FI61882C - Foerfarande foer framstaellning av antitrombotiskt verkande 3-iperazino-isokinoliner - Google Patents
Foerfarande foer framstaellning av antitrombotiskt verkande 3-iperazino-isokinoliner Download PDFInfo
- Publication number
- FI61882C FI61882C FI751067A FI751067A FI61882C FI 61882 C FI61882 C FI 61882C FI 751067 A FI751067 A FI 751067A FI 751067 A FI751067 A FI 751067A FI 61882 C FI61882 C FI 61882C
- Authority
- FI
- Finland
- Prior art keywords
- group
- general formula
- compound
- piperazino
- isoquinoline
- Prior art date
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- 238000005057 refrigeration Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 32
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims description 29
- 239000000460 chlorine Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 12
- -1 morpholino, thiomorpholino Chemical group 0.000 claims description 12
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 8
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000002252 acyl group Chemical group 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 6
- 150000003839 salts Chemical class 0.000 claims description 5
- DMQFFNUCAGFFGD-UHFFFAOYSA-N 4-(3-piperazin-1-ylisoquinolin-1-yl)-1,4-thiazinane 1-oxide Chemical compound C1CS(=O)CCN1C1=NC(N2CCNCC2)=CC2=CC=CC=C12 DMQFFNUCAGFFGD-UHFFFAOYSA-N 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 4
- 230000002785 anti-thrombosis Effects 0.000 claims description 4
- 239000003146 anticoagulant agent Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 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
- 235000005985 organic acids Nutrition 0.000 claims description 4
- YHIIJNLSGULWAA-UHFFFAOYSA-N 1,4-thiazinane 1-oxide Chemical group O=S1CCNCC1 YHIIJNLSGULWAA-UHFFFAOYSA-N 0.000 claims description 3
- PJPJVTSCAFZBGN-UHFFFAOYSA-N 3-piperazin-1-ylisoquinoline Chemical class C1CNCCN1C1=CC2=CC=CC=C2C=N1 PJPJVTSCAFZBGN-UHFFFAOYSA-N 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical group C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 claims description 3
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- 239000011737 fluorine Chemical group 0.000 claims description 2
- 229910052731 fluorine Inorganic materials 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 230000007062 hydrolysis Effects 0.000 claims description 2
- 238000006460 hydrolysis reaction Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
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- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 4
- IIQWLASQZORSAL-UHFFFAOYSA-N 4-(3-chloroisoquinolin-1-yl)morpholine Chemical compound N=1C(Cl)=CC2=CC=CC=C2C=1N1CCOCC1 IIQWLASQZORSAL-UHFFFAOYSA-N 0.000 description 3
- GUXMNMILBMRWQP-UHFFFAOYSA-N 4-(3-piperazin-1-ylisoquinolin-1-yl)thiomorpholine Chemical compound C1CNCCN1C1=CC2=CC=CC=C2C(N2CCSCC2)=N1 GUXMNMILBMRWQP-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011324 bead Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
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- 210000002381 plasma Anatomy 0.000 description 3
- 208000010110 spontaneous platelet aggregation Diseases 0.000 description 3
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- CZHOWRLLHOAYBE-UHFFFAOYSA-N 4-(3,5-dichloroisoquinolin-1-yl)thiomorpholine Chemical compound N=1C(Cl)=CC2=C(Cl)C=CC=C2C=1N1CCSCC1 CZHOWRLLHOAYBE-UHFFFAOYSA-N 0.000 description 2
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- 238000005054 agglomeration Methods 0.000 description 1
- 238000004220 aggregation Methods 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 230000029936 alkylation Effects 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004676 antithrombotic agent Drugs 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 239000003610 charcoal Substances 0.000 description 1
- UXTMROKLAAOEQO-UHFFFAOYSA-N chloroform;ethanol Chemical compound CCO.ClC(Cl)Cl UXTMROKLAAOEQO-UHFFFAOYSA-N 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000002474 experimental method Methods 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
- 239000007789 gas Substances 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 125000001841 imino group Chemical group [H]N=* 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000007530 organic bases Chemical group 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 230000009805 platelet accumulation Effects 0.000 description 1
- 210000004623 platelet-rich plasma Anatomy 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000012286 potassium permanganate Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000002516 radical scavenger Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Substances [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000006228 supernatant Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000005505 thiomorpholino group Chemical group 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- CUGZEDSDRBMZMY-UHFFFAOYSA-N trihydrate;hydrochloride Chemical compound O.O.O.Cl CUGZEDSDRBMZMY-UHFFFAOYSA-N 0.000 description 1
