HRP20020991A2 - N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de - Google Patents
N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de Download PDFInfo
- Publication number
- HRP20020991A2 HRP20020991A2 HR20020991A HRP20020991A HRP20020991A2 HR P20020991 A2 HRP20020991 A2 HR P20020991A2 HR 20020991 A HR20020991 A HR 20020991A HR P20020991 A HRP20020991 A HR P20020991A HR P20020991 A2 HRP20020991 A2 HR P20020991A2
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- Croatia
- Prior art keywords
- meaning
- residue
- cyanoethyl
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- -1 Beta-cyanoethyl Chemical group 0.000 title claims description 65
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 162
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 13
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 13
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 claims description 9
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 9
- 125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 9
- 125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 8
- 150000007522 mineralic acids Chemical class 0.000 claims description 8
- 150000007524 organic acids Chemical class 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 235000005985 organic acids Nutrition 0.000 claims description 6
- ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 5
- 230000000844 anti-bacterial effect Effects 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 239000000825 pharmaceutical preparation Substances 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
- 239000000010 aprotic solvent Substances 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000008096 xylene Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims 54
- 208000035143 Bacterial infection Diseases 0.000 claims 1
- 208000022362 bacterial infectious disease Diseases 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 156
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 144
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 102
- 239000002904 solvent Substances 0.000 description 53
- 229910021529 ammonia Inorganic materials 0.000 description 51
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 50
- 239000012043 crude product Substances 0.000 description 50
- 238000000524 positive electrospray ionisation mass spectrometry Methods 0.000 description 50
- 239000000741 silica gel Substances 0.000 description 50
- 229910002027 silica gel Inorganic materials 0.000 description 50
- 229940073584 methylene chloride Drugs 0.000 description 48
- 238000004587 chromatography analysis Methods 0.000 description 43
- 239000013078 crystal Substances 0.000 description 42
- 239000011541 reaction mixture Substances 0.000 description 39
- 238000002955 isolation Methods 0.000 description 37
- 238000003756 stirring Methods 0.000 description 37
- 229960003276 erythromycin Drugs 0.000 description 10
- 238000007792 addition Methods 0.000 description 8
- MDKCFLQDBWCQCV-UHFFFAOYSA-N benzyl isothiocyanate Chemical compound S=C=NCC1=CC=CC=C1 MDKCFLQDBWCQCV-UHFFFAOYSA-N 0.000 description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 7
- 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 6
- 229930006677 Erythromycin A Natural products 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- BDQNKCYCTYYMAA-UHFFFAOYSA-N 1-isocyanatonaphthalene Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1 BDQNKCYCTYYMAA-UHFFFAOYSA-N 0.000 description 5
