DD204924A5

DD204924A5 - Verfahren zur herstellung n-substituierter 2-pyridylindole

Verfahren zur herstellung n-substituierter 2-pyridylindole Download PDF

Info

Publication number: DD204924A5
Authority: DD; German Democratic Republic
Prior art keywords: pyridyl; formula; compound; methyl; indole
Prior art date: 1981-11-19

Application number

DD82244959A

Other languages

German (de)

English (en)

Inventor

Harris B Renfroe

Original Assignee

Ciba Geigy

Priority date

1981-11-19

Filing date

1982-11-17

Publication date

1983-12-14

1982-11-17 Application filed by Ciba Geigy filed Critical Ciba Geigy

1983-12-14 Publication of DD204924A5 publication Critical patent/DD204924A5/de

Links

-1 N-SUBSTITUTED 2-PYRIDYLINDOLE Chemical class 0.000 title claims abstract description 110
238000004519 manufacturing process Methods 0.000 title 1
150000001875 compounds Chemical class 0.000 claims abstract description 171
238000000034 method Methods 0.000 claims abstract description 62
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 60
125000000217 alkyl group Chemical group 0.000 claims abstract description 48
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 42
125000002947 alkylene group Chemical group 0.000 claims abstract description 40
239000001257 hydrogen Substances 0.000 claims abstract description 30
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 30
230000008569 process Effects 0.000 claims abstract description 25
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 21
125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
238000002360 preparation method Methods 0.000 claims abstract description 19
150000002431 hydrogen Chemical class 0.000 claims abstract description 18
125000000446 sulfanediyl group Chemical group *S* 0.000 claims abstract description 17
229910052736 halogen Inorganic materials 0.000 claims abstract description 12
150000002367 halogens Chemical class 0.000 claims abstract description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 6
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 4
239000000203 mixture Substances 0.000 claims description 84
150000003839 salts Chemical class 0.000 claims description 60
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 24
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 16
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 16
125000004970 halomethyl group Chemical group 0.000 claims description 15
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 14
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
CVVKIXNPXDBREE-UHFFFAOYSA-N 8-(3-methyl-2-pyridin-3-ylindol-1-yl)octanoic acid Chemical compound OC(=O)CCCCCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 CVVKIXNPXDBREE-UHFFFAOYSA-N 0.000 claims description 9
125000004450 alkenylene group Chemical group 0.000 claims description 9
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 8
229910052783 alkali metal Inorganic materials 0.000 claims description 7
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 7
125000004419 alkynylene group Chemical group 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 7
230000003287 optical effect Effects 0.000 claims description 7
101000588924 Anthopleura elegantissima Delta-actitoxin-Ael1a Proteins 0.000 claims description 6
150000001340 alkali metals Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000004076 pyridyl group Chemical group 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
OMUAELKYUGNZPY-UHFFFAOYSA-N 5-(3-methyl-2-pyridin-3-ylindol-1-yl)pentanoic acid Chemical compound OC(=O)CCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 OMUAELKYUGNZPY-UHFFFAOYSA-N 0.000 claims description 3
CKTVFPFGLZCDCS-UHFFFAOYSA-N 6-(3-methyl-2-pyridin-3-ylindol-1-yl)hexanoic acid Chemical compound OC(=O)CCCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 CKTVFPFGLZCDCS-UHFFFAOYSA-N 0.000 claims description 3
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
230000002452 interceptive effect Effects 0.000 claims description 3
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 3
239000001301 oxygen Substances 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
239000011593 sulfur Chemical group 0.000 claims description 3
125000005103 alkyl silyl group Chemical group 0.000 claims description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
125000004356 hydroxy functional group Chemical group O* 0.000 claims 7
125000004995 haloalkylthio group Chemical group 0.000 claims 1
108010069102 Thromboxane-A synthase Proteins 0.000 abstract description 15
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 13
230000002401 inhibitory effect Effects 0.000 abstract description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 5
206010002383 Angina Pectoris Diseases 0.000 abstract description 4
208000019695 Migraine disease Diseases 0.000 abstract description 4
208000007536 Thrombosis Diseases 0.000 abstract description 4
208000010125 myocardial infarction Diseases 0.000 abstract description 4
201000001320 Atherosclerosis Diseases 0.000 abstract description 3
206010003119 arrhythmia Diseases 0.000 abstract description 3
230000006793 arrhythmia Effects 0.000 abstract description 3
239000003814 drug Substances 0.000 abstract description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 121
