LU81987A1 - Derives de pyrazolo(1,5-c)quinazoline - Google Patents

Derives de pyrazolo(1,5-c)quinazoline Download PDF

Info

Publication number: LU81987A1
Authority: LU; Luxembourg
Prior art keywords: group; compound according; compound; quinazoline; hydrogen atom
Prior art date: 1978-12-13

Application number

LU81987A

Other languages

English (en)

French (fr)

Inventor

B Vogt

L Simpkins

Original Assignee

Squibb & Sons Inc

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.)

1978-12-13

Filing date

1979-12-12

Publication date

1980-04-22

1979-12-12 Application filed by Squibb & Sons Inc filed Critical Squibb & Sons Inc

1980-04-22 Publication of LU81987A1 publication Critical patent/LU81987A1/fr

Links

ONCMJWSDNCJMLL-UHFFFAOYSA-N pyrazolo[1,5-c]quinazoline Chemical class C12=CC=CC=C2N=CN2C1=CC=N2 ONCMJWSDNCJMLL-UHFFFAOYSA-N 0.000 title claims 2
150000001875 compounds Chemical class 0.000 claims description 52
-1 formate ester Chemical class 0.000 claims description 16
125000000217 alkyl group Chemical group 0.000 claims description 15
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 11
150000004702 methyl esters Chemical class 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
239000003795 chemical substances by application Substances 0.000 claims description 6
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims description 6
150000003839 salts Chemical class 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000005843 halogen group Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000003118 aryl group Chemical group 0.000 claims description 4
229910052744 lithium Inorganic materials 0.000 claims description 4
229910052708 sodium Inorganic materials 0.000 claims description 4
239000011734 sodium Substances 0.000 claims description 4
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
229910052801 chlorine Inorganic materials 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
DBNHFEOKGXMKHI-UHFFFAOYSA-N pyrazolo[1,5-c]quinazolin-2-ylmethanol Chemical compound C12=CC=CC=C2N=CN2C1=CC(CO)=N2 DBNHFEOKGXMKHI-UHFFFAOYSA-N 0.000 claims description 3
JIIIAFRTSJEZBL-UHFFFAOYSA-N pyrazolo[1,5-c]quinazoline-2-carboxylic acid Chemical compound C12=CC=CC=C2N=CN2C1=CC(C(=O)O)=N2 JIIIAFRTSJEZBL-UHFFFAOYSA-N 0.000 claims description 3
159000000000 sodium salts Chemical class 0.000 claims description 3
SIJIINJCWQAXKV-UHFFFAOYSA-N 5-phenylpyrazolo[1,5-c]quinazoline-2-carboxylic acid Chemical compound N12N=C(C(=O)O)C=C2C2=CC=CC=C2N=C1C1=CC=CC=C1 SIJIINJCWQAXKV-UHFFFAOYSA-N 0.000 claims description 2
206010027654 Allergic conditions Diseases 0.000 claims 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 claims description 2
230000000172 allergic effect Effects 0.000 claims description 2
208000010668 atopic eczema Diseases 0.000 claims description 2
125000004494 ethyl ester group Chemical group 0.000 claims description 2
230000007062 hydrolysis Effects 0.000 claims description 2
238000006460 hydrolysis reaction Methods 0.000 claims description 2
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
YTNBLSVLSJYVLB-UHFFFAOYSA-N quinazolin-2-ylmethanol Chemical compound C1=CC=CC2=NC(CO)=NC=C21 YTNBLSVLSJYVLB-UHFFFAOYSA-N 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims 2
241000124008 Mammalia Species 0.000 claims 1
125000004429 atom Chemical group 0.000 claims 1
150000001735 carboxylic acids Chemical class 0.000 claims 1
239000003937 drug carrier Substances 0.000 claims 1
239000013067 intermediate product Substances 0.000 claims 1
239000008194 pharmaceutical composition Substances 0.000 claims 1
108090000623 proteins and genes Proteins 0.000 claims 1
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 13
238000002844 melting Methods 0.000 description 12
230000008018 melting Effects 0.000 description 12
239000002244 precipitate Substances 0.000 description 12
238000001914 filtration Methods 0.000 description 11
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Substances OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
239000000706 filtrate Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 8
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
239000000047 product Substances 0.000 description 8
239000011541 reaction mixture Substances 0.000 description 8
NTYJJOPFIAHURM-UHFFFAOYSA-N Histamine Chemical compound NCCC1=CN=CN1 NTYJJOPFIAHURM-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000002775 capsule Substances 0.000 description 6
239000000460 chlorine Substances 0.000 description 6
239000012043 crude product Substances 0.000 description 6
235000019439 ethyl acetate Nutrition 0.000 description 6
239000007787 solid Substances 0.000 description 6
239000000243 solution Substances 0.000 description 6
239000000725 suspension Substances 0.000 description 5
239000003826 tablet Substances 0.000 description 5
ZYHQGITXIJDDKC-UHFFFAOYSA-N 2-[2-(2-aminophenyl)ethyl]aniline Chemical group NC1=CC=CC=C1CCC1=CC=CC=C1N ZYHQGITXIJDDKC-UHFFFAOYSA-N 0.000 description 4
