AU2004238528A1 - Novel 14 and 15 membered-ring compounds - Google Patents
Novel 14 and 15 membered-ring compounds Download PDFInfo
- Publication number
- AU2004238528A1 AU2004238528A1 AU2004238528A AU2004238528A AU2004238528A1 AU 2004238528 A1 AU2004238528 A1 AU 2004238528A1 AU 2004238528 A AU2004238528 A AU 2004238528A AU 2004238528 A AU2004238528 A AU 2004238528A AU 2004238528 A1 AU2004238528 A1 AU 2004238528A1
- Authority
- AU
- Australia
- Prior art keywords
- alkyl
- hydrogen
- optionally substituted
- ethyl
- oxo
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 150000001875 compounds Chemical class 0.000 title claims description 243
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 293
- 125000000217 alkyl group Chemical group 0.000 claims description 123
- 229910052739 hydrogen Inorganic materials 0.000 claims description 108
- 239000001257 hydrogen Substances 0.000 claims description 103
- -1 amine compound Chemical class 0.000 claims description 69
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
- 238000006243 chemical reaction Methods 0.000 claims description 62
- 125000000623 heterocyclic group Chemical group 0.000 claims description 55
- 238000000034 method Methods 0.000 claims description 49
- 125000003545 alkoxy group Chemical group 0.000 claims description 38
- 229960002626 clarithromycin Drugs 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 37
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 37
- 229960004099 azithromycin Drugs 0.000 claims description 32
- 229960003276 erythromycin Drugs 0.000 claims description 32
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000003342 alkenyl group Chemical group 0.000 claims description 23
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 23
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 22
- 241000282414 Homo sapiens Species 0.000 claims description 20
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
- 239000003814 drug Substances 0.000 claims description 18
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 18
- 229910052757 nitrogen Inorganic materials 0.000 claims description 17
- 238000011282 treatment Methods 0.000 claims description 16
- 239000008194 pharmaceutical composition Substances 0.000 claims description 15
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 14
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 13
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 12
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 12
- 125000004122 cyclic group Chemical group 0.000 claims description 12
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 12
- 125000006570 (C5-C6) heteroaryl group Chemical group 0.000 claims description 11
- 125000004429 atom Chemical group 0.000 claims description 11
- 239000003054 catalyst Substances 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 229910052770 Uranium Inorganic materials 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 10
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
- 125000006239 protecting group Chemical group 0.000 claims description 10
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 9
- 125000001072 heteroaryl group Chemical group 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 229910052760 oxygen Inorganic materials 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 241001465754 Metazoa Species 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 208000015181 infectious disease Diseases 0.000 claims description 6
- 230000000813 microbial effect Effects 0.000 claims description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
- 230000008569 process Effects 0.000 claims description 6
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 238000002560 therapeutic procedure Methods 0.000 claims description 6
- 230000000699 topical effect Effects 0.000 claims description 6
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 claims description 6
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 5
- 125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 claims description 5
- 238000011321 prophylaxis Methods 0.000 claims description 5
- 125000001424 substituent group Chemical group 0.000 claims description 5
- GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 4
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 4
- 101150065749 Churc1 gene Proteins 0.000 claims description 4
- 102100038239 Protein Churchill Human genes 0.000 claims description 4
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
- 230000009885 systemic effect Effects 0.000 claims description 4
