HRP950145A2 - New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof - Google Patents
New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof Download PDFInfo
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- HRP950145A2 HRP950145A2 HR950145A HRP950145A HRP950145A2 HR P950145 A2 HRP950145 A2 HR P950145A2 HR 950145 A HR950145 A HR 950145A HR P950145 A HRP950145 A HR P950145A HR P950145 A2 HRP950145 A2 HR P950145A2
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- 150000001875 compounds Chemical class 0.000 title claims description 76
- 238000000034 method Methods 0.000 title claims description 38
- 230000008569 process Effects 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 33
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical group ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 30
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
- 230000002829 reductive effect Effects 0.000 claims description 26
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 24
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 claims description 23
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 22
- 125000002252 acyl group Chemical group 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 22
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 21
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 18
- 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 claims description 18
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 18
- 239000012442 inert solvent Substances 0.000 claims description 18
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims description 17
- -1 R9 has the meaning H Chemical group 0.000 claims description 17
- 229960003276 erythromycin Drugs 0.000 claims description 17
- 229930006677 Erythromycin A Natural products 0.000 claims description 16
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 15
- 239000002253 acid Substances 0.000 claims description 15
- 150000007522 mineralic acids Chemical class 0.000 claims description 15
- 150000007524 organic acids Chemical class 0.000 claims description 15
- 229940093915 gynecological organic acid Drugs 0.000 claims description 14
- 235000005985 organic acids Nutrition 0.000 claims description 14
- 230000006179 O-acylation Effects 0.000 claims description 13
- 150000001805 chlorine compounds Chemical class 0.000 claims description 13
- 101100079984 Caenorhabditis elegans nhr-9 gene Proteins 0.000 claims description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 12
- 230000009471 action Effects 0.000 claims description 12
- 150000007529 inorganic bases Chemical class 0.000 claims description 12
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
- 150000007530 organic bases Chemical class 0.000 claims description 12
- 229910000027 potassium carbonate Inorganic materials 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000002904 solvent Substances 0.000 claims description 11
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 claims description 10
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 10
- 230000007062 hydrolysis Effects 0.000 claims description 10
- 238000006460 hydrolysis reaction Methods 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 10
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 10
- 229960000583 acetic acid Drugs 0.000 claims description 9
- 238000005917 acylation reaction Methods 0.000 claims description 9
- 125000004391 aryl sulfonyl group Chemical group 0.000 claims description 8
- 230000010933 acylation Effects 0.000 claims description 7
- 238000010531 catalytic reduction reaction Methods 0.000 claims description 7
- 239000012362 glacial acetic acid Substances 0.000 claims description 7
- 238000006140 methanolysis reaction Methods 0.000 claims description 7
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
- YKIOKAURTKXMSB-UHFFFAOYSA-N adams's catalyst Chemical group O=[Pt]=O YKIOKAURTKXMSB-UHFFFAOYSA-N 0.000 claims description 6
- 150000008064 anhydrides Chemical class 0.000 claims description 6
- 235000019253 formic acid Nutrition 0.000 claims description 6
- 238000007126 N-alkylation reaction Methods 0.000 claims description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 5
- 239000002168 alkylating agent Substances 0.000 claims description 4
