ES444389A1 - Penicillins their production and their medicinal use - Google Patents
Penicillins their production and their medicinal useInfo
- Publication number
- ES444389A1 ES444389A1 ES444389A ES444389A ES444389A1 ES 444389 A1 ES444389 A1 ES 444389A1 ES 444389 A ES444389 A ES 444389A ES 444389 A ES444389 A ES 444389A ES 444389 A1 ES444389 A1 ES 444389A1
- Authority
- ES
- Spain
- Prior art keywords
- carbon atoms
- amino
- alkyl
- see formula
- group
- 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 2
- 238000004519 manufacturing process Methods 0.000 title abstract 2
- 150000002960 penicillins Chemical class 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 13
- 125000000217 alkyl group Chemical group 0.000 abstract 8
- 125000003545 alkoxy group Chemical group 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 2
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical group 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 231100000252 nontoxic Toxicity 0.000 abstract 2
- 230000003000 nontoxic effect Effects 0.000 abstract 2
- 150000003839 salts Chemical class 0.000 abstract 2
- 239000002904 solvent Substances 0.000 abstract 2
- 229910052717 sulfur Chemical group 0.000 abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
- IOVCWXUNBOPUCH-UHFFFAOYSA-M Nitrite anion Chemical compound [O-]N=O IOVCWXUNBOPUCH-UHFFFAOYSA-M 0.000 abstract 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract 1
- 125000004423 acyloxy group Chemical group 0.000 abstract 1
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000003609 aryl vinyl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract 1
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 abstract 1
- CODNYICXDISAEA-UHFFFAOYSA-N bromine monochloride Chemical compound BrCl CODNYICXDISAEA-UHFFFAOYSA-N 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 125000000000 cycloalkoxy group Chemical group 0.000 abstract 1
- 229910052731 fluorine Inorganic materials 0.000 abstract 1
- 239000011737 fluorine Substances 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 1
- -1 nitro, amino Chemical group 0.000 abstract 1
- 229910052757 nitrogen Inorganic materials 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 229910052760 oxygen Inorganic materials 0.000 abstract 1
- 239000001301 oxygen Substances 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/32—One oxygen atom
- C07D233/38—One oxygen atom with acyl radicals or hetero atoms directly attached to ring nitrogen atoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Fodder In General (AREA)
Abstract
Process for the production of substituted hydroxybenzylpenicillins, of general formula I **(See formula)** where A is a group (see formula) or (see formula), x is hydrogen, alkyl with up to 10 carbon atoms, alkyl with up to 6 carbon atoms, with one hydrogen atom being from the alkyl group with up to 6 carbon atoms, with one hydrogen atom from the alkyl group being substituted by a nitro, amino, mono (lower) -alkyl-amino, dialkyl (lower) -amino group or a 1-pyridinium group; alkenyl with up to 10 carbon atoms, vinyl, cycloalkyl and cycloalkenyl with up to 10-carbon atoms, aryl vinyl, mono-, di- and trihalogenoalkyl lower, monoalkyl- (lower) -amino, dialkyl (lower) -amino, monoarylamino, arylalkyl - (lower) -amino, alkoxy with up to 8 carbon atoms, cycloalkoxy with up to 7 carbon atoms, aralkoxy