JP2008512422A - イミダゾール化合物並びにその塩及び擬似多形の製造方法 - Google Patents
イミダゾール化合物並びにその塩及び擬似多形の製造方法 Download PDFInfo
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- JP2008512422A JP2008512422A JP2007530670A JP2007530670A JP2008512422A JP 2008512422 A JP2008512422 A JP 2008512422A JP 2007530670 A JP2007530670 A JP 2007530670A JP 2007530670 A JP2007530670 A JP 2007530670A JP 2008512422 A JP2008512422 A JP 2008512422A
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- sertaconazole
- sertaconazole mononitrate
- water
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- -1 imidazole compound Chemical class 0.000 title description 2
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000003839 salts Chemical class 0.000 title description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title 2
- HAAITRDZHUANGT-UHFFFAOYSA-N 1-[2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl]imidazole;nitric acid Chemical compound O[N+]([O-])=O.ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 HAAITRDZHUANGT-UHFFFAOYSA-N 0.000 claims abstract description 49
- 238000000034 method Methods 0.000 claims abstract description 12
- 239000002245 particle Substances 0.000 claims abstract description 8
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 19
- JLGKQTAYUIMGRK-UHFFFAOYSA-N 1-{2-[(7-chloro-1-benzothiophen-3-yl)methoxy]-2-(2,4-dichlorophenyl)ethyl}imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=1C2=CC=CC(Cl)=C2SC=1)CN1C=NC=C1 JLGKQTAYUIMGRK-UHFFFAOYSA-N 0.000 claims description 12
- UKVLTPAGJIYSGN-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-2-imidazol-1-ylethanol Chemical compound C=1C=C(Cl)C=C(Cl)C=1C(O)CN1C=CN=C1 UKVLTPAGJIYSGN-UHFFFAOYSA-N 0.000 claims description 11
- 238000006243 chemical reaction Methods 0.000 claims description 11
- 239000000376 reactant Substances 0.000 claims description 11
- 229960005429 sertaconazole Drugs 0.000 claims description 11
- 239000012458 free base Substances 0.000 claims description 10
- OFKWTWJUANJQNU-UHFFFAOYSA-N 3-(bromomethyl)-7-chloro-1-benzothiophene Chemical compound ClC1=CC=CC2=C1SC=C2CBr OFKWTWJUANJQNU-UHFFFAOYSA-N 0.000 claims description 8
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 claims description 8
- 229910017604 nitric acid Inorganic materials 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 6
- SHFJWMWCIHQNCP-UHFFFAOYSA-M hydron;tetrabutylazanium;sulfate Chemical compound OS([O-])(=O)=O.CCCC[N+](CCCC)(CCCC)CCCC SHFJWMWCIHQNCP-UHFFFAOYSA-M 0.000 claims description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- 239000011343 solid material Substances 0.000 claims description 5
- 239000007864 aqueous solution Substances 0.000 claims description 3
- 238000001914 filtration Methods 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 238000001035 drying Methods 0.000 claims 2
- 238000001816 cooling Methods 0.000 claims 1
