NO116467B - - Google Patents
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- Publication number
- NO116467B NO116467B NO161854A NO16185466A NO116467B NO 116467 B NO116467 B NO 116467B NO 161854 A NO161854 A NO 161854A NO 16185466 A NO16185466 A NO 16185466A NO 116467 B NO116467 B NO 116467B
- Authority
- NO
- Norway
- Prior art keywords
- spiramycin
- hydrolysis
- group
- diesters
- monoesters
- Prior art date
Links
- ACTOXUHEUCPTEW-BWHGAVFKSA-N 2-[(4r,5s,6s,7r,9r,10r,11e,13e,16r)-6-[(2s,3r,4r,5s,6r)-5-[(2s,4r,5s,6s)-4,5-dihydroxy-4,6-dimethyloxan-2-yl]oxy-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-10-[(2s,5s,6r)-5-(dimethylamino)-6-methyloxan-2-yl]oxy-4-hydroxy-5-methoxy-9,16-dimethyl-2-o Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@@H](O)[C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)[C@@H]1CC[C@H](N(C)C)[C@@H](C)O1 ACTOXUHEUCPTEW-BWHGAVFKSA-N 0.000 claims description 35
- 239000004187 Spiramycin Substances 0.000 claims description 34
- 229930191512 spiramycin Natural products 0.000 claims description 34
- 229960001294 spiramycin Drugs 0.000 claims description 34
- 235000019372 spiramycin Nutrition 0.000 claims description 34
- 125000002252 acyl group Chemical group 0.000 claims description 9
- 230000007062 hydrolysis Effects 0.000 claims description 8
- 238000006460 hydrolysis reaction Methods 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 7
- 150000005690 diesters Chemical class 0.000 claims description 4
- 238000006136 alcoholysis reaction Methods 0.000 claims description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 12
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- -1 spiramycin diesters Chemical class 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- ZPCCSZFPOXBNDL-LWXQEXJOSA-N Spiramycin-II Natural products CO[C@H]1[C@@H](CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C)OC(=O)C ZPCCSZFPOXBNDL-LWXQEXJOSA-N 0.000 description 4
- HSZLKTCKAYXVBX-VPIGJTHDSA-N Spiramycin-III Natural products CCC(=O)O[C@@H]1CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@H](O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C)[C@H]1OC HSZLKTCKAYXVBX-VPIGJTHDSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- ZPCCSZFPOXBNDL-RSMXASMKSA-N spiramycin II Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]([C@H]([C@@H](CC=O)C[C@H]1C)O[C@H]1[C@@H]([C@H]([C@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@](C)(O)C2)[C@@H](C)O1)N(C)C)O)OC)OC(C)=O)[C@H]1CC[C@H](N(C)C)[C@H](C)O1 ZPCCSZFPOXBNDL-RSMXASMKSA-N 0.000 description 4
- 229950006796 spiramycin ii Drugs 0.000 description 4
- 229950003659 spiramycin iii Drugs 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HSZLKTCKAYXVBX-LYIMTGTFSA-N Spiramycin III Chemical compound O([C@H]1/C=C/C=C/C[C@@H](C)OC(=O)C[C@H]([C@@H]([C@@H](O[C@H]2[C@@H]([C@H]([C@H](O[C@@H]3O[C@@H](C)[C@H](O)[C@](C)(O)C3)[C@@H](C)O2)N(C)C)O)[C@@H](CC=O)C[C@H]1C)OC)OC(=O)CC)[C@H]1CC[C@H](N(C)C)[C@@H](C)O1 HSZLKTCKAYXVBX-LYIMTGTFSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- ACTOXUHEUCPTEW-ZOTSFZJCSA-N spiramycin I Natural products CO[C@H]1[C@H](O)CC(=O)O[C@H](C)CC=CC=C[C@H](O[C@H]2CC[C@@H]([C@@H](C)O2)N(C)C)[C@H](C)C[C@H](CC=O)[C@@H]1O[C@@H]3O[C@H](C)[C@@H](O[C@H]4C[C@@](C)(O)[C@@H](O)[C@H](C)O4)[C@@H]([C@H]3O)N(C)C ACTOXUHEUCPTEW-ZOTSFZJCSA-N 0.000 description 3
