CS216218B2 - Method of making the aminoizochinoline derivatives - Google Patents
Method of making the aminoizochinoline derivatives Download PDFInfo
- Publication number
- CS216218B2 CS216218B2 CS802538A CS253880A CS216218B2 CS 216218 B2 CS216218 B2 CS 216218B2 CS 802538 A CS802538 A CS 802538A CS 253880 A CS253880 A CS 253880A CS 216218 B2 CS216218 B2 CS 216218B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- group
- alkyl
- hydroxy
- carbon atoms
- alkyl groups
- Prior art date
Links
- 238000004519 manufacturing process Methods 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 24
- 239000002253 acid Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 7
- OSILBMSORKFRTB-UHFFFAOYSA-N isoquinolin-1-amine Chemical class C1=CC=C2C(N)=NC=CC2=C1 OSILBMSORKFRTB-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- -1 nitro, hydroxy Chemical group 0.000 claims description 20
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000001453 quaternary ammonium group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 9
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 8
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000003545 alkoxy group Chemical group 0.000 claims description 6
- 239000011230 binding agent Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 125000001424 substituent group Chemical group 0.000 claims description 6
- 125000004985 dialkyl amino alkyl group Chemical group 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- 125000003282 alkyl amino group Chemical group 0.000 claims description 4
- 150000007522 mineralic acids Chemical class 0.000 claims description 4
- 150000007524 organic acids Chemical class 0.000 claims description 4
- 125000003341 7 membered heterocyclic group Chemical group 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004429 atom Chemical group 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims 1
- 208000010513 Stupor Diseases 0.000 abstract description 2
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- 241000699670 Mus sp. Species 0.000 description 4
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- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
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- 239000012876 carrier material Substances 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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- UYXAWHWODHRRMR-UHFFFAOYSA-N hexobarbital Chemical compound O=C1N(C)C(=O)NC(=O)C1(C)C1=CCCCC1 UYXAWHWODHRRMR-UHFFFAOYSA-N 0.000 description 2
- 229960002456 hexobarbital Drugs 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
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- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- GZRKXKUVVPSREJ-UHFFFAOYSA-N pyridinylpiperazine Chemical compound C1CNCCN1C1=CC=CC=N1 GZRKXKUVVPSREJ-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 description 1
- HTALNGLVWLJHDB-UHFFFAOYSA-N 1-morpholin-4-ylisoquinolin-3-amine Chemical compound N=1C(N)=CC2=CC=CC=C2C=1N1CCOCC1 HTALNGLVWLJHDB-UHFFFAOYSA-N 0.000 description 1
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- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
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- 208000034819 Mobility Limitation Diseases 0.000 description 1
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- WERKSKAQRVDLDW-ANOHMWSOSA-N [(2s,3r,4r,5r)-2,3,4,5,6-pentahydroxyhexyl] (z)-octadec-9-enoate Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO WERKSKAQRVDLDW-ANOHMWSOSA-N 0.000 description 1
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- 125000001769 aryl amino group Chemical group 0.000 description 1
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- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
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- 229910000389 calcium phosphate Inorganic materials 0.000 description 1
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- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 125000006264 diethylaminomethyl group Chemical group [H]C([H])([H])C([H])([H])N(C([H])([H])*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
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- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
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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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- 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
