DE2531144C3 - 2,6-Dimethoxyphenylpenicillindiäthylaminoäthylester und Verfahren zu dessen Herstellung - Google Patents
2,6-Dimethoxyphenylpenicillindiäthylaminoäthylester und Verfahren zu dessen HerstellungInfo
- Publication number
- DE2531144C3 DE2531144C3 DE2531144A DE2531144A DE2531144C3 DE 2531144 C3 DE2531144 C3 DE 2531144C3 DE 2531144 A DE2531144 A DE 2531144A DE 2531144 A DE2531144 A DE 2531144A DE 2531144 C3 DE2531144 C3 DE 2531144C3
- Authority
- DE
- Germany
- Prior art keywords
- integral
- dimethoxyphenylpenicillin
- methicillin
- dimethoxyphenylpenicillindiethylaminoäthylester
- preparation
- 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
Links
- -1 2,6-Dimethoxyphenylpenicillin diethylaminoethyl ester Chemical class 0.000 claims description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RJQXTJLFIWVMTO-TYNCELHUSA-N Methicillin Chemical compound COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C(O)=O)C(C)(C)S[C@@H]21 RJQXTJLFIWVMTO-TYNCELHUSA-N 0.000 description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- 229960003085 meticillin Drugs 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 229930182555 Penicillin Natural products 0.000 description 4
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229940049954 penicillin Drugs 0.000 description 4
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
- OGYGFUAIIOPWQD-UHFFFAOYSA-N 1,3-thiazolidine Chemical group C1CSCN1 OGYGFUAIIOPWQD-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001447 alkali salts Chemical class 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 208000004396 mastitis Diseases 0.000 description 2
- 239000008267 milk Substances 0.000 description 2
- 235000013336 milk Nutrition 0.000 description 2
- 210000004080 milk Anatomy 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 1
- 241000283707 Capra Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 206010061218 Inflammation Diseases 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
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical group 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- AOGYCOYQMAVAFD-UHFFFAOYSA-N chlorocarbonic acid Chemical compound OC(Cl)=O AOGYCOYQMAVAFD-UHFFFAOYSA-N 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 235000013365 dairy product Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PUSKHXMZPOMNTQ-UHFFFAOYSA-N ethyl 2,1,3-benzoselenadiazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=C2N=[Se]=NC2=C1 PUSKHXMZPOMNTQ-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 230000004054 inflammatory process Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000003951 lactams Chemical group 0.000 description 1
- 210000005075 mammary gland Anatomy 0.000 description 1
- NRZPASQBOYNGHR-HWROMZCQSA-M methicillin sodium monohydrate Chemical compound O.[Na+].COC1=CC=CC(OC)=C1C(=O)N[C@@H]1C(=O)N2[C@@H](C([O-])=O)C(C)(C)S[C@@H]21 NRZPASQBOYNGHR-HWROMZCQSA-M 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000007039 two-step reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES428213A ES428213A1 (es) | 1974-07-12 | 1974-07-12 | Procedimiento para la obtencion de esteres dialquilaminoal-quilicos de penicilina. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2531144A1 DE2531144A1 (de) | 1976-01-29 |
| DE2531144B2 DE2531144B2 (de) | 1978-02-23 |
| DE2531144C3 true DE2531144C3 (de) | 1978-09-28 |
Family
ID=8467134
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2531144A Expired DE2531144C3 (de) | 1974-07-12 | 1975-07-11 | 2,6-Dimethoxyphenylpenicillindiäthylaminoäthylester und Verfahren zu dessen Herstellung |
Country Status (7)
| Country | Link |
|---|---|
| AR (1) | AR214390A1 (enrdf_load_stackoverflow) |
| CA (1) | CA1055928A (enrdf_load_stackoverflow) |
| CH (1) | CH595386A5 (enrdf_load_stackoverflow) |
| DE (1) | DE2531144C3 (enrdf_load_stackoverflow) |
| ES (1) | ES428213A1 (enrdf_load_stackoverflow) |
| FR (1) | FR2277582A1 (enrdf_load_stackoverflow) |
| GB (1) | GB1470154A (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4150157A (en) * | 1976-06-11 | 1979-04-17 | Beecham Group Limited | Penicillin compositions |
| GB1569421A (en) * | 1976-06-11 | 1980-06-18 | Beecham Group Ltd | Penicillin compositions |
| US4215120A (en) * | 1977-07-14 | 1980-07-29 | Beecham Group Limited | Penicillin esters and their preparation |
| JP5324463B2 (ja) | 2006-12-10 | 2013-10-23 | チョンシー ユー | β−ラクタム抗生物質の経皮送達システム |
| US9969751B2 (en) | 2009-06-10 | 2018-05-15 | Techfields Pharma Co., Ltd. | High penetration prodrug compositions of antimicrobials and antimicrobial-related compounds |
| RU2683934C2 (ru) | 2012-01-18 | 2019-04-03 | Текфилдз Фарма Ко., Лтд. | Композиции, содержащие пролекарства с высокой проницаемостью, и фармацевтическая композиция для лечения состояний легких |
-
1974
- 1974-07-12 ES ES428213A patent/ES428213A1/es not_active Expired
-
1975
- 1975-07-04 GB GB2833075A patent/GB1470154A/en not_active Expired
- 1975-07-04 AR AR259481A patent/AR214390A1/es active
- 1975-07-10 CH CH899975A patent/CH595386A5/xx not_active IP Right Cessation
- 1975-07-11 DE DE2531144A patent/DE2531144C3/de not_active Expired
- 1975-07-11 FR FR7521914A patent/FR2277582A1/fr active Granted
- 1975-07-11 CA CA231,318A patent/CA1055928A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| AR214390A1 (es) | 1979-06-15 |
| FR2277582A1 (fr) | 1976-02-06 |
| ES428213A1 (es) | 1976-07-16 |
| GB1470154A (en) | 1977-04-14 |
| CH595386A5 (enrdf_load_stackoverflow) | 1978-02-15 |
| DE2531144B2 (de) | 1978-02-23 |
| CA1055928A (en) | 1979-06-05 |
| DE2531144A1 (de) | 1976-01-29 |
| FR2277582B1 (enrdf_load_stackoverflow) | 1978-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |