CH572472A5 - Quinazoline cpds - useful as analgesics and antipyretics - Google Patents

Quinazoline cpds - useful as analgesics and antipyretics

Info

Publication number: CH572472A5
Authority: CH; Switzerland
Prior art keywords: general formula; quinazolinone; radical; reaction; compound
Prior art date: 1970-10-30

Application number

CH1557271A

Other languages

German (de)

English (en)

Original Assignee

Sumitomo Chemical Co

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.)

1970-10-30

Filing date

1971-10-26

Publication date

1976-02-13

1970-10-30 Priority claimed from JP9630470A external-priority patent/JPS4821953B1/ja

1970-12-11 Priority claimed from JP11446170A external-priority patent/JPS4821956B1/ja

1970-12-11 Priority claimed from JP11068970A external-priority patent/JPS4821955B1/ja

1971-10-26 Application filed by Sumitomo Chemical Co filed Critical Sumitomo Chemical Co

1976-02-13 Publication of CH572472A5 publication Critical patent/CH572472A5/de

Links

229940035676 analgesics Drugs 0.000 title description 2
239000000730 antalgic agent Substances 0.000 title 1
230000001754 anti-pyretic effect Effects 0.000 title 1
239000002221 antipyretic Substances 0.000 title 1
229940125716 antipyretic agent Drugs 0.000 title 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 title 1
-1 5-methylthienyl Chemical group 0.000 claims abstract description 25
238000006243 chemical reaction Methods 0.000 claims abstract description 11
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 6
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000002541 furyl group Chemical group 0.000 claims abstract description 3
125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
125000001544 thienyl group Chemical group 0.000 claims abstract description 3
150000001875 compounds Chemical class 0.000 claims description 18
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 12
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
150000003863 ammonium salts Chemical class 0.000 claims description 8
238000000034 method Methods 0.000 claims description 8
239000002904 solvent Substances 0.000 claims description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 6
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 6
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
229910021529 ammonia Inorganic materials 0.000 claims description 5
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 claims description 4
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 claims description 4
DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 claims description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 2
GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 claims description 2
150000001346 alkyl aryl ethers Chemical class 0.000 claims description 2
125000005037 alkyl phenyl group Chemical group 0.000 claims description 2
125000003277 amino group Chemical group 0.000 claims description 2
150000001983 dialkylethers Chemical class 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
239000000155 melt Substances 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
229910000027 potassium carbonate Inorganic materials 0.000 claims description 2
125000000168 pyrrolyl group Chemical group 0.000 claims description 2
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 claims description 2
239000011877 solvent mixture Substances 0.000 claims description 2
239000008096 xylene Substances 0.000 claims description 2
230000001419 dependent effect Effects 0.000 claims 2
150000003254 radicals Chemical class 0.000 claims 1
239000002253 acid Substances 0.000 abstract description 2
QMNUDYFKZYBWQX-UHFFFAOYSA-N 1H-quinazolin-4-one Chemical compound C1=CC=C2C(=O)N=CNC2=C1 QMNUDYFKZYBWQX-UHFFFAOYSA-N 0.000 abstract 1
MHBPJMUAIOKJNL-UHFFFAOYSA-N 1h-quinazoline-2-thione Chemical compound C1=CC=CC2=NC(S)=NC=C21 MHBPJMUAIOKJNL-UHFFFAOYSA-N 0.000 abstract 1
125000000392 cycloalkenyl group Chemical group 0.000 abstract 1
230000018044 dehydration Effects 0.000 abstract 1
238000006297 dehydration reaction Methods 0.000 abstract 1
230000026030 halogenation Effects 0.000 abstract 1
238000005658 halogenation reaction Methods 0.000 abstract 1
230000003301 hydrolyzing effect Effects 0.000 abstract 1
150000003246 quinazolines Chemical class 0.000 abstract 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
