PT690864E - Acido livre de ceftiofur cristalino - Google Patents
Acido livre de ceftiofur cristalino Download PDFInfo
- Publication number
- PT690864E PT690864E PT94910721T PT94910721T PT690864E PT 690864 E PT690864 E PT 690864E PT 94910721 T PT94910721 T PT 94910721T PT 94910721 T PT94910721 T PT 94910721T PT 690864 E PT690864 E PT 690864E
- Authority
- PT
- Portugal
- Prior art keywords
- crystalline
- ceftiofur
- free acid
- oil
- compound
- Prior art date
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- ZBHXIWJRIFEVQY-IHMPYVIRSA-N ceftiofur Chemical compound S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC(=O)C1=CC=CO1 ZBHXIWJRIFEVQY-IHMPYVIRSA-N 0.000 title claims abstract description 118
- 239000002253 acid Substances 0.000 title claims abstract description 115
- 229960005229 ceftiofur Drugs 0.000 title claims abstract description 109
- 238000000034 method Methods 0.000 claims abstract description 40
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 6
- 239000000203 mixture Substances 0.000 claims description 58
- 150000001875 compounds Chemical class 0.000 claims description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 30
- 238000002360 preparation method Methods 0.000 claims description 28
- KEQFDTJEEQKVLM-JUODUXDSSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-(furan-2-carbonylsulfanylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydron;chloride Chemical compound Cl.S([C@@H]1[C@@H](C(N1C=1C(O)=O)=O)NC(=O)\C(=N/OC)C=2N=C(N)SC=2)CC=1CSC(=O)C1=CC=CO1 KEQFDTJEEQKVLM-JUODUXDSSA-N 0.000 claims description 23
- 238000013268 sustained release Methods 0.000 claims description 20
- 239000012730 sustained-release form Substances 0.000 claims description 19
- 239000003921 oil Substances 0.000 claims description 18
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- 229960001356 ceftiofur hydrochloride Drugs 0.000 claims description 16
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
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- 235000012343 cottonseed oil Nutrition 0.000 claims description 4
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- 229930186147 Cephalosporin Natural products 0.000 abstract description 11
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- 238000013103 analytical ultracentrifugation Methods 0.000 description 13
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 12
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
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- NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
- 229940038472 dicalcium phosphate Drugs 0.000 description 1
- 229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
- 238000000113 differential scanning calorimetry Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
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- 125000001475 halogen functional group Chemical group 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
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- YGZIWEZFFBPCLN-UHFFFAOYSA-N n,3-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2$l^{5}-oxazaphosphinan-2-amine Chemical compound OOC1CCOP(=O)(NCCCl)N1CCCl YGZIWEZFFBPCLN-UHFFFAOYSA-N 0.000 description 1
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- 229960003742 phenol Drugs 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000001907 polarising light microscopy Methods 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
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- 230000002459 sustained effect Effects 0.000 description 1
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- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
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- 229940116362 tragacanth Drugs 0.000 description 1
