NO327522B1 - Tetrahydrokinolinanaloger, anvendelser derav samt sammensetning omfattende forbindelsen - Google Patents

Tetrahydrokinolinanaloger, anvendelser derav samt sammensetning omfattende forbindelsen Download PDF

Info

Publication number: NO327522B1
Authority: NO; Norway
Prior art keywords: benzo; oxazin; propyl; mmol; butylpiperidin
Prior art date: 2001-12-28

Application number

NO20043013A

Other languages

English (en)

Norwegian (no)

Other versions

NO20043013L (no

Inventor

Bo Lennart Mikael Friberg

Kristian Norup Koch

Bo-Ragnar Tolf

Niels Skjaerbaek

Original Assignee

Acadia Pharm Inc

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.)

2001-12-28

Filing date

2004-07-15

Publication date

2009-08-03

2004-07-15 Application filed by Acadia Pharm Inc filed Critical Acadia Pharm Inc

2004-07-28 Publication of NO20043013L publication Critical patent/NO20043013L/no

2009-08-03 Publication of NO327522B1 publication Critical patent/NO327522B1/no

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 426
239000000203 mixture Substances 0.000 title claims abstract description 99
125000000147 tetrahydroquinolinyl group Chemical class N1(CCCC2=CC=CC=C12)* 0.000 title abstract 2
102000014415 Muscarinic acetylcholine receptor Human genes 0.000 claims abstract description 35
108050003473 Muscarinic acetylcholine receptor Proteins 0.000 claims abstract description 35
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract description 29
201000010099 disease Diseases 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims description 72
XEKAWZARUWARND-UHFFFAOYSA-N 6h-oxazin-3-one Chemical compound O=C1NOCC=C1 XEKAWZARUWARND-UHFFFAOYSA-N 0.000 claims description 63
108010009685 Cholinergic Receptors Proteins 0.000 claims description 38
108020003175 receptors Proteins 0.000 claims description 37
102000005962 receptors Human genes 0.000 claims description 36
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 35
-1 (R)-4-[2-methyl-3-(4-propoxypiperidin-2-yl)propyl]-4H-benzo[1,4 ]thiazin-3-one Chemical compound 0.000 claims description 23
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 18
208000035475 disorder Diseases 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 12
208000028698 Cognitive impairment Diseases 0.000 claims description 11
208000010877 cognitive disease Diseases 0.000 claims description 11
239000001257 hydrogen Substances 0.000 claims description 10
229910052740 iodine Inorganic materials 0.000 claims description 10
201000000980 schizophrenia Diseases 0.000 claims description 10
239000003814 drug Substances 0.000 claims description 9
229910052736 halogen Inorganic materials 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
239000003446 ligand Substances 0.000 claims description 9
208000028017 Psychotic disease Diseases 0.000 claims description 8
230000004410 intraocular pressure Effects 0.000 claims description 8
239000000472 muscarinic agonist Substances 0.000 claims description 8
230000003551 muscarinic effect Effects 0.000 claims description 8
206010027175 memory impairment Diseases 0.000 claims description 7
208000024827 Alzheimer disease Diseases 0.000 claims description 6
