BG62699B1 - Метод за изомерация на 10-метиловия радикал в производните на еритромицина - Google Patents

Метод за изомерация на 10-метиловия радикал в производните на еритромицина Download PDF

Info

Publication number: BG62699B1
Authority: BG; Bulgaria
Prior art keywords: radical; methyl; hydrogen atom; carbon atoms; isomer
Prior art date: 1996-05-14

Application number

BG102925A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG102925A (en

Inventor

Yannick Benedetti

Jacques Lagouardat

Jacques Scholl

Original Assignee

Hoechst Marion Roussel

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.)

1996-05-14

Filing date

1998-11-13

Publication date

2000-05-31

1998-11-13 Application filed by Hoechst Marion Roussel filed Critical Hoechst Marion Roussel

1999-08-31 Publication of BG102925A publication Critical patent/BG102925A/xx

2000-05-31 Publication of BG62699B1 publication Critical patent/BG62699B1/bg

Links

238000000034 method Methods 0.000 title claims abstract description 25
238000006317 isomerization reaction Methods 0.000 title claims description 8
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 description 20
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 20
150000003254 radicals Chemical class 0.000 claims abstract description 20
150000001875 compounds Chemical class 0.000 claims abstract description 19
-1 NH2 radical Chemical class 0.000 claims abstract description 17
239000000203 mixture Substances 0.000 claims abstract description 17
WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical group [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 claims abstract description 9
239000003795 chemical substances by application Substances 0.000 claims abstract description 8
229910052799 carbon Inorganic materials 0.000 claims abstract description 7
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 69
125000004432 carbon atom Chemical group C* 0.000 claims description 16
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 claims description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 6
239000007864 aqueous solution Substances 0.000 claims description 5
229910052757 nitrogen Inorganic materials 0.000 claims description 5
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 claims description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
239000000243 solution Substances 0.000 claims description 4
LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 claims description 4
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 claims description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
229910000027 potassium carbonate Inorganic materials 0.000 claims description 3
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 claims description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 claims description 2
125000003118 aryl group Chemical group 0.000 claims description 2
229910000160 potassium phosphate Inorganic materials 0.000 claims description 2
235000011009 potassium phosphates Nutrition 0.000 claims description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 2
229910000029 sodium carbonate Inorganic materials 0.000 claims description 2
239000002904 solvent Substances 0.000 claims description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
101100241859 Mus musculus Oacyl gene Proteins 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
229910052739 hydrogen Inorganic materials 0.000 claims 1
239000001257 hydrogen Substances 0.000 claims 1
238000004519 manufacturing process Methods 0.000 abstract description 2
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
229960003276 erythromycin Drugs 0.000 description 9
230000009466 transformation Effects 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
230000003115 biocidal effect Effects 0.000 description 3
125000000335 thiazolyl group Chemical group 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 2
GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 1
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
125000004618 benzofuryl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 description 1
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
238000010276 construction Methods 0.000 description 1
ALEXXDVDDISNDU-JZYPGELDSA-N cortisol 21-acetate Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@@](C(=O)COC(=O)C)(O)[C@@]1(C)C[C@@H]2O ALEXXDVDDISNDU-JZYPGELDSA-N 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
125000005842 heteroatom Chemical group 0.000 description 1
238000004128 high performance liquid chromatography Methods 0.000 description 1
239000005457 ice water Substances 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
235000011181 potassium carbonates Nutrition 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000010926 purge Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
150000005622 tetraalkylammonium hydroxides Chemical class 0.000 description 1
125000001544 thienyl group Chemical group 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
238000009423 ventilation Methods 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
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof

Landscapes

Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Engineering & Computer Science (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BG102925A 1996-05-14 1998-11-13 Метод за изомерация на 10-метиловия радикал в производните на еритромицина BG62699B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
FR9605966A FR2748746B1 (fr)	1996-05-14	1996-05-14	Nouveau procede d'isomerisation du radical methyle en 10 de derives de l'erythromycine
PCT/FR1997/000840 WO1997043297A1 (fr)	1996-05-14	1997-05-13	Nouveau procede d'isomerisation du radical methyle en 10 de derives de l'erythromycine

Publications (2)

Publication Number	Publication Date
BG102925A BG102925A (en)	1999-08-31
BG62699B1 true BG62699B1 (bg)	2000-05-31

