CA2229786C - Zwitterionic forms of trovafloxacin - Google Patents
Zwitterionic forms of trovafloxacin Download PDFInfo
- Publication number
- CA2229786C CA2229786C CA002229786A CA2229786A CA2229786C CA 2229786 C CA2229786 C CA 2229786C CA 002229786 A CA002229786 A CA 002229786A CA 2229786 A CA2229786 A CA 2229786A CA 2229786 C CA2229786 C CA 2229786C
- Authority
- CA
- Canada
- Prior art keywords
- compound
- hygroscopic
- polymorph
- formula
- pentahydrate
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired - Fee Related
Links
- 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 title claims abstract description 22
- 229960000497 trovafloxacin Drugs 0.000 title claims abstract description 20
- 150000001875 compounds Chemical class 0.000 claims abstract description 39
- 238000000034 method Methods 0.000 claims abstract description 17
- 150000004686 pentahydrates Chemical class 0.000 claims abstract description 17
- 208000035143 Bacterial infection Diseases 0.000 claims abstract description 10
- 208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 9
- 241000124008 Mammalia Species 0.000 claims abstract description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 31
- 239000013078 crystal Substances 0.000 claims description 19
- 238000000634 powder X-ray diffraction Methods 0.000 claims description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical group CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 11
- 241001465754 Metazoa Species 0.000 claims description 9
- 230000001747 exhibiting effect Effects 0.000 claims description 9
- 239000002798 polar solvent Substances 0.000 claims description 9
- 238000010992 reflux Methods 0.000 claims description 9
- -1 t-butyloxycarbonyl Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 239000012452 mother liquor Substances 0.000 claims description 6
- 238000007605 air drying Methods 0.000 claims description 5
- 238000010533 azeotropic distillation Methods 0.000 claims description 5
- 238000001291 vacuum drying Methods 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 239000002253 acid Substances 0.000 claims description 4
- 125000006242 amine protecting group Chemical group 0.000 claims description 4
- 239000012454 non-polar solvent Substances 0.000 claims description 4
- 150000003839 salts Chemical class 0.000 claims description 4
- 239000000725 suspension Substances 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 3
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 125000006244 carboxylic acid protecting group Chemical group 0.000 claims description 3
- 239000012351 deprotecting agent Substances 0.000 claims description 3
- 239000003651 drinking water Substances 0.000 claims description 3
- 235000020188 drinking water Nutrition 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Chemical group O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 claims description 3
- 239000007900 aqueous suspension Substances 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 1
- 238000002360 preparation method Methods 0.000 abstract description 3
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000002002 slurry Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical group [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000001990 intravenous administration Methods 0.000 description 4
- 239000000546 pharmaceutical excipient Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 230000000844 anti-bacterial effect Effects 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 230000003115 biocidal effect Effects 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- 238000007918 intramuscular administration Methods 0.000 description 3
- ZFRUGZMCGCYBRC-UHFFFAOYSA-N 1h-1,8-naphthyridin-2-one Chemical compound C1=CC=NC2=NC(O)=CC=C21 ZFRUGZMCGCYBRC-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 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 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 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 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 229920002472 Starch Polymers 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000002775 capsule Substances 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 229940125898 compound 5 Drugs 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- 239000008101 lactose Substances 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 235000019698 starch Nutrition 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229960005021 trovafloxacin mesylate Drugs 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 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
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011369 resultant mixture Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- DYNZICQDCVYXFW-AHZSKCOESA-N trovafloxacin mesylate Chemical compound CS(O)(=O)=O.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 DYNZICQDCVYXFW-AHZSKCOESA-N 0.000 description 1
- 238000005406 washing Methods 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
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
-