208000010412 Glaucoma Diseases 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
206010012289 Dementia Diseases 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
239000008194 pharmaceutical composition Substances 0.000 claims description 5
TXOFHBFKLCFMAQ-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-3,4-dihydro-2h-quinoline Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=CC=C2CCC1 TXOFHBFKLCFMAQ-UHFFFAOYSA-N 0.000 claims description 4
MWLZHULTNCYKQM-UHFFFAOYSA-N 4-[3-(4-butylpiperidin-1-yl)propyl]-6-methyl-1,4-benzoxazin-3-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC(C)=CC=C2OCC1=O MWLZHULTNCYKQM-UHFFFAOYSA-N 0.000 claims description 4
206010003591 Ataxia Diseases 0.000 claims description 4
201000010374 Down Syndrome Diseases 0.000 claims description 4
201000011240 Frontotemporal dementia Diseases 0.000 claims description 4
208000023105 Huntington disease Diseases 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
208000002193 Pain Diseases 0.000 claims description 4
208000018737 Parkinson disease Diseases 0.000 claims description 4
208000000609 Pick Disease of the Brain Diseases 0.000 claims description 4
208000034972 Sudden Infant Death Diseases 0.000 claims description 4
206010042440 Sudden infant death syndrome Diseases 0.000 claims description 4
208000000323 Tourette Syndrome Diseases 0.000 claims description 4
206010044688 Trisomy 21 Diseases 0.000 claims description 4
125000001118 alkylidene group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
208000019116 sleep disease Diseases 0.000 claims description 4
230000016776 visual perception Effects 0.000 claims description 4
YNCUMUVPVKIJLP-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6,7-difluoro-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC(F)=C(F)C=C2CCC1=O YNCUMUVPVKIJLP-UHFFFAOYSA-N 0.000 claims description 3
MEOXVFZDJTUJMH-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-8-methyl-3,4-dihydro-2h-quinoline Chemical compound C1CC(CCCC)CCN1CCCN1C2=C(C)C=CC=C2CCC1 MEOXVFZDJTUJMH-UHFFFAOYSA-N 0.000 claims description 3
HGXZABSHMMUYFI-UHFFFAOYSA-N 4-[3-(4-butylpiperidin-1-yl)propyl]-6-methyl-2,3-dihydro-1,4-benzoxazine Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC(C)=CC=C2OCC1 HGXZABSHMMUYFI-UHFFFAOYSA-N 0.000 claims description 3
WYLPCQJNYSSZAZ-UHFFFAOYSA-N 6-acetyl-4-[3-(4-butylpiperidin-1-yl)propyl]-1,4-benzoxazin-3-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC(C(C)=O)=CC=C2OCC1=O WYLPCQJNYSSZAZ-UHFFFAOYSA-N 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
208000022925 sleep disturbance Diseases 0.000 claims description 3
FXQRTOMQCLGBMI-VUNUGTOJSA-N 1-[(2r)-2-methyl-3-(3-pentyl-8-azabicyclo[3.2.1]octan-8-yl)propyl]-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC=CC=C2N1C[C@H](C)CN1C2CCC1CC(CCCCC)C2 FXQRTOMQCLGBMI-VUNUGTOJSA-N 0.000 claims description 2
NZKYALUWOONMIL-QGZVFWFLSA-N 1-[(2r)-2-methyl-3-(4-propoxypiperidin-1-yl)propyl]quinolin-2-one Chemical compound C1CC(OCCC)CCN1C[C@@H](C)CN1C(=O)C=CC2=CC=CC=C21 NZKYALUWOONMIL-QGZVFWFLSA-N 0.000 claims description 2
