NO327756B1 - Aminometylkarboksylsyre-derivater, slike forbindelser for anvendelse i terapi, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdommer - Google Patents

Aminometylkarboksylsyre-derivater, slike forbindelser for anvendelse i terapi, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdommer Download PDF

Info

Publication number: NO327756B1
Authority: NO; Norway
Prior art keywords: methyl; phenyl; aminomethylcarboxylate; ylmethyl; acid derivative
Prior art date: 1998-07-31

Application number

NO20010514A

Other languages

English (en)

Norwegian (no)

Other versions

NO20010514L (no

NO20010514D0 (no

Inventor

Samuel George Gibson

Simon Nicholas Thorn

Robert Gilfillan

David Robert Jaap

Original Assignee

Organon Nv

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.)

1998-07-31

Filing date

2001-01-30

Publication date

2009-09-14

2001-01-30 Application filed by Organon Nv filed Critical Organon Nv

2001-01-30 Publication of NO20010514L publication Critical patent/NO20010514L/no

2001-01-30 Publication of NO20010514D0 publication Critical patent/NO20010514D0/no

2009-09-14 Publication of NO327756B1 publication Critical patent/NO327756B1/no

Links

DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical class NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 title claims description 54
239000003814 drug Substances 0.000 title claims description 6
238000002560 therapeutic procedure Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 title description 99
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 title description 5
201000010099 disease Diseases 0.000 title description 4
238000004519 manufacturing process Methods 0.000 title description 3
239000008194 pharmaceutical composition Substances 0.000 title 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 24
229910052744 lithium Inorganic materials 0.000 claims description 23
125000003118 aryl group Chemical group 0.000 claims description 20
125000000217 alkyl group Chemical group 0.000 claims description 18
239000001257 hydrogen Substances 0.000 claims description 18
229910052739 hydrogen Inorganic materials 0.000 claims description 18
125000003545 alkoxy group Chemical group 0.000 claims description 14
229910052736 halogen Inorganic materials 0.000 claims description 14
150000002367 halogens Chemical class 0.000 claims description 14
150000003839 salts Chemical class 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000001424 substituent group Chemical group 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
125000004104 aryloxy group Chemical group 0.000 claims description 8
HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 7
239000000825 pharmaceutical preparation Substances 0.000 claims description 7
238000002360 preparation method Methods 0.000 claims description 7
125000000753 cycloalkyl group Chemical group 0.000 claims description 6
150000002431 hydrogen Chemical class 0.000 claims description 6
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 4
230000004770 neurodegeneration Effects 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 3
206010012289 Dementia Diseases 0.000 claims description 3
208000023105 Huntington disease Diseases 0.000 claims description 3
208000002033 Myoclonus Diseases 0.000 claims description 3
208000018737 Parkinson disease Diseases 0.000 claims description 3
239000000654 additive Substances 0.000 claims description 3
230000019771 cognition Effects 0.000 claims description 3
206010015037 epilepsy Diseases 0.000 claims description 3
208000013403 hyperactivity Diseases 0.000 claims description 3
230000001771 impaired effect Effects 0.000 claims description 3
210000003205 muscle Anatomy 0.000 claims description 3
229910052760 oxygen Inorganic materials 0.000 claims description 3
230000002265 prevention Effects 0.000 claims description 3
208000008238 Muscle Spasticity Diseases 0.000 claims description 2
125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
208000015122 neurodegenerative disease Diseases 0.000 claims description 2
201000000980 schizophrenia Diseases 0.000 claims description 2
208000018198 spasticity Diseases 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 91
239000000203 mixture Substances 0.000 description 65
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 63
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 62
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 51
238000000034 method Methods 0.000 description 49
