NO319948B1 - 1-Arensulfonyl-2-aryl-pyrrolidin- og -piperidin-derivater for behandling av CNS-sykdommer - Google Patents

1-Arensulfonyl-2-aryl-pyrrolidin- og -piperidin-derivater for behandling av CNS-sykdommer Download PDF

Info

Publication number: NO319948B1
Authority: NO; Norway
Prior art keywords: pyrrolidine; phenyl; toluene; fluoro; sulfonyl
Prior art date: 1999-03-25

Application number

NO20014617A

Other languages

English (en)

Norwegian (no)

Other versions

NO20014617D0 (no

NO20014617L (no

Inventor

Juergen Wichmann

Vincent Mutel

Eric Vieira

Original Assignee

Hoffmann La Roche

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.)

1999-03-25

Filing date

2001-09-24

Publication date

2005-10-03

2001-09-24 Application filed by Hoffmann La Roche filed Critical Hoffmann La Roche

2001-09-24 Publication of NO20014617D0 publication Critical patent/NO20014617D0/no

2001-09-24 Publication of NO20014617L publication Critical patent/NO20014617L/no

2005-10-03 Publication of NO319948B1 publication Critical patent/NO319948B1/no

Links

RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 title claims description 45
208000015114 central nervous system disease Diseases 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 138
150000003839 salts Chemical class 0.000 claims description 26
125000000217 alkyl group Chemical group 0.000 claims description 11
239000003814 drug Substances 0.000 claims description 11
238000000034 method Methods 0.000 claims description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 10
229910052736 halogen Inorganic materials 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
OOVSRCPGHGCJAM-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-phenylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=CC=CC=2)CCC1 OOVSRCPGHGCJAM-UHFFFAOYSA-N 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 9
150000002367 halogens Chemical class 0.000 claims description 9
238000002360 preparation method Methods 0.000 claims description 9
229940079593 drug Drugs 0.000 claims description 8
YFHJJRUCGDZFIL-MAUKXSAKSA-N (2r,3s)-3-methyl-1-(4-methylphenyl)sulfonyl-2-phenylpyrrolidine Chemical compound C1([C@@H]2N(CC[C@@H]2C)S(=O)(=O)C=2C=CC(C)=CC=2)=CC=CC=C1 YFHJJRUCGDZFIL-MAUKXSAKSA-N 0.000 claims description 7
ZLRBSTSPRRCHES-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=C(OC)C(OC)=CC=C1C1N(S(=O)(=O)C=2C=CC(C)=CC=2)CCC1 ZLRBSTSPRRCHES-UHFFFAOYSA-N 0.000 claims description 7
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 claims description 7
230000001154 acute effect Effects 0.000 claims description 7
-1 (Ci-C7)-alkyl Chemical group 0.000 claims description 6
WRLSSXDFVXDSKD-UHFFFAOYSA-N 2-(4-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1C1N(S(=O)(=O)C=2C=CC(C)=CC=2)CCC1 WRLSSXDFVXDSKD-UHFFFAOYSA-N 0.000 claims description 6
208000002193 Pain Diseases 0.000 claims description 6
206010034010 Parkinsonism Diseases 0.000 claims description 6
238000006243 chemical reaction Methods 0.000 claims description 6
230000001684 chronic effect Effects 0.000 claims description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
125000001424 substituent group Chemical group 0.000 claims description 6
208000012902 Nervous system disease Diseases 0.000 claims description 5
208000025966 Neurological disease Diseases 0.000 claims description 5
208000027089 Parkinsonian disease Diseases 0.000 claims description 5
125000004093 cyano group Chemical group *C#N 0.000 claims description 5
125000000524 functional group Chemical group 0.000 claims description 5
229930195712 glutamate Natural products 0.000 claims description 5
230000002265 prevention Effects 0.000 claims description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
208000028017 Psychotic disease Diseases 0.000 claims description 4
206010002026 amyotrophic lateral sclerosis Diseases 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000004076 pyridyl group Chemical group 0.000 claims description 4
125000001544 thienyl group Chemical group 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 3
208000019901 Anxiety disease Diseases 0.000 claims description 3
208000000094 Chronic Pain Diseases 0.000 claims description 3
206010010904 Convulsion Diseases 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
208000012661 Dyskinesia Diseases 0.000 claims description 3
206010019196 Head injury Diseases 0.000 claims description 3
208000010496 Heart Arrest Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000013016 Hypoglycemia Diseases 0.000 claims description 3
206010021143 Hypoxia Diseases 0.000 claims description 3
208000019695 Migraine disease Diseases 0.000 claims description 3
208000007101 Muscle Cramp Diseases 0.000 claims description 3
206010057852 Nicotine dependence Diseases 0.000 claims description 3
208000026251 Opioid-Related disease Diseases 0.000 claims description 3
208000017442 Retinal disease Diseases 0.000 claims description 3
206010038923 Retinopathy Diseases 0.000 claims description 3
208000005392 Spasm Diseases 0.000 claims description 3
208000025569 Tobacco Use disease Diseases 0.000 claims description 3
206010046543 Urinary incontinence Diseases 0.000 claims description 3
206010047700 Vomiting Diseases 0.000 claims description 3
208000005298 acute pain Diseases 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
230000036506 anxiety Effects 0.000 claims description 3
