 A2 AR120291 A2 AR 120291A2
- Authority
- AR
- Argentina
- Prior art keywords
- methyl
- temperature
- aminosulfonyl
- pyridinyl
- phenyl
- Prior art date
Links
- OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 title abstract 2
- METKIMKYRPQLGS-UHFFFAOYSA-N atenolol Chemical compound CC(C)NCC(O)COC1=CC=C(CC(N)=O)C=C1 METKIMKYRPQLGS-UHFFFAOYSA-N 0.000 title 1
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 abstract 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- IVZKZONQVYTCKC-UHFFFAOYSA-N bay 57-1293 Chemical compound N=1C(C)=C(S(N)(=O)=O)SC=1N(C)C(=O)CC(C=C1)=CC=C1C1=CC=CC=N1 IVZKZONQVYTCKC-UHFFFAOYSA-N 0.000 abstract 3
- 239000013078 crystal Substances 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- QPIDAZSAUYNBAC-UHFFFAOYSA-N methanesulfonic acid;n-methyl-n-(4-methyl-5-sulfamoyl-1,3-thiazol-2-yl)-2-(4-pyridin-2-ylphenyl)acetamide;hydrate Chemical compound O.CS(O)(=O)=O.N=1C(C)=C(S(N)(=O)=O)SC=1N(C)C(=O)CC(C=C1)=CC=C1C1=CC=CC=N1 QPIDAZSAUYNBAC-UHFFFAOYSA-N 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 2
- HBXRPXYBMZDIQL-UHFFFAOYSA-N 1$l^{2}-borolane Chemical compound [B]1CCCC1 HBXRPXYBMZDIQL-UHFFFAOYSA-N 0.000 abstract 1
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 abstract 1
- 239000003153 chemical reaction reagent Substances 0.000 abstract 1
- 230000007774 longterm Effects 0.000 abstract 1
- 229940098779 methanesulfonic acid Drugs 0.000 abstract 1
- PPAJHCGEURRDOG-UHFFFAOYSA-N methanesulfonic acid;n-methyl-n-(4-methyl-5-sulfamoyl-1,3-thiazol-2-yl)-2-(4-pyridin-2-ylphenyl)acetamide Chemical compound CS(O)(=O)=O.N=1C(C)=C(S(N)(=O)=O)SC=1N(C)C(=O)CC(C=C1)=CC=C1C1=CC=CC=N1 PPAJHCGEURRDOG-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 150000004682 monohydrates Chemical class 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 abstract 1
- 238000003756 stirring Methods 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
- 150000003606 tin compounds Chemical class 0.000 abstract 1
- 231100000331 toxic Toxicity 0.000 abstract 1
- 230000002588 toxic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/427—Thiazoles not condensed and containing further heterocyclic rings
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4402—Non condensed pyridines; Hydrogenated derivatives thereof only substituted in position 2, e.g. pheniramine, bisacodyl
-
- 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
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/44—Non condensed pyridines; Hydrogenated derivatives thereof
- A61K31/4427—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems
- A61K31/4436—Non condensed pyridines; Hydrogenated derivatives thereof containing further heterocyclic ring systems containing a heterocyclic ring having sulfur as a ring hetero atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
- A61P31/22—Antivirals for DNA viruses for herpes viruses
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/38—Nitrogen atoms
- C07D277/44—Acylated amino or imino radicals
- C07D277/46—Acylated amino or imino radicals by carboxylic acids, or sulfur or nitrogen analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/13—Crystalline forms, e.g. polymorphs
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Virology (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Molecular Biology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
Síntesis mejorada y reducida de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)fenil] acetamida y la sal mesilato monohidrato de la misma usando reactivos derivados de ácido borónico o borolano y evitando compuestos orgánicos de estaño tóxicos. La sal mesilato monohidrato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)fenil]acetamida ha demostrado tener una estabilidad a largo plazo y una cinética de liberación mejoradas en composiciones farmacéuticas. Reivindicación 1: Método para preparar el monometanosulfonato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato cristalino de fórmula (1) caracterizado porque comprende los pasos de: a) proporcionar una mezcla de un solvente orgánico y agua que contiene N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)fenil]acetamida, donde