CA1175423A - Preparation de 23-desoxy-5-0-mycaminosyltylonolide - Google Patents

Preparation de 23-desoxy-5-0-mycaminosyltylonolide

Info

Publication number: CA1175423A
Authority: CA; Canada
Prior art keywords: dmot; dihydro; tylosin; domt; medium
Prior art date: 1980-06-12
Legal status (The legal status 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 status listed.): Expired

Application number

CA000436137A

Other languages

English (en)

Inventor

Eugene T. Seno

Richard H. Baltz

Gene M. Wild

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Eli Lilly and Co

Original Assignee

Eli Lilly and Co

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.)

1980-06-12

Filing date

1983-09-06

Publication date

1984-10-02

1980-06-12 Priority claimed from US06/156,855 external-priority patent/US4321362A/en

1981-06-09 Priority claimed from CA000379332A external-priority patent/CA1172190A/fr

1983-09-06 Application filed by Eli Lilly and Co filed Critical Eli Lilly and Co

1983-09-06 Priority to CA000436137A priority Critical patent/CA1175423A/fr

1984-10-02 Application granted granted Critical

1984-10-02 Publication of CA1175423A publication Critical patent/CA1175423A/fr

Status Expired legal-status Critical Current

Links

238000000034 method Methods 0.000 title claims abstract description 30
229930194936 Tylosin Natural products 0.000 claims abstract description 23
239000004182 Tylosin Substances 0.000 claims abstract description 23
WBPYTXDJUQJLPQ-VMXQISHHSA-N tylosin Chemical compound O([C@@H]1[C@@H](C)O[C@H]([C@@H]([C@H]1N(C)C)O)O[C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H](/C=C(\C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)CO[C@H]1[C@@H]([C@H](OC)[C@H](O)[C@@H](C)O1)OC)CC)[C@H]1C[C@@](C)(O)[C@@H](O)[C@H](C)O1 WBPYTXDJUQJLPQ-VMXQISHHSA-N 0.000 claims abstract description 23
229960004059 tylosin Drugs 0.000 claims abstract description 23
235000019375 tylosin Nutrition 0.000 claims abstract description 23
238000000855 fermentation Methods 0.000 claims description 19
230000004151 fermentation Effects 0.000 claims description 19
239000002253 acid Substances 0.000 claims description 18
FERSDKADYZRIAA-HISVIJAKSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15s,16r)-6-[(2r,3r,4s,5r,6r)-4-(dimethylamino)-3,5-dihydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde Chemical compound O=CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](C)[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 FERSDKADYZRIAA-HISVIJAKSA-N 0.000 claims description 3
239000003242 anti bacterial agent Substances 0.000 abstract description 7
238000005903 acid hydrolysis reaction Methods 0.000 abstract description 3
239000002609 medium Substances 0.000 description 21
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
150000003839 salts Chemical class 0.000 description 17
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238000004519 manufacturing process Methods 0.000 description 12
-1 acyl ester Chemical class 0.000 description 11
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238000007792 addition Methods 0.000 description 10
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NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 6
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235000016068 Berberis vulgaris Nutrition 0.000 description 2
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QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
OUYCCCASQSFEME-QMMMGPOBSA-N L-tyrosine Chemical compound OC(=O)[C@@H](N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-QMMMGPOBSA-N 0.000 description 2
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LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical group CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
ZUHRLTIPDRLJHR-UHFFFAOYSA-N Rosamicin Natural products CCC1OC(=O)CC(O)C(C)C(OC2OC(C)CC(C2O)N(C)C)C(CC=O)CC(C)C(=O)C=CC3OC3C1C ZUHRLTIPDRLJHR-UHFFFAOYSA-N 0.000 description 2
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003638 chemical reducing agent Substances 0.000 description 2
238000012258 culturing Methods 0.000 description 2
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IUPCWCLVECYZRV-JZMZINANSA-N rosaramicin Chemical compound O([C@@H]1[C@@H](C)[C@H](O)CC(=O)O[C@@H]([C@H]([C@@H]2O[C@@]2(C)/C=C/C(=O)[C@H](C)C[C@@H]1CC=O)C)CC)[C@@H]1O[C@H](C)C[C@H](N(C)C)[C@H]1O IUPCWCLVECYZRV-JZMZINANSA-N 0.000 description 2
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OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 2
BHKKSKOHRFHHIN-MRVPVSSYSA-N 1-[[2-[(1R)-1-aminoethyl]-4-chlorophenyl]methyl]-2-sulfanylidene-5H-pyrrolo[3,2-d]pyrimidin-4-one Chemical compound N[C@H](C)C1=C(CN2C(NC(C3=C2C=CN3)=O)=S)C=CC(=C1)Cl BHKKSKOHRFHHIN-MRVPVSSYSA-N 0.000 description 1
IIZPXYDJLKNOIY-JXPKJXOSSA-N 1-palmitoyl-2-arachidonoyl-sn-glycero-3-phosphocholine Chemical compound CCCCCCCCCCCCCCCC(=O)OC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OC(=O)CCC\C=C/C\C=C/C\C=C/C\C=C/CCCCC IIZPXYDJLKNOIY-JXPKJXOSSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
OBUIQEYZGMZXPJ-NPQHDNJNSA-N 2-[(4r,5s,6s,7r,9r,11e,13e,15s,16r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-16-ethyl-4-hydroxy-5,9,13,15-tetramethyl-2,10-dioxo-1-oxacyclohexadeca-11,13-dien-7-yl]acetaldehyde Chemical compound O=CC[C@H]1C[C@@H](C)C(=O)\C=C\C(\C)=C\[C@H](C)[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[C@@H](C)O1 OBUIQEYZGMZXPJ-NPQHDNJNSA-N 0.000 description 1
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229940067606 lecithin Drugs 0.000 description 1
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239000007788 liquid Substances 0.000 description 1
239000003120 macrolide antibiotic agent Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
150000002689 maleic acids Chemical class 0.000 description 1
150000002691 malonic acids Chemical class 0.000 description 1
239000000155 melt Substances 0.000 description 1
150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
IJUPCLYLISRDRA-ULAWRXDQSA-N mycaminose Chemical compound C[C@@H](O)[C@@H](O)[C@H](N(C)C)[C@@H](O)C=O IJUPCLYLISRDRA-ULAWRXDQSA-N 0.000 description 1
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
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
229940051027 pasteurella multocida Drugs 0.000 description 1
230000001717 pathogenic effect Effects 0.000 description 1
239000008188 pellet Substances 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
150000003022 phthalic acids Chemical class 0.000 description 1
229920001451 polypropylene glycol Polymers 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
244000144977 poultry Species 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000002265 prevention Effects 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
229950005855 repromicin Drugs 0.000 description 1
238000011160 research Methods 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
238000012807 shake-flask culturing Methods 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000007787 solid Substances 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000004455 soybean meal Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000008107 starch Substances 0.000 description 1
229940031000 streptococcus pneumoniae Drugs 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003444 succinic acids Chemical class 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
230000009105 vegetative growth Effects 0.000 description 1

Landscapes

Preparation Of Compounds By Using Micro-Organisms (AREA)

CA000436137A 1980-06-12 1983-09-06 Preparation de 23-desoxy-5-0-mycaminosyltylonolide Expired CA1175423A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA000436137A CA1175423A (fr)	1980-06-12	1983-09-06	Preparation de 23-desoxy-5-0-mycaminosyltylonolide

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US06/156,855 US4321362A (en)	1980-06-12	1980-06-12	De(mycinosyloxy)tylosin and process for its production
US156,855		1980-06-12
CA000379332A CA1172190A (fr)	1980-06-12	1981-06-09	De(mycinosyloxy)tylosine et methode de preparation
CA000436137A CA1175423A (fr)	1980-06-12	1983-09-06	Preparation de 23-desoxy-5-0-mycaminosyltylonolide

Related Parent Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000379332A Division CA1172190A (fr)	1980-06-12	1981-06-09	De(mycinosyloxy)tylosine et methode de preparation

Publications (1)

Publication Number	Publication Date
CA1175423A true CA1175423A (fr)	1984-10-02

Family

ID=27167079

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000436137A Expired CA1175423A (fr)	1980-06-12	1983-09-06	Preparation de 23-desoxy-5-0-mycaminosyltylonolide

Country Status (1)

Country	Link
CA (1)	CA1175423A (fr)

1983
- 1983-09-06 CA CA000436137A patent/CA1175423A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2001-10-02	MKEX	Expiry

Publication	Publication Date	Title
US4321362A (en)	1982-03-23	De(mycinosyloxy)tylosin and process for its production
EP0052005B1 (fr)	1985-01-30	Antibiotiques du type macrolide
US4299953A (en)	1981-11-10	Mycarosyltylactone
CA1172190A (fr)	1984-08-07	De(mycinosyloxy)tylosine et methode de preparation
US4385116A (en)	1983-05-24	Demethylmacrocin and process for its production
US4366247A (en)	1982-12-28	Process for preparing tylactone
CA1211731A (fr)	1986-09-23	Derives de de(mycinosyloxy)tylosine
US4431809A (en)	1984-02-14	Antibiotic A-33853 derivatives
US4486584A (en)	1984-12-04	Demethylmacrocin compounds and derivatives thereof
EP0045157B1 (fr)	1984-04-18	Antibiotiques macrolides, leur préparation et compositions vétérinaires les contenant
US4334019A (en)	1982-06-08	Process for producing de(mycinosyloxy)tylosin
US4419447A (en)	1983-12-06	Fermentation process for producing demycinosyltylosin
US4419508A (en)	1983-12-06	20-Dihydro-20-deoxy-23-demycinosyltylosin and process for its production
US4537957A (en)	1985-08-27	Process for the production of mycaminosyltylonolide
US4528369A (en)	1985-07-09	20-Dihydro-20-deoxy-23-de(mycinosyloxy)tylosin
CA1175422A (fr)	1984-10-02	Preparation de 5-0-mycaminosyl-tylonolide
EP0045205B1 (fr)	1984-10-03	Macrolides
US4572895A (en)	1986-02-25	Process for preparing an antibiotic complex by culturing actinomyces strain ATCC 39417
NZ197869A (en)	1984-04-27	5-0-mycarosyl-20-dihydro-20,23-dideoxytylonolide derivatives