ZA200501012B - Lincomycin derivatives possessing antibacterial activity - Google Patents
Lincomycin derivatives possessing antibacterial activity Download PDFInfo
- Publication number
- ZA200501012B ZA200501012B ZA200501012A ZA200501012A ZA200501012B ZA 200501012 B ZA200501012 B ZA 200501012B ZA 200501012 A ZA200501012 A ZA 200501012A ZA 200501012 A ZA200501012 A ZA 200501012A ZA 200501012 B ZA200501012 B ZA 200501012B
- Authority
- ZA
- South Africa
- Prior art keywords
- propyl
- methyl
- carboxylic acid
- trihydroxy
- pyran
- Prior art date
Links
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical class CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 title description 10
- 230000000844 anti-bacterial effect Effects 0.000 title description 6
- -1 monochlorophenyl Chemical group 0.000 claims description 83
- 150000001875 compounds Chemical class 0.000 claims description 82
- 125000000217 alkyl group Chemical group 0.000 claims description 76
- 238000000034 method Methods 0.000 claims description 25
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 23
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000001072 heteroaryl group Chemical class 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 20
- 241000124008 Mammalia Species 0.000 claims description 19
- 239000001257 hydrogen Substances 0.000 claims description 18
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 18
- 239000008194 pharmaceutical composition Substances 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 17
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- 239000000651 prodrug Substances 0.000 claims description 16
- 229940002612 prodrug Drugs 0.000 claims description 16
- 125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 15
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 15
- 125000001153 fluoro group Chemical group F* 0.000 claims description 15
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 208000015181 infectious disease Diseases 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052736 halogen Inorganic materials 0.000 claims description 12
- 150000002367 halogens Chemical class 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 125000000623 heterocyclic group Chemical class 0.000 claims description 10
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 10
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims description 9
- 150000002829 nitrogen Chemical class 0.000 claims description 9
- 150000002926 oxygen Chemical class 0.000 claims description 9
- 241000606123 Bacteroides thetaiotaomicron Species 0.000 claims description 8
- 241000588724 Escherichia coli Species 0.000 claims description 8
- 241000606768 Haemophilus influenzae Species 0.000 claims description 8
- 241000588655 Moraxella catarrhalis Species 0.000 claims description 8
- 241000191963 Staphylococcus epidermidis Species 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- 125000004966 cyanoalkyl group Chemical group 0.000 claims description 8
- 229940047650 haemophilus influenzae Drugs 0.000 claims description 8
- 230000005764 inhibitory process Effects 0.000 claims description 8
- 230000000813 microbial effect Effects 0.000 claims description 8
- 241000606124 Bacteroides fragilis Species 0.000 claims description 7
- 241000193163 Clostridioides difficile Species 0.000 claims description 7
- 241000194032 Enterococcus faecalis Species 0.000 claims description 7
- 241000191967 Staphylococcus aureus Species 0.000 claims description 7
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
- 229940032049 enterococcus faecalis Drugs 0.000 claims description 7
- 239000003937 drug carrier Substances 0.000 claims description 6
- 241000194031 Enterococcus faecium Species 0.000 claims description 5
- 241000193998 Streptococcus pneumoniae Species 0.000 claims description 5
- 229940031000 streptococcus pneumoniae Drugs 0.000 claims description 5
- 239000003814 drug Substances 0.000 claims description 4
- KJQAZPSDPJLGHW-UHFFFAOYSA-N 4-fluoro-n-[2-hydroxy-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-propylpyrrolidine-2-carboxamide Chemical compound C1C(CCC)(F)CNC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 KJQAZPSDPJLGHW-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 230000037396 body weight Effects 0.000 claims description 2
- 150000002148 esters Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 7
- FYEFLEUMNQBKHG-UHFFFAOYSA-N 2-(1-amino-2-methylpropyl)-6-methylsulfanyloxane-3,4,5-triol Chemical compound CSC1OC(C(N)C(C)C)C(O)C(O)C1O FYEFLEUMNQBKHG-UHFFFAOYSA-N 0.000 claims 5
- 241000194033 Enterococcus Species 0.000 claims 4
- MAWGMRQFCUEYCT-UHFFFAOYSA-N 1-methyl-4-propylpyrrolidine-2-carboxylic acid Chemical compound CCCC1CC(C(O)=O)N(C)C1 MAWGMRQFCUEYCT-UHFFFAOYSA-N 0.000 claims 2
- 241000194017 Streptococcus Species 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- LZDZOCRKNQTXBI-UHFFFAOYSA-N 1-(2-hydroxyethyl)-4-pentylpyrrolidine-2-carboxylic acid Chemical compound CCCCCC1CC(C(O)=O)N(CCO)C1 LZDZOCRKNQTXBI-UHFFFAOYSA-N 0.000 claims 1
- YYOLWMVXPPQURS-UHFFFAOYSA-N 1-(3-hydroxypropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]-4-pentylpyrrolidine-2-carboxamide Chemical compound OCCCN1CC(CCCCC)CC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 YYOLWMVXPPQURS-UHFFFAOYSA-N 0.000 claims 1
- 125000004778 2,2-difluoroethyl group Chemical group [H]C([H])(*)C([H])(F)F 0.000 claims 1
- ANZRZTWFDJJFFJ-UHFFFAOYSA-N 4-(2,2-difluoropentyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]pyrrolidine-2-carboxamide Chemical compound C1C(CC(F)(F)CCC)CNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 ANZRZTWFDJJFFJ-UHFFFAOYSA-N 0.000 claims 1
- XVBQNFFMLDHFHX-UHFFFAOYSA-N 4-(2-methylpropyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CC(C)C)C1 XVBQNFFMLDHFHX-UHFFFAOYSA-N 0.000 claims 1
- XMCHFJVAIUFQGV-UHFFFAOYSA-N 4-(3,3-difluoropentyl)-1-(2-hydroxyethyl)pyrrolidine-2-carboxylic acid Chemical compound CCC(F)(F)CCC1CC(C(O)=O)N(CCO)C1 XMCHFJVAIUFQGV-UHFFFAOYSA-N 0.000 claims 1
- SLDZCHBOKUWDPP-UHFFFAOYSA-N 4-(3,3-difluoropropyl)pyrrolidine-2-carboxylic acid Chemical compound OC(=O)C1CC(CCC(F)F)CN1 SLDZCHBOKUWDPP-UHFFFAOYSA-N 0.000 claims 1
- RUBRFXMUVYLMJU-UHFFFAOYSA-N 4-(3-ethyl-3-hydroxypentyl)piperidine-2-carboxylic acid Chemical compound CCC(O)(CC)CCC1CCNC(C(O)=O)C1 RUBRFXMUVYLMJU-UHFFFAOYSA-N 0.000 claims 1
- INWIUDFKJNUSAV-UHFFFAOYSA-N 4-(3-fluoropropoxy)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(OCCCF)CCN1 INWIUDFKJNUSAV-UHFFFAOYSA-N 0.000 claims 1
- JPGDJWQEAYQZIQ-UHFFFAOYSA-N 4-(4,4-difluorobutyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(CCCC(F)F)C1 JPGDJWQEAYQZIQ-UHFFFAOYSA-N 0.000 claims 1
- PHNLWUOHMQIXNG-UHFFFAOYSA-N 4-(4,4-difluoropentyl)pyrrolidine-2-carboxylic acid Chemical compound CC(F)(F)CCCC1CNC(C(O)=O)C1 PHNLWUOHMQIXNG-UHFFFAOYSA-N 0.000 claims 1
- UGMWCKUJRWVGMT-UHFFFAOYSA-N 4-(4-fluorobutoxy)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound OC1C(O)C(O)C(SC)OC1C(C(C)C)NC(=O)C1NCCC(OCCCCF)C1 UGMWCKUJRWVGMT-UHFFFAOYSA-N 0.000 claims 1
