WO2009136408A4 - Synergistic pharmaceutical cocrystals - Google Patents
Synergistic pharmaceutical cocrystals Download PDFInfo
- Publication number
- WO2009136408A4 WO2009136408A4 PCT/IN2009/000233 IN2009000233W WO2009136408A4 WO 2009136408 A4 WO2009136408 A4 WO 2009136408A4 IN 2009000233 W IN2009000233 W IN 2009000233W WO 2009136408 A4 WO2009136408 A4 WO 2009136408A4
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- infections
- norfloxacin
- acid
- ciprofloxacin
- pharmaceutical
- 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.)
- Ceased
Links
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
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/496—Non-condensed piperazines containing further heterocyclic rings, e.g. rifampin, thiothixene or sparfloxacin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/14—Particulate form, e.g. powders, Processes for size reducing of pure drugs or the resulting products, Pure drug nanoparticles
- A61K9/141—Intimate drug-carrier mixtures characterised by the carrier, e.g. ordered mixtures, adsorbates, solid solutions, eutectica, co-dried, co-solubilised, co-kneaded, co-milled, co-ground products, co-precipitates, co-evaporates, co-extrudates, co-melts; Drug nanoparticles with adsorbed surface modifiers
Landscapes
- Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
The present invention discloses synergistic pharmaceutical co crystals comprising soluble forms of broad-spectrum fluoroquinolone antibacterial agents namely Ciprofloxacin and Norfloxacin with small molecules that have unique physical properties and biological activity which differ from the active agent in pure form, process for preparation of the same and also discloses pharmaceutical compositions comprising these synergistic cocrystals.
Claims
1. Synergistic, soluble forms of pharmaceutical co-crystal compositions comprising a) at least one fluroquinolone compound selected from Ciprofloxacin and Norfloxacin and b) a co-crystal former selected from the group comprising of phenolics selected from the group consisting of resveratrol, Capsaicin, Chavibetol, Guaiacol, rosmarinic acid, anethole, chavicol, vanillin; flavonoids such as catechin hydrate, quercetin dihydrate chrysin, galangin, rutin, hesperidine; glycosides of quercetin, kaempferol, chrysin; monoterpenes such as geraniol, linalool, citral, camphor, menthol, ocimene, pinenes; aminoacids such as phenyl alanine, glutamic acid, glutamine, glycine; alkaloids such as piperine, Trigonelline, pilocarpene, atropine, Ephedrine; vitamins such as folic acid, pyridoxine, Pantothenic acid, tocoferol, biotin, ascorbic acid; neutraceuticals such as caffeine, monosaccharides, di and tri saccharides, citric acid, tartaric acid, hydroxy citric acid, and also other small molecules such as, cinnamic acid & its derivatives, curcumin, vanillin, piperonyl alcohol,, rosmarinic acid, adipic acid, Ajoene, alliin, lipoic acid, gallic acvid, proanthocyanines, zingiberene, isoflavones, cuminaldehyde, saponins(diosgenin, yamogenin, tigogenin)and rosmarinic acid.
2. The pharmaceutical co-crystals compositions as claimed in claim 1, wherein said fluroquinolone compound is Ciprofloxacin.
3. The pharmaceutical co-crystals compositions as claimed in claim 1, wherein said fluroquinolone compound is Norfloxacin.
4. The pharmaceutical co-crystals as claimed in claim 2, wherein said co-crystal is selected from the group comprising of Ciprofloxacin and eugenol; Ciprofloxacin and ferulic acid, Ciprofloxacin and isoferulic acid, Ciprofloxacin and citric acid, Ciprofloxacin and tartaric acid.
5. The pharmaceutical co-crystals compositions as claimed in claim 3, wherein said co-crystal is selected from the group comprising of Norfloxacin and eugenol; 33
Norfloxacin and ferulic acid; Norfloxacin and isoferulic acid; Norfloxacin and adipic acid; Norfloxacin and biotin; Norfloxacin and caffeine; Norfloxacin and catechin hydrate; Norfloxacin and citric acid; Norfloxacin and curcumin; Norfloxacin and geraniol; Norfloxacin and glutamic acid; Norfloxacin and glutamine; Norfloxacin and glycine; Norfloxacin and vanillin; Norfloxacin and phenyl alanine; Norfloxacin and piperonyl alcohol; Norfloxacin and quercitine dehydrate; Norfloxacin and resveratrol; or Norfloxacin and rosmarinic acid.
6. The pharmaceutical co-crystal composition according to claim 1, further comprising a pharmaceutically acceptable diluent, excipient or carrier.
7. A process for preparing a pharmaceutical co-crystal composition according to claim 6, comprising (a) hand grinding of fluoroquinoline compound and cocrystal former in 1:1 ratio in mortar pestle for 5 minutes for making the mixture homogenous; (b) crystallizing the homogenous mixture obtained in step (a) from suitable organic solvents selected from ethanol, methanol, isopropyl alcohol, dimethyl formamide, acetonitrile, dimethyl formamide- acetonitrile, tetrahydrofuran, dioxane under ambient to reflux conditions; (c) incorporating the co-crystals thus obtained in step (b) into a pharmaceutical composition using one or more suitable carriers/excipients.
8. Method for treating symptoms associated, with skin infections, chest infections, urinary tract infections, gastro-intestinaϊ infections, mycobacterial infections as well as eye infections, which method comprises administering 'an effective amount' of the 'Ciprofloxacin-cocrystals' according to claim 4, to the subject suffering from skin infections, chest infections, urinary tract infections, gastrointestinal infections, mycobacterial infections as well as eye infections.