230000036770 blood supply Effects 0.000 claims description 3
210000004556 brain Anatomy 0.000 claims description 3
230000003925 brain function Effects 0.000 claims description 3
208000010877 cognitive disease Diseases 0.000 claims description 3
230000036461 convulsion Effects 0.000 claims description 3
230000002950 deficient Effects 0.000 claims description 3
231100000040 eye damage Toxicity 0.000 claims description 3
230000006870 function Effects 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
230000007954 hypoxia Effects 0.000 claims description 3
206010027175 memory impairment Diseases 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
206010027599 migraine Diseases 0.000 claims description 3
201000005040 opiate dependence Diseases 0.000 claims description 3
230000035935 pregnancy Effects 0.000 claims description 3
201000000980 schizophrenia Diseases 0.000 claims description 3
208000020431 spinal cord injury Diseases 0.000 claims description 3
230000008673 vomiting Effects 0.000 claims description 3
DAEHFYNGSSBGSS-QGZVFWFLSA-N (2r)-2-(4-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1[C@@H](C=2C=CC(F)=CC=2)CCC1 DAEHFYNGSSBGSS-QGZVFWFLSA-N 0.000 claims description 2
UNWYOYFLGMANQV-INIZCTEOSA-N (2s)-1-(4-chlorophenyl)sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1[C@H]1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCC1 UNWYOYFLGMANQV-INIZCTEOSA-N 0.000 claims description 2
DAEHFYNGSSBGSS-KRWDZBQOSA-N (2s)-2-(4-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1[C@H](C=2C=CC(F)=CC=2)CCC1 DAEHFYNGSSBGSS-KRWDZBQOSA-N 0.000 claims description 2
XPKVLOSMAOEFKN-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-(3-fluorophenyl)pyrrolidine Chemical compound FC1=CC=CC(C2N(CCC2)S(=O)(=O)C=2C=CC(Cl)=CC=2)=C1 XPKVLOSMAOEFKN-UHFFFAOYSA-N 0.000 claims description 2
UNWYOYFLGMANQV-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCC1 UNWYOYFLGMANQV-UHFFFAOYSA-N 0.000 claims description 2
WRVWGBUXSYCFAD-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-(4-methylphenyl)pyrrolidine Chemical compound C1=CC(C)=CC=C1C1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCC1 WRVWGBUXSYCFAD-UHFFFAOYSA-N 0.000 claims description 2
RDWVMMDDZCMBGF-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-phenylpyrrolidine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2C=CC=CC=2)CCC1 RDWVMMDDZCMBGF-UHFFFAOYSA-N 0.000 claims description 2
WMCBPITWUUHVJB-UHFFFAOYSA-N 1-(4-chlorophenyl)sulfonyl-2-thiophen-2-ylpyrrolidine Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)N1C(C=2SC=CC=2)CCC1 WMCBPITWUUHVJB-UHFFFAOYSA-N 0.000 claims description 2
XZVSIWOHBXELCZ-UHFFFAOYSA-N 1-(4-ethylphenyl)sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(CC)=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 XZVSIWOHBXELCZ-UHFFFAOYSA-N 0.000 claims description 2
QJZKEMXDPJECSV-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-thiophen-2-ylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2SC=CC=2)CCC1 QJZKEMXDPJECSV-UHFFFAOYSA-N 0.000 claims description 2
RMZAYRXUTNJSDZ-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-thiophen-3-ylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C2=CSC=C2)CCC1 RMZAYRXUTNJSDZ-UHFFFAOYSA-N 0.000 claims description 2
OBQGFKZKOZCQEZ-UHFFFAOYSA-N 1-(benzenesulfonyl)-2-(4-chlorophenyl)pyrrolidine Chemical compound C1=CC(Cl)=CC=C1C1N(S(=O)(=O)C=2C=CC=CC=2)CCC1 OBQGFKZKOZCQEZ-UHFFFAOYSA-N 0.000 claims description 2
BGHFZDLZQPHUMK-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(Cl)C(F)=CC=2)CCC1 BGHFZDLZQPHUMK-UHFFFAOYSA-N 0.000 claims description 2
HIJIYGFBPRAJAP-UHFFFAOYSA-N 2-(3-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(F)C=CC=2)CCC1 HIJIYGFBPRAJAP-UHFFFAOYSA-N 0.000 claims description 2
QNROCOCNCGNWCU-UHFFFAOYSA-N 2-(3-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(C)C=CC=2)CCC1 QNROCOCNCGNWCU-UHFFFAOYSA-N 0.000 claims description 2
RQFMCSPTHHBBQD-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(C)C(Cl)=CC=2)CCC1 RQFMCSPTHHBBQD-UHFFFAOYSA-N 0.000 claims description 2
VYBSPEXXBNSDGV-UHFFFAOYSA-N 2-(4-chlorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=CC(Cl)=CC=2)CCC1 VYBSPEXXBNSDGV-UHFFFAOYSA-N 0.000 claims description 2
CXEDUPWPRWZRLR-UHFFFAOYSA-N 2-(4-ethylphenyl)-1-(4-fluorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(CC)=CC=C1C1N(S(=O)(=O)C=2C=CC(F)=CC=2)CCC1 CXEDUPWPRWZRLR-UHFFFAOYSA-N 0.000 claims description 2
YOFIMXZOJFOEKK-UHFFFAOYSA-N 2-(4-ethylphenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(CC)=CC=C1C1N(S(=O)(=O)C=2C=CC(C)=CC=2)CCC1 YOFIMXZOJFOEKK-UHFFFAOYSA-N 0.000 claims description 2
YKEZZMRBHZDMST-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(2-methylphenyl)sulfonylpyrrolidine Chemical compound CC1=CC=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 YKEZZMRBHZDMST-UHFFFAOYSA-N 0.000 claims description 2
MSYGBWPPRVPMSJ-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-fluorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(F)=CC=2)CCC1 MSYGBWPPRVPMSJ-UHFFFAOYSA-N 0.000 claims description 2
DAEHFYNGSSBGSS-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 DAEHFYNGSSBGSS-UHFFFAOYSA-N 0.000 claims description 2
PUYCZGIXVWVRSC-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-[4-(methoxymethyl)phenyl]sulfonylpyrrolidine Chemical compound C1=CC(COC)=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 PUYCZGIXVWVRSC-UHFFFAOYSA-N 0.000 claims description 2
