FI67221C - Foerfarande foer framstaellning av farmakologiskt aktiva tiadiazol- och oxadiazoltetrahydroisokinolinfoereningar - Google Patents
Foerfarande foer framstaellning av farmakologiskt aktiva tiadiazol- och oxadiazoltetrahydroisokinolinfoereningar Download PDFInfo
- Publication number
- FI67221C FI67221C FI802112A FI802112A FI67221C FI 67221 C FI67221 C FI 67221C FI 802112 A FI802112 A FI 802112A FI 802112 A FI802112 A FI 802112A FI 67221 C FI67221 C FI 67221C
- Authority
- FI
- Finland
- Prior art keywords
- tetrahydroisoquinoline
- acetyl
- thiadiazole
- amino
- hydrochloric acid
- Prior art date
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- 238000000034 method Methods 0.000 title claims description 10
- VLLMWSRANPNYQX-UHFFFAOYSA-N thiadiazole Chemical compound C1=CSN=N1.C1=CSN=N1 VLLMWSRANPNYQX-UHFFFAOYSA-N 0.000 title claims description 5
- 230000006611 pharmacological activation Effects 0.000 title 1
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- 238000002360 preparation method Methods 0.000 claims description 8
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- 239000007937 lozenge Substances 0.000 description 1
- 235000019359 magnesium stearate 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
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 208000010125 myocardial infarction Diseases 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 208000015238 neurotic disease Diseases 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 239000000312 peanut oil Substances 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 229950006768 phenylethanolamine Drugs 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 235000013772 propylene glycol Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000003340 retarding agent Substances 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000020374 simple syrup Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- SRRKNRDXURUMPP-UHFFFAOYSA-N sodium disulfide Chemical compound [Na+].[Na+].[S-][S-] SRRKNRDXURUMPP-UHFFFAOYSA-N 0.000 description 1
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 229940114926 stearate Drugs 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- UWYZHKAOTLEWKK-UHFFFAOYSA-N tetrahydro-isoquinoline Natural products C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M trans-cinnamate Chemical compound [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000003021 water soluble solvent 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
- A61P25/02—Drugs for disorders of the nervous system for peripheral neuropathies
-
- 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
- C07D217/04—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 with hydrocarbon or substituted hydrocarbon radicals attached to the ring nitrogen atom
-
- 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
- C07D217/06—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 with the ring nitrogen atom acylated by carboxylic or carbonic acids, or with sulfur or nitrogen analogues thereof, e.g. carbamates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5434379A | 1979-07-02 | 1979-07-02 | |
| US5434379 | 1979-07-02 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI802112A7 FI802112A7 (fi) | 1981-01-03 |
| FI67221B FI67221B (fi) | 1984-10-31 |
| FI67221C true FI67221C (fi) | 1985-02-11 |
Family
ID=21990408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI802112A FI67221C (fi) | 1979-07-02 | 1980-07-01 | Foerfarande foer framstaellning av farmakologiskt aktiva tiadiazol- och oxadiazoltetrahydroisokinolinfoereningar |
