FI105815B - Spikamysiinijohdannaisten valmistusmenetelmä ja siinä käytettävät välituotteet - Google Patents

Spikamysiinijohdannaisten valmistusmenetelmä ja siinä käytettävät välituotteet Download PDF

Info

Publication number: FI105815B
Authority: FI; Finland
Prior art keywords: purine; spicaminylamino; acid; mixture; added
Prior art date: 1991-07-12

Application number

FI923170A

Other languages

English (en)

Finnish (fi)

Swedish (sv)

Other versions

FI923170A (fi

FI923170A0 (fi

Inventor

Noboru Otake

Hiroyuki Kawai

Tomiko Kawasaki

Atsuo Odagawa

Masaru Kamishohara

Teruyuki Sakai

Original Assignee

Kirin Brewery

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.)

1991-07-12

Filing date

1992-07-09

Publication date

2000-10-13

1992-07-09 Application filed by Kirin Brewery filed Critical Kirin Brewery

1992-07-09 Publication of FI923170A0 publication Critical patent/FI923170A0/fi

1993-01-13 Publication of FI923170A publication Critical patent/FI923170A/fi

2000-10-13 Application granted granted Critical

2000-10-13 Publication of FI105815B publication Critical patent/FI105815B/fi

Links

YBZRLMLGUBIIDN-NZSGCTDASA-N spicamycin Chemical class O1[C@@H](C(O)CO)[C@H](NC(=O)CNC(=O)CCCCCCCCCCCCC(C)C)[C@@H](O)[C@@H](O)[C@H]1NC1=NC=NC2=C1N=CN2 YBZRLMLGUBIIDN-NZSGCTDASA-N 0.000 title claims abstract description 66
238000002360 preparation method Methods 0.000 title claims description 119
238000000034 method Methods 0.000 title claims description 55
230000008569 process Effects 0.000 title claims description 20
239000000543 intermediate Substances 0.000 title description 2
150000001875 compounds Chemical class 0.000 claims abstract description 74
150000003839 salts Chemical class 0.000 claims abstract description 38
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 27
125000000217 alkyl group Chemical group 0.000 claims abstract description 9
125000003342 alkenyl group Chemical group 0.000 claims abstract description 7
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
229910052760 oxygen Inorganic materials 0.000 claims abstract description 3
229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
KDCGOANMDULRCW-UHFFFAOYSA-N 7H-purine Chemical compound N1=CNC2=NC=NC2=C1 KDCGOANMDULRCW-UHFFFAOYSA-N 0.000 claims description 524
150000002148 esters Chemical class 0.000 claims description 139
239000002253 acid Substances 0.000 claims description 58
-1 trans-2,4-dodecadienoylglycyl Chemical group 0.000 claims description 51
150000001735 carboxylic acids Chemical class 0.000 claims description 9
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 7
238000007796 conventional method Methods 0.000 claims description 4
229910018540 Si C Inorganic materials 0.000 claims description 3
230000004913 activation Effects 0.000 claims description 3
229920001577 copolymer Polymers 0.000 claims description 3
125000003630 glycyl group Chemical group [H]N([H])C([H])([H])C(*)=O 0.000 claims description 3
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
229910052736 halogen Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
KHZAOWUHQARJQE-UHFFFAOYSA-N 6-n-[(4-aminophenyl)methyl]-9-methyl-2-n-[[3-(trifluoromethyl)phenyl]methyl]purine-2,6-diamine Chemical compound N1=C(NCC=2C=C(C=CC=2)C(F)(F)F)N=C2N(C)C=NC2=C1NCC1=CC=C(N)C=C1 KHZAOWUHQARJQE-UHFFFAOYSA-N 0.000 claims 1
PEEHTFAAVSWFBL-UHFFFAOYSA-N Maleimide Chemical compound O=C1NC(=O)C=C1 PEEHTFAAVSWFBL-UHFFFAOYSA-N 0.000 claims 1
125000005843 halogen group Chemical group 0.000 claims 1
125000000896 monocarboxylic acid group Chemical group 0.000 claims 1
230000000259 anti-tumor effect Effects 0.000 abstract description 14
239000002246 antineoplastic agent Substances 0.000 abstract description 8
231100001274 therapeutic index Toxicity 0.000 abstract description 4
DCERHCFNWRGHLK-UHFFFAOYSA-N C[Si](C)C Chemical compound C[Si](C)C DCERHCFNWRGHLK-UHFFFAOYSA-N 0.000 abstract 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 688
239000000203 mixture Substances 0.000 description 324
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 306
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 301
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 279
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 164
239000011541 reaction mixture Substances 0.000 description 161
