SK13972001A3 - Erytromycínové deriváty - Google Patents

Erytromycínové deriváty Download PDF

Info

Publication number: SK13972001A3
Authority: SK; Slovakia
Prior art keywords: group; substituted; alkyl group; represented; formula
Prior art date: 1999-04-08

Application number

SK1397-2001A

Other languages

English (en)

Slovak (sk)

Inventor

Hideo Kato

Noriyuki Kado

Toshihiko Yoshida

Akemi Nishimoto

Ken Narita

Original Assignee

Hokuriku Seiyaku Co., Ltd.

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1999-04-08

Filing date

2000-04-06

Publication date

2002-08-06

2000-04-06 Application filed by Hokuriku Seiyaku Co., Ltd. filed Critical Hokuriku Seiyaku Co., Ltd.

2002-08-06 Publication of SK13972001A3 publication Critical patent/SK13972001A3/sk

Links

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 title claims abstract description 21
125000000217 alkyl group Chemical group 0.000 claims abstract description 39
150000003839 salts Chemical class 0.000 claims abstract description 32
125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 18
125000003118 aryl group Chemical group 0.000 claims abstract description 18
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 14
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 13
239000003242 anti bacterial agent Substances 0.000 claims abstract description 11
239000003814 drug Substances 0.000 claims abstract description 11
125000002252 acyl group Chemical group 0.000 claims abstract description 10
125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 6
125000000278 alkyl amino alkyl group Chemical group 0.000 claims abstract description 6
125000006350 alkyl thio alkyl group Chemical group 0.000 claims abstract description 6
229910052717 sulfur Inorganic materials 0.000 claims abstract description 4
239000002253 acid Substances 0.000 claims description 29
238000002360 preparation method Methods 0.000 claims description 21
238000000034 method Methods 0.000 claims description 16
208000027531 mycobacterial infectious disease Diseases 0.000 claims description 9
239000004480 active ingredient Substances 0.000 claims description 7
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims 2
208000035473 Communicable disease Diseases 0.000 claims 1
241000894006 Bacteria Species 0.000 abstract description 12
230000000844 anti-bacterial effect Effects 0.000 abstract description 12
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 abstract description 11
229940079593 drug Drugs 0.000 abstract description 2
125000004430 oxygen atom Chemical group O* 0.000 abstract 2
125000004434 sulfur atom Chemical group 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 description 391
-1 nhexyl Chemical group 0.000 description 230
239000007787 solid Substances 0.000 description 139
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 121
150000001875 compounds Chemical class 0.000 description 117
230000000704 physical effect Effects 0.000 description 40
239000002904 solvent Substances 0.000 description 36
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 24
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
239000002585 base Substances 0.000 description 13
239000000243 solution Substances 0.000 description 13
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
125000004432 carbon atom Chemical group C* 0.000 description 12
150000002923 oximes Chemical class 0.000 description 12
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 12
101710094396 Hexon protein Proteins 0.000 description 11
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 10
238000005481 NMR spectroscopy Methods 0.000 description 9
239000011541 reaction mixture Substances 0.000 description 9
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 8
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
125000003545 alkoxy group Chemical group 0.000 description 8
229960002626 clarithromycin Drugs 0.000 description 8
AGOYDEPGAOXOCK-KCBOHYOISA-N clarithromycin 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)([C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)OC)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 AGOYDEPGAOXOCK-KCBOHYOISA-N 0.000 description 8
IMNFDUFMRHMDMM-UHFFFAOYSA-N n-heptane Substances CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 7
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 6
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
125000005605 benzo group Chemical group 0.000 description 6
229940125904 compound 1 Drugs 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
229910000030 sodium bicarbonate Inorganic materials 0.000 description 6
