NO309039B1 - Polymorfer av pro-legemidlet 6-N-(L-ALA-L-ALA)-trovafloxacin - Google Patents

Polymorfer av pro-legemidlet 6-N-(L-ALA-L-ALA)-trovafloxacin Download PDF

Info

Publication number: NO309039B1
Authority: NO; Norway
Prior art keywords: pii; polymorph; diffraction pattern; water; pro
Prior art date: 1995-08-29

Application number

NO980863A

Other languages

English (en)

Norwegian (no)

Other versions

NO980863L (no

NO980863D0 (no

Inventor

Timothy Norris

James John Mcgarry

Douglas John Meldrum Allen

Original Assignee

Pfizer

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.)

1995-08-29

Filing date

1998-02-27

Publication date

2000-12-04

1998-02-27 Application filed by Pfizer filed Critical Pfizer

1998-02-27 Publication of NO980863L publication Critical patent/NO980863L/no

1998-02-27 Publication of NO980863D0 publication Critical patent/NO980863D0/no

2000-12-04 Publication of NO309039B1 publication Critical patent/NO309039B1/no

Links

239000000651 prodrug Substances 0.000 title claims description 19
229940002612 prodrug Drugs 0.000 title claims description 19
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 29
238000000034 method Methods 0.000 claims description 19
150000004682 monohydrates Chemical class 0.000 claims description 19
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 18
238000002441 X-ray diffraction Methods 0.000 claims description 14
150000001875 compounds Chemical class 0.000 claims description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
WVPSKSLAZQPAKQ-CDMJZVDBSA-N trovafloxacin Chemical compound C([C@H]1[C@@H]([C@H]1C1)N)N1C(C(=CC=1C(=O)C(C(O)=O)=C2)F)=NC=1N2C1=CC=C(F)C=C1F WVPSKSLAZQPAKQ-CDMJZVDBSA-N 0.000 claims description 11
229960000497 trovafloxacin Drugs 0.000 claims description 11
208000035143 Bacterial infection Diseases 0.000 claims description 7
239000003960 organic solvent Substances 0.000 claims description 7
238000000634 powder X-ray diffraction Methods 0.000 claims description 7
239000002904 solvent Substances 0.000 claims description 7
208000022362 bacterial infectious disease Diseases 0.000 claims description 6
238000001291 vacuum drying Methods 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
239000002253 acid Substances 0.000 claims description 3
239000000825 pharmaceutical preparation Substances 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
150000007513 acids Chemical class 0.000 claims description 2
125000005907 alkyl ester group Chemical group 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
125000006724 (C1-C5) alkyl ester group Chemical group 0.000 claims 1
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
239000002002 slurry Substances 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 10
238000010992 reflux Methods 0.000 description 9
238000001914 filtration Methods 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
241001465754 Metazoa Species 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000000243 solution Substances 0.000 description 4
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
BZNDDHWTEVCBAD-BQBZGAKWSA-N (2s)-2-[[(2s)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]propanoic acid Chemical compound OC(=O)[C@H](C)NC(=O)[C@H](C)NC(=O)OC(C)(C)C BZNDDHWTEVCBAD-BQBZGAKWSA-N 0.000 description 2
GKQLYSROISKDLL-UHFFFAOYSA-N EEDQ Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)C=CC2=C1 GKQLYSROISKDLL-UHFFFAOYSA-N 0.000 description 2
-1 L- alaninamide- methanesulfonate Chemical compound 0.000 description 2
239000000654 additive Substances 0.000 description 2
230000001580 bacterial effect Effects 0.000 description 2
238000007918 intramuscular administration Methods 0.000 description 2
238000001990 intravenous administration Methods 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229940098779 methanesulfonic acid Drugs 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
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 1
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
229920002472 Starch Polymers 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
230000009286 beneficial effect Effects 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
239000002775 capsule Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000003086 colorant Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000003651 drinking water Substances 0.000 description 1
235000020188 drinking water Nutrition 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
239000008103 glucose Substances 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000008101 lactose Substances 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000725 suspension Substances 0.000 description 1
238000010998 test method Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/02—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing at least one abnormal peptide link
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K5/00—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof
- C07K5/04—Peptides containing up to four amino acids in a fully defined sequence; Derivatives thereof containing only normal peptide links
- C07K5/06—Dipeptides
- C07K5/06191—Dipeptides containing heteroatoms different from O, S, or N
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K38/00—Medicinal preparations containing peptides