- 229940100198 alkylating agent Drugs 0.000 claims description 4
- 239000003054 catalyst Substances 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- DENKGPBHLYFNGK-UHFFFAOYSA-N 4-bromobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Br)C=C1 DENKGPBHLYFNGK-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
- 238000010992 reflux Methods 0.000 claims description 3
- 125000002672 4-bromobenzoyl group Chemical group BrC1=CC=C(C(=O)*)C=C1 0.000 claims description 2
- 239000000908 ammonium hydroxide Substances 0.000 claims description 2
- 229910000510 noble metal Inorganic materials 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims 23
- 125000003172 aldehyde group Chemical group 0.000 claims 1
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 80
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 49
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 36
- 239000000047 product Substances 0.000 description 36
- 150000002923 oximes Chemical class 0.000 description 28
- 239000011541 reaction mixture Substances 0.000 description 27
- 238000005160 1H NMR spectroscopy Methods 0.000 description 24
- 239000000284 extract Substances 0.000 description 20
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 19
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 17
- 235000011114 ammonium hydroxide Nutrition 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 14
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- 239000000203 mixture Substances 0.000 description 14
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- 239000000126 substance Substances 0.000 description 14
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 13
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 13
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- 238000004587 chromatography analysis Methods 0.000 description 12
- 230000008020 evaporation Effects 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 11
- 239000012634 fragment Substances 0.000 description 10
- 235000015320 potassium carbonate Nutrition 0.000 description 10
- 239000012043 crude product Substances 0.000 description 9
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- 238000001035 drying Methods 0.000 description 5
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- 235000017557 sodium bicarbonate Nutrition 0.000 description 5
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- ILJSQTXMGCGYMG-UHFFFAOYSA-N triacetic acid Chemical compound CC(=O)CC(=O)CC(O)=O ILJSQTXMGCGYMG-UHFFFAOYSA-N 0.000 description 5
- 229910019020 PtO2 Inorganic materials 0.000 description 4
- MJOQJPYNENPSSS-XQHKEYJVSA-N [(3r,4s,5r,6s)-4,5,6-triacetyloxyoxan-3-yl] acetate Chemical compound CC(=O)O[C@@H]1CO[C@@H](OC(C)=O)[C@H](OC(C)=O)[C@H]1OC(C)=O MJOQJPYNENPSSS-XQHKEYJVSA-N 0.000 description 4
- 238000002955 isolation Methods 0.000 description 4
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 235000017550 sodium carbonate Nutrition 0.000 description 4
- HRKNNHYKWGYTEN-HOQMJRDDSA-N (2r,3s,4r,5r,8r,10r,11r,12s,13s,14r)-11-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-2-ethyl-3,4,10-trihydroxy-13-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,8,10,12,14-hexamethyl-1-oxa-6-azacyclopentadecan-15-one Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)NC[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 HRKNNHYKWGYTEN-HOQMJRDDSA-N 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- MQTOSJVFKKJCRP-BICOPXKESA-N azithromycin Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)N(C)C[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 MQTOSJVFKKJCRP-BICOPXKESA-N 0.000 description 3
- 229960004099 azithromycin Drugs 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 3
- 238000002451 electron ionisation mass spectrometry Methods 0.000 description 3
- 239000000543 intermediate Substances 0.000 description 3
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Natural products C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 3
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- TUXYZHVUPGXXQG-UHFFFAOYSA-M 4-bromobenzoate Chemical compound [O-]C(=O)C1=CC=C(Br)C=C1 TUXYZHVUPGXXQG-UHFFFAOYSA-M 0.000 description 2
- TWCMVXMQHSVIOJ-UHFFFAOYSA-N Aglycone of yadanzioside D Natural products COC(=O)C12OCC34C(CC5C(=CC(O)C(O)C5(C)C3C(O)C1O)C)OC(=O)C(OC(=O)C)C24 TWCMVXMQHSVIOJ-UHFFFAOYSA-N 0.000 description 2