SJQFFXJYSWEHGG-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methyl-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound CC1CCN(S(=O)(=O)C=2C=CC(C)=CC=2)C1C1=CC=C(F)C=C1 SJQFFXJYSWEHGG-UHFFFAOYSA-N 0.000 claims description 2
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 2
230000006806 disease prevention Effects 0.000 claims description 2
125000001624 naphthyl group Chemical group 0.000 claims description 2
125000006701 (C1-C7) alkyl group Chemical group 0.000 claims 2
LCBAARXFUPCPHC-UHFFFAOYSA-N 2-(3,4-difluorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(F)C(F)=CC=2)CCC1 LCBAARXFUPCPHC-UHFFFAOYSA-N 0.000 claims 1
239000000546 pharmaceutical excipient Substances 0.000 claims 1
239000007787 solid Substances 0.000 description 91
238000007429 general method Methods 0.000 description 88
YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 28
ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 4-chlorobenzenesulfonyl chloride Chemical compound ClC1=CC=C(S(Cl)(=O)=O)C=C1 ZLYBFBAHAQEEQQ-UHFFFAOYSA-N 0.000 description 24
ZDCXMSDSTZZWAX-UHFFFAOYSA-N 2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1C1NCCC1 ZDCXMSDSTZZWAX-UHFFFAOYSA-N 0.000 description 22
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
BFXHJFKKRGVUMU-UHFFFAOYSA-N 4-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=C(S(Cl)(=O)=O)C=C1 BFXHJFKKRGVUMU-UHFFFAOYSA-N 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000000203 mixture Substances 0.000 description 11
239000000243 solution Substances 0.000 description 8
239000000969 carrier Substances 0.000 description 7
108010010914 Metabotropic glutamate receptors Proteins 0.000 description 6
102000016193 Metabotropic glutamate receptors Human genes 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 5
239000007903 gelatin capsule Substances 0.000 description 5
239000000047 product Substances 0.000 description 5
GOHGDBAHAKTVDW-UHFFFAOYSA-N 1-[4-(chloromethyl)phenyl]sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(CCl)=CC=2)CCC1 GOHGDBAHAKTVDW-UHFFFAOYSA-N 0.000 description 4
OADZVVBVXBBMPW-UHFFFAOYSA-N 2-(3-fluorophenyl)pyrrolidine Chemical compound FC1=CC=CC(C2NCCC2)=C1 OADZVVBVXBBMPW-UHFFFAOYSA-N 0.000 description 4
GSOGADJIIMVREB-UHFFFAOYSA-N 2-[4-(trifluoromethyl)phenyl]pyrrolidine Chemical compound C1=CC(C(F)(F)F)=CC=C1C1NCCC1 GSOGADJIIMVREB-UHFFFAOYSA-N 0.000 description 4
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 4
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
239000012267 brine Substances 0.000 description 4
210000004027 cell Anatomy 0.000 description 4
239000012230 colorless oil Substances 0.000 description 4
229940049906 glutamate Drugs 0.000 description 4
238000004519 manufacturing process Methods 0.000 description 4
239000000825 pharmaceutical preparation Substances 0.000 description 4
229920005862 polyol Polymers 0.000 description 4
150000003077 polyols Chemical class 0.000 description 4
102000005962 receptors Human genes 0.000 description 4
108020003175 receptors Proteins 0.000 description 4
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
LIFJPSLQRGQNMM-UHFFFAOYSA-N 2-(2-Furanyl)pyrrolidine Chemical compound C1CCNC1C1=CC=CO1 LIFJPSLQRGQNMM-UHFFFAOYSA-N 0.000 description 3
NOJCVVKIBLHAGW-UHFFFAOYSA-N 2-(2-fluorophenyl)pyrrolidine Chemical compound FC1=CC=CC=C1C1NCCC1 NOJCVVKIBLHAGW-UHFFFAOYSA-N 0.000 description 3
PJWVATQQJDYNQI-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)pyrrolidine Chemical compound C1=C(Cl)C(F)=CC=C1C1NCCC1 PJWVATQQJDYNQI-UHFFFAOYSA-N 0.000 description 3
UUTBSNFHBOVJLI-UHFFFAOYSA-N 2-(3-methylphenyl)pyrrolidine Chemical compound CC1=CC=CC(C2NCCC2)=C1 UUTBSNFHBOVJLI-UHFFFAOYSA-N 0.000 description 3
CIHHGGKKRPPWSU-UHFFFAOYSA-N 2-(4-chlorophenyl)pyrrolidine Chemical compound C1=CC(Cl)=CC=C1C1NCCC1 CIHHGGKKRPPWSU-UHFFFAOYSA-N 0.000 description 3
QGZKNOIZEORCFG-UHFFFAOYSA-N 2-(4-fluorophenyl)-3-methylpyrrolidine Chemical compound CC1CCNC1C1=CC=C(F)C=C1 QGZKNOIZEORCFG-UHFFFAOYSA-N 0.000 description 3
TXFISDWSKUHPET-UHFFFAOYSA-N 2-(4-methylphenyl)pyrrolidine Chemical compound C1=CC(C)=CC=C1C1NCCC1 TXFISDWSKUHPET-UHFFFAOYSA-N 0.000 description 3
JUTDHSGANMHVIC-UHFFFAOYSA-N 2-phenylpyrrolidine Chemical compound C1CCNC1C1=CC=CC=C1 JUTDHSGANMHVIC-UHFFFAOYSA-N 0.000 description 3
BNUVOMNEUJWHCF-UHFFFAOYSA-N 2-thiophen-2-ylpyrrolidine Chemical compound C1CCNC1C1=CC=CS1 BNUVOMNEUJWHCF-UHFFFAOYSA-N 0.000 description 3
XXZBVULUYZUNDS-UHFFFAOYSA-N 2-thiophen-3-ylpyrrolidine Chemical compound C1CCNC1C1=CSC=C1 XXZBVULUYZUNDS-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000556 agonist Substances 0.000 description 3
150000001412 amines Chemical group 0.000 description 3
239000011575 calcium Substances 0.000 description 3
210000003169 central nervous system Anatomy 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
239000012043 crude product Substances 0.000 description 3
230000000694 effects Effects 0.000 description 3
239000007788 liquid Substances 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000002904 solvent Substances 0.000 description 3
ZDCXMSDSTZZWAX-SNVBAGLBSA-N (2r)-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1[C@@H]1NCCC1 ZDCXMSDSTZZWAX-SNVBAGLBSA-N 0.000 description 2
IBPIAQWYWUWFPS-LBPRGKRZSA-N (2s)-2-(4-ethylphenyl)pyrrolidine Chemical compound C1=CC(CC)=CC=C1[C@H]1NCCC1 IBPIAQWYWUWFPS-LBPRGKRZSA-N 0.000 description 2