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Biophysics (AREA)
Genetics & Genomics (AREA)
Proteomics, Peptides & Aminoacids (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Oncology (AREA)
Communicable Diseases (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Peptides Or Proteins (AREA)
Steroid Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

NO980863A 1995-08-29 1998-02-27 Polymorfer av pro-legemidlet 6-N-(L-ALA-L-ALA)-trovafloxacin NO309039B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US510995P	1995-08-29	1995-08-29
PCT/IB1996/000653 WO1997008191A1 (en)	1995-08-29	1996-07-05	Polymorphs of the prodrug 6-n-(l-ala-l-ala)-trovafloxacin

Publications (3)

Publication Number	Publication Date
NO980863L NO980863L (no)	1998-02-27
NO980863D0 NO980863D0 (no)	1998-02-27
NO309039B1 true NO309039B1 (no)	2000-12-04

Family

ID=21714229

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO980863A NO309039B1 (no)	1995-08-29	1998-02-27	Polymorfer av pro-legemidlet 6-N-(L-ALA-L-ALA)-trovafloxacin

Country Status (35)

Country	Link
US (1)	US6080756A (cs)
EP (1)	EP0847400B1 (cs)
JP (1)	JPH11509188A (cs)
KR (1)	KR100274736B1 (cs)
CN (1)	CN1193977A (cs)
AP (1)	AP639A (cs)
AR (1)	AR004507A1 (cs)
AT (1)	ATE208790T1 (cs)
AU (1)	AU696414B2 (cs)
BR (1)	BR9610283A (cs)
CA (1)	CA2230303C (cs)
CO (1)	CO4480740A1 (cs)
CZ (1)	CZ291524B6 (cs)
DE (1)	DE69617027T2 (cs)
DK (1)	DK0847400T3 (cs)
DZ (1)	DZ2088A1 (cs)
ES (1)	ES2164892T3 (cs)
GT (1)	GT199600061A (cs)
HR (1)	HRP960396A2 (cs)
HU (1)	HUP9900226A3 (cs)
IL (1)	IL122652A (cs)
MA (1)	MA23965A1 (cs)
NO (1)	NO309039B1 (cs)
NZ (1)	NZ310542A (cs)
OA (1)	OA10670A (cs)
PL (1)	PL185709B1 (cs)
PT (1)	PT847400E (cs)
RU (1)	RU2151152C1 (cs)
SK (1)	SK283354B6 (cs)
TN (1)	TNSN96110A1 (cs)
TR (1)	TR199800340T1 (cs)
UA (1)	UA48982C2 (cs)
WO (1)	WO1997008191A1 (cs)
YU (1)	YU48296A (cs)
ZA (1)	ZA967281B (cs)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HN1998000106A (es) *	1997-08-01	1999-01-08	Pfizer Prod Inc	Composiciones parenterales de alatroflaxacino
US6239141B1 (en) *	1999-06-04	2001-05-29	Pfizer Inc.	Trovafloxacin oral suspensions
CN105510497A (zh) *	2015-11-30	2016-04-20	精晶药业股份有限公司	L-丙氨酰-l-丙氨酸的定量检测方法

