GB1051723A - - Google Patents
Info
- Publication number
- GB1051723A GB1051723A GB1051723DA GB1051723A GB 1051723 A GB1051723 A GB 1051723A GB 1051723D A GB1051723D A GB 1051723DA GB 1051723 A GB1051723 A GB 1051723A
- Authority
- GB
- United Kingdom
- Prior art keywords
- acid
- prepared
- reacting
- chloride
- acetamido
- 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.)
- Active
Links
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 abstract 6
- 229930182555 Penicillin Natural products 0.000 abstract 5
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 150000002960 penicillins Chemical class 0.000 abstract 4
- -1 heterocyclic carboxylic acids Chemical class 0.000 abstract 3
- WYJOVVXUZNRJQY-UHFFFAOYSA-N 2-Acetylthiophene Chemical compound CC(=O)C1=CC=CS1 WYJOVVXUZNRJQY-UHFFFAOYSA-N 0.000 abstract 2
- GIWRVUADKUVEGU-UHFFFAOYSA-N 2-oxo-2-thiophen-2-ylacetic acid Chemical compound OC(=O)C(=O)C1=CC=CS1 GIWRVUADKUVEGU-UHFFFAOYSA-N 0.000 abstract 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 abstract 2
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 abstract 2
- 125000002252 acyl group Chemical group 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- JPJALAQPGMAKDF-UHFFFAOYSA-N selenium dioxide Chemical compound O=[Se]=O JPJALAQPGMAKDF-UHFFFAOYSA-N 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- OXHNLMTVIGZXSG-UHFFFAOYSA-N 1-Methylpyrrole Chemical compound CN1C=CC=C1 OXHNLMTVIGZXSG-UHFFFAOYSA-N 0.000 abstract 1
- GEZGAZKEOUKLBR-UHFFFAOYSA-N 1-phenylpyrrole Chemical compound C1=CC=CN1C1=CC=CC=C1 GEZGAZKEOUKLBR-UHFFFAOYSA-N 0.000 abstract 1
- LBDBFEJSQZIUOX-UHFFFAOYSA-N 2-(furan-2-yl)-2-oxoacetyl chloride Chemical compound ClC(=O)C(=O)C1=CC=CO1 LBDBFEJSQZIUOX-UHFFFAOYSA-N 0.000 abstract 1
- XVIVXBUHRORPKA-UHFFFAOYSA-N 2-oxo-2-(1-phenylpyrrol-2-yl)acetyl chloride Chemical compound ClC(=O)C(=O)C1=CC=CN1C1=CC=CC=C1 XVIVXBUHRORPKA-UHFFFAOYSA-N 0.000 abstract 1
- QNGCJXVRQJGLCX-UHFFFAOYSA-N 2-oxo-2-(1h-pyrrol-2-yl)acetyl chloride Chemical compound ClC(=O)C(=O)C1=CC=CN1 QNGCJXVRQJGLCX-UHFFFAOYSA-N 0.000 abstract 1
- SZNAAPJHZVKWKD-UHFFFAOYSA-N 2-oxo-2-thiophen-2-ylacetyl chloride Chemical compound ClC(=O)C(=O)C1=CC=CS1 SZNAAPJHZVKWKD-UHFFFAOYSA-N 0.000 abstract 1
- GUGQQGROXHPINL-UHFFFAOYSA-N 2-oxobutanoyl chloride Chemical compound CCC(=O)C(Cl)=O GUGQQGROXHPINL-UHFFFAOYSA-N 0.000 abstract 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 abstract 1
- 125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 abstract 1
- 125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 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
- 150000007513 acids Chemical class 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000004414 alkyl thio group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 230000000903 blocking effect Effects 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- 239000003638 chemical reducing agent Substances 0.000 abstract 1
- 125000000068 chlorophenyl group Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 238000005984 hydrogenation reaction Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- 231100000252 nontoxic Toxicity 0.000 abstract 1
- 230000003000 nontoxic effect Effects 0.000 abstract 1
- 229940049954 penicillin Drugs 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 229930192474 thiophene Natural products 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/60—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by oxygen atoms
-
- 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
-
- 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/48—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical
- C07D499/58—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical
- C07D499/64—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms
- C07D499/70—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with a carbon chain, substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, attached to the carboxamido radical substituted in alpha-position to the carboxamido radical by nitrogen atoms with hetero rings as additional substituents on the carbon 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
- C07D499/21—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 with a nitrogen atom directly attached in position 6 and a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D499/44—Compounds with an amino radical acylated by carboxylic acids, attached in position 6
- C07D499/76—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with hetero rings directly attached to the carboxamido radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Catalysts (AREA)
Abstract
1,051,723. Penicillins; heterocyclic carboxylic acids and derivatives thereof. BRISTOLMYERS CO. April 26, 1963 [April 27, 1962 (3)], No. 16612/63. Headings C2A and C2C. Penicillonic acids of the general formula wherein R<SP>1</SP> has the formula in which R<SP>5</SP> is a hydrogen atom, or an alkyl, alkanoyl, alkylsulphonyl, cycloalkyl, phenyl, chlorophenyl, or phenethyl group, and R<SP>2</SP>, R<SP>3</SP> and R<SP>4</SP> are selected from hydrogen or halogen atoms, nitro, alkyl, alkoxy, alkylthio, dialkylamino, alkanoylamino, alkanoyl, alkylsulphonyl, cycloalkyl, cycloalkoxy, or substituted or unsubstituted aryl, aralkyl, aryloxy or aralkyloxy groups, and their non-toxic salts, may be prepared by reacting in a suitable solvent 6- aminopenicillonic acid or a salt thereof with an acid, or functional equivalent thereof, having the general formula wherein R<SP>1</SP> is as above and X is where B is a blocking group removable by hydrogenation in the presence of a catalyst, and when X is hydrogenating in the presence of a catalyst, when X is reducing the carbonyl group with a borohydride reducing agent, and recovering the desired penicillin. The Specification describes the preparation of many penicillins of the above formula, of which the following are typical: 6 - [α - hydroxy - α - (2 - thienyl) acetamido], 6 - [α - hydroxy - α - (3 - furyl) acetamido], 6 - [α - hydroxy - α - (N - phenyl - 2 - pyrrolyl) acetamido] and 6 - [α - bydroxy - α - (4 - pyridyl) acetamido] penicillonic acid, and the Specification also describes the production of D- and L-diastereoisomers of the penicillins as well as mixtures of the two optically active forms. Pharmaceutical compositions comprise penicillins of the invention and conventional additives. Ethyl α-2-thienylglyoxylate is prepared by reacting thiophene with ethyl oxalyl chloride. It may be hydrolysed to produce α-2-thienylglyoxylic acid which may be converted to α-2- thienylglyoxylic acid chloride by treatment with thionyl chloride. α-2-Furylglyoxylic acid chloride is prepared by reacting furan with oxalyl chloride. α-(2-Thienyl) glyoxylic acid is prepared by reacting 2-acetylthiophene with selenium dioxide. 2-Pyrrolylglyoxylic acid chloride is prepared by reacting pyrrole with oxalyl chloride. N-Phenyl-2-pyrrolylglyoxylic acid chloride is prepared by reacting N-phenyl-pyrrole with oxalyl chloride. The N-methyl compound is prepared similarly from N-methyl pyrrole.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US19079562A | 1962-04-27 | 1962-04-27 | |
| US19077462A | 1962-04-27 | 1962-04-27 | |
| US19077662A | 1962-04-27 | 1962-04-27 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1051723A true GB1051723A (en) |
Family
ID=27392795
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB1051723D Active GB1051723A (en) | 1962-04-27 |
Country Status (4)
| Country | Link |
|---|---|
| CH (1) | CH436299A (en) |
| DE (1) | DE1289053B (en) |
| ES (1) | ES287497A1 (en) |
| GB (1) | GB1051723A (en) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254582A3 (en) * | 1986-07-24 | 1988-03-30 | Beecham Group Plc | 6 beta-(alpha-oximino)-acylamino penicillanic-acid derivatives and starting compounds |
| JP2011518818A (en) * | 2008-04-24 | 2011-06-30 | エフツージー リミテッド | Pyrrole antifungal agent |
| US10201524B2 (en) | 2014-11-21 | 2019-02-12 | F2G Limited | Antifungal agents |
| US10973821B2 (en) | 2016-05-25 | 2021-04-13 | F2G Limited | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE593222A (en) * | 1959-08-03 | 1961-01-20 | Pfizer & Co C | Antibiotics from the penicillin group |
| US2996501A (en) * | 1960-03-31 | 1961-08-15 | Doyle Frank Peter | Synthetic penicillins |
-
0
- GB GB1051723D patent/GB1051723A/en active Active
-
1963
- 1963-04-23 DE DE1963B0071594 patent/DE1289053B/en active Pending
- 1963-04-26 CH CH524163A patent/CH436299A/en unknown
- 1963-04-27 ES ES287497A patent/ES287497A1/en not_active Expired
Cited By (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0254582A3 (en) * | 1986-07-24 | 1988-03-30 | Beecham Group Plc | 6 beta-(alpha-oximino)-acylamino penicillanic-acid derivatives and starting compounds |
| US4918067A (en) * | 1986-07-24 | 1990-04-17 | Beecham Group P.L.C. | Heterocyclic substituted penicillin antibiotics |
| JP2011518818A (en) * | 2008-04-24 | 2011-06-30 | エフツージー リミテッド | Pyrrole antifungal agent |
| AU2009239778B2 (en) * | 2008-04-24 | 2014-03-13 | F2G Ltd | Pyrrole antifungal agents |
| US8993574B2 (en) | 2008-04-24 | 2015-03-31 | F2G Ltd | Pyrrole antifungal agents |
| US9452168B2 (en) | 2008-04-24 | 2016-09-27 | F2G Ltd | Pyrrole antifungal agents |
| US10201524B2 (en) | 2014-11-21 | 2019-02-12 | F2G Limited | Antifungal agents |
| US10596150B2 (en) | 2014-11-21 | 2020-03-24 | F2G Limited | Antifungal agents |
| US11065228B2 (en) | 2014-11-21 | 2021-07-20 | F2G Limited | Antifungal agents |
| US10973821B2 (en) | 2016-05-25 | 2021-04-13 | F2G Limited | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
Also Published As
| Publication number | Publication date |
|---|---|
| ES287497A1 (en) | 1963-12-01 |
| CH436299A (en) | 1967-05-31 |
| DE1289053B (en) | 1969-02-13 |
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