ZDCXMSDSTZZWAX-JTQLQIEISA-N (2s)-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1[C@H]1NCCC1 ZDCXMSDSTZZWAX-JTQLQIEISA-N 0.000 description 2
UOPALANXPTYMFE-UHFFFAOYSA-N 2-(2,4-dimethylphenyl)pyrrolidine Chemical compound CC1=CC(C)=CC=C1C1NCCC1 UOPALANXPTYMFE-UHFFFAOYSA-N 0.000 description 2
SZPJRABUCTXGIN-UHFFFAOYSA-N 2-(3,4-difluorophenyl)pyrrolidine Chemical compound C1=C(F)C(F)=CC=C1C1NCCC1 SZPJRABUCTXGIN-UHFFFAOYSA-N 0.000 description 2
SRTPGDGQKPCDMC-UHFFFAOYSA-N 2-(3-chlorophenyl)pyrrolidine Chemical compound ClC1=CC=CC(C2NCCC2)=C1 SRTPGDGQKPCDMC-UHFFFAOYSA-N 0.000 description 2
HCBLZPKEGFYHDN-UHFFFAOYSA-N 2-(4-methoxyphenyl)pyrrolidine Chemical compound C1=CC(OC)=CC=C1C1NCCC1 HCBLZPKEGFYHDN-UHFFFAOYSA-N 0.000 description 2
PKBPZLLTVPLQSC-UHFFFAOYSA-N 2-chloro-n,n-dimethyl-4-pyrrolidin-2-ylaniline Chemical compound C1=C(Cl)C(N(C)C)=CC=C1C1NCCC1 PKBPZLLTVPLQSC-UHFFFAOYSA-N 0.000 description 2
XFPXXGOGWPHMPH-UHFFFAOYSA-N 3-(dimethylamino)-1-(3-fluorophenyl)propan-1-one;hydrochloride Chemical compound Cl.CN(C)CCC(=O)C1=CC=CC(F)=C1 XFPXXGOGWPHMPH-UHFFFAOYSA-N 0.000 description 2
JZWZRZYTVFZHIA-UHFFFAOYSA-N 3-[1-(4-methylphenyl)sulfonylpyrrolidin-2-yl]pyridine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=NC=CC=2)CCC1 JZWZRZYTVFZHIA-UHFFFAOYSA-N 0.000 description 2
QXTQWYZHHMQSQH-UHFFFAOYSA-N 4-(bromomethyl)benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(CBr)C=C1 QXTQWYZHHMQSQH-UHFFFAOYSA-N 0.000 description 2
GDGNPIOGJLCICG-UHFFFAOYSA-N 4-pyrrolidin-2-ylpyridine Chemical compound C1CCNC1C1=CC=NC=C1 GDGNPIOGJLCICG-UHFFFAOYSA-N 0.000 description 2
208000030507 AIDS Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229910000564 Raney nickel Inorganic materials 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000013543 active substance Substances 0.000 description 2
239000000654 additive Substances 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
CBHOOMGKXCMKIR-UHFFFAOYSA-N azane;methanol Chemical compound N.OC CBHOOMGKXCMKIR-UHFFFAOYSA-N 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
239000008298 dragée Substances 0.000 description 2
239000003925 fat Substances 0.000 description 2
239000003823 glutamate receptor agonist Substances 0.000 description 2
239000003825 glutamate receptor antagonist Substances 0.000 description 2
238000005984 hydrogenation reaction Methods 0.000 description 2
238000002347 injection Methods 0.000 description 2
239000007924 injection Substances 0.000 description 2
239000008101 lactose Substances 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
238000005259 measurement Methods 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
239000002858 neurotransmitter agent Substances 0.000 description 2
MYKUKUCHPMASKF-UHFFFAOYSA-N nornicotine Chemical compound C1CCNC1C1=CC=CN=C1 MYKUKUCHPMASKF-UHFFFAOYSA-N 0.000 description 2
239000003921 oil Substances 0.000 description 2
235000019198 oils Nutrition 0.000 description 2
229910000033 sodium borohydride Inorganic materials 0.000 description 2
239000012279 sodium borohydride Substances 0.000 description 2
239000012258 stirred mixture Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000829 suppository Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000001993 wax Substances 0.000 description 2
UNWYOYFLGMANQV-MRXNPFEDSA-N (2r)-1-(4-chlorophenyl)sulfonyl-2-(4-fluorophenyl)pyrrolidine Chemical compound C1=CC(F)=CC=C1[C@@H]1N(S(=O)(=O)C=2C=CC(Cl)=CC=2)CCC1 UNWYOYFLGMANQV-MRXNPFEDSA-N 0.000 description 1
HCEKGPAHZCYRBZ-UHFFFAOYSA-N 1-(3-fluorophenyl)ethanone Chemical compound CC(=O)C1=CC=CC(F)=C1 HCEKGPAHZCYRBZ-UHFFFAOYSA-N 0.000 description 1
UNRGYFOCEIMEFF-UHFFFAOYSA-N 1-(4-methylphenyl)sulfonyl-2-[4-(trifluoromethyl)phenyl]pyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=CC(=CC=2)C(F)(F)F)CCC1 UNRGYFOCEIMEFF-UHFFFAOYSA-N 0.000 description 1
PVJZBZSCGJAWNG-UHFFFAOYSA-N 2,4,6-trimethylbenzenesulfonyl chloride Chemical compound CC1=CC(C)=C(S(Cl)(=O)=O)C(C)=C1 PVJZBZSCGJAWNG-UHFFFAOYSA-N 0.000 description 1
AFXDPDJNNABZGP-UHFFFAOYSA-N 2-(2-chlorophenyl)pyrrolidine Chemical compound ClC1=CC=CC=C1C1NCCC1 AFXDPDJNNABZGP-UHFFFAOYSA-N 0.000 description 1
KFUIACNQOMUCKR-UHFFFAOYSA-N 2-(2-fluorophenyl)-1-(4-fluorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C(C=2C(=CC=CC=2)F)CCC1 KFUIACNQOMUCKR-UHFFFAOYSA-N 0.000 description 1
LTITXVXGJJQFJC-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)pyrrolidine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1NCCC1 LTITXVXGJJQFJC-UHFFFAOYSA-N 0.000 description 1
CHEFZHGCDBJQFR-UHFFFAOYSA-N 2-(3-chloro-4-fluorophenyl)-1-(4-fluorophenyl)sulfonylpyrrolidine Chemical compound C1=CC(F)=CC=C1S(=O)(=O)N1C(C=2C=C(Cl)C(F)=CC=2)CCC1 CHEFZHGCDBJQFR-UHFFFAOYSA-N 0.000 description 1
DJJHVXPLTOQHNQ-UHFFFAOYSA-N 2-(3-chlorophenyl)-1-(4-methylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(C)=CC=C1S(=O)(=O)N1C(C=2C=C(Cl)C=CC=2)CCC1 DJJHVXPLTOQHNQ-UHFFFAOYSA-N 0.000 description 1
UBQOYOWWVWPKJE-UHFFFAOYSA-N 2-(4-chloro-3-methylphenyl)pyrrolidine Chemical compound C1=C(Cl)C(C)=CC(C2NCCC2)=C1 UBQOYOWWVWPKJE-UHFFFAOYSA-N 0.000 description 1
IBPIAQWYWUWFPS-UHFFFAOYSA-N 2-(4-ethylphenyl)pyrrolidine Chemical compound C1=CC(CC)=CC=C1C1NCCC1 IBPIAQWYWUWFPS-UHFFFAOYSA-N 0.000 description 1
NYGDFIMEPYMKOI-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-(4-propylphenyl)sulfonylpyrrolidine Chemical compound C1=CC(CCC)=CC=C1S(=O)(=O)N1C(C=2C=CC(F)=CC=2)CCC1 NYGDFIMEPYMKOI-UHFFFAOYSA-N 0.000 description 1
