UA71604C2

UA71604C2 - C-21 modified epothilones

C-21 modified epothilones Download PDF

Info

Publication number: UA71604C2
Authority: UA; Ukraine
Prior art keywords: group; thiazolyl; dihydroxy; methyl; dione
Prior art date: 1999-07-01

Application number

UA2001096489A

Other languages

English (en)

Ukrainian (uk)

Original Assignee

Biotechnologische Vorschung Mb

Bristol Mayers Squibb Co

Priority date

1999-07-01

Filing date

2000-02-17

Publication date

2004-12-15

2000-02-17 Application filed by Biotechnologische Vorschung Mb, Bristol Mayers Squibb Co filed Critical Biotechnologische Vorschung Mb

2000-02-17 Priority claimed from PCT/US2000/004068 external-priority patent/WO2000050423A1/en

2004-12-15 Publication of UA71604C2 publication Critical patent/UA71604C2/uk

Links

-1 C-21 modified epothilones Chemical class 0.000 title claims description 43
239000003814 drug Substances 0.000 claims abstract description 14
238000000034 method Methods 0.000 claims abstract description 13
229940124597 therapeutic agent Drugs 0.000 claims abstract description 8
150000001875 compounds Chemical class 0.000 claims description 131
125000000217 alkyl group Chemical group 0.000 claims description 127
125000000547 substituted alkyl group Chemical group 0.000 claims description 96
LZWPOLSJFGLQCE-UHFFFAOYSA-N heptadecane-5,9-dione Chemical compound CCCCCCCCC(=O)CCCC(=O)CCCC LZWPOLSJFGLQCE-UHFFFAOYSA-N 0.000 claims description 94
125000002252 acyl group Chemical group 0.000 claims description 71
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 59
125000003118 aryl group Chemical group 0.000 claims description 56
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 39
125000003107 substituted aryl group Chemical group 0.000 claims description 38
229910052799 carbon Inorganic materials 0.000 claims description 33
229910052739 hydrogen Inorganic materials 0.000 claims description 29
150000002118 epoxides Chemical class 0.000 claims description 24
229910052736 halogen Inorganic materials 0.000 claims description 24
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 24
125000000623 heterocyclic group Chemical group 0.000 claims description 23
150000002367 halogens Chemical class 0.000 claims description 21
230000015572 biosynthetic process Effects 0.000 claims description 20
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
201000010099 disease Diseases 0.000 claims description 18
206010028980 Neoplasm Diseases 0.000 claims description 17
150000003839 salts Chemical class 0.000 claims description 15
125000004429 atom Chemical group 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 13
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 11
201000011510 cancer Diseases 0.000 claims description 9
239000003085 diluting agent Substances 0.000 claims description 9
239000008194 pharmaceutical composition Substances 0.000 claims description 9
YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
230000000259 anti-tumor effect Effects 0.000 claims description 8
LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 claims description 7
239000002254 cytotoxic agent Substances 0.000 claims description 7
229940127089 cytotoxic agent Drugs 0.000 claims description 7
231100000599 cytotoxic agent Toxicity 0.000 claims description 7
125000003147 glycosyl group Chemical group 0.000 claims description 7
230000002062 proliferating effect Effects 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
239000002246 antineoplastic agent Substances 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
229910052757 nitrogen Inorganic materials 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
230000009467 reduction Effects 0.000 claims description 6
XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims description 4
230000004913 activation Effects 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
238000011161 development Methods 0.000 claims description 4
238000010534 nucleophilic substitution reaction Methods 0.000 claims description 4
239000012453 solvate Substances 0.000 claims description 4
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 claims description 3
230000006907 apoptotic process Effects 0.000 claims description 3
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 claims description 3
150000004677 hydrates Chemical class 0.000 claims description 3
125000001841 imino group Chemical group [H]N=* 0.000 claims description 3
150000002500 ions Chemical class 0.000 claims description 3
125000004430 oxygen atom Chemical group O* 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 claims description 2
210000004204 blood vessel Anatomy 0.000 claims description 2
239000003937 drug carrier Substances 0.000 claims description 2
