RO81225B - Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanic - Google Patents
Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanicInfo
- Publication number
- RO81225B RO81225B RO102404A RO10240480A RO81225B RO 81225 B RO81225 B RO 81225B RO 102404 A RO102404 A RO 102404A RO 10240480 A RO10240480 A RO 10240480A RO 81225 B RO81225 B RO 81225B
- Authority
- RO
- Romania
- Prior art keywords
- beta
- general formula
- substituted
- benzyl
- derivatives
- Prior art date
Links
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
-
- 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
- C07D499/04—Preparation
- C07D499/08—Modification of a carboxyl radical directly attached in position 2, e.g. esterification
-
- 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
- C07D499/74—Compounds with an amino radical acylated by carboxylic acids, attached in position 6 with carbocyclic rings directly attached to the carboxamido radical
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Catalysts (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Abstract
Procedeul pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpencilanic cu formula generala I: (vezi formula) sau a unei sari acceptabile farmaceutic, în care Y reprezinta R sau R3, R reprezinta 1-hidroxi-3-fenil-propil, alchilsulfoniloxi cu 1...4 atomi de carbon în grupa alchil, fenilsulfoniloximetil sau fenilsulfoniloximetilsubstituit cu metil, metoxi, fluor, clor, brom sau trifluormetil, R2 reprezinta O - OR R4 - CH - în care R3 reprezinta sulf, hidrogen, alcoxicarbonil, cu 2...4 atomi de carbon, benzil, fenilsulfonil substituit cu un radical amino, fluormetil, iar n reprezinta 2, consta în îndepartarea grupei benzil din compusul cu formula generalp II: (vezi formula) în care Y si n au semnificatiile de mai sus, cu conditia ca atunci cînd Y reprezinta R1, n care valoarea zero, prin hidrogenare în prezenta unui catalizator de paladiu în mediu de solvent organic inert ales dintre benzen, toluen sau maestecurile acestora la temepratura ambinata dupa care produsul astfel obtinut se transforma într-o sare bazica a acestuia prin metode cunoscute.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/086,864 US4287181A (en) | 1979-10-22 | 1979-10-22 | Derivatives of 6β-hydroxyalkylpenicillanic acids as β-lactamase inhibitors |
Publications (2)
Publication Number | Publication Date |
---|---|
RO81225A RO81225A (ro) | 1983-02-15 |
RO81225B true RO81225B (ro) | 1983-02-28 |
Family
ID=22201393
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RO102404A RO81225B (ro) | 1979-10-22 | 1980-10-22 | Procedeu pentru prepararea unor derivati ai acidului 6-beta-hidroxialchilpenicilanic |
RO108549A RO86176B (ro) | 1979-10-22 | 1980-10-22 | Procedeu pentru prepararea unor esteri ai acidului 6-beta-hidroxialchilpenicilanic |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
RO108549A RO86176B (ro) | 1979-10-22 | 1980-10-22 | Procedeu pentru prepararea unor esteri ai acidului 6-beta-hidroxialchilpenicilanic |
Country Status (38)
Country | Link |
---|---|
US (1) | US4287181A (ro) |
JP (2) | JPS5665892A (ro) |
KR (1) | KR840000797B1 (ro) |
AR (1) | AR227164A1 (ro) |
AT (2) | AT369372B (ro) |
AU (1) | AU519578B2 (ro) |
BE (1) | BE885812A (ro) |
