AU5435298A - 5-ht1f agonists - Google Patents

Info

Publication number

AU5435298A

AU5435298A AU54352/98A AU5435298A AU5435298A AU 5435298 A AU5435298 A AU 5435298A AU 54352/98 A AU54352/98 A AU 54352/98A AU 5435298 A AU5435298 A AU 5435298A AU 5435298 A AU5435298 A AU 5435298A

Authority

AU

Australia

Prior art keywords

phenyl

substituted

alkyl

pyrrolo

amino

Prior art date

1996-11-15

Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)

Abandoned

Links

• Espacenet
• Global Dossier
• Discuss

• 239000000556 agonist Substances 0.000 title abstract description 13
• 150000001875 compounds Chemical class 0.000 claims abstract description 247
• 238000000034 method Methods 0.000 claims abstract description 143
• 230000004913 activation Effects 0.000 claims abstract description 9
• 239000008194 pharmaceutical composition Substances 0.000 claims abstract description 5
• -1 4-substituted piperazine Chemical class 0.000 claims description 148
• 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 104
• 125000000217 alkyl group Chemical group 0.000 claims description 40
• 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 34
• DRTQHJPVMGBUCF-UCVXFZOQSA-N 1-[(2s,3s,4s,5s)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione Chemical compound O[C@H]1[C@H](O)[C@H](CO)O[C@@H]1N1C(=O)NC(=O)C=C1 DRTQHJPVMGBUCF-UCVXFZOQSA-N 0.000 claims description 26
• 125000002947 alkylene group Chemical group 0.000 claims description 26
• 206010015866 Extravasation Diseases 0.000 claims description 20
• 230000036251 extravasation Effects 0.000 claims description 20
• RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
• 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 16
• 208000002193 Pain Diseases 0.000 claims description 16
• 125000003342 alkenyl group Chemical group 0.000 claims description 16
• 125000001072 heteroaryl group Chemical group 0.000 claims description 15
• 125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 13
• GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 13
• 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 13
• YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
• NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
• 239000002253 acid Substances 0.000 claims description 12
• 150000003839 salts Chemical class 0.000 claims description 12
• 208000019695 Migraine disease Diseases 0.000 claims description 11
• 229910052739 hydrogen Inorganic materials 0.000 claims description 11
• 206010027599 migraine Diseases 0.000 claims description 11
• 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
• 241000124008 Mammalia Species 0.000 claims description 9
• 125000003545 alkoxy group Chemical group 0.000 claims description 9
• 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
• 230000005764 inhibitory process Effects 0.000 claims description 9
• 229910052757 nitrogen Inorganic materials 0.000 claims description 9
• 125000000753 cycloalkyl group Chemical group 0.000 claims description 8
• 208000035475 disorder Diseases 0.000 claims description 8
• 239000000546 pharmaceutical excipient Substances 0.000 claims description 8
• 239000012453 solvate Substances 0.000 claims description 8
• 125000000623 heterocyclic group Chemical group 0.000 claims description 7
• 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 7
• 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 6
• 125000005466 alkylenyl group Chemical group 0.000 claims description 6
• 125000004433 nitrogen atom Chemical group N* 0.000 claims description 6
• BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 6
• 101000941893 Felis catus Leucine-rich repeat and calponin homology domain-containing protein 1 Proteins 0.000 claims description 5
• 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
• 125000001624 naphthyl group Chemical group 0.000 claims description 5
• 125000000304 alkynyl group Chemical group 0.000 claims description 4
• 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 3
• 208000000094 Chronic Pain Diseases 0.000 claims description 3
• 239000003085 diluting agent Substances 0.000 claims description 3
• 230000001404 mediated effect Effects 0.000 claims description 3