with up to 8 carbon atoms, aryloxy, **(See formula)** n is an integer from zero to 2 inclusive and R1, R2 and R3 are each hydrogen, nitro, nitrite, amino, dialkyl (lower) -amino, dialkyl (lower) -aminocarbonyl, alkanoyl (lower) -amino, alkoxy (lower) -carbonyl, lower alkanoyloxy, lower alkyl, lower alkoxy, sulfamyl, chloro, bromine, iodine, fluorine or trifluoromethyl, Y is alkyl with up to 4 carbon atoms, alkenyl with up to 4 carbon atoms, vinyl, propenyl, cycloalkyl and cycloalkenyl with up to 6 carbon atoms, mono-, di and trihalogenoalkyl lower, aralkyl with up to 8 carbon atoms or aryl, (see graph) is a bivalent group **(See formula)** G is hydrogen or low molecular weight alkyl with up to 3 carbon atoms, indicating the arrow in the bivalent group (see graph) that in the link of the two free valences of (see graph) with the nitrogen atom and the carbon atom of the group (see formula) must not proceed in any way, but in the form characterized by the arrow, E is oxygen or sulfur, B is **(See formula)** and which, regarding the chirality center (see graph), they can be presented in the two possible configurations R and S and as mixtures of the resulting diastereomers, as well as their pharmaceutically tolerable non-toxic salts; characterized by that compounds of general formulas IV and V **(See formula)** in which B has the meaning indicated above or represents **(See formula)** (see graph) has the meaning specified above and R4, R5 and R6 represent alkyl with up to 6 carbon atoms, they are reacted with compounds of general formula VI or VII: **(See formula)** where X, Y, Z and E are defined as above and N represents halogen, azido, a group **(See formula)** in anhydrous solvents free of hydroxyl groups, or in solvents containing water or hydroxyl groups, with or without the addition of a base at a temperature of the range of approximately -20ºC to + 50ºC, and the penicillins thus obtained are eventually transformed into their non-toxic salts pharmaceutically tolerable. (Machine-translation by Google Translate, not legally binding)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722258973 DE2258973A1 (en) | 1972-12-01 | 1972-12-01 | PENICILLIN, THE METHOD FOR MANUFACTURING IT AND THEIR USE AS A MEDICINAL PRODUCT |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| ES444389A1 true ES444389A1 (en) | 1977-06-01 |
Family
ID=5863290
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES421006A Expired ES421006A1 (en) | 1972-12-01 | 1973-11-30 | Penicillins their production and their medicinal use |
| ES444389A Expired ES444389A1 (en) | 1972-12-01 | 1976-01-16 | Penicillins their production and their medicinal use |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| ES421006A Expired ES421006A1 (en) | 1972-12-01 | 1973-11-30 | Penicillins their production and their medicinal use |
Country Status (20)
| Country | Link |
|---|---|
| JP (2) | JPS576435B2 (en) |
| AR (2) | AR200161A1 (en) |
| AU (1) | AU6285673A (en) |
| BE (1) | BE807918A (en) |
| BG (1) | BG20812A3 (en) |
| CH (1) | CH601306A5 (en) |
| DD (1) | DD109221A5 (en) |
| DE (1) | DE2258973A1 (en) |
| EG (1) | EG11062A (en) |
| ES (2) | ES421006A1 (en) |
| FR (1) | FR2208647B1 (en) |
| GB (1) | GB1426199A (en) |
| IE (1) | IE38560B1 (en) |
| IL (1) | IL43708A (en) |
| LU (1) | LU68892A1 (en) |
| NL (1) | NL7316357A (en) |
| PH (1) | PH10188A (en) |
