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IL102520A - 8-vinyl-, 8-propenyl and 8-ethinyl-quinolone- carboxylic acids, their preparation, intermediates therefor and pharmaceutical compositions containing them - Google Patents

8-vinyl-, 8-propenyl and 8-ethinyl-quinolone- carboxylic acids, their preparation, intermediates therefor and pharmaceutical compositions containing them

Info

Publication number
IL102520A
IL102520A IL102520A IL10252092A IL102520A IL 102520 A IL102520 A IL 102520A IL 102520 A IL102520 A IL 102520A IL 10252092 A IL10252092 A IL 10252092A IL 102520 A IL102520 A IL 102520A
Authority
IL
Israel
Prior art keywords
methyl
alkyl
atoms
represents hydrogen
halogen
Prior art date
Application number
IL102520A
Other versions
IL102520A0 (en
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 IL102520A0 publication Critical patent/IL102520A0/en
Publication of IL102520A publication Critical patent/IL102520A/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
    • C07D215/20—Oxygen atoms
    • C07D215/22—Oxygen atoms attached in position 2 or 4
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
    • C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
    • C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen 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
    • C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C07D215/54—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3
    • C07D215/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen attached in position 3 with oxygen atoms in position 4
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/10—Anthelmintics
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/08—Bridged systems

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Tropical Medicine & Parasitology (AREA)
  • Communicable Diseases (AREA)
  • Oncology (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Quinoline Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Peptides Or Proteins (AREA)
  • Indole Compounds (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Paints Or Removers (AREA)

Abstract

Quinolonecarboxylic acid derivatives of the formula X1O FCOO-R2 YN X2R1 in which R1 represents straight-chain or branched C1-C4-alkyl which is optionally substituted by hydroxyl, halogen or C1-C3-alkoxy, or represents optionally halogen- or C1-C3-alkyl-substituted C3-C6 cycloalkyl, C2-C4-alkenyl, furthermore represents C1-C3-alkoxy, amino, monoalkylamino having 1 to 3 C atoms, dialkylamino having 2 to 6 C atoms, or phenyl which is optionally monosubstituted to trisubstituted by halogen, R2 represents hydrogen, alkyl having 1 to 4 carbon atoms or (5-methyl-2-oxo-1, 3-dioxol-4-yl)-methyl, X1 represents hydrogen, fluorine, chlorine, amino or methyl, X2 represents -C=CH-R3( R4 -C:C-R5 or -CH2CH=CH2, where R3 represents hydrogen, C1-C3-alkyl, C1-C3-alkoxy or alkoxymethyl having 1 to 3 C atoms in the alkoxy moiety, R4 represents hydrogen or halogen and R5 represents hydrogen, C1-C6-alkyl which is optionally monosubstituted to trisubstituted by halogen, or C2-C3-alkenyl, alkoxy having 1 to 3 C atoms, alkoxymethyl having 1 to 3 C atoms in the alkoxy moiety, halogen or trimethylsilyl, and Y represents where R6 represents hydrogen, optionally hydroxyl- or methoxy-substituted straight- chain or branched C1-C4-alkyl, cyclopropyl, oxoalkyl having 1 to 4 C atoms or acyl having 1 to 3 C atoms, R7 represents hydrogen, methyl, phenyl, thienyl or pyridyl, R8, R9 and R10 represents hydrogen or methyl, R9 R11 represents hydogen, methyl or -CH2-N R10 R12 represents hydrogen, methyl, amino, optionally hydroxyl-substituted alkyl- or dialkylamino having 1 or 2 C atoms in the alkyl moiety, aminomethyl, aminoethyl, optionally hydroxyl-substituted alkyl- or dialkylaminomethyl having 1 or 2 C atoms in the alkyl moiety or 1-imidazolyl, R13 represents hydrogen, hydroxyl, methoxy, methylthio or halogen, methyl or hydroxymethyl, R14 represents hydrogen or methyl, R15, R16, R17 represent hydrogen, methyl or ethyl, R18 represents hydroxyl, R16R16 NorCH2-N R17R17 R19 represents hydrogen, optionally hydroxyl-substituted C1-C3-alkyl, alkoxycarbonyl having 1 to 4 carbon atoms in the alkoxy moiety or C1-C3-acyl, R20 represents hydrogen, hydroxyl, R19 N R21 hydroxymethyl or R19 CH2-Nwhere R21 R21 denotes hydrogen or methyl, or Y represents halogen, A represents CH2, O or a direct bond and n represents 1 or 2, and their pharmaceutically acceptable hydrates and acid addition salts as well as the alkali metal salts, alkaline earth metal salts, silver salts and guanidinium salts. The compounds wherein Y is other then halogen have antibacterial activity.
IL102520A 1991-07-19 1992-07-16 8-vinyl-, 8-propenyl and 8-ethinyl-quinolone- carboxylic acids, their preparation, intermediates therefor and pharmaceutical compositions containing them IL102520A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE4123918A DE4123918A1 (en) 1991-07-19 1991-07-19 8-VINYL AND 8-ETHINYL-CHINOLON CARBONIC ACIDS

