NO320191B1 - Krystallmodifikasjon C 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 frmstilling derav, legemiddel inneholdende forbindelsen samt anvendelse av denne. - Google Patents
Krystallmodifikasjon C 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 frmstilling derav, legemiddel inneholdende forbindelsen samt anvendelse av denne. Download PDFInfo
- Publication number
- NO320191B1 NO320191B1 NO20014061A NO20014061A NO320191B1 NO 320191 B1 NO320191 B1 NO 320191B1 NO 20014061 A NO20014061 A NO 20014061A NO 20014061 A NO20014061 A NO 20014061A NO 320191 B1 NO320191 B1 NO 320191B1
- Authority
- NO
- Norway
- Prior art keywords
- ccdc
- modification
- oxo
- diazabicyclo
- cyclopropyl
- Prior art date
Links
- 230000004048 modification Effects 0.000 title claims abstract description 39
- 238000012986 modification Methods 0.000 title claims abstract description 39
- 239000013078 crystal Substances 0.000 title claims abstract description 22
- 238000000034 method Methods 0.000 title claims abstract description 8
- 239000003814 drug Substances 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title abstract description 5
- 150000001875 compounds Chemical class 0.000 title description 2
- 229940079593 drug Drugs 0.000 title 1
- 239000000843 powder Substances 0.000 claims abstract description 13
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 229940126601 medicinal product Drugs 0.000 claims description 3
- 238000002844 melting Methods 0.000 claims description 3
- 230000008018 melting Effects 0.000 claims description 3
- 230000011514 reflex Effects 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
- 230000004584 weight gain Effects 0.000 claims description 2
- 235000019786 weight gain Nutrition 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 1
- 239000000825 pharmaceutical preparation Substances 0.000 abstract description 2
- -1 nonan-8-yl Chemical group 0.000 abstract 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 description 24
- 239000007787 solid Substances 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- 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
- 238000004455 differential thermal analysis Methods 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 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
- 238000001035 drying Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 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
- 230000002730 additional effect Effects 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
- 244000052616 bacterial pathogen Species 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002274 desiccant Substances 0.000 description 1
- 238000010438 heat treatment Methods 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000243 solution 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 1
- 238000001291 vacuum drying Methods 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
-
- 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 |
|---|---|---|---|
| DE19908449A DE19908449A1 (de) | 1999-02-26 | 1999-02-26 | 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 |
| PCT/EP2000/001202 WO2000052009A1 (de) | 1999-02-26 | 2000-02-14 | Kristallmodifikation c 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- chinolincarbon |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NO20014061D0 NO20014061D0 (no) | 2001-08-21 |
| NO20014061L NO20014061L (no) | 2001-08-21 |
| NO320191B1 true NO320191B1 (no) | 2005-11-07 |
Family
ID=7899027
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO20014061A NO320191B1 (no) | 1999-02-26 | 2001-08-21 | Krystallmodifikasjon C 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 frmstilling derav, legemiddel inneholdende forbindelsen samt anvendelse av denne. |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US6649762B1 (uk) |
| EP (1) | EP1155018B1 (uk) |
| JP (1) | JP2002538158A (uk) |
| KR (1) | KR100756471B1 (uk) |
| CN (1) | CN1191253C (uk) |
| AT (1) | ATE226952T1 (uk) |
| AU (1) | AU763003B2 (uk) |
| BR (1) | BR0008493A (uk) |
| CA (1) | CA2362801A1 (uk) |
| CZ (1) | CZ299700B6 (uk) |
| DE (2) | DE19908449A1 (uk) |
| DK (1) | DK1155018T3 (uk) |
