DD210060A5 - Verfahren zur herstellung von 5-0-mycaminosyltylonolidderivaten - Google Patents

Verfahren zur herstellung von 5-0-mycaminosyltylonolidderivaten Download PDF

Info

Publication number: DD210060A5
Authority: DD; German Democratic Republic
Prior art keywords: formula; compound; optionally substituted; omt; deep
Prior art date: 1982-07-19

Application number

DD83253192A

Other languages

German (de)

English (en)

Inventor

Herbert A Kirst

John E Toth

Original Assignee

Lilly Co Eli

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.)

1982-07-19

Filing date

1983-07-19

Publication date

1984-05-30

1983-07-19 Application filed by Lilly Co Eli filed Critical Lilly Co Eli

1984-05-30 Publication of DD210060A5 publication Critical patent/DD210060A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 17
238000002360 preparation method Methods 0.000 title claims abstract description 11
WGUJDBLMJBJUQU-VKRLOHBMSA-N 5-O-mycaminosyltylonolide Chemical class O=CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](CO)[C@@H](CC)OC(=O)C[C@@H](O)[C@H](C)[C@H]1O[C@H]1[C@H](O)[C@@H](N(C)C)[C@H](O)[C@@H](C)O1 WGUJDBLMJBJUQU-VKRLOHBMSA-N 0.000 title 1
-1 phenylacetyl Chemical group 0.000 claims abstract description 67
150000001875 compounds Chemical class 0.000 claims abstract description 53
239000001257 hydrogen Substances 0.000 claims abstract description 20
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 20
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims abstract description 14
150000002431 hydrogen Chemical class 0.000 claims abstract description 13
125000002252 acyl group Chemical group 0.000 claims abstract description 9
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 9
JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 claims abstract description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 8
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 7
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
125000000217 alkyl group Chemical group 0.000 claims abstract description 4
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims abstract description 4
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims abstract description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 4
ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 claims abstract description 3
125000001589 carboacyl group Chemical group 0.000 claims abstract 5
150000001412 amines Chemical class 0.000 claims abstract 2
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims abstract 2
150000003839 salts Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
230000010933 acylation Effects 0.000 claims description 4
238000005917 acylation reaction Methods 0.000 claims description 4
125000000405 phenylalanyl group Chemical group 0.000 abstract description 4
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 74
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239000000243 solution Substances 0.000 description 34
239000000203 mixture Substances 0.000 description 18
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 14
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238000006243 chemical reaction Methods 0.000 description 12
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 12
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125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 7
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230000000269 nucleophilic effect Effects 0.000 description 7
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WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
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125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
ONBQEOIKXPHGMB-VBSBHUPXSA-N 1-[2-[(2s,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4,6-dihydroxyphenyl]-3-(4-hydroxyphenyl)propan-1-one Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@H]1OC1=CC(O)=CC(O)=C1C(=O)CCC1=CC=C(O)C=C1 ONBQEOIKXPHGMB-VBSBHUPXSA-N 0.000 description 3
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 3
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 3
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
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229910021554 Chromium(II) chloride Inorganic materials 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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125000004432 carbon atom Chemical group C* 0.000 description 3
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XBWRJSSJWDOUSJ-UHFFFAOYSA-L chromium(ii) chloride Chemical compound Cl[Cr]Cl XBWRJSSJWDOUSJ-UHFFFAOYSA-L 0.000 description 3
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JYAQWANEOPJVEY-LYFYHCNISA-N mycarose Chemical compound C[C@H](O)[C@H](O)[C@](C)(O)CC=O JYAQWANEOPJVEY-LYFYHCNISA-N 0.000 description 1
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FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
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LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
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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)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Communicable Diseases (AREA)
Pharmacology & Pharmacy (AREA)
Public Health (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Oncology (AREA)
Animal Behavior & Ethology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Saccharide Compounds (AREA)
Cephalosporin Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Peptides Or Proteins (AREA)
Transition And Organic Metals Composition Catalysts For Addition Polymerization (AREA)
Hydrogenated Pyridines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

DD83253192A 1982-07-19 1983-07-19 Verfahren zur herstellung von 5-0-mycaminosyltylonolidderivaten DD210060A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/399,657 US4459290A (en)	1982-07-19	1982-07-19	C-23-Modified derivatives of OMT, pharmaceutical compositions and method of use

Publications (1)

