SU539524A3 - Способ получени производных изохинолина - Google Patents

Способ получени производных изохинолина

Info

Publication number: SU539524A3
Authority: SU; USSR - Soviet Union
Prior art keywords: dihydroisoquinoline; amino; yield; solution; mixture
Prior art date: 1971-03-18

Application number

SU1755679A

Other languages

English (en)

Russian (ru)

Inventor

Винтерс Джорджио

Натанзон Джанджакомо

Одассо Джанфранко

Original Assignee

Группо Лепетит С.П.А. (Фирма)

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.)

1971-03-18

Filing date

1972-03-15

Publication date

1976-12-15

1972-03-15 Application filed by Группо Лепетит С.П.А. (Фирма) filed Critical Группо Лепетит С.П.А. (Фирма)

1976-12-15 Application granted granted Critical

1976-12-15 Publication of SU539524A3 publication Critical patent/SU539524A3/ru

Links

238000000034 method Methods 0.000 title description 6
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
239000000203 mixture Substances 0.000 description 12
239000000243 solution Substances 0.000 description 12
-1 hydroxy- Chemical class 0.000 description 11
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
125000000217 alkyl group Chemical group 0.000 description 7
239000000155 melt Substances 0.000 description 7
IYANYSZUKHQLKL-UHFFFAOYSA-N 3,4-dihydro-1h-isoquinolin-2-amine Chemical compound C1=CC=C2CN(N)CCC2=C1 IYANYSZUKHQLKL-UHFFFAOYSA-N 0.000 description 6
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
238000001816 cooling Methods 0.000 description 4
GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-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
239000002262 Schiff base Substances 0.000 description 3
150000004753 Schiff bases Chemical class 0.000 description 3
239000002253 acid Substances 0.000 description 3
DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
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 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
150000007513 acids Chemical class 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
125000003545 alkoxy group Chemical group 0.000 description 2
125000003282 alkyl amino group Chemical group 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical compound OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 2
229940092714 benzenesulfonic acid Drugs 0.000 description 2
238000009835 boiling Methods 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
OUQVKRKGTAUJQA-UHFFFAOYSA-N n-[(1-chloro-4-hydroxyisoquinolin-3-yl)carbonyl]glycine Chemical compound C1=CC=CC2=C(O)C(C(=O)NCC(=O)O)=NC(Cl)=C21 OUQVKRKGTAUJQA-UHFFFAOYSA-N 0.000 description 2
QKFJKGMPGYROCL-UHFFFAOYSA-N phenyl isothiocyanate Chemical compound S=C=NC1=CC=CC=C1 QKFJKGMPGYROCL-UHFFFAOYSA-N 0.000 description 2
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
238000010992 reflux Methods 0.000 description 2
229910000029 sodium carbonate Inorganic materials 0.000 description 2
229910052938 sodium sulfate Inorganic materials 0.000 description 2
235000011152 sodium sulphate Nutrition 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000725 suspension Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
BOMIIKYVZJCFQV-UHFFFAOYSA-N 1h-isoquinolin-2-amine Chemical compound C1=CC=C2C=CN(N)CC2=C1 BOMIIKYVZJCFQV-UHFFFAOYSA-N 0.000 description 1
PKRRIFLRGGRFQO-UHFFFAOYSA-N 2-(2-chloroethyl)benzoyl chloride Chemical compound ClCCC1=CC=CC=C1C(Cl)=O PKRRIFLRGGRFQO-UHFFFAOYSA-N 0.000 description 1
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
RKIDDEGICSMIJA-UHFFFAOYSA-N 4-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=C(Cl)C=C1 RKIDDEGICSMIJA-UHFFFAOYSA-N 0.000 description 1
CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 description 1
ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
229930194542 Keto Natural products 0.000 description 1
CRZQGDNQQAALAY-UHFFFAOYSA-N Me ester-Phenylacetic acid Natural products COC(=O)CC1=CC=CC=C1 CRZQGDNQQAALAY-UHFFFAOYSA-N 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
239000003929 acidic solution Substances 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000002252 acyl group Chemical group 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
125000002947 alkylene group Chemical group 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
150000003934 aromatic aldehydes Chemical class 0.000 description 1
125000003710 aryl alkyl group Chemical group 0.000 description 1
125000004429 atom Chemical group 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001558 benzoic acid derivatives Chemical class 0.000 description 1
PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
125000002843 carboxylic acid group Chemical group 0.000 description 1
150000001735 carboxylic acids Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
150000001912 cyanamides Chemical class 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
FDSGHYHRLSWSLQ-UHFFFAOYSA-N dichloromethane;propan-2-one Chemical compound ClCCl.CC(C)=O FDSGHYHRLSWSLQ-UHFFFAOYSA-N 0.000 description 1
YXEGAERXMNFHIX-UHFFFAOYSA-N ethyl 2-(2-chloroethyl)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1CCCl YXEGAERXMNFHIX-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
229940117360 ethyl pyruvate Drugs 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
238000001914 filtration Methods 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
239000012458 free base Substances 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
125000004970 halomethyl group Chemical group 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
229910000041 hydrogen chloride Inorganic materials 0.000 description 1
ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
GRHBQAYDJPGGLF-UHFFFAOYSA-N isothiocyanic acid Chemical compound N=C=S GRHBQAYDJPGGLF-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
229940117953 phenylisothiocyanate Drugs 0.000 description 1
125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
239000000047 product Substances 0.000 description 1
239000012279 sodium borohydride Substances 0.000 description 1
229910000033 sodium borohydride Inorganic materials 0.000 description 1
ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1

