JPS5862176A - 三環式キナゾリノン類 - Google Patents

三環式キナゾリノン類

Info

Publication number: JPS5862176A
Authority: JP; Japan
Prior art keywords: compound; formula; alkyl; hydrogen; group
Prior art date: 1981-09-16
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.): Pending

Application number

JP57160767A

Other languages

English (en)

Japanese (ja)

Inventor

ゴウエツ・エドウアルド・ハ−ドツトマン

ウイリアム・ジヨセフ・ホウリハン

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.)

Sandoz AG

Original Assignee

Sandoz AG

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.)

1981-09-16

Filing date

1982-09-14

Publication date

1983-04-13

1982-09-14 Application filed by Sandoz AG filed Critical Sandoz AG

1983-04-13 Publication of JPS5862176A publication Critical patent/JPS5862176A/ja

Status Pending legal-status Critical Current

Links

150000003246 quinazolines Chemical class 0.000 title 1
150000001875 compounds Chemical class 0.000 claims description 105
229910052739 hydrogen Inorganic materials 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 52
125000000217 alkyl group Chemical group 0.000 claims description 33
229910052736 halogen Inorganic materials 0.000 claims description 30
150000002367 halogens Chemical class 0.000 claims description 30
150000002431 hydrogen Chemical group 0.000 claims description 26
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 23
239000000460 chlorine Substances 0.000 claims description 19
229910052801 chlorine Inorganic materials 0.000 claims description 18
239000002253 acid Substances 0.000 claims description 17
239000012458 free base Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 15
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
239000000203 mixture Substances 0.000 claims description 12
125000001309 chloro group Chemical group Cl* 0.000 claims description 10
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
229940079593 drug Drugs 0.000 claims description 7
239000003814 drug Substances 0.000 claims description 7
238000004519 manufacturing process Methods 0.000 claims description 7
230000002936 tranquilizing effect Effects 0.000 claims description 7
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 5
125000000304 alkynyl group Chemical group 0.000 claims description 5
239000003204 tranquilizing agent Substances 0.000 claims description 5
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
239000011737 fluorine Substances 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 claims description 3
229940125725 tranquilizer Drugs 0.000 claims description 3
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 2
101150070189 CIN3 gene Proteins 0.000 claims description 2
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
MXOAEAUPQDYUQM-UHFFFAOYSA-N chlorphenesin Chemical group OCC(O)COC1=CC=C(Cl)C=C1 MXOAEAUPQDYUQM-UHFFFAOYSA-N 0.000 claims description 2
210000003625 skull Anatomy 0.000 claims 1
238000012360 testing method Methods 0.000 description 33
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 27
238000000034 method Methods 0.000 description 23
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 21
125000001424 substituent group Chemical group 0.000 description 17
238000002844 melting Methods 0.000 description 16
230000008018 melting Effects 0.000 description 16
239000000243 solution Substances 0.000 description 14
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 12
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
108090000839 GABA-A Receptors Proteins 0.000 description 10
102000004300 GABA-A Receptors Human genes 0.000 description 10
239000000047 product Substances 0.000 description 10
230000000694 effects Effects 0.000 description 8
239000007788 liquid Substances 0.000 description 7
FHBBETAOBPMWTJ-UHFFFAOYSA-N 1h-quinazolin-5-one Chemical compound N1C=NC=C2C(=O)C=CC=C21 FHBBETAOBPMWTJ-UHFFFAOYSA-N 0.000 description 6
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
229940049706 benzodiazepine Drugs 0.000 description 6
239000000872 buffer Substances 0.000 description 6
238000010992 reflux Methods 0.000 description 6
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 5
239000007983 Tris buffer Substances 0.000 description 5
238000002360 preparation method Methods 0.000 description 5
239000007787 solid Substances 0.000 description 5
LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 5
-1 7-chloro-1-(p-chlorobenzyl)-2,3-dihydroimidazo[2,1-b]quinazolin-5(IH)-one compound Chemical class 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
125000003342 alkenyl group Chemical group 0.000 description 4
150000001557 benzodiazepines Chemical class 0.000 description 4
210000004556 brain Anatomy 0.000 description 4
AAOVKJBEBIDNHE-UHFFFAOYSA-N diazepam Chemical compound N=1CC(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 AAOVKJBEBIDNHE-UHFFFAOYSA-N 0.000 description 4
229960003529 diazepam Drugs 0.000 description 4
229960002200 flunitrazepam Drugs 0.000 description 4
BTCSSZJGUNDROE-UHFFFAOYSA-N gamma-aminobutyric acid Chemical compound NCCCC(O)=O BTCSSZJGUNDROE-UHFFFAOYSA-N 0.000 description 4
238000005222 photoaffinity labeling Methods 0.000 description 4
230000009870 specific binding Effects 0.000 description 4
239000000725 suspension Substances 0.000 description 4
SBJIDFMJAUMHPU-UHFFFAOYSA-N 2,6-dichloro-3-(2-chloroethyl)quinazolin-4-one Chemical compound C1=C(Cl)C=C2C(=O)N(CCCl)C(Cl)=NC2=C1 SBJIDFMJAUMHPU-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
239000002249 anxiolytic agent Substances 0.000 description 3
230000027455 binding Effects 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
230000003993 interaction Effects 0.000 description 3
239000012044 organic layer Substances 0.000 description 3
239000008188 pellet Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
239000007858 starting material Substances 0.000 description 3
RELMFMZEBKVZJC-UHFFFAOYSA-N 1,2,3-trichlorobenzene Chemical compound ClC1=CC=CC(Cl)=C1Cl RELMFMZEBKVZJC-UHFFFAOYSA-N 0.000 description 2
SVUOLADPCWQTTE-UHFFFAOYSA-N 1h-1,2-benzodiazepine Chemical compound N1N=CC=CC2=CC=CC=C12 SVUOLADPCWQTTE-UHFFFAOYSA-N 0.000 description 2
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 2
