IL23089A - Derivatives of lincomycin and related antibiotics and processes for producing them - Google Patents

Derivatives of lincomycin and related antibiotics and processes for producing them

Info

Publication number: IL23089A
Authority: IL; Israel
Prior art keywords: methyl; formula; inclusive; trans; carbon atoms
Prior art date: 1964-04-13

Application number

IL23089A

Other languages

English (en)

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.)

1964-04-13

Filing date

1965-03-02

Publication date

1969-03-27

1965-03-02 Application filed by Upjohn Co filed Critical Upjohn Co

1969-03-27 Publication of IL23089A publication Critical patent/IL23089A/en

Links

238000000034 method Methods 0.000 title claims description 36
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 6
239000003242 anti bacterial agent Substances 0.000 title description 3
229940088710 antibiotic agent Drugs 0.000 title description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
-1 inclusive Chemical group 0.000 claims description 69
239000002253 acid Substances 0.000 claims description 63
150000001875 compounds Chemical class 0.000 claims description 50
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 42
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 42
125000004432 carbon atom Chemical group C* 0.000 claims description 39
229910052739 hydrogen Inorganic materials 0.000 claims description 21
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 20
239000001257 hydrogen Substances 0.000 claims description 19
229910014033 C-OH Inorganic materials 0.000 claims description 17
229910014570 C—OH Inorganic materials 0.000 claims description 17
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 claims description 14
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 14
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 12
150000008065 acid anhydrides Chemical class 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
239000004215 Carbon black (E152) Substances 0.000 claims description 10
229930195733 hydrocarbon Natural products 0.000 claims description 10
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 9
WQAQPCDUOCURKW-UHFFFAOYSA-N butanethiol Chemical compound CCCCS WQAQPCDUOCURKW-UHFFFAOYSA-N 0.000 claims description 7
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
150000007513 acids Chemical class 0.000 claims description 6
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 5
UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 claims description 5
229910052500 inorganic mineral Inorganic materials 0.000 claims description 5
239000011707 mineral Substances 0.000 claims description 5
GCZQHDFWKVMZOE-UHFFFAOYSA-N thiophen-2-ylmethanethiol Chemical compound SCC1=CC=CS1 GCZQHDFWKVMZOE-UHFFFAOYSA-N 0.000 claims description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical group CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 claims description 3
229910052799 carbon Inorganic materials 0.000 claims description 3
239000003153 chemical reaction reagent Substances 0.000 claims description 3
239000003795 chemical substances by application Substances 0.000 claims description 3
125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
DNJIEGIFACGWOD-UHFFFAOYSA-N ethanethiol Chemical compound CCS DNJIEGIFACGWOD-UHFFFAOYSA-N 0.000 claims description 3
150000002430 hydrocarbons Chemical class 0.000 claims 4
125000002252 acyl group Chemical group 0.000 claims 2
BSFODEXXVBBYOC-UHFFFAOYSA-N 8-[4-(dimethylamino)butan-2-ylamino]quinolin-6-ol Chemical group C1=CN=C2C(NC(CCN(C)C)C)=CC(O)=CC2=C1 BSFODEXXVBBYOC-UHFFFAOYSA-N 0.000 claims 1
101000740382 Homo sapiens Sciellin Proteins 0.000 claims 1
102100037235 Sciellin Human genes 0.000 claims 1
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
150000004820 halides Chemical class 0.000 claims 1
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 102
239000000203 mixture Substances 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 81
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 66
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 60
239000000243 solution Substances 0.000 description 50
238000002360 preparation method Methods 0.000 description 47
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 46
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 45
