ES331127A1 - 6-acylaminopenicillanic acids and process for preparing them - Google Patents
6-acylaminopenicillanic acids and process for preparing themInfo
- Publication number
- ES331127A1 ES331127A1 ES331127A ES331127A ES331127A1 ES 331127 A1 ES331127 A1 ES 331127A1 ES 331127 A ES331127 A ES 331127A ES 331127 A ES331127 A ES 331127A ES 331127 A1 ES331127 A1 ES 331127A1
- Authority
- ES
- Spain
- Prior art keywords
- acid
- penicillins
- alpha
- salt
- thienyl
- 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
- 239000002253 acid Substances 0.000 title abstract 4
- 150000007513 acids Chemical class 0.000 title 1
- 238000004519 manufacturing process Methods 0.000 title 1
- 229930182555 Penicillin Natural products 0.000 abstract 5
- 150000002960 penicillins Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical compound [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 abstract 1
- NGHVIOIJCVXTGV-UHFFFAOYSA-N 6beta-amino-penicillanic acid Natural products OC(=O)C1C(C)(C)SC2C(N)C(=O)N21 NGHVIOIJCVXTGV-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract 1
- 150000001342 alkaline earth metals Chemical class 0.000 abstract 1
- -1 amine salts Chemical class 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 150000002431 hydrogen Chemical group 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 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)
Abstract
The invention relates to [alpha]-thienyl-oxymethyl penicillins of formula wherein R1 and R2 are hydrogen or methyl and R3 is hydrogen, methyl or ethyl. The penicillins are produced by reacting 6-aminopenicillanic acid, or a salt thereof, with an [alpha]-thienyloxycarboxylic acid of formula or a functional derivative thereof, wherein R1, R2 and R3 have the above meanings and, if desired, liberating the free acid from the salt obtained or converting the free acid into a physiologically tolerable salt. Alkali metal, alkaline earth metal, ammonium and amine salts are specified. A typical penicillin is 6-[[alpha]- (thienyl - (3) - oxy) - butyrylamino]-penicillanic acid. The penicillins are acid-stable and have outstanding antibacterial activity. A pharmaceutical composition for human and animal use comprises one of the above [alpha]-thienyloxymethyl penicillins or a salt thereof, and a carrier.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0047191 | 1965-09-15 | ||
| DEF0048889 | 1966-04-07 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES331127A1 true ES331127A1 (en) | 1968-08-01 |
Family
ID=25976981
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES331127A Expired ES331127A1 (en) | 1965-09-15 | 1966-09-12 | 6-acylaminopenicillanic acids and process for preparing them |
Country Status (12)
| Country | Link |
|---|---|
| AT (1) | AT270862B (en) |
| BE (1) | BE686932A (en) |
| CH (1) | CH478147A (en) |
| DE (2) | DE1545858A1 (en) |
| DK (1) | DK123530B (en) |
| ES (1) | ES331127A1 (en) |
| FI (1) | FI48096C (en) |
| FR (2) | FR1502798A (en) |
| GB (1) | GB1144227A (en) |
| IL (1) | IL26476A (en) |
| NL (1) | NL6612969A (en) |
| SE (1) | SE327202B (en) |
-
1965
- 1965-09-15 DE DE19651545858 patent/DE1545858A1/en active Pending
-
1966
- 1966-04-07 DE DE19661670685 patent/DE1670685A1/en active Pending
- 1966-09-07 IL IL2647666A patent/IL26476A/en unknown
- 1966-09-12 CH CH1312866A patent/CH478147A/en not_active IP Right Cessation
- 1966-09-12 ES ES331127A patent/ES331127A1/en not_active Expired
- 1966-09-13 AT AT863866A patent/AT270862B/en active
- 1966-09-14 SE SE1233166A patent/SE327202B/xx unknown
- 1966-09-14 DK DK475766A patent/DK123530B/en unknown
- 1966-09-14 NL NL6612969A patent/NL6612969A/xx unknown
- 1966-09-15 FR FR76488A patent/FR1502798A/en not_active Expired
- 1966-09-15 FI FI241566A patent/FI48096C/en active
- 1966-09-15 GB GB41298/66A patent/GB1144227A/en not_active Expired
- 1966-09-15 BE BE686932D patent/BE686932A/xx unknown
- 1966-12-14 FR FR87361A patent/FR6067M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL6612969A (en) | 1967-03-16 |
| FI48096B (en) | 1974-02-28 |
| FR1502798A (en) | 1967-11-24 |
| AT270862B (en) | 1969-05-12 |
| FR6067M (en) | 1968-05-27 |
| GB1144227A (en) | 1969-03-05 |
| DK123530B (en) | 1972-07-03 |
| IL26476A (en) | 1969-11-12 |
| BE686932A (en) | 1967-03-15 |
| CH478147A (en) | 1969-09-15 |
| FI48096C (en) | 1974-06-10 |
| SE327202B (en) | 1970-08-17 |
| DE1545858A1 (en) | 1969-11-27 |
| DE1670685A1 (en) | 1970-12-03 |
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