- 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)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Epidemiology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Peptides Or Proteins (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Physical Water Treatments (AREA)
- Processing Of Solid Wastes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US297595P | 1995-08-29 | 1995-08-29 | |
| US60/002,975 | 1995-08-29 | ||
| PCT/IB1996/000756 WO1997007800A1 (en) | 1995-08-29 | 1996-07-29 | Zwitterionic forms of trovafloxacin |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2229786A1 CA2229786A1 (en) | 1997-03-06 |
| CA2229786C true CA2229786C (en) | 2002-02-19 |
Family
ID=21703460
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002229786A Expired - Fee Related CA2229786C (en) | 1995-08-29 | 1996-07-29 | Zwitterionic forms of trovafloxacin |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP0850060A1 (es) |
| JP (1) | JP3188476B2 (es) |
| KR (1) | KR100343909B1 (es) |
| CN (1) | CN1190889A (es) |
| AP (1) | AP636A (es) |
| AR (1) | AR003985A1 (es) |
| AU (1) | AU704115B2 (es) |
| BR (1) | BR9609998A (es) |
| CA (1) | CA2229786C (es) |
| CO (1) | CO4480739A1 (es) |
| CZ (1) | CZ56698A3 (es) |
| DZ (1) | DZ2087A1 (es) |
| GT (1) | GT199600072A (es) |
| HR (1) | HRP960395B1 (es) |
| HU (1) | HUP9900170A3 (es) |
| IL (1) | IL122651A (es) |
| MA (1) | MA23966A1 (es) |
| MY (1) | MY113874A (es) |
| NO (1) | NO309814B1 (es) |
| NZ (1) | NZ312199A (es) |
| OA (1) | OA10669A (es) |
| PE (1) | PE12598A1 (es) |
| PL (1) | PL325170A1 (es) |
| RU (1) | RU2144921C1 (es) |
| SK (1) | SK23898A3 (es) |
| TN (1) | TNSN96109A1 (es) |
| TR (1) | TR199800339T1 (es) |
| WO (1) | WO1997007800A1 (es) |
| YU (1) | YU48396A (es) |
| ZA (1) | ZA967282B (es) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HN1998000106A (es) | 1997-08-01 | 1999-01-08 | Pfizer Prod Inc | Composiciones parenterales de alatroflaxacino |
| US7019142B2 (en) | 1998-01-16 | 2006-03-28 | Pfizer Inc. | Process for preparing naphthyridones and intermediates |
| PA8466701A1 (es) * | 1998-01-21 | 2000-09-29 | Pfizer Prod Inc | Comprimido de mesilato de trovafloxacino |
| US6114531A (en) * | 1998-07-28 | 2000-09-05 | Pfizer Inc. | Process for preparing quinolone and naphthyridone carboxylic acids |
| HN1999000141A (es) * | 1998-09-03 | 2000-06-19 | Pfizer Prod Inc | Procedimiento para preparar sales de trovafloxacina de adicion de acidos. |
| US6239141B1 (en) | 1999-06-04 | 2001-05-29 | Pfizer Inc. | Trovafloxacin oral suspensions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS274601B2 (en) * | 1983-07-27 | 1991-09-15 | Dainippon Pharmaceutical Co | Method of 1,8-naphthyridine derivative production |
| AU623474B2 (en) * | 1989-01-16 | 1992-05-14 | Laboratoire Roger Bellon | New benzo(1,8)naphthyridine derivatives, their preparation and compositions containing them |
| US5164402A (en) * | 1989-08-16 | 1992-11-17 | Pfizer Inc | Azabicyclo quinolone and naphthyridinone carboxylic acids |
| DK0833837T3 (da) | 1995-06-15 | 2002-09-02 | Pfizer | Fremgangsmåde til fremstilling af derivater af azabicyclonaphthydridincarboxylsyre omfattende et dipeptid |
-
1996
- 1996-07-29 CA CA002229786A patent/CA2229786C/en not_active Expired - Fee Related
- 1996-07-29 NZ NZ312199A patent/NZ312199A/xx unknown
- 1996-07-29 SK SK238-98A patent/SK23898A3/sk unknown
- 1996-07-29 EP EP96923020A patent/EP0850060A1/en not_active Withdrawn
- 1996-07-29 BR BR9609998A patent/BR9609998A/pt unknown
- 1996-07-29 TR TR1998/00339T patent/TR199800339T1/xx unknown
- 1996-07-29 RU RU98103873/04A patent/RU2144921C1/ru not_active IP Right Cessation
- 1996-07-29 KR KR10-1998-0701468A patent/KR100343909B1/ko not_active Expired - Fee Related
- 1996-07-29 CZ CZ98566A patent/CZ56698A3/cs unknown
- 1996-07-29 CN CN96195624A patent/CN1190889A/zh active Pending
- 1996-07-29 AU AU63676/96A patent/AU704115B2/en not_active Ceased
- 1996-07-29 WO PCT/IB1996/000756 patent/WO1997007800A1/en not_active Ceased
- 1996-07-29 PL PL96325170A patent/PL325170A1/xx unknown
- 1996-07-29 IL IL12265196A patent/IL122651A/xx not_active IP Right Cessation
- 1996-07-29 HU HU9900170A patent/HUP9900170A3/hu unknown
- 1996-07-29 JP JP50343697A patent/JP3188476B2/ja not_active Expired - Fee Related
- 1996-08-23 GT GT199600072A patent/GT199600072A/es unknown
- 1996-08-26 AR ARP960104121A patent/AR003985A1/es unknown
- 1996-08-26 PE PE1996000633A patent/PE12598A1/es not_active Application Discontinuation
- 1996-08-28 ZA ZA9607282A patent/ZA967282B/xx unknown
- 1996-08-28 TN TNTNSN96109A patent/TNSN96109A1/fr unknown
- 1996-08-28 YU YU48396A patent/YU48396A/sh unknown
- 1996-08-28 DZ DZ960131A patent/DZ2087A1/fr active
- 1996-08-28 MY MYPI96003579A patent/MY113874A/en unknown
- 1996-08-28 MA MA24344A patent/MA23966A1/fr unknown
- 1996-08-29 CO CO96046149A patent/CO4480739A1/es unknown
- 1996-08-29 AP APAP/P/1996/000853A patent/AP636A/en active
- 1996-08-29 HR HR960395A patent/HRP960395B1/xx not_active IP Right Cessation
-
1998
- 1998-02-27 OA OA9800026A patent/OA10669A/en unknown
- 1998-02-27 NO NO980862A patent/NO309814B1/no not_active Application Discontinuation
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |