JPS6251650A - ヒドロピリジン誘導体、その製造法及び向知性薬 - Google Patents

ヒドロピリジン誘導体、その製造法及び向知性薬

Info

Publication number: JPS6251650A
Authority: JP; Japan
Prior art keywords: carboxylic acid; methyl; hydroxy; tetrahydro; ethyl ester
Prior art date: 1985-08-27
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.): Granted

Application number

JP19920286A

Other languages

English (en)

Japanese (ja)

Other versions

JPH055828B2 (da

Inventor

ゲオルグ・フォン・シュプレッハー

ヴォルフガング・フルーストル

アルミン・チュスト

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date (The priority date 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 date listed.)

1985-08-27

Filing date

1986-08-27

Publication date

1987-03-06

1986-08-27 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1987-03-06 Publication of JPS6251650A publication Critical patent/JPS6251650A/ja

1993-01-25 Publication of JPH055828B2 publication Critical patent/JPH055828B2/ja

Status Granted legal-status Critical Current

Links

239000003814 drug Substances 0.000 title claims description 12
238000004519 manufacturing process Methods 0.000 title claims description 10
229940079593 drug Drugs 0.000 title claims description 3
UCMIRNVEIXFBKS-UHFFFAOYSA-N beta-alanine Chemical class NCCC(O)=O UCMIRNVEIXFBKS-UHFFFAOYSA-N 0.000 title claims 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical class C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title description 13
-1 benzocyclobuten-1-ylidene residue Chemical group 0.000 claims description 216
239000000203 mixture Substances 0.000 claims description 119
150000001875 compounds Chemical class 0.000 claims description 118
150000003839 salts Chemical class 0.000 claims description 94
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 92
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 81
125000004432 carbon atom Chemical group C* 0.000 claims description 68
239000002253 acid Substances 0.000 claims description 60
238000000034 method Methods 0.000 claims description 58
125000000217 alkyl group Chemical group 0.000 claims description 49
125000003545 alkoxy group Chemical group 0.000 claims description 47
229910052736 halogen Inorganic materials 0.000 claims description 38
150000002367 halogens Chemical class 0.000 claims description 38
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 37
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 27
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 26
125000004423 acyloxy group Chemical group 0.000 claims description 25
229910052739 hydrogen Inorganic materials 0.000 claims description 24
239000001257 hydrogen Substances 0.000 claims description 23
125000002947 alkylene group Chemical group 0.000 claims description 21
125000005115 alkyl carbamoyl group Chemical group 0.000 claims description 20
125000004494 ethyl ester group Chemical group 0.000 claims description 20
239000000126 substance Substances 0.000 claims description 19
239000004480 active ingredient Substances 0.000 claims description 18
238000002360 preparation method Methods 0.000 claims description 16
125000004122 cyclic group Chemical group 0.000 claims description 15
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 15
125000001118 alkylidene group Chemical group 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 14
125000004130 indan-2-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])(*)C2([H])[H] 0.000 claims description 11
125000003277 amino group Chemical group 0.000 claims description 10
125000004429 atom Chemical group 0.000 claims description 9
239000000460 chlorine Substances 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
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 6
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
150000004702 methyl esters Chemical class 0.000 claims description 6
150000001450 anions Chemical class 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000001841 imino group Chemical group [H]N=* 0.000 claims description 5
125000004129 indan-1-yl group Chemical group [H]C1=C([H])C([H])=C2C(=C1[H])C([H])([H])C([H])([H])C2([H])* 0.000 claims description 5
239000005973 Carvone Substances 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 3