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
239000006188 syrup Substances 0.000 description 4
235000020357 syrup Nutrition 0.000 description 4
238000005406 washing Methods 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 3
239000004480 active ingredient Substances 0.000 description 3
230000003266 anti-allergic effect Effects 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
229960001340 histamine Drugs 0.000 description 3
239000000463 material Substances 0.000 description 3
239000000546 pharmaceutical excipient Substances 0.000 description 3
239000000843 powder Substances 0.000 description 3
ZHUCCRFRDUXTFA-UHFFFAOYSA-N 3-(2-aminophenyl)-1h-pyrazole-5-carboxylic acid Chemical compound NC1=CC=CC=C1C1=CC(C(O)=O)=NN1 ZHUCCRFRDUXTFA-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
206010002198 Anaphylactic reaction Diseases 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920002261 Corn starch Polymers 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
150000007933 aliphatic carboxylic acids Chemical class 0.000 description 2
230000036783 anaphylactic response Effects 0.000 description 2
208000003455 anaphylaxis Diseases 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
239000003610 charcoal Substances 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
239000008120 corn starch Substances 0.000 description 2
239000003599 detergent Substances 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000000796 flavoring agent Substances 0.000 description 2
235000013355 food flavoring agent Nutrition 0.000 description 2
235000003599 food sweetener Nutrition 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
210000003630 histaminocyte Anatomy 0.000 description 2
230000005764 inhibitory process Effects 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000007937 lozenge Substances 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
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
239000006187 pill Substances 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
229910000030 sodium bicarbonate Inorganic materials 0.000 description 2
235000017557 sodium bicarbonate Nutrition 0.000 description 2
239000003765 sweetening agent Substances 0.000 description 2
QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
NOGFHTGYPKWWRX-UHFFFAOYSA-N 2,2,6,6-tetramethyloxan-4-one Chemical compound CC1(C)CC(=O)CC(C)(C)O1 NOGFHTGYPKWWRX-UHFFFAOYSA-N 0.000 description 1
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
IJJWOSAXNHWBPR-HUBLWGQQSA-N 5-[(3as,4s,6ar)-2-oxo-1,3,3a,4,6,6a-hexahydrothieno[3,4-d]imidazol-4-yl]-n-(6-hydrazinyl-6-oxohexyl)pentanamide Chemical compound N1C(=O)N[C@@H]2[C@H](CCCCC(=O)NCCCCCC(=O)NN)SC[C@@H]21 IJJWOSAXNHWBPR-HUBLWGQQSA-N 0.000 description 1
HHSUIJCZPAWXDU-UHFFFAOYSA-N 5-methylpyrazolo[1,5-c]quinazoline-2-carboxylic acid Chemical compound C1=CC=C2C3=CC(C(O)=O)=NN3C(C)=NC2=C1 HHSUIJCZPAWXDU-UHFFFAOYSA-N 0.000 description 1
208000035285 Allergic Seasonal Rhinitis Diseases 0.000 description 1
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
241000416162 Astragalus gummifer Species 0.000 description 1
241000167854 Bourreria succulenta Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
241000282472 Canis lupus familiaris Species 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000019739 Dicalciumphosphate Nutrition 0.000 description 1
241000282326 Felis catus Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
240000001238 Gaultheria procumbens Species 0.000 description 1
235000007297 Gaultheria procumbens Nutrition 0.000 description 1
108010010803 Gelatin Proteins 0.000 description 1
208000001718 Immediate Hypersensitivity Diseases 0.000 description 1
125000002066 L-histidyl group Chemical group [H]N1C([H])=NC(C([H])([H])[C@](C(=O)[*])([H])N([H])[H])=C1[H] 0.000 description 1
235000010643 Leucaena leucocephala Nutrition 0.000 description 1
240000007472 Leucaena leucocephala Species 0.000 description 1
241000288982 Loris Species 0.000 description 1
244000246386 Mentha pulegium Species 0.000 description 1
235000016257 Mentha pulegium Nutrition 0.000 description 1
235000004357 Mentha x piperita Nutrition 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
241000700159 Rattus Species 0.000 description 1
101150098533 SOST gene Proteins 0.000 description 1
229920001800 Shellac Polymers 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
229920001615 Tragacanth Polymers 0.000 description 1
206010045240 Type I hypersensitivity Diseases 0.000 description 1
OEVHZSDDUAPTGG-UHFFFAOYSA-N [3-(2-aminophenyl)-1h-pyrazol-5-yl]methanol Chemical compound NC1=CC=CC=C1C1=CC(CO)=NN1 OEVHZSDDUAPTGG-UHFFFAOYSA-N 0.000 description 1
VPHONORSHWSPFO-UHFFFAOYSA-N [3-(2-aminophenyl)-1h-pyrazol-5-yl]methanol;hydrochloride Chemical compound Cl.NC1=CC=CC=C1C1=CC(CO)=NN1 VPHONORSHWSPFO-UHFFFAOYSA-N 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
239000000783 alginic acid Substances 0.000 description 1
235000010443 alginic acid Nutrition 0.000 description 1