- 101100010589 Bacillus anthracis dxr1 gene Proteins 0.000 claims description 3
- 101100294102 Caenorhabditis elegans nhr-2 gene Proteins 0.000 claims description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000004001 thioalkyl group Chemical group 0.000 claims description 3
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 196
- 239000000203 mixture Substances 0.000 description 125
- 239000000543 intermediate Substances 0.000 description 94
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 92
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 91
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 88
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 76
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 76
- 239000000243 solution Substances 0.000 description 73
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 65
- 239000007787 solid Substances 0.000 description 62
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 60
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 56
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 54
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 50
- 239000000741 silica gel Substances 0.000 description 49
- 229910002027 silica gel Inorganic materials 0.000 description 49
- 238000004587 chromatography analysis Methods 0.000 description 48
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 33
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 33
- 239000000047 product Substances 0.000 description 32
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 31
- 235000019439 ethyl acetate Nutrition 0.000 description 31
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- NKLCNNUWBJBICK-UHFFFAOYSA-N dess–martin periodinane Chemical compound C1=CC=C2I(OC(=O)C)(OC(C)=O)(OC(C)=O)OC(=O)C2=C1 NKLCNNUWBJBICK-UHFFFAOYSA-N 0.000 description 28
- 150000003839 salts Chemical class 0.000 description 28
- 229910052786 argon Inorganic materials 0.000 description 27
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 26
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 24
- 150000003254 radicals Chemical class 0.000 description 23
- 239000011541 reaction mixture Substances 0.000 description 22
- 230000002829 reductive effect Effects 0.000 description 22
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- 238000003756 stirring Methods 0.000 description 19
- 239000002253 acid Substances 0.000 description 18
- CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 18
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 18
- 239000000843 powder Substances 0.000 description 18
- 239000000725 suspension Substances 0.000 description 18
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical class OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 17
- 239000003480 eluent Substances 0.000 description 17
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 17
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 16
- 239000006260 foam Substances 0.000 description 16
- 229940044170 formate Drugs 0.000 description 16
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000012267 brine Substances 0.000 description 15
- 235000017557 sodium bicarbonate Nutrition 0.000 description 15
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 15
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 229960004132 diethyl ether Drugs 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
- 230000008020 evaporation Effects 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 238000001914 filtration Methods 0.000 description 13
- 235000019253 formic acid Nutrition 0.000 description 13
- 239000000463 material Substances 0.000 description 13
- 229920006395 saturated elastomer Polymers 0.000 description 13
- FEJUGLKDZJDVFY-UHFFFAOYSA-N 9-borabicyclo[3.3.1]nonane Substances C1CCC2CCCC1B2 FEJUGLKDZJDVFY-UHFFFAOYSA-N 0.000 description 12
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 ULGZDMOVFRHVEP-RWJQBGPGSA-N 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 12
- 239000012043 crude product Substances 0.000 description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000003208 petroleum Substances 0.000 description 12
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 12
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 11
- DTQVDTLACAAQTR-UHFFFAOYSA-M Trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-M 0.000 description 11
- 239000012074 organic phase Substances 0.000 description 11
- 239000008259 solid foam Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 10
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000002148 esters Chemical class 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 239000002244 precipitate Substances 0.000 description 10
