TW200827346A - Chemical compounds - Google Patents

Info

Publication number

TW200827346A

TW200827346A TW096140633A TW96140633A TW200827346A TW 200827346 A TW200827346 A TW 200827346A TW 096140633 A TW096140633 A TW 096140633A TW 96140633 A TW96140633 A TW 96140633A TW 200827346 A TW200827346 A TW 200827346A

Authority

TW

Taiwan

Prior art keywords

group

acetic acid

propylthio

pyridin

acid

Prior art date

2006-11-03

Links

• Espacenet
• Global Dossier
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• 150000001875 compounds Chemical class 0.000 title claims abstract description 166
• 238000000034 method Methods 0.000 claims abstract description 70
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 7
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Natural products CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 700
• 125000000217 alkyl group Chemical group 0.000 claims description 186
• -1 C!-3-alkoxy Chemical group 0.000 claims description 174
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 114
• 229910052757 nitrogen Inorganic materials 0.000 claims description 108
• PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Natural products NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 claims description 84
• 125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 82
• 125000001424 substituent group Chemical group 0.000 claims description 74
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 72
• 125000004093 cyano group Chemical group *C#N 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 70
• 239000001257 hydrogen Substances 0.000 claims description 69
• 125000003545 alkoxy group Chemical group 0.000 claims description 62
• 239000002253 acid Substances 0.000 claims description 58
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 55
• 229920006395 saturated elastomer Polymers 0.000 claims description 51
• 229910052760 oxygen Inorganic materials 0.000 claims description 49
• 239000001301 oxygen Substances 0.000 claims description 49
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 48
• 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 47
• 229910052717 sulfur Inorganic materials 0.000 claims description 47
• 239000011593 sulfur Substances 0.000 claims description 47
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 46
• 150000001412 amines Chemical class 0.000 claims description 46
• 125000005843 halogen group Chemical group 0.000 claims description 44
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 43
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 43
• 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 41
• 125000005842 heteroatom Chemical group 0.000 claims description 40
• 125000000623 heterocyclic group Chemical group 0.000 claims description 40
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 40
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
• VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 claims description 34
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 34
• XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 33
• BDAGIHXWWSANSR-UHFFFAOYSA-N formic acid Substances OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 32
• 150000003839 salts Chemical class 0.000 claims description 32
• 125000004122 cyclic group Chemical group 0.000 claims description 29
• 125000004575 3-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 27
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 27
• 125000001072 heteroaryl group Chemical group 0.000 claims description 26
• OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine group Chemical group NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 25
• 229910052799 carbon Inorganic materials 0.000 claims description 22
• 150000002148 esters Chemical class 0.000 claims description 22
• 238000011282 treatment Methods 0.000 claims description 22
• QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 21
• 125000003396 thiol group Chemical class [H]S* 0.000 claims description 21
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 20
• BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 20
• 239000000460 chlorine Substances 0.000 claims description 20
• 125000002950 monocyclic group Chemical group 0.000 claims description 19
• 208000001145 Metabolic Syndrome Diseases 0.000 claims description 18
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 18
• 201000000690 abdominal obesity-metabolic syndrome Diseases 0.000 claims description 18
• 235000019260 propionic acid Nutrition 0.000 claims description 18
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 16
• 125000003118 aryl group Chemical group 0.000 claims description 16
• 125000003386 piperidinyl group Chemical group 0.000 claims description 16
• 125000005073 adamantyl group Chemical group C12(CC3CC(CC(C1)C3)C2)* 0.000 claims description 15
• 125000003342 alkenyl group Chemical group 0.000 claims description 15
• 125000000304 alkynyl group Chemical group 0.000 claims description 15
• 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 claims description 15
• 230000002401 inhibitory effect Effects 0.000 claims description 14
• 239000003795 chemical substances by application Substances 0.000 claims description 13
• 125000006239 protecting group Chemical group 0.000 claims description 13
• 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
• 125000002619 bicyclic group Chemical group 0.000 claims description 12
• 235000019253 formic acid Nutrition 0.000 claims description 12
• 238000001727 in vivo Methods 0.000 claims description 12
• 125000004483 piperidin-3-yl group Chemical group N1CC(CCC1)* 0.000 claims description 12
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
