SK17122002A3 - Derivát heterocyklického aminoalkylpyridínu ako psychofarmaceutické činidlo, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje - Google Patents

Derivát heterocyklického aminoalkylpyridínu ako psychofarmaceutické činidlo, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje Download PDF

Info

Publication number: SK17122002A3
Authority: SK; Slovakia
Prior art keywords: ylmethyl; ethyl; pyridin; yloxy; indol
Prior art date: 2000-06-20

Application number

SK1712-2002A

Other languages

English (en)

Slovak (sk)

Inventor

Dieter Dorsch

Henning B�Ttcher

Michael Arlt

Rudolf Gottschlich

Christoph Seyfried

Gerd Bartoszyk

J�Rgen Harting

Original Assignee

Merck Patent Gmbh

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.)

2000-06-20

Filing date

2001-06-19

Publication date

2003-04-01

2001-06-19 Application filed by Merck Patent Gmbh filed Critical Merck Patent Gmbh

2003-04-01 Publication of SK17122002A3 publication Critical patent/SK17122002A3/sk

Links

-1 Heterocyclic aminoalkyl pyridine derivatives Chemical class 0.000 title claims abstract description 146
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 19
150000003839 salts Chemical class 0.000 claims abstract description 17
125000004122 cyclic group Chemical group 0.000 claims abstract description 16
239000003814 drug Substances 0.000 claims abstract description 13
239000012453 solvate Substances 0.000 claims abstract description 12
125000001544 thienyl group Chemical group 0.000 claims abstract description 7
125000003118 aryl group Chemical group 0.000 claims abstract description 5
229920006395 saturated elastomer Polymers 0.000 claims abstract description 5
125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims abstract description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 88
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 43
150000001412 amines Chemical class 0.000 claims description 35
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 20
238000011282 treatment Methods 0.000 claims description 19
238000002360 preparation method Methods 0.000 claims description 15
238000000034 method Methods 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 claims description 10
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 10
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 9
229910052801 chlorine Inorganic materials 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
239000001257 hydrogen Substances 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
229910052757 nitrogen Inorganic materials 0.000 claims description 7
208000028017 Psychotic disease Diseases 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 6
125000004432 carbon atom Chemical group C* 0.000 claims description 6
239000000460 chlorine Substances 0.000 claims description 6
229910052731 fluorine Inorganic materials 0.000 claims description 6
125000001041 indolyl group Chemical group 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000001301 oxygen Substances 0.000 claims description 6
229910052760 oxygen Inorganic materials 0.000 claims description 6
239000008194 pharmaceutical composition Substances 0.000 claims description 6
125000005493 quinolyl group Chemical group 0.000 claims description 6
125000004215 2,4-difluorophenyl group Chemical group [H]C1=C([H])C(*)=C(F)C([H])=C1F 0.000 claims description 5
208000019901 Anxiety disease Diseases 0.000 claims description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 5
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 5
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000011737 fluorine Substances 0.000 claims description 5
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
208000020016 psychiatric disease Diseases 0.000 claims description 5
201000000980 schizophrenia Diseases 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000001164 benzothiazolyl group Chemical group S1C(=NC2=C1C=CC=C2)* 0.000 claims description 4
210000003169 central nervous system Anatomy 0.000 claims description 4
