IL28709A - Process for the preparation of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes - Google Patents

Process for the preparation of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes

Info

Publication number: IL28709A
Authority: IL; Israel
Prior art keywords: phenyl; tetraazaphenalene; formula; mixture; atom
Prior art date: 1966-10-03

Application number

IL2870967A

Other languages

English (en)

Original Assignee

Ciba Geigy Ag

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.)

1966-10-03

Filing date

1967-10-02

Publication date

1973-01-30

1967-10-02 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1973-01-30 Publication of IL28709A publication Critical patent/IL28709A/en

Links

238000000034 method Methods 0.000 title claims description 20
238000002360 preparation method Methods 0.000 title claims description 6
DNPVEBBFVJUASY-UHFFFAOYSA-N ctk0i2885 Chemical class N1N=CC2=CC=CC3=CN=NC1=C32 DNPVEBBFVJUASY-UHFFFAOYSA-N 0.000 title description 5
-1 phenylhydrazino Chemical group 0.000 claims description 43
150000001875 compounds Chemical class 0.000 claims description 28
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 21
239000001257 hydrogen Substances 0.000 claims description 15
229910052739 hydrogen Inorganic materials 0.000 claims description 15
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
150000003839 salts Chemical group 0.000 claims description 14
229910052801 chlorine Inorganic materials 0.000 claims description 13
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 12
239000002253 acid Substances 0.000 claims description 12
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
239000007858 starting material Substances 0.000 claims description 12
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
239000000460 chlorine Substances 0.000 claims description 10
HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 claims description 9
229940067157 phenylhydrazine Drugs 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
150000001412 amines Chemical class 0.000 claims description 8
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 8
229910052794 bromium Inorganic materials 0.000 claims description 8
229910052757 nitrogen Inorganic materials 0.000 claims description 7
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 5
125000003118 aryl group Chemical group 0.000 claims description 5
150000003242 quaternary ammonium salts Chemical class 0.000 claims description 5
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 4
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
229910052799 carbon Inorganic materials 0.000 claims description 4
239000011737 fluorine Substances 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
125000003396 thiol group Chemical group [H]S* 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 3
125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 3
125000003277 amino group Chemical group 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 3
239000003085 diluting agent Substances 0.000 claims 2
239000008194 pharmaceutical composition Substances 0.000 claims 2
125000004429 atom Chemical group 0.000 claims 1
239000007795 chemical reaction product Substances 0.000 claims 1
ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 claims 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 90
239000000203 mixture Substances 0.000 description 79
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 58
239000000243 solution Substances 0.000 description 48
238000010992 reflux Methods 0.000 description 42
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 38
239000007787 solid Substances 0.000 description 34
239000002244 precipitate Substances 0.000 description 33
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 30
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
239000000047 product Substances 0.000 description 24
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 21
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
239000000706 filtrate Substances 0.000 description 19
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 18
238000003756 stirring Methods 0.000 description 18
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
238000006243 chemical reaction Methods 0.000 description 15
NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 13
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 13
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 12
239000013078 crystal Substances 0.000 description 12
239000000463 material Substances 0.000 description 12
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 12
IJAPPYDYQCXOEF-UHFFFAOYSA-N phthalazin-1(2H)-one Chemical compound C1=CC=C2C(=O)NN=CC2=C1 IJAPPYDYQCXOEF-UHFFFAOYSA-N 0.000 description 11
230000007717 exclusion Effects 0.000 description 10
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 9
238000001953 recrystallisation Methods 0.000 description 9
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 8
229960000583 acetic acid Drugs 0.000 description 8
238000009835 boiling Methods 0.000 description 8
239000003610 charcoal Substances 0.000 description 8
239000002904 solvent Substances 0.000 description 8
MDKXBBPLEGPIRI-UHFFFAOYSA-N ethoxyethane;methanol Chemical compound OC.CCOCC MDKXBBPLEGPIRI-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 6
PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 6
HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 6
239000012362 glacial acetic acid Substances 0.000 description 6
239000005457 ice water Substances 0.000 description 6
238000002844 melting Methods 0.000 description 6
230000008018 melting Effects 0.000 description 6
239000000725 suspension Substances 0.000 description 6
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 4
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
238000001816 cooling Methods 0.000 description 4
150000002148 esters Chemical class 0.000 description 4
238000001704 evaporation Methods 0.000 description 4
230000008020 evaporation Effects 0.000 description 4
239000006260 foam Substances 0.000 description 4
238000010438 heat treatment Methods 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
229910000030 sodium bicarbonate Inorganic materials 0.000 description 4
235000017557 sodium bicarbonate Nutrition 0.000 description 4
229910052938 sodium sulfate Inorganic materials 0.000 description 4
235000011152 sodium sulphate Nutrition 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
QSKWJTXWJJOJFP-UHFFFAOYSA-N chloroform;ethoxyethane Chemical compound ClC(Cl)Cl.CCOCC QSKWJTXWJJOJFP-UHFFFAOYSA-N 0.000 description 3
238000000354 decomposition reaction Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
238000001914 filtration Methods 0.000 description 3
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 3
229910000041 hydrogen chloride Inorganic materials 0.000 description 3
239000000155 melt Substances 0.000 description 3
150000007522 mineralic acids Chemical class 0.000 description 3
239000012452 mother liquor Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
150000007524 organic acids Chemical class 0.000 description 3
QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 3
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 3
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 3
150000003254 radicals Chemical class 0.000 description 3
229910000029 sodium carbonate Inorganic materials 0.000 description 3
JDOLHKIOQHFKFC-UHFFFAOYSA-N 1-hydroxy-3-oxo-1h-2-benzofuran-4-carboxylic acid Chemical compound C1=CC=C(C(O)=O)C2=C1C(O)OC2=O JDOLHKIOQHFKFC-UHFFFAOYSA-N 0.000 description 2
KTFJPMPXSYUEIP-UHFFFAOYSA-N 3-benzoylphthalic acid Chemical compound OC(=O)C1=CC=CC(C(=O)C=2C=CC=CC=2)=C1C(O)=O KTFJPMPXSYUEIP-UHFFFAOYSA-N 0.000 description 2
DBRDGLWIILLOHI-UHFFFAOYSA-N 4-chloro-12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound ClC=1N=NC=2N(N=CC3=CC=CC1C23)C DBRDGLWIILLOHI-UHFFFAOYSA-N 0.000 description 2
TWWAWPHAOPTQEU-UHFFFAOYSA-N 4-methyl-2-benzofuran-1,3-dione Chemical group CC1=CC=CC2=C1C(=O)OC2=O TWWAWPHAOPTQEU-UHFFFAOYSA-N 0.000 description 2
239000004342 Benzoyl peroxide Substances 0.000 description 2
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
JRNVZBWKYDBUCA-UHFFFAOYSA-N N-chlorosuccinimide Chemical compound ClN1C(=O)CCC1=O JRNVZBWKYDBUCA-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
235000011054 acetic acid Nutrition 0.000 description 2
230000002152 alkylating effect Effects 0.000 description 2
125000002947 alkylene group Chemical group 0.000 description 2
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