239000000741 silica gel Substances 0.000 description 151
229910002027 silica gel Inorganic materials 0.000 description 151
OKKJLVBELUTLKV-MZCSYVLQSA-N Deuterated methanol Chemical compound [2H]OC([2H])([2H])[2H] OKKJLVBELUTLKV-MZCSYVLQSA-N 0.000 description 146
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 136
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 133
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 123
239000003480 eluent Substances 0.000 description 123
239000000243 solution Substances 0.000 description 115
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 112
239000002904 solvent Substances 0.000 description 96
238000001819 mass spectrum Methods 0.000 description 90
238000002844 melting Methods 0.000 description 90
230000008018 melting Effects 0.000 description 90
238000000921 elemental analysis Methods 0.000 description 89
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 86
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 84
238000004821 distillation Methods 0.000 description 84
WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 description 80
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 78
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 75
239000000126 substance Substances 0.000 description 72
239000010410 layer Substances 0.000 description 71
238000002329 infrared spectrum Methods 0.000 description 70
DEVFVVLSBJSUNB-UHFFFAOYSA-N 7h-purine;hydrochloride Chemical compound Cl.N1=CNC2=NC=NC2=C1 DEVFVVLSBJSUNB-UHFFFAOYSA-N 0.000 description 65
BTJIUGUIPKRLHP-UHFFFAOYSA-N 4-nitrophenol Chemical compound OC1=CC=C([N+]([O-])=O)C=C1 BTJIUGUIPKRLHP-UHFFFAOYSA-N 0.000 description 61
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 56
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 54
OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 53
239000000047 product Substances 0.000 description 48
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 46
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 45
239000002244 precipitate Substances 0.000 description 45
238000001914 filtration Methods 0.000 description 42
239000000706 filtrate Substances 0.000 description 28
229910052757 nitrogen Inorganic materials 0.000 description 28
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 28
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 27
230000002378 acidificating effect Effects 0.000 description 27
150000004702 methyl esters Chemical class 0.000 description 27
238000003756 stirring Methods 0.000 description 27
NQTADLQHYWFPDB-UHFFFAOYSA-N N-Hydroxysuccinimide Chemical compound ON1C(=O)CCC1=O NQTADLQHYWFPDB-UHFFFAOYSA-N 0.000 description 24
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 24
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 22
238000010898 silica gel chromatography Methods 0.000 description 22
238000004587 chromatography analysis Methods 0.000 description 21
238000000862 absorption spectrum Methods 0.000 description 19
238000001816 cooling Methods 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 18
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical group NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 16
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 16
239000011734 sodium Substances 0.000 description 16
YBZRLMLGUBIIDN-UHFFFAOYSA-N spicamycin Natural products O1C(C(O)CO)C(NC(=O)CNC(=O)CCCCCCCCCCCCC(C)C)C(O)C(O)C1NC1=NC=NC2=C1NC=N2 YBZRLMLGUBIIDN-UHFFFAOYSA-N 0.000 description 15
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 14
239000012046 mixed solvent Substances 0.000 description 14
AOTMRIXFFOGWDT-UHFFFAOYSA-N omega-hydroxyhexadecanoic acid methyl ester Natural products COC(=O)CCCCCCCCCCCCCCCO AOTMRIXFFOGWDT-UHFFFAOYSA-N 0.000 description 14
238000010992 reflux Methods 0.000 description 13
UGAGPNKCDRTDHP-UHFFFAOYSA-N 16-hydroxyhexadecanoic acid Chemical compound OCCCCCCCCCCCCCCCC(O)=O UGAGPNKCDRTDHP-UHFFFAOYSA-N 0.000 description 12
NXXJDMWQIZZUGA-UHFFFAOYSA-N 6-n-benzyl-2-n-(1-phenylethyl)-7h-purine-2,6-diamine Chemical compound C=1C=CC=CC=1C(C)NC(N=C1N=CNC1=1)=NC=1NCC1=CC=CC=C1 NXXJDMWQIZZUGA-UHFFFAOYSA-N 0.000 description 12
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
206010028980 Neoplasm Diseases 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
235000017557 sodium bicarbonate Nutrition 0.000 description 12