KOFBVFFPLADGGO-DUSUDKPKSA-N (3r,4s,5r,6r)-6-[(1r,2r)-1-amino-2-hydroxypropyl]oxane-2,3,4,5-tetrol Chemical compound C[C@@H](O)[C@@H](N)[C@H]1OC(O)[C@H](O)[C@@H](O)[C@H]1O KOFBVFFPLADGGO-DUSUDKPKSA-N 0.000 description 43
235000011167 hydrochloric acid Nutrition 0.000 description 37
229960000443 hydrochloric acid Drugs 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 36
239000000047 product Substances 0.000 description 30
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
238000002844 melting Methods 0.000 description 21
230000008018 melting Effects 0.000 description 21
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 20
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
239000011541 reaction mixture Substances 0.000 description 19
239000003054 catalyst Substances 0.000 description 18
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 17
239000000706 filtrate Substances 0.000 description 17
238000004587 chromatography analysis Methods 0.000 description 16
229960002429 proline Drugs 0.000 description 15
239000007787 solid Substances 0.000 description 15
238000001914 filtration Methods 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 12
238000000855 fermentation Methods 0.000 description 12
230000004151 fermentation Effects 0.000 description 12
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
150000003839 salts Chemical class 0.000 description 12
HIQUUSNBAJBMPX-GWKQWKOUSA-N (2r,3s,4s,5r,6s,7r)-6-amino-2,3,4,5-tetrahydroxy-7-methoxyoctanal Chemical compound CO[C@H](C)[C@@H](N)[C@@H](O)[C@H](O)[C@H](O)[C@@H](O)C=O HIQUUSNBAJBMPX-GWKQWKOUSA-N 0.000 description 11
238000010992 reflux Methods 0.000 description 11
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 9
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 9
229910000564 Raney nickel Inorganic materials 0.000 description 9
239000013078 crystal Substances 0.000 description 9
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
239000002904 solvent Substances 0.000 description 9
PMBXCGGQNSVESQ-UHFFFAOYSA-N 1-Hexanethiol Chemical compound CCCCCCS PMBXCGGQNSVESQ-UHFFFAOYSA-N 0.000 description 8
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
239000012458 free base Substances 0.000 description 8
239000000463 material Substances 0.000 description 8
KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 7
239000007868 Raney catalyst Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
238000005406 washing Methods 0.000 description 7
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
238000004458 analytical method Methods 0.000 description 6
239000000284 extract Substances 0.000 description 6
150000002337 glycosamines Chemical class 0.000 description 6
238000001953 recrystallisation Methods 0.000 description 6
NDVLTYZPCACLMA-UHFFFAOYSA-N silver oxide Chemical compound [O-2].[Ag+].[Ag+] NDVLTYZPCACLMA-UHFFFAOYSA-N 0.000 description 6
239000000725 suspension Substances 0.000 description 6
238000004809 thin layer chromatography Methods 0.000 description 6
VMSQKUCYEMOKMM-HUQJOJSCSA-N 2-[(2s,3s,4r,5r,6s)-3,4,5-trihydroxy-6-[(1r,2r)-2-methoxy-1-[[(2s)-1-methylpyrrolidine-2-carbonyl]amino]propyl]oxan-2-yl]sulfanylethyl 2-hydroxybenzoate Chemical compound N([C@H]([C@@H](C)OC)[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@H](SCCOC(=O)C=2C(=CC=CC=2)O)O1)O)C(=O)[C@@H]1CCCN1C VMSQKUCYEMOKMM-HUQJOJSCSA-N 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
150000008064 anhydrides Chemical class 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
230000008020 evaporation Effects 0.000 description 5
238000005984 hydrogenation reaction Methods 0.000 description 5
POUMFISTNHIPTI-BOMBIWCESA-N hydron;(2s,4r)-n-[(1r,2r)-2-hydroxy-1-[(2r,3r,4s,5r,6r)-3,4,5-trihydroxy-6-methylsulfanyloxan-2-yl]propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide;chloride Chemical compound Cl.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 POUMFISTNHIPTI-BOMBIWCESA-N 0.000 description 5
229960001595 lincomycin hydrochloride Drugs 0.000 description 5
230000003287 optical effect Effects 0.000 description 5
229910052763 palladium Inorganic materials 0.000 description 5
238000003786 synthesis reaction Methods 0.000 description 5
MYRTYDVEIRVNKP-UHFFFAOYSA-N 1,2-Divinylbenzene Chemical compound C=CC1=CC=CC=C1C=C MYRTYDVEIRVNKP-UHFFFAOYSA-N 0.000 description 4
YOETUEMZNOLGDB-UHFFFAOYSA-N 2-methylpropyl carbonochloridate Chemical compound CC(C)COC(Cl)=O YOETUEMZNOLGDB-UHFFFAOYSA-N 0.000 description 4