235000019400 benzoyl peroxide Nutrition 0.000 description 2
WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000002026 chloroform extract Substances 0.000 description 2
239000012043 crude product Substances 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 2
229960001760 dimethyl sulfoxide Drugs 0.000 description 2
125000004494 ethyl ester group Chemical group 0.000 description 2
239000007789 gas Substances 0.000 description 2
229940093915 gynecological organic acid Drugs 0.000 description 2
239000012442 inert solvent Substances 0.000 description 2
239000002198 insoluble material Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
235000005985 organic acids Nutrition 0.000 description 2
XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
239000000843 powder Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
KZNICNPSHKQLFF-UHFFFAOYSA-N succinimide Chemical compound O=C1CCC(=O)N1 KZNICNPSHKQLFF-UHFFFAOYSA-N 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 2
238000004809 thin layer chromatography Methods 0.000 description 2
239000001124 (E)-prop-1-ene-1,2,3-tricarboxylic acid Substances 0.000 description 1
BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
UETOSPQPDSSVOC-UHFFFAOYSA-N 12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaen-4-one Chemical compound O=C1NN=C2N(N=CC=3C=CC=C1C23)C UETOSPQPDSSVOC-UHFFFAOYSA-N 0.000 description 1
AWGBNOQONQAYBG-UHFFFAOYSA-N 12-methyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,5,7,9(13),10-pentaene-4-thione Chemical compound S=C1NN=C2N(N=CC=3C=CC=C1C23)C AWGBNOQONQAYBG-UHFFFAOYSA-N 0.000 description 1
FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
LSECHLLXQGJTCE-UHFFFAOYSA-N 2,6-diformylbenzoic acid Chemical class OC(=O)C1=C(C=O)C=CC=C1C=O LSECHLLXQGJTCE-UHFFFAOYSA-N 0.000 description 1
HCBHQDKBSKYGCK-UHFFFAOYSA-N 2,6-dimethylbenzoic acid Chemical group CC1=CC=CC(C)=C1C(O)=O HCBHQDKBSKYGCK-UHFFFAOYSA-N 0.000 description 1
HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 description 1
UPSXAPQYNGXVBF-UHFFFAOYSA-N 2-bromobutane Chemical compound CCC(C)Br UPSXAPQYNGXVBF-UHFFFAOYSA-N 0.000 description 1
AKCRQHGQIJBRMN-UHFFFAOYSA-N 2-chloroaniline Chemical compound NC1=CC=CC=C1Cl AKCRQHGQIJBRMN-UHFFFAOYSA-N 0.000 description 1
BSPCSKHALVHRSR-UHFFFAOYSA-N 2-chlorobutane Chemical compound CCC(C)Cl BSPCSKHALVHRSR-UHFFFAOYSA-N 0.000 description 1
IQRUSQUYPCHEKN-UHFFFAOYSA-N 2-iodobutane Chemical compound CCC(C)I IQRUSQUYPCHEKN-UHFFFAOYSA-N 0.000 description 1
BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
LLZSSWCXDZEQMZ-UHFFFAOYSA-N 4-(3,4-dihydro-1H-isoquinolin-2-yl)-12-phenyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound C1(=CC=CC=C1)N1N=CC2=CC=CC3=C(N=NC1=C32)N3CC2=CC=CC=C2CC3 LLZSSWCXDZEQMZ-UHFFFAOYSA-N 0.000 description 1
JCYPECIVGRXBMO-UHFFFAOYSA-N 4-(dimethylamino)azobenzene Chemical compound C1=CC(N(C)C)=CC=C1N=NC1=CC=CC=C1 JCYPECIVGRXBMO-UHFFFAOYSA-N 0.000 description 1
BWJAOVUPAKDWMQ-UHFFFAOYSA-N 4-chloro-12-phenyl-2,3,11,12-tetrazatricyclo[7.3.1.05,13]trideca-1,3,5,7,9(13),10-hexaene Chemical compound ClC=1N=NC=2N(N=CC3=CC=CC1C23)C2=CC=CC=C2 BWJAOVUPAKDWMQ-UHFFFAOYSA-N 0.000 description 1
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 1
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
OWYWGLHRNBIFJP-UHFFFAOYSA-N Ipazine Chemical compound CCN(CC)C1=NC(Cl)=NC(NC(C)C)=N1 OWYWGLHRNBIFJP-UHFFFAOYSA-N 0.000 description 1
AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical class CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
229940091181 aconitic acid Drugs 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
125000005037 alkyl phenyl group Chemical group 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
229940040526 anhydrous sodium acetate Drugs 0.000 description 1
230000003276 anti-hypertensive effect Effects 0.000 description 1
239000002220 antihypertensive agent Substances 0.000 description 1
229940030600 antihypertensive agent Drugs 0.000 description 1
150000005840 aryl radicals Chemical class 0.000 description 1
238000010533 azeotropic distillation Methods 0.000 description 1
239000002585 base Substances 0.000 description 1
SLUNEGLMXGHOLY-UHFFFAOYSA-N benzene;hexane Chemical compound CCCCCC.C1=CC=CC=C1 SLUNEGLMXGHOLY-UHFFFAOYSA-N 0.000 description 1
