IL30614A - Compounds 2,4 - Diamino - 6 -) Transformed acetylamino (quinazoline and their preparation - Google Patents

Compounds 2,4 - Diamino - 6 -) Transformed acetylamino (quinazoline and their preparation

Info

Publication number: IL30614A
Authority: IL; Israel
Prior art keywords: diamino; quinazolinyl; formamide; methyl; formula
Prior art date: 1967-09-11

Application number

IL30614A

Other languages

English (en)

Hebrew (he)

Other versions

IL30614A0 (en

Original Assignee

Parke Davis & 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.)

1967-09-11

Filing date

1968-08-23

Publication date

1972-05-30

1968-08-23 Application filed by Parke Davis & Co filed Critical Parke Davis & Co

1968-10-24 Publication of IL30614A0 publication Critical patent/IL30614A0/xx

1972-05-30 Publication of IL30614A publication Critical patent/IL30614A/en

Links

125000004442 acylamino group Chemical group 0.000 title claims description 4
238000002360 preparation method Methods 0.000 title description 3
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 24
-1 2 ,4-Diamino-6-quinazolinyl Chemical group 0.000 claims description 22
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 21
238000000034 method Methods 0.000 claims description 18
238000010992 reflux Methods 0.000 claims description 18
150000003839 salts Chemical class 0.000 claims description 15
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical group COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 11
235000019253 formic acid Nutrition 0.000 claims description 11
125000000217 alkyl group Chemical group 0.000 claims description 10
229910052739 hydrogen Inorganic materials 0.000 claims description 10
239000001257 hydrogen Substances 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 9
239000012458 free base Substances 0.000 claims description 9
238000006243 chemical reaction Methods 0.000 claims description 7
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
239000003795 chemical substances by application Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
239000000460 chlorine Chemical group 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
239000011541 reaction mixture Substances 0.000 claims description 4
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical class 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000001624 naphthyl group Chemical group 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
150000002431 hydrogen Chemical group 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
125000004803 chlorobenzyl group Chemical group 0.000 claims 1
125000006286 dichlorobenzyl group Chemical group 0.000 claims 1
125000006178 methyl benzyl group Chemical group 0.000 claims 1
150000003246 quinazolines Chemical class 0.000 claims 1
125000001544 thienyl group Chemical group 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 40
239000000047 product Substances 0.000 description 32
239000000243 solution Substances 0.000 description 30
239000000203 mixture Substances 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 10
QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 10
239000003610 charcoal Substances 0.000 description 10
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
239000007858 starting material Substances 0.000 description 8
238000001953 recrystallisation Methods 0.000 description 7
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
238000001914 filtration Methods 0.000 description 6
239000003430 antimalarial agent Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
239000003054 catalyst Substances 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 5
208000009182 Parasitemia Diseases 0.000 description 4
208000030852 Parasitic disease Diseases 0.000 description 4
230000010933 acylation Effects 0.000 description 4
238000005917 acylation reaction Methods 0.000 description 4
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 4
239000012279 sodium borohydride Substances 0.000 description 4
229910000033 sodium borohydride Inorganic materials 0.000 description 4
239000007787 solid Substances 0.000 description 4
238000003756 stirring Methods 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
LJBWEZVYRBKOCI-UHFFFAOYSA-N 2,4,6-triaminoquinazoline Chemical compound N1=C(N)N=C(N)C2=CC(N)=CC=C21 LJBWEZVYRBKOCI-UHFFFAOYSA-N 0.000 description 3
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 3
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
239000012346 acetyl chloride Substances 0.000 description 3
230000000844 anti-bacterial effect Effects 0.000 description 3
230000000078 anti-malarial effect Effects 0.000 description 3
239000002585 base Substances 0.000 description 3
238000002425 crystallisation Methods 0.000 description 3
230000008025 crystallization Effects 0.000 description 3
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 3
239000000706 filtrate Substances 0.000 description 3
229940080818 propionamide Drugs 0.000 description 3
BWZAUXRKSMJLMH-UHFFFAOYSA-N 1,1-diethoxyethylbenzene Chemical compound CCOC(C)(OCC)C1=CC=CC=C1 BWZAUXRKSMJLMH-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
LOUPRKONTZGTKE-WZBLMQSHSA-N Quinine Chemical compound C([C@H]([C@H](C1)C=C)C2)C[N@@]1[C@@H]2[C@H](O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-WZBLMQSHSA-N 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000005484 gravity Effects 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000002831 pharmacologic agent Substances 0.000 description 2
QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 2
125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 2
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FWPIDFUJEMBDLS-UHFFFAOYSA-L tin(II) chloride dihydrate Chemical compound O.O.Cl[Sn]Cl FWPIDFUJEMBDLS-UHFFFAOYSA-L 0.000 description 2
TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
YWUNVHXKGMPHDM-AMTQNMNTSA-N (2s)-2-[[(2e,4e,6e,11r)-12-[(4s,4as,6r,8s,8ar)-4-[[(2s)-2-hydroxy-2-[(2r,5r,6r)-2-methoxy-5,6-dimethyl-4-methylideneoxan-2-yl]acetyl]amino]-8-methoxy-7,7-dimethyl-4a,6,8,8a-tetrahydro-4h-pyrano[3,2-d][1,3]dioxin-6-yl]-11-hydroxydodeca-2,4,6-trienoyl]amino Chemical compound CO[C@]1([C@H](O)C(=O)N[C@H]2OCO[C@@H]3[C@H](C([C@@H](C[C@H](O)CCC\C=C\C=C\C=C\C(=O)N[C@@H](CCCN=C(N)N)C(O)=O)O[C@@H]32)(C)C)OC)CC(=C)[C@@H](C)[C@@H](C)O1 YWUNVHXKGMPHDM-AMTQNMNTSA-N 0.000 description 1
IXHNFOOSLAWRBQ-UHFFFAOYSA-N (3,4-dichlorophenyl)methanamine Chemical compound NCC1=CC=C(Cl)C(Cl)=C1 IXHNFOOSLAWRBQ-UHFFFAOYSA-N 0.000 description 1