• 229910052760 oxygen Inorganic materials 0.000 claims description 3
• 125000005865 C2-C10alkynyl group Chemical group 0.000 claims description 2
• 239000003937 drug carrier Substances 0.000 claims description 2
• 230000002265 prevention Effects 0.000 claims 2
• ORJIHHLJBCQRBS-UHFFFAOYSA-N n-[3-(1-methylpiperidin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-yl]propanamide Chemical compound C12=NC(NC(=O)CC)=CC=C2NC=C1C1CCN(C)CC1 ORJIHHLJBCQRBS-UHFFFAOYSA-N 0.000 claims 1
• 239000000203 mixture Substances 0.000 abstract description 36
• 102100036311 5-hydroxytryptamine receptor 1F Human genes 0.000 abstract 2
• 101710138086 5-hydroxytryptamine receptor 1F Proteins 0.000 abstract 2
• LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 105
• OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 99
• JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 88
• LAOHESRIMKGEEK-UHFFFAOYSA-N 3-(1-methylpiperidin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C1CN(C)CCC1C1=CNC2=CC=C(N)N=C12 LAOHESRIMKGEEK-UHFFFAOYSA-N 0.000 description 67
• YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
• 230000002829 reductive effect Effects 0.000 description 47
• UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 44
• 102000005962 receptors Human genes 0.000 description 35
• 108020003175 receptors Proteins 0.000 description 35
• 239000007787 solid Substances 0.000 description 30
• QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 28
• 239000000243 solution Substances 0.000 description 28
• 239000000047 product Substances 0.000 description 27
• 239000011541 reaction mixture Substances 0.000 description 27
• HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 24
• WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 24
• XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 24
• XWIYUCRMWCHYJR-UHFFFAOYSA-N 1h-pyrrolo[3,2-b]pyridine Chemical compound C1=CC=C2NC=CC2=N1 XWIYUCRMWCHYJR-UHFFFAOYSA-N 0.000 description 22
• XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
• ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
• 230000027455 binding Effects 0.000 description 21
• 239000000538 analytical sample Substances 0.000 description 20
• QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
• 238000006243 chemical reaction Methods 0.000 description 18
• FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 17
• 238000002360 preparation method Methods 0.000 description 17
• HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 16
• 108090000623 proteins and genes Proteins 0.000 description 14
• VMCYEHPEFYPEMX-UHFFFAOYSA-N 3-piperidin-4-yl-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical class C12=NC(N)=CC=C2NC=C1C1CCNCC1 VMCYEHPEFYPEMX-UHFFFAOYSA-N 0.000 description 13
• XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
• 102000004169 proteins and genes Human genes 0.000 description 13
• VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
• KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 12
• YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
• 150000001412 amines Chemical class 0.000 description 12
• 239000006260 foam Substances 0.000 description 12
• 125000005843 halogen group Chemical group 0.000 description 12
• YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 12
• CZKLEJHVLCMVQR-UHFFFAOYSA-N 4-fluorobenzoyl chloride Chemical compound FC1=CC=C(C(Cl)=O)C=C1 CZKLEJHVLCMVQR-UHFFFAOYSA-N 0.000 description 11
• 241001024304 Mino Species 0.000 description 11
• 239000002585 base Substances 0.000 description 11
• 210000004027 cell Anatomy 0.000 description 11
• 230000000694 effects Effects 0.000 description 11
• 238000009472 formulation Methods 0.000 description 11
• KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 10
• 229940079593 drug Drugs 0.000 description 10
• 239000003814 drug Substances 0.000 description 10
• 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 9
• QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 9
• IWJYBYJQJDVZJQ-UHFFFAOYSA-N 3-[1-(2-phenylethyl)-3,6-dihydro-2h-pyridin-4-yl]-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C12=NC(N)=CC=C2NC=C1C(CC1)=CCN1CCC1=CC=CC=C1 IWJYBYJQJDVZJQ-UHFFFAOYSA-N 0.000 description 9
• VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 9
• RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
• 241000700159 Rattus Species 0.000 description 9
• ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
• 239000000908 ammonium hydroxide Substances 0.000 description 9
• 239000011780 sodium chloride Substances 0.000 description 9
• 239000002904 solvent Substances 0.000 description 9
• 125000001424 substituent group Chemical group 0.000 description 9
• NJMUUPUCFASQIY-UHFFFAOYSA-N tert-butyl 4-(5-amino-1h-pyrrolo[3,2-b]pyridin-3-yl)piperidine-1-carboxylate Chemical compound C1CN(C(=O)OC(C)(C)C)CCC1C1=CNC2=CC=C(N)N=C12 NJMUUPUCFASQIY-UHFFFAOYSA-N 0.000 description 9
• HGHIDQUDWLHDTK-UHFFFAOYSA-N 3-[1-(2-phenylethyl)piperidin-4-yl]-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C12=NC(N)=CC=C2NC=C1C(CC1)CCN1CCC1=CC=CC=C1 HGHIDQUDWLHDTK-UHFFFAOYSA-N 0.000 description 8
• CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
• 125000003118 aryl group Chemical group 0.000 description 8
• 239000004615 ingredient Substances 0.000 description 8
• 239000012528 membrane Substances 0.000 description 8
• KWYUFKZDYYNOTN-UHFFFAOYSA-M potassium hydroxide Inorganic materials [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 8
• RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 8
• 238000010898 silica gel chromatography Methods 0.000 description 8
• 238000012360 testing method Methods 0.000 description 8
• 238000011282 treatment Methods 0.000 description 8
• 210000000427 trigeminal ganglion Anatomy 0.000 description 8
• FUNPYCZDNCZXQT-UHFFFAOYSA-N 3-(1,2,3,6-tetrahydropyridin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical class C12=NC(N)=CC=C2NC=C1C1=CCNCC1 FUNPYCZDNCZXQT-UHFFFAOYSA-N 0.000 description 7
• ZKMWKEXDFNWIHM-UHFFFAOYSA-N 3-(1-ethylpiperidin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C1CN(CC)CCC1C1=CNC2=CC=C(N)N=C12 ZKMWKEXDFNWIHM-UHFFFAOYSA-N 0.000 description 7
• 241001465754 Metazoa Species 0.000 description 7
• VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
• 239000004480 active ingredient Substances 0.000 description 7
• 238000003556 assay Methods 0.000 description 7
• ZOOSILUVXHVRJE-UHFFFAOYSA-N cyclopropanecarbonyl chloride Chemical compound ClC(=O)C1CC1 ZOOSILUVXHVRJE-UHFFFAOYSA-N 0.000 description 7
• 239000008188 pellet Substances 0.000 description 7
• 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
• 229940076279 serotonin Drugs 0.000 description 7
• OFTKFKYVSBNYEC-UHFFFAOYSA-N 2-furoyl chloride Chemical compound ClC(=O)C1=CC=CO1 OFTKFKYVSBNYEC-UHFFFAOYSA-N 0.000 description 6
• ANJMITTWHAIIIU-UHFFFAOYSA-N 3-(1-ethyl-3,6-dihydro-2h-pyridin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C1N(CC)CCC(C=2C3=NC(N)=CC=C3NC=2)=C1 ANJMITTWHAIIIU-UHFFFAOYSA-N 0.000 description 6
• 102000040125 5-hydroxytryptamine receptor family Human genes 0.000 description 6
• 108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 6
• WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
• QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
• UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
• 241001269524 Dura Species 0.000 description 6
• OHCQJHSOBUTRHG-KGGHGJDLSA-N FORSKOLIN Chemical compound O=C([C@@]12O)C[C@](C)(C=C)O[C@]1(C)[C@@H](OC(=O)C)[C@@H](O)[C@@H]1[C@]2(C)[C@@H](O)CCC1(C)C OHCQJHSOBUTRHG-KGGHGJDLSA-N 0.000 description 6
• TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 6
• DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 6
• PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 6
• 230000015572 biosynthetic process Effects 0.000 description 6
• 235000013877 carbamide Nutrition 0.000 description 6
• 238000004587 chromatography analysis Methods 0.000 description 6
• 238000005984 hydrogenation reaction Methods 0.000 description 6
• 230000000638 stimulation Effects 0.000 description 6
• QIQITDHWZYEEPA-UHFFFAOYSA-N thiophene-2-carbonyl chloride Chemical compound ClC(=O)C1=CC=CS1 QIQITDHWZYEEPA-UHFFFAOYSA-N 0.000 description 6
• UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 6
• 125000004938 5-pyridyl group Chemical group N1=CC=CC(=C1)* 0.000 description 5