- 238000007873 sieving Methods 0.000 claims 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 claims 1
- 229910001948 sodium oxide Inorganic materials 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 238000002360 preparation method Methods 0.000 description 7
- 239000000725 suspension Substances 0.000 description 6
- 239000000499 gel Substances 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 238000002441 X-ray diffraction Methods 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000006072 paste Substances 0.000 description 3
- 239000008194 pharmaceutical composition Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002324 mouth wash Substances 0.000 description 2
- 229940051866 mouthwash Drugs 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
- 239000000606 toothpaste Substances 0.000 description 2
- 229940044977 vaginal tablet Drugs 0.000 description 2
- 239000000003 vaginal tablet Substances 0.000 description 2
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- 208000034423 Delivery Diseases 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 239000003788 bath preparation Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006189 buccal tablet Substances 0.000 description 1
- 238000001311 chemical methods and process Methods 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000007405 data analysis Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 239000002360 explosive Substances 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 238000001000 micrograph Methods 0.000 description 1
- 238000000386 microscopy Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 230000003232 mucoadhesive effect Effects 0.000 description 1
- 229940041676 mucosal spray Drugs 0.000 description 1
- 238000002703 mutagenesis Methods 0.000 description 1
- 231100000350 mutagenesis Toxicity 0.000 description 1
- FGHSTPNOXKDLKU-UHFFFAOYSA-N nitric acid;hydrate Chemical compound O.O[N+]([O-])=O FGHSTPNOXKDLKU-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000007935 oral tablet Substances 0.000 description 1
- 239000011505 plaster Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007901 soft capsule Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000012916 structural analysis Methods 0.000 description 1
- 239000006190 sub-lingual tablet Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- ZZIZZTHXZRDOFM-XFULWGLBSA-N tamsulosin hydrochloride Chemical compound [H+].[Cl-].CCOC1=CC=CC=C1OCCN[C@H](C)CC1=CC=C(OC)C(S(N)(=O)=O)=C1 ZZIZZTHXZRDOFM-XFULWGLBSA-N 0.000 description 1
- CMQCNTNASCDNGR-UHFFFAOYSA-N toluene;hydrate Chemical compound O.CC1=CC=CC=C1 CMQCNTNASCDNGR-UHFFFAOYSA-N 0.000 description 1
- 229940034610 toothpaste Drugs 0.000 description 1
- 229940044959 vaginal cream Drugs 0.000 description 1
- 239000000522 vaginal cream Substances 0.000 description 1
- 230000009677 vaginal delivery Effects 0.000 description 1
- 229940044952 vaginal foam Drugs 0.000 description 1
- 239000000259 vaginal foam Substances 0.000 description 1
- 229940044950 vaginal gel Drugs 0.000 description 1
- 239000000029 vaginal gel Substances 0.000 description 1
- 229940098946 vaginal ointment Drugs 0.000 description 1
- 239000006216 vaginal suppository Substances 0.000 description 1
- 229940120293 vaginal suppository Drugs 0.000 description 1
Classifications
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
- A61K31/381—Heterocyclic compounds having sulfur as a ring hetero atom having five-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/50—1,3-Diazoles; Hydrogenated 1,3-diazoles
-
- 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
- A61K31/38—Heterocyclic compounds having sulfur as a ring hetero atom
-
- 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
- A61K31/415—1,2-Diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Epidemiology (AREA)
- Plant Pathology (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Agronomy & Crop Science (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Catalysts (AREA)
Abstract
Description
セルタコナゾール一硝酸塩一水和物(V)(セルタコナゾール一硝酸塩疑似多形)
2Lフラスコに、308mLのトルエン、100gの1−(2,4−ジクロロフェニル)−2−(1H−イミダゾール−1−イル)−エタノール(II)(0.389モル)及び6.67gのテトラブチルアンモニウム硫酸水素塩(IV、Z=HSO4)(0.0196モル)を装入した。次いで、155gの水酸化ナトリウム(純度49%、1.905モル)を添加した。この混合物を35〜40℃で15分間加熱し撹拌した。111.11gの3−ブロモメチル−7−クロロベンゾ[b]チオフェン(III)(0.425モル)及び595mLのトルエンを含む溶液を、37から40℃の反応塊温度を保ちながら、少なくとも30分間かけて添加した。添加の後、この系を37から40℃で2.5時間保ち、その後、水(635mL)を添加した。この混合物を5〜10℃の反応塊温度に冷却し、沈殿したセルタコナゾールをろ過し水及び冷却したトルエン(5〜10℃)で洗浄して、179.7gの湿ったセルタコナゾール遊離塩基(161.7g乾燥時)を得た。
IR(赤外線):Omnic2.1ソフトウエアで作動するデータベースを備えたMagna−IR 550 Nicoletスペクトロメーターを使用した。セルタコナゾール一硝酸塩(I)と比較したセルタコナゾール一硝酸塩一水和物(V)の記録されたIRスペクトルが、図2/5に示されている。
温度範囲:110〜180℃
加熱速度:10℃/分
窒素気流:100mL/分
セルタコナゾール一硝酸塩(I)と比べたセルタコナゾール一硝酸塩一水和物(V)の記録されたDSCが、図3/5に示されている。
セルタコナゾール一硝酸塩一水和物(V)及びセルタコナゾール一硝酸塩(I)の顕微鏡写真が図4/5に示されている。
セルタコナゾール一硝酸塩一水和物(V)及びセルタコナゾール一硝酸塩(I)のX線回折が図5/5に示されている。セルタコナゾール一硝酸塩一水和物(V)の結晶データ及び構造解析が表2に示されている。
セルタコナゾール一硝酸塩(I)
先述の通り得られたセルタコナゾール一硝酸塩一水和物(V)(215.9g 0.344モル)を、991mLの無水エタノール及び150mLの水に溶解した。この混合物を75〜80℃に加熱し、次いで10℃に約6〜8時間冷却しておいた、2.8Lの水及び1.7gの60%硝酸を含む別の溶液に添加した。添加を完了後、この混合物を10℃で15分間撹拌した。得られた物質をろ過し65℃で乾燥し、ふるいにかけ、85℃で最終的に乾燥して、162.2gのセルタコナゾール一硝酸塩(I)を得た。収率93.9%。全収率83.3%。粒子サイズは、全体のサンプルの40%が10μm、全体のサンプルの95%が30μmであった。MP158〜160℃。調製した生成物のセルタコナゾール一硝酸塩の得られた含有率は>99.5%であった。
Claims (7)
- セルタコナゾール一硝酸塩(I)の製造方法であって、
(i)1−(2,4−ジクロロフェニル)−2−(1H−イミダゾール−1−イル)−エタノール(II)を、トルエン中においてテトラブチルアンモニウム硫酸水素塩(IV、Z=HSO4)及び水酸化ナトリウムの存在下、30〜45℃で、3−ブロモメチル−7−クロロベンゾ[b]チオフェン(III)と反応させ、水を添加し、この混合物を0〜15℃の反応塊温度に冷却し、ろ過し、得られた固形物質を水及びトルエンで洗浄し、このように得られたセルタコナゾール遊離塩基を無水エタノール中で完全に溶解するまで還流し、この反応塊を60〜80℃に加熱し、水を添加し、さらに5〜15℃に冷却し、形成した固形物質をろ過し、エタノール及び水の混合物で洗浄し、得られた純粋なセルタコナゾール遊離塩基を無水エタノール中に70〜80℃で再溶解し、この混合物を65〜75℃の反応塊温度で冷却し、その後60%の硝酸を含有する水溶液を添加し、その温度を10〜20分間保ち、pH2未満を維持し、この混合物を5〜15℃で冷却し、この温度を30分から2時間維持し、続いてろ過し洗浄してセルタコナゾール一硝酸塩一水和物(V)を得るステップ;及び
