GB1428187A - 6-aminopenicillanic acid derivatives and process for the preparation of the same - Google Patents
6-aminopenicillanic acid derivatives and process for the preparation of the sameInfo
- Publication number
- GB1428187A GB1428187A GB3270673A GB3270673A GB1428187A GB 1428187 A GB1428187 A GB 1428187A GB 3270673 A GB3270673 A GB 3270673A GB 3270673 A GB3270673 A GB 3270673A GB 1428187 A GB1428187 A GB 1428187A
- Authority
- GB
- United Kingdom
- Prior art keywords
- substituted
- group
- alkyl
- hydrogen
- amino
- 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
- NGHVIOIJCVXTGV-ALEPSDHESA-N 6-aminopenicillanic acid Chemical class [O-]C(=O)[C@H]1C(C)(C)S[C@@H]2[C@H]([NH3+])C(=O)N21 NGHVIOIJCVXTGV-ALEPSDHESA-N 0.000 title abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 3
- 229910052760 oxygen Inorganic materials 0.000 abstract 3
- 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
- 238000005917 acylation reaction Methods 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 230000003213 activating effect Effects 0.000 abstract 1
- 230000004913 activation Effects 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 125000004429 atom Chemical group 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 229910052801 chlorine Inorganic materials 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000002184 metal Chemical group 0.000 abstract 1
- ZJAOAACCNHFJAH-UHFFFAOYSA-N phosphonoformic acid Chemical class OC(=O)P(O)(O)=O ZJAOAACCNHFJAH-UHFFFAOYSA-N 0.000 abstract 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 1
- IVRIRQXJSNCSPQ-UHFFFAOYSA-N propan-2-yl carbonochloridate Chemical compound CC(C)OC(Cl)=O IVRIRQXJSNCSPQ-UHFFFAOYSA-N 0.000 abstract 1
- 230000000630 rising effect Effects 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- -1 tertiary amino cation Chemical class 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 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
-
- 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
- C07F9/6536—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having nitrogen and sulfur atoms with or without oxygen atoms, as the only ring hetero atoms
- C07F9/6539—Five-membered rings
- C07F9/6541—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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
1428187 6-Aminopenicillanic acid derivatives POLITECHNIKA GDANSKA 9 July 1973 [21 July 1972] 32706/73 Heading C2P Novel 6-aminopenicillanic acid derivatives of the general formula where each of R<SP>1</SP> and R<SP>2</SP> is independently a hydrogen atom, or substituted or non-substituted alkyl group, aryl group, aralkyl or a heterocyclic group or together R<SP>1</SP> and R<SP>2</SP> form the O,O<SP>1</SP>-diphenyl group, Me is a cation, e.g. a hydrogen or metal atom or a tertiary amino cation and P is a substituted phosphoric acid radical having the formula where each of X and Y is independently a hydroxy, alkoxy, aryloxy, alkyl, aryl, aralkyl, heterocyclic or a substituted or non-substituted amino group, and Z is an oxygen or sulphur atom, with the provision that, when Z is oxygen and R<SP>2</SP> is hydrogen, R<SP>1</SP> shall not be hydrogen, C 1 -C 3 alkyl, phenyl or substituted phenyl in which the substituent is chlorine, bromine, fluorine, C 1 -C 3 alkyl, C 1 -C 3 alkoxy or trifluoromethyl, may be prepared by acylating 6-amino-penicillanic acid or a salt thereof with a phosphonocarboxylic acid derivative having the formula where R<SP>1</SP>, R<SP>2</SP>, P, X, Y, Z and Me are as defined above and Akt is any group which can be replaced by the radical of 6-amino-penicillanic acid or a salt thereof. The acylation reaction may be carried out under the influence of an activating agent, e.g. ethyl or isopropyl chloroformate and optionally an activation catalyst, e.g. a tertiary amine, and at a temperature in the region of - 20‹ C., and the acylation reaction proceeds at - 60‹ C. rising to ambient temperature.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL15687072A PL84886B1 (en) | 1972-07-21 | 1972-07-21 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1428187A true GB1428187A (en) | 1976-03-17 |
Family
ID=19959474
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3270673A Expired GB1428187A (en) | 1972-07-21 | 1973-07-09 | 6-aminopenicillanic acid derivatives and process for the preparation of the same |
Country Status (7)
| Country | Link |
|---|---|
| JP (1) | JPS4985087A (en) |
| CS (1) | CS185624B2 (en) |
| DD (1) | DD106651A5 (en) |
| DE (1) | DE2333309C3 (en) |
| GB (1) | GB1428187A (en) |
| HU (1) | HU169754B (en) |
| PL (1) | PL84886B1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2141124A (en) * | 1983-05-17 | 1984-12-12 | Chinoin Gyogyszer Es Vegyeszet | Phosphorus containing semisynthetic cephalosporanic and penicillanic derivatives |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ZA80905B (en) * | 1979-03-01 | 1981-02-25 | Beecham Group Ltd | Penicillin derivatives |
-
1972
- 1972-07-21 PL PL15687072A patent/PL84886B1/pl unknown
-
1973
- 1973-06-18 CS CS438373A patent/CS185624B2/en unknown
- 1973-06-29 DE DE19732333309 patent/DE2333309C3/en not_active Expired
- 1973-07-09 GB GB3270673A patent/GB1428187A/en not_active Expired
- 1973-07-19 DD DD17236273A patent/DD106651A5/xx unknown
- 1973-07-20 JP JP8245673A patent/JPS4985087A/ja active Pending
- 1973-07-20 HU HUPO000546 patent/HU169754B/hu unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2141124A (en) * | 1983-05-17 | 1984-12-12 | Chinoin Gyogyszer Es Vegyeszet | Phosphorus containing semisynthetic cephalosporanic and penicillanic derivatives |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2333309C3 (en) | 1979-01-18 |
| DD106651A5 (en) | 1974-06-20 |
| PL84886B1 (en) | 1976-04-30 |
| HU169754B (en) | 1977-02-28 |
| JPS4985087A (en) | 1974-08-15 |
| DE2333309A1 (en) | 1974-02-14 |
| CS185624B2 (en) | 1978-10-31 |
| DE2333309B2 (en) | 1978-05-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |