FI56688C - Foerfarande foer framstaellning av metyl-n-acetyl-2,3,4-tri-o-acetyl-7-deoxi-7-snrxr3-alfa-tiolinkosaminider som aer anvaendbara foer framstaellning av 7-deoxi-7-rsn-linkomyciner - Google Patents
Foerfarande foer framstaellning av metyl-n-acetyl-2,3,4-tri-o-acetyl-7-deoxi-7-snrxr3-alfa-tiolinkosaminider som aer anvaendbara foer framstaellning av 7-deoxi-7-rsn-linkomyciner Download PDFInfo
- Publication number
- FI56688C FI56688C FI1700/72A FI170072A FI56688C FI 56688 C FI56688 C FI 56688C FI 1700/72 A FI1700/72 A FI 1700/72A FI 170072 A FI170072 A FI 170072A FI 56688 C FI56688 C FI 56688C
- Authority
- FI
- Finland
- Prior art keywords
- acetyl
- methyl
- deoxy
- tri
- sulfide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 19
- -1 aliphatic hydrocarbon radical Chemical class 0.000 claims description 76
- 125000004432 carbon atom Chemical group C* 0.000 claims description 19
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 11
- 238000002360 preparation method Methods 0.000 claims description 7
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 229920006395 saturated elastomer Polymers 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- 125000001931 aliphatic group Chemical group 0.000 claims 1
- 125000003118 aryl group Chemical group 0.000 claims 1
- 150000005840 aryl radicals Chemical class 0.000 claims 1
- 125000003396 thiol group Chemical class [H]S* 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 87
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 76
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 74
- 150000001875 compounds Chemical class 0.000 description 32
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 28
- 238000004458 analytical method Methods 0.000 description 28
- 235000019441 ethanol Nutrition 0.000 description 27
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 24
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 238000010438 heat treatment Methods 0.000 description 21
- 238000001819 mass spectrum Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 15
- 238000000638 solvent extraction Methods 0.000 description 12
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 10
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 10
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 9
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- ROSSIHMZZJOVOU-UHFFFAOYSA-N 2-(methylthio)propane Chemical group CSC(C)C ROSSIHMZZJOVOU-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical group CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 4
- SJJZGKUOHPJHDH-UHFFFAOYSA-N 2-methylsulfanylethanethiol Chemical group CSCCS SJJZGKUOHPJHDH-UHFFFAOYSA-N 0.000 description 3
- BNOCQOAIEGGKKK-UHFFFAOYSA-N 4-(3-hydroxybutylsulfanyl)butan-2-ol Chemical group CC(O)CCSCCC(C)O BNOCQOAIEGGKKK-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- OPMRTBDRQRSNDN-UHFFFAOYSA-N Diethyl trisulfide Chemical group CCSSSCC OPMRTBDRQRSNDN-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 150000003568 thioethers Chemical class 0.000 description 3
- VLSYQLPMYBNHCJ-UHFFFAOYSA-N 4-methylsulfanylbutane-1-thiol Chemical group CSCCCCS VLSYQLPMYBNHCJ-UHFFFAOYSA-N 0.000 description 2
