IL39658A - 7 deoxy-7(s)-alkylthio-lincosaminide and lincomycin derivatives process for their preparation and pharmaceutical compositions containing 7-deoxy-7(s)-alkylthio-lincomycines - Google Patents
7 deoxy-7(s)-alkylthio-lincosaminide and lincomycin derivatives process for their preparation and pharmaceutical compositions containing 7-deoxy-7(s)-alkylthio-lincomycinesInfo
- Publication number
- IL39658A IL39658A IL39658A IL3965872A IL39658A IL 39658 A IL39658 A IL 39658A IL 39658 A IL39658 A IL 39658A IL 3965872 A IL3965872 A IL 3965872A IL 39658 A IL39658 A IL 39658A
- Authority
- IL
- Israel
- Prior art keywords
- methyl
- thio
- sulfide
- deoxy
- ethyl
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 89
- 239000008194 pharmaceutical composition Substances 0.000 title claims 2
- 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 description 5
- 238000002360 preparation method Methods 0.000 title description 2
- -1 furfuryl Chemical group 0.000 claims abstract description 166
- 239000002253 acid Substances 0.000 claims abstract description 38
- 150000003839 salts Chemical class 0.000 claims abstract description 17
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 90
- 150000001875 compounds Chemical class 0.000 claims description 66
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 37
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 36
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 claims description 34
- 238000010438 heat treatment Methods 0.000 claims description 25
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052799 carbon Inorganic materials 0.000 claims description 14
- 239000007858 starting material Substances 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000004215 Carbon black (E152) Substances 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 239000001301 oxygen Substances 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 5
- 239000011593 sulfur Substances 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 125000002252 acyl group Chemical group 0.000 claims description 4
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims description 3
- 125000001118 alkylidene group Chemical group 0.000 claims 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 125000001589 carboacyl group Chemical group 0.000 abstract description 3
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 2
- 125000003342 alkenyl group Chemical group 0.000 abstract description 2
- 229940069428 antacid Drugs 0.000 abstract description 2
- 239000003159 antacid agent Substances 0.000 abstract description 2
- 239000000872 buffer Substances 0.000 abstract description 2
- 229920005749 polyurethane resin Polymers 0.000 abstract description 2
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 abstract 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 abstract 1
- 125000004183 alkoxy alkyl group Chemical group 0.000 abstract 1
- 125000006350 alkyl thio alkyl group Chemical group 0.000 abstract 1
- 230000005494 condensation Effects 0.000 abstract 1
- 238000009833 condensation Methods 0.000 abstract 1
- 125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000002541 furyl group Chemical group 0.000 abstract 1
- 230000002401 inhibitory effect Effects 0.000 abstract 1
- 239000000575 pesticide Substances 0.000 abstract 1
- 125000006413 ring segment Chemical group 0.000 abstract 1
- 125000001544 thienyl group Chemical group 0.000 abstract 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 116
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 70
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 38
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 34
- 238000004949 mass spectrometry Methods 0.000 description 32
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 32
- 235000019441 ethanol Nutrition 0.000 description 30
- 239000012458 free base Substances 0.000 description 29
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 27
- 238000004458 analytical method Methods 0.000 description 25
- 229940015849 thiophene Drugs 0.000 description 25
- 239000002904 solvent Substances 0.000 description 24
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 22
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 22
- 238000009826 distribution Methods 0.000 description 19
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 16
