NO134985B - - Google Patents
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- Publication number
- NO134985B NO134985B NO209/71A NO20971A NO134985B NO 134985 B NO134985 B NO 134985B NO 209/71 A NO209/71 A NO 209/71A NO 20971 A NO20971 A NO 20971A NO 134985 B NO134985 B NO 134985B
- Authority
- NO
- Norway
- Prior art keywords
- group
- general formula
- salt
- alkyl
- denotes
- Prior art date
Links
- 125000000217 alkyl group Chemical group 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 6
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 6
- -1 methylenedioxy group Chemical group 0.000 claims description 5
- 229910052763 palladium Inorganic materials 0.000 claims description 5
- NKSZCPBUWGZONP-UHFFFAOYSA-N 3,4-dihydroisoquinoline Chemical class C1=CC=C2C=NCCC2=C1 NKSZCPBUWGZONP-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000012458 free base Substances 0.000 claims description 2
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 4
- 150000002537 isoquinolines Chemical class 0.000 description 4
- VPKAHUMPZYVNIV-UHFFFAOYSA-N 1,4-dihydroisoquinoline Chemical class C1=CC=C2CC=NCC2=C1 VPKAHUMPZYVNIV-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000002425 crystallisation Methods 0.000 description 2
- 230000008025 crystallization Effects 0.000 description 2
- 238000010828 elution Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 150000003526 tetrahydroisoquinolines Chemical class 0.000 description 2
- 206010011224 Cough Diseases 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 1
- 125000005605 benzo group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 206010061592 cardiac fibrillation Diseases 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 230000002600 fibrillogenic effect Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002391 heterocyclic compounds Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical compound C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- WLDFBDNWPZFNJD-UHFFFAOYSA-N n-(3,4-dihydroisoquinolin-1-yl)-n',n'-diethylethane-1,2-diamine Chemical compound C1=CC=C2C(NCCN(CC)CC)=NCCC2=C1 WLDFBDNWPZFNJD-UHFFFAOYSA-N 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000021962 pH elevation Effects 0.000 description 1
- 238000004810 partition chromatography Methods 0.000 description 1
- 230000003285 pharmacodynamic effect Effects 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- C07D217/22—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the nitrogen-containing ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7002128A FR2076625A5 (de) | 1970-01-21 | 1970-01-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| NO134985B true NO134985B (de) | 1976-10-11 |
| NO134985C NO134985C (de) | 1977-01-19 |
Family
ID=9049388
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO209/71A NO134985C (de) | 1970-01-21 | 1971-01-20 |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US3748333A (de) |
| JP (1) | JPS5330716B1 (de) |
| AT (1) | AT299951B (de) |
| BE (1) | BE761827A (de) |
| CA (1) | CA939672A (de) |
| CH (1) | CH521346A (de) |
| DE (1) | DE2102794C3 (de) |
| DK (1) | DK136064B (de) |
| ES (1) | ES387500A1 (de) |
| FI (1) | FI48734C (de) |
| FR (1) | FR2076625A5 (de) |
| GB (1) | GB1284051A (de) |
| IL (1) | IL36027A (de) |
| NL (1) | NL162903C (de) |
| NO (1) | NO134985C (de) |
| SE (1) | SE360079B (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2314985A1 (de) * | 1973-03-26 | 1974-10-17 | Hoechst Ag | 1-(imidazol-1-yl)-isochinoline und verfahren zu ihrer herstellung |
| GB8908229D0 (en) * | 1989-04-12 | 1989-05-24 | Smithkline Beckman Intercredit | Compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2666059A (en) * | 1950-08-11 | 1954-01-12 | American Cyanamid Co | Anilinoisoquinolines and processes of preparing the same |
| US2823235A (en) * | 1955-05-10 | 1958-02-11 | Du Pont | Hydrogenation of nitro compounds to amines and catalyst therefor |
| US3452026A (en) * | 1966-03-15 | 1969-06-24 | Bristol Myers Co | Substituted 1,2,3,4-tetrahydroquinolines |
| GB1244501A (en) * | 1968-03-09 | 1971-09-02 | Aspro Nicholas Ltd | Heterocyclic amines |
-
1970
- 1970-01-21 FR FR7002128A patent/FR2076625A5/fr not_active Expired
- 1970-10-29 FI FI702917A patent/FI48734C/fi active
-
1971
- 1971-01-13 NL NL7100449.A patent/NL162903C/xx active
- 1971-01-19 JP JP133871A patent/JPS5330716B1/ja active Pending
- 1971-01-19 GB GB2580/71A patent/GB1284051A/en not_active Expired
- 1971-01-19 US US00107859A patent/US3748333A/en not_active Expired - Lifetime
- 1971-01-20 CH CH81271A patent/CH521346A/fr not_active IP Right Cessation
- 1971-01-20 DK DK24071AA patent/DK136064B/da unknown
- 1971-01-20 BE BE761827A patent/BE761827A/xx unknown
- 1971-01-20 IL IL36027A patent/IL36027A/xx unknown
- 1971-01-20 NO NO209/71A patent/NO134985C/no unknown
- 1971-01-20 SE SE00647/71A patent/SE360079B/xx unknown
- 1971-01-20 CA CA103244A patent/CA939672A/en not_active Expired
- 1971-01-21 ES ES387500A patent/ES387500A1/es not_active Expired
- 1971-01-21 AT AT48071A patent/AT299951B/de not_active IP Right Cessation
- 1971-01-21 DE DE2102794A patent/DE2102794C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7100449A (de) | 1971-07-23 |
| CA939672A (en) | 1974-01-08 |
| IL36027A0 (en) | 1971-03-24 |
| FI48734B (de) | 1974-09-02 |
| ES387500A1 (es) | 1973-05-01 |
| DE2102794C3 (de) | 1979-04-19 |
| DK136064C (de) | 1978-01-23 |
| JPS5330716B1 (de) | 1978-08-29 |
| DK136064B (da) | 1977-08-08 |
| US3748333A (en) | 1973-07-24 |
| CH521346A (fr) | 1972-04-15 |
| DE2102794A1 (de) | 1971-07-29 |
| NO134985C (de) | 1977-01-19 |
| DE2102794B2 (de) | 1978-08-24 |
| GB1284051A (en) | 1972-08-02 |
| NL162903C (nl) | 1980-07-15 |
| SE360079B (de) | 1973-09-17 |
| AT299951B (de) | 1972-07-10 |
| BE761827A (fr) | 1971-07-20 |
| FI48734C (fi) | 1974-12-10 |
| FR2076625A5 (de) | 1971-10-15 |
| IL36027A (en) | 1974-03-14 |
| NL162903B (nl) | 1980-02-15 |
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