BG65134B1 - Производни и аналози на галантамин - Google Patents

Info

Publication number

BG65134B1

BG65134B1 BG106155A BG10615501A BG65134B1 BG 65134 B1 BG65134 B1 BG 65134B1 BG 106155 A BG106155 A BG 106155A BG 10615501 A BG10615501 A BG 10615501A BG 65134 B1 BG65134 B1 BG 65134B1

Authority

BG

Bulgaria

Prior art keywords

group

alkyl

nmr

mmol

sph

Prior art date

2000-03-31

Links

• Espacenet
• Global Dossier
• Discuss

• ASUTZQLVASHGKV-UHFFFAOYSA-N galanthamine hydrochloride Natural products O1C(=C23)C(OC)=CC=C2CN(C)CCC23C1CC(O)C=C2 ASUTZQLVASHGKV-UHFFFAOYSA-N 0.000 title description 22
• 150000001875 compounds Chemical class 0.000 claims abstract description 96
• 239000000203 mixture Substances 0.000 claims abstract description 83
• 238000002360 preparation method Methods 0.000 claims abstract description 34
• 239000013543 active substance Substances 0.000 claims abstract description 14
• 239000003814 drug Substances 0.000 claims abstract description 10
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 557
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 291
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 262
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 237
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 156
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 142
• -1 aralkoxy Chemical group 0.000 claims description 125
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 116
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 114
• 239000002904 solvent Substances 0.000 claims description 107
• 229910052757 nitrogen Inorganic materials 0.000 claims description 93
• 238000000034 method Methods 0.000 claims description 92
• 239000000460 chlorine Substances 0.000 claims description 75
• AIXQQSTVOSFSMO-RBOXIYTFSA-N Norgalanthamine Chemical compound O1C(=C23)C(OC)=CC=C2CNCC[C@]23[C@@H]1C[C@@H](O)C=C2 AIXQQSTVOSFSMO-RBOXIYTFSA-N 0.000 claims description 74
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 72
• 239000013078 crystal Substances 0.000 claims description 71
• 229910052739 hydrogen Inorganic materials 0.000 claims description 71
• CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 48
• 125000001424 substituent group Chemical group 0.000 claims description 46
• 239000000725 suspension Substances 0.000 claims description 45
• 229910052799 carbon Inorganic materials 0.000 claims description 40
• 229910052760 oxygen Inorganic materials 0.000 claims description 37
• IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 35
• 239000001257 hydrogen Substances 0.000 claims description 34
• 239000003208 petroleum Substances 0.000 claims description 31
• 239000002253 acid Substances 0.000 claims description 29
• YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 28
• 229910052717 sulfur Inorganic materials 0.000 claims description 26
• RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 24
• 125000000217 alkyl group Chemical group 0.000 claims description 22
• 238000004821 distillation Methods 0.000 claims description 22
• 150000002431 hydrogen Chemical class 0.000 claims description 22
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 21
• OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 20
• 125000000623 heterocyclic group Chemical group 0.000 claims description 17
• 229910052801 chlorine Inorganic materials 0.000 claims description 16
• 125000004122 cyclic group Chemical group 0.000 claims description 14
• 229910052731 fluorine Inorganic materials 0.000 claims description 14
• 206010021143 Hypoxia Diseases 0.000 claims description 13
• 230000007850 degeneration Effects 0.000 claims description 13
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 13
• 150000003839 salts Chemical class 0.000 claims description 13
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
• UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 125000003710 aryl alkyl group Chemical group 0.000 claims description 12
• 230000015572 biosynthetic process Effects 0.000 claims description 12
• 201000010099 disease Diseases 0.000 claims description 12
• 125000005842 heteroatom Chemical group 0.000 claims description 12
• 125000000547 substituted alkyl group Chemical group 0.000 claims description 12
• 238000003786 synthesis reaction Methods 0.000 claims description 12
• 125000003118 aryl group Chemical group 0.000 claims description 11
• 229910052794 bromium Inorganic materials 0.000 claims description 11
• 239000007790 solid phase Substances 0.000 claims description 11
• RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 claims description 10
• AIXQQSTVOSFSMO-UHFFFAOYSA-N N-norgalanthamine Natural products O1C(=C23)C(OC)=CC=C2CNCCC23C1CC(O)C=C2 AIXQQSTVOSFSMO-UHFFFAOYSA-N 0.000 claims description 9
• NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 9
• FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 9
• 230000001640 apoptogenic effect Effects 0.000 claims description 9
• QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
• 230000000694 effects Effects 0.000 claims description 9
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 9
• 239000001301 oxygen Substances 0.000 claims description 9
• 229920006395 saturated elastomer Polymers 0.000 claims description 9
• 239000011593 sulfur Substances 0.000 claims description 9
• FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims description 8
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 8
• 150000001408 amides Chemical class 0.000 claims description 8
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 230000002265 prevention Effects 0.000 claims description 8