(ii)セルタコナゾール一硝酸塩一水和物をエタノール及び水の混合物中に溶解し、この反応塊を75〜80℃に加熱し、この混合物を5〜15℃に冷却された硝酸の水溶液に添加し、ろ過し、60〜70℃で乾燥し、ふるいにかけ、80〜90℃で最終的に乾燥するステップ
を含む上記方法。 - 反応物II:反応物IIIのモル比が0.85から0.95である、請求項1に記載の方法。
- 触媒(IV、Z=HSO4):限定反応物(II)のモル比が0.025から0.060である、請求項1及び2のいずれか一項に記載の方法。
- 触媒(IV、Z=HSO4):限定反応物(II)のモル比が0.045から0.055である、請求項3に記載の方法。
- 触媒(IV、Z=HSO4):限定反応物(II)のモル比が0.050である、請求項3に記載の方法。
- その粒子サイズが、全体のサンプルの少なくとも40%(v:v)が10μm以下、且つ全体のサンプルの少なくとも95%(v:v)が30μm以下である、請求項1から5までのいずれか一項に従って得られるセルタコナゾール一硝酸塩(I)。
- セルタコナゾール一硝酸塩一水和物(V)。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
ES200402183 | 2004-09-13 | ||
ES200402183A ES2249991B1 (es) | 2004-09-13 | 2004-09-13 | Procedimiento de fabricacion de compuestos imidazolicos, sus sales y sus pseudopolimorfos. |
PCT/EP2005/009825 WO2006029812A1 (en) | 2004-09-13 | 2005-09-13 | Method for manufacturing imidazole compounds and salts and pseudopolymorphs thereof |
Publications (2)
Publication Number | Publication Date |
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JP2008512422A true JP2008512422A (ja) | 2008-04-24 |
JP4866355B2 JP4866355B2 (ja) | 2012-02-01 |
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JP2007530670A Active JP4866355B2 (ja) | 2004-09-13 | 2005-09-13 | イミダゾール化合物並びにその塩及び擬似多形の製造方法 |
Country Status (24)
Country | Link |
---|---|
US (1) | US7829726B2 (ja) |
EP (1) | EP1788876B1 (ja) |
JP (1) | JP4866355B2 (ja) |
KR (1) | KR100861436B1 (ja) |
CN (1) | CN100579966C (ja) |
AR (1) | AR053093A1 (ja) |
AT (1) | ATE431076T1 (ja) |
AU (1) | AU2005284331B2 (ja) |
BR (1) | BRPI0515254A (ja) |
CA (1) | CA2577253C (ja) |
DE (1) | DE602005014491D1 (ja) |
DK (1) | DK1788876T3 (ja) |
ES (1) | ES2249991B1 (ja) |
HK (1) | HK1104765A1 (ja) |
MX (1) | MX2007002924A (ja) |
NO (1) | NO337950B1 (ja) |
PA (1) | PA8645401A1 (ja) |
PE (1) | PE20060690A1 (ja) |
PL (1) | PL1788876T3 (ja) |
PT (1) | PT1788876E (ja) |
RU (1) | RU2357965C2 (ja) |
TW (1) | TWI357813B (ja) |
UY (1) | UY29116A1 (ja) |
WO (1) | WO2006029812A1 (ja) |
Families Citing this family (6)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2010066756A1 (en) * | 2008-12-09 | 2010-06-17 | Ferrer Internacional, S.A. | Polymorph ii of an antifungal compound |
US10437922B2 (en) * | 2015-12-03 | 2019-10-08 | Workday, Inc. | Spreadsheet with unit based conversions |
CN113501814A (zh) * | 2021-07-30 | 2021-10-15 | 海南海神同洲制药有限公司 | 一种硝酸舍他康唑的纯化方法 |
CN113501815A (zh) * | 2021-07-30 | 2021-10-15 | 海南海神同洲制药有限公司 | 一种硝酸舍他康唑晶型的制备方法 |
CN113816947A (zh) * | 2021-08-25 | 2021-12-21 | 海南海神同洲制药有限公司 | 一种硝酸舍他康唑的重结晶方法 |
CN113735843B (zh) * | 2021-09-07 | 2023-05-26 | 海南海神同洲制药有限公司 | 一种低熔点硝酸舍他康唑的制备方法 |
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JPH09510234A (ja) * | 1995-01-04 | 1997-10-14 | フエルレル インターナショナル,ソシエダッド アノニマ | 1−[2,4−ジクロロ−β−[(7−クロロベンゾ[b]チエニ−3−イル)メトキシ]フェネチル]イミダゾール・1硝酸塩の同質異像B及びC |
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