NO126620B - - Google Patents

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Publication number: NO126620B
Authority: NO; Norway
Prior art keywords: acid; carbon atoms; alkyl; carbon; triphenylphosphine
Prior art date: 1967-12-22

Application number

NO05106/68A

Other languages

English (en)

Norwegian (no)

Inventor

Robert David Birkenmeyer

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.)

1967-12-22

Filing date

1968-12-20

Publication date

1973-03-05

1968-12-20 Application filed by Upjohn Co filed Critical Upjohn Co

1973-03-05 Publication of NO126620B publication Critical patent/NO126620B/no

Links

239000002253 acid Substances 0.000 claims description 23
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 22
125000004432 carbon atom Chemical group C* 0.000 claims description 18
150000001875 compounds Chemical class 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 16
-1 diphenyl-(p-methoxyphenyl)-methyl Chemical group 0.000 claims description 14
238000000034 method Methods 0.000 claims description 13
125000000217 alkyl group Chemical group 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 8
229910052739 hydrogen Inorganic materials 0.000 claims description 8
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 6
229910052799 carbon Inorganic materials 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 4
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
229910052794 bromium Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
238000007327 hydrogenolysis reaction Methods 0.000 claims description 4
239000012442 inert solvent Substances 0.000 claims description 4
239000001301 oxygen Substances 0.000 claims description 4
229910052760 oxygen Inorganic materials 0.000 claims description 4
125000001424 substituent group Chemical group 0.000 claims description 4
DZJXKISLUDYJSV-UHFFFAOYSA-N [N].C1CCNC1 Chemical compound [N].C1CCNC1 DZJXKISLUDYJSV-UHFFFAOYSA-N 0.000 claims description 3
230000029936 alkylation Effects 0.000 claims description 3
238000005804 alkylation reaction Methods 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000001118 alkylidene group Chemical group 0.000 claims description 2
125000003710 aryl alkyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical group II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 20
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 12
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
OJMMVQQUTAEWLP-KIDUDLJLSA-N lincomycin Chemical compound 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 description 10
239000000243 solution Substances 0.000 description 10
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 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
229960005287 lincomycin Drugs 0.000 description 9
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 8
239000012458 free base Substances 0.000 description 7
239000007787 solid Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HJUGFYREWKUQJT-UHFFFAOYSA-N tetrabromomethane Chemical compound BrC(Br)(Br)Br HJUGFYREWKUQJT-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000011521 glass Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
230000000844 anti-bacterial effect Effects 0.000 description 4
239000002026 chloroform extract Substances 0.000 description 4
238000004587 chromatography analysis Methods 0.000 description 4
KDLRVYVGXIQJDK-AWPVFWJPSA-N clindamycin Chemical compound CN1C[C@H](CCC)C[C@H]1C(=O)N[C@H]([C@H](C)Cl)[C@@H]1[C@H](O)[C@H](O)[C@@H](O)[C@@H](SC)O1 KDLRVYVGXIQJDK-AWPVFWJPSA-N 0.000 description 4
