GB1353493A - Penicillins - Google Patents
PenicillinsInfo
- Publication number
- GB1353493A GB1353493A GB1353493DA GB1353493A GB 1353493 A GB1353493 A GB 1353493A GB 1353493D A GB1353493D A GB 1353493DA GB 1353493 A GB1353493 A GB 1353493A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acetic acid
- amino
- acid
- reacting
- prepared
- 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 3
- 150000002960 penicillins Chemical class 0.000 title abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 9
- 239000002253 acid Substances 0.000 abstract 5
- 150000003839 salts Chemical class 0.000 abstract 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- -1 acetoxymethyl Chemical group 0.000 abstract 3
- LOZWAPSEEHRYPG-UHFFFAOYSA-N 1,4-dithiane Chemical compound C1CSCCS1 LOZWAPSEEHRYPG-UHFFFAOYSA-N 0.000 abstract 2
- SRMWKNUAAAAUED-UHFFFAOYSA-N 2-amino-2-piperidin-4-ylacetic acid Chemical compound OC(=O)C(N)C1CCNCC1 SRMWKNUAAAAUED-UHFFFAOYSA-N 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 2
- 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 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- 241001465754 Metazoa Species 0.000 abstract 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 abstract 2
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 150000002148 esters Chemical class 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 abstract 1
- SNFHZTJIKWJOJC-UHFFFAOYSA-N 2-amino-2-(1,4-dithian-2-yl)acetic acid Chemical compound NC(C(=O)O)C1SCCSC1 SNFHZTJIKWJOJC-UHFFFAOYSA-N 0.000 abstract 1
- ZUEHYZHEPPUITG-UHFFFAOYSA-N 2-amino-2-(thian-2-yl)acetic acid Chemical compound OC(=O)C(N)C1CCCCS1 ZUEHYZHEPPUITG-UHFFFAOYSA-N 0.000 abstract 1
- AXPLBJKDQVVEBD-UHFFFAOYSA-N 2-amino-2-(thian-4-yl)acetic acid Chemical compound OC(=O)C(N)C1CCSCC1 AXPLBJKDQVVEBD-UHFFFAOYSA-N 0.000 abstract 1
- XLZJPHKIECMDPG-UHFFFAOYSA-N 2-azaniumyl-2-(oxan-4-yl)acetate Chemical compound OC(=O)C(N)C1CCOCC1 XLZJPHKIECMDPG-UHFFFAOYSA-N 0.000 abstract 1
- BPTCAQMPNJVACB-UHFFFAOYSA-N 2-azaniumyl-2-pyridin-4-ylacetate Chemical compound OC(=O)C(N)C1=CC=NC=C1 BPTCAQMPNJVACB-UHFFFAOYSA-N 0.000 abstract 1
- PXACTUVBBMDKRW-UHFFFAOYSA-N 4-bromobenzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=C(Br)C=C1 PXACTUVBBMDKRW-UHFFFAOYSA-N 0.000 abstract 1
- KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 abstract 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 abstract 1
- 241000894006 Bacteria Species 0.000 abstract 1
- 241000283690 Bos taurus Species 0.000 abstract 1
- KTOKPIICMXUILF-UHFFFAOYSA-N C(C)(=O)NC(C(=O)OCC)(C(=O)OCC)[Na] Chemical compound C(C)(=O)NC(C(=O)OCC)(C(=O)OCC)[Na] KTOKPIICMXUILF-UHFFFAOYSA-N 0.000 abstract 1
- XRAZNMVMBYWDLH-UHFFFAOYSA-N CCC(CC)C(NC(C(O)=O)(C(O)=O)[Na])=O Chemical compound CCC(CC)C(NC(C(O)=O)(C(O)=O)[Na])=O XRAZNMVMBYWDLH-UHFFFAOYSA-N 0.000 abstract 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 abstract 1
- 208000035473 Communicable disease Diseases 0.000 abstract 1
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 abstract 1
- 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 abstract 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 abstract 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 239000005864 Sulphur Substances 0.000 abstract 1
- YPWFISCTZQNZAU-UHFFFAOYSA-N Thiane Chemical compound C1CCSCC1 YPWFISCTZQNZAU-UHFFFAOYSA-N 0.000 abstract 1
- JVVXZOOGOGPDRZ-SLFFLAALSA-N [(1R,4aS,10aR)-1,4a-dimethyl-7-propan-2-yl-2,3,4,9,10,10a-hexahydrophenanthren-1-yl]methanamine Chemical compound NC[C@]1(C)CCC[C@]2(C)C3=CC=C(C(C)C)C=C3CC[C@H]21 JVVXZOOGOGPDRZ-SLFFLAALSA-N 0.000 abstract 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 abstract 1
- 229910052782 aluminium Inorganic materials 0.000 abstract 1
- 239000004411 aluminium Substances 0.000 abstract 1
- 239000001099 ammonium carbonate Substances 0.000 abstract 1
- 235000012501 ammonium carbonate Nutrition 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000005161 aryl oxy carbonyl group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000011575 calcium Substances 0.000 abstract 1
