CH634069A5 - Process for preparing novel 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines - Google Patents

Process for preparing novel 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines Download PDF

Info

Publication number: CH634069A5
Authority: CH; Switzerland
Prior art keywords: methyl; phenyl; quinolinyl; pyrrolo; pyridinyl
Prior art date: 1976-07-09

Application number

CH850677A

Other languages

German (de)

English (en)

Inventor

Kurt Willi Ledig

Original Assignee

American Home Prod

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.)

1976-07-09

Filing date

1977-07-08

Publication date

1983-01-14

1977-07-08 Application filed by American Home Prod filed Critical American Home Prod

1982-05-10 Priority to CH289482A priority Critical patent/CH636616A5/de

1982-05-10 Priority to CH289382A priority patent/CH635842A5/de

1983-01-14 Publication of CH634069A5 publication Critical patent/CH634069A5/de

Links

AMQWKZUAOLLUPP-UHFFFAOYSA-N 7h-pyrrolo[3,2-f]quinazoline-1,3-diamine Chemical class C1=CC2=NC(N)=NC(N)=C2C2=C1NC=C2 AMQWKZUAOLLUPP-UHFFFAOYSA-N 0.000 title description 14
238000004519 manufacturing process Methods 0.000 title 1
-1 2-methyl-l-propenyl Chemical group 0.000 claims description 261
150000001875 compounds Chemical class 0.000 claims description 98
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 46
238000000034 method Methods 0.000 claims description 41
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 33
150000003839 salts Chemical class 0.000 claims description 28
229910000104 sodium hydride Inorganic materials 0.000 claims description 20
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical group [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 19
239000012312 sodium hydride Substances 0.000 claims description 19
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000001541 3-thienyl group Chemical group S1C([H])=C([*])C([H])=C1[H] 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
239000000460 chlorine Substances 0.000 claims description 12
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 11
229910052783 alkali metal Inorganic materials 0.000 claims description 11
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 11
229910052794 bromium Inorganic materials 0.000 claims description 11
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 10
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 9
239000011737 fluorine Substances 0.000 claims description 9
229910052731 fluorine Inorganic materials 0.000 claims description 9
239000002585 base Substances 0.000 claims description 8
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
230000008569 process Effects 0.000 claims description 8
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 7
KPCZJLGGXRGYIE-UHFFFAOYSA-N [C]1=CC=CN=C1 Chemical group [C]1=CC=CN=C1 KPCZJLGGXRGYIE-UHFFFAOYSA-N 0.000 claims description 7
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 7
229910052740 iodine Inorganic materials 0.000 claims description 7
125000006184 2,5-dimethyl benzyl group Chemical group [H]C1=C(C([H])=C(C(=C1[H])C([H])([H])[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 6
125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 claims description 6
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
SZPWXAOBLNYOHY-UHFFFAOYSA-N [C]1=CC=NC2=CC=CC=C12 Chemical group [C]1=CC=NC2=CC=CC=C12 SZPWXAOBLNYOHY-UHFFFAOYSA-N 0.000 claims description 6
150000001340 alkali metals Chemical class 0.000 claims description 6
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
125000003564 m-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C(C#N)=C1[H])C([H])([H])* 0.000 claims description 6
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 6
125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 claims description 6
231100000252 nontoxic Toxicity 0.000 claims description 6
230000003000 nontoxic effect Effects 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
125000001917 2,4-dinitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1*)[N+]([O-])=O)[N+]([O-])=O 0.000 claims description 5
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 5
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 5
125000005605 benzo group Chemical group 0.000 claims description 5
239000011630 iodine Substances 0.000 claims description 5
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 5
