MX2007007573A

MX2007007573A - Indoles de 3-cicloalquilcarbonilo en la forma de ligandos de receptor canabinoide.

Indoles de 3-cicloalquilcarbonilo en la forma de ligandos de receptor canabinoide.

Info

Publication number: MX2007007573A
Authority: MX; Mexico
Prior art keywords: tetramethylcyclopropyl; indol; methanone; mmol; tetrahydro
Prior art date: 2004-12-21

Application number

MX2007007573A

Other languages

English (en)

Spanish (es)

Inventor

Michael J Dart

Jennifer M Pace

Karin Tietje

Michael D Meyer

Original Assignee

Abbott Lab

Priority date

2004-12-21

Filing date

2005-12-21

Publication date

2007-07-24

2005-12-21 Application filed by Abbott Lab filed Critical Abbott Lab

2007-07-24 Publication of MX2007007573A publication Critical patent/MX2007007573A/es

Links

239000003446 ligand Substances 0.000 title claims abstract description 10
102000018208 Cannabinoid Receptor Human genes 0.000 title description 15
108050007331 Cannabinoid receptor Proteins 0.000 title description 15
150000001875 compounds Chemical class 0.000 claims abstract description 339
208000002193 Pain Diseases 0.000 claims abstract description 30
230000036407 pain Effects 0.000 claims abstract description 30
238000011282 treatment Methods 0.000 claims abstract description 27
-1 carboxyalkylcarbonyl Chemical group 0.000 claims description 558
125000000217 alkyl group Chemical group 0.000 claims description 208
239000001257 hydrogen Substances 0.000 claims description 104
229910052739 hydrogen Inorganic materials 0.000 claims description 104
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 95
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 74
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 72
IQBFNXYAKGOFOB-UHFFFAOYSA-N 2,2,3,3-tetramethylcyclopropane-1-carbaldehyde Chemical compound CC1(C)C(C=O)C1(C)C IQBFNXYAKGOFOB-UHFFFAOYSA-N 0.000 claims description 69
125000003545 alkoxy group Chemical group 0.000 claims description 53
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 50
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 45
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 41
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 39
238000000034 method Methods 0.000 claims description 39
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 claims description 37
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 37
125000003710 aryl alkyl group Chemical group 0.000 claims description 37
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 36
125000001188 haloalkyl group Chemical group 0.000 claims description 35
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 35
WSFSSNUMVMOOMR-BJUDXGSMSA-N methanone Chemical compound O=[11CH2] WSFSSNUMVMOOMR-BJUDXGSMSA-N 0.000 claims description 35
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 33
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 32
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 32
125000000623 heterocyclic group Chemical group 0.000 claims description 30
125000001072 heteroaryl group Chemical group 0.000 claims description 29
125000004446 heteroarylalkyl group Chemical group 0.000 claims description 27
125000003118 aryl group Chemical group 0.000 claims description 26
125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 26
229910052736 halogen Inorganic materials 0.000 claims description 26
150000002367 halogens Chemical group 0.000 claims description 26
229910052757 nitrogen Inorganic materials 0.000 claims description 26
125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 25
125000000753 cycloalkyl group Chemical group 0.000 claims description 25
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 24
125000003342 alkenyl group Chemical group 0.000 claims description 23
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 23
125000004438 haloalkoxy group Chemical group 0.000 claims description 23
239000002253 acid Substances 0.000 claims description 22
241000124008 Mammalia Species 0.000 claims description 21
125000005093 alkyl carbonyl alkyl group Chemical group 0.000 claims description 20
125000000304 alkynyl group Chemical group 0.000 claims description 20