150000002500 ions Chemical class 0.000 description 45
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 37
239000002904 solvent Substances 0.000 description 37
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 37
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 29
XEKOWRVHYACXOJ-UHFFFAOYSA-N ethyl acetate Substances CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 28
239000011734 sodium Substances 0.000 description 27
239000000284 extract Substances 0.000 description 23
238000006243 chemical reaction Methods 0.000 description 17
238000004440 column chromatography Methods 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 16
239000000377 silicon dioxide Substances 0.000 description 16
235000019441 ethanol Nutrition 0.000 description 15
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
239000004471 Glycine Substances 0.000 description 14
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 14
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
238000010992 reflux Methods 0.000 description 14
239000007787 solid Substances 0.000 description 14
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
-1 buty I Chemical group 0.000 description 13
239000003921 oil Substances 0.000 description 13
239000002253 acid Substances 0.000 description 12
238000001816 cooling Methods 0.000 description 12
239000012043 crude product Substances 0.000 description 12
150000002148 esters Chemical class 0.000 description 11
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 11
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
FJDQFPXHSGXQBY-UHFFFAOYSA-L caesium carbonate Chemical compound [Cs+].[Cs+].[O-]C([O-])=O FJDQFPXHSGXQBY-UHFFFAOYSA-L 0.000 description 8
229910000024 caesium carbonate Inorganic materials 0.000 description 8
230000014759 maintenance of location Effects 0.000 description 8
239000003208 petroleum Substances 0.000 description 8
229920006395 saturated elastomer Polymers 0.000 description 8
239000012298 atmosphere Substances 0.000 description 7
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
210000004027 cell Anatomy 0.000 description 7
229910052757 nitrogen Inorganic materials 0.000 description 7
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 6
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 6
BRZYSWJRSDMWLG-CAXSIQPQSA-N geneticin Chemical compound O1C[C@@](O)(C)[C@H](NC)[C@@H](O)[C@H]1O[C@@H]1[C@@H](O)[C@H](O[C@@H]2[C@@H]([C@@H](O)[C@H](O)[C@@H](C(C)O)O2)N)[C@@H](N)C[C@H]1N BRZYSWJRSDMWLG-CAXSIQPQSA-N 0.000 description 6
238000006460 hydrolysis reaction Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
QMGVPVSNSZLJIA-FVWCLLPLSA-N strychnine Chemical compound O([C@H]1CC(N([C@H]2[C@H]1[C@H]1C3)C=4C5=CC=CC=4)=O)CC=C1CN1[C@@H]3[C@]25CC1 QMGVPVSNSZLJIA-FVWCLLPLSA-N 0.000 description 6
102000011714 Glycine Receptors Human genes 0.000 description 5
108010076533 Glycine Receptors Proteins 0.000 description 5
229910052794 bromium Inorganic materials 0.000 description 5
125000004432 carbon atom Chemical group C* 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
QOPVNWQGBQYBBP-UHFFFAOYSA-N chloroethyl chloroformate Chemical compound CC(Cl)OC(Cl)=O QOPVNWQGBQYBBP-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
230000007062 hydrolysis Effects 0.000 description 5
239000000047 product Substances 0.000 description 5
102000005962 receptors Human genes 0.000 description 5
108020003175 receptors Proteins 0.000 description 5
IVLXQGJVBGMLRR-UHFFFAOYSA-N 2-aminoacetic acid;hydron;chloride Chemical compound Cl.NCC(O)=O IVLXQGJVBGMLRR-UHFFFAOYSA-N 0.000 description 4
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 4
108010063380 Glycine Plasma Membrane Transport Proteins Proteins 0.000 description 4
102000010726 Glycine Plasma Membrane Transport Proteins Human genes 0.000 description 4
239000012981 Hank's balanced salt solution Substances 0.000 description 4
UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
101710083171 Sodium- and chloride-dependent glycine transporter 1 Proteins 0.000 description 4
102100023145 Sodium- and chloride-dependent glycine transporter 1 Human genes 0.000 description 4
101710083167 Sodium- and chloride-dependent glycine transporter 2 Proteins 0.000 description 4
102100028886 Sodium- and chloride-dependent glycine transporter 2 Human genes 0.000 description 4
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
238000004296 chiral HPLC Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000006260 foam Substances 0.000 description 4