- 238000013519 translation Methods 0.000 description 1
- 150000004684 trihydrates Chemical class 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- 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
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Virology (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US3329193A | 1993-03-12 | 1993-03-12 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PT690864E true PT690864E (pt) | 2001-11-30 |
Family
ID=21869579
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PT94910721T PT690864E (pt) | 1993-03-12 | 1994-03-07 | Acido livre de ceftiofur cristalino |
Country Status (31)
| Country | Link |
|---|---|
| US (1) | US5721359A (en:Method) |
| EP (1) | EP0690864B1 (en:Method) |
| JP (1) | JP3852946B2 (en:Method) |
| KR (1) | KR100296810B1 (en:Method) |
| CN (1) | CN1055090C (en:Method) |
| AT (1) | ATE202109T1 (en:Method) |
| AU (1) | AU694419B2 (en:Method) |
| BR (1) | BR1101034A (en:Method) |
| CA (1) | CA2155322C (en:Method) |
| CZ (1) | CZ289332B6 (en:Method) |
| DE (2) | DE69427469T2 (en:Method) |
| DK (1) | DK0690864T3 (en:Method) |
| ES (1) | ES2157254T3 (en:Method) |
| FI (1) | FI120307B (en:Method) |
| FR (1) | FR05C0045I2 (en:Method) |
| GR (1) | GR3036514T3 (en:Method) |
| HU (1) | HU222244B1 (en:Method) |
| IL (1) | IL108910A (en:Method) |
| LU (1) | LU91206I2 (en:Method) |
| LV (1) | LV12889B (en:Method) |
| NL (1) | NL300208I2 (en:Method) |
| NO (2) | NO313199B1 (en:Method) |
| NZ (1) | NZ263002A (en:Method) |
| PL (1) | PL184611B1 (en:Method) |
| PT (1) | PT690864E (en:Method) |
| RU (1) | RU2136685C1 (en:Method) |
| SI (1) | SI0690864T1 (en:Method) |
| SK (1) | SK283674B6 (en:Method) |
| TW (1) | TW267170B (en:Method) |
| WO (1) | WO1994020505A1 (en:Method) |
| ZA (1) | ZA941586B (en:Method) |
Families Citing this family (73)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5736151A (en) * | 1996-12-09 | 1998-04-07 | Pharmacia & Upjohn Company | Antibiotic oil suspensions |
| US6074657A (en) * | 1997-03-20 | 2000-06-13 | Pharmacia & Upjohn Company | Administration of an injectable antibiotic in the ear of an animal |
| MXPA03002055A (es) * | 2000-09-12 | 2004-12-13 | Upjohn Co | Composicion farmaceutica con excipiente modificado. |
| US7829100B2 (en) * | 2000-09-12 | 2010-11-09 | Teagarden Dirk L | Pharmaceutical composition having modified carrier |
| KR100423895B1 (ko) * | 2001-02-19 | 2004-03-24 | 주식회사 엘지생명과학 | 셉티오퍼 하이드로클로라이드의 현탁제 조성물 |
| CA2453182A1 (en) * | 2001-07-10 | 2003-01-23 | Meredith L. Greene | Crystalline thiazine oxazolidinones |
| JP4159988B2 (ja) | 2001-08-15 | 2008-10-01 | ファルマシア・アンド・アップジョン・カンパニー・エルエルシー | Ｎ−［２−（ジエチルアミノ）エチル］−５−［（５−フルオロ−１，２−ジヒドロ−２−オキソ−３ｈ−インドール−３−イリデン）メチル］−２，４−ジメチル−１ｈ−ピロール−３−カルボキシアミドのリンゴ酸塩を含む結晶、その製法およびその組成物 |
| KR20040097187A (ko) | 2002-03-21 | 2004-11-17 | 파마시아 앤드 업존 캄파니 | 동물의 귀로의 주사가능한 항생제의 투여 방법 |
| US20040022815A1 (en) * | 2002-08-05 | 2004-02-05 | Orchid Health Care | Novel pharmaceutical composition of ceftiofur |
| KR20040015622A (ko) * | 2002-08-13 | 2004-02-19 | 대한뉴팜(주) | 세프티오푸르나트륨을 활성성분으로 함유하는 현탁주사액조성물 |
| US20040115822A1 (en) * | 2002-09-12 | 2004-06-17 | Schapaugh Randal Lee | Methods of measuring the dissolution rate of an analyte in a non-aqueous liquid composition |
| US7659061B2 (en) * | 2002-11-19 | 2010-02-09 | Pharmacia & Upjohn Company | Pharmaceutical compositions having a modified vehicle |
| US20040115837A1 (en) * | 2002-11-27 | 2004-06-17 | Schapaugh Randal Lee | Methods of measuring the dissolution rate of an analyte in a non-aqueous liquid composition |
| US7842791B2 (en) * | 2002-12-19 | 2010-11-30 | Nancy Jean Britten | Dispersible pharmaceutical compositions |