- GBLFYXOKFMMTMV-UHFFFAOYSA-N 4-methylsulfanylbutyl acetate Chemical group CSCCCCOC(C)=O GBLFYXOKFMMTMV-UHFFFAOYSA-N 0.000 description 2
- OTQVGYMGQKHLMY-UHFFFAOYSA-N Cyclopentyl-1-thiaethane Chemical compound CSC1CCCC1 OTQVGYMGQKHLMY-UHFFFAOYSA-N 0.000 description 2
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 2
- ZERULLAPCVRMCO-UHFFFAOYSA-N Dipropyl sulfide Chemical compound CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 2
- 229910004373 HOAc Inorganic materials 0.000 description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- PFRGXCVKLLPLIP-UHFFFAOYSA-N diallyl disulfide Chemical compound C=CCSSCC=C PFRGXCVKLLPLIP-UHFFFAOYSA-N 0.000 description 2
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 2
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 2
- 229920001021 polysulfide Polymers 0.000 description 2
- 239000005077 polysulfide Substances 0.000 description 2
- 150000008117 polysulfides Polymers 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- 150000003573 thiols Chemical class 0.000 description 2
- QEJZCKJXVYGWMY-UHFFFAOYSA-N (cyclopentyldisulfanyl)cyclopentane Chemical compound C1CCCC1SSC1CCCC1 QEJZCKJXVYGWMY-UHFFFAOYSA-N 0.000 description 1
- JIZDZCFZPMIBPK-UHFFFAOYSA-N 1,3-bis(methylsulfanyl)propane Chemical group CSCCCSC JIZDZCFZPMIBPK-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OBDMURXBJLOXCR-UHFFFAOYSA-N 1-(3,3-dimethyl-2-sulfanylbutyl)sulfanyl-3,3-dimethylbutane-2-thiol Chemical group C(C)(C)(C)C(CSCC(C(C)(C)C)S)S OBDMURXBJLOXCR-UHFFFAOYSA-N 0.000 description 1
- ZOASGOXWEHUTKZ-UHFFFAOYSA-N 1-(Methylthio)-propane Chemical compound CCCSC ZOASGOXWEHUTKZ-UHFFFAOYSA-N 0.000 description 1
- WEGOLYBUWCMMMY-UHFFFAOYSA-N 1-bromo-2-propanol Chemical compound CC(O)CBr WEGOLYBUWCMMMY-UHFFFAOYSA-N 0.000 description 1
- FIUYYKGOPZCCRI-UHFFFAOYSA-N 1-methoxy-2-methylsulfanylethane Chemical compound COCCSC FIUYYKGOPZCCRI-UHFFFAOYSA-N 0.000 description 1
- BKCNDTDWDGQHSD-UHFFFAOYSA-N 2-(tert-butyldisulfanyl)-2-methylpropane Chemical group CC(C)(C)SSC(C)(C)C BKCNDTDWDGQHSD-UHFFFAOYSA-N 0.000 description 1
- DBTWOTKWIVISQR-UHFFFAOYSA-N 2-bromopropan-1-ol Chemical compound CC(Br)CO DBTWOTKWIVISQR-UHFFFAOYSA-N 0.000 description 1
- CJFVCTVYZFTORU-UHFFFAOYSA-N 2-methyl-2-methylsulfanylpropane Chemical group CSC(C)(C)C CJFVCTVYZFTORU-UHFFFAOYSA-N 0.000 description 1
- CQIKBSVHIBIPGY-UHFFFAOYSA-N 2-methylsulfanylethyl acetate Chemical group CSCCOC(C)=O CQIKBSVHIBIPGY-UHFFFAOYSA-N 0.000 description 1
- WBBPRCNXBQTYLF-UHFFFAOYSA-N 2-methylthioethanol Chemical group CSCCO WBBPRCNXBQTYLF-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- LNMBCRKRCIMQLW-UHFFFAOYSA-N 2-tert-butylsulfanyl-2-methylpropane Chemical compound CC(C)(C)SC(C)(C)C LNMBCRKRCIMQLW-UHFFFAOYSA-N 0.000 description 1
- LPZQTNIAYMRVMF-UHFFFAOYSA-N 3-methylthiopropyl acetate Chemical group CSCCCOC(C)=O LPZQTNIAYMRVMF-UHFFFAOYSA-N 0.000 description 1
- UPORRSVUKDLQKW-UHFFFAOYSA-N 4-(3-acetyloxybutylsulfanyl)butan-2-yl acetate Chemical compound C(C)(=O)OC(CCSCCC(OC(C)=O)C)C UPORRSVUKDLQKW-UHFFFAOYSA-N 0.000 description 1
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 1
- VNFYMAPAENTMMO-UHFFFAOYSA-N 5-chloro-2-methylquinoline Chemical group ClC1=CC=CC2=NC(C)=CC=C21 VNFYMAPAENTMMO-UHFFFAOYSA-N 0.000 description 1
- WDRIJARUHRPIDA-UHFFFAOYSA-N 5-methylsulfanylpentyl acetate Chemical group CSCCCCCOC(C)=O WDRIJARUHRPIDA-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical class CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- CUDSBWGCGSUXDB-UHFFFAOYSA-N Dibutyl disulfide Chemical group CCCCSSCCCC CUDSBWGCGSUXDB-UHFFFAOYSA-N 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical compound S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- LZAZXBXPKRULLB-UHFFFAOYSA-N Diisopropyl disulfide Chemical compound CC(C)SSC(C)C LZAZXBXPKRULLB-UHFFFAOYSA-N 0.000 description 1
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical group CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 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 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- LTGPFZWZZNUIIK-LURJTMIESA-N Lysol Chemical compound NCCCC[C@H](N)CO LTGPFZWZZNUIIK-LURJTMIESA-N 0.000 description 1
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
- QQBIOCGHCKNYGP-UHFFFAOYSA-N Methylsulfanylcyclohexane Chemical compound CSC1CCCCC1 QQBIOCGHCKNYGP-UHFFFAOYSA-N 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- HREHPDVXTLYQKG-UHFFFAOYSA-N [2-[(2-acetyloxycyclohexyl)methylsulfanylmethyl]cyclohexyl] acetate Chemical compound C(C)(=O)OC1C(CCCC1)CSCC1C(CCCC1)OC(C)=O HREHPDVXTLYQKG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- ANZYICWUZDRSKW-UHFFFAOYSA-N acetic acid 2-methylsulfanylethanethiol Chemical compound C(C)(=O)O.CSCCS ANZYICWUZDRSKW-UHFFFAOYSA-N 0.000 description 1
- 229940008075 allyl sulfide Drugs 0.000 description 1
- 125000004069 aziridinyl group Chemical group 0.000 description 1
- LKMCJXXOBRCATQ-UHFFFAOYSA-N benzylsulfanylbenzene Chemical group C=1C=CC=CC=1CSC1=CC=CC=C1 LKMCJXXOBRCATQ-UHFFFAOYSA-N 0.000 description 1
- LUFPJJNWMYZRQE-UHFFFAOYSA-N benzylsulfanylmethylbenzene Chemical group C=1C=CC=CC=1CSCC1=CC=CC=C1 LUFPJJNWMYZRQE-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- SMTOKHQOVJRXLK-UHFFFAOYSA-N butane-1,4-dithiol Chemical compound SCCCCS SMTOKHQOVJRXLK-UHFFFAOYSA-N 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 238000006698 hydrazinolysis reaction Methods 0.000 description 1
- 229910000037 hydrogen sulfide Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N methyl acetate Chemical compound COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 238000007069 methylation reaction Methods 0.000 description 1
- AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical compound CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 239000005297 pyrex Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- RMBAVIFYHOYIFM-UHFFFAOYSA-M sodium methanethiolate Chemical compound [Na+].[S-]C RMBAVIFYHOYIFM-UHFFFAOYSA-M 0.000 description 1
- 239000012453 solvate Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003463 sulfur Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 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)
- Genetics & Genomics (AREA)
- Molecular Biology (AREA)
- Engineering & Computer Science (AREA)
- Biochemistry (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Crystallography & Structural Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15610071A | 1971-06-23 | 1971-06-23 | |
| US15610071 | 1971-06-23 | ||
| US16190971A | 1971-07-12 | 1971-07-12 | |
| US16190971 | 1971-07-12 | ||
| US19899071A | 1971-11-15 | 1971-11-15 | |
| US19899071 | 1971-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| FI56688B FI56688B (fi) | 1979-11-30 |
| FI56688C true FI56688C (fi) | 1980-03-10 |
Family
ID=27387802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI1700/72A FI56688C (fi) | 1971-06-23 | 1972-06-14 | Foerfarande foer framstaellning av metyl-n-acetyl-2,3,4-tri-o-acetyl-7-deoxi-7-snrxr3-alfa-tiolinkosaminider som aer anvaendbara foer framstaellning av 7-deoxi-7-rsn-linkomyciner |
Country Status (14)
| Country | Link |
|---|---|
| JP (1) | JPS5724359B1 (enExample) |
| AR (1) | AR192797A1 (enExample) |
| BE (1) | BE785375A (enExample) |
| CA (1) | CA971956A (enExample) |
| CH (1) | CH587286A5 (enExample) |
| DE (1) | DE2229950C2 (enExample) |
| FI (1) | FI56688C (enExample) |
| FR (1) | FR2143295A1 (enExample) |
| IL (1) | IL39658A (enExample) |
| NL (1) | NL176678C (enExample) |
| NO (1) | NO138949C (enExample) |
| PH (2) | PH11975A (enExample) |
| SE (2) | SE384685B (enExample) |
| YU (1) | YU36743B (enExample) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE977645C (de) * | 1954-03-12 | 1967-11-30 | Brown | Ruecklauf-Magnetverstaerker in Doppelwegschaltung |
| JPS5859309A (ja) * | 1981-10-02 | 1983-04-08 | Toyota Motor Corp | モノリス触媒保持構造 |
| JPS60107313U (ja) * | 1983-12-21 | 1985-07-22 | マツダ株式会社 | 触媒コンバ−タ |
| JPS60159815U (ja) * | 1984-04-02 | 1985-10-24 | トヨタ自動車株式会社 | 車輌の排気ガス浄化コンバ−タ |
| JPS63117U (enExample) * | 1986-06-19 | 1988-01-05 | ||
| US7871982B2 (en) | 2005-12-09 | 2011-01-18 | Meiji Seika Kaisha, Ltd. | Lincomycin derivatives and antimicrobial agents comprising the same as active ingredient |
| US7867980B2 (en) | 2007-05-31 | 2011-01-11 | Meiji Seika Kaisha, Ltd. | Lincosamide derivatives and antimicrobial agents comprising the same as active ingredient |
| WO2008146917A1 (ja) | 2007-05-31 | 2008-12-04 | Meiji Seika Kaisha, Ltd. | リンコマイシン誘導体及びこれを有効成分とする抗菌剤 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4839417A (enExample) * | 1971-06-23 | 1973-06-09 |
-
1969
- 1969-12-19 SE SE6917642A patent/SE384685B/xx unknown
-
1972
- 1972-06-02 CA CA143,734A patent/CA971956A/en not_active Expired
- 1972-06-09 IL IL39658A patent/IL39658A/en unknown
- 1972-06-14 CH CH884172A patent/CH587286A5/xx not_active IP Right Cessation
- 1972-06-14 FI FI1700/72A patent/FI56688C/fi active
- 1972-06-19 NL NLAANVRAGE7208333,A patent/NL176678C/xx not_active IP Right Cessation
- 1972-06-20 DE DE2229950A patent/DE2229950C2/de not_active Expired
- 1972-06-22 JP JP6190172A patent/JPS5724359B1/ja active Pending
- 1972-06-22 YU YU1660/72A patent/YU36743B/xx unknown
- 1972-06-22 FR FR7222565A patent/FR2143295A1/fr active Granted
- 1972-06-22 NO NO2230/72A patent/NO138949C/no unknown
- 1972-06-22 AR AR242688A patent/AR192797A1/es active
- 1972-06-22 SE SE6917642A patent/SE384686B/xx unknown
- 1972-06-23 PH PH13637A patent/PH11975A/en unknown
- 1972-06-23 BE BE785375A patent/BE785375A/xx not_active IP Right Cessation
-
1976
- 1976-07-22 PH PH18720A patent/PH13663A/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5724359B1 (enExample) | 1982-05-24 |
| CA971956A (en) | 1975-07-29 |
| FR2143295A1 (en) | 1973-02-02 |
| DE2229950C2 (de) | 1983-09-15 |