• 125000003003 spiro group Chemical group 0.000 claims description 11
• 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 10
• 239000003814 drug Substances 0.000 claims description 10
• 125000005592 polycycloalkyl group Chemical group 0.000 claims description 10
• 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 10
• JAEIBKXSIXOLOL-UHFFFAOYSA-N pyrrolidin-1-ium-3-carboxylate Chemical compound OC(=O)C1CCNC1 JAEIBKXSIXOLOL-UHFFFAOYSA-N 0.000 claims description 10
• 239000000126 substance Substances 0.000 claims description 10
• 241001465754 Metazoa Species 0.000 claims description 9
• SIKJAQJRHWYJAI-UHFFFAOYSA-N benzopyrrole Natural products C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 9
• 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 claims description 9
• 125000006413 ring segment Chemical group 0.000 claims description 9
• 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 8
• 125000004076 pyridyl group Chemical group 0.000 claims description 8
• ORILYTVJVMAKLC-UHFFFAOYSA-N adamantane Chemical compound C1C(C2)CC3CC1CC2C3 ORILYTVJVMAKLC-UHFFFAOYSA-N 0.000 claims description 7
• 125000003277 amino group Chemical group 0.000 claims description 7
• 125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 7
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
• 229960005286 carbaryl Drugs 0.000 claims description 7
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 7
• 241000282412 Homo Species 0.000 claims description 6
• 208000008589 Obesity Diseases 0.000 claims description 6
• 125000003282 alkyl amino group Chemical group 0.000 claims description 6
• UIJGNTRUPZPVNG-UHFFFAOYSA-N benzenecarbothioic s-acid Chemical compound SC(=O)C1=CC=CC=C1 UIJGNTRUPZPVNG-UHFFFAOYSA-N 0.000 claims description 6
• CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 claims description 6
• 125000004432 carbon atom Chemical group C* 0.000 claims description 6
• NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 claims description 6
• 206010012601 diabetes mellitus Diseases 0.000 claims description 6
• 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 6
• 238000004519 manufacturing process Methods 0.000 claims description 6
• 235000020824 obesity Nutrition 0.000 claims description 6
• 150000003254 radicals Chemical class 0.000 claims description 6
• 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 description 6
• BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 claims description 5
• OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
• KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 5
• DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 claims description 5
• 229910052736 halogen Inorganic materials 0.000 claims description 5
• 150000002367 halogens Chemical class 0.000 claims description 5
• PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 5
• RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 5
• 229910052747 lanthanoid Inorganic materials 0.000 claims description 5
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
• 229910052707 ruthenium Inorganic materials 0.000 claims description 5
• 239000002689 soil Substances 0.000 claims description 5
• RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 5
• 125000001544 thienyl group Chemical group 0.000 claims description 5
• FYCRNRZIEVLZDO-BYPYZUCNSA-N (2s)-morpholin-4-ium-2-carboxylate Chemical compound OC(=O)[C@@H]1CNCCO1 FYCRNRZIEVLZDO-BYPYZUCNSA-N 0.000 claims description 4
• GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
• 239000003085 diluting agent Substances 0.000 claims description 4
• WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 claims description 4
• 150000002602 lanthanoids Chemical class 0.000 claims description 4
• 125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 4
• PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical compound [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 claims description 4
• 150000003573 thiols Chemical class 0.000 claims description 4
• 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
• JIMXXGFJRDUSRO-UHFFFAOYSA-N adamantane-1-carboxylic acid Chemical compound C1C(C2)CC3CC2CC1(C(=O)O)C3 JIMXXGFJRDUSRO-UHFFFAOYSA-N 0.000 claims description 3
• 125000004981 cycloalkylmethyl group Chemical group 0.000 claims description 3
• HJSLFCCWAKVHIW-UHFFFAOYSA-N cyclohexane-1,3-dione Chemical compound O=C1CCCC(=O)C1 HJSLFCCWAKVHIW-UHFFFAOYSA-N 0.000 claims description 3
• 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 3
• 230000001225 therapeutic effect Effects 0.000 claims description 3
• 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
• NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
• YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Natural products C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 claims description 2
• 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 2
• 201000001320 Atherosclerosis Diseases 0.000 claims description 2
• 239000005632 Capric acid (CAS 334-48-5) Substances 0.000 claims description 2
• ZUSWDTWYONAOPH-UHFFFAOYSA-N [2-(trifluoromethyl)phenyl]hydrazine;hydrochloride Chemical group [Cl-].[NH3+]NC1=CC=CC=C1C(F)(F)F ZUSWDTWYONAOPH-UHFFFAOYSA-N 0.000 claims description 2
• QZWNXXINFABALM-UHFFFAOYSA-N adamantan-2-amine Chemical compound C1C(C2)CC3CC1C(N)C2C3 QZWNXXINFABALM-UHFFFAOYSA-N 0.000 claims description 2
• WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 2
• 125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 claims description 2
• HXEACLLIILLPRG-RXMQYKEDSA-N l-pipecolic acid Natural products OC(=O)[C@H]1CCCCN1 HXEACLLIILLPRG-RXMQYKEDSA-N 0.000 claims description 2
• 150000002923 oximes Chemical class 0.000 claims description 2