239000012071 phase Substances 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
238000004458 analytical method Methods 0.000 description 3
239000008346 aqueous phase Substances 0.000 description 3
239000002585 base Substances 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical class 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
239000000047 product Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
229920006395 saturated elastomer Polymers 0.000 description 3
WSWCOQWTEOXDQX-UHFFFAOYSA-N 2,4-Hexadienoic acid Chemical compound CC=CC=CC(O)=O WSWCOQWTEOXDQX-UHFFFAOYSA-N 0.000 description 2
XJMMNTGIMDZPMU-UHFFFAOYSA-N 3-methylglutaric acid Chemical compound OC(=O)CC(C)CC(O)=O XJMMNTGIMDZPMU-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
ASQDBXOWEFHEPB-UHFFFAOYSA-N [C].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 Chemical compound [C].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 ASQDBXOWEFHEPB-UHFFFAOYSA-N 0.000 description 2
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 2
JOHCVVJGGSABQY-UHFFFAOYSA-N carbon tetraiodide Chemical compound IC(I)(I)I JOHCVVJGGSABQY-UHFFFAOYSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
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 2
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
229960001595 lincomycin hydrochloride Drugs 0.000 description 2
238000005649 metathesis reaction Methods 0.000 description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
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 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
PNGLEYLFMHGIQO-UHFFFAOYSA-M sodium;3-(n-ethyl-3-methoxyanilino)-2-hydroxypropane-1-sulfonate;dihydrate Chemical compound O.O.[Na+].[O-]S(=O)(=O)CC(O)CN(CC)C1=CC=CC(OC)=C1 PNGLEYLFMHGIQO-UHFFFAOYSA-M 0.000 description 2
238000000638 solvent extraction Methods 0.000 description 2
235000000346 sugar Nutrition 0.000 description 2
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
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 1
BHQCQFFYRZLCQQ-UHFFFAOYSA-N (3alpha,5alpha,7alpha,12alpha)-3,7,12-trihydroxy-cholan-24-oic acid Natural products OC1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 BHQCQFFYRZLCQQ-UHFFFAOYSA-N 0.000 description 1
WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 1
FRPZMMHWLSIFAZ-UHFFFAOYSA-N 10-undecenoic acid Chemical compound OC(=O)CCCCCCCCC=C FRPZMMHWLSIFAZ-UHFFFAOYSA-N 0.000 description 1
ZJWUEJOPKFYFQD-UHFFFAOYSA-N 2-hydroxy-3-phenylbenzoic acid Chemical compound OC(=O)C1=CC=CC(C=2C=CC=CC=2)=C1O ZJWUEJOPKFYFQD-UHFFFAOYSA-N 0.000 description 1
LGERKUYJCZOBTB-UHFFFAOYSA-N 2-hydroxy-5-phenylbenzoic acid Chemical compound C1=C(O)C(C(=O)O)=CC(C=2C=CC=CC=2)=C1 LGERKUYJCZOBTB-UHFFFAOYSA-N 0.000 description 1
ZRPLANDPDWYOMZ-UHFFFAOYSA-N 3-cyclopentylpropionic acid Chemical compound OC(=O)CCC1CCCC1 ZRPLANDPDWYOMZ-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
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
LSPHULWDVZXLIL-UHFFFAOYSA-N Camphoric acid Natural products CC1(C)C(C(O)=O)CCC1(C)C(O)=O LSPHULWDVZXLIL-UHFFFAOYSA-N 0.000 description 1
239000004380 Cholic acid Substances 0.000 description 1
WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
239000005639 Lauric acid Substances 0.000 description 1
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 1
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 1
235000021314 Palmitic acid Nutrition 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
229930182475 S-glycoside Natural products 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
