DE2411260A1 - Verfahren zur gewinnung von salzen von antibiotika mit natuerlichen aminosaeuren - Google Patents
Verfahren zur gewinnung von salzen von antibiotika mit natuerlichen aminosaeurenInfo
- Publication number
- DE2411260A1 DE2411260A1 DE2411260A DE2411260A DE2411260A1 DE 2411260 A1 DE2411260 A1 DE 2411260A1 DE 2411260 A DE2411260 A DE 2411260A DE 2411260 A DE2411260 A DE 2411260A DE 2411260 A1 DE2411260 A1 DE 2411260A1
- Authority
- DE
- Germany
- Prior art keywords
- antibiotics
- amino acids
- solvent
- natural amino
- water
- 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.)
- Pending
Links
- 150000003839 salts Chemical class 0.000 title claims description 15
- 238000000034 method Methods 0.000 title claims description 7
- 150000001413 amino acids Chemical class 0.000 title claims description 5
- 239000003242 anti bacterial agent Substances 0.000 title claims description 5
- 229940088710 antibiotic agent Drugs 0.000 title claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000004475 Arginine Substances 0.000 claims description 9
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 claims description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 8
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 claims description 8
- 239000004472 Lysine Substances 0.000 claims description 8
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000012454 non-polar solvent Substances 0.000 claims description 3
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 2
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 0.000 claims description 2
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 claims description 2
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005368 heteroarylthio group Chemical group 0.000 claims description 2
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 claims description 2
- 239000003208 petroleum Substances 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims 2
- AXPZDYVDTMMLNB-UHFFFAOYSA-N Benzyl ethyl ether Chemical compound CCOCC1=CC=CC=C1 AXPZDYVDTMMLNB-UHFFFAOYSA-N 0.000 claims 1
- 238000001914 filtration Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000000203 mixture Substances 0.000 claims 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
- 239000011877 solvent mixture Substances 0.000 claims 1
- 239000000243 solution Substances 0.000 description 11
- 239000000725 suspension Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- -1 amino acid salts Chemical class 0.000 description 5
- 238000003756 stirring Methods 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- XIURVHNZVLADCM-WPZCJLIBSA-N (6r)-3-(acetyloxymethyl)-8-oxo-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid Chemical compound C1([C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C(O)=O)NC(=O)CC1=CC=CS1 XIURVHNZVLADCM-WPZCJLIBSA-N 0.000 description 3
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 238000004090 dissolution Methods 0.000 description 3
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 230000003115 biocidal effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 1
- 229940047526 cephalexin monohydrate Drugs 0.000 description 1
- YGBFLZPYDUKSPT-MRVPVSSYSA-N cephalosporanic acid Chemical compound S1CC(COC(=O)C)=C(C(O)=O)N2C(=O)C[C@H]21 YGBFLZPYDUKSPT-MRVPVSSYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000004108 freeze drying Methods 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 150000004682 monohydrates Chemical class 0.000 description 1
- 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
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 150000003462 sulfoxides Chemical class 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES412429A ES412429A1 (es) | 1973-03-08 | 1973-03-08 | Un procedimiento para la obtencion de sales de antibioticoscon aminoacidos de naturaleza basica. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2411260A1 true DE2411260A1 (de) | 1974-09-12 |
Family
ID=8463621
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2411260A Pending DE2411260A1 (de) | 1973-03-08 | 1974-03-08 | Verfahren zur gewinnung von salzen von antibiotika mit natuerlichen aminosaeuren |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JPS5029726A (enrdf_load_stackoverflow) |
| DE (1) | DE2411260A1 (enrdf_load_stackoverflow) |
| ES (1) | ES412429A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2220533B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1445803A (enrdf_load_stackoverflow) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235900A (en) * | 1978-11-15 | 1980-11-25 | E. R. Squibb & Sons, Inc. | Cephradine compositions |
| DE3112168A1 (de) * | 1980-04-01 | 1982-01-14 | Dobfar S.p.A., 20059 Vimercate, Milano | Cephadroxylsalze mit aminosaeuren |
| DE3110190A1 (de) * | 1980-04-01 | 1982-02-18 | Dobfar S.p.A., 20059 Vimercate, Milano | Cephapirinsalze mit aminosaeuren und verfahren zu deren herstellung |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2308368A1 (fr) * | 1975-04-21 | 1976-11-19 | Gallardo Antonio Sa | Sel soluble de la cephalexine comme antibiotique injectable |
| US5244891A (en) * | 1985-08-05 | 1993-09-14 | Bristol-Myers Squibb Company | Injectable compositions of cefepime dihydrochloride hydrate |
| IT1204751B (it) * | 1986-01-03 | 1989-03-10 | Therapicon Srl | Derivati idrosolubili dell'acido 4,5 -difenil- 2 -ossazolpropionico,loro preparazione ed utilizzo in composizioni farmaceutiche |
| JP2520385B2 (ja) * | 1989-01-30 | 1996-07-31 | パーザー ファーマスーティカル カンパニー リミテッド | ３―置換基―７―置換したアミノ基セファロスポラナシ酸誘導体のアルカリ金属塩の製造法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3984403A (en) * | 1972-06-30 | 1976-10-05 | Takeda Chemical Industries, Ltd. | Arginine and lysine salts of acid cephalosporins |
-
1973
- 1973-03-08 ES ES412429A patent/ES412429A1/es not_active Expired
-
1974
- 1974-03-08 JP JP49027013A patent/JPS5029726A/ja active Pending
- 1974-03-08 DE DE2411260A patent/DE2411260A1/de active Pending
- 1974-03-08 FR FR7409584A patent/FR2220533B1/fr not_active Expired
- 1974-03-08 GB GB1046474A patent/GB1445803A/en not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4235900A (en) * | 1978-11-15 | 1980-11-25 | E. R. Squibb & Sons, Inc. | Cephradine compositions |
| DE3112168A1 (de) * | 1980-04-01 | 1982-01-14 | Dobfar S.p.A., 20059 Vimercate, Milano | Cephadroxylsalze mit aminosaeuren |
| DE3110190A1 (de) * | 1980-04-01 | 1982-02-18 | Dobfar S.p.A., 20059 Vimercate, Milano | Cephapirinsalze mit aminosaeuren und verfahren zu deren herstellung |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2220533B1 (enrdf_load_stackoverflow) | 1978-11-10 |
| ES412429A1 (es) | 1976-01-01 |
| JPS5029726A (enrdf_load_stackoverflow) | 1975-03-25 |
| GB1445803A (en) | 1976-08-11 |
| FR2220533A1 (enrdf_load_stackoverflow) | 1974-10-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OGA | New person/name/address of the applicant | ||
| OHN | Withdrawal |