HRP20201594T1 - Novi kristalni oblik soli 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1h-pirol-3-il)-n- metilmetanamina - Google Patents
Novi kristalni oblik soli 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1h-pirol-3-il)-n- metilmetanamina Download PDFInfo
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- HRP20201594T1 HRP20201594T1 HRP20201594TT HRP20201594T HRP20201594T1 HR P20201594 T1 HRP20201594 T1 HR P20201594T1 HR P20201594T T HRP20201594T T HR P20201594TT HR P20201594 T HRP20201594 T HR P20201594T HR P20201594 T1 HRP20201594 T1 HR P20201594T1
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- Prior art keywords
- pyrrol
- difluorophenyl
- fluorophenyl
- sulfonyl
- methoxy
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- OUNXGNDVWVPCOL-UHFFFAOYSA-N 1-[5-(2,4-difluorophenyl)-1-(3-fluorophenyl)sulfonyl-4-methoxypyrrol-3-yl]-N-methylmethanamine Chemical class FC1=C(C=CC(=C1)F)C1=C(C(=CN1S(=O)(=O)C1=CC(=CC=C1)F)CNC)OC OUNXGNDVWVPCOL-UHFFFAOYSA-N 0.000 title 1
- 239000013078 crystal Substances 0.000 claims 7
- 238000002441 X-ray diffraction Methods 0.000 claims 6
- 238000000113 differential scanning calorimetry Methods 0.000 claims 6
- 230000000977 initiatory effect Effects 0.000 claims 6
- 239000000843 powder Substances 0.000 claims 6
- QJINUJZXHUKGHS-WLHGVMLRSA-N (E)-but-2-enedioic acid 1-[5-(2,4-difluorophenyl)-1-(3-fluorophenyl)sulfonyl-4-methoxypyrrol-3-yl]-N-methylmethanamine Chemical compound OC(=O)\C=C\C(O)=O.CNCc1cn(c(c1OC)-c1ccc(F)cc1F)S(=O)(=O)c1cccc(F)c1 QJINUJZXHUKGHS-WLHGVMLRSA-N 0.000 claims 4
- BOHTZYBQQDVIRI-UHFFFAOYSA-N 1-[5-(2,4-difluorophenyl)-1-(3-fluorophenyl)sulfonyl-4-methoxypyrrol-3-yl]-N-methylmethanamine hydrochloride Chemical compound Cl.CNCc1cn(c(c1OC)-c1ccc(F)cc1F)S(=O)(=O)c1cccc(F)c1 BOHTZYBQQDVIRI-UHFFFAOYSA-N 0.000 claims 4
- LSVWZWATNOUXTH-UHFFFAOYSA-N 1-[5-(2,4-difluorophenyl)-1-(3-fluorophenyl)sulfonyl-4-methoxypyrrol-3-yl]-N-methylmethanamine 2,3-dihydroxybutanedioic acid Chemical compound OC(C(O)C(O)=O)C(O)=O.CNCc1cn(c(c1OC)-c1ccc(F)cc1F)S(=O)(=O)c1cccc(F)c1 LSVWZWATNOUXTH-UHFFFAOYSA-N 0.000 claims 2
- YMGMDJOHRYZJMN-UHFFFAOYSA-N butanedioic acid 1-[5-(2,4-difluorophenyl)-1-(3-fluorophenyl)sulfonyl-4-methoxypyrrol-3-yl]-N-methylmethanamine Chemical compound OC(=O)CCC(O)=O.CNCc1cn(c(c1OC)-c1ccc(F)cc1F)S(=O)(=O)c1cccc(F)c1 YMGMDJOHRYZJMN-UHFFFAOYSA-N 0.000 claims 2
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
-
- 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
- A61K31/40—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with one nitrogen as the only ring hetero atom, e.g. sulpiride, succinimide, tolmetin, buflomedil
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Pyrrole Compounds (AREA)
Claims (12)
1. Kristalni oblik I 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin hidroklorida koji ima vrhove kuteva difrakcije (2θ±0.2°) od 5.8°, 9.7°, 10.0°, 12.8°, 13.2°, 17.4° I 18.5° na difraktogramu praha dobivenom difrakcijom X-zraka.
2. Kristalni oblik I 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin hidroklorida sukladno zahtjevu 1,
pri čemu kristalni oblik I ima endotermnu temperature inicijacije od 215.02±3°C i pokazuje maksimum endotermnog vrhunca za endotermnu temperaturu od 217.11±3 °C u analizi diferencijalne skenirajuće kalorimetrije.
3. Kristalni oblik II 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin hidroklorida koji ima vrhove kuteva difrakcije (2θ±0.2°) od 9.2°, 10.0°, 12.9° i 20.2° na difraktogramu praha dobivenom difrakcijom X-zraka.
4. Kristalni oblik II 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin hidroklorida sukladno zahtjevu 3,
pri čemu kristalni oblik II ima endotermnu temperature inicijacije od 213.14±3°C i pokazuje maksimum endotermnog vrhunca za endotermnu temperaturu od 215.7±3°C u analizi diferencijalne skenirajuće kalorimetrije.
