JPS6159637B2 - - Google Patents

Info

Publication number: JPS6159637B2
Authority: JP; Japan
Prior art keywords: reaction; group; chloroform; acid; water
Prior art date: 1979-11-13
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

JP54146642A

Other languages

English (en)

Japanese (ja)

Other versions

JPS5671099A (en

Inventor

Hideo Sakakibara

Tatsuro Fujiwara

Susumu Watanabe

Tetsuo Matsuda

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.)

Toyo Jozo KK

Original Assignee

Toyo Jozo KK

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.)

1979-11-13

Filing date

1979-11-13

Publication date

1986-12-17

1979-11-13 Application filed by Toyo Jozo KK filed Critical Toyo Jozo KK

1979-11-13 Priority to JP14664279A priority Critical patent/JPS5671099A/ja

1980-08-29 Priority to NL8004922A priority patent/NL8004922A/nl

1980-09-02 Priority to DE19803033032 priority patent/DE3033032A1/de

1980-09-05 Priority to US06/184,375 priority patent/US4345069A/en

1980-09-09 Priority to GB8029019A priority patent/GB2058765B/en

1980-09-17 Priority to FR8019987A priority patent/FR2465747A1/fr

1980-09-17 Priority to CA000360427A priority patent/CA1192542A/en

1980-09-18 Priority to CH699780A priority patent/CH645650A5/de

1980-09-18 Priority to IT24738/80A priority patent/IT1141057B/it

1980-09-19 Priority to ES495214A priority patent/ES8205793A1/es

1981-06-13 Publication of JPS5671099A publication Critical patent/JPS5671099A/ja

1981-07-01 Priority to ES503606A priority patent/ES503606A0/es

1986-12-17 Publication of JPS6159637B2 publication Critical patent/JPS6159637B2/ja

Status Granted legal-status Critical Current

Links

150000003839 salts Chemical class 0.000 claims description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
238000006243 chemical reaction Methods 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 9
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000047 product Substances 0.000 description 7
238000004809 thin layer chromatography Methods 0.000 description 7
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
235000011114 ammonium hydroxide Nutrition 0.000 description 6
150000001875 compounds Chemical class 0.000 description 6
238000000034 method Methods 0.000 description 6
239000000203 mixture Substances 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
229930194936 Tylosin Natural products 0.000 description 5
239000004182 Tylosin Substances 0.000 description 5
230000008034 disappearance Effects 0.000 description 5
-1 phosphoric acid Chemical class 0.000 description 5
239000000741 silica gel Substances 0.000 description 5
229910002027 silica gel Inorganic materials 0.000 description 5
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 description 5
229960004059 tylosin Drugs 0.000 description 5
235000019375 tylosin Nutrition 0.000 description 5
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 4
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 4
239000003960 organic solvent Substances 0.000 description 4
239000011701 zinc Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000000843 powder Substances 0.000 description 3
238000000746 purification Methods 0.000 description 3
235000009518 sodium iodide Nutrition 0.000 description 3
239000002904 solvent Substances 0.000 description 3
238000003756 stirring Methods 0.000 description 3
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
241000192125 Firmicutes Species 0.000 description 1
WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
235000011054 acetic acid Nutrition 0.000 description 1
NJUISRMVIKYYCN-UHFFFAOYSA-N acetic acid;chloroform;methanol;hydrate Chemical compound O.OC.CC(O)=O.ClC(Cl)Cl NJUISRMVIKYYCN-UHFFFAOYSA-N 0.000 description 1
239000003463 adsorbent Substances 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000003674 animal food additive Substances 0.000 description 1
230000000844 anti-bacterial effect Effects 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
235000003704 aspartic acid Nutrition 0.000 description 1
OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
230000003115 biocidal effect Effects 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
235000015165 citric acid Nutrition 0.000 description 1
238000004440 column chromatography Methods 0.000 description 1
IJKVHSBPTUYDLN-UHFFFAOYSA-N dihydroxy(oxo)silane Chemical compound O[Si](O)=O IJKVHSBPTUYDLN-UHFFFAOYSA-N 0.000 description 1
230000000694 effects Effects 0.000 description 1
235000013922 glutamic acid Nutrition 0.000 description 1
239000004220 glutamic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000012264 purified product Substances 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
239000002994 raw material Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229940126585 therapeutic drug Drugs 0.000 description 1
238000007070 tosylation reaction Methods 0.000 description 1

Landscapes

Fodder In General (AREA)
Saccharide Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

JP14664279A 1979-09-19 1979-11-13 20-deoxodesmycosin Granted JPS5671099A (en)

Priority Applications (11)

Application Number	Priority Date	Filing Date	Title
JP14664279A JPS5671099A (en)	1979-11-13	1979-11-13	20-deoxodesmycosin
NL8004922A NL8004922A (nl)	1979-09-19	1980-08-29	Deformyltylosinederivaten.
DE19803033032 DE3033032A1 (de)	1979-09-19	1980-09-02	Deformyltylosinderivate
US06/184,375 US4345069A (en)	1979-09-19	1980-09-05	Deformyltylosin derivatives
GB8029019A GB2058765B (en)	1979-09-19	1980-09-09	Deformyltylosin derivatives
FR8019987A FR2465747A1 (fr)	1979-09-19	1980-09-17	Derives de deformyltylosine utiles notamment comme antibiotiques
CA000360427A CA1192542A (en)	1979-09-19	1980-09-17	Deformyltylosin derivatives
CH699780A CH645650A5 (de)	1979-09-19	1980-09-18	Deformyltylosinderivate.
IT24738/80A IT1141057B (it)	1979-09-19	1980-09-18	Derivati di deformiltilosina e loro preparazione
ES495214A ES8205793A1 (es)	1979-09-19	1980-09-19	Procedimiento para la obtencion de nuevos derivados defor- miltilosinos
ES503606A ES503606A0 (es)	1979-09-19	1981-07-01	Procedimiento de produccion de 20-deoxo-4-semicaroriltilomiao de una sal de la misma.

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP14664279A JPS5671099A (en)	1979-11-13	1979-11-13	20-deoxodesmycosin

Publications (2)

Publication Number	Publication Date
JPS5671099A JPS5671099A (en)	1981-06-13
JPS6159637B2 true JPS6159637B2 (zh)	1986-12-17

Family

ID=15412334

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP14664279A Granted JPS5671099A (en)	1979-09-19	1979-11-13	20-deoxodesmycosin

Country Status (1)

Country	Link
JP (1)	JPS5671099A (zh)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4443436A (en) *	1982-09-13	1984-04-17	Eli Lilly And Company	C-20-Modified macrolide derivatives of the macrolide antibiotics tylosin, desmycosin, macrocin, and lactenocin
ZA841277B (en) *	1983-02-28	1985-09-25	Lilly Co Eli	C-20-and c-23-modified macrolide derivatives

1979
- 1979-11-13 JP JP14664279A patent/JPS5671099A/ja active Granted

Also Published As

Publication number	Publication date
JPS5671099A (en)	1981-06-13

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