Country Status (30)
| Country | Link |
|---|---|
| EP (1) | EP0023761B1 (cs) |
| JP (1) | JPS5610192A (cs) |
| KR (1) | KR840000396B1 (cs) |
| AR (1) | AR225925A1 (cs) |
| AT (1) | ATE6515T1 (cs) |
| AU (1) | AU531641B2 (cs) |
| BG (1) | BG51250A3 (cs) |
| CA (1) | CA1129415A (cs) |
| CS (1) | CS215064B2 (cs) |
| DD (1) | DD151750A5 (cs) |
| DE (1) | DE3066826D1 (cs) |
| DK (1) | DK151029C (cs) |
| ES (1) | ES492971A0 (cs) |
| FI (1) | FI67221C (cs) |
| GR (1) | GR69206B (cs) |
| HU (1) | HU179382B (cs) |
| IE (1) | IE50290B1 (cs) |
| IL (1) | IL60426A (cs) |
| IN (1) | IN160542B (cs) |
| MX (1) | MX6317E (cs) |
| NO (1) | NO801951L (cs) |
| NZ (1) | NZ194156A (cs) |
| PH (1) | PH17042A (cs) |
| PL (2) | PL127098B1 (cs) |
| PT (1) | PT71458A (cs) |
| RO (1) | RO79707A (cs) |
| SU (1) | SU1072809A3 (cs) |
| YU (1) | YU171180A (cs) |
| ZA (1) | ZA802987B (cs) |
| ZW (1) | ZW14680A1 (cs) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4352809A (en) * | 1981-09-04 | 1982-10-05 | Smithkline Corporation | Method of producing alpha2 antagonism |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3939164A (en) * | 1974-02-08 | 1976-02-17 | Smithkline Corporation | 7 AND 8-Halo substituted 1,2,3,4-tetrahydroisoquinoline compounds |
| US3988339A (en) * | 1974-02-08 | 1976-10-26 | Smithkline Corporation | Pharmaceutical compositions and methods of inhibiting phenylethanolamine N-methyltransferase |
-
1980
- 1980-05-20 ZA ZA00802987A patent/ZA802987B/xx unknown
- 1980-06-25 CS CS804525A patent/CS215064B2/cs unknown
- 1980-06-25 JP JP8720980A patent/JPS5610192A/ja active Pending
- 1980-06-25 CA CA354,710A patent/CA1129415A/en not_active Expired
- 1980-06-25 PH PH24191A patent/PH17042A/en unknown
- 1980-06-26 DE DE8080302140T patent/DE3066826D1/de not_active Expired
- 1980-06-26 PT PT71458A patent/PT71458A/pt unknown
- 1980-06-26 EP EP80302140A patent/EP0023761B1/en not_active Expired
- 1980-06-26 DK DK274280A patent/DK151029C/da not_active IP Right Cessation
- 1980-06-26 AT AT80302140T patent/ATE6515T1/de not_active IP Right Cessation
- 1980-06-26 IN IN485/DEL/80A patent/IN160542B/en unknown
- 1980-06-26 AU AU59677/80A patent/AU531641B2/en not_active Ceased
- 1980-06-26 NZ NZ194156A patent/NZ194156A/xx unknown
- 1980-06-27 IL IL60426A patent/IL60426A/xx unknown
- 1980-06-27 ZW ZW146/80A patent/ZW14680A1/xx unknown
- 1980-06-27 NO NO801951A patent/NO801951L/no unknown
- 1980-06-28 KR KR1019800002551A patent/KR840000396B1/ko not_active Expired
- 1980-06-30 DD DD80222268A patent/DD151750A5/de unknown
- 1980-06-30 AR AR281587A patent/AR225925A1/es active
- 1980-06-30 RO RO80101552A patent/RO79707A/ro unknown
- 1980-06-30 IE IE1352/80A patent/IE50290B1/en unknown
- 1980-07-01 YU YU01711/80A patent/YU171180A/xx unknown
- 1980-07-01 HU HU80801631A patent/HU179382B/hu unknown
- 1980-07-01 FI FI802112A patent/FI67221C/fi not_active IP Right Cessation
- 1980-07-01 SU SU802942953A patent/SU1072809A3/ru active
- 1980-07-01 BG BG048339A patent/BG51250A3/bg unknown
- 1980-07-01 PL PL1980225377A patent/PL127098B1/pl unknown
- 1980-07-01 PL PL23061980A patent/PL230619A1/xx unknown
- 1980-07-01 ES ES492971A patent/ES492971A0/es active Granted
- 1980-07-01 GR GR62330A patent/GR69206B/el unknown
- 1980-07-02 MX MX808900U patent/MX6317E/es unknown
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: SMITHKLINE BECKMAN CORPORATION |