JP2014528948A5 - - Google Patents
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- Publication number
- JP2014528948A5 JP2014528948A5 JP2014532361A JP2014532361A JP2014528948A5 JP 2014528948 A5 JP2014528948 A5 JP 2014528948A5 JP 2014532361 A JP2014532361 A JP 2014532361A JP 2014532361 A JP2014532361 A JP 2014532361A JP 2014528948 A5 JP2014528948 A5 JP 2014528948A5
- Authority
- JP
- Japan
- Prior art keywords
- methyl
- reagent
- aminosulfonyl
- thiazol
- pyridinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 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 claims description 4
- LVLDBZCFWNSVLJ-UHFFFAOYSA-N 4-methyl-2-(methylamino)-1,3-thiazole-5-sulfonamide Chemical compound CNC1=NC(C)=C(S(N)(=O)=O)S1 LVLDBZCFWNSVLJ-UHFFFAOYSA-N 0.000 claims description 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 10
- 238000000034 method Methods 0.000 claims 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims 6
- 150000001642 boronic acid derivatives Chemical class 0.000 claims 5
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 4
- 125000004432 carbon atom Chemical group C* 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 3
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims 3
- HBXRPXYBMZDIQL-UHFFFAOYSA-N 1$l^{2}-borolane Chemical compound [B]1CCCC1 HBXRPXYBMZDIQL-UHFFFAOYSA-N 0.000 claims 2
- KPAUORDXNFURBA-UHFFFAOYSA-N 2-(4-pyridin-2-ylphenyl)acetic acid Chemical compound C1=CC(CC(=O)O)=CC=C1C1=CC=CC=N1 KPAUORDXNFURBA-UHFFFAOYSA-N 0.000 claims 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims 2
- 229940126062 Compound A Drugs 0.000 claims 2
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims 2
- 239000012445 acidic reagent Substances 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 2
- VBXDEEVJTYBRJJ-UHFFFAOYSA-N diboronic acid Chemical compound OBOBO VBXDEEVJTYBRJJ-UHFFFAOYSA-N 0.000 claims 2
- 229940098779 methanesulfonic acid Drugs 0.000 claims 2
- 239000000203 mixture Substances 0.000 claims 2
- 239000003960 organic solvent Substances 0.000 claims 2
- -1 pyridine compound Chemical class 0.000 claims 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- OLDXRTOEUPVZKB-UHFFFAOYSA-N B1CCCC1 Chemical compound B1CCCC1 OLDXRTOEUPVZKB-UHFFFAOYSA-N 0.000 claims 1
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
- 101150003085 Pdcl gene Proteins 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- BIOOXWXQBSHAMB-UHFFFAOYSA-N borinane Chemical compound B1CCCCC1 BIOOXWXQBSHAMB-UHFFFAOYSA-N 0.000 claims 1
- 238000001816 cooling Methods 0.000 claims 1
- 230000008878 coupling Effects 0.000 claims 1
- 238000010168 coupling process Methods 0.000 claims 1
- 238000005859 coupling reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 230000008030 elimination Effects 0.000 claims 1
- 238000003379 elimination reaction Methods 0.000 claims 1
- 238000002156 mixing Methods 0.000 claims 1
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 239000000546 pharmaceutical excipient Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims 1
- 239000002904 solvent Substances 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 238000003756 stirring Methods 0.000 claims 1
- 230000002194 synthesizing effect Effects 0.000 claims 1
- 0 *Cc(cc1)ccc1I Chemical compound *Cc(cc1)ccc1I 0.000 description 4
- CENMEJUYOOMFFZ-UHFFFAOYSA-N B1Oc(cccc2)c2O1 Chemical compound B1Oc(cccc2)c2O1 CENMEJUYOOMFFZ-UHFFFAOYSA-N 0.000 description 1
Applications Claiming Priority (3)
| 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 |
| EP11007823.5 | 2011-09-26 | ||
| PCT/EP2012/068938 WO2013045479A1 (en) | 2011-09-26 | 2012-09-26 | N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)phenyl]acetamide mesylate monohydrate |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016249351A Division JP6353022B2 (ja) | 2011-09-26 | 2016-12-22 | Ｎ−［５−（アミノスルホニル）−４−メチル−１，３−チアゾール−２−イル］−ｎ−メチル−２−［４−（２−ピリジニル）フェニル］アセトアミドメシレート一水和物 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| JP2014528948A JP2014528948A (ja) | 2014-10-30 |
