KR100908796B1 - 아세트산아닐리드 유도체의 α형 또는 β형 결정 - Google Patents
아세트산아닐리드 유도체의 α형 또는 β형 결정 Download PDFInfo
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- KR100908796B1 KR100908796B1 KR1020047006428A KR20047006428A KR100908796B1 KR 100908796 B1 KR100908796 B1 KR 100908796B1 KR 1020047006428 A KR1020047006428 A KR 1020047006428A KR 20047006428 A KR20047006428 A KR 20047006428A KR 100908796 B1 KR100908796 B1 KR 100908796B1
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- Prior art keywords
- crystals
- ethyl
- amino
- hydroxy
- aminothiazol
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- 239000013078 crystal Substances 0.000 title claims abstract description 136
- -1 anilide acetate derivatives Chemical class 0.000 title claims abstract description 77
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 34
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims abstract description 25
- 238000000634 powder X-ray diffraction Methods 0.000 claims abstract description 14
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 8
- 238000010521 absorption reaction Methods 0.000 claims abstract description 7
- 239000003472 antidiabetic agent Substances 0.000 claims abstract description 4
- 229940125708 antidiabetic agent Drugs 0.000 claims abstract 3
- 239000003937 drug carrier Substances 0.000 claims 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims 1
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- 239000000543 intermediate Substances 0.000 abstract description 6
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- 239000002994 raw material Substances 0.000 abstract description 4
- 206010022489 Insulin Resistance Diseases 0.000 abstract description 3
- 238000009776 industrial production Methods 0.000 abstract description 3
- 208000008589 Obesity Diseases 0.000 abstract description 2
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- 235000020824 obesity Nutrition 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000023597 hemostasis Effects 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 17
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- 239000000203 mixture Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 238000001914 filtration Methods 0.000 description 8
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 7
- 239000008103 glucose Substances 0.000 description 7
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- QILVTBCJVNFIDP-NTISSMGPSA-N (1r)-2-[2-(4-aminophenyl)ethylamino]-1-phenylethanol;hydrochloride Chemical compound Cl.C1=CC(N)=CC=C1CCNC[C@H](O)C1=CC=CC=C1 QILVTBCJVNFIDP-NTISSMGPSA-N 0.000 description 6
- FPQQSJJWHUJYPU-UHFFFAOYSA-N 3-(dimethylamino)propyliminomethylidene-ethylazanium;chloride Chemical compound Cl.CCN=C=NCCCN(C)C FPQQSJJWHUJYPU-UHFFFAOYSA-N 0.000 description 6
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Chemical compound N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 2
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- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
- 239000006187 pill Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 2
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- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- JVMHULJEYUQYSH-UHFFFAOYSA-N 2-(4-nitrophenyl)ethylazanium;chloride Chemical compound Cl.NCCC1=CC=C([N+]([O-])=O)C=C1 JVMHULJEYUQYSH-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
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- FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 1
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
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- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000003931 anilides Chemical class 0.000 description 1
- 230000003178 anti-diabetic effect Effects 0.000 description 1
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- 230000003579 anti-obesity Effects 0.000 description 1
- 239000003524 antilipemic agent Substances 0.000 description 1
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 239000012141 concentrate Substances 0.000 description 1
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- 238000009505 enteric coating Methods 0.000 description 1
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- 235000001727 glucose Nutrition 0.000 description 1
- 229940116332 glucose oxidase Drugs 0.000 description 1
- 235000019420 glucose oxidase Nutrition 0.000 description 1
- 229960002897 heparin Drugs 0.000 description 1
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- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 201000001421 hyperglycemia Diseases 0.000 description 1
- 229940125396 insulin Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
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- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
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- 229940127557 pharmaceutical product Drugs 0.000 description 1
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
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- 229910052697 platinum Inorganic materials 0.000 description 1
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- 238000005070 sampling Methods 0.000 description 1
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Images
Classifications
-
- 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
- C07D277/40—Unsubstituted amino or imino radicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Diabetes (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Health & Medical Sciences (AREA)
- Hematology (AREA)
- Obesity (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Emergency Medicine (AREA)
- Endocrinology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Thiazole And Isothizaole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Steroid Compounds (AREA)
Abstract
Description
결정 격자 간격 | 상대강도 | 결정 격자 간격 | 상대강도 |
5.32 | 강함 | 19.04 | 약간 강함 |
8.08 | 강함 | 20.20 | 약간 강함 |
15.28 | 약간 강함 | 23.16 | 약간 강함 |
17.88 | 약간 강함 | 24.34 | 약간 강함 |
결정 격자 간격 | 상대강도 | 결정 격자 간격 | 상대강도 |
9.68 | 중간 정도 | 22.10 | 중간 정도 |
19.76 | 약간 강함 | 23.52 | 중간 정도 |
20.72 | 중간 정도 |
Claims (12)
- 삭제
- DSC 분석시 142 내지 146℃에서 열흡수 피크를 갖는, (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 α형 결정.