230000006870 function Effects 0.000 description 4
239000011591 potassium Substances 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000725 suspension Substances 0.000 description 4
WJKHJLXJJJATHN-UHFFFAOYSA-N triflic anhydride Chemical compound FC(F)(F)S(=O)(=O)OS(=O)(=O)C(F)(F)F WJKHJLXJJJATHN-UHFFFAOYSA-N 0.000 description 4
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 3
108010078791 Carrier Proteins Proteins 0.000 description 3
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 3
102000004868 N-Methyl-D-Aspartate Receptors Human genes 0.000 description 3
108090001041 N-Methyl-D-Aspartate Receptors Proteins 0.000 description 3
QMGVPVSNSZLJIA-UHFFFAOYSA-N Nux Vomica Natural products C1C2C3C4N(C=5C6=CC=CC=5)C(=O)CC3OCC=C2CN2C1C46CC2 QMGVPVSNSZLJIA-UHFFFAOYSA-N 0.000 description 3
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
241001279009 Strychnos toxifera Species 0.000 description 3
230000002378 acidificating effect Effects 0.000 description 3
125000003277 amino group Chemical group 0.000 description 3
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 3
229910002091 carbon monoxide Inorganic materials 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
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
DEQYTNZJHKPYEZ-UHFFFAOYSA-N ethyl acetate;heptane Chemical compound CCOC(C)=O.CCCCCCC DEQYTNZJHKPYEZ-UHFFFAOYSA-N 0.000 description 3
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
239000010410 layer Substances 0.000 description 3
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
229920000137 polyphosphoric acid Polymers 0.000 description 3
229910000027 potassium carbonate Inorganic materials 0.000 description 3
108090000623 proteins and genes Proteins 0.000 description 3
230000009467 reduction Effects 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
239000011780 sodium chloride Substances 0.000 description 3
239000012258 stirred mixture Substances 0.000 description 3
229960005453 strychnine Drugs 0.000 description 3
LVEYOSJUKRVCCF-UHFFFAOYSA-N 1,3-bis(diphenylphosphino)propane Chemical compound C=1C=CC=CC=1P(C=1C=CC=CC=1)CCCP(C=1C=CC=CC=1)C1=CC=CC=C1 LVEYOSJUKRVCCF-UHFFFAOYSA-N 0.000 description 2
PIKNVEVCWAAOMJ-UHFFFAOYSA-N 3-fluorobenzaldehyde Chemical compound FC1=CC=CC(C=O)=C1 PIKNVEVCWAAOMJ-UHFFFAOYSA-N 0.000 description 2
SFUDEIQDDYJRKV-UHFFFAOYSA-N 4-(3-fluorophenyl)butanoic acid Chemical compound OC(=O)CCCC1=CC=CC(F)=C1 SFUDEIQDDYJRKV-UHFFFAOYSA-N 0.000 description 2
VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
206010019196 Head injury Diseases 0.000 description 2
101000631937 Homo sapiens Sodium- and chloride-dependent glycine transporter 2 Proteins 0.000 description 2
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 2
WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 2
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
239000008186 active pharmaceutical agent Substances 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
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238000004458 analytical method Methods 0.000 description 2
230000037396 body weight Effects 0.000 description 2
UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 2
JPOXNPPZZKNXOV-UHFFFAOYSA-N bromochloromethane Chemical compound ClCBr JPOXNPPZZKNXOV-UHFFFAOYSA-N 0.000 description 2
244000309464 bull Species 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
229910052801 chlorine Inorganic materials 0.000 description 2
238000003776 cleavage reaction Methods 0.000 description 2
230000001276 controlling effect Effects 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
229940079593 drug Drugs 0.000 description 2
238000010931 ester hydrolysis Methods 0.000 description 2
OAMZXMDZZWGPMH-UHFFFAOYSA-N ethyl acetate;toluene Chemical compound CCOC(C)=O.CC1=CC=CC=C1 OAMZXMDZZWGPMH-UHFFFAOYSA-N 0.000 description 2
230000002964 excitative effect Effects 0.000 description 2
239000012530 fluid Substances 0.000 description 2
239000012458 free base Substances 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
229930195712 glutamate Natural products 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
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229910052500 inorganic mineral Inorganic materials 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000007788 liquid Substances 0.000 description 2
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
230000004060 metabolic process Effects 0.000 description 2
