EP0000149A1 - Verfahren zur Herstellung von Chinazolinon-oxid-derivaten - Google Patents

Verfahren zur Herstellung von Chinazolinon-oxid-derivaten Download PDF

Info

Publication number: EP0000149A1
Authority: EP; European Patent Office
Prior art keywords: quinazolinone; formula; chloro; phenyl; mole
Prior art date: 1977-06-16
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 Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Withdrawn

Application number

EP78100163A

Other languages

English (en)

French (fr)

Inventor

William Joseph Middleton

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.)

EIDP Inc

Original Assignee

EI Du Pont de Nemours and 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.)

1977-06-16

Filing date

1978-06-15

Publication date

1979-01-10

1978-06-15 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1979-01-10 Publication of EP0000149A1 publication Critical patent/EP0000149A1/de

Status Withdrawn legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims description 7
FTAHQVWNRWZINV-UHFFFAOYSA-N 1-hydroxyquinazolin-2-one Chemical class C1=CC=C2C=NC(=O)N(O)C2=C1 FTAHQVWNRWZINV-UHFFFAOYSA-N 0.000 title description 7
150000001875 compounds Chemical class 0.000 claims abstract description 14
239000012948 isocyanate Substances 0.000 claims description 10
150000002513 isocyanates Chemical class 0.000 claims description 10
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
239000002253 acid Substances 0.000 claims description 7
239000007795 chemical reaction product Substances 0.000 claims description 7
125000004432 carbon atom Chemical group C* 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 4
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 3
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims description 2
229910052799 carbon Inorganic materials 0.000 claims 1
238000000034 method Methods 0.000 abstract description 12
PZOZHMBWLDUJCP-UHFFFAOYSA-N 3-fluoro-1H-1,2-benzodiazepine Chemical class FC1=NNC2=C(C=C1)C=CC=C2 PZOZHMBWLDUJCP-UHFFFAOYSA-N 0.000 abstract description 3
229940035363 muscle relaxants Drugs 0.000 abstract description 2
239000003158 myorelaxant agent Substances 0.000 abstract description 2
229940125723 sedative agent Drugs 0.000 abstract description 2
239000000932 sedative agent Substances 0.000 abstract description 2
239000003204 tranquilizing agent Substances 0.000 abstract description 2
230000002936 tranquilizing effect Effects 0.000 abstract description 2
239000000543 intermediate Substances 0.000 abstract 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 56
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 33
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 22
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 18
239000013078 crystal Substances 0.000 description 18
239000007787 solid Substances 0.000 description 16
PFNXVIDDDAFQRQ-UHFFFAOYSA-N C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 PFNXVIDDDAFQRQ-UHFFFAOYSA-N 0.000 description 12
239000011541 reaction mixture Substances 0.000 description 12
239000000203 mixture Substances 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZUWXHHBROGLWNH-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-phenylmethanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 ZUWXHHBROGLWNH-UHFFFAOYSA-N 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 3