Publication Number	Publication Date
DD210060A5 true DD210060A5 (de)	1984-05-30

Family

ID=23580431

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD83253192A DD210060A5 (de)	1982-07-19	1983-07-19	Verfahren zur herstellung von 5-0-mycaminosyltylonolidderivaten

Country Status (19)

Country	Link
US (1)	US4459290A (fr)
EP (1)	EP0099747B1 (fr)
JP (1)	JPS5931795A (fr)
KR (1)	KR850000967B1 (fr)
AT (1)	ATE25689T1 (fr)
AU (1)	AU1693483A (fr)
CA (1)	CA1202965A (fr)
DD (1)	DD210060A5 (fr)
DE (1)	DE3369997D1 (fr)
DK (1)	DK330383D0 (fr)
ES (1)	ES524196A0 (fr)
FI (1)	FI832603A7 (fr)
GB (1)	GB2123828B (fr)
GR (1)	GR78388B (fr)
NZ (1)	NZ204939A (fr)
PH (1)	PH19929A (fr)
PL (1)	PL243090A1 (fr)
PT (1)	PT77039A (fr)
ZA (1)	ZA835217B (fr)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4515941A (en) *	1982-04-07	1985-05-07	Toyo Jozo Kabushiki Kaisha	23-Demycinosyldesmycosin derivatives
JPS59141596A (ja) *	1983-02-03	1984-08-14	Toyo Jozo Co Ltd	３−ｏ−アシル−４″−デオキシデスマイコシン誘導体およびその製法
US4629786A (en) *	1983-02-28	1986-12-16	Eli Lilly And Company	C-20- and C-23 modified macrolide derivatives
DE3310533A1 (de) *	1983-03-23	1984-09-27	Bayer Ag, 5090 Leverkusen	Organisch-chemische verbindungen und verfahren zu ihrer herstellung
JPS6098540A (ja) *	1983-11-04	1985-06-01	Mitsubishi Electric Corp	磁気記録再生装置
JPS60115038A (ja) *	1983-11-26	1985-06-21	Mitsubishi Electric Corp	磁気録画再生装置
US4604380A (en) *	1985-01-18	1986-08-05	Eli Lilly And Company	C-23-substituted mycaminosyltylonolide compounds, pharmaceutical compositions and methods of use
US4581345A (en) *	1985-04-08	1986-04-08	Merck & Co., Inc.	Avermectin 8,9-cyclopropyl compounds, pharmaceutical composition and therapeutic methods of use
US6753415B2 (en)	2002-04-19	2004-06-22	Enanta Pharmaceuticals, Inc.	23-O-substituted 5-O-mycaminosyltylonide derivatives
US8053418B2 (en)	2005-01-24	2011-11-08	Microbial Chemistry Research Foundation	Anti-penicillin resistant pneumococci agent and novel 16-membered macrolide derivative

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
BE667952A (fr) *	1964-08-05
US4252898A (en) *	1979-05-23	1981-02-24	Eli Lilly And Company	Antibiotics A6888C and A6888X
JPS56122397A (en) *	1980-02-29	1981-09-25	Satoshi Omura	Marcolides
US4321362A (en) *	1980-06-12	1982-03-23	Eli Lilly And Company	De(mycinosyloxy)tylosin and process for its production
US4438109A (en) *	1980-07-25	1984-03-20	Zaidan Hojin Biseibutsu Kagaku Kenkyu Kai	Tylosin derivatives
US4341770A (en) *	1981-04-20	1982-07-27	Eli Lilly And Company	Method of controlling ureaplasma infections
US4341771A (en) *	1981-04-20	1982-07-27	Eli Lilly And Company	Method of controlling Pasteurella infections
AU551142B2 (en) *	1981-07-09	1986-04-17	Zaidan Hojin Biseibutsu Kagaku Kenkyukai	Tylosin derivatives

1982
- 1982-07-19 US US06/399,657 patent/US4459290A/en not_active Expired - Fee Related
1983
- 1983-07-18 AU AU16934/83A patent/AU1693483A/en not_active Abandoned
- 1983-07-18 ZA ZA835217A patent/ZA835217B/xx unknown
- 1983-07-18 KR KR1019830003275A patent/KR850000967B1/ko not_active Expired
- 1983-07-18 PT PT77039A patent/PT77039A/pt unknown
- 1983-07-18 FI FI832603A patent/FI832603A7/fi not_active Application Discontinuation
- 1983-07-18 EP EP83304154A patent/EP0099747B1/fr not_active Expired
- 1983-07-18 DE DE8383304154T patent/DE3369997D1/de not_active Expired
- 1983-07-18 DK DK3303/83A patent/DK330383D0/da not_active Application Discontinuation
- 1983-07-18 NZ NZ204939A patent/NZ204939A/en unknown
- 1983-07-18 GB GB08319307A patent/GB2123828B/en not_active Expired
- 1983-07-18 CA CA000432588A patent/CA1202965A/fr not_active Expired
- 1983-07-18 JP JP58131792A patent/JPS5931795A/ja active Pending
- 1983-07-18 GR GR71961A patent/GR78388B/el unknown
- 1983-07-18 ES ES524196A patent/ES524196A0/es active Granted
- 1983-07-18 AT AT83304154T patent/ATE25689T1/de not_active IP Right Cessation
- 1983-07-18 PH PH29240A patent/PH19929A/en unknown
- 1983-07-19 PL PL24309083A patent/PL243090A1/xx unknown
- 1983-07-19 DD DD83253192A patent/DD210060A5/de unknown

Also Published As

Publication number	Publication date
ES8504840A1 (es)	1985-05-01
CA1202965A (fr)	1986-04-08
KR850000967B1 (ko)	1985-07-02
GB2123828A (en)	1984-02-08
PL243090A1 (en)	1984-07-16
GB8319307D0 (en)	1983-08-17
FI832603A0 (fi)	1983-07-18
JPS5931795A (ja)	1984-02-20
DE3369997D1 (en)	1987-04-09
EP0099747A1 (fr)	1984-02-01
ATE25689T1 (de)	1987-03-15
US4459290A (en)	1984-07-10
EP0099747B1 (fr)	1987-03-04
FI832603A7 (fi)	1984-01-20
PH19929A (en)	1986-08-14
GB2123828B (en)	1985-11-13
NZ204939A (en)	1986-08-08
KR840005463A (ko)	1984-11-12
PT77039A (en)	1983-08-01
ES524196A0 (es)	1985-05-01
AU1693483A (en)	1984-01-26
ZA835217B (en)	1984-03-28
DK330383D0 (da)	1983-07-18
GR78388B (fr)	1984-09-26

Publication	Publication Date	Title
DE69733422T2 (de)	2006-05-04	6-0-substituierte ketoliden mit antibakteriellen wirkung
DE69832486T2 (de)	2006-07-27	C-4"-substitutierte macrolid-derivate
DE69114198T2 (de)	1996-06-27	O-Methylderivate von Azithromycin A, Verfahren und Zwischenverbindungen zu ihrer Herstellung und deren Verwendung zur Herstellung von Heilmitteln.
US4512982A (en)	1985-04-23	9α-Aza-9α-homoerythromycin compounds, pharmaceutical composition and therapeutic method
DE60220180T2 (de)	2008-01-17	14 bis 15 gliedrige makrolide mit antibakterieller aktivität
DE60123277T2 (de)	2007-09-13	Makrolidantibiotika
DE69315839T2 (de)	1998-04-09	Derivate von 16-gliedrigen antibiotischen macroliden
DE69824201T2 (de)	2005-09-22	Neue 9a-azalide
US5215980A (en)	1993-06-01	10-AZA-9-deoxo-11-deoxy-erythromycin A and derivatives thereof
DD210284A5 (de)	1984-06-06	Verfahren zur herstellung von 20-aminomakrolidderivaten
DD210060A5 (de)	1984-05-30	Verfahren zur herstellung von 5-0-mycaminosyltylonolidderivaten
DE69402714T2 (de)	1997-07-31	Amid-derivate von 16-gliedrige heterocyclen als antibiotische macrolide
DE2804508C2 (de)	1982-06-24	Epimere 4"-substituierte Aminoderivate des Oleandomycins und deren Verwendung als antibakterielle Wirkstoffe
DD210283A5 (de)	1984-06-06	Verfahren zur herstellung von 20-aminotylosin-derivaten
DD211565A5 (de)	1984-07-18	Verfahren zur herstellung von 4"-epi-erythromycin a und derivaten hiervon als brauchbare antibakterielle mittel
DE69022845T2 (de)	1996-06-13	Erythromycinderivate.
NZ207259A (en)	1987-02-20	C-20 and c-23 modified macrolides
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