CS269989B2 - Method of 3-(4-cyano-4-phenylalkyl)tetrahydroisoquinoline derivatives production - Google Patents

Method of 3-(4-cyano-4-phenylalkyl)tetrahydroisoquinoline derivatives production Download PDF

Info

Publication number: CS269989B2
Authority: CS; Czechoslovakia
Prior art keywords: formula; compound; dimethoxyphenyl; acid; isopropyl
Prior art date: 1985-12-02

Application number

CS868817A

Other languages

Czech (cs)

English (en)

Other versions

CS881786A2 (en

Inventor

Robin D Clark

Joseph M Muchowski

Fang-Ting Chiu

John O Gardner

Jacob Berger

Original Assignee

Syntex Inc

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.)

1985-12-02

Filing date

1986-12-01

Publication date

1990-05-14

1986-12-01 Application filed by Syntex Inc filed Critical Syntex Inc

1989-09-12 Publication of CS881786A2 publication Critical patent/CS881786A2/cs

1990-05-14 Publication of CS269989B2 publication Critical patent/CS269989B2/cs

Links

238000000034 method Methods 0.000 title claims description 30
238000004519 manufacturing process Methods 0.000 title claims description 3
150000001875 compounds Chemical class 0.000 claims abstract description 77
239000002253 acid Substances 0.000 claims abstract description 23
150000003839 salts Chemical class 0.000 claims abstract description 20
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 33
238000002360 preparation method Methods 0.000 claims description 20
125000003762 3,4-dimethoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C(OC([H])([H])[H])C([H])=C1* 0.000 claims description 19
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 6
235000019253 formic acid Nutrition 0.000 claims description 6
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QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
WLJVXDMOQOGPHL-UHFFFAOYSA-N benzyl-alpha-carboxylic acid Natural products OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
210000004556 brain Anatomy 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
125000002057 carboxymethyl group Chemical group [H]OC(=O)C([H])([H])[*] 0.000 description 1
210000001627 cerebral artery Anatomy 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
229930016911 cinnamic acid Natural products 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
238000001816 cooling Methods 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
WZHCOOQXZCIUNC-UHFFFAOYSA-N cyclandelate Chemical class C1C(C)(C)CC(C)CC1OC(=O)C(O)C1=CC=CC=C1 WZHCOOQXZCIUNC-UHFFFAOYSA-N 0.000 description 1
239000003405 delayed action preparation Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
239000008121 dextrose Substances 0.000 description 1
239000002552 dosage form Substances 0.000 description 1
210000000613 ear canal Anatomy 0.000 description 1
238000002592 echocardiography Methods 0.000 description 1
230000002526 effect on cardiovascular system Effects 0.000 description 1
CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical compound CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
239000002024 ethyl acetate extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
239000012467 final product Substances 0.000 description 1
150000004673 fluoride salts Chemical class 0.000 description 1
150000002221 fluorine Chemical class 0.000 description 1
235000011087 fumaric acid Nutrition 0.000 description 1
150000002238 fumaric acids Chemical class 0.000 description 1
235000011187 glycerol Nutrition 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 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
230000036543 hypotension Effects 0.000 description 1
230000001939 inductive effect Effects 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
238000010253 intravenous injection Methods 0.000 description 1
238000002955 isolation Methods 0.000 description 1
125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 description 1
210000005053 lamin Anatomy 0.000 description 1
239000010410 layer Substances 0.000 description 1
238000011866 long-term treatment Methods 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
235000019359 magnesium stearate Nutrition 0.000 description 1
229910052943 magnesium sulfate Inorganic materials 0.000 description 1
