BG63848B1 - 1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни - Google Patents

1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни Download PDF

Info

Publication number: BG63848B1
Authority: BG; Bulgaria
Prior art keywords: formula; alkyl; hydrogen; radical; compounds
Prior art date: 1997-04-08

Application number

BG103213A

Other languages

Bulgarian (bg)

English (en)

Other versions

BG103213A (en

Inventor

Ludo Kennis

Christopher Love

Francois BISCHOFF

Original Assignee

Janssen Pharmaceutica N.V.

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.)

1997-04-08

Filing date

1999-02-25

Publication date

2003-03-31

1999-02-25 Application filed by Janssen Pharmaceutica N.V. filed Critical Janssen Pharmaceutica N.V.

2000-05-31 Publication of BG103213A publication Critical patent/BG103213A/xx

2003-03-31 Publication of BG63848B1 publication Critical patent/BG63848B1/bg

Links

OGOWMVYFFWEWQT-UHFFFAOYSA-N 1,2,3,4-tetrahydro-[1]benzofuro[3,2-c]pyridine Chemical class O1C2=CC=CC=C2C2=C1CCNC2 OGOWMVYFFWEWQT-UHFFFAOYSA-N 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 96
-1 nitro, hydroxy Chemical group 0.000 claims abstract description 49
239000000203 mixture Substances 0.000 claims abstract description 48
150000003839 salts Chemical class 0.000 claims abstract description 28
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
239000001257 hydrogen Substances 0.000 claims abstract description 27
238000002360 preparation method Methods 0.000 claims abstract description 20
229910052736 halogen Inorganic materials 0.000 claims abstract description 18
150000002367 halogens Chemical class 0.000 claims abstract description 18
150000001204 N-oxides Chemical class 0.000 claims abstract description 12
150000002431 hydrogen Chemical class 0.000 claims abstract description 12
239000003814 drug Substances 0.000 claims abstract description 6
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 4
125000000217 alkyl group Chemical group 0.000 claims description 33
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 16
238000000034 method Methods 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 10
239000002585 base Substances 0.000 claims description 10
239000004480 active ingredient Substances 0.000 claims description 8
125000003545 alkoxy group Chemical group 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
208000018737 Parkinson disease Diseases 0.000 claims description 6
125000001118 alkylidene group Chemical group 0.000 claims description 6
239000003937 drug carrier Substances 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 5
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
238000007126 N-alkylation reaction Methods 0.000 claims description 4
230000002378 acidificating effect Effects 0.000 claims description 4
239000012458 free base Substances 0.000 claims description 4
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
125000004173 1-benzimidazolyl group Chemical group [H]C1=NC2=C([H])C([H])=C([H])C([H])=C2N1* 0.000 claims description 3
125000005196 alkyl carbonyloxy group Chemical group 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
231100000252 nontoxic Toxicity 0.000 claims description 3
230000003000 nontoxic effect Effects 0.000 claims description 3
125000006619 (C1-C6) dialkylamino group Chemical group 0.000 claims description 2
WGSMVIHKBMAWRN-UHFFFAOYSA-N 2,3,3a,4-tetrahydro-1-benzofuran Chemical compound C1C=CC=C2OCCC21 WGSMVIHKBMAWRN-UHFFFAOYSA-N 0.000 claims description 2
ZYXHQIPQIKTEDI-UHFFFAOYSA-N 3-[2-(3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridin-2-yl)ethyl]-2-methylpyrido[1,2-a]pyrimidin-4-one Chemical compound O1C2=CC=CC=C2C(C2)=C1CCN2CCC(C1=O)=C(C)N=C2N1C=CC=C2 ZYXHQIPQIKTEDI-UHFFFAOYSA-N 0.000 claims description 2
208000020401 Depressive disease Diseases 0.000 claims description 2
125000002252 acyl group Chemical group 0.000 claims description 2
230000002152 alkylating effect Effects 0.000 claims description 2
125000005002 aryl methyl group Chemical group 0.000 claims description 2
125000000958 aryl methylene group Chemical group 0.000 claims description 2
239000003153 chemical reaction reagent Substances 0.000 claims description 2
239000008240 homogeneous mixture Substances 0.000 claims description 2
150000003222 pyridines Chemical class 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
230000009466 transformation Effects 0.000 claims description 2
125000004174 2-benzimidazolyl group Chemical group [H]N1C(*)=NC2=C([H])C([H])=C([H])C([H])=C12 0.000 claims 1
FPQNWBCHCMEAKI-UHFFFAOYSA-N 3-[2-(3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridin-2-yl)ethyl]-2,7-dimethylpyrido[1,2-a]pyrimidin-4-one Chemical compound O1C2=CC=CC=C2C(C2)=C1CCN2CCC1=C(C)N=C2C=CC(C)=CN2C1=O FPQNWBCHCMEAKI-UHFFFAOYSA-N 0.000 claims 1
125000001153 fluoro group Chemical group F* 0.000 claims 1
125000002887 hydroxy group Chemical group [H]O* 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
125000006239 protecting group Chemical group 0.000 claims 1
JUQLTPCYUFPYKE-UHFFFAOYSA-N ritanserin Chemical compound CC=1N=C2SC=CN2C(=O)C=1CCN(CC1)CCC1=C(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 JUQLTPCYUFPYKE-UHFFFAOYSA-N 0.000 claims 1
230000008685 targeting Effects 0.000 claims 1
238000000844 transformation Methods 0.000 claims 1
230000000694 effects Effects 0.000 abstract description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
239000000674 adrenergic antagonist Substances 0.000 abstract 1
239000000543 intermediate Substances 0.000 description 39
150000003254 radicals Chemical class 0.000 description 30
239000000243 solution Substances 0.000 description 30
239000002904 solvent Substances 0.000 description 26
108020003175 receptors Proteins 0.000 description 23
102000005962 receptors Human genes 0.000 description 23
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
239000000460 chlorine Substances 0.000 description 20
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 13
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 12
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 12
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 10
230000005764 inhibitory process Effects 0.000 description 10
239000012044 organic layer Substances 0.000 description 10
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
230000027455 binding Effects 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
241000700159 Rattus Species 0.000 description 8
108010037444 diisopropylglutathione ester Proteins 0.000 description 8
239000003480 eluent Substances 0.000 description 8
239000008194 pharmaceutical composition Substances 0.000 description 8
239000002244 precipitate Substances 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical class Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000000741 silica gel Substances 0.000 description 7
229910002027 silica gel Inorganic materials 0.000 description 7
SFLSHLFXELFNJZ-QMMMGPOBSA-N (-)-norepinephrine Chemical compound NC[C@H](O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-QMMMGPOBSA-N 0.000 description 6
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002552 dosage form Substances 0.000 description 6
239000010410 layer Substances 0.000 description 6
229960002748 norepinephrine Drugs 0.000 description 6
SFLSHLFXELFNJZ-UHFFFAOYSA-N norepinephrine Natural products NCC(O)C1=CC=C(O)C(O)=C1 SFLSHLFXELFNJZ-UHFFFAOYSA-N 0.000 description 6
238000010992 reflux Methods 0.000 description 6
238000003756 stirring Methods 0.000 description 6
BPICBUSOMSTKRF-UHFFFAOYSA-N xylazine Chemical compound CC1=CC=CC(C)=C1NC1=NCCCS1 BPICBUSOMSTKRF-UHFFFAOYSA-N 0.000 description 6
229960001600 xylazine Drugs 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 5
239000002775 capsule Substances 0.000 description 5
210000003169 central nervous system Anatomy 0.000 description 5
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
239000001530 fumaric acid Substances 0.000 description 5
235000011087 fumaric acid Nutrition 0.000 description 5
239000003446 ligand Substances 0.000 description 5
238000002844 melting Methods 0.000 description 5
230000008018 melting Effects 0.000 description 5