| JP2014528948A5 true JP2014528948A5 (enExample) | 2015-10-15 |
| JP6161614B2 JP6161614B2 (ja) | 2017-07-12 |
Family
ID=46889067
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2014532361A Active JP6161614B2 (ja) | 2011-09-26 | 2012-09-26 | Ｎ−［５−（アミノスルホニル）−４−メチル−１，３−チアゾール−２−イル］−ｎ−メチル−２−［４−（２−ピリジニル）フェニル］アセトアミドメシレート一水和物 |
| JP2016249351A Active JP6353022B2 (ja) | 2011-09-26 | 2016-12-22 | Ｎ−［５−（アミノスルホニル）−４−メチル−１，３−チアゾール−２−イル］−ｎ−メチル−２−［４−（２−ピリジニル）フェニル］アセトアミドメシレート一水和物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP2016249351A Active JP6353022B2 (ja) | 2011-09-26 | 2016-12-22 | Ｎ−［５−（アミノスルホニル）−４−メチル−１，３−チアゾール−２−イル］−ｎ−メチル−２−［４−（２−ピリジニル）フェニル］アセトアミドメシレート一水和物 |
Country Status (29)
| Country | Link |
|---|---|
| US (1) | US9340535B2 (enExample) |
| EP (3) | EP2573086A1 (enExample) |
| JP (2) | JP6161614B2 (enExample) |
| KR (4) | KR20190104249A (enExample) |
| CN (2) | CN105541829A (enExample) |
| AR (3) | AR088043A1 (enExample) |
| AU (2) | AU2012314536B2 (enExample) |
| BR (1) | BR112014003245B1 (enExample) |
| CA (1) | CA2791142C (enExample) |
| CL (1) | CL2014000149A1 (enExample) |
| DK (2) | DK2602258T3 (enExample) |
| ES (2) | ES2462492T3 (enExample) |
| HK (1) | HK1220978A1 (enExample) |
| HR (1) | HRP20140351T1 (enExample) |
| IL (2) | IL230152A (enExample) |
| IN (1) | IN2014DN01993A (enExample) |
| JO (2) | JO3037B1 (enExample) |
| MX (2) | MX338736B (enExample) |
| MY (2) | MY185063A (enExample) |
| PE (1) | PE20141148A1 (enExample) |
| PH (2) | PH12014500567A1 (enExample) |
| PL (2) | PL2598501T3 (enExample) |
| PT (1) | PT2598501E (enExample) |
| RU (2) | RU2669388C1 (enExample) |
| SG (1) | SG10201407430TA (enExample) |
| TW (2) | TWI567070B (enExample) |
| UA (2) | UA119574C2 (enExample) |
| WO (1) | WO2013045479A1 (enExample) |
| ZA (2) | ZA201401773B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| EP3440063B1 (en) * | 2016-04-06 | 2020-08-05 | Innovative Molecules GmbH | Aminothiazole derivatives useful as antiviral agents |
| DK3848369T3 (da) * | 2016-11-28 | 2023-03-27 | Aicuris Gmbh & Co Kg | N-[5-(aminosulfonyl)-4-methyl-1,3-thiazol-2-yl]-n-methyl-2-[4-(2-pyridinyl)-phenyl]-acetamid-fri base hæmihydrat, fremgangsmåder til fremstilling og anvendelser deraf |
| PL3544977T3 (pl) | 2016-11-28 | 2021-11-08 | Aicuris Gmbh & Co. Kg | Sól maleinianowa wolnej zasady n-[5-(aminosulfonylo)-4-metylo-1,3-tiazol-2-ilo]-n-metylo-2-[4-(2-pirydynylo)fe¬nylo]acetamidu, preparaty farmaceutyczne, sposoby wytwarzania oraz ich zastosowania do leczenia wirusa opryszczki |
| AR110250A1 (es) * | 2016-11-28 | 2019-03-13 | 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 |
| KR102335327B1 (ko) | 2017-04-28 | 2021-12-03 | 현대자동차 주식회사 | 수냉식 이지알 쿨러 |
| BR112019028013A2 (pt) | 2017-06-28 | 2020-07-07 | Aicuris Anti-Infective Cures Gmbh | dispositivos aplicáveis intravaginalmente que compreendem compostos antivirais |
| CR20200154A (es) | 2017-10-05 | 2020-05-24 | Innovative Molecules Gmbh | Enantiómeros de tiazoles sustituidos como compuestos antivirales |
| WO2020007355A1 (zh) | 2018-07-06 | 2020-01-09 | 南京明德新药研发有限公司 | 噻唑类化合物的晶型及其应用 |
| 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 |
| AU2021241823B2 (en) * | 2020-03-26 | 2025-07-24 | Aic316 Gmbh | Ophthalmic formulation comprising N-(5-(aminosulfonyl)-4-methyl-1,3- thiazol-2-yl)-N-methyl-2-(4-(2-pyridinyl)phenyl)acetamide hemihydrate |
| CN119816497A (zh) | 2022-08-29 | 2025-04-11 | 组装生物科学股份有限公司 | 普瑞利韦的新的结晶形式 |
| CN119731171A (zh) | 2022-08-29 | 2025-03-28 | 组装生物科学股份有限公司 | 普瑞利韦的新的结晶形式 |
| JP2025530762A (ja) | 2022-08-29 | 2025-09-17 | アセンブリー・バイオサイエンシーズ・インコーポレイテッド | ヘルペスウイルス用医薬組成物 |