235000017557 sodium bicarbonate Nutrition 0.000 description 6
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical class OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 5
239000013256 coordination polymer Substances 0.000 description 5
239000013078 crystal Substances 0.000 description 5
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 5
239000004210 ether based solvent Substances 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
239000002798 polar solvent Substances 0.000 description 5
125000006239 protecting group Chemical group 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
229910052938 sodium sulfate Inorganic materials 0.000 description 5
235000011152 sodium sulphate Nutrition 0.000 description 5
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 4
229930006677 Erythromycin A Natural products 0.000 description 4
HOPRXXXSABQWAV-UHFFFAOYSA-N anhydrous collidine Natural products CC1=CC=NC(C)=C1C HOPRXXXSABQWAV-UHFFFAOYSA-N 0.000 description 4
125000004104 aryloxy group Chemical group 0.000 description 4
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000002512 chemotherapy Methods 0.000 description 4
UTBIMNXEDGNJFE-UHFFFAOYSA-N collidine Natural products CC1=CC=C(C)C(C)=N1 UTBIMNXEDGNJFE-UHFFFAOYSA-N 0.000 description 4
238000004440 column chromatography Methods 0.000 description 4
238000001816 cooling Methods 0.000 description 4
HPYNZHMRTTWQTB-UHFFFAOYSA-N dimethylpyridine Natural products CC1=CC=CN=C1C HPYNZHMRTTWQTB-UHFFFAOYSA-N 0.000 description 4
201000010099 disease Diseases 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
229960003276 erythromycin Drugs 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
125000005843 halogen group Chemical group 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
239000000546 pharmaceutical excipient Substances 0.000 description 4
239000000741 silica gel Substances 0.000 description 4
229910002027 silica gel Inorganic materials 0.000 description 4
229960001866 silicon dioxide Drugs 0.000 description 4
229910000029 sodium carbonate Inorganic materials 0.000 description 4
235000017550 sodium carbonate Nutrition 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
GFYHSKONPJXCDE-UHFFFAOYSA-N sym-collidine Natural products CC1=CN=C(C)C(C)=C1 GFYHSKONPJXCDE-UHFFFAOYSA-N 0.000 description 4
ISXOBTBCNRIIQO-UHFFFAOYSA-N tetrahydrothiophene 1-oxide Chemical compound O=S1CCCC1 ISXOBTBCNRIIQO-UHFFFAOYSA-N 0.000 description 4
230000001225 therapeutic effect Effects 0.000 description 4
XULIXFLCVXWHRF-UHFFFAOYSA-N 1,2,2,6,6-pentamethylpiperidine Chemical compound CN1C(C)(C)CCCC1(C)C XULIXFLCVXWHRF-UHFFFAOYSA-N 0.000 description 3
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
208000001388 Opportunistic Infections Diseases 0.000 description 3
239000002202 Polyethylene glycol Substances 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 3
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 3
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
UMFITLNWRPIUFW-CYPONQCLSA-N [H][C@@]1(C[C@@](C)(OC)[C@@]([H])(OC(C)=O)[C@H](C)O1)O[C@]1([H])[C@H](C)C(=O)O[C@]([H])(CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@]([H])(O[C@]2([H])O[C@H](C)C[C@@]([H])([C@H]2O)N(C)C)[C@H]1C Chemical compound [H][C@@]1(C[C@@](C)(OC)[C@@]([H])(OC(C)=O)[C@H](C)O1)O[C@]1([H])[C@H](C)C(=O)O[C@]([H])(CC)[C@@](C)(O)[C@H](O)[C@@H](C)C(=O)[C@H](C)C[C@@](C)(O)[C@]([H])(O[C@]2([H])O[C@H](C)C[C@@]([H])([C@H]2O)N(C)C)[C@H]1C UMFITLNWRPIUFW-CYPONQCLSA-N 0.000 description 3
KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
125000005098 aryl alkoxy carbonyl group Chemical group 0.000 description 3
125000005161 aryl oxy carbonyl group Chemical group 0.000 description 3
239000003759 ester based solvent Substances 0.000 description 3
239000003889 eye drop Substances 0.000 description 3
229940012356 eye drops Drugs 0.000 description 3
235000011187 glycerol Nutrition 0.000 description 3
150000008282 halocarbons Chemical class 0.000 description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
208000015181 infectious disease Diseases 0.000 description 3
239000007924 injection Substances 0.000 description 3
238000002347 injection Methods 0.000 description 3
150000007529 inorganic bases Chemical class 0.000 description 3
125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 3
239000003120 macrolide antibiotic agent Substances 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
150000007530 organic bases Chemical class 0.000 description 3
229920001223 polyethylene glycol Polymers 0.000 description 3