229920000615 alginic acid Polymers 0.000 description 1
229960001126 alginic acid Drugs 0.000 description 1
150000004781 alginic acids Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
125000005907 alkyl ester group Chemical group 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
239000000043 antiallergic agent Substances 0.000 description 1
239000000739 antihistaminic agent Substances 0.000 description 1
229940125715 antihistaminic agent Drugs 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
208000010216 atopic IgE responsiveness Diseases 0.000 description 1
238000009835 boiling Methods 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
125000004799 bromophenyl group Chemical group 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000001506 calcium phosphate Substances 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
235000019693 cherries Nutrition 0.000 description 1
239000007958 cherry flavor Substances 0.000 description 1
229940112822 chewing gum Drugs 0.000 description 1
235000015218 chewing gum Nutrition 0.000 description 1
125000000068 chlorophenyl group Chemical group 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
JJCFRYNCJDLXIK-UHFFFAOYSA-N cyproheptadine Chemical compound C1CN(C)CCC1=C1C2=CC=CC=C2C=CC2=CC=CC=C21 JJCFRYNCJDLXIK-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
NEFBYIFKOOEVPA-UHFFFAOYSA-K dicalcium phosphate Chemical compound [Ca+2].[Ca+2].[O-]P([O-])([O-])=O NEFBYIFKOOEVPA-UHFFFAOYSA-K 0.000 description 1
229940038472 dicalcium phosphate Drugs 0.000 description 1
229910000390 dicalcium phosphate Inorganic materials 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000010685 fatty oil Substances 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
235000013305 food Nutrition 0.000 description 1
239000000499 gel Substances 0.000 description 1
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239000008273 gelatin Substances 0.000 description 1
239000007903 gelatin capsule Substances 0.000 description 1
235000019322 gelatine Nutrition 0.000 description 1
235000011852 gelatine desserts Nutrition 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
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239000005457 ice water Substances 0.000 description 1
208000026278 immune system disease Diseases 0.000 description 1
239000003701 inert diluent Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
238000007912 intraperitoneal administration Methods 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
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150000002500 ions Chemical class 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
125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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210000004072 lung Anatomy 0.000 description 1
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-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
125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000001280 n-hexyl group Chemical group C(CCCCC)* 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
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
230000003472 neutralizing effect Effects 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
125000004430 oxygen atom Chemical group O* 0.000 description 1
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
238000007911 parenteral administration Methods 0.000 description 1
239000002245 particle Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
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OKXPYKHKJCATPX-UHFFFAOYSA-N quinazoline-2-carboxylic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=NC=C21 OKXPYKHKJCATPX-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
206010039083 rhinitis Diseases 0.000 description 1
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
239000004208 shellac Substances 0.000 description 1
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239000000741 silica gel Substances 0.000 description 1
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210000003491 skin Anatomy 0.000 description 1
239000002002 slurry Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002904 solvent Substances 0.000 description 1
241000894007 species Species 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003431 steroids Chemical class 0.000 description 1
238000003756 stirring Methods 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
230000029305 taxis Effects 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
238000004809 thin layer chromatography Methods 0.000 description 1
239000003981 vehicle Substances 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
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Pulmonology (AREA)
Engineering & Computer Science (AREA)
Bioinformatics & Cheminformatics (AREA)
Immunology (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)
Nitrogen Condensed Heterocyclic Rings (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