NRISRXVCQOEFLF-UHFFFAOYSA-N 2-(4-fluorophenyl)-1-[4-(trifluoromethyl)phenyl]sulfonylpyrrolidine Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(=CC=2)C(F)(F)F)CCC1 NRISRXVCQOEFLF-UHFFFAOYSA-N 0.000 description 1
WHDQAARCOMELQA-UHFFFAOYSA-N 2-[1-(4-fluorophenyl)sulfonylpyrrolidin-2-yl]-n,n-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1C1N(S(=O)(=O)C=2C=CC(F)=CC=2)CCC1 WHDQAARCOMELQA-UHFFFAOYSA-N 0.000 description 1
JKMHFZQWWAIEOD-UHFFFAOYSA-N 2-[4-(2-hydroxyethyl)piperazin-1-yl]ethanesulfonic acid Chemical compound OCC[NH+]1CCN(CCS([O-])(=O)=O)CC1 JKMHFZQWWAIEOD-UHFFFAOYSA-N 0.000 description 1
ACTPYQBSHREABL-UHFFFAOYSA-N 2-chloro-4-[1-(4-fluorophenyl)sulfonylpyrrolidin-2-yl]-n,n-dimethylaniline Chemical compound C1=C(Cl)C(N(C)C)=CC=C1C1N(S(=O)(=O)C=2C=CC(F)=CC=2)CCC1 ACTPYQBSHREABL-UHFFFAOYSA-N 0.000 description 1
NQAYCMBZPAARNO-UHFFFAOYSA-N 2-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1C#N NQAYCMBZPAARNO-UHFFFAOYSA-N 0.000 description 1
NJRJPZKFAIONIU-UHFFFAOYSA-N 2-fluoro-n,n-dimethyl-4-pyrrolidin-2-ylaniline Chemical compound C1=C(F)C(N(C)C)=CC=C1C1NCCC1 NJRJPZKFAIONIU-UHFFFAOYSA-N 0.000 description 1
XHKOEWNUOUBFPH-UHFFFAOYSA-N 2-fluoro-n,n-dimethyl-4-pyrrolidin-2-ylaniline;4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1.C1=C(F)C(N(C)C)=CC=C1C1NCCC1 XHKOEWNUOUBFPH-UHFFFAOYSA-N 0.000 description 1
ZSZKAQCISWFDCQ-UHFFFAOYSA-N 2-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC=C1S(Cl)(=O)=O ZSZKAQCISWFDCQ-UHFFFAOYSA-N 0.000 description 1
HDECRAPHCDXMIJ-UHFFFAOYSA-N 2-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC=C1S(Cl)(=O)=O HDECRAPHCDXMIJ-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
GNYVVCRRZRVBDD-UHFFFAOYSA-N 3-chloro-4-methylbenzenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1Cl GNYVVCRRZRVBDD-UHFFFAOYSA-N 0.000 description 1
OKYSUJVCDXZGKE-UHFFFAOYSA-N 3-fluorobenzenesulfonyl chloride Chemical compound FC1=CC=CC(S(Cl)(=O)=O)=C1 OKYSUJVCDXZGKE-UHFFFAOYSA-N 0.000 description 1
KFPMLWUKHQMEBU-UHFFFAOYSA-N 3-methylbenzenesulfonyl chloride Chemical compound CC1=CC=CC(S(Cl)(=O)=O)=C1 KFPMLWUKHQMEBU-UHFFFAOYSA-N 0.000 description 1
YCVQQVZXSUCOFF-UHFFFAOYSA-N 4-(3-fluorophenyl)-4-oxobutanenitrile Chemical compound FC1=CC=CC(C(=O)CCC#N)=C1 YCVQQVZXSUCOFF-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
IYTNNJUECQRDAI-UHFFFAOYSA-N 4-(hydroxymethyl)benzenesulfonyl chloride Chemical compound OCC1=CC=C(S(Cl)(=O)=O)C=C1 IYTNNJUECQRDAI-UHFFFAOYSA-N 0.000 description 1
OZDCZHDOIBUGAJ-UHFFFAOYSA-N 4-(trifluoromethyl)benzenesulfonyl chloride Chemical compound FC(F)(F)C1=CC=C(S(Cl)(=O)=O)C=C1 OZDCZHDOIBUGAJ-UHFFFAOYSA-N 0.000 description 1
UQYHRSLTSNXPPU-UHFFFAOYSA-N 4-[2-(4-fluorophenyl)pyrrolidin-1-yl]sulfonylbenzonitrile Chemical compound C1=CC(F)=CC=C1C1N(S(=O)(=O)C=2C=CC(=CC=2)C#N)CCC1 UQYHRSLTSNXPPU-UHFFFAOYSA-N 0.000 description 1
FXVDNCRTKXMSEZ-UHFFFAOYSA-N 4-acetylbenzenesulfonyl chloride Chemical compound CC(=O)C1=CC=C(S(Cl)(=O)=O)C=C1 FXVDNCRTKXMSEZ-UHFFFAOYSA-N 0.000 description 1
KMMHZIBWCXYAAH-UHFFFAOYSA-N 4-bromobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(Br)C=C1 KMMHZIBWCXYAAH-UHFFFAOYSA-N 0.000 description 1
DBMFYTQPPBBKHI-UHFFFAOYSA-N 4-cyanobenzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=C(C#N)C=C1 DBMFYTQPPBBKHI-UHFFFAOYSA-N 0.000 description 1
LACFLXDRFOQEFZ-UHFFFAOYSA-N 4-ethylbenzenesulfonyl chloride Chemical compound CCC1=CC=C(S(Cl)(=O)=O)C=C1 LACFLXDRFOQEFZ-UHFFFAOYSA-N 0.000 description 1
DTJVECUKADWGMO-UHFFFAOYSA-N 4-methoxybenzenesulfonyl chloride Chemical compound COC1=CC=C(S(Cl)(=O)=O)C=C1 DTJVECUKADWGMO-UHFFFAOYSA-N 0.000 description 1
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
CETRNHJIXGITKR-UHFFFAOYSA-N 4-propan-2-ylbenzenesulfonyl chloride Chemical compound CC(C)C1=CC=C(S(Cl)(=O)=O)C=C1 CETRNHJIXGITKR-UHFFFAOYSA-N 0.000 description 1
LEFGAGRZHLNPLS-UHFFFAOYSA-N 4-propylbenzenesulfonyl chloride Chemical compound CCCC1=CC=C(S(Cl)(=O)=O)C=C1 LEFGAGRZHLNPLS-UHFFFAOYSA-N 0.000 description 1
DKVORXXCYFHXCN-UHFFFAOYSA-N 5-(3-fluorophenyl)-3,4-dihydro-2h-pyrrole Chemical compound FC1=CC=CC(C=2CCCN=2)=C1 DKVORXXCYFHXCN-UHFFFAOYSA-N 0.000 description 1
WDYVUKGVKRZQNM-UHFFFAOYSA-N 6-phosphonohexylphosphonic acid Chemical compound OP(O)(=O)CCCCCCP(O)(O)=O WDYVUKGVKRZQNM-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
239000006144 Dulbecco’s modiﬁed Eagle's medium Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
102000003688 G-Protein-Coupled Receptors Human genes 0.000 description 1
108090000045 G-Protein-Coupled Receptors Proteins 0.000 description 1
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
239000007995 HEPES buffer Substances 0.000 description 1
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
102000004310 Ion Channels Human genes 0.000 description 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
108010065028 Metabotropic Glutamate 5 Receptor Proteins 0.000 description 1
102100036837 Metabotropic glutamate receptor 2 Human genes 0.000 description 1
102100038352 Metabotropic glutamate receptor 3 Human genes 0.000 description 1
102100038354 Metabotropic glutamate receptor 4 Human genes 0.000 description 1
102100038357 Metabotropic glutamate receptor 5 Human genes 0.000 description 1
102100038300 Metabotropic glutamate receptor 6 Human genes 0.000 description 1