201000010099 disease Diseases 0.000 claims description 4
125000001153 fluoro group Chemical group F* 0.000 claims description 4
125000001207 fluorophenyl group Chemical group 0.000 claims description 4
125000005956 isoquinolyl group Chemical group 0.000 claims description 4
238000004519 manufacturing process Methods 0.000 claims description 4
229910052700 potassium Inorganic materials 0.000 claims description 4
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
239000002552 dosage form Substances 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
125000004433 nitrogen atom Chemical group N* 0.000 claims description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 claims description 2
JMLKDAANYBHEKO-UHFFFAOYSA-N Cl.Cl.O1C(=O)C=CC2=CC=CC=C12 Chemical compound Cl.Cl.O1C(=O)C=CC2=CC=CC=C12 JMLKDAANYBHEKO-UHFFFAOYSA-N 0.000 claims description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
SJSWRKNSCWKNIR-UHFFFAOYSA-N azane;dihydrochloride Chemical compound N.Cl.Cl SJSWRKNSCWKNIR-UHFFFAOYSA-N 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000000609 carbazolyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 claims description 2
125000000332 coumarinyl group Chemical group O1C(=O)C(=CC2=CC=CC=C12)* 0.000 claims description 2
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 2
OOBJYGFGWDCDQC-UHFFFAOYSA-N n-[[5-(2,4-difluorophenyl)pyridin-3-yl]methyl]-2-[(2-methyl-1h-indol-4-yl)oxy]ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2NC(C)=CC2=C1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C=C1F OOBJYGFGWDCDQC-UHFFFAOYSA-N 0.000 claims description 2
YCJFOKQBGVKRGS-UHFFFAOYSA-N n-[[5-(3-fluorophenyl)pyridin-3-yl]methyl]-2-quinolin-7-yloxyethanamine;hydrochloride Chemical compound Cl.FC1=CC=CC(C=2C=C(CNCCOC=3C=C4N=CC=CC4=CC=3)C=NC=2)=C1 YCJFOKQBGVKRGS-UHFFFAOYSA-N 0.000 claims description 2
ULEXDYMWKMJLQT-UHFFFAOYSA-N n-[[5-(3-fluorophenyl)pyridin-3-yl]methyl]-2-quinolin-8-yloxyethanamine;hydrochloride Chemical compound Cl.FC1=CC=CC(C=2C=C(CNCCOC=3C4=NC=CC=C4C=CC=3)C=NC=2)=C1 ULEXDYMWKMJLQT-UHFFFAOYSA-N 0.000 claims description 2
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 claims description 2
XPXUHRONTFMAID-UHFFFAOYSA-N pyridine-3-carbonyl bromide Chemical compound BrC(=O)C1=CC=CN=C1 XPXUHRONTFMAID-UHFFFAOYSA-N 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000003944 tolyl group Chemical group 0.000 claims description 2
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims 2
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound 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 claims 2
125000004211 3,5-difluorophenyl group Chemical group [H]C1=C(F)C([H])=C(*)C([H])=C1F 0.000 claims 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
XKTYVOCTMXSZSY-UHFFFAOYSA-N 5-[2-[[5-(4-fluorophenyl)pyridin-3-yl]methylamino]ethoxy]-1-methyl-3h-indol-2-one;dihydrochloride Chemical compound Cl.Cl.C=1C=C2N(C)C(=O)CC2=CC=1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C=C1 XKTYVOCTMXSZSY-UHFFFAOYSA-N 0.000 claims 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 claims 1
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
JINBYESILADKFW-UHFFFAOYSA-N aminomalonic acid Chemical compound OC(=O)C(N)C(O)=O JINBYESILADKFW-UHFFFAOYSA-N 0.000 claims 1
239000010426 asphalt Substances 0.000 claims 1
MIHBFANPMPEZEI-UHFFFAOYSA-N benzonitrile dihydrochloride Chemical compound Cl.Cl.N#CC1=CC=CC=C1 MIHBFANPMPEZEI-UHFFFAOYSA-N 0.000 claims 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims 1
MTZWZZDYFDTGAM-UHFFFAOYSA-N ethyl 7-[2-[[5-(3-cyanophenyl)pyridin-3-yl]methylamino]ethoxy]-1h-indole-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.C=12NC(C(=O)OCC)=CC2=CC=CC=1OCCNCC(C=1)=CN=CC=1C1=CC=CC(C#N)=C1 MTZWZZDYFDTGAM-UHFFFAOYSA-N 0.000 claims 1
DGDHJNXBJGNIKI-UHFFFAOYSA-N ethyl 7-[2-[[5-(3-fluorophenyl)pyridin-3-yl]methylamino]ethoxy]-1h-indole-2-carboxylate;dihydrochloride Chemical compound Cl.Cl.C=12NC(C(=O)OCC)=CC2=CC=CC=1OCCNCC(C=1)=CN=CC=1C1=CC=CC(F)=C1 DGDHJNXBJGNIKI-UHFFFAOYSA-N 0.000 claims 1