239000011981 lindlar catalyst Substances 0.000 claims description 2
229910000073 phosphorus hydride Inorganic materials 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims 2
101100311260 Caenorhabditis elegans sti-1 gene Proteins 0.000 claims 1
239000004593 Epoxy Substances 0.000 claims 1
238000005984 hydrogenation reaction Methods 0.000 claims 1
230000001939 inductive effect Effects 0.000 claims 1
230000002401 inhibitory effect Effects 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
229930013356 epothilone Natural products 0.000 abstract description 29
HESCAJZNRMSMJG-KKQRBIROSA-N epothilone A Chemical class C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(C)=N1 HESCAJZNRMSMJG-KKQRBIROSA-N 0.000 abstract description 14
238000002360 preparation method Methods 0.000 abstract description 5
229940121375 antifungal agent Drugs 0.000 abstract description 3
230000000843 anti-fungal effect Effects 0.000 abstract description 2
239000003429 antifungal agent Substances 0.000 abstract description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 81
239000000203 mixture Substances 0.000 description 68
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
239000000243 solution Substances 0.000 description 54
238000006243 chemical reaction Methods 0.000 description 51
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 44
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 37
150000003883 epothilone derivatives Chemical class 0.000 description 32
239000002904 solvent Substances 0.000 description 30
241000282414 Homo sapiens Species 0.000 description 28
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
238000005481 NMR spectroscopy Methods 0.000 description 23
239000000741 silica gel Substances 0.000 description 19
229910002027 silica gel Inorganic materials 0.000 description 19
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 17
239000011541 reaction mixture Substances 0.000 description 16
239000011734 sodium Substances 0.000 description 16
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
238000004364 calculation method Methods 0.000 description 15
238000002474 experimental method Methods 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 14
239000007864 aqueous solution Substances 0.000 description 13
239000012300 argon atmosphere Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000012044 organic layer Substances 0.000 description 12
OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-Lutidine Substances CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 11
125000001424 substituent group Chemical group 0.000 description 11
238000003786 synthesis reaction Methods 0.000 description 11
UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 10
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 10
210000004027 cell Anatomy 0.000 description 10
238000004587 chromatography analysis Methods 0.000 description 10
239000012043 crude product Substances 0.000 description 10
FCCNKYGSMOSYPV-OKOHHBBGSA-N epothilone e Chemical compound C/C([C@@H]1C[C@@H]2O[C@@H]2CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CO)=N1 FCCNKYGSMOSYPV-OKOHHBBGSA-N 0.000 description 10
239000003921 oil Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
FCCNKYGSMOSYPV-DEDISHTHSA-N (-)-Epothilone E Natural products O=C1[C@H](C)[C@H](O)[C@@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(CO)sc2)/C)OC(=O)C[C@H](O)C1(C)C FCCNKYGSMOSYPV-DEDISHTHSA-N 0.000 description 9
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-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
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
239000002585 base Substances 0.000 description 9
239000003795 chemical substances by application Substances 0.000 description 9
FCCNKYGSMOSYPV-UHFFFAOYSA-N epothilone E Natural products O1C(=O)CC(O)C(C)(C)C(=O)C(C)C(O)C(C)CCCC2OC2CC1C(C)=CC1=CSC(CO)=N1 FCCNKYGSMOSYPV-UHFFFAOYSA-N 0.000 description 9
239000000725 suspension Substances 0.000 description 9
238000005160 1H NMR spectroscopy Methods 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
125000003710 aryl alkyl group Chemical group 0.000 description 8
239000013058 crude material Substances 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000001257 hydrogen Substances 0.000 description 8
NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 8
239000012074 organic phase Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000007787 solid Substances 0.000 description 8
239000007858 starting material Substances 0.000 description 8
239000000047 product Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
229940125782 compound 2 Drugs 0.000 description 6
229940125810 compound 20 Drugs 0.000 description 6
125000004122 cyclic group Chemical group 0.000 description 6
229940079593 drug Drugs 0.000 description 6
JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 6
239000003381 stabilizer Substances 0.000 description 6
PFJFPBDHCFMQPN-RGJAOAFDSA-N (1s,3s,7s,10r,11s,12s,16r)-3-[(e)-1-[2-(aminomethyl)-1,3-thiazol-4-yl]prop-1-en-2-yl]-7,11-dihydroxy-8,8,10,12,16-pentamethyl-4,17-dioxabicyclo[14.1.0]heptadecane-5,9-dione Chemical compound C/C([C@@H]1C[C@@H]2O[C@]2(C)CCC[C@@H]([C@@H]([C@@H](C)C(=O)C(C)(C)[C@@H](O)CC(=O)O1)O)C)=C\C1=CSC(CN)=N1 PFJFPBDHCFMQPN-RGJAOAFDSA-N 0.000 description 5
NWIBSHFKIJFRCO-WUDYKRTCSA-N Mytomycin Chemical compound C1N2C(C(C(C)=C(N)C3=O)=O)=C3[C@@H](COC(N)=O)[C@@]2(OC)[C@@H]2[C@H]1N2 NWIBSHFKIJFRCO-WUDYKRTCSA-N 0.000 description 5
229910052786 argon Inorganic materials 0.000 description 5
229940125773 compound 10 Drugs 0.000 description 5
125000005842 heteroatom Chemical group 0.000 description 5
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 5
239000003112 inhibitor Substances 0.000 description 5
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 5
239000010410 layer Substances 0.000 description 5
230000001590 oxidative effect Effects 0.000 description 5
229910052760 oxygen Inorganic materials 0.000 description 5
IWZSHWBGHQBIML-ZGGLMWTQSA-N (3S,8S,10R,13S,14S,17S)-17-isoquinolin-7-yl-N,N,10,13-tetramethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-amine Chemical compound CN(C)[C@H]1CC[C@]2(C)C3CC[C@@]4(C)[C@@H](CC[C@@H]4c4ccc5ccncc5c4)[C@@H]3CC=C2C1 IWZSHWBGHQBIML-ZGGLMWTQSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000004391 aryl sulfonyl group Chemical group 0.000 description 4
239000012298 atmosphere Substances 0.000 description 4
239000011230 binding agent Substances 0.000 description 4
XTEOJPUYZWEXFI-UHFFFAOYSA-N butyl n-[3-[4-(imidazol-1-ylmethyl)phenyl]-5-(2-methylpropyl)thiophen-2-yl]sulfonylcarbamate Chemical compound S1C(CC(C)C)=CC(C=2C=CC(CN3C=NC=C3)=CC=2)=C1S(=O)(=O)NC(=O)OCCCC XTEOJPUYZWEXFI-UHFFFAOYSA-N 0.000 description 4
150000001732 carboxylic acid derivatives Chemical class 0.000 description 4
239000003153 chemical reaction reagent Substances 0.000 description 4
238000010828 elution Methods 0.000 description 4
HESCAJZNRMSMJG-HGYUPSKWSA-N epothilone A Natural products O=C1[C@H](C)[C@H](O)[C@H](C)CCC[C@H]2O[C@H]2C[C@@H](/C(=C\c2nc(C)sc2)/C)OC(=O)C[C@H](O)C1(C)C HESCAJZNRMSMJG-HGYUPSKWSA-N 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
NNPPMTNAJDCUHE-UHFFFAOYSA-N isobutane Chemical compound CC(C)C NNPPMTNAJDCUHE-UHFFFAOYSA-N 0.000 description 4
208000032839 leukemia Diseases 0.000 description 4
239000002244 precipitate Substances 0.000 description 4
239000003755 preservative agent Substances 0.000 description 4
229940002612 prodrug Drugs 0.000 description 4
239000000651 prodrug Substances 0.000 description 4
125000004076 pyridyl group Chemical group 0.000 description 4
238000006722 reduction reaction Methods 0.000 description 4
239000003826 tablet Substances 0.000 description 4
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
XWKFPIODWVPXLX-UHFFFAOYSA-N 2-methyl-5-methylpyridine Natural products CC1=CC=C(C)N=C1 XWKFPIODWVPXLX-UHFFFAOYSA-N 0.000 description 3
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical class [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
241000282412 Homo Species 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
201000004681 Psoriasis Diseases 0.000 description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 3
239000013543 active substance Substances 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
150000001450 anions Chemical class 0.000 description 3
206010003246 arthritis Diseases 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000012230 colorless oil Substances 0.000 description 3
UAOMVDZJSHZZME-UHFFFAOYSA-N diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000945 filler Substances 0.000 description 3
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 3
230000009036 growth inhibition Effects 0.000 description 3
125000002883 imidazolyl group Chemical group 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229960004857 mitomycin Drugs 0.000 description 3
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Chemical group 0.000 description 3
238000007911 parenteral administration Methods 0.000 description 3
230000002035 prolonged effect Effects 0.000 description 3
125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 3
229910052717 sulfur Inorganic materials 0.000 description 3
238000004809 thin layer chromatography Methods 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 2
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