IL93936A - History of 9-dioxo-21,9-epoxy - erythromycin, method of preparation History of 11-oxo and 11-hydroxy, and pharmaceutical preparations containing them - Google Patents

History of 9-dioxo-21,9-epoxy - erythromycin, method of preparation History of 11-oxo and 11-hydroxy, and pharmaceutical preparations containing them

Info

Publication number: IL93936A
Authority: IL; Israel
Prior art keywords: deoxo; epoxy; amino; mmol; erythromycin
Prior art date: 1989-03-28

Application number

IL9393690A

Other languages

English (en)

Hebrew (he)

Other versions

IL93936A0 (en

Original Assignee

Abbott Lab

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.)

1989-03-28

Filing date

1990-03-28

Publication date

1994-06-24

1990-03-28 Application filed by Abbott Lab filed Critical Abbott Lab

1990-12-23 Publication of IL93936A0 publication Critical patent/IL93936A0/xx

1994-06-24 Publication of IL93936A publication Critical patent/IL93936A/en

Links

238000000034 method Methods 0.000 title claims abstract description 71
239000008194 pharmaceutical composition Substances 0.000 title claims description 6
238000002360 preparation method Methods 0.000 title description 6
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 claims abstract description 96
150000001875 compounds Chemical class 0.000 claims description 150
229960003276 erythromycin Drugs 0.000 claims description 81
-1 phenylmethoxy Chemical group 0.000 claims description 77
229930006677 Erythromycin A Natural products 0.000 claims description 61
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 35
239000001257 hydrogen Substances 0.000 claims description 29
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
208000015181 infectious disease Diseases 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 10
150000003839 salts Chemical class 0.000 claims description 10
150000002148 esters Chemical class 0.000 claims description 9
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 5
150000002431 hydrogen Chemical group 0.000 claims description 5
229910052760 oxygen Inorganic materials 0.000 claims description 5
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
230000001580 bacterial effect Effects 0.000 claims description 4
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 3
230000002906 microbiologic effect Effects 0.000 claims description 3
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 2
210000000481 breast Anatomy 0.000 claims 1
239000000203 mixture Substances 0.000 abstract description 59
239000004593 Epoxy Substances 0.000 abstract description 4
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 270
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 169
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 149
239000000243 solution Substances 0.000 description 127
239000000047 product Substances 0.000 description 90
239000011541 reaction mixture Substances 0.000 description 80
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 78
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 68
UIIMBOGNXHQVGW-UHFFFAOYSA-M sodium bicarbonate Substances [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 67
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 58
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 57
101150041968 CDC13 gene Proteins 0.000 description 53
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 52
239000000908 ammonium hydroxide Substances 0.000 description 52
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 45
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238000011282 treatment Methods 0.000 description 44
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 38
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229910000030 sodium bicarbonate Inorganic materials 0.000 description 37
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 36
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 36
241000191967 Staphylococcus aureus Species 0.000 description 35
239000002904 solvent Substances 0.000 description 35
235000017557 sodium bicarbonate Nutrition 0.000 description 34
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239000012267 brine Substances 0.000 description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 33
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238000006243 chemical reaction Methods 0.000 description 30
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KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 26
239000010410 layer Substances 0.000 description 26
125000001743 benzylic group Chemical group 0.000 description 25
YKAVHPRGGAUFDN-JTQLBUQXSA-N 24464-30-0 Chemical class 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 22
239000011521 glass Substances 0.000 description 22
239000003054 catalyst Substances 0.000 description 21
235000019439 ethyl acetate Nutrition 0.000 description 21
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 20
241000589517 Pseudomonas aeruginosa Species 0.000 description 20
239000012044 organic layer Substances 0.000 description 20
239000002798 polar solvent Substances 0.000 description 20
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QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 19
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 19
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 18
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 17
238000004128 high performance liquid chromatography Methods 0.000 description 16
238000003756 stirring Methods 0.000 description 16
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 15
229910000564 Raney nickel Inorganic materials 0.000 description 15
239000012043 crude product Substances 0.000 description 15
239000003480 eluent Substances 0.000 description 15
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125000002887 hydroxy group Chemical group [H]O* 0.000 description 15
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WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 13
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239000000725 suspension Substances 0.000 description 13
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 12
241000588724 Escherichia coli Species 0.000 description 12
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
150000001412 amines Chemical class 0.000 description 12
239000012442 inert solvent Substances 0.000 description 12
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 11
150000001299 aldehydes Chemical class 0.000 description 11
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238000003786 synthesis reaction Methods 0.000 description 10
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235000017281 sodium acetate Nutrition 0.000 description 9
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239000000843 powder Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 7
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238000005160 1H NMR spectroscopy Methods 0.000 description 6
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241001465754 Metazoa Species 0.000 description 6
238000005481 NMR spectroscopy Methods 0.000 description 6
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VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
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ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
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SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 description 1
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238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
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150000007524 organic acids Chemical class 0.000 description 1
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239000003960 organic solvent Substances 0.000 description 1
239000012285 osmium tetroxide Substances 0.000 description 1
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239000000312 peanut oil Substances 0.000 description 1
PJNZPQUBCPKICU-UHFFFAOYSA-N phosphoric acid;potassium Chemical compound [K].OP(O)(O)=O PJNZPQUBCPKICU-UHFFFAOYSA-N 0.000 description 1
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229920005862 polyol Polymers 0.000 description 1
150000003077 polyols Chemical class 0.000 description 1
229920001296 polysiloxane Polymers 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
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239000003380 propellant Substances 0.000 description 1
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238000011321 prophylaxis Methods 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
125000004076 pyridyl group Chemical group 0.000 description 1
238000010791 quenching Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
210000000664 rectum Anatomy 0.000 description 1
238000000611 regression analysis Methods 0.000 description 1
235000005713 safflower oil Nutrition 0.000 description 1
239000003813 safflower oil Substances 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
235000019345 sodium thiosulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
235000010356 sorbitol Nutrition 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000003206 sterilizing agent Substances 0.000 description 1
239000007929 subcutaneous injection Substances 0.000 description 1
238000010254 subcutaneous injection Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
230000009885 systemic effect Effects 0.000 description 1
235000012976 tarts Nutrition 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
OSBSFAARYOCBHB-UHFFFAOYSA-N tetrapropylammonium Chemical compound CCC[N+](CCC)(CCC)CCC OSBSFAARYOCBHB-UHFFFAOYSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
231100001274 therapeutic index Toxicity 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
230000000699 topical effect Effects 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
231100000816 toxic dose Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000004665 trialkylsilyl group Chemical group 0.000 description 1
210000003454 tympanic membrane Anatomy 0.000 description 1
229940070710 valerate Drugs 0.000 description 1
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
235000019871 vegetable fat Nutrition 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000011787 zinc oxide Substances 0.000 description 1
235000014692 zinc oxide Nutrition 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
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/08—Hetero rings containing eight or more ring members, e.g. erythromycins
- 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

