UA77265C2

UA77265C2 - Pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group

Pyrrolopyrimidine or pyrrolopyridine derivative substituted with a cyclic amino group Download PDF

Info

Publication number: UA77265C2
Authority: UA; Ukraine
Prior art keywords: pyrrolo; alkyl; piperidin; dimethyl; hydrogen
Prior art date: 2002-12-26

Application number

UA20040907464A

Other languages

English (en)

Ukrainian (uk)

Priority date

2002-12-26

Filing date

2003-12-24

Publication date

2006-11-15

2003-12-24 Application filed filed Critical

2006-11-15 Publication of UA77265C2 publication Critical patent/UA77265C2/uk

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125000003277 amino group Chemical group 0.000 title claims abstract description 126
125000004122 cyclic group Chemical group 0.000 title claims abstract description 126
XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical group C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 title claims abstract description 19
KDOPAZIWBAHVJB-UHFFFAOYSA-N 5h-pyrrolo[3,2-d]pyrimidine Chemical group C1=NC=C2NC=CC2=N1 KDOPAZIWBAHVJB-UHFFFAOYSA-N 0.000 title claims abstract description 7
239000005557 antagonist Substances 0.000 claims abstract description 4
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 695
-1 saturated cyclic amine Chemical class 0.000 claims description 407
229910052739 hydrogen Inorganic materials 0.000 claims description 328
239000001257 hydrogen Substances 0.000 claims description 292
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 265
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims description 140
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 138
150000001875 compounds Chemical class 0.000 claims description 114
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 113
239000000203 mixture Substances 0.000 claims description 90
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 80
125000001424 substituent group Chemical group 0.000 claims description 73
229910052736 halogen Inorganic materials 0.000 claims description 71
150000002367 halogens Chemical class 0.000 claims description 71
125000000217 alkyl group Chemical group 0.000 claims description 63
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 62
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 62
150000003839 salts Chemical class 0.000 claims description 52
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 52
150000002431 hydrogen Chemical class 0.000 claims description 45
150000004677 hydrates Chemical class 0.000 claims description 39
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 38
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 37
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 35
125000004432 carbon atom Chemical group C* 0.000 claims description 32
125000004093 cyano group Chemical group *C#N 0.000 claims description 31
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 31
125000004076 pyridyl group Chemical group 0.000 claims description 25
239000000460 chlorine Substances 0.000 claims description 23
125000001072 heteroaryl group Chemical group 0.000 claims description 23
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 22
229910052801 chlorine Inorganic materials 0.000 claims description 22
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 21
125000003118 aryl group Chemical group 0.000 claims description 20
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 11
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 8
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 8
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 7
125000002252 acyl group Chemical group 0.000 claims description 6
150000004944 pyrrolopyrimidines Chemical class 0.000 claims description 6
229910000147 aluminium phosphate Inorganic materials 0.000 claims description 5
125000005129 aryl carbonyl group Chemical group 0.000 claims description 5
125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 5
GYSCBCSGKXNZRH-UHFFFAOYSA-N 1-benzothiophene-2-carboxamide Chemical compound C1=CC=C2SC(C(=O)N)=CC2=C1 GYSCBCSGKXNZRH-UHFFFAOYSA-N 0.000 claims description 4
GHVNFZFCNZKVNT-UHFFFAOYSA-N Decanoic acid Natural products CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 claims description 4
230000009471 action Effects 0.000 claims description 4
BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims description 4
SIOXPEMLGUPBBT-UHFFFAOYSA-N picolinic acid Chemical compound OC(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-N 0.000 claims description 4
229910052717 sulfur Inorganic materials 0.000 claims description 4
MYLBTCQBKAKUTJ-UHFFFAOYSA-N 7-methyl-6,8-bis(methylsulfanyl)pyrrolo[1,2-a]pyrazine Chemical compound C1=CN=CC2=C(SC)C(C)=C(SC)N21 MYLBTCQBKAKUTJ-UHFFFAOYSA-N 0.000 claims description 3
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 claims description 3
RMIODHQZRUFFFF-UHFFFAOYSA-N methoxyacetic acid Chemical compound COCC(O)=O RMIODHQZRUFFFF-UHFFFAOYSA-N 0.000 claims description 3
SMHORIXQSMDYEY-UHFFFAOYSA-N 2-ethylheptanenitrile Chemical compound CCCCCC(CC)C#N SMHORIXQSMDYEY-UHFFFAOYSA-N 0.000 claims description 2
125000000753 cycloalkyl group Chemical group 0.000 claims description 2
MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical compound C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 2