FXQRTOMQCLGBMI-RHWCECPXSA-N 1-[(2r)-2-methyl-3-[(5s)-3-pentyl-8-azabicyclo[3.2.1]octan-8-yl]propyl]-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC=CC=C2N1C[C@H](C)CN1C2CC[C@@]1([H])CC(CCCCC)C2 FXQRTOMQCLGBMI-RHWCECPXSA-N 0.000 claims description 2
HSLYCGUTBLBYTN-GOSISDBHSA-N 1-[(2r)-3-(4-butylidenepiperidin-1-yl)-2-methylpropyl]-3,4-dihydroquinolin-2-one Chemical compound C1CC(=CCCC)CCN1C[C@@H](C)CN1C2=CC=CC=C2CCC1=O HSLYCGUTBLBYTN-GOSISDBHSA-N 0.000 claims description 2
IHLHPDRDNZXLAE-GOSISDBHSA-N 1-[(2r)-3-(4-butylpiperidin-1-yl)-2-methylpropyl]-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1C[C@@H](C)CN1C2=CC=CC=C2CCC1=O IHLHPDRDNZXLAE-GOSISDBHSA-N 0.000 claims description 2
SRKALIZPNPUZEJ-GOSISDBHSA-N 1-[(2r)-3-(4-butylpiperidin-1-yl)-2-methylpropyl]quinolin-2-one Chemical compound C1CC(CCCC)CCN1C[C@@H](C)CN1C(=O)C=CC2=CC=CC=C21 SRKALIZPNPUZEJ-GOSISDBHSA-N 0.000 claims description 2
SGFQQSNKTBRUJC-KCUKBOBISA-N 1-[(2r)-3-[(5s)-3-butyl-8-azabicyclo[3.2.1]octan-8-yl]-2-methylpropyl]-3,4-dihydroquinolin-2-one Chemical compound O=C1CCC2=CC=CC=C2N1C[C@H](C)CN1C2CC[C@@]1([H])CC(CCCC)C2 SGFQQSNKTBRUJC-KCUKBOBISA-N 0.000 claims description 2
YOTILWOHUIXLJA-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-5-methyl-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=CC(C)=C2CCC1=O YOTILWOHUIXLJA-UHFFFAOYSA-N 0.000 claims description 2
MQFBIAVAEYCENS-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-5-methylquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=C(C)C=CC=C21 MQFBIAVAEYCENS-UHFFFAOYSA-N 0.000 claims description 2
QUMKVHHSGVRIAI-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-chloro-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=C(Cl)C=C2CCC1=O QUMKVHHSGVRIAI-UHFFFAOYSA-N 0.000 claims description 2
ZUNUJRXKIMEFOR-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-chloroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC(Cl)=CC=C21 ZUNUJRXKIMEFOR-UHFFFAOYSA-N 0.000 claims description 2
YHMFTXQANNXSGR-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-fluoro-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=C(F)C=C2CCC1=O YHMFTXQANNXSGR-UHFFFAOYSA-N 0.000 claims description 2
SCXLXWKKBFERQU-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-fluoroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC(F)=CC=C21 SCXLXWKKBFERQU-UHFFFAOYSA-N 0.000 claims description 2
TXYQIYLASATZKE-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-methoxy-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=C(OC)C=C2CCC1=O TXYQIYLASATZKE-UHFFFAOYSA-N 0.000 claims description 2
GLLHSSWRIZFAGK-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-methoxyquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC(OC)=CC=C21 GLLHSSWRIZFAGK-UHFFFAOYSA-N 0.000 claims description 2
VDYIOTYBOLHCNC-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-methyl-3,4-dihydro-2h-quinoline Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC=C(C)C=C2CCC1 VDYIOTYBOLHCNC-UHFFFAOYSA-N 0.000 claims description 2
GFUWVKQYSBLEAN-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-6-methylquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC(C)=CC=C21 GFUWVKQYSBLEAN-UHFFFAOYSA-N 0.000 claims description 2
