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 PDF

Info

Publication number: DK173182A
Authority: DK; Denmark
Prior art keywords: chem; hydrogen; carbon atoms; preparing; acid addition
Prior art date: 1981-04-20

Application number

DK173182A

Other languages

English (en)

Other versions

DK152133B (da

DK152133C (da

Inventor

A A Nagel

Original Assignee

Pfizer

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.)

1981-04-20

Filing date

1982-04-19

Publication date

1982-10-21

1982-04-19 Application filed by Pfizer filed Critical Pfizer

1982-10-21 Publication of DK173182A publication Critical patent/DK173182A/da

1988-02-01 Publication of DK152133B publication Critical patent/DK152133B/da

1988-07-11 Application granted granted Critical

1988-07-11 Publication of DK152133C publication Critical patent/DK152133C/da

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)
Genetics & Genomics (AREA)
Engineering & Computer Science (AREA)
Biotechnology (AREA)
Chemical Kinetics & Catalysis (AREA)
Pharmacology & Pharmacy (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Oncology (AREA)
Communicable Diseases (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.

DK173182A 1981-04-20 1982-04-19 Analogifremgangsmaade til fremstilling af oleandomycinderivater eller farmaceutisk acceptable syreadditionssalte deraf DK152133C (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/255,620 US4336368A (en)	1981-04-20	1981-04-20	4 Deoxy-4-methylene oleandomycin and derivatives thereof
US25562081		1981-04-20

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)

* Cited by examiner, † Cited by third party
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 Pharma Co Ltd	Erythromycin-a-derivate und verfahren zu ihrer herstellung.
SI9010556B (sl) *	1990-03-21	1998-10-31	Pliva	Oleandomicin oksimi in postopek za njihovo pripravo
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)

* Cited by examiner, † Cited by third party
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
US4166901A (en) *	1978-01-03	1979-09-04	Pfizer Inc.	4"-Deoxy-4"-arylglyoxamido- and aroylthioformamido derivatives of oleandomycin and its esters
US4124755A (en) *	1978-01-03	1978-11-07	Pfizer Inc.	11-Alkanoyl-4"-deoxy-4"-isonitrilo-oleandomycin derivatives

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 AT AT82301987T patent/ATE8147T1/de not_active IP Right Cessation
- 1982-04-16 EP EP82301987A patent/EP0063489B1/en not_active Expired
- 1982-04-16 DE DE8282301987T patent/DE3260297D1/de not_active Expired
- 1982-04-19 DK DK173182A patent/DK152133C/da active IP Right Grant
- 1982-04-19 JP JP57065232A patent/JPS57181096A/ja active Granted
- 1982-04-19 IE IE916/82A patent/IE52912B1/en unknown

Also Published As

Publication number	Publication date
EP0063489A1 (en)	1982-10-27
IE52912B1 (en)	1988-04-13
JPS6219438B2 (da)	1987-04-28
IE820916L (en)	1982-10-20
US4336368A (en)	1982-06-22
DE3260297D1 (en)	1984-08-02
EP0063489B1 (en)	1984-06-27
GR76472B (da)	1984-08-10
ATE8147T1 (de)	1984-07-15
DK152133B (da)	1988-02-01
JPS57181096A (en)	1982-11-08
DK152133C (da)	1988-07-11

Legal Events

Date	Code	Title	Description
1991-12-16	PBP	Patent lapsed
2000-03-06	B1	Patent granted (law 1993)

Publication	Publication Date	Title
DE2966954D1 (en)	1984-06-07	Alkyl derivatives of c-076 compounds, their preparation and their use as antiparasitic agents
KR830009107A (ko)	1983-12-17	2-페넴 화합물의 제조방법
ES474215A1 (es)	1979-04-01	Procedimiento para la preparacion de derivados imidazolile- tiloxialcoxilicos y sus analogos con agrupacion tio
JPS5731665A (en)	1982-02-20	2-position substituted 4-hydroxy-3-quinoline carboxylic acid novel derivative, manufacture, use as drug and composition and novel intermediate containing same
SE7600954L (sv)	1976-08-02	Tetrahydroisokinolinderivat och forfarande for framstellning derav
CA2125288A1 (en)	1994-07-07	Serotoninergic ergoline derivatives
DK152133C (da)	1988-07-11	Analogifremgangsmaade til fremstilling af oleandomycinderivater eller farmaceutisk acceptable syreadditionssalte deraf
SE8302474L (sv)	1983-12-04	Nya derivat av 4-hydroxi-3-kinolein-karboxylsyraderivat, substituerade i 2-stellning framstellning derav, anvendning derav som lekemedel samt kompositioner innehallande dem samt erhallna mellanprodukter
IL60584A (en)	1983-09-30	N-aminoalkylindole derivatives,their preparation and pharmaceutical compositions containing them
ES8304973A1 (es)	1983-03-16	Un procedimiento para la preparacion de nuevos derivados de tiocarbapenem 3-sustituidos.
ATE19879T1 (de)	1986-06-15	Furyloxazolylessigsaeure-derivate, verfahren zu deren herstellung und diese enthaltende pharmazeutische zusammensetzungen.
NZ234450A (en)	1991-10-25	Substituted pyrrolo(2,1-b)thiazole derivatives, intermediates and pharmaceutical compositions
AU555636B2 (en)	1986-10-02	1-aryloxy-3-alkynylamino-propan-2-ols
SE7903297L (sv)	1979-12-21	Beta-laktam-foreningar
IT1247137B (it)	1994-12-12	Derivati dell'acido 5-fenil-1h-pirazol-4-propionico, loro preparazione e loro impiego come medicamenti
IL94935A0 (en)	1991-04-15	Novel acrylic acid salts,a process for their preparation and pharmaceutical compositions containing them
IT1127317B (it)	1986-05-21	Formilderivati di idrazinopeniciline
ATE41151T1 (de)	1989-03-15	3,4-dihydro-2,5,7,8-tetramethyl-2h-1benzopyranderivate und verfahren zu ihrer herstellung.
IL66633A0 (en)	1982-12-31	1-aryloxy-3-alkylamino-propan-2-ols,their preparation and pharmaceutical compositions containing them
GB2022075A (en)	1979-12-12	Lactam-N-acetic acids and the preparation thereof
IL59046A (en)	1985-03-31	Process for the preparation of 7-sulfonimidoyl xanthone-2-carboxylic acid derivatives