241000227653 Lycopersicon Species 0.000 description 4
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000003957 anion exchange resin Substances 0.000 description 4
238000003556 assay Methods 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000009826 distribution Methods 0.000 description 4
150000003840 hydrochlorides Chemical class 0.000 description 4
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 4
229910000041 hydrogen chloride Inorganic materials 0.000 description 4
229910052759 nickel Inorganic materials 0.000 description 4
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
239000001103 potassium chloride Substances 0.000 description 4
235000011164 potassium chloride Nutrition 0.000 description 4
238000003756 stirring Methods 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-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
235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
241001465754 Metazoa Species 0.000 description 3
GGLZPLKKBSSKCX-UHFFFAOYSA-N S-ethylhomocysteine Chemical compound CCSCCC(N)C(O)=O GGLZPLKKBSSKCX-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
229920002472 Starch Polymers 0.000 description 3
AYFVYJQAPQTCCC-UHFFFAOYSA-N Threonine Natural products CC(O)C(N)C(O)=O AYFVYJQAPQTCCC-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
235000013405 beer Nutrition 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
238000009835 boiling Methods 0.000 description 3
ZTQSAGDEMFDKMZ-UHFFFAOYSA-N butyric aldehyde Natural products CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 3
XTEGARKTQYYJKE-UHFFFAOYSA-N chloric acid Chemical compound OCl(=O)=O XTEGARKTQYYJKE-UHFFFAOYSA-N 0.000 description 3
229940005991 chloric acid Drugs 0.000 description 3
239000002026 chloroform extract Substances 0.000 description 3
238000009833 condensation Methods 0.000 description 3
230000005494 condensation Effects 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
238000004821 distillation Methods 0.000 description 3
WNAHIZMDSQCWRP-UHFFFAOYSA-N dodecane-1-thiol Chemical compound CCCCCCCCCCCCS WNAHIZMDSQCWRP-UHFFFAOYSA-N 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
239000005457 ice water Substances 0.000 description 3
235000015110 jellies Nutrition 0.000 description 3
239000008274 jelly Substances 0.000 description 3
229960005287 lincomycin Drugs 0.000 description 3
KZCOBXFFBQJQHH-UHFFFAOYSA-N octane-1-thiol Chemical compound CCCCCCCCS KZCOBXFFBQJQHH-UHFFFAOYSA-N 0.000 description 3
229920001467 poly(styrenesulfonates) Polymers 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
230000001681 protective effect Effects 0.000 description 3
238000000746 purification Methods 0.000 description 3
230000035484 reaction time Effects 0.000 description 3
229910001923 silver oxide Inorganic materials 0.000 description 3
239000008107 starch Substances 0.000 description 3
235000019698 starch Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
AEEIMWYSDWZKAT-HJTGYUAHSA-N (2r,3r,4s,5r,6r)-2-[(1r,2r)-1-amino-2-hydroxypropyl]-6-methylsulfanyloxane-3,4,5-triol Chemical compound CS[C@H]1O[C@H]([C@H](N)[C@@H](C)O)[C@H](O)[C@H](O)[C@H]1O AEEIMWYSDWZKAT-HJTGYUAHSA-N 0.000 description 2
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
HFXAFXVXPMUQCQ-BYPYZUCNSA-N 4-oxo-L-proline Chemical class OC(=O)[C@@H]1CC(=O)CN1 HFXAFXVXPMUQCQ-BYPYZUCNSA-N 0.000 description 2
IKHGUXGNUITLKF-UHFFFAOYSA-N Acetaldehyde Chemical compound CC=O IKHGUXGNUITLKF-UHFFFAOYSA-N 0.000 description 2
229920001817 Agar Polymers 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 2
FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
VMSQKUCYEMOKMM-UHFFFAOYSA-N Celesticetin Natural products O1C(SCCOC(=O)C=2C(=CC=CC=2)O)C(O)C(O)C(O)C1C(C(C)OC)NC(=O)C1CCCN1C VMSQKUCYEMOKMM-UHFFFAOYSA-N 0.000 description 2
XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
VPIAKHNXCOTPAY-UHFFFAOYSA-N Heptane-1-thiol Chemical compound CCCCCCCS VPIAKHNXCOTPAY-UHFFFAOYSA-N 0.000 description 2
AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
NBBJYMSMWIIQGU-UHFFFAOYSA-N Propionic aldehyde Chemical compound CCC=O NBBJYMSMWIIQGU-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
241000187399 Streptomyces lincolnensis Species 0.000 description 2
238000000862 absorption spectrum Methods 0.000 description 2
239000008272 agar Substances 0.000 description 2
239000003513 alkali Substances 0.000 description 2
