ES407851A1 - Penicillins their production and their medicinal use - Google Patents

Penicillins their production and their medicinal use

Info

Publication number
ES407851A1
ES407851A1 ES407851A ES407851A ES407851A1 ES 407851 A1 ES407851 A1 ES 407851A1 ES 407851 A ES407851 A ES 407851A ES 407851 A ES407851 A ES 407851A ES 407851 A1 ES407851 A1 ES 407851A1
Authority
ES
Spain
Prior art keywords
see formula
carbon atoms
formula
group
compounds
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
Application number
ES407851A
Other languages
Spanish (es)
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer AG
Original Assignee
Bayer AG
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Bayer AG filed Critical Bayer AG
Publication of ES407851A1 publication Critical patent/ES407851A1/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/06—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D239/08—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine 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 directly attached in position 2
    • C07D239/10—Oxygen or sulfur atoms
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P21/00—Drugs for disorders of the muscular or neuromuscular system
    • A61P21/06—Anabolic agents
    • 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
    • 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
    • C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
    • C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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
    • C07D333/30—Hetero atoms other than halogen
    • C07D333/34—Sulfur atoms
    • 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
    • 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 System
    • 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

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Public Health (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Oncology (AREA)
  • Communicable Diseases (AREA)
  • Endocrinology (AREA)
  • Engineering & Computer Science (AREA)
  • Bioinformatics & Cheminformatics (AREA)
  • Neurology (AREA)
  • Orthopedic Medicine & Surgery (AREA)
  • Physical Education & Sports Medicine (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Fodder In General (AREA)

Abstract

Procedure for obtaining penicillins, of general formula I **(See formula)** in which A represents a group **(See formula)** X represents a group (see formula), And a group (see formula), Z a group (see formula), Q1 a group (see formula) and Q2 a group **(See formula)** in which formulas represent: R a linear or branched alkyl radical with up to 5 carbon atoms, hydrogen, provided that X is not at the same time -CO-, alkyl with up to 10 carbon atoms, cycloalkenyl with up to 10 carbon atoms, cycloalkenyl with up to 10 carbon atoms, vinyl, aryl vinyl, monohalogeno lower alkyl, dihalogeno lower alkyl, trihalogeno lower alkyl H2N-, R-NH-, (see formula), aryl-NH-, arylalkyl (lower) -amino, alkoxy with up to 8 carbon atoms, provided that X is not at the same time -SO2-, aralkoxy with up to 8 carbon atoms, provided that X is not at the same time -SO2-, cycloalkoxy with up to 7 carbon atoms, provided that X is not at the same time -SO2-, aryloxy, provided that X is not at the same time -SO2-, one of the groups ROV-, RSV-, N = CV-, RO-CO-V-, H2N-CO-V-, R-NH-CO-V-, (see formula), **(See formula)** V a bivalent organic radical with 1 to 3 carbon atoms, n an integer from 0 to 2 inclusive, R2 and R3 each represent hydrogen, alkyl and alkenyl each with up to 8 carbon, vinyl, ring, propenyl, cycloalkyl atoms And cycloalkenyl each having up to 6 carbon atoms, mono-, di- and trihalogenoalkyl or aryl, R4, R5 and R6 each represent hydrogen, nitro, nitrile, (see formula), (see formula), R-CO-NH-, RO-CO-, R-CO-O-, R-, RO-, H2N-SO2-, chlorine, bromine, iodine, fluorine or trifluoromethyl, and G represents hydrogen or R, meaning the arrow on the divalent intermediate piece (see formula) that the ligation of two atoms caused by the two free valences of this intermediate piece is not arbitrary, but must proceed in the way characterized by the arrow, B is a group of the formula **(See formula)** R7, R8 and R9 represent hydrogen, halogen, R-, R-O-, R-S-, R-SO-, R-SO2-, nitro, (see formula), R-CO-NH-, HO, R-CO-O-, having R the meaning indicated above, and its non-toxic pharmaceutically acceptable salts, the penicillins of the general formula I and their non-toxic pharmaceutically tolerable salts being able to present, regarding the chirality center (see formula), in the two possible configurations R and S and as mixtures of the resulting diastereomers; characterized in that a compound chosen from compounds of general formula II is reacted **(See formula)** and the condensation products of compounds of the general formula II with carbonyl compounds, such as acetone, chosen from compounds of the general formula III **(See formula)** and compounds of general formulas IV and V **(See formula)** in which formulas B and G have the meanings indicated above and R10, R11 and R12 represent alkyl with up to 6 carbon atoms, with compounds chosen from the general formulas VI, VII, VIII, IX and X **(See formula)** in which A, Q1, Q2, R1, R2, X, Y and Z have the meanings indicated above, and W represents halogen, azide or a group (see formula), the reaction being carried out, in the case of the application of the compounds of the general formulas II and III, in anhydrous or aqueous solvents, in the presence of a base, and in the case of the application of compounds of the formulas General IV and V, in anhydrous and hydroxyl group-free solvents with or without the addition of a base, at temperatures in the range of about -50º to + 50ºC. (Machine-translation by Google Translate, not legally binding)
ES407851A 1971-10-23 1972-10-21 Penicillins their production and their medicinal use Expired ES407851A1 (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE2152967A DE2152967C3 (en) 1971-10-23 1971-10-23 Acylureidopenicillins