Landscapes

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

IL9393690A 1989-03-28 1990-03-28 History of 9-dioxo-21,9-epoxy - erythromycin, method of preparation History of 11-oxo and 11-hydroxy, and pharmaceutical preparations containing them IL93936A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US32947389A	1989-03-28	1989-03-28

Publications (2)

Publication Number	Publication Date
IL93936A0 IL93936A0 (en)	1990-12-23
IL93936A true IL93936A (en)	1994-06-24

Family

ID=23285572

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9393690A IL93936A (en)	1989-03-28	1990-03-28	History of 9-dioxo-21,9-epoxy - erythromycin, method of preparation History of 11-oxo and 11-hydroxy, and pharmaceutical preparations containing them

Country Status (14)

Country	Link
US (1)	US5288709A (de)
EP (1)	EP0465581B1 (de)
JP (1)	JPH04504259A (de)
KR (1)	KR920701229A (de)
AT (1)	ATE128714T1 (de)
AU (1)	AU623764B2 (de)
CA (1)	CA2049359A1 (de)
DE (1)	DE69022845T2 (de)
DK (1)	DK0465581T3 (de)
ES (1)	ES2080140T3 (de)
GR (1)	GR1000519B (de)
IL (1)	IL93936A (de)
NZ (1)	NZ233117A (de)
WO (1)	WO1990011288A1 (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0549040A1 (de) *	1991-12-20	1993-06-30	Merck & Co. Inc.	Verfahren zur Herstellung von 4"-Derivaten von 9-Deoxo-8a-Aza-8a-Alkyl-8a-Homoerythromycin A
FR2713226B1 (fr) *	1993-12-03	1996-01-05	Roussel Uclaf	Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.
CN1166172A (zh) *	1995-08-03	1997-11-26	达德化学系统公司	奎尼定缀合物及其在免疫测定中的应用
EP0895999A1 (de)	1997-08-06	1999-02-10	Pfizer Products Inc.	C-4"-substituierte Macrolidantibiotica
GB0127349D0 (en) *	2001-11-14	2002-01-02	Glaxo Group Ltd	Macrolides
WO2003090760A1 (en) *	2002-04-25	2003-11-06	Abbott Laboratories	Oxolide antibacterials
SI1532131T1 (sl) *	2002-08-29	2009-04-30	Pfizer	Motilidne spojine
GB0310984D0 (en) *	2003-05-13	2003-06-18	Glaxo Group Ltd	Novel compounds
ES2278319T3 (es) *	2003-05-13	2007-08-01	Glaxo Group Limited	Nuevos compuestos con 14 y 15 miembros en el anillo.
GB0310986D0 (en) *	2003-05-13	2003-06-18	Glaxo Group Ltd	Novel compounds
GB0310980D0 (en) *	2003-05-13	2003-06-18	Glaxo Group Ltd	Novel compounds
CN107365338B (zh) *	2016-08-12	2021-03-19	西安世纪盛康药业有限公司	一类红霉素a-6,9-9,12-螺缩酮衍生物及其制备方法和应用
CN114504585A (zh) *	2020-11-16	2022-05-17	中国人民解放军海军军医大学	一种大环内酯类衍生物在制备减重降糖药物中的应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB1451798A (en) *	1973-08-02	1976-10-06	Ici Ltd	Prostanoic acid derivatives
US3963696A (en) *	1975-02-21	1976-06-15	Abbott Laboratories	6,6A-AND 6,7-Anhydroerythromycin B and derivatives thereof
EP0184921A3 (de) *	1984-12-08	1986-10-29	Beecham Group Plc	Erythromycinderivate
US5008249A (en) *	1985-08-31	1991-04-16	Kitasato Kenkyusho	Therapeutic method of stimulating digestive tract contractile motion in mammals
SE519436C2 (sv) *	2001-04-09	2003-02-25	Anoto Ab	Penna med på pennan löstagbart anordnade medel för byte av i pennan anordnat bläckstift, samt förfarande för stiftbyte