- YDNLNVZZTACNJX-UHFFFAOYSA-N isocyanatomethylbenzene Chemical compound O=C=NCC1=CC=CC=C1 YDNLNVZZTACNJX-UHFFFAOYSA-N 0.000 description 5
- GRUOGLPIAPZLHJ-UHFFFAOYSA-N 1-Isothiocyanato-3-phenylpropane Chemical compound S=C=NCCCC1=CC=CC=C1 GRUOGLPIAPZLHJ-UHFFFAOYSA-N 0.000 description 4
- GONOHGQPZFXJOJ-SNVBAGLBSA-N 1-[(1r)-1-isocyanatoethyl]naphthalene Chemical compound C1=CC=C2C([C@H](N=C=O)C)=CC=CC2=C1 GONOHGQPZFXJOJ-SNVBAGLBSA-N 0.000 description 4
- OLBJNSPBWLCTOT-UHFFFAOYSA-N 2,4-dichloro-1-isocyanatobenzene Chemical compound ClC1=CC=C(N=C=O)C(Cl)=C1 OLBJNSPBWLCTOT-UHFFFAOYSA-N 0.000 description 4
- XIXJQNFTNSQTBT-UHFFFAOYSA-N 2-isocyanatonaphthalene Chemical compound C1=CC=CC2=CC(N=C=O)=CC=C21 XIXJQNFTNSQTBT-UHFFFAOYSA-N 0.000 description 4
- GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 4
- QAADZYUXQLUXFX-UHFFFAOYSA-N N-phenylmethylthioformamide Natural products S=CNCC1=CC=CC=C1 QAADZYUXQLUXFX-UHFFFAOYSA-N 0.000 description 4
- DUVOZUPPHBRJJO-UHFFFAOYSA-N ethyl 2-isocyanatoacetate Chemical compound CCOC(=O)CN=C=O DUVOZUPPHBRJJO-UHFFFAOYSA-N 0.000 description 4
- 238000000338 in vitro Methods 0.000 description 4
- IZJDOKYDEWTZSO-UHFFFAOYSA-N phenethyl isothiocyanate Chemical compound S=C=NCCC1=CC=CC=C1 IZJDOKYDEWTZSO-UHFFFAOYSA-N 0.000 description 4
- GZWGTVZRRFPVAS-UHFFFAOYSA-N 1-isocyanato-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1N=C=O GZWGTVZRRFPVAS-UHFFFAOYSA-N 0.000 description 3
- MJJXWPHZDBIHIM-UHFFFAOYSA-N 5-isocyanato-1,2,3-trimethoxybenzene Chemical compound COC1=CC(N=C=O)=CC(OC)=C1OC MJJXWPHZDBIHIM-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 3
- 241000894006 Bacteria Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 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 2
- 238000004440 column chromatography Methods 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- YVTFLQUPRIIRFE-QUMKBVJLSA-N erythronolide A Chemical compound CC[C@H]1OC(=O)[C@H](C)[C@@H](O)[C@H](C)[C@@H](O)[C@](C)(O)C[C@@H](C)C(=O)[C@H](C)[C@@H](O)[C@]1(C)O YVTFLQUPRIIRFE-QUMKBVJLSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 239000003120 macrolide antibiotic agent Substances 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000008194 pharmaceutical composition Substances 0.000 description 2
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
- 238000001556 precipitation Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- 238000010898 silica gel chromatography Methods 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- JBDOSUUXMYMWQH-UHFFFAOYSA-N 1-naphthyl isothiocyanate Chemical compound C1=CC=C2C(N=C=S)=CC=CC2=C1 JBDOSUUXMYMWQH-UHFFFAOYSA-N 0.000 description 1
- RTMXPNYHPHIDHX-UHFFFAOYSA-N 2-isothiocyanatonaphthalene Chemical compound C1=CC=CC2=CC(N=C=S)=CC=C21 RTMXPNYHPHIDHX-UHFFFAOYSA-N 0.000 description 1
- YKAVHPRGGAUFDN-JTQLBUQXSA-N 24464-30-0 Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]2(C)O[C@]3([C@@H]([C@H]2O)C)[C@H](C)C[C@](O3)(C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C)CC)[C@H]1C[C@@](C)(OC)[C@@H](O)[C@H](C)O1 YKAVHPRGGAUFDN-JTQLBUQXSA-N 0.000 description 1
- 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 1
- 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 1
- COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