239000000203 mixture Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
IXVBNJRBXHFFPQ-UHFFFAOYSA-N 6-chloro-1-(cyclopropylmethyl)-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 IXVBNJRBXHFFPQ-UHFFFAOYSA-N 0.000 description 2
USFZMSVCRYTOJT-UHFFFAOYSA-N Ammonium acetate Chemical compound N.CC(O)=O USFZMSVCRYTOJT-UHFFFAOYSA-N 0.000 description 2
239000005695 Ammonium acetate Substances 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
229940043376 ammonium acetate Drugs 0.000 description 2
235000019257 ammonium acetate Nutrition 0.000 description 2
230000003110 anti-inflammatory effect Effects 0.000 description 2
210000003169 central nervous system Anatomy 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
239000003814 drug Substances 0.000 description 2
229940079593 drug Drugs 0.000 description 2
230000000694 effects Effects 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
VYMDGNCVAMGZFE-UHFFFAOYSA-N phenylbutazonum Chemical compound O=C1C(CCCC)C(=O)N(C=2C=CC=CC=2)N1C1=CC=CC=C1 VYMDGNCVAMGZFE-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
ZLUDRXRHDQZAKL-UHFFFAOYSA-N 1-(2-ethoxyethyl)-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CCOCC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 ZLUDRXRHDQZAKL-UHFFFAOYSA-N 0.000 description 1
ZTOBFOBNWLGKRC-UHFFFAOYSA-N 1-(2-methylsulfanylethyl)-6-nitro-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(CCSC)C2=CC=C([N+]([O-])=O)C=C2C=1C1=CC=CC=C1 ZTOBFOBNWLGKRC-UHFFFAOYSA-N 0.000 description 1
PBPBRPFGQMBDGR-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-(4-methylphenyl)quinazolin-2-one Chemical compound C1=CC(C)=CC=C1C(C1=CC=CC=C11)=NC(=O)N1CC1CC1 PBPBRPFGQMBDGR-UHFFFAOYSA-N 0.000 description 1
LOKAHOZNNXGVKK-UHFFFAOYSA-N 1-(cyclopropylmethyl)-4-phenyl-6-(trifluoromethyl)quinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(C(F)(F)F)=CC=C2N1CC1CC1 LOKAHOZNNXGVKK-UHFFFAOYSA-N 0.000 description 1
OSCJNCWKJPGCKI-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-methylsulfonyl-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(S(=O)(=O)C)=CC=C2N1CC1CC1 OSCJNCWKJPGCKI-UHFFFAOYSA-N 0.000 description 1
DOZCBTHHFJNFKO-UHFFFAOYSA-N 1-(cyclopropylmethyl)-6-nitro-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC([N+](=O)[O-])=CC=C2N1CC1CC1 DOZCBTHHFJNFKO-UHFFFAOYSA-N 0.000 description 1
125000004807 2-methylethylene group Chemical group [H]C([H])([H])C([H])([*:2])C([H])([H])[*:1] 0.000 description 1
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 description 1
FPCMUNFMVCWNTR-UHFFFAOYSA-N 6-chloro-1-(cyclobutylmethyl)-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CCC1 FPCMUNFMVCWNTR-UHFFFAOYSA-N 0.000 description 1
IOFSXAIXGKVWRX-UHFFFAOYSA-N 6-chloro-1-(cyclohexylmethyl)-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CCCCC1 IOFSXAIXGKVWRX-UHFFFAOYSA-N 0.000 description 1
OELMMDOLCBRQCO-UHFFFAOYSA-N 6-chloro-1-(cyclopentylmethyl)-4-phenylquinazolin-2-one Chemical compound O=C1N=C(C=2C=CC=CC=2)C2=CC(Cl)=CC=C2N1CC1CCCC1 OELMMDOLCBRQCO-UHFFFAOYSA-N 0.000 description 1
BUTMHCQEUBPARZ-UHFFFAOYSA-N 6-chloro-1-(cyclopropylmethyl)-4-(2-fluorophenyl)quinazolin-2-one Chemical compound FC1=CC=CC=C1C(C1=CC(Cl)=CC=C11)=NC(=O)N1CC1CC1 BUTMHCQEUBPARZ-UHFFFAOYSA-N 0.000 description 1
JEELEJOSVAMLJW-UHFFFAOYSA-N 6-chloro-1-(cyclopropylmethyl)-4-(4-methoxyphenyl)quinazolin-2-one Chemical compound C1=CC(OC)=CC=C1C(C1=CC(Cl)=CC=C11)=NC(=O)N1CC1CC1 JEELEJOSVAMLJW-UHFFFAOYSA-N 0.000 description 1
MOAFDYCEKVOEGF-UHFFFAOYSA-N 6-chloro-1-(cyclopropylmethyl)-4-(furan-2-yl)quinazolin-2-one Chemical compound O=C1N=C(C=2OC=CC=2)C2=CC(Cl)=CC=C2N1CC1CC1 MOAFDYCEKVOEGF-UHFFFAOYSA-N 0.000 description 1
RWKBGEDLPCUBAT-UHFFFAOYSA-N 6-chloro-1-(methoxymethyl)-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(COC)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 RWKBGEDLPCUBAT-UHFFFAOYSA-N 0.000 description 1
MKBSFUYZLQSDOM-UHFFFAOYSA-N 6-chloro-4-(2-chlorophenyl)-1-(cyclopropylmethyl)quinazolin-2-one Chemical compound C1(CC1)CN1C(N=C(C2=CC(=CC=C12)Cl)C1=C(C=CC=C1)Cl)=O MKBSFUYZLQSDOM-UHFFFAOYSA-N 0.000 description 1
MTZXSQLPSCPIKR-UHFFFAOYSA-N 6-chloro-4-(3-chlorophenyl)-1-(cyclopropylmethyl)quinazolin-2-one Chemical compound ClC1=CC=CC(C=2C3=CC(Cl)=CC=C3N(CC3CC3)C(=O)N=2)=C1 MTZXSQLPSCPIKR-UHFFFAOYSA-N 0.000 description 1