125000006505 p-cyanobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C#N)C([H])([H])* 0.000 claims description 5
229910052708 sodium Inorganic materials 0.000 claims description 5
KDDQRKBRJSGMQE-UHFFFAOYSA-N 4-thiazolyl Chemical group [C]1=CSC=N1 KDDQRKBRJSGMQE-UHFFFAOYSA-N 0.000 claims description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 4
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 4
125000004307 pyrazin-2-yl group Chemical group [H]C1=C([H])N=C(*)C([H])=N1 0.000 claims description 4
125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 claims description 4
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 3
150000002431 hydrogen Chemical group 0.000 claims description 3
125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
BTSVMLPWCFPJJL-UHFFFAOYSA-N ethoxy-methoxy-propoxy-lambda3-chlorane Chemical compound CCCOCl(OC)OCC BTSVMLPWCFPJJL-UHFFFAOYSA-N 0.000 claims description 2
239000003513 alkali Substances 0.000 claims 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 93
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 87
238000009835 boiling Methods 0.000 description 43
241000699670 Mus sp. Species 0.000 description 37
238000002844 melting Methods 0.000 description 37
230000008018 melting Effects 0.000 description 37
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 36
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
238000000354 decomposition reaction Methods 0.000 description 29
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 28
239000000243 solution Substances 0.000 description 26
238000012360 testing method Methods 0.000 description 22
241001465754 Metazoa Species 0.000 description 21
150000004985 diamines Chemical class 0.000 description 20
239000012043 crude product Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 19
238000001953 recrystallisation Methods 0.000 description 17
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical group CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
230000000844 anti-bacterial effect Effects 0.000 description 15
239000006185 dispersion Substances 0.000 description 15
239000002480 mineral oil Substances 0.000 description 15
235000010446 mineral oil Nutrition 0.000 description 15
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
239000011541 reaction mixture Substances 0.000 description 14
OCCUSFFIPSNZJD-UHFFFAOYSA-N 2,4-dihydroquinazoline-1,3-diamine Chemical class C1=CC=C2CN(N)CN(N)C2=C1 OCCUSFFIPSNZJD-UHFFFAOYSA-N 0.000 description 13
239000007787 solid Substances 0.000 description 13
229960000583 acetic acid Drugs 0.000 description 12
238000000338 in vitro Methods 0.000 description 12
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 11
230000000694 effects Effects 0.000 description 11
208000015181 infectious disease Diseases 0.000 description 11
239000000047 product Substances 0.000 description 11
239000008280 blood Substances 0.000 description 10
210000004369 blood Anatomy 0.000 description 10
150000001805 chlorine compounds Chemical class 0.000 description 10
239000000203 mixture Substances 0.000 description 10
230000004083 survival effect Effects 0.000 description 10
239000000725 suspension Substances 0.000 description 10
241000224017 Plasmodium berghei Species 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
230000034994 death Effects 0.000 description 9
231100000517 death Toxicity 0.000 description 9
229920001817 Agar Polymers 0.000 description 8
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000008272 agar Substances 0.000 description 8
239000012362 glacial acetic acid Substances 0.000 description 8
125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 7
241000588770 Proteus mirabilis Species 0.000 description 7
238000010790 dilution Methods 0.000 description 7
239000012895 dilution Substances 0.000 description 7
238000003756 stirring Methods 0.000 description 7
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
239000003153 chemical reaction reagent Substances 0.000 description 6
201000004792 malaria Diseases 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
230000035945 sensitivity Effects 0.000 description 6
159000000000 sodium salts Chemical class 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
239000002168 alkylating agent Substances 0.000 description 5
229940100198 alkylating agent Drugs 0.000 description 5