208000004296 neuralgia Diseases 0.000 claims description 18
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 18
208000021722 neuropathic pain Diseases 0.000 claims description 17
125000002102 aryl alkyloxo group Chemical group 0.000 claims description 16
125000004963 sulfonylalkyl group Chemical group 0.000 claims description 16
125000005243 carbonyl alkyl group Chemical group 0.000 claims description 15
125000004181 carboxyalkyl group Chemical group 0.000 claims description 15
125000005113 hydroxyalkoxy group Chemical group 0.000 claims description 15
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 claims description 14
208000001294 Nociceptive Pain Diseases 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 13
125000005358 mercaptoalkyl group Chemical group 0.000 claims description 13
125000001424 substituent group Chemical group 0.000 claims description 13
125000004966 cyanoalkyl group Chemical group 0.000 claims description 12
125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 11
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 10
125000002947 alkylene group Chemical group 0.000 claims description 10
125000005335 azido alkyl group Chemical group 0.000 claims description 10
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 10
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 10
HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 claims description 10
244000250129 Trigonella foenum graecum Species 0.000 claims description 9
235000001484 Trigonella foenum graecum Nutrition 0.000 claims description 9
229910052799 carbon Inorganic materials 0.000 claims description 9
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 9
210000000987 immune system Anatomy 0.000 claims description 9
206010028980 Neoplasm Diseases 0.000 claims description 8
201000010099 disease Diseases 0.000 claims description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 8
125000003396 thiol group Chemical class [H]S* 0.000 claims description 8
125000005144 cycloalkylsulfonyl group Chemical group 0.000 claims description 7
239000008194 pharmaceutical composition Substances 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
239000003937 drug carrier Substances 0.000 claims description 6
125000004043 oxo group Chemical group O=* 0.000 claims description 6
HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
125000004217 4-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1OC([H])([H])[H])C([H])([H])* 0.000 claims description 5
DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims description 5
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
125000005110 aryl thio group Chemical group 0.000 claims description 5
125000004104 aryloxy group Chemical group 0.000 claims description 5
125000005019 carboxyalkenyl group Chemical group 0.000 claims description 5
125000000000 cycloalkoxy group Chemical group 0.000 claims description 5
125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 5
125000005553 heteroaryloxy group Chemical group 0.000 claims description 5
125000005143 heteroarylsulfonyl group Chemical group 0.000 claims description 5
125000006497 3-methoxybenzyl group Chemical group [H]C1=C([H])C(=C([H])C(OC([H])([H])[H])=C1[H])C([H])([H])* 0.000 claims description 4
208000012902 Nervous system disease Diseases 0.000 claims description 4
208000025966 Neurological disease Diseases 0.000 claims description 4
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 4
125000005140 aralkylsulfonyl group Chemical group 0.000 claims description 4
125000004659 aryl alkyl thio group Chemical group 0.000 claims description 4
125000005129 aryl carbonyl group Chemical group 0.000 claims description 4
125000005160 aryl oxy alkyl group Chemical group 0.000 claims description 4
125000005164 aryl thioalkyl group Chemical group 0.000 claims description 4
125000004858 cycloalkoxyalkyl group Chemical group 0.000 claims description 4
125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 4
125000005114 heteroarylalkoxy group Chemical group 0.000 claims description 4
125000005326 heteroaryloxy alkyl group Chemical group 0.000 claims description 4