125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims 1
QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 claims 1
OLBHVQQQULOUHG-UHFFFAOYSA-N n-[[5-(2,4-difluorophenyl)pyridin-3-yl]methyl]-2-(2-methylquinolin-8-yl)oxyethanamine;hydrochloride Chemical compound Cl.C12=NC(C)=CC=C2C=CC=C1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C=C1F OLBHVQQQULOUHG-UHFFFAOYSA-N 0.000 claims 1
HXGFKRYZIKWWKK-UHFFFAOYSA-N n-[[5-(3-fluorophenyl)pyridin-3-yl]methyl]-2-(2-methylquinolin-8-yl)oxyethanamine;hydrochloride Chemical compound Cl.C12=NC(C)=CC=C2C=CC=C1OCCNCC(C=1)=CN=CC=1C1=CC=CC(F)=C1 HXGFKRYZIKWWKK-UHFFFAOYSA-N 0.000 claims 1
FNLAGYUEHNSBSX-UHFFFAOYSA-N n-[[5-(3-fluorophenyl)pyridin-3-yl]methyl]-2-[(2-methyl-1h-indol-4-yl)oxy]ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2NC(C)=CC2=C1OCCNCC(C=1)=CN=CC=1C1=CC=CC(F)=C1 FNLAGYUEHNSBSX-UHFFFAOYSA-N 0.000 claims 1
VLFNVQGSIZMQIX-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-(2-methylquinolin-8-yl)oxyethanamine;hydrochloride Chemical compound Cl.C12=NC(C)=CC=C2C=CC=C1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C=C1 VLFNVQGSIZMQIX-UHFFFAOYSA-N 0.000 claims 1
OTPCNRWIDXAFKF-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-[(2-methyl-1h-indol-4-yl)oxy]ethanamine;hydrochloride Chemical compound Cl.C1=CC=C2NC(C)=CC2=C1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C=C1 OTPCNRWIDXAFKF-UHFFFAOYSA-N 0.000 claims 1
WCICOQNBAKGXCE-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-quinolin-6-yloxyethanamine;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC(F)=CC=C1C1=CN=CC(CNCCOC=2C=C3C=CC=NC3=CC=2)=C1 WCICOQNBAKGXCE-UHFFFAOYSA-N 0.000 claims 1
BAPINESIHRRZSV-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-quinolin-8-yloxyethanamine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=CN=CC(CNCCOC=2C3=NC=CC=C3C=CC=2)=C1 BAPINESIHRRZSV-UHFFFAOYSA-N 0.000 claims 1
125000004430 oxygen atom Chemical group O* 0.000 claims 1
229940095064 tartrate Drugs 0.000 claims 1
125000004434 sulfur atom Chemical group 0.000 abstract description 3
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 22
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 description 20
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
239000000243 solution Substances 0.000 description 18
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HFGSLGHKPPLCGC-UHFFFAOYSA-N n-[[5-(3,4-difluorophenyl)pyridin-3-yl]methyl]-2-[(2-methyl-1h-indol-4-yl)oxy]ethanamine Chemical compound C1=CC=C2NC(C)=CC2=C1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C(F)=C1 HFGSLGHKPPLCGC-UHFFFAOYSA-N 0.000 description 1
XVBJFERASMOBDN-UHFFFAOYSA-N n-[[5-(3-fluorophenyl)pyridin-3-yl]methyl]-2-[(2-methyl-1h-indol-4-yl)oxy]ethanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2NC(C)=CC2=C1OCCNCC(C=1)=CN=CC=1C1=CC=CC(F)=C1 XVBJFERASMOBDN-UHFFFAOYSA-N 0.000 description 1
ZIITYSXIZAFQKO-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-(1h-indol-7-yloxy)ethanamine;hydrochloride Chemical compound Cl.C1=CC(F)=CC=C1C1=CN=CC(CNCCOC=2C=3NC=CC=3C=CC=2)=C1 ZIITYSXIZAFQKO-UHFFFAOYSA-N 0.000 description 1
SFWKEPQFWURGOS-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-[(2-methyl-1h-indol-4-yl)oxy]ethanamine;dihydrochloride Chemical compound Cl.Cl.C1=CC=C2NC(C)=CC2=C1OCCNCC(C=1)=CN=CC=1C1=CC=C(F)C=C1 SFWKEPQFWURGOS-UHFFFAOYSA-N 0.000 description 1
XXRLEOFWQYRZFD-UHFFFAOYSA-N n-[[5-(4-fluorophenyl)pyridin-3-yl]methyl]-2-isoquinolin-5-yloxyethanamine;trihydrochloride Chemical compound Cl.Cl.Cl.C1=CC(F)=CC=C1C1=CN=CC(CNCCOC=2C3=CC=NC=C3C=CC=2)=C1 XXRLEOFWQYRZFD-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
230000001537 neural effect Effects 0.000 description 1
239000002858 neurotransmitter agent Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
230000003287 optical effect Effects 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
230000003204 osmotic effect Effects 0.000 description 1
125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