229910052731 fluorine Inorganic materials 0.000 claims description 2
239000002464 receptor antagonist Substances 0.000 claims description 2
229940044551 receptor antagonist Drugs 0.000 claims description 2
229960004756 ethanol Drugs 0.000 claims 43
KCTZOTUQSGYWLV-UHFFFAOYSA-N N1C=NC=C2N=CC=C21 Chemical group N1C=NC=C2N=CC=C21 KCTZOTUQSGYWLV-UHFFFAOYSA-N 0.000 claims 17
150000005255 pyrrolopyridines Chemical class 0.000 claims 11
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 2
125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
241001404126 Gyas Species 0.000 claims 1
239000013543 active substance Substances 0.000 claims 1
229910052799 carbon Inorganic materials 0.000 claims 1
238000004651 near-field scanning optical microscopy Methods 0.000 claims 1
229910052698 phosphorus Inorganic materials 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
238000012876 topography Methods 0.000 claims 1
201000010099 disease Diseases 0.000 abstract description 16
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 16
102100021752 Corticoliberin Human genes 0.000 abstract description 14
206010008118 cerebral infarction Diseases 0.000 abstract description 10
208000019901 Anxiety disease Diseases 0.000 abstract description 6
208000024827 Alzheimer disease Diseases 0.000 abstract description 5
201000006474 Brain Ischemia Diseases 0.000 abstract description 5
206010048962 Brain oedema Diseases 0.000 abstract description 5
206010008120 Cerebral ischaemia Diseases 0.000 abstract description 5
208000030814 Eating disease Diseases 0.000 abstract description 5
208000019454 Feeding and Eating disease Diseases 0.000 abstract description 5
208000023105 Huntington disease Diseases 0.000 abstract description 5
206010020772 Hypertension Diseases 0.000 abstract description 5
206010061218 Inflammation Diseases 0.000 abstract description 5
208000018737 Parkinson disease Diseases 0.000 abstract description 5
208000027418 Wounds and injury Diseases 0.000 abstract description 5
230000036506 anxiety Effects 0.000 abstract description 5
208000006752 brain edema Diseases 0.000 abstract description 5
208000026106 cerebrovascular disease Diseases 0.000 abstract description 5
235000014632 disordered eating Nutrition 0.000 abstract description 5
206010013663 drug dependence Diseases 0.000 abstract description 5
206010015037 epilepsy Diseases 0.000 abstract description 5
230000004054 inflammatory process Effects 0.000 abstract description 5
208000018556 stomach disease Diseases 0.000 abstract description 5
208000011117 substance-related disease Diseases 0.000 abstract description 5
201000004384 Alopecia Diseases 0.000 abstract description 4
108010056643 Corticotropin-Releasing Hormone Receptors Proteins 0.000 abstract description 4
201000004624 Dermatitis Diseases 0.000 abstract description 4
231100000360 alopecia Toxicity 0.000 abstract description 4
208000002551 irritable bowel syndrome Diseases 0.000 abstract description 4
201000000980 schizophrenia Diseases 0.000 abstract description 4
208000019116 sleep disease Diseases 0.000 abstract description 4
239000003795 chemical substances by application Substances 0.000 abstract description 3
230000000069 prophylactic effect Effects 0.000 abstract description 3
206010052428 Wound Diseases 0.000 abstract description 2
230000001225 therapeutic effect Effects 0.000 abstract description 2
230000036039 immunity Effects 0.000 abstract 1
239000012071 phase Substances 0.000 description 380
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 184
230000014759 maintenance of location Effects 0.000 description 158
238000004128 high performance liquid chromatography Methods 0.000 description 153
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 134
239000005695 Ammonium acetate Substances 0.000 description 134
235000019257 ammonium acetate Nutrition 0.000 description 134
229940043376 ammonium acetate Drugs 0.000 description 134
239000007864 aqueous solution Substances 0.000 description 122
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 121
VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 85
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 74
239000002904 solvent Substances 0.000 description 69
229960000583 acetic acid Drugs 0.000 description 62
235000011054 acetic acid Nutrition 0.000 description 61
229910021529 ammonia Inorganic materials 0.000 description 59
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 52
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
239000012442 inert solvent Substances 0.000 description 33
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 32
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 31
239000000243 solution Substances 0.000 description 30
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 28
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 26
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 24
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 23
239000002244 precipitate Substances 0.000 description 23
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 21
206010028980 Neoplasm Diseases 0.000 description 19
201000011510 cancer Diseases 0.000 description 19
150000001408 amides Chemical class 0.000 description 18
239000000741 silica gel Substances 0.000 description 18
229910002027 silica gel Inorganic materials 0.000 description 18
239000000055 Corticotropin-Releasing Hormone Substances 0.000 description 17
