CN105669803A - 酮内酯化合物 - Google Patents
酮内酯化合物 Download PDFInfo
- Publication number
- CN105669803A CN105669803A CN201610004950.0A CN201610004950A CN105669803A CN 105669803 A CN105669803 A CN 105669803A CN 201610004950 A CN201610004950 A CN 201610004950A CN 105669803 A CN105669803 A CN 105669803A
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- CN
- China
- Prior art keywords
- compound
- base
- chemical formula
- thiadiazoles
- pyridine
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 469
- 239000003835 ketolide antibiotic agent Substances 0.000 title abstract description 16
- 239000001257 hydrogen Substances 0.000 claims abstract description 54
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 52
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 51
- 229910052731 fluorine Chemical group 0.000 claims abstract description 43
- 239000011737 fluorine Chemical group 0.000 claims abstract description 42
- 238000000034 method Methods 0.000 claims abstract description 42
- 239000011203 carbon fibre reinforced carbon Substances 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 37
- 125000003118 aryl group Chemical group 0.000 claims abstract description 31
- 208000015181 infectious disease Diseases 0.000 claims abstract description 31
- 239000012453 solvate Substances 0.000 claims abstract description 24
- 125000001153 fluoro group Chemical group F* 0.000 claims abstract description 23
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 9
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 239000000126 substance Substances 0.000 claims description 337
- 239000000203 mixture Substances 0.000 claims description 145
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 143
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 111
- -1 hydrogen Chemical class 0.000 claims description 99
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 73
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 43
- 125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 41
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 40
- 238000002360 preparation method Methods 0.000 claims description 40
- 229960003276 erythromycin Drugs 0.000 claims description 32
- 229930006677 Erythromycin A Natural products 0.000 claims description 30
- 238000011282 treatment Methods 0.000 claims description 18
- 239000003814 drug Substances 0.000 claims description 12
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 11
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 11
- 150000004867 thiadiazoles Chemical class 0.000 claims description 10
- 241000894006 Bacteria Species 0.000 claims description 9
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 244000005700 microbiome Species 0.000 claims description 6
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 claims description 3
- 241000233866 Fungi Species 0.000 claims description 3
- 241000221696 Sclerotinia sclerotiorum Species 0.000 claims description 3
- 241000235342 Saccharomycetes Species 0.000 claims description 2
- 210000000936 intestine Anatomy 0.000 claims description 2
- 230000000845 anti-microbial effect Effects 0.000 abstract description 2
- 230000000813 microbial effect Effects 0.000 abstract description 2
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 abstract 1
- 150000004677 hydrates Chemical class 0.000 abstract 1
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 169
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 129
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 113
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 101
- XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 81
- 238000003756 stirring Methods 0.000 description 73
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 62
- 238000006243 chemical reaction Methods 0.000 description 60
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 57
- 239000000376 reactant Substances 0.000 description 54
- 239000007787 solid Substances 0.000 description 53
- 239000002904 solvent Substances 0.000 description 53
- 239000001301 oxygen Substances 0.000 description 51
- 229910052760 oxygen Inorganic materials 0.000 description 51
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 49
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 46
- 239000000243 solution Substances 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
- 239000012044 organic layer Substances 0.000 description 45
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 41
- 239000012043 crude product Substances 0.000 description 39
- 238000001819 mass spectrum Methods 0.000 description 34
- 239000000725 suspension Substances 0.000 description 34
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 29
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 27
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 26
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 26
