NO320314B1 - Krystallmodifikasjon D av 8-cyano-1-cyklopropyl-7-(1S,6S-2,8- diazabicyklo-/4.3.0/-nonan-8-yl)-6-fluor-1,4-dihydro-4-okso-3-kinolinkarboksylsyre, fremgangsmate for fremstilling derav, legemiddel inneholdende modifikasjonen samt anvendelse av denne. - Google Patents
Krystallmodifikasjon D av 8-cyano-1-cyklopropyl-7-(1S,6S-2,8- diazabicyklo-/4.3.0/-nonan-8-yl)-6-fluor-1,4-dihydro-4-okso-3-kinolinkarboksylsyre, fremgangsmate for fremstilling derav, legemiddel inneholdende modifikasjonen samt anvendelse av denne. Download PDFInfo
- Publication number
- NO320314B1 NO320314B1 NO20014059A NO20014059A NO320314B1 NO 320314 B1 NO320314 B1 NO 320314B1 NO 20014059 A NO20014059 A NO 20014059A NO 20014059 A NO20014059 A NO 20014059A NO 320314 B1 NO320314 B1 NO 320314B1
- Authority
- NO
- Norway
- Prior art keywords
- ccdc
- modification
- diazabicyclo
- cyclopropyl
- dihydro
- Prior art date
Links
- 238000012986 modification Methods 0.000 title claims description 37
- 230000004048 modification Effects 0.000 title claims description 37
- 239000013078 crystal Substances 0.000 title claims description 18
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title description 7
- 239000003814 drug Substances 0.000 title description 4
- 229940079593 drug Drugs 0.000 title description 2
- IGRCWJPBLWGNPX-UHFFFAOYSA-N 3-(2-chlorophenyl)-n-(4-chlorophenyl)-n,5-dimethyl-1,2-oxazole-4-carboxamide Chemical compound C=1C=C(Cl)C=CC=1N(C)C(=O)C1=C(C)ON=C1C1=CC=CC=C1Cl IGRCWJPBLWGNPX-UHFFFAOYSA-N 0.000 claims description 33
- 239000007787 solid Substances 0.000 claims description 19
- 239000000843 powder Substances 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 229940126601 medicinal product Drugs 0.000 claims description 5
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 239000002244 precipitate Substances 0.000 claims description 3
- 230000009466 transformation Effects 0.000 claims description 3
- 239000003242 anti bacterial agent Substances 0.000 claims description 2
- 239000000969 carrier Substances 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 230000011514 reflex Effects 0.000 claims description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 239000000203 mixture Substances 0.000 description 5
- 238000004455 differential thermal analysis Methods 0.000 description 4
- KSCPLKVBWDOSAI-NKWVEPMBSA-N (4as,7as)-2,3,4,4a,5,6,7,7a-octahydro-1h-pyrrolo[3,4-b]pyridine Chemical compound N1CCC[C@H]2CNC[C@H]21 KSCPLKVBWDOSAI-NKWVEPMBSA-N 0.000 description 3
- PXTYIFUOEXJZEN-UHFFFAOYSA-N 7-chloro-8-cyano-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound C12=C(C#N)C(Cl)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 PXTYIFUOEXJZEN-UHFFFAOYSA-N 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000000634 powder X-ray diffraction Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000013543 active substance Substances 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
- 239000007864 aqueous solution Substances 0.000 description 1
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 239000012154 double-distilled water Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 235000012907 honey Nutrition 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- -1 polyethylene Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000011343 solid material Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000002076 thermal analysis method Methods 0.000 description 1
