UA75407C2 - Heteroaryl derivatives of pyridine and pyrimidine, pharmaceutical composition and use thereof - Google Patents

Heteroaryl derivatives of pyridine and pyrimidine, pharmaceutical composition and use thereof Download PDF

Info

Publication number: UA75407C2
Authority: UA; Ukraine
Prior art keywords: piperazin; dioxin; chloro; dihydrobenzo; cyano
Prior art date: 2001-06-29

Application number

UA20031211984A

Other languages

English (en)

Ukrainian (uk)

Inventor

Einer Knud Moltsen

Original Assignee

Lundbeck & Co As H

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2001-06-29

Filing date

2002-06-27

Publication date

2006-04-17

2002-06-27 Application filed by Lundbeck & Co As H filed Critical Lundbeck & Co As H

2006-04-17 Publication of UA75407C2 publication Critical patent/UA75407C2/uk

Links

125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 10
JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 title claims description 49
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 title claims description 25
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 title claims description 7
239000008194 pharmaceutical composition Substances 0.000 title claims description 7
150000001875 compounds Chemical class 0.000 claims abstract description 79
208000012902 Nervous system disease Diseases 0.000 claims abstract description 9
208000025966 Neurological disease Diseases 0.000 claims abstract description 8
208000028017 Psychotic disease Diseases 0.000 claims abstract description 8
208000019906 panic disease Diseases 0.000 claims abstract description 8
208000019022 Mood disease Diseases 0.000 claims abstract description 7
208000021384 Obsessive-Compulsive disease Diseases 0.000 claims abstract description 7
206010041250 Social phobia Diseases 0.000 claims abstract description 6
208000030814 Eating disease Diseases 0.000 claims abstract description 5
208000019454 Feeding and Eating disease Diseases 0.000 claims abstract description 5
235000014632 disordered eating Nutrition 0.000 claims abstract description 5
125000004194 piperazin-1-yl group Chemical group [H]N1C([H])([H])C([H])([H])N(*)C([H])([H])C1([H])[H] 0.000 claims description 88
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 67
GZPHSAQLYPIAIN-UHFFFAOYSA-N 3-pyridinecarbonitrile Chemical compound N#CC1=CC=CN=C1 GZPHSAQLYPIAIN-UHFFFAOYSA-N 0.000 claims description 38
238000000034 method Methods 0.000 claims description 27
-1 hydroxy, formyl Chemical group 0.000 claims description 22
150000003839 salts Chemical class 0.000 claims description 21
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
239000000203 mixture Substances 0.000 claims description 17
229910052739 hydrogen Inorganic materials 0.000 claims description 16
239000001257 hydrogen Substances 0.000 claims description 16
239000002253 acid Substances 0.000 claims description 15
125000004705 ethylthio group Chemical group C(C)S* 0.000 claims description 15
229960003638 dopamine Drugs 0.000 claims description 14
150000002431 hydrogen Chemical class 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 12
150000002367 halogens Chemical class 0.000 claims description 12
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 11
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 10
125000002252 acyl group Chemical group 0.000 claims description 10
201000010099 disease Diseases 0.000 claims description 10
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 10
208000035475 disorder Diseases 0.000 claims description 9
241001465754 Metazoa Species 0.000 claims description 8
239000000654 additive Substances 0.000 claims description 8
125000004093 cyano group Chemical group *C#N 0.000 claims description 8
208000011688 Generalised anxiety disease Diseases 0.000 claims description 6
125000004442 acylamino group Chemical group 0.000 claims description 6
125000006598 aminocarbonylamino group Chemical group 0.000 claims description 6
208000029364 generalized anxiety disease Diseases 0.000 claims description 6
229940126601 medicinal product Drugs 0.000 claims description 6
125000000449 nitro group Chemical group [O-][N+](*)=O 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
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 6
230000000996 additive effect Effects 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
239000003085 diluting agent Substances 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 4
230000008485 antagonism Effects 0.000 claims description 4
229910052801 chlorine Inorganic materials 0.000 claims description 4
239000000460 chlorine Substances 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 4
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 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 3
230000002301 combined effect Effects 0.000 claims description 3
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
230000008517 inhibition of serotonin uptake Effects 0.000 claims description 3
150000002825 nitriles Chemical class 0.000 claims description 3
GBXQPDCOMJJCMJ-UHFFFAOYSA-M trimethyl-[6-(trimethylazaniumyl)hexyl]azanium;bromide Chemical compound [Br-].C[N+](C)(C)CCCCCC[N+](C)(C)C GBXQPDCOMJJCMJ-UHFFFAOYSA-M 0.000 claims description 3
XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical compound [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims description 2
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
125000005842 heteroatom Chemical group 0.000 claims description 2
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 2
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
229960002715 nicotine Drugs 0.000 claims description 2
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Natural products CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
229930192474 thiophene Natural products 0.000 claims description 2
125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims 1
HGUFODBRKLSHSI-UHFFFAOYSA-N 2,3,7,8-tetrachloro-dibenzo-p-dioxin Chemical compound O1C2=CC(Cl)=C(Cl)C=C2OC2=C1C=C(Cl)C(Cl)=C2 HGUFODBRKLSHSI-UHFFFAOYSA-N 0.000 claims 1
208000017194 Affective disease Diseases 0.000 claims 1
241000790917 Dioxys <bee> Species 0.000 claims 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
125000004193 piperazinyl group Chemical group 0.000 claims 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims 1
229940002612 prodrug Drugs 0.000 claims 1
239000000651 prodrug Substances 0.000 claims 1
238000012876 topography Methods 0.000 claims 1
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238000004895 liquid chromatography mass spectrometry Methods 0.000 description 66
108020003175 receptors Proteins 0.000 description 20
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