| RO (2) | RO65197A (en) |
| SU (1) | SU523640A3 (en) |
| ZA (1) | ZA739121B (en) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5852996B2 (en) * | 1975-03-25 | 1983-11-26 | バイエル・アクチエンゲゼルシヤフト | Beta-lactams and antibacterial agents |
| DE2658905A1 (en) * | 1976-12-24 | 1978-10-19 | Bayer Ag | BETA-LACTAM-ANTIBIOTICA, METHOD FOR MANUFACTURING IT AND ITS USE AS A MEDICINAL PRODUCT |
| DE2810083A1 (en) | 1978-03-08 | 1979-09-20 | Bayer Ag | BETA-LACTAM COMPOUNDS |
| US4229348A (en) * | 1978-05-26 | 1980-10-21 | Chugai Seiyaku Kabushiki Kaisha | Penicillanic acid derivatives |
| ZA795477B (en) * | 1978-10-16 | 1981-03-25 | Bristol Myers Co | Antibacterial agents |
| JPS5732289A (en) | 1980-08-05 | 1982-02-20 | Chugai Pharmaceut Co Ltd | Alpha-substituted ureidobenzylpenicillin |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE790440A (en) * | 1971-10-23 | 1973-04-24 | Bayer Ag |
-
1972
- 1972-12-01 DE DE19722258973 patent/DE2258973A1/en active Pending
-
1973
- 1973-11-12 PH PH15218A patent/PH10188A/en unknown
- 1973-11-23 AU AU62856/73A patent/AU6285673A/en not_active Expired
- 1973-11-27 IL IL7343708A patent/IL43708A/en unknown
- 1973-11-27 BG BG25084A patent/BG20812A3/xx unknown
- 1973-11-28 BE BE138262A patent/BE807918A/en unknown
- 1973-11-28 RO RO7376805A patent/RO65197A/en unknown
- 1973-11-28 RO RO7385228A patent/RO72164A/en unknown
- 1973-11-29 LU LU68892A patent/LU68892A1/xx unknown
- 1973-11-29 NL NL7316357A patent/NL7316357A/xx not_active Application Discontinuation
- 1973-11-29 CH CH1678673A patent/CH601306A5/xx not_active IP Right Cessation
- 1973-11-29 JP JP13314673A patent/JPS576435B2/ja not_active Expired
- 1973-11-29 EG EG452/73A patent/EG11062A/en active
- 1973-11-29 DD DD174978A patent/DD109221A5/xx unknown
- 1973-11-29 JP JP48133147A patent/JPS4986519A/ja active Pending
- 1973-11-29 SU SU1972067A patent/SU523640A3/en active
- 1973-11-30 ES ES421006A patent/ES421006A1/en not_active Expired
- 1973-11-30 AR AR251293A patent/AR200161A1/en active
- 1973-11-30 IE IE2174/73A patent/IE38560B1/en unknown
- 1973-11-30 FR FR7342743A patent/FR2208647B1/fr not_active Expired
- 1973-11-30 GB GB5566873A patent/GB1426199A/en not_active Expired
- 1973-11-30 ZA ZA739121A patent/ZA739121B/en unknown
-
1974
- 1974-01-01 AR AR255998A patent/AR205450A1/en active
-
1976
- 1976-01-16 ES ES444389A patent/ES444389A1/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7316357A (en) | 1974-06-05 |
| IE38560L (en) | 1974-06-01 |
| DE2258973A1 (en) | 1974-06-06 |
| IE38560B1 (en) | 1978-04-12 |
| AR205450A1 (en) | 1976-05-07 |
| DD109221A5 (en) | 1974-10-20 |
| AR200161A1 (en) | 1974-10-24 |
| GB1426199A (en) | 1976-02-25 |
| JPS49116091A (en) | 1974-11-06 |
| CH601306A5 (en) | 1978-07-14 |
| ZA739121B (en) | 1974-10-30 |
| BG20812A3 (en) | 1975-12-20 |
| JPS4986519A (en) | 1974-08-19 |
| FR2208647A1 (en) | 1974-06-28 |
| RO72164A (en) | 1983-08-03 |
| JPS576435B2 (en) | 1982-02-04 |
| IL43708A0 (en) | 1974-03-14 |
| RO72164B (en) | 1983-07-30 |
| SU523640A3 (en) | 1976-07-30 |
| BE807918A (en) | 1974-05-28 |
| RO65197A (en) | 1982-09-09 |
| PH10188A (en) | 1976-09-23 |
| ES421006A1 (en) | 1976-07-16 |
| EG11062A (en) | 1977-08-15 |
| FR2208647B1 (en) | 1977-10-28 |
| IL43708A (en) | 1977-02-28 |
| LU68892A1 (en) | 1974-02-11 |
| AU6285673A (en) | 1975-05-29 |
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