GB1335718A - Penicillin esters salts thereof and methods for their preparation - Google Patents
Penicillin esters salts thereof and methods for their preparationInfo
- Publication number
- GB1335718A GB1335718A GB1335871A GB1335718DA GB1335718A GB 1335718 A GB1335718 A GB 1335718A GB 1335871 A GB1335871 A GB 1335871A GB 1335718D A GB1335718D A GB 1335718DA GB 1335718 A GB1335718 A GB 1335718A
- Authority
- GB
- United Kingdom
- Prior art keywords
- penicillin
- formula
- reacting
- amidinopenicillin
- penicillinate
- 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 Penicillin esters salts Chemical class 0.000 title abstract 2
- 229930182555 Penicillin Natural products 0.000 abstract 6
- 229940049954 penicillin Drugs 0.000 abstract 6
- 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 5
- 150000001875 compounds Chemical class 0.000 abstract 4
- 150000003839 salts Chemical class 0.000 abstract 4
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 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
- 125000005278 alkyl sulfonyloxy group Chemical group 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 125000005279 aryl sulfonyloxy group Chemical group 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 239000003937 drug carrier Substances 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000008024 pharmaceutical diluent Substances 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/084—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings
- C07D295/088—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms attached to the same carbon chain, which is not interrupted by carbocyclic rings to an acyclic saturated chain
-
- 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)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1335718 Penicillin pencillinates LOVENS KEMISKE FABRIK PRODUKTIONSAKTIESELSKAB 20 April 1972 [5 May 1971] 13358/71 Heading C2A Novel amidinopenicillin penicillinates having the Formula (I) wherein R 1 and R 2 each represents an optionally substituted C 1 -C 6 alkyl radical, or an optionally substituted C 3 -C 10 cycloalkyl or (C 3 -C 10 cycloalkyl) alkyl radical, or R 1 and R 2 together with the common nitrogen atom represent a heterocycle having 4-8 carbons, and R 3 is the residue of the 6-acylamino group of a known natural or synthetic penicillin and salts thereof, are prepared by either (a) reacting the base salt of the penicillin moieties of the compound (I) with a compound YCH 2 Cl wherein Y is Br, I, or an alkyl- or aryl-sulphonyloxy group, to give the corresponding penicillin chloromethyl ester and then reacting the latter with the base salt of the other of the penicillin moieties of the compound (I); or (b) reacting a 6-aminopenicillanic acid penicillinate with an amidinating agent of formula in which R 1 and R 2 are as defined above and R 5 is O or S; or (c) reacting an amidinopenicillin 6-amino-penicillinate with an N-acylating agent of formula R 3 COOH or a functional derivative thereof. The amidinopenicillin chloromethyl esters of Formula (VI) which are an intermediate in procedure (a) hereinbefore, R 1 and R 2 having the aforesaid meanings, are themselves novel compounds. Pharmaceutical compositions having antibacterial activity comprise a penicillin penicillinate of Formula (I) above or a non-toxic salt thereof together with a pharmaceutical carrier or diluent.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1335871 | 1971-05-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1335718A true GB1335718A (en) | 1973-10-31 |
Family
ID=10021514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1335871A Expired GB1335718A (en) | 1971-05-05 | 1971-04-20 | Penicillin esters salts thereof and methods for their preparation |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3869449A (en) |
| JP (1) | JPS5541240B1 (en) |
| CA (1) | CA1112569A (en) |
| DE (1) | DE2221912A1 (en) |
| DK (1) | DK140481B (en) |
| FR (1) | FR2135339B1 (en) |
