SI20640A - Novi derivati eritromicina, postopek za njihovo pripravo in njihova uporaba kot zdravila - Google Patents

Novi derivati eritromicina, postopek za njihovo pripravo in njihova uporaba kot zdravila Download PDF

Info

Publication number: SI20640A
Authority: SI; Slovenia
Prior art keywords: formula; methyl; compound; dideoxy; compounds
Prior art date: 1998-11-10

Application number

SI9920091A

Other languages

English (en)

Slovenian (sl)

Inventor

Constantin Agouridas

Alexis Denis

Claude Fromentin

Original Assignee

Aventis Pharma S.A.

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.)

1998-11-10

Filing date

1999-11-09

Publication date

2002-02-28

1999-11-09 Application filed by Aventis Pharma S.A. filed Critical Aventis Pharma S.A.

2002-02-28 Publication of SI20640A publication Critical patent/SI20640A/sl

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 description 12
239000003814 drug Substances 0.000 title claims description 10
238000002360 preparation method Methods 0.000 title claims description 10
229940079593 drug Drugs 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 30
239000002253 acid Substances 0.000 claims abstract description 11
150000003839 salts Chemical class 0.000 claims abstract description 10
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
239000000126 substance Substances 0.000 claims abstract description 6
150000007513 acids Chemical class 0.000 claims abstract description 4
125000005843 halogen group Chemical group 0.000 claims abstract description 4
229960003276 erythromycin Drugs 0.000 claims description 13
-1 acyl radical Chemical class 0.000 claims description 5
UKJLNMAFNRKWGR-UHFFFAOYSA-N cyclohexatrienamine Chemical group NC1=CC=C=C[CH]1 UKJLNMAFNRKWGR-UHFFFAOYSA-N 0.000 claims description 5
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
238000000034 method Methods 0.000 claims description 4
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 claims description 4
239000008194 pharmaceutical composition Substances 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 claims description 3
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
230000003115 biocidal effect Effects 0.000 abstract description 2
239000000654 additive Substances 0.000 abstract 1
230000000996 additive effect Effects 0.000 abstract 1
239000000047 product Substances 0.000 description 32
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000203 mixture Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 6
239000000243 solution Substances 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
239000000546 pharmaceutical excipient Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
206010002383 Angina Pectoris Diseases 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
235000019359 magnesium stearate Nutrition 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000454 talc Substances 0.000 description 3
229910052623 talc Inorganic materials 0.000 description 3
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
241000295644 Staphylococcaceae Species 0.000 description 2
206010041925 Staphylococcal infections Diseases 0.000 description 2
241000193998 Streptococcus pneumoniae Species 0.000 description 2
241000193996 Streptococcus pyogenes Species 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
230000001154 acute effect Effects 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical compound C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 2
125000001841 imino group Chemical group [H]N=* 0.000 description 2
208000015181 infectious disease Diseases 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
CSYNQJPENMOLHR-UHFFFAOYSA-N n,n-diethylethanamine;ethyl acetate Chemical compound CCOC(C)=O.CCN(CC)CC CSYNQJPENMOLHR-UHFFFAOYSA-N 0.000 description 2
XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 2
239000012429 reaction media Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
229940031000 streptococcus pneumoniae Drugs 0.000 description 2
235000012222 talc Nutrition 0.000 description 2
LDMOEFOXLIZJOW-UHFFFAOYSA-N 1-dodecanesulfonic acid Chemical compound CCCCCCCCCCCCS(O)(=O)=O LDMOEFOXLIZJOW-UHFFFAOYSA-N 0.000 description 1
UXFWTIGUWHJKDD-UHFFFAOYSA-N 2-(4-bromobutyl)isoindole-1,3-dione Chemical compound C1=CC=C2C(=O)N(CCCCBr)C(=O)C2=C1 UXFWTIGUWHJKDD-UHFFFAOYSA-N 0.000 description 1
MBUPVGIGAMCMBT-UHFFFAOYSA-N 2-bromo-1-(4-nitrophenyl)ethanone Chemical compound [O-][N+](=O)C1=CC=C(C(=O)CBr)C=C1 MBUPVGIGAMCMBT-UHFFFAOYSA-N 0.000 description 1
QGACMDJNLPUDIP-UHFFFAOYSA-N 4-[1-(4-aminobutyl)imidazol-4-yl]aniline Chemical compound NCCCCN1C=NC(C=2C=CC(N)=CC=2)=C1 QGACMDJNLPUDIP-UHFFFAOYSA-N 0.000 description 1
FNLBIRUBMLUNQC-UHFFFAOYSA-N 5-(4-nitrophenyl)-1h-imidazole Chemical compound C1=CC([N+](=O)[O-])=CC=C1C1=CN=CN1 FNLBIRUBMLUNQC-UHFFFAOYSA-N 0.000 description 1
208000002874 Acne Vulgaris Diseases 0.000 description 1
201000004813 Bronchopneumonia Diseases 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
206010007882 Cellulitis Diseases 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000606768 Haemophilus influenzae Species 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
208000005141 Otitis Diseases 0.000 description 1
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 1
208000035109 Pneumococcal Infections Diseases 0.000 description 1
206010035664 Pneumonia Diseases 0.000 description 1
206010039587 Scarlet Fever Diseases 0.000 description 1
206010040047 Sepsis Diseases 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
206010066409 Staphylococcal skin infection Diseases 0.000 description 1
206010061372 Streptococcal infection Diseases 0.000 description 1
206010052428 Wound Diseases 0.000 description 1
208000027418 Wounds and injury Diseases 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
239000001785 acacia senegal l. willd gum Substances 0.000 description 1
206010000496 acne Diseases 0.000 description 1
239000013543 active substance Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
239000008135 aqueous vehicle Substances 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
230000001580 bacterial effect Effects 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
206010006451 bronchitis Diseases 0.000 description 1
238000009924 canning Methods 0.000 description 1
239000002775 capsule Substances 0.000 description 1
150000007942 carboxylates Chemical class 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
210000000038 chest Anatomy 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000006071 cream Substances 0.000 description 1
239000012043 crude product Substances 0.000 description 1
WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
239000012895 dilution Substances 0.000 description 1
238000010790 dilution Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
208000019258 ear infection Diseases 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
150000002148 esters Chemical group 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
230000001815 facial effect Effects 0.000 description 1
230000004720 fertilization Effects 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
229940047650 haemophilus influenzae Drugs 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000011534 incubation Methods 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
206010022000 influenza Diseases 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
238000002955 isolation Methods 0.000 description 1
239000008101 lactose Substances 0.000 description 1
230000003211 malignant effect Effects 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
230000000813 microbial effect Effects 0.000 description 1
210000004400 mucous membrane Anatomy 0.000 description 1
OVQABVAKPIYHIG-UHFFFAOYSA-N n-(benzenesulfonyl)benzenesulfonamide Chemical compound C=1C=CC=CC=1S(=O)(=O)NS(=O)(=O)C1=CC=CC=C1 OVQABVAKPIYHIG-UHFFFAOYSA-N 0.000 description 1
239000002687 nonaqueous vehicle Substances 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 1
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 1
239000012188 paraffin wax Substances 0.000 description 1
230000000144 pharmacologic effect Effects 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
230000002685 pulmonary effect Effects 0.000 description 1
238000011403 purification operation Methods 0.000 description 1
230000001698 pyrogenic effect Effects 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
208000013223 septicemia Diseases 0.000 description 1
201000009890 sinusitis Diseases 0.000 description 1
235000019980 sodium acid phosphate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
- 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
- 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
- C07H1/00—Processes for the preparation of sugar derivatives
- 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)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Oncology (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Communicable Diseases (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)