- WQXFUDJPHDVMJK-UHFFFAOYSA-N 4-(4-fluorobutyl)piperidine-2-carboxylic acid Chemical compound OC(=O)C1CC(CCCCF)CCN1 WQXFUDJPHDVMJK-UHFFFAOYSA-N 0.000 claims 1
- YPPFOXPVFKYERL-UHFFFAOYSA-N 4-butoxy-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(OCCCC)CCNC1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 YPPFOXPVFKYERL-UHFFFAOYSA-N 0.000 claims 1
- YJGGBMKCNMLJBD-UHFFFAOYSA-N 4-butylpiperidine-2-carboxylic acid Chemical compound CCCCC1CCNC(C(O)=O)C1 YJGGBMKCNMLJBD-UHFFFAOYSA-N 0.000 claims 1
- SMZHNCMPICENER-UHFFFAOYSA-N 4-butylpyrrolidine-2-carboxylic acid Chemical compound CCCCC1CNC(C(O)=O)C1 SMZHNCMPICENER-UHFFFAOYSA-N 0.000 claims 1
- HRHIKSLSMMWSSH-UHFFFAOYSA-N 4-cyclohexylpiperidine-2-carboxylic acid Chemical compound C1CNC(C(=O)O)CC1C1CCCCC1 HRHIKSLSMMWSSH-UHFFFAOYSA-N 0.000 claims 1
- QHKALQVBKFZCGF-UHFFFAOYSA-N 4-ethyl-1-(2-hydroxyethyl)-n-[2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CC)CCN(CCO)C1C(=O)NC(C(C)C)C1C(O)C(O)C(O)C(SC)O1 QHKALQVBKFZCGF-UHFFFAOYSA-N 0.000 claims 1
- HOFQFGGCTRQYCC-UHFFFAOYSA-N 4-ethyl-n-[2-hydroxy-2-methyl-1-(3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl)propyl]piperidine-2-carboxamide Chemical compound C1C(CC)CCNC1C(=O)NC(C(C)(C)O)C1C(O)C(O)C(O)C(SC)O1 HOFQFGGCTRQYCC-UHFFFAOYSA-N 0.000 claims 1
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- KLVAZDORKYWHGN-UHFFFAOYSA-N 4-pentylpiperidine-2-carboxylic acid Chemical compound CCCCCC1CCNC(C(O)=O)C1 KLVAZDORKYWHGN-UHFFFAOYSA-N 0.000 claims 1
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- 125000001624 naphthyl group Chemical group 0.000 description 1
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- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- AEKHNNJSMVVESS-UHFFFAOYSA-N o-trimethylsilylhydroxylamine Chemical compound C[Si](C)(C)ON AEKHNNJSMVVESS-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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- 239000002674 ointment Substances 0.000 description 1
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- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- IUGYQRQAERSCNH-UHFFFAOYSA-N pivalic acid Chemical compound CC(C)(C)C(O)=O IUGYQRQAERSCNH-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011698 potassium fluoride Substances 0.000 description 1
- 235000003270 potassium fluoride Nutrition 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- WSHYKIAQCMIPTB-UHFFFAOYSA-M potassium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate Chemical compound [K+].[O-]C=1C2=CC=CC=C2OC(=O)C=1C(CC(=O)C)C1=CC=CC=C1 WSHYKIAQCMIPTB-UHFFFAOYSA-M 0.000 description 1
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- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
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- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 229910052705 radium Inorganic materials 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 229960004889 salicylic acid Drugs 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 239000011343 solid material Substances 0.000 description 1
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- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 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
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- ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000001425 triazolyl group Chemical group 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- LEIMLDGFXIOXMT-UHFFFAOYSA-N trimethylsilyl cyanide Chemical compound C[Si](C)(C)C#N LEIMLDGFXIOXMT-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