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125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
230000001242 postsynaptic effect Effects 0.000 description 1
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
102000004196 processed proteins & peptides Human genes 0.000 description 1
108090000765 processed proteins & peptides Proteins 0.000 description 1
238000012545 processing Methods 0.000 description 1
235000019260 propionic acid Nutrition 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
208000020016 psychiatric disease Diseases 0.000 description 1
238000000746 purification Methods 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
238000004366 reverse phase liquid chromatography Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000003345 scintillation counting Methods 0.000 description 1
238000012163 sequencing technique Methods 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
230000000946 synaptic effect Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
238000010189 synthetic method Methods 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
230000002123 temporal effect Effects 0.000 description 1
CXWXQJXEFPUFDZ-UHFFFAOYSA-N tetralin Chemical compound C1=CC=C2CCCCC2=C1 CXWXQJXEFPUFDZ-UHFFFAOYSA-N 0.000 description 1
229940124597 therapeutic agent Drugs 0.000 description 1
ARYHTUPFQTUBBG-UHFFFAOYSA-N thiophen-2-ylboronic acid Chemical compound OB(O)C1=CC=CS1 ARYHTUPFQTUBBG-UHFFFAOYSA-N 0.000 description 1
210000001519 tissue Anatomy 0.000 description 1
231100000331 toxic Toxicity 0.000 description 1
230000002588 toxic effect Effects 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000000844 transformation Methods 0.000 description 1
QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
238000001665 trituration Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
- C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
- 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
- A61P25/08—Antiepileptics; Anticonvulsants
- 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
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/02—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton
- C07C229/04—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated
- C07C229/06—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton
- C07C229/10—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings
- C07C229/14—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to acyclic carbon atoms of the same carbon skeleton the carbon skeleton being acyclic and saturated having only one amino and one carboxyl group bound to the carbon skeleton the nitrogen atom of the amino group being further bound to acyclic carbon atoms or to carbon atoms of rings other than six-membered aromatic rings to carbon atoms of carbon skeletons containing rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
- C07C229/38—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino groups bound to acyclic carbon atoms and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
- C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C255/58—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
- C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D311/04—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring
- C07D311/58—Benzo[b]pyrans, not hydrogenated in the carbocyclic ring other than with oxygen or sulphur atoms in position 2 or 4
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D317/70—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with ring systems containing two or more relevant rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/06—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring carbon atoms
- C07D333/14—Radicals substituted by singly bound hetero atoms other than halogen
- C07D333/20—Radicals substituted by singly bound hetero atoms other than halogen by nitrogen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07B—GENERAL METHODS OF ORGANIC CHEMISTRY; APPARATUS THEREFOR
- C07B2200/00—Indexing scheme relating to specific properties of organic compounds
- C07B2200/07—Optical isomers
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2602/00—Systems containing two condensed rings
- C07C2602/02—Systems containing two condensed rings the rings having only two atoms in common
- C07C2602/04—One of the condensed rings being a six-membered aromatic ring
- C07C2602/10—One of the condensed rings being a six-membered aromatic ring the other ring being six-membered, e.g. tetraline