230000002285 radioactive effect Effects 0.000 description 5
239000011734 sodium Substances 0.000 description 5
239000000725 suspension Substances 0.000 description 5
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 4
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
150000007513 acids Chemical class 0.000 description 4
230000000903 blocking effect Effects 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
230000001965 increasing effect Effects 0.000 description 4
238000002347 injection Methods 0.000 description 4
239000007924 injection Substances 0.000 description 4
LXCFILQKKLGQFO-UHFFFAOYSA-N methylparaben Chemical compound COC(=O)C1=CC=C(O)C=C1 LXCFILQKKLGQFO-UHFFFAOYSA-N 0.000 description 4
239000003921 oil Substances 0.000 description 4
235000019198 oils Nutrition 0.000 description 4
230000011514 reflex Effects 0.000 description 4
230000002441 reversible effect Effects 0.000 description 4
239000011780 sodium chloride Substances 0.000 description 4
230000001225 therapeutic effect Effects 0.000 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 description 3
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000005557 antagonist Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000003054 catalyst Substances 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
208000035475 disorder Diseases 0.000 description 3
238000003818 flash chromatography Methods 0.000 description 3
239000008103 glucose Substances 0.000 description 3
239000011777 magnesium Substances 0.000 description 3
229910052757 nitrogen Inorganic materials 0.000 description 3
150000002978 peroxides Chemical class 0.000 description 3
229910052700 potassium Inorganic materials 0.000 description 3
239000011591 potassium Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000002287 radioligand Substances 0.000 description 3
239000007787 solid Substances 0.000 description 3
239000012453 solvate Substances 0.000 description 3
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WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 2
CUJPFPXNDSIBPG-UHFFFAOYSA-N 1,3-propanediyl Chemical group [CH2]C[CH2] CUJPFPXNDSIBPG-UHFFFAOYSA-N 0.000 description 2
OMIVCRYZSXDGAB-UHFFFAOYSA-N 1,4-butanediyl Chemical group [CH2]CC[CH2] OMIVCRYZSXDGAB-UHFFFAOYSA-N 0.000 description 2
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical compound O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 description 2
PBIUDEUWYGBHDW-UHFFFAOYSA-N 2-chloro-1-pyridin-3-ylethanone;hydrochloride Chemical compound Cl.ClCC(=O)C1=CC=CN=C1 PBIUDEUWYGBHDW-UHFFFAOYSA-N 0.000 description 2
OWHRXGOUYLKIPH-UHFFFAOYSA-N 2-cyclohexa-1,5-dien-1-ylacetic acid Chemical compound OC(=O)CC1=CCCC=C1 OWHRXGOUYLKIPH-UHFFFAOYSA-N 0.000 description 2
LHXOGIFWWOEQTM-UHFFFAOYSA-N 2-methyl-6-nitro-3,4-dihydro-1h-[1]benzofuro[3,2-c]pyridine Chemical compound O1C2=C([N+]([O-])=O)C=CC=C2C2=C1CCN(C)C2 LHXOGIFWWOEQTM-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
208000024827 Alzheimer disease Diseases 0.000 description 2
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241000282472 Canis lupus familiaris Species 0.000 description 2
GJSURZIOUXUGAL-UHFFFAOYSA-N Clonidine Chemical compound ClC1=CC=CC(Cl)=C1NC1=NCCN1 GJSURZIOUXUGAL-UHFFFAOYSA-N 0.000 description 2
208000010228 Erectile Dysfunction Diseases 0.000 description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
241001465754 Metazoa Species 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 2
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric Acid Chemical compound [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 2
239000000654 additive Substances 0.000 description 2
239000000556 agonist Substances 0.000 description 2
230000008485 antagonism Effects 0.000 description 2
239000008346 aqueous phase Substances 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
238000009835 boiling Methods 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
210000004027 cell Anatomy 0.000 description 2
210000004978 chinese hamster ovary cell Anatomy 0.000 description 2