YVFZJEZNDYOHAO-UHFFFAOYSA-N ethyl 1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]piperidine-3-carboxylate Chemical compound C1C(C(=O)OCC)CCCN1CC1=CC2=CC=C(OC)C=C12 YVFZJEZNDYOHAO-UHFFFAOYSA-N 0.000 claims description 3
125000006239 protecting group Chemical group 0.000 claims description 3
QCEJPTXCLKCXIW-IAGOWNOFSA-N ethyl (3r,4r)-4-hydroxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]piperidine-3-carboxylate Chemical compound C1C[C@@H](O)[C@H](C(=O)OCC)CN1CC1=CC2=CC=C(OC)C=C12 QCEJPTXCLKCXIW-IAGOWNOFSA-N 0.000 claims description 2
FWXQRMJNMBKTJI-UHFFFAOYSA-N methyl 1-[(5-methoxy-2,3-dihydro-1h-inden-2-yl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1CC1CC2=CC(OC)=CC=C2C1 FWXQRMJNMBKTJI-UHFFFAOYSA-N 0.000 claims description 2
ZOHQIWWFJAUEMC-UHFFFAOYSA-N methyl 1-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1CC1C2=CC(OC)=CC=C2CC1 ZOHQIWWFJAUEMC-UHFFFAOYSA-N 0.000 claims description 2
DQCMEJMRRQLZEU-UHFFFAOYSA-N methyl 1-[2-(2,3-dihydro-1h-inden-1-yl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1CCC1C2=CC=CC=C2CC1 DQCMEJMRRQLZEU-UHFFFAOYSA-N 0.000 claims description 2
229920006395 saturated elastomer Polymers 0.000 claims description 2
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 9
150000002431 hydrogen Chemical class 0.000 claims 5
GVAVPPMSQKUHIR-UHFFFAOYSA-N methyl 1-(5-methoxy-2,3-dihydro-1h-inden-2-yl)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1C1CC2=CC(OC)=CC=C2C1 GVAVPPMSQKUHIR-UHFFFAOYSA-N 0.000 claims 2
239000000546 pharmaceutical excipient Substances 0.000 claims 2
AWXYKOIYQGUKOH-UHFFFAOYSA-N 4-hydroxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]piperidine-3-carboxamide Chemical compound C=12C=C(OC)C=CC2=CC=1CN1CCC(O)C(C(N)=O)C1 AWXYKOIYQGUKOH-UHFFFAOYSA-N 0.000 claims 1
150000001413 amino acids Chemical class 0.000 claims 1
150000001555 benzenes Chemical group 0.000 claims 1
UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical group C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims 1
125000004144 cyclobuten-1-yl group Chemical group [H]C1=C(*)C([H])([H])C1([H])[H] 0.000 claims 1
OVJUZXSMKYBBCD-IAGOWNOFSA-N ethyl (3r,4r)-1-(7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenylmethyl)-4-methylsulfonyloxypiperidine-3-carboxylate Chemical compound C1C[C@@H](OS(C)(=O)=O)[C@H](C(=O)OCC)CN1CC1=C(C=CC=C2)C2=C1 OVJUZXSMKYBBCD-IAGOWNOFSA-N 0.000 claims 1
HTCQTXXDDFUSPS-DNQXCXABSA-N ethyl (3r,4r)-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-4-phenylmethoxypiperidine-3-carboxylate Chemical compound O([C@@H]1CCN(CC=2C3=CC(OC)=CC=C3C=2)C[C@H]1C(=O)OCC)CC1=CC=CC=C1 HTCQTXXDDFUSPS-DNQXCXABSA-N 0.000 claims 1
KZMAPSUZQICBIM-RTBURBONSA-N ethyl (3r,4r)-4-acetyloxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]piperidine-3-carboxylate Chemical compound C1C[C@@H](OC(C)=O)[C@H](C(=O)OCC)CN1CC1=CC2=CC=C(OC)C=C12 KZMAPSUZQICBIM-RTBURBONSA-N 0.000 claims 1
CRPLVAZTGBGPKN-QZTJIDSGSA-N ethyl (3r,4r)-4-hydroxy-1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]piperidine-3-carboxylate Chemical compound C1C[C@@H](O)[C@H](C(=O)OCC)CN1CCC1=CC2=CC=C(OC)C=C12 CRPLVAZTGBGPKN-QZTJIDSGSA-N 0.000 claims 1
VEKLYJBJGWOCKQ-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)-4-hydroxy-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1C1=C(C=CC=C2)C2=C1 VEKLYJBJGWOCKQ-UHFFFAOYSA-N 0.000 claims 1
SCNWHQUVRCDFNX-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenylmethyl)-4-hydroxy-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1=C(C=CC=C2)C2=C1 SCNWHQUVRCDFNX-UHFFFAOYSA-N 0.000 claims 1
MDCMFWDHSQCGGZ-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1,3,5,7-tetraenylmethyl)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=CCCN1CC1=CC2=CC=CC=C12 MDCMFWDHSQCGGZ-UHFFFAOYSA-N 0.000 claims 1
WLCPBCHFDPDGDI-UHFFFAOYSA-N ethyl 1-[(4-chloro-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]-4-hydroxy-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1=C(C=C(Cl)C=C2)C2=C1 WLCPBCHFDPDGDI-UHFFFAOYSA-N 0.000 claims 1
LFDJBPPJFWTQOS-UHFFFAOYSA-N ethyl 1-[(5-methoxy-2,3-dihydro-1h-inden-2-yl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1CC2=CC(OC)=CC=C2C1 LFDJBPPJFWTQOS-UHFFFAOYSA-N 0.000 claims 1
MWOJEEMOXIJYKO-UHFFFAOYSA-N ethyl 1-[(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=CCCN1CC1C2=CC(OC)=CC=C2CCC1 MWOJEEMOXIJYKO-UHFFFAOYSA-N 0.000 claims 1
JNCKCUQZAHDEMO-UHFFFAOYSA-N ethyl 1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=CCCN1CCC1=CC2=CC=C(OC)C=C12 JNCKCUQZAHDEMO-UHFFFAOYSA-N 0.000 claims 1
VRXDWIHGAORJGV-UHFFFAOYSA-N ethyl 4-amino-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(N)CCN1CC1=CC2=CC=C(OC)C=C12 VRXDWIHGAORJGV-UHFFFAOYSA-N 0.000 claims 1
JULBLEVTDJCOGP-UHFFFAOYSA-N ethyl 4-hydroxy-1-(6-methoxy-2,3-dihydro-1h-inden-1-yl)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1C1C2=CC(OC)=CC=C2CC1 JULBLEVTDJCOGP-UHFFFAOYSA-N 0.000 claims 1
MIRANYBANLDUOZ-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1=C(C=C(OC)C=C2)C2=C1 MIRANYBANLDUOZ-UHFFFAOYSA-N 0.000 claims 1
XFKGDMODQINPDC-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(4-methoxy-7-methyl-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1(C)C2=CC(OC)=CC=C2C1 XFKGDMODQINPDC-UHFFFAOYSA-N 0.000 claims 1
FVIDBUBWKWQWFC-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(4-methoxy-8-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1=C(C=CC(OC)=C2)C2=C1 FVIDBUBWKWQWFC-UHFFFAOYSA-N 0.000 claims 1
LIRIVFMHBLEIGF-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(5-methoxy-2,3-dihydro-1H-inden-2-yl)methyl]-3,6-dihydro-2H-pyridine-5-carboxylate Chemical compound C(C)OC(=O)C=1CN(CCC1O)CC1CC2=CC(=CC=C2C1)OC LIRIVFMHBLEIGF-UHFFFAOYSA-N 0.000 claims 1
HZABDQRYRHROBD-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1C2=CC(OC)=CC=C2CC1 HZABDQRYRHROBD-UHFFFAOYSA-N 0.000 claims 1
KSCSVTXFNVHEPS-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC1C2=CC(OC)=CC=C2CCC1 KSCSVTXFNVHEPS-UHFFFAOYSA-N 0.000 claims 1
GPKMTQAGCOVWSO-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]-3,6-dihydro-2H-pyridine-5-carboxylate Chemical compound C(C)OC(=O)C=1CN(CCC1O)CC1CC2=CC(=CC=C2CC1)OC GPKMTQAGCOVWSO-UHFFFAOYSA-N 0.000 claims 1
YLZCHDCWYIEPJG-UHFFFAOYSA-N ethyl 4-hydroxy-1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CCC1=CC2=CC=C(OC)C=C12 YLZCHDCWYIEPJG-UHFFFAOYSA-N 0.000 claims 1
OXQYTYRKYRXTJB-UHFFFAOYSA-N ethyl 4-hydroxy-1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4-trienylidene)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OCC)=C(O)CCN1CC=C1C2=CC(OC)=CC=C2C1 OXQYTYRKYRXTJB-UHFFFAOYSA-N 0.000 claims 1
UIVWVTQOGSSCLH-UHFFFAOYSA-N ethyl 4-hydroxy-1-[2-(6-methoxy-2,3-dihydro-1H-inden-1-yl)ethyl]-3,6-dihydro-2H-pyridine-5-carboxylate Chemical compound C(C)OC(=O)C=1CN(CCC1O)CCC1CCC2=CC=C(C=C12)OC UIVWVTQOGSSCLH-UHFFFAOYSA-N 0.000 claims 1
UUZUBCCNOUACBN-UHFFFAOYSA-N ethyl 4-imino-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]piperidine-3-carboxylate Chemical compound C1CC(=N)C(C(=O)OCC)CN1CC1=CC2=CC=C(OC)C=C12 UUZUBCCNOUACBN-UHFFFAOYSA-N 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
PJXPLQDWGMEUTM-UHFFFAOYSA-N methyl 1-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1C1CC2=CC(OC)=CC=C2CC1 PJXPLQDWGMEUTM-UHFFFAOYSA-N 0.000 claims 1
JTOFVGPEDUADTD-UHFFFAOYSA-N methyl 1-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1CC1C2=CC(OC)=CC=C2CC1 JTOFVGPEDUADTD-UHFFFAOYSA-N 0.000 claims 1
KXGSKLBVPJMYNX-UHFFFAOYSA-N methyl 1-[(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1CC1CC2=CC(OC)=CC=C2CC1 KXGSKLBVPJMYNX-UHFFFAOYSA-N 0.000 claims 1
UNHYONJIHFBGAS-UHFFFAOYSA-N methyl 4-hydroxy-1-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=C(O)CCN1C1CC2=CC(OC)=CC=C2CC1 UNHYONJIHFBGAS-UHFFFAOYSA-N 0.000 claims 1
DCFGTZIAKOCQEP-UHFFFAOYSA-N methyl 4-hydroxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]-3,6-dihydro-2H-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=C(O)CCN1CC1=C(C=C(OC)C=C2)C2=C1 DCFGTZIAKOCQEP-UHFFFAOYSA-N 0.000 claims 1
VVEIESYVPHIUHK-UHFFFAOYSA-N methyl 4-hydroxy-1-[(6-methoxy-2,3-dihydro-1H-inden-1-yl)methyl]-3,6-dihydro-2H-pyridine-5-carboxylate Chemical compound COC(=O)C=1CN(CCC1O)CC1CCC2=CC=C(C=C12)OC VVEIESYVPHIUHK-UHFFFAOYSA-N 0.000 claims 1
BNKXWOULDSELIW-UHFFFAOYSA-N methyl 4-hydroxy-1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=C(O)CCN1CCC1=C(C=C(OC)C=C2)C2=C1 BNKXWOULDSELIW-UHFFFAOYSA-N 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 268
239000000243 solution Substances 0.000 description 175
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 173
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 159
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 133
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 127
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 71
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 63
238000004821 distillation Methods 0.000 description 62
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 56
238000002844 melting Methods 0.000 description 53
230000008018 melting Effects 0.000 description 53
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 51
239000011541 reaction mixture Substances 0.000 description 50
239000007858 starting material Substances 0.000 description 49
239000012074 organic phase Substances 0.000 description 42
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 40
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 39
239000003921 oil Substances 0.000 description 39
235000019198 oils Nutrition 0.000 description 39
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 38
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 36
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 35
238000006243 chemical reaction Methods 0.000 description 34
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 33
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 32
229910052938 sodium sulfate Inorganic materials 0.000 description 32
235000011152 sodium sulphate Nutrition 0.000 description 32
239000002585 base Substances 0.000 description 30
238000003756 stirring Methods 0.000 description 26
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239000003513 alkali Substances 0.000 description 1
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150000001342 alkaline earth metals Chemical class 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
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230000015572 biosynthetic process Effects 0.000 description 1
SIPUZPBQZHNSDW-UHFFFAOYSA-N bis(2-methylpropyl)aluminum Chemical compound CC(C)C[Al]CC(C)C SIPUZPBQZHNSDW-UHFFFAOYSA-N 0.000 description 1
238000009835 boiling Methods 0.000 description 1
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical class B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
MCQRPQCQMGVWIQ-UHFFFAOYSA-N boron;methylsulfanylmethane Chemical compound [B].CSC MCQRPQCQMGVWIQ-UHFFFAOYSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 description 1
125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 1
229910000024 caesium carbonate Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
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FUFJGUQYACFECW-UHFFFAOYSA-L calcium hydrogenphosphate Chemical compound [Ca+2].OP([O-])([O-])=O FUFJGUQYACFECW-UHFFFAOYSA-L 0.000 description 1
235000011010 calcium phosphates Nutrition 0.000 description 1
CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical compound [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
239000008116 calcium stearate Substances 0.000 description 1
235000013539 calcium stearate Nutrition 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
229920002301 cellulose acetate Polymers 0.000 description 1
KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
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125000001309 chloro group Chemical group Cl* 0.000 description 1
101150113676 chr1 gene Proteins 0.000 description 1
238000011097 chromatography purification Methods 0.000 description 1
239000008119 colloidal silica Substances 0.000 description 1
239000012230 colorless oil Substances 0.000 description 1
239000000470 constituent Substances 0.000 description 1
150000001879 copper Chemical class 0.000 description 1
239000013058 crude material Substances 0.000 description 1
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230000018044 dehydration Effects 0.000 description 1
238000006297 dehydration reaction Methods 0.000 description 1
239000008367 deionised water Substances 0.000 description 1
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235000019700 dicalcium phosphate Nutrition 0.000 description 1
150000001991 dicarboxylic acids Chemical class 0.000 description 1
239000002027 dichloromethane extract Substances 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
MKRTXPORKIRPDG-UHFFFAOYSA-N diphenylphosphoryl azide Chemical compound C=1C=CC=CC=1P(=O)(N=[N+]=[N-])C1=CC=CC=C1 MKRTXPORKIRPDG-UHFFFAOYSA-N 0.000 description 1
239000007884 disintegrant Substances 0.000 description 1
BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 1
229910000397 disodium phosphate Inorganic materials 0.000 description 1
235000019800 disodium phosphate Nutrition 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
150000002081 enamines Chemical class 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
DNKPAQBOARFDJT-HZPDHXFCSA-N ethyl (3r,4r)-1-(7-bicyclo[4.2.0]octa-1,3,5,7-tetraenylmethyl)-4-hydroxypiperidine-3-carboxylate Chemical compound C1C[C@@H](O)[C@H](C(=O)OCC)CN1CC1=CC2=CC=CC=C12 DNKPAQBOARFDJT-HZPDHXFCSA-N 0.000 description 1
YNWQBGTWCQVLSY-UHFFFAOYSA-N ethyl 1,2,3,4-tetrahydronaphthalene-2-carboxylate Chemical compound C1=CC=C2CC(C(=O)OCC)CCC2=C1 YNWQBGTWCQVLSY-UHFFFAOYSA-N 0.000 description 1
ICYQMWVPBPXAIC-UHFFFAOYSA-N ethyl 1,2,3,4-tetrahydropyridine-3-carboxylate Chemical compound CCOC(=O)C1CNC=CC1 ICYQMWVPBPXAIC-UHFFFAOYSA-N 0.000 description 1
UCDCRCODJIZPFI-UHFFFAOYSA-N ethyl 1,2,3,4-tetrahydropyridine-3-carboxylate hydrochloride Chemical compound Cl.C(C)OC(=O)C1CNC=CC1 UCDCRCODJIZPFI-UHFFFAOYSA-N 0.000 description 1
ZBYKDEIZQLFOCC-UHFFFAOYSA-N ethyl 1-(6-methoxy-2,3-dihydro-1h-inden-1-yl)-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1C1C2=CC(OC)=CC=C2CC1 ZBYKDEIZQLFOCC-UHFFFAOYSA-N 0.000 description 1
PHNNMNHXCOKKPQ-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1,3,5,7-tetraenyl)-4-hydroxy-3,6-dihydro-2h-pyridine-5-carboxylate;hydrochloride Chemical compound Cl.C1C(C(=O)OCC)=C(O)CCN1C1=CC2=CC=CC=C12 PHNNMNHXCOKKPQ-UHFFFAOYSA-N 0.000 description 1
KUGXCLDIAZDCJR-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1,3,5,7-tetraenylmethyl)-3,6-dihydro-2h-pyridine-5-carboxylate;hydrochloride Chemical compound Cl.C1C(C(=O)OCC)=CCCN1CC1=CC2=CC=CC=C12 KUGXCLDIAZDCJR-UHFFFAOYSA-N 0.000 description 1
YUTJOUFGLJSDCN-UHFFFAOYSA-N ethyl 1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-4-oxopiperidine-3-carboxylate Chemical class C1CC(=O)C(C(=O)OCC)CN1CC1=CC2=CC=C(OC)C=C12 YUTJOUFGLJSDCN-UHFFFAOYSA-N 0.000 description 1
ZKRUKDKIBJNCNR-UHFFFAOYSA-N ethyl 1-[(4-methoxy-7-methyl-7-bicyclo[4.2.0]octa-1(6),2,4-trienyl)methyl]-4-oxopiperidine-3-carboxylate;hydrochloride Chemical compound Cl.C1CC(=O)C(C(=O)OCC)CN1CC1(C)C2=CC(OC)=CC=C2C1 ZKRUKDKIBJNCNR-UHFFFAOYSA-N 0.000 description 1
IHHNVXLMUQNSJK-UHFFFAOYSA-N ethyl 1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]-4-oxopiperidine-3-carboxylate;hydrochloride Chemical compound Cl.C1CC(=O)C(C(=O)OCC)CN1CCC1=CC2=CC=C(OC)C=C12 IHHNVXLMUQNSJK-UHFFFAOYSA-N 0.000 description 1
DUMNOWYWTAYLJN-UHFFFAOYSA-N ethyl 2-oxopiperidine-3-carboxylate Chemical compound CCOC(=O)C1CCCNC1=O DUMNOWYWTAYLJN-UHFFFAOYSA-N 0.000 description 1
PRLPNFBICXAAKY-UHFFFAOYSA-N ethyl 3-[(3-methoxy-5-methyl-8-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methylamino]propanoate Chemical compound C1=C(OC)C=C(C)C2=C1C(CNCCC(=O)OCC)=C2 PRLPNFBICXAAKY-UHFFFAOYSA-N 0.000 description 1
QJHILYFSUYFSTN-UHFFFAOYSA-N ethyl 3-[(4-chloro-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methylamino]propanoate Chemical compound C1=C(Cl)C=C2C(CNCCC(=O)OCC)=CC2=C1 QJHILYFSUYFSTN-UHFFFAOYSA-N 0.000 description 1
KPAUNAAAGPHSFP-UHFFFAOYSA-N ethyl 3-[(4-hydroxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methylamino]propanoate Chemical compound C1=C(O)C=C2C(CNCCC(=O)OCC)=CC2=C1 KPAUNAAAGPHSFP-UHFFFAOYSA-N 0.000 description 1
RBAYLWRNGVVTJT-UHFFFAOYSA-N ethyl 3-[(4-methoxy-8-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methylamino]propanoate Chemical compound COC1=CC=C2C(CNCCC(=O)OCC)=CC2=C1 RBAYLWRNGVVTJT-UHFFFAOYSA-N 0.000 description 1
IUQKIDPYUBLAEF-UHFFFAOYSA-N ethyl 3-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)amino]propanoate Chemical compound C1=C(OC)C=C2C(NCCC(=O)OCC)CCC2=C1 IUQKIDPYUBLAEF-UHFFFAOYSA-N 0.000 description 1
WHGRJHAMJSCNKR-UHFFFAOYSA-N ethyl 3-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methylamino]propanoate Chemical compound C1=C(OC)C=C2C(CNCCC(=O)OCC)CCC2=C1 WHGRJHAMJSCNKR-UHFFFAOYSA-N 0.000 description 1
YXXQAWWAJOPZMX-UHFFFAOYSA-M ethyl 4-ethoxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]pyridin-1-ium-3-carboxylate;4-methylbenzenesulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1.C1=C(OCC)C(C(=O)OCC)=C[N+](CC=2C3=CC(OC)=CC=C3C=2)=C1 YXXQAWWAJOPZMX-UHFFFAOYSA-M 0.000 description 1