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2548664B1 (fr) *	1983-07-06	1986-03-21	Provesan Sa	Derives 7-(pyrrol-l-yl) des acides l-ethyl-1,4-dihydro-4-oxoquinoleine-3-carboxyliques et l-ethyl-1,4-dihydro-4-oxo-(1,8-naphtyridine)-3-carboxyliques substitues, leur preparation et leur application en tant que medicaments
JPH0635458B2 (ja) *	1985-02-15	1994-05-11	大日本製薬株式会社	ピリドンカルボン酸誘導体、そのエステルおよびその塩
NZ232091A (en) *	1989-01-16	1990-12-21	Bellon Labor Sa Roger	7-fluoro-8-(piperazin-1-yl)-4-oxo-1,4-dihydro-benzo(b)(1,8)naphthyridine-3-carboxylic acid derivatives, preparation and pharmaceutical compositions thereof
US5164402A (en) *	1989-08-16	1992-11-17	Pfizer Inc	Azabicyclo quinolone and naphthyridinone carboxylic acids

1996
- 1996-07-05 US US09/011,370 patent/US6080756A/en not_active Expired - Fee Related
- 1996-07-05 DK DK96918806T patent/DK0847400T3/da active
- 1996-07-05 UA UA98021016A patent/UA48982C2/uk unknown
- 1996-07-05 RU RU98103462/04A patent/RU2151152C1/ru not_active IP Right Cessation
- 1996-07-05 CA CA002230303A patent/CA2230303C/en not_active Expired - Fee Related
- 1996-07-05 CZ CZ1998552A patent/CZ291524B6/cs not_active IP Right Cessation
- 1996-07-05 PT PT96918806T patent/PT847400E/pt unknown
- 1996-07-05 NZ NZ310542A patent/NZ310542A/en unknown
- 1996-07-05 AT AT96918806T patent/ATE208790T1/de not_active IP Right Cessation
- 1996-07-05 BR BR9610283A patent/BR9610283A/pt not_active Application Discontinuation
- 1996-07-05 AU AU61351/96A patent/AU696414B2/en not_active Ceased
- 1996-07-05 JP JP9504021A patent/JPH11509188A/ja active Pending
- 1996-07-05 DE DE69617027T patent/DE69617027T2/de not_active Expired - Fee Related
- 1996-07-05 HU HU9900226A patent/HUP9900226A3/hu unknown
- 1996-07-05 EP EP96918806A patent/EP0847400B1/en not_active Expired - Lifetime
- 1996-07-05 IL IL12265296A patent/IL122652A/xx not_active IP Right Cessation
- 1996-07-05 PL PL96325203A patent/PL185709B1/pl unknown
- 1996-07-05 KR KR1019980701467A patent/KR100274736B1/ko not_active Expired - Fee Related
- 1996-07-05 WO PCT/IB1996/000653 patent/WO1997008191A1/en not_active Ceased
- 1996-07-05 ES ES96918806T patent/ES2164892T3/es not_active Expired - Lifetime
- 1996-07-05 SK SK237-98A patent/SK283354B6/sk unknown
- 1996-07-05 CN CN96196577A patent/CN1193977A/zh active Pending
- 1996-07-05 TR TR1998/00340T patent/TR199800340T1/xx unknown
- 1996-08-09 GT GT199600061A patent/GT199600061A/es unknown
- 1996-08-23 AR ARP960104085A patent/AR004507A1/es unknown
- 1996-08-28 DZ DZ960132A patent/DZ2088A1/fr active
- 1996-08-28 MA MA24343A patent/MA23965A1/fr unknown
- 1996-08-28 YU YU48296A patent/YU48296A/sh unknown
- 1996-08-28 TN TNTNSN96110A patent/TNSN96110A1/fr unknown
- 1996-08-28 ZA ZA9607281A patent/ZA967281B/xx unknown
- 1996-08-29 AP APAP/P/1996/000854A patent/AP639A/en active
- 1996-08-29 HR HR60/005,109A patent/HRP960396A2/hr not_active Application Discontinuation
- 1996-08-29 CO CO96046150A patent/CO4480740A1/es unknown
1998
- 1998-02-27 NO NO980863A patent/NO309039B1/no unknown
- 1998-02-27 OA OA9800027A patent/OA10670A/en unknown