Publications (1)

Publication Number Publication Date
ES407851A1 true ES407851A1 (en) 1975-10-01

Family

ID=5823251

Family Applications (1)

Application Number Title Priority Date Filing Date
ES407851A Expired ES407851A1 (en) 1971-10-23 1972-10-21 Penicillins their production and their medicinal use

Country Status (31)

Country Link
JP (2) JPS57843B2 (en)
AR (1) AR195805A1 (en)
AT (1) AT320152B (en)
BE (1) BE790440A (en)
BG (2) BG20813A3 (en)
CA (1) CA1019323A (en)
CH (1) CH579089A5 (en)
CS (1) CS188883B2 (en)
CY (1) CY947A (en)
DD (1) DD106044B3 (en)
DE (1) DE2152967C3 (en)
DK (1) DK134992C (en)
EG (1) EG10826A (en)
ES (1) ES407851A1 (en)
FI (1) FI56839C (en)
FR (1) FR2157908B1 (en)
GB (1) GB1392849A (en)
HK (1) HK18578A (en)
HU (1) HU167986B (en)
IE (1) IE37123B1 (en)
IL (1) IL40628A (en)
KE (1) KE2824A (en)
LU (1) LU66332A1 (en)
NO (1) NO143909C (en)
PH (1) PH9893A (en)
PL (2) PL93574B1 (en)
RO (2) RO60670A (en)
SE (1) SE412236B (en)
SU (1) SU527139A3 (en)
YU (1) YU264072A (en)
ZA (1) ZA727473B (en)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3974141A (en) * 1971-10-23 1976-08-10 Bayer Aktiengesellschaft Penicillins
US3983105A (en) * 1971-10-23 1976-09-28 Bayer Aktiengesellschaft Penicillins
US3974142A (en) * 1971-10-23 1976-08-10 Bayer Aktiengesellschaft Penicillins
US3978056A (en) * 1971-10-23 1976-08-31 Bayer Aktiengesellschaft Penicillins
US4009272A (en) * 1971-10-23 1977-02-22 Bayer Aktiengesellschaft Penicillins
US3972869A (en) * 1971-10-23 1976-08-03 Bayer Aktiengesellschaft Penicillins
US3972870A (en) * 1971-10-23 1976-08-03 Bayer Aktiengesellschaft Penicillins
NL175419C (en) * 1971-10-23 1984-11-01 Bayer Ag METHOD FOR PREPARING OR MANUFACTURING ANTIBIOTIC ACTIVE PHARMACEUTICAL PREPARATIONS AND METHOD FOR PREPARING ANTIBIOTIC ACTIVE ALPHA-SUBSTITUTED 6- (ALFA- (3-ACYLUREIDO) -PETYL-ACIDYL-ACIDYL-ACIDYL)
DE2258973A1 (en) * 1972-12-01 1974-06-06 Bayer Ag PENICILLIN, THE METHOD FOR MANUFACTURING IT AND THEIR USE AS A MEDICINAL PRODUCT
JPS587637B2 (en) * 1973-12-27 1983-02-10 住友化学工業株式会社 Shinkipenicillin no Seihou
DE2407715C2 (en) * 1974-02-18 1982-12-02 Bayer Ag, 5090 Leverkusen Cephalosporins, processes for their production, as well as pharmaceuticals
IL47168A (en) * 1974-05-09 1979-07-25 Toyama Chemical Co Ltd Mono or dioxo piperazino(thio)carbonylamino derivatives ofpenicillins and cephalosporins and process for producing the same
DE2525541C2 (en) * 1975-06-07 1984-01-12 Bayer Ag, 5090 Leverkusen β-lactam antibiotics, processes for their preparation and pharmaceuticals containing them
DE2810083A1 (en) 1978-03-08 1979-09-20 Bayer Ag BETA-LACTAM COMPOUNDS
GB0420722D0 (en) * 2004-09-17 2004-10-20 Addex Pharmaceuticals Sa Novel allosteric modulators
EP1780213A1 (en) * 2005-10-27 2007-05-02 3M Innovative Properties Company Silicon-urea-azolides, their preparation and use in the preparation of silicones with isocyanate terminal groups
TWI417095B (en) 2006-03-15 2013-12-01 Janssen Pharmaceuticals Inc 1,4-disubstituted 3-cyano-pyridone derivatives and their use as positive allosteric modulators of mglur2-receptors
TW200845978A (en) 2007-03-07 2008-12-01 Janssen Pharmaceutica Nv 3-cyano-4-(4-tetrahydropyran-phenyl)-pyridin-2-one derivatives
TW200900065A (en) 2007-03-07 2009-01-01 Janssen Pharmaceutica Nv 3-cyano-4-(4-pyridinyloxy-phenyl)-pyridin-2-one derivatives
TW200922566A (en) 2007-09-14 2009-06-01 Ortho Mcneil Janssen Pharm 1,3 disubstituted 4-(aryl-X-phenyl)-1H-pyridin-2-ones
JP5433579B2 (en) 2007-09-14 2014-03-05 ジャンセン ファーマシューティカルズ， インコーポレイテッド． 1,3-disubstituted-4-phenyl-1H-pyridin-2-one
TWI445532B (en) 2007-09-14 2014-07-21 Janssen Pharmaceuticals Inc 1',3'-disubstituted-4-phenyl-3,4,5,6-tetrahydro-2h, 1'h-[1,4'] bipyridinyl-2'-ones
ES2637794T3 (en) 2007-11-14 2017-10-17 Janssen Pharmaceuticals, Inc. Imidazo [1,2-A] pyridine derivatives and their use as positive allosteric modulators of MGLUR2 receptors
CA2735764C (en) 2008-09-02 2016-06-14 Ortho-Mcneil-Janssen Pharmaceuticals, Inc. 3-azabicyclo[3.1.0]hexyl derivatives as modulators of metabotropic glutamate receptors
ES2466341T3 (en) 2008-10-16 2014-06-10 Janssen Pharmaceuticals, Inc. Indole and benzomorpholine derivatives as modulators of metabotropic glutamate receptors
WO2010060589A1 (en) 2008-11-28 2010-06-03 Ortho-Mcneil-Janssen Pharmaceuticals, Inc. Indole and benzoxazine derivatives as modulators of metabotropic glutamate receptors
SG176018A1 (en) 2009-05-12 2011-12-29 Janssen Pharmaceuticals Inc 1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
MY153913A (en) 2009-05-12 2015-04-15 Janssen Pharmaceuticals Inc 7-aryl-1,2,4-triazolo[4,3-a]pyridine derivatives and their use as positive allosteric modulators of mglur2 receptors
MX2011011964A (en) 2009-05-12 2012-02-23 Janssen Pharmaceuticals Inc 1,2,4-triazolo [4,3-a] pyridine derivatives and their use for the treatment or prevention of neurological and psychiatric disorders.
KR102102972B1 (en) * 2009-06-10 2020-04-22 테크필즈 바이오켐 코., 엘티디. High penetration compositions or prodrugs of antimicrobials and antimicrobial-related compounds
ES2536433T3 (en) 2010-11-08 2015-05-25 Janssen Pharmaceuticals, Inc. 1,2,4-Triazolo [4,3-a] pyridine derivatives and their use as positive allosteric modulators of mGluR2 receptors
PL2649069T3 (en) 2010-11-08 2016-01-29 Janssen Pharmaceuticals Inc 1,2,4-TRIAZOLO[4,3-a]PYRIDINE DERIVATIVES AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
JP5852666B2 (en) 2010-11-08 2016-02-03 ジヤンセン・フアーマシユーチカルズ・インコーポレーテツド 1,2,4-Triazolo [4,3-a] pyridine derivatives and their use as positive allosteric modulators of the mGluR2 receptor
JO3368B1 (en) 2013-06-04 2019-03-13 Janssen Pharmaceutica Nv 6,7-DIHYDROPYRAZOLO[1,5-a]PYRAZIN-4(5H)-ONE COMPOUNDS AND THEIR USE AS NEGATIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
JO3367B1 (en) 2013-09-06 2019-03-13 Janssen Pharmaceutica Nv 1,2,4-TRIAZOLO[4,3-a]PYRIDINE COMPOUNDS AND THEIR USE AS POSITIVE ALLOSTERIC MODULATORS OF MGLUR2 RECEPTORS
DK3096790T3 (en) 2014-01-21 2019-10-07 Janssen Pharmaceutica Nv COMBINATIONS INCLUDING POSITIVE ALLOSTERIC MODULATORS OR ORTHOSTERIC AGONISTS OF METABOTROP GLUTAMATERG SUBTYPE 2 RECEPTOR AND APPLICATION OF THESE
UA127921C2 (en) 2014-01-21 2024-02-14 Янссен Фармацевтика Нв Combinations containing positive allosteric modulators or orthosteric agonists of metabotropic glutamatergic receptor subtype 2 and their use

