CA1248101A - Aminoalkoxybenzopyranones utilises comme agents antipsychotiques et anxiolytiques - Google Patents

Aminoalkoxybenzopyranones utilises comme agents antipsychotiques et anxiolytiques

Info

Publication number: CA1248101A
Authority: CA; Canada
Prior art keywords: formula; lower alkyl; compound; substituted; halogen
Prior art date: 1985-06-18
Legal status (The legal status 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 status listed.): Expired

Application number

CA000502293A

Other languages

English (en)

Inventor

Lawrence D. Wise

Horace A. Dewald

Thomas G. Heffner

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Warner Lambert Co LLC

Original Assignee

Warner Lambert Co LLC

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.)

1985-06-18

Filing date

1986-02-20

Publication date

1989-01-03

1985-06-18 Priority claimed from US06/745,971 external-priority patent/US4701456A/en

1986-02-20 Application filed by Warner Lambert Co LLC filed Critical Warner Lambert Co LLC

1989-01-03 Application granted granted Critical

1989-01-03 Publication of CA1248101A publication Critical patent/CA1248101A/fr

Status Expired legal-status Critical Current

Links

230000000561 anti-psychotic effect Effects 0.000 title claims description 4
239000002249 anxiolytic agent Substances 0.000 title description 7
239000000164 antipsychotic agent Substances 0.000 title description 3
125000000217 alkyl group Chemical group 0.000 claims abstract description 23
-1 4-pyridinyl Chemical group 0.000 claims abstract description 21
229910052736 halogen Inorganic materials 0.000 claims abstract description 16
150000002367 halogens Chemical class 0.000 claims abstract description 16
238000000034 method Methods 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
238000002360 preparation method Methods 0.000 claims abstract description 11
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims abstract description 9
125000004527 pyrimidin-4-yl group Chemical group N1=CN=C(C=C1)* 0.000 claims abstract description 9
125000004528 pyrimidin-5-yl group Chemical group N1=CN=CC(=C1)* 0.000 claims abstract description 9
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims abstract description 8
CWDWFSXUQODZGW-UHFFFAOYSA-N 5-thiazolyl Chemical group [C]1=CN=CS1 CWDWFSXUQODZGW-UHFFFAOYSA-N 0.000 claims abstract description 7
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims abstract description 5
125000003682 3-furyl group Chemical group O1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 5
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims abstract description 5
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
150000001875 compounds Chemical class 0.000 claims description 50
150000003839 salts Chemical class 0.000 claims description 15
239000002253 acid Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 6
239000001257 hydrogen Substances 0.000 claims description 6
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
150000001412 amines Chemical class 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
239000003795 chemical substances by application Substances 0.000 claims description 3
239000003937 drug carrier Substances 0.000 claims description 3
125000001246 bromo group Chemical group Br* 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
230000003472 neutralizing effect Effects 0.000 claims description 2
FZXJUTVHCBPUBM-UHFFFAOYSA-N 7-[3-(4-thiophen-2-yl-3,6-dihydro-2h-pyridin-1-yl)propoxy]chromen-2-one Chemical compound C1=C2OC(=O)C=CC2=CC=C1OCCCN(CC=1)CCC=1C1=CC=CS1 FZXJUTVHCBPUBM-UHFFFAOYSA-N 0.000 claims 1
150000002431 hydrogen Chemical group 0.000 claims 1
208000019901 Anxiety disease Diseases 0.000 abstract description 5
230000036506 anxiety Effects 0.000 abstract description 5
208000028017 Psychotic disease Diseases 0.000 abstract description 2
201000000980 schizophrenia Diseases 0.000 abstract description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
235000013305 food Nutrition 0.000 description 9
239000000243 solution Substances 0.000 description 9
241000700159 Rattus Species 0.000 description 8
230000000694 effects Effects 0.000 description 8
239000003826 tablet Substances 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
241001465754 Metazoa Species 0.000 description 5
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 5
239000002775 capsule Substances 0.000 description 5
239000012458 free base Substances 0.000 description 5
239000000203 mixture Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
239000002904 solvent Substances 0.000 description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
FXRDPPFLWGSMQT-UHFFFAOYSA-N benzo[f]chromen-3-one Chemical compound C1=CC=C2C(C=CC(O3)=O)=C3C=CC2=C1 FXRDPPFLWGSMQT-UHFFFAOYSA-N 0.000 description 3
239000007788 liquid Substances 0.000 description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
230000035939 shock Effects 0.000 description 3
239000000725 suspension Substances 0.000 description 3
MJKVTPMWOKAVMS-UHFFFAOYSA-N 3-hydroxy-1-benzopyran-2-one Chemical compound C1=CC=C2OC(=O)C(O)=CC2=C1 MJKVTPMWOKAVMS-UHFFFAOYSA-N 0.000 description 2
HSHNITRMYYLLCV-UHFFFAOYSA-N 4-methylumbelliferone Chemical compound C1=C(O)C=CC2=C1OC(=O)C=C2C HSHNITRMYYLLCV-UHFFFAOYSA-N 0.000 description 2
HBOHLHVRTOKAGX-UHFFFAOYSA-N 4-thiophen-2-yl-1,2,3,4-tetrahydropyridine Chemical compound C1=CNCCC1C1=CC=CS1 HBOHLHVRTOKAGX-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
DPXJVFZANSGRMM-UHFFFAOYSA-N acetic acid;2,3,4,5,6-pentahydroxyhexanal;sodium Chemical compound [Na].CC(O)=O.OCC(O)C(O)C(O)C(O)C=O DPXJVFZANSGRMM-UHFFFAOYSA-N 0.000 description 2