235000019341 magnesium sulphate Nutrition 0.000 description 1
VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
239000011976 maleic acid Substances 0.000 description 1
239000001630 malic acid Substances 0.000 description 1
IWYDHOAUDWTVEP-UHFFFAOYSA-N mandelic acid Chemical compound OC(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-N 0.000 description 1
QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
NBTOZLQBSIZIKS-UHFFFAOYSA-N methoxide Chemical compound [O-]C NBTOZLQBSIZIKS-UHFFFAOYSA-N 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
206010027599 migraine Diseases 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
230000010016 myocardial function Effects 0.000 description 1
238000011587 new zealand white rabbit Methods 0.000 description 1
229910000510 noble metal Inorganic materials 0.000 description 1
231100000252 nontoxic Toxicity 0.000 description 1
230000003000 nontoxic effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
125000005489 p-toluenesulfonic acid group Chemical class 0.000 description 1
230000001575 pathological effect Effects 0.000 description 1
239000000312 peanut oil Substances 0.000 description 1
229960002275 pentobarbital sodium Drugs 0.000 description 1
230000036581 peripheral resistance Effects 0.000 description 1
239000000825 pharmaceutical preparation Substances 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
229960003424 phenylacetic acid Drugs 0.000 description 1
239000003279 phenylacetic acid Substances 0.000 description 1
SONNWYBIRXJNDC-VIFPVBQESA-N phenylephrine Chemical compound CNC[C@H](O)C1=CC=CC(O)=C1 SONNWYBIRXJNDC-VIFPVBQESA-N 0.000 description 1
229960001802 phenylephrine Drugs 0.000 description 1
239000006187 pill Substances 0.000 description 1
230000008092 positive effect Effects 0.000 description 1
JTTWNTXHFYNETH-UHFFFAOYSA-N propyl 4-methylbenzenesulfonate Chemical compound CCCOS(=O)(=O)C1=CC=C(C)C=C1 JTTWNTXHFYNETH-UHFFFAOYSA-N 0.000 description 1
229940107700 pyruvic acid Drugs 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
238000012216 screening Methods 0.000 description 1
239000008159 sesame oil Substances 0.000 description 1
235000011803 sesame oil Nutrition 0.000 description 1
235000020183 skimmed milk Nutrition 0.000 description 1
239000010802 sludge Substances 0.000 description 1
RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
239000003549 soybean oil Substances 0.000 description 1
235000012424 soybean oil Nutrition 0.000 description 1
230000002269 spontaneous effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000007920 subcutaneous administration Methods 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000829 suppository Substances 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
239000003826 tablet Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
150000003526 tetrahydroisoquinolines Chemical class 0.000 description 1
150000003530 tetrahydroquinolines Chemical class 0.000 description 1
125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
238000012546 transfer Methods 0.000 description 1
238000002604 ultrasonography Methods 0.000 description 1
238000010200 validation analysis Methods 0.000 description 1
230000002792 vascular Effects 0.000 description 1
230000000304 vasodilatating effect Effects 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
210000003462 vein Anatomy 0.000 description 1
229960001722 verapamil Drugs 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/10—Drugs for disorders of the cardiovascular system for treating ischaemic or atherosclerotic diseases, e.g. antianginal drugs, coronary vasodilators, drugs for myocardial infarction, retinopathy, cerebrovascula insufficiency, renal arteriosclerosis
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/12—Antihypertensives
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Veterinary Medicine (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
General Chemical & Material Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Chemical Kinetics & Catalysis (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Cardiology (AREA)
Heart & Thoracic Surgery (AREA)
Urology & Nephrology (AREA)
Vascular Medicine (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

