DE2167181C3 - Methyl-N-acetyl-6,7-aziridino-6-desamino-7-desoxy-2,3,4-tri-0-acetyl- -thiolincosaminid und Verfahren zu dessen Herstellung - Google Patents
Methyl-N-acetyl-6,7-aziridino-6-desamino-7-desoxy-2,3,4-tri-0-acetyl- -thiolincosaminid und Verfahren zu dessen HerstellungInfo
- Publication number
- DE2167181C3 DE2167181C3 DE2167181A DE2167181A DE2167181C3 DE 2167181 C3 DE2167181 C3 DE 2167181C3 DE 2167181 A DE2167181 A DE 2167181A DE 2167181 A DE2167181 A DE 2167181A DE 2167181 C3 DE2167181 C3 DE 2167181C3
- Authority
- DE
- Germany
- Prior art keywords
- acetyl
- deoxy
- methyl
- aziridino
- thiolincosaminide
- Prior art date
- 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
Links
- 238000000034 method Methods 0.000 title description 6
- 238000002360 preparation method Methods 0.000 title description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 8
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-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
- 239000002253 acid Substances 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 229960000583 acetic acid Drugs 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000000844 anti-bacterial effect Effects 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000006698 hydrazinolysis reaction Methods 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- LNQCUTNLHUQZLR-OZJWLQQPSA-N iridin Chemical group OC1=C(OC)C(OC)=CC(C=2C(C3=C(O)C(OC)=C(O[C@H]4[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O4)O)C=C3OC=2)=O)=C1 LNQCUTNLHUQZLR-OZJWLQQPSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000006140 methanolysis reaction Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3863—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms
- C08G18/3865—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms
- C08G18/3868—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms containing groups having one sulfur atom between two carbon atoms the sulfur atom belonging to a sulfide group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Medicinal Chemistry (AREA)
- Crystallography & Structural Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biochemistry (AREA)
- Polymers & Plastics (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Cephalosporin Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US2611970A | 1970-04-06 | 1970-04-06 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2167181B1 DE2167181B1 (de) | 1980-11-27 |
| DE2167181C3 true DE2167181C3 (de) | 1981-07-02 |
Family
ID=21830031
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2167181A Expired DE2167181C3 (de) | 1970-04-06 | 1971-04-02 | Methyl-N-acetyl-6,7-aziridino-6-desamino-7-desoxy-2,3,4-tri-0-acetyl- -thiolincosaminid und Verfahren zu dessen Herstellung |
| DE2167182A Expired DE2167182C3 (de) | 1970-04-06 | 1971-04-02 | Methyl-N-acetyl-2,3,4-tri-O-acetyl-7-desoxy-7(S)-methoxy-α-thiolincosaminid und Verfahren zu dessen Herstellung |
| DE2116066A Expired DE2116066C3 (de) | 1970-04-06 | 1971-04-02 | 7-Desoxy-7(S)-methoxy-lincomycin, dessen Säureadditionssalze und Verfahren zu deren Herstellung |
| DE2167180A Expired DE2167180C3 (de) | 1970-04-06 | 1971-04-02 | Methyl-7-desoxy-7(S)-methoxy-α-thiolincosaminid und Verfahren zu dessen Herstellung |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2167182A Expired DE2167182C3 (de) | 1970-04-06 | 1971-04-02 | Methyl-N-acetyl-2,3,4-tri-O-acetyl-7-desoxy-7(S)-methoxy-α-thiolincosaminid und Verfahren zu dessen Herstellung |
| DE2116066A Expired DE2116066C3 (de) | 1970-04-06 | 1971-04-02 | 7-Desoxy-7(S)-methoxy-lincomycin, dessen Säureadditionssalze und Verfahren zu deren Herstellung |
| DE2167180A Expired DE2167180C3 (de) | 1970-04-06 | 1971-04-02 | Methyl-7-desoxy-7(S)-methoxy-α-thiolincosaminid und Verfahren zu dessen Herstellung |
Country Status (14)
| Country | Link |
|---|---|
| US (1) | US3702322A (enExample) |
| JP (1) | JPS5527071B1 (enExample) |
| BE (1) | BE765370A (enExample) |
| CA (1) | CA945149A (enExample) |
| CH (2) | CH556325A (enExample) |