239000000243 solution Substances 0.000 description 118
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 84
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 78
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 67
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 63
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 62
235000002639 sodium chloride Nutrition 0.000 description 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 48
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
239000007858 starting material Substances 0.000 description 38
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 36
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 36
239000002253 acid Substances 0.000 description 31
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 30
229910052943 magnesium sulfate Inorganic materials 0.000 description 30
235000019341 magnesium sulphate Nutrition 0.000 description 30
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 28
229920006395 saturated elastomer Polymers 0.000 description 28
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 25
239000000725 suspension Substances 0.000 description 25
239000000284 extract Substances 0.000 description 24
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
239000002585 base Substances 0.000 description 21
238000006243 chemical reaction Methods 0.000 description 21
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
150000002148 esters Chemical class 0.000 description 18
229910052757 nitrogen Inorganic materials 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 16
125000005907 alkyl ester group Chemical group 0.000 description 16
239000002904 solvent Substances 0.000 description 16
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 15
238000001816 cooling Methods 0.000 description 15
239000000047 product Substances 0.000 description 15
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 14
239000003921 oil Substances 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
239000011780 sodium chloride Substances 0.000 description 14
239000012312 sodium hydride Substances 0.000 description 14
229910000104 sodium hydride Inorganic materials 0.000 description 14
230000005764 inhibitory process Effects 0.000 description 13
WMFOQBRAJBCJND-UHFFFAOYSA-M lithium hydroxide Inorganic materials [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 13
229910052799 carbon Inorganic materials 0.000 description 12
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 12
229910000041 hydrogen chloride Inorganic materials 0.000 description 12
238000009833 condensation Methods 0.000 description 11
230000005494 condensation Effects 0.000 description 11
230000007062 hydrolysis Effects 0.000 description 11
238000006460 hydrolysis reaction Methods 0.000 description 11
239000005457 ice water Substances 0.000 description 11
229910000030 sodium bicarbonate Inorganic materials 0.000 description 11
235000017557 sodium bicarbonate Nutrition 0.000 description 11
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 10
239000000706 filtrate Substances 0.000 description 10
239000000543 intermediate Substances 0.000 description 10
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 10
238000010992 reflux Methods 0.000 description 10
AOQRSYDGSPJRIH-UHFFFAOYSA-N 3-methyl-2-pyridin-3-yl-1h-indole Chemical compound N1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 AOQRSYDGSPJRIH-UHFFFAOYSA-N 0.000 description 9
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
239000010410 layer Substances 0.000 description 9
239000000155 melt Substances 0.000 description 9
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 9
239000002480 mineral oil Substances 0.000 description 9
235000010446 mineral oil Nutrition 0.000 description 9
239000011343 solid material Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 8
150000007513 acids Chemical class 0.000 description 8
XEYBRNLFEZDVAW-ARSRFYASSA-N dinoprostone Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1C\C=C/CCCC(O)=O XEYBRNLFEZDVAW-ARSRFYASSA-N 0.000 description 8
239000007788 liquid Substances 0.000 description 8
230000002829 reductive effect Effects 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-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
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
239000003795 chemical substances by application Substances 0.000 description 7
KAQKFAOMNZTLHT-VVUHWYTRSA-N epoprostenol Chemical compound O1C(=CCCCC(O)=O)C[C@@H]2[C@@H](/C=C/[C@@H](O)CCCCC)[C@H](O)C[C@@H]21 KAQKFAOMNZTLHT-VVUHWYTRSA-N 0.000 description 7
239000012259 ether extract Substances 0.000 description 7
238000001704 evaporation Methods 0.000 description 7
230000008020 evaporation Effects 0.000 description 7
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 7
239000000126 substance Substances 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 6
SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 6
241000124008 Mammalia Species 0.000 description 6
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
241000700159 Rattus Species 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000004480 active ingredient Substances 0.000 description 6
239000008346 aqueous phase Substances 0.000 description 6
238000009835 boiling Methods 0.000 description 6
244000309464 bull Species 0.000 description 6
