IL30069A - Quinazoline compounds and methods for their production - Google Patents
Quinazoline compounds and methods for their productionInfo
- Publication number
- IL30069A IL30069A IL30069A IL3006968A IL30069A IL 30069 A IL30069 A IL 30069A IL 30069 A IL30069 A IL 30069A IL 3006968 A IL3006968 A IL 3006968A IL 30069 A IL30069 A IL 30069A
- Authority
- IL
- Israel
- Prior art keywords
- solution
- diamino
- quinazoline
- product
- collected
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 8
- 238000004519 manufacturing process Methods 0.000 title description 3
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 title 1
- JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 15
- 159000000021 acetate salts Chemical class 0.000 claims description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000000460 chlorine Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 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
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 3
- 150000002367 halogens Chemical class 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 125000003852 3-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(Cl)=C1[H])C([H])([H])* 0.000 claims description 2
- 125000002541 furyl group Chemical group 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 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
- 125000001544 thienyl group Chemical group 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 117
- 239000000243 solution Substances 0.000 description 84
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 78
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 56
- 239000000047 product Substances 0.000 description 53
- 239000000203 mixture Substances 0.000 description 40
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 38
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 32
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 32
- 235000010288 sodium nitrite Nutrition 0.000 description 19
- 239000003610 charcoal Substances 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 16
- 239000012458 free base Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 12
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 238000000746 purification Methods 0.000 description 9
- 238000010992 reflux Methods 0.000 description 9
- 239000000725 suspension Substances 0.000 description 9
- -1 HEW QUINAZOLINE COMPOUNDS Chemical class 0.000 description 8
- 238000002425 crystallisation Methods 0.000 description 8
- 230000008025 crystallization Effects 0.000 description 8
- 239000007858 starting material Substances 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 7
- 239000002244 precipitate Substances 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 6
- 239000002585 base Substances 0.000 description 5
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 4
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 4
- 239000003430 antimalarial agent Substances 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 238000009835 boiling Methods 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000000706 filtrate Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- LYLCQCMWHDZXFW-UHFFFAOYSA-N 5-methylquinazoline-2,4,6-triamine Chemical compound NC1=NC(N)=C2C(C)=C(N)C=CC2=N1 LYLCQCMWHDZXFW-UHFFFAOYSA-N 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 241000224017 Plasmodium berghei Species 0.000 description 3
- 230000000078 anti-malarial effect Effects 0.000 description 3
- QMNFFXRFOJIOKZ-UHFFFAOYSA-N cycloguanil Chemical compound CC1(C)N=C(N)N=C(N)N1C1=CC=C(Cl)C=C1 QMNFFXRFOJIOKZ-UHFFFAOYSA-N 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 238000000926 separation method Methods 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- 239000007787 solid Substances 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
- WQWQHJNUHQEGTN-UHFFFAOYSA-N 2-chloro-6-methylbenzonitrile Chemical compound CC1=CC=CC(Cl)=C1C#N WQWQHJNUHQEGTN-UHFFFAOYSA-N 0.000 description 2
- DXPQTHAFYUTZRR-UHFFFAOYSA-N 2-methylquinazoline Chemical compound C1=CC=CC2=NC(C)=NC=C21 DXPQTHAFYUTZRR-UHFFFAOYSA-N 0.000 description 2