239000011736 potassium bicarbonate Substances 0.000 description 3
235000015497 potassium bicarbonate Nutrition 0.000 description 3
229910000028 potassium bicarbonate Inorganic materials 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
235000011181 potassium carbonates Nutrition 0.000 description 3
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 3
JQXXHWHPUNPDRT-WLSIYKJHSA-N rifampicin Chemical compound O([C@](C1=O)(C)O/C=C/[C@@H]([C@H]([C@@H](OC(C)=O)[C@H](C)[C@H](O)[C@H](C)[C@@H](O)[C@@H](C)\C=C\C=C(C)/C(=O)NC=2C(O)=C3C([O-])=C4C)C)OC)C4=C1C3=C(O)C=2\C=N\N1CC[NH+](C)CC1 JQXXHWHPUNPDRT-WLSIYKJHSA-N 0.000 description 3
229960001225 rifampicin Drugs 0.000 description 3
238000001228 spectrum Methods 0.000 description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
125000005301 thienylmethyl group Chemical group [H]C1=C([H])C([H])=C(S1)C([H])([H])* 0.000 description 3
229920002134 Carboxymethyl cellulose Polymers 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
239000012346 acetyl chloride Substances 0.000 description 2
150000008065 acid anhydrides Chemical class 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
235000010948 carboxy methyl cellulose Nutrition 0.000 description 2
239000008112 carboxymethyl-cellulose Substances 0.000 description 2
CVBHEIRZLPKMSH-SNWVVRALSA-N erythromycin acistrate 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)OC(C)=O)[C@H]1C)(C)O)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 CVBHEIRZLPKMSH-SNWVVRALSA-N 0.000 description 2
239000003885 eye ointment Substances 0.000 description 2
125000000524 functional group Chemical group 0.000 description 2
239000008187 granular material Substances 0.000 description 2
239000001866 hydroxypropyl methyl cellulose Substances 0.000 description 2
235000010979 hydroxypropyl methyl cellulose Nutrition 0.000 description 2
229920003088 hydroxypropyl methyl cellulose Polymers 0.000 description 2
UFVKGYZPFZQRLF-UHFFFAOYSA-N hydroxypropyl methyl cellulose Chemical compound OC1C(O)C(OC)OC(CO)C1OC1C(O)C(O)C(OC2C(C(O)C(OC3C(C(O)C(O)C(CO)O3)O)C(CO)O2)O)C(CO)O1 UFVKGYZPFZQRLF-UHFFFAOYSA-N 0.000 description 2
229940090044 injection Drugs 0.000 description 2
125000006352 iso-propylthiomethyl group Chemical group [H]C([H])([H])C([H])(SC([H])([H])*)C([H])([H])[H] 0.000 description 2
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
239000011780 sodium chloride Substances 0.000 description 2
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125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
125000004344 phenylpropyl group Chemical group 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
239000004014 plasticizer Substances 0.000 description 1
229920000435 poly(dimethylsiloxane) Polymers 0.000 description 1
235000013809 polyvinylpolypyrrolidone Nutrition 0.000 description 1
229920000523 polyvinylpolypyrrolidone Polymers 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
230000000069 prophylactic effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
NRTYMEPCRDJMPZ-UHFFFAOYSA-N pyridine;2,2,2-trifluoroacetic acid Chemical compound C1=CC=NC=C1.OC(=O)C(F)(F)F NRTYMEPCRDJMPZ-UHFFFAOYSA-N 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000719 pyrrolidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000005493 quinolyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229960005224 roxithromycin Drugs 0.000 description 1
CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical class OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 1
125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229960004029 silicic acid Drugs 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
150000003890 succinate salts Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
238000001356 surgical procedure Methods 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
238000012360 testing method Methods 0.000 description 1
TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical class CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
239000001069 triethyl citrate Substances 0.000 description 1
VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
235000013769 triethyl citrate Nutrition 0.000 description 1
WTVXIBRMWGUIMI-UHFFFAOYSA-N trifluoro($l^{1}-oxidanylsulfonyl)methane Chemical group [O]S(=O)(=O)C(F)(F)F WTVXIBRMWGUIMI-UHFFFAOYSA-N 0.000 description 1
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-M valerate Chemical class CCCCC([O-])=O NQPDZGIKBAWPEJ-UHFFFAOYSA-M 0.000 description 1
230000029812 viral genome replication Effects 0.000 description 1
239000001993 wax Substances 0.000 description 1

