CA1094068A - Process for preparing quinazolinone oxides - Google Patents

Process for preparing quinazolinone oxides

Info

Publication number: CA1094068A
Authority: CA; Canada
Prior art keywords: quinazolinone; formula; phenyl; chloro; 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.): Expired

Application number

CA305,471A

Other languages

English (en)

French (fr)

Inventor

William J. 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

1978-06-14

Publication date

1981-01-20

1978-06-14 Application filed by EI Du Pont de Nemours and Co filed Critical EI Du Pont de Nemours and Co

1981-01-20 Application granted granted Critical

1981-01-20 Publication of CA1094068A publication Critical patent/CA1094068A/en

Status Expired legal-status Critical Current

Links

238000004519 manufacturing process Methods 0.000 title claims abstract description 8
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 12
150000002513 isocyanates Chemical class 0.000 claims description 12
AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 8
150000003839 salts Chemical class 0.000 claims description 8
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 5
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
238000010438 heat treatment Methods 0.000 claims description 2
DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 claims 1
238000000034 method Methods 0.000 abstract description 12
AVRPFRMDMNDIDH-UHFFFAOYSA-N 1h-quinazolin-2-one Chemical compound C1=CC=CC2=NC(O)=NC=C21 AVRPFRMDMNDIDH-UHFFFAOYSA-N 0.000 abstract description 3
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
238000002360 preparation method Methods 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 59
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 30
WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 22
IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 20
239000013078 crystal Substances 0.000 description 18
239000007787 solid Substances 0.000 description 15
239000011541 reaction mixture Substances 0.000 description 13
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 9
238000006243 chemical reaction Methods 0.000 description 8
239000012258 stirred mixture Substances 0.000 description 8
239000000203 mixture Substances 0.000 description 7
MAOBFOXLCJIFLV-UHFFFAOYSA-N (2-aminophenyl)-phenylmethanone Chemical class NC1=CC=CC=C1C(=O)C1=CC=CC=C1 MAOBFOXLCJIFLV-UHFFFAOYSA-N 0.000 description 5
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 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
125000006367 bivalent amino carbonyl group Chemical group [H]N([*:1])C([*:2])=O 0.000 description 4
-1 bromo-3,4-dihydro-4-hydroxy-3-methyl-4-phenyl-2(lH)-quinazolinone Chemical compound 0.000 description 4
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 4
239000000843 powder Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007858 starting material Substances 0.000 description 4
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
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
235000013877 carbamide Nutrition 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 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
239000002904 solvent Substances 0.000 description 3
150000003672 ureas Chemical class 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 2
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 2
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
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 2
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 2
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 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
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-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
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
WUDNUHPRLBTKOJ-UHFFFAOYSA-N ethyl isocyanate Chemical compound CCN=C=O WUDNUHPRLBTKOJ-UHFFFAOYSA-N 0.000 description 2
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 2
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 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
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
LUBJCRLGQSPQNN-UHFFFAOYSA-N 1-Phenylurea Chemical compound NC(=O)NC1=CC=CC=C1 LUBJCRLGQSPQNN-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
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
QULACHKCJILTKA-UHFFFAOYSA-N 4-hydroxy-4-phenyl-1,3-dihydroquinazolin-2-one Chemical compound OC1(NC(NC2=CC=CC=C12)=O)C1=CC=CC=C1 QULACHKCJILTKA-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
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
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
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 1
101150041968 CDC13 gene Proteins 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
241000124008 Mammalia Species 0.000 description 1
UJUXLLZXKQSEMC-UHFFFAOYSA-N N=C=O.O=C1N=CC2=CC=CC=C2N1 Chemical compound N=C=O.O=C1N=CC2=CC=CC=C2N1 UJUXLLZXKQSEMC-UHFFFAOYSA-N 0.000 description 1
229910017912 NH2OH Inorganic materials 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
238000009835 boiling Methods 0.000 description 1
239000003638 chemical reducing agent Substances 0.000 description 1
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 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
229960004592 isopropanol Drugs 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 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
239000000376 reactant Substances 0.000 description 1
230000036647 reaction Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
102200073741 rs121909602 Human genes 0.000 description 1
238000001228 spectrum 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
CYTQBVOFDCPGCX-UHFFFAOYSA-N trimethyl phosphite Chemical compound COP(OC)OC CYTQBVOFDCPGCX-UHFFFAOYSA-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

Landscapes

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

CA305,471A 1977-06-16 1978-06-14 Process for preparing quinazolinone oxides Expired CA1094068A (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US80707677A	1977-06-16	1977-06-16
US807,076		1991-12-13

Publications (1)

Publication Number	Publication Date
CA1094068A true CA1094068A (en)	1981-01-20

Family

ID=25195510

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA305,471A Expired CA1094068A (en)	1977-06-16	1978-06-14	Process for preparing quinazolinone oxides

Country Status (16)

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

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP3553062A1 (en)	2018-04-09	2019-10-16	Chemical Intelligence Limited	Antimicrobial and anticancer cationic phthalocyanine compounds

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS4946633B2 (es) *	1971-08-17	1974-12-11

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 IT IT24615/78A patent/IT1098341B/it active
- 1978-06-15 NO NO782087A patent/NO782087L/no unknown
- 1978-06-15 SU SU782627504A patent/SU797575A3/ru active
- 1978-06-15 AT AT436678A patent/ATA436678A/de not_active Application Discontinuation
- 1978-06-15 EP EP78100163A patent/EP0000149A1/en not_active Withdrawn
- 1978-06-15 ES ES470828A patent/ES470828A1/es not_active Expired
- 1978-06-15 NZ NZ187581A patent/NZ187581A/xx unknown
- 1978-06-15 ZA ZA00783438A patent/ZA783438B/xx unknown
- 1978-06-15 PT PT68174A patent/PT68174A/pt unknown
- 1978-06-16 PL PL1978207682A patent/PL113420B1/pl not_active IP Right Cessation
- 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

Also Published As

Publication number	Publication date
GR64944B (en)	1980-06-10
AU3709278A (en)	1979-12-20
JPS545988A (en)	1979-01-17
PT68174A (en)	1978-07-01
DK176378A (da)	1978-12-17
EP0000149A1 (en)	1979-01-10
NO782087L (no)	1978-12-19
ES470828A1 (es)	1979-10-01
ZA783438B (en)	1979-06-27
ATA436678A (de)	1981-01-15
FI781928A7 (fi)	1978-12-17
SU797575A3 (ru)	1981-01-15
IT1098341B (it)	1985-09-07
IT7824615A0 (it)	1978-06-15
NZ187581A (en)	1980-11-28
PL113420B1 (en)	1980-12-31
PL207682A1 (pl)	1979-05-07

Publication	Publication Date	Title
Sellstedt et al.	1975	Oxanilic acids, a new series of orally active antiallergic agents
WO1994005628A1 (en)	1994-03-17	Synthesis of 2-substituted quinazoline compounds (such as terazosin) and meobentine and bethanidine and intermediates therefor
US3988345A (en)	1976-10-26	Imidazoline derivatives and the preparation thereof
US4258187A (en)	1981-03-24	Process for preparing quinazolinone oxides
Leiby	1985	Synthesis of 3-amino-4 (3H)-quinazolinones from N-(2-carbomethoxyphenyl) imidate esters
CA1094068A (en)	1981-01-20	Process for preparing quinazolinone oxides
US3450700A (en)	1969-06-17	2-tertiary amino-4h-3,1-benzoxazin-4-ones
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