LU81987A 1978-12-13 1979-12-12 Derives de pyrazolo(1,5-c)quinazoline LU81987A1 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US96964278		1978-12-13
US05/969,642 US4198412A (en)	1978-12-13	1978-12-13	Pyrazolo [1,5-C] quinazoline derivatives and their use in treating allergic conditions

Publications (1)

Publication Number	Publication Date
LU81987A1 true LU81987A1 (fr)	1980-04-22

Family

ID=25515802

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LU81987A LU81987A1 (fr)	1978-12-13	1979-12-12	Derives de pyrazolo(1,5-c)quinazoline

Country Status (15)

Country	Link
US (1)	US4198412A (ja)
JP (1)	JPS5583787A (ja)
AU (1)	AU5359379A (ja)
BE (1)	BE880607A (ja)
CA (1)	CA1122215A (ja)
DE (1)	DE2950234A1 (ja)
DK (1)	DK529179A (ja)
FR (1)	FR2444038A1 (ja)
GB (1)	GB2039896A (ja)
IT (1)	IT1164093B (ja)
LU (1)	LU81987A1 (ja)
NL (1)	NL7908940A (ja)
NO (1)	NO794064L (ja)
SE (1)	SE7910255L (ja)
ZA (1)	ZA796589B (ja)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU178523B (en) *	1979-05-18	1982-05-28	Egyt Gyogyszervegyeszeti Gyar	Process for preparing new pyrazolo-quinazoline derivatives
CN103130810B (zh) *	2013-03-11	2015-02-25	河南师范大学	一种吡唑并[1,5-c]喹唑啉类化合物的合成方法
JP6211189B2 (ja) *	2013-07-17	2017-10-11	ヒソン・マテリアル・リミテッドＨｅｅｓｕｎｇＭａｔｅｒｉａｌＬｔｄ．	窒素含有多環式化合物およびそれを用いた有機発光素子

Family Cites Families (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3313815A (en) *	1964-05-04	1967-04-11	Sterling Drug Inc	8-chloropyrazolo-[1, 5-c]quinazoline derivatives and methods of preparing same
US3899508A (en) *	1974-04-12	1975-08-12	Lilly Co Eli	5-(2-Aminophenyl)pyrazole-3-carboxylic acids and esters thereof
US3895027A (en) *	1974-04-12	1975-07-15	Lilly Co Eli	Process for preparing pyrazole-3-carboxylic acids
US4076818A (en) *	1976-07-02	1978-02-28	E. R. Squibb & Sons, Inc.	Pyrazolo [1,5-C]quinazoline derivatives and related compounds
US4129653A (en) *	1977-01-05	1978-12-12	Ortho Pharmaceutical Corporation	Substituted pyrrolo [1,2-c] quinazolines and pharmaceutical compositions and methods employing them
US4110452A (en) *	1977-10-17	1978-08-29	E. R. Squibb & Sons, Inc.	Pyrazolo (1,5-c) quinazoline derivatives and related compounds
US4112098A (en) *	1977-10-17	1978-09-05	E. R. Squibb & Sons, Inc.	Pyrazolo[1,5-c]quinazoline derivatives and related compounds
US4128644A (en) *	1977-07-29	1978-12-05	E. R. Squibb & Sons, Inc.	Pyrazolo(1,5-c)quinazoline derivatives and related compounds

1978
- 1978-12-13 US US05/969,642 patent/US4198412A/en not_active Expired - Lifetime
1979
- 1979-12-03 CA CA000341087A patent/CA1122215A/en not_active Expired
- 1979-12-04 ZA ZA00796589A patent/ZA796589B/xx unknown
- 1979-12-07 AU AU53593/79A patent/AU5359379A/en not_active Abandoned
- 1979-12-07 GB GB7942375A patent/GB2039896A/en not_active Withdrawn
- 1979-12-12 SE SE7910255A patent/SE7910255L/xx unknown
- 1979-12-12 IT IT51070/79A patent/IT1164093B/it active
- 1979-12-12 DK DK529179A patent/DK529179A/da unknown
- 1979-12-12 NL NL7908940A patent/NL7908940A/nl not_active Application Discontinuation
- 1979-12-12 NO NO794064A patent/NO794064L/no unknown
- 1979-12-12 LU LU81987A patent/LU81987A1/fr unknown
- 1979-12-13 DE DE19792950234 patent/DE2950234A1/de not_active Withdrawn
- 1979-12-13 JP JP16264879A patent/JPS5583787A/ja active Pending
- 1979-12-13 FR FR7930624A patent/FR2444038A1/fr not_active Withdrawn
- 1979-12-13 BE BE0/198559A patent/BE880607A/fr unknown