Classifications

- 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
- 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

Landscapes

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

SK1397-2001A 1999-04-08 2000-04-06 Erytromycínové deriváty SK13972001A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
JP10072699		1999-04-08
PCT/JP2000/002226 WO2000061593A1 (fr)	1999-04-08	2000-04-06	Derives d'erythromycine

Publications (1)

Publication Number	Publication Date
SK13972001A3 true SK13972001A3 (sk)	2002-08-06

Family

ID=14281635

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1397-2001A SK13972001A3 (sk)	1999-04-08	2000-04-06	Erytromycínové deriváty

Country Status (19)

Country	Link
EP (1)	EP1167375A4 (fr)
KR (1)	KR20020007333A (fr)
CN (1)	CN1343216A (fr)
AR (1)	AR023264A1 (fr)
AU (1)	AU3671000A (fr)
BG (1)	BG105919A (fr)
BR (1)	BR0010518A (fr)
CA (1)	CA2367319A1 (fr)
CZ (1)	CZ20013497A3 (fr)
HK (1)	HK1045697A1 (fr)
HU (1)	HUP0201116A3 (fr)
IL (1)	IL145256A0 (fr)
NO (1)	NO20014362L (fr)
NZ (1)	NZ513998A (fr)
PL (1)	PL354409A1 (fr)
SK (1)	SK13972001A3 (fr)
TR (1)	TR200102572T2 (fr)
WO (1)	WO2000061593A1 (fr)
ZA (1)	ZA200107346B (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP4025548B2 (ja) *	2000-02-24	2007-12-19	アボット・ラボラトリーズ	多薬剤耐性菌株に対して有用な抗感染症薬
US6946446B2 (en)	2000-02-24	2005-09-20	Abbott Laboratories	Anti-infective agents useful against multidrug-resistant strains of bacteria
JP2002173498A (ja) *	2000-09-27	2002-06-21	Hokuriku Seiyaku Co Ltd	エリスロマイシン誘導体
UY27429A1 (es) *	2001-09-05	2003-10-31	Hokuriku Pharmaceutical	Medicamento para el tratamiento terapéutico o preventivo de la tuberculosis que comprende un derivado de eritromicina
CA2801100A1 (fr)	2003-03-10	2004-09-23	Optimer Pharmaceuticals, Inc.	Macrolides et procedes de preparation associes
WO2004108744A2 (fr) *	2003-05-19	2004-12-16	Prasad K Deshpande	Azalides et azaketolides possedant une activite antimicrobienne
US7547679B2 (en)	2005-05-10	2009-06-16	Glaxosmithkline Istrazivacki Center Zagreb D.O.O	Ether linked macrolides useful for the treatment of microbial infections
AU2008316830B2 (en)	2007-10-25	2016-03-17	Cempra Pharmaceuticals, Inc.	Process for the preparation of macrolide antibacterial agents
CN102245195B (zh)	2008-10-24	2016-01-13	森普拉制药公司	使用含三唑的大环内酯的生物防御
US9937194B1 (en)	2009-06-12	2018-04-10	Cempra Pharmaceuticals, Inc.	Compounds and methods for treating inflammatory diseases
CN102724874B (zh)	2009-09-10	2018-06-01	森普拉制药公司	治疗疟疾、结核病和mac疾病的方法
CN102917708B (zh) *	2010-05-20	2015-11-25	森普拉制药公司	制备大环内酯和酮内酯及其中间体的方法
US9815863B2 (en)	2010-09-10	2017-11-14	Cempra Pharmaceuticals, Inc.	Hydrogen bond forming fluoro ketolides for treating diseases
KR20140139083A (ko)	2012-03-27	2014-12-04	셈프라 파마슈티컬스, 인크.	마크롤라이드계 항생제를 투여하기 위한 비경구 제제
CA2905975A1 (fr)	2013-03-14	2014-09-25	Cempra Pharmaceuticals, Inc.	Procedes pour traiter des maladies respiratoires et formulations pour la mise en oeuvre de ceux-ci
JP6675973B2 (ja)	2013-03-15	2020-04-08	センプラファーマシューティカルズ，インコーポレイテッド	マクロライド抗菌薬を調製するための集束的な方法
EP2984087A1 (fr) *	2013-04-10	2016-02-17	Probiotic Pharmaceuticals APS	Dérivés antimicrobiens d'azithromycine à effet pharmaceutique non antibiotique