- PLMKQQMDOMTZGG-UHFFFAOYSA-N Astrantiagenin E-methylester Natural products CC12CCC(O)C(C)(CO)C1CCC1(C)C2CC=C2C3CC(C)(C)CCC3(C(=O)OC)CCC21C PLMKQQMDOMTZGG-UHFFFAOYSA-N 0.000 description 2
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- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 2
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- QKLXBIHSGMPUQS-FGZHOGPDSA-M (3r,5r)-7-[4-(4-fluorophenyl)-2,5-dimethyl-1-phenylpyrrol-3-yl]-3,5-dihydroxyheptanoate Chemical compound CC1=C(CC[C@@H](O)C[C@@H](O)CC([O-])=O)C(C=2C=CC(F)=CC=2)=C(C)N1C1=CC=CC=C1 QKLXBIHSGMPUQS-FGZHOGPDSA-M 0.000 description 1
- PNHBRYIAJCYNDA-VQCQRNETSA-N (4r)-6-[2-[2-ethyl-4-(4-fluorophenyl)-6-phenylpyridin-3-yl]ethyl]-4-hydroxyoxan-2-one Chemical compound C([C@H](O)C1)C(=O)OC1CCC=1C(CC)=NC(C=2C=CC=CC=2)=CC=1C1=CC=C(F)C=C1 PNHBRYIAJCYNDA-VQCQRNETSA-N 0.000 description 1
- MNIPVWXWSPXERA-IDNZQHFXSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecanoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)CCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 MNIPVWXWSPXERA-IDNZQHFXSA-N 0.000 description 1
- QOLHWXNSCZGWHK-BWBORTOCSA-N (6r,7r)-1-[(4s,5r)-4-acetyloxy-5-methyl-3-methylidene-6-phenylhexyl]-4,7-dihydroxy-6-(11-phenoxyundecylcarbamoyloxy)-2,8-dioxabicyclo[3.2.1]octane-3,4,5-tricarboxylic acid Chemical compound C([C@@H](C)[C@H](OC(C)=O)C(=C)CCC12[C@@H]([C@@H](OC(=O)NCCCCCCCCCCCOC=3C=CC=CC=3)C(O1)(C(O)=O)C(O)(C(O2)C(O)=O)C(O)=O)O)C1=CC=CC=C1 QOLHWXNSCZGWHK-BWBORTOCSA-N 0.000 description 1
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- YLLRPQWLASQXSI-UHFFFAOYSA-N 3-(4b,8a,9,9a-tetrahydro-4aH-pyrido[2,3-b]indol-4-ylamino)phenol Chemical compound Oc1cccc(NC2=CC=NC3NC4C=CC=CC4C23)c1 YLLRPQWLASQXSI-UHFFFAOYSA-N 0.000 description 1
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- IDRYSCOQVVUBIJ-PPGFLMPOSA-N erythromycin B Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@H]([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)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 IDRYSCOQVVUBIJ-PPGFLMPOSA-N 0.000 description 1
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- 125000000468 ketone group Chemical group 0.000 description 1
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- 238000013508 migration Methods 0.000 description 1
- QAPTWHXHEYAIKG-RCOXNQKVSA-N n-[(1r,2s,5r)-5-(tert-butylamino)-2-[(3s)-2-oxo-3-[[6-(trifluoromethyl)quinazolin-4-yl]amino]pyrrolidin-1-yl]cyclohexyl]acetamide Chemical compound CC(=O)N[C@@H]1C[C@H](NC(C)(C)C)CC[C@@H]1N1C(=O)[C@@H](NC=2C3=CC(=CC=C3N=CN=2)C(F)(F)F)CC1 QAPTWHXHEYAIKG-RCOXNQKVSA-N 0.000 description 1
- XZMHJYWMCRQSSI-UHFFFAOYSA-N n-[5-[2-(3-acetylanilino)-1,3-thiazol-4-yl]-4-methyl-1,3-thiazol-2-yl]benzamide Chemical compound CC(=O)C1=CC=CC(NC=2SC=C(N=2)C2=C(N=C(NC(=O)C=3C=CC=CC=3)S2)C)=C1 XZMHJYWMCRQSSI-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000006485 reductive methylation reaction Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000006265 spirocyclization reaction Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Oncology (AREA)
- Animal Behavior & Ethology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Communicable Diseases (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Priority Applications (13)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR950145A HRP950145A2 (en) | 1995-03-27 | 1995-03-27 | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
| SI9500358A SI9500358A (en) | 1995-03-27 | 1995-11-21 | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
| BG100164A BG62333B1 (bg) | 1995-03-27 | 1995-11-24 | Нови съединения от клас секомакролиди и секоазалиди и методза получаването им |
| CZ953134A CZ313495A3 (en) | 1995-03-27 | 1995-11-27 | Compounds of secomacrolide and secoazalide class and process for preparing thereof |
| EP95118869A EP0735041A1 (fr) | 1995-03-27 | 1995-11-30 | Composés de la classe sécomacrolide et sécoazalide et un procédé pour leur préparation |
| CA002164152A CA2164152C (fr) | 1995-03-27 | 1995-11-30 | Composes de la classe des secomacrolides et des secoazalides; methode de preparation |
| SK1521-95A SK152195A3 (en) | 1995-03-27 | 1995-12-01 | Compounds of the secomacrolide and secoazalide class and preparaton method thereof |