SI9920091A 1998-11-10 1999-11-09 Novi derivati eritromicina, postopek za njihovo pripravo in njihova uporaba kot zdravila SI20640A (sl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9814145A FR2785612A1 (fr)	1998-11-10	1998-11-10	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
PCT/FR1999/002718 WO2000027857A2 (fr)	1998-11-10	1999-11-09	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments

Publications (1)

Publication Number	Publication Date
SI20640A true SI20640A (sl)	2002-02-28

Family

ID=9532584

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SI9920091A SI20640A (sl)	1998-11-10	1999-11-09	Novi derivati eritromicina, postopek za njihovo pripravo in njihova uporaba kot zdravila

Country Status (28)

Country	Link
US (2)	US6455505B2 (de)
EP (1)	EP1016669B1 (de)
JP (1)	JP4698783B2 (de)
KR (1)	KR100567695B1 (de)
CN (2)	CN1240708C (de)
AR (1)	AR025814A1 (de)
AT (1)	ATE232879T1 (de)
AU (1)	AU766138B2 (de)
BR (1)	BR9915236A (de)
CA (1)	CA2350651C (de)
CZ (1)	CZ20011622A3 (de)
DE (1)	DE69905447T2 (de)
DK (1)	DK1016669T3 (de)
EA (1)	EA200100533A1 (de)
ES (1)	ES2189365T3 (de)
FR (1)	FR2785612A1 (de)
HR (1)	HRP20010335B1 (de)
HU (1)	HUP0104035A3 (de)
IL (2)	IL142996A0 (de)
NO (1)	NO20012272L (de)
NZ (1)	NZ511609A (de)
PL (1)	PL348098A1 (de)
PT (1)	PT1016669E (de)
SI (1)	SI20640A (de)
TR (1)	TR200101286T2 (de)
TW (1)	TWI237027B (de)
WO (1)	WO2000027857A2 (de)
ZA (1)	ZA200103801B (de)

