GB1140663A - Lincomycin derivatives - Google Patents
Lincomycin derivativesInfo
- Publication number
- GB1140663A GB1140663A GB5299/66A GB529966A GB1140663A GB 1140663 A GB1140663 A GB 1140663A GB 5299/66 A GB5299/66 A GB 5299/66A GB 529966 A GB529966 A GB 529966A GB 1140663 A GB1140663 A GB 1140663A
- Authority
- GB
- United Kingdom
- Prior art keywords
- group
- acid addition
- cycloalkyl
- addition salts
- compounds
- 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
- OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical class CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@@H](C)O)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 OJMMVQQUTAEWLP-KIDUDLJLSA-N 0.000 title abstract 2
- 150000003839 salts Chemical class 0.000 abstract 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 3
- -1 diphenyl (p-methoxyphenyl) methyl Chemical group 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 1
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 1
- OJMMVQQUTAEWLP-UHFFFAOYSA-N Lincomycin Natural products CN1CC(CCC)CC1C(=O)NC(C(C)O)C1C(O)C(O)C(O)C(SC)O1 OJMMVQQUTAEWLP-UHFFFAOYSA-N 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000001118 alkylidene group Chemical group 0.000 abstract 1
- 229940069428 antacid Drugs 0.000 abstract 1
- 239000003159 antacid agent Substances 0.000 abstract 1
- 230000001458 anti-acid effect Effects 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 abstract 1
- 230000003115 biocidal effect Effects 0.000 abstract 1
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- 239000003112 inhibitor Substances 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 229960005287 lincomycin Drugs 0.000 abstract 1
- 125000006503 p-nitrobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1[N+]([O-])=O)C([H])([H])* 0.000 abstract 1
- 230000003071 parasitic effect Effects 0.000 abstract 1
- 238000005554 pickling Methods 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 abstract 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 abstract 1
Classifications
-
- 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)
- Biotechnology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1,140,663. Halo-lincomycin derivatives. UPJOHN CO. 7 Feb., 1966 [8 Feb., 1965; 1 Dec., 1965], No. 5299/66. Heading C2C. The invention comprises compounds of formula wherein R is a C 1-20 alkyl, C 3-8 cycloalkyl, C 4-8 cycloalkyl-alkyl, or C 7-12 aralkyl group and Ac is hydrogen or the acyl radical of an acid of one of the formulµ wherein R 1 and R 2 are C 1-20 alkylidene, C 3-8 cycloalkylidene, C 4-8 cycloalkyl-alkylidene or C 7-12 aralkylidene groups, R 3 is hydrogen or a group -HR 2 , and Z is an optionally substituted hydrocarbonyloxycarbonyl group or a trityl, diphenyl (p-methoxyphenyl) methyl, bis-(p-methoxyphenyl) phenyl-methyl, benzyl or p-nitrobenzyl group, and their preparation by reaction of the corresponding hydroxy compounds with thionyl chloride followed by heating, with if desired previous or subsequent interconversion of the group AcNH-. Inversion occurs in the reaction with thionyl chloride. Acid addition salts are also disclosed. The compounds of the invention closely analogous to lincomycin have antibiotic properties, and various products have buffer or antacid properties, react with isocyanates to form or modify polyurethanes or have surface active properties. The thiocyanic acid addition salts when condensed with formaldehyde form pickling inhibitors, the fluosilicic acid addition salt has mothproofing activity and the hexafluoroarsenic acid and hexafluorophosphoric acid addition salts have parasitic activity.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US43118465A | 1965-02-08 | 1965-02-08 | |
| US51128865A | 1965-12-01 | 1965-12-01 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1140663A true GB1140663A (en) | 1969-01-22 |
Family
ID=27028919
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5299/66A Expired GB1140663A (en) | 1965-02-08 | 1966-02-07 | Lincomycin derivatives |
Country Status (14)
| Country | Link |
|---|---|
| AT (1) | AT277457B (en) |
| BE (1) | BE676154A (en) |
| BR (1) | BR6676992D0 (en) |
| CH (1) | CH481072A (en) |
| DE (2) | DE1795740C2 (en) |
| DK (1) | DK136118B (en) |
| ES (1) | ES322754A1 (en) |
| FI (1) | FI48466C (en) |
| GB (1) | GB1140663A (en) |
| IL (1) | IL25011A (en) |
| NO (1) | NO123608B (en) |
| OA (1) | OA01910A (en) |
| SE (1) | SE300619B (en) |
| YU (1) | YU32779B (en) |
-
1966
- 1966-01-18 IL IL25011A patent/IL25011A/en unknown
- 1966-01-24 YU YU0122/66A patent/YU32779B/en unknown
- 1966-01-29 DE DE1795740A patent/DE1795740C2/en not_active Expired
- 1966-01-29 DE DE1620620A patent/DE1620620C3/en not_active Expired
- 1966-01-31 AT AT85966A patent/AT277457B/en not_active IP Right Cessation
- 1966-02-01 CH CH133866A patent/CH481072A/en not_active IP Right Cessation
- 1966-02-07 BR BR176992/66A patent/BR6676992D0/en unknown
- 1966-02-07 NO NO161593A patent/NO123608B/no unknown
- 1966-02-07 DK DK62166AA patent/DK136118B/en unknown
- 1966-02-07 SE SE1529/66A patent/SE300619B/xx unknown
- 1966-02-07 OA OA52347A patent/OA01910A/en unknown
- 1966-02-07 GB GB5299/66A patent/GB1140663A/en not_active Expired
- 1966-02-07 BE BE676154D patent/BE676154A/xx not_active IP Right Cessation
- 1966-02-08 ES ES0322754A patent/ES322754A1/en not_active Expired
- 1966-02-08 FI FI660305A patent/FI48466C/en active
Also Published As
| Publication number | Publication date |
|---|---|
| DE1620620A1 (en) | 1970-04-23 |
| YU32779B (en) | 1975-08-31 |
| DE1795740B1 (en) | 1974-10-17 |
| DK136118C (en) | 1978-02-13 |
| DE1795779B2 (en) | 1977-05-05 |
| NO123608B (en) | 1971-12-20 |
| DE1795740C2 (en) | 1975-06-12 |
| DE1620620C3 (en) | 1975-05-28 |
| DE1795779A1 (en) | 1975-04-10 |
| SE300619B (en) | 1968-05-06 |
| BR6676992D0 (en) | 1973-09-18 |
| DE1620620B2 (en) | 1974-09-26 |
| AT277457B (en) | 1969-12-29 |
| OA01910A (en) | 1970-02-04 |
| BE676154A (en) | 1966-08-08 |
| ES322754A1 (en) | 1966-11-16 |
| IL25011A (en) | 1971-10-20 |
| FI48466C (en) | 1974-10-10 |
| FI48466B (en) | 1974-07-01 |
| CH481072A (en) | 1969-11-15 |
| YU12266A (en) | 1975-02-28 |
| DK136118B (en) | 1977-08-15 |
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