- FBKSHXJRRCENPH-UHFFFAOYSA-N 2-nitroquinazoline Chemical compound C1=CC=CC2=NC([N+](=O)[O-])=NC=C21 FBKSHXJRRCENPH-UHFFFAOYSA-N 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- 241000193996 Streptococcus pyogenes Species 0.000 description 2
- STIAPHVBRDNOAJ-UHFFFAOYSA-N carbamimidoylazanium;carbonate Chemical compound NC(N)=N.NC(N)=N.OC(O)=O STIAPHVBRDNOAJ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 229950004734 cycloguanil Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
- WFPZPJSADLPSON-UHFFFAOYSA-N dinitrogen tetraoxide Chemical compound [O-][N+](=O)[N+]([O-])=O WFPZPJSADLPSON-UHFFFAOYSA-N 0.000 description 2
- LZDSILRDTDCIQT-UHFFFAOYSA-N dinitrogen trioxide Chemical compound [O-][N+](=O)N=O LZDSILRDTDCIQT-UHFFFAOYSA-N 0.000 description 2
- 238000011065 in-situ storage Methods 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- XELRMPRLCPFTBH-UHFFFAOYSA-N quinazoline-2,4-diamine Chemical class C1=CC=CC2=NC(N)=NC(N)=C21 XELRMPRLCPFTBH-UHFFFAOYSA-N 0.000 description 2
- 150000003246 quinazolines Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003457 sulfones Chemical class 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
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- 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 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-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
- 125000006479 2-pyridyl methyl group Chemical group [H]C1=C([H])C([H])=C([H])C(=N1)C([H])([H])* 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
- XCBMRNHSLMDGRI-UHFFFAOYSA-N 5-chloro-6-nitroquinazoline-2,4-diamine Chemical compound ClC1=C([N+]([O-])=O)C=CC2=NC(N)=NC(N)=C21 XCBMRNHSLMDGRI-UHFFFAOYSA-N 0.000 description 1
- JZWXVYNQIJJTKF-UHFFFAOYSA-N 5-chloroquinazoline-2,4,6-triamine Chemical compound N1=C(N)N=C(N)C2=C(Cl)C(N)=CC=C21 JZWXVYNQIJJTKF-UHFFFAOYSA-N 0.000 description 1
- VEVDQDKAMWPQSF-UHFFFAOYSA-N 5-chloroquinazoline-2,4-diamine Chemical compound ClC1=CC=CC2=NC(N)=NC(N)=C21 VEVDQDKAMWPQSF-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
- OKJFZWRYGNARBE-UHFFFAOYSA-N 6-n-(naphthalen-2-ylmethyl)quinazoline-2,4,6-triamine Chemical compound C1=CC=CC2=CC(CNC3=CC4=C(N)N=C(N=C4C=C3)N)=CC=C21 OKJFZWRYGNARBE-UHFFFAOYSA-N 0.000 description 1
- PHOOCTYKNRQQDX-UHFFFAOYSA-N 6-n-[(3-methylphenyl)methyl]quinazoline-2,4,6-triamine Chemical compound CC1=CC=CC(CNC=2C=C3C(N)=NC(N)=NC3=CC=2)=C1 PHOOCTYKNRQQDX-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
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 206010001935 American trypanosomiasis Diseases 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 208000024699 Chagas disease Diseases 0.000 description 1
- 241000588724 Escherichia coli Species 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GZBDBKVGURLUDF-UHFFFAOYSA-N NC1=NC2=CC(=C(C(=C2C(=N1)N)C)CC1=CC=CC=C1)N Chemical compound NC1=NC2=CC(=C(C(=C2C(=N1)N)C)CC1=CC=CC=C1)N GZBDBKVGURLUDF-UHFFFAOYSA-N 0.000 description 1
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical group O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 1
- 206010034133 Pathogen resistance Diseases 0.000 description 1
- 241000224028 Plasmodium cynomolgi Species 0.000 description 1
- 241000607142 Salmonella Species 0.000 description 1
- 239000002262 Schiff base Substances 0.000 description 1
- 150000004753 Schiff bases Chemical class 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 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
- GJOPNLHZECVGKC-UHFFFAOYSA-N acetic acid;quinazoline Chemical compound CC(O)=O.N1=CN=CC2=CC=CC=C21 GJOPNLHZECVGKC-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000002141 anti-parasite Effects 0.000 description 1
- 239000003096 antiparasitic agent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 238000011260 co-administration Methods 0.000 description 1
- ROSHZDSDUDVRGH-UHFFFAOYSA-N cyanamide;dihydrochloride Chemical compound Cl.Cl.NC#N ROSHZDSDUDVRGH-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 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
- 230000000694 effects Effects 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 238000005984 hydrogenation reaction Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 201000004792 malaria Diseases 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- WCZAXBXVDLKQGV-UHFFFAOYSA-N n,n-dimethyl-2-(7-oxobenzo[c]fluoren-5-yl)oxyethanamine oxide Chemical compound C12=CC=CC=C2C(OCC[N+](C)([O-])C)=CC2=C1C1=CC=CC=C1C2=O WCZAXBXVDLKQGV-UHFFFAOYSA-N 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 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