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 1
KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
229940073608 benzyl chloride Drugs 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
230000036772 blood pressure Effects 0.000 description 1
239000011449 brick Substances 0.000 description 1
KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000002837 carbocyclic group Chemical group 0.000 description 1
125000004432 carbon atom Chemical group C* 0.000 description 1
239000002327 cardiovascular agent Substances 0.000 description 1
229940125692 cardiovascular agent Drugs 0.000 description 1
210000003169 central nervous system Anatomy 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
GTZCVFVGUGFEME-IWQZZHSRSA-N cis-aconitic acid Chemical compound OC(=O)C\C(C(O)=O)=C\C(O)=O GTZCVFVGUGFEME-IWQZZHSRSA-N 0.000 description 1
239000013058 crude material Substances 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
125000000950 dibromo group Chemical group Br* 0.000 description 1
125000004188 dichlorophenyl group Chemical group 0.000 description 1
DENRZWYUOJLTMF-UHFFFAOYSA-N diethyl sulfate Chemical compound CCOS(=O)(=O)OCC DENRZWYUOJLTMF-UHFFFAOYSA-N 0.000 description 1
HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
125000004212 difluorophenyl group Chemical group 0.000 description 1
230000010339 dilation Effects 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
238000004821 distillation Methods 0.000 description 1
239000012153 distilled water Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
ZKQFHRVKCYFVCN-UHFFFAOYSA-N ethoxyethane;hexane Chemical compound CCOCC.CCCCCC ZKQFHRVKCYFVCN-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
239000012458 free base Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
BHEPBYXIRTUNPN-UHFFFAOYSA-N hydridophosphorus(.) (triplet) Chemical compound [PH] BHEPBYXIRTUNPN-UHFFFAOYSA-N 0.000 description 1
230000003301 hydrolyzing effect Effects 0.000 description 1
238000005286 illumination Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
238000002329 infrared spectrum Methods 0.000 description 1
229910003480 inorganic solid Inorganic materials 0.000 description 1
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
239000004310 lactic acid Substances 0.000 description 1
235000014655 lactic acid Nutrition 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
239000001630 malic acid Substances 0.000 description 1
235000011090 malic acid Nutrition 0.000 description 1
238000010907 mechanical stirring Methods 0.000 description 1
229940098779 methanesulfonic acid Drugs 0.000 description 1
VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical group COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
WHQSYGRFZMUQGQ-UHFFFAOYSA-N n,n-dimethylformamide;hydrate Chemical compound O.CN(C)C=O WHQSYGRFZMUQGQ-UHFFFAOYSA-N 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 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
230000002093 peripheral effect Effects 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
239000011833 salt mixture Substances 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
239000012265 solid product Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
125000001424 substituent group Chemical group 0.000 description 1
125000003107 substituted aryl group Chemical group 0.000 description 1
229960002317 succinimide Drugs 0.000 description 1
PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-N sulfonic acid Chemical class OS(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-N 0.000 description 1
239000001117 sulphuric acid Substances 0.000 description 1
235000011149 sulphuric acid Nutrition 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
IMCGHZIGRANKHV-AJNGGQMLSA-N tert-butyl (3s,5s)-2-oxo-5-[(2s,4s)-5-oxo-4-propan-2-yloxolan-2-yl]-3-propan-2-ylpyrrolidine-1-carboxylate Chemical compound O1C(=O)[C@H](C(C)C)C[C@H]1[C@H]1N(C(=O)OC(C)(C)C)C(=O)[C@H](C(C)C)C1 IMCGHZIGRANKHV-AJNGGQMLSA-N 0.000 description 1
230000001225 therapeutic effect Effects 0.000 description 1
101150068774 thyX gene Proteins 0.000 description 1
GTZCVFVGUGFEME-UHFFFAOYSA-N trans-aconitic acid Natural products OC(=O)CC(C(O)=O)=CC(O)=O GTZCVFVGUGFEME-UHFFFAOYSA-N 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
230000002792 vascular Effects 0.000 description 1

Classifications

- 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
- C07D487/06—Peri-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

IL2870967A 1966-10-03 1967-10-02 Process for the preparation of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes IL28709A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US58398066A	1966-10-03	1966-10-03

Publications (1)

Publication Number	Publication Date
IL28709A true IL28709A (en)	1973-01-30

Family

ID=24335405

Family Applications (2)

Application Number	Title	Priority Date	Filing Date
IL2870967A IL28709A (en)	1966-10-03	1967-10-02	Process for the preparation of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes
IL2871067A IL28710A (en)	1966-10-03	1967-10-02	Process for the production of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes

Family Applications After (1)

Application Number	Title	Priority Date	Filing Date
IL2871067A IL28710A (en)	1966-10-03	1967-10-02	Process for the production of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes

Country Status (14)

Country	Link
AT (3)	AT273981B (fr)
BE (2)	BE704585A (fr)
CH (2)	CH515909A (fr)
DE (2)	DE1695039A1 (fr)
DK (2)	DK120755B (fr)
ES (2)	ES345680A1 (fr)
FI (2)	FI47769C (fr)
FR (3)	FR1550404A (fr)
GB (2)	GB1204522A (fr)
GR (2)	GR37758B (fr)
IL (2)	IL28709A (fr)
NL (2)	NL6713378A (fr)
NO (1)	NO122482B (fr)
SE (2)	SE335346B (fr)

1967
- 1967-09-30 CH CH1363967A patent/CH515909A/de not_active IP Right Cessation
- 1967-09-30 CH CH1364067A patent/CH486477A/de not_active IP Right Cessation
- 1967-10-02 GB GB44680/67A patent/GB1204522A/en not_active Expired
- 1967-10-02 ES ES345680A patent/ES345680A1/es not_active Expired
- 1967-10-02 AT AT891667A patent/AT273981B/de active
- 1967-10-02 GR GR670137758A patent/GR37758B/el unknown
- 1967-10-02 SE SE1346167A patent/SE335346B/xx unknown
- 1967-10-02 GR GR670137757A patent/GR37757B/el unknown
- 1967-10-02 DK DK487767A patent/DK120755B/da unknown
- 1967-10-02 FI FI263167A patent/FI47769C/fi active
- 1967-10-02 FR FR1550404D patent/FR1550404A/fr not_active Expired
- 1967-10-02 BE BE704585D patent/BE704585A/xx unknown
- 1967-10-02 IL IL2870967A patent/IL28709A/en unknown
- 1967-10-02 NL NL6713378A patent/NL6713378A/xx unknown
- 1967-10-02 IL IL2871067A patent/IL28710A/en unknown
- 1967-10-02 GB GB4467967A patent/GB1208114A/en not_active Expired
- 1967-10-02 DE DE19671695039 patent/DE1695039A1/de active Pending
- 1967-10-02 NL NL6713374A patent/NL6713374A/xx unknown
- 1967-10-02 DE DE19671695038 patent/DE1695038A1/de active Pending
- 1967-10-02 ES ES345681A patent/ES345681A1/es not_active Expired
- 1967-10-02 FI FI263267A patent/FI47770C/fi active
- 1967-10-02 AT AT891467A patent/AT273980B/de active
- 1967-10-02 NO NO16994967A patent/NO122482B/no unknown
- 1967-10-02 BE BE704584D patent/BE704584A/xx unknown
- 1967-10-02 AT AT880368A patent/AT276411B/de active
- 1967-10-02 DK DK487867A patent/DK123653B/da unknown
- 1967-10-02 SE SE1346067A patent/SE329401B/xx unknown
- 1967-12-29 FR FR134301A patent/FR7211M/fr not_active Expired
- 1967-12-29 FR FR134300A patent/FR7210M/fr not_active Expired

