SU862820A3 - Способ получени производных изохинолини - Google Patents

Способ получени производных изохинолини Download PDF

Info

Publication number: SU862820A3
Authority: SU; USSR - Soviet Union
Prior art keywords: mixture; filtered; mmol; ether; bromide
Prior art date: 1977-08-01

Application number

SU782646252A

Other languages

English (en)

Russian (ru)

Inventor

Дж. Савариз Джон

Дж.Китз Ричард

Джинберг Сара

Original Assignee

Дзе Массачусетс Дженерал Хоспитал (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.)

1977-08-01

Filing date

1978-07-31

Publication date

1981-09-07

1978-07-31 Application filed by Дзе Массачусетс Дженерал Хоспитал (Фирма) filed Critical Дзе Массачусетс Дженерал Хоспитал (Фирма)

1981-09-07 Application granted granted Critical

1981-09-07 Publication of SU862820A3 publication Critical patent/SU862820A3/ru

Links

AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical class C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 title 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 22
150000001875 compounds Chemical class 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
230000002441 reversible effect Effects 0.000 abstract description 2
125000003545 alkoxy group Chemical group 0.000 abstract 2
125000004432 carbon atom Chemical group C* 0.000 abstract 2
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 1
125000000217 alkyl group Chemical group 0.000 abstract 1
150000001450 anions Chemical class 0.000 abstract 1
239000003937 drug carrier Substances 0.000 abstract 1
229910052739 hydrogen Inorganic materials 0.000 abstract 1
239000001257 hydrogen Substances 0.000 abstract 1
230000003387 muscular Effects 0.000 abstract 1
239000000842 neuromuscular blocking agent Substances 0.000 abstract 1
238000001356 surgical procedure Methods 0.000 abstract 1
239000000203 mixture Substances 0.000 description 22
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
239000011347 resin Substances 0.000 description 13
229920005989 resin Polymers 0.000 description 13
-1 3-chloropropyl Chemical group 0.000 description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
238000009835 boiling Methods 0.000 description 11
239000002253 acid Substances 0.000 description 10
238000002360 preparation method Methods 0.000 description 10
239000007787 solid Substances 0.000 description 10
239000000243 solution Substances 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 9
CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 8
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
150000002148 esters Chemical class 0.000 description 7
229910052709 silver Inorganic materials 0.000 description 7
239000004332 silver Substances 0.000 description 7
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
239000002244 precipitate Substances 0.000 description 6
239000000047 product Substances 0.000 description 6
125000005806 3,4,5-trimethoxybenzyl group Chemical group [H]C1=C(OC([H])([H])[H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1C([H])([H])* 0.000 description 5
150000001649 bromium compounds Chemical group 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
238000010438 heat treatment Methods 0.000 description 5
239000012535 impurity Substances 0.000 description 5
239000000463 material Substances 0.000 description 5
238000001556 precipitation Methods 0.000 description 5
GGCZERPQGJTIQP-UHFFFAOYSA-N sodium;9,10-dioxoanthracene-2-sulfonic acid Chemical compound [Na+].C1=CC=C2C(=O)C3=CC(S(=O)(=O)O)=CC=C3C(=O)C2=C1 GGCZERPQGJTIQP-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
230000008707 rearrangement Effects 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
239000002344 surface layer Substances 0.000 description 4
XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
238000002156 mixing Methods 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000000126 substance Substances 0.000 description 3
HGXJNYNUTHMEOS-UHFFFAOYSA-N (4-propanoyloxyphenyl) propanoate Chemical compound CCC(=O)OC1=CC=C(OC(=O)CC)C=C1 HGXJNYNUTHMEOS-UHFFFAOYSA-N 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