DYPCOCOEFYSJHP-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-1-methyl-3-phenylurea Chemical compound C=1C=C(Cl)C=C(C(=O)C=2C=CC=CC=2)C=1N(C)C(=O)NC1=CC=CC=C1 DYPCOCOEFYSJHP-UHFFFAOYSA-N 0.000 description 3
CCEBWDWBJVBYFJ-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-3-propan-2-ylurea Chemical compound CC(C)NC(=O)NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 CCEBWDWBJVBYFJ-UHFFFAOYSA-N 0.000 description 3
QIDCJFIPAIPVRT-UHFFFAOYSA-N 6-bromo-4-hydroxy-3-methyl-4-phenyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Br)C=C2C1(O)C1=CC=CC=C1 QIDCJFIPAIPVRT-UHFFFAOYSA-N 0.000 description 3
PIKZXHWPRIJZJN-UHFFFAOYSA-N 6-chloro-1-methyl-3-oxido-4-phenylquinazolin-3-ium-2-one Chemical compound [O-][N+]=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 PIKZXHWPRIJZJN-UHFFFAOYSA-N 0.000 description 3
BYLRNYNRGXIPPV-UHFFFAOYSA-N 6-chloro-3-ethyl-4-hydroxy-4-phenyl-1h-quinazolin-2-one Chemical compound CCN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 BYLRNYNRGXIPPV-UHFFFAOYSA-N 0.000 description 3
LOVPZNFLGAXZGT-UHFFFAOYSA-N 6-chloro-4-ethoxy-3,4-diphenyl-1h-quinazolin-2-one Chemical compound O=C1NC2=CC=C(Cl)C=C2C(OCC)(C=2C=CC=CC=2)N1C1=CC=CC=C1 LOVPZNFLGAXZGT-UHFFFAOYSA-N 0.000 description 3
AWSGAAUIGPHERF-UHFFFAOYSA-N 6-chloro-4-hydroxy-3-methyl-4-phenyl-1h-quinazolin-2-one Chemical compound CN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1 AWSGAAUIGPHERF-UHFFFAOYSA-N 0.000 description 3
ZXBWHSQNFXUCLP-UHFFFAOYSA-N C1=CC=C2NC(=O)[N+]([O-])=CC2=C1 Chemical class C1=CC=C2NC(=O)[N+]([O-])=CC2=C1 ZXBWHSQNFXUCLP-UHFFFAOYSA-N 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000002244 precipitate Substances 0.000 description 3
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
JRTXZECHXRHMEP-UHFFFAOYSA-N C12=CC(Br)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 Chemical compound C12=CC(Br)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1 JRTXZECHXRHMEP-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
BNFUPOXNFMFOLD-UHFFFAOYSA-N N=C=O.NC1=CC=CC=C1C(=O)C1=CC=CC=C1 Chemical compound N=C=O.NC1=CC=CC=C1C(=O)C1=CC=CC=C1 BNFUPOXNFMFOLD-UHFFFAOYSA-N 0.000 description 2
WPNMLCMTDCANOZ-UHFFFAOYSA-N [5-chloro-2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1 WPNMLCMTDCANOZ-UHFFFAOYSA-N 0.000 description 2
150000001298 alcohols Chemical class 0.000 description 2
238000009835 boiling Methods 0.000 description 2
235000013877 carbamide Nutrition 0.000 description 2
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
150000007524 organic acids Chemical class 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
239000000047 product Substances 0.000 description 2
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 2
239000002904 solvent Substances 0.000 description 2
150000003672 ureas Chemical class 0.000 description 2
LXJVUGANBDAASB-UHFFFAOYSA-N (2-amino-5-bromophenyl)-phenylmethanone Chemical compound NC1=CC=C(Br)C=C1C(=O)C1=CC=CC=C1 LXJVUGANBDAASB-UHFFFAOYSA-N 0.000 description 1
GTGMXPIQRQSORU-UHFFFAOYSA-N (2-amino-5-chlorophenyl)-(2-fluorophenyl)methanone Chemical compound NC1=CC=C(Cl)C=C1C(=O)C1=CC=CC=C1F GTGMXPIQRQSORU-UHFFFAOYSA-N 0.000 description 1
125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
