GB924612A - Penicillins - Google Patents
PenicillinsInfo
- Publication number
- GB924612A GB924612A GB4356260A GB4356260A GB924612A GB 924612 A GB924612 A GB 924612A GB 4356260 A GB4356260 A GB 4356260A GB 4356260 A GB4356260 A GB 4356260A GB 924612 A GB924612 A GB 924612A
- Authority
- GB
- United Kingdom
- Prior art keywords
- chlorophenyl
- methyl
- penicillins
- phosphorodichloridate
- formula
- 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
- 229930182555 Penicillin Natural products 0.000 title abstract 7
- 150000002960 penicillins Chemical class 0.000 title abstract 5
- -1 aromatic phosphorodichloridate derivative Chemical class 0.000 abstract 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 abstract 3
- 231100000252 nontoxic Toxicity 0.000 abstract 3
- 230000003000 nontoxic effect Effects 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 230000003993 interaction Effects 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 229940049954 penicillin Drugs 0.000 abstract 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 abstract 2
- AFINAILKDBCXMX-PBHICJAKSA-N (2s,3r)-2-amino-3-hydroxy-n-(4-octylphenyl)butanamide Chemical compound CCCCCCCCC1=CC=C(NC(=O)[C@@H](N)[C@@H](C)O)C=C1 AFINAILKDBCXMX-PBHICJAKSA-N 0.000 abstract 1
- XPWBLZXBPJOLMJ-UHFFFAOYSA-N 1-chloro-2-[chloro(methoxy)phosphoryl]oxybenzene Chemical compound COP(Cl)(=O)OC1=CC=CC=C1Cl XPWBLZXBPJOLMJ-UHFFFAOYSA-N 0.000 abstract 1
- VLDPXPPHXDGHEW-UHFFFAOYSA-N 1-chloro-2-dichlorophosphoryloxybenzene Chemical compound ClC1=CC=CC=C1OP(Cl)(Cl)=O VLDPXPPHXDGHEW-UHFFFAOYSA-N 0.000 abstract 1
- YSOXJTIJJTYMOP-UHFFFAOYSA-N 2-dichlorophosphoryloxybenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1OP(Cl)(Cl)=O YSOXJTIJJTYMOP-UHFFFAOYSA-N 0.000 abstract 1
- 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
- RGBHNFTXUZGMSG-UHFFFAOYSA-N CC[ClH]P(O)(OC1=CC=CC(C)=C1)=O Chemical class CC[ClH]P(O)(OC1=CC=CC(C)=C1)=O RGBHNFTXUZGMSG-UHFFFAOYSA-N 0.000 abstract 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 abstract 1
- BFCGRHIEUYNMLL-UHFFFAOYSA-N P(OC1=C(C=CC=C1)C(=O)OC(C)C)(OC(C)C)(=O)Cl Chemical class P(OC1=C(C=CC=C1)C(=O)OC(C)C)(OC(C)C)(=O)Cl BFCGRHIEUYNMLL-UHFFFAOYSA-N 0.000 abstract 1
- 239000002775 capsule Substances 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- ITVPBBDAZKBMRP-UHFFFAOYSA-N chloro-dioxido-oxo-$l^{5}-phosphane;hydron Chemical class OP(O)(Cl)=O ITVPBBDAZKBMRP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003085 diluting agent Substances 0.000 abstract 1
- 239000006185 dispersion Substances 0.000 abstract 1
- 239000000839 emulsion Substances 0.000 abstract 1
- 239000008187 granular material Substances 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 abstract 1
- 239000011777 magnesium Substances 0.000 abstract 1
- 229910052749 magnesium Inorganic materials 0.000 abstract 1
- RQRPRIKQSPWNKO-UHFFFAOYSA-N methyl 4-dichlorophosphoryloxybenzoate Chemical compound COC(=O)C1=CC=C(OP(Cl)(Cl)=O)C=C1 RQRPRIKQSPWNKO-UHFFFAOYSA-N 0.000 abstract 1
- 235000010270 methyl p-hydroxybenzoate Nutrition 0.000 abstract 1
- 239000004292 methyl p-hydroxybenzoate Substances 0.000 abstract 1
- LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 abstract 1
- 239000002674 ointment Substances 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 239000000843 powder Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000000725 suspension Substances 0.000 abstract 1
- 239000003826 tablet Substances 0.000 abstract 1
- 238000002560 therapeutic procedure Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6561—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings
- C07F9/65611—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing systems of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring or ring system, with or without other non-condensed hetero rings containing the ring system (X = CH2, O, S, NH) optionally with an additional double bond and/or substituents, e.g. penicillins and analogs
-
- 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)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Relates to penicillins of the formula <FORM:0924612/IV(a)/1> wherein R1 and R2, which are different, stand for alkyl, aryl or aralkyl radicals, optionally substituted, and the salts thereof. The Specification contains many examples of penicillins of the above formula, of which the following are typical: 6-(O-2-chlorophenyl-O1- methylphosphoramidyl) - penicillanic acid 6(O-methyl-O1-2-chloroethylphosphoramidyl)-penicillanic acid and 6-(O-2-chlorophenyl-O1- cyclohexylphosphoramidyl) -penicillanic acid. The penicillins may be made by the interaction of 6-aminopenicillanic acid with a phosphoric acid derivative of the formula <FORM:0924612/IV(a)/2> wherein X stands for a halogen atom such as chlorine. The following phosphorochloridate derivatives are obtained by the interaction of the corresponding aromatic phosphorodichloridate derivative with the corresponding alcohol: 2-chlorophenyl 2-methoxy-ethyl, 2-chlorophenyl cyclohexyl-, 4-methoxycarbonylphenyl isopropyl-, 3-tolyl methyl- and 3-tolyl ethyl-phosphorochloridates. 2-Chlorophenyl methyl phosphorochloridate may be prepared by reacting sodium methoxide with 2-chlorophenyl phosphorodichloridate. 2-Methoxycarbonylphenyl methyl and 2-isopropoxycarbonylphenyl isopropyl phosphorochloridates are prepared by the action of methanol and isopropanol respectively on 2- chlorocarbonylphenyl phosphorodichloridate. 4- Methoxycarbonylphenyl phosphorodichloridate may be prepared by reacting methyl p-hydroxybenzoate with phosphorus oxychloride in the presence of magnesium.ALSO:Pharmaceutical compositions comprise one or more penicillins of the formula <FORM:0924612/VI/1> wherein R1 and R2, which are different, stand for alkyl, aryl or aralkyl radicals, optionally substituted (see Group IV (b)) or a non-toxic salt thereof, in admixture with an inert non-toxic diluent or carrier. The compositions may also contain at least one known penicillin or a non-toxic salt thereof. The compositions may be in any of the forms suitable for penicillin therapy such as tablets, granules, capsules, dispersible powders for the preparation of aqueous dispersions, solutions, suspensions, emulsions or ointments.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4356260A GB924612A (en) | 1960-12-19 | 1960-12-19 | Penicillins |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB4356260A GB924612A (en) | 1960-12-19 | 1960-12-19 | Penicillins |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB924612A true GB924612A (en) | 1963-04-24 |
Family
ID=10429303
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB4356260A Expired GB924612A (en) | 1960-12-19 | 1960-12-19 | Penicillins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB924612A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121746A1 (en) * | 1971-01-11 | 1972-08-25 | Lilly Co Eli | |
| FR2217342A1 (en) * | 1972-11-15 | 1974-09-06 | Sumitomo Chemical Co |
-
1960
- 1960-12-19 GB GB4356260A patent/GB924612A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2121746A1 (en) * | 1971-01-11 | 1972-08-25 | Lilly Co Eli | |
| FR2217342A1 (en) * | 1972-11-15 | 1974-09-06 | Sumitomo Chemical Co |
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