CS868817A 1985-12-02 1986-12-01 Method of 3-(4-cyano-4-phenylalkyl)tetrahydroisoquinoline derivatives production CS269989B2 (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US06/803,464 US4613606A (en)	1985-12-02	1985-12-02	Tetrahydroisoquinoline derivatives

Publications (2)

Publication Number	Publication Date
CS881786A2 CS881786A2 (en)	1989-09-12
CS269989B2 true CS269989B2 (en)	1990-05-14

Family

ID=25186568

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CS868817A CS269989B2 (en)	1985-12-02	1986-12-01	Method of 3-(4-cyano-4-phenylalkyl)tetrahydroisoquinoline derivatives production

Country Status (5)

Country	Link
US (1)	US4613606A (ja)
JP (1)	JPS62155247A (ja)
CS (1)	CS269989B2 (ja)
SU (2)	SU1598875A3 (ja)
ZA (1)	ZA869059B (ja)

Families Citing this family (10)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4667038A (en) *	1985-12-02	1987-05-19	Syntex (U.S.A.) Inc.	Tetrahydroisoquinoline derivatives
US4978793A (en) *	1988-06-23	1990-12-18	W. R. Grace & Co.-Conn.	Novel process for the preparation of serinol
US5135944A (en) *	1989-06-21	1992-08-04	Syntex (U.S.A.) Inc.	Bis(benzylpyrrolidine) derivatives useful for treating congestive heart failure and acute renal failure
US5100912A (en) *	1990-05-14	1992-03-31	Syntex (U.S.A.) Inc.	Bis(benzylpyrrolidine) derivatives as dopamine agonists
US5093355A (en) *	1989-10-30	1992-03-03	Syntex (U.S.A.) Inc.	Benzylpyrrolidine derivatives as dopamine agonists
CA2061260A1 (en) *	1991-02-27	1992-08-28	Kiyofumi Ishikawa	Isoquinoline derivatives
US5362736A (en) *	1991-02-27	1994-11-08	Banyu Pharmaceutical Co., Ltd.	Isoquinoline derivatives
DE19719817A1 (de) *	1997-05-13	1998-11-19	Hoechst Ag	Substituierte 6- und 7-Aminotetrahydroisochinolincarbonsäuren
JP2004511465A (ja)	2000-10-10	2004-04-15	カリックス　セラピューティックス　インコーポレイテッド	三環式化合物およびその使用
WO2007059372A2 (en) *	2005-11-09	2007-05-24	St. Jude Children's Research Hospital	Use of chloroquine to treat metabolic syndrome

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1802804A1 (de) *	1968-10-12	1970-06-11	Knoll Ag	1-[3'-Cyan-3'-(2'',3''-dimethoxyphenyl)-4'-methylpentyl]-2-methyl-6,7-dimethoxy-1,2,3,4-Tetrahydroisochinolin
DE2854210C2 (de) *	1978-12-15	1984-08-09	Degussa Ag, 6000 Frankfurt	Verfahren zur Herstellung von aromatisch oder heteroaromatisch substituierten Acetonitrilen

1985
- 1985-12-02 US US06/803,464 patent/US4613606A/en not_active Expired - Fee Related
1986
- 1986-12-01 JP JP61287554A patent/JPS62155247A/ja active Pending
- 1986-12-01 CS CS868817A patent/CS269989B2/cs unknown
- 1986-12-01 SU SU864028618A patent/SU1598875A3/ru active
- 1986-12-01 ZA ZA869059A patent/ZA869059B/xx unknown
1988
- 1988-05-20 SU SU884355735A patent/SU1591806A3/ru active

Also Published As

Publication number	Publication date
SU1591806A3 (ru)	1990-09-07
US4613606A (en)	1986-09-23
JPS62155247A (ja)	1987-07-10
CS881786A2 (en)	1989-09-12
ZA869059B (en)	1988-07-27
SU1598875A3 (ru)	1990-10-07

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EP0389352B1 (fr)	1994-04-13	Dérivés fluoro-4 benzoiques, leurs procédés de préparation et les compositions pharmaceutiques qui les contiennent
KR860001761B1 (ko)	1986-10-21	광학활성 카바졸 유도체의 제조방법
TWI840423B (zh)	2024-05-01	甲狀腺素受體β促效劑化合物
EP0302788B1 (fr)	1992-02-05	Dérivés de [(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 9H-pyrido[3,4-b]indole, leur préparation et leur application en thérapeutique
JPH0739387B2 (ja)	1995-05-01	新規１−ベンジル−アミノアルキル−ピロリジノン化合物及びその製造方法
SK46793A3 (en)	1994-02-02	Regenarative melting tank and method of working
EP0351255B1 (fr)	1993-10-13	Dérivés de [(pipéridinyl-4)méthyl]-2 tétrahydro-1,2,3,4 isoquinoléine, leur préparation et leur application en thérapeutique
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NZ195329A (en)	1984-05-31	6,7-benzomorphan derivatives and pharmaceutical compositions
SU1598875A3 (ru)	1990-10-07	Способ получени производных тетрагидроизохинолина или их фармацевтически приемлемых кислотно-аддитивных солей
EP0136198A1 (fr)	1985-04-03	Dérivés de triazolo pyrimidine, leur procédé de préparation et leur application thérapeutique en tant que toni-cardiaques
US5693640A (en)	1997-12-02	Pyridazino-indole derivatives
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US3499906A (en)	1970-03-10	5,9-diethyl-2'-hydroxy-2-substituted-6,7-benzomorphans
HU176231B (en)	1981-01-28	Process for producing 4a-aryl-octahydro-1h-2-pyridine derivatives
HU197312B (en)	1989-03-28	Process for producing tetrahydroisoquinoline derivatives and pharmaceuticals comprising such active ingredient
EP0074711B1 (en)	1986-01-15	Benzodioxane-imidazoline compounds, their preparation and use
JPS6212773A (ja)	1987-01-21	ヘキセン酸、その製造法及びこれを含有する製薬組成物
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