239000004480 active ingredient Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000001768 carboxy methyl cellulose Substances 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
235000020186 condensed milk Nutrition 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
239000000463 material Substances 0.000 description 2
229920000609 methyl cellulose Polymers 0.000 description 2
239000001923 methylcellulose Substances 0.000 description 2
235000010981 methylcellulose Nutrition 0.000 description 2
239000002798 polar solvent Substances 0.000 description 2
229910000027 potassium carbonate Inorganic materials 0.000 description 2
230000002787 reinforcement Effects 0.000 description 2
239000011734 sodium Substances 0.000 description 2
229910052708 sodium Inorganic materials 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
235000019812 sodium carboxymethyl cellulose Nutrition 0.000 description 2
229920001027 sodium carboxymethylcellulose Polymers 0.000 description 2
239000000126 substance Substances 0.000 description 2
239000000375 suspending agent Substances 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
230000001225 therapeutic effect Effects 0.000 description 2
125000005309 thioalkoxy group Chemical group 0.000 description 2
MHCVCKDNQYMGEX-UHFFFAOYSA-N 1,1'-biphenyl;phenoxybenzene Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC=CC=1OC1=CC=CC=C1 MHCVCKDNQYMGEX-UHFFFAOYSA-N 0.000 description 1
HXCBKQXAXRRHQW-UHFFFAOYSA-N 7-(3-chloropropoxy)chromen-2-one Chemical compound C1=CC(=O)OC2=CC(OCCCCl)=CC=C21 HXCBKQXAXRRHQW-UHFFFAOYSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
COVZYZSDYWQREU-UHFFFAOYSA-N Busulfan Chemical compound CS(=O)(=O)OCCCCOS(C)(=O)=O COVZYZSDYWQREU-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
239000004375 Dextrin Substances 0.000 description 1
229920001353 Dextrin Polymers 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
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 1
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
206010039897 Sedation Diseases 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
239000000159 acid neutralizing agent Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
238000010171 animal model Methods 0.000 description 1
230000000049 anti-anxiety effect Effects 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000037396 body weight Effects 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
229940110456 cocoa butter Drugs 0.000 description 1
235000019868 cocoa butter Nutrition 0.000 description 1
239000003086 colorant Substances 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical class C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
235000019425 dextrin Nutrition 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000000839 emulsion Substances 0.000 description 1
LBAQSKZHMLAFHH-UHFFFAOYSA-N ethoxyethane;hydron;chloride Chemical compound Cl.CCOCC LBAQSKZHMLAFHH-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
230000007717 exclusion Effects 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
235000013355 food flavoring agent Nutrition 0.000 description 1
229920000159 gelatin Polymers 0.000 description 1
239000008273 gelatin Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000008187 granular material Substances 0.000 description 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 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000013067 intermediate product Substances 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([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
150000002576 ketones Chemical class 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000000314 lubricant Substances 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
239000001095 magnesium carbonate Substances 0.000 description 1
229910000021 magnesium carbonate Inorganic materials 0.000 description 1
230000000873 masking effect Effects 0.000 description 1
238000004949 mass spectrometry Methods 0.000 description 1
238000002844 melting Methods 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
239000008267 milk Substances 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
239000003176 neuroleptic agent Substances 0.000 description 1
230000000701 neuroleptic effect Effects 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000006186 oral dosage form Substances 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000006201 parenteral dosage form Substances 0.000 description 1
239000001814 pectin Substances 0.000 description 1
235000010987 pectin Nutrition 0.000 description 1
229920001277 pectin Polymers 0.000 description 1
230000035699 permeability Effects 0.000 description 1
239000008177 pharmaceutical agent Substances 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
239000003880 polar aprotic solvent Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
239000002516 radical scavenger Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 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
230000036280 sedation Effects 0.000 description 1
230000011664 signaling Effects 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
230000000087 stabilizing effect Effects 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000829 suppository Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 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
239000002562 thickening agent Substances 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
239000011345 viscous material Substances 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