1990
- 1990-03-28 WO PCT/US1990/001658 patent/WO1990011288A1/en not_active Ceased
- 1990-03-28 AT AT90906030T patent/ATE128714T1/de not_active IP Right Cessation
- 1990-03-28 KR KR1019910701206A patent/KR920701229A/ko not_active Ceased
- 1990-03-28 DK DK90906030.3T patent/DK0465581T3/da active
- 1990-03-28 IL IL9393690A patent/IL93936A/en not_active IP Right Cessation
- 1990-03-28 AU AU54028/90A patent/AU623764B2/en not_active Ceased
- 1990-03-28 NZ NZ233117A patent/NZ233117A/en unknown
- 1990-03-28 GR GR900100232A patent/GR1000519B/el unknown
- 1990-03-28 DE DE69022845T patent/DE69022845T2/de not_active Expired - Fee Related
- 1990-03-28 ES ES90906030T patent/ES2080140T3/es not_active Expired - Lifetime
- 1990-03-28 US US07/743,424 patent/US5288709A/en not_active Expired - Fee Related
- 1990-03-28 CA CA002049359A patent/CA2049359A1/en not_active Abandoned
- 1990-03-28 JP JP2505715A patent/JPH04504259A/ja active Pending
- 1990-03-28 EP EP90906030A patent/EP0465581B1/de not_active Expired - Lifetime

Also Published As

Publication number	Publication date
KR920701229A (ko)	1992-08-11
EP0465581A1 (de)	1992-01-15
AU5402890A (en)	1990-10-22
DE69022845D1 (en)	1995-11-09
WO1990011288A1 (en)	1990-10-04
EP0465581A4 (en)	1992-05-13
GR900100232A (en)	1990-07-31
JPH04504259A (ja)	1992-07-30
DE69022845T2 (de)	1996-06-13
CA2049359A1 (en)	1990-09-29
ATE128714T1 (de)	1995-10-15
ES2080140T3 (es)	1996-02-01
IL93936A0 (en)	1990-12-23
DK0465581T3 (da)	1996-02-12
NZ233117A (en)	1991-05-28
GR1000519B (el)	1992-08-25
US5288709A (en)	1994-02-22
EP0465581B1 (de)	1995-10-04
AU623764B2 (en)	1992-05-21

Legal Events

Date	Code	Title	Description
1996-07-23	KB	Patent renewed
2001-06-14	RH	Patent void

Publication	Publication Date	Title
EP0638585B1 (de)	1996-11-13	5-0-desosaminylerythronolide a derivate
US4742049A (en)	1988-05-03	Semisynthetic erythromycin antibiotics
CA2253338C (en)	2007-05-08	6-o-substituted erythromycins and method for making them
US7129221B2 (en)	2006-10-31	6,11-bicyclic erythromycin derivatives
EP1015467B1 (de)	2004-01-07	6,9-verbrückte erythromycin-derivate
EP0465581B1 (de)	1995-10-04	Erythromycinderivate
AU1286799A (en)	1999-05-17	6,11-bridged erythromycin derivatives
US6420535B1 (en)	2002-07-16	6-O-carbamate ketolide derivatives
US4740502A (en)	1988-04-26	Semisynthetic erythromycin antibiotics
EP0201166A1 (de)	1986-11-12	Erythromycin-Derivate
EP1206476B1 (de)	2006-01-04	9a-azalide mit antibakterieller wirkung
CA2378671C (en)	2007-04-24	6-o-carbamate ketolide derivatives
EP1328535B1 (de)	2007-08-15	Makrolide
US20070270484A1 (en)	2007-11-22	3'-N-Substituted-3-O-Substituted Erythronolide a Derivatives
AU714176B2 (en)	1999-12-23	3-deoxy-3-descladinose derivatives of erythromycins A and B
HU196823B (en)	1989-01-30	Process for producing n-hydroxy-11-aza-10-deoxo-10-dihydro-erythromycin-a-n'-oxide
CA2235942C (en)	2005-12-06	Tricyclic erythromycin derivatives
EP0321185A2 (de)	1989-06-21	Erythromycin-Derivate
WO2001030793A1 (en)	2001-05-03	Hygromycin a prodrugs
MXPA00002216A (en)	2001-03-05	3-descladinose 6-o-substituded erythromycin derivatives