- 229950001955 spiramycin i Drugs 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 238000000862 absorption spectrum Methods 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000008065 acid anhydrides Chemical class 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 2
- 230000003301 hydrolyzing effect Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 239000003929 acidic solution Substances 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- DDQFXRYVNIPXRQ-UHFFFAOYSA-L cyclopenta-1,3-diene;dichlorozirconium(2+);1,2,3,5,5-pentamethylcyclopenta-1,3-diene Chemical compound Cl[Zr+2]Cl.C1C=CC=[C-]1.CC1=[C-]C(C)(C)C(C)=C1C DDQFXRYVNIPXRQ-UHFFFAOYSA-L 0.000 description 1
- 230000020176 deacylation Effects 0.000 description 1
- 238000005947 deacylation reaction Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 239000003120 macrolide antibiotic agent Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1161965 | 1965-03-02 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO116467B true NO116467B (de) | 1969-03-31 |
Family
ID=11782921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO161854A NO116467B (de) | 1965-03-02 | 1966-02-25 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3424743A (de) |
| BE (1) | BE677200A (de) |
| BR (1) | BR6677484D0 (de) |
| CH (1) | CH463531A (de) |
| DE (1) | DE1543712A1 (de) |
| DK (1) | DK113717B (de) |
| GB (1) | GB1135445A (de) |
| NL (1) | NL6602711A (de) |
| NO (1) | NO116467B (de) |
| SE (1) | SE350042B (de) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI56187C (fi) * | 1970-07-02 | 1979-12-10 | Takeda Chemical Industries Ltd | Foerfarande foer framstaellning av antibiotiskt aktiva estrar av makrolidglykosiderna b-5050 eller tetrahydro b-5050 |
| US4092473A (en) * | 1975-08-01 | 1978-05-30 | Sanraku Ocean Co., Ltd. | Tylosin derivatives and their manufacturing process |
| CN102260308B (zh) * | 2010-05-25 | 2014-05-28 | 沈阳同联集团有限公司 | 左旋异戊酰螺旋霉素iii、其制剂、制备方法及应用 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3011947A (en) * | 1955-11-30 | 1961-12-05 | Rhone Poulenc Sa | Separation of spiramycins by countercurrent distribution |
| US3000786A (en) * | 1957-06-14 | 1961-09-19 | Ciba Pharm Prod Inc | Process for making tetrahydro-spiramycin a |
| US3318866A (en) * | 1964-04-13 | 1967-05-09 | Upjohn Co | Process for making partial o-acylates of lincomycin |
-
1966
- 1966-02-25 NO NO161854A patent/NO116467B/no unknown
- 1966-02-28 CH CH285266A patent/CH463531A/fr unknown
- 1966-03-01 BE BE677200D patent/BE677200A/xx not_active IP Right Cessation
- 1966-03-01 DE DE19661543712 patent/DE1543712A1/de not_active Withdrawn
- 1966-03-02 DK DK108066AA patent/DK113717B/da unknown
- 1966-03-02 SE SE02716/66A patent/SE350042B/xx unknown
- 1966-03-02 GB GB9169/66A patent/GB1135445A/en not_active Expired
- 1966-03-02 NL NL6602711A patent/NL6602711A/xx unknown
- 1966-03-02 US US531290A patent/US3424743A/en not_active Expired - Lifetime
- 1966-03-02 BR BR177484/66A patent/BR6677484D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB1135445A (en) | 1968-12-04 |
| BR6677484D0 (pt) | 1973-09-11 |
| NL6602711A (de) | 1966-09-05 |
| US3424743A (en) | 1969-01-28 |
| DE1543712A1 (de) | 1969-12-11 |
| BE677200A (de) | 1966-08-01 |
| DK113717B (da) | 1969-04-21 |
| CH463531A (fr) | 1968-10-15 |
| SE350042B (de) | 1972-10-16 |
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