PL82863B1 - - Google Patents
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- Publication number
- PL82863B1 PL82863B1 PL1971146572A PL14657271A PL82863B1 PL 82863 B1 PL82863 B1 PL 82863B1 PL 1971146572 A PL1971146572 A PL 1971146572A PL 14657271 A PL14657271 A PL 14657271A PL 82863 B1 PL82863 B1 PL 82863B1
- Authority
- PL
- Poland
- Prior art keywords
- transition metal
- formula
- ions
- oxime
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 claims description 16
- 150000002923 oximes Chemical class 0.000 claims description 8
- 229910001428 transition metal ion Inorganic materials 0.000 claims description 6
- KYTWXIARANQMCA-PGYIPVOXSA-N (3r,4s,5s,6r,7r,9r,10z,11s,12r,13s,14r)-6-[(2s,3r,4s,6r)-4-(dimethylamino)-3-hydroxy-6-methyloxan-2-yl]oxy-14-ethyl-7,12,13-trihydroxy-10-hydroxyimino-4-[(2r,4r,5s,6s)-5-hydroxy-4-methoxy-4,6-dimethyloxan-2-yl]oxy-3,5,7,9,11,13-hexamethyl-oxacyclotetradec Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)C(=N\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 KYTWXIARANQMCA-PGYIPVOXSA-N 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- 238000002360 preparation method Methods 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 150000002466 imines Chemical class 0.000 claims description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052750 molybdenum Inorganic materials 0.000 claims description 2
- 239000011733 molybdenum Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims description 2
- 150000003623 transition metal compounds Chemical class 0.000 claims 3
- UUFQTNFCRMXOAE-UHFFFAOYSA-N 1-methylmethylene Chemical compound C[CH] UUFQTNFCRMXOAE-UHFFFAOYSA-N 0.000 claims 1
- 229910001430 chromium ion Inorganic materials 0.000 claims 1
- 229910001456 vanadium ion Inorganic materials 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 8
- XCLJRCAJSCMIND-JCTYMORFSA-N (9S)-erythromycyclamine Chemical compound O([C@@H]1[C@@H](C)C(=O)O[C@@H]([C@@]([C@H](O)[C@@H](C)[C@@H](N)[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 XCLJRCAJSCMIND-JCTYMORFSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- ULGZDMOVFRHVEP-RWJQBGPGSA-N Erythromycin Chemical compound 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 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910000497 Amalgam Inorganic materials 0.000 description 2
- USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
- 239000005695 Ammonium acetate Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 229940043376 ammonium acetate Drugs 0.000 description 2
- 235000019257 ammonium acetate Nutrition 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 229960003276 erythromycin Drugs 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 238000004809 thin layer chromatography Methods 0.000 description 2
- 230000007704 transition Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910052725 zinc Inorganic materials 0.000 description 2
- 239000011701 zinc Substances 0.000 description 2
- 206010007882 Cellulitis Diseases 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- 229910021555 Chromium Chloride Inorganic materials 0.000 description 1
- ZOYWWAGVGBSJDL-UHFFFAOYSA-N D-desosamine Natural products CC1CC(N(C)C)C(O)C(O)O1 ZOYWWAGVGBSJDL-UHFFFAOYSA-N 0.000 description 1
- IDRYSCOQVVUBIJ-UHFFFAOYSA-N Erythromycin-B Natural products CC1C(OC2C(C(CC(C)O2)N(C)C)O)C(C)(O)CC(C)C(=O)C(C)C(O)C(C)C(CC)OC(=O)C(C)C1OC1CC(C)(OC)C(O)C(C)O1 IDRYSCOQVVUBIJ-UHFFFAOYSA-N 0.000 description 1
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000295644 Staphylococcaceae Species 0.000 description 1
- 229910021550 Vanadium Chloride Inorganic materials 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- UNTBPXHCXVWYOI-UHFFFAOYSA-O azanium;oxido(dioxo)vanadium Chemical compound [NH4+].[O-][V](=O)=O UNTBPXHCXVWYOI-UHFFFAOYSA-O 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 239000012928 buffer substance Substances 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- QSWDMMVNRMROPK-UHFFFAOYSA-K chromium(3+) trichloride Chemical compound [Cl-].[Cl-].[Cl-].[Cr+3] QSWDMMVNRMROPK-UHFFFAOYSA-K 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- VTJCSBJRQLZNHE-CSMHCCOUSA-N desosamine Chemical group C[C@@H](O)C[C@H](N(C)C)[C@@H](O)C=O VTJCSBJRQLZNHE-CSMHCCOUSA-N 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- -1 erythromycin B oxime Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- RPESBQCJGHJMTK-UHFFFAOYSA-I pentachlorovanadium Chemical compound [Cl-].[Cl-].[Cl-].[Cl-].[Cl-].[V+5] RPESBQCJGHJMTK-UHFFFAOYSA-I 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- YONPGGFAJWQGJC-UHFFFAOYSA-K titanium(iii) chloride Chemical compound Cl[Ti](Cl)Cl YONPGGFAJWQGJC-UHFFFAOYSA-K 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- INCPMRSWRODNTN-UHFFFAOYSA-N trichloro-$l^{3}-chlorane Chemical compound ClCl(Cl)Cl INCPMRSWRODNTN-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 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)
