JPH055828B2

JPH055828B2 -

Info

Publication number: JPH055828B2
Authority: JP; Japan
Prior art keywords: carboxylic acid; methyl; hydroxy; ethyl ester; acid ethyl
Prior art date: 1985-08-27
Legal status : Expired - Lifetime

Application number

JP61199202A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6251650A (ja

Inventor

Fuon Shupuretsuhaa Georugu

Furuusutoru Uorufugangu

Chusuto Arumin

Current Assignee

Novartis AG

Original Assignee

Ciba Geigy AG

Priority date

1985-08-27

Filing date

1986-08-27

Publication date

1993-01-25

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

-1 pyridoyloxy Chemical group 0.000 claims description 230
239000000203 mixture Substances 0.000 claims description 143
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 130
150000001875 compounds Chemical class 0.000 claims description 122
150000003839 salts Chemical class 0.000 claims description 122
239000002253 acid Substances 0.000 claims description 74
238000000034 method Methods 0.000 claims description 74
125000003545 alkoxy group Chemical group 0.000 claims description 67
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 67
125000000217 alkyl group Chemical group 0.000 claims description 65
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 50
125000004432 carbon atom Chemical group C* 0.000 claims description 49
229910052736 halogen Inorganic materials 0.000 claims description 43
150000002367 halogens Chemical group 0.000 claims description 42
238000006243 chemical reaction Methods 0.000 claims description 41
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 38
229910052739 hydrogen Inorganic materials 0.000 claims description 31
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 30
239000001257 hydrogen Substances 0.000 claims description 30
125000004423 acyloxy group Chemical group 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 25
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 25
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 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 18
125000001118 alkylidene group Chemical group 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 15
125000004122 cyclic group Chemical group 0.000 claims description 14
238000004519 manufacturing process Methods 0.000 claims description 14
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 13
230000001777 nootropic effect Effects 0.000 claims description 11
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 claims description 10
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 9
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 9
125000006239 protecting group Chemical group 0.000 claims description 7
125000000043 benzamido group Chemical group [H]N([*])C(=O)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
125000001231 benzoyloxy group Chemical group C(C1=CC=CC=C1)(=O)O* 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000001841 imino group Chemical group [H]N=* 0.000 claims description 6
239000002664 nootropic agent Substances 0.000 claims description 6
230000008569 process Effects 0.000 claims description 6
239000005973 Carvone Substances 0.000 claims description 5
150000001450 anions Chemical class 0.000 claims description 5
125000003739 carbamimidoyl group Chemical group C(N)(=N)* 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
238000003797 solvolysis reaction Methods 0.000 claims description 5
UMIVXZPTRXBADB-UHFFFAOYSA-N benzocyclobutene Chemical compound C1=CC=C2CCC2=C1 UMIVXZPTRXBADB-UHFFFAOYSA-N 0.000 claims description 4
PZGOWXPGHVSKNO-UHFFFAOYSA-N 4-methoxybicyclo[4.2.0]octa-1(6),2,4-triene Chemical compound COC1=CC=C2CCC2=C1 PZGOWXPGHVSKNO-UHFFFAOYSA-N 0.000 claims description 3
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 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
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 description 3
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 description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 2
125000004466 alkoxycarbonylamino group Chemical group 0.000 claims 12
125000005194 alkoxycarbonyloxy group Chemical group 0.000 claims 8
125000005236 alkanoylamino group Chemical group 0.000 claims 5
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 2
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 2
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 2
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 2
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 2
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 2
