NO126483B - - Google Patents

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Publication number: NO126483B
Authority: NO; Norway
Prior art keywords: compounds; compound; tetrahydroisoquinoline; acid; mixture
Prior art date: 1968-01-31

Application number

NO30369A

Other languages

English (en)

Norwegian (no)

Inventor

Eisaku Yamato

Masao Wada

Original Assignee

Tanabe Seiyaku Co

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.)

1968-01-31

Filing date

1969-01-27

Publication date

1973-02-12

1969-01-27 Application filed by Tanabe Seiyaku Co filed Critical Tanabe Seiyaku Co

1973-02-12 Publication of NO126483B publication Critical patent/NO126483B/no

Links

-1 methoxyphenyl Chemical group 0.000 claims description 29
150000001875 compounds Chemical class 0.000 claims description 27
239000000203 mixture Substances 0.000 claims description 18
238000000034 method Methods 0.000 claims description 17
125000000217 alkyl group Chemical group 0.000 claims description 7
125000001931 aliphatic group Chemical group 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000002252 acyl group Chemical group 0.000 claims description 3
VYFYYTLLBUKUHU-UHFFFAOYSA-N dopamine Chemical compound NCCC1=CC=C(O)C(O)=C1 VYFYYTLLBUKUHU-UHFFFAOYSA-N 0.000 claims description 3
238000002360 preparation method Methods 0.000 claims description 3
230000002378 acidificating effect Effects 0.000 claims description 2
125000005805 dimethoxy phenyl group Chemical group 0.000 claims description 2
239000012442 inert solvent Substances 0.000 claims description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
125000001680 trimethoxyphenyl group Chemical group 0.000 claims description 2
125000003039 tetrahydroisoquinolinyl group Chemical class C1(NCCC2=CC=CC=C12)* 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 29
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 21
239000000243 solution Substances 0.000 description 19
238000002844 melting Methods 0.000 description 15
230000008018 melting Effects 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
239000003208 petroleum Substances 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000013078 crystal Substances 0.000 description 6
238000004519 manufacturing process Methods 0.000 description 6
238000010992 reflux Methods 0.000 description 6
150000003526 tetrahydroisoquinolines Chemical class 0.000 description 6
CTENFNNZBMHDDG-UHFFFAOYSA-N Dopamine hydrochloride Chemical compound Cl.NCCC1=CC=C(O)C(O)=C1 CTENFNNZBMHDDG-UHFFFAOYSA-N 0.000 description 5
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000001816 cooling Methods 0.000 description 5
239000002904 solvent Substances 0.000 description 5
238000003756 stirring Methods 0.000 description 5
239000007864 aqueous solution Substances 0.000 description 4
229940049953 phenylacetate Drugs 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
239000007858 starting material Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000005457 ice water Substances 0.000 description 3
229960003424 phenylacetic acid Drugs 0.000 description 3
239000003279 phenylacetic acid Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
BHHGXPLMPWCGHP-UHFFFAOYSA-N Phenethylamine Natural products NCCC1=CC=CC=C1 BHHGXPLMPWCGHP-UHFFFAOYSA-N 0.000 description 2
238000006796 Pomeranz-Fritsch reaction Methods 0.000 description 2
XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
238000006359 acetalization reaction Methods 0.000 description 2
238000005917 acylation reaction Methods 0.000 description 2
229910052783 alkali metal Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000007810 chemical reaction solvent Substances 0.000 description 2
239000012230 colorless oil Substances 0.000 description 2
WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
230000007062 hydrolysis Effects 0.000 description 2
238000006460 hydrolysis reaction Methods 0.000 description 2
AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 2
238000006053 organic reaction Methods 0.000 description 2
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
238000007363 ring formation reaction Methods 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
GWCFOZUNGBECRW-UHFFFAOYSA-N 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound C1=C(OC)C(OC)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 GWCFOZUNGBECRW-UHFFFAOYSA-N 0.000 description 1
ZVTWHNLKDVOCNW-UHFFFAOYSA-N 1-[(3,5-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound COC1=CC(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 ZVTWHNLKDVOCNW-UHFFFAOYSA-N 0.000 description 1
FWQAUIPLDHTNCB-UHFFFAOYSA-N 1-[(4-methoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound C1=CC(OC)=CC=C1CC1C2=CC(O)=C(O)C=C2CCN1 FWQAUIPLDHTNCB-UHFFFAOYSA-N 0.000 description 1
GGGSEBXTKMTNBW-UHFFFAOYSA-N 1-benzyl-1,2,3,4-tetrahydroisoquinoline-6,7-diol Chemical compound C1=2C=C(O)C(O)=CC=2CCNC1CC1=CC=CC=C1 GGGSEBXTKMTNBW-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
MODKMHXGCGKTLE-UHFFFAOYSA-N N-acetylphenylethylamine Chemical class CC(=O)NCCC1=CC=CC=C1 MODKMHXGCGKTLE-UHFFFAOYSA-N 0.000 description 1
238000006929 Pictet-Spengler synthesis reaction Methods 0.000 description 1
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
230000010933 acylation Effects 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
150000001340 alkali metals Chemical group 0.000 description 1
208000006673 asthma Diseases 0.000 description 1
IZTUINVRJSCOIR-UHFFFAOYSA-N benzylisoquinoline Chemical compound N=1C=CC2=CC=CC=C2C=1CC1=CC=CC=C1 IZTUINVRJSCOIR-UHFFFAOYSA-N 0.000 description 1
229940124630 bronchodilator Drugs 0.000 description 1
239000000168 bronchodilator agent Substances 0.000 description 1
239000000496 cardiotonic agent Substances 0.000 description 1
230000003177 cardiotonic effect Effects 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
239000002026 chloroform extract Substances 0.000 description 1
238000006482 condensation reaction Methods 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
230000000994 depressogenic effect Effects 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
PHSQGRIKRCUPMR-UHFFFAOYSA-N ethyl 2-(3,4,5-trimethoxyphenyl)acetate Chemical compound CCOC(=O)CC1=CC(OC)=C(OC)C(OC)=C1 PHSQGRIKRCUPMR-UHFFFAOYSA-N 0.000 description 1
239000000284 extract Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
235000019253 formic acid Nutrition 0.000 description 1
230000022244 formylation Effects 0.000 description 1
238000006170 formylation reaction Methods 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
UHSXRTHJCJGEKG-UHFFFAOYSA-N hydron;1-[(3,4,5-trimethoxyphenyl)methyl]-1,2,3,4-tetrahydroisoquinoline-6,7-diol;chloride Chemical compound Cl.COC1=C(OC)C(OC)=CC(CC2C3=CC(O)=C(O)C=C3CCN2)=C1 UHSXRTHJCJGEKG-UHFFFAOYSA-N 0.000 description 1
125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
238000003402 intramolecular cyclocondensation reaction Methods 0.000 description 1
238000011835 investigation Methods 0.000 description 1
150000002537 isoquinolines Chemical class 0.000 description 1
239000011707 mineral Substances 0.000 description 1
235000010755 mineral Nutrition 0.000 description 1
MBFUSGLXKQWVDW-UHFFFAOYSA-N norsalsolinol Chemical class C1CNCC2=C1C=C(O)C(O)=C2 MBFUSGLXKQWVDW-UHFFFAOYSA-N 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
229940117803 phenethylamine Drugs 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
239000000126 substance Substances 0.000 description 1
238000003786 synthesis reaction Methods 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D217/00—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems
- C07D217/02—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with only hydrogen atoms or radicals containing only carbon and hydrogen atoms, directly attached to carbon atoms of the nitrogen-containing ring; Alkylene-bis-isoquinolines