Also Published As

Publication number	Publication date
AU5359379A (en)	1980-06-19
NO794064L (no)	1980-06-16
IT7951070A0 (it)	1979-12-12
IT1164093B (it)	1987-04-08
NL7908940A (nl)	1980-06-17
DE2950234A1 (de)	1980-06-26
BE880607A (fr)	1980-06-13
FR2444038A1 (fr)	1980-07-11
SE7910255L (sv)	1980-06-14
GB2039896A (en)	1980-08-20
DK529179A (da)	1980-06-14
ZA796589B (en)	1980-11-26
US4198412A (en)	1980-04-15
CA1122215A (en)	1982-04-20
JPS5583787A (en)	1980-06-24

Publication	Publication Date	Title
EP0172096B1 (fr)	1989-01-25	Dérivés d'acylaminométhyl-3 imidazo[1,2-a]pyridines, leur préparation et leur application en thérapeutique
US5124347A (en)	1992-06-23	3-5-ditertiarybutylphenyl-4-hydroxymethylidene derivatives of 1,3-dihydro-2H-indole-2-ones as antiinflammatory agents
EP0501892B1 (fr)	1996-07-24	Dérivés hétérocycliques diazotés N-substitués par un groupement biphénylméthyle, leur préparation, les compositions pharmaceutiques en contenant
EP0010029B1 (fr)	1982-11-17	Ellipticines substituées en position 1 par une chaîne polyaminée, leur synthèse et médicaments les contenant
JPS6323881A (ja)	1988-02-01	１，２，３，３ａ，８，８ａ−ヘキサヒドロ−３ａ，８（および１，３ａ，８）−ジ（およびトリ）メチルピロロ〔２，３−ｂ〕インド−ルおよびそれらの製造法
LU79761A1 (fr)	1980-01-22	Procede de preparation de nouveaux composes de phtalazine et de composition pharmaceutique les contenant
CH653025A5 (fr)	1985-12-13	Oxazolidine-2,4-diones substituees en position 5 douees d'activite hypoglycemique.
CA2104883A1 (fr)	1994-02-28	Derives d'acide thienyl ou pyrrolyl carboxyliques, leur preparation et medicaments les contenant
FR2498601A1 (fr)	1982-07-30	Nouveaux chromannes substitues utiles notamment comme anti-inflammatoires
FR2665441A1 (fr)	1992-02-07	Derives de la n-sulfonyl indoline, leur preparation, les compositions pharmaceutiques en contenant.
EP0611766A1 (fr)	1994-08-24	Dérivés de 2-amido-thiazoles polysubstitués, procédé de préparation, composition pharmaceutique et utilisation de ces dérivés pour la préparation d'un médicament
JPH0471073B2 (ja)	1992-11-12
WO1979000319A1 (fr)	1979-06-14	Nouvelles indolo (2, 3-a) quinolizidines, leur preparation et leur utilisation therapeutique
MC1969A1 (fr)	1989-09-29	Procedes pour preparer des composes antitumoraux,formulation pharmaceutique contenant ces composes,leurs utilisations en medecine et pharmacie,et composes intermediaires pour leur preparation
WO1997025329A1 (fr)	1997-07-17	DERIVES DE 5H,10H-IMIDAZO[1,2-a]INDOLO[3,2-e]PYRAZINE-4-ONE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
CH649994A5 (fr)	1985-06-28	Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant.
EP0021857B1 (fr)	1982-12-22	Dérivés de l'indole, leur préparation et medicaments les contenant
EP0018857B1 (fr)	1983-01-19	Pyrimido et imidazo-pyrido-indole-diones, leur préparation et leur application en thérapeutique
LU82419A1 (fr)	1980-07-31	Pyrido(1,2-a)pyrimidines substituees
IE49800B1 (en)	1985-12-25	Benzimidazolone derivatives,process for their preparation and pharmaceutical compositions containing them
JPS6399057A (ja)	1988-04-30	グリシン誘導体
EP0233800B1 (fr)	1990-02-28	Dérivés d'imidazo[1,2-a]quinoléines, leur préparation et leur application en thérapeutique
JPH02169571A (ja)	1990-06-29	置換アリルアミン誘導体
EP0772615A1 (fr)	1997-05-14	DERIVES D'ACIDE IMIDAZO 1,2-a]INDENO 1,2-e]PYRAZINE-2-CARBOXYLIQUE, LEUR PREPARATION ET LES MEDICAMENTS LES CONTENANT
MC1616A1 (fr)	1985-07-18	Derives d'imidazobenzodiazepine