229940024606 amino acid Drugs 0.000 description 2
235000001014 amino acid Nutrition 0.000 description 2
150000001413 amino acids Chemical class 0.000 description 2
230000000845 anti-microbial effect Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
YHASWHZGWUONAO-UHFFFAOYSA-N butanoyl butanoate Chemical compound CCCC(=O)OC(=O)CCC YHASWHZGWUONAO-UHFFFAOYSA-N 0.000 description 2
RBHJBMIOOPYDBQ-UHFFFAOYSA-N carbon dioxide;propan-2-one Chemical compound O=C=O.CC(C)=O RBHJBMIOOPYDBQ-UHFFFAOYSA-N 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
NQGIJDNPUZEBRU-UHFFFAOYSA-N dodecanoyl chloride Chemical compound CCCCCCCCCCCC(Cl)=O NQGIJDNPUZEBRU-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000012259 ether extract Substances 0.000 description 2
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 2
FCZCIXQGZOUIDN-UHFFFAOYSA-N ethyl 2-diethoxyphosphinothioyloxyacetate Chemical compound CCOC(=O)COP(=S)(OCC)OCC FCZCIXQGZOUIDN-UHFFFAOYSA-N 0.000 description 2
238000000605 extraction Methods 0.000 description 2
229960001031 glucose Drugs 0.000 description 2
MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid group Chemical group C(CCCCCC)(=O)O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 2
ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
238000007327 hydrogenolysis reaction Methods 0.000 description 2
230000003301 hydrolyzing effect Effects 0.000 description 2
WQGHBXNTZFIOSX-UHFFFAOYSA-N hygric acid Natural products CN1CCCC1CC(O)=O WQGHBXNTZFIOSX-UHFFFAOYSA-N 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
244000005700 microbiome Species 0.000 description 2
FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 description 2
QJAOYSPHSNGHNC-UHFFFAOYSA-N octadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCCCS QJAOYSPHSNGHNC-UHFFFAOYSA-N 0.000 description 2
CBFCDTFDPHXCNY-UHFFFAOYSA-N octyldodecane Natural products CCCCCCCCCCCCCCCCCCCC CBFCDTFDPHXCNY-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
239000008188 pellet Substances 0.000 description 2
DUCKXCGALKOSJF-UHFFFAOYSA-N pentanoyl pentanoate Chemical compound CCCCC(=O)OC(=O)CCCC DUCKXCGALKOSJF-UHFFFAOYSA-N 0.000 description 2
239000012071 phase Substances 0.000 description 2
229910052697 platinum Inorganic materials 0.000 description 2
KJRCEJOSASVSRA-UHFFFAOYSA-N propane-2-thiol Chemical compound CC(C)S KJRCEJOSASVSRA-UHFFFAOYSA-N 0.000 description 2
150000003242 quaternary ammonium salts Chemical group 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
229920006395 saturated elastomer Polymers 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012453 solvate Substances 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000006228 supernatant Substances 0.000 description 2
239000008399 tap water Substances 0.000 description 2
235000020679 tap water Nutrition 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 2
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
ZDPHROOEEOARMN-UHFFFAOYSA-N undecanoic acid Chemical compound CCCCCCCCCCC(O)=O ZDPHROOEEOARMN-UHFFFAOYSA-N 0.000 description 2
NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
JAUFWTSSYRTLLB-UHFFFAOYSA-N (2-phenylacetyl) 2-phenylacetate Chemical compound C=1C=CC=CC=1CC(=O)OC(=O)CC1=CC=CC=C1 JAUFWTSSYRTLLB-UHFFFAOYSA-N 0.000 description 1
PQIGORVEAYDDPB-VHSXEESVSA-N (2R,4S)-4-butyl-1-ethylpyrrolidine-2-carboxylic acid Chemical compound C(CCC)[C@H]1C[C@@H](N(C1)CC)C(=O)O PQIGORVEAYDDPB-VHSXEESVSA-N 0.000 description 1
HFXAFXVXPMUQCQ-SCSAIBSYSA-N (2r)-4-oxopyrrolidin-1-ium-2-carboxylate Chemical compound OC(=O)[C@H]1CC(=O)CN1 HFXAFXVXPMUQCQ-SCSAIBSYSA-N 0.000 description 1
IRVKSIZCDZXHDE-UHFFFAOYSA-N (3-chloro-2-nitrophenyl) benzoate Chemical compound C(C1=CC=CC=C1)(=O)OC1=C(C(=CC=C1)Cl)[N+](=O)[O-] IRVKSIZCDZXHDE-UHFFFAOYSA-N 0.000 description 1
QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 description 1
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 1
ZRKMQKLGEQPLNS-UHFFFAOYSA-N 1-Pentanethiol Chemical compound CCCCCS ZRKMQKLGEQPLNS-UHFFFAOYSA-N 0.000 description 1
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-PPJXEINESA-N 2-phenylacetic acid Chemical compound O[14C](=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-PPJXEINESA-N 0.000 description 1
XMIIGOLPHOKFCH-UHFFFAOYSA-N 3-phenylpropionic acid Chemical compound OC(=O)CCC1=CC=CC=C1 XMIIGOLPHOKFCH-UHFFFAOYSA-N 0.000 description 1
QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 description 1
ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
GIMDYESITSFSDT-QWHCGFSZSA-N C(CCCCC)[C@H]1C[C@@H](N(C1)CCC)C(=O)O Chemical compound C(CCCCC)[C@H]1C[C@@H](N(C1)CCC)C(=O)O GIMDYESITSFSDT-QWHCGFSZSA-N 0.000 description 1
GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
241001121515 Celes Species 0.000 description 1
ONIBWKKTOPOVIA-SCSAIBSYSA-N D-Proline Chemical compound OC(=O)[C@H]1CCCN1 ONIBWKKTOPOVIA-SCSAIBSYSA-N 0.000 description 1
229930182820 D-proline Natural products 0.000 description 1
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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 1
239000005909 Kieselgur Substances 0.000 description 1
125000000174 L-prolyl group Chemical class [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 description 1
AYFVYJQAPQTCCC-GBXIJSLDSA-N L-threonine Chemical compound C[C@@H](O)[C@H](N)C(O)=O AYFVYJQAPQTCCC-GBXIJSLDSA-N 0.000 description 1
206010024264 Lethargy Diseases 0.000 description 1
239000001888 Peptone Substances 0.000 description 1
108010080698 Peptones Proteins 0.000 description 1
239000004793 Polystyrene Substances 0.000 description 1
108010009736 Protein Hydrolysates Proteins 0.000 description 1
229910021607 Silver chloride Inorganic materials 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
244000127759 Spondias lutea Species 0.000 description 1
241000187747 Streptomyces Species 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000004473 Threonine Substances 0.000 description 1
241000223229 Trichophyton rubrum Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
RMQXUAYCXLDUKS-WCCKRBBISA-N [N].OC(=O)[C@@H]1CCCN1 Chemical compound [N].OC(=O)[C@@H]1CCCN1 RMQXUAYCXLDUKS-WCCKRBBISA-N 0.000 description 1
150000001266 acyl halides Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
OBETXYAYXDNJHR-UHFFFAOYSA-N alpha-ethylcaproic acid Natural products CCCCC(CC)C(O)=O OBETXYAYXDNJHR-UHFFFAOYSA-N 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
239000000908 ammonium hydroxide Substances 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000004599 antimicrobial Substances 0.000 description 1
230000036528 appetite Effects 0.000 description 1
235000019789 appetite Nutrition 0.000 description 1
239000012223 aqueous fraction Substances 0.000 description 1
239000003125 aqueous solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical class [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 1
239000002585 base Substances 0.000 description 1
239000003637 basic solution Substances 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 description 1
125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
125000001246 bromo group Chemical group Br* 0.000 description 1
239000000872 buffer Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
VTYYLEPIZMXCLO-UHFFFAOYSA-L calcium carbonate Substances [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
150000001721 carbon Chemical group 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
150000001728 carbonyl compounds Chemical class 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
239000005018 casein Substances 0.000 description 1
BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 1
235000021240 caseins Nutrition 0.000 description 1
230000003197 catalytic effect Effects 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
FZFAMSAMCHXGEF-UHFFFAOYSA-N chloro formate Chemical compound ClOC=O FZFAMSAMCHXGEF-UHFFFAOYSA-N 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
235000012343 cottonseed oil Nutrition 0.000 description 1
239000002385 cottonseed oil Substances 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
VTXVGVNLYGSIAR-UHFFFAOYSA-N decane-1-thiol Chemical compound CCCCCCCCCCS VTXVGVNLYGSIAR-UHFFFAOYSA-N 0.000 description 1
238000010908 decantation Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
150000004252 dithioacetals Chemical class 0.000 description 1
238000010828 elution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
230000002255 enzymatic effect Effects 0.000 description 1
OMAYPGGVIXHKRO-UHFFFAOYSA-N ethanethiol Chemical compound [CH2]CS OMAYPGGVIXHKRO-UHFFFAOYSA-N 0.000 description 1
229940093495 ethanethiol Drugs 0.000 description 1
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
210000003918 fraction a Anatomy 0.000 description 1
210000000540 fraction c Anatomy 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