229940066842 petrolatum Drugs 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
150000003016 phosphoric acids Chemical class 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000003755 preservative agent Substances 0.000 description 1
150000003141 primary amines Chemical class 0.000 description 1
239000000651 prodrug Substances 0.000 description 1
229940002612 prodrug Drugs 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
238000000159 protein binding assay Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
QJZUKDFHGGYHMC-UHFFFAOYSA-N pyridine-3-carbaldehyde Chemical compound O=CC1=CC=CN=C1 QJZUKDFHGGYHMC-UHFFFAOYSA-N 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
BKTTWZADZNUOBW-UHFFFAOYSA-N roxindole Chemical compound C=12[CH]C(O)=CC=C2N=CC=1CCCCN(CC=1)CCC=1C1=CC=CC=C1 BKTTWZADZNUOBW-UHFFFAOYSA-N 0.000 description 1
229950000366 roxindole Drugs 0.000 description 1
230000000698 schizophrenic effect Effects 0.000 description 1
125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000003521 serotonin 5-HT1 receptor agonist Substances 0.000 description 1
230000001568 sexual effect Effects 0.000 description 1
208000019116 sleep disease Diseases 0.000 description 1
239000011734 sodium Substances 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
239000008347 soybean phospholipid Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
235000000346 sugar Nutrition 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
QKSQWQOAUQFORH-UHFFFAOYSA-N tert-butyl n-[(2-methylpropan-2-yl)oxycarbonylimino]carbamate Chemical compound CC(C)(C)OC(=O)N=NC(=O)OC(C)(C)C QKSQWQOAUQFORH-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
238000011200 topical administration Methods 0.000 description 1
239000000196 tragacanth Substances 0.000 description 1
235000010487 tragacanth Nutrition 0.000 description 1
229940116362 tragacanth Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/62—Oxygen or sulfur atoms
- C07D213/63—One oxygen atom
- C07D213/64—One oxygen atom attached in position 2 or 6
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P15/08—Drugs for genital or sexual disorders; Contraceptives for gonadal disorders or for enhancing fertility, e.g. inducers of ovulation or of spermatogenesis
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- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- A—HUMAN NECESSITIES
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- A61P15/12—Drugs for genital or sexual disorders; Contraceptives for climacteric disorders
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/06—Antimigraine agents
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
- A61P25/16—Anti-Parkinson drugs
- A—HUMAN NECESSITIES
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- A—HUMAN NECESSITIES
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- 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
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P5/06—Drugs for disorders of the endocrine system of the anterior pituitary hormones, e.g. TSH, ACTH, FSH, LH, PRL, GH
- A—HUMAN NECESSITIES
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- A61P9/00—Drugs for disorders of the cardiovascular system
- 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
- 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
- A61P9/12—Antihypertensives
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/36—Radicals substituted by singly-bound nitrogen atoms
- C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
- 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
- C07D401/12—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 linked by a chain containing hetero atoms as chain links
- 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
- C07D405/12—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 linked by a chain containing hetero atoms as chain links
- 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
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

