YU45568B - PROCEDURE FOR OBTAINING BETA-LACTAM ANTIBIOTICS - Google Patents
PROCEDURE FOR OBTAINING BETA-LACTAM ANTIBIOTICSInfo
- Publication number
- YU45568B YU45568B YU173983A YU173983A YU45568B YU 45568 B YU45568 B YU 45568B YU 173983 A YU173983 A YU 173983A YU 173983 A YU173983 A YU 173983A YU 45568 B YU45568 B YU 45568B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- hydrogen
- group
- acyl
- sulfonation
- compound
- Prior art date
Links
- 239000003782 beta lactam antibiotic agent Substances 0.000 title abstract 2
- 238000000034 method Methods 0.000 title abstract 2
- 239000002132 β-lactam antibiotic Substances 0.000 title abstract 2
- 229940124586 β-lactam antibiotics Drugs 0.000 title abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 7
- 239000001257 hydrogen Substances 0.000 abstract 7
- -1 mercaptomethyl Chemical group 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 abstract 3
- 125000002252 acyl group Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000203 mixture Substances 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 abstract 2
- 238000007363 ring formation reaction Methods 0.000 abstract 2
- 238000006277 sulfonation reaction Methods 0.000 abstract 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003277 amino group Chemical group 0.000 abstract 1
- 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 150000001768 cations Chemical class 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 238000007796 conventional method Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 125000004970 halomethyl group Chemical group 0.000 abstract 1
- 150000002431 hydrogen Chemical class 0.000 abstract 1
- 125000002346 iodo group Chemical group I* 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 abstract 1
- 239000002798 polar solvent Substances 0.000 abstract 1
- 229910000027 potassium carbonate Inorganic materials 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- 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
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/10—Compounds having one or more C—Si linkages containing nitrogen having a Si-N linkage
-
- 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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/10—Nitrogen as only ring hetero atom
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Microbiology (AREA)
- General Chemical & Material Sciences (AREA)
- Bioinformatics & Cheminformatics (AREA)
- General Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
POSTUPAK ZA DOBIVANJE BETA-LAKTAMSKIH ANTIBIOTIKA opšte formule: u kojoj je: R1 acil ili vodonik ili sa -NH- grupom predstavlja zaštićenu amino grupu; R2 je vodonik; jedan od R3 i R4 je vodonik a drugi je vodonik ili alkil, cikloalkil ili fenil; pri čemu grupa može biti supstituisana sa halogenom ili metil, halometil, merkaptometil ili benzil grupom ili njenih trifenilmetiltio derivatom azidometil i aminometil grupom, ili je jedan od R3 i R4 vodonik a drugi je alkoksikarbonil, alken-1-il, alkin-1-il, 2-feniletenil ili 2-feniletinil; i M+ je vodonik ili katjon, na značen time, što se jedinjenje formule: u kojoj su R1, R3 i R4 kao što je definisano gore a V je odlazeća grupa kao što je metansulfonil, benzolsulfonil, toluolsulfonil, hloro bromo ili jodo, podvrgava sulfonovanju i obrazovanju prstena, pri čemu se pomenuto sulfonovanje vrši tretiranjem jedinjenja sa sumportrioksidnim kompleksom ili sa ekvivalentnim sredstvom za sulfonovanje u prisustvu takvog organskog rastvarača kao što je piridin ili smeše organskih rastvarača, poželjno smeše takvog polarnog rastvarača kao što je dimetilformamid i takvog halogenovanog ugljovodonika kao što je dihlormetan, dok se pomenuto obrazovanje prstena vrši tretiranjem sa takvom bazom kao što je kalijum-karbonat, i kada je R1 u dobivenom proizvodu vodonik, prevodi se pomenuti proizvod u njegov acil derivat, gde je R1 acil, konvencionalnim postupcima. Prijava sadrži još 29 patentnih zahteva.A process for the preparation of BETA-LACTAM ANTIBIOTICS of the general formula: wherein: R 1 is acyl or hydrogen or with an -NH- group represents a protected amino group; R2 is hydrogen; one of R3 and R4 is hydrogen and