- Engineering & Computer Science (AREA)
- Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1752970 | 1970-04-13 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| PL82863B1 true PL82863B1 (en:Method) | 1975-10-31 |
Family
ID=10096769
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL1971146572A PL82863B1 (en:Method) | 1970-04-13 | 1971-03-01 |
Country Status (21)
| Country | Link |
|---|---|
| US (1) | US3780019A (en:Method) |
| JP (1) | JPS5343516B1 (en:Method) |
| AT (1) | AT306922B (en:Method) |
| BE (1) | BE763131A (en:Method) |
| BR (1) | BR7101247D0 (en:Method) |
| CA (1) | CA952517A (en:Method) |
| CH (1) | CH526533A (en:Method) |
| CS (1) | CS190356B2 (en:Method) |
| DE (1) | DE2106616A1 (en:Method) |
| DK (1) | DK130467B (en:Method) |
| FR (1) | FR2086006B1 (en:Method) |
| GB (1) | GB1341022A (en:Method) |
| IE (1) | IE35378B1 (en:Method) |
| IL (1) | IL36286A (en:Method) |
| NL (1) | NL7102292A (en:Method) |
| PL (1) | PL82863B1 (en:Method) |
| RO (1) | RO58354A (en:Method) |
| SE (1) | SE376003B (en:Method) |
| SU (1) | SU584778A3 (en:Method) |
| YU (1) | YU35774B (en:Method) |
| ZA (1) | ZA71762B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FI72346C (fi) * | 1981-01-09 | 1987-05-11 | Pierrel Spa | Saett att framstaella nya halvsyntetiska makrolidantibiotika. |
| HUT42502A (en) * | 1985-03-12 | 1987-07-28 | Beecham Group Plc | Process for preparing new erythromycine derivatives |
| IL81395A0 (en) * | 1986-02-03 | 1987-08-31 | Lilly Co Eli | Novel derivatives of erythromycylamine |
| US5110800A (en) * | 1986-02-18 | 1992-05-05 | Eli Lilly And Company | Derivatives of erythromycylamine |
| US5075289A (en) * | 1988-06-07 | 1991-12-24 | Abbott Laboratories | 9-r-azacyclic erythromycin antibiotics |
| CN106188187A (zh) * | 2016-07-31 | 2016-12-07 | 合肥远志医药科技开发有限公司 | 一种地红霉素工业化生产方法 |
-
1970
- 1970-12-31 GB GB1752970*[A patent/GB1341022A/en not_active Expired
-
1971
- 1971-02-08 ZA ZA710762A patent/ZA71762B/xx unknown
- 1971-02-09 IE IE145/71A patent/IE35378B1/xx unknown
- 1971-02-09 CA CA104,875A patent/CA952517A/en not_active Expired
- 1971-02-12 DE DE19712106616 patent/DE2106616A1/de active Pending
- 1971-02-18 BE BE763131A patent/BE763131A/xx unknown
- 1971-02-22 NL NL7102292A patent/NL7102292A/xx unknown
- 1971-02-24 IL IL7136286A patent/IL36286A/xx unknown
- 1971-02-24 CS CS711373A patent/CS190356B2/cs unknown
- 1971-02-25 SU SU7101627128A patent/SU584778A3/ru active
- 1971-02-26 CH CH286871A patent/CH526533A/fr not_active IP Right Cessation
- 1971-02-26 YU YU485/71A patent/YU35774B/xx unknown
- 1971-02-26 AT AT169571A patent/AT306922B/de not_active IP Right Cessation
- 1971-03-01 RO RO197166112A patent/RO58354A/ro unknown
- 1971-03-01 PL PL1971146572A patent/PL82863B1/pl unknown
- 1971-03-01 DK DK91871AA patent/DK130467B/da unknown
- 1971-03-01 BR BR1247/71*[A patent/BR7101247D0/pt unknown
- 1971-03-01 JP JP7110335A patent/JPS5343516B1/ja active Pending
- 1971-03-01 FR FR7106912A patent/FR2086006B1/fr not_active Expired
- 1971-03-15 SE SE7103305A patent/SE376003B/xx unknown
- 1971-03-17 US US00125400A patent/US3780019A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| SU584778A3 (ru) | 1977-12-15 |
| CS190356B2 (en) | 1979-05-31 |
| CH526533A (fr) | 1972-08-15 |
| NL7102292A (en:Method) | 1971-10-15 |
| BR7101247D0 (pt) | 1973-04-05 |
| BE763131A (en:Method) | 1971-08-18 |
| YU48571A (en) | 1980-10-31 |
| SE376003B (en:Method) | 1975-05-05 |
| ZA71762B (en) | 1972-03-29 |
| IL36286A (en) | 1975-02-10 |
| GB1341022A (en) | 1973-12-19 |
| YU35774B (en) | 1981-06-30 |
| US3780019A (en) | 1973-12-18 |
| FR2086006B1 (en:Method) | 1975-06-06 |
| IL36286A0 (en) | 1971-04-28 |
| RO58354A (en:Method) | 1975-08-15 |
| AT306922B (de) | 1973-04-25 |
| IE35378L (en) | 1971-10-13 |
| FR2086006A1 (en:Method) | 1971-12-31 |
| CA952517A (en) | 1974-08-06 |
| DE2106616A1 (de) | 1971-11-04 |
| DK130467B (da) | 1975-02-24 |
| IE35378B1 (en) | 1976-02-04 |
| DK130467C (en:Method) | 1975-07-28 |
| JPS5343516B1 (en:Method) | 1978-11-20 |
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