CS195349B2 - Method of producing 3-alkyl-5-isoquinolyliminothiazolo/3,4-b/isoquinolines - Google Patents
Method of producing 3-alkyl-5-isoquinolyliminothiazolo/3,4-b/isoquinolines Download PDFInfo
- Publication number
- CS195349B2 CS195349B2 CS78323A CS32378A CS195349B2 CS 195349 B2 CS195349 B2 CS 195349B2 CS 78323 A CS78323 A CS 78323A CS 32378 A CS32378 A CS 32378A CS 195349 B2 CS195349 B2 CS 195349B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- compounds
- isoquinoline
- formula
- tetrahydro
- doses
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 9
- 150000002537 isoquinolines Chemical class 0.000 title 1
- -1 3-methyl-5-isoquinolylimino Chemical group 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 11
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 6
- 238000006243 chemical reaction Methods 0.000 claims description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 claims description 4
- 238000001914 filtration Methods 0.000 claims description 3
- 239000000203 mixture Substances 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims 3
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 claims 3
- 241000700159 Rattus Species 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims 2
- 241000699670 Mus sp. Species 0.000 claims 2
- 230000000202 analgesic effect Effects 0.000 claims 2
- 230000003110 anti-inflammatory effect Effects 0.000 claims 2
- 230000001754 anti-pyretic effect Effects 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- GHESMRYCQSFSSF-UHFFFAOYSA-N isoquinolin-2-ium;iodide Chemical compound [I-].C1=[NH+]C=CC2=CC=CC=C21 GHESMRYCQSFSSF-UHFFFAOYSA-N 0.000 claims 2
- 238000002844 melting Methods 0.000 claims 2
- 230000008018 melting Effects 0.000 claims 2
- 238000003756 stirring Methods 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- RKZRSFDITVGOHP-JTQLQIEISA-N (10as)-1,5,10,10a-tetrahydro-[1,3]thiazolo[3,4-b]isoquinoline-3-thione Chemical compound C1=CC=C2CN3C(=S)SC[C@@H]3CC2=C1 RKZRSFDITVGOHP-JTQLQIEISA-N 0.000 claims 1
- WRIZFUVYABPOLN-UHFFFAOYSA-N 2h-isoquinoline-3-thione Chemical compound C1=CC=C2C=NC(S)=CC2=C1 WRIZFUVYABPOLN-UHFFFAOYSA-N 0.000 claims 1
- ZQLKOMXEZYQQBJ-UHFFFAOYSA-N 3-methylisoquinolin-5-amine Chemical compound C1=CC=C2C=NC(C)=CC2=C1N ZQLKOMXEZYQQBJ-UHFFFAOYSA-N 0.000 claims 1
- DBPRXNKINFIMQS-UHFFFAOYSA-M 3-methylsulfanyl-1,5,10,10a-tetrahydro-[1,3]thiazolo[3,4-b]isoquinolin-4-ium;iodide Chemical compound [I-].C1C2=CC=CC=C2CC2[N+]1=C(SC)SC2 DBPRXNKINFIMQS-UHFFFAOYSA-M 0.000 claims 1
- 238000004587 chromatography analysis Methods 0.000 claims 1
- 238000002425 crystallisation Methods 0.000 claims 1
- 230000008025 crystallization Effects 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 239000003814 drug Substances 0.000 claims 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 claims 1
- 235000019341 magnesium sulphate Nutrition 0.000 claims 1
- 239000012074 organic phase Substances 0.000 claims 1
- 230000000144 pharmacologic effect Effects 0.000 claims 1
- 238000000053 physical method Methods 0.000 claims 1
- 239000002244 precipitate Substances 0.000 claims 1
- 231100000161 signs of toxicity Toxicity 0.000 claims 1
- 239000007787 solid Substances 0.000 claims 1
- 239000000725 suspension Substances 0.000 claims 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N tetrahydrofuran Substances C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- 231100000419 toxicity Toxicity 0.000 claims 1