5. Kristalni oblik 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin sukcinata koji ima vrhove kuteva difrakcije (2θ±0.2°) od 8.0°, 11.2°, 12.0°, 14.9°, 22.1° i 24.1° na difraktogramu praha dobivenom difrakcijom X-zraka.
6. Kristalni oblik 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin sukcinata sukladno zahtjevu 5,
pri čemu kristalni oblik ima endotermnu temperature inicijacije od 132.3±3°C i pokazuje maksimum endotermnog vrhunca za endotermnu temperaturu od 133.9±3°C pri analizi diferencijalne skenirajuće kalorimetrije.
7. Kristalni oblik 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin tartrata koji ima vrhove kuteva difrakcije (2θ±0.2°) od 11.7°, 21.5° i 23.5° na difraktogramu praha dobivenom difrakcijom X-zraka.
8. Kristalni oblik 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin tartrata sukladno zahtjevu 7,
pri čemu kristalni oblik ima endotermnu temperature inicijacije od 146.34±3°C i pokazuje maksimum endotermnog vrhunca za endotermnu temperaturu od 148.27±3°C pri analizi diferencijalne skenirajuće kalorimetrije.
9. Kristalni oblik I 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin fumarata koji ima vrhove kuteva difrakcije (2θ±0.2°) od 7.9°, 11.9° i 24.0° na difraktogramu praha dobivenom difrakcijom X-zraka.
10. Kristalni oblik I 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin fumarata sukladno zahtjevu 9,
pri čemu kristalni oblik i ima endotermnu temperature inicijacije od 164.97±3°C i pokazuje maksimum endotermnog vrhunca za endotermnu temperaturu od 167.46±3°C pri analizi diferencijalne skenirajuće kalorimetrije.
11. Kristalni oblik II 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin fumarata koji ima vrhove kuteva difrakcije (2θ±0.2°) od 8.4°, 10.5° i 19.02° na difraktogramu praha dobivenom difrakcijom X-zraka.
12. Kristalni oblik II 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1H-pirol-3-il)-N-metilmetanamin fumarata sukladno zahtjevu 11,
pri čemu kristalni oblik II ima endotermnu temperature inicijacije od 179.47±3°C i pokazuje maksimum endotermnog vrhunca za endotermnu temperaturu od 189.05±3°C pri analizi diferencijalne skenirajuće kalorimetrije.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| KR1020160036080A KR102081920B1 (ko) | 2016-03-25 | 2016-03-25 | 1-(5-(2,4-다이플루오로페닐)-1-((3-플루오로페닐)술포닐)-4-메톡시-1h-피롤-3-일)-n-메틸메탄아민 염의 신규한 결정형 |
| PCT/KR2017/002914 WO2017164576A1 (en) | 2016-03-25 | 2017-03-17 | Novel crystalline form of 1-(5-(2,4-difluorophenyl)-l-((3- fluorophenyl)sulfonyl)-4-methoxy-1h-pyrrol-3-yl)-n- methylmethanamine salt |
| EP17770546.4A EP3433233B1 (en) | 2016-03-25 | 2017-03-17 | Novel crystalline form of 1-(5-(2,4-difluorophenyl)-1-((3- fluorophenyl)sulfonyl)-4-methoxy-1h-pyrrol-3-yl)-n- methylmethanamine salt |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20201594T1 true HRP20201594T1 (hr) | 2020-12-11 |
Family
ID=59900401
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HRP20201594TT HRP20201594T1 (hr) | 2016-03-25 | 2020-10-06 | Novi kristalni oblik soli 1-(5-(2,4-difluorofenil)-1-((3-fluorofenil)sulfonil)-4-metoksi-1h-pirol-3-il)-n- metilmetanamina |
Country Status (32)
| Country | Link |
|---|---|
| US (6) | US10336695B2 (hr) |
| EP (1) | EP3433233B1 (hr) |
| JP (1) | JP6554617B2 (hr) |
| KR (1) | KR102081920B1 (hr) |
| CN (1) | CN108602772B (hr) |
| AR (1) | AR107963A1 (hr) |