Landscapes

Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Plural Heterocyclic Compounds (AREA)

SU1755679A 1971-03-18 1972-03-15 Способ получени производных изохинолина SU539524A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT2193171		1971-03-18

Publications (1)

Publication Number	Publication Date
SU539524A3 true SU539524A3 (ru)	1976-12-15

Family

ID=11188981

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU1755679A SU539524A3 (ru)	1971-03-18	1972-03-15	Способ получени производных изохинолина

Country Status (4)

Country	Link
AT (1)	AT319945B (de)
CA (1)	CA984390A (de)
SU (1)	SU539524A3 (de)
ZA (1)	ZA72986B (de)

1972
- 1972-02-15 ZA ZA720986A patent/ZA72986B/xx unknown
- 1972-03-15 SU SU1755679A patent/SU539524A3/ru active
- 1972-03-16 AT AT224072A patent/AT319945B/de not_active IP Right Cessation
- 1972-03-17 CA CA137,383A patent/CA984390A/en not_active Expired

Also Published As

Publication number	Publication date
ZA72986B (en)	1972-10-25
AT319945B (de)	1975-01-10
CA984390A (en)	1976-02-24

Publication	Publication Date	Title
EP0109023B1 (de)	1987-03-25	Isochinolin-sulfonamidderivate und Verfahren für ihre Herstellung
KR940000828B1 (ko)	1994-02-02	항혈전성 강심제 이미다조 퀴놀린의 제조방법
SU451244A3 (ru)	1974-11-25	Способ получени производных фенилимидазолилалкила
SHERMAN	1961	5-Nitro-2-furyl-substituted 1, 3, 4-Oxadiazoles, 1, 3, 4-Thiadiazoles, and 1, 3, 5-Triazines1
US3632645A (en)	1972-01-04	Substituted phenylacetyl derivatives of guanidine o-alkylisoureas s-alkylisothioureas and p-nitrobenzylisothiourea
FI59990C (fi)	1981-11-10	Foerfarande foer framstaellning av pao centralnervsystemet verkande racemiska eller optiskt aktiva arylpiperaziner samt deras syraadditionssalter
US4188486A (en)	1980-02-12	2-Substituted benzimidazole compounds
JPH0471914B2 (de)	1992-11-16
CA1337426C (en)	1995-10-24	Process for the preparation of herbicidal 2-(4,4- disubstituted 5-oxo-2-imidazolin-2-yl)benzoic, nicotinic and quinoline-3-carboxylic acids, esters and salts
FI81578C (fi)	1990-11-12	Foerfarande foer framstaellning av nya fosfodiesterasinhibierande 1,2,3,5-tetrahydroimidazo/2,1-b/ kinazolinderivat.
PL142626B1 (en)	1987-11-30	Method of obtaining novel derivatives of aminoguanidine
SU539528A3 (ru)	1976-12-15	Способ получени производных 2оксазолина
US4291039A (en)	1981-09-22	Tetrahydro β-carbolines having anti-hypertensive activity
US3673188A (en)	1972-06-27	Heterocyclic amidoximes
US3468888A (en)	1969-09-23	2-substituted pyrimido(1,2-a) benzimidazoles
FI85473B (fi)	1992-01-15	Foerfarande foer framstaellning av nya terapeutiskt anvaendbara 4-(isoxazolyl)-tiazol-2-oxaminsyraderivat och mellanprodukter.
US3449357A (en)	1969-06-10	2-((2,6-substituted)phenoxymethyl)-2-imidazolines
SE410460B (sv)	1979-10-15	Forfarande for framstellning av imidazoforeningar
SU368752A1 (de)
SU470959A3 (ru)	1975-05-15	Способ получени 3-амино- 2-пиразолиновых производных или их солей
US3740413A (en)	1973-06-19	2-benzimidazolecarboxamides
SU591150A3 (ru)	1978-01-30	Способ получени производных нитроимидазолилтриазолопиридазина или их солей
KR100235376B1 (ko)	1999-12-15	2-아미노나프티리딘 유도체 그의 제조 방법
US3886147A (en)	1975-05-27	Tranquilizers
US3182063A (en)	1965-05-04	Substituted 4-thiazolidinones and process therefor