SAARQEYWLYTQFL-UHFFFAOYSA-N 2,6-dichloro-4-(2-chloroethoxy)quinazoline Chemical compound C1=C(Cl)C=C2C(OCCCl)=NC(Cl)=NC2=C1 SAARQEYWLYTQFL-UHFFFAOYSA-N 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
PPTYJKAXVCCBDU-UHFFFAOYSA-N Rohypnol Chemical compound N=1CC(=O)N(C)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1F PPTYJKAXVCCBDU-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
239000005557 antagonist Substances 0.000 description 2
239000002585 base Substances 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
210000001638 cerebellum Anatomy 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 description 2
239000002552 dosage form Substances 0.000 description 2
230000002349 favourable effect Effects 0.000 description 2
229960003692 gamma aminobutyric acid Drugs 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000012528 membrane Substances 0.000 description 2
230000009871 nonspecific binding Effects 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
239000008196 pharmacological composition Substances 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
KDDNKZCVYQDGKE-UHFFFAOYSA-N (2-chlorophenyl)methanamine Chemical compound NCC1=CC=CC=C1Cl KDDNKZCVYQDGKE-UHFFFAOYSA-N 0.000 description 1
125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 description 1
MPPPKRYCTPRNTB-UHFFFAOYSA-N 1-bromobutane Chemical compound CCCCBr MPPPKRYCTPRNTB-UHFFFAOYSA-N 0.000 description 1
QKNYBSVHEMOAJP-UHFFFAOYSA-N 2-amino-2-(hydroxymethyl)propane-1,3-diol;hydron;chloride Chemical compound Cl.OCC(N)(CO)CO QKNYBSVHEMOAJP-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
MOEOKTGHYZNPJC-UHFFFAOYSA-N 8-chloro-1-ethyl-3,4-dihydro-2H-pyrimido[2,1-b]quinazolin-6-one Chemical class ClC=1C=C2C(N3C(=NC2=CC1)N(CCC3)CC)=O MOEOKTGHYZNPJC-UHFFFAOYSA-N 0.000 description 1
RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
208000019901 Anxiety disease Diseases 0.000 description 1
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 1
244000132059 Carica parviflora Species 0.000 description 1
235000014653 Carica parviflora Nutrition 0.000 description 1
241000282693 Cercopithecidae Species 0.000 description 1
206010010904 Convulsion Diseases 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
241000023320 Luma <angiosperm> Species 0.000 description 1
101100038125 Mus musculus Rora gene Proteins 0.000 description 1
101100508851 Oryza sativa subsp. japonica CIN6 gene Proteins 0.000 description 1
240000002834 Paulownia tomentosa Species 0.000 description 1
241001474791 Proboscis Species 0.000 description 1
101100439738 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CIC1 gene Proteins 0.000 description 1
206010041349 Somnolence Diseases 0.000 description 1
230000032683 aging Effects 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
230000036506 anxiety Effects 0.000 description 1
230000000949 anxiolytic effect Effects 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
238000003556 assay Methods 0.000 description 1
VEQAGSPCZANNDR-UHFFFAOYSA-N azepine-1-sulfonamide Chemical compound NS(=O)(=O)N1C=CC=CC=C1 VEQAGSPCZANNDR-UHFFFAOYSA-N 0.000 description 1
238000011001 backwashing Methods 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
239000008280 blood Substances 0.000 description 1
210000004369 blood Anatomy 0.000 description 1
230000003182 bronchodilatating effect Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 1
239000001110 calcium chloride Substances 0.000 description 1
229910001628 calcium chloride Inorganic materials 0.000 description 1
244000309466 calf Species 0.000 description 1
239000002775 capsule Substances 0.000 description 1
239000000969 carrier Substances 0.000 description 1
210000001159 caudate nucleus Anatomy 0.000 description 1
239000003874 central nervous system depressant Substances 0.000 description 1
230000002490 cerebral effect Effects 0.000 description 1
238000006243 chemical reaction Methods 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000000973 chemotherapeutic effect Effects 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000013068 control sample Substances 0.000 description 1
230000036461 convulsion Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000001316 cycloalkyl alkyl group Chemical group 0.000 description 1
125000004981 cycloalkylmethyl group Chemical group 0.000 description 1
229960003638 dopamine Drugs 0.000 description 1
230000005496 eutectics Effects 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000001747 exhibiting effect Effects 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
108010045196 flunitrazepam receptor Proteins 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000003365 glass fiber Substances 0.000 description 1
UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 1
229960002456 hexobarbital Drugs 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
210000003140 lateral ventricle Anatomy 0.000 description 1
238000012417 linear regression Methods 0.000 description 1
239000006166 lysate Substances 0.000 description 1
229910001629 magnesium chloride Inorganic materials 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
230000003340 mental effect Effects 0.000 description 1
229910021645 metal ion Inorganic materials 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
FGDYAAXXBPMZDU-UHFFFAOYSA-N n,n-dimethylacetamide;ethanol Chemical compound CCO.CN(C)C(C)=O FGDYAAXXBPMZDU-UHFFFAOYSA-N 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
239000000546 pharmaceutical excipient Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
239000001103 potassium chloride Substances 0.000 description 1
235000011164 potassium chloride Nutrition 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
230000011514 reflex Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
230000001624 sedative effect Effects 0.000 description 1
238000013207 serial dilution Methods 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
238000013268 sustained release Methods 0.000 description 1
239000012730 sustained-release form Substances 0.000 description 1
238000012353 t test Methods 0.000 description 1
230000002123 temporal effect Effects 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
- 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
- A61P25/20—Hypnotics; Sedatives

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Anesthesiology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

JP57160767A 1981-09-16 1982-09-14 三環式キナゾリノン類 Pending JPS5862176A (ja)

Applications Claiming Priority (5)

Application Number	Priority Date	Filing Date
US30248381A	1981-09-16	1981-09-16
US302486		1981-09-16
US302485		1981-09-16
US302483		1981-09-16
US302484		2002-11-22

Publications (1)

Publication Number	Publication Date
JPS5862176A true JPS5862176A (ja)	1983-04-13

Family

ID=23167906

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP57160767A Pending JPS5862176A (ja)	1981-09-16	1982-09-14	三環式キナゾリノン類

Country Status (4)

Country	Link
JP (1)	JPS5862176A (fr)
BE (1)	BE894374A (fr)
PH (1)	PH19259A (fr)
ZA (1)	ZA826819B (fr)

1982
- 1982-09-10 PH PH27853A patent/PH19259A/en unknown
- 1982-09-13 BE BE1/10588A patent/BE894374A/fr not_active IP Right Cessation
- 1982-09-14 JP JP57160767A patent/JPS5862176A/ja active Pending
- 1982-09-16 ZA ZA826819A patent/ZA826819B/xx unknown

Also Published As

Publication number	Publication date
ZA826819B (en)	1984-04-25
PH19259A (en)	1986-02-19
BE894374A (fr)	1983-03-14

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NL1031384C2 (nl)	2007-01-23	Gesubstitueerde aryl-1,4-pyrazinederivaten.
KR20020011986A (ko)	2002-02-09	5-치환된 아릴피리미딘
JPS5862176A (ja)	1983-04-13	三環式キナゾリノン類
US4859671A (en)	1989-08-22	2-substituted 1,2-benzisothiazol-3(2H)-one 1,1-dioxide useful as an anxiolytic agent
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US4451448A (en)	1984-05-29	1-Substituted tricyclic quinazolinones useful as tranquilizers
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US4451464A (en)	1984-05-29	Trifluoromethyl substituted tricyclic quinazolinones useful as tranquilizers
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GB2105721A (en)	1983-03-30	Tricyclic quinazolinones