JTXCUPSQGHJJKG-UHFFFAOYSA-N 6-chloro-4-cyclohexyl-1-(cyclopropylmethyl)quinazolin-2-one Chemical compound O=C1N=C(C2CCCCC2)C2=CC(Cl)=CC=C2N1CC1CC1 JTXCUPSQGHJJKG-UHFFFAOYSA-N 0.000 description 1
NNAANZLIHAKYCZ-UHFFFAOYSA-N 7-chloro-1-(cyclopropylmethyl)-4-phenylquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2C(C=2C=CC=CC=2)=NC(=O)N1CC1CC1 NNAANZLIHAKYCZ-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
239000004254 Ammonium phosphate Substances 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
BHNUZVRAGLGPOO-UHFFFAOYSA-N CCOCCN(C(OCC)=O)C(C=CC(Cl)=C1)=C1C(C(C=CC=C1)=C1F)=O Chemical compound CCOCCN(C(OCC)=O)C(C=CC(Cl)=C1)=C1C(C(C=CC=C1)=C1F)=O BHNUZVRAGLGPOO-UHFFFAOYSA-N 0.000 description 1
NTURVSFTOYPGON-UHFFFAOYSA-N Dihydroquinazoline Chemical class C1=CC=C2C=NCNC2=C1 NTURVSFTOYPGON-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
CZOUOTQLAVTGLC-UHFFFAOYSA-N O=C1N=CC2=CC(Cl)=CC=C2N1C1=NC=CC=C1 Chemical compound O=C1N=CC2=CC(Cl)=CC=C2N1C1=NC=CC=C1 CZOUOTQLAVTGLC-UHFFFAOYSA-N 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
OXGHFUIEUYTKBX-UHFFFAOYSA-N [5-chloro-2-(2-ethoxyethylamino)phenyl]-(2-fluorophenyl)methanone Chemical compound CCOCCNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F OXGHFUIEUYTKBX-UHFFFAOYSA-N 0.000 description 1
230000001154 acute effect Effects 0.000 description 1
231100000403 acute toxicity Toxicity 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
BVCZEBOGSOYJJT-UHFFFAOYSA-N ammonium carbamate Chemical compound [NH4+].NC([O-])=O BVCZEBOGSOYJJT-UHFFFAOYSA-N 0.000 description 1
239000001099 ammonium carbonate Substances 0.000 description 1
235000012501 ammonium carbonate Nutrition 0.000 description 1
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 1
229910000148 ammonium phosphate Inorganic materials 0.000 description 1
235000019289 ammonium phosphates Nutrition 0.000 description 1
230000001760 anti-analgesic effect Effects 0.000 description 1
239000002260 anti-inflammatory agent Substances 0.000 description 1
229940121363 anti-inflammatory agent Drugs 0.000 description 1
GSEZYWGNEACOIW-UHFFFAOYSA-N bis(2-aminophenyl)methanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1N GSEZYWGNEACOIW-UHFFFAOYSA-N 0.000 description 1
230000000740 bleeding effect 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
239000002775 capsule Substances 0.000 description 1
KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
235000010418 carrageenan Nutrition 0.000 description 1
229920001525 carrageenan Polymers 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
125000004775 chlorodifluoromethyl group Chemical group FC(F)(Cl)* 0.000 description 1
231100000160 chronic toxicity Toxicity 0.000 description 1
230000007665 chronic toxicity Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 description 1
MNNHAPBLZZVQHP-UHFFFAOYSA-N diammonium hydrogen phosphate Chemical compound [NH4+].[NH4+].OP([O-])([O-])=O MNNHAPBLZZVQHP-UHFFFAOYSA-N 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000008298 dragée Substances 0.000 description 1
RIFGWPKJUGCATF-UHFFFAOYSA-N ethyl chloroformate Chemical compound CCOC(Cl)=O RIFGWPKJUGCATF-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
125000004705 ethylthio group Chemical group C(C)S* 0.000 description 1
210000003608 fece Anatomy 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
125000001207 fluorophenyl group Chemical group 0.000 description 1
125000005059 halophenyl group Chemical group 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
239000000543 intermediate 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
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
239000007788 liquid Substances 0.000 description 1
231100000053 low toxicity Toxicity 0.000 description 1
125000006431 methyl cyclopropyl group Chemical group 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000000041 non-steroidal anti-inflammatory agent Substances 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000000243 solution Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1
231100000456 subacute toxicity Toxicity 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 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
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/78—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 2
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