- 239000000651 prodrug Substances 0.000 description 10
- 229940002612 prodrug Drugs 0.000 description 10
- 238000000746 purification Methods 0.000 description 10
- 238000004007 reversed phase HPLC Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- 239000012453 solvate Substances 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 9
- 238000009472 formulation Methods 0.000 description 9
- 229910052763 palladium Inorganic materials 0.000 description 9
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 9
- 229910000027 potassium carbonate Inorganic materials 0.000 description 9
- 239000001632 sodium acetate Substances 0.000 description 9
- 235000017281 sodium acetate Nutrition 0.000 description 9
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 8
- 229910002092 carbon dioxide Inorganic materials 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 239000003120 macrolide antibiotic agent Substances 0.000 description 8
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- 239000001569 carbon dioxide Substances 0.000 description 7
- 229950010035 davercin Drugs 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- 239000003826 tablet Substances 0.000 description 7
- SCZNXLWKYFICFV-UHFFFAOYSA-N 1,2,3,4,5,7,8,9-octahydropyrido[1,2-b]diazepine Chemical compound C1CCCNN2CCCC=C21 SCZNXLWKYFICFV-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 229920000858 Cyclodextrin Polymers 0.000 description 6
- 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 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 241000193996 Streptococcus pyogenes Species 0.000 description 6
- 239000008351 acetate buffer Substances 0.000 description 6
- 239000004480 active ingredient Substances 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 238000010828 elution Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000002808 molecular sieve Substances 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 6
- 229930006677 Erythromycin A Natural products 0.000 description 5
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 5
- 229920002472 Starch Polymers 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002775 capsule Substances 0.000 description 5
- 239000000460 chlorine Substances 0.000 description 5
- 239000003937 drug carrier Substances 0.000 description 5
- 239000000796 flavoring agent Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 238000002953 preparative HPLC Methods 0.000 description 5
- 239000011369 resultant mixture Substances 0.000 description 5
- 239000011780 sodium chloride Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 229940032147 starch Drugs 0.000 description 5
- 239000008107 starch Substances 0.000 description 5
- 235000019698 starch Nutrition 0.000 description 5
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 5
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
- AMKGKYQBASDDJB-UHFFFAOYSA-N 9$l^{2}-borabicyclo[3.3.1]nonane Chemical compound C1CCC2CCCC1[B]2 AMKGKYQBASDDJB-UHFFFAOYSA-N 0.000 description 4
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 4
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- 125000001113 thiadiazolyl group Chemical group 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000003871 white petrolatum Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 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
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GBGB0310986.5A GB0310986D0 (en) | 2003-05-13 | 2003-05-13 | Novel compounds |
| GB0310986.5 | 2003-05-13 | ||
| PCT/EP2004/005082 WO2004101586A1 (en) | 2003-05-13 | 2004-05-11 | Novel 14 and 15 membered-ring compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| AU2004238528A1 true AU2004238528A1 (en) | 2004-11-25 |
Family
ID=9957984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| AU2004238528A Abandoned AU2004238528A1 (en) | 2003-05-13 | 2004-05-11 | Novel 14 and 15 membered-ring compounds |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US7569550B2 (enExample) |
| EP (1) | EP1628988B1 (enExample) |
| JP (1) | JP2007502313A (enExample) |
| KR (1) | KR20060026407A (enExample) |
| CN (1) | CN1849328A (enExample) |
| AR (1) | AR044309A1 (enExample) |
| AT (1) | ATE341560T1 (enExample) |
| AU (1) | AU2004238528A1 (enExample) |
| BR (1) | BRPI0410246A (enExample) |
| CA (1) | CA2525452A1 (enExample) |
| CL (1) | CL2004001010A1 (enExample) |
| DE (1) | DE602004002696T2 (enExample) |
| DK (1) | DK1628988T3 (enExample) |
| ES (1) | ES2273255T3 (enExample) |
| GB (1) | GB0310986D0 (enExample) |