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 17
229910052740 iodine Inorganic materials 0.000 description 17
ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 16
229910052751 metal Inorganic materials 0.000 description 16
239000002184 metal Substances 0.000 description 16
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 14
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 14
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 13
101000957708 Catostomus commersonii Corticoliberin-2 Proteins 0.000 description 13
230000015572 biosynthetic process Effects 0.000 description 13
238000001816 cooling Methods 0.000 description 13
239000011541 reaction mixture Substances 0.000 description 13
239000003480 eluent Substances 0.000 description 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Substances [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-diisopropylethylamine Substances CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 11
150000002170 ethers Chemical class 0.000 description 11
239000000706 filtrate Substances 0.000 description 11
229930195733 hydrocarbon Natural products 0.000 description 11
150000002430 hydrocarbons Chemical class 0.000 description 11
229910052757 nitrogen Inorganic materials 0.000 description 11
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 10
239000012074 organic phase Substances 0.000 description 10
238000003786 synthesis reaction Methods 0.000 description 10
150000001298 alcohols Chemical class 0.000 description 9
238000010992 reflux Methods 0.000 description 9
239000007787 solid Substances 0.000 description 9
239000000725 suspension Substances 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 8
239000012267 brine Substances 0.000 description 8
150000007529 inorganic bases Chemical class 0.000 description 8
238000000034 method Methods 0.000 description 8
235000011118 potassium hydroxide Nutrition 0.000 description 8
230000007958 sleep Effects 0.000 description 8
235000011121 sodium hydroxide Nutrition 0.000 description 8
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 8
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 7
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 7
RQPZNWPYLFFXCP-UHFFFAOYSA-L barium dihydroxide Chemical compound [OH-].[OH-].[Ba+2] RQPZNWPYLFFXCP-UHFFFAOYSA-L 0.000 description 7
229910001863 barium hydroxide Inorganic materials 0.000 description 7
238000004440 column chromatography Methods 0.000 description 7
NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical compound [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
239000011736 potassium bicarbonate Substances 0.000 description 7
235000015497 potassium bicarbonate Nutrition 0.000 description 7
229910000028 potassium bicarbonate Inorganic materials 0.000 description 7
229910000027 potassium carbonate Inorganic materials 0.000 description 7
235000011181 potassium carbonates Nutrition 0.000 description 7
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 7
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
235000017550 sodium carbonate Nutrition 0.000 description 7
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 7
239000012312 sodium hydride Substances 0.000 description 7
229910000104 sodium hydride Inorganic materials 0.000 description 7
235000010469 Glycine max Nutrition 0.000 description 6
239000007818 Grignard reagent Substances 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 6
238000009739 binding Methods 0.000 description 6
150000004795 grignard reagents Chemical class 0.000 description 6
238000004811 liquid chromatography Methods 0.000 description 6
125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 6
230000035939 shock Effects 0.000 description 6
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 6
241001446467 Mama Species 0.000 description 5
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
230000027455 binding Effects 0.000 description 5
239000003153 chemical reaction reagent Substances 0.000 description 5
125000004785 fluoromethoxy group Chemical group [H]C([H])(F)O* 0.000 description 5
239000011521 glass Substances 0.000 description 5
210000000987 immune system Anatomy 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
239000008096 xylene Substances 0.000 description 5
HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 4
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 4
CONWVZWHEGJGII-UHFFFAOYSA-N C(C1=CC(C(=O)O)=CC=C1)(=O)O.CCCCCC Chemical compound C(C1=CC(C(=O)O)=CC=C1)(=O)O.CCCCCC CONWVZWHEGJGII-UHFFFAOYSA-N 0.000 description 4
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
108020004414 DNA Proteins 0.000 description 4
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 4
241000282320 Panthera leo Species 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
230000006378 damage Effects 0.000 description 4
239000012528 membrane Substances 0.000 description 4
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 4
238000002360 preparation method Methods 0.000 description 4
229920006395 saturated elastomer Polymers 0.000 description 4
210000003625 skull Anatomy 0.000 description 4
229910052708 sodium Inorganic materials 0.000 description 4
238000004809 thin layer chromatography Methods 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
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