SK1712-2002A 2000-06-20 2001-06-19 Derivát heterocyklického aminoalkylpyridínu ako psychofarmaceutické činidlo, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje SK17122002A3 (sk)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE10029371A DE10029371A1 (de)	2000-06-20	2000-06-20	Heterocyclische Aminoalkylpyridinderivate als Psychopharmaka
PCT/EP2001/006915 WO2001098293A1 (fr)	2000-06-20	2001-06-19	Derives d'aminoalkylpyridine heterocycliques utilises comme medicaments psychotropes

Publications (1)

Publication Number	Publication Date
SK17122002A3 true SK17122002A3 (sk)	2003-04-01

Family

ID=7645750

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SK1712-2002A SK17122002A3 (sk)	2000-06-20	2001-06-19	Derivát heterocyklického aminoalkylpyridínu ako psychofarmaceutické činidlo, spôsob jeho prípravy, jeho použitie a farmaceutický prostriedok, ktorý ho obsahuje

Country Status (21)

Country	Link
US (1)	US6960599B2 (fr)
EP (1)	EP1292592B1 (fr)
JP (1)	JP5160715B2 (fr)
KR (1)	KR20030011092A (fr)
CN (1)	CN1437595A (fr)
AR (1)	AR028968A1 (fr)
AT (1)	ATE506357T1 (fr)
AU (2)	AU7845701A (fr)
BR (1)	BR0111816A (fr)
CA (1)	CA2410594C (fr)
CZ (1)	CZ20023955A3 (fr)
DE (2)	DE10029371A1 (fr)
ES (1)	ES2363668T3 (fr)
HU (1)	HUP0301316A2 (fr)
MX (1)	MXPA02012262A (fr)
NO (1)	NO20026104L (fr)
PL (1)	PL358672A1 (fr)
RU (1)	RU2003100514A (fr)
SK (1)	SK17122002A3 (fr)
WO (1)	WO2001098293A1 (fr)
ZA (1)	ZA200209727B (fr)

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US6800652B2 (en)	2002-08-16	2004-10-05	Pfizer Inc.	Diaryl compounds
GB0219154D0 (en) *	2002-08-16	2002-09-25	Pfizer Ltd	Diaryl compounds
DE10254596A1 (de)	2002-11-22	2004-06-03	Merck Patent Gmbh	Indolderivate
JP4896518B2 (ja) *	2002-12-13	2012-03-14	ワイエム・バイオサイエンシズ・オーストラリア・ピーティーワイ・リミテッド	ニコチンアミド系キナーゼ阻害薬
KR100679480B1 (ko) *	2004-05-18	2007-02-07	엄기형	지하층 바닥에 시공되는 배수판
US8152380B2 (en) *	2006-07-07	2012-04-10	Federal-Mogul World Wide, Inc.	Sleeve bearing assembly and method of construction
KR101043454B1 (ko) *	2009-07-10	2011-06-23	현대산업개발 주식회사	건축 지하구조물의 마감 조립체
WO2012129491A1 (fr) *	2011-03-24	2012-09-27	Abbott Laboratories	Modulateurs de trpv3
US12084472B2 (en)	2015-12-18	2024-09-10	Ardelyx, Inc.	Substituted 4-phenyl pyridine compounds as non-systemic TGR5 agonists
TWI773657B (zh)	2015-12-18	2022-08-11	美商亞德利克斯公司	作爲非全身ｔｇｒ５促效劑之經取代之4-苯基吡啶化合物

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US5002935A (en)	1987-12-30	1991-03-26	University Of Florida	Improvements in redox systems for brain-targeted drug delivery
US5177088A (en)	1991-04-17	1993-01-05	Hoechst-Roussel Pharmaceuticals Incorporated	Substituted 3-(pyridinylamino)-indoles
TW203047B (fr) *	1991-06-21	1993-04-01	American Home Prod
JPH05125024A (ja) *	1991-11-05	1993-05-21	Yamanouchi Pharmaceut Co Ltd	新規なアリールオキシアルキルアミン誘導体又はその塩
JPH05255302A (ja) *	1992-03-09	1993-10-05	Yamanouchi Pharmaceut Co Ltd	新規なクロマニルオキシアルキルアミン誘導体
DE4226527A1 (de) *	1992-08-11	1994-02-17	Merck Patent Gmbh	1,4-Benzodioxanderivate
JPH07309867A (ja) *	1994-05-19	1995-11-28	Asahi Chem Ind Co Ltd	トリプタミン誘導体およびその用途
SI0707007T1 (en)	1994-10-14	2002-04-30	Merck Patent Gmbh	(R)-(-)-2-(5-(4-fluorophenyl)-3-pyridylmethylaminomethyl)chromane as CNS active agent
JPH0940648A (ja) *	1995-08-02	1997-02-10	Yamanouchi Pharmaceut Co Ltd	新規な８−（２−アミノアルコキシ）キノリン誘導体
EP0923548B1 (fr) *	1996-08-27	2003-03-12	Wyeth	4-aminoethoxy indoles utilises en tant qu'agonistes du recepteur d2 de la dopamine et en tant que ligands des recepteurs 5ht 1a