WVBYGXUIAPERIY-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-7-(trifluoromethyl)-3,4-dihydro-2h-quinoline Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC(C(F)(F)F)=CC=C2CCC1 WVBYGXUIAPERIY-UHFFFAOYSA-N 0.000 claims description 2
PJIFKJDCZGBHBO-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-7-fluoroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC=C(F)C=C21 PJIFKJDCZGBHBO-UHFFFAOYSA-N 0.000 claims description 2
VYTXPOOGEGYQRB-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-7-methyl-3,4-dihydroquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C2=CC(C)=CC=C2CCC1=O VYTXPOOGEGYQRB-UHFFFAOYSA-N 0.000 claims description 2
VKYZQEOQJGJZPD-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]-7-methylquinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC=C(C)C=C21 VKYZQEOQJGJZPD-UHFFFAOYSA-N 0.000 claims description 2
KARBNIZJWDKJOB-UHFFFAOYSA-N 1-[3-(4-butylpiperidin-1-yl)propyl]quinolin-2-one Chemical compound C1CC(CCCC)CCN1CCCN1C(=O)C=CC2=CC=CC=C21 KARBNIZJWDKJOB-UHFFFAOYSA-N 0.000 claims description 2
FSCRFGXDIRFQDC-UHFFFAOYSA-N 1-[3-(4-propoxypiperidin-1-yl)propyl]-3,4-dihydroquinolin-2-one Chemical compound C1CC(OCCC)CCN1CCCN1C2=CC=CC=C2CCC1=O FSCRFGXDIRFQDC-UHFFFAOYSA-N 0.000 claims description 2
ZMKJMFRUYMOVGG-UHFFFAOYSA-N 1-[3-(4-propoxypiperidin-1-yl)propyl]quinolin-2-one Chemical compound C1CC(OCCC)CCN1CCCN1C(=O)C=CC2=CC=CC=C21 ZMKJMFRUYMOVGG-UHFFFAOYSA-N 0.000 claims description 2
ROZHCBMQKZYZMM-FTTSTGDASA-N 4-[(2r)-2-hydroxy-3-[(5s)-3-pentyl-8-bicyclo[3.2.1]octanyl]propyl]-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=CC=C2N1C[C@H](O)CC1C2CC[C@@]1([H])CC(CCCCC)C2 ROZHCBMQKZYZMM-FTTSTGDASA-N 0.000 claims description 2
FGBIFXLAXVQGAA-YXOXRFPUSA-N 4-[(2r)-2-methyl-3-(3-pentyl-8-azabicyclo[3.2.1]octan-8-yl)propyl]-1,4-benzothiazin-3-one Chemical compound O=C1CSC2=CC=CC=C2N1C[C@H](C)CN1C2CCC1CC(CCCCC)C2 FGBIFXLAXVQGAA-YXOXRFPUSA-N 0.000 claims description 2
PFTCOZDBHUZQQU-YXOXRFPUSA-N 4-[(2r)-2-methyl-3-(3-pentyl-8-azabicyclo[3.2.1]octan-8-yl)propyl]-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=CC=C2N1C[C@H](C)CN1C2CCC1CC(CCCCC)C2 PFTCOZDBHUZQQU-YXOXRFPUSA-N 0.000 claims description 2
IOMURWOGEVETLA-MRXNPFEDSA-N 4-[(2r)-2-methyl-3-(4-propoxypiperidin-1-yl)propyl]-1,4-benzoxazin-3-one Chemical compound C1CC(OCCC)CCN1C[C@@H](C)CN1C2=CC=CC=C2OCC1=O IOMURWOGEVETLA-MRXNPFEDSA-N 0.000 claims description 2
FGBIFXLAXVQGAA-OSIBBQKWSA-N 4-[(2r)-2-methyl-3-[(5s)-3-pentyl-8-azabicyclo[3.2.1]octan-8-yl]propyl]-1,4-benzothiazin-3-one Chemical compound O=C1CSC2=CC=CC=C2N1C[C@H](C)CN1C2CC[C@@]1([H])CC(CCCCC)C2 FGBIFXLAXVQGAA-OSIBBQKWSA-N 0.000 claims description 2
FKGNEHONLNMRPP-NEYBNPPJSA-N 4-[(2r)-3-(3-butyl-8-azabicyclo[3.2.1]octan-8-yl)-2-methylpropyl]-1,4-benzothiazin-3-one Chemical compound O=C1CSC2=CC=CC=C2N1C[C@H](C)CN1C2CCC1CC(CCCC)C2 FKGNEHONLNMRPP-NEYBNPPJSA-N 0.000 claims description 2
YXSQVNRXUABSEX-NEYBNPPJSA-N 4-[(2r)-3-(3-butyl-8-azabicyclo[3.2.1]octan-8-yl)-2-methylpropyl]-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=CC=C2N1C[C@H](C)CN1C2CCC1CC(CCCC)C2 YXSQVNRXUABSEX-NEYBNPPJSA-N 0.000 claims description 2
ZPOXVXSWGFFXLW-WZOHVRDPSA-N 4-[(2r)-3-(3-butyl-8-azabicyclo[3.2.1]octan-8-yl)-2-methylpropyl]-6-fluoro-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=C(F)C=C2N1C[C@H](C)CN1C2CCC1CC(CCCC)C2 ZPOXVXSWGFFXLW-WZOHVRDPSA-N 0.000 claims description 2
SDAFFZUFSQQHJE-YXOXRFPUSA-N 4-[(2r)-3-(3-butyl-8-azabicyclo[3.2.1]octan-8-yl)-2-methylpropyl]-6-methyl-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=C(C)C=C2N1C[C@H](C)CN1C2CCC1CC(CCCC)C2 SDAFFZUFSQQHJE-YXOXRFPUSA-N 0.000 claims description 2
ZUHZENGPTIELTD-QGZVFWFLSA-N 4-[(2r)-3-(4-butylidenepiperidin-1-yl)-2-methylpropyl]-1,4-benzoxazin-3-one Chemical compound C1CC(=CCCC)CCN1C[C@@H](C)CN1C2=CC=CC=C2OCC1=O ZUHZENGPTIELTD-QGZVFWFLSA-N 0.000 claims description 2
QOMKJCYISJVKNU-MRXNPFEDSA-N 4-[(2r)-3-(4-butylidenepiperidin-1-yl)-2-methylpropyl]-6-fluoro-1,4-benzoxazin-3-one Chemical compound C1CC(=CCCC)CCN1C[C@@H](C)CN1C2=CC(F)=CC=C2OCC1=O QOMKJCYISJVKNU-MRXNPFEDSA-N 0.000 claims description 2
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TZQASLNOZTZKGX-GOSISDBHSA-N 4-[(2r)-3-(4-butylidenepiperidin-1-yl)-2-methylpropyl]-6-methyl-1,4-benzoxazin-3-one Chemical compound C1CC(=CCCC)CCN1C[C@@H](C)CN1C2=CC(C)=CC=C2OCC1=O TZQASLNOZTZKGX-GOSISDBHSA-N 0.000 claims description 2
MOKHWUTZXFHWQC-MRXNPFEDSA-N 4-[(2r)-3-(4-butylidenepiperidin-1-yl)-2-methylpropyl]-7-fluoro-1,4-benzoxazin-3-one Chemical compound C1CC(=CCCC)CCN1C[C@@H](C)CN1C2=CC=C(F)C=C2OCC1=O MOKHWUTZXFHWQC-MRXNPFEDSA-N 0.000 claims description 2
VHSRFVWBSZIFMP-QGZVFWFLSA-N 4-[(2r)-3-(4-butylpiperidin-1-yl)-2-methylpropyl]-1,4-benzothiazin-3-one Chemical compound C1CC(CCCC)CCN1C[C@@H](C)CN1C2=CC=CC=C2SCC1=O VHSRFVWBSZIFMP-QGZVFWFLSA-N 0.000 claims description 2
NOHKUUXFQYNDKR-QGZVFWFLSA-N 4-[(2r)-3-(4-butylpiperidin-1-yl)-2-methylpropyl]-1,4-benzoxazin-3-one Chemical compound C1CC(CCCC)CCN1C[C@@H](C)CN1C2=CC=CC=C2OCC1=O NOHKUUXFQYNDKR-QGZVFWFLSA-N 0.000 claims description 2
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NSORNLXBCFBCIH-GOSISDBHSA-N 4-[(2r)-3-(4-butylpiperidin-1-yl)-2-methylpropyl]-6-methyl-1,4-benzoxazin-3-one Chemical compound C1CC(CCCC)CCN1C[C@@H](C)CN1C2=CC(C)=CC=C2OCC1=O NSORNLXBCFBCIH-GOSISDBHSA-N 0.000 claims description 2
NMZXWRLUQQYBTA-MRXNPFEDSA-N 4-[(2r)-3-(4-butylpiperidin-1-yl)-2-methylpropyl]-7-fluoro-1,4-benzoxazin-3-one Chemical compound C1CC(CCCC)CCN1C[C@@H](C)CN1C2=CC=C(F)C=C2OCC1=O NMZXWRLUQQYBTA-MRXNPFEDSA-N 0.000 claims description 2
PGJITJKDIUDZTD-OVZGMEQFSA-N 4-[(2r)-3-[(5s)-3-butoxy-8-azabicyclo[3.2.1]octan-8-yl]-2-methylpropyl]-6-fluoro-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=C(F)C=C2N1C[C@H](C)CN1C2CC[C@@]1([H])CC(OCCCC)C2 PGJITJKDIUDZTD-OVZGMEQFSA-N 0.000 claims description 2
FKGNEHONLNMRPP-SOAISFHBSA-N 4-[(2r)-3-[(5s)-3-butyl-8-azabicyclo[3.2.1]octan-8-yl]-2-methylpropyl]-1,4-benzothiazin-3-one Chemical compound O=C1CSC2=CC=CC=C2N1C[C@H](C)CN1C2CC[C@@]1([H])CC(CCCC)C2 FKGNEHONLNMRPP-SOAISFHBSA-N 0.000 claims description 2
ZPOXVXSWGFFXLW-PYXOFJJQSA-N 4-[(2r)-3-[(5s)-3-butyl-8-azabicyclo[3.2.1]octan-8-yl]-2-methylpropyl]-6-fluoro-1,4-benzoxazin-3-one Chemical compound O=C1COC2=CC=C(F)C=C2N1C[C@H](C)CN1C2CC[C@@]1([H])CC(CCCC)C2 ZPOXVXSWGFFXLW-PYXOFJJQSA-N 0.000 claims description 2
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Classifications