- 238000001757 thermogravimetry curve Methods 0.000 description 1
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- 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
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19908448A DE19908448A1 (de) | 1999-02-26 | 1999-02-26 | Kristallmodifikation D von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicylo[4.3.0)nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chino incarbonsäure |
| PCT/EP2000/001203 WO2000052010A1 (de) | 1999-02-26 | 2000-02-14 | Kristallmodifikation d von 8-cyan-1-cyclopropyl-7- (1s, 6s- 2,8- diazabicyclo- [4.3.0] nonan -8-yl) -6-fluor -1,4- dihydro -4-oxo -3-c hinolincarbonsäure |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20014059L NO20014059L (no) | 2001-08-21 |
| NO20014059D0 NO20014059D0 (no) | 2001-08-21 |
| NO320314B1 true NO320314B1 (no) | 2005-11-21 |
Family
ID=7899026
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20014059A NO320314B1 (no) | 1999-02-26 | 2001-08-21 | Krystallmodifikasjon D av 8-cyano-1-cyklopropyl-7-(1S,6S-2,8- diazabicyklo-/4.3.0/-nonan-8-yl)-6-fluor-1,4-dihydro-4-okso-3-kinolinkarboksylsyre, fremgangsmate for fremstilling derav, legemiddel inneholdende modifikasjonen samt anvendelse av denne. |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US6492391B1 (de) |
| EP (1) | EP1159277A1 (de) |
| JP (1) | JP2002538159A (de) |
| KR (1) | KR100756474B1 (de) |
| CN (1) | CN1217944C (de) |
| AU (1) | AU760710B2 (de) |
| BR (1) | BR0008520A (de) |
| CA (1) | CA2362804A1 (de) |
| CZ (1) | CZ20013065A3 (de) |
| DE (1) | DE19908448A1 (de) |
| HK (1) | HK1045158B (de) |
| HU (1) | HUP0200053A3 (de) |
| IL (1) | IL144528A0 (de) |
| NO (1) | NO320314B1 (de) |
| NZ (1) | NZ513749A (de) |
| PL (1) | PL349394A1 (de) |
| RU (1) | RU2248357C2 (de) |
| SK (1) | SK11942001A3 (de) |
| TR (1) | TR200102435T2 (de) |
| UA (1) | UA71606C2 (de) |
| WO (1) | WO2000052010A1 (de) |
| ZA (1) | ZA200106050B (de) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE19854356A1 (de) | 1998-11-25 | 2000-05-31 | Bayer Ag | Kristallmodifikation A von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo-/4.3.0/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19854355A1 (de) | 1998-11-25 | 2000-05-31 | Bayer Ag | Kristallmodifikation B von 8-Cyan-1-cyclopropyl-7-(1S, 6S-2,8-diazabicyclo-/4.3.O/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19908449A1 (de) | 1999-02-26 | 2000-08-31 | Bayer Ag | Kristallmodifikation C von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicylo-[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chino/incarbonsäure |
| DE102004015981A1 (de) * | 2004-04-01 | 2005-10-20 | Bayer Healthcare Ag | Neue kirstalline Form von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| JP7257322B2 (ja) | 2017-02-13 | 2023-04-13 | バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | プラドフロキサシンを含有する液体組成物 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2676521B2 (ja) | 1988-03-22 | 1997-11-17 | 北陸製薬株式会社 | キノロンカルボン酸化合物ｉ型結晶の製造法 |
| HUT77946A (hu) * | 1994-11-18 | 1998-12-28 | Pharmacia & Upjohn Co. | Fluor-kinolon-származék fizikailag stabil, szilárd formája |
| JP4338217B2 (ja) * | 1996-02-23 | 2009-10-07 | バイエル・アニマル・ヘルス・ゲゼルシヤフト・ミツト・ベシユレンクテル・ハフツング | 置換可能な８―シアノ―１―シクロプロピル―７―（２，８―ジアザビシクロ―［４．３．０］―ノナン―８―イル）―６―フルオロ―１，４―ジヒドロ―４―オキソ―３―キノリンカルボン酸およびそれらの誘導体 |