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- 150000003751 zinc Chemical class 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
-
- 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
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US40377002P | 2002-08-15 | 2002-08-15 |
Publications (1)
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ZA200501012B true ZA200501012B (en) | 2006-10-25 |
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Family Applications (1)
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ZA200501012A ZA200501012B (en) | 2002-08-15 | 2003-08-15 | Lincomycin derivatives possessing antibacterial activity |
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US (1) | US7164011B2 (es) |
EP (1) | EP1529052A2 (es) |
JP (1) | JP2006504673A (es) |
KR (1) | KR20050056195A (es) |
CN (1) | CN1315859C (es) |
AU (1) | AU2003265475B2 (es) |
BR (1) | BR0313725A (es) |
CA (1) | CA2493799A1 (es) |
EA (1) | EA200500353A1 (es) |
IL (1) | IL166476A (es) |
MX (1) | MXPA05001689A (es) |
NO (1) | NO20051289L (es) |
NZ (1) | NZ538141A (es) |
WO (1) | WO2004016632A2 (es) |
ZA (1) | ZA200501012B (es) |
Families Citing this family (13)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7199105B2 (en) | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
WO2004016632A2 (en) | 2002-08-15 | 2004-02-26 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
EP1654268A2 (en) * | 2003-06-17 | 2006-05-10 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
AU2004261550A1 (en) * | 2003-06-17 | 2005-02-10 | Vicuron Pharmaceuticals, Inc. | Novel lincomycin derivatives possessing antimicrobial activity |
US7199106B2 (en) | 2003-06-17 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antimicrobial activity |
US7256177B2 (en) | 2003-06-17 | 2007-08-14 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
US7361743B2 (en) | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
JP5064237B2 (ja) * | 2005-12-09 | 2012-10-31 | Meiji Seikaファルマ株式会社 | リンコマイシン誘導体およびこれを有効成分とする抗菌剤 |
EP2151447A4 (en) * | 2007-05-31 | 2012-09-05 | Meiji Seika Kaisha | LINCOMYCIN DERIVATIVES AND ANTIBACTERIAL AGENTS CONTAINING SAME AS ACTIVE INGREDIENTS |
JP5290166B2 (ja) * | 2007-05-31 | 2013-09-18 | Meiji Seikaファルマ株式会社 | リンコサミド誘導体及びこれを有効成分とする抗菌剤 |
CN101555223B (zh) * | 2009-04-17 | 2011-06-01 | 北京化工大学 | 一种吡利霉素中间体及其制备方法 |
EP2809156B1 (en) * | 2011-12-08 | 2017-05-24 | The Board of Regents of The University of Texas System | Allosteric modulators of 5-hydroxytryptamine 2c receptor (5-ht2cr) |
CN105566411B (zh) * | 2014-11-07 | 2020-11-13 | 中国科学院上海有机化学研究所 | 林可霉素生物合成中间产物及其制法和用途 |
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US29558A (en) * | 1860-08-14 | Bread-slicer | ||
US2851463A (en) * | 1956-04-09 | 1958-09-09 | Upjohn Co | Desalicetin and salts, and hydrocarbon carboxylic acid esters |
US2928844A (en) * | 1958-02-24 | 1960-03-15 | Upjohn Co | Celesticetin, its salts and method of preparation |
US3086912A (en) * | 1961-07-03 | 1963-04-23 | Upjohn Co | Antibiotic lincolnensin and method of production |
US3268556A (en) * | 1964-04-13 | 1966-08-23 | Upjohn Co | Novel lincomycin derivatives |
NL128232C (es) * | 1964-04-13 | |||
US3255174A (en) * | 1964-04-13 | 1966-06-07 | Upjohn Co | 7-0-methyl-n-acyl-3, 4-o-isopropylidene-1-deoxy-lincosamines |
NL146501C (es) * | 1964-07-01 | |||
US3380992A (en) * | 1965-06-14 | 1968-04-30 | Upjohn Co | Lincomycin derivatives and process for preparing same |
US3764672A (en) * | 1964-08-05 | 1973-10-09 | Upjohn Co | Composition and process of treatment using lincomycin derivatives |
