DE1239291B - Verfahren zur Herstellung von Guanyl-hydrazonen aromatischer polycyclischer Carbonylverbindungen - Google Patents
Verfahren zur Herstellung von Guanyl-hydrazonen aromatischer polycyclischer CarbonylverbindungenInfo
- Publication number
- DE1239291B DE1239291B DE1964F0042610 DEF0042610A DE1239291B DE 1239291 B DE1239291 B DE 1239291B DE 1964F0042610 DE1964F0042610 DE 1964F0042610 DE F0042610 A DEF0042610 A DE F0042610A DE 1239291 B DE1239291 B DE 1239291B
- Authority
- DE
- Germany
- Prior art keywords
- general formula
- radical
- branched
- alicyclic
- salts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- -1 aromatic polycyclic carbonyl compounds Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 7
- 238000002360 preparation method Methods 0.000 title claims description 5
- MXWHMTNPTTVWDM-NXOFHUPFSA-N mitoguazone Chemical compound NC(N)=N\N=C(/C)\C=N\N=C(N)N MXWHMTNPTTVWDM-NXOFHUPFSA-N 0.000 title description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 8
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000007857 hydrazones Chemical class 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 150000007513 acids Chemical class 0.000 claims description 5
- 125000002723 alicyclic group Chemical group 0.000 claims description 5
- 231100000252 nontoxic Toxicity 0.000 claims description 5
- 230000003000 nontoxic effect Effects 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 229930194542 Keto Natural products 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims description 2
- 150000001491 aromatic compounds Chemical class 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000007859 condensation product Substances 0.000 claims description 2
- 150000001912 cyanamides Chemical class 0.000 claims description 2
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- 125000000468 ketone group Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- 125000004434 sulfur atom Chemical group 0.000 claims description 2
- 150000003583 thiosemicarbazides Chemical class 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000000354 decomposition reaction Methods 0.000 description 8
- 241000700199 Cavia porcellus Species 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 210000004165 myocardium Anatomy 0.000 description 6
- 210000002837 heart atrium Anatomy 0.000 description 5
- 230000009090 positive inotropic effect Effects 0.000 description 5
- 231100000419 toxicity Toxicity 0.000 description 5
- 230000001988 toxicity Effects 0.000 description 5
- 241000700198 Cavia Species 0.000 description 4
- 206010062575 Muscle contracture Diseases 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 208000006111 contracture Diseases 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000003254 radicals Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- XWZKPVAYNUXKCZ-UHFFFAOYSA-N 1-(5-acetylnaphthalen-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1C(C)=O XWZKPVAYNUXKCZ-UHFFFAOYSA-N 0.000 description 3
- 108091006112 ATPases Proteins 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 102000057290 Adenosine Triphosphatases Human genes 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- RZGGOKRYQZPJQD-UHFFFAOYSA-N (6-benzoylpyren-1-yl)-phenylmethanone Chemical compound C=1C=C(C2=C34)C=CC3=C(C(=O)C=3C=CC=CC=3)C=CC4=CC=C2C=1C(=O)C1=CC=CC=C1 RZGGOKRYQZPJQD-UHFFFAOYSA-N 0.000 description 2
- XRHLZWNTCOKXCJ-UHFFFAOYSA-N 1-(5-acetyl-2,6-dihydroxynaphthalen-1-yl)ethanone Chemical compound OC1=CC=C2C(C(=O)C)=C(O)C=CC2=C1C(C)=O XRHLZWNTCOKXCJ-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- MGRRGKWPEVFJSH-UHFFFAOYSA-N 10-(10-oxoanthracen-9-ylidene)anthracen-9-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC=C2C1=C1C2=CC=CC=C2C(=O)C2=CC=CC=C21 MGRRGKWPEVFJSH-UHFFFAOYSA-N 0.000 description 2
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 2
- UBDZFAGVPPMTIT-UHFFFAOYSA-N 2-aminoguanidine;hydron;chloride Chemical compound [Cl-].NC(N)=N[NH3+] UBDZFAGVPPMTIT-UHFFFAOYSA-N 0.000 description 2
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 2
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 230000000747 cardiac effect Effects 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- KZTYYGOKRVBIMI-UHFFFAOYSA-N diphenyl sulfone Chemical compound C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- QNXSIUBBGPHDDE-UHFFFAOYSA-N indan-1-one Chemical compound C1=CC=C2C(=O)CCC2=C1 QNXSIUBBGPHDDE-UHFFFAOYSA-N 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-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
