CA1040199A - 1,5-diazocine derivatives and process for the preparation thereof - Google Patents

1,5-diazocine derivatives and process for the preparation thereof

Info

Publication number: CA1040199A
Authority: CA; Canada
Prior art keywords: process according; formula; formaldehyde; compounds; general formula
Prior art date: 1973-03-30
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.): Expired

Application number

CA196,127A

Other languages

English (en)

French (fr)

Other versions

CA196127S (en

Inventor

Antal Toth

Agnes Udvardy

Gabor Horvath

Agoston David

Istvan Hermecz

Zoltan Meszaros

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Chinoin Private Co Ltd

Original Assignee

Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

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.)

1973-03-30

Filing date

1974-03-27

Publication date

1978-10-10

1974-03-27 Application filed by Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt filed Critical Chinoin Gyogyszer es Vegyeszeti Termekek Gyara Zrt

1978-10-10 Application granted granted Critical

1978-10-10 Publication of CA1040199A publication Critical patent/CA1040199A/en

Status Expired legal-status Critical Current

Links

238000002360 preparation method Methods 0.000 title claims abstract description 6
238000000034 method Methods 0.000 title claims description 20
LLLMDRXIQZOTJE-UHFFFAOYSA-N 1,5-diazocine Chemical class C1=CN=CC=CN=C1 LLLMDRXIQZOTJE-UHFFFAOYSA-N 0.000 title description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims abstract description 34
150000001875 compounds Chemical class 0.000 claims abstract description 24
150000003839 salts Chemical class 0.000 claims abstract description 12
239000002253 acid Substances 0.000 claims abstract description 9
229930040373 Paraformaldehyde Natural products 0.000 claims abstract description 6
229920002866 paraformaldehyde Polymers 0.000 claims abstract description 6
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 5
125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
239000007858 starting material Substances 0.000 claims description 5
239000007864 aqueous solution Substances 0.000 claims description 3
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
239000007787 solid Substances 0.000 claims description 2
238000006243 chemical reaction Methods 0.000 claims 5
239000000126 substance Substances 0.000 claims 3
NCVXEYAKRVJMTQ-UHFFFAOYSA-N 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-3,4-dihydroisoquinoline Chemical compound C1=C(OCC)C(OCC)=CC=C1CC1=NCCC2=CC(OCC)=C(OCC)C=C12 NCVXEYAKRVJMTQ-UHFFFAOYSA-N 0.000 claims 1
BQIIGTSQOCWPDH-UHFFFAOYSA-N 1-benzyl-3,4-dihydroisoquinoline Chemical compound N=1CCC2=CC=CC=C2C=1CC1=CC=CC=C1 BQIIGTSQOCWPDH-UHFFFAOYSA-N 0.000 claims 1
239000012736 aqueous medium Substances 0.000 claims 1
239000000376 reactant Substances 0.000 claims 1
239000000543 intermediate Substances 0.000 abstract description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 4
238000002844 melting Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000243 solution Substances 0.000 description 3
STBFLOYKRMKBRN-UHFFFAOYSA-N 1-[(3,4-diethoxyphenyl)methyl]-6,7-diethoxy-3,4-dihydroisoquinolin-2-ium;chloride Chemical compound [Cl-].C1=C(OCC)C(OCC)=CC=C1CC1=[NH+]CCC2=CC(OCC)=C(OCC)C=C12 STBFLOYKRMKBRN-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
229960000583 acetic acid Drugs 0.000 description 2
239000002585 base Substances 0.000 description 2
239000007853 buffer solution Substances 0.000 description 2
238000009833 condensation Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
239000013078 crystal Substances 0.000 description 2
229910052739 hydrogen Inorganic materials 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
150000007522 mineralic acids Chemical class 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
IOEPOEDBBPRAEI-UHFFFAOYSA-N 1,2-dihydroisoquinoline Chemical class C1=CC=C2CNC=CC2=C1 IOEPOEDBBPRAEI-UHFFFAOYSA-N 0.000 description 1
WQQZXCXGKCQGFU-UHFFFAOYSA-N 1-benzyl-3,4-dihydroisoquinoline;hydrochloride Chemical compound Cl.N=1CCC2=CC=CC=C2C=1CC1=CC=CC=C1 WQQZXCXGKCQGFU-UHFFFAOYSA-N 0.000 description 1
CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical class Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
239000008346 aqueous phase Substances 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 1
239000004327 boric acid Substances 0.000 description 1
244000309464 bull Species 0.000 description 1
238000002512 chemotherapy Methods 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
150000003840 hydrochlorides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
239000011707 mineral Substances 0.000 description 1
239000000203 mixture Substances 0.000 description 1
229940099990 ogen Drugs 0.000 description 1
-1 organic acid salts Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
150000007530 organic bases Chemical class 0.000 description 1
239000012074 organic phase Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
239000002904 solvent Substances 0.000 description 1
238000005292 vacuum distillation Methods 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
- C07D471/14—Ortho-condensed systems
- 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
- C07D487/12—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 three hetero rings
- C07D487/14—Ortho-condensed systems

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CA196,127A 1973-03-30 1974-03-27 1,5-diazocine derivatives and process for the preparation thereof Expired CA1040199A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
HUCI001362 HU166689B (de)	1973-03-30	1973-03-30

Publications (1)

Publication Number	Publication Date
CA1040199A true CA1040199A (en)	1978-10-10

Family

ID=10994474

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA196,127A Expired CA1040199A (en)	1973-03-30	1974-03-27	1,5-diazocine derivatives and process for the preparation thereof

Country Status (9)

Country	Link
JP (1)	JPS5035184A (de)
AT (1)	AT337187B (de)
CA (1)	CA1040199A (de)
CH (1)	CH590281A5 (de)
ES (1)	ES424658A1 (de)
FR (1)	FR2223368B1 (de)
GB (1)	GB1468392A (de)
HU (1)	HU166689B (de)
SU (1)	SU511857A3 (de)

1973
- 1973-03-30 HU HUCI001362 patent/HU166689B/hu unknown
1974
- 1974-03-19 GB GB1214974A patent/GB1468392A/en not_active Expired
- 1974-03-26 ES ES424658A patent/ES424658A1/es not_active Expired
- 1974-03-26 FR FR7410248A patent/FR2223368B1/fr not_active Expired
- 1974-03-27 CA CA196,127A patent/CA1040199A/en not_active Expired
- 1974-03-27 AT AT252574A patent/AT337187B/de not_active IP Right Cessation
- 1974-03-29 CH CH447074A patent/CH590281A5/xx not_active IP Right Cessation
- 1974-03-29 SU SU2011086A patent/SU511857A3/ru active
- 1974-03-30 JP JP3658374A patent/JPS5035184A/ja active Pending

Also Published As

Publication number	Publication date
GB1468392A (en)	1977-03-23
HU166689B (de)	1975-05-28
JPS5035184A (de)	1975-04-03
CH590281A5 (de)	1977-07-29
FR2223368B1 (de)	1976-06-25
ES424658A1 (es)	1976-06-01
SU511857A3 (ru)	1976-04-25
FR2223368A1 (de)	1974-10-25
ATA252574A (de)	1976-10-15
AT337187B (de)	1977-06-10

Publication	Publication Date	Title
SU659081A3 (ru)	1979-04-25	Способ получени фенилэтиламинов или их солей
SU906376A3 (ru)	1982-02-15	Способ получени производных 2-нитроаминопиримидона-4
US3931181A (en)	1976-01-06	2,4-Diamino-5-benzylpyrimidines
CA2005355A1 (en)	1990-06-22	Reduction of piperidine-dion-derivatives and intermediates
Kaczka et al.	1956	Novobiocin. III. Cyclonovobiocic acid, a methyl glycoside, and other reaction products
PL89037B1 (de)	1976-10-30
US2538341A (en)	1951-01-16	Method for producing 1-hydroxyisoquinolines
SU428602A3 (ru)	1974-05-15	Способ получения основпозамещенных производных 1
PL75064B1 (de)	1974-12-31
US4486597A (en)	1984-12-04	Method for the production of nuclear substituted cinnamoylanthranilic acid derivatives
Taborsky	1961	Preparation of 5-Hydroxy-4, 6-dimethyl-3-pyridinemethanol (4-Desoxypyridoxine) by the use of Hydrazine
US2640830A (en)	1953-06-02	S-hydroxy-x
US2942001A (en)	1960-06-21	Piperazo-pyridazines
US4658035A (en)	1987-04-14	Preparation of 2-alkyl-4,5-dihydroxymethylimidazoles
CA1237432A (en)	1988-05-31	Isoquinoline derivatives, process for their preparation and pharmaceutical compositions containing them
USRE29467E (en)	1977-11-08	Benzylcyano-amides
SU691087A3 (ru)	1979-10-05	Способ получени производных 6,7диметокси-1,2,3,4-тетрагидро-1-изохинолин-ацетамида или их солей
CA1071627A (en)	1980-02-12	Pyrimidine derivatives
Manske et al.	1951	The Alkaloids of Fumariaceous Plants. XLVI. The Structure of Glaucentrine
US3507887A (en)	1970-04-21	Process of preparing 2-alkyl quinizarins and 2-aryl-methylene quinizarins
CA1092117A (en)	1980-12-23	Method for the production of 6,7-dimethoxy-4-amino-2- ¬4-(2-furoyl)-1-piperazinyl\| quinazoline having an antihypertensive effect
CA2044603A1 (en)	1991-05-18	Method for the preparation of .alpha.,.beta.-unsaturated ketones
SU511857A3 (ru)	1976-04-25	Способ получени производных 1,5-диазоцина
US3991082A (en)	1976-11-09	4-Substituted-2,3-dihydro-1-benzoxepin-3,5-diones and tautomers
US3933807A (en)	1976-01-20	Preparation of cyanophenols