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NO860901L (no) *	1985-03-12	1986-09-15	Beecham Group Plc	Fremgangsmaate for fremstilling av farmasoeytisk aktive erytromycinderivater.
GB8506380D0 (en) *	1985-03-12	1985-04-11	Beecham Group Plc	Chemical compounds
US5302705A (en) *	1989-10-07	1994-04-12	Taisho Pharmaceutical Co., Ltd.	6-O-methylerythromycin a oxime derivatives
US5719272A (en) *	1996-04-02	1998-02-17	Abbott Laboratories	2'-protected 3'-dimethylamine, 9-etheroxime erythromycin A derivatives
EP0895999A1 (fr) *	1997-08-06	1999-02-10	Pfizer Products Inc.	Macrolides antibiotiques substitués C"-4

2000
- 2000-04-05 AR ARP000101551A patent/AR023264A1/es unknown
- 2000-04-06 SK SK1397-2001A patent/SK13972001A3/sk unknown
- 2000-04-06 NZ NZ513998A patent/NZ513998A/xx not_active Application Discontinuation
- 2000-04-06 PL PL00354409A patent/PL354409A1/xx unknown
- 2000-04-06 KR KR1020017011771A patent/KR20020007333A/ko not_active Withdrawn
- 2000-04-06 BR BR0010518-0A patent/BR0010518A/pt not_active IP Right Cessation
- 2000-04-06 AU AU36710/00A patent/AU3671000A/en not_active Abandoned
- 2000-04-06 IL IL14525600A patent/IL145256A0/xx unknown
- 2000-04-06 CN CN00805014A patent/CN1343216A/zh active Pending
- 2000-04-06 HU HU0201116A patent/HUP0201116A3/hu unknown
- 2000-04-06 HK HK02107210.7A patent/HK1045697A1/zh unknown
- 2000-04-06 EP EP20000915372 patent/EP1167375A4/fr not_active Withdrawn
- 2000-04-06 CA CA002367319A patent/CA2367319A1/fr not_active Abandoned
- 2000-04-06 TR TR2001/02572T patent/TR200102572T2/xx unknown
- 2000-04-06 CZ CZ20013497A patent/CZ20013497A3/cs unknown
- 2000-04-06 WO PCT/JP2000/002226 patent/WO2000061593A1/fr not_active Ceased
2001
- 2001-09-05 ZA ZA200107346A patent/ZA200107346B/xx unknown
- 2001-09-07 NO NO20014362A patent/NO20014362L/no not_active Application Discontinuation
- 2001-09-19 BG BG105919A patent/BG105919A/xx unknown

