IL23907A - Lincomycin analogues and a process for their production - Google Patents

Lincomycin analogues and a process for their production

Info

Publication number: IL23907A
Authority: IL; Israel
Prior art keywords: compound; formula; carbon; given; group
Prior art date: 1964-08-05

Application number

IL23907A

Other languages

English (en)

Hebrew (he)

Original Assignee

Upjohn Co

Priority date (The priority date 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 date listed.)

1964-08-05

Filing date

1965-07-07

Publication date

1971-05-26

1964-08-05 Priority claimed from US387776A external-priority patent/US3366624A/en

1965-06-14 Priority claimed from US463934A external-priority patent/US3380992A/en

1965-07-07 Application filed by Upjohn Co filed Critical Upjohn Co

1971-05-26 Publication of IL23907A publication Critical patent/IL23907A/en

Links

238000000034 method Methods 0.000 title claims description 53
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 description 13
150000001875 compounds Chemical class 0.000 claims description 201
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 135
-1 diphenyl benzyl Chemical group 0.000 claims description 111
239000002253 acid Substances 0.000 claims description 76
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 70
238000007792 addition Methods 0.000 claims description 63
229910052799 carbon Inorganic materials 0.000 claims description 59
150000003839 salts Chemical group 0.000 claims description 59
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 58
239000012458 free base Substances 0.000 claims description 51
125000000217 alkyl group Chemical group 0.000 claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 34
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 29
239000003054 catalyst Substances 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 19
229910052739 hydrogen Inorganic materials 0.000 claims description 19
239000002585 base Substances 0.000 claims description 18
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 18
125000003710 aryl alkyl group Chemical group 0.000 claims description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
125000001118 alkylidene group Chemical group 0.000 claims description 10
238000006698 hydrazinolysis reaction Methods 0.000 claims description 10
238000010438 heat treatment Methods 0.000 claims description 9
229910052763 palladium Inorganic materials 0.000 claims description 9
229910052697 platinum Inorganic materials 0.000 claims description 9
239000003153 chemical reaction reagent Substances 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
230000029936 alkylation Effects 0.000 claims description 5
238000005804 alkylation reaction Methods 0.000 claims description 5
238000007327 hydrogenolysis reaction Methods 0.000 claims description 5
230000003301 hydrolyzing effect Effects 0.000 claims description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
230000002152 alkylating effect Effects 0.000 claims description 3
230000001681 protective effect Effects 0.000 claims description 3
239000004305 biphenyl Substances 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
230000001590 oxidative effect Effects 0.000 claims description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
125000006239 protecting group Chemical group 0.000 claims description 2
ZUXNHFFVQWADJL-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methoxyethyl)-n-(4-phenyl-1,3-thiazol-2-yl)benzamide Chemical compound N=1C(C=2C=CC=CC=2)=CSC=1N(CCOC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 ZUXNHFFVQWADJL-UHFFFAOYSA-N 0.000 claims 1
KRVSOGSZCMJSLX-UHFFFAOYSA-L chromic acid Substances O[Cr](O)(=O)=O KRVSOGSZCMJSLX-UHFFFAOYSA-L 0.000 claims 1
AWJWCTOOIBYHON-UHFFFAOYSA-N furo[3,4-b]pyrazine-5,7-dione Chemical compound C1=CN=C2C(=O)OC(=O)C2=N1 AWJWCTOOIBYHON-UHFFFAOYSA-N 0.000 claims 1
229910052736 halogen Inorganic materials 0.000 claims 1
150000002367 halogens Chemical class 0.000 claims 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 149
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 96
239000000243 solution Substances 0.000 description 71
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 63
239000000203 mixture Substances 0.000 description 61
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 52
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 51
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 48
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 45
238000002844 melting Methods 0.000 description 34
230000008018 melting Effects 0.000 description 34
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000013078 crystal Substances 0.000 description 29
239000002904 solvent Substances 0.000 description 27
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 23
239000000706 filtrate Substances 0.000 description 23
VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 23
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 22
239000011541 reaction mixture Substances 0.000 description 21
239000007787 solid Substances 0.000 description 20
238000001914 filtration Methods 0.000 description 19
239000000047 product Substances 0.000 description 18
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 17
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 16
238000006243 chemical reaction Methods 0.000 description 16
230000003287 optical effect Effects 0.000 description 16
238000004809 thin layer chromatography Methods 0.000 description 16
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 description 14
235000011167 hydrochloric acid Nutrition 0.000 description 14
229960000443 hydrochloric acid Drugs 0.000 description 14
239000000463 material Substances 0.000 description 13
238000010992 reflux Methods 0.000 description 13
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 12
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 11
229960005287 lincomycin Drugs 0.000 description 11
239000003921 oil Substances 0.000 description 11
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
230000000844 anti-bacterial effect Effects 0.000 description 10
238000004821 distillation Methods 0.000 description 10
238000005406 washing Methods 0.000 description 10
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 9
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
238000004587 chromatography analysis Methods 0.000 description 9
239000000499 gel Substances 0.000 description 9
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 9
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 9
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 9
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 8
238000003556 assay Methods 0.000 description 8
230000003115 biocidal effect Effects 0.000 description 8
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 8
238000009826 distribution Methods 0.000 description 8
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 8
229910000041 hydrogen chloride Inorganic materials 0.000 description 8
230000007935 neutral effect Effects 0.000 description 8
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 8
238000000926 separation method Methods 0.000 description 8
239000007858 starting material Substances 0.000 description 8
WPWHSFAFEBZWBB-UHFFFAOYSA-N 1-butyl radical Chemical compound [CH2]CCC WPWHSFAFEBZWBB-UHFFFAOYSA-N 0.000 description 7
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 7
229910052794 bromium Inorganic materials 0.000 description 7
238000001816 cooling Methods 0.000 description 7
238000000921 elemental analysis Methods 0.000 description 7
239000000284 extract Substances 0.000 description 7
125000004435 hydrogen atom Chemical group [H]* 0.000 description 7
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 7
238000001953 recrystallisation Methods 0.000 description 7
229960001866 silicon dioxide Drugs 0.000 description 7
238000003756 stirring Methods 0.000 description 7
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 6
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
150000007513 acids Chemical class 0.000 description 6
235000019628 coolness Nutrition 0.000 description 6
238000002425 crystallisation Methods 0.000 description 6
230000008025 crystallization Effects 0.000 description 6
238000001704 evaporation Methods 0.000 description 6
239000007789 gas Substances 0.000 description 6
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 6