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 2
JFBZZYORKLGCOK-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1,3,5,7-tetraenyl)-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1C1=CC2=CC=CC=C12 JFBZZYORKLGCOK-UHFFFAOYSA-N 0.000 claims 2
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 2
GYNOOWYMUBHFHF-UHFFFAOYSA-N ethyl 1-(7-bicyclo[4.2.0]octa-1,3,5,7-tetraenylmethyl)-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1=CC2=CC=CC=C12 GYNOOWYMUBHFHF-UHFFFAOYSA-N 0.000 claims 2
FKIJREGCUZPRLB-UHFFFAOYSA-N ethyl 1-[(3-methoxy-5-methyl-8-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1=CC2=C1C=C(OC)C=C2C FKIJREGCUZPRLB-UHFFFAOYSA-N 0.000 claims 2
FXBUXUOZKHERJT-UHFFFAOYSA-N ethyl 1-[(4-chloro-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1=CC2=CC=C(Cl)C=C12 FXBUXUOZKHERJT-UHFFFAOYSA-N 0.000 claims 2
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 2
XEPPCWBHENIJRW-UHFFFAOYSA-N ethyl 1-[(4-methoxy-8-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1=CC2=CC(OC)=CC=C12 XEPPCWBHENIJRW-UHFFFAOYSA-N 0.000 claims 2
QAOYFXZQEHSYTI-UHFFFAOYSA-N ethyl 1-[(6-methoxy-2,3-dihydro-1h-inden-1-yl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1C2=CC(OC)=CC=C2CC1 QAOYFXZQEHSYTI-UHFFFAOYSA-N 0.000 claims 2
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 2
BMHQHXGIIIROGI-UHFFFAOYSA-N ethyl 1-[(7-methoxy-1,2,3,4-tetrahydronaphthalen-1-yl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CC1C2=CC(OC)=CC=C2CCC1 BMHQHXGIIIROGI-UHFFFAOYSA-N 0.000 claims 2
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 2
NHMNSYNQCSJACM-UHFFFAOYSA-N ethyl 1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CCC1=CC2=CC=C(OC)C=C12 NHMNSYNQCSJACM-UHFFFAOYSA-N 0.000 claims 2
HPFSJRSDRANYQS-UHFFFAOYSA-N ethyl 1-[2-(6-methoxy-2,3-dihydro-1h-inden-1-yl)ethyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OCC)CN1CCC1C2=CC(OC)=CC=C2CC1 HPFSJRSDRANYQS-UHFFFAOYSA-N 0.000 claims 2
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 2
CPNJBZSRVHFBSX-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(4-hydroxy-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(O)C=C2)C2=C1 CPNJBZSRVHFBSX-UHFFFAOYSA-N 0.000 claims 2
XFOSFGLRDKGMEG-UHFFFAOYSA-N ethyl 4-hydroxy-1-[(4-methoxy-2-methyl-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=C2C)C2=C1 XFOSFGLRDKGMEG-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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 2
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
UNLLAMJDGOZEEH-UHFFFAOYSA-N methyl 1-(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1C1CC2=CC(OC)=CC=C2CC1 UNLLAMJDGOZEEH-UHFFFAOYSA-N 0.000 claims 2
LDTDZOMQBSFRAP-UHFFFAOYSA-N methyl 1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1CC1=CC2=CC=C(OC)C=C12 LDTDZOMQBSFRAP-UHFFFAOYSA-N 0.000 claims 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 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 2
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 2
DIAVOXYNTHHDFL-UHFFFAOYSA-N methyl 1-[(7-methoxy-1,2,3,4-tetrahydronaphthalen-2-yl)methyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1CC1CC2=CC(OC)=CC=C2CC1 DIAVOXYNTHHDFL-UHFFFAOYSA-N 0.000 claims 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 2
BFQJBEYGXCVWOG-UHFFFAOYSA-N methyl 1-[2-(4-methoxy-7-bicyclo[4.2.0]octa-1(6),2,4,7-tetraenyl)ethyl]-4-oxopiperidine-3-carboxylate Chemical compound C1CC(=O)C(C(=O)OC)CN1CCC1=CC2=CC=C(OC)C=C12 BFQJBEYGXCVWOG-UHFFFAOYSA-N 0.000 claims 2
SDYHCWDOLLRGHT-UHFFFAOYSA-N methyl 1-[2-(6-methoxy-2,3-dihydro-1h-inden-1-yl)ethyl]-3,6-dihydro-2h-pyridine-5-carboxylate Chemical compound C1C(C(=O)OC)=CCCN1CCC1C2=CC(OC)=CC=C2CC1 SDYHCWDOLLRGHT-UHFFFAOYSA-N 0.000 claims 2
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 2
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 2
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 2
BCDBHIAXYFPJCT-UHFFFAOYSA-N methyl piperidine-3-carboxylate Chemical compound COC(=O)C1CCCNC1 BCDBHIAXYFPJCT-UHFFFAOYSA-N 0.000 claims 2
YBVLHYSOWMKSBK-UHFFFAOYSA-N 1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]piperidin-4-one Chemical compound C12=CC(OC)=CC=C2C=C1CN1CCC(=O)CC1 YBVLHYSOWMKSBK-UHFFFAOYSA-N 0.000 claims 1
RMZQUHGQYLQKIC-UHFFFAOYSA-N 1-[(4-methoxy-7-bicyclo[4.2.0]octa-1(8),2,4,6-tetraenyl)methyl]piperidine-3-carboxylic acid Chemical compound C12=CC(OC)=CC=C2C=C1CN1CCCC(C(O)=O)C1 RMZQUHGQYLQKIC-UHFFFAOYSA-N 0.000 claims 1
101100490437 Mus musculus Acvrl1 gene Proteins 0.000 claims 1
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