• BGMZTBKXOFFTBJ-UHFFFAOYSA-N 6-methyl-5-nitropyridin-2-amine Chemical compound CC1=NC(N)=CC=C1[N+]([O-])=O BGMZTBKXOFFTBJ-UHFFFAOYSA-N 0.000 description 5
• CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 description 5
• 241000700198 Cavia Species 0.000 description 5
• 150000001204 N-oxides Chemical class 0.000 description 5
• WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 5
• 239000012346 acetyl chloride Substances 0.000 description 5
• 238000004458 analytical method Methods 0.000 description 5
• 150000008064 anhydrides Chemical class 0.000 description 5
• 239000008346 aqueous phase Substances 0.000 description 5
• 239000004202 carbamide Substances 0.000 description 5
• 125000004093 cyano group Chemical group *C#N 0.000 description 5
• 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
• 239000000706 filtrate Substances 0.000 description 5
• 238000005755 formation reaction Methods 0.000 description 5
• BTUIFMCWPFMNRG-UHFFFAOYSA-N furan-3-carbonyl chloride Chemical compound ClC(=O)C=1C=COC=1 BTUIFMCWPFMNRG-UHFFFAOYSA-N 0.000 description 5
• 239000001257 hydrogen Substances 0.000 description 5
• 238000002347 injection Methods 0.000 description 5
• 239000007924 injection Substances 0.000 description 5
• 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
• 239000012074 organic phase Substances 0.000 description 5
• 239000012071 phase Substances 0.000 description 5
• 238000010992 reflux Methods 0.000 description 5
• 229920006395 saturated elastomer Polymers 0.000 description 5
• QTWBEVAYYDZLQL-UHFFFAOYSA-N thiophene-3-carbonyl chloride Chemical compound ClC(=O)C=1C=CSC=1 QTWBEVAYYDZLQL-UHFFFAOYSA-N 0.000 description 5
• XOFLBQFBSOEHOG-UUOKFMHZSA-N γS-GTP Chemical compound C1=2NC(N)=NC(=O)C=2N=CN1[C@@H]1O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(O)=S)[C@@H](O)[C@H]1O XOFLBQFBSOEHOG-UUOKFMHZSA-N 0.000 description 5
• PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 4
• VDFCYSIJRNRTTL-UHFFFAOYSA-N 3-(1-methyl-3,6-dihydro-2h-pyridin-4-yl)-1h-pyrrolo[3,2-b]pyridin-5-amine Chemical compound C1N(C)CCC(C=2C3=NC(N)=CC=C3NC=2)=C1 VDFCYSIJRNRTTL-UHFFFAOYSA-N 0.000 description 4
• DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 4
• VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
• MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 4
• KFSLWBXXFJQRDL-UHFFFAOYSA-N Peracetic acid Chemical compound CC(=O)OO KFSLWBXXFJQRDL-UHFFFAOYSA-N 0.000 description 4
• PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
• 239000007983 Tris buffer Substances 0.000 description 4
• RTTSQSBCRXBLAU-UHFFFAOYSA-N carbamoyl bromide Chemical compound NC(Br)=O RTTSQSBCRXBLAU-UHFFFAOYSA-N 0.000 description 4
• 230000003247 decreasing effect Effects 0.000 description 4
• 150000002081 enamines Chemical class 0.000 description 4
• 238000001914 filtration Methods 0.000 description 4
• BNTRVUUJBGBGLZ-UHFFFAOYSA-N hydron;pyridine-4-carbonyl chloride;chloride Chemical compound Cl.ClC(=O)C1=CC=NC=C1 BNTRVUUJBGBGLZ-UHFFFAOYSA-N 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
• 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
• 235000019341 magnesium sulphate Nutrition 0.000 description 4
• 125000004482 piperidin-4-yl group Chemical group N1CCC(CC1)* 0.000 description 4
• BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
• 229920000642 polymer Polymers 0.000 description 4
• 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 4
• 239000000523 sample Substances 0.000 description 4
• 239000003762 serotonin receptor affecting agent Substances 0.000 description 4
• 239000000741 silica gel Substances 0.000 description 4
• 229910002027 silica gel Inorganic materials 0.000 description 4
• 229910052938 sodium sulfate Inorganic materials 0.000 description 4
• 235000011152 sodium sulphate Nutrition 0.000 description 4
• KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 description 4
• 239000000725 suspension Substances 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
• LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 4
• 239000003981 vehicle Substances 0.000 description 4
• 239000003039 volatile agent Substances 0.000 description 4
• 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 3
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