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WJMRXKHVNFRWSK-UHFFFAOYSA-N ethyl 4-hydroxy-1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate;hydrochloride Chemical compound Cl.C1C(C(=O)OCC)=C(O)CCN1CCC1=CC2=CC=C(OC)C=C12 WJMRXKHVNFRWSK-UHFFFAOYSA-N 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
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230000012953 feeding on blood of other organism Effects 0.000 description 1
238000001914 filtration Methods 0.000 description 1
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229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000006260 foam Substances 0.000 description 1
238000009472 formulation Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000004108 freeze drying Methods 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
238000005469 granulation Methods 0.000 description 1
230000003179 granulation Effects 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
150000004677 hydrates Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
238000007327 hydrogenolysis reaction Methods 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
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230000003100 immobilizing effect Effects 0.000 description 1
238000011065 in-situ storage Methods 0.000 description 1
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
229910052742 iron Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004922 lacquer Substances 0.000 description 1
238000011068 loading method Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
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VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
229910052987 metal hydride Inorganic materials 0.000 description 1
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238000001465 metallisation Methods 0.000 description 1
DOXOETUWVNVADB-UHFFFAOYSA-N methyl 1,2,3,6-tetrahydropyridine-5-carboxylate;hydrobromide Chemical compound Br.COC(=O)C1=CCCNC1 DOXOETUWVNVADB-UHFFFAOYSA-N 0.000 description 1
UETBHHQIDQZJSU-UHFFFAOYSA-N methyl 3-[(5-methoxy-2,3-dihydro-1h-inden-2-yl)methylamino]propanoate Chemical class C1=C(OC)C=C2CC(CNCCC(=O)OC)CC2=C1 UETBHHQIDQZJSU-UHFFFAOYSA-N 0.000 description 1
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OWUIBIXITPBQDN-UHFFFAOYSA-N methyl 4-hydroxy-1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-3,6-dihydro-2h-pyridine-5-carboxylate;hydrochloride Chemical compound Cl.C1C(C(=O)OC)=C(O)CCN1CC1=CC2=CC=C(OC)C=C12 OWUIBIXITPBQDN-UHFFFAOYSA-N 0.000 description 1
JXRBXNDFMVNTGU-UHFFFAOYSA-N methyl 6-methoxy-2,3-dihydro-1h-indene-1-carboxylate Chemical compound C1=C(OC)C=C2C(C(=O)OC)CCC2=C1 JXRBXNDFMVNTGU-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 1
BCDBHIAXYFPJCT-UHFFFAOYSA-N methyl piperidine-3-carboxylate Chemical compound COC(=O)C1CCCNC1 BCDBHIAXYFPJCT-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
244000005700 microbiome Species 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
239000003607 modifier Substances 0.000 description 1
125000002950 monocyclic group Chemical group 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
ULWOJODHECIZAU-UHFFFAOYSA-N n,n-diethylpropan-2-amine Chemical group CCN(CC)C(C)C ULWOJODHECIZAU-UHFFFAOYSA-N 0.000 description 1
AJUXDFHPVZQOGF-UHFFFAOYSA-N n,n-dimethyl-1-naphthylamine Chemical compound C1=CC=C2C(N(C)C)=CC=CC2=C1 AJUXDFHPVZQOGF-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
SSNISTUBYRMYDY-UHFFFAOYSA-N n-methyl-1-naphthalen-2-ylmethanamine Chemical compound C1=CC=CC2=CC(CNC)=CC=C21 SSNISTUBYRMYDY-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
RMHJJUOPOWPRBP-UHFFFAOYSA-N naphthalene-1-carboxamide Chemical compound C1=CC=C2C(C(=O)N)=CC=CC2=C1 RMHJJUOPOWPRBP-UHFFFAOYSA-N 0.000 description 1
UFWIBTONFRDIAS-UHFFFAOYSA-N naphthalene-acid Natural products C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 1
239000002547 new drug Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
230000001777 nootropic effect Effects 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
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239000000049 pigment Substances 0.000 description 1
XIMLAVRHZBUYBE-UHFFFAOYSA-N piperidin-2-one;hydrate;hydrochloride Chemical compound O.Cl.O=C1CCCCN1 XIMLAVRHZBUYBE-UHFFFAOYSA-N 0.000 description 1
