NL172660B - METHOD FOR PREPARING AN ANTIBIOTICALLY ACTIVE PHARMACEUTICAL PREPARATION AND METHOD FOR PREPARING A 6-ALFA-(3-ACYLUREIDO)ACETYLAMINO PENICILLAN ACID DERIVATIVE. - Google Patents
METHOD FOR PREPARING AN ANTIBIOTICALLY ACTIVE PHARMACEUTICAL PREPARATION AND METHOD FOR PREPARING A 6-ALFA-(3-ACYLUREIDO)ACETYLAMINO PENICILLAN ACID DERIVATIVE.Info
- Publication number
- NL172660B NL172660B NLAANVRAGE7107175,A NL7107175A NL172660B NL 172660 B NL172660 B NL 172660B NL 7107175 A NL7107175 A NL 7107175A NL 172660 B NL172660 B NL 172660B
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- NL
- Netherlands
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- carbon atoms
- formulμ
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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
- C07D499/64—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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- C07D499/68—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 aromatic rings as additional substituents on the carbon chain
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Cephalosporin Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Abstract
1301961 Preparation of ureido penicillins BAYER AG 25 May 1971 [25 May 1970 22 Aug 1970 1 Feb 1971 3 Feb 1971 9 March 1971] 16880/71 Heading C2A The invention comprises a process for the preparation of penicillins of Fomula (I) and salts thereof, which process comprises reacting a compound of Formula (52) or a condensation product of such a compound with a carbonyl compound, preferably acetone, of general formula (53) or a compound of general formula (54) or (55) at a temperature of -20‹ C. to +50‹ C. with a compound of general formula (57) or (58) or in a solvent and in the presence of a base when a compound of general fromula (52) or (53) is used, and in an anydrous solvent free of hydroxyl groups with or without the presence of a base when a compound of general formula (54) or (55) is used; and when a salt is derived converting the penicillin thus produced into the desired salt. In the above formulµ, A denotes a group of general formula wherein X is hydrogen or an alkyl, alkenyl, cycloalkyl or cycloalkenyl group with up to ten carbon atoms, or a vinyl, arylvinyl, mono-, di- or tri-haloalkyl, monoalkylamino, dialkylamino, monoarylamino or arylalkylamino group, or an alkoxy or aralkoxy group with up to eight carbon atoms, or a cycloalkoxy group with up to 7 carbon atoms, or an aryloxy group, or a group having one of the general formulae in which formulµ V is a divalent radical with one to three carbon atoms, n is 0, 1 or 2 and R 1 , R 2 and R 3 , which may be the same or different, each denote a hydrogen, chlorine, bromine, iodine or fluorine atom or a nitro, nitrile, dialkylamino, dialkylaminocarbonyl, alkanoylamino, alkoxycarbonyl, alkanoxyloxy, alkyl, alkoxy with up to 6 carbon atoms, sulphamyl or trifluoromethyl, Y is an alkyl, alkenyl, cycloalkyl or cycloalkenyl group with up to 10 carbon atoms, or a vinyl, propenyl, mono-, di- or trihalo alkyl group with up to 8 carbon atoms ; #Z- denotes a divalent group having one of the general formulµ in which n is an integer from 3 to 5 and the arrow of the divalent group Z means that the linkage of the two free valencies of the group #Z- with the nitrogen and carbon atoms of the group of general formula (3) is not arbitrary, but is orientated as indicated by the arrow; E denotes an oxygen or sulphur atom; and Q denotes a divalent radical ; particularly a radical having one of the general formulµ in which general formulµ G is a hydrogen atom or a C 1 -C 6 alkyl group, the arrow means that the linkage of the two free valencies of the group Q with the two nitrogen atoms of the group of Formula (4) is orientated as indicated by the arrow; and M is a group having one of the general formulµ In the above formulµ B denotes a phenyl group or a phenyl or thienyl group substituted by an alkyl, alkoxy or alkylthio group having 1 to 6 carbon atoms; and C* is a carbon atom which constitutes a chirality centre which can be in either of the two possible R- and S- configurations, R 4 , R 5 and R 6 are C 1 -C 6 alkyl groups and w is a halogen atom or an azide group. The invention also comprises D-α-(3- acetyl - 3 - methyl - ureido) - benzyl - penicillin, D - α - (3 - dimethylaminocarbonyl - 3 - methylureido) - benzylpenicillin, D - α - (pyrrolid - 2- on - 1 yl - carbonylamino) - benzylpencillin and D - α - (imidazolidin - 2 - on - 1 - yl - carbonylamino) benzylpenicillin and the sodium salts thereof. Phermaceutical compositions containing at least one of the above penicillins as antibiotically active ingredient have been prepared.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2025414A DE2025414C3 (en) | 1970-05-25 | 1970-05-25 | Cyclic acylureidophenylacetamidopenicillanic acids |