| GB (1) | GB1335718A (en) |
| NL (1) | NL7205957A (en) |
| SE (1) | SE417098B (en) |
| ZA (1) | ZA722545B (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1579931A (en) * | 1976-04-15 | 1980-11-26 | Leo Pharm Prod Ltd | Bis-penicillanoyl-oxy-alkanes |
| US4345071A (en) * | 1976-06-29 | 1982-08-17 | Leo Pharmaceutical Products, Ltd. A/S | Derivatives of penicillanic acid |
| LU77362A1 (en) * | 1977-05-17 | 1979-01-19 | ||
| US4407751A (en) * | 1979-02-13 | 1983-10-04 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Fabrik Produktionsaktieselskab) | Processes for preparing β-lactams |
| IE49371B1 (en) * | 1979-02-13 | 1985-09-18 | Leo Pharm Prod Ltd | 6-(azacycloalkyl-or azabicycloalkyl-methyl imino)penicillanic acid esters |
| IE49880B1 (en) * | 1979-02-13 | 1986-01-08 | Leo Pharm Prod Ltd | Penicillin derivatives |
| US4244951A (en) * | 1979-05-16 | 1981-01-13 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| US4309347A (en) * | 1979-05-16 | 1982-01-05 | Pfizer Inc. | Penicillanoyloxymethyl penicillanate 1,1,1',1'-tetraoxide |
| US4377524A (en) * | 1979-05-16 | 1983-03-22 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| DE3051044C2 (en) * | 1979-06-19 | 1989-03-30 | Leo Pharmaceutical Products Ltd. A/S (Loevens Kemiske Fabrik Produktionsaktieselskab), Ballerup, Dk | |
| US4340539A (en) * | 1980-01-21 | 1982-07-20 | Bristol-Myers Company | Derivatives of 6-bromo penicillanic acid |
| US4432903A (en) * | 1980-09-08 | 1984-02-21 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| US4488994A (en) * | 1980-09-08 | 1984-12-18 | Pfizer Inc. | Bis-esters of methanediol with penicillins and penicillanic acid 1,1-dioxide |
| US4323499A (en) * | 1981-01-05 | 1982-04-06 | Pfizer Inc. | 6-(2-Aryl-2-(1,1-dioxopenicillanoyloxy-methoxycarbonyl)acetamido penicillanic acids |
| US4540687A (en) * | 1981-09-09 | 1985-09-10 | Pfizer Inc. | Antibacterial 6'-(2-amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds |
| US4582829A (en) * | 1981-09-09 | 1986-04-15 | Pfizer Inc. | Antibacterial 6'-(2-amino-2-[4-acyloxyphenyl]acetamido)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds |
| CA2379650C (en) * | 1999-07-30 | 2008-09-02 | Eisai Co., Ltd. | Process for producing a basic antibiotic inorganic acid salt, and oxalate intermediate |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3669978A (en) * | 1970-05-28 | 1972-06-13 | American Home Prod | Process for the production of semi-synthetic penicillin intermediate |
| US3704290A (en) * | 1970-12-09 | 1972-11-28 | American Home Prod | 6-(1 - substituted aminocycloalkane-carboxamido)-penicillanic acid and salts |
| US3770722A (en) * | 1971-10-04 | 1973-11-06 | Pfizer | 6 - (alpha - (aryl substituted)acylamino-acylamino)penicillanic acidsand derivatives thereof |
-
1971
- 1971-04-20 GB GB1335871A patent/GB1335718A/en not_active Expired
-
1972
- 1972-04-13 US US243855A patent/US3869449A/en not_active Expired - Lifetime
- 1972-04-17 ZA ZA722545A patent/ZA722545B/en unknown
- 1972-04-20 DK DK193172A patent/DK140481B/en unknown
- 1972-04-26 CA CA140,652A patent/CA1112569A/en not_active Expired
- 1972-05-02 JP JP4337972A patent/JPS5541240B1/ja active Pending
- 1972-05-03 NL NL7205957A patent/NL7205957A/xx not_active Application Discontinuation
- 1972-05-04 SE SE7205896A patent/SE417098B/en unknown
- 1972-05-04 DE DE19722221912 patent/DE2221912A1/en not_active Withdrawn
- 1972-05-05 FR FR7216200A patent/FR2135339B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2135339A1 (en) | 1972-12-15 |
| FR2135339B1 (en) | 1975-06-20 |
| DE2221912A1 (en) | 1972-11-16 |
| JPS5541240B1 (en) | 1980-10-22 |
| DK140481B (en) | 1979-09-10 |
| CA1112569A (en) | 1981-11-17 |
| SE417098B (en) | 1981-02-23 |
| ZA722545B (en) | 1973-01-31 |
| NL7205957A (en) | 1972-11-07 |
| US3869449A (en) | 1975-03-04 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed [section 19, patents act 1949] | ||
| PCNP | Patent ceased through non-payment of renewal fee |