102100038294 Metabotropic glutamate receptor 7 Human genes 0.000 description 1
102100037636 Metabotropic glutamate receptor 8 Human genes 0.000 description 1
229920000168 Microcrystalline cellulose Polymers 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
229930040373 Paraformaldehyde Natural products 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
235000021355 Stearic acid Nutrition 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
AMJRSUWJSRKGNO-UHFFFAOYSA-N acetyloxymethyl 2-[n-[2-(acetyloxymethoxy)-2-oxoethyl]-2-[2-[2-[bis[2-(acetyloxymethoxy)-2-oxoethyl]amino]-5-(2,7-dichloro-3-hydroxy-6-oxoxanthen-9-yl)phenoxy]ethoxy]-4-methylanilino]acetate Chemical compound CC(=O)OCOC(=O)CN(CC(=O)OCOC(C)=O)C1=CC=C(C)C=C1OCCOC1=CC(C2=C3C=C(Cl)C(=O)C=C3OC3=CC(O)=C(Cl)C=C32)=CC=C1N(CC(=O)OCOC(C)=O)CC(=O)OCOC(C)=O AMJRSUWJSRKGNO-UHFFFAOYSA-N 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
239000004480 active ingredient Substances 0.000 description 1
230000000996 additive effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940024606 amino acid Drugs 0.000 description 1
150000001413 amino acids Chemical class 0.000 description 1
230000003042 antagnostic effect Effects 0.000 description 1
239000003963 antioxidant agent Substances 0.000 description 1
239000012131 assay buffer Substances 0.000 description 1
150000007514 bases Chemical class 0.000 description 1
150000005524 benzylchlorides Chemical class 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
239000000872 buffer Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000002299 complementary DNA Substances 0.000 description 1
239000008120 corn starch Substances 0.000 description 1
230000001419 dependent effect Effects 0.000 description 1
XHFGWHUWQXTGAT-UHFFFAOYSA-N dimethylamine hydrochloride Natural products CNC(C)C XHFGWHUWQXTGAT-UHFFFAOYSA-N 0.000 description 1
IQDGSYLLQPDQDV-UHFFFAOYSA-N dimethylazanium;chloride Chemical compound Cl.CNC IQDGSYLLQPDQDV-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
235000003599 food sweetener Nutrition 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000001530 fumaric acid Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
229960002989 glutamic acid Drugs 0.000 description 1
125000001183 hydrocarbyl group Chemical group 0.000 description 1
150000002431 hydrogen Chemical class 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
230000003993 interaction Effects 0.000 description 1
229960004903 invert sugar Drugs 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003446 ligand Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
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
230000000873 masking effect Effects 0.000 description 1
108010038421 metabotropic glutamate receptor 2 Proteins 0.000 description 1
108010038445 metabotropic glutamate receptor 3 Proteins 0.000 description 1
108010038422 metabotropic glutamate receptor 4 Proteins 0.000 description 1
108010038450 metabotropic glutamate receptor 6 Proteins 0.000 description 1
108010038449 metabotropic glutamate receptor 7 Proteins 0.000 description 1
108010038448 metabotropic glutamate receptor 8 Proteins 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
235000019813 microcrystalline cellulose Nutrition 0.000 description 1
239000008108 microcrystalline cellulose Substances 0.000 description 1
229940016286 microcrystalline cellulose Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
OPECTNGATDYLSS-UHFFFAOYSA-N naphthalene-2-sulfonyl chloride Chemical compound C1=CC=CC2=CC(S(=O)(=O)Cl)=CC=C21 OPECTNGATDYLSS-UHFFFAOYSA-N 0.000 description 1
210000002569 neuron Anatomy 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
239000010502 orange oil Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
229920002866 paraformaldehyde Polymers 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035790 physiological processes and functions Effects 0.000 description 1
150000003053 piperidines Chemical class 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
239000000018 receptor agonist Substances 0.000 description 1
229940044601 receptor agonist Drugs 0.000 description 1
239000002464 receptor antagonist Substances 0.000 description 1
229940044551 receptor antagonist Drugs 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229930000044 secondary metabolite Natural products 0.000 description 1
210000002265 sensory receptor cell Anatomy 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008117 stearic acid Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003765 sweetening agent Substances 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical class C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
238000005303 weighing Methods 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/24—Antidepressants
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/34—Tobacco-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
- A61P25/36—Opioid-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/46—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with hetero atoms directly attached to the ring nitrogen atom
- C07D207/48—Sulfur atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
- 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
- C07D417/04—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 directly linked by a ring-member-to-ring-member bond