the other is hydrogen or alkyl, cycloalkyl or phenyl; wherein the group may be substituted by halogen or methyl, halomethyl, mercaptomethyl or benzyl group or its triphenylmethylthio derivative azidomethyl and aminomethyl group, or one of R3 and R4 is hydrogen and the other is alkoxycarbonyl, alken-1-yl, alkyn-1-yl , 2-phenylethenyl or 2-phenylethynyl; and M + is hydrogen or a cation, characterized in that the compound of formula: wherein R 1, R 3 and R 4 are as defined above and V is a leaving group such as methanesulfonyl, benzenesulfonyl, toluenesulfonyl, chloro bromo or iodo, is subjected to sulfonation and ring formation, said sulfonation being performed by treating the compound with a sulfortrioxide complex or equivalent sulfonating agent in the presence of such an organic solvent as pyridine or mixtures of organic solvents, preferably mixtures of such a polar solvent such as dimethylformamide and such is dichloromethane, while said ring formation is carried out by treatment with such a base as potassium carbonate, and when R 1 in the product obtained is hydrogen, said product is converted into its acyl derivative, where R 1 is acyl, by conventional methods. The application contains another 29 patent claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US11927680A | 1980-02-07 | 1980-02-07 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU173983A YU173983A (en) | 1984-04-30 |
| YU45568B true YU45568B (en) | 1992-07-20 |
Family
ID=22383507
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU173983A YU45568B (en) | 1980-02-07 | 1983-08-23 | PROCEDURE FOR OBTAINING BETA-LACTAM ANTIBIOTICS |
Country Status (10)
| Country | Link |
|---|---|
| BE (1) | BE887428A (en) |
| BG (2) | BG36785A3 (en) |
| CA (1) | CA1340253C (en) |
| CS (2) | CS244105B2 (en) |
| HU (1) | HU191029B (en) |
| PL (2) | PL126840B1 (en) |
| RO (1) | RO86528B (en) |
| SU (1) | SU1272981A3 (en) |
| YU (1) | YU45568B (en) |
| ZA (1) | ZA81808B (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1982001873A1 (en) * | 1980-12-05 | 1982-06-10 | Takeda Chemical Industries Ltd | 1-sulfo-2-oxoazetidine derivatives and process for their preparation |
| US4673739A (en) * | 1980-12-05 | 1987-06-16 | Takeda Chemical Industries, Ltd. | 4-carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
| US4782147A (en) * | 1980-12-05 | 1988-11-01 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
| US4675397A (en) * | 1980-12-05 | 1987-06-23 | Takeda Chemical Industries, Ltd. | 1-sulfo-2-oxoazetidine derivatives and their production |
| US4572801A (en) * | 1981-04-30 | 1986-02-25 | Takeda Chemical Industries, Ltd. | 4-Carbamoyloxymethyl-1-sulfo-2-oxoazetidine derivatives and their production |
-
1981
- 1981-02-06 SU SU813248001A patent/SU1272981A3/en active
- 1981-02-06 PL PL1981229569A patent/PL126840B1/en unknown
- 1981-02-06 RO RO111297A patent/RO86528B/en unknown
- 1981-02-06 PL PL1981234758A patent/PL128184B1/en unknown
- 1981-02-06 ZA ZA00810808A patent/ZA81808B/en unknown
- 1981-02-06 CS CS81909A patent/CS244105B2/en unknown
- 1981-02-06 CS CS849615A patent/CS244146B2/en unknown
- 1981-02-06 HU HU81296A patent/HU191029B/en unknown
- 1981-02-06 BG BG050700A patent/BG36785A3/en unknown
- 1981-02-06 BG BG061668A patent/BG36930A3/en unknown
- 1981-02-06 BE BE0/203736A patent/BE887428A/en not_active IP Right Cessation
-
1983
- 1983-08-23 YU YU173983A patent/YU45568B/en unknown
-
1996
- 1996-08-28 CA CA000617057A patent/CA1340253C/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| BG36930A3 (en) | 1985-02-15 |
| HU191029B (en) | 1986-12-28 |
| YU173983A (en) | 1984-04-30 |
| RO86528B (en) | 1985-04-01 |
| PL234758A1 (en) | 1982-08-02 |
| CS961584A2 (en) | 1985-08-31 |
| CS90981A2 (en) | 1985-09-17 |
| BE887428A (en) | 1981-08-06 |
| CS244105B2 (en) | 1986-07-17 |
| RO86528A (en) | 1985-03-15 |
| CA1340253C (en) | 1998-12-15 |
| HUT35669A (en) | 1985-07-29 |
| PL128184B1 (en) | 1984-01-31 |
| ZA81808B (en) | 1982-02-24 |
| CS244146B2 (en) | 1986-07-17 |
| SU1272981A3 (en) | 1986-11-23 |
| PL126840B1 (en) | 1983-09-30 |
| BG36785A3 (en) | 1985-01-15 |
| PL229569A1 (en) | 1982-05-24 |
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