KR100939743B1 - 1,2-디히드로피리딘 화합물의 결정 및 그 제조 방법 - Google Patents
1,2-디히드로피리딘 화합물의 결정 및 그 제조 방법 Download PDFInfo
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- KR100939743B1 KR100939743B1 KR1020067020395A KR20067020395A KR100939743B1 KR 100939743 B1 KR100939743 B1 KR 100939743B1 KR 1020067020395 A KR1020067020395 A KR 1020067020395A KR 20067020395 A KR20067020395 A KR 20067020395A KR 100939743 B1 KR100939743 B1 KR 100939743B1
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- Prior art keywords
- pyridyl
- phenyl
- cyanophenyl
- diffraction
- crystal
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- NHWKTZWOSIVHOL-UHFFFAOYSA-N O=C(C=C1)NC=C1c1ncccc1 Chemical compound O=C(C=C1)NC=C1c1ncccc1 NHWKTZWOSIVHOL-UHFFFAOYSA-N 0.000 description 1
- JHBMGQOABUXDND-UHFFFAOYSA-N O=C(C=CC(c1ncccc1)=C1)N1c1ccccc1 Chemical compound O=C(C=CC(c1ncccc1)=C1)N1c1ccccc1 JHBMGQOABUXDND-UHFFFAOYSA-N 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
-
- 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
Abstract
Description
사용 원료 | 사용 목적 | 0.5 mg정 | 1.0 mg정 | 2.0 mg정 |
본 발명 화합물*1 | 토약 | 0.5 mg | 1.0 mg | 2.0 mg |
젖당 | 부형제 | 80.0 mg | 79.5 mg | 78.5 mg |
저치환도 히드록시프로필셀룰로오스 | 붕괴제 | 9.0 mg | 9.0 mg | 9.0 mg |
폴리비닐피롤리돈 | 결합제 | 5.0 mg | 5.0 mg | 5.0 mg |
저치환도 히드록시프로필셀룰로오스 | 붕괴제 | 5.0 mg | 5.0 mg | 5.0 mg |
스테아르산마그네슘 | 활택제 | 0.5 mg | 0.5 mg | 0.5 mg |
정제수 | 용매 | 적량 | 적량 | 적량 |
코팅 기재*2 | 코팅제 | 5.0 mg | 5.0 mg | 5.0 mg |
정제수 | 용매 | 적량 | 적량 | 적량 |
합계 | 105 mg | 105 mg | 적량 |
Claims (25)
- 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 8.7°에서 회절 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정.
- 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 12.5°에서 회절 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정.
- 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 8.7° 및 12.5°에서 회절 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정.
- 적외 흡수 스펙트럼(KBr법)에 있어서, 파수 1588±1 cm-1에서 흡수 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정.
- 적외 흡수 스펙트럼(KBr법)에 있어서, 파수 1588±1 cm-1 및 751±1 cm-1에서 흡수 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정.
- 13C 고체 NMR 스펙트럼에 있어서, 화학 시프트 146.7 ppm 및 123.3 ppm에서 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정.
- 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온을, 알코올계 용매, 알킬케톤계 용매 및 물로 이루어진 군에서 선택되는 1 또는 2의 용매를 결정화 용매로서 이용하여 결정화하는 것을 특징으로 하는 제1항 내지 제6항 중 어느 한 항에 기재한 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 수화물 결정의 제조 방법.
- 제7항에 있어서, 결정화 용매가 아세톤과 물의 혼합 용매인 제조 방법.
- 제7항에 있어서, 결정화 용매가 아세톤과 물(체적비 37:3∼24:16)의 혼합 용매인 제조 방법.
- 제7항에 있어서, 결정화를 60∼-30℃에서 실시하는 것을 특징으로 하는 제조 방법.
- 제7항에 있어서, 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온을 결정화 용매에 용해한 용액을 50℃ 이상에서 가열한 후, 40∼5℃/시간의 냉각 속도로 10∼-20℃까지 냉각시키는 것을 특징으로 하는 제조 방법.
- 제7항에 있어서, 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 중량에 대한 용량비로 10∼50배량(v/w)의 결정화 용매를 이용하는 것을 특징으로 하는 제조 방법.