2000
- 2000-06-20 DE DE10029371A patent/DE10029371A1/de not_active Withdrawn
2001
- 2001-06-19 RU RU2003100514/04A patent/RU2003100514A/ru not_active Application Discontinuation
- 2001-06-19 MX MXPA02012262A patent/MXPA02012262A/es unknown
- 2001-06-19 CA CA2410594A patent/CA2410594C/fr not_active Expired - Fee Related
- 2001-06-19 CN CN01811541A patent/CN1437595A/zh active Pending
- 2001-06-19 JP JP2002504249A patent/JP5160715B2/ja not_active Expired - Fee Related
- 2001-06-19 AT AT01956484T patent/ATE506357T1/de active
- 2001-06-19 US US10/311,286 patent/US6960599B2/en not_active Expired - Fee Related
- 2001-06-19 AU AU7845701A patent/AU7845701A/xx active Pending
- 2001-06-19 CZ CZ20023955A patent/CZ20023955A3/cs unknown
- 2001-06-19 HU HU0301316A patent/HUP0301316A2/hu unknown
- 2001-06-19 SK SK1712-2002A patent/SK17122002A3/sk unknown
- 2001-06-19 PL PL01358672A patent/PL358672A1/xx unknown
- 2001-06-19 WO PCT/EP2001/006915 patent/WO2001098293A1/fr not_active Ceased
- 2001-06-19 AU AU2001278457A patent/AU2001278457B2/en not_active Ceased
- 2001-06-19 KR KR1020027017265A patent/KR20030011092A/ko not_active Withdrawn
- 2001-06-19 BR BR0111816-1A patent/BR0111816A/pt not_active IP Right Cessation
- 2001-06-19 EP EP01956484A patent/EP1292592B1/fr not_active Expired - Lifetime
- 2001-06-19 ES ES01956484T patent/ES2363668T3/es not_active Expired - Lifetime
- 2001-06-19 DE DE50115858T patent/DE50115858D1/de not_active Expired - Lifetime
- 2001-06-20 AR ARP010102933A patent/AR028968A1/es unknown
2002
- 2002-11-29 ZA ZA200209727A patent/ZA200209727B/en unknown
- 2002-12-19 NO NO20026104A patent/NO20026104L/no not_active Application Discontinuation

Also Published As

Publication number	Publication date
ES2363668T3 (es)	2011-08-11
HUP0301316A2 (hu)	2003-08-28
BR0111816A (pt)	2003-06-24
CA2410594C (fr)	2010-10-26
CZ20023955A3 (cs)	2003-05-14
WO2001098293A1 (fr)	2001-12-27
DE10029371A1 (de)	2002-01-03
KR20030011092A (ko)	2003-02-06
JP5160715B2 (ja)	2013-03-13
PL358672A1 (en)	2004-08-09
ATE506357T1 (de)	2011-05-15
AU2001278457B2 (en)	2006-10-19
MXPA02012262A (es)	2003-04-25
AR028968A1 (es)	2003-05-28
NO20026104D0 (no)	2002-12-19
RU2003100514A (ru)	2004-07-20
DE50115858D1 (de)	2011-06-01
US20040019044A1 (en)	2004-01-29
AU2001278457C1 (en)	2002-01-02
CA2410594A1 (fr)	2001-12-27
JP2004501148A (ja)	2004-01-15
CN1437595A (zh)	2003-08-20
US6960599B2 (en)	2005-11-01
ZA200209727B (en)	2004-03-30
EP1292592B1 (fr)	2011-04-20
NO20026104L (no)	2002-12-19
AU7845701A (en)	2002-01-02
EP1292592A1 (fr)	2003-03-19

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