229910000030 sodium bicarbonate Inorganic materials 0.000 description 12
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 12
238000001704 evaporation Methods 0.000 description 11
230000008020 evaporation Effects 0.000 description 11
239000001257 hydrogen Substances 0.000 description 11
229910052739 hydrogen Inorganic materials 0.000 description 11
NTNUDYROPUKXNA-UHFFFAOYSA-N methyl 2-(triphenyl-$l^{5}-phosphanylidene)acetate Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)(=CC(=O)OC)C1=CC=CC=C1 NTNUDYROPUKXNA-UHFFFAOYSA-N 0.000 description 11
238000000746 purification Methods 0.000 description 11
GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 description 10
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 10
101150065749 Churc1 gene Proteins 0.000 description 10
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 10
102100038239 Protein Churchill Human genes 0.000 description 10
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000002585 base Substances 0.000 description 10
238000002347 injection Methods 0.000 description 10
239000007924 injection Substances 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
MUCMKTPAZLSKTL-UHFFFAOYSA-N (3RS)-3-hydroxydodecanoic acid Natural products CCCCCCCCCC(O)CC(O)=O MUCMKTPAZLSKTL-UHFFFAOYSA-N 0.000 description 9
JGHSBPIZNUXPLA-UHFFFAOYSA-N 2-hydroxyhexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)C(O)=O JGHSBPIZNUXPLA-UHFFFAOYSA-N 0.000 description 9
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 9
239000004471 Glycine Chemical group 0.000 description 9
239000012043 crude product Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000000843 powder Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
ZDHCZVWCTKTBRY-UHFFFAOYSA-N 12-hydroxylauric acid Chemical compound OCCCCCCCCCCCC(O)=O ZDHCZVWCTKTBRY-UHFFFAOYSA-N 0.000 description 8
BZUNJUAMQZRJIP-UHFFFAOYSA-N 15-hydroxypentadecanoic acid Chemical compound OCCCCCCCCCCCCCCC(O)=O BZUNJUAMQZRJIP-UHFFFAOYSA-N 0.000 description 8
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 8
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 8
206010009944 Colon cancer Diseases 0.000 description 8
241001465754 Metazoa Species 0.000 description 8
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 8
239000001110 calcium chloride Substances 0.000 description 8
229910001628 calcium chloride Inorganic materials 0.000 description 8
FUKUFMFMCZIRNT-UHFFFAOYSA-N hydron;methanol;chloride Chemical compound Cl.OC FUKUFMFMCZIRNT-UHFFFAOYSA-N 0.000 description 8
WQCYAHKAJFZVCO-UHFFFAOYSA-N methyl 15-hydroxypentadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCO WQCYAHKAJFZVCO-UHFFFAOYSA-N 0.000 description 8
WORJEOGGNQDSOE-ASTXPPQBSA-N trichloro(deuterio)methane;trideuterio(deuteriooxy)methane Chemical compound [2H]C(Cl)(Cl)Cl.[2H]OC([2H])([2H])[2H] WORJEOGGNQDSOE-ASTXPPQBSA-N 0.000 description 8
WNLVXSRACLAFOL-AQASXUMVSA-N (2e,4e)-tetradeca-2,4-dienoic acid Chemical compound CCCCCCCCC\C=C\C=C\C(O)=O WNLVXSRACLAFOL-AQASXUMVSA-N 0.000 description 7
VRPJIFMKZZEXLR-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxycarbonylamino]acetic acid Chemical compound CC(C)(C)OC(=O)NCC(O)=O VRPJIFMKZZEXLR-UHFFFAOYSA-N 0.000 description 7
125000003277 amino group Chemical group 0.000 description 7
239000007864 aqueous solution Substances 0.000 description 7
229910052799 carbon Inorganic materials 0.000 description 7
239000000460 chlorine Substances 0.000 description 7
208000029742 colonic neoplasm Diseases 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
QJRRBVNPIKYRQJ-UHFFFAOYSA-N 10-methylundecanoic acid Chemical compound CC(C)CCCCCCCCC(O)=O QJRRBVNPIKYRQJ-UHFFFAOYSA-N 0.000 description 6
YYKBWYBUCFHYPR-UHFFFAOYSA-N 12-bromododecanoic acid Chemical compound OC(=O)CCCCCCCCCCCBr YYKBWYBUCFHYPR-UHFFFAOYSA-N 0.000 description 6
OFOWUDSDZLONKT-UHFFFAOYSA-N 12-oxo-octadecanoic acid Chemical compound CCCCCCC(=O)CCCCCCCCCCC(O)=O OFOWUDSDZLONKT-UHFFFAOYSA-N 0.000 description 6
PNNLLDRVJFDXNL-UHFFFAOYSA-N 16-Fluorohexadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCF PNNLLDRVJFDXNL-UHFFFAOYSA-N 0.000 description 6
SUBCFFCOIUCDQV-UHFFFAOYSA-N 2-n-[(3-fluorophenyl)methyl]-6-n-[(4-nitrophenyl)methyl]-7h-purine-2,6-diamine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CNC1=NC(NCC=2C=C(F)C=CC=2)=NC2=C1NC=N2 SUBCFFCOIUCDQV-UHFFFAOYSA-N 0.000 description 6