| DE (4) | DE2167181C3 (enExample) |
| DK (1) | DK134489B (enExample) |
| ES (1) | ES389524A1 (enExample) |
| FR (1) | FR2092009B1 (enExample) |
| GB (1) | GB1311438A (enExample) |
| IL (1) | IL36435A (enExample) |
| NL (1) | NL170960C (enExample) |
| SE (2) | SE385011B (enExample) |
| ZA (1) | ZA711709B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3853843A (en) * | 1972-12-13 | 1974-12-10 | Upjohn Co | Derivatives of thiolincosaminide compounds |
| US3870699A (en) * | 1973-03-06 | 1975-03-11 | Upjohn Co | Lincomycin analogs |
| DE60204897T2 (de) * | 2001-08-28 | 2006-05-11 | Pharmacia Corp. | Kristalline freie base von clindamycin |
| US7199105B2 (en) * | 2002-08-15 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| NZ538141A (en) * | 2002-08-15 | 2007-06-29 | Vicuron Pharm Inc | Lincomycin derivatives possessing antibacterial activity |
| US7199106B2 (en) | 2003-06-17 | 2007-04-03 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antimicrobial activity |
| US7256177B2 (en) | 2003-06-17 | 2007-08-14 | Vicuron Pharmaceuticals, Inc. | Lincomycin derivatives possessing antibacterial activity |
| US7361743B2 (en) * | 2004-02-11 | 2008-04-22 | Pfizer Inc | Lincomycin derivatives possessing antibacterial activity |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1467501A (fr) * | 1965-10-20 | 1967-01-27 | Upjohn Co | 7-halogéno-7-deoxylincomycine et 7-halogéno-7-dexoyepilincomycine, leurs analogues et isomères et leurs procédés de fabrication |
-
1970
- 1970-04-06 US US26119A patent/US3702322A/en not_active Expired - Lifetime
-
1971
- 1971-03-03 CA CA106,780A patent/CA945149A/en not_active Expired
- 1971-03-16 ZA ZA711709A patent/ZA711709B/xx unknown
- 1971-03-18 IL IL36435A patent/IL36435A/xx unknown
- 1971-03-19 CH CH405671A patent/CH556325A/xx not_active IP Right Cessation
- 1971-03-19 CH CH854674A patent/CH554858A/xx not_active IP Right Cessation
- 1971-03-24 ES ES389524A patent/ES389524A1/es not_active Expired
- 1971-03-30 NL NLAANVRAGE7104221,A patent/NL170960C/xx not_active IP Right Cessation
- 1971-03-31 DK DK155471AA patent/DK134489B/da unknown
- 1971-04-02 JP JP1974471A patent/JPS5527071B1/ja active Pending
- 1971-04-02 DE DE2167181A patent/DE2167181C3/de not_active Expired
- 1971-04-02 DE DE2167182A patent/DE2167182C3/de not_active Expired
- 1971-04-02 DE DE2116066A patent/DE2116066C3/de not_active Expired
- 1971-04-02 DE DE2167180A patent/DE2167180C3/de not_active Expired
- 1971-04-05 SE SE7104406A patent/SE385011B/xx unknown
- 1971-04-05 FR FR7111975A patent/FR2092009B1/fr not_active Expired
- 1971-04-06 BE BE765370A patent/BE765370A/xx not_active IP Right Cessation
- 1971-04-19 GB GB2553471*A patent/GB1311438A/en not_active Expired
-
1973
- 1973-10-08 SE SE7313667A patent/SE409209B/xx unknown
Non-Patent Citations (1)
| Title |
|---|
| NICHTS ERMITTELT * |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2167180B1 (de) | 1980-12-18 |
| NL170960B (nl) | 1982-08-16 |
| CH556325A (de) | 1974-11-29 |
| SE409209B (sv) | 1979-08-06 |
| DE2167180C3 (de) | 1981-07-30 |
| DE2116066A1 (de) | 1971-11-04 |
| ES389524A1 (es) | 1974-03-16 |
| DE2167181B1 (de) | 1980-11-27 |
| DK134489C (enExample) | 1977-04-25 |
| IL36435A (en) | 1975-04-25 |
| BE765370A (fr) | 1971-10-06 |
| FR2092009B1 (enExample) | 1974-09-27 |
| FR2092009A1 (enExample) | 1972-01-21 |
| DE2167182C3 (de) | 1981-09-17 |
| IL36435A0 (en) | 1971-05-26 |
| JPS5527071B1 (enExample) | 1980-07-17 |
| NL7104221A (enExample) | 1971-10-08 |
| DK134489B (da) | 1976-11-15 |
| DE2167182B1 (de) | 1981-01-08 |
| DE2116066C3 (de) | 1980-11-13 |
| DE2116066B2 (de) | 1980-01-17 |
| ZA711709B (en) | 1972-01-26 |
| CA945149A (en) | 1974-04-09 |
| GB1311438A (en) | 1973-03-28 |
| NL170960C (nl) | 1983-01-17 |
| US3702322A (en) | 1972-11-07 |
| CH554858A (de) | 1974-10-15 |
| SE385011B (sv) | 1976-05-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| OI | Miscellaneous see part 1 | ||
| OD | Request for examination | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |