TWI532739B - 用於合成ｎ－［５－（胺磺醯基）－４－甲基－１，３－噻唑－２－基］－ｎ－甲基－２－［４－（２－吡啶基）苯基］乙醯胺之方法 - Google Patents
用於合成ｎ－［５－（胺磺醯基）－４－甲基－１，３－噻唑－２－基］－ｎ－甲基－２－［４－（２－吡啶基）苯基］乙醯胺之方法 Download PDFInfo
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- TWI532739B TWI532739B TW101134784A TW101134784A TWI532739B TW I532739 B TWI532739 B TW I532739B TW 101134784 A TW101134784 A TW 101134784A TW 101134784 A TW101134784 A TW 101134784A TW I532739 B TWI532739 B TW I532739B
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- Prior art keywords
- methyl
- phenyl
- thiazol
- pyridyl
- acetamide
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 24
- 230000015572 biosynthetic process Effects 0.000 title claims description 19
- 238000003786 synthesis reaction Methods 0.000 title claims description 17
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 title description 8
- 229960005489 paracetamol Drugs 0.000 title description 4
- OIXMUQLVDNPHNS-UHFFFAOYSA-N methanesulfonic acid;hydrate Chemical compound O.CS(O)(=O)=O OIXMUQLVDNPHNS-UHFFFAOYSA-N 0.000 claims description 47
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims description 35
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- DZNBZPKZOBDXEL-UHFFFAOYSA-N dicyclohexyl-(2-dicyclohexylphosphanylphenyl)phosphane Chemical compound C1CCCCC1P(C=1C(=CC=CC=1)P(C1CCCCC1)C1CCCCC1)C1CCCCC1 DZNBZPKZOBDXEL-UHFFFAOYSA-N 0.000 claims description 14
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Classifications
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- 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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/12—Antivirals
- A61P31/20—Antivirals for DNA viruses
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- 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
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- 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
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- 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
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- Veterinary Medicine (AREA)
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- Animal Behavior & Ethology (AREA)
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- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
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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 (2)
| Publication Number | Publication Date |
|---|---|
| TW201317234A TW201317234A (zh) | 2013-05-01 |
| TWI532739B true TWI532739B (zh) | 2016-05-11 |
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| TW101134784A TWI532739B (zh) | 2011-09-26 | 2012-09-21 | 用於合成ｎ－［５－（胺磺醯基）－４－甲基－１，３－噻唑－２－基］－ｎ－甲基－２－［４－（２－吡啶基）苯基］乙醯胺之方法 |
| TW105109173A TWI567070B (zh) | 2011-09-26 | 2012-09-21 | 結晶ｎ-﹝５-（胺磺醯基）-４-甲基-１，３-噻唑-２-基﹞-ｎ-甲基-２-﹝４-（２-吡啶基）苯基﹞乙醯胺甲烷磺酸單水化物、其組合物、其用途以及包括其的醫藥組成物 |
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| TW105109173A TWI567070B (zh) | 2011-09-26 | 2012-09-21 | 結晶ｎ-﹝５-（胺磺醯基）-４-甲基-１，３-噻唑-２-基﹞-ｎ-甲基-２-﹝４-（２-吡啶基）苯基﹞乙醯胺甲烷磺酸單水化物、其組合物、其用途以及包括其的醫藥組成物 |
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| EP (3) | EP2573086A1 (enExample) |
| JP (2) | JP6161614B2 (enExample) |
| KR (4) | KR20180088530A (enExample) |
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| SG (1) | SG10201407430TA (enExample) |
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| 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 |
| PH12018501979B1 (en) * | 2016-04-06 | 2023-05-05 | Innovative Molecules Gmbh | Aminothiazole derivatives useful as antiviral agents |
| ES2877854T3 (es) | 2016-11-28 | 2021-11-17 | Aicuris Gmbh & Co Kg | Una sal de maleato de la base libre de N-[5-(aminosulfonil)-4-metil-1,3-tiazol-2-il]-N-metil-2-[4-(2-piridinil)-fenil]-acetamida, formulaciones farmacéuticas, procedimientos de fabricación y usos de las mismas para el tratamiento de los virus del herpes |
| TWI811800B (zh) * | 2016-11-28 | 2023-08-11 | 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]-乙醯胺游離鹼半水合物、製造方法及其用途 |
| TW201825095A (zh) * | 2016-11-28 | 2018-07-16 | 德商艾庫里斯抗感染治療有限公司 | 包含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]-乙醯胺之局部醫藥調配物 |
| KR102335327B1 (ko) | 2017-04-28 | 2021-12-03 | 현대자동차 주식회사 | 수냉식 이지알 쿨러 |
| WO2019002486A1 (en) * | 2017-06-28 | 2019-01-03 | Aicuris Anti-Infective Cures Gmbh | Intravaginally applicable devices comprising antiviral compounds |
| PL3692039T3 (pl) | 2017-10-05 | 2023-04-17 | Innovative Molecules Gmbh | Enancjomery podstawionych tiazoli jako związki przeciwwirusowe |
| 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 |
| CN112996854B (zh) * | 2018-09-19 | 2024-08-30 | 摩登纳特斯有限公司 | 高纯度peg脂质和其用途 |
| 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 |
| EP4096632A1 (en) * | 2020-03-26 | 2022-12-07 | 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 |
| JP2025527942A (ja) | 2022-08-29 | 2025-08-25 | 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 | 新規な結晶形態 |
| JP2025527943A (ja) | 2022-08-29 | 2025-08-25 | 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 | 新規な結晶形態 |
| EP4580601A1 (en) | 2022-08-29 | 2025-07-09 | Assembly Biosciences, Inc. | Pharmaceutical compositions for herpes virus |
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| 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 |
| JP2009539881A (ja) * | 2006-06-09 | 2009-11-19 | アイコス コーポレイション | Ｄｐ−２アンタゴニストとしての置換フェニル酢酸 |
| 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 |
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2011
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2012
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- 2012-09-26 JP JP2014532361A patent/JP6161614B2/ja active Active
- 2012-09-26 KR KR1020187021891A patent/KR20180088530A/ko not_active Ceased
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- 2012-09-26 HR HRP20140351AT patent/HRP20140351T1/hr unknown
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- 2012-09-26 UA UAA201704493A patent/UA119574C2/uk unknown
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2013
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2014
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2015
- 2015-11-24 AU AU2015260762A patent/AU2015260762B2/en active Active
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2016
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2019
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2020
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