DE3018340A1 - Kristallines additionssalz und verfahren zu dessen herstellung - Google Patents
Kristallines additionssalz und verfahren zu dessen herstellungInfo
- Publication number
- DE3018340A1 DE3018340A1 DE19803018340 DE3018340A DE3018340A1 DE 3018340 A1 DE3018340 A1 DE 3018340A1 DE 19803018340 DE19803018340 DE 19803018340 DE 3018340 A DE3018340 A DE 3018340A DE 3018340 A1 DE3018340 A1 DE 3018340A1
- Authority
- DE
- Germany
- Prior art keywords
- acid
- crystalline
- compound
- munich
- dipl
- 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.)
- Withdrawn
Links
- 150000003839 salts Chemical class 0.000 title claims description 30
- 238000000034 method Methods 0.000 title claims description 28
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 24
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 18
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 10
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 10
- 239000011780 sodium chloride Substances 0.000 claims description 9
- 239000011975 tartaric acid Substances 0.000 claims description 9
- 235000002906 tartaric acid Nutrition 0.000 claims description 9
- -1 2-aminothiazol-4-yl Chemical group 0.000 claims description 8
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 claims description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims 2
- JJXRANHOCVAFMF-SNVBAGLBSA-N 2,2-dimethylpropanoyloxymethyl (6R)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Chemical compound CC(C)(C)C(=O)OCOC(=O)C1=CCS[C@@H]2CC(=O)N12 JJXRANHOCVAFMF-SNVBAGLBSA-N 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 28
- 239000002253 acid Substances 0.000 description 21
- 239000013078 crystal Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 239000000047 product Substances 0.000 description 11
- 239000000843 powder Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000012982 x-ray structure analysis Methods 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000000921 elemental analysis Methods 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 5
- 239000002198 insoluble material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 229930186147 Cephalosporin Natural products 0.000 description 2
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 229940124587 cephalosporin Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 150000004683 dihydrates Chemical class 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 210000001035 gastrointestinal tract Anatomy 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- 208000035143 Bacterial infection Diseases 0.000 description 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N DMSO Substances CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- 229920002153 Hydroxypropyl cellulose Polymers 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 208000022362 bacterial infectious disease Diseases 0.000 description 1
- 239000001110 calcium chloride Substances 0.000 description 1
- 229910001628 calcium chloride Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 150000003841 chloride salts Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000004688 heptahydrates Chemical class 0.000 description 1
- 150000004687 hexahydrates Chemical class 0.000 description 1
- 239000001863 hydroxypropyl cellulose Substances 0.000 description 1
- 235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- PELJISAVHGXLAL-UHFFFAOYSA-N iodomethyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OCI PELJISAVHGXLAL-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 235000012054 meals Nutrition 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 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
- C07D501/36—Methylene radicals, substituted by sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP5948179A JPS55151588A (en) | 1979-05-14 | 1979-05-14 | Preparation of cephalosporin salt crystal |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE3018340A1 true DE3018340A1 (de) | 1980-11-27 |
Family
ID=13114535
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19803018340 Withdrawn DE3018340A1 (de) | 1979-05-14 | 1980-05-13 | Kristallines additionssalz und verfahren zu dessen herstellung |
Country Status (20)
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GR78221B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1980-02-01 | 1984-09-26 | Ciba Geigy Ag | |
| US4616008A (en) * | 1984-05-02 | 1986-10-07 | Takeda Chemical Industries, Ltd. | Antibacterial solid composition for oral administration |
| US4910301A (en) * | 1985-08-05 | 1990-03-20 | Bristol-Myers Company | Cefepime cephalosporin salts |
| US5244891A (en) * | 1985-08-05 | 1993-09-14 | Bristol-Myers Squibb Company | Injectable compositions of cefepime dihydrochloride hydrate |
| CA1284994C (en) * | 1985-08-05 | 1991-06-18 | Murray Arthur Kaplan | Cephalosporin salts and injectable compositions |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS603314B2 (ja) * | 1976-08-31 | 1985-01-26 | 武田薬品工業株式会社 | セフアロスポリン誘導体およびその製造法 |
| US4189479A (en) * | 1977-12-22 | 1980-02-19 | Takeda Chemical Industries, Ltd. | Cephalosporin esters |
-
1979
- 1979-05-14 JP JP5948179A patent/JPS55151588A/ja active Pending
-
1980
- 1980-05-03 GR GR61865A patent/GR68203B/el unknown
- 1980-05-06 NZ NZ193634A patent/NZ193634A/xx unknown
- 1980-05-06 US US06/147,053 patent/US4316018A/en not_active Expired - Lifetime
- 1980-05-12 ES ES491386A patent/ES491386A0/es active Granted
- 1980-05-12 SE SE8003548A patent/SE8003548L/ not_active Application Discontinuation
- 1980-05-13 DE DE19803018340 patent/DE3018340A1/de not_active Withdrawn
- 1980-05-13 BE BE1/9820A patent/BE883250A/fr unknown
- 1980-05-13 IT IT22020/80A patent/IT1132053B/it active
- 1980-05-13 NO NO801428A patent/NO801428L/no unknown
- 1980-05-13 NL NL8002758A patent/NL8002758A/nl not_active Application Discontinuation
- 1980-05-13 DK DK209380A patent/DK209380A/da unknown
- 1980-05-13 GB GB8015741A patent/GB2052483A/en not_active Withdrawn
- 1980-05-14 SU SU802921250A patent/SU973024A3/ru active
- 1980-05-14 FR FR8010921A patent/FR2456746A1/fr not_active Withdrawn
- 1980-05-14 ZA ZA00802874A patent/ZA802874B/xx unknown
- 1980-05-14 PT PT71241A patent/PT71241B/pt unknown
- 1980-05-14 AU AU58380/80A patent/AU5838080A/en not_active Abandoned
- 1980-05-14 AT AT0259180A patent/AT367427B/de not_active IP Right Cessation
- 1980-05-14 FI FI801563A patent/FI801563A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| AT367427B (de) | 1982-07-12 |
| NO801428L (no) | 1980-11-17 |
| PT71241B (en) | 1982-06-08 |
| FI801563A7 (fi) | 1980-11-15 |
| SU973024A3 (ru) | 1982-11-07 |
| ATA259180A (de) | 1981-11-15 |
| IT1132053B (it) | 1986-06-25 |
| IT8022020A0 (it) | 1980-05-13 |
| DK209380A (da) | 1980-11-15 |
| GR68203B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1981-11-10 |
| SE8003548L (sv) | 1980-11-15 |
| NZ193634A (en) | 1982-05-25 |
| JPS55151588A (en) | 1980-11-26 |
| NL8002758A (nl) | 1980-11-18 |
| US4316018A (en) | 1982-02-16 |
| ES8102132A1 (es) | 1980-12-16 |
| ZA802874B (en) | 1980-12-31 |
| GB2052483A (en) | 1981-01-28 |
| ES491386A0 (es) | 1980-12-16 |
| BE883250A (fr) | 1980-11-13 |
| PT71241A (en) | 1980-06-01 |
| AU5838080A (en) | 1980-11-20 |
| FR2456746A1 (fr) | 1980-12-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8139 | Disposal/non-payment of the annual fee |