• 208000024827 Alzheimer disease Diseases 0.000 claims description 7
• 210000004027 cell Anatomy 0.000 claims description 7
• 239000003960 organic solvent Substances 0.000 claims description 7
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 6
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 6
• YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 6
• 125000003545 alkoxy group Chemical group 0.000 claims description 6
• 150000001413 amino acids Chemical group 0.000 claims description 6
• 210000004556 brain Anatomy 0.000 claims description 6
• 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
• 239000011737 fluorine Substances 0.000 claims description 6
• DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 claims description 6
• 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
• 208000023105 Huntington disease Diseases 0.000 claims description 5
• BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 claims description 5
• 208000006011 Stroke Diseases 0.000 claims description 5
• 208000030886 Traumatic Brain injury Diseases 0.000 claims description 5
• 125000003277 amino group Chemical group 0.000 claims description 5
• 206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 5
• 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
• 206010012601 diabetes mellitus Diseases 0.000 claims description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
• 230000007954 hypoxia Effects 0.000 claims description 5
• NOESYZHRGYRDHS-UHFFFAOYSA-N insulin Substances N1C(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(NC(=O)CN)C(C)CC)CSSCC(C(NC(CO)C(=O)NC(CC(C)C)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CCC(N)=O)C(=O)NC(CC(C)C)C(=O)NC(CCC(O)=O)C(=O)NC(CC(N)=O)C(=O)NC(CC=2C=CC(O)=CC=2)C(=O)NC(CSSCC(NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2C=CC(O)=CC=2)NC(=O)C(CC(C)C)NC(=O)C(C)NC(=O)C(CCC(O)=O)NC(=O)C(C(C)C)NC(=O)C(CC(C)C)NC(=O)C(CC=2NC=NC=2)NC(=O)C(CO)NC(=O)CNC2=O)C(=O)NCC(=O)NC(CCC(O)=O)C(=O)NC(CCCNC(N)=N)C(=O)NCC(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC=CC=3)C(=O)NC(CC=3C=CC(O)=CC=3)C(=O)NC(C(C)O)C(=O)N3C(CCC3)C(=O)NC(CCCCN)C(=O)NC(C)C(O)=O)C(=O)NC(CC(N)=O)C(O)=O)=O)NC(=O)C(C(C)CC)NC(=O)C(CO)NC(=O)C(C(C)O)NC(=O)C1CSSCC2NC(=O)C(CC(C)C)NC(=O)C(NC(=O)C(CCC(N)=O)NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(N)CC=1C=CC=CC=1)C(C)C)CC1=CN=CN1 NOESYZHRGYRDHS-UHFFFAOYSA-N 0.000 claims description 5
• 201000006417 multiple sclerosis Diseases 0.000 claims description 5
• 230000009529 traumatic brain injury Effects 0.000 claims description 5
• 206010002091 Anaesthesia Diseases 0.000 claims description 4
• 206010002660 Anoxia Diseases 0.000 claims description 4
• 241000976983 Anoxia Species 0.000 claims description 4
• 206010003497 Asphyxia Diseases 0.000 claims description 4
• 208000003174 Brain Neoplasms Diseases 0.000 claims description 4
• ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
• 206010008748 Chorea Diseases 0.000 claims description 4
• PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
• 208000010496 Heart Arrest Diseases 0.000 claims description 4
• 102000004877 Insulin Human genes 0.000 claims description 4
• 108090001061 Insulin Proteins 0.000 claims description 4
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
• 206010027202 Meningitis bacterial Diseases 0.000 claims description 4
• KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims description 4
• 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 4
• 230000037005 anaesthesia Effects 0.000 claims description 4
• 230000007953 anoxia Effects 0.000 claims description 4
• 201000009904 bacterial meningitis Diseases 0.000 claims description 4
• 125000004432 carbon atom Chemical group C* 0.000 claims description 4
• 230000001413 cellular effect Effects 0.000 claims description 4
• 238000002512 chemotherapy Methods 0.000 claims description 4
• 208000012601 choreatic disease Diseases 0.000 claims description 4
• MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 claims description 4
• HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 4
• LPIQUOYDBNQMRZ-UHFFFAOYSA-N cyclopentene Chemical compound C1CC=CC1 LPIQUOYDBNQMRZ-UHFFFAOYSA-N 0.000 claims description 4
• 206010015037 epilepsy Diseases 0.000 claims description 4
• 125000000524 functional group Chemical group 0.000 claims description 4
• 229910052736 halogen Inorganic materials 0.000 claims description 4
• 150000002367 halogens Chemical class 0.000 claims description 4
• 229940125396 insulin Drugs 0.000 claims description 4
• 210000003205 muscle Anatomy 0.000 claims description 4
• SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 claims description 4
• 210000002569 neuron Anatomy 0.000 claims description 4
• 235000015097 nutrients Nutrition 0.000 claims description 4
• 231100000572 poisoning Toxicity 0.000 claims description 4
• 230000000607 poisoning effect Effects 0.000 claims description 4
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
• 150000003254 radicals Chemical class 0.000 claims description 4
• 238000001959 radiotherapy Methods 0.000 claims description 4
• 238000006467 substitution reaction Methods 0.000 claims description 4
• 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 claims description 4
• 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 claims description 4
• WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
• XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
• XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 3