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DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
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201000010099 disease Diseases 0.000 description 2
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ANCBHJKEYPZCTE-UHFFFAOYSA-N ethyl 5-carbamoyl-4-methyl-2-[(2,3,4,5,6-pentafluorobenzoyl)amino]thiophene-3-carboxylate Chemical compound CC1=C(C(N)=O)SC(NC(=O)C=2C(=C(F)C(F)=C(F)C=2F)F)=C1C(=O)OCC ANCBHJKEYPZCTE-UHFFFAOYSA-N 0.000 description 2
239000011737 fluorine Substances 0.000 description 2
229910052731 fluorine Inorganic materials 0.000 description 2
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239000011630 iodine Substances 0.000 description 2
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JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
239000008101 lactose Substances 0.000 description 2
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229910052749 magnesium Inorganic materials 0.000 description 2
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
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VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
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230000003518 presynaptic effect Effects 0.000 description 2
235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 2
QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 2
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238000010956 selective crystallization Methods 0.000 description 2
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CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
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BJOIZNZVOZKDIG-MDEJGZGSSA-N reserpine Chemical compound O([C@H]1[C@@H]([C@H]([C@H]2C[C@@H]3C4=C([C]5C=CC(OC)=CC5=N4)CCN3C[C@H]2C1)C(=O)OC)OC)C(=O)C1=CC(OC)=C(OC)C(OC)=C1 BJOIZNZVOZKDIG-MDEJGZGSSA-N 0.000 description 1
229960003147 reserpine Drugs 0.000 description 1
MDMGHDFNKNZPAU-UHFFFAOYSA-N roserpine Natural products C1C2CN3CCC(C4=CC=C(OC)C=C4N4)=C4C3CC2C(OC(C)=O)C(OC)C1OC(=O)C1=CC(OC)=C(OC)C(OC)=C1 MDMGHDFNKNZPAU-UHFFFAOYSA-N 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
229940076279 serotonin Drugs 0.000 description 1
230000019491 signal transduction Effects 0.000 description 1
238000010898 silica gel chromatography Methods 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
PFUVRDFDKPNGAV-UHFFFAOYSA-N sodium peroxide Chemical compound [Na+].[Na+].[O-][O-] PFUVRDFDKPNGAV-UHFFFAOYSA-N 0.000 description 1
ILJOYZVVZZFIKA-UHFFFAOYSA-M sodium;1,1-dioxo-1,2-benzothiazol-3-olate;hydrate Chemical compound O.[Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 ILJOYZVVZZFIKA-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
239000008223 sterile water Substances 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
150000008163 sugars Chemical class 0.000 description 1
IHCDKJZZFOUARO-UHFFFAOYSA-M sulfacetamide sodium Chemical compound O.[Na+].CC(=O)[N-]S(=O)(=O)C1=CC=C(N)C=C1 IHCDKJZZFOUARO-UHFFFAOYSA-M 0.000 description 1
239000011593 sulfur Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
208000024891 symptom 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
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
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
- C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/10—Drugs for genital or sexual disorders; Contraceptives for impotence
- 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
- 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
- A61P25/24—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
- A61P27/00—Drugs for disorders of the senses
- A61P27/02—Ophthalmic agents
- A61P27/06—Antiglaucoma agents or miotics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P5/00—Drugs for disorders of the endocrine system
- A61P5/48—Drugs for disorders of the endocrine system of the pancreatic hormones
- A61P5/50—Drugs for disorders of the endocrine system of the pancreatic hormones for increasing or potentiating the activity of insulin
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Landscapes