- C07D217/24—Oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Veterinary Medicine (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Biomedical Technology (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU79EE2647A HU178522B (en) | 1979-04-11 | 1979-04-11 | Process for producing amino-isoquinoline derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS216218B2 true CS216218B2 (en) | 1982-10-29 |
Family
ID=10995839
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS802538A CS216218B2 (en) | 1979-04-11 | 1980-04-11 | Method of making the aminoizochinoline derivatives |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US4324894A (it) |
| JP (1) | JPS55149261A (it) |
| AT (1) | AT374798B (it) |
| AU (1) | AU535462B2 (it) |
| BE (1) | BE882674A (it) |
| CH (1) | CH643833A5 (it) |
| CS (1) | CS216218B2 (it) |
| DD (1) | DD150055A5 (it) |
| DE (1) | DE3013998A1 (it) |
| ES (1) | ES8103047A1 (it) |
| FR (1) | FR2453855A1 (it) |
| GB (1) | GB2048256B (it) |
| GR (1) | GR68197B (it) |
| HU (1) | HU178522B (it) |
| IT (1) | IT1148788B (it) |
| NL (1) | NL8002119A (it) |
| SU (1) | SU1033001A3 (it) |
| YU (1) | YU100280A (it) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE69839887D1 (de) | 1997-10-02 | 2008-09-25 | Eisai R&D Man Co Ltd | Kondensierte pyridinderivate |
| CN101578266B (zh) * | 2006-12-27 | 2013-10-30 | 塞诺菲-安万特股份有限公司 | 环烷基胺取代的异喹啉和异喹啉酮衍生物 |
| WO2008115593A1 (en) * | 2007-03-21 | 2008-09-25 | The University Of Montana | 1-[(2'-substituted)-piperazin-1'-yl]-isoquinolines as norepinephrine transporter inhibitor therapeutics and positron emission tomography imaging agents |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2593798A (en) * | 1947-05-22 | 1952-04-22 | Searle & Co | Aminoalkylamino isoquinoline compounds |
| CH344259A (de) * | 1955-12-21 | 1960-01-31 | Geigy Ag J R | Verfahren und Mittel zur Beeinflussung des Pflanzenwachstums |
| BE788608A (fr) * | 1971-09-09 | 1973-03-08 | Koninklijke Pharma Fab Nv | Aminoisoquinoleines |
| US3991063A (en) * | 1971-09-09 | 1976-11-09 | Wijbe Thomas Nauta | Aminoisoquinolines |
| AU465390B2 (en) | 1971-12-31 | 1975-09-10 | Ici Australia Limited | Isoquinolines |
| US3930837A (en) * | 1971-12-31 | 1976-01-06 | Ici Australia Limited | 3-chloro-5-acetamidaisoquinoline as a herbicide |
| AT342057B (de) * | 1974-04-25 | 1978-03-10 | Thomae Gmbh Dr K | Verfahren zur herstellung von neuen 3-piperazino-isochinolinen und deren salzen |
-
1979
- 1979-04-11 HU HU79EE2647A patent/HU178522B/hu not_active IP Right Cessation
-
1980
- 1980-03-31 GB GB8010793A patent/GB2048256B/en not_active Expired
- 1980-04-08 BE BE1/9778A patent/BE882674A/fr not_active IP Right Cessation
- 1980-04-10 US US06/138,843 patent/US4324894A/en not_active Expired - Lifetime
- 1980-04-10 IT IT21285/80A patent/IT1148788B/it active
- 1980-04-10 CH CH274280A patent/CH643833A5/de not_active IP Right Cessation
- 1980-04-10 DD DD80220351A patent/DD150055A5/de unknown
- 1980-04-10 FR FR8008052A patent/FR2453855A1/fr active Granted
- 1980-04-10 AU AU57302/80A patent/AU535462B2/en not_active Ceased
- 1980-04-11 ES ES490506A patent/ES8103047A1/es not_active Expired
- 1980-04-11 NL NL8002119A patent/NL8002119A/nl not_active Application Discontinuation
- 1980-04-11 JP JP4695780A patent/JPS55149261A/ja active Pending
- 1980-04-11 YU YU01002/80A patent/YU100280A/xx unknown
- 1980-04-11 DE DE19803013998 patent/DE3013998A1/de not_active Withdrawn
- 1980-04-11 AT AT0197280A patent/AT374798B/de not_active IP Right Cessation
- 1980-04-11 GR GR61658A patent/GR68197B/el unknown
- 1980-04-11 SU SU802905799A patent/SU1033001A3/ru active
- 1980-04-11 CS CS802538A patent/CS216218B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU100280A (en) | 1983-10-31 |
| AU5730280A (en) | 1980-10-16 |
| IT8021285A0 (it) | 1980-04-10 |
| DD150055A5 (de) | 1981-08-12 |
| HU178522B (en) | 1982-05-28 |
| JPS55149261A (en) | 1980-11-20 |
| ES490506A0 (es) | 1981-02-16 |
| NL8002119A (nl) | 1980-10-14 |
| GB2048256B (en) | 1983-05-18 |
| GR68197B (it) | 1981-11-10 |
| SU1033001A3 (ru) | 1983-07-30 |
| ATA197280A (de) | 1983-10-15 |
| FR2453855B1 (it) | 1983-08-26 |
| CH643833A5 (de) | 1984-06-29 |
| ES8103047A1 (es) | 1981-02-16 |
| BE882674A (fr) | 1980-10-08 |
| AU535462B2 (en) | 1984-03-22 |
| US4324894A (en) | 1982-04-13 |
| IT1148788B (it) | 1986-12-03 |
| DE3013998A1 (de) | 1980-12-11 |
| AT374798B (de) | 1984-05-25 |
| GB2048256A (en) | 1980-12-10 |
| FR2453855A1 (fr) | 1980-11-07 |
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