TW201204362A

TW201204362A - New chemical compounds

New chemical compounds Download PDF

Info

Publication number: TW201204362A
Authority: TW; Taiwan
Prior art keywords: group; alkyl; tret; lcmsbas1; doc
Prior art date: 2010-04-21

Application number

TW100113756A

Other languages

English (en)

Chinese (zh)

Inventor

Harald Engelhardt

Christiane Kofink

Darryl Mcconnell

Original Assignee

Boehringer Ingelheim Int

Priority date

2010-04-21

Filing date

2011-04-20

Publication date

2012-02-01

2011-04-20 Application filed by Boehringer Ingelheim Int filed Critical Boehringer Ingelheim Int

2012-02-01 Publication of TW201204362A publication Critical patent/TW201204362A/zh

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 147
238000011282 treatment Methods 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 6
239000000825 pharmaceutical preparation Substances 0.000 claims abstract description 6
-1 homomorpholinyl Chemical group 0.000 claims description 181
125000000217 alkyl group Chemical group 0.000 claims description 168
239000001257 hydrogen Substances 0.000 claims description 88
229910052739 hydrogen Inorganic materials 0.000 claims description 88
125000000623 heterocyclic group Chemical group 0.000 claims description 64
125000004122 cyclic group Chemical group 0.000 claims description 63
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
125000000753 cycloalkyl group Chemical group 0.000 claims description 61
239000000203 mixture Substances 0.000 claims description 56
125000001072 heteroaryl group Chemical group 0.000 claims description 52
125000003118 aryl group Chemical group 0.000 claims description 50
125000003342 alkenyl group Chemical group 0.000 claims description 39
125000001424 substituent group Chemical group 0.000 claims description 36
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 35
206010028980 Neoplasm Diseases 0.000 claims description 34
125000000304 alkynyl group Chemical group 0.000 claims description 34
150000003839 salts Chemical class 0.000 claims description 33
239000000460 chlorine Chemical group 0.000 claims description 29
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 25
229910052736 halogen Inorganic materials 0.000 claims description 22
150000002367 halogens Chemical class 0.000 claims description 22
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
239000013543 active substance Substances 0.000 claims description 19
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 19
239000002689 soil Substances 0.000 claims description 18
150000002431 hydrogen Chemical class 0.000 claims description 16
125000003386 piperidinyl group Chemical group 0.000 claims description 15
125000002947 alkylene group Chemical group 0.000 claims description 14
201000011510 cancer Diseases 0.000 claims description 13
125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 13
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 13
125000004193 piperazinyl group Chemical group 0.000 claims description 13
150000001412 amines Chemical class 0.000 claims description 12
125000002757 morpholinyl group Chemical group 0.000 claims description 12
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
239000000126 substance Substances 0.000 claims description 12
229910052799 carbon Inorganic materials 0.000 claims description 11
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 11
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 10
125000001188 haloalkyl group Chemical group 0.000 claims description 9
125000005842 heteroatom Chemical group 0.000 claims description 9
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical group [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 8
229910052801 chlorine Inorganic materials 0.000 claims description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 8
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 claims description 7
MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 7
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 claims description 7
230000002265 prevention Effects 0.000 claims description 7
RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 7
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 6
125000002393 azetidinyl group Chemical group 0.000 claims description 6
239000000546 pharmaceutical excipient Substances 0.000 claims description 6
238000007363 ring formation reaction Methods 0.000 claims description 6
125000003396 thiol group Chemical group [H]S* 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 5
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
125000006574 non-aromatic ring group Chemical group 0.000 claims description 5
229910052786 argon Inorganic materials 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 3
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 3
208000023275 Autoimmune disease Diseases 0.000 claims description 3
206010061218 Inflammation Diseases 0.000 claims description 3
150000001335 aliphatic alkanes Chemical class 0.000 claims description 3
150000001345 alkine derivatives Chemical class 0.000 claims description 3
239000000824 cytostatic agent Substances 0.000 claims description 3
230000001085 cytostatic effect Effects 0.000 claims description 3
230000001472 cytotoxic effect Effects 0.000 claims description 3
RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 claims description 3
PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 3
RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 3
208000015181 infectious disease Diseases 0.000 claims description 3
230000004054 inflammatory process Effects 0.000 claims description 3
NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 3
125000003566 oxetanyl group Chemical group 0.000 claims description 3
125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims description 3
125000000041 C6-C10 aryl group Chemical group 0.000 claims description 2
231100000433 cytotoxic Toxicity 0.000 claims description 2
238000004519 manufacturing process Methods 0.000 claims description 2
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
150000003254 radicals Chemical class 0.000 claims description 2
229910052701 rubidium Inorganic materials 0.000 claims description 2
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 2
125000004550 quinolin-6-yl group Chemical group N1=CC=CC2=CC(=CC=C12)* 0.000 claims 8
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims 7
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 claims 5
235000005152 nicotinamide Nutrition 0.000 claims 4
239000011570 nicotinamide Substances 0.000 claims 4
125000006612 decyloxy group Chemical group 0.000 claims 3
125000001041 indolyl group Chemical group 0.000 claims 3
125000004361 3,4,5-trifluorophenyl group Chemical group [H]C1=C(F)C(F)=C(F)C([H])=C1* 0.000 claims 2
241000156724 Antirhea Species 0.000 claims 2
125000004212 difluorophenyl group Chemical group 0.000 claims 2
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims 1
KGQJMEJSCKDBQR-UHFFFAOYSA-N 2h-oxazine-4-carboxamide Chemical compound NC(=O)C1=CNOC=C1 KGQJMEJSCKDBQR-UHFFFAOYSA-N 0.000 claims 1
125000001397 3-pyrrolyl group Chemical group [H]N1C([H])=C([*])C([H])=C1[H] 0.000 claims 1
JLAKCHGEEBPDQI-UHFFFAOYSA-N 4-(4-fluorobenzyl)piperidine Chemical compound C1=CC(F)=CC=C1CC1CCNCC1 JLAKCHGEEBPDQI-UHFFFAOYSA-N 0.000 claims 1
241001091551 Clio Species 0.000 claims 1
SSUSPADGCMXUMM-UHFFFAOYSA-N N1=CN=CC(=C1)CCCCCCCCCCN Chemical compound N1=CN=CC(=C1)CCCCCCCCCCN SSUSPADGCMXUMM-UHFFFAOYSA-N 0.000 claims 1
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims 1
DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims 1
125000005418 aryl aryl group Chemical group 0.000 claims 1
239000004305 biphenyl Substances 0.000 claims 1
229910052797 bismuth Inorganic materials 0.000 claims 1
JCXGWMGPZLAOME-UHFFFAOYSA-N bismuth atom Chemical compound [Bi] JCXGWMGPZLAOME-UHFFFAOYSA-N 0.000 claims 1
239000004202 carbamide Substances 0.000 claims 1
125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
239000003550 marker Substances 0.000 claims 1
YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims 1
229960003540 oxyquinoline Drugs 0.000 claims 1
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims 1
125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims 1
QDXGKRWDQCEABB-UHFFFAOYSA-N pyrimidine-5-carboxamide Chemical compound NC(=O)C1=CN=CN=C1 QDXGKRWDQCEABB-UHFFFAOYSA-N 0.000 claims 1
125000004547 quinazolin-6-yl group Chemical group N1=CN=CC2=CC(=CC=C12)* 0.000 claims 1
MCJGNVYPOGVAJF-UHFFFAOYSA-N quinolin-8-ol Chemical compound C1=CN=C2C(O)=CC=CC2=C1 MCJGNVYPOGVAJF-UHFFFAOYSA-N 0.000 claims 1
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims 1
BOLDJAUMGUJJKM-LSDHHAIUSA-N renifolin D Natural products CC(=C)[C@@H]1Cc2c(O)c(O)ccc2[C@H]1CC(=O)c3ccc(O)cc3O BOLDJAUMGUJJKM-LSDHHAIUSA-N 0.000 claims 1
102200046712 rs752492870 Human genes 0.000 claims 1
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims 1
241000894007 species Species 0.000 claims 1
125000004360 trifluorophenyl group Chemical group 0.000 claims 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 10
201000010099 disease Diseases 0.000 abstract description 9
230000004663 cell proliferation Effects 0.000 abstract description 7
230000002159 abnormal effect Effects 0.000 abstract description 4
238000004128 high performance liquid chromatography Methods 0.000 description 232
238000000034 method Methods 0.000 description 198
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 191
235000019439 ethyl acetate Nutrition 0.000 description 95
SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 90
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 63
229910001868 water Inorganic materials 0.000 description 62
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 57
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 50
239000011541 reaction mixture Substances 0.000 description 46
239000002904 solvent Substances 0.000 description 44
230000002194 synthesizing effect Effects 0.000 description 43
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 41
238000006243 chemical reaction Methods 0.000 description 40
125000004432 carbon atom Chemical group C* 0.000 description 38
210000004027 cell Anatomy 0.000 description 31
239000002585 base Substances 0.000 description 29
238000004587 chromatography analysis Methods 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 26
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 25
XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 description 25
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
239000002253 acid Substances 0.000 description 24
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
238000000589 high-performance liquid chromatography-mass spectrometry Methods 0.000 description 21
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 19
239000012074 organic phase Substances 0.000 description 19
239000003480 eluent Substances 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 17
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 16
101001117146 Homo sapiens [Pyruvate dehydrogenase (acetyl-transferring)] kinase isozyme 1, mitochondrial Proteins 0.000 description 16
239000000243 solution Substances 0.000 description 16
102100037263 3-phosphoinositide-dependent protein kinase 1 Human genes 0.000 description 15
101000600756 Homo sapiens 3-phosphoinositide-dependent protein kinase 1 Proteins 0.000 description 15
238000001514 detection method Methods 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 14
239000002244 precipitate Substances 0.000 description 14
229920006395 saturated elastomer Polymers 0.000 description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
239000003643 water by type Substances 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 12
238000003786 synthesis reaction Methods 0.000 description 12
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 11
125000001183 hydrocarbyl group Chemical group 0.000 description 11
238000006467 substitution reaction Methods 0.000 description 11
KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 10
BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical compound OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 10
235000019253 formic acid Nutrition 0.000 description 10
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 10
238000003756 stirring Methods 0.000 description 10
108091008611 Protein Kinase B Proteins 0.000 description 9
102100033810 RAC-alpha serine/threonine-protein kinase Human genes 0.000 description 9
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 9
239000007789 gas Substances 0.000 description 9
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 9
230000035755 proliferation Effects 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 8
RWZYAGGXGHYGMB-UHFFFAOYSA-N anthranilic acid Chemical compound NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 description 8
150000001733 carboxylic acid esters Chemical class 0.000 description 8
230000005764 inhibitory process Effects 0.000 description 8
RHQTYPIWELTMCE-UHFFFAOYSA-N n-prop-2-ynyldecan-1-amine Chemical compound CCCCCCCCCCNCC#C RHQTYPIWELTMCE-UHFFFAOYSA-N 0.000 description 8
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
239000012996 alamarblue reagent Substances 0.000 description 7
235000012538 ammonium bicarbonate Nutrition 0.000 description 7
125000004429 atom Chemical group 0.000 description 7
150000001732 carboxylic acid derivatives Chemical class 0.000 description 7
125000000392 cycloalkenyl group Chemical group 0.000 description 7
239000008101 lactose Substances 0.000 description 7
239000007937 lozenge Substances 0.000 description 7
238000004949 mass spectrometry Methods 0.000 description 7
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 7
229910000069 nitrogen hydride Inorganic materials 0.000 description 7
238000007127 saponification reaction Methods 0.000 description 7
239000007858 starting material Substances 0.000 description 7
KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
206010003571 Astrocytoma Diseases 0.000 description 6
229920002261 Corn starch Polymers 0.000 description 6
239000007821 HATU Substances 0.000 description 6
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208000009956 adenocarcinoma Diseases 0.000 description 6
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 6
239000008120 corn starch Substances 0.000 description 6
229940099112 cornstarch Drugs 0.000 description 6
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 6
239000000047 product Substances 0.000 description 6
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 6
125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 6
229910000104 sodium hydride Inorganic materials 0.000 description 6
238000012360 testing method Methods 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 5
206010006417 Bronchial carcinoma Diseases 0.000 description 5
QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 5
102000004190 Enzymes Human genes 0.000 description 5
108090000790 Enzymes Proteins 0.000 description 5
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
206010025323 Lymphomas Diseases 0.000 description 5
206010039491 Sarcoma Diseases 0.000 description 5
239000012317 TBTU Substances 0.000 description 5
CLZISMQKJZCZDN-UHFFFAOYSA-N [benzotriazol-1-yloxy(dimethylamino)methylidene]-dimethylazanium Chemical compound C1=CC=C2N(OC(N(C)C)=[N+](C)C)N=NC2=C1 CLZISMQKJZCZDN-UHFFFAOYSA-N 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
125000002619 bicyclic group Chemical group 0.000 description 5
208000003362 bronchogenic carcinoma Diseases 0.000 description 5
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 description 5
238000005859 coupling reaction Methods 0.000 description 5
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 5
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 5
125000006575 electron-withdrawing group Chemical group 0.000 description 5
OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 5
FABUFPQFXZVHFB-PVYNADRNSA-N ixabepilone 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)N1)O)C)=C\C1=CSC(C)=N1 FABUFPQFXZVHFB-PVYNADRNSA-N 0.000 description 5
235000019359 magnesium stearate Nutrition 0.000 description 5
238000001819 mass spectrum Methods 0.000 description 5
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