Health & Medical Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Public Health (AREA)
Pharmacology & Pharmacy (AREA)
Veterinary Medicine (AREA)
General Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Biomedical Technology (AREA)
Diabetes (AREA)
Endocrinology (AREA)
Hematology (AREA)
Obesity (AREA)
Reproductive Health (AREA)
Ophthalmology & Optometry (AREA)
Psychiatry (AREA)
Emergency Medicine (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Hospice & Palliative Care (AREA)
Psychology (AREA)
Gynecology & Obstetrics (AREA)
Cardiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

BG103213A 1997-04-08 1999-02-25 1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни BG63848B1 (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
EP97201045		1997-04-08
PCT/EP1998/002136 WO1998045297A1 (en)	1997-04-08	1998-04-02	1,2,3,4-TETRAHYDRO-BENZOFURO[3,2-c]PYRIDINE DERIVATIVES__

Publications (2)

Publication Number	Publication Date
BG103213A BG103213A (en)	2000-05-31
BG63848B1 true BG63848B1 (bg)	2003-03-31

Family

ID=8228191

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG103213A BG63848B1 (bg)	1997-04-08	1999-02-25	1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни

Country Status (31)

Country	Link
US (1)	US6156757A (id)
EP (1)	EP1019408B1 (id)
JP (1)	JP3287577B2 (id)
KR (1)	KR100315975B1 (id)
CN (1)	CN1097053C (id)
AP (1)	AP1138A (id)
AR (1)	AR012576A1 (id)
AT (1)	ATE270294T1 (id)
AU (1)	AU727599B2 (id)
BG (1)	BG63848B1 (id)
BR (1)	BR9806263A (id)
CA (1)	CA2264598C (id)
CZ (1)	CZ290008B6 (id)
DE (1)	DE69824872T2 (id)
EE (1)	EE03691B1 (id)
ES (1)	ES2224391T3 (id)
GE (1)	GEP20022823B (id)
HU (1)	HUP0003624A3 (id)
ID (1)	ID22131A (id)
IL (1)	IL128701A0 (id)
MY (1)	MY120033A (id)
NO (1)	NO322826B1 (id)
NZ (1)	NZ334501A (id)
PL (1)	PL189549B1 (id)
RU (1)	RU2198175C2 (id)
SK (1)	SK283621B6 (id)
TR (1)	TR199900644T2 (id)
TW (1)	TW589315B (id)
UA (1)	UA52681C2 (id)
WO (1)	WO1998045297A1 (id)
ZA (1)	ZA982969B (id)

Families Citing this family (15)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
UA52681C2 (uk) *	1997-04-08	2003-01-15	Янссен Фармацевтика Н.В.	Похідні 1,2,3,4-тетрагідро-бензофуро[3,2,-c]піридину, спосіб їх одержання та фармацевтична композиція на їх основі
ID28451A (id) *	1998-10-06	2001-05-24	Janssen Pharmaceutica Nv	Trisiklik piperidin-δ3 sebagai bahan farmasi
UA70334C2 (en)	1998-10-06	2004-10-15	Janssen Pharmaceutica N V Jans	BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS BENZOTHIENO[3,2-c]PYRIDINES AS a2 ANTAGONISTS
AU765751B2 (en) *	1998-12-21	2003-09-25	Janssen Pharmaceutica N.V.	Benzisoxazoles and phenones as alpha2-antagonists
EP1404679A2 (en)	2001-07-05	2004-04-07	PHARMACIA & UPJOHN COMPANY	(hetero)aryl substituted benzofurans as 5-ht ligands
ATE521593T1 (de) *	2002-04-03	2011-09-15	Orion Corp	Verwendung eines alfa2-adrenorezeptorantagonisten bei mit dem zns zusammenhängenden erkrankungen
JP4690043B2 (ja) *	2002-10-04	2011-06-01	プラナバイオテクノロジーリミティッド	神経に対し活性な化合物
WO2005100355A1 (ja)	2004-04-12	2005-10-27	Taisho Pharmaceutical Co., Ltd.	環状アミン化合物
RU2409582C2 (ru) *	2004-08-31	2011-01-20	Глэксо Груп Лимитед	Конденсированные трициклические производные для лечения психотических расстройств
EP2535330A3 (en) *	2006-10-23	2012-12-26	Takeda Pharmaceutical Company Limited	Iminopyridine derivative and use thereof
US8481569B2 (en)	2008-04-23	2013-07-09	Takeda Pharmaceutical Company Limited	Iminopyridine derivatives and use thereof
AR071392A1 (es) *	2008-04-23	2010-06-16	Takeda Pharmaceutical	Derivados de iminopiridina y su uso
US8575186B2 (en) *	2009-10-05	2013-11-05	Albany Molecular Research, Inc.	Epiminocycloalkyl[b] indole derivatives as serotonin sub-type 6 (5-HT6) modulators and uses thereof
EP2668191A4 (en)	2011-01-19	2014-08-20	Albany Molecular Res Inc	BENZOFURO- [3,2-C-] PYRIDINES AND RELATED ANALOGS AS SEROTONIN-SUBTYPE-6 (5-HT6) MODULATORS FOR THE TREATMENT OF ADIPOSITAS, METABOLISM SYNDROME, COGNITION AND SCHIZOPHRENIA
GB201704325D0 (en) *	2017-03-17	2017-05-03	Argonaut Therapeutics Ltd	Compounds