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1770620A1 (en) * 1968-06-12 1971-11-11 Bayer Ag New penicillins

Also Published As

Publication number Publication date
CY947A (en) 1978-06-23
YU264072A (en) 1982-06-18
DE2152967A1 (en) 1973-05-03
PL93574B1 (en) 1977-06-30
PH9893A (en) 1976-06-08
EG10826A (en) 1976-12-31
AR195805A1 (en) 1973-11-09
DD106044B3 (en) 1990-07-18
AU4806472A (en) 1974-04-26
ZA727473B (en) 1973-07-25
DK134992C (en) 1977-07-18
IE37123L (en) 1973-04-23
RO63066A (en) 1978-06-15
FR2157908A1 (en) 1973-06-08
IL40628A (en) 1976-08-31
PL89056B1 (en) 1976-10-30
DE2152967B2 (en) 1981-02-19
SU527139A3 (en) 1976-08-30
BG20813A3 (en) 1975-12-20
FR2157908B1 (en) 1976-03-19
RO60670A (en) 1976-10-15
NO143909C (en) 1981-05-06
JPS4849787A (en) 1973-07-13
LU66332A1 (en) 1973-01-23
JPS4849910A (en) 1973-07-14
HK18578A (en) 1978-04-14
JPS55391B2 (en) 1980-01-08
NO143909B (en) 1981-01-26
JPS57843B2 (en) 1982-01-08
CS188883B2 (en) 1979-03-30
BE790440A (en) 1973-04-24
CH579089A5 (en) 1976-08-31
DK134992B (en) 1977-02-21
BG21609A3 (en) 1976-07-20
GB1392849A (en) 1975-04-30
IE37123B1 (en) 1977-05-11
IL40628A0 (en) 1972-12-29
FI56839C (en) 1980-04-10
DE2152967C3 (en) 1981-11-19
DD106044A5 (en) 1974-05-20
FI56839B (en) 1979-12-31
HU167986B (en) 1976-02-28
AT320152B (en) 1975-01-27
CA1019323A (en) 1977-10-18
KE2824A (en) 1978-04-07
SE412236B (en) 1980-02-25

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