HVWGGPRWKSHASF-UHFFFAOYSA-N Sulfuric acid, monooctadecyl ester Chemical compound CCCCCCCCCCCCCCCCCCOS(O)(=O)=O HVWGGPRWKSHASF-UHFFFAOYSA-N 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003513 alkali Substances 0.000 description 1
230000002152 alkylating effect Effects 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000000538 analytical sample Substances 0.000 description 1
JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
229940069428 antacid Drugs 0.000 description 1
239000003159 antacid agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
229940092714 benzenesulfonic acid Drugs 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
239000000872 buffer Substances 0.000 description 1
LSPHULWDVZXLIL-QUBYGPBYSA-N camphoric acid Chemical compound CC1(C)[C@H](C(O)=O)CC[C@]1(C)C(O)=O LSPHULWDVZXLIL-QUBYGPBYSA-N 0.000 description 1
KHAVLLBUVKBTBG-UHFFFAOYSA-N caproleic acid Natural products OC(=O)CCCCCCCC=C KHAVLLBUVKBTBG-UHFFFAOYSA-N 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
BHQCQFFYRZLCQQ-OELDTZBJSA-N cholic acid Chemical compound C([C@H]1C[C@H]2O)[C@H](O)CC[C@]1(C)[C@@H]1[C@@H]2[C@@H]2CC[C@H]([C@@H](CCC(O)=O)C)[C@@]2(C)[C@@H](O)C1 BHQCQFFYRZLCQQ-OELDTZBJSA-N 0.000 description 1
229960002471 cholic acid Drugs 0.000 description 1
235000019416 cholic acid Nutrition 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
238000001816 cooling Methods 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
NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical compound OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
KXGVEGMKQFWNSR-UHFFFAOYSA-N deoxycholic acid Natural products C1CC2CC(O)CCC2(C)C2C1C1CCC(C(CCC(O)=O)C)C1(C)C(O)C2 KXGVEGMKQFWNSR-UHFFFAOYSA-N 0.000 description 1
MZGNSEAPZQGJRB-UHFFFAOYSA-N dimethyldithiocarbamic acid Chemical compound CN(C)C(S)=S MZGNSEAPZQGJRB-UHFFFAOYSA-N 0.000 description 1
238000009826 distribution Methods 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
238000005658 halogenation reaction Methods 0.000 description 1
GOYAALBIXFNQOR-UHFFFAOYSA-N hexadecylsulfamic acid Chemical compound CCCCCCCCCCCCCCCCNS(O)(=O)=O GOYAALBIXFNQOR-UHFFFAOYSA-N 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
238000002156 mixing Methods 0.000 description 1
WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
HHMAJEQKYRNURJ-UHFFFAOYSA-N octadecylsulfamic acid Chemical compound CCCCCCCCCCCCCCCCCC[NH2+]S([O-])(=O)=O HHMAJEQKYRNURJ-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
230000000590 parasiticidal effect Effects 0.000 description 1
239000002297 parasiticide Substances 0.000 description 1
238000005554 pickling Methods 0.000 description 1
229940075930 picrate Drugs 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229920005749 polyurethane resin Polymers 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000000746 purification Methods 0.000 description 1
238000011084 recovery Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000000523 sample Substances 0.000 description 1
239000012453 solvate Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
238000004809 thin layer chromatography Methods 0.000 description 1
150000003569 thioglycosides Chemical class 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000017105 transposition Effects 0.000 description 1
229960002703 undecylenic acid Drugs 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/14—Acyclic radicals, not substituted by cyclic structures attached to a sulfur, selenium or tellurium atom of a saccharide radical
- C07H15/16—Lincomycin; Derivatives thereof

Landscapes

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

NO05106/68A 1967-12-22 1968-12-20 NO126620B (da)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US69272867A	1967-12-22	1967-12-22

Publications (1)

Publication Number	Publication Date
NO126620B true NO126620B (da)	1973-03-05

Family

ID=24781767

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO05106/68A NO126620B (da)	1967-12-22	1968-12-20

Country Status (14)

Country	Link
US (1)	US3475407A (da)
AT (1)	AT283594B (da)
BE (1)	BE725798A (da)
BR (1)	BR6805054D0 (da)
CH (1)	CH513149A (da)
CS (1)	CS152463B2 (da)
DK (1)	DK133783B (da)
ES (1)	ES360945A1 (da)
FI (1)	FI52460C (da)
NL (1)	NL6818208A (da)
NO (1)	NO126620B (da)
OA (1)	OA02960A (da)
SE (2)	SE382065B (da)
YU (1)	YU33006B (da)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
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US3692767A (en) *	1970-05-06	1972-09-19	Upjohn Co	Process for making lincomycin and analogs thereof and novel compounds obtained thereby
US4568741A (en) *	1984-05-15	1986-02-04	The Upjohn Company	Synthesis of 7-halo-7-deoxylincomycins
US4621075A (en) *	1984-11-28	1986-11-04	The Procter & Gamble Company	Gel-form topical antibiotic compositions
US5446028A (en) *	1985-12-12	1995-08-29	Dermik Laboratories, Inc.	Anti-acne method and composition
US6013637A (en) *	1998-06-12	2000-01-11	Dermik Laboratories Inc.	Anti-acne method and composition
EP1390084B1 (en)	2001-05-01	2011-03-23	A.V. Topchiev Institute of Petrochemical Synthesis	Two-phase, water-absorbent bioadhesive composition
US20030073648A1 (en) *	2001-08-28	2003-04-17	Chao Robert S.	Crystaline clindamycin free base
US7164011B2 (en) *	2002-08-15	2007-01-16	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
US7199105B2 (en) *	2002-08-15	2007-04-03	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
ES2637956T3 (es)	2003-01-24	2017-10-18	Stiefel Research Australia Pty Ltd	Espuma farmacéutica
US7256177B2 (en) *	2003-06-17	2007-08-14	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antibacterial activity
US7199106B2 (en)	2003-06-17	2007-04-03	Vicuron Pharmaceuticals, Inc.	Lincomycin derivatives possessing antimicrobial activity
RU2380092C2 (ru)	2004-01-30	2010-01-27	Кориум Интернэшнл, Инк.	Быстро растворяющаяся пленка для доставки активного агента
US7361743B2 (en) *	2004-02-11	2008-04-22	Pfizer Inc	Lincomycin derivatives possessing antibacterial activity
US20060078616A1 (en) *	2004-08-30	2006-04-13	Georgewill Dawaye A	Thermoreversible pharmaceutical formulation for anti-microbial agents comprising poloxamer polymers and hydroxy fatty acid ester of polyethylene glycol
AU2005306397A1 (en) *	2004-11-19	2006-05-26	Aventis Pharmaceuticals Inc.	Antibiotic compounds, compositions and medical uses
EP2010133B1 (en)	2006-03-31	2016-05-04	Stiefel Research Australia Pty Ltd	Foamable suspension gel
CN103172683B (zh) *	2013-04-10	2015-10-21	浙江海翔药业股份有限公司	一种盐酸克林霉素的制备方法
CA2957970A1 (en)	2014-08-15	2016-02-18	The Johns Hopkins University Technology Ventures	Composite material for tissue restoration
WO2016025786A1 (en)	2014-08-15	2016-02-18	The Johns Hopkins University	Post-surgical imaging marker
EP4091639A1 (en)	2015-08-17	2022-11-23	The Johns Hopkins University	In situ forming composite material for tissue restoration
EP3337426B1 (en)	2015-08-17	2025-04-30	The Johns Hopkins University	Mesenchymal cell-binding composite material for tissue restoration
EP3790602A1 (en)	2018-05-09	2021-03-17	The Johns Hopkins University	Nanofiber-hydrogel composites for cell and tissue delivery
IL307979B2 (en)	2018-05-09	2025-08-01	Univ Johns Hopkins	Nanofiber-hydrogel composites for enhanced soft tissue replacement and regeneration

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3282917A (en) *	1964-08-17	1966-11-01	Upjohn Co	Methyl n-(1-alkyl-4-alkoxy-prolyl)-alpha-thiolincosaminide compounds and process therefor

1967
- 1967-12-22 US US692728A patent/US3475407A/en not_active Expired - Lifetime
1968
- 1968-11-15 YU YU2678/68A patent/YU33006B/xx unknown
- 1968-11-27 FI FI683386A patent/FI52460C/fi active
- 1968-11-30 ES ES360945A patent/ES360945A1/es not_active Expired
- 1968-12-12 SE SE7115885A patent/SE382065B/xx unknown
- 1968-12-12 SE SE17035/68A patent/SE368199B/xx unknown
- 1968-12-18 NL NL6818208A patent/NL6818208A/xx unknown
- 1968-12-18 CH CH1889368A patent/CH513149A/de not_active IP Right Cessation
- 1968-12-19 AT AT1237968A patent/AT283594B/de not_active IP Right Cessation
- 1968-12-20 BR BR205054/68A patent/BR6805054D0/pt unknown
- 1968-12-20 NO NO05106/68A patent/NO126620B/no unknown
- 1968-12-20 OA OA53458A patent/OA02960A/xx unknown
- 1968-12-20 BE BE725798D patent/BE725798A/xx not_active IP Right Cessation
- 1968-12-20 DK DK629168AA patent/DK133783B/da unknown
- 1968-12-21 CS CS8736A patent/CS152463B2/cs unknown

Also Published As

Publication number	Publication date
US3475407A (en)	1969-10-28
CS152463B2 (da)	1973-12-19
OA02960A (fr)	1970-12-15
DK133783B (da)	1976-07-19
FI52460C (fi)	1977-09-12
BR6805054D0 (pt)	1973-02-08
SE382065B (sv)	1976-01-12
AT283594B (de)	1970-08-10
ES360945A1 (es)	1970-08-16
YU267868A (en)	1975-08-31
SE368199B (da)	1974-06-24
NL6818208A (da)	1969-06-24
DK133783C (da)	1976-12-27
BE725798A (da)	1969-06-20
YU33006B (en)	1976-03-31
CH513149A (de)	1971-09-30
FI52460B (da)	1977-05-31

Publication	Publication Date	Title
NO126620B (da)	1973-03-05
Kim et al.	1988	Monosubstituted guanidines from primary amines and aminoiminomethanesulfonic acid
US3544551A (en)	1970-12-01	7-mercapto-7-deoxylincomycins and process for preparing the same
NO137440B (no)	1977-11-21	Analogifremgangsm}te for fremstilling av terapeutisk aktive pleuromutiliner
US3509127A (en)	1970-04-28	Isologs of lincomycins and process for preparing the same
CH500203A (de)	1970-12-15	Verfahren zur Herstellung von Nucleosiden
EP0080818A1 (en)	1983-06-08	Erythromycin B derivatives
IL28910A (en)	1971-08-25	Lincomycin-2-phosphates and process for preparing them
DE69014064T2 (de)	1995-05-18	Benzopyranon-beta-D-thioxyloside, Verfahren zu ihrer Herstellung und ihre therapeutische Verwendung.
NO148109B (no)	1983-05-02	Fremgangsmaate ved fremstilling av 5`deoksy-5-fluoridin
US4882316A (en)	1989-11-21	Pyrimidine derivatives
EP0080819B1 (en)	1985-01-16	11-0-alkylerythromycin a derivatives
DE2836913A1 (de)	1979-03-15	Desoxyneamine
DE602004002692T2 (de)	2007-09-06	Verfahren zur Herstellung von Topiramate
DE69803979T2 (de)	2003-02-06	Verfahren zur herstellung von carboxamido-4-azasteroiden
AU615521B2 (en)	1991-10-03	Compounds used in the preparation of nifedipine
DE69419674T2 (de)	2000-04-06	Optisch aktive 1,4-Dihydropyridinderivate und Verfahren zu ihrer Herstellung
US4849512A (en)	1989-07-18	3-acylamino-3-deoxyallose derivatives
US4189433A (en)	1980-02-19	4-Hydroxy-1,2-benzisothiazoles and their manufacture
DE69314947T2 (de)	1998-03-05	2-aminozuckermakrolid-derivate
CN105330704B (zh)	2019-05-10	2-脱氧-d-葡萄糖的制备方法
NO823213L (no)	1983-04-05	Fremgangsmaate for fremstilling av antranilsyreestere
Catesby et al.	1961	Some glycosyl derivatives of piperazine
DE2752115A1 (de)	1978-06-01	Antitumorglycoside und verfahren zu deren herstellung
DE1620620C3 (de)	1975-05-28	Verfahren zur Herstellung von 7-Chlor-7deoxylincomycin und -epilincomycin sowie deren Isomeren und Analoga