| NL7208333A (enExample) | 1972-12-28 |
| SE384686B (sv) | 1976-05-17 |
| NL176678B (nl) | 1984-12-17 |
| DE2229950A1 (de) | 1972-12-28 |
| YU36743B (en) | 1984-08-31 |
| YU166072A (en) | 1982-06-18 |
| AR192797A1 (es) | 1973-03-14 |
| CH587286A5 (enExample) | 1977-04-29 |
| NO138949B (no) | 1978-09-04 |
| PH11975A (en) | 1978-09-28 |
| FI56688B (fi) | 1979-11-30 |
| IL39658A0 (en) | 1972-08-30 |
| IL39658A (en) | 1977-04-29 |
| NO138949C (no) | 1978-12-13 |
| PH13663A (en) | 1980-08-26 |
| NL176678C (nl) | 1985-05-17 |
| SE384685B (sv) | 1976-05-17 |
| FR2143295B1 (enExample) | 1977-12-23 |
| BE785375A (fr) | 1972-12-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Davis et al. | Chemistry of sulfenic acids. 7. Reason for the high reactivity of sulfenic acids. Stabilization by intramolecular hydrogen bonding and electronegativity effects | |
| Mathey et al. | Phosphaferrocene | |
| FI56688C (fi) | Foerfarande foer framstaellning av metyl-n-acetyl-2,3,4-tri-o-acetyl-7-deoxi-7-snrxr3-alfa-tiolinkosaminider som aer anvaendbara foer framstaellning av 7-deoxi-7-rsn-linkomyciner | |
| AU2007220114B2 (en) | Novel 11 beta - hydroxyandrosta-4-ene-3-ones | |
| US4861765A (en) | 21-alkyl-, cycloalkyl- or aryl-substituted thio steroids and pharmaceutical compositions containing them | |
| KR890000678B1 (ko) | 소염 작용을 가진 17,17-비스(치환티오)안드로스텐 및 그의 제조방법 | |
| CA1329598C (en) | Retinoid carboxylic esters | |
| PT88580B (pt) | Processo para a preparacao de derivados de 1,3-ditio(oxatio ou dioxo)lano uteis como antagonistas de leucotrieno ltd4 e ltb4 | |
| SE8008524L (sv) | 4-pregnen-derivat, ett forfarande for deras framstellning, beredning och metod for behandling av inflammatoriska tillstand | |
| Wood | New components in defensive secretion of the striped skunk, Mephitis mephitis | |
| GB1603566A (en) | Steroidal naphthalenes | |
| Anthoni et al. | Synthesis of 4-methylthio-1, 2-dithiolane and 5-methylthio-1, 2, 3-trithiane. Two naturally occurring bioactive compounds | |
| US3915954A (en) | Derivatives of lincomycin and its analogs and process | |
| Paul et al. | Cysteine derivatives with reactive groups as potential antitumor agents | |
| Wilson et al. | A convenient preparation of unsymmetrically substituted pyrroles, furans, and thiophenes | |
| NOëL et al. | The chemistry of the 1, 2-dithiole ring | |
| CH503000A (de) | Verfahren zur Darstellung schwefelhaltiger Anlagerungsverbindungen des Allens und deren Verwendung | |
| Segall et al. | Oxidation of sulfallate and related alkyl dialkyldithiocarbamates to dialkylformamides via sulfine and iminium ion intermediates | |
| Hauptmann et al. | Some Mercaptols of Simple Cyclic Ketones | |
| US3183148A (en) | Combating nematodes with carbamate hetero-sulfur compounds | |
| Still et al. | Photochemical reduction of. beta.-and. gamma.-oxo sulfones | |
| EP0150461A2 (de) | Schwefelhaltige 6-Ketoprostaglandine | |
| Hürzeler et al. | Glyconothio‐O‐lactones. Part I. Preparation and reactions with nucleophiles | |
| CH631184A5 (de) | Verfahren zur herstellung von alkyl-(7r,s)-7-deoxy-7-(omega-substituiert-alkylthio)-alpha-thiolincosaminiden. | |
| Roush et al. | Trichothecene degradation studies: synthesis of 12, 13-deoxyanguidine and 12, 13-deoxyverrucarol |