Also Published As

Publication number	Publication date
OA10670A (en)	2000-11-06
WO1997008191A1 (en)	1997-03-06
UA48982C2 (uk)	2002-09-16
SK283354B6 (sk)	2003-06-03
RU2151152C1 (ru)	2000-06-20
IL122652A (en)	2000-01-31
PT847400E (pt)	2002-03-28
KR100274736B1 (ko)	2000-12-15
AU6135196A (en)	1997-03-19
CZ291524B6 (cs)	2003-03-12
KR19990044231A (ko)	1999-06-25
US6080756A (en)	2000-06-27
MX9801665A (es)	1998-08-30
BR9610283A (pt)	1999-03-16
CN1193977A (zh)	1998-09-23
CZ55298A3 (cs)	1999-02-17
ATE208790T1 (de)	2001-11-15
MA23965A1 (fr)	1997-04-01
PL185709B1 (pl)	2003-07-31
SK23798A3 (en)	1999-05-07
HRP960396A2 (en)	1998-04-30
HUP9900226A2 (hu)	1999-05-28
DE69617027T2 (de)	2002-03-21
CA2230303C (en)	2001-07-24
AP639A (en)	1998-04-14
TR199800340T1 (xx)	1998-06-22
NO980863L (no)	1998-02-27
ZA967281B (en)	1998-03-02
DZ2088A1 (fr)	2002-07-22
CO4480740A1 (es)	1997-07-09
DK0847400T3 (da)	2002-03-25
TNSN96110A1 (fr)	2005-03-15
NZ310542A (en)	1999-09-29
JPH11509188A (ja)	1999-08-17
EP0847400A1 (en)	1998-06-17
PL325203A1 (en)	1998-07-06
ES2164892T3 (es)	2002-03-01
IL122652A0 (en)	1996-08-16
AU696414B2 (en)	1998-09-10
YU48296A (sh)	1998-12-23
NO980863D0 (no)	1998-02-27
AP9600854A0 (en)	1996-10-31
EP0847400B1 (en)	2001-11-14
HUP9900226A3 (en)	1999-11-29
AR004507A1 (es)	1998-12-16
CA2230303A1 (en)	1997-03-06
GT199600061A (es)	1998-01-31
DE69617027D1 (de)	2001-12-20

Publication	Publication Date	Title
US5763454A (en)	1998-06-09	Crystal form of anhydrous 7-( 1α,5α,6α!-6-amino-3-azabicyclo 3.1.0!hex-3-yl)-6-fluoro-1-(2,4-difluorophenyl)-1,4-dihydro-4-oxo-1,8 naphthyridine-3-carboxylic acid, methanessulfonic acid salt
CA3127448C (en)	2024-06-04	Mtorc modulators and uses thereof
BG104105A (bg)	2000-08-31	Алатрофлоксацинови парентерални състави
US6080756A (en)	2000-06-27	Polymorphs of the prodrug 6-N-(L-ALA-L-ALA)-trovafloxacin
AU704115B2 (en)	1999-04-15	Zwitterionic forms of trovafloxacin
AP788A (en)	1999-12-03	Novel crystal form of anhydrous 7-(1a, 5a, 6a)-6-Amino-3-Azabicyclo(3.1.0) hex-3-YI)-6-Fluoro-1-(2,4- Difluorophenyl)-1,4-Dihydro-4-Oxo-1, 8-Naphthyridine-3-Carboxylic Acid, Methanesulfonic acid salt.
MXPA98001665A (en)	1998-11-12	Polymorphoses of profarmaco of 6-n- (l-ala-l-ala) -trovafloxacin, procedure for its preparation and use of mis
MXPA98001664A (en)	1998-11-12	Zwitterionic forms of trovafloxacin, procedure for its preparation, compositions that contain them and use of the mis