230000000694 effects Effects 0.000 description 12
230000005764 inhibitory process Effects 0.000 description 10
239000000243 solution Substances 0.000 description 10
125000000217 alkyl group Chemical group 0.000 description 9
238000012360 testing method Methods 0.000 description 9
230000003042 antagnostic effect Effects 0.000 description 8
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 8
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XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
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OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 4
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210000004027 cell Anatomy 0.000 description 4
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108091032151 5-hydroxytryptamine receptor family Proteins 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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239000002585 base Substances 0.000 description 3
210000004556 brain Anatomy 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 3
238000004440 column chromatography Methods 0.000 description 3
238000002347 injection Methods 0.000 description 3
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LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 3
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VYKKXFKBCJQVGU-UHFFFAOYSA-N 4,6-dimethyl-2-(2-oxoethylsulfanyl)pyridine-3-carbonitrile Chemical compound CC1=CC(C)=C(C#N)C(SCC=O)=N1 VYKKXFKBCJQVGU-UHFFFAOYSA-N 0.000 description 2
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230000003291 dopaminomimetic effect Effects 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
238000001035 drying Methods 0.000 description 1
239000000975 dye Substances 0.000 description 1
230000000695 effect on serotonin Effects 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
230000008713 feedback mechanism Effects 0.000 description 1
238000011049 filling Methods 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
238000013467 fragmentation Methods 0.000 description 1
238000006062 fragmentation reaction Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000002541 furyl group Chemical group 0.000 description 1
JVZRCNQLWOELDU-UHFFFAOYSA-N gamma-Phenylpyridine Natural products C1=CC=CC=C1C1=CC=NC=C1 JVZRCNQLWOELDU-UHFFFAOYSA-N 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
235000012907 honey Nutrition 0.000 description 1
230000003054 hormonal effect Effects 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
125000002883 imidazolyl group Chemical group 0.000 description 1
125000001041 indolyl group Chemical group 0.000 description 1
239000003112 inhibitor Substances 0.000 description 1
239000011630 iodine Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
238000004255 ion exchange chromatography Methods 0.000 description 1
208000028867 ischemia Diseases 0.000 description 1
230000000302 ischemic effect Effects 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
125000001786 isothiazolyl group Chemical group 0.000 description 1
239000007951 isotonicity adjuster Substances 0.000 description 1
125000000842 isoxazolyl group Chemical group 0.000 description 1
239000008101 lactose Substances 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
238000001819 mass spectrum Methods 0.000 description 1
239000011159 matrix material Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
WZHJKEUHNJHDLS-QTGUNEKASA-N metergoline Chemical compound C([C@H]1CN([C@H]2[C@@H](C=3C=CC=C4N(C)C=C(C=34)C2)C1)C)NC(=O)OCC1=CC=CC=C1 WZHJKEUHNJHDLS-QTGUNEKASA-N 0.000 description 1
229960004650 metergoline Drugs 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001624 naphthyl group Chemical group 0.000 description 1
239000006199 nebulizer Substances 0.000 description 1
210000001577 neostriatum Anatomy 0.000 description 1
230000009871 nonspecific binding Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
239000004031 partial agonist Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000003386 piperidinyl group Chemical group 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229920001592 potato starch Polymers 0.000 description 1
239000000843 powder Substances 0.000 description 1
238000012545 processing Methods 0.000 description 1
238000000746 purification Methods 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
125000004076 pyridyl group Chemical group 0.000 description 1
WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
125000000168 pyrrolyl group Chemical group 0.000 description 1
230000002285 radioactive effect Effects 0.000 description 1
238000006268 reductive amination reaction Methods 0.000 description 1
230000002441 reversible effect Effects 0.000 description 1
238000012552 review Methods 0.000 description 1
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
229940124834 selective serotonin reuptake inhibitor Drugs 0.000 description 1
230000000862 serotonergic effect Effects 0.000 description 1
230000013275 serotonin uptake Effects 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012321 sodium triacetoxyborohydride Substances 0.000 description 1
229950001675 spiperone Drugs 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
208000011580 syndromic disease Diseases 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
150000003892 tartrate salts Chemical class 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
125000003831 tetrazolyl group Chemical group 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
VOVUARRWDCVURC-UHFFFAOYSA-N thiirane Chemical compound C1CS1 VOVUARRWDCVURC-UHFFFAOYSA-N 0.000 description 1
238000004448 titration Methods 0.000 description 1
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 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
- C07D401/12—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
- C07D405/14—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 three or more hetero rings
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- A61P1/14—Prodigestives, e.g. acids, enzymes, appetite stimulants, antidyspeptics, tonics, antiflatulents
- 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
- A61P25/04—Centrally acting analgesics, e.g. opioids
- 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
- A61P25/18—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
- A61P25/22—Anxiolytics
- 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
- A61P25/32—Alcohol-abuse
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- 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
- 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
- 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
- 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
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Landscapes

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

UA20031211984A 2001-06-29 2002-06-27 Heteroaryl derivatives of pyridine and pyrimidine, pharmaceutical composition and use thereof UA75407C2 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DKPA200101036		2001-06-29
PCT/DK2002/000435 WO2003002556A1 (en)	2001-06-29	2002-06-27	Novel heteroaryl derivatives, their preparation and use

Publications (1)

Publication Number	Publication Date
UA75407C2 true UA75407C2 (en)	2006-04-17

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UA20031211984A UA75407C2 (en)	2001-06-29	2002-06-27	Heteroaryl derivatives of pyridine and pyrimidine, pharmaceutical composition and use thereof

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US (2)	US20040248883A1 (de)
EP (1)	EP1399438B1 (de)
JP (1)	JP2004535449A (de)
KR (1)	KR20040019026A (de)
CN (1)	CN1310909C (de)
AT (1)	ATE312094T1 (de)
AU (1)	AU2002344949B2 (de)
BG (1)	BG108531A (de)
BR (1)	BR0210401A (de)
CA (1)	CA2451228A1 (de)
CZ (1)	CZ2004156A3 (de)
DE (1)	DE60207857T2 (de)
DK (1)	DK1399438T3 (de)
EA (1)	EA006203B1 (de)
ES (1)	ES2252471T3 (de)
HU (1)	HUP0400344A2 (de)
IL (1)	IL158828A0 (de)
IS (1)	IS2425B (de)
MX (1)	MXPA03011769A (de)
NO (1)	NO326514B1 (de)
NZ (1)	NZ529460A (de)
PL (1)	PL365249A1 (de)
SI (1)	SI1399438T1 (de)
SK (1)	SK652004A3 (de)
UA (1)	UA75407C2 (de)
WO (1)	WO2003002556A1 (de)

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CA2451229C (en) *	2001-06-29	2009-02-10	H. Lundbeck A/S	Indole derivatives
DK1408976T5 (da) *	2001-07-20	2011-01-10	Psychogenics Inc	Behandling af ADHD (Attention deficit hyperactivity disorder)
DE112004001191B4 (de) *	2003-07-02	2017-11-09	Corus Pharma Inc.	Verfahren zur Herstellung des L-Lysin-Salzes von Aztreonam und Verfahren zur Bestimmung des Verunreinigungsgrads in einem amorphen Aztreonam Lysin-Salz
US7160888B2 (en)	2003-08-22	2007-01-09	Warner Lambert Company Llc	[1,8]naphthyridin-2-ones and related compounds for the treatment of schizophrenia
ES2331144T3 (es)	2004-11-26	2009-12-22	Janssen Pharmaceutica Nv	Derivados de isoxazolina-indol con actividad antipsicotica y ansiolitica mejorada.
CN102822167A (zh)	2010-01-04	2012-12-12	埃南蒂亚有限公司	用于制备利伐沙班的方法及其中间体
JP5546678B2 (ja)	2010-04-12	2014-07-09	ロッテケミカルコーポレーション	チオフェン−縮合環シクロペンタジエニルリガンドを含む遷移金属化合物を使用したポリプロピレンの製造方法
KR100986301B1 (ko)	2010-04-12	2010-10-07	아주대학교산학협력단	테트라하이드로퀴놀린 유도체로부터 유래한 티오펜-축합고리 싸이클로펜타디에닐 4족 금속 화합물 및 이를 이용한 올레핀 중합
JP5567209B2 (ja)	2010-04-12	2014-08-06	ロッテケミカルコーポレーション	オレフィン重合用担持触媒およびこれを用いたポリオレフィンの製造方法
US8916662B2 (en)	2010-04-12	2014-12-23	Lotte Chemical Corporation	Method for preparing olefin-diene copolymer using transition metal compound containing thiophene-fused cyclopentadienyl ligand
JP5567208B2 (ja)	2010-04-12	2014-08-06	ロッテケミカルコーポレーション	オレフィン重合用触媒組成物およびこれを用いたポリオレフィンの製造方法