239000003054 catalyst Substances 0.000 description 6
125000001309 chloro group Chemical group Cl* 0.000 description 6
229960001123 epoprostenol Drugs 0.000 description 6
239000012442 inert solvent Substances 0.000 description 6
238000000746 purification Methods 0.000 description 6
239000000741 silica gel Substances 0.000 description 6
229910002027 silica gel Inorganic materials 0.000 description 6
238000003756 stirring Methods 0.000 description 6
OLGGLCIDAMICTA-UHFFFAOYSA-N 2-pyridin-2-yl-1h-indole Chemical class N1C2=CC=CC=C2C=C1C1=CC=CC=N1 OLGGLCIDAMICTA-UHFFFAOYSA-N 0.000 description 5
OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 5
102000004005 Prostaglandin-endoperoxide synthases Human genes 0.000 description 5
108090000459 Prostaglandin-endoperoxide synthases Proteins 0.000 description 5
229920002472 Starch Polymers 0.000 description 5
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 5
150000008044 alkali metal hydroxides Chemical class 0.000 description 5
125000004849 alkoxymethyl group Chemical group 0.000 description 5
150000001408 amides Chemical class 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
238000004587 chromatography analysis Methods 0.000 description 5
239000012043 crude product Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
238000000338 in vitro Methods 0.000 description 5
150000002825 nitriles Chemical class 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
230000000144 pharmacologic effect Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
235000019698 starch Nutrition 0.000 description 5
238000004809 thin layer chromatography Methods 0.000 description 5
RZWIIPASKMUIAC-VQTJNVASSA-N thromboxane Chemical compound CCCCCCCC[C@H]1OCCC[C@@H]1CCCCCCC RZWIIPASKMUIAC-VQTJNVASSA-N 0.000 description 5
VDNKJMUNLKAGAM-UHFFFAOYSA-N 1-pyridin-3-ylpropan-1-one Chemical compound CCC(=O)C1=CC=CN=C1 VDNKJMUNLKAGAM-UHFFFAOYSA-N 0.000 description 4
KDWAJWXWMMNKHA-UHFFFAOYSA-N 2-pyridin-3-yl-1h-indole Chemical compound N1C2=CC=CC=C2C=C1C1=CC=CN=C1 KDWAJWXWMMNKHA-UHFFFAOYSA-N 0.000 description 4
LMWHTGAOTBAQOJ-UHFFFAOYSA-N 5-(3-methyl-2-pyridin-3-ylindol-1-yl)pentanenitrile Chemical compound N#CCCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 LMWHTGAOTBAQOJ-UHFFFAOYSA-N 0.000 description 4
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
102000003960 Ligases Human genes 0.000 description 4
108090000364 Ligases Proteins 0.000 description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 4
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
229960000583 acetic acid Drugs 0.000 description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
229940114079 arachidonic acid Drugs 0.000 description 4
230000015572 biosynthetic process Effects 0.000 description 4
239000000872 buffer Substances 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
150000001735 carboxylic acids Chemical class 0.000 description 4
239000000460 chlorine Substances 0.000 description 4
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
238000011534 incubation Methods 0.000 description 4
125000001041 indolyl group Chemical group 0.000 description 4
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 4
239000012044 organic layer Substances 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 4
230000002285 radioactive effect Effects 0.000 description 4
230000009467 reduction Effects 0.000 description 4
239000008107 starch Substances 0.000 description 4
238000003786 synthesis reaction Methods 0.000 description 4
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 4
229920002554 vinyl polymer Polymers 0.000 description 4
229910052725 zinc Inorganic materials 0.000 description 4
239000011701 zinc Substances 0.000 description 4
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 3
VPPVMRLURFAFBM-UHFFFAOYSA-N 6-(3-methyl-2-pyridin-3-ylindol-1-yl)hexan-1-ol Chemical compound OCCCCCCN1C2=CC=CC=C2C(C)=C1C1=CC=CN=C1 VPPVMRLURFAFBM-UHFFFAOYSA-N 0.000 description 3
HCZUCEOVPTXFOU-UHFFFAOYSA-N 6-(5-chloro-3-methyl-2-pyridin-3-ylindol-1-yl)hexanoic acid Chemical compound OC(=O)CCCCCN1C2=CC=C(Cl)C=C2C(C)=C1C1=CC=CN=C1 HCZUCEOVPTXFOU-UHFFFAOYSA-N 0.000 description 3
BKJFDZSBZWHRNH-UHFFFAOYSA-N 8-bromooctanoic acid Chemical compound OC(=O)CCCCCCCBr BKJFDZSBZWHRNH-UHFFFAOYSA-N 0.000 description 3
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 3
102000004190 Enzymes Human genes 0.000 description 3
108090000790 Enzymes Proteins 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
241001494479 Pecora Species 0.000 description 3
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
125000005042 acyloxymethyl group Chemical group 0.000 description 3
125000004414 alkyl thio group Chemical group 0.000 description 3
125000005530 alkylenedioxy group Chemical group 0.000 description 3
229910021529 ammonia Inorganic materials 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
150000003863 ammonium salts Chemical class 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
239000002775 capsule Substances 0.000 description 3
239000001569 carbon dioxide Substances 0.000 description 3
229910002092 carbon dioxide Inorganic materials 0.000 description 3
239000003153 chemical reaction reagent Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
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