| HR (1) | HRP20060448T3 (enExample) |
| MX (1) | MXPA05012163A (enExample) |
| PL (1) | PL1628988T3 (enExample) |
| PT (1) | PT1628988E (enExample) |
| RU (1) | RU2005134908A (enExample) |
| WO (1) | WO2004101586A1 (enExample) |
| ZA (1) | ZA200509079B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0424961D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| GB0424958D0 (en) * | 2004-11-11 | 2004-12-15 | Glaxo Group Ltd | Novel compounds |
| EP1851236B1 (en) * | 2005-01-13 | 2010-08-04 | GlaxoSmithKline istrazivacki centar Zagreb d.o.o. | Macrolides with anti-inflammatory activity |
| WO2006120541A1 (en) * | 2005-05-10 | 2006-11-16 | Glaxosmithkline Istrazivacki Centar Zagreb D.O.O. | Ether linked macrolides useful for the treatment of microbial infections |
| PE20070802A1 (es) * | 2005-11-09 | 2007-10-19 | Glaxo Group Ltd | Derivados de eritromicina 4''-sustituidos como agentes antimicrobianos |
| EP1945652A1 (en) * | 2005-11-09 | 2008-07-23 | Glaxo Group Limited | Macrolones |
| EP2384333B1 (en) | 2009-01-30 | 2013-04-17 | Glaxo Group Limited | Anti-inflammatory macrolide |
| CN111574575B (zh) * | 2020-04-29 | 2022-05-17 | 北京理工大学 | 一种含有大环内酯基的喹喏酮衍生物、制备方法及应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| ATE128714T1 (de) * | 1989-03-28 | 1995-10-15 | Abbott Lab | Erythromycinderivate. |
| WO1996034007A1 (es) * | 1995-04-27 | 1996-10-31 | Laboratorios Aranda, S.A. De C.V. | Derivados de quinolonilcarboxieritromicina y composiciones farmaceuticas que los contienen |
| CA2253451A1 (en) * | 1996-05-07 | 1997-11-13 | Abbott Laboratories | 3-descladinose-2,3-anhydroerythromycin derivatives |
| GB0025688D0 (en) * | 2000-10-19 | 2000-12-06 | Glaxo Group Ltd | Macrolides |
| WO2003014136A1 (en) * | 2001-08-08 | 2003-02-20 | Taisho Pharmaceutical Co., Ltd. | 11a-AZALIDE COMPOUNDS AND PROCESS FOR PRODUCING THE SAME |
| GB0127349D0 (en) * | 2001-11-14 | 2002-01-02 | Glaxo Group Ltd | Macrolides |
-
2003
- 2003-05-13 GB GBGB0310986.5A patent/GB0310986D0/en not_active Ceased
-
2004
- 2004-05-11 RU RU2005134908/04A patent/RU2005134908A/ru not_active Application Discontinuation
- 2004-05-11 CL CL200401010A patent/CL2004001010A1/es unknown
- 2004-05-11 AT AT04732102T patent/ATE341560T1/de not_active IP Right Cessation
- 2004-05-11 HR HR20060448T patent/HRP20060448T3/xx unknown
- 2004-05-11 BR BRPI0410246-0A patent/BRPI0410246A/pt not_active IP Right Cessation
- 2004-05-11 DE DE602004002696T patent/DE602004002696T2/de not_active Expired - Lifetime
- 2004-05-11 CA CA002525452A patent/CA2525452A1/en not_active Abandoned
- 2004-05-11 US US10/556,645 patent/US7569550B2/en not_active Expired - Fee Related
- 2004-05-11 PL PL04732102T patent/PL1628988T3/pl unknown
- 2004-05-11 EP EP04732102A patent/EP1628988B1/en not_active Expired - Lifetime
- 2004-05-11 JP JP2006529794A patent/JP2007502313A/ja active Pending
- 2004-05-11 PT PT04732102T patent/PT1628988E/pt unknown
- 2004-05-11 AU AU2004238528A patent/AU2004238528A1/en not_active Abandoned
- 2004-05-11 DK DK04732102T patent/DK1628988T3/da active
- 2004-05-11 CN CNA2004800192646A patent/CN1849328A/zh active Pending
- 2004-05-11 AR ARP040101614A patent/AR044309A1/es not_active Application Discontinuation
- 2004-05-11 KR KR1020057021593A patent/KR20060026407A/ko not_active Withdrawn
- 2004-05-11 WO PCT/EP2004/005082 patent/WO2004101586A1/en not_active Ceased
- 2004-05-11 ES ES04732102T patent/ES2273255T3/es not_active Expired - Lifetime
- 2004-05-11 MX MXPA05012163A patent/MXPA05012163A/es active IP Right Grant
-
2005
- 2005-11-09 ZA ZA200509079A patent/ZA200509079B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US20070185117A1 (en) | 2007-08-09 |
| ATE341560T1 (de) | 2006-10-15 |
| AR044309A1 (es) | 2005-09-07 |
| CA2525452A1 (en) | 2004-11-25 |
| HRP20060448T3 (hr) | 2007-03-31 |
| GB0310986D0 (en) | 2003-06-18 |
| EP1628988A1 (en) | 2006-03-01 |
| MXPA05012163A (es) | 2006-05-19 |
| CL2004001010A1 (es) | 2005-03-18 |
| CN1849328A (zh) | 2006-10-18 |
| RU2005134908A (ru) | 2006-06-27 |
| DE602004002696T2 (de) | 2007-08-16 |
| PL1628988T3 (pl) | 2007-03-30 |
| ES2273255T3 (es) | 2007-05-01 |
| DK1628988T3 (da) | 2007-02-05 |
| ZA200509079B (en) | 2007-02-28 |
| DE602004002696D1 (de) | 2006-11-16 |
| WO2004101586A1 (en) | 2004-11-25 |
| EP1628988B1 (en) | 2006-10-04 |
| KR20060026407A (ko) | 2006-03-23 |
| BRPI0410246A (pt) | 2006-05-16 |
| JP2007502313A (ja) | 2007-02-08 |
| US7569550B2 (en) | 2009-08-04 |
| PT1628988E (pt) | 2007-01-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK1 | Application lapsed section 142(2)(a) - no request for examination in relevant period |