- 239000000052 vinegar Substances 0.000 description 1
- 235000021419 vinegar Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2420012A DE2420012C3 (de) | 1974-04-25 | 1974-04-25 | Isochinoline |
| DE2420012 | 1974-04-25 | ||
| DE2503961 | 1975-01-31 | ||
| DE19752503961 DE2503961C3 (de) | 1975-01-31 | 1975-01-31 | Isochinoline |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| FI751067A7 FI751067A7 (is") | 1975-10-26 |
| FI61882B FI61882B (fi) | 1982-06-30 |
| FI61882C true FI61882C (fi) | 1982-10-11 |
Family
ID=25767041
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| FI751067A FI61882C (fi) | 1974-04-25 | 1975-04-09 | Foerfarande foer framstaellning av antitrombotiskt verkande 3-iperazino-isokinoliner |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US3975524A (is") |
| JP (1) | JPS584020B2 (is") |
| AT (1) | AT342057B (is") |
| BG (1) | BG25081A3 (is") |
| CA (1) | CA1051893A (is") |
| CH (2) | CH613965A5 (is") |
| CS (1) | CS193512B2 (is") |
| DD (1) | DD119047A5 (is") |
| DK (1) | DK140841B (is") |
| ES (2) | ES436317A1 (is") |
| FI (1) | FI61882C (is") |
| FR (1) | FR2268524B1 (is") |
| GB (1) | GB1466227A (is") |
| HU (1) | HU170231B (is") |
| IE (1) | IE41409B1 (is") |
| IL (1) | IL47155A (is") |
| NL (1) | NL7504016A (is") |
| NO (1) | NO142403C (is") |
| PH (1) | PH10885A (is") |
| PL (1) | PL93821B1 (is") |
| RO (1) | RO66020A (is") |
| SE (1) | SE404926B (is") |
| SU (1) | SU557756A3 (is") |
| YU (1) | YU105375A (is") |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2811312A1 (de) * | 1978-03-16 | 1979-09-27 | Hoechst Ag | Neue isochinolinderivate, verfahren zu ihrer herstellung und ihre verwendung zur herstellung von arzneimitteln |
| DE2818403A1 (de) * | 1978-04-27 | 1979-11-08 | Hoechst Ag | Neue isochinolinderivate und verfahren zu ihrer herstellung |
| HU178522B (en) * | 1979-04-11 | 1982-05-28 | Egyt Gyogyszervegyeszeti Gyar | Process for producing amino-isoquinoline derivatives |
| DE3034001A1 (de) * | 1980-09-10 | 1982-04-22 | Hoechst Ag, 6000 Frankfurt | Isochinolinderivate, verfahren zu ihrer hersellung, sie enthaltende pharmazeutische zubereitungen und ihre verwendung |
| US4656173A (en) * | 1985-04-24 | 1987-04-07 | Bristol-Myers Company | Antipsychotic benzisothiazole S-oxide compound |
| ATE404539T1 (de) | 1997-10-02 | 2008-08-15 | Eisai R&D Man Co Ltd | Kondensierte pyridinderivate |
| FR2864080B1 (fr) * | 2003-12-23 | 2006-02-03 | Sanofi Synthelabo | Derives de 1-piperazine-et-1-homopiperazine-carboxylates, leur preparation et leur application en therapeutique |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3751417A (en) * | 1971-08-12 | 1973-08-07 | American Cyanamid Co | 1-acyl-3-(2-(4-phenyl-1-piperazinyl)ethyl)indolines |
-
1975
- 1975-03-04 AT AT163975A patent/AT342057B/de not_active IP Right Cessation
- 1975-04-04 NL NL7504016A patent/NL7504016A/xx not_active Application Discontinuation
- 1975-04-04 ES ES436317A patent/ES436317A1/es not_active Expired
- 1975-04-08 BG BG029588A patent/BG25081A3/xx unknown
- 1975-04-09 FI FI751067A patent/FI61882C/fi not_active IP Right Cessation
- 1975-04-11 SU SU2121918A patent/SU557756A3/ru active
- 1975-04-11 US US05/567,234 patent/US3975524A/en not_active Expired - Lifetime
- 1975-04-11 DK DK157975AA patent/DK140841B/da not_active IP Right Cessation
- 1975-04-16 PH PH17065A patent/PH10885A/en unknown
- 1975-04-23 DD DD185646A patent/DD119047A5/xx unknown
- 1975-04-23 RO RO7582052A patent/RO66020A/ro unknown
- 1975-04-23 CH CH515575A patent/CH613965A5/xx not_active IP Right Cessation
- 1975-04-24 GB GB1708575A patent/GB1466227A/en not_active Expired
- 1975-04-24 CA CA225,579A patent/CA1051893A/en not_active Expired
- 1975-04-24 SE SE7504779A patent/SE404926B/xx unknown
- 1975-04-24 JP JP50050160A patent/JPS584020B2/ja not_active Expired
- 1975-04-24 YU YU01053/75A patent/YU105375A/xx unknown
- 1975-04-24 NO NO751473A patent/NO142403C/no unknown
- 1975-04-24 PL PL1975179891A patent/PL93821B1/pl unknown
- 1975-04-24 HU HUTO1001A patent/HU170231B/hu unknown
- 1975-04-24 IL IL47155A patent/IL47155A/xx unknown
- 1975-04-25 CS CS752918A patent/CS193512B2/cs unknown
- 1975-04-25 FR FR7513095A patent/FR2268524B1/fr not_active Expired
- 1975-04-25 IE IE933/75A patent/IE41409B1/en unknown
- 1975-07-01 ES ES439038A patent/ES439038A1/es not_active Expired
-
1979
- 1979-02-14 CH CH142979A patent/CH615180A5/de not_active IP Right Cessation
Also Published As
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MM | Patent lapsed |
Owner name: DR. KARL THOMAE GESELLSCHAFT MIT |