US3282917A (en) * | 1964-08-17 | 1966-11-01 | Upjohn Co | Methyl n-(1-alkyl-4-alkoxy-prolyl)-alpha-thiolincosaminide compounds and process therefor |
NL140527B (nl) * | 1965-02-08 | 1973-12-17 | Upjohn Co | Werkwijze ter bereiding van aan lincomycine verwante verbindingen. |
US3496163A (en) * | 1965-02-08 | 1970-02-17 | Upjohn Co | 7-halo-7-deoxylincomycins and process for preparing the same |
US3502648A (en) * | 1965-02-08 | 1970-03-24 | Upjohn Co | 7-halo-7-deoxythiolincosaminides and process for preparing the same |
US3435025A (en) * | 1966-03-18 | 1969-03-25 | Upjohn Co | 7-deoxylincomycin and analogs and isomers thereof and process for making the same |
US3475407A (en) * | 1967-12-22 | 1969-10-28 | Upjohn Co | Process for preparing 7(r)- and 7(s)-halolincomycins |
US3544551A (en) * | 1968-04-30 | 1970-12-01 | Upjohn Co | 7-mercapto-7-deoxylincomycins and process for preparing the same |
US3509127A (en) * | 1968-04-30 | 1970-04-28 | Upjohn Co | Isologs of lincomycins and process for preparing the same |
US3555007A (en) * | 1968-07-22 | 1971-01-12 | Upjohn Co | 7-deoxy-7-halo lincomycin d derivatives |
US3549615A (en) * | 1968-10-17 | 1970-12-22 | Upjohn Co | Lincomycin derivatives and process for producing the same |
US3702322A (en) * | 1970-04-06 | 1972-11-07 | Upjohn Co | Derivatives of lincomycin and its analogs and process |
DE2118636A1 (de) | 1970-04-20 | 1971-11-04 | The Upjohn Co., Kalamazoo, Mich. (V.StA.) | 3-Nucleotide von Lincomycin und deren Analogen, Verfahren zu ihrer Herstellung und ihre Verwendung in therapeutischen Präparaten |
US3692767A (en) * | 1970-05-06 | 1972-09-19 | Upjohn Co | Process for making lincomycin and analogs thereof and novel compounds obtained thereby |
US3714141A (en) * | 1970-05-26 | 1973-01-30 | Upjohn Co | Process for making 7-halolincomycins |
US3674647A (en) * | 1970-10-07 | 1972-07-04 | Upjohn Co | Preparation of lincomycin analogues |
US3715346A (en) * | 1970-11-18 | 1973-02-06 | Upjohn Co | Process for the preparation of lincomycin compounds |
US3671647A (en) * | 1971-03-24 | 1972-06-20 | Upjohn Co | Lincomycin 3-nucleotides and the salts thereof |
US3787390A (en) * | 1971-06-23 | 1974-01-22 | Upjohn Co | Analogs of lincomycin and process |
US3892730A (en) * | 1971-06-23 | 1975-07-01 | Upjohn Co | 1{40 -({62 -hydroxyethyl)-1{40 -demethyl clindamycin 2-acylates |
US3856943A (en) * | 1971-06-23 | 1974-12-24 | Upjohn Co | Compositions and process |
US3892729A (en) * | 1971-06-23 | 1975-07-01 | Upjohn Co | 1{40 (Beta-hydroxyethyl)-1{40 -demethyl clindamycin 2-phosphates |
US3915954A (en) * | 1971-11-15 | 1975-10-28 | Upjohn Co | Derivatives of lincomycin and its analogs and process |
BE793630A (fr) * | 1972-01-03 | 1973-07-03 | Upjohn Co | Nouvel antibiotique de la classe des celesticetines et son procede de preparation |
US3853843A (en) * | 1972-12-13 | 1974-12-10 | Upjohn Co | Derivatives of thiolincosaminide compounds |
US3849396A (en) * | 1973-01-08 | 1974-11-19 | Upjohn Co | Lincomycin and clindamycin 1-o-ethers |
US3870699A (en) * | 1973-03-06 | 1975-03-11 | Upjohn Co | Lincomycin analogs |
US3833475A (en) * | 1973-04-23 | 1974-09-03 | Upjohn Co | Process for preparing lincomycin |
US4271266A (en) * | 1974-06-10 | 1981-06-02 | The Upjohn Manufacturing Company | Process for preparing lincomycin |
US4031304A (en) * | 1976-01-30 | 1977-06-21 | The Upjohn Company | Process for preparing lincomycin derivatives |
US4278789A (en) * | 1979-11-23 | 1981-07-14 | The Upjohn Company | Lincomycin compounds |