| ES (1) | ES2181644T3 (uk) |
| HK (1) | HK1044948B (uk) |
| HU (1) | HUP0200006A3 (uk) |
| IL (2) | IL144702A0 (uk) |
| NO (1) | NO320191B1 (uk) |
| NZ (1) | NZ513750A (uk) |
| PL (1) | PL349368A1 (uk) |
| PT (1) | PT1155018E (uk) |
| RU (1) | RU2248356C2 (uk) |
| SK (1) | SK285562B6 (uk) |
| TR (1) | TR200102434T2 (uk) |
| UA (1) | UA70356C2 (uk) |
| WO (1) | WO2000052009A1 (uk) |
| ZA (1) | ZA200106289B (uk) |
Families Citing this family (6)
| 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 |
| DE19908448A1 (de) | 1999-02-26 | 2000-08-31 | Bayer Ag | 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 |
| 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 |
| DE102006049520A1 (de) * | 2006-10-20 | 2008-04-24 | Bayer Healthcare Ag | Verfahren zur Herstellung von Pradofloxacin |
Family Cites Families (9)
| 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 |
| AU709057B2 (en) * | 1994-11-18 | 1999-08-19 | Pharmacia & Upjohn Company | A new physically stable solid form of a fluoroquinolone |
| DE19546249A1 (de) * | 1995-12-12 | 1997-06-19 | Bayer Ag | Neue Kristallmodifikation des 1-Cyclopropyl-7-([S,S]-2,8-diazabicyclo[4,3,0]non-8-yl)-6-fluor-1,4-dihydro-8-methoxy-4-oxo-3-chinolincarbonsäure Hydrochlorid (CDCH), Verfahren zu dessen Herstellung und diese enthaltende pharmazeutische Zubereitungen |
| DE19633805A1 (de) * | 1996-02-23 | 1997-08-28 | Bayer Ag | Gegenenenfalls substituierte 8-Cyan-l-cyclopropyl-7-(2,8-diazabicyclo-[4.3.0]-nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäuren und ihre Derivate |
| DE59708771D1 (de) * | 1996-02-23 | 2003-01-02 | Bayer Ag | Gegebenenfalls substituierte 8-cyan-1-cyclopropyl-7-(2,8-diazabicyclo- 4.3.0]-nonan-8-yl)-6-fluor-1,4-dihydro-4-oxo-3-chinolincarbonsäuren und ihre derivate |
| 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 |
| DE19908448A1 (de) | 1999-02-26 | 2000-08-31 | Bayer Ag | 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 |
| 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 |
-
1999
- 1999-02-26 DE DE19908449A patent/DE19908449A1/de not_active Withdrawn
-
2000
- 2000-02-14 UA UA2001096578A patent/UA70356C2/uk unknown
- 2000-02-14 IL IL14470200A patent/IL144702A0/xx active IP Right Grant
- 2000-02-14 KR KR1020017009811A patent/KR100756471B1/ko not_active IP Right Cessation
- 2000-02-14 BR BR0008493-0A patent/BR0008493A/pt not_active Application Discontinuation
- 2000-02-14 EP EP00909166A patent/EP1155018B1/de not_active Expired - Lifetime
- 2000-02-14 WO PCT/EP2000/001202 patent/WO2000052009A1/de active IP Right Grant
- 2000-02-14 HU HU0200006A patent/HUP0200006A3/hu unknown
- 2000-02-14 AU AU31543/00A patent/AU763003B2/en not_active Ceased
- 2000-02-14 CA CA002362801A patent/CA2362801A1/en not_active Abandoned
- 2000-02-14 PL PL00349368A patent/PL349368A1/xx not_active Application Discontinuation
- 2000-02-14 US US09/914,090 patent/US6649762B1/en not_active Expired - Fee Related
- 2000-02-14 JP JP2000602235A patent/JP2002538158A/ja not_active Withdrawn
- 2000-02-14 RU RU2001126300/04A patent/RU2248356C2/ru not_active IP Right Cessation
- 2000-02-14 CZ CZ20013064A patent/CZ299700B6/cs not_active IP Right Cessation
- 2000-02-14 SK SK1195-2001A patent/SK285562B6/sk unknown
- 2000-02-14 TR TR2001/02434T patent/TR200102434T2/xx unknown
- 2000-02-14 DE DE50000700T patent/DE50000700D1/de not_active Expired - Fee Related
- 2000-02-14 DK DK00909166T patent/DK1155018T3/da active
- 2000-02-14 AT AT00909166T patent/ATE226952T1/de not_active IP Right Cessation
- 2000-02-14 CN CNB008043558A patent/CN1191253C/zh not_active Expired - Fee Related
- 2000-02-14 NZ NZ513750A patent/NZ513750A/en unknown
- 2000-02-14 PT PT00909166T patent/PT1155018E/pt unknown
- 2000-02-14 ES ES00909166T patent/ES2181644T3/es not_active Expired - Lifetime
-
2001
- 2001-07-31 ZA ZA200106289A patent/ZA200106289B/en unknown
- 2001-08-02 IL IL144702A patent/IL144702A/en not_active IP Right Cessation
- 2001-08-21 NO NO20014061A patent/NO320191B1/no unknown
-
2002
- 2002-09-04 HK HK02106521.3A patent/HK1044948B/zh not_active IP Right Cessation
Also Published As
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