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Veterinary Medicine (AREA)
Animal Behavior & Ethology (AREA)
Public Health (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Health & Medical Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Psychiatry (AREA)
Addiction (AREA)
Pain & Pain Management (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Cardiology (AREA)
Hematology (AREA)
Vascular Medicine (AREA)
Emergency Medicine (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Obesity (AREA)
Psychology (AREA)
Hospice & Palliative Care (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Pyrrole Compounds (AREA)
Hydrogenated Pyridines (AREA)

NO20014617A 1999-03-25 2001-09-24 1-Arensulfonyl-2-aryl-pyrrolidin- og -piperidin-derivater for behandling av CNS-sykdommer NO319948B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP99106004		1999-03-25
PCT/EP2000/002431 WO2000058285A1 (en)	1999-03-25	2000-03-18	1-arenesulfonyl-2-aryl-pyrrolidine and piperidine derivatives for the treatment of cns disorders

Publications (3)

Publication Number	Publication Date
NO20014617D0 NO20014617D0 (no)	2001-09-24
NO20014617L NO20014617L (no)	2001-09-24
NO319948B1 true NO319948B1 (no)	2005-10-03

Family

ID=8237852

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20014617A NO319948B1 (no)	1999-03-25	2001-09-24	1-Arensulfonyl-2-aryl-pyrrolidin- og -piperidin-derivater for behandling av CNS-sykdommer

Country Status (34)

Country	Link
US (1)	US6284785B1 (es)
EP (1)	EP1165510B1 (es)
JP (1)	JP3590589B2 (es)
KR (1)	KR100452648B1 (es)
CN (1)	CN1150165C (es)
AR (1)	AR028817A1 (es)
AT (1)	ATE305451T1 (es)
AU (1)	AU765212B2 (es)
BR (1)	BR0009278A (es)
CA (1)	CA2368418C (es)
CO (1)	CO5050296A1 (es)
CZ (1)	CZ20013402A3 (es)
DE (1)	DE60022867T2 (es)
DK (1)	DK1165510T3 (es)
ES (1)	ES2249249T3 (es)
HK (1)	HK1044944B (es)
HR (1)	HRP20010682A2 (es)
HU (1)	HUP0200284A3 (es)
IL (1)	IL145301A0 (es)
JO (1)	JO2274B1 (es)
MA (1)	MA26779A1 (es)
MX (1)	MXPA01009623A (es)
MY (1)	MY125295A (es)
NO (1)	NO319948B1 (es)
NZ (1)	NZ514037A (es)
PE (1)	PE20001583A1 (es)
PL (1)	PL204436B1 (es)
RU (1)	RU2248350C2 (es)
SI (1)	SI1165510T1 (es)
TR (1)	TR200102789T2 (es)
TW (1)	TW575561B (es)
WO (1)	WO2000058285A1 (es)
YU (1)	YU67601A (es)
ZA (1)	ZA200107689B (es)

Families Citing this family (24)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US7459473B2 (en)	1998-06-03	2008-12-02	Glia Med, Inc.	N-linked sulfonamides of N-heterocyclic carboxylic acids or carboxylic acid isosteres
US6589978B2 (en) *	2000-06-30	2003-07-08	Hoffman-La Roche Inc.	1-sulfonyl pyrrolidine derivatives
US20040267010A1 (en) *	2001-02-02	2004-12-30	Forbes Ian Thomson	Sulfonamide compounds, their preparation and use
TW200302717A (en) *	2002-02-06	2003-08-16	Schering Corp	Novel gamma secretase inhibitors
WO2005030128A2 (en) *	2003-09-23	2005-04-07	Merck & Co., Inc.	Pyrazole modulators of metabotropic glutamate receptors
KR20060124712A (ko) *	2004-02-20	2006-12-05	노파르티스 아게	신경퇴행 및 인지 장애를 치료하기 위한 ｄｐｐ ⅳ 억제제
CA2567343A1 (en) *	2004-05-20	2005-12-01	Elan Pharmaceuticals, Inc.	N-cyclic sulfonamido inhibitors of gamma secretase
KR101178747B1 (ko)	2004-09-30	2012-09-03	다케다 야쿠힌 고교 가부시키가이샤	프로톤 펌프 저해제
EP1928437A2 (en)	2005-08-26	2008-06-11	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation
EP2258359A3 (en)	2005-08-26	2011-04-06	Braincells, Inc.	Neurogenesis by muscarinic receptor modulation with sabcomelin
PT1919865E (pt)	2005-08-30	2011-07-11	Takeda Pharmaceutical	Derivados de 1h-pirrole substituídos com 1-heterociclilsulfonilo, 2-aminometilo, 5-(hetero)arilo como inibidores da secreção ácida
JP2009512711A (ja)	2005-10-21	2009-03-26	ブレインセルス，インコーポレイティド	Ｐｄｅ阻害による神経新生の調節
WO2007053596A1 (en)	2005-10-31	2007-05-10	Braincells, Inc.	Gaba receptor mediated modulation of neurogenesis
US20100216734A1 (en)	2006-03-08	2010-08-26	Braincells, Inc.	Modulation of neurogenesis by nootropic agents
EP2026813A2 (en)	2006-05-09	2009-02-25	Braincells, Inc.	5 ht receptor mediated neurogenesis
WO2007134136A2 (en)	2006-05-09	2007-11-22	Braincells, Inc.	Neurogenesis by modulating angiotensin
WO2008030651A1 (en)	2006-09-08	2008-03-13	Braincells, Inc.	Combinations containing a 4-acylaminopyridine derivative
US20100184806A1 (en)	2006-09-19	2010-07-22	Braincells, Inc.	Modulation of neurogenesis by ppar agents
US8933105B2 (en)	2007-02-28	2015-01-13	Takeda Pharmaceutical Company Limited	Pyrrole compounds
PT2318390E (pt)	2008-08-27	2013-07-10	Takeda Pharmaceutical	Compostos de pirrole
WO2010099217A1 (en)	2009-02-25	2010-09-02	Braincells, Inc.	Modulation of neurogenesis using d-cycloserine combinations
GB201702221D0 (en)	2017-02-10	2017-03-29	Univ Of Sussex	Compounds
US10603313B2 (en) *	2017-07-31	2020-03-31	Chiromics, LLC	Allosteric modulators of the mu opioid receptor
GB201803340D0 (en)	2018-03-01	2018-04-18	Univ Of Sussex	Compounds

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DK167393B1 (da) *	1985-12-30	1993-10-25	Roussel Uclaf	1-sulfonyl-2-oxo-pyrrolidinderivater, deres fremstilling og farmaceutiske praeparater med indhold deraf
US5194439A (en) *	1990-04-06	1993-03-16	John Wyeth & Brother Limited	N-(2,3-dihydro-1,4-benzodioxinyl)-N-substituted aminopyrido-fused cycloalkanes
EP0618905B1 (en) *	1991-12-18	1995-10-04	Schering Corporation	Imidazolyl-alkyl-piperazine and -diazepine derivatives as histamine h3 agonists/antagonists
FR2685325B1 (fr) *	1991-12-20	1994-02-04	Adir Cie	Nouveaux derives de pyrrolidine, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
GB9612884D0 (en) *	1996-06-20	1996-08-21	Smithkline Beecham Plc	Novel compounds