XHPPBGZNBZMKNH-UHFFFAOYSA-N 1,2-dihydro-1,2-benzodiazepin-3-one Chemical compound C1=CC(O)=NNC2=CC=CC=C21 XHPPBGZNBZMKNH-UHFFFAOYSA-N 0.000 description 1
OKYIKPYUCUWSDO-UHFFFAOYSA-N 1-(2-benzoyl-4-chlorophenyl)-3-phenylurea Chemical compound C=1C=CC=CC=1C(=O)C1=CC(Cl)=CC=C1NC(=O)NC1=CC=CC=C1 OKYIKPYUCUWSDO-UHFFFAOYSA-N 0.000 description 1
ZQXCQTAELHSNAT-UHFFFAOYSA-N 1-chloro-3-nitro-5-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC(Cl)=CC(C(F)(F)F)=C1 ZQXCQTAELHSNAT-UHFFFAOYSA-N 0.000 description 1
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical class C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
GSLTVFIVJMCNBH-UHFFFAOYSA-N 2-isocyanatopropane Chemical compound CC(C)N=C=O GSLTVFIVJMCNBH-UHFFFAOYSA-N 0.000 description 1
KVBZGDNWBRCXHF-UHFFFAOYSA-N 3-oxidoquinazolin-3-ium Chemical compound C1=CC=CC2=C[N+]([O-])=CN=C21 KVBZGDNWBRCXHF-UHFFFAOYSA-N 0.000 description 1
ZNBNBTIDJSKEAM-UHFFFAOYSA-N 4-[7-hydroxy-2-[5-[5-[6-hydroxy-6-(hydroxymethyl)-3,5-dimethyloxan-2-yl]-3-methyloxolan-2-yl]-5-methyloxolan-2-yl]-2,8-dimethyl-1,10-dioxaspiro[4.5]decan-9-yl]-2-methyl-3-propanoyloxypentanoic acid Chemical compound C1C(O)C(C)C(C(C)C(OC(=O)CC)C(C)C(O)=O)OC11OC(C)(C2OC(C)(CC2)C2C(CC(O2)C2C(CC(C)C(O)(CO)O2)C)C)CC1 ZNBNBTIDJSKEAM-UHFFFAOYSA-N 0.000 description 1
SDEBYHVDMCQKNZ-UHFFFAOYSA-N 4-methoxy-6-piperazin-1-ylpyrimidine;hydrochloride Chemical compound Cl.C1=NC(OC)=CC(N2CCNCC2)=N1 SDEBYHVDMCQKNZ-UHFFFAOYSA-N 0.000 description 1
JSTXCWJWQKRPIU-UHFFFAOYSA-N 6-chloro-1-methyl-4-phenylquinazolin-2-one Chemical compound N=1C(=O)N(C)C2=CC=C(Cl)C=C2C=1C1=CC=CC=C1 JSTXCWJWQKRPIU-UHFFFAOYSA-N 0.000 description 1
WQKHERPPDYPMNX-UHFFFAOYSA-N 6-chloro-3,4-dihydro-2h-naphthalen-1-one Chemical compound O=C1CCCC2=CC(Cl)=CC=C21 WQKHERPPDYPMNX-UHFFFAOYSA-N 0.000 description 1
YKTGQUPZGACWEI-UHFFFAOYSA-N 6-chloro-3-ethyl-4-(2-fluorophenyl)-4-hydroxy-1h-quinazolin-2-one Chemical compound CCN1C(=O)NC2=CC=C(Cl)C=C2C1(O)C1=CC=CC=C1F YKTGQUPZGACWEI-UHFFFAOYSA-N 0.000 description 1
PUOYDTRFCAVAPT-UHFFFAOYSA-N 6-chloro-4-hydroxy-1,3-dimethyl-4-phenylquinazolin-2-one Chemical compound C12=CC(Cl)=CC=C2N(C)C(=O)N(C)C1(O)C1=CC=CC=C1 PUOYDTRFCAVAPT-UHFFFAOYSA-N 0.000 description 1
-1 6-substituted-4-phenylquinazolinone 3-oxides Chemical class 0.000 description 1
VDKXMYMQSHUBMT-UHFFFAOYSA-N C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1F Chemical compound C12=CC(Cl)=CC=C2NC(=O)[N+]([O-])=C1C1=CC=CC=C1F VDKXMYMQSHUBMT-UHFFFAOYSA-N 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
AGKPGIOZNCJFTQ-UHFFFAOYSA-N [2-(methylamino)phenyl]-phenylmethanone Chemical compound CNC1=CC=CC=C1C(=O)C1=CC=CC=C1 AGKPGIOZNCJFTQ-UHFFFAOYSA-N 0.000 description 1
239000005456 alcohol based solvent Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001914 filtration Methods 0.000 description 1
QBRSFUSGKXVSPM-UHFFFAOYSA-N hydroxylamine;hydrobromide Chemical compound Br.ON QBRSFUSGKXVSPM-UHFFFAOYSA-N 0.000 description 1
150000002443 hydroxylamines Chemical class 0.000 description 1
229910000378 hydroxylammonium sulfate Inorganic materials 0.000 description 1
XSXHWVKGUXMUQE-UHFFFAOYSA-N osmium dioxide Inorganic materials O=[Os]=O XSXHWVKGUXMUQE-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 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
- C07D239/80—Oxygen atoms
- C07D239/82—Oxygen atoms with an aryl radical attached in position 4