229910000027 potassium carbonate Inorganic materials 0.000 description 6
235000011181 potassium carbonates Nutrition 0.000 description 6
238000002360 preparation method Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
239000012453 solvate Substances 0.000 description 6
238000000638 solvent extraction Methods 0.000 description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 5
101100515517 Arabidopsis thaliana XI-I gene Proteins 0.000 description 5
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical class C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 5
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 5
238000004458 analytical method Methods 0.000 description 5
239000000538 analytical sample Substances 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000002704 decyl group Chemical group [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])* 0.000 description 5
229960001760 dimethyl sulfoxide Drugs 0.000 description 5
239000012259 ether extract Substances 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000000855 fermentation Methods 0.000 description 5
230000004151 fermentation Effects 0.000 description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
125000001400 nonyl 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])[H] 0.000 description 5
229960002429 proline Drugs 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
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 description 5
125000002948 undecyl 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])[H] 0.000 description 5
GNPWCZOXLLXPNA-RETOTEICSA-N CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SCC)[C@H](O)[C@@H](O)[C@H]1O Chemical compound CCC[C@@H]1C[C@H](N(C)C1)C(=O)N[C@H]([C@@H](C)O)[C@H]1O[C@H](SCC)[C@H](O)[C@@H](O)[C@H]1O GNPWCZOXLLXPNA-RETOTEICSA-N 0.000 description 4
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
FHBOKMJKJSSKHN-UHFFFAOYSA-N Lincomycin C Natural products CCCC1CC(NC(=O)C(C(C)O)C2OC(SCC)C(O)C(O)C2O)N(C)C1 FHBOKMJKJSSKHN-UHFFFAOYSA-N 0.000 description 4
229930193140 Neomycin Natural products 0.000 description 4
101000881330 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) Dynein heavy chain, cytoplasmic Proteins 0.000 description 4
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 4
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 4
OCBFFGCSTGGPSQ-UHFFFAOYSA-N [CH2]CC Chemical compound [CH2]CC OCBFFGCSTGGPSQ-UHFFFAOYSA-N 0.000 description 4
239000003957 anion exchange resin Substances 0.000 description 4
239000003242 anti bacterial agent Substances 0.000 description 4
125000000753 cycloalkyl group Chemical group 0.000 description 4
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 4
125000003438 dodecyl group Chemical group [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])* 0.000 description 4
230000000694 effects Effects 0.000 description 4
150000004820 halides Chemical class 0.000 description 4
150000003840 hydrochlorides Chemical class 0.000 description 4
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
238000005649 metathesis reaction Methods 0.000 description 4
229960004927 neomycin Drugs 0.000 description 4
125000002347 octyl 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])[H] 0.000 description 4
239000012071 phase Substances 0.000 description 4
235000015497 potassium bicarbonate Nutrition 0.000 description 4
229910000028 potassium bicarbonate Inorganic materials 0.000 description 4
239000011736 potassium bicarbonate Substances 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
238000000746 purification Methods 0.000 description 4
230000002829 reductive effect Effects 0.000 description 4
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
125000006201 3-phenylpropyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 3
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical class [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 3
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 3
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 3
239000004793 Polystyrene Substances 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
239000007868 Raney catalyst Substances 0.000 description 3
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 3
229910000564 Raney nickel Inorganic materials 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000003377 acid catalyst Substances 0.000 description 3
150000001348 alkyl chlorides Chemical class 0.000 description 3
150000001350 alkyl halides Chemical class 0.000 description 3
150000001351 alkyl iodides Chemical class 0.000 description 3
235000013405 beer Nutrition 0.000 description 3
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 3
125000001589 carboacyl group Chemical group 0.000 description 3
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238000004519 manufacturing process Methods 0.000 description 1
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239000012452 mother liquor Substances 0.000 description 1
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238000006386 neutralization reaction Methods 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 1
125000001402 nonanoyl group Chemical group O=C([*])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 1
TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
125000005740 oxycarbonyl group Chemical group [*:1]OC([*:2])=O 0.000 description 1
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 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
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238000004810 partition chromatography Methods 0.000 description 1
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239000008363 phosphate buffer Substances 0.000 description 1
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BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
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235000018102 proteins Nutrition 0.000 description 1
108090000623 proteins and genes Proteins 0.000 description 1
102000004169 proteins and genes Human genes 0.000 description 1
150000003214 pyranose derivatives Chemical group 0.000 description 1
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 1
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230000035484 reaction time Effects 0.000 description 1
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238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000009738 saturating Methods 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000002195 soluble material Substances 0.000 description 1
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239000008107 starch Substances 0.000 description 1
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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 1
125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
239000010414 supernatant solution Substances 0.000 description 1
150000003569 thioglycosides Chemical class 0.000 description 1
238000004448 titration Methods 0.000 description 1
125000002889 tridecyl 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])[H] 0.000 description 1
229940086542 triethylamine Drugs 0.000 description 1
XMQSELBBYSAURN-UHFFFAOYSA-M triphenyl(propyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(CCC)C1=CC=CC=C1 XMQSELBBYSAURN-UHFFFAOYSA-M 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
241001446247 uncultured actinomycete Species 0.000 description 1
RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 1
125000000297 undecanoyl group Chemical group O=C([*])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 1
238000005292 vacuum distillation Methods 0.000 description 1
238000010792 warming Methods 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
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Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/70—Carbohydrates; Sugars; Derivatives thereof
- 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
- 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
- C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
- C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
- C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G73/1067—Wholly aromatic polyimides, i.e. having both tetracarboxylic and diamino moieties aromatically bound
- C08G73/1071—Wholly aromatic polyimides containing oxygen in the form of ether bonds in the main chain
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

