DK173182A - Fremgangsmaade til fremstilling af 4"-deoxy-4"-methylen-oleandomycin-forbindelser eller syreadditionssalte deraf - Google Patents
Fremgangsmaade til fremstilling af 4"-deoxy-4"-methylen-oleandomycin-forbindelser eller syreadditionssalte deraf Download PDFInfo
- Publication number
- DK173182A DK173182A DK173182A DK173182A DK173182A DK 173182 A DK173182 A DK 173182A DK 173182 A DK173182 A DK 173182A DK 173182 A DK173182 A DK 173182A DK 173182 A DK173182 A DK 173182A
- Authority
- DK
- Denmark
- Prior art keywords
- chem
- hydrogen
- carbon atoms
- preparing
- acid addition
- Prior art date
Links
- 239000002253 acid Substances 0.000 title abstract description 3
- 150000003839 salts Chemical class 0.000 title abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 9
- 239000001257 hydrogen Substances 0.000 abstract description 8
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 2
- RZPAKFUAFGMUPI-KGIGTXTPSA-N oleandomycin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1[C@@H](C)C(=O)O[C@H](C)[C@H](C)[C@H](O)[C@@H](C)C(=O)[C@]2(OC2)C[C@H](C)[C@H](O[C@H]2[C@@H]([C@H](C[C@@H](C)O2)N(C)C)O)[C@H]1C RZPAKFUAFGMUPI-KGIGTXTPSA-N 0.000 abstract description 2
- 125000005544 phthalimido group Chemical group 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 5
- RZPAKFUAFGMUPI-UHFFFAOYSA-N Oleandomycin Natural products O1C(C)C(O)C(OC)CC1OC1C(C)C(=O)OC(C)C(C)C(O)C(C)C(=O)C2(OC2)CC(C)C(OC2C(C(CC(C)O2)N(C)C)O)C1C RZPAKFUAFGMUPI-UHFFFAOYSA-N 0.000 abstract 1
- 239000004104 Oleandomycin Substances 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 229940088710 antibiotic agent Drugs 0.000 abstract 1
- 125000001246 bromo group Chemical group Br* 0.000 abstract 1
- 125000001589 carboacyl group Chemical group 0.000 abstract 1
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 1
- 229960002351 oleandomycin Drugs 0.000 abstract 1
- 235000019367 oleandomycin Nutrition 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- Engineering & Computer Science (AREA)
- Genetics & Genomics (AREA)
- Oncology (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Animal Behavior & Ethology (AREA)
- Communicable Diseases (AREA)
- Pharmacology & Pharmacy (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Description
brom, C^-C^ alkyl eller C^-C^ alkoxy; R$ er hydrogen eller
Rg er hydrogen, -COCH^,
eller
; R^ og R^, når de tages sammen med tilknytningsnitrogenatomet, er phthal-imido; og n er 0 eller 1, omsætter man i et inert opløsningsmiddel og i nærvær af en passende base den tilsvarende V-oxo-forbindelse med et dialkylphosphat med formlen (R°D)2P(0)CH2X, hvori R° er C^-C^ alkyl, hvorefter der hydrolyseres og i påkommende tilfælde hydroxylbeskyttelses- qruppe i 11- og 2-stillingen i oleandomycinkernen fjernes, eventuelt efterfulgt af dannelse af syreadditionssalte.