- 238000000605 extraction Methods 0.000 description 26
- 239000010410 layer Substances 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
- JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 22
- AMXOYNBUYSYVKV-UHFFFAOYSA-M lithium bromide Chemical compound [Li+].[Br-] AMXOYNBUYSYVKV-UHFFFAOYSA-M 0.000 description 22
- 238000004128 high performance liquid chromatography Methods 0.000 description 20
- 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 19
- 239000007864 aqueous solution Substances 0.000 description 19
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 17
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000000967 suction filtration Methods 0.000 description 16
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 15
- 239000003513 alkali Substances 0.000 description 15
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 14
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 14
- 150000007530 organic bases Chemical class 0.000 description 14
- 238000010898 silica gel chromatography Methods 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 239000012279 sodium borohydride Substances 0.000 description 13
- 229910000033 sodium borohydride Inorganic materials 0.000 description 13
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- GRJJQCWNZGRKAU-UHFFFAOYSA-N pyridin-1-ium;fluoride Chemical compound F.C1=CC=NC=C1 GRJJQCWNZGRKAU-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 11
- 229910052799 carbon Inorganic materials 0.000 description 11
- 238000004140 cleaning Methods 0.000 description 11
- 238000001704 evaporation Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 238000012545 processing Methods 0.000 description 11
- 235000017557 sodium bicarbonate Nutrition 0.000 description 11
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
- 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 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 10
- 241000193998 Streptococcus pneumoniae Species 0.000 description 10
- 239000000706 filtrate Substances 0.000 description 10
- CFHGBZLNZZVTAY-UHFFFAOYSA-N lawesson's reagent Chemical compound C1=CC(OC)=CC=C1P1(=S)SP(=S)(C=2C=CC(OC)=CC=2)S1 CFHGBZLNZZVTAY-UHFFFAOYSA-N 0.000 description 10
- 238000012544 monitoring process Methods 0.000 description 10
- 239000011734 sodium Substances 0.000 description 10
- LJVAJPDWBABPEJ-PNUFFHFMSA-N telithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N(CCCCN3C=C(N=C3)C=3C=NC=CC=3)[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O LJVAJPDWBABPEJ-PNUFFHFMSA-N 0.000 description 10
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 9
- 239000000460 chlorine Substances 0.000 description 9
- 229910052801 chlorine Inorganic materials 0.000 description 9
- 229940083668 ketek Drugs 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
- 241000606768 Haemophilus influenzae Species 0.000 description 8
- 201000005010 Streptococcus pneumonia Diseases 0.000 description 8
- 241000193996 Streptococcus pyogenes Species 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- 238000010511 deprotection reaction Methods 0.000 description 8
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 8
- 229910052763 palladium Inorganic materials 0.000 description 8
- HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
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- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 239000007832 Na2SO4 Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 7
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- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 description 5
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- PENDGIOBPJLVBT-ONLVEXIXSA-N (1r,2r,4r,6r,7r,8r,10r,13r,14s)-7-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-13-ethyl-2,4,6,8,10,14-hexamethyl-6-[(e)-3-quinolin-3-ylprop-2-enoxy]-12,15-dioxa-17-azabicyclo[12.3.0]heptadecane-3,9,11,16-tetrone Chemical compound O([C@@H]1[C@@H](C)C(=O)[C@@H](C)C(=O)O[C@@H]([C@]2(OC(=O)N[C@@H]2[C@@H](C)C(=O)[C@H](C)C[C@@]1(C)OC\C=C\C=1C=C2C=CC=CC2=NC=1)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O PENDGIOBPJLVBT-ONLVEXIXSA-N 0.000 description 4
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- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 4
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- 239000007858 starting material Substances 0.000 description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
- FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 4
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- KAESVJOAVNADME-UHFFFAOYSA-N 1H-pyrrole Natural products C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 3
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 3
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Classifications
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- 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