229910052697 platinum Inorganic materials 0.000 description 1
229940093429 polyethylene glycol 6000 Drugs 0.000 description 1
IUBQJLUDMLPAGT-UHFFFAOYSA-N potassium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([K])[Si](C)(C)C IUBQJLUDMLPAGT-UHFFFAOYSA-N 0.000 description 1
CHWRSCGUEQEHOH-UHFFFAOYSA-N potassium oxide Chemical compound [O-2].[K+].[K+] CHWRSCGUEQEHOH-UHFFFAOYSA-N 0.000 description 1
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230000003449 preventive effect Effects 0.000 description 1
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YYFIGOPUHPDIBO-UHFFFAOYSA-N propanoic acid;hydrochloride Chemical compound Cl.CCC(O)=O YYFIGOPUHPDIBO-UHFFFAOYSA-N 0.000 description 1
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230000000069 prophylactic effect Effects 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
230000001337 psychedelic effect Effects 0.000 description 1
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229910052703 rhodium Inorganic materials 0.000 description 1
239000010948 rhodium Substances 0.000 description 1
MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
229940100486 rice starch Drugs 0.000 description 1
229910052707 ruthenium Inorganic materials 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
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239000001632 sodium acetate Substances 0.000 description 1
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229940005550 sodium alginate Drugs 0.000 description 1
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 1
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 1
BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
229910001415 sodium ion Inorganic materials 0.000 description 1
NASFKTWZWDYFER-UHFFFAOYSA-N sodium;hydrate Chemical compound O.[Na] NASFKTWZWDYFER-UHFFFAOYSA-N 0.000 description 1
239000007901 soft capsule Substances 0.000 description 1
239000007790 solid phase Substances 0.000 description 1
238000007614 solvation Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
241000894007 species Species 0.000 description 1
KXCAEQNNTZANTK-UHFFFAOYSA-N stannane Chemical compound [SnH4] KXCAEQNNTZANTK-UHFFFAOYSA-N 0.000 description 1
239000000021 stimulant Substances 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
150000008163 sugars Chemical class 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
229910052717 sulfur Inorganic materials 0.000 description 1
229910021653 sulphate ion Inorganic materials 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YBRBMKDOPFTVDT-UHFFFAOYSA-N tert-butylamine Chemical compound CC(C)(C)N YBRBMKDOPFTVDT-UHFFFAOYSA-N 0.000 description 1
NYBWUHOMYZZKOR-UHFFFAOYSA-N tes-adt Chemical class C1=C2C(C#C[Si](CC)(CC)CC)=C(C=C3C(SC=C3)=C3)C3=C(C#C[Si](CC)(CC)CC)C2=CC2=C1SC=C2 NYBWUHOMYZZKOR-UHFFFAOYSA-N 0.000 description 1
UNWZKBKTIYBBRV-UHFFFAOYSA-N tetraazanium;tetrachloride Chemical compound [NH4+].[NH4+].[NH4+].[NH4+].[Cl-].[Cl-].[Cl-].[Cl-] UNWZKBKTIYBBRV-UHFFFAOYSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
239000011135 tin Substances 0.000 description 1
229910052718 tin Inorganic materials 0.000 description 1
229910000083 tin tetrahydride Inorganic materials 0.000 description 1
229910052719 titanium Inorganic materials 0.000 description 1
239000004408 titanium dioxide Substances 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
229940078499 tricalcium phosphate Drugs 0.000 description 1
235000019731 tricalcium phosphate Nutrition 0.000 description 1
229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
CPRPKIMXLHBUGA-UHFFFAOYSA-N triethyltin Chemical group CC[Sn](CC)CC CPRPKIMXLHBUGA-UHFFFAOYSA-N 0.000 description 1
239000005051 trimethylchlorosilane Substances 0.000 description 1
JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
239000003981 vehicle Substances 0.000 description 1
239000000052 vinegar Substances 0.000 description 1
235000021419 vinegar Nutrition 0.000 description 1
238000010792 warming Methods 0.000 description 1
229940100445 wheat starch Drugs 0.000 description 1
229940102001 zinc bromide Drugs 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Hydrogenated Pyridines (AREA)
Pyridine Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

JP19920286A 1985-08-27 1986-08-27 ヒドロピリジン誘導体、その製造法及び向知性薬 Granted JPS6251650A (ja)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH3669/85-5		1985-08-27
CH366985		1985-08-27
CH2586/86-3		1986-06-26

Publications (2)

Publication Number	Publication Date
JPS6251650A true JPS6251650A (ja)	1987-03-06
JPH055828B2 JPH055828B2 (da)	1993-01-25

Family

ID=4260962

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP19920286A Granted JPS6251650A (ja)	1985-08-27	1986-08-27	ヒドロピリジン誘導体、その製造法及び向知性薬

Country Status (3)

Country	Link
JP (1)	JPS6251650A (da)
DD (1)	DD259189A5 (da)
ZA (1)	ZA866442B (da)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07159A (ja) *	1991-08-30	1995-01-06	Noritake Co Ltd	篩い作動式焙煎機における炒成機構

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57179141A (en) *	1981-04-28	1982-11-04	Takeda Chem Ind Ltd	Bicyclic compound and its preparation

1986
- 1986-08-25 DD DD86293839A patent/DD259189A5/de not_active IP Right Cessation
- 1986-08-26 ZA ZA866442A patent/ZA866442B/xx unknown
- 1986-08-27 JP JP19920286A patent/JPS6251650A/ja active Granted

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS57179141A (en) *	1981-04-28	1982-11-04	Takeda Chem Ind Ltd	Bicyclic compound and its preparation

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPH07159A (ja) *	1991-08-30	1995-01-06	Noritake Co Ltd	篩い作動式焙煎機における炒成機構

Also Published As

Publication number	Publication date
JPH055828B2 (da)	1993-01-25
DD259189A5 (de)	1988-08-17
ZA866442B (en)	1987-04-29

Publication	Publication Date	Title
US4954502A (en)	1990-09-04	1-indolyalkyl-4-(substituted-pyridinyl)piperazines
US6479480B1 (en)	2002-11-12	Phenylindole derivatives as 5-ht2a receptor ligands
JPS63146874A (ja)	1988-06-18	インドール誘導体
JPS6289679A (ja)	1987-04-24	ピペリジン誘導体
BG60472B2 (bg)	1995-04-28	Производни на 1-(циклохексил или циклохексенил)-4-арил-4- пиперидинкарбоксилова киселина
US5670522A (en)	1997-09-23	Dopamine receptor subtype ligands
EP0674514A1 (en)	1995-10-04	Use of aryloxyalkyl substituted cyclic amines as calcium channel antagonists and new phenyloxyalkyl piperidin derivatives
NO146359B (no)	1982-06-07	Analogifremgangsmaate ved fremstilling av terapeutisk aktive cyproheptadinderivater
HU186523B (en)	1985-08-28	Process for producing quinoline derivatives
US4251538A (en)	1981-02-17	Indolealkylamines and processes for their preparation
AU644296B2 (en)	1993-12-02	2-(1-piperidyl)ethanol derivatives, their preparation and their therapeutic application
JPS638382A (ja)	1988-01-14	水素添加された１−ベンゾオキサシクロアルキルピリジンカルボン酸化合物，その製造方法及び該化合物を含む医薬製剤
US5760035A (en)	1998-06-02	Therapeutic agents
US4243666A (en)	1981-01-06	4-Amino-2-piperidino-quinazolines
JP5586591B2 (ja)	2014-09-10	アラルキルアルコールピペリジン誘導体及びその抗うつ病薬物としての使用
NO173988B (no)	1993-11-22	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrrolidinderivater
JPH05320139A (ja)	1993-12-03	シクロヘプトイミダゾ−ル誘導体及びその製造方法並びにこれを含有する薬剤
US5789595A (en)	1998-08-04	Tetrahydroisoquinoline derivative and medical preparation containing the same
JPS6251650A (ja)	1987-03-06	ヒドロピリジン誘導体、その製造法及び向知性薬
JPH07508517A (ja)	1995-09-21	新規ニコチン酸エステル
IE904230A1 (en)	1991-06-05	Azacyclic derivatives
JPS604170B2 (ja)	1985-02-01	１，２− ジフエニルエタノ−ルアミン誘導体の製法
KR910000034B1 (ko)	1991-01-19	하이드로피리딘 유도체의 제조방법
JPH0516429B2 (da)	1993-03-04
SG192510A1 (en)	2013-08-30	Ethanamine compounds and their use for treating depression

JPS6251650A - ヒドロピリジン誘導体、その製造法及び向知性薬 - Google Patents

Info

Links

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Applications Claiming Priority (3)

Publications (2)

Family

ID=4260962

Family Applications (1)

Country Status (3)

Cited By (1)

Citations (1)

Patent Citations (1)

Cited By (1)

Also Published As

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