Publications (2)

Publication Number Publication Date
IL102520A0 IL102520A0 (en) 1993-01-14
IL102520A true IL102520A (en) 1997-07-13

Family

ID=6436512

Family Applications (1)

Application Number Title Priority Date Filing Date
IL102520A IL102520A (en) 1991-07-19 1992-07-16 8-vinyl-, 8-propenyl and 8-ethinyl-quinolone- carboxylic acids, their preparation, intermediates therefor and pharmaceutical compositions containing them

Country Status (22)

Country Link
EP (1) EP0523512B1 (en)
JP (1) JP3174405B2 (en)
KR (1) KR100240608B1 (en)
AT (1) ATE147733T1 (en)
AU (1) AU658901B2 (en)
CA (1) CA2073993A1 (en)
CZ (1) CZ282037B6 (en)
DE (2) DE4123918A1 (en)
DK (1) DK0523512T3 (en)
ES (1) ES2097835T3 (en)
FI (1) FI103043B1 (en)
GR (1) GR3022305T3 (en)
HU (1) HU219910B (en)
IE (1) IE80557B1 (en)
IL (1) IL102520A (en)
MX (1) MX9204110A (en)
NO (1) NO302886B1 (en)
PL (1) PL171910B1 (en)
RU (1) RU2077533C1 (en)
SK (1) SK219192A3 (en)
TW (1) TW201309B (en)
ZA (1) ZA925351B (en)

Families Citing this family (20)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE4121214A1 (en) * 1991-06-27 1993-01-14 Bayer Ag 7-AZAISOINDOLINYL CHINOLONE AND NAPHTHYRIDONE CARBONIC ACID DERIVATIVES
DE4230804A1 (en) * 1992-09-15 1994-03-17 Bayer Ag 7-isoindolinyl quinolone and naphthyridone derivatives
DE4303657A1 (en) * 1993-02-09 1994-08-11 Bayer Ag New quinolone and naphthyridonecarboxylic acid derivatives
KR950018003A (en) * 1993-12-09 1995-07-22 스미스클라인 비참 피엘씨 Novel quinolone derivatives and methods for their preparation
DE4418510A1 (en) * 1994-05-27 1995-11-30 Bayer Ag 1,9-bridged thiazolol [3,4-a] quinoline derivatives
DE4425659A1 (en) * 1994-07-20 1996-01-25 Bayer Ag New N1-diverse 6-fluoro-8-difluoromethoxy substituted quinolonecarboxylic acids
DE4427530A1 (en) * 1994-08-04 1996-02-08 Bayer Ag New 7-tri:cyclic amino-quinolone or naphthyridone derivs
CA2247020C (en) * 1996-02-23 2005-11-08 Bayer Aktiengesellschaft Possibly substituted 8-cyano-1-cyclopropyl-7-(2,8-diazabicyclo-[4.3.0]-nonan-8-yl)-6-fluoro-1,4-dihydro-4-oxo-3-quinolin carboxylic acids and their derivatives
ES2224235T3 (en) * 1996-04-19 2005-03-01 Wakunaga Pharmaceutical Co., Ltd. NEW DERIVATIVES OF THE PYRIDONACARBOXILIC ACID OR ITS ANTIBACTERIAL SALTS AND AGENTS CONTAINING THE SAME AS ACTIVE INGREDIENTS.
WO1998024781A1 (en) * 1996-12-04 1998-06-11 Daiichi Pharmaceutical Co., Ltd. Substituted aminomethylpyrrolidine derivatives
MY138335A (en) 1997-09-15 2009-05-29 Procter & Gamble Antimicrobial quinolones, their compositions and uses
AU2004272414B2 (en) 2003-09-10 2009-05-28 Kyorin Pharmaceutical Co., Ltd. 7-(4-substituted 3- cyclopropylaminomethyl-1- pyrrolidinyl) quinolonecarboxylic acid derivative
RU2420524C2 (en) * 2005-05-19 2011-06-10 Дайити Санкио Компани, Лимитед Tri- or tetpa-substituted-3-aminopyrrolidine derivatives
US7563805B2 (en) * 2005-05-19 2009-07-21 Daiichi Pharmaceutical Co., Ltd. Tri-, tetra-substituted-3-aminopyrrolidine derivative
US7842818B2 (en) 2005-09-28 2010-11-30 Daiichi Sankyo Company, Limited Process for preparation of tetrasubstituted 5-azaspiro[2.4]- heptane derivatives and optically active intermediates thereof
EP1999125A2 (en) 2006-03-28 2008-12-10 The Procter and Gamble Company A coupling process for preparing quinolone intermediates
WO2007110834A2 (en) 2006-03-28 2007-10-04 The Procter & Gamble Company Malate salts, and polymorphs of (3s,5s)-7-[3-amino-5-methyl-piperidinyl]-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid
EP2149571A4 (en) 2007-05-24 2010-09-01 Kyorin Seiyaku Kk MUTILINE DERIVATIVE HAVING CARBOXYLIC ACID STRUCTURE HETEROCYCLIC AROMATIC CORE SUBSTITUTED AT POSITION 14
CA3099610A1 (en) * 2018-05-09 2019-11-14 Bayer Animal Health Gmbh New quinoline derivatives
RU2757741C1 (en) * 2021-03-01 2021-10-21 Федеральное государственное бюджетное учреждение науки Институт химической биологии и фундаментальной медицины Сибирского отделения Российской академии наук (ИХБФМ СО РАН) Ciprofloxacin derivative with antibacterial activity against antibiotic-resistant strains of microorganisms