2000
- 2000-03-13 TW TW89104504A patent/TW575561B/zh active
- 2000-03-18 WO PCT/EP2000/002431 patent/WO2000058285A1/en not_active Ceased
- 2000-03-18 IL IL14530100A patent/IL145301A0/xx unknown
- 2000-03-18 DE DE60022867T patent/DE60022867T2/de not_active Expired - Lifetime
- 2000-03-18 RU RU2001126570/04A patent/RU2248350C2/ru not_active IP Right Cessation
- 2000-03-18 PL PL350679A patent/PL204436B1/pl not_active IP Right Cessation
- 2000-03-18 YU YU67601A patent/YU67601A/sh unknown
- 2000-03-18 MX MXPA01009623A patent/MXPA01009623A/es active IP Right Grant
- 2000-03-18 CA CA002368418A patent/CA2368418C/en not_active Expired - Fee Related
- 2000-03-18 AT AT00910863T patent/ATE305451T1/de active
- 2000-03-18 BR BR0009278-9A patent/BR0009278A/pt active Search and Examination
- 2000-03-18 DK DK00910863T patent/DK1165510T3/da active
- 2000-03-18 HK HK02106320.6A patent/HK1044944B/zh not_active IP Right Cessation
- 2000-03-18 TR TR2001/02789T patent/TR200102789T2/xx unknown
- 2000-03-18 JP JP2000607988A patent/JP3590589B2/ja not_active Expired - Fee Related
- 2000-03-18 HU HU0200284A patent/HUP0200284A3/hu unknown
- 2000-03-18 HR HR20010682A patent/HRP20010682A2/hr not_active Application Discontinuation
- 2000-03-18 CN CNB008055300A patent/CN1150165C/zh not_active Expired - Fee Related
- 2000-03-18 SI SI200030753T patent/SI1165510T1/sl unknown
- 2000-03-18 EP EP00910863A patent/EP1165510B1/en not_active Expired - Lifetime
- 2000-03-18 AU AU32915/00A patent/AU765212B2/en not_active Ceased
- 2000-03-18 CZ CZ20013402A patent/CZ20013402A3/cs unknown
- 2000-03-18 ES ES00910863T patent/ES2249249T3/es not_active Expired - Lifetime
- 2000-03-18 KR KR10-2001-7012227A patent/KR100452648B1/ko not_active Expired - Fee Related
- 2000-03-20 PE PE2000000241A patent/PE20001583A1/es not_active Application Discontinuation
- 2000-03-22 CO CO00020380A patent/CO5050296A1/es unknown
- 2000-03-23 JO JO200025A patent/JO2274B1/en active
- 2000-03-23 MY MYPI20001145A patent/MY125295A/en unknown
- 2000-03-23 AR ARP000101297A patent/AR028817A1/es unknown
- 2000-03-24 US US09/534,380 patent/US6284785B1/en not_active Expired - Fee Related
2001
- 2001-09-18 ZA ZA200107689A patent/ZA200107689B/xx unknown
- 2001-09-24 NO NO20014617A patent/NO319948B1/no unknown
- 2001-09-25 MA MA26339A patent/MA26779A1/fr unknown
2004
- 2004-01-30 NZ NZ514037A patent/NZ514037A/xx unknown

Also Published As

Publication number	Publication date
JP2002540191A (ja)	2002-11-26
AU765212B2 (en)	2003-09-11
HUP0200284A3 (en)	2003-04-28
HUP0200284A2 (en)	2002-06-29
JO2274B1 (en)	2005-04-07
MA26779A1 (fr)	2004-12-20
TW575561B (en)	2004-02-11
CN1150165C (zh)	2004-05-19
RU2248350C2 (ru)	2005-03-20
US6284785B1 (en)	2001-09-04
MY125295A (en)	2006-07-31
DE60022867T2 (de)	2006-06-22
AR028817A1 (es)	2003-05-28
CA2368418C (en)	2009-03-10
EP1165510B1 (en)	2005-09-28
KR100452648B1 (ko)	2004-10-12
PE20001583A1 (es)	2001-01-15
JP3590589B2 (ja)	2004-11-17
DE60022867D1 (de)	2006-02-09
HK1044944B (zh)	2004-10-21
NZ514037A (en)	2004-01-30
ES2249249T3 (es)	2006-04-01
BR0009278A (pt)	2001-12-26
CZ20013402A3 (cs)	2002-03-13
PL204436B1 (pl)	2010-01-29
CO5050296A1 (es)	2001-06-27
WO2000058285A1 (en)	2000-10-05
PL350679A1 (en)	2003-01-27
YU67601A (sh)	2004-09-03
KR20010108403A (ko)	2001-12-07
MXPA01009623A (es)	2002-05-06
DK1165510T3 (da)	2006-02-06
ZA200107689B (en)	2002-12-18
NO20014617D0 (no)	2001-09-24
SI1165510T1 (sl)	2005-12-31
ATE305451T1 (de)	2005-10-15
CA2368418A1 (en)	2000-10-05
CN1345311A (zh)	2002-04-17
NO20014617L (no)	2001-09-24
HK1044944A1 (en)	2002-11-08
IL145301A0 (en)	2002-06-30
AU3291500A (en)	2000-10-16
HRP20010682A2 (en)	2002-10-31
TR200102789T2 (tr)	2002-04-22
EP1165510A1 (en)	2002-01-02

Publication	Publication Date	Title
NO319948B1 (no)	2005-10-03	1-Arensulfonyl-2-aryl-pyrrolidin- og -piperidin-derivater for behandling av CNS-sykdommer
AU638795B2 (en)	1993-07-08	3-arylcarbonyl-1h-indoles useful as therapeutic agents
AU650182B2 (en)	1994-06-09	Novel azaheterocyclylmethyl-chromans
TW200800898A (en)	2008-01-01	11-Beta HSD1 inhibitors
CZ129590A3 (en)	1995-05-17	Substituted pyrrolidine derivative, process of its preparation, intermediates of such process and pharmaceutical composition containing thereof
EP0964863B1 (de)	2003-05-21	Oxazolidinone als 5-ht2a-antagonisten
EP0546389A1 (de)	1993-06-16	Piperidylmethyl substituierte Chromanderivate als Wirkstoffe zur Behandlung von Erkrankungen des Zentralnervensystems
CN108137543B (zh)	2021-11-23	选择性nr2b拮抗剂
JP2005082508A (ja)	2005-03-31	２−アルコキシ−６−アミノ−５−ハロゲノ−ｎ−（１−置換−４−ピペリジニル）ピリジン−３−カルボキサミド誘導体およびそれを含有する医薬組成物
EP1137412A2 (en)	2001-10-04	Substituted nitrogen heterocyclic compounds and therapeutic uses thereof
JPH03184961A (ja)	1991-08-12	化合物
JP2022505401A (ja)	2022-01-14	ムスカリンｍ１受容体陽性アロステリックモジュレーターとしてのピロロ－ピリダジン誘導体
US6656958B2 (en)	2003-12-02	Substituted pyridine compounds useful for controlling chemical synaptic transmission
CA2397798C (en)	2011-01-04	Substituted pyridine compounds useful for controlling chemical synaptic transmission