- 229930193140 Neomycin Natural products 0.000 description 14
- 229960004927 neomycin Drugs 0.000 description 13
- 239000000243 solution Substances 0.000 description 13
- HTIRHQRTDBPHNZ-UHFFFAOYSA-N Dibutyl sulfide Chemical compound CCCCSCCCC HTIRHQRTDBPHNZ-UHFFFAOYSA-N 0.000 description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 125000004705 ethylthio group Chemical group C(C)S* 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 8
- CETBSQOFQKLHHZ-UHFFFAOYSA-N Diethyl disulfide Chemical compound CCSSCC CETBSQOFQKLHHZ-UHFFFAOYSA-N 0.000 description 8
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Natural products CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000006243 chemical reaction Methods 0.000 description 7
- ROSSIHMZZJOVOU-UHFFFAOYSA-N 2-(methylthio)propane Chemical compound CSC(C)C ROSSIHMZZJOVOU-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- JETFNRIIPBNRAT-UHFFFAOYSA-N butylsulfanylbenzene Chemical compound CCCCSC1=CC=CC=C1 JETFNRIIPBNRAT-UHFFFAOYSA-N 0.000 description 6
- LJSQFQKUNVCTIA-UHFFFAOYSA-N diethyl sulfide Chemical compound CCSCC LJSQFQKUNVCTIA-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- ZERULLAPCVRMCO-UHFFFAOYSA-N sulfure de di n-propyle Natural products CCCSCCC ZERULLAPCVRMCO-UHFFFAOYSA-N 0.000 description 6
- HNKJADCVZUBCPG-UHFFFAOYSA-N thioanisole Chemical compound CSC1=CC=CC=C1 HNKJADCVZUBCPG-UHFFFAOYSA-N 0.000 description 6
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 5
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 5
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- RUZLIIJDZBWWSA-INIZCTEOSA-N methyl 2-[[(1s)-1-(7-methyl-2-morpholin-4-yl-4-oxopyrido[1,2-a]pyrimidin-9-yl)ethyl]amino]benzoate Chemical group COC(=O)C1=CC=CC=C1N[C@@H](C)C1=CC(C)=CN2C(=O)C=C(N3CCOCC3)N=C12 RUZLIIJDZBWWSA-INIZCTEOSA-N 0.000 description 5
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 5
- 238000004809 thin layer chromatography Methods 0.000 description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 4
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 229960000583 acetic acid Drugs 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 239000012362 glacial acetic acid Substances 0.000 description 4
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 4
- 229960000443 hydrochloric acid Drugs 0.000 description 4
- 229960005287 lincomycin Drugs 0.000 description 4
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 4
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
- 150000003568 thioethers Chemical class 0.000 description 4
- UIYCHXAGWOYNNA-UHFFFAOYSA-N vinyl sulfide Chemical compound C=CSC=C UIYCHXAGWOYNNA-UHFFFAOYSA-N 0.000 description 4
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 3
- XJIRSLHMKBUGMR-UHFFFAOYSA-N 1-ethylsulfanylbutane Chemical compound CCCCSCC XJIRSLHMKBUGMR-UHFFFAOYSA-N 0.000 description 3
- VHMYGROEIUZTQW-UHFFFAOYSA-N 1-methylsulfanylpropan-2-ol Chemical compound CSCC(C)O VHMYGROEIUZTQW-UHFFFAOYSA-N 0.000 description 3
- QIAZGMDOMXLGBB-UHFFFAOYSA-N 1-propan-2-ylsulfanylbutane Chemical compound CCCCSC(C)C QIAZGMDOMXLGBB-UHFFFAOYSA-N 0.000 description 3
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- 239000005711 Benzoic acid Substances 0.000 description 3
- OTQVGYMGQKHLMY-UHFFFAOYSA-N Cyclopentyl-1-thiaethane Chemical compound CSC1CCCC1 OTQVGYMGQKHLMY-UHFFFAOYSA-N 0.000 description 3
- OPMRTBDRQRSNDN-UHFFFAOYSA-N Diethyl trisulfide Chemical compound CCSSSCC OPMRTBDRQRSNDN-UHFFFAOYSA-N 0.000 description 3
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 3
- 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 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 101000881330 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) Dynein heavy chain, cytoplasmic Proteins 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 235000010233 benzoic acid Nutrition 0.000 description 3
- 230000004071 biological effect Effects 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000001273 butane Substances 0.000 description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 3
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 239000000284 extract Substances 0.000 description 3
- RGXCTRIQQODGIZ-UHFFFAOYSA-O isodesmosine Chemical compound OC(=O)C(N)CCCC[N+]1=CC(CCC(N)C(O)=O)=CC(CCC(N)C(O)=O)=C1CCCC(N)C(O)=O RGXCTRIQQODGIZ-UHFFFAOYSA-O 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- AMBKPYJJYUKNFI-UHFFFAOYSA-N methylsulfanylethene Chemical compound CSC=C AMBKPYJJYUKNFI-UHFFFAOYSA-N 0.000 description 3