Definitions

the present invention relates to an improved process for making the quinazolinone 3-oxides of formula (1), above, and an alternate process for making the quinazolinone 3-oxides of formula (3), above.
the present invention relates to an improved process for preparing 6-substituted-4-phenylquinazolinone 3-oxides by the treatment of 2-aminobenzophenone-isocyanate reaction products with hydroxylamine salts.
A is an organic or inorganic acid with a pKa of less than 2.
Quinazolinone oxides of formula IV can be prepared by heating a solution or mixture of 2-aminobenzo- phenoneisocyanate reaction products (of Formula II or III) and an acid addition salt of hydroxylamine in an alcohol solvent.
the reaction is conveniently carried out at the reflux temperature of the alcohol solvent, but temperatures from 40° to 200°C are operable.
Alcohol solvents useful for this reaction include, but are not limited to, ethanol, methanol, propanol, isopropanol, butanol, 2-methoxyethanol, ethylene glycol, and propylene glycol.
Salts of hydroxylamine useful in this reaction include salts with organic or inorganic acids having a pKa of less than 2, such as hydroxylamine hydrochloride, hydroxylamine hydrobromide and hydroxylamine sulfate.
the time required for the reaction varies from a few minutes when more reactive isocyanate adducts or higher boiling alcohols are used, to a few days or even weeks when less reactive isocyanate adducts or lower boiling alcohols are used.
the product quinazolinone oxides can be isolated from the reaction mixture by conventional means. In most cases, the quinazolinone oxides are considerably less soluble than the'reactants, and will precipitate during the course of the reaction. When this occurs, the product quinazolinone oxides can be isolated by simply filtering the reaction mixture.
the 2-aminobenzophenone-isocyanate adducts used as starting materials can be prepared by the reaction of 2-aminobenzophenones with organic isocyanates as illustrated in the following Examples cr as described by Sulkowski et al. J. Org. Chem., 27 4424 (1962) or by Metlesics et al., J. Org. Chem., 31 1007 (1966).
the compounds of formula IV can be prepared by heating a compound of formula II in a suitable alcohol followed by treatment with a suitable acid addition salt of hydroxylamine.
R 2 0 H is lower aliphatic alcohol of 1-6 carbon atoms, preferably methanol or ethanol.
Table I shows additional ureas and hydroxyquinazo- linones which can be prepared by the process disclosed and exemplified above using the appropriate aminobenzophenone and a suitable organic isocyanate.
Table II shows additional quinazolinone oxides which can be prepared by the process disclosed and exemplified above using the appropriate isocyanate adduct and hydroxylamine or a suitable salt thereof.

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pretreatment Of Seeds And Plants (AREA)
Solid-Sorbent Or Filter-Aiding Compositions (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)

EP78100163A 1977-06-16 1978-06-15 Verfahren zur Herstellung von Chinazolinon-oxid-derivaten Withdrawn EP0000149A1 (de)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80707677A	1977-06-16	1977-06-16
US807076		1991-12-13

Publications (1)

Publication Number	Publication Date
EP0000149A1 true EP0000149A1 (de)	1979-01-10

Family

ID=25195510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
EP78100163A Withdrawn EP0000149A1 (de)	1977-06-16	1978-06-15	Verfahren zur Herstellung von Chinazolinon-oxid-derivaten