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Neurology (AREA)
Biomedical Technology (AREA)
Neurosurgery (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Psychiatry (AREA)
Pain & Pain Management (AREA)
Psychology (AREA)
Physical Education & Sports Medicine (AREA)
Orthopedic Medicine & Surgery (AREA)
Hospice & Palliative Care (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds Containing Sulfur Atoms (AREA)
Pyrane Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

NO20010514A 1998-07-31 2001-01-30 Aminometylkarboksylsyre-derivater, slike forbindelser for anvendelse i terapi, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdommer NO327756B1 (no)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP98306149		1998-07-31
PCT/EP1999/005477 WO2000007978A1 (en)	1998-07-31	1999-07-26	Aminomethylcarboxylic acid derivatives

Publications (3)

Publication Number	Publication Date
NO20010514L NO20010514L (no)	2001-01-30
NO20010514D0 NO20010514D0 (no)	2001-01-30
NO327756B1 true NO327756B1 (no)	2009-09-14

Family

ID=8234975

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO20010514A NO327756B1 (no)	1998-07-31	2001-01-30	Aminometylkarboksylsyre-derivater, slike forbindelser for anvendelse i terapi, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdommer

Country Status (28)

Country	Link
US (1)	US6410592B1 (da)
EP (1)	EP1100769B1 (da)
JP (1)	JP4290340B2 (da)
KR (1)	KR100640031B1 (da)
CN (1)	CN1191232C (da)
AR (1)	AR049670A1 (da)
AT (1)	ATE228995T1 (da)
AU (1)	AU762759B2 (da)
BR (1)	BR9912621A (da)
CA (1)	CA2337041C (da)
CO (1)	CO5080746A1 (da)
CZ (1)	CZ301620B6 (da)
DE (1)	DE69904335T2 (da)
DK (1)	DK1100769T3 (da)
ES (1)	ES2189462T3 (da)
HK (1)	HK1035525A1 (da)
HU (1)	HUP0102766A3 (da)
ID (1)	ID26978A (da)
IL (1)	IL140358A0 (da)
NO (1)	NO327756B1 (da)
NZ (1)	NZ509568A (da)
PL (1)	PL198041B1 (da)
PT (1)	PT1100769E (da)
RU (1)	RU2225389C2 (da)
SK (1)	SK286474B6 (da)
TR (1)	TR200100270T2 (da)
TW (1)	TW555757B (da)
WO (1)	WO2000007978A1 (da)