BG (2) | BG38639A3 (ro) |
CA (2) | CA1144159A (ro) |
CH (2) | CH646175A5 (ro) |
CS (2) | CS219291B2 (ro) |
DD (1) | DD154542A5 (ro) |
DE (1) | DE3039504C2 (ro) |
DK (1) | DK389480A (ro) |
ES (1) | ES496166A0 (ro) |
FI (1) | FI71156C (ro) |
FR (1) | FR2467852A1 (ro) |
GB (3) | GB2061930B (ro) |
GR (1) | GR70714B (ro) |
GT (1) | GT198065892A (ro) |
HU (1) | HU183236B (ro) |
IE (3) | IE51027B1 (ro) |
IL (1) | IL61307A (ro) |
IN (1) | IN154918B (ro) |
IT (1) | IT1149259B (ro) |
LU (1) | LU82880A1 (ro) |
MX (1) | MX6094E (ro) |
NL (1) | NL183358C (ro) |
NO (1) | NO159019C (ro) |
NZ (1) | NZ195307A (ro) |
PH (5) | PH16219A (ro) |
PL (2) | PL129534B1 (ro) |
PT (1) | PT71946B (ro) |
RO (2) | RO81225B (ro) |
SE (1) | SE451455B (ro) |
SU (2) | SU1122227A3 (ro) |
YU (2) | YU41743B (ro) |
ZA (1) | ZA806452B (ro) |
Families Citing this family (32)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
IE49768B1 (en) * | 1979-05-21 | 1985-12-11 | Leo Pharm Prod Ltd | 6beta-halopenicillanic acid derivatives |
GB2076812A (en) * | 1980-05-22 | 1981-12-09 | Ciba Geigy Ag | Penam-dioxide compounds, processes for their manufacture, and their use |
US4444687A (en) * | 1981-06-08 | 1984-04-24 | Bristol-Myers Company | 2β-Chloromethyl-2α-methylpenam-3α-carboxylic acid sulfone methylene diol mixed esters |
ZA826687B (en) * | 1981-09-14 | 1983-07-27 | Pfizer | Beta-lactamase inhibiting 2-beta-substituted-2-alpha-methyl 5(r)penam-3-alpha-carboxylic acid 1,1-dioxides and intermediates therefor |
US4351840A (en) | 1981-09-18 | 1982-09-28 | Pfizer Inc. | Antibacterial esters of resorcinol with ampicillin and penicillanic acid 1,1-dioxide derivatives |
JPS58109490A (ja) * | 1981-12-21 | 1983-06-29 | Sankyo Co Ltd | ペニシリン誘導体 |
RO87705A (ro) * | 1982-01-11 | 1985-10-31 | Pfizer Inc,Us | Procedeu pentru prepararea unor derivati ai acidului 6-aminoalchilpenicilanic 1,1-dioxid |
US4452796A (en) * | 1982-06-14 | 1984-06-05 | Pfizer Inc. | 6-Aminoalkylpenicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
US4377590A (en) * | 1982-05-10 | 1983-03-22 | Pfizer Inc. | Derivatives of ampicillin and amoxicillin with beta-lactamase inhibitors |
US4502990A (en) * | 1983-06-06 | 1985-03-05 | Pfizer Inc. | Process for 6-(aminomethyl)penicillanic acid 1,1-dioxide and derivatives thereof |
US4588527A (en) * | 1983-06-06 | 1986-05-13 | Pfizer Inc. | Process for preparing penicillanic acid 1,1-dioxide derivatives |
US4536393A (en) * | 1983-06-06 | 1985-08-20 | Pfizer Inc. | 6-(Aminomethyl)penicillanic acid 1,1-dioxide esters and intermediates therefor |
US4499017A (en) * | 1983-06-06 | 1985-02-12 | Pfizer Inc. | Beta-lactamase inhibiting 6-(alkoxyamino-methyl) penicillanic acid 1,1-dioxide and derivatives |
US4502988A (en) * | 1983-08-08 | 1985-03-05 | Eli Lilly And Company | Oxidation process |
US4826833A (en) * | 1984-01-30 | 1989-05-02 | Pfizer Inc. | 6-(Substituted)methylene-penicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof |
EP0150984B1 (en) * | 1984-01-30 | 1991-09-11 | Pfizer Inc. | 6-(substituted) methylenepenicillanic and 6-(substituted) hydroxymethylpenicillanic acids and derivatives thereof |
ES8604972A1 (es) * | 1984-01-30 | 1986-02-16 | Pfizer | Un procedimiento para la preparacion de acidos 6-metilen-(sustituido) penicilanicos y derivados de los mismos. |
US5015473A (en) * | 1984-01-30 | 1991-05-14 | Pfizer Inc. | 6-(substituted)methylenepenicillanic and 6-(substituted)hydroxymethylpenicillanic acids and derivatives thereof |
US4503040A (en) * | 1984-02-27 | 1985-03-05 | Pfizer Inc. | 6-(Aminoacyloxymethyl)penicillanic acid 1,1-dioxides as beta-lactamase inhibitors |
US4847247A (en) * | 1984-07-30 | 1989-07-11 | Merck & Co., Inc. | Penicillin derivatives as anti-inflammatory and antidegenerative agents |
US4590073A (en) * | 1984-10-22 | 1986-05-20 | Pfizer Inc. | 6-substituted penicillanic acid 1,1-dioxide compounds |
US4591459A (en) * | 1984-12-03 | 1986-05-27 | Pfizer Inc. | Intermediates for 6-(aminoacyloxymethyl) penicillanic acid 1,1-dioxides |
US4675186A (en) | 1985-04-18 | 1987-06-23 | Pfizer Inc. | 6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives |
US4762921A (en) * | 1985-04-18 | 1988-08-09 | Pfizer Inc. | 6-(1-acyl-1-hydroxymethyl)penicillanic acid derivatives |
US4613462A (en) * | 1985-07-02 | 1986-09-23 | Pfizer, Inc. | 6-substituted penicillanic acid 1,1-dioxide compounds |
US4782050A (en) * | 1987-01-27 | 1988-11-01 | Pfizer Inc. | 6-beta(substituted)-(S)-hydroxymethylpenicillanic acids and derivatives thereof |
ES2031589T3 (es) * | 1987-01-27 | 1992-12-16 | Pfizer Inc. | Acidos 6-beta-(sustituyente)-(s)-hidroximetil-penicilanicos y sus derivados. |
US6395726B1 (en) | 1999-01-26 | 2002-05-28 | American Cyanamid Company | 3,6-disubstituted penam sulfone derivatives |
PA8579701A1 (es) * | 2002-08-23 | 2005-05-24 | Pfizer Prod Inc | Profarmaco inhibidor de beta-lactamasa |
CA2528065A1 (en) * | 2003-06-05 | 2004-12-16 | Pfizer Products Inc. | Beta-lactamase inhibitor prodrug |
ES2398258T3 (es) * | 2007-03-09 | 2013-03-14 | Otsuka Chemical Co., Ltd. | Procedimiento para producir un compuesto 6-hidroxieltil penam |
CN109422765B (zh) * | 2017-09-05 | 2020-08-28 | 香港理工大学深圳研究院 | C类β-内酰胺酶抑制剂及其制备方法和应用 |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5749555B2 (ro) * | 1973-04-04 | 1982-10-22 | ||
US4207323A (en) * | 1975-11-21 | 1980-06-10 | Merck & Co., Inc. | 6-Substituted methyl penicillins, derivatives and analogues thereof |
US4053468A (en) * | 1976-02-25 | 1977-10-11 | Smithkline Corporation | Process for preparing 7-oxo cephalosporins and 6-oxo penicillins |
US4093625A (en) * | 1976-08-09 | 1978-06-06 | Massachusetts Institute Of Technology | 6-Sulfur analogs of penicillins and cephalosporins |
US4123539A (en) * | 1977-12-29 | 1978-10-31 | Merck & Co., Inc. | 6-Ethylpenicillanic acid |
US4272439A (en) * | 1978-06-02 | 1981-06-09 | Schering Corporation | 6-(Substituted-hydroxymethylene penams) |
JPS5598186A (en) * | 1979-01-10 | 1980-07-25 | Beecham Group Ltd | Manufacture of penicillin derivative |
GB2076812A (en) * | 1980-05-22 | 1981-12-09 | Ciba Geigy Ag | Penam-dioxide compounds, processes for their manufacture, and their use |
-
1979
- 1979-10-22 US US06/086,864 patent/US4287181A/en not_active Expired - Lifetime
-
1980
- 1980-09-12 DK DK389480A patent/DK389480A/da not_active Application Discontinuation
- 1980-10-08 IN IN736/DEL/80A patent/IN154918B/en unknown
- 1980-10-11 GR GR63135A patent/GR70714B/el unknown
- 1980-10-16 GB GB33342A patent/GB2061930B/en not_active Expired