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- C07D451/00—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof
- C07D451/02—Heterocyclic compounds containing 8-azabicyclo [3.2.1] octane, 9-azabicyclo [3.3.1] nonane, or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane or granatane alkaloids, scopolamine; Cyclic acetals thereof containing not further condensed 8-azabicyclo [3.2.1] octane or 3-oxa-9-azatricyclo [3.3.1.0<2,4>] nonane ring systems, e.g. tropane; Cyclic acetals thereof
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
Medicinal Chemistry (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Ophthalmology & Optometry (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Anesthesiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

NO20043013A 2001-12-28 2004-07-15 Tetrahydrokinolinanaloger, anvendelser derav samt sammensetning omfattende forbindelsen NO327522B1 (no)

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US34472201P	2001-12-28	2001-12-28
PCT/US2002/041617 WO2003057672A2 (en)	2001-12-28	2002-12-23	Tetrahydroquinoline analogues as muscarinic agonists

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US (3)	US7307075B2 (xx)
EP (1)	EP1461318B9 (xx)
JP (1)	JP4509565B2 (xx)
KR (1)	KR100972614B1 (xx)
CN (1)	CN100402032C (xx)
AT (1)	ATE304533T1 (xx)
AU (1)	AU2002359875B2 (xx)
BR (1)	BR0215430A (xx)
CA (1)	CA2470578C (xx)
DE (1)	DE60206198T2 (xx)
DK (1)	DK1461318T3 (xx)
ES (1)	ES2251624T3 (xx)
HK (1)	HK1074573A1 (xx)
IL (2)	IL162616A0 (xx)
MX (1)	MXPA04006281A (xx)
NO (1)	NO327522B1 (xx)
NZ (1)	NZ533566A (xx)
RU (1)	RU2292346C2 (xx)
WO (1)	WO2003057672A2 (xx)
ZA (1)	ZA200405024B (xx)

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US7550459B2 (en) *	2001-12-28	2009-06-23	Acadia Pharmaceuticals, Inc.	Tetrahydroquinoline analogues as muscarinic agonists
US7307075B2 (en)	2001-12-28	2007-12-11	Acadia Pharmaceuticals Inc.	Tetrahydroquinoline analogues as muscarinic agonists
KR20050112116A (ko) *	2003-03-28	2005-11-29	아카디아 파마슈티칼스 인코포레이티드	통증 관리를 위한 무스카린성 ｍ1 리셉터 작용제
JP5398984B2 (ja) *	2005-06-24	2014-01-29	富山化学工業株式会社	新規な含窒素複素環化合物およびその塩
EP2258359A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation with sabcomelin
JP2009506069A (ja) *	2005-08-26	2009-02-12	ブレインセルス，インコーポレイティド	ムスカリン性受容体調節による神経発生
CA2625153A1 (en)	2005-10-21	2007-04-26	Braincells, Inc.	Modulation of neurogenesis by pde inhibition
US20070112017A1 (en)	2005-10-31	2007-05-17	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
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US20030176418A1 (en)	2003-09-18
US7576078B2 (en)	2009-08-18
JP2005519060A (ja)	2005-06-30
WO2003057672A2 (en)	2003-07-17
CN1635891A (zh)	2005-07-06
DE60206198T2 (de)	2006-06-14
CA2470578A1 (en)	2003-07-17
KR100972614B1 (ko)	2010-07-27
US20060199810A1 (en)	2006-09-07
BR0215430A (pt)	2004-12-14
IL162616A0 (en)	2005-11-20
ATE304533T1 (de)	2005-09-15
US7307075B2 (en)	2007-12-11
HK1074573A1 (en)	2005-11-18
IL162616A (en)	2011-06-30
RU2004123203A (ru)	2006-01-20
NZ533566A (en)	2007-03-30
US7576100B2 (en)	2009-08-18
KR20040070287A (ko)	2004-08-06
DE60206198D1 (de)	2005-10-20
EP1461318B9 (en)	2005-12-28
NO20043013L (no)	2004-07-28
AU2002359875B2 (en)	2009-01-08
DK1461318T3 (da)	2006-01-09
MXPA04006281A (es)	2004-09-27
AU2002359875A1 (en)	2003-07-24
ES2251624T3 (es)	2006-05-01
EP1461318B1 (en)	2005-09-14
WO2003057672A3 (en)	2003-11-13
CN100402032C (zh)	2008-07-16
US20060199813A1 (en)	2006-09-07
EP1461318A2 (en)	2004-09-29
JP4509565B2 (ja)	2010-07-21
ZA200405024B (en)	2005-07-27
RU2292346C2 (ru)	2007-01-27
CA2470578C (en)	2010-10-12

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KR20180067561A (ko)	2018-06-20	치료 화합물 및 그의 사용 방법
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