| DE19712104580 DE2104580C3 (en) | 1971-02-01 | 1971-02-01 | Acylureidopenicillins |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| NL7107175A NL7107175A (en) | 1971-11-29 |
| NL172660B true NL172660B (en) | 1983-05-02 |
| NL172660C NL172660C (en) | 1983-10-03 |
Family
ID=25759178
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NLAANVRAGE7107175,A NL172660C (en) | 1970-05-25 | 1971-05-25 | METHOD FOR PREPARING AN ANTIBIOTICALLY ACTIVE PHARMACEUTICAL PREPARATION AND METHOD FOR PREPARING A 6-ALFA-(3-ACYLUREIDO)ACETYLAMINO PENICILLAN ACID DERIVATIVE. |
Country Status (28)
| Country | Link |
|---|---|
| JP (1) | JPS5538357B1 (en) |
| AR (2) | AR195267A1 (en) |
| AT (1) | AT307617B (en) |
| BE (1) | BE767647A (en) |
| BG (1) | BG23220A3 (en) |
| CA (1) | CA943128A (en) |
| CH (1) | CH562249A5 (en) |
| CS (1) | CS171230B2 (en) |
| CY (1) | CY829A (en) |
| DD (1) | DD91497B3 (en) |
| DK (1) | DK133679C (en) |
| EG (1) | EG10856A (en) |
| ES (4) | ES391532A1 (en) |
| FI (1) | FI54484C (en) |
| FR (1) | FR2100681B1 (en) |
| GB (1) | GB1301961A (en) |
| HU (1) | HU162205B (en) |
| IE (1) | IE35311B1 (en) |
| IL (1) | IL36905A (en) |
| KE (1) | KE2592A (en) |
| LU (1) | LU63203A1 (en) |
| NL (1) | NL172660C (en) |
| NO (1) | NO141164C (en) |
| PH (1) | PH14794A (en) |
| RO (2) | RO62689A (en) |
| SE (1) | SE395896B (en) |
| SU (1) | SU472507A3 (en) |
| YU (1) | YU130271A (en) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2354219A1 (en) * | 1973-10-30 | 1975-05-07 | Bayer Ag | BETA-LACTAM-ANTIBIOTICA, A PROCESS FOR THEIR MANUFACTURING AND ITS USE AS A MEDICINAL PRODUCT |
| US4039673A (en) | 1973-10-30 | 1977-08-02 | Bayer Aktiengesellschaft | Penicillins and cephalosporins and their production |
| GB1486349A (en) * | 1974-11-28 | 1977-09-21 | Bayer Ag | Beta-lactam antibiotics process for their preparation and their use as medicaments |
| DE2658906A1 (en) * | 1976-12-24 | 1978-07-06 | Bayer Ag | BETA-LACTAM ANTIBIOTICS, THE METHOD OF MANUFACTURING AND THEIR USE AS A MEDICINAL PRODUCT |
| GB1584400A (en) * | 1976-12-24 | 1981-02-11 | Bayer Ag | (2-oxo-imidazoliden-1-yl(carbonylamino)-acetamido-cephalosporins and penicillins |
| CA1133896A (en) * | 1978-05-26 | 1982-10-19 | Nobuhiro Oi | Penicillanic acid derivative and process for preparing the same |
| JPS5732289A (en) | 1980-08-05 | 1982-02-20 | Chugai Pharmaceut Co Ltd | Alpha-substituted ureidobenzylpenicillin |
-
1971
- 1971-04-23 CH CH599071A patent/CH562249A5/xx not_active IP Right Cessation
- 1971-05-13 BG BG017580A patent/BG23220A3/en unknown
- 1971-05-19 EG EG209/71A patent/EG10856A/en active
- 1971-05-19 CS CS3646A patent/CS171230B2/cs unknown
- 1971-05-20 SU SU1661304A patent/SU472507A3/en active
- 1971-05-21 IE IE643/71A patent/IE35311B1/en unknown
- 1971-05-21 FI FI1401/71A patent/FI54484C/en active
- 1971-05-21 LU LU63203D patent/LU63203A1/xx unknown
- 1971-05-24 PH PH12493A patent/PH14794A/en unknown
- 1971-05-24 YU YU01302/71A patent/YU130271A/en unknown
- 1971-05-24 IL IL7136905A patent/IL36905A/en unknown
- 1971-05-24 DD DD71155301A patent/DD91497B3/en unknown
- 1971-05-24 SE SE7106667A patent/SE395896B/en unknown
- 1971-05-24 AR AR235756A patent/AR195267A1/en active
- 1971-05-24 NO NO1945/71A patent/NO141164C/en unknown
- 1971-05-24 DK DK251071A patent/DK133679C/en active
- 1971-05-25 RO RO7100078134A patent/RO62689A/en unknown
- 1971-05-25 CY CY829A patent/CY829A/en unknown
- 1971-05-25 BE BE767647A patent/BE767647A/xx not_active IP Right Cessation
- 1971-05-25 AT AT450471A patent/AT307617B/en not_active IP Right Cessation
- 1971-05-25 RO RO67014A patent/RO59157A/ro unknown
- 1971-05-25 FR FR7118932A patent/FR2100681B1/fr not_active Expired
- 1971-05-25 HU HUBA2591A patent/HU162205B/hu unknown
- 1971-05-25 CA CA113,784A patent/CA943128A/en not_active Expired
- 1971-05-25 GB GB1688071A patent/GB1301961A/en not_active Expired
- 1971-05-25 ES ES391532A patent/ES391532A1/en not_active Expired
- 1971-05-25 JP JP3524471A patent/JPS5538357B1/ja active Pending
- 1971-05-25 NL NLAANVRAGE7107175,A patent/NL172660C/en not_active IP Right Cessation
-
1972
- 1972-05-24 ES ES403125A patent/ES403125A1/en not_active Expired
- 1972-05-24 ES ES403124A patent/ES403124A1/en not_active Expired
- 1972-05-24 ES ES403126A patent/ES403126A1/en not_active Expired
-
1973
- 1973-09-14 AR AR250097A patent/AR195946A1/en active
-
1975
- 1975-12-22 KE KE2592*UA patent/KE2592A/en unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| V1 | Lapsed because of non-payment of the annual fee |