238000004945 emulsification Methods 0.000 description 2
125000001033 ether group Chemical group 0.000 description 2
239000012458 free base Substances 0.000 description 2
239000011521 glass Substances 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
KGPAYJZAMGEDIQ-UHFFFAOYSA-N laudanosine Natural products C1=C(OC)C(OC)=CC=C1CC1C2=CC(OC)=C(OC)C=C2CCN1C KGPAYJZAMGEDIQ-UHFFFAOYSA-N 0.000 description 2
238000002844 melting Methods 0.000 description 2
230000008018 melting Effects 0.000 description 2
230000035484 reaction time Effects 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000011701 zinc Substances 0.000 description 2
229910052725 zinc Inorganic materials 0.000 description 2
KTXHVIOWGMWEEY-UHFFFAOYSA-N (4-propanoyloxyphenyl) propanoate;silver Chemical compound [Ag].CCC(=O)OC1=CC=C(OC(=O)CC)C=C1 KTXHVIOWGMWEEY-UHFFFAOYSA-N 0.000 description 1
DIVRAHZSTAIUNB-UHFFFAOYSA-N 3-[3-(2-carboxyethyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=CC(CCC(O)=O)=C1 DIVRAHZSTAIUNB-UHFFFAOYSA-N 0.000 description 1
DFOCUWFSRVQSNI-UHFFFAOYSA-N 3-[4-(2-carboxyethyl)phenyl]propanoic acid Chemical compound OC(=O)CCC1=CC=C(CCC(O)=O)C=C1 DFOCUWFSRVQSNI-UHFFFAOYSA-N 0.000 description 1
101100520660 Drosophila melanogaster Poc1 gene Proteins 0.000 description 1
101000686031 Homo sapiens Proto-oncogene tyrosine-protein kinase ROS Proteins 0.000 description 1
MFESCIUQSIBMSM-UHFFFAOYSA-N I-BCP Chemical class ClCCCBr MFESCIUQSIBMSM-UHFFFAOYSA-N 0.000 description 1
KGPAYJZAMGEDIQ-KRWDZBQOSA-N Laudanosine Chemical compound C1=C(OC)C(OC)=CC=C1C[C@H]1C2=CC(OC)=C(OC)C=C2CCN1C KGPAYJZAMGEDIQ-KRWDZBQOSA-N 0.000 description 1
102100023347 Proto-oncogene tyrosine-protein kinase ROS Human genes 0.000 description 1
101100520662 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) PBA1 gene Proteins 0.000 description 1
KACHGUUUPUYOLN-UHFFFAOYSA-N [Ag].CCC(=O)OC1=CC=CC(OC(=O)CC)=C1 Chemical compound [Ag].CCC(=O)OC1=CC=CC(OC(=O)CC)=C1 KACHGUUUPUYOLN-UHFFFAOYSA-N 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
238000006243 chemical reaction Methods 0.000 description 1
239000012065 filter cake Substances 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
FGPUFQRNZGCKQV-UHFFFAOYSA-N n-[2-(3,4-dimethoxyphenyl)ethyl]-2-(3,4,5-trimethoxyphenyl)acetamide Chemical compound C1=C(OC)C(OC)=CC=C1CCNC(=O)CC1=CC(OC)=C(OC)C(OC)=C1 FGPUFQRNZGCKQV-UHFFFAOYSA-N 0.000 description 1
SNMVRZFUUCLYTO-UHFFFAOYSA-N n-propyl chloride Chemical compound CCCCl SNMVRZFUUCLYTO-UHFFFAOYSA-N 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000012260 resinous material Substances 0.000 description 1
239000012266 salt solution Substances 0.000 description 1
239000011345 viscous material Substances 0.000 description 1
UGZADUVQMDAIAO-UHFFFAOYSA-L zinc hydroxide Chemical compound [OH-].[OH-].[Zn+2] UGZADUVQMDAIAO-UHFFFAOYSA-L 0.000 description 1
229940007718 zinc hydroxide Drugs 0.000 description 1
229910021511 zinc hydroxide Inorganic materials 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/12—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring
- C07D217/18—Aralkyl radicals
- C07D217/20—Aralkyl radicals with oxygen atoms directly attached to the aromatic ring of said aralkyl radical, e.g. papaverine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Medicinal Chemistry (AREA)
Pain & Pain Management (AREA)
Orthopedic Medicine & Surgery (AREA)
Physical Education & Sports Medicine (AREA)
Bioinformatics & Cheminformatics (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Neurology (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Other In-Based Heterocyclic Compounds (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

SU782646252A 1977-08-01 1978-07-31 Способ получени производных изохинолини SU862820A3 (ru)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US82079477A	1977-08-01	1977-08-01

Publications (1)

Publication Number	Publication Date
SU862820A3 true SU862820A3 (ru)	1981-09-07

Family

ID=25231743

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
SU782646252A SU862820A3 (ru)	1977-08-01	1978-07-31	Способ получени производных изохинолини

Country Status (21)