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Quinoline Compounds (AREA)

NO30369A 1968-01-31 1969-01-27 NO126483B (cs)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP588968		1968-01-31

Publications (1)

Publication Number	Publication Date
NO126483B true NO126483B (cs)	1973-02-12

Family

ID=11623444

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NO30369A NO126483B (cs)	1968-01-31	1969-01-27

Country Status (9)

Country	Link
AT (1)	AT286987B (cs)
CH (1)	CH521345A (cs)
CS (2)	CS159754B2 (cs)
DK (1)	DK135765B (cs)
ES (1)	ES363129A1 (cs)
FI (1)	FI49165C (cs)
NL (1)	NL6901221A (cs)
NO (1)	NO126483B (cs)
SE (1)	SE352889B (cs)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8518635D0 (en) *	1985-07-23	1985-08-29	Smithkline Beckman Corp	Chemical compounds
GB8518634D0 (en) *	1985-07-23	1985-08-29	Smithkline Beckman Corp	Chemical compounds

1969
- 1969-01-22 SE SE85369A patent/SE352889B/xx unknown
- 1969-01-23 FI FI20769A patent/FI49165C/fi active
- 1969-01-24 NL NL6901221A patent/NL6901221A/xx unknown
- 1969-01-27 NO NO30369A patent/NO126483B/no unknown
- 1969-01-28 CS CS53969A patent/CS159754B2/cs unknown
- 1969-01-28 CS CS872372A patent/CS159755B2/cs unknown
- 1969-01-30 ES ES363129A patent/ES363129A1/es not_active Expired
- 1969-01-30 DK DK51769A patent/DK135765B/da not_active IP Right Cessation
- 1969-01-30 AT AT94169A patent/AT286987B/de active
- 1969-01-31 CH CH155569A patent/CH521345A/de not_active IP Right Cessation

Also Published As

Publication number	Publication date
SE352889B (cs)	1973-01-15
FI49165C (fi)	1975-04-10
CH521345A (de)	1972-04-15
ES363129A1 (es)	1970-11-16
DK135765C (cs)	1977-11-28
AT286987B (de)	1971-01-11
NL6901221A (cs)	1969-08-04
FI49165B (cs)	1974-12-31
DK135765B (da)	1977-06-20
CS159755B2 (cs)	1975-01-31
CS159754B2 (cs)	1975-01-31

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