Also Published As

Publication number	Publication date
KR20020007333A (ko)	2002-01-26
HUP0201116A3 (en)	2003-03-28
HUP0201116A2 (en)	2002-08-28
ZA200107346B (en)	2002-11-27
HK1045697A1 (zh)	2002-12-06
IL145256A0 (en)	2002-06-30
NZ513998A (en)	2001-09-28
BG105919A (en)	2002-06-28
EP1167375A1 (fr)	2002-01-02
PL354409A1 (en)	2004-01-12
EP1167375A4 (fr)	2002-10-30
AU3671000A (en)	2000-11-14
CZ20013497A3 (cs)	2002-05-15
CN1343216A (zh)	2002-04-03
AR023264A1 (es)	2002-09-04
NO20014362L (no)	2001-12-04
NO20014362D0 (no)	2001-09-07
BR0010518A (pt)	2002-01-08
WO2000061593A1 (fr)	2000-10-19
TR200102572T2 (tr)	2002-02-21
CA2367319A1 (fr)	2000-10-19

Publication	Publication Date	Title
SK13972001A3 (sk)	2002-08-06	Erytromycínové deriváty
CA3021061C (fr)	2023-10-24	Derives d'amphotericine b
EP3848366A1 (fr)	2021-07-14	Composé agoniste de protéine sting à activité élevée
JP7618553B2 (ja)	2025-01-21	ラパマイシン誘導体
EP3265083B1 (fr)	2022-07-06	Analogues de depsipeptide d'urée substitués à utiliser en tant qu'activateurs de l'endopeptidase clpp
EP2569324A1 (fr)	2013-03-20	Dérivés d'aminoglycoside
DE69610145T2 (de)	2001-06-07	Benzo-kondensierte Azepinon-und Piperidinonverbindungen, nützlich als ACE-und NEP-Inhibitoren
EP1165601A2 (fr)	2002-01-02	Promedicaments d'inhibiteurs de la thrombine
EP3506922B1 (fr)	2024-05-08	Analogues de depsipeptide d'urée substitués à utiliser en tant qu'activateurs de l'endopeptidase clpp
EP2692728A1 (fr)	2014-02-05	Nouveau dérivé de furanone
EP4406962A1 (fr)	2024-07-31	Inhibiteur de protéase peptidomimétique macrocyclique et son utilisation
AU2014252462A1 (en)	2015-10-01	Azithromycin antimicrobial derivatives with non-antibiotic pharmaceutical effect
EP3704103A1 (fr)	2020-09-09	Inhibiteurs de kinase pour le traitement de troubles du système nerveux central et périphérique
JP2000351794A (ja)	2000-12-19	エリスロマイシン誘導体
EP1044985A1 (fr)	2000-10-18	Derives d'erythromycine
US20040127433A1 (en)	2004-07-01	Erythromycin derivative and medicament comprising the same
EP4089079A1 (fr)	2022-11-16	Inhibiteur de ror gamma t, son procédé de préparation et son utilisation
JP7495758B2 (ja)	2024-06-05	マクロライド化合物及びその慢性呼吸器疾患の治療用途
WO2018067663A2 (fr)	2018-04-12	Cétolides à activité antibactrienne
MXPA01009306A (es)	2002-03-26	Derivados de eritromicina
CA2235942C (fr)	2005-12-06	Derives tricycliques d'erythromycine
JPH05117280A (ja)	1993-05-14	アミノ酸置換チアゼトキノリン−３−カルボン酸誘導体
HK40048031A (en)	2021-11-26	Highly active sting protein agonist compound
HK1244248B (en)	2021-09-10	Derivatives of amphotericin b
JPH08104638A (ja)	1996-04-23	Ｉｌ−５産生抑制剤