- 229910052791 calcium Inorganic materials 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 235000015872 dietary supplement Nutrition 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 abstract 1
- 229940091173 hydantoin Drugs 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 208000004396 mastitis Diseases 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 150000003961 organosilicon compounds Chemical class 0.000 abstract 1
- LMYJGUNNJIDROI-UHFFFAOYSA-N oxan-4-ol Chemical compound OC1CCOCC1 LMYJGUNNJIDROI-UHFFFAOYSA-N 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000011591 potassium Substances 0.000 abstract 1
- 229910052700 potassium Inorganic materials 0.000 abstract 1
- NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract 1
- 244000144977 poultry Species 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- MFDFERRIHVXMIY-UHFFFAOYSA-N procaine Chemical compound CCN(CC)CCOC(=O)C1=CC=C(N)C=C1 MFDFERRIHVXMIY-UHFFFAOYSA-N 0.000 abstract 1
- 229960004919 procaine Drugs 0.000 abstract 1
- BGUWFUQJCDRPTL-UHFFFAOYSA-N pyridine-4-carbaldehyde Chemical compound O=CC1=CC=NC=C1 BGUWFUQJCDRPTL-UHFFFAOYSA-N 0.000 abstract 1
- 239000011734 sodium Substances 0.000 abstract 1
- 229910052708 sodium Inorganic materials 0.000 abstract 1
- 229910000104 sodium hydride Inorganic materials 0.000 abstract 1
- 239000012312 sodium hydride Substances 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D339/00—Heterocyclic compounds containing rings having two sulfur atoms as the only ring hetero atoms
- C07D339/08—Six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/08—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms
- C07D211/18—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D211/34—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hydrocarbon or substituted hydrocarbon radicals directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring carbon atoms with hydrocarbon radicals, substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/04—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D309/08—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D309/10—Oxygen atoms
- C07D309/12—Oxygen atoms only hydrogen atoms and one oxygen atom directly attached to ring carbon atoms, e.g. tetrahydropyranyl ethers
-
- 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
1353493 Penicillins BEECHAM GROUP Ltd 22 June 1972 [9 July 1971] 32245/71 Headings C2A and C2C Novel α-amino-penicillins of formula wherein R represents a fully saturated heterocyclic radical, and pharmaceutically acceptable salts and esters thereof, may be prepared by reacting 6-aminopenicillanic acid, or a salt thereof, or the reaction product of 6-aminopenicillanic acid with an organo silicon compound, with a reactive derivative of an acid of the general formula wherein X is a nitrogen-containing group, and subsequently converting X into a primary amino group. The fully saturated heterocyclic radical may have the formulµ wherein Z is oxygen, sulphur or wherein R<SP>1</SP> is hydrogen, C 1-6 alkyl, aryl, arylalkyl or aryloxy carbonyl. Specified salts include sodium, potassium, calcium, aluminium, ammonium, triethylamine, procaine, dibenzylamine, N - benzyl - # - phenethylamine, 1- ephenamine, N,N<SP>1</SP>-dibenzylethylenediamine, dehydro-abietylamine and N-N<SP>1</SP>-bis-dehydro-abietylethylenediamine salts, and esters include acetoxymethyl and pivaloyloxymethyl esters. α - Amino - 1 - thiacyclohexan - 2 - yl acetic acid and α - amino - 1,4 - dithian - 2 - yl acetic acid are prepared by reacting thiacyclohexane and 1,4-dithian respectively with chlorine to give a chlorine complex which, when reacted with diethylacetamido sodiomalonate, sodium hydride and dimethylformamide, forms the desired acid. α - Amino - 1 - thiacyclohex - 4 - yl acetic acid is prepared by reacting thiacyclohexan-4-ol