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Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
General Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Molecular Biology (AREA)
Biochemistry (AREA)
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IL23907A 1964-08-05 1965-07-07 Lincomycin analogues and a process for their production IL23907A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US387776A US3366624A (en)	1964-08-05	1964-08-05	Lincomycin derivatives and process for preparing same
US463934A US3380992A (en)	1965-06-14	1965-06-14	Lincomycin derivatives and process for preparing same

Publications (1)

Publication Number	Publication Date
IL23907A true IL23907A (en)	1971-05-26

Family

ID=27012015

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL23907A IL23907A (en)	1964-08-05	1965-07-07	Lincomycin analogues and a process for their production
IL33548A IL33548A (en)	1964-08-05	1965-07-07	Galactopyranosides which are intermediates for lincomycin

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
IL33548A IL33548A (en)	1964-08-05	1965-07-07	Galactopyranosides which are intermediates for lincomycin

Country Status (11)

Country	Link
BE (1)	BE667948A (de)
BR (1)	BR6571854D0 (de)
CH (1)	CH478115A (de)
DE (1)	DE1620607A1 (de)
DK (1)	DK129936B (de)
ES (1)	ES316092A1 (de)
FR (2)	FR1503519A (de)
GB (2)	GB1118307A (de)
IL (2)	IL23907A (de)
NL (1)	NL6510036A (de)
SE (3)	SE317377B (de)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7018988B2 (en)	2000-03-27	2006-03-28	Applied Research Systems Ars Holding N.V.	Pharmaceutically active pyrrolidine derivatives as Bax inhibitors
HRP20020705A2 (en)	2000-03-27	2004-12-31	Applied Research Systems	Pharmaceutically active pyrrolidine derivatives
CN110606865B (zh) *	2018-06-14	2026-05-15	四川科伦药物研究院有限公司	盐酸克林霉素杂质的制备方法

1965
- 1965-07-07 IL IL23907A patent/IL23907A/en unknown
- 1965-07-07 IL IL33548A patent/IL33548A/en unknown
- 1965-07-14 GB GB4196/68A patent/GB1118307A/en not_active Expired
- 1965-07-14 GB GB29882/65A patent/GB1118306A/en not_active Expired
- 1965-07-21 CH CH1024565A patent/CH478115A/de not_active IP Right Cessation
- 1965-08-03 DE DE19651620607 patent/DE1620607A1/de active Pending
- 1965-08-03 DK DK398465AA patent/DK129936B/da unknown
- 1965-08-03 SE SE10155/65A patent/SE317377B/xx unknown
- 1965-08-03 SE SE7028/67A patent/SE324654B/xx unknown
- 1965-08-03 NL NL6510036A patent/NL6510036A/xx unknown
- 1965-08-03 SE SE7026/67A patent/SE324569B/xx unknown
- 1965-08-03 ES ES0316092A patent/ES316092A1/es not_active Expired
- 1965-08-04 FR FR27269A patent/FR1503519A/fr not_active Expired
- 1965-08-05 BR BR171854/65A patent/BR6571854D0/pt unknown
- 1965-08-05 BE BE667948A patent/BE667948A/xx unknown
- 1965-11-04 FR FR37330A patent/FR5777M/fr not_active Expired

Also Published As

Publication number	Publication date
GB1118306A (en)	1968-06-26
BE667948A (de)	1966-02-07
CH478115A (de)	1969-09-15
SE324654B (de)	1970-06-08
FR5777M (de)	1968-03-18
NL6510036A (de)	1966-02-07
ES316092A1 (es)	1965-11-16
IL33548A (en)	1972-04-27
GB1118307A (en)	1968-06-26
FR1503519A (fr)	1967-12-01
DE1620607A1 (de)	1970-05-14
DK129936C (de)	1975-05-20
SE324569B (de)	1970-06-08
SE317377B (de)	1969-11-17
BR6571854D0 (pt)	1973-10-25
DK129936B (da)	1974-12-02

Publication	Publication Date	Title
US3496163A (en)	1970-02-17	7-halo-7-deoxylincomycins and process for preparing the same
US3380992A (en)	1968-04-30	Lincomycin derivatives and process for preparing same
IL28910A (en)	1971-08-25	Lincomycin-2-phosphates and process for preparing them
NO126620B (de)	1973-03-05
US3435025A (en)	1969-03-25	7-deoxylincomycin and analogs and isomers thereof and process for making the same
US3268556A (en)	1966-08-23	Novel lincomycin derivatives
US3282917A (en)	1966-11-01	Methyl n-(1-alkyl-4-alkoxy-prolyl)-alpha-thiolincosaminide compounds and process therefor
CH648854A5 (de)	1985-04-15	Antibiotisch wirksame aminoglykoside.
EP0316128B1 (de)	1993-03-03	Antibakterielle 9-Deoxy-9a-allyl und Propargyl-9a-aza-9a-homoerythromycin-A-Derivate
US3364197A (en)	1968-01-16	2-hydroxyethyl 6, 8-dideoxy-6-(4-substituted-1-2-pyrrolidinecarboxamido)-7-o-methyl-1-thio-d-erythro-alpha-d-galacto-octopyranosides and process for producing them
US3366624A (en)	1968-01-30	Lincomycin derivatives and process for preparing same
US3361739A (en)	1968-01-02	Lincomycin derivatives and processes for preparing the same
US3817979A (en)	1974-06-18	7-0-demethylcelesticetin derivatives
US4060682A (en)	1977-11-29	Process for the synthetic production of 3-deoxy derivative of an aminoglycosidic antibiotic
US4125706A (en)	1978-11-14	Novel process for the preparation of 1-N-(alpha-substituted-omega-aminoacyl)-3'-deoxyribostamycin
US4465848A (en)	1984-08-14	Spectinomycin compounds
US3346635A (en)	1967-10-10	Mercaptals of 6-amino-6, 8-dideoxy-d-erythro-d-galacto-aldehydooctose and nu-acyl derivatives
DE1620607A1 (de)	1970-05-14	Verfahren zur Herstellung von Lincomycin und analogen Verbindungen
US3306892A (en)	1967-02-28	Process for the production of 6,8-dideoxy-6-(1,4-dialkyl-l-2-pyrrolidine-car-boxamido)-1-thio-d-erythro-alpha-d-galac-to-octopyranosides
US3574186A (en)	1971-04-06	Process for making 7-chloro-7-deoxylincomycin and related compounds and novel intermediates produced therein
US4482545A (en)	1984-11-13	Isoefrotomycin, process of preparation, pharmaceutical composition and method of using same
DE1620620C3 (de)	1975-05-28	Verfahren zur Herstellung von 7-Chlor-7deoxylincomycin und -epilincomycin sowie deren Isomeren und Analoga
US3726858A (en)	1973-04-10	Delta 4',alpha-analogs of lincomycin
US6008333A (en)	1999-12-28	Preparation of glucosaminyl muramic acid derivatives
US3415811A (en)	1968-12-10	Antibiotic lincomycin k and process for the production thereof