| JP7320088A JPH08269078A (ja) | 1995-03-27 | 1995-12-08 | 新規なセコマクロライド及びセコアザリド系化合物、その製造方法並びにその製造用中間体 |
| RO95-02215A RO116017B1 (ro) | 1995-03-27 | 1995-12-18 | Derivati de secomacrolide si secoazalide, procedeu de preparare a acestora si intermediar |
| CN95121122A CN1053911C (zh) | 1995-03-27 | 1995-12-21 | 闭大环内酯和闭氮杂内酯类新化合物以及它们的制备方法 |
| RU95122457A RU2130936C1 (ru) | 1995-03-27 | 1995-12-21 | 9а-азалидные фрагменты макролидных антибиотиков класса азалидов, способ их получения и промежуточные соединения для их получения |
| PL96312209A PL312209A1 (en) | 1995-03-27 | 1996-01-09 | Novel compounds of seccomacrolydes and seccoazalydes class, intermediate compounds and method of obtaining them |
| US08/611,781 US5721346A (en) | 1995-03-27 | 1996-03-07 | Compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR950145A HRP950145A2 (en) | 1995-03-27 | 1995-03-27 | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP950145A2 true HRP950145A2 (en) | 1997-08-31 |
Family
ID=10946231
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR950145A HRP950145A2 (en) | 1995-03-27 | 1995-03-27 | New compounds of the secomacrolide and secoazalide class and a process for the preparation thereof |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US5721346A (fr) |
| EP (1) | EP0735041A1 (fr) |
| JP (1) | JPH08269078A (fr) |
| CN (1) | CN1053911C (fr) |
| BG (1) | BG62333B1 (fr) |
| CA (1) | CA2164152C (fr) |
| CZ (1) | CZ313495A3 (fr) |
| HR (1) | HRP950145A2 (fr) |
| PL (1) | PL312209A1 (fr) |
| RO (1) | RO116017B1 (fr) |
| RU (1) | RU2130936C1 (fr) |
| SI (1) | SI9500358A (fr) |
| SK (1) | SK152195A3 (fr) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP970141A2 (en) * | 1997-03-12 | 1999-02-28 | Banić-Tomaueić Zrinka | New secomacrolydes of erythromicin a, and a process for the preparation thereof |
| CZ211798A3 (cs) * | 1997-07-16 | 1999-02-17 | Pliva, Farmaceutska, Kemijska, Prehrambena I Kozmetička Industrije, Dioničko Društvo | Lineární 8a-sekoazalidy a způsob jejich výroby |
| HUP0104192A3 (en) | 1998-11-03 | 2003-12-29 | Pfizer Prod Inc | Novel macrolide antibiotics |
| JPWO2005019238A1 (ja) * | 2003-08-22 | 2006-10-19 | 明治製菓株式会社 | 新規アザライド及びアザラクタム誘導体とその製造法 |
| GB201608236D0 (en) * | 2016-05-11 | 2016-06-22 | Fidelta D O O | Seco macrolide compounds |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210235A (en) * | 1992-08-26 | 1993-05-11 | Merck & Co., Inc. | Methods of elaborating erythromycin fragments into amine-containing fragments of azalide antibiotics |
| WO1994015617A1 (fr) * | 1993-01-11 | 1994-07-21 | Merck & Co., Inc. | Antibiotiques macrolides 8a-aza et 9a-aza, et leurs procedes de preparation et d'utilisation |
-
1995
- 1995-03-27 HR HR950145A patent/HRP950145A2/hr not_active Application Discontinuation
- 1995-11-21 SI SI9500358A patent/SI9500358A/sl unknown
- 1995-11-24 BG BG100164A patent/BG62333B1/bg unknown
- 1995-11-27 CZ CZ953134A patent/CZ313495A3/cs unknown
- 1995-11-30 CA CA002164152A patent/CA2164152C/fr not_active Expired - Fee Related
- 1995-11-30 EP EP95118869A patent/EP0735041A1/fr not_active Withdrawn
- 1995-12-01 SK SK1521-95A patent/SK152195A3/sk unknown
- 1995-12-08 JP JP7320088A patent/JPH08269078A/ja active Pending
- 1995-12-18 RO RO95-02215A patent/RO116017B1/ro unknown
- 1995-12-21 RU RU95122457A patent/RU2130936C1/ru active
- 1995-12-21 CN CN95121122A patent/CN1053911C/zh not_active Expired - Fee Related
-
1996
- 1996-01-09 PL PL96312209A patent/PL312209A1/xx unknown
- 1996-03-07 US US08/611,781 patent/US5721346A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| SK152195A3 (en) | 1997-07-09 |
| CZ313495A3 (en) | 1997-08-13 |
| BG100164A (bg) | 1996-11-29 |
| CN1133294A (zh) | 1996-10-16 |
| CA2164152A1 (fr) | 1996-09-28 |
| EP0735041A1 (fr) | 1996-10-02 |
| CA2164152C (fr) | 2000-03-28 |
| SI9500358A (en) | 1996-10-31 |
| CN1053911C (zh) | 2000-06-28 |
| RU2130936C1 (ru) | 1999-05-27 |
| PL312209A1 (en) | 1996-09-30 |
| US5721346A (en) | 1998-02-24 |
| BG62333B1 (bg) | 1999-08-31 |
| RO116017B1 (ro) | 2000-09-29 |
| JPH08269078A (ja) | 1996-10-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1OB | Publication of a patent application | ||
| AIPI | Request for the grant of a patent on the basis of a substantive examination of a patent application | ||
| ODBC | Application rejected |