Forbindelserne udviser antibakteriel virkning såvel in vitro som in vivo, især over for grampositive, men også visse gramnegative bakterier og lader sig anvende såvel teknisk som som lægemiddelbestanddel.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25562081 | 1981-04-20 | ||
| US06/255,620 US4336368A (en) | 1981-04-20 | 1981-04-20 | 4 Deoxy-4-methylene oleandomycin and derivatives thereof |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK173182A true DK173182A (da) | 1982-10-21 |
| DK152133B DK152133B (da) | 1988-02-01 |
| DK152133C DK152133C (da) | 1988-07-11 |
Family
ID=22969153
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK173182A DK152133C (da) | 1981-04-20 | 1982-04-19 | Analogifremgangsmaade til fremstilling af oleandomycinderivater eller farmaceutisk acceptable syreadditionssalte deraf |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US4336368A (da) |
| EP (1) | EP0063489B1 (da) |
| JP (1) | JPS57181096A (da) |
| AT (1) | ATE8147T1 (da) |
| DE (1) | DE3260297D1 (da) |
| DK (1) | DK152133C (da) |
| GR (1) | GR76472B (da) |
| IE (1) | IE52912B1 (da) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4429116A (en) * | 1982-12-27 | 1984-01-31 | Pfizer Inc. | Alkylated oleandomycin containing compounds |
| US4640910A (en) * | 1985-11-12 | 1987-02-03 | Abbott Laboratories | Erythromycin A silylated compounds and method of use |
| DE3782994T2 (de) | 1986-09-18 | 1993-04-08 | Taisho Pharmaceutical Co Ltd | Erythromycin-a-derivate und verfahren zu ihrer herstellung. |
| YU55690A (en) * | 1990-03-21 | 1990-12-31 | Pliva Pharm & Chem Works | Process for preparing oleandomycin oxime |
| US5872229A (en) | 1995-11-21 | 1999-02-16 | Abbott Laboratories | Process for 6-O-alkylation of erythromycin derivatives |
| US5929219A (en) | 1997-09-10 | 1999-07-27 | Abbott Laboratories | 9-hydrazone and 9-azine erythromycin derivatives and a process of making the same |
| US6732014B2 (en) | 2001-02-27 | 2004-05-04 | Crane Co. | System for accomplishing product detection |
| US8548625B2 (en) | 2001-08-23 | 2013-10-01 | Crane Merchandising Systems, Inc. | Optical vend sensing system for product delivery detection |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4085119A (en) * | 1977-02-04 | 1978-04-18 | Pfizer Inc. | 4-Substituted amino derivatives of oleandomycin |
| US4090017A (en) * | 1977-02-04 | 1978-05-16 | Pfizer Inc. | 4-Deoxy-4-substituted amino derivatives of oleandomycin |
| US4124755A (en) * | 1978-01-03 | 1978-11-07 | Pfizer Inc. | 11-Alkanoyl-4"-deoxy-4"-isonitrilo-oleandomycin derivatives |
| US4166901A (en) * | 1978-01-03 | 1979-09-04 | Pfizer Inc. | 4"-Deoxy-4"-arylglyoxamido- and aroylthioformamido derivatives of oleandomycin and its esters |
-
1981
- 1981-04-20 US US06/255,620 patent/US4336368A/en not_active Expired - Lifetime
-
1982
- 1982-04-13 GR GR67907A patent/GR76472B/el unknown
- 1982-04-16 DE DE8282301987T patent/DE3260297D1/de not_active Expired
- 1982-04-16 AT AT82301987T patent/ATE8147T1/de not_active IP Right Cessation
- 1982-04-16 EP EP82301987A patent/EP0063489B1/en not_active Expired
- 1982-04-19 IE IE916/82A patent/IE52912B1/en unknown
- 1982-04-19 DK DK173182A patent/DK152133C/da active IP Right Grant
- 1982-04-19 JP JP57065232A patent/JPS57181096A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| EP0063489A1 (en) | 1982-10-27 |
| DK152133C (da) | 1988-07-11 |
| IE820916L (en) | 1982-10-20 |
| IE52912B1 (en) | 1988-04-13 |
| EP0063489B1 (en) | 1984-06-27 |
| JPS57181096A (en) | 1982-11-08 |
| DK152133B (da) | 1988-02-01 |
| GR76472B (da) | 1984-08-10 |
| US4336368A (en) | 1982-06-22 |
| ATE8147T1 (de) | 1984-07-15 |
| JPS6219438B2 (da) | 1987-04-28 |
| DE3260297D1 (en) | 1984-08-02 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PBP | Patent lapsed | ||
| B1 | Patent granted (law 1993) |