- 230000001988 toxicity Effects 0.000 claims 1
- 239000003960 organic solvent Substances 0.000 description 6
- 239000002253 acid Substances 0.000 description 4
- 125000004414 alkyl thio group Chemical group 0.000 description 4
- 229910052801 chlorine Inorganic materials 0.000 description 4
- 125000001309 chloro group Chemical group Cl* 0.000 description 4
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 3
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical group I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 3
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- ZSKDXMLMMQFHGW-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-3-ylmethanol Chemical compound C1=CC=C2CNC(CO)CC2=C1 ZSKDXMLMMQFHGW-UHFFFAOYSA-N 0.000 description 1
- RKZRSFDITVGOHP-UHFFFAOYSA-N 1,5,10,10a-tetrahydro-[1,3]thiazolo[3,4-b]isoquinoline-3-thione Chemical compound C1=CC=C2CN3C(=S)SCC3CC2=C1 RKZRSFDITVGOHP-UHFFFAOYSA-N 0.000 description 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 1
- TZEYHTCZIQZAPS-UHFFFAOYSA-N [1,3]thiazolo[4,5-h]isoquinoline Chemical class C1=CN=CC2=C(SC=N3)C3=CC=C21 TZEYHTCZIQZAPS-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 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
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 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
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- GNWXVOQHLPBSSR-UHFFFAOYSA-N oxolane;toluene Chemical compound C1CCOC1.CC1=CC=CC=C1 GNWXVOQHLPBSSR-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems
-
- 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
-
- 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
- C07D217/14—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals
- C07D217/16—Heterocyclic compounds containing isoquinoline or hydrogenated isoquinoline ring systems with radicals, substituted by hetero atoms, attached to carbon atoms of the nitrogen-containing ring other than aralkyl radicals substituted by oxygen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7701516A FR2378030A1 (fr) | 1977-01-20 | 1977-01-20 | Nouveau derive de l'isoquinoleine, sa preparation et les compositions qui le contiennent |
| FR7739028A FR2412545A1 (fr) | 1977-12-23 | 1977-12-23 | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS195349B2 true CS195349B2 (en) | 1980-01-31 |
Family
ID=26219809
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS78323A CS195349B2 (en) | 1977-01-20 | 1978-01-17 | Method of producing 3-alkyl-5-isoquinolyliminothiazolo/3,4-b/isoquinolines |
| CS785983A CS195350B2 (en) | 1977-01-20 | 1978-01-17 | Method of producing 3-alkyl-5-isoquinolyliminothiazolo/3,4-b/isoquinolines |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS785983A CS195350B2 (en) | 1977-01-20 | 1978-01-17 | Method of producing 3-alkyl-5-isoquinolyliminothiazolo/3,4-b/isoquinolines |
Country Status (25)
| Country | Link |
|---|---|
| US (1) | US4153698A (de) |
| JP (1) | JPS5914037B2 (de) |
| AR (2) | AR217460A1 (de) |
| AT (1) | AT361481B (de) |
| AU (1) | AU510044B2 (de) |
| CA (1) | CA1091674A (de) |
| CH (1) | CH633010A5 (de) |
| CS (2) | CS195349B2 (de) |
| DE (1) | DE2802453C3 (de) |
| DK (1) | DK143343C (de) |
| ES (2) | ES466192A1 (de) |
| FI (1) | FI62314C (de) |
| GB (1) | GB1574281A (de) |
| GR (1) | GR61726B (de) |
| HU (1) | HU174219B (de) |
| IE (1) | IE46375B1 (de) |
| IL (1) | IL53841A (de) |
| LU (1) | LU78895A1 (de) |
| NL (1) | NL7800383A (de) |
| NO (1) | NO780202L (de) |