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* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4688803A (en) *	1984-06-25	1987-08-25	Ollington Robert F	Casino game table and dice
FR2570701B1 (fr) *	1984-09-27	1987-05-22	Synthelabo	Derives de furo(3,2-c)pyridines, leur preparation et leur application en therapeutique
US4686226A (en) *	1985-09-03	1987-08-11	Merck & Co., Inc.	Substituted benzo[b]furo- and benzo[b]thieno quinolizines
RU2045529C1 (ru) *	1988-04-26	1995-10-10	Ниссан Кемикал Индастриз Лтд.	Способ получения мевалонолактоновых производных
US4985422A (en) *	1988-04-27	1991-01-15	Glaxo Group Limited	Lactam derivatives
DE4308451A1 (de) *	1992-09-10	1994-04-14	Bayer Ag	3-Aryl-pyron-Derivate
UA52681C2 (uk) *	1997-04-08	2003-01-15	Янссен Фармацевтика Н.В.	Похідні 1,2,3,4-тетрагідро-бензофуро[3,2,-c]піридину, спосіб їх одержання та фармацевтична композиція на їх основі

1998
- 1998-02-04 UA UA99031180A patent/UA52681C2/uk unknown
- 1998-04-02 EE EEP199900114A patent/EE03691B1/xx not_active IP Right Cessation
- 1998-04-02 ES ES98921458T patent/ES2224391T3/es not_active Expired - Lifetime
- 1998-04-02 AU AU74307/98A patent/AU727599B2/en not_active Expired
- 1998-04-02 CA CA002264598A patent/CA2264598C/en not_active Expired - Lifetime
- 1998-04-02 RU RU99107290/04A patent/RU2198175C2/ru active
- 1998-04-02 JP JP54240698A patent/JP3287577B2/ja not_active Expired - Fee Related
- 1998-04-02 EP EP98921458A patent/EP1019408B1/en not_active Expired - Lifetime
- 1998-04-02 TR TR1999/00644T patent/TR199900644T2/xx unknown
- 1998-04-02 DE DE69824872T patent/DE69824872T2/de not_active Expired - Lifetime
- 1998-04-02 SK SK287-99A patent/SK283621B6/sk not_active IP Right Cessation
- 1998-04-02 IL IL12870198A patent/IL128701A0/xx not_active IP Right Cessation
- 1998-04-02 GE GEAP19985020A patent/GEP20022823B/en unknown
- 1998-04-02 KR KR1019997002086A patent/KR100315975B1/ko not_active Expired - Fee Related
- 1998-04-02 CN CN98801286A patent/CN1097053C/zh not_active Expired - Lifetime
- 1998-04-02 US US09/402,593 patent/US6156757A/en not_active Expired - Lifetime
- 1998-04-02 HU HU0003624A patent/HUP0003624A3/hu unknown
- 1998-04-02 CZ CZ1999682A patent/CZ290008B6/cs not_active IP Right Cessation
- 1998-04-02 BR BR9806263-8A patent/BR9806263A/pt not_active Application Discontinuation
- 1998-04-02 NZ NZ334501A patent/NZ334501A/en unknown
- 1998-04-02 AT AT98921458T patent/ATE270294T1/de not_active IP Right Cessation
- 1998-04-02 WO PCT/EP1998/002136 patent/WO1998045297A1/en not_active Ceased
- 1998-04-02 PL PL98332382A patent/PL189549B1/pl unknown
- 1998-04-02 ID IDW990147D patent/ID22131A/id unknown
- 1998-04-02 AP APAP/P/1999/001650A patent/AP1138A/en active
- 1998-04-03 MY MYPI98001502A patent/MY120033A/en unknown
- 1998-04-07 ZA ZA9802969A patent/ZA982969B/xx unknown
- 1998-04-07 TW TW087105162A patent/TW589315B/zh not_active IP Right Cessation
- 1998-04-07 AR ARP980101598A patent/AR012576A1/es active IP Right Grant
1999
- 1999-02-23 NO NO19990859A patent/NO322826B1/no not_active IP Right Cessation
- 1999-02-25 BG BG103213A patent/BG63848B1/bg unknown