- 208000035473 Communicable disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- 241000495778 Escherichia faecalis Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000588655 Moraxella catarrhalis Species 0.000 description 1
- 150000001204 N-oxides Chemical class 0.000 description 1
- 241000193996 Streptococcus pyogenes Species 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 229960004099 azithromycin Drugs 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000037396 body weight Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- PFOARMALXZGCHY-UHFFFAOYSA-N homoegonol Natural products C1=C(OC)C(OC)=CC=C1C1=CC2=CC(CCCO)=CC(OC)=C2O1 PFOARMALXZGCHY-UHFFFAOYSA-N 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- 239000007927 intramuscular injection Substances 0.000 description 1
- 238000010255 intramuscular injection Methods 0.000 description 1
- 150000007931 macrolactones Chemical group 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- 244000000010 microbial pathogen Species 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 1
- 150000004893 oxazines Chemical class 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000006265 spirocyclization reaction Methods 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 230000007723 transport mechanism Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- 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
-
- 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
-
- 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
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Priority Applications (26)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20020991A HRP20020991A2 (en) | 2002-12-12 | 2002-12-12 | N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de |
| US10/538,376 US7342000B2 (en) | 2002-12-12 | 2003-12-10 | Semisynthetic macrolide antibiotics of the azalide series |
| JP2004558858A JP2006510660A (ja) | 2002-12-12 | 2003-12-10 | ９−デオキソ−９−ジヒドロ−９ａ−アザ−９ａ−ホモエリスロマイシンＡ及び５−Ｏ−デソサミニル−９−デオキソ−９−ジヒドロ−９ａ−アザ−９ａ−ホモエリスロノリドＡのＮ″−置換９ａ−Ｎ−（Ｎ´−カルバモイル−γ−アミノプロピル）、９ａ−Ｎ−（Ｎ´−チオカルバモイル−γ−アミノプロピル）、９ａ−Ｎ−［Ｎ´−（β−シアノエチル）−Ｎ´−カルバモイル−γ−アミノプロピル］及び９ａ−Ｎ−［Ｎ´−（β−シアノエチル）−Ｎ´−チオカルバモイル−γ−アミノプロピル］誘導体 |
| DK03778598T DK1585753T3 (da) | 2002-12-12 | 2003-12-10 | Hidtil ukendte, semisyntetiske makrolidantibiotika af azalidserien |
| PCT/HR2003/000062 WO2004052904A2 (en) | 2002-12-12 | 2003-12-10 | Novel semisynthetic macrolide antibiotics of the azalide series |
| ES03778598T ES2266883T3 (es) | 2002-12-12 | 2003-12-10 | Nuevos antibioticos semisinteticos aza-macrolidos. |
| CA002509599A CA2509599A1 (en) | 2002-12-12 | 2003-12-10 | Novel semisynthetic macrolide antibiotics of the azalide series |
| ARP030104537A AR042351A1 (es) | 2002-12-12 | 2003-12-10 | "DERIVADOS N" SUSTITUIDOS 9A-N- (N' CARBAMOIL - GAMMA - AMINOPROPIL) , 9A - N- ( N'- TIOCARBAMOIL- GAMMA- AMINOPROPIL), 9 A - N- [N' - ( a- CIANOETIL) - N' - CARBAMOIL . GAMMA- AMINOPROPIL ] DE 9- DEOXO- 9- DIHIDRO 9A - AZA- 9A- HOMOERITROMICINA A Y 5 - O- DESOMINIL- 9- DEOXO- 9- DIHIDRO-9 A - AZA- |
| KR1020057010623A KR20050085555A (ko) | 2002-12-12 | 2003-12-10 | 아잘라이드 계열의 신규한 반합성 마크로라이드 항생제 |
| PL377322A PL377322A1 (pl) | 2002-12-12 | 2003-12-10 | N"-podstawione pochodne 9a-N-(N'-karbamoilo-<$Egamma>-aminopropylowe), 9a-N-(N'-tiokarbamoilo-<$Egamma>-aminopropylowe), 9a-N-[N'-(ß-cyjanoetylo)-N'-karbamoilo-<$Egamma>-aminopropylowe] i 9a-N-[N'-(ß-cyjanoetylo)-N'-tiokarbamoilo-<$Egamma>-aminopropylowe] 9-deokso-9-dihydro-9a-aza-9a-homoerytromycyny A i 5-0-desos-aminylo-9-deokso-9-dihydro-9a-aza-9a-homoerytronolidu A |