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
MEJVTQKBWPYBFG-UHFFFAOYSA-N 2-amino-6-chlorobenzonitrile Chemical compound NC1=CC=CC(Cl)=C1C#N MEJVTQKBWPYBFG-UHFFFAOYSA-N 0.000 description 1
DXPQTHAFYUTZRR-UHFFFAOYSA-N 2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC=C21 DXPQTHAFYUTZRR-UHFFFAOYSA-N 0.000 description 1
ZWUSBSHBFFPRNE-UHFFFAOYSA-N 3,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C=C1Cl ZWUSBSHBFFPRNE-UHFFFAOYSA-N 0.000 description 1
MXJSTEGEEJRPOJ-UHFFFAOYSA-N 3-(3,4-dichlorophenyl)propanamide Chemical compound NC(=O)CCC1=CC=C(Cl)C(Cl)=C1 MXJSTEGEEJRPOJ-UHFFFAOYSA-N 0.000 description 1
SNGQYBKGJMHFNB-UHFFFAOYSA-N 5-chloro-6-n-[(3,4-dichlorophenyl)methyl]quinazoline-2,4,6-triamine Chemical compound C1=CC2=NC(N)=NC(N)=C2C(Cl)=C1NCC1=CC=C(Cl)C(Cl)=C1 SNGQYBKGJMHFNB-UHFFFAOYSA-N 0.000 description 1
BUYNQWWHXMVWEE-UHFFFAOYSA-N 5-chloroquinazoline Chemical compound C1=NC=C2C(Cl)=CC=CC2=N1 BUYNQWWHXMVWEE-UHFFFAOYSA-N 0.000 description 1
SPRYSWBJUMKGMP-UHFFFAOYSA-N 5-methyl-6-nitroquinazoline-2,4-diamine Chemical compound NC1=NC(N)=C2C(C)=C([N+]([O-])=O)C=CC2=N1 SPRYSWBJUMKGMP-UHFFFAOYSA-N 0.000 description 1
LTSQDQVTNREIAO-UHFFFAOYSA-N 6-n-[(3,4-dichlorophenyl)methyl]quinazoline-2,4,6-triamine Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1NCC1=CC=C(Cl)C(Cl)=C1 LTSQDQVTNREIAO-UHFFFAOYSA-N 0.000 description 1
PTWJNRZKGULCMJ-UHFFFAOYSA-N 6-n-benzylquinazoline-2,4,6-triamine Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1NCC1=CC=CC=C1 PTWJNRZKGULCMJ-UHFFFAOYSA-N 0.000 description 1
YZMJNZRTRWPJFY-UHFFFAOYSA-N 6-nitroquinazoline-2,4-diamine Chemical compound C1=C([N+]([O-])=O)C=CC2=NC(N)=NC(N)=C21 YZMJNZRTRWPJFY-UHFFFAOYSA-N 0.000 description 1
235000001258 Cinchona calisaya Nutrition 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
241000424103 Parapercis colias Species 0.000 description 1
241000224017 Plasmodium berghei Species 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
239000002262 Schiff base Substances 0.000 description 1
150000004753 Schiff bases Chemical class 0.000 description 1
229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
241000223109 Trypanosoma cruzi Species 0.000 description 1
DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
150000001241 acetals Chemical class 0.000 description 1
159000000021 acetate salts Chemical class 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
239000003242 anti bacterial agent Substances 0.000 description 1
239000003096 antiparasitic agent Substances 0.000 description 1
229940125687 antiparasitic agent Drugs 0.000 description 1
229940124578 antitrypanosomal agent Drugs 0.000 description 1
239000003702 antitrypanosomal agent Substances 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 description 1
STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 1
125000001589 carboacyl group Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
LOUPRKONTZGTKE-UHFFFAOYSA-N cinchonine Natural products C1C(C(C2)C=C)CCN2C1C(O)C1=CC=NC2=CC=C(OC)C=C21 LOUPRKONTZGTKE-UHFFFAOYSA-N 0.000 description 1
230000000052 comparative effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
ROSHZDSDUDVRGH-UHFFFAOYSA-N cyanamide;dihydrochloride Chemical compound Cl.Cl.NC#N ROSHZDSDUDVRGH-UHFFFAOYSA-N 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
239000000645 desinfectant Substances 0.000 description 1
230000037213 diet Effects 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
201000010099 disease Diseases 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
DNQSGXVJKQBSMT-UHFFFAOYSA-L disodium;3-carboxy-1-[(3-carboxy-2-oxidonaphthalen-1-yl)methyl]naphthalen-2-olate;hydrate Chemical compound O.[Na+].[Na+].C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3[O-])C(=O)O)=C([O-])C(C(O)=O)=CC2=C1 DNQSGXVJKQBSMT-UHFFFAOYSA-L 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000003814 drug Substances 0.000 description 1
229940079593 drug Drugs 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
150000004820 halides Chemical class 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000000155 melt Substances 0.000 description 1
238000002844 melting Methods 0.000 description 1
230000008018 melting Effects 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
HUBJNGKWZKMSOR-UHFFFAOYSA-N n-quinazolin-2-ylformamide Chemical compound C1=CC=CC2=NC(NC=O)=NC=C21 HUBJNGKWZKMSOR-UHFFFAOYSA-N 0.000 description 1
229930194314 onnamide Natural products 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 description 1
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910003446 platinum oxide Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
125000005344 pyridylmethyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 0.000 description 1
CZAAKPFIWJXPQT-UHFFFAOYSA-N quinazolin-2-amine Chemical compound C1=CC=CC2=NC(N)=NC=C21 CZAAKPFIWJXPQT-UHFFFAOYSA-N 0.000 description 1
229960000948 quinine Drugs 0.000 description 1
239000000376 reactant Substances 0.000 description 1
239000012265 solid product Substances 0.000 description 1
238000012289 standard assay Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000001119 stannous chloride Substances 0.000 description 1
235000011150 stannous chloride Nutrition 0.000 description 1
230000001954 sterilising effect Effects 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
230000001629 suppression Effects 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000006188 syrup Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/495—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with two or more nitrogen atoms as the only ring heteroatoms, e.g. piperazine or tetrazines
- A61K31/505—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim
- A61K31/517—Pyrimidines; Hydrogenated pyrimidines, e.g. trimethoprim ortho- or peri-condensed with carbocyclic ring systems, e.g. quinazoline, perimidine
- 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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/88—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
- C07D239/86—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in position 4
- C07D239/94—Nitrogen 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
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Epidemiology (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Plural Heterocyclic Compounds (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