- RDOWQLZANAYVLL-UHFFFAOYSA-N phenanthridine Chemical compound C1=CC=C2C3=CC=CC=C3C=NC2=C1 RDOWQLZANAYVLL-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- VOICENUZWLJCFE-UHFFFAOYSA-N (10-benzoylanthracen-9-yl)-phenylmethanone Chemical compound C=12C=CC=CC2=C(C(=O)C=2C=CC=CC=2)C2=CC=CC=C2C=1C(=O)C1=CC=CC=C1 VOICENUZWLJCFE-UHFFFAOYSA-N 0.000 description 1
- DKSJRIWNWIRVCV-UHFFFAOYSA-N (4-benzoylnaphthalen-1-yl)-phenylmethanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C2=CC=CC=C2C=1C(=O)C1=CC=CC=C1 DKSJRIWNWIRVCV-UHFFFAOYSA-N 0.000 description 1
- OUACHDIGJXGWRQ-UHFFFAOYSA-N (5-benzoyl-2,6-dimethylnaphthalen-1-yl)-phenylmethanone Chemical compound C(C1=CC=CC=C1)(=O)C1=C(C=CC2=C(C(=CC=C12)C)C(C1=CC=CC=C1)=O)C OUACHDIGJXGWRQ-UHFFFAOYSA-N 0.000 description 1
- UJBRSMKKNNODOP-UHFFFAOYSA-N (5-benzoyl-4,8-dihydroxynaphthalen-1-yl)-phenylmethanone Chemical compound C12=C(O)C=CC(C(=O)C=3C=CC=CC=3)=C2C(O)=CC=C1C(=O)C1=CC=CC=C1 UJBRSMKKNNODOP-UHFFFAOYSA-N 0.000 description 1
- OOSBCICQIJKSIO-UHFFFAOYSA-N (5-benzoylnaphthalen-1-yl)-phenylmethanone Chemical compound C=1C=CC2=C(C(=O)C=3C=CC=CC=3)C=CC=C2C=1C(=O)C1=CC=CC=C1 OOSBCICQIJKSIO-UHFFFAOYSA-N 0.000 description 1
- CYNRPHCWSKPLMN-UHFFFAOYSA-N (5-benzoylnaphthalen-2-yl)-phenylmethanone Chemical compound C=1C=C2C(C(=O)C=3C=CC=CC=3)=CC=CC2=CC=1C(=O)C1=CC=CC=C1 CYNRPHCWSKPLMN-UHFFFAOYSA-N 0.000 description 1
- RIGLBTSLVXOXPB-UHFFFAOYSA-N (6-benzoylnaphthalen-2-yl)-phenylmethanone Chemical compound C=1C=C2C=C(C(=O)C=3C=CC=CC=3)C=CC2=CC=1C(=O)C1=CC=CC=C1 RIGLBTSLVXOXPB-UHFFFAOYSA-N 0.000 description 1
- OTXHZHQQWQTQMW-UHFFFAOYSA-N (diaminomethylideneamino)azanium;hydrogen carbonate Chemical compound OC([O-])=O.N[NH2+]C(N)=N OTXHZHQQWQTQMW-UHFFFAOYSA-N 0.000 description 1
- JXPLNQNUEKAHEV-UHFFFAOYSA-N 1,5-diacetylanthracene-9,10-dione Chemical compound O=C1C2=C(C(C)=O)C=CC=C2C(=O)C2=C1C=CC=C2C(=O)C JXPLNQNUEKAHEV-UHFFFAOYSA-N 0.000 description 1
- GLGJFVRVRGKNPI-UHFFFAOYSA-N 1,8-diacetylanthracene-9,10-dione Chemical compound O=C1C2=CC=CC(C(C)=O)=C2C(=O)C2=C1C=CC=C2C(=O)C GLGJFVRVRGKNPI-UHFFFAOYSA-N 0.000 description 1
- JBCVRTMLHPWTJI-UHFFFAOYSA-N 1-(10-acetylanthracen-9-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=C(C=CC=C3)C3=C(C(C)=O)C2=C1 JBCVRTMLHPWTJI-UHFFFAOYSA-N 0.000 description 1
- GVAAPWYZIXMWLZ-UHFFFAOYSA-N 1-(8-acetylanthracen-1-yl)ethanone Chemical compound C1=CC(C(C)=O)=C2C=C3C(C(=O)C)=CC=CC3=CC2=C1 GVAAPWYZIXMWLZ-UHFFFAOYSA-N 0.000 description 1
- FQORHEMAUBKTGC-UHFFFAOYSA-N 1-(8-acetylnaphthalen-1-yl)ethanone Chemical compound C1=CC(C(C)=O)=C2C(C(=O)C)=CC=CC2=C1 FQORHEMAUBKTGC-UHFFFAOYSA-N 0.000 description 1
- UBNPGDBUJBXYRX-UHFFFAOYSA-N 10-benzoyl-10h-anthracen-9-one Chemical compound C12=CC=CC=C2C(=O)C2=CC=CC=C2C1C(=O)C1=CC=CC=C1 UBNPGDBUJBXYRX-UHFFFAOYSA-N 0.000 description 1
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- TZMSYXZUNZXBOL-UHFFFAOYSA-N 10H-phenoxazine Chemical compound C1=CC=C2NC3=CC=CC=C3OC2=C1 TZMSYXZUNZXBOL-UHFFFAOYSA-N 0.000 description 1
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- 125000004429 atom Chemical group 0.000 description 1
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- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
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- 239000002368 cardiac glycoside Substances 0.000 description 1
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- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- KMSRVXJGTIRNNK-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen carbonate Chemical compound NC(N)=N.OC(O)=O KMSRVXJGTIRNNK-UHFFFAOYSA-N 0.000 description 1
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- 239000000284 extract Substances 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 229910000042 hydrogen bromide Inorganic materials 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
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- 238000002844 melting Methods 0.000 description 1
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- 150000007522 mineralic acids Chemical class 0.000 description 1
- PYHRFGZORIHOMQ-UHFFFAOYSA-N naphthalene-1,8-dicarbaldehyde Chemical compound C1=CC(C=O)=C2C(C=O)=CC=CC2=C1 PYHRFGZORIHOMQ-UHFFFAOYSA-N 0.000 description 1