ORTRWBYBJVGVQC-UHFFFAOYSA-N hexadecane-1-thiol Chemical compound CCCCCCCCCCCCCCCCS ORTRWBYBJVGVQC-UHFFFAOYSA-N 0.000 description 1
239000002035 hexane extract Substances 0.000 description 1
239000002044 hexane fraction Substances 0.000 description 1
238000006698 hydrazinolysis reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000003456 ion exchange resin Substances 0.000 description 1
229920003303 ion-exchange polymer Polymers 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
239000010699 lard oil Substances 0.000 description 1
XCOBTUNSZUJCDH-UHFFFAOYSA-B lithium magnesium sodium silicate Chemical compound [Li+].[Li+].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[OH-].[Na+].[Na+].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].[Mg+2].O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3.O1[Si](O2)([O-])O[Si]3([O-])O[Si]1([O-])O[Si]2([O-])O3 XCOBTUNSZUJCDH-UHFFFAOYSA-B 0.000 description 1
238000005649 metathesis reaction Methods 0.000 description 1
FBBDOOHMGLLEGJ-UHFFFAOYSA-N methane;hydrochloride Chemical compound C.Cl FBBDOOHMGLLEGJ-UHFFFAOYSA-N 0.000 description 1
LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
235000013379 molasses Nutrition 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
ZWLPBLYKEWSWPD-UHFFFAOYSA-N o-toluic acid Chemical compound CC1=CC=CC=C1C(O)=O ZWLPBLYKEWSWPD-UHFFFAOYSA-N 0.000 description 1
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 1
239000003960 organic solvent Substances 0.000 description 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 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
230000000590 parasiticidal effect Effects 0.000 description 1
239000002297 parasiticide Substances 0.000 description 1
235000011837 pasties Nutrition 0.000 description 1
235000019319 peptone Nutrition 0.000 description 1
239000008363 phosphate buffer Substances 0.000 description 1
238000005554 pickling Methods 0.000 description 1
244000000003 plant pathogen Species 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920002223 polystyrene Polymers 0.000 description 1
229920005749 polyurethane resin Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
235000013930 proline Nutrition 0.000 description 1
150000003148 prolines Chemical class 0.000 description 1
125000001500 prolyl group Chemical group [H]N1C([H])(C(=O)[*])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
WYVAMUWZEOHJOQ-UHFFFAOYSA-N propionic anhydride Chemical compound CCC(=O)OC(=O)CC WYVAMUWZEOHJOQ-UHFFFAOYSA-N 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000001172 regenerating effect Effects 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
238000012552 review Methods 0.000 description 1
239000000523 sample Substances 0.000 description 1
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 1
229910001958 silver carbonate Inorganic materials 0.000 description 1
HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical group C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 1
230000004936 stimulating effect Effects 0.000 description 1
150000003440 styrenes Chemical class 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
GEKDEMKPCKTKEC-UHFFFAOYSA-N tetradecane-1-thiol Chemical compound CCCCCCCCCCCCCCS GEKDEMKPCKTKEC-UHFFFAOYSA-N 0.000 description 1
RMVRSNDYEFQCLF-UHFFFAOYSA-N thiophenol Chemical class SC1=CC=CC=C1 RMVRSNDYEFQCLF-UHFFFAOYSA-N 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
125000005270 trialkylamine group Chemical group 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
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 1
DGJTZXXNXZVULP-UHFFFAOYSA-N undecanoyl undecanoate Chemical compound CCCCCCCCCCC(=O)OC(=O)CCCCCCCCCC DGJTZXXNXZVULP-UHFFFAOYSA-N 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
229940005605 valeric acid Drugs 0.000 description 1
HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
210000005253 yeast cell Anatomy 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/04—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D207/10—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Crystallography & Structural Chemistry (AREA)
Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Engineering & Computer Science (AREA)
Biochemistry (AREA)
Biotechnology (AREA)
General Health & Medical Sciences (AREA)
Genetics & Genomics (AREA)
Molecular Biology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