239000003814 drug Substances 0.000 description 5
150000004820 halides Chemical class 0.000 description 5
239000012299 nitrogen atmosphere Substances 0.000 description 5
230000004044 response Effects 0.000 description 5
125000005809 3,4,5-trimethoxyphenyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 description 4
125000004861 4-isopropyl phenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 4
125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 4
ZWFDKDJACHDCTD-UHFFFAOYSA-N 7-benzylpyrrolo[3,2-f]quinazoline-1,3-diamine Chemical compound C1=2C=CC3=NC(N)=NC(N)=C3C=2C=CN1CC1=CC=CC=C1 ZWFDKDJACHDCTD-UHFFFAOYSA-N 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical class CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 4
238000005481 NMR spectroscopy Methods 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
238000004821 distillation Methods 0.000 description 4
229940079593 drug Drugs 0.000 description 4
238000002474 experimental method Methods 0.000 description 4
239000001963 growth medium Substances 0.000 description 4
230000035876 healing Effects 0.000 description 4
WVDDGKGOMKODPV-UHFFFAOYSA-N hydroxymethyl benzene Natural products OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 description 4
238000001727 in vivo Methods 0.000 description 4
239000000463 material Substances 0.000 description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 4
231100001160 nonlethal Toxicity 0.000 description 4
125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 4
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
231100000331 toxic Toxicity 0.000 description 4
230000002588 toxic effect Effects 0.000 description 4
PECXPZGFZFGDRD-UHFFFAOYSA-N 2-(chloromethyl)-1,4-dimethylbenzene Chemical compound CC1=CC=C(C)C(CCl)=C1 PECXPZGFZFGDRD-UHFFFAOYSA-N 0.000 description 3
BSQLQMLFTHJVKS-UHFFFAOYSA-N 2-chloro-1,3-benzothiazole Chemical compound C1=CC=C2SC(Cl)=NC2=C1 BSQLQMLFTHJVKS-UHFFFAOYSA-N 0.000 description 3
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 3
125000004198 2-fluorophenyl group Chemical group [H]C1=C([H])C(F)=C(*)C([H])=C1[H] 0.000 description 3
125000004204 2-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C([H])=C1[H] 0.000 description 3
125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 3
125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 3
125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 3
125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 3
125000004207 3-methoxyphenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(OC([H])([H])[H])=C1[H] 0.000 description 3
241000588724 Escherichia coli Species 0.000 description 3
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
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 3
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
230000001580 bacterial effect Effects 0.000 description 3
WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 3
239000012267 brine Substances 0.000 description 3
125000004093 cyano group Chemical group *C#N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
239000002609 medium Substances 0.000 description 3
NIQQIJXGUZVEBB-UHFFFAOYSA-N methanol;propan-2-one Chemical compound OC.CC(C)=O NIQQIJXGUZVEBB-UHFFFAOYSA-N 0.000 description 3
125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 3
125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
125000000636 p-nitrophenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)[N+]([O-])=O 0.000 description 3
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 3
239000007858 starting material Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
230000002195 synergetic effect Effects 0.000 description 3
238000010998 test method Methods 0.000 description 3
231100000419 toxicity Toxicity 0.000 description 3
230000001988 toxicity Effects 0.000 description 3
238000005406 washing Methods 0.000 description 3
HGKPAXHJTMHWAH-UHFFFAOYSA-N 1-(bromomethyl)-4-methylsulfonylbenzene Chemical compound CS(=O)(=O)C1=CC=C(CBr)C=C1 HGKPAXHJTMHWAH-UHFFFAOYSA-N 0.000 description 2
LBMKFQMJURUPKC-UHFFFAOYSA-N 1-(chloromethyl)-4-(trifluoromethoxy)benzene Chemical compound FC(F)(F)OC1=CC=C(CCl)C=C1 LBMKFQMJURUPKC-UHFFFAOYSA-N 0.000 description 2
VWVZFHRDLPHBEG-UHFFFAOYSA-N 1-(chloromethyl)-4-methylsulfanylbenzene Chemical compound CSC1=CC=C(CCl)C=C1 VWVZFHRDLPHBEG-UHFFFAOYSA-N 0.000 description 2