- 제7항에 있어서, 60℃ 이하에서 종결정(種結晶)을 첨가하는 것을 특징으로 하는 제조 방법.
- 제7항에 있어서, 결정화한 후, 감압 건조시키는 것을 특징으로 하는 제조 방법.
- 제7항에 있어서, 결정화 및 감압 건조시킨 후, 대기 중에 방치하는 것을 특징으로 하는 제조 방법.
- 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 10.3°에서 회절 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 무수물 결정.
- 제16항에 있어서, 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 19.1°에서 회절 피크를 더 갖는 것인 결정.
- 13C 고체 NMR 스펙트럼에 있어서, 화학 시프트 149.0 ppm 및 125.6 ppm에서 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 무수물 결정.
- 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 16.7°에서 회절 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 무수물 결정.
- 제19항에 있어서, 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 12.9° 및 24.9°에서 회절 피크를 더 갖는 것인 결정.
- 적외 흡수 스펙트럼(KBr법)에 있어서, 파수 1658±1 cm-1에서 흡수 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 무수물 결 정.
- 제21항에 있어서, 적외 흡수 스펙트럼(KBr법)에 있어서, 파수 501±1 cm-1에서 흡수 피크를 더 갖는 것인 결정.
- 13C 고체 NMR 스펙트럼에 있어서, 화학 시프트 145.9 ppm 및 137.7 ppm에서 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 무수물 결정.
- 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 23.7° 및 25.0°에서 회절 피크를 갖는 3-(2-시아노페닐)-5-(2-피리딜)-1-페닐-1,2-디히드로피리딘-2-온의 무수물 결정.
- 제24항에 있어서, 분말 X선 회절에 있어서, 회절 각도(2θ±0.2°) 5.7° 및 9.5°에서 회절 피크를 더 갖는 것인 결정.
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KR20070008617A KR20070008617A (ko) | 2007-01-17 |
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KR1020067027447A KR101187218B1 (ko) | 2004-07-06 | 2005-07-05 | 1,2-디하이드로피리딘-2-온 화합물의 제조 방법 |
KR1020067020395A KR100939743B1 (ko) | 2004-07-06 | 2005-07-05 | 1,2-디히드로피리딘 화합물의 결정 및 그 제조 방법 |
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US (3) | US8304548B2 (ko) |
EP (3) | EP2586771A3 (ko) |
JP (3) | JPWO2006004107A1 (ko) |
KR (2) | KR101187218B1 (ko) |
CN (7) | CN1984890A (ko) |
AT (1) | ATE547405T1 (ko) |
AU (2) | AU2005258385B2 (ko) |
BR (1) | BRPI0510254B8 (ko) |
CA (2) | CA2570177C (ko) |
CY (1) | CY1114313T1 (ko) |
DK (1) | DK1764361T3 (ko) |
ES (1) | ES2404697T3 (ko) |
HK (2) | HK1102127A1 (ko) |
HR (1) | HRP20130363T1 (ko) |
IL (2) | IL180024A (ko) |
JO (1) | JO2832B1 (ko) |
ME (1) | ME01520B (ko) |
MX (1) | MXPA06014458A (ko) |
MY (1) | MY148809A (ko) |
NO (1) | NO339101B1 (ko) |
NZ (1) | NZ550720A (ko) |
PL (2) | PL1764361T3 (ko) |
PT (1) | PT1764361E (ko) |
RS (1) | RS52752B (ko) |
RU (1) | RU2323930C1 (ko) |
SI (2) | SI1772450T1 (ko) |
TW (1) | TW200606144A (ko) |
WO (2) | WO2006004107A1 (ko) |
ZA (1) | ZA200609274B (ko) |
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WO2021240540A1 (en) | 2020-05-26 | 2021-12-02 | Celagenex Research (India) Pvt. Ltd. | Novel synergistic nutritional compositions for treating seizures and chronic inflammatory diseases |
GR1010285B (el) * | 2021-05-31 | 2022-08-24 | Elpen Αε Φαρμακευτικη Βιομηχανια, | Στερεες φαρμακοτεχνικες μορφες περαμπανελης |
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