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/335—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin
- A61K31/35—Heterocyclic compounds having oxygen as the only ring hetero atom, e.g. fungichromin having six-membered rings with one oxygen as the only ring hetero atom
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H23/00—Compounds containing boron, silicon or a metal, e.g. chelates or vitamin B12
-
- 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
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- General Health & Medical Sciences (AREA)
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- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Molecular Biology (AREA)
- Biotechnology (AREA)
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- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
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Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IN3352/MUM/2010 | 2010-12-09 | ||
| IN3352MU2010 | 2010-12-09 |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201180066627.1A Division CN103384676B (zh) | 2010-12-09 | 2011-02-03 | 酮内酯化合物 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN105669803A true CN105669803A (zh) | 2016-06-15 |
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| CN201180066627.1A Active CN103384676B (zh) | 2010-12-09 | 2011-02-03 | 酮内酯化合物 |
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| Application Number | Title | Priority Date | Filing Date |
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| CN201180066627.1A Active CN103384676B (zh) | 2010-12-09 | 2011-02-03 | 酮内酯化合物 |
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| EP (2) | EP2673285B1 (enExample) |
| JP (2) | JP5851516B2 (enExample) |
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| CN (2) | CN105669803A (enExample) |
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| BR (1) | BR112013014392B1 (enExample) |
| CA (2) | CA2820451C (enExample) |
| DK (1) | DK2673285T3 (enExample) |
| ES (1) | ES2642287T3 (enExample) |
| HU (1) | HUE036658T2 (enExample) |
| MX (1) | MX348084B (enExample) |
| NZ (1) | NZ623574A (enExample) |
| PL (1) | PL2673285T3 (enExample) |
| PT (1) | PT2673285T (enExample) |
| RU (1) | RU2601550C2 (enExample) |
| WO (1) | WO2012076989A1 (enExample) |
| ZA (1) | ZA201304150B (enExample) |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ587490A (en) * | 2010-08-20 | 2013-03-28 | Greentide Ltd | Anti-Microbial Compounds containing compounds with a sugar substituent |
| WO2012127351A1 (en) * | 2011-03-22 | 2012-09-27 | Wockhardt Limited | Process for preparation of ketolide compounds |
| US9346828B2 (en) | 2013-06-07 | 2016-05-24 | Wisconsin Alumni Research Foundation | Forazolines, compositions thereof and uses thereof |
| NZ739026A (en) | 2015-07-27 | 2019-03-29 | Chong Kun Dang Pharmaceutical Corp | 1,3,4-oxadiazole sulfonamide derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same |
| PL3330259T3 (pl) * | 2015-07-27 | 2021-02-08 | Chong Kun Dang Pharmaceutical Corp. | Związek pochodna amidowa 1,3,4-oksadiazolu jako inhibitor deacetylazy histonowej 6 i kompozycja farmaceutyczna go zawierająca |
| KR101799005B1 (ko) | 2015-07-27 | 2017-11-17 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 설프아마이드 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
| BR112018002304B1 (pt) | 2015-08-04 | 2023-12-19 | Chong Kun Dang Pharmaceutical Corp | Compostos de derivado de 1,3,4-oxadiazol como inibidor de histona desacetilase 6 e a composição farmacêutica que compreende os mesmos |
| WO2017065473A1 (en) | 2015-10-12 | 2017-04-20 | Chong Kun Dang Pharmaceutical Corp. | Oxadiazole amine derivative compounds as histone deacetylase 6 inhibitor, and the pharmaceutical composition comprising the same |
| EP3402467A1 (en) * | 2016-01-12 | 2018-11-21 | Wockhardt Limited | Pharmaceutical compositions |
| WO2017122127A1 (en) * | 2016-01-12 | 2017-07-20 | Wockhardt Limited | Pharmaceutical compositions |
| EP3402487A1 (en) * | 2016-01-12 | 2018-11-21 | Wockhardt Limited | Pharmaceutical compositions for the treatment of bacterial infections |
| US20210122777A1 (en) * | 2017-03-16 | 2021-04-29 | Wockhardt Limited | A process for preparing ketolide compounds |
| KR102316234B1 (ko) | 2018-07-26 | 2021-10-22 | 주식회사 종근당 | 히스톤 탈아세틸화효소 6 억제제로서의 1,3,4-옥사다이아졸 유도체 화합물 및 이를 포함하는 약제학적 조성물 |
| MX2021014315A (es) | 2019-05-31 | 2022-01-04 | Chong Kun Dang Pharmaceutical Corp | Compuestos derivados de 1,3,4-oxadiazol homoftalimida como inhibidores de histona desacetilasa 6, y la composicion farmaceutica que comprende los mismos. |
| AU2020380395A1 (en) | 2019-11-05 | 2022-05-26 | Dermira, Inc. | MrgprX2 antagonists for the treatment of inflammatory disorders |
| WO2021092264A1 (en) * | 2019-11-05 | 2021-05-14 | Dermira, Inc. | MrgprX2 ANTAGONISTS AND USES THEREOF |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1235162A (zh) * | 1998-04-08 | 1999-11-17 | 赫斯特·马里恩·鲁索公司 | 新的红霉素的衍生物 |
| CN101541331A (zh) * | 2006-08-24 | 2009-09-23 | 沃克哈特研究中心 | 具有抗微生物活性的新颖大环内酯和酮内酯 |
| WO2009137787A1 (en) * | 2008-05-09 | 2009-11-12 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives |
| CN101855219A (zh) * | 2007-09-17 | 2010-10-06 | 英安塔制药有限公司 | 6，11-桥联的联芳大环内酯类 |
| WO2010136971A1 (en) * | 2009-05-27 | 2010-12-02 | Wockhardt Research Centre | Ketolide compounds having antimicrobial activity |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2473525A1 (fr) | 1980-01-11 | 1981-07-17 | Roussel Uclaf | Nouvelles oximes derivees de l'erythromycine, leur procede de preparation et leur application comme medicaments |
| US4331803A (en) | 1980-06-04 | 1982-05-25 | Taisho Pharmaceutical Co., Ltd. | Novel erythromycin compounds |
| YU43006B (en) | 1981-03-06 | 1989-02-28 | Pliva Pharm & Chem Works | Process for preparing n-methyl-11-aza-10-deoxo-10-dihydro erythromycin and derivatives thereof |
| FR2719587B1 (fr) | 1994-05-03 | 1996-07-12 | Roussel Uclaf | Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments. |
| BR9711661A (pt) | 1996-09-04 | 1999-08-24 | Abbott Lab | Composto composi-Æo farmac-utica e processos para controlar uma infec-Æo bacteriana em um mam¡fero e para preparar um composto |
| WO1999021870A1 (en) * | 1997-10-29 | 1999-05-06 | Taisho Pharmaceutical Co., Ltd. | Erythromycin a 11, 12-carbamate derivatives |
| HRP980189B1 (en) * | 1998-04-06 | 2004-04-30 | Pliva Pharm & Chem Works | Novel 15-membered lactams ketolides |
| US6740642B2 (en) | 2000-08-22 | 2004-05-25 | Basilea Parmaceutica Ag | Macrolides with antibacterial activity |
| US20040077557A1 (en) | 2000-12-21 | 2004-04-22 | Sulejman Ali | Macrolide antibiotics |
| GB0031312D0 (en) | 2000-12-21 | 2001-02-07 | Glaxo Group Ltd | Macrolides |
| GB0127349D0 (en) | 2001-11-14 | 2002-01-02 | Glaxo Group Ltd | Macrolides |
| US6995143B2 (en) | 2002-02-28 | 2006-02-07 | Basilea Pharmaceutica Ag | Macrolides with antibacterial activity |
| US6727229B2 (en) | 2002-08-19 | 2004-04-27 | Enanta Pharmaceuticals, Inc. | 11,12-substituted lactone ketolide derivatives having antibacterial activity |
| WO2004108744A2 (en) * | 2003-05-19 | 2004-12-16 | Prasad K Deshpande | Azalides and azaketolides having antimicrobial activity |
| EP1794171A2 (en) * | 2004-07-28 | 2007-06-13 | Ranbaxy Laboratories, Ltd. | Ketolide derivatives as antibacterial agents |
-
2011
- 2011-02-03 RU RU2013131234/04A patent/RU2601550C2/ru active
- 2011-02-03 ES ES11708092.9T patent/ES2642287T3/es active Active
- 2011-02-03 AU AU2011340204A patent/AU2011340204B2/en not_active Ceased
- 2011-02-03 JP JP2013542630A patent/JP5851516B2/ja not_active Expired - Fee Related
- 2011-02-03 KR KR1020137016527A patent/KR101657751B1/ko not_active Expired - Fee Related
- 2011-02-03 MX MX2013006461A patent/MX348084B/es active IP Right Grant
- 2011-02-03 EP EP11708092.9A patent/EP2673285B1/en active Active
- 2011-02-03 PT PT117080929T patent/PT2673285T/pt unknown
- 2011-02-03 US US13/991,762 patent/US9175031B2/en active Active
- 2011-02-03 HU HUE11708092A patent/HUE036658T2/hu unknown
- 2011-02-03 CN CN201610004950.0A patent/CN105669803A/zh active Pending
- 2011-02-03 EP EP17164547.6A patent/EP3216798A3/en not_active Withdrawn
- 2011-02-03 DK DK11708092.9T patent/DK2673285T3/en active
- 2011-02-03 PL PL11708092T patent/PL2673285T3/pl unknown
- 2011-02-03 CA CA2820451A patent/CA2820451C/en not_active Expired - Fee Related
- 2011-02-03 BR BR112013014392-4A patent/BR112013014392B1/pt active IP Right Grant
- 2011-02-03 NZ NZ623574A patent/NZ623574A/en not_active IP Right Cessation
- 2011-02-03 CA CA2964104A patent/CA2964104A1/en not_active Abandoned
- 2011-02-03 WO PCT/IB2011/050464 patent/WO2012076989A1/en not_active Ceased
- 2011-02-03 CN CN201180066627.1A patent/CN103384676B/zh active Active
-
2013
- 2013-06-06 ZA ZA2013/04150A patent/ZA201304150B/en unknown
-
2015
- 2015-07-06 JP JP2015135252A patent/JP6102991B2/ja not_active Expired - Fee Related
- 2015-09-19 US US14/859,254 patent/US20160083412A1/en not_active Abandoned
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1235162A (zh) * | 1998-04-08 | 1999-11-17 | 赫斯特·马里恩·鲁索公司 | 新的红霉素的衍生物 |
| CN101541331A (zh) * | 2006-08-24 | 2009-09-23 | 沃克哈特研究中心 | 具有抗微生物活性的新颖大环内酯和酮内酯 |
| CN101855219A (zh) * | 2007-09-17 | 2010-10-06 | 英安塔制药有限公司 | 6，11-桥联的联芳大环内酯类 |
| WO2009137787A1 (en) * | 2008-05-09 | 2009-11-12 | Enanta Pharmaceuticals, Inc. | Processes for the preparation of 2-fluoro 6-11 bicyclic erythromycin derivatives |
| WO2010136971A1 (en) * | 2009-05-27 | 2010-12-02 | Wockhardt Research Centre | Ketolide compounds having antimicrobial activity |
Non-Patent Citations (1)
| Title |
|---|
| 顾觉奋，等: "新一代大环内酯类抗生素——酮内酯类简介", 《抗感染药学》 * |
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Application publication date: 20160615 |