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 PDF

Info

Publication number: NO320314B1
Authority: NO; Norway
Prior art keywords: ccdc; modification; diazabicyclo; cyclopropyl; dihydro
Prior art date: 1999-02-26

Application number

NO20014059A

Other languages

English (en)

Norwegian (no)

Other versions

NO20014059L (no

NO20014059D0 (no

Inventor

Thomas Himmler

Hubert Rast

Original Assignee

Bayer Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-02-26

Filing date

2001-08-21

Publication date

2005-11-21

2001-08-21 Application filed by Bayer Ag filed Critical Bayer Ag

2001-08-21 Publication of NO20014059L publication Critical patent/NO20014059L/no

2001-08-21 Publication of NO20014059D0 publication Critical patent/NO20014059D0/no

2005-11-21 Publication of NO320314B1 publication Critical patent/NO320314B1/no

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)

NO20014059A 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. NO320314B1 (no)

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 (ru)
EP (1)	EP1159277A1 (ru)
JP (1)	JP2002538159A (ru)
KR (1)	KR100756474B1 (ru)
CN (1)	CN1217944C (ru)
AU (1)	AU760710B2 (ru)
BR (1)	BR0008520A (ru)
CA (1)	CA2362804A1 (ru)
CZ (1)	CZ20013065A3 (ru)
DE (1)	DE19908448A1 (ru)
HK (1)	HK1045158B (ru)
HU (1)	HUP0200053A3 (ru)
IL (1)	IL144528A0 (ru)
NO (1)	NO320314B1 (ru)
NZ (1)	NZ513749A (ru)
PL (1)	PL349394A1 (ru)
RU (1)	RU2248357C2 (ru)
SK (1)	SK11942001A3 (ru)
TR (1)	TR200102435T2 (ru)
UA (1)	UA71606C2 (ru)
WO (1)	WO2000052010A1 (ru)
ZA (1)	ZA200106050B (ru)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
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
RU2019128568A (ru)	2017-02-13	2021-03-15	Байер Энимэл Хельс ГмбХ	Жидкая композиция, содержащая прадофлоксацин

Family Cites Families (7)

* Cited by examiner, † Cited by third party
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
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
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 AU AU31544/00A patent/AU760710B2/en not_active Ceased
- 2000-02-14 HU HU0200053A patent/HUP0200053A3/hu unknown
- 2000-02-14 CZ CZ20013065A patent/CZ20013065A3/cs unknown
- 2000-02-14 JP JP2000602236A patent/JP2002538159A/ja not_active Withdrawn
- 2000-02-14 WO PCT/EP2000/001203 patent/WO2000052010A1/de not_active Application Discontinuation
- 2000-02-14 EP EP00909167A patent/EP1159277A1/de not_active Withdrawn
- 2000-02-14 RU RU2001126301/04A patent/RU2248357C2/ru not_active IP Right Cessation
- 2000-02-14 CA CA002362804A patent/CA2362804A1/en not_active Abandoned
- 2000-02-14 UA UA2001096577A patent/UA71606C2/ru unknown
- 2000-02-14 BR BR0008520-0A patent/BR0008520A/pt not_active IP Right Cessation
- 2000-02-14 CN CN00804306XA patent/CN1217944C/zh not_active Expired - Fee Related
- 2000-02-14 KR KR1020017009632A patent/KR100756474B1/ko not_active IP Right Cessation
- 2000-02-14 SK SK1194-2001A patent/SK11942001A3/sk not_active Application Discontinuation
- 2000-02-14 US US09/914,031 patent/US6492391B1/en not_active Expired - Fee Related
- 2000-02-14 NZ NZ513749A patent/NZ513749A/en unknown
- 2000-02-14 IL IL14452800A patent/IL144528A0/xx not_active IP Right Cessation
- 2000-02-14 PL PL00349394A patent/PL349394A1/xx not_active Application Discontinuation
- 2000-02-14 TR TR2001/02435T patent/TR200102435T2/xx 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
WO2000052010A1 (de)	2000-09-08
CN1341116A (zh)	2002-03-20
HK1045158B (zh)	2006-04-21
AU3154400A (en)	2000-09-21
DE19908448A1 (de)	2000-08-31
PL349394A1 (en)	2002-07-15
CZ20013065A3 (cs)	2002-01-16
HUP0200053A3 (en)	2003-01-28
HUP0200053A2 (hu)	2002-05-29
NZ513749A (en)	2003-10-31
RU2248357C2 (ru)	2005-03-20
BR0008520A (pt)	2001-12-18
EP1159277A1 (de)	2001-12-05
JP2002538159A (ja)	2002-11-12
KR20010093300A (ko)	2001-10-27
UA71606C2 (ru)	2004-12-15
SK11942001A3 (sk)	2001-12-03
HK1045158A1 (en)	2002-11-15
NO20014059L (no)	2001-08-21
US6492391B1 (en)	2002-12-10
KR100756474B1 (ko)	2007-09-07
CA2362804A1 (en)	2000-09-08
AU760710B2 (en)	2003-05-22
IL144528A0 (en)	2002-05-23
ZA200106050B (en)	2002-07-24
CN1217944C (zh)	2005-09-07
TR200102435T2 (tr)	2002-01-21
NO20014059D0 (no)	2001-08-21

Publication	Publication Date	Title
NO320314B1 (no)	2005-11-21	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.
NO320191B1 (no)	2005-11-07	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.
NO318065B1 (no)	2005-01-31	Krystallmodifikasjon B 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-quinolinkarboksylsyre
CA2351712C (en)	2011-07-12	Crystal modification a of 8-cyano-1-cyclopropyl-7-(1s,6s-2,8-diazabicylo-[4.3.0]nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid
WO2014193866A1 (en)	2014-12-04	Crystalline form of n,n-dicyclopropyl-4-(1,5-dimethyl-1 h-pyrazol-3-ylamino)-6-ethyl-1 -methyl-1,6-dihydroimidazo[4,5- d]fy rrolo[2,3-b]pyridine-7-carboxamide for the treatment of myeloproliferative disorders
MXPA01008650A (en)	2002-05-09	Crystal modification d of 8-cyano-1-cyclopropyl-7- (1s, 6s- 2,8- diazabicyclo- [4.3.0]nonan-8-yl) -6-fluoro -1,4-dihydro -4-oxo -3-quinoline carboxylic acid
MXPA01008651A (en)	2002-05-09	Crystal modification c of 8-cyano-1-cyclopropyl-7- (1s, 6s-2,8- diazabicyclo -[4.3.0]nonan-8-yl) -6-fluoro-1,4-dihydro-4-oxo-3-quinoline carboxylic
MXPA01005230A (en)	2003-11-07	Crystal modification a of 8-cyano-1- cyclopropyl -7-(1s,6s-2, 8-diazabicyclo [4.3.0]nonan -8-yl)-6- fluoro-1, 4-dihydro- 4-oxo-3- quinoline carboxylic acid
MXPA01005229A (en)	2002-03-26	Crystal modification b of 8-cyano-1- cyclopropyl -7-(1s,6s-2, 8-diazabicyclo [4.3.0]nonan -8-yl)-6- fluoro-1,4- dihydro-4- oxo-3-quinoline carboxylic acid