Country	Link
JP (1)	JPS5455577A (de)
AT (1)	AT368496B (de)
AU (1)	AU523706B2 (de)
BE (1)	BE869415A (de)
CA (1)	CA1113096A (de)
DD (1)	DD143254A5 (de)
DE (1)	DE2833505A1 (de)
DK (1)	DK339078A (de)
ES (1)	ES472229A1 (de)
FI (1)	FI782363A7 (de)
FR (1)	FR2399429A1 (de)
GB (1)	GB2002758B (de)
IE (1)	IE47014B1 (de)
IL (1)	IL55254A (de)
LU (1)	LU80062A1 (de)
MC (1)	MC1197A1 (de)
NL (1)	NL7808067A (de)
PL (1)	PL121492B1 (de)
SE (1)	SE7808267L (de)
SU (1)	SU862820A3 (de)
ZA (1)	ZA784331B (de)

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA1125287A (en) *	1978-07-21	1982-06-08	John J. Savarese	Bis isoquinolinium compositions and methods of use
US4235906A (en)	1978-07-21	1980-11-25	Massachusetts General Hospital	Bis-isoquinolinium compounds, compositions and methods of use
JPS5645459A (en) *	1979-09-20	1981-04-25	Otsuka Pharmaceut Co Ltd	Cyclic amine
JPS5899465A (ja) *	1981-11-23	1983-06-13	ザ・ウエルカム・フアウンデ−シヨン・リミテツド	イソキノリン誘導体
GB8418303D0 (en) *	1984-07-18	1984-08-22	Wellcome Found	Compounds
JPH0555438A (ja) *	1991-08-26	1993-03-05	Rohm Co Ltd	電子部品のリード端子構造
CN1203061C (zh) *	1997-03-25	2005-05-25	艾弗拉药品公司	取代异喹啉类，其制备方法，药物组合物及其制药用途
AU2007328210B2 (en) *	2006-12-06	2012-11-22	Cornell Research Foundation, Inc.	Intermediate duration neuromuscular blocking agents and antagonists thereof
US8592451B2 (en)	2009-03-17	2013-11-26	Cornell University	Reversible nondepolarizing neuromuscular blockade agents and methods for their use
US9220700B2 (en)	2009-08-19	2015-12-29	Cornell University	Cysteine for physiological injection
CN114057642B (zh) *	2021-12-10	2023-03-28	广东嘉博制药有限公司	一种米库氯铵中间体的合成方法

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS5156762U (de) *	1974-10-28	1976-05-04

1978
- 1978-07-31 NL NL787808067A patent/NL7808067A/xx not_active Application Discontinuation
- 1978-07-31 FR FR7822577A patent/FR2399429A1/fr active Granted
- 1978-07-31 DK DK339078A patent/DK339078A/da not_active Application Discontinuation
- 1978-07-31 ZA ZA00784331A patent/ZA784331B/xx unknown
- 1978-07-31 DD DD78207041A patent/DD143254A5/de unknown
- 1978-07-31 BE BE189624A patent/BE869415A/xx not_active IP Right Cessation
- 1978-07-31 SE SE7808267A patent/SE7808267L/xx unknown
- 1978-07-31 JP JP9353778A patent/JPS5455577A/ja active Pending
- 1978-07-31 AU AU38476/78A patent/AU523706B2/en not_active Expired
- 1978-07-31 MC MC781316A patent/MC1197A1/fr unknown
- 1978-07-31 DE DE19782833505 patent/DE2833505A1/de not_active Withdrawn
- 1978-07-31 IE IE1550/78A patent/IE47014B1/en unknown
- 1978-07-31 ES ES472229A patent/ES472229A1/es not_active Expired
- 1978-07-31 AT AT0555478A patent/AT368496B/de not_active IP Right Cessation
- 1978-07-31 GB GB7831697A patent/GB2002758B/en not_active Expired
- 1978-07-31 PL PL1978208757A patent/PL121492B1/pl unknown
- 1978-07-31 CA CA308,434A patent/CA1113096A/en not_active Expired
- 1978-07-31 IL IL55254A patent/IL55254A/xx unknown
- 1978-07-31 SU SU782646252A patent/SU862820A3/ru active
- 1978-07-31 FI FI782363A patent/FI782363A7/fi not_active Application Discontinuation
- 1978-07-31 LU LU80062A patent/LU80062A1/xx unknown

