JP2780800B2 - セフタジジムジ塩酸塩ギ酸溶媒和物 - Google Patents
セフタジジムジ塩酸塩ギ酸溶媒和物Info
- Publication number
- JP2780800B2 JP2780800B2 JP1024143A JP2414389A JP2780800B2 JP 2780800 B2 JP2780800 B2 JP 2780800B2 JP 1024143 A JP1024143 A JP 1024143A JP 2414389 A JP2414389 A JP 2414389A JP 2780800 B2 JP2780800 B2 JP 2780800B2
- Authority
- JP
- Japan
- Prior art keywords
- formic acid
- ceftazidime
- dihydrochloride
- solvate
- crystalline
- 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 - Lifetime
Links
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 title claims abstract description 96
- 235000019253 formic acid Nutrition 0.000 title claims abstract description 48
- 239000012453 solvate Substances 0.000 title claims abstract description 46
- JLZLIGALAZXURA-ZYMGEXDGSA-N (6r,7r)-7-[[(2z)-2-(2-amino-1,3-thiazol-4-yl)-2-(2-carboxylatopropan-2-yloxyimino)acetyl]amino]-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;hydron;dihydrochloride Chemical compound Cl.Cl.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 JLZLIGALAZXURA-ZYMGEXDGSA-N 0.000 title claims abstract description 45
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims abstract description 40
- NMVPEQXCMGEDNH-TZVUEUGBSA-N ceftazidime pentahydrate Chemical compound O.O.O.O.O.S([C@@H]1[C@@H](C(N1C=1C([O-])=O)=O)NC(=O)\C(=N/OC(C)(C)C(O)=O)C=2N=C(N)SC=2)CC=1C[N+]1=CC=CC=C1 NMVPEQXCMGEDNH-TZVUEUGBSA-N 0.000 claims abstract description 14
- 229960000484 ceftazidime Drugs 0.000 claims abstract description 13
- -1 2-aminothiazole-4 -Yl Chemical class 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 14
- 238000002425 crystallisation Methods 0.000 claims description 11
- 230000008025 crystallization Effects 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 10
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 6
- 238000004519 manufacturing process Methods 0.000 claims description 5
- 238000002441 X-ray diffraction Methods 0.000 claims description 4
- 238000002329 infrared spectrum Methods 0.000 claims description 4
- 239000013078 crystal Substances 0.000 claims description 3
- 238000002156 mixing Methods 0.000 claims description 2
- 150000004686 pentahydrates Chemical class 0.000 abstract description 5
- 238000002360 preparation method Methods 0.000 abstract description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 22
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000000543 intermediate Substances 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- LZTRCELOJRDYMQ-UHFFFAOYSA-N triphenylmethanol Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(O)C1=CC=CC=C1 LZTRCELOJRDYMQ-UHFFFAOYSA-N 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- KGWHMDCQVDMTNZ-UHFFFAOYSA-N 2-(butylcarbamoylamino)acetic acid Chemical compound CCCCNC(=O)NCC(O)=O KGWHMDCQVDMTNZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 229960003547 ceftazidime pentahydrate Drugs 0.000 description 2
- 239000003610 charcoal Substances 0.000 description 2
- 238000006073 displacement reaction Methods 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 239000012258 stirred mixture Substances 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000894006 Bacteria Species 0.000 description 1
- 108020004256 Beta-lactamase Proteins 0.000 description 1
- LRKHKETXQNDOKF-IODBXWCGSA-N CC(C)(O\N=C(\C(=O)N[C@H]1[C@H]2SC=C(C[n+]3ccccc3)C(N2C1=O)C([O-])=O)c1csc(N)n1)C(O)=O Chemical compound CC(C)(O\N=C(\C(=O)N[C@H]1[C@H]2SC=C(C[n+]3ccccc3)C(N2C1=O)C([O-])=O)c1csc(N)n1)C(O)=O LRKHKETXQNDOKF-IODBXWCGSA-N 0.000 description 1
- 229930186147 Cephalosporin Natural products 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 102000006635 beta-lactamase Human genes 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 229940124587 cephalosporin Drugs 0.000 description 1
- 150000001780 cephalosporins Chemical class 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000010981 drying operation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000006748 scratching Methods 0.000 description 1
- 230000002393 scratching effect Effects 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/38—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof
- C07D501/46—Methylene radicals, substituted by nitrogen atoms; Lactams thereof with the 2-carboxyl group; Methylene radicals substituted by nitrogen-containing hetero rings attached by the ring nitrogen atom; Quaternary compounds thereof with the 7-amino radical acylated by carboxylic acids containing hetero rings
-
- 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
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB888802622A GB8802622D0 (en) | 1988-02-05 | 1988-02-05 | Chemical compound |
| GB8802622 | 1988-02-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01308284A JPH01308284A (ja) | 1989-12-12 |
| JP2780800B2 true JP2780800B2 (ja) | 1998-07-30 |
Family
ID=10631146
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP1024143A Expired - Lifetime JP2780800B2 (ja) | 1988-02-05 | 1989-02-03 | セフタジジムジ塩酸塩ギ酸溶媒和物 |
Country Status (9)
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5069905B2 (ja) | 2003-01-21 | 2012-11-07 | アプテュイト （ウエスト ラファイエット）、エルエルシー | 新規な共結晶化 |
| WO2005089375A2 (en) | 2004-03-12 | 2005-09-29 | S.S.C.I., Inc. | Screening for solid forms by ultrasound crystallization and cocrystallization using ultrasound |
| HUP0700353A2 (en) | 2007-05-18 | 2008-12-29 | Richter Gedeon Nyrt | Metabolites of (thio)carbamoyl-cyclohexane derivatives |
| KR20130115393A (ko) * | 2008-02-21 | 2013-10-21 | 미쓰비시 타나베 파마 코퍼레이션 | 경구 투여용 고형 제제 |
| PL2317852T3 (pl) | 2008-07-16 | 2015-05-29 | Richter Gedeon Nyrt | Preparaty farmaceutyczne zawierające ligandy receptora dopaminy |
| US11274087B2 (en) | 2016-07-08 | 2022-03-15 | Richter Gedeon Nyrt. | Industrial process for the preparation of cariprazine |
| US11547707B2 (en) | 2019-04-10 | 2023-01-10 | Richter Gedeon Nyrt. | Carbamoyl cyclohexane derivatives for treating autism spectrum disorder |
| KR20210015065A (ko) | 2019-07-31 | 2021-02-10 | 김윤성 | 운전자의 개성을 표현하고 운전자, 보행자, 자동차를 보호하기 위한 차량용 보호 케이스 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR228726A1 (es) * | 1978-05-26 | 1983-04-15 | Glaxo Group Ltd | Procedimiento para la preparacion del antibiotico(6r,7r)-7-((z)-2-(2-aminotiazol-4-il)-2-(2-carboxiprop-2-oxiimino)acetamido)-3-(1-piridiniometil)cef-3-em-4-carboxilato |
| US4329453A (en) * | 1979-10-02 | 1982-05-11 | Glaxo Group Limited | Cephalosporin antibiotic |
| DE3037104C2 (de) * | 1979-10-02 | 1986-04-30 | Glaxo Group Ltd., London | Kristallines Bishydrochlorid von (6R,7R)-7-[(Z)-2-(2-Aminothiazol-4-yl)-2-(2-carboxyprop-2-oximino)acetamido]-3-(1-pyridiniummethyl)ceph-3-em-4-carboxylat |
| GB2132616B (en) * | 1982-12-27 | 1986-08-06 | Lilly Co Eli | Improvements in or relating to novel cephalosporin intermediates |
| US4537959A (en) * | 1984-03-26 | 1985-08-27 | Eli Lilly And Company | Crystalline cephalosporin antibiotic salt |
| CA1236089A (en) * | 1984-06-25 | 1988-05-03 | Perry C. Heath | Ceftazidime |
| US4616080A (en) * | 1984-07-02 | 1986-10-07 | Eli Lilly And Company | Simplified process of forming crystalline ceftazidime pentahydrate |
-
1988
- 1988-02-05 GB GB888802622A patent/GB8802622D0/en active Pending
-
1989
- 1989-02-02 ES ES89301004T patent/ES2072293T3/es not_active Expired - Lifetime
- 1989-02-02 AT AT89301004T patent/ATE122678T1/de not_active IP Right Cessation
- 1989-02-02 DE DE68922629T patent/DE68922629T2/de not_active Expired - Lifetime
- 1989-02-02 EP EP89301004A patent/EP0327358B1/en not_active Expired - Lifetime
- 1989-02-03 JP JP1024143A patent/JP2780800B2/ja not_active Expired - Lifetime
- 1989-02-03 US US07/305,541 patent/US4943632A/en not_active Expired - Lifetime
- 1989-02-04 TW TW078100842A patent/TW266212B/zh active
- 1989-02-04 KR KR1019890001322A patent/KR0123015B1/ko not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| EP0327358B1 (en) | 1995-05-17 |
| EP0327358A3 (en) | 1991-04-03 |
| EP0327358A2 (en) | 1989-08-09 |
| ATE122678T1 (de) | 1995-06-15 |
| JPH01308284A (ja) | 1989-12-12 |
| ES2072293T3 (es) | 1995-07-16 |
| DE68922629D1 (de) | 1995-06-22 |
| GB8802622D0 (en) | 1988-03-02 |
| US4943632A (en) | 1990-07-24 |
| TW266212B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1995-12-21 |
| KR0123015B1 (ko) | 1997-11-13 |
| KR890013031A (ko) | 1989-09-21 |
| DE68922629T2 (de) | 1995-10-19 |
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