| DE19854356A1 (de) | 1998-11-25 | 2000-05-31 | Bayer Ag | Kristallmodifikation A von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicyclo-/4.3.0/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19854355A1 (de) | 1998-11-25 | 2000-05-31 | Bayer Ag | Kristallmodifikation B von 8-Cyan-1-cyclopropyl-7-(1S, 6S-2,8-diazabicyclo-/4.3.O/nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäure |
| DE19908449A1 (de) | 1999-02-26 | 2000-08-31 | Bayer Ag | Kristallmodifikation C von 8-Cyan-1-cyclopropyl-7-(1S,6S-2,8-diazabicylo-[4.3.0]nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chino/incarbonsäure |
| JP2001242582A (ja) * | 2000-02-25 | 2001-09-07 | Fuji Photo Film Co Ltd | ハロゲン化銀写真感光材料およびその現像処理方法 |
-
1999
- 1999-02-26 DE DE19908448A patent/DE19908448A1/de not_active Withdrawn
-
2000
- 2000-02-14 PL PL00349394A patent/PL349394A1/xx not_active Application Discontinuation
- 2000-02-14 UA UA2001096577A patent/UA71606C2/uk unknown
- 2000-02-14 CZ CZ20013065A patent/CZ20013065A3/cs unknown
- 2000-02-14 WO PCT/EP2000/001203 patent/WO2000052010A1/de not_active Application Discontinuation
- 2000-02-14 US US09/914,031 patent/US6492391B1/en not_active Expired - Fee Related
- 2000-02-14 IL IL14452800A patent/IL144528A0/xx not_active IP Right Cessation
- 2000-02-14 SK SK1194-2001A patent/SK11942001A3/sk not_active Application Discontinuation
- 2000-02-14 EP EP00909167A patent/EP1159277A1/de not_active Withdrawn
- 2000-02-14 KR KR1020017009632A patent/KR100756474B1/ko not_active IP Right Cessation
- 2000-02-14 CN CN00804306XA patent/CN1217944C/zh not_active Expired - Fee Related
- 2000-02-14 RU RU2001126301/04A patent/RU2248357C2/ru not_active IP Right Cessation
- 2000-02-14 NZ NZ513749A patent/NZ513749A/en unknown
- 2000-02-14 BR BR0008520-0A patent/BR0008520A/pt not_active IP Right Cessation
- 2000-02-14 TR TR2001/02435T patent/TR200102435T2/xx unknown
- 2000-02-14 JP JP2000602236A patent/JP2002538159A/ja not_active Withdrawn
- 2000-02-14 CA CA002362804A patent/CA2362804A1/en not_active Abandoned
- 2000-02-14 AU AU31544/00A patent/AU760710B2/en not_active Ceased
- 2000-02-14 HU HU0200053A patent/HUP0200053A3/hu unknown
-
2001
- 2001-07-24 ZA ZA200106050A patent/ZA200106050B/en unknown
- 2001-08-21 NO NO20014059A patent/NO320314B1/no unknown
-
2002
- 2002-09-12 HK HK02106690.8A patent/HK1045158B/zh not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002538159A (ja) | 2002-11-12 |
| KR20010093300A (ko) | 2001-10-27 |
| ZA200106050B (en) | 2002-07-24 |
| IL144528A0 (en) | 2002-05-23 |
| HK1045158B (zh) | 2006-04-21 |
| WO2000052010A1 (de) | 2000-09-08 |
| US6492391B1 (en) | 2002-12-10 |
| CN1217944C (zh) | 2005-09-07 |
| RU2248357C2 (ru) | 2005-03-20 |
| UA71606C2 (uk) | 2004-12-15 |
| AU3154400A (en) | 2000-09-21 |
| NO20014059L (no) | 2001-08-21 |
| CZ20013065A3 (cs) | 2002-01-16 |
| NZ513749A (en) | 2003-10-31 |
| HUP0200053A3 (en) | 2003-01-28 |
| NO20014059D0 (no) | 2001-08-21 |
| HUP0200053A2 (hu) | 2002-05-29 |
| DE19908448A1 (de) | 2000-08-31 |
| CN1341116A (zh) | 2002-03-20 |
| KR100756474B1 (ko) | 2007-09-07 |
| BR0008520A (pt) | 2001-12-18 |
| PL349394A1 (en) | 2002-07-15 |
| SK11942001A3 (sk) | 2001-12-03 |
| AU760710B2 (en) | 2003-05-22 |
| TR200102435T2 (tr) | 2002-01-21 |
| HK1045158A1 (en) | 2002-11-15 |
| CA2362804A1 (en) | 2000-09-08 |
| EP1159277A1 (de) | 2001-12-05 |
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