PH26519A - Novel antimicrobial fluoroquinolonyl cephems - Google Patents

Novel antimicrobial fluoroquinolonyl cephems Download PDF

Info

Publication number: PH26519A
Authority: PH; Philippines
Prior art keywords: amino; oxo; acetyl; carbonyl; methyl
Prior art date: 1988-10-24

Application number

PH39400A

Other languages

English (en)

Inventor

Demuth Thomas Prosser Jr

Ronald Eugene White

Original Assignee

Norwich Eaton Pharma

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.)

1988-10-24

Filing date

1989-10-24

Publication date

1992-08-07

1989-10-24 Application filed by Norwich Eaton Pharma filed Critical Norwich Eaton Pharma

1992-08-07 Publication of PH26519A publication Critical patent/PH26519A/en

Links

150000001782 cephems Chemical class 0.000 title abstract description 40
230000000845 anti-microbial effect Effects 0.000 title abstract description 17
150000001875 compounds Chemical class 0.000 claims description 15
150000002148 esters Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 6
150000004677 hydrates Chemical class 0.000 claims description 3
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 70
125000000623 heterocyclic group Chemical group 0.000 abstract description 30
229910052739 hydrogen Inorganic materials 0.000 abstract description 30
239000001257 hydrogen Substances 0.000 abstract description 26
229910052736 halogen Inorganic materials 0.000 abstract description 15
150000002367 halogens Chemical class 0.000 abstract description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 9
125000003545 alkoxy group Chemical group 0.000 abstract description 8
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract description 6
125000004093 cyano group Chemical group *C#N 0.000 abstract description 3
GLUUGHFHXGJENI-UHFFFAOYSA-N diethylenediamine Natural products C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract description 3
NGXSWUFDCSEIOO-UHFFFAOYSA-N pyrrolidin-3-amine Chemical compound NC1CCNC1 NGXSWUFDCSEIOO-UHFFFAOYSA-N 0.000 abstract description 2
OQCUGPQOZNYIMV-UHFFFAOYSA-N pyrrolidin-3-ylmethanamine Chemical compound NCC1CCNC1 OQCUGPQOZNYIMV-UHFFFAOYSA-N 0.000 abstract description 2
238000006467 substitution reaction Methods 0.000 abstract description 2
150000002431 hydrogen Chemical class 0.000 abstract 1
150000004885 piperazines Chemical class 0.000 abstract 1
-1 hydrocarbon chain radical Chemical class 0.000 description 73
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 39
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 29
239000000203 mixture Substances 0.000 description 29
125000000217 alkyl group Chemical group 0.000 description 24
125000002837 carbocyclic group Chemical group 0.000 description 19
208000015181 infectious disease Diseases 0.000 description 17
239000000243 solution Substances 0.000 description 17
239000004599 antimicrobial Substances 0.000 description 16
125000004435 hydrogen atom Chemical class [H]* 0.000 description 16
238000000034 method Methods 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
125000003342 alkenyl group Chemical group 0.000 description 14
229940088710 antibiotic agent Drugs 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
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IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
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125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 10
229910052757 nitrogen Inorganic materials 0.000 description 10
125000001424 substituent group Chemical group 0.000 description 10
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125000004432 carbon atom Chemical group C* 0.000 description 7
238000011161 development Methods 0.000 description 7
230000018109 developmental process Effects 0.000 description 7
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 7
239000002552 dosage form Substances 0.000 description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
230000000813 microbial effect Effects 0.000 description 7
125000004203 4-hydroxyphenyl group Chemical group [H]OC1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 6
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125000005842 heteroatom Chemical group 0.000 description 6
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238000007911 parenteral administration Methods 0.000 description 6
LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical group C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 description 6
238000003756 stirring Methods 0.000 description 6
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238000006243 chemical reaction Methods 0.000 description 5
201000010099 disease Diseases 0.000 description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
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238000002512 chemotherapy Methods 0.000 description 4
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230000000694 effects Effects 0.000 description 4
125000004446 heteroarylalkyl group Chemical group 0.000 description 4
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239000001301 oxygen Substances 0.000 description 4
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GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 3
101150065749 Churc1 gene Proteins 0.000 description 3
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
102100038239 Protein Churchill Human genes 0.000 description 3
125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 3
150000001408 amides Chemical class 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
230000008901 benefit Effects 0.000 description 3
229910052799 carbon Inorganic materials 0.000 description 3
229910002091 carbon monoxide Inorganic materials 0.000 description 3
239000000969 carrier Substances 0.000 description 3
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239000002244 precipitate Substances 0.000 description 3
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
239000000376 reactant Substances 0.000 description 3
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
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SCNWTQPZTZMXBG-UHFFFAOYSA-N 2-methyloct-2-enoic acid Chemical compound CCCCCC=C(C)C(O)=O SCNWTQPZTZMXBG-UHFFFAOYSA-N 0.000 description 2
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208000026935 allergic disease Diseases 0.000 description 2
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239000011230 binding agent Substances 0.000 description 1
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125000001246 bromo group Chemical group Br* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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239000011575 calcium Substances 0.000 description 1
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AZZMGZXNTDTSME-JUZDKLSSSA-M cefotaxime sodium Chemical compound [Na+].N([C@@H]1C(N2C(=C(COC(C)=O)CS[C@@H]21)C([O-])=O)=O)C(=O)\C(=N/OC)C1=CSC(N)=N1 AZZMGZXNTDTSME-JUZDKLSSSA-M 0.000 description 1
SYLKGLMBLAAGSC-QLVMHMETSA-N cefsulodin Chemical compound C1=CC(C(=O)N)=CC=[N+]1CC1=C(C([O-])=O)N2C(=O)[C@@H](NC(=O)[C@@H](C=3C=CC=CC=3)S(O)(=O)=O)[C@H]2SC1 SYLKGLMBLAAGSC-QLVMHMETSA-N 0.000 description 1
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VUFGUVLLDPOSBC-XRZFDKQNSA-M cephalothin sodium Chemical compound [Na+].N([C@H]1[C@@H]2N(C1=O)C(=C(CS2)COC(=O)C)C([O-])=O)C(=O)CC1=CC=CS1 VUFGUVLLDPOSBC-XRZFDKQNSA-M 0.000 description 1
NVRSPIKUPKOSIY-UHFFFAOYSA-N chembl1743348 Chemical compound CC=1N=NOC=1O NVRSPIKUPKOSIY-UHFFFAOYSA-N 0.000 description 1
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DIOIOSKKIYDRIQ-UHFFFAOYSA-N ciprofloxacin hydrochloride Chemical compound Cl.C12=CC(N3CCNCC3)=C(F)C=C2C(=O)C(C(=O)O)=CN1C1CC1 DIOIOSKKIYDRIQ-UHFFFAOYSA-N 0.000 description 1
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230000001419 dependent effect Effects 0.000 description 1
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LVGKNOAMLMIIKO-QXMHVHEDSA-N ethyl oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OCC LVGKNOAMLMIIKO-QXMHVHEDSA-N 0.000 description 1
229940093471 ethyl oleate Drugs 0.000 description 1
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239000000945 filler Substances 0.000 description 1
239000012467 final product Substances 0.000 description 1
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238000009472 formulation Methods 0.000 description 1
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125000000524 functional group Chemical group 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
239000000499 gel Substances 0.000 description 1
125000005223 heteroarylcarbonyl group Chemical group 0.000 description 1
125000005224 heteroarylcarbonylamino group Chemical group 0.000 description 1
239000003752 hydrotrope Substances 0.000 description 1
238000007654 immersion Methods 0.000 description 1
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238000007912 intraperitoneal administration Methods 0.000 description 1
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239000006210 lotion Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