el solvente orgánico se selecciona preferentemente del grupo formado por MeOH, EtOH, n-PrOH, i-PrOH, acetonitrilo, THF y acetona, b) agregar ácido metanosulfónico a la mezcla del paso a) a una temperatura elevada, preferentemente a una temperatura comprendida entre 30ºC y 90ºC, más preferentemente a una temperatura comprendida entre 35ºC y 80ºC, aún más preferentemente a una temperatura comprendida entre 40ºC y 70ºC, y aún más preferentemente a una temperatura entre 45ºC y 60ºC, y con mayor preferencia aún a una temperatura entre 50ºC y 55ºC, para obtener una solución supersaturada de mesilato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)-fenil]acetamida, c) opcionalmente agregar cristales de monometanosulfonato de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)-fenil]acetamida monohidrato a la solución supersaturada obtenida en el paso b) a una temperatura elevada comprendida entre 30ºC y 90ºC, preferentemente a una temperatura comprendida entre 35ºC y 80ºC, más preferentemente a una temperatura comprendida entre 40ºC y 70ºC, aún más preferentemente a una temperatura entre 45ºC y 60ºC, y con mayor preferencia aún a una temperatura entre 50ºC y 55ºC, d) opcionalmente agitar moderadamente a lentamente la solución supersaturada obtenida en el paso b) o el paso c), e) enfriar lentamente la solución supersaturada obtenida en el paso b), el paso c) o el paso d) hasta temperatura ambiente, f) filtrar los cristales resultantes y lavarlos con alcohol / agua, y g) opcionalmente secar los cristales al vacío a una temperatura entre 20ºC y 60ºC, preferentemente comenzando a 20ºC y finalizando a 60ºC.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP11007823A EP2573086A1 (en) | 2011-09-26 | 2011-09-26 | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AR120291A2 true AR120291A2 (es) | 2022-02-09 |
Family
ID=46889067
Family Applications (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120103551A AR088043A1 (es) | 2011-09-26 | 2012-09-26 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
| ARP190102595A AR116394A2 (es) | 2011-09-26 | 2019-09-13 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
| ARP200102938A AR120291A2 (es) | 2011-09-26 | 2020-10-23 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-triazol-2-il]n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
Family Applications Before (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ARP120103551A AR088043A1 (es) | 2011-09-26 | 2012-09-26 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
| ARP190102595A AR116394A2 (es) | 2011-09-26 | 2019-09-13 | Mesilato de n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)fenil]acetamida monohidrato |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US9340535B2 (es) |
| EP (3) | EP2573086A1 (es) |
| JP (2) | JP6161614B2 (es) |
| KR (4) | KR20180088530A (es) |
| CN (2) | CN103842359B (es) |
| AR (3) | AR088043A1 (es) |
| AU (2) | AU2012314536B2 (es) |
| BR (1) | BR112014003245B1 (es) |
| CA (1) | CA2791142C (es) |
| CL (1) | CL2014000149A1 (es) |
| DK (2) | DK2598501T3 (es) |
| ES (2) | ES2466221T3 (es) |
| HK (1) | HK1220978A1 (es) |
| HR (1) | HRP20140351T1 (es) |
| IL (2) | IL230152A (es) |
| IN (1) | IN2014DN01993A (es) |
| JO (2) | JO3037B1 (es) |
| MX (2) | MX371088B (es) |
| MY (2) | MY190878A (es) |
| PE (1) | PE20141148A1 (es) |
| PH (2) | PH12014500567A1 (es) |
| PL (2) | PL2598501T3 (es) |
| PT (1) | PT2598501E (es) |
| RU (2) | RU2620604C2 (es) |
| SG (1) | SG10201407430TA (es) |
| TW (2) | TWI567070B (es) |
| UA (2) | UA119574C2 (es) |
| WO (1) | WO2013045479A1 (es) |
| ZA (2) | ZA201401773B (es) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP2573085A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(aminosulfonyl)-4methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl] acetamide mesylate monohydrate having a specific particle size distribution range and a specific surface area range |
| EP2573086A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
| AR108175A1 (es) * | 2016-04-06 | 2018-07-25 | Innovative Molecules Gmbh | Compuestos antivíricos de tiazol acetamida |
