CH337853A - Verfahren zur Herstellung von 9-substituierten 1,10-Diaza-anthracenen - Google Patents
Verfahren zur Herstellung von 9-substituierten 1,10-Diaza-anthracenenInfo
- Publication number
- CH337853A CH337853A CH337853DA CH337853A CH 337853 A CH337853 A CH 337853A CH 337853D A CH337853D A CH 337853DA CH 337853 A CH337853 A CH 337853A
- Authority
- CH
- Switzerland
- Prior art keywords
- diaza
- hydroxy
- hydroxyamine
- anthracene
- propylamino
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 25
- -1 9-substituted 1,10-diaza-anthracenes Chemical class 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 6
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 15
- 150000001875 compounds Chemical class 0.000 claims description 12
- 150000003839 salts Chemical class 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- KINQZTCWWGMDOS-UHFFFAOYSA-N benzo[b][1,5]naphthyridine Chemical group C1=CC=NC2=CC3=CC=CC=C3N=C21 KINQZTCWWGMDOS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- HJEZEUXGJDXVQD-UHFFFAOYSA-N 3-(3-aminopropylamino)propane-1,2-diol Chemical compound NCCCNCC(O)CO HJEZEUXGJDXVQD-UHFFFAOYSA-N 0.000 claims description 3
- LHIJANUOQQMGNT-UHFFFAOYSA-N aminoethylethanolamine Chemical compound NCCNCCO LHIJANUOQQMGNT-UHFFFAOYSA-N 0.000 claims description 3
- SZVPAOGRUWWLIJ-UHFFFAOYSA-N 1-(2-aminoethylamino)-2-methylpropan-2-ol Chemical compound CC(C)(O)CNCCN SZVPAOGRUWWLIJ-UHFFFAOYSA-N 0.000 claims description 2
- GHKSKVKCKMGRDU-UHFFFAOYSA-N 2-(3-aminopropylamino)ethanol Chemical compound NCCCNCCO GHKSKVKCKMGRDU-UHFFFAOYSA-N 0.000 claims description 2
- XNFWIOGJYCWFBP-UHFFFAOYSA-N 3-(2-aminoethylamino)propane-1,2-diol Chemical compound NCCNCC(O)CO XNFWIOGJYCWFBP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 2
- CWKVFRNCODQPDB-UHFFFAOYSA-N 1-(2-aminoethylamino)propan-2-ol Chemical compound CC(O)CNCCN CWKVFRNCODQPDB-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 239000013078 crystal Substances 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000000243 solution Substances 0.000 description 9
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- KHPZCNJKNIHKPI-UHFFFAOYSA-N 7,10-dichloro-2-methoxybenzo[b][1,5]naphthyridine Chemical compound C1=C(Cl)C=CC2=C(Cl)C3=NC(OC)=CC=C3N=C21 KHPZCNJKNIHKPI-UHFFFAOYSA-N 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N monoethyl amine Natural products CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 5
- 238000009835 boiling Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229930003836 cresol Natural products 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 150000003739 xylenols Chemical class 0.000 description 3
- MQKHDOIYZNMNCO-UHFFFAOYSA-N 10-chloro-2-methoxybenzo[b][1,5]naphthyridine Chemical compound C1=CC=CC2=C(Cl)C3=NC(OC)=CC=C3N=C21 MQKHDOIYZNMNCO-UHFFFAOYSA-N 0.000 description 2
- WWVCYITZVMBKKZ-UHFFFAOYSA-N 2-butoxy-7,10-dichlorobenzo[b][1,5]naphthyridine Chemical compound C1=C(Cl)C=CC2=C(Cl)C3=NC(OCCCC)=CC=C3N=C21 WWVCYITZVMBKKZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 125000004990 dihydroxyalkyl group Chemical group 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 239000012458 free base Substances 0.000 description 2
- 239000012433 hydrogen halide Substances 0.000 description 2
- 229910000039 hydrogen halide Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- RRFCKDPJVCKSJN-UHFFFAOYSA-N 1-(3-aminopropylamino)propan-2-ol Chemical compound CC(O)CNCCCN RRFCKDPJVCKSJN-UHFFFAOYSA-N 0.000 description 1
- XJAYJPQWYAJJDM-UHFFFAOYSA-N 2-[2-[(7-chloro-2-methoxybenzo[b][1,5]naphthyridin-10-yl)amino]ethylamino]ethanol;dihydrochloride Chemical compound Cl.Cl.C1=C(Cl)C=CC2=C(NCCNCCO)C3=NC(OC)=CC=C3N=C21 XJAYJPQWYAJJDM-UHFFFAOYSA-N 0.000 description 1
- SSZWWUDQMAHNAQ-UHFFFAOYSA-N 3-chloropropane-1,2-diol Chemical compound OCC(O)CCl SSZWWUDQMAHNAQ-UHFFFAOYSA-N 0.000 description 1
- XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 1
- IGZHANSFKZYWKS-UHFFFAOYSA-N 7-chloro-2-methoxy-10-phenoxybenzo[b][1,5]naphthyridine Chemical compound C12=NC(OC)=CC=C2N=C2C=C(Cl)C=CC2=C1OC1=CC=CC=C1 IGZHANSFKZYWKS-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000000968 intestinal effect Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 208000014837 parasitic helminthiasis infectious disease Diseases 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000011084 recovery Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 201000004409 schistosomiasis Diseases 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2005254A GB769023A (en) | 1954-07-08 | 1954-07-08 | Improvements in or relating to substituted 1.10-diaza-anthracenes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH337853A true CH337853A (de) | 1959-04-30 |
Family
ID=10139561
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH337853D CH337853A (de) | 1954-07-08 | 1955-07-08 | Verfahren zur Herstellung von 9-substituierten 1,10-Diaza-anthracenen |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE539617A (fr) |
| CH (1) | CH337853A (fr) |
| DE (1) | DE1000387C2 (fr) |
| FR (1) | FR1167511A (fr) |
| GB (1) | GB769023A (fr) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3155685B2 (ja) * | 1995-07-20 | 2001-04-16 | 財団法人山形県企業振興公社 | ペルオキシダーゼの測定方法 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE512362A (fr) * | 1952-06-25 | 1954-01-22 | Ward | Aza acridines comportant un substituant en meso et leur preparation. |
-
1954
- 1954-07-08 GB GB2005254A patent/GB769023A/en not_active Expired
-
1955
- 1955-07-07 FR FR1167511D patent/FR1167511A/fr not_active Expired
- 1955-07-07 DE DE1955W0017038 patent/DE1000387C2/de not_active Expired
- 1955-07-07 BE BE539617A patent/BE539617A/fr unknown
- 1955-07-08 CH CH337853D patent/CH337853A/de unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DE1000387C2 (de) | 1957-06-27 |
| DE1000387B (de) | 1957-01-10 |
| FR1167511A (fr) | 1958-11-26 |
| BE539617A (fr) | 1959-07-17 |
| GB769023A (en) | 1957-02-27 |
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