Also Published As

Publication number	Publication date
BE869415A (fr)	1979-01-31
GB2002758A (en)	1979-02-28
PL121492B1 (en)	1982-05-31
GB2002758B (en)	1982-02-03
AU523706B2 (en)	1982-08-12
LU80062A1 (fr)	1979-05-15
IE47014B1 (en)	1983-11-30
ZA784331B (en)	1979-12-27
FR2399429B1 (de)	1981-07-17
ES472229A1 (es)	1979-03-16
ATA555478A (de)	1982-02-15
AT368496B (de)	1982-10-11
DD143254A5 (de)	1980-08-13
DE2833505A1 (de)	1979-04-05
NL7808067A (nl)	1979-02-05
MC1197A1 (fr)	1979-03-19
SE7808267L (sv)	1979-02-02
FR2399429A1 (fr)	1979-03-02
JPS5455577A (en)	1979-05-02
IL55254A (en)	1983-03-31
DK339078A (da)	1979-02-02
IL55254A0 (en)	1978-09-29
PL208757A1 (pl)	1979-06-04
IE781550L (en)	1979-02-01
CA1113096A (en)	1981-11-24
FI782363A7 (fi)	1979-02-02
AU3847678A (en)	1980-02-07

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JPS60246386A (ja)	1985-12-06	新規ピロロ―ベンズイミダゾール、これを含有する心臓―および循環器疾患の予防ないしは治療用医薬
US3266990A (en)	1966-08-16	Derivatives of quinazoline
US2489235A (en)	1949-11-22	Synthesis of biotin
CA1184910A (en)	1985-04-02	Tricyclic cytosine derivatives for combatting circulatory illnesses
SU873887A3 (ru)	1981-10-15	Способ получени производных имидазо/2,1-в/тиазолина или имидазо /2,1-в/тиазина или их кислотно-аддитивных солей,в виде смеси изомеров или отдельных изомеров
SU566524A3 (ru)	1977-07-25	Способ получени производных пиридо(1,2-а)-пиримидина или их солей
DE3335472C2 (de)	1989-08-03
US2895956A (en)	1959-07-21	Synthesis of furoquinoline derivatives
EP0138137B1 (de)	1987-07-22	4-Thioxo-benzopyrano(2,3-d)pyrimidin-derivate sowie Verfahren zu deren Herstellung
SU578869A3 (ru)	1977-10-30	Способ получени 4-окси-3-нитрокарбостирилов
US3108108A (en)	1963-10-22	Aza analogues of polynuclear o-quinones
US3997547A (en)	1976-12-14	Phenylimino-2H-quinolizines
US2728769A (en)	1955-12-27	Alkoxybenzylisoquinolines and salts thereof
CA2054569A1 (en)	1992-05-08	Process for preparing benzo¬c\|phenanthridinium derivatives, and novel compounds prepared by said process
US3379735A (en)	1968-04-23	Sulfamyl aniline derivatives
Dutcher et al.	1944	Gliotoxin, the antibiotic principle of Gliocladium fimbriatum. IV. The structure of gliotoxin: The action of selenium
Beaton et al.	1987	Preparation and hydrogen bonding studies of phenylhydrazone derivatives of alloxan: crystal and molecular structure of pyrimidine-2 (1 H), 4 (3 H), 5, 6-tetraone 5-(2-nitrophenyl) hydrazone
US4137411A (en)	1979-01-30	Preparation of 2,4-diamino-5-(4-amino-3,5-substituted-benzyl)-pyrimidines
US3205236A (en)	1965-09-07	Process of preparation of /j-alkylated tryptamines
Allison et al.	1954	The preparation and properties of 1: 2: 3: 4-tetrahydro-1-methyl-4-oxoquinoline
JPS6058919B2 (ja)	1985-12-23	フタリジル−イソキノリン誘導体、その製造法及びそれを含有する医薬
HU176214B (en)	1981-01-28	Process for producing new 5,6-dihydro-imidazo-square bracket-5,1-a-square bracket closed-isoquinolin derivatives
HU181054B (en)	1983-05-30	Process for producing triptamine derivatives
SU385970A1 (ru)	1973-06-14	Способ получения производных дибензимидазо-
DE726008C (de)	1942-10-06	Verfahren zur Herstellung von papaverinartig wirkenden Tetrahydroisochinolinverbindungen