NZ536402A

NZ536402A - 6,11 bicyclic erythromycin derivatives

6,11 bicyclic erythromycin derivatives

Info

Publication number: NZ536402A
Authority: NZ; New Zealand
Prior art keywords: compound; formula; taken together; attached; carbon atom
Prior art date: 2002-05-13

Application number

NZ536402A

Other languages

English (en)

Inventor

Yat Sun Or

Guoqiang Wang

Ly Tam Phan

Deqiang Niu

Nha Huu Vo

Yao-Ling Qiu

Jay Judson Farmer

Ying Hou

Original Assignee

Enanta Pharm Inc

Priority date

2002-05-13

Filing date

2003-05-13

Publication date

2006-08-31

2003-05-13 Application filed by Enanta Pharm Inc filed Critical Enanta Pharm Inc

2003-05-13 Priority claimed from PCT/US2003/014914 external-priority patent/WO2003095466A1/en

2006-08-31 Publication of NZ536402A publication Critical patent/NZ536402A/en

Links

-1 bicyclic erythromycin derivatives Chemical class 0.000 title claims abstract description 50
150000001875 compounds Chemical class 0.000 claims abstract description 395
229910052799 carbon Inorganic materials 0.000 claims abstract description 199
238000000034 method Methods 0.000 claims abstract description 79
208000035143 Bacterial infection Diseases 0.000 claims abstract description 17
208000022362 bacterial infectious disease Diseases 0.000 claims abstract description 17
230000008569 process Effects 0.000 claims abstract description 16
150000003839 salts Chemical class 0.000 claims abstract description 16
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 12
150000002148 esters Chemical class 0.000 claims abstract description 8
239000000651 prodrug Substances 0.000 claims abstract description 7
229940002612 prodrug Drugs 0.000 claims abstract description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 143
125000001072 heteroaryl group Chemical group 0.000 claims description 70
239000000203 mixture Substances 0.000 claims description 67
239000002904 solvent Substances 0.000 claims description 62
229910052736 halogen Inorganic materials 0.000 claims description 54
150000002367 halogens Chemical class 0.000 claims description 54
125000004432 carbon atom Chemical group C* 0.000 claims description 51
125000003118 aryl group Chemical group 0.000 claims description 44
238000006243 chemical reaction Methods 0.000 claims description 41
125000001424 substituent group Chemical group 0.000 claims description 40
125000003107 substituted aryl group Chemical group 0.000 claims description 37
229910052739 hydrogen Inorganic materials 0.000 claims description 33
239000001257 hydrogen Substances 0.000 claims description 33
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 32
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
229910052757 nitrogen Inorganic materials 0.000 claims description 32
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 30
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 29
125000006239 protecting group Chemical group 0.000 claims description 28
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 26
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 24
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 23
239000003153 chemical reaction reagent Substances 0.000 claims description 23
229910052760 oxygen Inorganic materials 0.000 claims description 23
229910052717 sulfur Inorganic materials 0.000 claims description 23
125000005842 heteroatom Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
238000010992 reflux Methods 0.000 claims description 17
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
239000003054 catalyst Substances 0.000 claims description 16
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 15
239000000010 aprotic solvent Substances 0.000 claims description 14
239000003814 drug Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
125000004400 (C1-C12) alkyl group Chemical group 0.000 claims description 11
239000002168 alkylating agent Substances 0.000 claims description 11
229940100198 alkylating agent Drugs 0.000 claims description 11
125000000753 cycloalkyl group Chemical group 0.000 claims description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
238000003756 stirring Methods 0.000 claims description 10
239000002585 base Substances 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 7
239000003937 drug carrier Substances 0.000 claims description 7
229910052763 palladium Inorganic materials 0.000 claims description 7
YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 6
229910052805 deuterium Inorganic materials 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
230000004048 modification Effects 0.000 claims description 5
238000012986 modification Methods 0.000 claims description 5
125000004433 nitrogen atom Chemical group N* 0.000 claims description 5
239000003586 protic polar solvent Substances 0.000 claims description 5
125000006710 (C2-C12) alkenyl group Chemical group 0.000 claims description 4
125000006711 (C2-C12) alkynyl group Chemical group 0.000 claims description 4
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
239000003638 chemical reducing agent Substances 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
GNCMDULONSRFBV-FXBDTBDDSA-N C(C)(=O)O[C@]([C@](CC=O)(C)OC)(O)[C@@H](O)C Chemical compound C(C)(=O)O[C@]([C@](CC=O)(C)OC)(O)[C@@H](O)C GNCMDULONSRFBV-FXBDTBDDSA-N 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 3
239000000284 extract Substances 0.000 claims description 3
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 2
125000004404 heteroalkyl group Chemical group 0.000 claims description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 2
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims 1
230000007717 exclusion Effects 0.000 claims 1
239000002480 mineral oil Substances 0.000 claims 1
235000010446 mineral oil Nutrition 0.000 claims 1
238000007248 oxidative elimination reaction Methods 0.000 claims 1
125000004548 quinolin-3-yl group Chemical group N1=CC(=CC2=CC=CC=C12)* 0.000 claims 1
230000000844 anti-bacterial effect Effects 0.000 abstract description 8
150000001721 carbon Chemical group 0.000 description 144
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 89
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 55
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 54
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 50
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 50
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 50
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208000015181 infectious disease Diseases 0.000 description 43
235000019439 ethyl acetate Nutrition 0.000 description 30
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QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 26
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 24
235000019441 ethanol Nutrition 0.000 description 20
239000011541 reaction mixture Substances 0.000 description 20
239000012267 brine Substances 0.000 description 18
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 18
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 17
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 17
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 17
ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical class 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 16
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
239000012074 organic phase Substances 0.000 description 16
238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
239000003795 chemical substances by application Substances 0.000 description 15
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 14
229940086542 triethylamine Drugs 0.000 description 14
101150041968 CDC13 gene Proteins 0.000 description 13
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 13
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
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230000000694 effects Effects 0.000 description 12
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241000251468 Actinopterygii Species 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 11
229940079593 drug Drugs 0.000 description 11
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238000003786 synthesis reaction Methods 0.000 description 11
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 10
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201000010099 disease Diseases 0.000 description 10
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 10
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 description 10
229910000030 sodium bicarbonate Inorganic materials 0.000 description 10
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235000011152 sodium sulphate Nutrition 0.000 description 10
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 9
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