Country Status (16)

Country	Link
EP (1)	EP0000149A1 (de)
JP (1)	JPS545988A (de)
AT (1)	ATA436678A (de)
AU (1)	AU3709278A (de)
CA (1)	CA1094068A (de)
DK (1)	DK176378A (de)
ES (1)	ES470828A1 (de)
FI (1)	FI781928A7 (de)
GR (1)	GR64944B (de)
IT (1)	IT1098341B (de)
NO (1)	NO782087L (de)
NZ (1)	NZ187581A (de)
PL (1)	PL113420B1 (de)
PT (1)	PT68174A (de)
SU (1)	SU797575A3 (de)
ZA (1)	ZA783438B (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12410177B2 (en)	2018-04-09	2025-09-09	Bmg (British Medical Group) Limited	Antimicrobial and anticancer cationic phthalocyanine compounds

Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH573412A5 (en) *	1971-08-17	1976-03-15	Sumitomo Chemical Co	1-substd 4-aryl-2(1h) quinazolinones - anti-inflammatories, analgesics, uricosurics, andantivirals

1978
- 1978-04-24 DK DK176378A patent/DK176378A/da unknown
- 1978-06-14 CA CA305,471A patent/CA1094068A/en not_active Expired
- 1978-06-14 AU AU37092/78A patent/AU3709278A/en active Pending
- 1978-06-15 AT AT436678A patent/ATA436678A/de not_active Application Discontinuation
- 1978-06-15 ES ES470828A patent/ES470828A1/es not_active Expired
- 1978-06-15 NO NO782087A patent/NO782087L/no unknown
- 1978-06-15 IT IT24615/78A patent/IT1098341B/it active
- 1978-06-15 PT PT68174A patent/PT68174A/pt unknown
- 1978-06-15 ZA ZA00783438A patent/ZA783438B/xx unknown
- 1978-06-15 SU SU782627504A patent/SU797575A3/ru active
- 1978-06-15 NZ NZ187581A patent/NZ187581A/xx unknown
- 1978-06-15 EP EP78100163A patent/EP0000149A1/de not_active Withdrawn
- 1978-06-16 FI FI781928A patent/FI781928A7/fi not_active Application Discontinuation
- 1978-06-16 GR GR56539A patent/GR64944B/el unknown
- 1978-06-16 JP JP7367978A patent/JPS545988A/ja active Pending
- 1978-06-16 PL PL1978207682A patent/PL113420B1/pl not_active IP Right Cessation

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CH573412A5 (en) *	1971-08-17	1976-03-15	Sumitomo Chemical Co	1-substd 4-aryl-2(1h) quinazolinones - anti-inflammatories, analgesics, uricosurics, andantivirals

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US12410177B2 (en)	2018-04-09	2025-09-09	Bmg (British Medical Group) Limited	Antimicrobial and anticancer cationic phthalocyanine compounds

Also Published As

Publication number	Publication date
IT1098341B (it)	1985-09-07
GR64944B (en)	1980-06-10
PT68174A (en)	1978-07-01
CA1094068A (en)	1981-01-20
DK176378A (da)	1978-12-17
PL207682A1 (pl)	1979-05-07
NO782087L (no)	1978-12-19
NZ187581A (en)	1980-11-28
ATA436678A (de)	1981-01-15
ES470828A1 (es)	1979-10-01
FI781928A7 (fi)	1978-12-17
PL113420B1 (en)	1980-12-31
SU797575A3 (ru)	1981-01-15
ZA783438B (en)	1979-06-27
IT7824615A0 (it)	1978-06-15
AU3709278A (en)	1979-12-20
JPS545988A (en)	1979-01-17