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 229960001866 silicon dioxide Drugs 0.000 description 3
- 238000000638 solvent extraction Methods 0.000 description 3
- 229960005349 sulfur Drugs 0.000 description 3
- 235000001508 sulfur Nutrition 0.000 description 3
- 239000006188 syrup Substances 0.000 description 3
- 235000020357 syrup Nutrition 0.000 description 3
- 150000003573 thiols Chemical class 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- QEJZCKJXVYGWMY-UHFFFAOYSA-N (cyclopentyldisulfanyl)cyclopentane Chemical compound C1CCCC1SSC1CCCC1 QEJZCKJXVYGWMY-UHFFFAOYSA-N 0.000 description 2
- BAQDEJZTORKSME-UHFFFAOYSA-N 1,2-bis(methylsulfanyl)propane Chemical compound CSCC(C)SC BAQDEJZTORKSME-UHFFFAOYSA-N 0.000 description 2
- ZOASGOXWEHUTKZ-UHFFFAOYSA-N 1-(Methylthio)-propane Chemical compound CCCSC ZOASGOXWEHUTKZ-UHFFFAOYSA-N 0.000 description 2
- FOJGPFUFFHWGFQ-UHFFFAOYSA-N 1-(Methylthio)pentane Chemical compound CCCCCSC FOJGPFUFFHWGFQ-UHFFFAOYSA-N 0.000 description 2
- UPYPTOCXMIWHSG-UHFFFAOYSA-N 1-dodecylsulfanyldodecane Chemical compound CCCCCCCCCCCCSCCCCCCCCCCCC UPYPTOCXMIWHSG-UHFFFAOYSA-N 0.000 description 2
- OIRKGXWQBSPXLQ-UHFFFAOYSA-N 1-ethylsulfanyl-2-methylpropane Chemical compound CCSCC(C)C OIRKGXWQBSPXLQ-UHFFFAOYSA-N 0.000 description 2
- ZDDDFDQTSXYYSE-UHFFFAOYSA-N 1-ethylsulfanylpropane Chemical compound CCCSCC ZDDDFDQTSXYYSE-UHFFFAOYSA-N 0.000 description 2
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- FJDWJOQOEZRIDJ-UHFFFAOYSA-N 1-methylsulfanylheptane Chemical compound CCCCCCCSC FJDWJOQOEZRIDJ-UHFFFAOYSA-N 0.000 description 2
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- NZUQQADVSXWVNW-UHFFFAOYSA-N 2-ethylsulfanylpropane Chemical compound CCSC(C)C NZUQQADVSXWVNW-UHFFFAOYSA-N 0.000 description 2
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- UQRLAGGSKUVKMJ-UHFFFAOYSA-N 2-methylpropylsulfanylbenzene Chemical compound CC(C)CSC1=CC=CC=C1 UQRLAGGSKUVKMJ-UHFFFAOYSA-N 0.000 description 2
- NHXRHICGDFDMHS-UHFFFAOYSA-N 2-methylpropylsulfanylcyclopentane Chemical compound CC(C)CSC1CCCC1 NHXRHICGDFDMHS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N 2-propanol Substances CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 2
- FXIHXPKPLPKPJH-UHFFFAOYSA-N 3-methylsulfanylpropane-1,2-diol Chemical compound CSCC(O)CO FXIHXPKPLPKPJH-UHFFFAOYSA-N 0.000 description 2
- CZUGFKJYCPYHHV-UHFFFAOYSA-N 3-methylthiopropanol Chemical compound CSCCCO CZUGFKJYCPYHHV-UHFFFAOYSA-N 0.000 description 2
- SXIFAEWFOJETOA-UHFFFAOYSA-N 4-hydroxy-butyl Chemical group [CH2]CCCO SXIFAEWFOJETOA-UHFFFAOYSA-N 0.000 description 2
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- JSASXSHMJYRPCM-UHFFFAOYSA-N r-3-(methylthio)-1-hexanol Chemical compound CCCC(SC)CCO JSASXSHMJYRPCM-UHFFFAOYSA-N 0.000 description 1
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- 125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
- 125000003639 thymyl group Chemical group C1(=CC(C)=CC=C1C(C)C)* 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
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- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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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 (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US15610071A | 1971-06-23 | 1971-06-23 | |
| US16190971A | 1971-07-12 | 1971-07-12 | |
| US19899071A | 1971-11-15 | 1971-11-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL39658A0 IL39658A0 (en) | 1972-08-30 |
| IL39658A true IL39658A (en) | 1977-04-29 |
Family
ID=27387802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL39658A IL39658A (en) | 1971-06-23 | 1972-06-09 | 7 deoxy-7(s)-alkylthio-lincosaminide and lincomycin derivatives process for their preparation and pharmaceutical compositions containing 7-deoxy-7(s)-alkylthio-lincomycines |
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 |
| NO138949C (no) | 1978-12-13 |
| PH13663A (en) | 1980-08-26 |
| NL176678C (nl) | 1985-05-17 |
| SE384685B (sv) | 1976-05-17 |
| FI56688C (fi) | 1980-03-10 |
| FR2143295B1 (enExample) | 1977-12-23 |
| BE785375A (fr) | 1972-12-27 |
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