229940041033 macrolides Drugs 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
235000010270 methyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004292 methyl p-hydroxybenzoate Substances 0.000 description 1
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244000000010 microbial pathogen Species 0.000 description 1
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210000000214 mouth Anatomy 0.000 description 1
210000004877 mucosa Anatomy 0.000 description 1
SBLHFLBMDYPOJU-UHFFFAOYSA-N n-(pyrrolidin-1-ylmethyl)ethanamine Chemical compound CCNCN1CCCC1 SBLHFLBMDYPOJU-UHFFFAOYSA-N 0.000 description 1
SLWAVUFGAXSVPX-UHFFFAOYSA-N n-methyl-1-pyrrolidin-1-ylmethanamine Chemical compound CNCN1CCCC1 SLWAVUFGAXSVPX-UHFFFAOYSA-N 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
229940127285 new chemical entity Drugs 0.000 description 1
108020004707 nucleic acids Proteins 0.000 description 1
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239000002777 nucleoside Substances 0.000 description 1
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239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
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229960004236 pefloxacin Drugs 0.000 description 1
230000035699 permeability Effects 0.000 description 1
150000002988 phenazines Chemical class 0.000 description 1
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
125000005633 phthalidyl group Chemical group 0.000 description 1
150000004291 polyenes Chemical class 0.000 description 1
229920000570 polyether Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001184 polypeptide Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000008569 process Effects 0.000 description 1
CAEWJEXPFKNBQL-UHFFFAOYSA-N prop-2-enyl carbonochloridate Chemical compound ClC(=O)OCC=C CAEWJEXPFKNBQL-UHFFFAOYSA-N 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
239000004405 propyl p-hydroxybenzoate Substances 0.000 description 1
235000013772 propylene glycol Nutrition 0.000 description 1
229960003415 propylparaben Drugs 0.000 description 1
238000001243 protein synthesis Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
150000003248 quinolines Chemical class 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
230000008439 repair process Effects 0.000 description 1
230000003362 replicative effect Effects 0.000 description 1
208000020029 respiratory tract infectious disease Diseases 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000001509 sodium citrate Substances 0.000 description 1
NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000003892 spreading Methods 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
238000005556 structure-activity relationship Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000019364 tetracycline Nutrition 0.000 description 1
150000003522 tetracyclines Chemical class 0.000 description 1
229940040944 tetracyclines Drugs 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000003396 thiol group Chemical class [H]S* 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
125000003944 tolyl group Chemical group 0.000 description 1
230000014616 translation Effects 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
MBYLVOKEDDQJDY-UHFFFAOYSA-N tris(2-aminoethyl)amine Chemical compound NCCN(CCN)CCN MBYLVOKEDDQJDY-UHFFFAOYSA-N 0.000 description 1
208000019206 urinary tract infection Diseases 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
238000005303 weighing Methods 0.000 description 1
125000005023 xylyl group Chemical group 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group
- C07D501/34—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group with the 7-amino radical acylated by carboxylic acids containing hetero rings
- 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
- C07D501/00—Heterocyclic compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D501/14—Compounds having a nitrogen atom directly attached in position 7
- C07D501/16—Compounds having a nitrogen atom directly attached in position 7 with a double bond between positions 2 and 3
- C07D501/20—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids
- C07D501/24—7-Acylaminocephalosporanic or substituted 7-acylaminocephalosporanic acids in which the acyl radicals are derived from carboxylic acids with hydrocarbon radicals, substituted by hetero atoms or hetero rings, attached in position 3
- C07D501/26—Methylene radicals, substituted by oxygen atoms; Lactones thereof with the 2-carboxyl group

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)
Cephalosporin Compounds (AREA)
Medicinal Preparation (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Compositions Of Macromolecular Compounds (AREA)

PH39400A 1988-10-24 1989-10-24 Novel antimicrobial fluoroquinolonyl cephems PH26519A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US26194988A	1988-10-24	1988-10-24
US41802589A	1989-10-12	1989-10-12

Publications (1)

Publication Number	Publication Date
PH26519A true PH26519A (en)	1992-08-07

Family

ID=26948930

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
PH39400A PH26519A (en)	1988-10-24	1989-10-24	Novel antimicrobial fluoroquinolonyl cephems

Country Status (14)

Country	Link
EP (1)	EP0366640B1 (de)
JP (1)	JPH03503421A (de)
KR (1)	KR0139638B1 (de)
AT (1)	ATE176473T1 (de)
AU (1)	AU620651B2 (de)
CA (1)	CA2001204A1 (de)
DE (1)	DE68928925T2 (de)
DK (1)	DK527389A (de)
ES (1)	ES2129388T3 (de)
GR (1)	GR3030052T3 (de)
NZ (1)	NZ231113A (de)
PH (1)	PH26519A (de)
SG (1)	SG54293A1 (de)
WO (1)	WO1990004595A1 (de)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5147871A (en) *	1986-07-03	1992-09-15	Hoffmann La-Roche, Inc.	Anti-bacterial cephalosporin compounds
US5336768A (en) *	1988-05-24	1994-08-09	Hoffmann-La Roche Inc.	Antibacterial cephalosporin compounds
CS273349B2 (en) *	1988-03-31	1991-03-12	Hoffmann La Roche	Method of cephalosporin's new derivatives production
EP0997466A1 (de) *	1988-10-24	2000-05-03	PROCTER & GAMBLE PHARMACEUTICALS, INC.	Antimikrobielle Laktamchinolone
US5180719A (en) *	1988-10-24	1993-01-19	Norwich Eaton Pharmaceuticals, Inc.	Antimicrobial quinolonyl lactam esters
US5491139A (en) *	1988-10-24	1996-02-13	The Procter & Gamble Company	Antimicrobial quinolonyl lactams
CA2001203C (en) *	1988-10-24	2001-02-13	Thomas P. Demuth, Jr.	Novel antimicrobial dithiocarbamoyl quinolones
US5273973A (en) *	1988-10-24	1993-12-28	Norwich Eaton Pharmaceuticals, Inc.	Antimicrobial quinolonyl esters
US5328908A (en) *	1988-10-24	1994-07-12	Procter & Gamble Pharmaceuticals, Inc.	Antimicrobial quinolone thioureas
US5159077A (en) *	1989-07-21	1992-10-27	Hoffmann-La Roche Inc.	Penam antibacterial compounds
US5162523A (en) *	1989-07-21	1992-11-10	Hoffmann-La Roche Inc.	Cephalosporin antibacterial compounds
DK0525057T3 (da) *	1990-04-18	2000-07-31	Procter & Gamble Pharma	Antimikrobielle quinolonyllactamer
US5066800A (en) *	1990-04-27	1991-11-19	Hoffmann-La Roche Inc.	Qunoline intermediates useful therein for synthesizing antibacterial compounds
WO1993007154A1 (en) *	1991-10-01	1993-04-15	Procter & Gamble Pharmaceuticals, Inc.	Process for making antimicrobial quinolonyl lactams
DE4234330A1 (de) *	1992-10-12	1994-04-14	Bayer Ag	Chinoloncarbonsäuren
FR2873695A1 (fr) *	2004-07-30	2006-02-03	Palumed Sa	Molecules hybrides qa ou q est une aminoquinoleine et a est un antibiotique ou un inhibiteur de resistance), leur synthese et leurs utilisations en tant qu'agent antibacterien
GB201818410D0 (en) *	2018-11-12	2018-12-26	Imperial Innovations Ltd	Compounds

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS565485A (en) *	1979-06-27	1981-01-20	Dainippon Pharmaceut Co Ltd	Cephalosporin derivative and its salt
JPS565484A (en) *	1979-06-27	1981-01-20	Dainippon Pharmaceut Co Ltd	Cephalosporin derivative and its salt
ZA874696B (en) *	1986-07-03	1988-01-04	F. Hoffmann-La Roche & Co. Aktiengesellschaft	Acyl derivatives
JP2676082B2 (ja) *	1987-12-25	1997-11-12	住友化学工業株式会社	ゴキブリ防除用マイクロカプセル剤
NZ227470A (en) *	1987-12-28	1991-06-25	Hoffmann La Roche	Acyl derivatives of substituted cephem compounds; pharmaceutical compositions and methods for preparation and treatment
CA2001203C (en) *	1988-10-24	2001-02-13	Thomas P. Demuth, Jr.	Novel antimicrobial dithiocarbamoyl quinolones
EP0997466A1 (de) *	1988-10-24	2000-05-03	PROCTER & GAMBLE PHARMACEUTICALS, INC.	Antimikrobielle Laktamchinolone
EP0366193A3 (de) *	1988-10-24	1992-01-08	Norwich Eaton Pharmaceuticals, Inc.	Antimikrobielle Quinolonyllactame

1989
- 1989-10-20 AT AT89870151T patent/ATE176473T1/de not_active IP Right Cessation
- 1989-10-20 DE DE68928925T patent/DE68928925T2/de not_active Expired - Fee Related
- 1989-10-20 SG SG1996007907A patent/SG54293A1/en unknown
- 1989-10-20 EP EP89870151A patent/EP0366640B1/de not_active Expired - Lifetime
- 1989-10-20 ES ES89870151T patent/ES2129388T3/es not_active Expired - Lifetime
- 1989-10-23 CA CA002001204A patent/CA2001204A1/en not_active Abandoned
- 1989-10-24 DK DK527389A patent/DK527389A/da not_active Application Discontinuation
- 1989-10-24 KR KR1019890015236A patent/KR0139638B1/ko not_active Expired - Fee Related
- 1989-10-24 AU AU43697/89A patent/AU620651B2/en not_active Ceased
- 1989-10-24 NZ NZ231113A patent/NZ231113A/en unknown
- 1989-10-24 PH PH39400A patent/PH26519A/en unknown
- 1989-10-24 JP JP2501184A patent/JPH03503421A/ja active Pending
- 1989-10-24 WO PCT/US1989/004768 patent/WO1990004595A1/en not_active Ceased
1999
- 1999-04-26 GR GR990401132T patent/GR3030052T3/el unknown

Also Published As

Publication number	Publication date
KR900006347A (ko)	1990-05-08
SG54293A1 (en)	1998-11-16
DE68928925T2 (de)	1999-08-26
WO1990004595A1 (en)	1990-05-03
EP0366640B1 (de)	1999-02-03
AU620651B2 (en)	1992-02-20
AU4369789A (en)	1990-04-26
JPH03503421A (ja)	1991-08-01
ATE176473T1 (de)	1999-02-15
CA2001204A1 (en)	1990-04-24
EP0366640A3 (de)	1992-01-02
ES2129388T3 (es)	1999-06-16
GR3030052T3 (en)	1999-07-30
NZ231113A (en)	1992-06-25
EP0366640A2 (de)	1990-05-02
DK527389D0 (da)	1989-10-24
DE68928925D1 (de)	1999-03-18
DK527389A (da)	1990-04-25
KR0139638B1 (ko)	1998-06-01

Publication	Publication Date	Title
CA2001225C (en)	2000-12-19	Antimicrobial lactam-quinolones
AU659996B2 (en)	1995-06-08	Antimicrobial quinolone thioureas
CA2001205C (en)	2000-10-17	Antimicrobial quinolonyl lactams
PH26519A (en)	1992-08-07	Novel antimicrobial fluoroquinolonyl cephems
US5180719A (en)	1993-01-19	Antimicrobial quinolonyl lactam esters
EP0366641B1 (de)	2000-07-05	Antimikrobielle Quinolonyllactamester
EP0525057B1 (de)	2000-06-14	Antimikrobielle chinolonyl-lactame
US5147871A (en)	1992-09-15	Anti-bacterial cephalosporin compounds
HK1013067A (en)	1999-08-13	Novel antimicrobial fluoroquinolonyl cephems
IL92091A (en)	1995-10-31	Quinolonyl lactam esters and pharmaceutical preparations containing them
KR0162984B1 (ko)	1998-12-01	항미생물성 퀴놀로닐 락탐 에스테르 및 이를 함유하는 조성물
HK1013984B (en)	2001-03-30	Novel antimicrobial quinolonyl lactam esters
PH26648A (en)	1992-09-04	Acyl derivatives
IL92032A (en)	1995-10-31	Lactam-quinolones and pharmaceutical compositions containing them
IL92031A (en)	1995-12-08	Quinolonil for cuttings and pharmaceutical preparations containing them
HK1013066A (en)	1999-08-13	Novel antimicrobial lactam-quinolones
HU211676A9 (hu)	1995-12-28	Mikrobaellenes kinolonil-laktám-észterek