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 4
230000004968 inflammatory condition Effects 0.000 claims description 4
230000004112 neuroprotection Effects 0.000 claims description 4
208000023504 respiratory system disease Diseases 0.000 claims description 4
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 claims description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 3
125000005278 alkyl sulfonyloxy group Chemical group 0.000 claims description 3
125000005099 aryl alkyl carbonyl group Chemical group 0.000 claims description 3
125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 3
125000004484 1-methylpiperidin-4-yl group Chemical group CN1CCC(CC1)* 0.000 claims description 2
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
125000004202 aminomethyl group Chemical group [H]N([H])C([H])([H])* 0.000 claims description 2
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
208000026278 immune system disease Diseases 0.000 claims description 2
125000001147 pentyl group Chemical group C(CCCC)* 0.000 claims description 2
239000000651 prodrug Substances 0.000 claims description 2
229940002612 prodrug Drugs 0.000 claims description 2
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
BKNVRCWFHMBUMV-UHFFFAOYSA-N 4-methylbenzenesulfonic acid;2,2,3,3-tetramethylcyclopropane-1-carbaldehyde Chemical compound CC1(C)C(C=O)C1(C)C.CC1=CC=C(S(O)(=O)=O)C=C1 BKNVRCWFHMBUMV-UHFFFAOYSA-N 0.000 claims 3
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims 3
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 claims 2
ZQWPRMPSCMSAJU-UHFFFAOYSA-N methyl cyclohexanecarboxylate Chemical compound COC(=O)C1CCCCC1 ZQWPRMPSCMSAJU-UHFFFAOYSA-N 0.000 claims 2
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims 2
LHOIIJVCNHUAKH-UHFFFAOYSA-N 1-(2-morpholin-4-ylethyl)-3-(2,2,3,3-tetramethylcyclopropanecarbonyl)indole-7-carboxylic acid Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC(=C11)C(O)=O)=CN1CCN1CCOCC1 LHOIIJVCNHUAKH-UHFFFAOYSA-N 0.000 claims 1
ZZTPACIJHCBASD-UHFFFAOYSA-N 1-(oxan-4-ylmethyl)-3-(2,2,3,3-tetramethylcyclopropanecarbonyl)indole-5-carbonitrile Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(=CC=C11)C#N)=CN1CC1CCOCC1 ZZTPACIJHCBASD-UHFFFAOYSA-N 0.000 claims 1
SQVULLNHMLRVEY-UHFFFAOYSA-N 2-morpholin-4-ylethyl 1-(2-morpholin-4-ylethyl)-3-(2,2,3,3-tetramethylcyclopropanecarbonyl)indole-7-carboxylate Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC(=C11)C(=O)OCCN2CCOCC2)=CN1CCN1CCOCC1 SQVULLNHMLRVEY-UHFFFAOYSA-N 0.000 claims 1
QFKHXFSKJAJGEQ-UHFFFAOYSA-N 3-[2-[3-(2,2,3,3-tetramethylcyclopropanecarbonyl)indol-1-yl]ethyl]-1,3-oxazolidin-2-one Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC=C11)=CN1CCN1C(=O)OCC1 QFKHXFSKJAJGEQ-UHFFFAOYSA-N 0.000 claims 1
RRANDYHKXBZJMN-UHFFFAOYSA-N 6-[3-(2,2,3,3-tetramethylcyclopropanecarbonyl)indol-1-yl]hexan-2-one Chemical compound C12=CC=CC=C2N(CCCCC(=O)C)C=C1C(=O)C1C(C)(C)C1(C)C RRANDYHKXBZJMN-UHFFFAOYSA-N 0.000 claims 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims 1
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims 1
ZUNGEUNLBOIWPV-UHFFFAOYSA-N [1-(1,3-benzodioxol-5-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC=C11)=CN1CC1=CC=C(OCO2)C2=C1 ZUNGEUNLBOIWPV-UHFFFAOYSA-N 0.000 claims 1
XJEDISSEYPBTDT-UHFFFAOYSA-N [1-(1,3-benzothiazol-2-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC=C11)=CN1CC1=NC2=CC=CC=C2S1 XJEDISSEYPBTDT-UHFFFAOYSA-N 0.000 claims 1
CRKREDUOEUERNW-UHFFFAOYSA-N [1-(2,3-dihydro-1,4-benzodioxin-6-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC=C11)=CN1CC1=CC=C(OCCO2)C2=C1 CRKREDUOEUERNW-UHFFFAOYSA-N 0.000 claims 1
RENOYULSYYKUBU-UHFFFAOYSA-N [1-(2-methoxyethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound C12=CC=CC=C2N(CCOC)C=C1C(=O)C1C(C)(C)C1(C)C RENOYULSYYKUBU-UHFFFAOYSA-N 0.000 claims 1
MMUASABJIUTYHM-UHFFFAOYSA-N [1-(2-piperidin-1-ylethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC=C11)=CN1CCN1CCCCC1 MMUASABJIUTYHM-UHFFFAOYSA-N 0.000 claims 1
SCUHAQSPCRNNFM-UHFFFAOYSA-N [1-(3,4-dihydroxybutyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C1=CN(CCC(O)CO)C2=CC=CC=C12 SCUHAQSPCRNNFM-UHFFFAOYSA-N 0.000 claims 1