| NZ (1) | NZ186282A (de) |
| OA (1) | OA05859A (de) |
| PT (1) | PT67545B (de) |
| SE (1) | SE7800681L (de) |
| SU (2) | SU730309A3 (de) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| SU797580A3 (ru) * | 1977-11-10 | 1981-01-15 | Рон-Пуленк Эндюстри (Фирма) | Способ получени производных изохино-лиНА, иХ СОлЕй, РАцЕМАТОВ или ОпТичЕС-КиХ изОМЕРОВ |
| FR2456098A2 (fr) * | 1977-12-23 | 1980-12-05 | Rhone Poulenc Ind | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions pharmaceutiques qui les contiennent |
| NL7908655A (nl) * | 1978-12-07 | 1980-06-10 | Rhone Poulenc Ind | Nieuwe thienopyridine-derivaten, de bereiding ervan, alsmede farmaceutische preparaten, die de nieuwe derivaten bevatten. |
| GB2048880A (en) * | 1979-05-09 | 1980-12-17 | Rhone Poulenc Ind | Isoquinoline derivatives |
| FR2456111A1 (fr) * | 1979-05-09 | 1980-12-05 | Rhone Poulenc Ind | Nouveaux derives de l'indole, leur preparation et les medicaments qui les contiennent |
| NZ195721A (en) * | 1979-12-04 | 1982-09-14 | Rhone Poulenc Ind | Thiazolo(3,4-b)isoquinoline derivatives and pharmaceutical compositions |
| US4269842A (en) * | 1979-12-05 | 1981-05-26 | Rhone-Poulenc Industries | Method for treating rhinoviral complaints |
| US6582728B1 (en) * | 1992-07-08 | 2003-06-24 | Inhale Therapeutic Systems, Inc. | Spray drying of macromolecules to produce inhaleable dry powders |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA05403A (fr) * | 1975-08-06 | 1981-02-28 | Rhone Poulenc Ind | Nouveaux dérivés de la thiazolo [3,4-b] isoquinoléine et leur procédé de préparation. |
-
1978
- 1978-01-12 NL NL7800383A patent/NL7800383A/xx not_active Application Discontinuation
- 1978-01-17 CS CS78323A patent/CS195349B2/cs unknown
- 1978-01-17 CS CS785983A patent/CS195350B2/cs unknown
- 1978-01-17 OA OA56380A patent/OA05859A/xx unknown
- 1978-01-18 GR GR55196A patent/GR61726B/el unknown
- 1978-01-18 IL IL53841A patent/IL53841A/xx unknown
- 1978-01-19 SU SU782567352A patent/SU730309A3/ru active
- 1978-01-19 LU LU78895A patent/LU78895A1/xx unknown
- 1978-01-19 CH CH56178A patent/CH633010A5/fr not_active IP Right Cessation
- 1978-01-19 CA CA295,296A patent/CA1091674A/fr not_active Expired
- 1978-01-19 AT AT39378A patent/AT361481B/de not_active IP Right Cessation
- 1978-01-19 HU HU78RO958A patent/HU174219B/hu unknown
- 1978-01-19 PT PT67545A patent/PT67545B/pt unknown
- 1978-01-19 GB GB2241/78A patent/GB1574281A/en not_active Expired
- 1978-01-19 DK DK27178A patent/DK143343C/da not_active IP Right Cessation
- 1978-01-19 SE SE7800681A patent/SE7800681L/xx unknown
- 1978-01-19 NO NO780202A patent/NO780202L/no unknown
- 1978-01-20 FI FI780182A patent/FI62314C/fi not_active IP Right Cessation
- 1978-01-20 JP JP53005113A patent/JPS5914037B2/ja not_active Expired
- 1978-01-20 DE DE2802453A patent/DE2802453C3/de not_active Expired
- 1978-01-20 AU AU32611/78A patent/AU510044B2/en not_active Expired
- 1978-01-20 IE IE126/78A patent/IE46375B1/en unknown
- 1978-01-20 NZ NZ186282A patent/NZ186282A/xx unknown
- 1978-01-20 US US05/871,136 patent/US4153698A/en not_active Expired - Lifetime
- 1978-01-20 ES ES466192A patent/ES466192A1/es not_active Expired
- 1978-01-20 AR AR270785A patent/AR217460A1/es active
- 1978-04-07 ES ES468630A patent/ES468630A1/es not_active Expired
-
1979
- 1979-02-05 AR AR275407A patent/AR219963A1/es active
- 1979-02-08 SU SU792720496A patent/SU776560A3/ru active
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