Also Published As

Publication number	Publication date
AP9901650A0 (en)	1999-09-30
TW589315B (en)	2004-06-01
SK28799A3 (en)	2001-03-12
BG103213A (en)	2000-05-31
CZ68299A3 (cs)	2000-08-16
ID22131A (id)	1999-09-09
CN1237179A (zh)	1999-12-01
UA52681C2 (uk)	2003-01-15
KR20000036076A (ko)	2000-06-26
HUP0003624A2 (hu)	2001-04-28
KR100315975B1 (ko)	2001-12-22
NO990859L (no)	1999-09-30
EP1019408B1 (en)	2004-06-30
DE69824872T2 (de)	2005-09-01
WO1998045297A1 (en)	1998-10-15
ATE270294T1 (de)	2004-07-15
ES2224391T3 (es)	2005-03-01
PL332382A1 (en)	1999-09-13
RU2198175C2 (ru)	2003-02-10
AU727599B2 (en)	2000-12-14
CA2264598A1 (en)	1998-10-15
TR199900644T2 (xx)	2000-09-21
CZ290008B6 (cs)	2002-05-15
GEP20022823B (en)	2002-10-25
SK283621B6 (sk)	2003-10-07
AU7430798A (en)	1998-10-30
EE03691B1 (et)	2002-04-15
JP2000505115A (ja)	2000-04-25
PL189549B1 (pl)	2005-08-31
DE69824872D1 (de)	2004-08-05
CA2264598C (en)	2006-10-24
HUP0003624A3 (en)	2002-09-30
JP3287577B2 (ja)	2002-06-04
IL128701A0 (en)	2000-01-31
NZ334501A (en)	2000-06-23
US6156757A (en)	2000-12-05
NO322826B1 (no)	2006-12-11
BR9806263A (pt)	2000-04-04
NO990859D0 (no)	1999-02-23
ZA982969B (en)	1999-10-07
MY120033A (en)	2005-08-30
EP1019408A1 (en)	2000-07-19
AR012576A1 (es)	2000-11-08
CN1097053C (zh)	2002-12-25
EE9900114A (et)	1999-12-15
AP1138A (en)	2003-01-17

Publication	Publication Date	Title
BG63848B1 (bg)	2003-03-31	1,2,3,4-тетрахидро-бензофуро[3,2-с]пиридинови производни
EP3240783B1 (en)	2018-11-21	New benzimidazole derivatives as antihistamine agents
CZ2000726A3 (cs)	2000-07-12	Tetrahydro-gama-karboliny a způsob jejich přípravy
RU2230744C2 (ru)	2004-06-20	Трициклические δ3-пиперидины, способы их получения и фармацевтическая композиция на их основе
BG64871B1 (bg)	2006-07-31	Трициклични делта 3-пиперидини, като лекарства
JP4580555B2 (ja)	2010-11-17	α２アンタゴニストとしてのベンゾチエノ［３，２−ｃ］ピリジン類
MXPA01003514A (en)	2001-12-04	BENZOTHIENO[3,2-c]PYRIDINES AS&agr;2
HK1039113B (en)	2007-07-20	Benzothieno[3,2-c]pyridines as alpha2 antagonists
HK1240223A1 (en)	2018-05-18	New benzimidazole derivatives as antihistamine agents
HK1240223B (en)	2019-09-06	New benzimidazole derivatives as antihistamine agents
HK1038009B (en)	2004-12-24	Tricyclic delta3-piperidines as pharmaceuticals