WKGOPZYVTPKHLN-UHFFFAOYSA-N 1-[4-(methoxymethyl)phenyl]ethanone Chemical compound COCC1=CC=C(C(C)=O)C=C1 WKGOPZYVTPKHLN-UHFFFAOYSA-N 0.000 description 2
DDGRAFHHXYIQQR-UHFFFAOYSA-N 1-chloro-3-(chloromethyl)benzene Chemical compound ClCC1=CC=CC(Cl)=C1 DDGRAFHHXYIQQR-UHFFFAOYSA-N 0.000 description 2
PWKNBLFSJAVFAB-UHFFFAOYSA-N 1-fluoro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1F PWKNBLFSJAVFAB-UHFFFAOYSA-N 0.000 description 2
125000001617 2,3-dimethoxy phenyl group Chemical group [H]C1=C([H])C(*)=C(OC([H])([H])[H])C(OC([H])([H])[H])=C1[H] 0.000 description 2
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 2
VOHILFSOWRNVJJ-UHFFFAOYSA-N 2-(bromomethyl)oxolane Chemical compound BrCC1CCCO1 VOHILFSOWRNVJJ-UHFFFAOYSA-N 0.000 description 2
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 2
HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 2
UMLFTCYAQPPZER-UHFFFAOYSA-N 4-(bromomethyl)benzonitrile Chemical compound BrCC1=CC=C(C#N)C=C1 UMLFTCYAQPPZER-UHFFFAOYSA-N 0.000 description 2
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208000035143 Bacterial infection Diseases 0.000 description 1
239000005711 Benzoic acid Substances 0.000 description 1
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LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 1
241000790917 Dioxys <bee> Species 0.000 description 1
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241000531795 Salmonella enterica subsp. enterica serovar Paratyphi A Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
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239000003929 acidic solution Substances 0.000 description 1
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230000003113 alkalizing effect Effects 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
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238000005804 alkylation reaction Methods 0.000 description 1
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235000019270 ammonium chloride Nutrition 0.000 description 1
230000000842 anti-protozoal effect Effects 0.000 description 1
239000003904 antiprotozoal agent Substances 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000005002 aryl methyl group Chemical group 0.000 description 1
DCBDOYDVQJVXOH-UHFFFAOYSA-N azane;1h-indole Chemical compound N.C1=CC=C2NC=CC2=C1 DCBDOYDVQJVXOH-UHFFFAOYSA-N 0.000 description 1
208000022362 bacterial infectious disease Diseases 0.000 description 1
MDOQHOZVXXKAES-UHFFFAOYSA-N benzene;pyridine;thionyl dichloride Chemical compound ClS(Cl)=O.C1=CC=CC=C1.C1=CC=NC=C1 MDOQHOZVXXKAES-UHFFFAOYSA-N 0.000 description 1
235000010233 benzoic acid Nutrition 0.000 description 1
235000019400 benzoyl peroxide Nutrition 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
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239000000872 buffer Substances 0.000 description 1
201000011510 cancer Diseases 0.000 description 1
239000002775 capsule Substances 0.000 description 1
230000000747 cardiac effect Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
125000001309 chloro group Chemical group Cl* 0.000 description 1
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 1
WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Chemical compound ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
239000003086 colorant Substances 0.000 description 1
239000013078 crystal Substances 0.000 description 1
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230000008025 crystallization Effects 0.000 description 1
229950004734 cycloguanil Drugs 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
235000005911 diet Nutrition 0.000 description 1
230000037213 diet Effects 0.000 description 1
238000007865 diluting Methods 0.000 description 1
125000005805 dimethoxy phenyl group Chemical group 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
239000003937 drug carrier Substances 0.000 description 1
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
TWQLMAJROCNXEA-UHFFFAOYSA-N ethyl 4-(bromomethyl)benzoate Chemical compound CCOC(=O)C1=CC=C(CBr)C=C1 TWQLMAJROCNXEA-UHFFFAOYSA-N 0.000 description 1
UMPRJGKLMUDRHL-UHFFFAOYSA-N ethyl 4-fluorobenzoate Chemical compound CCOC(=O)C1=CC=C(F)C=C1 UMPRJGKLMUDRHL-UHFFFAOYSA-N 0.000 description 1
125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
230000029142 excretion Effects 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000004744 fabric Substances 0.000 description 1