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AR075442A1 (es)	2009-02-16	2011-03-30	Abbott Gmbh & Co Kg	Derivados de aminotetralina, composiciones farmaceuticas que las contienen y sus usos en terapia
EP2380595A1 (en)	2010-04-19	2011-10-26	Nlife Therapeutics S.L.	Compositions and methods for selective delivery of oligonucleotide molecules to specific neuron types
US9051280B2 (en)	2010-08-13	2015-06-09	AbbVie Deutschland GmbH & Co. KG	Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy
US8877794B2 (en)	2010-08-13	2014-11-04	Abbott Laboratories	Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy
US8883839B2 (en) *	2010-08-13	2014-11-11	Abbott Laboratories	Tetraline and indane derivatives, pharmaceutical compositions containing them, and their use in therapy
US8846743B2 (en) *	2010-08-13	2014-09-30	Abbott Laboratories	Aminoindane derivatives, pharmaceutical compositions containing them, and their use in therapy
US9045459B2 (en)	2010-08-13	2015-06-02	AbbVie Deutschland GmbH & Co. KG	Phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy
WO2013020930A1 (en) *	2011-08-05	2013-02-14	Abbott Gmbh & Co. Kg	Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy
WO2013064206A1 (de)	2011-11-01	2013-05-10	Merck Patent Gmbh	Organische elektrolumineszenzvorrichtung
KR102310368B1 (ko)	2011-11-17	2021-10-07	메르크 파텐트 게엠베하	스피로디히드로아크리딘 유도체 및 이의 유기 전계발광 소자용 재료로서의 용도
WO2013072520A1 (en)	2011-11-18	2013-05-23	AbbVie Deutschland GmbH & Co. KG	N-substituted aminobenzocycloheptene, aminotetraline, aminoindane and phenalkylamine derivatives, pharmaceutical compositions containing them, and their use in therapy
US9365512B2 (en)	2012-02-13	2016-06-14	AbbVie Deutschland GmbH & Co. KG	Isoindoline derivatives, pharmaceutical compositions containing them, and their use in therapy
WO2013139431A1 (de)	2012-03-23	2013-09-26	Merck Patent Gmbh	9,9'-spirobixanthenderivate für elektrolumineszenzvorrichtungen
US9650334B2 (en)	2013-03-15	2017-05-16	Abbvie Inc.	Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy
US9656955B2 (en)	2013-03-15	2017-05-23	Abbvie Inc.	Pyrrolidine derivatives, pharmaceutical compositions containing them, and their use in therapy
MX2016004934A (es)	2013-10-17	2016-12-20	Abbvie Deutschland	Derivados de aminotetralina y aminoindano, composiciones farmaceuticas que los contienen, y su uso en terapia.
AU2014336153A1 (en)	2013-10-17	2016-04-28	AbbVie Deutschland GmbH & Co. KG	Aminochromane, aminothiochromane and amino-1,2,3,4-tetrahydroquinoline derivatives, pharmaceutical compositions containing them, and their use in therapy
CN104844471B (zh) *	2015-04-21	2017-05-03	苏州远智医药科技有限公司	一种作为dor受体拮抗剂的化合物
US10226442B2 (en) *	2017-07-10	2019-03-12	Syneurx International (Taiwan) Corp.	Lithium salts of N-substituted glycine compounds and uses thereof
CN111108105B (zh)	2017-09-22	2023-03-31	朱比兰特埃皮帕德有限公司	作为pad抑制剂的杂环化合物
FI3697785T3 (fi)	2017-10-18	2023-04-03	Jubilant Epipad LLC	Imidatsopyridiiniyhdisteitä pad:n estäjinä
CN111386265A (zh)	2017-11-06	2020-07-07	朱比连特普罗德尔有限责任公司	作为pd1/pd-l1活化的抑制剂的嘧啶衍生物
LT3704120T (lt)	2017-11-24	2024-06-25	Jubilant Episcribe Llc	Heterocikliniai junginiai kaip prmt5 inhibitoriai
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1999
- 1999-07-23 TW TW088112566A patent/TW555757B/zh not_active IP Right Cessation
- 1999-07-26 CA CA002337041A patent/CA2337041C/en not_active Expired - Lifetime
- 1999-07-26 AT AT99939419T patent/ATE228995T1/de active
- 1999-07-26 HU HU0102766A patent/HUP0102766A3/hu unknown
- 1999-07-26 IL IL14035899A patent/IL140358A0/xx not_active IP Right Cessation
- 1999-07-26 US US09/744,520 patent/US6410592B1/en not_active Expired - Lifetime
- 1999-07-26 KR KR1020017001327A patent/KR100640031B1/ko not_active IP Right Cessation
- 1999-07-26 NZ NZ509568A patent/NZ509568A/en not_active IP Right Cessation
- 1999-07-26 TR TR2001/00270T patent/TR200100270T2/xx unknown
- 1999-07-26 BR BR9912621-4A patent/BR9912621A/pt not_active Application Discontinuation
- 1999-07-26 PT PT99939419T patent/PT1100769E/pt unknown
- 1999-07-26 ES ES99939419T patent/ES2189462T3/es not_active Expired - Lifetime
- 1999-07-26 AU AU53724/99A patent/AU762759B2/en not_active Expired
- 1999-07-26 CN CNB998086649A patent/CN1191232C/zh not_active Expired - Lifetime
- 1999-07-26 CZ CZ20010398A patent/CZ301620B6/cs not_active IP Right Cessation
- 1999-07-26 SK SK149-2001A patent/SK286474B6/sk not_active IP Right Cessation
- 1999-07-26 EP EP99939419A patent/EP1100769B1/en not_active Expired - Lifetime
- 1999-07-26 ID IDW20010234A patent/ID26978A/id unknown
- 1999-07-26 DE DE69904335T patent/DE69904335T2/de not_active Expired - Lifetime
- 1999-07-26 RU RU2001105536/04A patent/RU2225389C2/ru not_active IP Right Cessation
- 1999-07-26 WO PCT/EP1999/005477 patent/WO2000007978A1/en active Search and Examination
- 1999-07-26 DK DK99939419T patent/DK1100769T3/da active
- 1999-07-26 PL PL345794A patent/PL198041B1/pl not_active IP Right Cessation
- 1999-07-26 JP JP2000563613A patent/JP4290340B2/ja not_active Expired - Lifetime
- 1999-07-29 AR ARP990103756A patent/AR049670A1/es active IP Right Grant
- 1999-07-30 CO CO99048379A patent/CO5080746A1/es unknown
2001
- 2001-01-30 NO NO20010514A patent/NO327756B1/no not_active IP Right Cessation
- 2001-09-04 HK HK01106227A patent/HK1035525A1/xx not_active IP Right Cessation