| BRPI0408716B1 (pt) * | 2003-03-27 | 2017-08-29 | Basilea Pharmaceutica Ag. | Cefalosporin in crystalline form, process for its preparation and its uses, and preparation of cephalosporin |
| KR101836467B1 (ko) * | 2004-03-25 | 2018-03-08 | 아스텔라스세이야쿠 가부시키가이샤 | 솔리페나신 또는 그의 염의 고형 제제용 조성물 |
| US7815939B2 (en) | 2005-07-20 | 2010-10-19 | Astellas Pharma Inc. | Coated fine particles containing drug for intrabuccally fast disintegrating dosage forms |
| WO2007042917A1 (en) * | 2005-10-12 | 2007-04-19 | Orchid Chemicals And Pharmaceuticals Limited | Crystalline sodium salt of cephalosporin antibiotic |
| US8470809B2 (en) * | 2005-10-12 | 2013-06-25 | Orchid Chemicals & Pharmaceuticals Limited | Crystalline sodium salt of cephalosporin antibiotic |
| ES2442926T3 (es) | 2007-08-22 | 2014-02-14 | Astrazeneca Ab | Derivados de ciclopropilamida `978 |
| WO2010036427A1 (en) | 2008-06-17 | 2010-04-01 | Brigham Young University | Cationic steroid antimicrobial diagnostic, detection, screening and imaging methods |
| EP2324034A4 (en) * | 2008-08-22 | 2012-05-16 | Orchid Chemicals & Pharm Ltd | CRYSTALLINE SODIUM SALT OF CEPHALOSPORIN ANTIBIOTIC |
| NZ592984A (en) * | 2008-11-19 | 2012-12-21 | Merial Ltd | Formulations comprising ceftiofur and ketoprofen or ceftiofur and benzyl alcohol |
| EA018907B1 (ru) * | 2009-01-30 | 2013-11-29 | ГЛЭКСОСМИТКЛАЙН ЭлЭлСи | Кристаллический гидрохлорид n-{(1s)-2-амино-1-[(3-фторфенил)метил]этил}-5-хлор-4-(4-хлор-1-метил-1h-пиразол-5-ил)-2-тиофенкарбоксамида |
| TW201039825A (en) | 2009-02-20 | 2010-11-16 | Astrazeneca Ab | Cyclopropyl amide derivatives 983 |
| SG183231A1 (en) * | 2010-02-18 | 2012-09-27 | Astrazeneca Ab | Solid forms comprising a cyclopropyl amide derivative |
| WO2011102794A1 (en) | 2010-02-18 | 2011-08-25 | Astrazeneca Ab | Processes for making cyclopropyl amide derivatives and intermediates associated therewith |
| CN103649097A (zh) * | 2011-05-02 | 2014-03-19 | 佐蒂斯有限责任公司 | 用作抗菌剂的新型头孢菌素类 |
| BR112014001444A2 (pt) | 2011-07-20 | 2017-07-18 | Univ Brigham Young | compostos hidrofóbicos de ceragenina e dispositivos que incorporam os mesmos |
| JP6038154B2 (ja) | 2011-09-13 | 2016-12-07 | ブリガム・ヤング・ユニバーシティＢｒｉｇｈａｍ Ｙｏｕｎｇ Ｕｎｉｖｅｒｓｉｔｙ | 骨疾患および破断骨治療のための組成物 |
| US9603859B2 (en) | 2011-09-13 | 2017-03-28 | Brigham Young University | Methods and products for increasing the rate of healing of tissue wounds |
| KR101966293B1 (ko) | 2011-09-13 | 2019-04-08 | 브라이엄 영 유니버시티 | 손상조직 치유용 제품 |
| US9694019B2 (en) | 2011-09-13 | 2017-07-04 | Brigham Young University | Compositions and methods for treating bone diseases and broken bones |
| BR112014015144B1 (pt) | 2011-12-21 | 2018-03-27 | Brigham Young University | Composição aquosa para cuidado oral, uso de um composto esteroide catiônico e método não- terapêutico de redução de compostos voláteis de enxofre |
| CN102584855B (zh) * | 2012-02-16 | 2014-06-25 | 青岛科技大学 | 一种改进的头孢噻呋的制备方法 |
| US9533063B1 (en) | 2012-03-01 | 2017-01-03 | Brigham Young University | Aerosols incorporating ceragenin compounds and methods of use thereof |
| EP2846634A2 (en) | 2012-05-02 | 2015-03-18 | Brigham Young University | Ceragenin particulate materials and methods for making same |
| WO2014062960A1 (en) | 2012-10-17 | 2014-04-24 | Brigham Young University | Treatment and prevention of mastitis |
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1994
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- 1994-03-07 KR KR1019950703858A patent/KR100296810B1/ko not_active Expired - Lifetime
- 1994-03-07 AT AT94910721T patent/ATE202109T1/de active
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- 1994-03-07 RU RU95121942A patent/RU2136685C1/ru active
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