• HXEACLLIILLPRG-UHFFFAOYSA-N pipecolic acid Chemical compound OC(=O)C1CCCCN1 HXEACLLIILLPRG-UHFFFAOYSA-N 0.000 claims description 2
• 230000000069 prophylactic effect Effects 0.000 claims description 2
• 229910052703 rhodium Inorganic materials 0.000 claims description 2
• 239000010948 rhodium Substances 0.000 claims description 2
• MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 2
• 150000002431 hydrogen Chemical class 0.000 claims 5
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
• KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 claims 3
• VRDBIJCCXDEZJN-UHFFFAOYSA-N 2-piperidin-1-ylacetic acid Chemical compound OC(=O)CN1CCCCC1 VRDBIJCCXDEZJN-UHFFFAOYSA-N 0.000 claims 1
• QWFCVBMSMZUVFU-UHFFFAOYSA-N 3-azoniabicyclo[3.1.0]hexane-6-carboxylate Chemical compound C1NCC2C(C(=O)O)C21 QWFCVBMSMZUVFU-UHFFFAOYSA-N 0.000 claims 1
• WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 claims 1
• KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical compound NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 claims 1
• NMEZJSDUZQOPFE-UHFFFAOYSA-N Cyclohex-1-enecarboxylic acid Chemical compound OC(=O)C1=CCCCC1 NMEZJSDUZQOPFE-UHFFFAOYSA-N 0.000 claims 1
• MVVAPWHFZKPBCW-UHFFFAOYSA-N N=NC=NN.C1(CCCCC1)N Chemical compound N=NC=NN.C1(CCCCC1)N MVVAPWHFZKPBCW-UHFFFAOYSA-N 0.000 claims 1
• 241000124033 Salix Species 0.000 claims 1
• 150000001336 alkenes Chemical class 0.000 claims 1
• GONOPSZTUGRENK-UHFFFAOYSA-N benzyl(trichloro)silane Chemical compound Cl[Si](Cl)(Cl)CC1=CC=CC=C1 GONOPSZTUGRENK-UHFFFAOYSA-N 0.000 claims 1
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cis-cyclohexene Natural products C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims 1
• FHEPZBIUHGLJMP-UHFFFAOYSA-N cyclohexene Chemical compound [CH]1CCCC=C1 FHEPZBIUHGLJMP-UHFFFAOYSA-N 0.000 claims 1
• 125000004705 ethylthio group Chemical group C(C)S* 0.000 claims 1
• 125000001153 fluoro group Chemical group F* 0.000 claims 1
• 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims 1
• FUZZWVXGSFPDMH-UHFFFAOYSA-N n-hexanoic acid Natural products CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims 1
• 125000000719 pyrrolidinyl group Chemical group 0.000 claims 1
• 125000000446 sulfanediyl group Chemical group *S* 0.000 claims 1
• NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 claims 1
• 230000005764 inhibitory process Effects 0.000 abstract description 9
• 230000008569 process Effects 0.000 abstract description 5
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 388
• IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 350
• 239000000543 intermediate Substances 0.000 description 229
• 235000019439 ethyl acetate Nutrition 0.000 description 194
• 238000004128 high performance liquid chromatography Methods 0.000 description 165
• 238000005481 NMR spectroscopy Methods 0.000 description 146
• 238000005160 1H NMR spectroscopy Methods 0.000 description 127
• 238000004949 mass spectrometry Methods 0.000 description 95
• 239000000243 solution Substances 0.000 description 89
• 239000002585 base Substances 0.000 description 65
• 239000007858 starting material Substances 0.000 description 56
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 54
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 53
• 101150041968 CDC13 gene Proteins 0.000 description 52
• HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 52
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 49
• 239000000203 mixture Substances 0.000 description 45
• QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 42
• WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 41
• 239000000725 suspension Substances 0.000 description 41
• 238000006243 chemical reaction Methods 0.000 description 40
• 239000011541 reaction mixture Substances 0.000 description 40
• 239000007787 solid Substances 0.000 description 37
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
• 239000012044 organic layer Substances 0.000 description 31
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 30
• 239000012043 crude product Substances 0.000 description 29
• OJCSPXHYDFONPU-UHFFFAOYSA-N etoac etoac Chemical compound CCOC(C)=O.CCOC(C)=O OJCSPXHYDFONPU-UHFFFAOYSA-N 0.000 description 24
• 238000003818 flash chromatography Methods 0.000 description 24
• BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 24
• 239000007789 gas Substances 0.000 description 23
• 238000002360 preparation method Methods 0.000 description 23
• JYGXADMDTFJGBT-VWUMJDOOSA-N hydrocortisone Chemical compound O=C1CC[C@]2(C)[C@H]3[C@@H](O)C[C@](C)([C@@](CC4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 JYGXADMDTFJGBT-VWUMJDOOSA-N 0.000 description 22
• IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
• 239000002904 solvent Substances 0.000 description 21
• 230000000694 effects Effects 0.000 description 20
• 239000000523 sample Substances 0.000 description 17
• 125000003670 adamantan-2-yl group Chemical group [H]C1([H])C(C2([H])[H])([H])C([H])([H])C3([H])C([*])([H])C1([H])C([H])([H])C2([H])C3([H])[H] 0.000 description 15
• 150000001721 carbon Chemical group 0.000 description 15
• 238000001704 evaporation Methods 0.000 description 15
• 230000008020 evaporation Effects 0.000 description 15
• 239000003112 inhibitor Substances 0.000 description 15
• 239000000047 product Substances 0.000 description 15
• CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
• 239000003921 oil Substances 0.000 description 14
• 235000019198 oils Nutrition 0.000 description 14
• 229910000027 potassium carbonate Inorganic materials 0.000 description 14
• DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 description 13
• 230000002829 reductive effect Effects 0.000 description 13
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