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4123536A (en) * 1977-12-14 1978-10-31 Warner-Lambert Company Dialkyl ({[3-(alkoxycarbonyl)-1,4-dihydro-4-oxo-8-quinolinyl]amino}methylene)propanedioates
DE3705621C2 (en) * 1986-02-25 1997-01-09 Otsuka Pharma Co Ltd Heterocyclic substituted quinolonecarboxylic acid derivatives
JPS62215572A (en) * 1986-03-17 1987-09-22 Kyorin Pharmaceut Co Ltd Quinolone carboxylic acid derivative
US5047538A (en) * 1990-04-12 1991-09-10 Warner-Lambert Company Quinolinecarboxylic acid antibacterial agents

Also Published As

Publication number Publication date
KR930002320A (en) 1993-02-22
NO302886B1 (en) 1998-05-04
FI923268L (en) 1993-01-20
TW201309B (en) 1993-03-01
PL171910B1 (en) 1997-06-30
EP0523512A1 (en) 1993-01-20
CZ282037B6 (en) 1997-04-16
CA2073993A1 (en) 1993-01-20
ZA925351B (en) 1993-04-28
JPH05262738A (en) 1993-10-12
AU1966392A (en) 1993-01-21
GR3022305T3 (en) 1997-04-30
MX9204110A (en) 1993-08-01
NO922639D0 (en) 1992-07-03
RU2077533C1 (en) 1997-04-20
FI103043B (en) 1999-04-15
IE80557B1 (en) 1998-09-23
AU658901B2 (en) 1995-05-04
HU9202349D0 (en) 1992-10-28
DK0523512T3 (en) 1997-06-30
IE922348A1 (en) 1993-01-27
ATE147733T1 (en) 1997-02-15
IL102520A0 (en) 1993-01-14
HUT61741A (en) 1993-03-01
NO922639L (en) 1993-01-20
FI103043B1 (en) 1999-04-15
DE59207880D1 (en) 1997-02-27
CZ219192A3 (en) 1993-02-17
KR100240608B1 (en) 2000-03-02
ES2097835T3 (en) 1997-04-16
HU219910B (en) 2001-09-28
DE4123918A1 (en) 1993-01-21
EP0523512B1 (en) 1997-01-15
JP3174405B2 (en) 2001-06-11
SK279221B6 (en) 1998-08-05
PL295331A1 (en) 1993-07-12
SK219192A3 (en) 1998-08-05
FI923268A0 (en) 1992-07-16

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Legal Events

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KB Patent renewed
KB Patent renewed
MM9K Patent not in force due to non-payment of renewal fees