- 238000007911 parenteral administration Methods 0.000 description 1
- 239000002831 pharmacologic agent Substances 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- WKSAUQYGYAYLPV-UHFFFAOYSA-N pyrimethamine Chemical compound CCC1=NC(N)=NC(N)=C1C1=CC=C(Cl)C=C1 WKSAUQYGYAYLPV-UHFFFAOYSA-N 0.000 description 1
- 229960000611 pyrimethamine Drugs 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000012289 standard assay Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- SEEPANYCNGTZFQ-UHFFFAOYSA-N sulfadiazine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)NC1=NC=CC=N1 SEEPANYCNGTZFQ-UHFFFAOYSA-N 0.000 description 1
- 229960004306 sulfadiazine Drugs 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 230000002195 synergetic effect Effects 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
- C07D239/95—Quinazolines; Hydrogenated quinazolines with hetero atoms directly attached in positions 2 and 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB24462/67A GB1141249A (en) | 1967-05-25 | 1967-05-25 | New quinazoline compounds and methods for their production |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL30069A0 IL30069A0 (en) | 1968-07-25 |
| IL30069A true IL30069A (en) | 1972-02-29 |
Family
ID=10212087
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL30069A IL30069A (en) | 1967-05-25 | 1968-05-24 | Quinazoline compounds and methods for their production |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3560502A (en:Method) |
| BE (1) | BE715667A (en:Method) |
| CH (1) | CH477452A (en:Method) |
| DE (1) | DE1770490C3 (en:Method) |
| DK (1) | DK116285B (en:Method) |
| ES (1) | ES354273A1 (en:Method) |
| FR (2) | FR1605537A (en:Method) |
| GB (1) | GB1141249A (en:Method) |
| IL (1) | IL30069A (en:Method) |
| NL (1) | NL6807380A (en:Method) |
| SE (1) | SE328291B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4071477A (en) * | 1976-06-10 | 1978-01-31 | Ciba-Geigy Corporation | Hydantoin diglycidyl compounds |
| HU180439B (en) * | 1977-12-29 | 1983-03-28 | Chinoin Gyogyszer Es Vegyeszet | Process for producing 9-amino-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives |
| US4376858A (en) * | 1980-10-31 | 1983-03-15 | Warner Lambert Company | 2-4-Diamino-5-methyl-6-[(3,4,5-trimethoxyanilino)methyl]quinazoline salts |
| GB8910722D0 (en) * | 1989-05-10 | 1989-06-28 | Smithkline Beckman Intercredit | Compounds |
| IL108630A0 (en) * | 1993-02-18 | 1994-05-30 | Fmc Corp | Insecticidal substituted 2,4-diaminoquinazolines |
| US6017922A (en) * | 1998-05-18 | 2000-01-25 | U.S. Bioscience, Inc. | Thermally stable trimetrexates and processes for producing the same |
-
1967
- 1967-05-25 GB GB24462/67A patent/GB1141249A/en not_active Expired
-
1968
- 1968-05-24 DE DE1770490A patent/DE1770490C3/de not_active Expired
- 1968-05-24 ES ES354273A patent/ES354273A1/es not_active Expired
- 1968-05-24 BE BE715667D patent/BE715667A/xx unknown
- 1968-05-24 NL NL6807380A patent/NL6807380A/xx unknown
- 1968-05-24 IL IL30069A patent/IL30069A/en unknown
- 1968-05-24 CH CH774068A patent/CH477452A/fr not_active IP Right Cessation
- 1968-05-24 FR FR152946A patent/FR1605537A/fr not_active Expired
- 1968-05-24 SE SE06998/68A patent/SE328291B/xx unknown
- 1968-05-24 US US731727A patent/US3560502A/en not_active Expired - Lifetime
- 1968-05-24 DK DK244268AA patent/DK116285B/da unknown
- 1968-08-23 FR FR163942A patent/FR7710M/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1770490A1 (de) | 1972-03-02 |
| US3560502A (en) | 1971-02-02 |
| DE1770490B2 (de) | 1974-01-10 |
| IL30069A0 (en) | 1968-07-25 |
| FR1605537A (en:Method) | 1979-02-23 |
| CH477452A (fr) | 1969-08-31 |
| DE1770490C3 (de) | 1974-08-01 |
| SE328291B (en:Method) | 1970-09-14 |
| FR7710M (en:Method) | 1970-02-23 |
| GB1141249A (en) | 1969-01-29 |
| NL6807380A (en:Method) | 1968-11-26 |
| ES354273A1 (es) | 1969-11-01 |
| BE715667A (en:Method) | 1968-10-16 |
| DK116285B (da) | 1969-12-29 |
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