230000002550 fecal effect Effects 0.000 description 1
239000000796 flavoring agent Substances 0.000 description 1
235000019634 flavors Nutrition 0.000 description 1
229960000304 folic acid Drugs 0.000 description 1
235000019152 folic acid Nutrition 0.000 description 1
239000011724 folic acid Substances 0.000 description 1
238000002753 four-day suppressive test Methods 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
239000008103 glucose Substances 0.000 description 1
150000002391 heterocyclic compounds Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002054 inoculum Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
239000007928 intraperitoneal injection Substances 0.000 description 1
238000011835 investigation Methods 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 0.000 description 1
239000008101 lactose Substances 0.000 description 1
239000007791 liquid phase Substances 0.000 description 1
229910052744 lithium Inorganic materials 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
125000005905 mesyloxy group Chemical group 0.000 description 1
239000000401 methanolic extract Substances 0.000 description 1
125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000004048 modification Effects 0.000 description 1
238000012986 modification Methods 0.000 description 1
239000012452 mother liquor Substances 0.000 description 1
230000037023 motor activity Effects 0.000 description 1
LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 1
239000012457 nonaqueous media Substances 0.000 description 1
QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
235000019198 oils Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000012044 organic layer Substances 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
230000003071 parasitic effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
239000013641 positive control Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
229910000105 potassium hydride Inorganic materials 0.000 description 1
LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
239000000843 powder Substances 0.000 description 1
201000003004 ptosis Diseases 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
150000003246 quinazolines Chemical class 0.000 description 1
230000008929 regeneration Effects 0.000 description 1
238000011069 regeneration method Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
229920005989 resin Polymers 0.000 description 1
239000011347 resin Substances 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
GRONZTPUWOOUFQ-UHFFFAOYSA-M sodium;methanol;hydroxide Chemical compound [OH-].[Na+].OC GRONZTPUWOOUFQ-UHFFFAOYSA-M 0.000 description 1
239000007909 solid dosage form Substances 0.000 description 1
239000008174 sterile solution Substances 0.000 description 1
239000008223 sterile water Substances 0.000 description 1
239000011550 stock solution Substances 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000003457 sulfones Chemical class 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000335 thiazolyl group Chemical group 0.000 description 1
125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
125000001680 trimethoxyphenyl group Chemical group 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/18—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carboxylic acids, or sulfur or nitrogen analogues thereof
- C07D295/182—Radicals derived from carboxylic acids
- C07D295/185—Radicals derived from carboxylic acids from aliphatic carboxylic acids
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/02—Nutrients, e.g. vitamins, minerals
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/08—Indoles; Hydrogenated indoles with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/30—Indoles; Hydrogenated indoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to carbon atoms of the hetero ring
- C07D209/32—Oxygen atoms
- C07D209/34—Oxygen atoms in position 2
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Life Sciences & Earth Sciences (AREA)
Public Health (AREA)
General Health & Medical Sciences (AREA)
Animal Behavior & Ethology (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Communicable Diseases (AREA)
Oncology (AREA)
Obesity (AREA)
Engineering & Computer Science (AREA)
Hematology (AREA)
Diabetes (AREA)
Bioinformatics & Cheminformatics (AREA)
Nutrition Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Plural Heterocyclic Compounds (AREA)