Families Citing this family (22)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK1147121T3 (da) *	1999-01-27	2004-04-13	Pfizer Prod Inc	Ketolidantibiotika
EE200100613A (et)	1999-05-24	2003-02-17	Pfizer Products Inc.	13-metüülerütromütsiini derivaadid
EP1167376B1 (de)	2000-06-30	2004-07-14	Pfizer Products Inc.	Makrolid-Antibiotika
JP2004017020A (ja) *	2002-06-20	2004-01-22	Sony Corp	コーティング方法および被コーティング粒子
US7601695B2 (en)	2003-03-10	2009-10-13	Optimer Pharmaceuticals, Inc.	Antibacterial agents
WO2006080954A1 (en) *	2004-07-28	2006-08-03	Ranbaxy Laboratories Limited	Ketolide derivatives as antibacterial agents
WO2006046112A2 (en) *	2004-10-25	2006-05-04	Ranbaxy Laboratories Limited	Ketolide derivatives as antibacterial agents
AU2008316830B2 (en)	2007-10-25	2016-03-17	Cempra Pharmaceuticals, Inc.	Process for the preparation of macrolide antibacterial agents
CN107854477A (zh)	2008-10-24	2018-03-30	森普拉制药公司	使用含三唑的大环内酯治疗抗性疾病的方法
US9937194B1 (en)	2009-06-12	2018-04-10	Cempra Pharmaceuticals, Inc.	Compounds and methods for treating inflammatory diseases
US9480679B2 (en)	2009-09-10	2016-11-01	Cempra Pharmaceuticals, Inc.	Methods for treating malaria, tuberculosis and MAC diseases
HRP20160168T1 (hr)	2010-03-22	2016-03-25	Cempra Pharmaceuticals Inc	Kristalne forme makrolida i njihova uporaba
BR112012029586A2 (pt)	2010-05-20	2016-08-02	Cempra Pharmaceuticals Inc	processos para preparar macrolídeos e cetolídeos e intermediários dos mesmos
KR20130120458A (ko)	2010-09-10	2013-11-04	셈프라 파마슈티컬스, 인크.	질환을 치료하기 위한 수소결합 형성 플루오로 케토라이드
WO2013148891A1 (en)	2012-03-27	2013-10-03	Cempra Pharmaceuticals, Inc.	Parenteral formulations for administering macrolide antibiotics
WO2014152326A1 (en)	2013-03-14	2014-09-25	Cempra Pharmaceuticals, Inc.	Methods for treating respiratory diseases and formulations therefor
AU2014233240B2 (en)	2013-03-15	2018-08-09	Cempra Pharmaceuticals, Inc.	Convergent processes for preparing macrolide antibacterial agents
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1998
- 1998-11-10 FR FR9814145A patent/FR2785612A1/fr active Pending
1999
- 1999-11-03 US US09/433,146 patent/US6455505B2/en not_active Expired - Lifetime
- 1999-11-08 TW TW088119491A patent/TWI237027B/zh not_active IP Right Cessation
- 1999-11-09 DK DK99402783T patent/DK1016669T3/da active
- 1999-11-09 CA CA2350651A patent/CA2350651C/fr not_active Expired - Lifetime
- 1999-11-09 EA EA200100533A patent/EA200100533A1/ru unknown
- 1999-11-09 EP EP99402783A patent/EP1016669B1/de not_active Expired - Lifetime
- 1999-11-09 DE DE69905447T patent/DE69905447T2/de not_active Expired - Lifetime
- 1999-11-09 SI SI9920091A patent/SI20640A/sl not_active IP Right Cessation
- 1999-11-09 CN CNB998154393A patent/CN1240708C/zh not_active Expired - Lifetime
- 1999-11-09 WO PCT/FR1999/002718 patent/WO2000027857A2/fr not_active Ceased
- 1999-11-09 TR TR2001/01286T patent/TR200101286T2/xx unknown
- 1999-11-09 PT PT99402783T patent/PT1016669E/pt unknown
- 1999-11-09 HU HU0104035A patent/HUP0104035A3/hu unknown
- 1999-11-09 ES ES99402783T patent/ES2189365T3/es not_active Expired - Lifetime
- 1999-11-09 CN CNB200510128838XA patent/CN100351238C/zh not_active Expired - Lifetime
- 1999-11-09 HR HR990077A patent/HRP20010335B1/xx not_active IP Right Cessation
- 1999-11-09 BR BR9915236-3A patent/BR9915236A/pt active Search and Examination
- 1999-11-09 KR KR1020017005854A patent/KR100567695B1/ko not_active Expired - Lifetime
- 1999-11-09 AU AU10526/00A patent/AU766138B2/en not_active Expired
- 1999-11-09 IL IL14299699A patent/IL142996A0/xx active IP Right Grant
- 1999-11-09 JP JP31801599A patent/JP4698783B2/ja not_active Expired - Lifetime
- 1999-11-09 NZ NZ511609A patent/NZ511609A/en unknown
- 1999-11-09 PL PL99348098A patent/PL348098A1/xx not_active Application Discontinuation
- 1999-11-09 AT AT99402783T patent/ATE232879T1/de active
- 1999-11-09 CZ CZ20011622A patent/CZ20011622A3/cs unknown
- 1999-11-10 AR ARP990105702A patent/AR025814A1/es not_active Application Discontinuation
2000
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2001
- 2001-05-06 IL IL142996A patent/IL142996A/en not_active IP Right Cessation
- 2001-05-09 NO NO20012272A patent/NO20012272L/no not_active Application Discontinuation
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Also Published As

Publication number	Publication date
AU766138B2 (en)	2003-10-09
ATE232879T1 (de)	2003-03-15
CA2350651C (fr)	2010-07-20
TWI237027B (en)	2005-08-01
EA200100533A1 (ru)	2001-10-22
US20020013281A1 (en)	2002-01-31
CN1333782A (zh)	2002-01-30
PT1016669E (pt)	2003-07-31
DE69905447T2 (de)	2003-07-24
CN1814592A (zh)	2006-08-09
WO2000027857A2 (fr)	2000-05-18
KR100567695B1 (ko)	2006-04-05
NO20012272D0 (no)	2001-05-09
EP1016669A1 (de)	2000-07-05
HRP20010335B1 (en)	2003-08-31
CN1240708C (zh)	2006-02-08
CZ20011622A3 (cs)	2001-09-12
JP2000143689A (ja)	2000-05-26
WO2000027857A3 (fr)	2000-08-17
HUP0104035A3 (en)	2003-12-29
NZ511609A (en)	2003-07-25
CA2350651A1 (fr)	2000-05-18
DK1016669T3 (da)	2003-05-26
IL142996A0 (en)	2002-04-21
ES2189365T3 (es)	2003-07-01
EP1016669B1 (de)	2003-02-19
KR20010080970A (ko)	2001-08-25
FR2785612A1 (fr)	2000-05-12
US20020028781A1 (en)	2002-03-07
US6407257B1 (en)	2002-06-18
CN100351238C (zh)	2007-11-28
NO20012272L (no)	2001-07-10
JP4698783B2 (ja)	2011-06-08
AR025814A1 (es)	2002-12-18
HRP20010335A2 (en)	2002-06-30
ZA200103801B (en)	2002-05-10
US6455505B2 (en)	2002-09-24
BR9915236A (pt)	2002-01-08
PL348098A1 (en)	2002-05-06
HUP0104035A2 (hu)	2002-02-28
TR200101286T2 (tr)	2001-09-21
AU1052600A (en)	2000-05-29
IL142996A (en)	2006-12-10
DE69905447D1 (de)	2003-03-27

Legal Events

Date	Code	Title	Description
2005-01-10	IF	Valid on the event date
2005-10-31	KO00	Lapse of patent	Effective date: 20050822

Publication	Publication Date	Title
AU766138B2 (en)	2003-10-09	Novel erythromycin derivatives, preparation method and use as medicines
JP2992540B2 (ja)	1999-12-20	新規なエリスロマイシン誘導体、それらの製造法及び薬剤としての使用
JPH06199887A (ja)	1994-07-19	新規なエリスロマイシン誘導体、それらの製造法及びそれらの薬剤としての用途
AU772171B2 (en)	2004-04-08	New derivatives of erythromycin, their preparation process and their use as medicaments
US6313101B1 (en)	2001-11-06	Derivatives of erythromycin, their preparation process and their use as medicaments
JPH08231583A (ja)	1996-09-10	新規なエリスロマイシン誘導体、それらの製造法及び薬剤としての使用
FR2732684A1 (fr)	1996-10-11	Nouveaux derives de l'erythromycine, leur procede de preparation et leur application comme medicaments
KR20000068014A (ko)	2000-11-25	신규 에리트로마이신 유도체, 그의 제조방법 및 의약으로서의용도
JP2001506620A (ja)	2001-05-22	新規なエリスロマイシン誘導体、それらの製造方法及びそれらの医薬としての利用
KR20000062286A (ko)	2000-10-25	신규한 에리트로마이신 유도체, 제조 방법 및 의약품으로서 용도
JP2003534231A (ja)	2003-11-18	新規の６−デオキシエリスロマイシン誘導体、それらの製造方法及びそれらの薬剤としての使用
CZ417699A3 (cs)	2000-06-14	Nové deriváty erythromycinu, způsob jejich přípravy a jejich použití jako léčiv
HK1010732B (en)	2000-05-19	Erythromycin derivatives, their process of preparation and their use as medicaments