Family

ID=9492104

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG102925A BG62699B1 (bg)	1996-05-14	1998-11-13	Метод за изомерация на 10-метиловия радикал в производните на еритромицина

Country Status (28)

Country	Link
US (1)	US6022965A (de)
EP (1)	EP0912591B1 (de)
JP (1)	JP3304098B2 (de)
KR (1)	KR100457757B1 (de)
CN (1)	CN1160366C (de)
AT (1)	ATE213251T1 (de)
AU (1)	AU720721B2 (de)
BG (1)	BG62699B1 (de)
BR (1)	BR9709243A (de)
CA (1)	CA2254795C (de)
CZ (1)	CZ289644B6 (de)
DE (1)	DE69710468T2 (de)
DK (1)	DK0912591T3 (de)
EA (1)	EA000939B1 (de)
ES (1)	ES2171943T3 (de)
FR (1)	FR2748746B1 (de)
GE (1)	GEP20012418B (de)
HU (1)	HU226676B1 (de)
IL (1)	IL126796A0 (de)
NO (1)	NO310823B1 (de)
NZ (1)	NZ332411A (de)
PL (1)	PL183467B1 (de)
PT (1)	PT912591E (de)
SK (1)	SK283649B6 (de)
TR (1)	TR199802297T2 (de)
UA (1)	UA55412C2 (de)
WO (1)	WO1997043297A1 (de)
YU (1)	YU49500B (de)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
AU5299499A (en)	1998-09-22	2000-04-10	Pfizer Products Inc.	Carbamate and carbazate ketolide antibiotics
AP2001002222A0 (en)	1999-01-27	2001-09-30	Pfizer Prod Inc	Ketolide antibiotics.
US6395710B1 (en)	1999-04-16	2002-05-28	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6590083B1 (en)	1999-04-16	2003-07-08	Ortho-Mcneil Pharmaceutical, Inc.	Ketolide antibacterials
US6514944B2 (en)	1999-04-16	2003-02-04	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6451768B1 (en)	1999-04-16	2002-09-17	Kosan Biosciences, Inc.	Macrolide antiinfective agents
US6939861B2 (en)	1999-04-16	2005-09-06	Kosan Biosciences, Inc.	Amido macrolides
IL145739A0 (en) *	1999-05-24	2002-07-25	Pfizer Prod Inc	13-methyl-erythromycin derivatives
EP1146051A3 (de) *	2000-04-10	2001-10-31	Pfizer Products Inc.	Erythromycin A-Derivate
US20020115621A1 (en) *	2000-08-07	2002-08-22	Wei-Gu Su	Macrolide antibiotics
EP2716647A3 (de) *	2004-02-27	2014-08-20	Rib-X Pharmaceuticals, Inc.	Makrocyclische Verbindungen Und Verfahren Zu Deren Herstellung Und Anwendung
EP2233493A1 (de) *	2004-12-21	2010-09-29	Pfizer Products Inc.	Makrolide
US8470985B2 (en)	2005-08-24	2013-06-25	Rib-X Pharmaceuticals, Inc.	Triazole compounds and methods of making and using the same

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR2718450B1 (fr) *	1994-04-08	1997-01-10	Roussel Uclaf	Nouveaux dérivés de l'érythromycine, leur procédé de préparation et leur application comme médicaments.