Also Published As

Publication number	Publication date
CA2337041A1 (en)	2000-02-17
DE69904335T2 (de)	2003-10-09
KR20010072137A (ko)	2001-07-31
CN1309631A (zh)	2001-08-22
CO5080746A1 (es)	2001-09-25
TW555757B (en)	2003-10-01
HUP0102766A2 (hu)	2001-12-28
US6410592B1 (en)	2002-06-25
CA2337041C (en)	2009-05-26
CN1191232C (zh)	2005-03-02
DE69904335D1 (en)	2003-01-16
AR049670A1 (es)	2006-08-30
NO20010514L (no)	2001-01-30
AU762759B2 (en)	2003-07-03
PT1100769E (pt)	2003-04-30
AU5372499A (en)	2000-02-28
SK286474B6 (sk)	2008-11-06
HK1035525A1 (en)	2001-11-30
ES2189462T3 (es)	2003-07-01
BR9912621A (pt)	2001-04-24
JP2002522412A (ja)	2002-07-23
ID26978A (id)	2001-02-22
EP1100769A1 (en)	2001-05-23
PL198041B1 (pl)	2008-05-30
CZ2001398A3 (cs)	2001-07-11
ATE228995T1 (de)	2002-12-15
JP4290340B2 (ja)	2009-07-01
DK1100769T3 (da)	2003-03-24
EP1100769B1 (en)	2002-12-04
TR200100270T2 (tr)	2001-05-21
IL140358A0 (en)	2002-02-10
NZ509568A (en)	2003-05-30
HUP0102766A3 (en)	2002-11-28
RU2225389C2 (ru)	2004-03-10
KR100640031B1 (ko)	2006-10-31
NO20010514D0 (no)	2001-01-30
WO2000007978A1 (en)	2000-02-17
SK1492001A3 (en)	2001-08-06
PL345794A1 (en)	2002-01-02
CZ301620B6 (cs)	2010-05-05

Publication	Publication Date	Title
NO327756B1 (no)	2009-09-14	Aminometylkarboksylsyre-derivater, slike forbindelser for anvendelse i terapi, farmasoytiske preparater inneholdende slike samt anvendelse av slike for fremstilling av medikament for behandling av sykdommer
EP1232160B1 (en)	2008-06-18	Spiro(2h-1-benzopyran-2,4'-piperidine)derivates as glycine transport inhibitors
NZ223647A (en)	1991-06-25	3-amino-dihydro-(1)-benzo-pyrans
AU736716B2 (en)	2001-08-02	New heterocyclic compounds, a process for their preparation and pharmaceutical compositions containing them
NO324562B1 (no)	2007-11-19	Nye substituerte heterocykliske forbindelser, fremgangsmate ved deres fremstilling og farmasoytiske sammensetninger inneholdende dem
US5641785A (en)	1997-06-24	Oxazoloquinolinone derivatives, their preparation and their therapeutic application as inhibitors of monoamine oxidase
KR960011392B1 (ko)	1996-08-22	티오펜 카복스아미드 화합물 및 이의 제조방법
MXPA01001174A (en)	2001-12-13	Aminomethylcarboxylic acid derivatives
Bös et al.	1998	Syntheses of O‐Methylasparvenone‐Derived Serotonin‐Receptor Antagonists
RU2164915C2 (ru)	2001-04-10	Производные 4н-пирана, смесь их изомеров, отдельные изомеры и их соли
WO2001036428A1 (en)	2001-05-25	Silylated heterocyclic compounds
CN102947301A (zh)	2013-02-27	喹嗪烷和吲嗪烷衍生物
JPWO2002024641A1 (ja)	2004-01-29	セロトニン受容体親和性を有する三環性インドール化合物
JP3034556B2 (ja)	2000-04-17	医薬用化合物類
US6028112A (en)	2000-02-22	Spirocyclopropyl fluorenes as melatonergic agents
NO301327B1 (no)	1997-10-13	Tienocyklopentanonoksimetere, og farmasöytiske blandinger som inneholder dem
WO2009109648A1 (en)	2009-09-11	Process for preparing compounds containing a hydronaphtalene structure with an unsymmetrically substituted benzene ring
EP0371594A1 (en)	1990-06-06	Thiophene-carboxamide derivatives and their pharmaceutical use

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