| WO2018096170A1 (en) * | 2016-11-28 | 2018-05-31 | Aicuris Anti-Infective Cures Gmbh | N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)-phenyl]-acetamide free base hemihydrate, methods of manufacture and uses thereof |
| UY37497A (es) * | 2016-11-28 | 2018-06-29 | Aicuris Anti Infective Cures Gmbh | Formulación tópica que comprende n-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-n-metil-2-[4-(2-piridinil)-fenil]-acetamida |
| TWI808591B (zh) | 2016-11-28 | 2023-07-11 | 德商艾庫瑞斯公司 | N-[5-(胺基磺醯基)-4-甲基-1,3-噻唑-2-基]-n-甲基-2-[4-(2-吡啶基)-苯基]-乙醯胺之游離鹼之硫酸鹽、其醫藥調配物及其用途 |
| KR102335327B1 (ko) | 2017-04-28 | 2021-12-03 | 현대자동차 주식회사 | 수냉식 이지알 쿨러 |
| IL271725B2 (en) * | 2017-06-28 | 2025-09-01 | Aicuris Anti Infective Cures Ag | Intravaginally applicable devices comprising antiviral compounds |
| EP4209491A1 (en) | 2017-10-05 | 2023-07-12 | Innovative Molecules GmbH | Enantiomers of substituted thiazoles as antiviral compounds |
| KR102535452B1 (ko) * | 2018-07-06 | 2023-05-26 | 파에노 테라퓨틱스 씨오., 엘티디. | 티아졸 화합물의 결정형 및 이의 응용 |
| EP4509118A3 (en) * | 2018-09-19 | 2025-05-14 | ModernaTX, Inc. | High-purity peg lipids and uses thereof |
| TW202038947A (zh) | 2018-11-28 | 2020-11-01 | 德商創新分子有限責任公司 | 在與溶瘤病毒之組合療法中治療癌症的解旋酶引子酶抑制劑 |
| WO2021191320A1 (en) * | 2020-03-26 | 2021-09-30 | Aicuris Gmbh & Co. Kg | Ophthalmic formulation comprising n-[5-(aminosulfonyl)-4-methyl-1,3- thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide hemihydrate |
| US20260070900A1 (en) | 2022-08-29 | 2026-03-12 | Assembly Biosciences, Inc. | A novel crystalline form of pritelivir |
| EP4581031A1 (en) | 2022-08-29 | 2025-07-09 | Assembly Biosciences, Inc. | A novel crystalline form of pritelivir |
| AU2023332667A1 (en) | 2022-08-29 | 2025-03-13 | Assembly Biosciences, Inc. | Pharmaceutical compositions for herpes virus |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DOP2000000109A (es) | 1999-12-23 | 2002-08-30 | Gerald Kleymann | Derivados de tiazolilamida |
| DE10129714A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Topische Anwendung von Thiazolylamiden |
| DE10129716A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Kombinationspräparate zur Herpes-Behandlung |
| DE10129717A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Kombinationspräparate zur Herpes-Behandlung |
| DE10131128A1 (de) * | 2001-06-28 | 2003-01-16 | Bayer Ag | Sekundäre Sulfonamide |
| GB0423653D0 (en) * | 2004-10-25 | 2004-11-24 | Piramed Ltd | Pharmaceutical compounds |
| DE102005014248A1 (de) | 2005-03-30 | 2006-10-05 | Aicuris Gmbh & Co. Kg | Pharmazeutische Zubereitung von N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamid |
| JP2007314516A (ja) * | 2006-04-25 | 2007-12-06 | Daiichi Sankyo Co Ltd | ２以上の置換基を有するベンゼン化合物を含有する医薬 |
| EA200802417A1 (ru) * | 2006-06-09 | 2009-06-30 | Икос Корпорейшн | Замещенные фенилуксусные кислоты как dp-2-антагонисты |
| AR070127A1 (es) * | 2008-01-11 | 2010-03-17 | Novartis Ag | Pirrolo - pirimidinas y pirrolo -piridinas |
| UA103918C2 (en) * | 2009-03-02 | 2013-12-10 | Айерем Элелси | N-(hetero)aryl, 2-(hetero)aryl-substituted acetamides for use as wnt signaling modulators |
| EP2573085A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(aminosulfonyl)-4methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl] acetamide mesylate monohydrate having a specific particle size distribution range and a specific surface area range |
| EP2573086A1 (en) * | 2011-09-26 | 2013-03-27 | AiCuris GmbH & Co. KG | N-[5-(Aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-N-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
-
2011
- 2011-09-26 EP EP11007823A patent/EP2573086A1/en not_active Withdrawn
-
2012
- 2012-09-21 TW TW105109173A patent/TWI567070B/zh active
- 2012-09-21 TW TW101134784A patent/TWI532739B/zh active
- 2012-09-23 JO JOP/2012/0276A patent/JO3037B1/ar active
- 2012-09-26 JP JP2014532361A patent/JP6161614B2/ja active Active
- 2012-09-26 WO PCT/EP2012/068938 patent/WO2013045479A1/en not_active Ceased
- 2012-09-26 PL PL12762300T patent/PL2598501T3/pl unknown
- 2012-09-26 MY MYPI2017702805A patent/MY190878A/en unknown
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