IL23089A 1964-04-13 1965-03-02 Derivatives of lincomycin and related antibiotics and processes for producing them IL23089A (en)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US35948864A	1964-04-13	1964-04-13
US35944764A	1964-04-13	1964-04-13
US36959964A	1964-05-22	1964-05-22
US420104A US3268556A (en)	1964-04-13	1964-12-21	Novel lincomycin derivatives

Publications (1)

Publication Number	Publication Date
IL23089A true IL23089A (en)	1969-03-27

Family

ID=27502927

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL23089A IL23089A (en)	1964-04-13	1965-03-02	Derivatives of lincomycin and related antibiotics and processes for producing them

Country Status (9)

Country	Link
US (1)	US3268556A (de)
BE (1)	BE664296A (de)
CH (1)	CH454857A (de)
DE (1)	DE1518408A1 (de)
FR (1)	FR1509917A (de)
GB (2)	GB1105942A (de)
IL (1)	IL23089A (de)
NL (1)	NL6504608A (de)
SE (3)	SE303747B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3509256A (en) *	1969-01-08	1970-04-28	Upjohn Co	Lincomycin-2-phosphate antibiotic compositions and process of treatment
US3939163A (en) *	1973-12-28	1976-02-17	Ciba-Geigy Corporation	Metal salts of hindered piperidine carboxylic acids and stabilized compositions
US4071560A (en) *	1975-03-19	1978-01-31	American Cyanamid Company	Diaminoalditols useful in the preparation of antibacterial antibiotics AM31α, AM31β, and AM31γ
DE3538451A1 (de) *	1985-10-29	1987-05-07	Sueddeutsche Zucker Ag	Fettsaeureamide von aminopolyolen als nichtionogene tenside
KR20050056195A (ko) *	2002-08-15	2005-06-14	비큐론 파마슈티컬스 인코포레이티드	항박테리아 작용을 갖는 링코마이신 유도체
US7199105B2 (en) *	2002-08-15	2007-04-03	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
OA13179A (en) *	2003-06-17	2006-12-13	Vicuron Pharm Inc	Novel lincomycin derivatives possessing antimicrobial activity.
CN1823083B (zh) *	2003-06-17	2010-05-26	维库罗恩医药品公司	具备抗微生物活性的林可霉素衍生物
US7199106B2 (en)	2003-06-17	2007-04-03	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antimicrobial activity
US7256177B2 (en) *	2003-06-17	2007-08-14	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
US7361743B2 (en) *	2004-02-11	2008-04-22	Pfizer Inc	Lincomycin derivatives possessing antibacterial activity

1964
- 1964-12-21 US US420104A patent/US3268556A/en not_active Expired - Lifetime
1965
- 1965-03-02 IL IL23089A patent/IL23089A/en unknown
- 1965-03-23 GB GB12312/65A patent/GB1105942A/en not_active Expired
- 1965-03-23 GB GB38129/67A patent/GB1105943A/en not_active Expired
- 1965-03-30 CH CH434065A patent/CH454857A/de unknown
- 1965-04-10 DE DE19651518408 patent/DE1518408A1/de active Pending
- 1965-04-12 FR FR12928A patent/FR1509917A/fr not_active Expired
- 1965-04-12 SE SE4771/65A patent/SE303747B/xx unknown
- 1965-04-12 NL NL6504608A patent/NL6504608A/xx unknown
- 1965-05-21 BE BE664296A patent/BE664296A/xx unknown
1967
- 1967-04-03 SE SE4610/67A patent/SE308915B/xx unknown
- 1967-04-12 SE SE4611/67A patent/SE302967B/xx unknown

Also Published As

Publication number	Publication date
FR1509917A (fr)	1968-01-19
NL6504608A (de)	1965-10-14
SE302967B (de)	1968-08-12
BE664296A (de)	1965-11-22
GB1105942A (en)	1968-03-13
DE1518408A1 (de)	1969-08-21
SE303747B (de)	1968-09-09
CH454857A (de)	1968-04-30
SE308915B (de)	1969-03-03
US3268556A (en)	1966-08-23
GB1105943A (en)	1968-03-13

Publication	Publication Date	Title
US3496163A (en)	1970-02-17	7-halo-7-deoxylincomycins and process for preparing the same
EA001356B1 (ru)	2001-02-26	Дигликозилированные 1,2-диолы как псевдосоединения сиалил- lewis x и сиалил-lewis a
IL23089A (en)	1969-03-27	Derivatives of lincomycin and related antibiotics and processes for producing them
IL28910A (en)	1971-08-25	Lincomycin-2-phosphates and process for preparing them
US3380992A (en)	1968-04-30	Lincomycin derivatives and process for preparing same
US3671647A (en)	1972-06-20	Lincomycin 3-nucleotides and the salts thereof
US3435025A (en)	1969-03-25	7-deoxylincomycin and analogs and isomers thereof and process for making the same
US4187299A (en)	1980-02-05	Fortimicin E
EP0044477B1 (de)	1984-02-08	Verfahren zur Herstellung von Antibiotika und so hergestellte Antibiotika
US3817979A (en)	1974-06-18	7-0-demethylcelesticetin derivatives
US4283529A (en)	1981-08-11	3-O-Demethyl derivatives of Sannamycin C and antibiotic AX-127B-1
US3260747A (en)	1966-07-12	Process for preparing scyllo-inosamine
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
US3361739A (en)	1968-01-02	Lincomycin derivatives and processes for preparing the same
US3366624A (en)	1968-01-30	Lincomycin derivatives and process for preparing same
US3346635A (en)	1967-10-10	Mercaptals of 6-amino-6, 8-dideoxy-d-erythro-d-galacto-aldehydooctose and nu-acyl derivatives
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
IL23907A (en)	1971-05-26	Lincomycin analogues and a process for their production
DE69314947T2 (de)	1998-03-05	2-aminozuckermakrolid-derivate
US3692777A (en)	1972-09-19	5h-pyrrolo {8 2,1-c{9 {8 1,4{9 {0 benzodiazepin-5-ones
US4847284A (en)	1989-07-11	Antifungal fermentation product and derivatives and compositions thereof
EP0138708B1 (de)	1988-08-03	Isoefrotomycin
US3706729A (en)	1972-12-19	Antibiotics and processes for their preparation
US3969515A (en)	1976-07-13	Antibiotic U-48,266
EP0130554B1 (de)	1988-02-24	Physiologisch aktive Substanz, Verfahren zu ihrer Herstellung und pharmazeutische Zubereitung, die sie enthält