IL30614A 1967-09-11 1968-08-23 Compounds 2,4 - Diamino - 6 -) Transformed acetylamino (quinazoline and their preparation IL30614A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB41436/67A GB1161644A (en)	1967-09-11	1967-09-11	Quinazoline Compounds and process means for producing the same

Publications (2)

Publication Number	Publication Date
IL30614A0 IL30614A0 (en)	1968-10-24
IL30614A true IL30614A (en)	1972-05-30

Family

ID=10419677

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL30614A IL30614A (en)	1967-09-11	1968-08-23	Compounds 2,4 - Diamino - 6 -) Transformed acetylamino (quinazoline and their preparation

Country Status (12)

Country	Link
US (1)	US3546224A (fr)
BE (1)	BE720645A (fr)
CH (1)	CH491931A (fr)
DE (1)	DE1795309B2 (fr)
DK (1)	DK121085B (fr)
ES (1)	ES357983A1 (fr)
FR (1)	FR1589711A (fr)
GB (1)	GB1161644A (fr)
IL (1)	IL30614A (fr)
NL (1)	NL6812978A (fr)
SE (1)	SE336797B (fr)
YU (1)	YU32091B (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5430148A (en) *	1992-03-31	1995-07-04	Agouron Pharmaceuticals, Inc.	Antiproliferative quinazolines
IL108630A0 (en) *	1993-02-18	1994-05-30	Fmc Corp	Insecticidal substituted 2,4-diaminoquinazolines

