BG64707B1 - 2-хало-6-о-заместени кетолидни производни - Google Patents

2-хало-6-о-заместени кетолидни производни Download PDF

Info

Publication number: BG64707B1
Authority: BG; Bulgaria
Prior art keywords: compound; formula; quinolinyl; xef; hydrogen
Prior art date: 1997-10-29

Application number

BG104434A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG104434A (en

Inventor

Ly Phan

Yat Sun Or

Daniel Chu

Jacob Plattner

Yan Chen

Richard Clark

Original Assignee

Abbott Laboratories

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.)

1997-10-29

Filing date

2000-05-15

Publication date

2005-12-30

2000-05-15 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

2001-01-31 Publication of BG104434A publication Critical patent/BG104434A/xx

2005-12-30 Publication of BG64707B1 publication Critical patent/BG64707B1/bg

Links

239000003835 ketolide antibiotic agent Substances 0.000 title claims abstract description 11
150000001875 compounds Chemical class 0.000 claims abstract description 309
150000003839 salts Chemical class 0.000 claims abstract description 18
239000003814 drug Substances 0.000 claims abstract description 15
238000002360 preparation method Methods 0.000 claims abstract description 12
208000035143 Bacterial infection Diseases 0.000 claims abstract description 9
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 9
239000003937 drug carrier Substances 0.000 claims abstract description 9
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
229910052727 yttrium Inorganic materials 0.000 claims description 246
-1 N-protected amino Chemical group 0.000 claims description 194
229910052739 hydrogen Inorganic materials 0.000 claims description 61
239000001257 hydrogen Substances 0.000 claims description 59
125000001072 heteroaryl group Chemical group 0.000 claims description 38
125000003118 aryl group Chemical group 0.000 claims description 37
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 34
238000000034 method Methods 0.000 claims description 31
239000003153 chemical reaction reagent Substances 0.000 claims description 25
125000006239 protecting group Chemical group 0.000 claims description 17
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical group [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000004076 pyridyl group Chemical group 0.000 claims description 11
238000011282 treatment Methods 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 10
125000004663 dialkyl amino group Chemical group 0.000 claims description 10
230000002140 halogenating effect Effects 0.000 claims description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
MBVFRSJFKMJRHA-UHFFFAOYSA-N 4-fluoro-1-benzofuran-7-carbaldehyde Chemical group FC1=CC=C(C=O)C2=C1C=CO2 MBVFRSJFKMJRHA-UHFFFAOYSA-N 0.000 claims description 9
CJYQZTZSYREQBD-UHFFFAOYSA-N n-fluorobenzenesulfonamide Chemical compound FNS(=O)(=O)C1=CC=CC=C1 CJYQZTZSYREQBD-UHFFFAOYSA-N 0.000 claims description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 9
229910000104 sodium hydride Inorganic materials 0.000 claims description 9
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 8
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239000012312 sodium hydride Substances 0.000 claims description 6
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 5
235000019253 formic acid Nutrition 0.000 claims description 5
125000004593 naphthyridinyl group Chemical group N1=C(C=CC2=CC=CN=C12)* 0.000 claims description 5
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125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 5
LQZMLBORDGWNPD-UHFFFAOYSA-N N-iodosuccinimide Chemical compound IN1C(=O)CCC1=O LQZMLBORDGWNPD-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
KNLOWMNWRKBVKP-UHFFFAOYSA-N 1-fluoro-2h-pyridine;trifluoromethanesulfonic acid Chemical compound FN1CC=CC=C1.OS(=O)(=O)C(F)(F)F KNLOWMNWRKBVKP-UHFFFAOYSA-N 0.000 claims description 3
229910019093 NaOCl Inorganic materials 0.000 claims description 3
SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 claims description 3
238000005303 weighing Methods 0.000 claims description 3
VCEAGMYKGZNUFL-UHFFFAOYSA-N 1,2,2,3,3,4,4,5,5,6,6-undecafluoropiperidine Chemical compound FN1C(F)(F)C(F)(F)C(F)(F)C(F)(F)C1(F)F VCEAGMYKGZNUFL-UHFFFAOYSA-N 0.000 claims description 2
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238000010511 deprotection reaction Methods 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims 7
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239000002585 base Substances 0.000 description 20
238000002474 experimental method Methods 0.000 description 19
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239000002904 solvent Substances 0.000 description 17
238000006243 chemical reaction Methods 0.000 description 16
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
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229910052757 nitrogen Inorganic materials 0.000 description 13
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229910002027 silica gel Inorganic materials 0.000 description 11
125000003107 substituted aryl group Chemical group 0.000 description 11
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 10
239000002253 acid Substances 0.000 description 10
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 9
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239000000546 pharmaceutical excipient Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
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150000001502 aryl halides Chemical class 0.000 description 8
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241000699670 Mus sp. Species 0.000 description 7
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 7
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VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 7
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239000008101 lactose Substances 0.000 description 6
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239000000843 powder Substances 0.000 description 6
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VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 4
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125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
235000001968 nicotinic acid Nutrition 0.000 description 1
239000011664 nicotinic acid Substances 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
125000006574 non-aromatic ring group Chemical group 0.000 description 1
231100000344 non-irritating Toxicity 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
229940049964 oleate Drugs 0.000 description 1
239000004006 olive oil Substances 0.000 description 1
235000008390 olive oil Nutrition 0.000 description 1
229940041678 oral spray Drugs 0.000 description 1
239000000668 oral spray Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
238000006053 organic reaction Methods 0.000 description 1
235000006408 oxalic acid Nutrition 0.000 description 1
125000000160 oxazolidinyl group Chemical group 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
230000001590 oxidative effect Effects 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
PMJHHCWVYXUKFD-UHFFFAOYSA-N penta-1,3-diene Chemical compound CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 1
125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
JRKICGRDRMAZLK-UHFFFAOYSA-L peroxydisulfate Chemical compound [O-]S(=O)(=O)OOS([O-])(=O)=O JRKICGRDRMAZLK-UHFFFAOYSA-L 0.000 description 1
WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
125000004193 piperazinyl group Chemical group 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
IUGYQRQAERSCNH-UHFFFAOYSA-M pivalate Chemical compound CC(C)(C)C([O-])=O IUGYQRQAERSCNH-UHFFFAOYSA-M 0.000 description 1
229950010765 pivalate Drugs 0.000 description 1
229920002647 polyamide Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
CBMSDILKECEMOT-UHFFFAOYSA-N potassium;2-methylpropan-1-olate Chemical compound [K+].CC(C)C[O-] CBMSDILKECEMOT-UHFFFAOYSA-N 0.000 description 1
WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
230000002265 prevention Effects 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-UHFFFAOYSA-N 0.000 description 1
239000003380 propellant Substances 0.000 description 1
125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
229940090181 propyl acetate Drugs 0.000 description 1
125000006308 propyl amino group Chemical group 0.000 description 1
239000003223 protective agent Substances 0.000 description 1
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000003072 pyrazolidinyl group Chemical group 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
238000012797 qualification Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
125000001453 quaternary ammonium group Chemical group 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
230000009467 reduction Effects 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000010703 silicon Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 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
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
239000004296 sodium metabisulphite Substances 0.000 description 1
JXAZAUKOWVKTLO-UHFFFAOYSA-L sodium pyrosulfate Chemical compound [Na+].[Na+].[O-]S(=O)(=O)OS([O-])(=O)=O JXAZAUKOWVKTLO-UHFFFAOYSA-L 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
239000001384 succinic acid Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000011593 sulfur Chemical group 0.000 description 1
125000004434 sulfur atom Chemical group 0.000 description 1
XTQHKBHJIVJGKJ-UHFFFAOYSA-N sulfur monoxide Chemical class S=O XTQHKBHJIVJGKJ-UHFFFAOYSA-N 0.000 description 1
239000013589 supplement Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
229940095064 tartrate Drugs 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
125000000037 tert-butyldiphenylsilyl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1[Si]([H])([*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
238000011287 therapeutic dose Methods 0.000 description 1
125000001984 thiazolidinyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
230000009466 transformation Effects 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
238000011269 treatment regimen Methods 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
AAPLIUHOKVUFCC-UHFFFAOYSA-N trimethylsilanol Chemical compound C[Si](C)(C)O AAPLIUHOKVUFCC-UHFFFAOYSA-N 0.000 description 1
COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
210000001215 vagina Anatomy 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- A61K31/7042—Compounds having saccharide radicals and heterocyclic rings
- A61K31/7048—Compounds having saccharide radicals and heterocyclic rings having oxygen as a ring hetero atom, e.g. leucoglucosan, hesperidin, erythromycin, nystatin, digitoxin or digoxin
- 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
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Veterinary Medicine (AREA)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)

BG104434A 1997-10-29 2000-05-15 2-хало-6-о-заместени кетолидни производни BG64707B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US95988197A	1997-10-29	1997-10-29
US15423998A	1998-09-16	1998-09-16

Publications (2)

Publication Number	Publication Date
BG104434A BG104434A (en)	2001-01-31
BG64707B1 true BG64707B1 (bg)	2005-12-30

Family

ID=26851273

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG104434A BG64707B1 (bg)	1997-10-29	2000-05-15	2-хало-6-о-заместени кетолидни производни

Country Status (24)

Country	Link
EP (1)	EP1027362B1 (fr)
JP (1)	JP2001521039A (fr)
KR (1)	KR100536420B1 (fr)
CN (1)	CN1240707C (fr)
AR (1)	AR015994A1 (fr)
AT (1)	ATE298760T1 (fr)
AU (1)	AU751448B2 (fr)
BG (1)	BG64707B1 (fr)
BR (1)	BR9813319A (fr)
CA (1)	CA2307788C (fr)
CO (1)	CO4990960A1 (fr)
CZ (1)	CZ300063B6 (fr)
DE (1)	DE69830739T2 (fr)
DK (1)	DK1027362T3 (fr)
ES (1)	ES2244094T3 (fr)
HU (1)	HUP0004282A3 (fr)
IL (1)	IL135519A0 (fr)
NO (1)	NO20002190L (fr)
NZ (1)	NZ503822A (fr)
PL (1)	PL191453B1 (fr)
PT (1)	PT1027362E (fr)
SK (1)	SK286397B6 (fr)
TR (1)	TR200001142T2 (fr)
WO (1)	WO1999021871A1 (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
USRE39743E1 (en) *	1998-10-15	2007-07-24	Aventis Pharma S.A.	2-halogenated derivatives of 5-0 desosaminyl-erythronolide a, their preparation process and their antibiotic use
FR2784682B1 (fr) *	1998-10-15	2002-12-06	Hoechst Marion Roussel Inc	Nouveaux derives 2-halogene de 5-0-desosaminylerythronolide a, leur procede de preparation et leur application comme medicaments
US6939861B2 (en)	1999-04-16	2005-09-06	Kosan Biosciences, Inc.	Amido macrolides
US6395710B1 (en)	1999-04-16	2002-05-28	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6514944B2 (en)	1999-04-16	2003-02-04	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6451768B1 (en)	1999-04-16	2002-09-17	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6569836B2 (en)	1999-12-02	2003-05-27	Abbott Laboratories	6-O-alkyl-2-nor-2-substituted ketolide derivatives
DE60039122D1 (de) *	1999-12-02	2008-07-17	Abbott Lab	6-o-alkyl-2-nor-2-substituierte ketolidderivate
JP2001261694A (ja) *	2000-03-06	2001-09-26	Pfizer Prod Inc	ケトライド抗生物質
US6605707B1 (en) *	2000-03-23	2003-08-12	Abbott Laboratories	Process for the preparation of 6-O-propargyl erythromycin derivatives
TR200401847T4 (tr)	2000-06-30	2004-09-21	Pfizer Products Inc.	Makrolit antibiyotikler.
US6472372B1 (en)	2000-12-06	2002-10-29	Ortho-Mcneil Pharmaceuticals, Inc.	6-O-Carbamoyl ketolide antibacterials
CN1589277A (zh)	2001-09-17	2005-03-02	奥索-麦克尼尔药品公司	6－o－氨基甲酸酯－11,12－内酯－酮内酯抗菌剂
AU2002346475A1 (en)	2001-12-05	2003-06-23	Ortho-Mcneil Pharmaceutical, Inc.	6-o-acyl ketolide derivatives of erythromycine useful as antibacterials
MXPA04007883A (es) *	2002-02-13	2004-11-26	Abbott Lab	Compuestos antimicrobianos de macrolido.
WO2003090761A1 (fr) *	2002-04-25	2003-11-06	Abbott Laboratories	Antibacteriens 9-oxime macrolide
WO2003090760A1 (fr) *	2002-04-25	2003-11-06	Abbott Laboratories	Composes antibacteriens a base d'oxolide
WO2004078771A1 (fr) *	2003-03-07	2004-09-16	Taisho Pharmaceutical Co., Ltd.	Derive de ketolide 2-fluoro-6-o-substitue
JP2007254285A (ja) *	2004-03-16	2007-10-04	Taisho Pharmaceut Co Ltd	２−フルオロ−６−ｏ−置換ケトライド誘導体
RU2011153353A (ru) *	2009-05-27	2013-07-10	Вокхардт Рисерч Сентер	Кетолидные соединения, обладающие противомикробной активностью

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8506380D0 (en) *	1985-03-12	1985-04-11	Beecham Group Plc	Chemical compounds
IL99995A (en) *	1990-11-21	1997-11-20	Roussel Uclaf	Erythromycin derivatives, their preparation and pharmaceutical compositions containing them
US5631355A (en) *	1992-04-22	1997-05-20	Taisho Pharmaceutical Co., Ltd.	5-O-desosaminylerythronolide a derivatives
FR2742757B1 (fr) *	1995-12-22	1998-01-30	Roussel Uclaf	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments

1998
- 1998-10-27 CO CO98062730A patent/CO4990960A1/es unknown
- 1998-10-28 AR ARP980105407A patent/AR015994A1/es unknown
- 1998-10-29 ES ES98956338T patent/ES2244094T3/es not_active Expired - Lifetime
- 1998-10-29 EP EP98956338A patent/EP1027362B1/fr not_active Expired - Lifetime
- 1998-10-29 CN CNB988127326A patent/CN1240707C/zh not_active Expired - Fee Related
- 1998-10-29 DK DK98956338T patent/DK1027362T3/da active
- 1998-10-29 WO PCT/US1998/022989 patent/WO1999021871A1/fr not_active Ceased
- 1998-10-29 BR BR9813319-5A patent/BR9813319A/pt not_active Application Discontinuation
- 1998-10-29 HU HU0004282A patent/HUP0004282A3/hu unknown
- 1998-10-29 TR TR2000/01142T patent/TR200001142T2/xx unknown
- 1998-10-29 AT AT98956338T patent/ATE298760T1/de not_active IP Right Cessation
- 1998-10-29 CZ CZ20001525A patent/CZ300063B6/cs not_active IP Right Cessation
- 1998-10-29 NZ NZ503822A patent/NZ503822A/xx unknown
- 1998-10-29 IL IL13551998A patent/IL135519A0/xx not_active IP Right Cessation
- 1998-10-29 PT PT98956338T patent/PT1027362E/pt unknown
- 1998-10-29 JP JP2000517980A patent/JP2001521039A/ja active Pending
- 1998-10-29 CA CA002307788A patent/CA2307788C/fr not_active Expired - Fee Related
- 1998-10-29 KR KR10-2000-7004613A patent/KR100536420B1/ko not_active Expired - Fee Related
- 1998-10-29 DE DE69830739T patent/DE69830739T2/de not_active Expired - Lifetime
- 1998-10-29 PL PL340290A patent/PL191453B1/pl not_active IP Right Cessation
- 1998-10-29 SK SK633-2000A patent/SK286397B6/sk not_active IP Right Cessation
- 1998-10-29 AU AU12881/99A patent/AU751448B2/en not_active Ceased
2000
- 2000-04-27 NO NO20002190A patent/NO20002190L/no not_active Application Discontinuation
- 2000-05-15 BG BG104434A patent/BG64707B1/bg unknown

Also Published As

Publication number	Publication date
CZ300063B6 (cs)	2009-01-21
CA2307788C (fr)	2008-05-20
ATE298760T1 (de)	2005-07-15
CA2307788A1 (fr)	1999-05-06
EP1027362A1 (fr)	2000-08-16
ES2244094T3 (es)	2005-12-01
AU1288199A (en)	1999-05-17
PL340290A1 (en)	2001-01-29
CZ20001525A3 (cs)	2000-10-11
BG104434A (en)	2001-01-31
CN1240707C (zh)	2006-02-08
IL135519A0 (en)	2001-05-20
DK1027362T3 (da)	2005-10-31
KR100536420B1 (ko)	2005-12-16
HUP0004282A3 (en)	2001-10-29
NO20002190D0 (no)	2000-04-27
KR20010015793A (ko)	2001-02-26
HK1031383A1 (en)	2001-06-15
CN1283199A (zh)	2001-02-07
DE69830739T2 (de)	2006-04-20
BR9813319A (pt)	2000-08-22
HUP0004282A2 (hu)	2001-04-28
WO1999021871A1 (fr)	1999-05-06
EP1027362B1 (fr)	2005-06-29
PL191453B1 (pl)	2006-05-31
TR200001142T2 (tr)	2000-09-21
AR015994A1 (es)	2001-05-30
SK6332000A3 (en)	2000-09-12
NO20002190L (no)	2000-06-29
AU751448B2 (en)	2002-08-15
DE69830739D1 (de)	2005-08-04
JP2001521039A (ja)	2001-11-06
NZ503822A (en)	2002-12-20
CO4990960A1 (es)	2000-12-26
SK286397B6 (sk)	2008-09-05
PT1027362E (pt)	2005-08-31

Publication	Publication Date	Title
US6124269A (en)	2000-09-26	2-Halo-6-O-substituted ketolide derivatives
EP1027362B1 (fr)	2005-06-29	2-halo ketolides avec substitution -6-o
EP1015467B1 (fr)	2004-01-07	Derives d'erythromycine pontes en 6,9
EP1025114B1 (fr)	2004-02-25	Derives d'erythromycine cetolides, modifies en n-3' et substitues en o-6, possedant une activite antibacterienne
SK13162001A3 (sk)	2001-12-03	6-o-substituované makrolidy majúce antibakteriálnu aktivitu
AU1286799A (en)	1999-05-17	6,11-bridged erythromycin derivatives
US6034069A (en)	2000-03-07	3-'N-modified 6-O-substituted erythromycin ketolide derivatives having antibacterial activity
EP1181300B1 (fr)	2003-09-17	Derives ketolide de 6-o-carbamate
US6569836B2 (en)	2003-05-27	6-O-alkyl-2-nor-2-substituted ketolide derivatives
US5780604A (en)	1998-07-14	11,12-cyclic phosphite or phosphate derivatives of erythromycin and related macrolides
EP1233971B1 (fr)	2008-06-04	Derives 6-o-alkyl-2-nor-2- substitues de ketolides
HK1031383B (en)	2006-04-28	2-halo-6-o-subsituted ketolide derivatives
WO2001063539A2 (fr)	2001-08-30	Agents anti-infectieux utiles contre des souches de bacteries resistant a l'action de plusieurs medicaments
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