FLCAAEFYUCAUDK-UHFFFAOYSA-N [1-(3-hydroxypropyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C1=CN(CCCO)C2=CC=CC=C12 FLCAAEFYUCAUDK-UHFFFAOYSA-N 0.000 claims 1
WANDNEPYDGEKEF-UHFFFAOYSA-N [1-(3-phenylmethoxypropyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=CC=C11)=CN1CCCOCC1=CC=CC=C1 WANDNEPYDGEKEF-UHFFFAOYSA-N 0.000 claims 1
WYTIDVDJAWZZNN-UHFFFAOYSA-N [1-(5-azidopentyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C1=CN(CCCCCN=[N+]=[N-])C2=CC=CC=C12 WYTIDVDJAWZZNN-UHFFFAOYSA-N 0.000 claims 1
QFMHNGZEDPTVME-UHFFFAOYSA-N [1-(oxan-4-ylmethyl)-4-phenylmethoxyindol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=C(OCC=2C=CC=CC=2)C=CC=C11)=CN1CC1CCOCC1 QFMHNGZEDPTVME-UHFFFAOYSA-N 0.000 claims 1
DKGVGTDAGUCMNK-UHFFFAOYSA-N [1-(oxan-4-ylmethyl)-5-phenylmethoxyindol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(OCC=2C=CC=CC=2)=CC=C11)=CN1CC1CCOCC1 DKGVGTDAGUCMNK-UHFFFAOYSA-N 0.000 claims 1
GWKGBPWEUPDTSJ-UHFFFAOYSA-N [1-(oxan-4-ylmethyl)-6-phenylmethoxyindol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC=C(OCC=2C=CC=CC=2)C=C11)=CN1CC1CCOCC1 GWKGBPWEUPDTSJ-UHFFFAOYSA-N 0.000 claims 1
BYPMRDDODQUEJN-UHFFFAOYSA-N [1-[2-(1-methylimidazol-2-yl)ethyl]indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CN1C=CN=C1CCN1C2=CC=CC=C2C(C(=O)C2C(C2(C)C)(C)C)=C1 BYPMRDDODQUEJN-UHFFFAOYSA-N 0.000 claims 1
VILJBPYHJLDTOV-OAQYLSRUSA-N [1-[[(2r)-oxolan-2-yl]methyl]-5-phenylmethoxyindol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(OCC=2C=CC=CC=2)=CC=C11)=CN1C[C@@H]1OCCC1 VILJBPYHJLDTOV-OAQYLSRUSA-N 0.000 claims 1
BRXJBOGZEFKWPQ-UHFFFAOYSA-N [4-hydroxy-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=C(O)C=CC=C11)=CN1CC1CCOCC1 BRXJBOGZEFKWPQ-UHFFFAOYSA-N 0.000 claims 1
SCYABQWAXMJBKI-UHFFFAOYSA-N [5-(3-methoxyphenyl)-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound COC1=CC=CC(C=2C=C3C(C(=O)C4C(C4(C)C)(C)C)=CN(CC4CCOCC4)C3=CC=2)=C1 SCYABQWAXMJBKI-UHFFFAOYSA-N 0.000 claims 1
OGLYPVVVWXXRJW-UHFFFAOYSA-N [5-(4-bromobutoxy)-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(OCCCCBr)=CC=C11)=CN1CC1CCOCC1 OGLYPVVVWXXRJW-UHFFFAOYSA-N 0.000 claims 1
IRTBNEISJSBZBS-UHFFFAOYSA-N [5-(aminomethyl)-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(CN)=CC=C11)=CN1CC1CCOCC1 IRTBNEISJSBZBS-UHFFFAOYSA-N 0.000 claims 1
FRSWCIYESSAJBI-UHFFFAOYSA-N [5-(methoxymethyl)-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound C1=C(C(=O)C2C(C2(C)C)(C)C)C2=CC(COC)=CC=C2N1CC1CCOCC1 FRSWCIYESSAJBI-UHFFFAOYSA-N 0.000 claims 1
XCWLLVVZCVZVHA-UHFFFAOYSA-N [5-amino-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(N)=CC=C11)=CN1CC1CCOCC1 XCWLLVVZCVZVHA-UHFFFAOYSA-N 0.000 claims 1
ZMEPEBXUHCNCIK-UHFFFAOYSA-N [5-bromo-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(Br)=CC=C11)=CN1CC1CCOCC1 ZMEPEBXUHCNCIK-UHFFFAOYSA-N 0.000 claims 1
IJADFXIQDFOUAG-UHFFFAOYSA-N [5-chloro-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(Cl)=CC=C11)=CN1CC1CCOCC1 IJADFXIQDFOUAG-UHFFFAOYSA-N 0.000 claims 1
RSALASLNYRMGOC-UHFFFAOYSA-N [5-fluoro-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound CC1(C)C(C)(C)C1C(=O)C(C1=CC(F)=CC=C11)=CN1CC1CCOCC1 RSALASLNYRMGOC-UHFFFAOYSA-N 0.000 claims 1
YGUUURKMKPALCH-UHFFFAOYSA-N [5-hydroxy-6-methoxy-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound C1=C(C(=O)C2C(C2(C)C)(C)C)C=2C=C(O)C(OC)=CC=2N1CC1CCOCC1 YGUUURKMKPALCH-UHFFFAOYSA-N 0.000 claims 1
LXIGKLBRCLUENK-UHFFFAOYSA-N [5-methoxy-1-(2-morpholin-4-ylethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound C1=C(C(=O)C2C(C2(C)C)(C)C)C2=CC(OC)=CC=C2N1CCN1CCOCC1 LXIGKLBRCLUENK-UHFFFAOYSA-N 0.000 claims 1
SHHVJVSDLZXOHR-UHFFFAOYSA-N [5-methoxy-1-(oxan-4-ylmethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound C1=C(C(=O)C2C(C2(C)C)(C)C)C2=CC(OC)=CC=C2N1CC1CCOCC1 SHHVJVSDLZXOHR-UHFFFAOYSA-N 0.000 claims 1
AMKZZDIDSQZZBA-UHFFFAOYSA-N [6-methoxy-1-(2-morpholin-4-ylethyl)indol-3-yl]-(2,2,3,3-tetramethylcyclopropyl)methanone Chemical compound C12=CC(OC)=CC=C2C(C(=O)C2C(C2(C)C)(C)C)=CN1CCN1CCOCC1 AMKZZDIDSQZZBA-UHFFFAOYSA-N 0.000 claims 1
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