1967
- 1967-09-11 GB GB41436/67A patent/GB1161644A/en not_active Expired
1968
- 1968-08-23 IL IL30614A patent/IL30614A/en unknown
- 1968-09-02 FR FR1589711D patent/FR1589711A/fr not_active Expired
- 1968-09-04 CH CH1325168A patent/CH491931A/fr not_active IP Right Cessation
- 1968-09-09 US US767028A patent/US3546224A/en not_active Expired - Lifetime
- 1968-09-10 BE BE720645D patent/BE720645A/xx unknown
- 1968-09-10 DK DK434968AA patent/DK121085B/da unknown
- 1968-09-10 ES ES357983A patent/ES357983A1/es not_active Expired
- 1968-09-10 SE SE12135/68A patent/SE336797B/xx unknown
- 1968-09-10 YU YU2110/68A patent/YU32091B/xx unknown
- 1968-09-10 DE DE1795309A patent/DE1795309B2/de active Granted
- 1968-09-11 NL NL6812978A patent/NL6812978A/xx unknown

Also Published As

Publication number	Publication date
NL6812978A (fr)	1969-03-13
DE1795309C3 (fr)	1974-10-24
FR1589711A (fr)	1970-04-06
DE1795309A1 (de)	1972-04-13
BE720645A (fr)	1969-02-17
ES357983A1 (es)	1970-04-01
YU211068A (en)	1973-10-31
IL30614A0 (en)	1968-10-24
SE336797B (fr)	1971-07-19
YU32091B (en)	1974-04-30
GB1161644A (en)	1969-08-13
DK121085B (da)	1971-09-06
DE1795309B2 (de)	1974-03-14
US3546224A (en)	1970-12-08
CH491931A (fr)	1970-06-15

Publication	Publication Date	Title
ES2201112T3 (es)	2004-03-16	Nuevos derivados de pirimidina y procedimientos para su preparacion.
CA2368413C (fr)	2008-07-29	Derives de pyrimido [6,1-a] isoquinolein-4-one et leur utilisation en medecine
DE69025723T2 (de)	1996-10-31	N-(Pyrrolo(2-3-d)pyrimidin-3-ylacyl)-Glutaminsäurederivate
US3993656A (en)	1976-11-23	1,8-Naphthyridine compounds
US4782055A (en)	1988-11-01	Imidazopyridine compounds useful in the treatment of ulcers
US5223503A (en)	1993-06-29	6-substituted pyrido[2,3-d]pyrimidines as antineoplastic agents
US3485842A (en)	1969-12-23	Heterocyclic compounds and means for producing the same
US7105528B2 (en)	2006-09-12	Benzo [g] quinoline derivatives for treating glaucoma and myopia
Vaughan et al.	1949	Triazolo and imidiazopyridines
US4150154A (en)	1979-04-17	Amidinoureas
US4183932A (en)	1980-01-15	Fused quinazolinones and preparation thereof
US3560502A (en)	1971-02-02	New quinazoline compounds and methods for their production
US4208520A (en)	1980-06-17	7-(Substituted)-7H-pyrrolo[3,2-f]quinazoline-1,3-diamines
US3288792A (en)	1966-11-29	Method of preparing 2, 4-diamino-6-alkylpyrido (2, 3-d) pyrimidines
US3546224A (en)	1970-12-08	Novel quinazoline compounds and process means for producing the same
DeGraw et al.	1974	Potential antileprotic agents. 3. Inhibition of mycobacterial dihydrofolic reductase by 2, 4-diamino-5-methyl-6-alkylquinazolines
Elpern et al.	1959	Strong analgesics. The preparation of some ethyl 1-anilinoalkyl-4-phenylpiperidine-4-carboxylates
CA2351644A1 (fr)	2000-05-25	Derives de pyrimidine et leurs procedes de preparation
US4066645A (en)	1978-01-03	Derivatives of pyrazolo [1,5-a]pyrido[3,4-e]pyrimidine
US4912135A (en)	1990-03-27	Amide compounds
Bolhofer et al.	1983	Inhibitors of gastric acid secretion: antisecretory 2-pyridylurea derivatives
CA1133483A (fr)	1982-10-12	Agents neuroleptiques a base d'hexahydro-trans- pyridoindole
US5071849A (en)	1991-12-10	Dihydropyrimidothiazine derivatives
Elslager et al.	1964	Synthetic Schistosomicides. VI. 4-Substituted 1-(Dialkylaminoalkylamino) naphthalenes1
GB2024815A (en)	1980-01-16	Imidazolylethoxy derivatives of pyrazolo-(o,4-b)pyridine-5-methanols