| AT03778598T ATE327999T1 (de) | 2002-12-12 | 2003-12-10 | Neue halbsynthetische macrolidantibiotika der azalidreihe |
| MXPA05006220A MXPA05006220A (es) | 2002-12-12 | 2003-12-10 | Nuevos antibioticos macrolidos semisinteticos de la serie de azalidas. |
| BR0316569-8A BR0316569A (pt) | 2002-12-12 | 2003-12-10 | 9a-n-(n'-carbamoil-gama-aminopropila), 9a-n-(n'-tiocarbamoil-gama-aminopropila), 9a-n-[n'-(beta-cianoetil)-n'-carbamoil-gama-aminoprop ila] e 9a-n-[n'-(beta-cianoetil)-n'-tiocarbamoil-gama-aminop ropila] n"-substituìdas derivadas de 9-desoxo-9-diidro-9a-aza-9a-homoeritromicina a e 5-o-desosaminil-9-desoxo-9-diidro-9a-aza-9a-homoerit ronolida a |
| EP03778598A EP1585753B1 (en) | 2002-12-12 | 2003-12-10 | Novel semisynthetic macrolide antibiotics of the azalide series |
| DE60305741T DE60305741T2 (de) | 2002-12-12 | 2003-12-10 | Neue halbsynthetische macrolidantibiotika der azalidreihe |
| CNB2003801057628A CN100335489C (zh) | 2002-12-12 | 2003-12-10 | 半合成的氮杂环内酯系列的大环内酯类抗生素 |
| SI200330295T SI1585753T1 (sl) | 2002-12-12 | 2003-12-10 | Novi polsintetski makrolidni antibiotiki iz vrsteazalidov |
| PT03778598T PT1585753E (pt) | 2002-12-12 | 2003-12-10 | Novos antibioticos macrolidos semi-sinteticos da serie dos azalidos |
| AU2003285599A AU2003285599A1 (en) | 2002-12-12 | 2003-12-10 | Novel semisynthetic macrolide antibiotics of the azalide series |
| YU80204A RS80204A (en) | 2002-12-12 | 2003-12-10 | N"-substituted 9a-n-(n'-carbamoyl-y- aminopropyl),9a-n-(n'- thiocarbamoyl-y- aminoproyl),9a-n-/n'-(beta-cyanoethyl)-n'- carbamoyl-y-aminopropyl/ |
| RU2005121892/04A RU2328503C2 (ru) | 2002-12-12 | 2003-12-10 | N''-ЗАМЕЩЕННЫЕ 9a-N-(N'-КАРБАМОИЛ-ГАММА-АМИНОПРОПИЛЬНЫЕ) И 9a-N-(N'-ТИОКАРБАМОИЛ-ГАММА-АМИНОПРОПИЛЬНЫЕ), ПРОИЗВОДНЫЕ 9-ДЕЗОКСО-9-ДИГИДРО-9a-АЗА-9a-ГОМОЭРИТРОМИЦИНА A И 5-O-ДЕЗОЗАМИНИЛ-9-ДЕЗОКСО-9-ДИГИДРО-9a-АЗА-9a-ГОМОЭРИТРОНОЛИДА A |
| CL200302585A CL2003002585A1 (es) | 2002-12-12 | 2003-12-11 | Compuestos n" derivados de 9a-n-(n'-{carbamoil o tiocarbamoil}-gamma-aminpropil), 9a-n-[n'-(beta-cianoetil)-n'-{carbaoil o tiocarbamoil}-gamma-aminopropil] de 9-deoxo-9-dihidro-9a-aza-9a-homoeritromicina a y 5-o- desosaminil-9-deoxo-9-dihidro-9a-aza- |
| IS7875A IS2309B (is) | 2002-12-12 | 2005-05-31 | Ný hálfsmíðuð makrólíð sýklalyf úr asalíð röðunum |
| CO05067476A CO5640139A2 (es) | 2002-12-12 | 2005-07-08 | Nuevos antibioticos macrolidos semisinteticos de la serie de azalidas |
| HK06106121A HK1086273A1 (en) | 2002-12-12 | 2006-05-26 | Semisynthetic macrolide antibiotics of the azalideseries |
| CY20061101203T CY1106321T1 (el) | 2002-12-12 | 2006-08-25 | Νεα αντιβιοτικα ημισυνθετικου μακρολιδιου της σειρας των αζαλιδων |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HR20020991A HRP20020991A2 (en) | 2002-12-12 | 2002-12-12 | N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HRP20020991A2 true HRP20020991A2 (en) | 2005-02-28 |
Family
ID=32500425
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HR20020991A HRP20020991A2 (en) | 2002-12-12 | 2002-12-12 | N"-Substituted 9a-N-(N'-carbamoyl-Gamma-aminopropyl), 9a-N-(N'? -thiocarbamoyl-Gamma-aminopropyl), 9a-N-(N'-((Beta-cyanoethyl)-N'-carbamoyl-Gamma? -aminopropyl) and 9a-N-(N'-(Beta-cyanoethyl)-N'-thiocarbamoyl-Gamma? -aminopropyl) derivatives of 9-de |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US7342000B2 (pt) |
| EP (1) | EP1585753B1 (pt) |