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FR2667068B1 (fr) *	1990-09-26	1994-09-09	Adir	Nouvelles amines alkyl heterocycliques, leur procede de preparation et les compositions pharmaceutiques qui les contiennent.
CA2451229C (en)	2001-06-29	2009-02-10	H. Lundbeck A/S	Indole derivatives

2002
- 2002-06-27 WO PCT/DK2002/000435 patent/WO2003002556A1/en not_active Ceased
- 2002-06-27 MX MXPA03011769A patent/MXPA03011769A/es active IP Right Grant
- 2002-06-27 SI SI200230265T patent/SI1399438T1/sl unknown
- 2002-06-27 US US10/482,764 patent/US20040248883A1/en not_active Abandoned
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- 2002-06-27 NZ NZ529460A patent/NZ529460A/en unknown
- 2002-06-27 CA CA002451228A patent/CA2451228A1/en not_active Abandoned
- 2002-06-27 IL IL15882802A patent/IL158828A0/xx unknown
- 2002-06-27 AT AT02742849T patent/ATE312094T1/de not_active IP Right Cessation
- 2002-06-27 DE DE60207857T patent/DE60207857T2/de not_active Expired - Fee Related
- 2002-06-27 UA UA20031211984A patent/UA75407C2/uk unknown
- 2002-06-27 EP EP02742849A patent/EP1399438B1/de not_active Expired - Lifetime
- 2002-06-27 CN CNB028129946A patent/CN1310909C/zh not_active Expired - Fee Related
- 2002-06-27 JP JP2003508937A patent/JP2004535449A/ja active Pending
- 2002-06-27 BR BR0210401-6A patent/BR0210401A/pt not_active IP Right Cessation
- 2002-06-27 KR KR10-2003-7017125A patent/KR20040019026A/ko not_active Abandoned
- 2002-06-27 PL PL02365249A patent/PL365249A1/xx unknown
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- 2002-06-27 EA EA200400102A patent/EA006203B1/ru not_active IP Right Cessation
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- 2002-06-27 ES ES02742849T patent/ES2252471T3/es not_active Expired - Lifetime
- 2002-06-27 CZ CZ2004156A patent/CZ2004156A3/cs unknown
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Also Published As

Publication number	Publication date
JP2004535449A (ja)	2004-11-25
IS2425B (is)	2008-10-15
CN1520410A (zh)	2004-08-11
CN1310909C (zh)	2007-04-18
SK652004A3 (en)	2004-09-08
AU2002344949B2 (en)	2007-05-24
EA200400102A1 (ru)	2004-04-29
US20080027071A1 (en)	2008-01-31
DK1399438T3 (da)	2006-04-18
EA006203B1 (ru)	2005-10-27
NO20035673D0 (no)	2003-12-18
ES2252471T3 (es)	2006-05-16
CZ2004156A3 (cs)	2004-05-12
BG108531A (bg)	2004-08-31
EP1399438A1 (de)	2004-03-24
BR0210401A (pt)	2004-08-17
NO326514B1 (no)	2008-12-22
WO2003002556A1 (en)	2003-01-09
MXPA03011769A (es)	2004-04-02
US7393845B2 (en)	2008-07-01
US20040248883A1 (en)	2004-12-09
EP1399438B1 (de)	2005-12-07
KR20040019026A (ko)	2004-03-04
NZ529460A (en)	2005-09-30
ATE312094T1 (de)	2005-12-15
CA2451228A1 (en)	2003-01-09
HK1068622A1 (en)	2005-04-29
PL365249A1 (en)	2004-12-27
NO20035673L (no)	2003-12-18
IL158828A0 (en)	2004-05-12
IS7021A (is)	2003-11-10
DE60207857D1 (de)	2006-01-12
DE60207857T2 (de)	2006-07-20
HUP0400344A2 (hu)	2004-09-28
SI1399438T1 (sl)	2006-04-30

Publication	Publication Date	Title
US7393845B2 (en)	2008-07-01	Heteroaryl derivates, their preparation and use
RU2333198C2 (ru)	2008-09-10	Производные бензамида или фармацевтически приемлемые соли указанного производного, фармацевтическая композиция на их основе и применение
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