- MNZMMCVIXORAQL-UHFFFAOYSA-N naphthalene-2,6-diol Chemical compound C1=C(O)C=CC2=CC(O)=CC=C21 MNZMMCVIXORAQL-UHFFFAOYSA-N 0.000 description 1
- WSPGRORDDACGQK-UHFFFAOYSA-N naphthalene-2,7-dicarbaldehyde Chemical compound C1=CC(C=O)=CC2=CC(C=O)=CC=C21 WSPGRORDDACGQK-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- LOOWWKXPYHZZDM-UHFFFAOYSA-N pentacene-5,12-dione Chemical compound O=C1C2=CC=CC=C2C=C2C1=CC1=CC3=CC=CC=C3C(=O)C1=C2 LOOWWKXPYHZZDM-UHFFFAOYSA-N 0.000 description 1
- FUTARTAINOHELR-UHFFFAOYSA-N perylene-3,10-dione Chemical compound C12=CC=CC(C(=O)C=C3)=C2C3=C2C3=C1C=CC=C3C(=O)C=C2 FUTARTAINOHELR-UHFFFAOYSA-N 0.000 description 1
- 150000005041 phenanthrolines Chemical class 0.000 description 1
- 150000002988 phenazines Chemical class 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- AHXIPWMNLOHFTN-UHFFFAOYSA-N phenyl-(4,5,8-tribenzoylnaphthalen-1-yl)methanone Chemical compound C=1C=C(C(=O)C=2C=CC=CC=2)C2=C(C(=O)C=3C=CC=CC=3)C=CC(C(=O)C=3C=CC=CC=3)=C2C=1C(=O)C1=CC=CC=C1 AHXIPWMNLOHFTN-UHFFFAOYSA-N 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 150000003246 quinazolines Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229930002534 steroid glycoside Natural products 0.000 description 1
- 150000008143 steroidal glycosides Chemical class 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003456 sulfonamides Chemical class 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C281/00—Derivatives of carbonic acid containing functional groups covered by groups C07C269/00 - C07C279/00 in which at least one nitrogen atom of these functional groups is further bound to another nitrogen atom not being part of a nitro or nitroso group
- C07C281/16—Compounds containing any of the groups, e.g. aminoguanidine
- C07C281/18—Compounds containing any of the groups, e.g. aminoguanidine the other nitrogen atom being further doubly-bound to a carbon atom, e.g. guanylhydrazones
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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 ring carbon atoms
- C07D233/44—Nitrogen atoms not forming part of a nitro radical
- C07D233/52—Nitrogen atoms not forming part of a nitro radical with hetero atoms directly attached to said nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/76—Dibenzothiophenes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB1053035D GB1053035A (enrdf_load_stackoverflow) | 1964-04-15 | ||
| DE1964F0042610 DE1239291B (de) | 1964-04-15 | 1964-04-15 | Verfahren zur Herstellung von Guanyl-hydrazonen aromatischer polycyclischer Carbonylverbindungen |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE1964F0042610 DE1239291B (de) | 1964-04-15 | 1964-04-15 | Verfahren zur Herstellung von Guanyl-hydrazonen aromatischer polycyclischer Carbonylverbindungen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1239291B true DE1239291B (de) | 1967-04-27 |
Family
ID=7099171
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1964F0042610 Pending DE1239291B (de) | 1964-04-15 | 1964-04-15 | Verfahren zur Herstellung von Guanyl-hydrazonen aromatischer polycyclischer Carbonylverbindungen |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1239291B (enrdf_load_stackoverflow) |
| GB (1) | GB1053035A (enrdf_load_stackoverflow) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3686222A1 (en) * | 2012-10-19 | 2020-07-29 | Zeon Corporation | Polymerizable compound, polymerizable composition, polymer, and optically anisotropic substance |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4258181A (en) * | 1978-09-05 | 1981-03-24 | American Cyanamid Company | Substituted 9,10-anthracenebishydrazones |
| FR2446285A1 (fr) * | 1978-09-05 | 1980-08-08 | American Cyanamid Co | Anthracene bis-(carbonyl-9,10-hydrazones) utiles comme agents antitumoraux |
-
0
- GB GB1053035D patent/GB1053035A/en active Active
-
1964
- 1964-04-15 DE DE1964F0042610 patent/DE1239291B/de active Pending
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP3686222A1 (en) * | 2012-10-19 | 2020-07-29 | Zeon Corporation | Polymerizable compound, polymerizable composition, polymer, and optically anisotropic substance |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1053035A (enrdf_load_stackoverflow) |
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