US4310660A (en) * | 1980-05-19 | 1982-01-12 | The Upjohn Company | Lincomycin compounds |
US4309533A (en) * | 1980-05-19 | 1982-01-05 | The Upjohn Company | Lincomycin compounds |
US4293547A (en) * | 1980-08-25 | 1981-10-06 | The Upjohn Company | Method of treating malaria |
US4317903A (en) * | 1981-01-26 | 1982-03-02 | The Upjohn Company | Process for the purification of lincomycin |
US4383109A (en) * | 1981-04-20 | 1983-05-10 | The Upjohn Company | Lincomycin nucleotides |
US4464466A (en) * | 1981-04-20 | 1984-08-07 | The Upjohn Company | Process of producing lincomycin nucleotides |
US4430495A (en) * | 1982-09-17 | 1984-02-07 | The Upjohn Company | Process for preparing lincomycin and clindamycin ribonucleotides |
US4568741A (en) * | 1984-05-15 | 1986-02-04 | The Upjohn Company | Synthesis of 7-halo-7-deoxylincomycins |
CN1004002B (zh) * | 1984-11-29 | 1989-04-26 | 厄普约翰公司 | 制备7-卤-7-去氧林可霉素及其类似化合物的改进方法 |
AU2725988A (en) | 1987-11-20 | 1989-06-14 | Upjohn Company, The | Derivatives of lincosaminide antibiotics |
CA2319495A1 (en) | 1998-06-08 | 1999-12-16 | Advanced Medicine, Inc. | Multibinding inhibitors of microsomal triglyceride transferase protein |
US7199105B2 (en) * | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
WO2004016632A2 (en) | 2002-08-15 | 2004-02-26 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
AU2004261550A1 (en) | 2003-06-17 | 2005-02-10 | Vicuron Pharmaceuticals, Inc. | Novel lincomycin derivatives possessing antimicrobial activity |
EP1654268A2 (en) | 2003-06-17 | 2006-05-10 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
-
2003
- 2003-08-15 WO PCT/US2003/025820 patent/WO2004016632A2/en active Application Filing
- 2003-08-15 US US10/642,807 patent/US7164011B2/en not_active Expired - Fee Related
- 2003-08-15 KR KR1020057002309A patent/KR20050056195A/ko not_active Application Discontinuation
- 2003-08-15 JP JP2004529541A patent/JP2006504673A/ja active Pending
- 2003-08-15 ZA ZA200501012A patent/ZA200501012B/en unknown
- 2003-08-15 CA CA002493799A patent/CA2493799A1/en not_active Abandoned
- 2003-08-15 MX MXPA05001689A patent/MXPA05001689A/es active IP Right Grant
- 2003-08-15 NZ NZ538141A patent/NZ538141A/en unknown
- 2003-08-15 BR BRPI0313725-2A patent/BR0313725A/pt not_active IP Right Cessation
- 2003-08-15 EA EA200500353A patent/EA200500353A1/ru unknown
- 2003-08-15 CN CNB038212935A patent/CN1315859C/zh not_active Expired - Fee Related
- 2003-08-15 AU AU2003265475A patent/AU2003265475B2/en not_active Ceased
- 2003-08-15 EP EP03788609A patent/EP1529052A2/en not_active Withdrawn
-
2005
- 2005-01-25 IL IL166476A patent/IL166476A/en not_active IP Right Cessation
- 2005-03-14 NO NO20051289A patent/NO20051289L/no unknown
Also Published As
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---|---|
US20040116690A1 (en) | 2004-06-17 |
WO2004016632A8 (en) | 2004-09-30 |
US7164011B2 (en) | 2007-01-16 |
CN1681832A (zh) | 2005-10-12 |
JP2006504673A (ja) | 2006-02-09 |
WO2004016632A3 (en) | 2004-06-24 |
EA200500353A1 (ru) | 2006-06-30 |
AU2003265475B2 (en) | 2009-08-27 |
AU2003265475A1 (en) | 2004-03-03 |
NZ538141A (en) | 2007-06-29 |
MXPA05001689A (es) | 2005-05-27 |
WO2004016632B1 (en) | 2004-08-19 |
BR0313725A (pt) | 2006-06-13 |
KR20050056195A (ko) | 2005-06-14 |
NO20051289L (no) | 2005-05-09 |
WO2004016632A2 (en) | 2004-02-26 |
CN1315859C (zh) | 2007-05-16 |
EP1529052A2 (en) | 2005-05-11 |
CA2493799A1 (en) | 2004-02-26 |
IL166476A (en) | 2010-05-31 |
IL166476A0 (en) | 2006-01-15 |
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