Also Published As

Publication number	Publication date
CH486477A (de)	1970-02-28
CH515909A (de)	1971-11-30
GR37758B (el)	1969-07-11
DE1695038A1 (de)	1971-04-08
DK120755B (da)	1971-07-12
GB1208114A (en)	1970-10-07
ES345681A1 (es)	1968-11-16
SE335346B (fr)	1971-05-24
BE704585A (fr)	1968-04-02
AT276411B (de)	1969-11-25
DK123653B (da)	1972-07-17
FI47770B (fr)	1973-11-30
ES345680A1 (es)	1968-11-16
FR7211M (fr)	1969-08-25
AT273980B (de)	1969-09-10
NL6713374A (fr)	1968-04-04
FI47769C (fi)	1974-03-11
SE329401B (fr)	1970-10-12
IL28710A (en)	1973-01-30
FI47770C (fi)	1974-03-11
NO122482B (fr)	1971-07-05
NL6713378A (fr)	1968-04-04
GR37757B (el)	1969-07-11
FR1550404A (fr)	1968-12-20
BE704584A (fr)	1968-04-02
GB1204522A (en)	1970-09-09
DE1695039A1 (de)	1971-04-08
FR7210M (fr)	1969-08-25
AT273981B (de)	1969-09-10
FI47769B (fr)	1973-11-30

Publication	Publication Date	Title
US3896145A (en)	1975-07-22	Carbazoles
EP0263352A1 (fr)	1988-04-13	Imidazo-benzoxazinones, leur préparation et médicaments contenant ces composés
NO173445B (no)	1993-09-06	Analogifremgangsmaate for fremstilling av terapeutisk aktive kinolinkarboksylsyrederivater
NO152373B (no)	1985-06-10	Analogifremgangsmaate for fremstilling av farmakologisk aktive 8-fenyl-purin-derivater
PL119501B1 (en)	1982-01-30	Process for manufacturing novel,condensed pyrimidine derivatives pirimidina
US3681360A (en)	1972-08-01	Antiviral substituted acridanones
HUP0002650A2 (hu)	2001-01-29	4-Oxo-3,5-dihidro-4H-piridazino[4,5-b]-indol-1-acetamid-származékok, eljárás a vegyületek előállítására és a vegyületeket tartalmazó gyógyszerkészítmények
US4086353A (en)	1978-04-25	Certain azolinylamino (azolidinylimino) indazoles
EP0003016B1 (fr)	1981-12-30	Dérivés de la pyrazino-benzoxazépine et -benzothiazépine, leurs procédés de préparation et compositions pharmaceutiques les contenant
IE49788B1 (en)	1985-12-11	6-substituted 11-alkylene-morphanthridines,their preparation and therapeutic agents containing these compounds
GB1568398A (en)	1980-05-29	Triazolo pyridazine derivatives
US4376121A (en)	1983-03-08	Antiallerigically-active imidazothienopyrimidine derivatives
US3862171A (en)	1975-01-21	6-phenyl-4h-s-triazolo(1,5-a)(1,4)benzodiazepine-2-carboxylic acids and their esters
NO780395L (no)	1978-08-07	Oksadiazolpyrimidin-derivater.
US3847923A (en)	1974-11-12	N-(1-(3-cyano-3,3-diphenylpropyl)-4-phenylpiperidine-4-carbonyloxy)succinimide and glutarimide
US3458515A (en)	1969-07-29	Piperazine substituted pyrroles
IL28709A (en)	1973-01-30	Process for the preparation of 1,2,8,9-tetraazaphenalenes and new 1,2,8,9-tetraazaphenalenes
PL69663B1 (fr)	1973-08-31
CS207671B2 (en)	1981-08-31	Method of making the piperazinylchinazoline derivatives
US3711473A (en)	1973-01-16	3-hydrazino-1,2,8,9-tetraazaphenalenes
US4362727A (en)	1982-12-07	5-Substituted 9-cyanomethylene-dithieno[3,4-b:4,3-e]-azepines and therapeutic agents which contain these compounds
JPS60169480A (ja)	1985-09-02	イミダゾ−ル誘導体
NO152843B (no)	1985-08-19	Analogifremgangsmaate for fremstilling av terapeutisk aktive pyrimidopyrimidiner
US3304304A (en)	1967-02-14	Quinazolone derivatives
US3291824A (en)	1966-12-13	Nu-(2-halo-lower alkanoyl) anthranilic acid derivatives