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Date	Code	Title	Description
1978-11-15	PUAI	Public reference made under article 153(3) epc to a published international application that has entered the european phase	Free format text: ORIGINAL CODE: 0009012
1979-01-10	AK	Designated contracting states	Kind code of ref document: A1 Designated state(s): BE CH DE FR GB LU NL SE
1979-08-22	17P	Request for examination filed
1981-06-30	STAA	Information on the status of an ep patent application or granted ep patent	Free format text: STATUS: THE APPLICATION HAS BEEN WITHDRAWN
1981-09-02	18W	Application withdrawn	Withdrawal date: 19810626
2007-08-08	RIN1	Information on inventor provided before grant (corrected)	Inventor name: MIDDLETON, WILLIAM JOSEPH

Publication	Publication Date	Title
US3988345A (en)	1976-10-26	Imidazoline derivatives and the preparation thereof
US4258187A (en)	1981-03-24	Process for preparing quinazolinone oxides
US4472400A (en)	1984-09-18	Triazoloquinazolones having antihistaminic and bronchospasmolytic activity
CA1215365A (en)	1986-12-16	Triazoloquinazolinones, their preparation and pharmaceutical formulations containing these compounds
FI77456C (fi)	1989-03-10	Foerfarande foer framstaellning av terapeutiskt anvaendbara 3-/2-/4-(2-metoxifenyl) -1-piperazinyl/etyl/-2,4-(1h,3h)-kinazolindionderivat.
KOSASAYAMA et al.	1979	Cyclic guanidines. IV. Synthesis of hypoglycemic N-benzhydryl bicyclic guanidines
US2455396A (en)	1948-12-07	Organic nitrogen compounds and methods for obtaining same
EP0000149A1 (de)	1979-01-10	Verfahren zur Herstellung von Chinazolinon-oxid-derivaten
US3549635A (en)	1970-12-22	Preparation of substituted-2(1h)-quinazolinones
US3450700A (en)	1969-06-17	2-tertiary amino-4h-3,1-benzoxazin-4-ones
US4228167A (en)	1980-10-14	Diuretic and vasodilating tricyclic quinazolines
EP0253396B1 (de)	1993-03-17	Verfahren zur Herstellung von 5,6-substituierten-2,4-Chinazolindiaminen und Zwischenprodukten
EP0086647B1 (de)	1986-09-17	Pyrimidin-Verbindungen, ihre Herstellung und diese enthaltende pharmazeutische Zusammenstellungen
DE2508333A1 (de)	1975-09-04	Triazolo eckige klammer auf 4,3-a eckige klammer zu chinazoline
US3793326A (en)	1974-02-19	3,4-dihydro-6,7-substituted-2,2,3-lower alkyl-4-oxo-(2h)-quinazolecarboxylic acid derivatives useful as analgesic and tranquilizer agents
US4268511A (en)	1981-05-19	3-Amino(1H,3H)quinazoline-2,4-dione derivatives and their therapeutic applications
US5283248A (en)	1994-02-01	Amino substituted pyrimido[1,6-2]benzimidazoles
US3525748A (en)	1970-08-25	Certain 2-amino-3-phenyl-3,4-dihydroquinazolin-4-ones
US3061641A (en)	1962-10-30	Anilinoalkyl-ureas
HU206090B (en)	1992-08-28	Process for producing new 1-phenyl-1,4-dihydro-3-amino-4-oxopyridazine derivatives and pharmaceutical compositions comprising such compounds as active ingredient
US3629262A (en)	1971-12-21	Process for preparing 4-phenyl-quinazolines
Shaker	2000	Synthesis and transformation of 2-thioxopyrimido [4, 5-d] pyrimidines
US4510143A (en)	1985-04-09	Antiallergic pyrimido[1,2-a]quinoxalin-2-carboxylic acid derivatives
US3464996A (en)	1969-09-02	6h - dibenzo(c,g)(1,2,5)thiadiazocine - 5,5-dioxides and method for their production
US12012400B2 (en)	2024-06-18	Method of the preparation of fused multicyclic compounds

EP0000149A1 - Verfahren zur Herstellung von Chinazolinon-oxid-derivaten - Google Patents

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