- 1980-10-17 GT GT198065892A patent/GT198065892A/es unknown
- 1980-10-20 CS CS807098A patent/CS219291B2/cs unknown
- 1980-10-20 YU YU2676/80A patent/YU41743B/xx unknown
- 1980-10-20 PH PH24748A patent/PH16219A/en unknown
- 1980-10-20 CA CA000362762A patent/CA1144159A/en not_active Expired
- 1980-10-20 NZ NZ195307A patent/NZ195307A/en unknown
- 1980-10-20 JP JP14677480A patent/JPS5665892A/ja active Granted
- 1980-10-20 SE SE8007354A patent/SE451455B/sv not_active IP Right Cessation
- 1980-10-20 AR AR282932A patent/AR227164A1/es active
- 1980-10-20 DE DE3039504A patent/DE3039504C2/de not_active Expired
- 1980-10-20 AT AT0518580A patent/AT369372B/de not_active IP Right Cessation
- 1980-10-20 IL IL61307A patent/IL61307A/xx unknown
- 1980-10-21 PL PL1980227420A patent/PL129534B1/pl unknown
- 1980-10-21 IE IE293/85A patent/IE51027B1/en unknown
- 1980-10-21 IE IE2174/80A patent/IE51026B1/en unknown
- 1980-10-21 PT PT71946A patent/PT71946B/pt unknown
- 1980-10-21 PL PL1980235907A patent/PL129638B1/pl unknown
- 1980-10-21 FR FR8022477A patent/FR2467852A1/fr active Granted
- 1980-10-21 BE BE0/202544A patent/BE885812A/fr not_active IP Right Cessation
- 1980-10-21 IE IE2229/85A patent/IE51028B1/en unknown
- 1980-10-21 HU HU802552A patent/HU183236B/hu not_active IP Right Cessation
- 1980-10-21 MX MX809112U patent/MX6094E/es unknown
- 1980-10-21 AU AU63548/80A patent/AU519578B2/en not_active Ceased
- 1980-10-21 BG BG8361372A patent/BG38639A3/xx unknown
- 1980-10-21 NO NO803136A patent/NO159019C/no unknown
- 1980-10-21 KR KR1019800004041A patent/KR840000797B1/ko active
- 1980-10-21 SU SU802999190A patent/SU1122227A3/ru active
- 1980-10-21 IT IT25488/80A patent/IT1149259B/it active
- 1980-10-21 FI FI803311A patent/FI71156C/fi not_active IP Right Cessation
- 1980-10-21 ZA ZA00806452A patent/ZA806452B/xx unknown
- 1980-10-21 BG BG8049416A patent/BG35189A3/xx unknown
- 1980-10-22 ES ES496166A patent/ES496166A0/es active Granted
- 1980-10-22 NL NLAANVRAGE8005810,A patent/NL183358C/xx not_active IP Right Cessation
- 1980-10-22 RO RO102404A patent/RO81225B/ro unknown
- 1980-10-22 CH CH788180A patent/CH646175A5/fr not_active IP Right Cessation
- 1980-10-22 RO RO108549A patent/RO86176B/ro unknown
- 1980-10-22 LU LU82880A patent/LU82880A1/fr unknown
- 1980-10-22 DD DD80224691A patent/DD154542A5/de unknown
-
1981
- 1981-06-05 CS CS814222A patent/CS219292B2/cs unknown
- 1981-08-26 SU SU813325756A patent/SU1026654A3/ru active
- 1981-11-06 PH PH26449A patent/PH17317A/en unknown
- 1981-11-06 PH PH26450A patent/PH17458A/en unknown
- 1981-11-06 PH PH26451A patent/PH18316A/en unknown
- 1981-11-06 PH PH26448A patent/PH17315A/en unknown
-
1982
- 1982-01-13 AT AT0010882A patent/AT374479B/de not_active IP Right Cessation
- 1982-12-17 CA CA000418062A patent/CA1163924A/en not_active Expired
-
1983
- 1983-03-21 YU YU671/83A patent/YU42075B/xx unknown
- 1983-06-21 GB GB08316829A patent/GB2128986B/en not_active Expired
- 1983-06-21 GB GB08316830A patent/GB2129421B/en not_active Expired
-
1984
- 1984-03-06 CH CH1089/84A patent/CH647242A5/fr not_active IP Right Cessation
-
1986
- 1986-02-06 JP JP61024914A patent/JPS61178988A/ja active Pending
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