| AU (1) | AU2017238918B2 (hr) |
| BR (1) | BR112018069461A2 (hr) |
| CA (1) | CA3014745C (hr) |
| CL (3) | CL2018002416A1 (hr) |
| CO (1) | CO2018008833A2 (hr) |
| DO (1) | DOP2018000190A (hr) |
| EA (1) | EA029995B1 (hr) |
| ES (1) | ES2818902T3 (hr) |
| HK (1) | HK1254393A1 (hr) |
| HR (1) | HRP20201594T1 (hr) |
| HU (1) | HUE053502T2 (hr) |
| JO (1) | JOP20170070B1 (hr) |
| MA (1) | MA43833B1 (hr) |
| MX (1) | MX2018009219A (hr) |
| MY (1) | MY196299A (hr) |
| NZ (1) | NZ745266A (hr) |
| PE (1) | PE20190170A1 (hr) |
| PH (1) | PH12018501846B1 (hr) |
| PL (1) | PL3433233T3 (hr) |
| PT (1) | PT3433233T (hr) |
| RS (1) | RS60884B1 (hr) |
| SG (1) | SG11201806966SA (hr) |
| SI (1) | SI3433233T1 (hr) |
| TN (1) | TN2018000288A1 (hr) |
| TW (1) | TWI626234B (hr) |
| WO (1) | WO2017164576A1 (hr) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR102081920B1 (ko) | 2016-03-25 | 2020-02-26 | 주식회사 대웅제약 | 1-(5-(2,4-다이플루오로페닐)-1-((3-플루오로페닐)술포닐)-4-메톡시-1h-피롤-3-일)-n-메틸메탄아민 염의 신규한 결정형 |
| KR102233456B1 (ko) | 2017-05-31 | 2021-03-29 | 주식회사 대웅제약 | 4-메톡시피롤 유도체의 중간체 제조 방법 |
| KR102233455B1 (ko) * | 2017-06-21 | 2021-03-29 | 주식회사 대웅제약 | 4-메톡시피롤 유도체의 중간체 제조 방법 |
| KR102126576B1 (ko) * | 2018-09-19 | 2020-06-24 | 주식회사 대웅제약 | 4-메톡시 피롤 유도체의 제조 방법 |
| EP4079293A4 (en) * | 2019-12-18 | 2024-01-03 | Daewoong Pharmaceutical Co., Ltd. | LIQUID PHARMACEUTICAL COMPOSITION OF 1-(5-(2,4-DIFLUORPHENYL)-1-((3-FLUOROPHENYL)SULFONYL)-4-METHOXY-1H-PYRROL-3-YL)-N-METHYLMETHANEAMINE |
| CN117820193A (zh) * | 2022-09-29 | 2024-04-05 | 安徽皓元药业有限公司 | 一种非苏拉赞盐酸盐晶型a及其制备方法 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CA2582777A1 (en) * | 2004-09-30 | 2006-04-06 | Takeda Pharmaceutical Company Limited | Proton pump inhibitors |
| ME00610B (me) | 2005-08-30 | 2011-12-20 | Takeda Pharmaceuticals Co | 1 –heterociklilsulfonil, 2 –aminometil, 5– (hetero–) aril supstituisan 1–h–pirol derivati kao inhibitori lučenja kiseline |
| JP5207964B2 (ja) * | 2006-03-31 | 2013-06-12 | 武田薬品工業株式会社 | 酸分泌抑制薬 |
| US20100113524A1 (en) * | 2006-09-19 | 2010-05-06 | Garst Michael E | Prodrugs of proton pump inhibitors including the (1h-pyrrol-1-yl)-1h-benzimidazole moiety |
| US8933105B2 (en) * | 2007-02-28 | 2015-01-13 | Takeda Pharmaceutical Company Limited | Pyrrole compounds |
| KR20150084974A (ko) | 2012-11-19 | 2015-07-22 | 장쑤 한서 파마슈티칼 캄파니 리미티드 | 피롤 설폰아미드 유도체, 이의 제조 방법, 및 이의 의학적 적용 |
| KR102084185B1 (ko) | 2013-08-29 | 2020-03-04 | 주식회사 대웅제약 | 테트라히드로사이클로펜타피롤 유도체 및 이의 제조방법 |
| CN104447491B (zh) * | 2014-11-19 | 2017-06-23 | 连云港恒运医药有限公司 | 含吡咯环质子泵抑制剂的半富马酸盐及其中间体和医药用途 |
| CN104447490B (zh) * | 2014-11-19 | 2017-06-06 | 连云港恒运医药有限公司 | 一种质子泵抑制剂的晶型、制备中间体及其合成方法和医药用途 |
| KR101613245B1 (ko) * | 2015-04-27 | 2016-04-18 | 주식회사 대웅제약 | 신규의 4-메톡시 피롤 유도체 또는 이의 염 및 이를 포함하는 약학 조성물 |
| KR20170113040A (ko) * | 2016-03-25 | 2017-10-12 | 주식회사 대웅제약 | 1-(5-(2,4-다이플루오로페닐)-1-((3-플루오로페닐)술포닐)-4-메톡시-1h-피롤-3-일)-n-메틸메탄아민의 신규한 산부가염 |
| KR102081920B1 (ko) | 2016-03-25 | 2020-02-26 | 주식회사 대웅제약 | 1-(5-(2,4-다이플루오로페닐)-1-((3-플루오로페닐)술포닐)-4-메톡시-1h-피롤-3-일)-n-메틸메탄아민 염의 신규한 결정형 |
| KR102233456B1 (ko) | 2017-05-31 | 2021-03-29 | 주식회사 대웅제약 | 4-메톡시피롤 유도체의 중간체 제조 방법 |
| KR102233455B1 (ko) | 2017-06-21 | 2021-03-29 | 주식회사 대웅제약 | 4-메톡시피롤 유도체의 중간체 제조 방법 |
| KR102126576B1 (ko) | 2018-09-19 | 2020-06-24 | 주식회사 대웅제약 | 4-메톡시 피롤 유도체의 제조 방법 |
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