- 분말 X선 회절시 2θ(°)에 대해 5.32, 8.08, 15.28, 17.88, 19.04, 20.20, 23.16 및 24.34 부근에서 주 피크를 갖는, (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 α형 결정.
- DSC 분석시 142 내지 146℃에서 열흡수 피크를 갖고, 분말 X선 회절시 2θ(°)에 대해 5.32, 8.08, 15.28, 17.88, 19.04, 20.20, 23.16 및 24.34 부근에서 주 피크를 갖는, (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 α형 결정.
- 삭제
- 제2항 내지 제4항 중 어느 한 항에 따르는 (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 α형 결정과 약제학적으로 허용되는 담체를 함유하는 당뇨병 치료제.
- 삭제
- DSC 분석시 90 내지 110℃ 및 142 내지 146℃에서 열흡수 피크를 갖는, (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 β형 결정.
- 분말 X선 회절시 2θ(°)에 대해 9.68, 19.76, 20.72, 22.10 및 23.52 부근에서 주 피크를 갖는, (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 β형 결정.
- DSC 분석시 90 내지 110℃ 및 142 내지 146℃에서 열흡수 피크를 갖고, 분말 X선 회절시 2θ(°)에 대해 9.68, 19.76, 20.72, 22.10 및 23.52 부근에서 주 피크를 갖는, (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미 노]에틸]아세트산아닐리드의 β형 결정.
- 삭제
- 제8항 내지 제10항 중 어느 한 항에 따르는 (R)-2-(2-아미노티아졸-4-일)-4'-[2-[(2-하이드록시-2-페닐에틸)아미노]에틸]아세트산아닐리드의 β형 결정과 약제학적으로 허용되는 담체를 함유하는 당뇨병 치료제.
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JP2001332914 | 2001-10-30 | ||
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PCT/JP2002/011217 WO2003037881A1 (fr) | 2001-10-30 | 2002-10-29 | Cristal a forme $g(a) ou $g(b) d'un derive acetanilinide |
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KR20050040837A KR20050040837A (ko) | 2005-05-03 |
KR100908796B1 true KR100908796B1 (ko) | 2009-07-22 |
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US (2) | US7342117B2 (ko) |
EP (3) | EP1440969A4 (ko) |
JP (1) | JP3800220B2 (ko) |
KR (1) | KR100908796B1 (ko) |
CN (1) | CN1243740C (ko) |
AU (1) | AU2002344419C1 (ko) |
BR (1) | BRPI0213570B8 (ko) |
CA (1) | CA2464068C (ko) |
ES (1) | ES2404071T3 (ko) |
HU (1) | HU230481B1 (ko) |
MX (1) | MXPA04003936A (ko) |
NO (1) | NO326965B1 (ko) |
PL (1) | PL218982B1 (ko) |
RU (1) | RU2303033C2 (ko) |
TW (1) | TW200300020A (ko) |
WO (1) | WO2003037881A1 (ko) |
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KR20200117091A (ko) | 2019-04-02 | 2020-10-14 | 제이투에이치바이오텍 (주) | 미라베그론 전구체 약물 화합물 및 이의 과민성 방광 질환의 치료 또는 개선을 위한 의약 용도 |
KR20220081033A (ko) | 2020-12-08 | 2022-06-15 | 주식회사 한서켐 | 미라베그론 α형 결정의 제조방법 |
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