1996
- 1996-05-14 FR FR9605966A patent/FR2748746B1/fr not_active Expired - Lifetime
1997
- 1997-05-13 ES ES97924078T patent/ES2171943T3/es not_active Expired - Lifetime
- 1997-05-13 CA CA002254795A patent/CA2254795C/fr not_active Expired - Lifetime
- 1997-05-13 AU AU29663/97A patent/AU720721B2/en not_active Expired
- 1997-05-13 IL IL12679697A patent/IL126796A0/xx not_active IP Right Cessation
- 1997-05-13 TR TR1998/02297T patent/TR199802297T2/xx unknown
- 1997-05-13 US US09/180,641 patent/US6022965A/en not_active Expired - Lifetime
- 1997-05-13 AT AT97924078T patent/ATE213251T1/de active
- 1997-05-13 SK SK1530-98A patent/SK283649B6/sk not_active IP Right Cessation
- 1997-05-13 NZ NZ332411A patent/NZ332411A/xx not_active IP Right Cessation
- 1997-05-13 UA UA98126445A patent/UA55412C2/uk unknown
- 1997-05-13 DK DK97924078T patent/DK0912591T3/da active
- 1997-05-13 YU YU50398A patent/YU49500B/sh unknown
- 1997-05-13 JP JP54059497A patent/JP3304098B2/ja not_active Expired - Lifetime
- 1997-05-13 PT PT97924078T patent/PT912591E/pt unknown
- 1997-05-13 GE GEAP19974602A patent/GEP20012418B/en unknown
- 1997-05-13 CZ CZ19983557A patent/CZ289644B6/cs not_active IP Right Cessation
- 1997-05-13 DE DE69710468T patent/DE69710468T2/de not_active Expired - Lifetime
- 1997-05-13 HU HU9901158A patent/HU226676B1/hu unknown
- 1997-05-13 PL PL97329809A patent/PL183467B1/pl unknown
- 1997-05-13 BR BR9709243A patent/BR9709243A/pt not_active Application Discontinuation
- 1997-05-13 WO PCT/FR1997/000840 patent/WO1997043297A1/fr not_active Ceased
- 1997-05-13 EA EA199801008A patent/EA000939B1/ru not_active IP Right Cessation
- 1997-05-13 KR KR10-1998-0709175A patent/KR100457757B1/ko not_active Expired - Lifetime
- 1997-05-13 CN CNB971963835A patent/CN1160366C/zh not_active Expired - Lifetime
- 1997-05-13 EP EP97924078A patent/EP0912591B1/de not_active Expired - Lifetime
1998
- 1998-11-10 NO NO19985253A patent/NO310823B1/no not_active IP Right Cessation
- 1998-11-13 BG BG102925A patent/BG62699B1/bg unknown

Also Published As

Publication number	Publication date
NO310823B1 (no)	2001-09-03
PL329809A1 (en)	1999-04-12
NO985253L (no)	1998-11-10
GEP20012418B (en)	2001-04-25
EA000939B1 (ru)	2000-06-26
EP0912591A1 (de)	1999-05-06
NZ332411A (en)	1999-07-29
JP2000510142A (ja)	2000-08-08
SK153098A3 (en)	1999-05-07
UA55412C2 (uk)	2003-04-15
PT912591E (pt)	2002-07-31
CZ289644B6 (cs)	2002-03-13
PL183467B1 (pl)	2002-06-28
FR2748746B1 (fr)	1998-08-14
IL126796A0 (en)	1999-08-17
NO985253D0 (no)	1998-11-10
CA2254795C (fr)	2004-07-20
WO1997043297A1 (fr)	1997-11-20
CN1160366C (zh)	2004-08-04
ATE213251T1 (de)	2002-02-15
CN1225097A (zh)	1999-08-04
DE69710468T2 (de)	2002-08-22
EP0912591B1 (de)	2002-02-13
DE69710468D1 (de)	2002-03-21
BR9709243A (pt)	1999-08-10
CA2254795A1 (fr)	1997-11-20
KR20000011025A (ko)	2000-02-25
BG102925A (en)	1999-08-31
US6022965A (en)	2000-02-08
DK0912591T3 (da)	2002-07-08
TR199802297T2 (xx)	1999-02-22
AU2966397A (en)	1997-12-05
JP3304098B2 (ja)	2002-07-22
HUP9901158A3 (en)	1999-11-29
AU720721B2 (en)	2000-06-08
SK283649B6 (sk)	2003-11-04
YU49500B (sh)	2006-08-17
EA199801008A1 (ru)	1999-04-29
ES2171943T3 (es)	2002-09-16
HUP9901158A1 (hu)	1999-08-30
YU50398A (en)	1999-11-22
KR100457757B1 (ko)	2004-12-16
CZ355798A3 (cs)	1999-02-17
FR2748746A1 (fr)	1997-11-21
HU226676B1 (en)	2009-06-29

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CA1226279A (en)	1987-09-01	Method for preparing 6-0-methyl-2'-0, n-bis (benzyloxycarbonyl)-n-demethylerythromycin a
US4064143A (en)	1977-12-20	Oleandomycin derivatives
CN114349725A (zh)	2022-04-15	一种合成3,3-二取代苯酞的方法
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CA2359967C (en)	2011-08-30	Method for preparing an aza-macrolide with 4"(r)nh2
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