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 |
| DE10129716A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Kombinationspräparate zur Herpes-Behandlung |
| DE10129714A1 (de) * | 2001-06-22 | 2003-01-02 | Bayer Ag | Topische Anwendung von Thiazolylamiden |
| 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 |
| AU2007257841A1 (en) * | 2006-06-09 | 2007-12-21 | Icos Corporation | Substituted phenyl acetic acids as DP-2 antagonists |
| 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 IN IN1993DEN2014 patent/IN2014DN01993A/en unknown
- 2012-09-26 MX MX2014003389A patent/MX338736B/es active IP Right Grant
- 2012-09-26 WO PCT/EP2012/068938 patent/WO2013045479A1/en not_active Ceased
- 2012-09-26 MY MYPI2014000656A patent/MY185063A/en unknown
- 2012-09-26 PT PT127623007T patent/PT2598501E/pt unknown
- 2012-09-26 KR KR1020197025387A patent/KR20190104249A/ko not_active Ceased
- 2012-09-26 RU RU2017114501A patent/RU2669388C1/ru active
- 2012-09-26 DK DK13157396.6T patent/DK2602258T3/da active
- 2012-09-26 ES ES12762300.7T patent/ES2462492T3/es active Active
- 2012-09-26 ES ES13157396.6T patent/ES2466221T3/es active Active
- 2012-09-26 PL PL12762300T patent/PL2598501T3/pl unknown
- 2012-09-26 UA UAA201704493A patent/UA119574C2/uk unknown
- 2012-09-26 EP EP13157396.6A patent/EP2602258B8/en active Active
- 2012-09-26 CN CN201511005819.8A patent/CN105541829A/zh active Pending
- 2012-09-26 HR HRP20140351AT patent/HRP20140351T1/hr unknown
- 2012-09-26 PH PH1/2014/500567A patent/PH12014500567A1/en unknown
- 2012-09-26 BR BR112014003245-9A patent/BR112014003245B1/pt active IP Right Grant
- 2012-09-26 SG SG10201407430TA patent/SG10201407430TA/en unknown
- 2012-09-26 KR KR1020147004026A patent/KR101768295B1/ko active Active
- 2012-09-26 RU RU2014107430A patent/RU2620604C2/ru active
- 2012-09-26 CA CA2791142A patent/CA2791142C/en active Active
- 2012-09-26 DK DK12762300.7T patent/DK2598501T3/da active
- 2012-09-26 AU AU2012314536A patent/AU2012314536B2/en active Active
- 2012-09-26 UA UAA201404411A patent/UA115317C2/uk unknown
- 2012-09-26 CN CN201280046744.6A patent/CN103842359B/zh active Active
- 2012-09-26 PE PE2014000390A patent/PE20141148A1/es active IP Right Grant
- 2012-09-26 AR ARP120103551A patent/AR088043A1/es not_active Application Discontinuation
- 2012-09-26 EP EP12762300.7A patent/EP2598501B1/en active Active
- 2012-09-26 PL PL13157396T patent/PL2602258T3/pl unknown
- 2012-09-26 KR KR1020187021891A patent/KR20180088530A/ko not_active Ceased
- 2012-09-26 JP JP2014532361A patent/JP6161614B2/ja active Active
- 2012-09-26 KR KR1020177012548A patent/KR20170055565A/ko not_active Ceased
- 2012-09-26 US US14/347,287 patent/US9340535B2/en active Active
- 2012-09-26 MX MX2015016192A patent/MX371088B/es unknown
- 2012-09-26 MY MYPI2017702805A patent/MY190878A/en unknown
-
2013
- 2013-12-24 IL IL230152A patent/IL230152A/en active IP Right Grant
-
2014
- 2014-01-20 CL CL2014000149A patent/CL2014000149A1/es unknown
- 2014-03-11 ZA ZA2014/01773A patent/ZA201401773B/en unknown
- 2014-09-01 IL IL234405A patent/IL234405A/en active IP Right Grant
- 2014-09-02 HK HK16109165.2A patent/HK1220978A1/zh unknown
- 2014-11-27 ZA ZA2014/08734A patent/ZA201408734B/en unknown
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2015
- 2015-11-24 AU AU2015260762A patent/AU2015260762B2/en active Active
- 2015-12-16 PH PH12015502801A patent/PH12015502801A1/en unknown
-
2016
- 2016-06-07 JO JOP/2016/0114A patent/JO3734B1/ar active
- 2016-12-22 JP JP2016249351A patent/JP6353022B2/ja active Active
-
2019
- 2019-09-13 AR ARP190102595A patent/AR116394A2/es not_active Application Discontinuation
-
2020
- 2020-10-23 AR ARP200102938A patent/AR120291A2/es unknown
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