HU183330B - Process for producing new of 2,4,8-triazaphenalenium-salts - Google Patents

Process for producing new of 2,4,8-triazaphenalenium-salts Download PDF

Info

Publication number: HU183330B
Authority: HU; Hungary
Prior art keywords: formula; alkyl; hydrogen; phenyl; alkoxy
Prior art date: 1981-02-13

Application number

HU35281A

Other languages

English (en)

Hungarian (hu)

Inventor

Istvan Bitter

Bela Pete

Istvan Hermecz

Zoltan Meszaros

Agnes Horvath

DEBRECZY Lelle VASVARINE

Original Assignee

Chinoin Gyogyszer Es Vegyeszet

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.)

1981-02-13

Filing date

1981-02-13

Publication date

1984-04-28

1981-02-13 Application filed by Chinoin Gyogyszer Es Vegyeszet filed Critical Chinoin Gyogyszer Es Vegyeszet

1981-02-13 Priority to HU35281A priority Critical patent/HU183330B/hu

1982-02-09 Priority to AT47682A priority patent/AT381094B/de

1982-02-11 Priority to FR8202236A priority patent/FR2499993B1/fr

1982-02-11 Priority to GB8203978A priority patent/GB2093024B/en

1982-02-12 Priority to BE0/207301A priority patent/BE892120A/fr

1982-02-12 Priority to CH89682A priority patent/CH653031A5/de

1984-04-28 Publication of HU183330B publication Critical patent/HU183330B/hu

Links

238000000034 method Methods 0.000 title claims description 9
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 29
239000001257 hydrogen Substances 0.000 claims abstract description 29
150000001875 compounds Chemical class 0.000 claims abstract description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 18
150000002431 hydrogen Chemical class 0.000 claims abstract description 17
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 14
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 12
150000003839 salts Chemical class 0.000 claims abstract description 12
229910052736 halogen Inorganic materials 0.000 claims abstract description 11
150000002367 halogens Chemical class 0.000 claims abstract description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 9
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 6
125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 3
125000000217 alkyl group Chemical group 0.000 claims description 11
-1 ammonium ions Chemical class 0.000 claims description 7
150000001540 azides Chemical class 0.000 claims description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 6
VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical group OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 6
238000002360 preparation method Methods 0.000 claims description 6
239000002904 solvent Substances 0.000 claims description 6
229910002651 NO3 Inorganic materials 0.000 claims description 5
NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 claims description 5
ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 5
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 claims description 5
125000003545 alkoxy group Chemical group 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
VFMCUTPRJLZEEW-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine Chemical class C1=CC=CN2CC=CN=C21 VFMCUTPRJLZEEW-UHFFFAOYSA-N 0.000 claims description 2
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 claims description 2
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000005843 halogen group Chemical group 0.000 claims description 2
230000003287 optical effect Effects 0.000 claims description 2
229910052700 potassium Inorganic materials 0.000 claims description 2
239000011591 potassium Substances 0.000 claims description 2
229910052708 sodium Inorganic materials 0.000 claims description 2
239000011734 sodium Substances 0.000 claims description 2
239000000460 chlorine Substances 0.000 claims 2
150000008518 pyridopyrimidines Chemical class 0.000 claims 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
150000001450 anions Chemical group 0.000 abstract description 3
125000003710 aryl alkyl group Chemical group 0.000 abstract 2
125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
230000001088 anti-asthma Effects 0.000 abstract 1
150000002825 nitriles Chemical class 0.000 abstract 1
239000000126 substance Substances 0.000 abstract 1
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 33
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 23
239000000047 product Substances 0.000 description 13
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000000921 elemental analysis Methods 0.000 description 6
238000004458 analytical method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
239000000203 mixture Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
125000001424 substituent group Chemical group 0.000 description 4
DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 3
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 3
150000001805 chlorine compounds Chemical group 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
CSOYDALHEQEMAK-UHFFFAOYSA-N 2h-pyrimidine-1-carboxylic acid Chemical compound OC(=O)N1CN=CC=C1 CSOYDALHEQEMAK-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000001914 filtration Methods 0.000 description 2
238000011081 inoculation Methods 0.000 description 2
239000000543 intermediate Substances 0.000 description 2
FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
229940126585 therapeutic drug Drugs 0.000 description 2
LRJPMJWJATWOEW-JTTJXQCZSA-N (2r)-2-[[4-[[[2-(2,4-dioxo-1h-quinazolin-3-yl)acetyl]amino]methyl]cyclohexanecarbonyl]amino]-4-methylsulfanylbutanoic acid Chemical compound C1CC(C(=O)N[C@H](CCSC)C(O)=O)CCC1CNC(=O)CN1C(=O)C2=CC=CC=C2NC1=O LRJPMJWJATWOEW-JTTJXQCZSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
FPXDWQCNXFONMN-UHFFFAOYSA-N 4h-pyrido[1,2-a]pyrimidine-3-carboxylic acid Chemical compound C1=CC=CN2CC(C(=O)O)=CN=C21 FPXDWQCNXFONMN-UHFFFAOYSA-N 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
238000005481 NMR spectroscopy Methods 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001447 alkali salts Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
238000005349 anion exchange Methods 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
244000309464 bull Species 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
KNZYMKYLCIPERV-UHFFFAOYSA-N dichloromethanimine;hydrochloride Chemical compound [Cl-].ClC(Cl)=[NH2+] KNZYMKYLCIPERV-UHFFFAOYSA-N 0.000 description 1
230000029087 digestion Effects 0.000 description 1
125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
LJQKCYFTNDAAPC-UHFFFAOYSA-N ethanol;ethyl acetate Chemical compound CCO.CCOC(C)=O LJQKCYFTNDAAPC-UHFFFAOYSA-N 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000001640 fractional crystallisation Methods 0.000 description 1
PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
239000010931 gold Substances 0.000 description 1
229910052737 gold Inorganic materials 0.000 description 1
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000002156 mixing Methods 0.000 description 1
HXTGGPKOEKKUQO-UHFFFAOYSA-N n-methyl-1-phenylmethanimine Chemical compound CN=CC1=CC=CC=C1 HXTGGPKOEKKUQO-UHFFFAOYSA-N 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
235000010333 potassium nitrate Nutrition 0.000 description 1
239000004323 potassium nitrate Substances 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
BAZAXWOYCMUHIX-UHFFFAOYSA-M sodium perchlorate Chemical compound [Na+].[O-]Cl(=O)(=O)=O BAZAXWOYCMUHIX-UHFFFAOYSA-M 0.000 description 1
229910001488 sodium perchlorate Inorganic materials 0.000 description 1
239000007858 starting material Substances 0.000 description 1
150000003573 thiols Chemical class 0.000 description 1
230000017105 transposition Effects 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
- C07D471/12—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 three hetero rings
- C07D471/16—Peri-condensed systems
- 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
- C07D471/22—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 systems contains four or more hetero rings

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)

HU35281A 1981-02-13 1981-02-13 Process for producing new of 2,4,8-triazaphenalenium-salts HU183330B (en)

Priority Applications (6)

Application Number	Priority Date	Filing Date	Title
HU35281A HU183330B (en)	1981-02-13	1981-02-13	Process for producing new of 2,4,8-triazaphenalenium-salts
AT47682A AT381094B (de)	1981-02-13	1982-02-09	Verfahren zur herstellung von neuen 2, 4, 8-triazaphenalenium-salzen sowie von deren geometrischen und optischen isomeren
FR8202236A FR2499993B1 (fr)	1981-02-13	1982-02-11	Sels de 2, 4, 8-triazaphenalenium et procede pour leur preparation
GB8203978A GB2093024B (en)	1981-02-13	1982-02-11	2,4,8-triazaphenalenium salts and their preparation
BE0/207301A BE892120A (fr)	1981-02-13	1982-02-12	Sels de 2,4,8-triazaphenalenium et procede pour leur preparation
CH89682A CH653031A5 (en)	1981-02-13	1982-02-12	2,4,8-Triazaphenalenium salts and process for their preparation

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HU35281A HU183330B (en)	1981-02-13	1981-02-13	Process for producing new of 2,4,8-triazaphenalenium-salts

Publications (1)

Publication Number	Publication Date
HU183330B true HU183330B (en)	1984-04-28

Family

ID=10949203

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
HU35281A HU183330B (en)	1981-02-13	1981-02-13	Process for producing new of 2,4,8-triazaphenalenium-salts

Country Status (6)

Country	Link
AT (1)	AT381094B (de)
BE (1)	BE892120A (de)
CH (1)	CH653031A5 (de)
FR (1)	FR2499993B1 (de)
GB (1)	GB2093024B (de)
HU (1)	HU183330B (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4698092A (en) *	1986-01-24	1987-10-06	American Cynamid Company	5H-imidazo[2',1':4,3]imidazo-[1,5a]pyridin-6-ium salts and their use as herbicidal agents
RU2498986C2 (ru) *	2011-07-20	2013-11-20	Учреждение Российской Академии Наук Институт Проблем Химической Физики Ран (Ипхф Ран)	ТЕТРАЦИАНОЗАМЕЩЕННЫЕ 1,4,9b-ТРИАЗАФЕНАЛЕНЫ И СПОСОБ ИХ ПОЛУЧЕНИЯ

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
HU180439B (en) *	1977-12-29	1983-03-28	Chinoin Gyogyszer Es Vegyeszet	Process for producing 9-amino-pyrido-square bracket-1,2-a-square bracket closed-pyrimidine derivatives
HU185925B (en) *	1977-12-29	1985-04-28	Chinoin Gyogyszer Es Vegyeszet	Process for preparing compounds with nitrogen bridge head

1981
- 1981-02-13 HU HU35281A patent/HU183330B/hu not_active IP Right Cessation
1982
- 1982-02-09 AT AT47682A patent/AT381094B/de not_active IP Right Cessation
- 1982-02-11 FR FR8202236A patent/FR2499993B1/fr not_active Expired
- 1982-02-11 GB GB8203978A patent/GB2093024B/en not_active Expired
- 1982-02-12 CH CH89682A patent/CH653031A5/de not_active IP Right Cessation
- 1982-02-12 BE BE0/207301A patent/BE892120A/fr unknown

Also Published As

Publication number	Publication date
ATA47682A (de)	1986-01-15
GB2093024B (en)	1984-09-05
FR2499993B1 (fr)	1985-09-06
CH653031A5 (en)	1985-12-13
FR2499993A1 (fr)	1982-08-20
BE892120A (fr)	1982-05-27
GB2093024A (en)	1982-08-25
AT381094B (de)	1986-08-25

Legal Events

Date	Code	Title	Description
1990-06-28	HU90	Patent valid on 900628
1991-01-28	HMM4	Cancellation of final prot. due to non-payment of fee

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