DDSBPUYZPWNNGH-UHFFFAOYSA-N 6-n-[(4-nitrophenyl)methyl]-2-n-[[3-(trifluoromethyl)phenyl]methyl]-7h-purine-2,6-diamine Chemical compound C1=CC([N+](=O)[O-])=CC=C1CNC1=NC(NCC=2C=C(C=CC=2)C(F)(F)F)=NC2=C1NC=N2 DDSBPUYZPWNNGH-UHFFFAOYSA-N 0.000 description 6
PAQVSQYFIQLOMC-UHFFFAOYSA-N 7H-purine 2,2,2-trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F.N1C=NC2=NC=NC=C12 PAQVSQYFIQLOMC-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 6
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 6
150000002431 hydrogen Chemical class 0.000 description 6
231100000682 maximum tolerated dose Toxicity 0.000 description 6
238000011218 seed culture Methods 0.000 description 6
238000001228 spectrum Methods 0.000 description 6
FPGGTKZVZWFYPV-UHFFFAOYSA-M tetrabutylammonium fluoride Chemical compound [F-].CCCC[N+](CCCC)(CCCC)CCCC FPGGTKZVZWFYPV-UHFFFAOYSA-M 0.000 description 6
TUNFSRHWOTWDNC-UHFFFAOYSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCCC(O)=O TUNFSRHWOTWDNC-UHFFFAOYSA-N 0.000 description 6
BWZVCCNYKMEVEX-UHFFFAOYSA-N 2,4,6-Trimethylpyridine Chemical compound CC1=CC(C)=NC(C)=C1 BWZVCCNYKMEVEX-UHFFFAOYSA-N 0.000 description 5
LDNZLGJRIGQKHL-UHFFFAOYSA-N 7H-purin-1-ium bromide Chemical compound [Br-].[NH+]1=CN=C2N=CNC2=C1 LDNZLGJRIGQKHL-UHFFFAOYSA-N 0.000 description 5
229940126062 Compound A Drugs 0.000 description 5
NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
JWIPGAFCGUDKEY-UHFFFAOYSA-L O[Cr](Cl)(=O)=O.C1=CC=NC=C1 Chemical compound O[Cr](Cl)(=O)=O.C1=CC=NC=C1 JWIPGAFCGUDKEY-UHFFFAOYSA-L 0.000 description 5
YDZIJQXINJLRLL-UHFFFAOYSA-N alpha-hydroxydodecanoic acid Natural products CCCCCCCCCCC(O)C(O)=O YDZIJQXINJLRLL-UHFFFAOYSA-N 0.000 description 5
239000000010 aprotic solvent Substances 0.000 description 5
239000012298 atmosphere Substances 0.000 description 5
238000006243 chemical reaction Methods 0.000 description 5
SIHHLZPXQLFPMC-UHFFFAOYSA-N chloroform;methanol;hydrate Chemical compound O.OC.ClC(Cl)Cl SIHHLZPXQLFPMC-UHFFFAOYSA-N 0.000 description 5
239000003814 drug Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 4
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 description 4
LTXSBXRSRAOCSA-UHFFFAOYSA-N 15-chloropentadecanoic acid Chemical compound OC(=O)CCCCCCCCCCCCCCCl LTXSBXRSRAOCSA-UHFFFAOYSA-N 0.000 description 4
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
DPRAYRYQQAXQPE-UHFFFAOYSA-N 2-bromohexadecanoic acid Chemical compound CCCCCCCCCCCCCCC(Br)C(O)=O DPRAYRYQQAXQPE-UHFFFAOYSA-N 0.000 description 4
VMDJHUIQKPMKOC-UHFFFAOYSA-N 2-chlorododecanoic acid Chemical compound CCCCCCCCCCC(Cl)C(O)=O VMDJHUIQKPMKOC-UHFFFAOYSA-N 0.000 description 4
LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
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239000003242 anti bacterial agent Substances 0.000 description 1
229940088710 antibiotic agent Drugs 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
230000003078 antioxidant effect Effects 0.000 description 1
ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
239000012300 argon atmosphere Substances 0.000 description 1
230000008901 benefit Effects 0.000 description 1
230000037396 body weight Effects 0.000 description 1
ICXXXLGATNSZAV-UHFFFAOYSA-N butylazanium;chloride Chemical compound [Cl-].CCCC[NH3+] ICXXXLGATNSZAV-UHFFFAOYSA-N 0.000 description 1
DVECBJCOGJRVPX-UHFFFAOYSA-N butyryl chloride Chemical compound CCCC(Cl)=O DVECBJCOGJRVPX-UHFFFAOYSA-N 0.000 description 1
AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
239000000920 calcium hydroxide Substances 0.000 description 1
229910001861 calcium hydroxide Inorganic materials 0.000 description 1
150000001718 carbodiimides Chemical class 0.000 description 1
150000001721 carbon Chemical class 0.000 description 1
235000011089 carbon dioxide Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
229940105329 carboxymethylcellulose Drugs 0.000 description 1
229940084030 carboxymethylcellulose calcium Drugs 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
238000001311 chemical methods and process Methods 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 1
235000013985 cinnamic acid Nutrition 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
SECPZKHBENQXJG-UHFFFAOYSA-N cis-palmitoleic acid Natural products CCCCCCC=CCCCCCCCC(O)=O SECPZKHBENQXJG-UHFFFAOYSA-N 0.000 description 1
230000007012 clinical effect Effects 0.000 description 1
229940125773 compound 10 Drugs 0.000 description 1
229940125898 compound 5 Drugs 0.000 description 1
239000000498 cooling water Substances 0.000 description 1
LSXDOTMGLUJQCM-UHFFFAOYSA-M copper(i) iodide Chemical compound I[Cu] LSXDOTMGLUJQCM-UHFFFAOYSA-M 0.000 description 1
230000008878 coupling Effects 0.000 description 1
238000010168 coupling process Methods 0.000 description 1
238000005859 coupling reaction Methods 0.000 description 1
230000009849 deactivation Effects 0.000 description 1
MMFCJPPRCYDLLZ-UHFFFAOYSA-N dec-2-enal Natural products CCCCCCCC=CC=O MMFCJPPRCYDLLZ-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000019700 dicalcium phosphate Nutrition 0.000 description 1
XLQDQRMFMXYSQS-UHFFFAOYSA-N dichloromethane;hydrochloride Chemical compound Cl.ClCCl XLQDQRMFMXYSQS-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
230000029087 digestion Effects 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
238000001647 drug administration Methods 0.000 description 1
230000000694 effects Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
WXYUYUQGAHWVJH-UHFFFAOYSA-N ethyl 2,2-difluoro-3-hydroxyhexadecanoate Chemical compound CCCCCCCCCCCCCC(O)C(F)(F)C(=O)OCC WXYUYUQGAHWVJH-UHFFFAOYSA-N 0.000 description 1
AJJNEBRSGQHJRN-UHFFFAOYSA-N ethyl 2,2-difluoro-3-hydroxytetradecanoate Chemical compound CCCCCCCCCCCC(O)C(F)(F)C(=O)OCC AJJNEBRSGQHJRN-UHFFFAOYSA-N 0.000 description 1
235000019325 ethyl cellulose Nutrition 0.000 description 1
229920001249 ethyl cellulose Polymers 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
238000000855 fermentation Methods 0.000 description 1
230000004151 fermentation Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000002367 halogens Chemical group 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
239000001863 hydroxypropyl cellulose Substances 0.000 description 1
235000010977 hydroxypropyl cellulose Nutrition 0.000 description 1
125000001841 imino group Chemical group [H]N=* 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
238000011081 inoculation Methods 0.000 description 1
238000001361 intraarterial administration Methods 0.000 description 1
238000007918 intramuscular administration Methods 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
208000032839 leukemia Diseases 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
239000000347 magnesium hydroxide Substances 0.000 description 1
229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
230000014759 maintenance of location Effects 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
238000004519 manufacturing process Methods 0.000 description 1
239000000463 material Substances 0.000 description 1
238000005259 measurement Methods 0.000 description 1
238000002483 medication Methods 0.000 description 1
UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
WVJKHCGMRZGIJH-UHFFFAOYSA-N methanetriamine Chemical compound NC(N)N WVJKHCGMRZGIJH-UHFFFAOYSA-N 0.000 description 1
ACUIYXOOZPHRRA-ZBMVRHCNSA-N methyl (2e,4e)-hexadeca-2,4-dienoate Chemical compound CCCCCCCCCCC\C=C\C=C\C(=O)OC ACUIYXOOZPHRRA-ZBMVRHCNSA-N 0.000 description 1
CKTWGIPZKUEHIY-BUHFOSPRSA-N methyl (E)-tetradec-2-enoate Chemical compound CCCCCCCCCCC\C=C\C(=O)OC CKTWGIPZKUEHIY-BUHFOSPRSA-N 0.000 description 1
FZKILUWDXTYCDR-OUKQBFOZSA-N methyl (e)-tridec-2-enoate Chemical compound CCCCCCCCCC\C=C\C(=O)OC FZKILUWDXTYCDR-OUKQBFOZSA-N 0.000 description 1
CDVCDJPEYGTVIQ-UHFFFAOYSA-N methyl 12-fluorododecanoate Chemical compound COC(=O)CCCCCCCCCCCF CDVCDJPEYGTVIQ-UHFFFAOYSA-N 0.000 description 1
RVWOWEQKPMPWMQ-UHFFFAOYSA-N methyl 12-hydroxyoctadecanoate Chemical compound CCCCCCC(O)CCCCCCCCCCC(=O)OC RVWOWEQKPMPWMQ-UHFFFAOYSA-N 0.000 description 1
XTHMUQUQYMNREB-UHFFFAOYSA-N methyl 12-phenoxydodecanoate Chemical compound COC(=O)CCCCCCCCCCCOC1=CC=CC=C1 XTHMUQUQYMNREB-UHFFFAOYSA-N 0.000 description 1
SPDQFFNKPDVVNV-UHFFFAOYSA-N methyl 13-bromotridecanoate Chemical compound COC(=O)CCCCCCCCCCCCBr SPDQFFNKPDVVNV-UHFFFAOYSA-N 0.000 description 1
KABAILADUUZJOR-UHFFFAOYSA-N methyl 13-chlorotridecanoate Chemical compound COC(=O)CCCCCCCCCCCCCl KABAILADUUZJOR-UHFFFAOYSA-N 0.000 description 1
NRYDSONQCARRAQ-UHFFFAOYSA-N methyl 14-bromotetradecanoate Chemical compound COC(=O)CCCCCCCCCCCCCBr NRYDSONQCARRAQ-UHFFFAOYSA-N 0.000 description 1
CZWCOVYSFRIKQU-UHFFFAOYSA-N methyl 14-chlorotetradecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCl CZWCOVYSFRIKQU-UHFFFAOYSA-N 0.000 description 1
BMQGDAFDSTWKOS-UHFFFAOYSA-N methyl 15-azidopentadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCN=[N+]=[N-] BMQGDAFDSTWKOS-UHFFFAOYSA-N 0.000 description 1
BVQSDPDEVQSPMW-UHFFFAOYSA-N methyl 15-bromopentadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCBr BVQSDPDEVQSPMW-UHFFFAOYSA-N 0.000 description 1
VCJJWNCEIHFSOU-UHFFFAOYSA-N methyl 15-chloropentadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCCl VCJJWNCEIHFSOU-UHFFFAOYSA-N 0.000 description 1
ZYTQDEJMRYPSHE-UHFFFAOYSA-N methyl 16-bromohexadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCCBr ZYTQDEJMRYPSHE-UHFFFAOYSA-N 0.000 description 1
BOGBHASNNSOTPN-UHFFFAOYSA-N methyl 16-cyanohexadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCCC#N BOGBHASNNSOTPN-UHFFFAOYSA-N 0.000 description 1
ZFMXTBUVHPFAOV-UHFFFAOYSA-N methyl 16-fluorohexadecanoate Chemical compound COC(=O)CCCCCCCCCCCCCCCF ZFMXTBUVHPFAOV-UHFFFAOYSA-N 0.000 description 1
PEHGTPWGKJZZIV-UHFFFAOYSA-N methyl 2-(4-methylphenyl)sulfonyloxydodecanoate Chemical compound CCCCCCCCCCC(C(=O)OC)OS(=O)(=O)C1=CC=C(C)C=C1 PEHGTPWGKJZZIV-UHFFFAOYSA-N 0.000 description 1
RTABFVHVABARDD-UHFFFAOYSA-N methyl 2-fluorohexadecanoate Chemical compound CCCCCCCCCCCCCCC(F)C(=O)OC RTABFVHVABARDD-UHFFFAOYSA-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
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
235000012149 noodles Nutrition 0.000 description 1
239000002777 nucleoside Substances 0.000 description 1
150000003833 nucleoside derivatives Chemical class 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
229940055726 pantothenic acid Drugs 0.000 description 1
235000019161 pantothenic acid Nutrition 0.000 description 1
239000011713 pantothenic acid Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
229950008882 polysorbate Drugs 0.000 description 1
239000001267 polyvinylpyrrolidone Substances 0.000 description 1
235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
239000011698 potassium fluoride Substances 0.000 description 1
235000003270 potassium fluoride Nutrition 0.000 description 1
239000012286 potassium permanganate Substances 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
230000002335 preservative effect Effects 0.000 description 1
KPBSJEBFALFJTO-UHFFFAOYSA-N propane-1-sulfonyl chloride Chemical compound CCCS(Cl)(=O)=O KPBSJEBFALFJTO-UHFFFAOYSA-N 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
125000006239 protecting group Chemical group 0.000 description 1
125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 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
239000000376 reactant Substances 0.000 description 1
230000001603 reducing effect Effects 0.000 description 1
238000011160 research Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000035945 sensitivity Effects 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
235000009518 sodium iodide Nutrition 0.000 description 1
239000001540 sodium lactate Substances 0.000 description 1
235000011088 sodium lactate Nutrition 0.000 description 1
229940005581 sodium lactate Drugs 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
239000004094 surface-active agent Substances 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
UHUFTBALEZWWIH-UHFFFAOYSA-N tetradecanal Chemical compound CCCCCCCCCCCCCC=O UHUFTBALEZWWIH-UHFFFAOYSA-N 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
NRTLTGGGUQIRRT-UHFFFAOYSA-N triethylazanium;bromide Chemical compound [Br-].CC[NH+](CC)CC NRTLTGGGUQIRRT-UHFFFAOYSA-N 0.000 description 1
RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H19/00—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof
- C07H19/02—Compounds containing a hetero ring sharing one ring hetero atom with a saccharide radical; Nucleosides; Mononucleotides; Anhydro-derivatives thereof sharing nitrogen
- C07H19/04—Heterocyclic radicals containing only nitrogen atoms as ring hetero atom
- C07H19/16—Purine radicals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P35/00—Antineoplastic agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/02—Heterocyclic radicals containing only nitrogen as ring hetero atoms

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Molecular Biology (AREA)
Genetics & Genomics (AREA)
Biotechnology (AREA)
Biochemistry (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Medicinal Chemistry (AREA)
General Chemical & Material Sciences (AREA)
Public Health (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Preparation Of Compounds By Using Micro-Organisms (AREA)
Saccharide Compounds (AREA)
Medicines Containing Material From Animals Or Micro-Organisms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

FI923170A 1991-07-12 1992-07-09 Spikamysiinijohdannaisten valmistusmenetelmä ja siinä käytettävät välituotteet FI105815B (fi)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
JP19890391		1991-07-12
JP19890391		1991-07-12
JP32684591		1991-11-15
JP32684591		1991-11-15
JP11066592		1992-04-03
JP4110665A JP2783722B2 (ja)	1991-07-12	1992-04-03	スピカマイシン誘導体およびそれを含む抗腫瘍剤

Publications (3)

Publication Number	Publication Date
FI923170A0 FI923170A0 (fi)	1992-07-09
FI923170A FI923170A (fi)	1993-01-13
FI105815B true FI105815B (fi)	2000-10-13

Family

ID=27311786

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
FI923170A FI105815B (fi)	1991-07-12	1992-07-09	Spikamysiinijohdannaisten valmistusmenetelmä ja siinä käytettävät välituotteet

Country Status (16)

Country	Link
US (2)	US5461036A (hu)
EP (1)	EP0525479B1 (hu)
JP (1)	JP2783722B2 (hu)
KR (1)	KR100253050B1 (hu)
AT (1)	ATE159948T1 (hu)
AU (1)	AU657551B2 (hu)
CA (1)	CA2073567C (hu)
DE (1)	DE69222992T2 (hu)
DK (1)	DK0525479T3 (hu)
ES (1)	ES2111019T3 (hu)
FI (1)	FI105815B (hu)
GR (1)	GR3025293T3 (hu)
HK (1)	HK1001729A1 (hu)
HU (1)	HU221808B1 (hu)
NO (1)	NO178500C (hu)
SG (1)	SG52704A1 (hu)

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US7017208B2 (en) *	1995-08-04	2006-03-28	Hill-Rom Services, Inc.	Hospital bed
US5905069A (en) *	1998-01-26	1999-05-18	The General Hospital Corporation	Methods of decreasing or preventing pain using spicamycin or derivatives thereof
ES2281591T3 (es) *	1999-01-22	2007-10-01	Kirin Beer Kabushiki Kaisha	Derivados de n-((quinolinil)oxil)-fenil)-urea y de n-((quinazolinil)oxil)-fenil)-urea con actividad antitumoral.
DE60144383D1 (de) *	2000-09-20	2011-05-19	Gen Hospital Corp	Methoden zur verminderung oder verhinderung von schmerzen mit spicamycin-derivaten
US20060074014A1 (en) *	2002-11-18	2006-04-06	Vicuron Pharmaceuticals Inc.	Dalbavancin compositions for treatment of bacterial infections
MXPA05005338A (es) *	2002-11-18	2005-12-14	Vicuron Pharm Inc	Metodos para administrar dalbavancin para el tratamiento de infecciones bacterianas.
EP2295400A3 (en) *	2003-09-11	2012-10-24	Invista Technologies S.à.r.l.	Process of hydrocyanation of unsaturated carboxylic acid derivatives
JP4608651B2 (ja) *	2004-06-24	2011-01-12	財団法人ヒューマンサイエンス振興財団	抗ガン作用を有する化合物、その製造方法及び抗ガン剤
US8119829B2 (en) *	2004-09-08	2012-02-21	Invista North America S.A.R.L.	Process of hydrocyanation of unsaturated carboxylic acid derivatives
WO2010042212A2 (en)	2008-10-10	2010-04-15	Dara Biosciences, Inc.	Methods for treating or preventing pain using spicamycin derivatives
EP2597082A1 (de)	2011-11-24	2013-05-29	Symrise AG	Verbindungen zur Maskierung eines unangenehmen Geschmacks
CN104822369A (zh) *	2012-08-09	2015-08-05	达拉生物科学公司	包含穗霉素衍生物的组合物及其使用方法
WO2015061481A1 (en)	2013-10-23	2015-04-30	Dara Biosciences, Inc.	Methods of treating liquid tumors using compositions comprising spicamycin derivatives
CN110386874B (zh) *	2018-04-16	2022-10-04	湖北金鹤化工有限公司	一种12-酮基硬脂酸酯及其制备方法

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Publication number	Priority date	Publication date	Assignee	Title
US3155647A (en)	1963-07-24	1964-11-03	Olin Mathieson	Septaciding and derivatives thereof
US3264195A (en) *	1963-07-24	1966-08-02	Squibb & Sons Inc	Process for the preparation of septacidin and derivatives
US4086416A (en) *	1977-05-17	1978-04-25	Stanford Research Institute	Septacidin analogs
JPS59161389A (ja) *	1983-03-07	1984-09-12	Eisai Co Ltd	７−カルボキシメトキシフエニルアセトアミドセフエム誘導体，その製造法およびそれからなる抗菌剤
JPS59161396A (ja)	1983-03-04	1984-09-12	Kirin Brewery Co Ltd	新規抗生物質スピカマイシン
US4975434A (en) *	1986-05-27	1990-12-04	The United States Of America As Represented By The Secretary Of The Department Of Health And Human Services	Antiviral and anticancer cyclopentenyl cytosine
WO1990015811A1 (en)	1989-06-16	1990-12-27	Kirin Beer Kabushiki Kaisha	Spicamycin x and its use

1992
- 1992-04-03 JP JP4110665A patent/JP2783722B2/ja not_active Expired - Lifetime
- 1992-07-08 US US07/910,640 patent/US5461036A/en not_active Expired - Lifetime
- 1992-07-08 NO NO922674A patent/NO178500C/no not_active IP Right Cessation
- 1992-07-09 FI FI923170A patent/FI105815B/fi active
- 1992-07-10 ES ES92111782T patent/ES2111019T3/es not_active Expired - Lifetime
- 1992-07-10 AT AT92111782T patent/ATE159948T1/de active
- 1992-07-10 CA CA002073567A patent/CA2073567C/en not_active Expired - Lifetime
- 1992-07-10 SG SG1996008096A patent/SG52704A1/en unknown
- 1992-07-10 DE DE69222992T patent/DE69222992T2/de not_active Expired - Lifetime
- 1992-07-10 AU AU19600/92A patent/AU657551B2/en not_active Ceased
- 1992-07-10 HU HU9202285A patent/HU221808B1/hu not_active IP Right Cessation
- 1992-07-10 DK DK92111782.6T patent/DK0525479T3/da active
- 1992-07-10 EP EP92111782A patent/EP0525479B1/en not_active Expired - Lifetime
- 1992-07-11 KR KR1019920012373A patent/KR100253050B1/ko not_active IP Right Cessation
1995
- 1995-04-26 US US08/429,303 patent/US5631238A/en not_active Expired - Lifetime
1997
- 1997-11-06 GR GR970401503T patent/GR3025293T3/el unknown
1998
- 1998-01-21 HK HK98100557A patent/HK1001729A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
ATE159948T1 (de)	1997-11-15
KR100253050B1 (ko)	2000-04-15
US5631238A (en)	1997-05-20
HU221808B1 (hu)	2003-01-28
HUT61773A (en)	1993-03-01
NO922674D0 (no)	1992-07-08
JPH05186494A (ja)	1993-07-27
NO178500B (no)	1996-01-02
JP2783722B2 (ja)	1998-08-06
AU1960092A (en)	1993-01-14
NO922674L (no)	1993-01-13
SG52704A1 (en)	1998-09-28
CA2073567A1 (en)	1993-01-13
DE69222992T2 (de)	1998-03-05
EP0525479B1 (en)	1997-11-05
ES2111019T3 (es)	1998-03-01
HU9202285D0 (en)	1992-10-28
FI923170A (fi)	1993-01-13
DE69222992D1 (de)	1997-12-11
KR930002370A (ko)	1993-02-23
US5461036A (en)	1995-10-24
AU657551B2 (en)	1995-03-16
HK1001729A1 (en)	1998-07-03
EP0525479A1 (en)	1993-02-03
CA2073567C (en)	1998-05-05
NO178500C (no)	1996-04-10
DK0525479T3 (da)	1998-04-20
GR3025293T3 (en)	1998-02-27
FI923170A0 (fi)	1992-07-09

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