9. Method for treating symptoms associated with urinary tract infections, stomach infections, mycobacterial infections as well as eye infections, which method comprises administering 'an effective amount' of the 'Norfloxacin-cocrystals' according to claim 5, to the subject suffering from urinary tract infections stomach infections, mycobacterial infections as well as eye infections.
10. The method according to claim 8 or 9, wherein said subject is human.
11. Use of the composition comprising Ciprofloxacin co-crystals according to claim 4, in preparing the medicament intend to treat wide spectrum of bacterial infections selected from skin infections, chest infections, urinary tract infections, eye infections, mycobacterial infections and gastro-intestinal system infections.
12. Use of the composition comprising Norfloxacin co-crystals according to claim 5 in preparing the medicament intend to treat wide spectrum of bacterial infections selected from urinary tract infections, eye infections, mycobacterial infections as well as stomach infections.
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN883/CHE/2008 | 2008-04-09 | ||
| IN883CH2008 | 2008-04-09 | ||
| IN2012/CHE/2008 | 2008-08-19 | ||
| IN2012CH2008 | 2008-08-19 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| WO2009136408A1 WO2009136408A1 (en) | 2009-11-12 |
| WO2009136408A4 true WO2009136408A4 (en) | 2010-01-21 |
Family
ID=41264485
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/IN2009/000233 Ceased WO2009136408A1 (en) | 2008-04-09 | 2009-04-09 | Synergistic pharmaceutical cocrystals |
Country Status (1)
| Country | Link |
|---|---|
| WO (1) | WO2009136408A1 (en) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110105600A1 (en) * | 2009-10-29 | 2011-05-05 | Glykon Technologies Group, Llc | Synergistic composition of (-)-hydroxycitric acid with monoterpene and a method to enhance satiety |
| MX2011004759A (en) * | 2011-05-04 | 2012-11-21 | Senosiain S A De C V Lab | Novel antibiotic solid forms. |
| CN102342910B (en) * | 2011-10-03 | 2012-09-19 | 白求恩医科大学制药厂 | Levofloxacin hydrochloride injection pharmaceutical composition and preparation method thereof |
| US20150322033A1 (en) * | 2012-11-13 | 2015-11-12 | Juntendo Educational Foundation | Antibacterial agent |
| CN103265483A (en) * | 2013-05-24 | 2013-08-28 | 常州大学 | Co-crystal of norfloxacin and phthalic acid and preparation method thereof |
| CN103864683B (en) * | 2014-02-14 | 2015-07-01 | 博瑞生物医药泰兴市有限公司 | Medicine eutectic of ciprofloxacin and salicylic acid and preparation process thereof |
| WO2017001991A1 (en) * | 2015-06-29 | 2017-01-05 | Crystalmorphix Technologies Pvt. Ltd | Cocrystals of trigonelline |
| CN105777711B (en) * | 2016-04-07 | 2018-08-14 | 常州大学 | A kind of pharmaceutical co-crystals body and preparation method thereof of Lomefloxacin and 5-F- M-phthalic acids |
| CN106995409A (en) * | 2017-03-31 | 2017-08-01 | 常州大学 | Improve the preparation method and structure of the phthalic acid pharmaceutical co-crystals body of Ciprofloxacin solubility |
| CN107089946B (en) * | 2017-05-05 | 2020-04-03 | 浙江科技学院 | Norfloxacin and vanillin eutectic crystal and preparation method thereof |
| WO2020086890A1 (en) | 2018-10-24 | 2020-04-30 | Sundeep Dugar | Co-crystals comprising epicatechin and a carboxy-n-heterocyclic co-crystal former |
| CN112851666B (en) * | 2019-11-28 | 2023-11-03 | 中国医学科学院药物研究所 | Apixaban and quercetin co-crystal and its preparation method and its composition and use |
| CN114891024A (en) * | 2021-08-03 | 2022-08-12 | 青岛市食品药品检验研究院（青岛市药品不良反应监测中心、青岛市实验动物和动物实验中心） | A kind of levofloxacin-nicotinic acid drug co-crystal and preparation method thereof |
| CN114031515B (en) * | 2021-11-29 | 2022-10-21 | 河北大学 | Acetaminophen-ibuprofen pharmaceutical co-crystal and preparation method thereof |
| CN118852110B (en) * | 2024-09-25 | 2024-12-03 | 吉林大学 | Sparfloxacin-cinnamic acid eutectic, and preparation method and application thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL80459A (en) * | 1986-10-30 | 1991-04-15 | Abic Ltd | Water-soluble adduct of norfloxacin and nicotinic acid |
| ES2127036B1 (en) * | 1994-03-21 | 1999-11-16 | Ind Quimica Agropecuaria S A | NORFLOXACINE ADDUCT SOLUBLE IN WATER. |
| US7838532B2 (en) * | 2005-05-18 | 2010-11-23 | Mpex Pharmaceuticals, Inc. | Aerosolized fluoroquinolones and uses thereof |
| CN1785193A (en) * | 2005-11-21 | 2006-06-14 | 沈阳药科大学 | Amino acid (-) ofloxacin water soluble salt |
| CN101386593B (en) * | 2007-09-14 | 2012-09-05 | 刘力 | Norfloxacin glutamate hydrate and preparation and use thereof |
-
2009
- 2009-04-09 WO PCT/IN2009/000233 patent/WO2009136408A1/en not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2009136408A1 (en) | 2009-11-12 |
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