• 150000008575 L-amino acids Chemical class 0.000 claims description 3
• 208000005374 Poisoning Diseases 0.000 claims description 3
• 125000003342 alkenyl group Chemical group 0.000 claims description 3
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
• 125000000304 alkynyl group Chemical group 0.000 claims description 3
• 125000004104 aryloxy group Chemical group 0.000 claims description 3
• GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
• 238000002425 crystallisation Methods 0.000 claims description 3
• 230000008025 crystallization Effects 0.000 claims description 3
• 238000005516 engineering process Methods 0.000 claims description 3
• 150000002148 esters Chemical class 0.000 claims description 3
• 238000001640 fractional crystallisation Methods 0.000 claims description 3
• 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
• 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
• 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
• 229930192474 thiophene Natural products 0.000 claims description 3
• 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
• 229920002554 vinyl polymer Polymers 0.000 claims description 3
• 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
• GWYPDXLJACEENP-UHFFFAOYSA-N 1,3-cycloheptadiene Chemical compound C1CC=CC=CC1 GWYPDXLJACEENP-UHFFFAOYSA-N 0.000 claims description 2
• DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 claims description 2
• GVNVAWHJIKLAGL-UHFFFAOYSA-N 2-(cyclohexen-1-yl)cyclohexan-1-one Chemical compound O=C1CCCCC1C1=CCCCC1 GVNVAWHJIKLAGL-UHFFFAOYSA-N 0.000 claims description 2
• 125000005330 8 membered heterocyclic group Chemical group 0.000 claims description 2
• HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 2
• DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
• 101150065749 Churc1 gene Proteins 0.000 claims description 2
• FEWJPZIEWOKRBE-XIXRPRMCSA-N Mesotartaric acid Chemical compound OC(=O)[C@@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-XIXRPRMCSA-N 0.000 claims description 2
• 206010028980 Neoplasm Diseases 0.000 claims description 2
• CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
• 208000018737 Parkinson disease Diseases 0.000 claims description 2
• PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims description 2
• 102100038239 Protein Churchill Human genes 0.000 claims description 2
• CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
• 125000002723 alicyclic group Chemical group 0.000 claims description 2
• 125000001931 aliphatic group Chemical group 0.000 claims description 2
• HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
• ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
• 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 claims description 2
• 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
• ZXIJMRYMVAMXQP-UHFFFAOYSA-N cycloheptene Chemical compound C1CCC=CCC1 ZXIJMRYMVAMXQP-UHFFFAOYSA-N 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
• 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 2
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• 125000001153 fluoro group Chemical group F* 0.000 claims description 2
• 150000002240 furans Chemical class 0.000 claims description 2
• FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
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• 125000002636 imidazolinyl group Chemical group 0.000 claims description 2
• 125000002883 imidazolyl group Chemical group 0.000 claims description 2
• 125000000842 isoxazolyl group Chemical group 0.000 claims description 2
• HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 claims description 2
• 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
• 125000001624 naphthyl group Chemical group 0.000 claims description 2
• 125000006574 non-aromatic ring group Chemical group 0.000 claims description 2
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• 108090000765 processed proteins & peptides Proteins 0.000 claims description 2
• BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims description 2
• 125000003373 pyrazinyl group Chemical group 0.000 claims description 2
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• 125000002098 pyridazinyl group Chemical group 0.000 claims description 2
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• 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 2
• 125000005017 substituted alkenyl group Chemical group 0.000 claims description 2
• 125000004426 substituted alkynyl group Chemical group 0.000 claims description 2
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• 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 125000003831 tetrazolyl group Chemical group 0.000 claims description 2
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• 125000001425 triazolyl group Chemical group 0.000 claims description 2
• 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
• 239000008096 xylene Substances 0.000 claims description 2
• 229910002091 carbon monoxide Inorganic materials 0.000 claims 6
• 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 4
• 125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims 3
• 125000005647 linker group Chemical group 0.000 claims 3
• 239000008177 pharmaceutical agent Substances 0.000 claims 3
• GQSARBOWRIBUBV-UHFFFAOYSA-N 1-hydroxy-4,5-dihydroimidazole Chemical compound ON1CCN=C1 GQSARBOWRIBUBV-UHFFFAOYSA-N 0.000 claims 1
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• 125000005196 alkyl carbonyloxy group Chemical group 0.000 claims 1
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