CH1557271A 1970-10-30 1971-10-26 Quinazoline cpds - useful as analgesics and antipyretics CH572472A5 (en)

Applications Claiming Priority (7)

Application Number	Priority Date	Filing Date
JP9630670		1970-10-30
JP9630470A JPS4821953B1 (cs)	1970-10-30	1970-10-30
JP9630570		1970-10-30
JP11446170A JPS4821956B1 (cs)	1970-12-11	1970-12-11
JP11068970A JPS4821955B1 (cs)	1970-12-11	1970-12-11
JP12996570		1970-12-28
JP640071		1971-02-13

Publications (1)

Publication Number	Publication Date
CH572472A5 true CH572472A5 (en)	1976-02-13

Family

ID=27563354

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1557271A CH572472A5 (en)	1970-10-30	1971-10-26	Quinazoline cpds - useful as analgesics and antipyretics

Country Status (3)

Country	Link
CH (1)	CH572472A5 (cs)
DD (1)	DD95382A5 (cs)
HU (1)	HU163176B (cs)

1971
- 1971-10-26 CH CH1557271A patent/CH572472A5/de not_active IP Right Cessation
- 1971-10-29 HU HUSU000688 patent/HU163176B/hu unknown
- 1971-10-29 DD DD15865771A patent/DD95382A5/xx unknown

Also Published As

Publication number	Publication date
DD95382A5 (cs)	1973-02-05
HU163176B (cs)	1973-06-28

Legal Events

Date	Code	Title	Description
1985-06-28	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
EP0266558A2 (de)	1988-05-11	5-Alkylbenzimidazole, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel
DE2165056C3 (de)	1975-01-23	Verfahren zur Herstellung von CMnazollnonen
DE2319278A1 (de)	1974-11-07	Diuretisches und antihypertensives mittel
DE1620442B2 (de)	1974-11-14	Verfahren zur Herstellung von 1-Acylindolverbindungen
EP0047328A1 (de)	1982-03-17	1H- und 2H-Indazolderivate und diese enthaltendes Arzneimittel
DE1670200A1 (de)	1972-03-02	Neue arylsubstituierte Piperazinylcarbonsaeureanilide und Verfahren zu deren Herstellung
DE2713933A1 (de)	1977-10-06	Benzoguanamin-derivate
DE1023039B (de)	1958-01-23	Verfahren zur Herstellung von 5-Piperazino-pyridazon-(6)-verbindungen
CH572472A5 (en)	1976-02-13	Quinazoline cpds - useful as analgesics and antipyretics
DE2730467A1 (de)	1979-01-18	Benzylpyrimidine, verfahren zu ihrer herstellung und diese enthaltende arzneimittel
AT312615B (de)	1974-01-10	Verfahren zur Herstellung von neuen 2(1H)-Chinazolinonen
EP0121490B1 (de)	1988-03-02	Substituierte 6-Aryl-1,2,4-triazolo[4,3-b]pyridazine, ihre Herstellung und Verwendung
DE2746550A1 (de)	1978-04-20	Im benzolring gegebenenfalls substituierte eckige klammer auf (5-phenyl- 2-oxyzolyl)-methylenamino eckige klammer zu -imidazolin-2,4-dione
CH634069A5 (en)	1983-01-14	Process for preparing novel 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines
EP0007438A1 (de)	1980-02-06	Neue substituierte 2-Phenylamino-imidazoline-(2), deren Säureadditionssalze, diese enthaltende Arzneimittel und Verfahren zur Herstellung derselben
DE2265242C2 (de)	1983-03-10	Verfahren zur Herstellung von tautomeren 4-Phenyl-1,3-dihydro-2H-1,5-benzodiazepin-2-thionen
DE2319280A1 (de)	1974-11-07	1-substituierte pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE2319281A1 (de)	1974-11-07	Diuretisches und antihypertensives mittel
DE2019719C3 (de)	1975-07-03	1,3,4-Substituierte 5-Dimethylaminouracile und Verfahren zu ihrer Herstellung
CH574418A5 (en)	1976-04-15	3, 4- dihydro-2 (1h)-quin azolinones - anti-inflammatories and analge
DE1695092B2 (de)	1978-08-31	N-(4-Sulfonamidophenyl)-a-alkylsuccinimide und deren Salze mit Basen, Verfahren zu ihrer Herstellung und pharmazeutische Zusammensetzungen
AT301557B (de)	1972-09-11	Verfahren zur Herstellung von neuen Chinazolinderivaten bzw. von Säureadditionssalzen hievon
DE2230792A1 (de)	1974-01-17	3-amino-pyrazolone-(5), verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel
DE1620179A1 (de)	1970-05-21	Verfahren zur Herstellung neuer basischer Derivate des Benzoxazins
AT373588B (de)	1984-02-10	Verfahren zur herstellung von neuen substituierten 1-benzoyl-2-phenylimino-imidazolidinen und von deren salzen