CH850677A 1976-07-09 1977-07-08 Process for preparing novel 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines CH634069A5 (en)

Priority Applications (2)

Application Number	Priority Date	Filing Date	Title
CH289482A CH636616A5 (en)	1976-07-09	1982-05-10	Process for preparing 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines
CH289382A CH635842A5 (en)	1976-07-09	1982-05-10	Process for preparing novel 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date
US70400176A	1976-07-09	1976-07-09
US70400276A	1976-07-09	1976-07-09
GB5382176		1976-12-23
US78498777A	1977-04-06	1977-04-06

Publications (1)

Publication Number	Publication Date
CH634069A5 true CH634069A5 (en)	1983-01-14

Family

ID=27449036

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH850677A CH634069A5 (en)	1976-07-09	1977-07-08	Process for preparing novel 7-substituted 7H-pyrrolo[3,2-f]quinazoline-1,3-diamines

Country Status (13)

Country	Link
JP (1)	JPS539796A (es)
AU (1)	AU507828B2 (es)
BE (1)	BE856647A (es)
CA (1)	CA1093555A (es)
CH (1)	CH634069A5 (es)
DE (1)	DE2731039A1 (es)
DK (1)	DK309977A (es)
FR (1)	FR2357563A1 (es)
IE (1)	IE45427B1 (es)
IN (1)	IN147488B (es)
MX (1)	MX5133E (es)
NL (1)	NL7707658A (es)
PH (1)	PH13539A (es)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0639075A1 (en) *	1990-11-14	1995-02-22	Chiron Corporation	Specific inhibition of dihydrofolate reductase and compounds therefor
KR100810468B1 (ko) *	2001-10-10	2008-03-07	씨제이제일제당 (주)	사이클로옥시게나제-2의 저해제로서 선택성이 뛰어난1ｈ-인돌 유도체
US7262297B2 (en) *	2003-05-15	2007-08-28	Hoffmann-La Roche Inc.	Diaminopyrroloquinazolines compounds as protein tyrosine phosphatase inhibitors
US11077109B2 (en) *	2017-08-01	2021-08-03	The Trustees Of Princeton University	Compounds having antibacterial activity and methods of use

1977
- 1977-06-29 IE IE1345/77A patent/IE45427B1/en unknown
- 1977-07-01 AU AU26687/77A patent/AU507828B2/en not_active Expired
- 1977-07-04 CA CA281,981A patent/CA1093555A/en not_active Expired
- 1977-07-07 PH PH19967A patent/PH13539A/en unknown
- 1977-07-08 NL NL7707658A patent/NL7707658A/xx not_active Application Discontinuation
- 1977-07-08 MX MX775882U patent/MX5133E/es unknown
- 1977-07-08 BE BE179213A patent/BE856647A/xx not_active IP Right Cessation
- 1977-07-08 CH CH850677A patent/CH634069A5/de not_active IP Right Cessation
- 1977-07-08 DK DK309977A patent/DK309977A/da not_active Application Discontinuation
- 1977-07-08 FR FR7721232A patent/FR2357563A1/fr active Granted
- 1977-07-08 DE DE19772731039 patent/DE2731039A1/de not_active Withdrawn
- 1977-07-09 JP JP8247077A patent/JPS539796A/ja active Granted
- 1977-11-15 IN IN1610/CAL/77A patent/IN147488B/en unknown

Also Published As

Publication number	Publication date
JPS6254111B2 (es)	1987-11-13
PH13539A (en)	1980-06-26
IE45427B1 (en)	1982-08-25
IE45427L (en)	1978-10-06
FR2357563B1 (es)	1983-03-11
NL7707658A (nl)	1978-01-11
JPS539796A (en)	1978-01-28
CA1093555A (en)	1981-01-13
DK309977A (da)	1978-01-10
BE856647A (fr)	1978-01-09
AU2668777A (en)	1979-01-04
DE2731039A1 (de)	1978-01-19
MX5133E (es)	1983-03-28
IN147488B (es)	1980-03-15
AU507828B2 (en)	1980-02-28
FR2357563A1 (fr)	1978-02-03

Publication	Publication Date	Title
DE69305344T2 (de)	1997-02-20	Antianginale purinone
DE69603240T2 (de)	2000-01-05	Neue deazapurinderivate; eine neue klasse von crf1-spezifischen liganden
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