| JP (1) | JP2006510660A (pt) |
| KR (1) | KR20050085555A (pt) |
| CN (1) | CN100335489C (pt) |
| AR (1) | AR042351A1 (pt) |
| AT (1) | ATE327999T1 (pt) |
| AU (1) | AU2003285599A1 (pt) |
| BR (1) | BR0316569A (pt) |
| CA (1) | CA2509599A1 (pt) |
| CL (1) | CL2003002585A1 (pt) |
| CO (1) | CO5640139A2 (pt) |
| CY (1) | CY1106321T1 (pt) |
| DE (1) | DE60305741T2 (pt) |
| DK (1) | DK1585753T3 (pt) |
| ES (1) | ES2266883T3 (pt) |
| HK (1) | HK1086273A1 (pt) |
| HR (1) | HRP20020991A2 (pt) |
| IS (1) | IS2309B (pt) |
| MX (1) | MXPA05006220A (pt) |
| PL (1) | PL377322A1 (pt) |
| PT (1) | PT1585753E (pt) |
| RS (1) | RS80204A (pt) |
| RU (1) | RU2328503C2 (pt) |
| WO (1) | WO2004052904A2 (pt) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| HRP20020885B1 (en) | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| DE602006016231D1 (de) * | 2005-01-14 | 2010-09-30 | Glaxosmithkline Zagreb | 9a-carbamoyl-y-aminopropyl- und 9a-thiocarbamoyl-y-aminopropyl-azalide mit antimalaria-aktivität |
| US20080200404A1 (en) * | 2005-01-14 | 2008-08-21 | Mirjana Bukvic Krajacic | Novel Antimalarial 9A-Carbamoyl-Aminoalkyl and 9A-Thiocarbamoyl-Aminoalkyl Azalides |
| JP2009535395A (ja) * | 2006-05-03 | 2009-10-01 | グラクソスミスクライン・イストラジヴァッキ・センタル・ザグレブ・ドルズバ・ゼー・オメイェノ・オドゴヴォルノスティオ | ９ａ−置換アザリド |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| YU43116B (en) | 1979-04-02 | 1989-04-30 | Pliva Pharm & Chem Works | Process for preparing 11-aza-4-o-cladinosyl-6-o-desosaminyl-15-ethyl-7,13,14-trihydroxy-3,5,7,9,12,14-hexamethyl-oxacyclopentadecane-2-one(11-aza-10-deox |
| 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 |
| BE892397A (nl) | 1982-03-08 | 1982-07-01 | Marchand Paul | Wereldwijde draadloze telefonie voor 10 miljard abonnees |
| US4474768A (en) | 1982-07-19 | 1984-10-02 | Pfizer Inc. | N-Methyl 11-aza-10-deoxo-10-dihydro-erytromycin A, intermediates therefor |
| US4492688A (en) | 1983-11-25 | 1985-01-08 | Pfizer Inc. | Antibacterial cyclic ethers of 9-deoxo-9a-aza-9a-homoerythromycin A and intermediates therefor |
| US4464527A (en) * | 1983-06-30 | 1984-08-07 | Pfizer Inc. | Antibacterial 9-deoxo-9a-alkyl-9a-aza-9a-homoerythromycin A derivatives and intermediates therefore |
| MX13723A (es) | 1987-11-10 | 1993-05-01 | Pfizer | Procedimiento para preparar derivados de 9-desoxo-9a-alil- y propargil-9a-aza-9a-homoeritromicina a |
| HRP931480B1 (en) | 1993-12-08 | 1997-08-31 | Sour Pliva | 9a-N-(N'-CARBAMONYL) and 9a-N-(N'-THIOCARBAMONYL) DERIVATES OF 9-DEOXO-9a-HOMOERYTHROMYCIN A |
| WO1997035590A1 (en) * | 1996-03-25 | 1997-10-02 | Platt Chris E | 10-aza-9-deoxo-11-deoxy-erythromycin a and derivatives combined with sulfisoxazole |
| HRP990130B1 (en) | 1999-05-03 | 2004-06-30 | Pliva D D | HALOGEN DERIVATIVES 9a-N-(N'-ARYLCARBAMOYL)- AND 9a-N-(N'-ARYLTHIOCARBAMOYL)-9-DEOXO-9a-AZA-9a OF HOMOERYTHROMYCIN A |
| ATE345350T1 (de) * | 2000-12-21 | 2006-12-15 | Glaxo Group Ltd | Makrolidantibiotika |
| HRP20010146B1 (en) | 2001-02-28 | 2005-10-31 | Pliva D.D. | 9a-N-(N'-(PHENYLSULFONYL)CARBAMOYL) DERIVATIVES OF 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHROMYCIN A AND OF 5-O-DESOSAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERYTHRONOLIDE A |
| HRP20020885B1 (en) | 2002-11-11 | 2007-05-31 | GlaxoSmithKline istra�iva�ki centar Zagreb d.o.o. | SUBSTITUTED 9a-N-{N'-[4-(SULFONYL)PHENYLCARBAMOYL]}DERIVATIVES 9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHROMYCIN A AND 5-O-DESOZAMINYL-9-DEOXO-9-DIHYDRO-9a-AZA-9a-HOMOERITHRONOLIDE A |
| HRP20020886A2 (en) | 2002-11-11 | 2005-06-30 | PLIVA-ISTRAŽIVAČKI INSTITUT d.o.o. | SUBSTITUTED 9a-N-[N'-(BENZENSULFONYL)CARBAMOYL-γ-AMINOPROPYL) AND 9a-N(N' -(?-CYANOETHIL)-N' -(b |
-
2002
- 2002-12-12 HR HR20020991A patent/HRP20020991A2/hr not_active Application Discontinuation
-
2003
- 2003-12-10 PT PT03778598T patent/PT1585753E/pt unknown
- 2003-12-10 PL PL377322A patent/PL377322A1/pl unknown
- 2003-12-10 MX MXPA05006220A patent/MXPA05006220A/es active IP Right Grant
- 2003-12-10 DK DK03778598T patent/DK1585753T3/da active
- 2003-12-10 BR BR0316569-8A patent/BR0316569A/pt not_active IP Right Cessation
- 2003-12-10 DE DE60305741T patent/DE60305741T2/de not_active Expired - Fee Related
- 2003-12-10 WO PCT/HR2003/000062 patent/WO2004052904A2/en active IP Right Grant
- 2003-12-10 RS YU80204A patent/RS80204A/sr unknown
- 2003-12-10 AT AT03778598T patent/ATE327999T1/de not_active IP Right Cessation
- 2003-12-10 CA CA002509599A patent/CA2509599A1/en not_active Abandoned
- 2003-12-10 AU AU2003285599A patent/AU2003285599A1/en not_active Abandoned
- 2003-12-10 JP JP2004558858A patent/JP2006510660A/ja active Pending
- 2003-12-10 US US10/538,376 patent/US7342000B2/en not_active Expired - Fee Related
- 2003-12-10 RU RU2005121892/04A patent/RU2328503C2/ru not_active IP Right Cessation
- 2003-12-10 ES ES03778598T patent/ES2266883T3/es not_active Expired - Lifetime
- 2003-12-10 AR ARP030104537A patent/AR042351A1/es not_active Application Discontinuation
- 2003-12-10 CN CNB2003801057628A patent/CN100335489C/zh not_active Expired - Fee Related
- 2003-12-10 EP EP03778598A patent/EP1585753B1/en not_active Expired - Lifetime
- 2003-12-10 KR KR1020057010623A patent/KR20050085555A/ko not_active Application Discontinuation
- 2003-12-11 CL CL200302585A patent/CL2003002585A1/es unknown
-
2005
- 2005-05-31 IS IS7875A patent/IS2309B/is unknown
- 2005-07-08 CO CO05067476A patent/CO5640139A2/es not_active Application Discontinuation
-
2006
- 2006-05-26 HK HK06106121A patent/HK1086273A1/xx not_active IP Right Cessation
- 2006-08-25 CY CY20061101203T patent/CY1106321T1/el unknown
Also Published As
| Publication number | Publication date |
|---|---|
| RS80204A (en) | 2006-12-15 |
| CY1106321T1 (el) | 2011-10-12 |
| CA2509599A1 (en) | 2004-06-24 |
| CN1726222A (zh) | 2006-01-25 |
| BR0316569A (pt) | 2005-10-04 |
| ES2266883T3 (es) | 2007-03-01 |
| CN100335489C (zh) | 2007-09-05 |
| IS7875A (is) | 2005-05-31 |
| AU2003285599A1 (en) | 2004-06-30 |
| CL2003002585A1 (es) | 2005-01-28 |
| DE60305741T2 (de) | 2007-06-14 |
| IS2309B (is) | 2007-10-15 |
| AU2003285599A8 (en) | 2004-06-30 |
| EP1585753B1 (en) | 2006-05-31 |
| MXPA05006220A (es) | 2005-11-17 |
| EP1585753A2 (en) | 2005-10-19 |
| US7342000B2 (en) | 2008-03-11 |
| AR042351A1 (es) | 2005-06-15 |
| RU2328503C2 (ru) | 2008-07-10 |
| WO2004052904A3 (en) | 2004-09-02 |
| KR20050085555A (ko) | 2005-08-29 |
| DK1585753T3 (da) | 2006-10-02 |
| WO2004052904A2 (en) | 2004-06-24 |
| JP2006510660A (ja) | 2006-03-30 |
| DE60305741D1 (de) | 2006-07-06 |
| US20060252709A1 (en) | 2006-11-09 |
| CO5640139A2 (es) | 2006-05-31 |
| HK1086273A1 (en) | 2006-09-15 |
| PT1585753E (pt) | 2006-08-31 |
| PL377322A1 (pl) | 2006-01-23 |
| ATE327999T1 (de) | 2006-06-15 |
| RU2005121892A (ru) | 2006-01-20 |
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