CA000502293A 1985-06-18 1986-02-20 Aminoalkoxybenzopyranones utilises comme agents antipsychotiques et anxiolytiques Expired CA1248101A (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US06/745,971 US4701456A (en)	1984-09-19	1985-06-18	Aminoalkoxybenzopyranones as antipsychotic and anxiolytic agents
US745,971		1985-06-18

Publications (1)

Publication Number	Publication Date
CA1248101A true CA1248101A (fr)	1989-01-03

Family

ID=24999002

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000502293A Expired CA1248101A (fr)	1985-06-18	1986-02-20	Aminoalkoxybenzopyranones utilises comme agents antipsychotiques et anxiolytiques

Country Status (2)

Country	Link
CN (1)	CN1007351B (fr)
CA (1)	CA1248101A (fr)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100393716C (zh) *	2006-05-18	2008-06-11	中国药科大学	香豆素衍生物、其制备方法及作为α1受体拮抗剂的用途
AU2010279963A1 (en) *	2009-08-04	2012-02-23	Dainippon Sumitomo Pharma Co., Ltd.	Benzyl piperidine compound
CN102050809B (zh) *	2009-11-03	2014-12-17	中国医学科学院药物研究所	拮抗cklf1/ccr4相互作用的3-哌嗪基香豆素衍生物
CN102206214B (zh) *	2011-04-07	2014-03-12	华中科技大学	苯并吡喃酮类衍生物及其应用
CN102267966B (zh) *	2011-08-01	2013-02-27	华中科技大学	取代的苯并吡喃酮类衍生物及其应用
CN104059046B (zh) *	2013-03-18	2017-02-08	江苏恩华药业股份有限公司	黄酮类衍生物及其应用
EP2991635B1 (fr) *	2013-05-03	2017-04-12	F. Hoffmann-La Roche AG	Dérivés d'isoquinoline de stimulation de la neurogenèse
AU2014314799B2 (en) *	2013-08-27	2017-05-25	Shenyang Research Institute Of Chemical Industry Co., Ltd.	Applications of substituent benzyloxy group containing ether compounds for preparing antitumor drugs

1985
- 1985-09-17 CN CN 85106970 patent/CN1007351B/zh not_active Expired
1986
- 1986-02-20 CA CA000502293A patent/CA1248101A/fr not_active Expired

Also Published As

Publication number	Publication date
CN1007351B (zh)	1990-03-28
CN85106970A (zh)	1987-04-01

Legal Events

Date	Code	Title	Description
2006-02-20	MKEX	Expiry

Publication	Publication Date	Title
EP0175541B1 (fr)	1989-02-22	Amino-alkoxybenzopyranones et procédés pour leur préparation
US4018929A (en)	1977-04-19	3-Loweralkylcarbamylsulfonamido-4-phenylaminopyridine-N-oxides, derivatives thereof and pharmaceutical compositions containing same
US4904784A (en)	1990-02-27	Active compounds
KR100566854B1 (ko)	2006-04-03	5-ｈｔ 수용체 리간드 및 그의 용도
US5302724A (en)	1994-04-12	Antitumor compositions and methods of treatment
HK186596A (en)	1996-10-11	Pyridine and pyridine n-oxide derivatives of diarylmethyl- piperidines or piperazines, compositions and use thereof
CA1168232A (fr)	1984-05-29	Derives de l'isoquinoline, methode de preparation, compositions pharmaceutiques les renfermant et usages
WO1999048887A1 (fr)	1999-09-30	Agents anorexigenes a base d'imidazolones: derives heteroaryles iii
EP0119050B1 (fr)	1989-03-22	Agents dihydropyridine anti-ischaémiques et anti-hypertensifs
CA1248101A (fr)	1989-01-03	Aminoalkoxybenzopyranones utilises comme agents antipsychotiques et anxiolytiques
DD226285A5 (de)	1985-08-21	Verfahren zur herstellung von 1,4-dihydropyridinen
WO1986004582A1 (fr)	1986-08-14	Acylhydrazones de pyridinyle anthelmintiques, procede d'utilisation et compositions
US4835154A (en)	1989-05-30	1-aralykyl-5-piperazinylmethyl-2-mercaptoimidazoles and 2-alkylthioimidazoles and their use as dopamine-βhydroxylase inhibitors
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