with p-bromobenzenesulphonyl chloride or benzenesulphonyl chloride to produce the p-bromobenzenesulphonate or benzenesulphonate respectively which, when reacted with dimethylformamide and diethylacetamidosodiomalonate, forms the desired acid. α-Amino-tetra-hydropyran-4-yl acetic acid is prepared by reacting 4- hydroxytetrahydropyran with benzenesulphonyl chloride to produce the benzenesulphonate which, when reacted with diethyl acetamidosodiomalonate and dimethyl formamide, forms the desired acid. α-Amino-piperid-4-yl acetic acid is prepared by reacting pyridine-4-aldehyde with potassium cyanide and ammonium carbonate to give the hydantoin which is hydrolysed to α - aminopyrid - 4 - yl acetic acid which is hydrogenated to the desired acid. Bis - N,N<SP>1</SP>- benzyloxycarbonyl - α - aminopiperid - 4 - yl acetic acid is prepared by reacting α-aminopiperid-4-yl acetic acid with benzyl chloroformate. The above penicillins are useful as antibacterial agents, nutritional supplements in animal food, agents for the treatment of mastitis in cattle and as therapeutic agents in poultry and animals in the treatment of infectious diseases caused by Gram-positive and Gram-negative bacteria.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3224571 | 1971-07-09 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1353493A true GB1353493A (en) | 1974-05-15 |
Family
ID=10335587
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1353493D Expired GB1353493A (en) | 1971-07-09 | 1971-07-09 | Penicillins |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1353493A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0033066A3 (en) * | 1980-01-07 | 1981-09-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Penicillin derivatives, intermediates for their preparation, pharmaceutical compositions containing them, their preparation and their use |
| WO2003010130A1 (en) * | 2001-07-24 | 2003-02-06 | Pharmacore, Inc. | Amino acid derivatives |
| JP2006045107A (en) * | 2004-08-04 | 2006-02-16 | Ube Ind Ltd | Method for producing 4-tetrahydropyranylglycine |
| CN111675641A (en) * | 2020-06-04 | 2020-09-18 | 宁夏农林科学院农业资源与环境研究所（宁夏土壤与植物营养重点实验室） | Monocyclic beta-lactam compound, monocyclic lactam compound salt and preparation method thereof |
| US11547704B2 (en) | 2016-06-08 | 2023-01-10 | Glaxosmithkline Intellectual Property Development Limited | Chemical compounds |
| CN118290656A (en) * | 2024-04-23 | 2024-07-05 | 吴桥县齐源纤维素有限公司 | A kind of cellulose ether and preparation method thereof |
-
1971
- 1971-07-09 GB GB1353493D patent/GB1353493A/en not_active Expired
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0033066A3 (en) * | 1980-01-07 | 1981-09-23 | F. HOFFMANN-LA ROCHE & CO. Aktiengesellschaft | Penicillin derivatives, intermediates for their preparation, pharmaceutical compositions containing them, their preparation and their use |
| WO2003010130A1 (en) * | 2001-07-24 | 2003-02-06 | Pharmacore, Inc. | Amino acid derivatives |
| US6809207B2 (en) | 2001-07-24 | 2004-10-26 | Pharmacore, Inc. | Amino acid derivatives |
| JP2006045107A (en) * | 2004-08-04 | 2006-02-16 | Ube Ind Ltd | Method for producing 4-tetrahydropyranylglycine |
| US11547704B2 (en) | 2016-06-08 | 2023-01-10 | Glaxosmithkline Intellectual Property Development Limited | Chemical compounds |
| CN111675641A (en) * | 2020-06-04 | 2020-09-18 | 宁夏农林科学院农业资源与环境研究所（宁夏土壤与植物营养重点实验室） | Monocyclic beta-lactam compound, monocyclic lactam compound salt and preparation method thereof |
| CN111675641B (en) * | 2020-06-04 | 2023-09-08 | 宁夏农林科学院农业资源与环境研究所（宁夏土壤与植物营养重点实验室） | Monocyclic beta-lactam compound, monocyclic lactam compound salt and preparation method thereof |
| CN118290656A (en) * | 2024-04-23 | 2024-07-05 | 吴桥县齐源纤维素有限公司 | A kind of cellulose ether and preparation method thereof |
| CN118290656B (en) * | 2024-04-23 | 2024-11-01 | 吴桥县齐源纤维素有限公司 | Cellulose ether and preparation method thereof |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |