NO783770L - Nye derivater av isokinolin. - Google Patents
Nye derivater av isokinolin.Info
- Publication number
- NO783770L NO783770L NO783770A NO783770A NO783770L NO 783770 L NO783770 L NO 783770L NO 783770 A NO783770 A NO 783770A NO 783770 A NO783770 A NO 783770A NO 783770 L NO783770 L NO 783770L
- Authority
- NO
- Norway
- Prior art keywords
- tetrahydroisoquinoline
- denotes
- isoquinolyl
- general formula
- prepared
- Prior art date
Links
- -1 5-isoquinolyl group Chemical group 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 13
- 150000003839 salts Chemical class 0.000 claims description 13
- 239000000203 mixture Substances 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 7
- UWYZHKAOTLEWKK-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinoline Chemical compound C1=CC=C2CNCCC2=C1 UWYZHKAOTLEWKK-UHFFFAOYSA-N 0.000 claims description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 150000001450 anions Chemical class 0.000 claims description 2
- 239000012458 free base Substances 0.000 claims description 2
- 125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims 1
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 claims 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 36
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 18
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 15
- 239000013078 crystal Substances 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 12
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- 239000003960 organic solvent Substances 0.000 description 12
- 238000002844 melting Methods 0.000 description 11
- 230000008018 melting Effects 0.000 description 11
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 11
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- FXYVQWOZDXZAMJ-UHFFFAOYSA-N 3-(2-hydroxyethyl)-n-(3-methylisoquinolin-5-yl)-3,4-dihydro-1h-isoquinoline-2-carbothioamide Chemical compound C1C2=CC=CC=C2CC(CCO)N1C(=S)NC1=C2C=C(C)N=CC2=CC=C1 FXYVQWOZDXZAMJ-UHFFFAOYSA-N 0.000 description 8
- 238000001914 filtration Methods 0.000 description 8
- 238000003756 stirring Methods 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 6
- 238000004587 chromatography analysis Methods 0.000 description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 description 5
- DTVYNUOOZIKEEX-UHFFFAOYSA-N 5-aminoisoquinoline Chemical compound N1=CC=C2C(N)=CC=CC2=C1 DTVYNUOOZIKEEX-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- ZSKDXMLMMQFHGW-UHFFFAOYSA-N 1,2,3,4-tetrahydroisoquinolin-3-ylmethanol Chemical compound C1=CC=C2CNC(CO)CC2=C1 ZSKDXMLMMQFHGW-UHFFFAOYSA-N 0.000 description 3
- VMSZFBSYWXMXRF-UHFFFAOYSA-N 3-isothiocyanatopyridine Chemical compound S=C=NC1=CC=CN=C1 VMSZFBSYWXMXRF-UHFFFAOYSA-N 0.000 description 3
- ATSCEYAYNPGBMA-UHFFFAOYSA-N 5-isothiocyanato-3-methylisoquinoline Chemical compound C1=CC=C2C=NC(C)=CC2=C1N=C=S ATSCEYAYNPGBMA-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 3
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 3
- COLNVLDHVKWLRT-QMMMGPOBSA-N L-phenylalanine Chemical compound OC(=O)[C@@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-QMMMGPOBSA-N 0.000 description 3
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- 239000001530 fumaric acid Substances 0.000 description 3
- 239000013067 intermediate product Substances 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- WKACBLSJQCIWIQ-UHFFFAOYSA-N 2-(1,2,3,4-tetrahydroisoquinolin-3-yl)ethanol Chemical compound C1=CC=C2CNC(CCO)CC2=C1 WKACBLSJQCIWIQ-UHFFFAOYSA-N 0.000 description 2
- OCXFCZZVRFBTFJ-UHFFFAOYSA-N 5-isothiocyanato-3-octylisoquinoline Chemical compound C1=CC=C2C=NC(CCCCCCCC)=CC2=C1N=C=S OCXFCZZVRFBTFJ-UHFFFAOYSA-N 0.000 description 2
- CDWXWNNRMUQYSO-UHFFFAOYSA-N 5-isothiocyanato-3-propylisoquinoline Chemical compound C1=CC=C2C=NC(CCC)=CC2=C1N=C=S CDWXWNNRMUQYSO-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 125000004429 atom Chemical group 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- XMBWDFGMSWQBCA-UHFFFAOYSA-M iodide Chemical compound [I-] XMBWDFGMSWQBCA-UHFFFAOYSA-M 0.000 description 2
- 229940006461 iodide ion Drugs 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 150000002540 isothiocyanates Chemical class 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 2
- COLNVLDHVKWLRT-UHFFFAOYSA-N phenylalanine Natural products OC(=O)C(N)CC1=CC=CC=C1 COLNVLDHVKWLRT-UHFFFAOYSA-N 0.000 description 2
- 229960005190 phenylalanine Drugs 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 238000007363 ring formation reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- IKARIJVTSITGIZ-UHFFFAOYSA-N 3-(2-hydroxyethyl)-n-(3-octylisoquinolin-5-yl)-3,4-dihydro-1h-isoquinoline-2-carbothioamide Chemical compound C1C2=CC=CC=C2CC(CCO)N1C(=S)NC1=C2C=C(CCCCCCCC)N=CC2=CC=C1 IKARIJVTSITGIZ-UHFFFAOYSA-N 0.000 description 1
- RVABZEGEZFSECS-UHFFFAOYSA-N 3-(2-hydroxyethyl)-n-pyridin-3-yl-3,4-dihydro-1h-isoquinoline-2-carbothioamide Chemical compound OCCC1CC2=CC=CC=C2CN1C(=S)NC1=CC=CN=C1 RVABZEGEZFSECS-UHFFFAOYSA-N 0.000 description 1
- NXPGJFIKBCDNOJ-UHFFFAOYSA-N 3-octylisoquinolin-5-amine Chemical compound C1=CC=C2C=NC(CCCCCCCC)=CC2=C1N NXPGJFIKBCDNOJ-UHFFFAOYSA-N 0.000 description 1
- SSIPWNMRZDPBHH-UHFFFAOYSA-N 3-propylisoquinolin-5-amine Chemical compound C1=CC=C2C=NC(CCC)=CC2=C1N SSIPWNMRZDPBHH-UHFFFAOYSA-N 0.000 description 1
- PYPHDJNEFGUASN-UHFFFAOYSA-N 3h-isoquinoline-4-thione Chemical compound C1=CC=C2C(=S)CN=CC2=C1 PYPHDJNEFGUASN-UHFFFAOYSA-N 0.000 description 1
- ASNHGEVAWNWCRQ-UHFFFAOYSA-N 4-(hydroxymethyl)oxolane-2,3,4-triol Chemical compound OCC1(O)COC(O)C1O ASNHGEVAWNWCRQ-UHFFFAOYSA-N 0.000 description 1
- JTBAQPOKEMZAEQ-UHFFFAOYSA-N 5-isocyanatoisoquinoline Chemical compound N1=CC=C2C(N=C=O)=CC=CC2=C1 JTBAQPOKEMZAEQ-UHFFFAOYSA-N 0.000 description 1
- AMDNKJRTCIBIMK-UHFFFAOYSA-N 5-isothiocyanatoisoquinoline Chemical compound N1=CC=C2C(N=C=S)=CC=CC2=C1 AMDNKJRTCIBIMK-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- COLNVLDHVKWLRT-MRVPVSSYSA-N D-phenylalanine Chemical compound OC(=O)[C@H](N)CC1=CC=CC=C1 COLNVLDHVKWLRT-MRVPVSSYSA-N 0.000 description 1
- 229930182832 D-phenylalanine Natural products 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 230000000202 analgesic effect Effects 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 239000002260 anti-inflammatory agent Substances 0.000 description 1
- 229940121363 anti-inflammatory agent Drugs 0.000 description 1
- 230000003110 anti-inflammatory effect Effects 0.000 description 1
- 230000001754 anti-pyretic effect Effects 0.000 description 1
- 239000002221 antipyretic Substances 0.000 description 1
- 229940125716 antipyretic agent Drugs 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
- 244000309464 bull Species 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000012320 chlorinating reagent Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 description 1
- 150000002537 isoquinolines Chemical class 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000155 melt 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
- 235000010755 mineral Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 238000000053 physical method Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 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]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pain & Pain Management (AREA)
- Engineering & Computer Science (AREA)
- Neurology (AREA)
- Immunology (AREA)
- Biomedical Technology (AREA)
- Pulmonology (AREA)
- Neurosurgery (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Plural Heterocyclic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7733890A FR2408615A1 (fr) | 1977-11-10 | 1977-11-10 | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent |
| FR7823469A FR2433023A2 (fr) | 1978-08-09 | 1978-08-09 | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO783770L true NO783770L (no) | 1979-05-11 |
Family
ID=26220294
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO783770A NO783770L (no) | 1977-11-10 | 1978-11-09 | Nye derivater av isokinolin. |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4189480A (da) |
| JP (1) | JPS5476596A (da) |
| AR (2) | AR218943A1 (da) |
| AT (1) | AT365601B (da) |
| AU (1) | AU521104B2 (da) |
| CA (1) | CA1112642A (da) |
| CH (1) | CH635590A5 (da) |
| CS (1) | CS203934B2 (da) |
| DE (1) | DE2848926C3 (da) |
| DK (1) | DK499878A (da) |
| ES (2) | ES474985A1 (da) |
| FI (1) | FI63588C (da) |
| GB (1) | GB2007660B (da) |
| GR (1) | GR66033B (da) |
| HU (1) | HU175414B (da) |
| IL (1) | IL55903A (da) |
| IT (1) | IT1100206B (da) |
| LU (1) | LU80497A1 (da) |
| NL (1) | NL7810922A (da) |
| NO (1) | NO783770L (da) |
| NZ (1) | NZ188865A (da) |
| OA (1) | OA06082A (da) |
| PL (2) | PL113229B1 (da) |
| PT (1) | PT68769A (da) |
| SE (1) | SE7811595L (da) |
| SU (2) | SU797580A3 (da) |
| YU (2) | YU259478A (da) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1980000840A1 (en) * | 1978-10-12 | 1980-05-01 | Sandoz Ag | N-substituted cyclic amines,their preparation and pharmaceuticals containing them |
| FR2456110A2 (fr) * | 1979-05-09 | 1980-12-05 | Rhone Poulenc Ind | Nouveaux derives de l'isoquinoleine, leur preparation et les compositions qui les contiennent |
| FR2456111A1 (fr) * | 1979-05-09 | 1980-12-05 | Rhone Poulenc Ind | Nouveaux derives de l'indole, leur preparation et les medicaments qui les contiennent |
| DE3722827A1 (de) * | 1987-07-07 | 1989-01-19 | Schering Ag | Anellierte imino-azole und imino-azine, verfahren zu ihrer herstellung und ihre verwendung als mittel mit herbizider wirkung |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4147862A (en) * | 1974-09-18 | 1979-04-03 | Matsushita Electric Industrial Co., Ltd. | Method of preparing styryl-like compounds |
| NL169076C (nl) * | 1975-08-06 | 1982-06-01 | Rhone Poulenc Ind | Werkwijze voor het bereiden of vervaardigen van farmacologische preparaten met een analgetische en antipyretische werking, alsmede werkwijze voor het bereiden van geneeskrachtige verbindingen, welke geschikt zijn voor gebruik in dergelijke preparaten. |
| NL7800383A (nl) * | 1977-01-20 | 1978-07-24 | Rhone Poulenc Ind | Nieuwe isochinolinederivaten, de bereiding ervan en preparaten die de isochinolinederivaten bevatten. |
| NL7800385A (nl) * | 1977-02-04 | 1978-08-08 | Rhone Poulenc Ind | Nieuwe indoolderivaten, werkwijzen ter berei- ding ervan en preparaten die de nieuwe deriva- ten bevatten. |
-
1978
- 1978-10-26 SU SU782677515A patent/SU797580A3/ru active
- 1978-10-30 CA CA314,858A patent/CA1112642A/fr not_active Expired
- 1978-11-01 OA OA56648A patent/OA06082A/xx unknown
- 1978-11-02 NL NL7810922A patent/NL7810922A/xx not_active Application Discontinuation
- 1978-11-07 YU YU02594/78A patent/YU259478A/xx unknown
- 1978-11-08 PL PL1978210788A patent/PL113229B1/pl unknown
- 1978-11-08 GR GR57611A patent/GR66033B/el unknown
- 1978-11-08 IL IL55903A patent/IL55903A/xx unknown
- 1978-11-08 JP JP13684978A patent/JPS5476596A/ja active Granted
- 1978-11-08 AU AU41471/78A patent/AU521104B2/en not_active Expired
- 1978-11-08 PL PL1978215703A patent/PL113230B1/pl unknown
- 1978-11-08 CS CS787273A patent/CS203934B2/cs unknown
- 1978-11-08 US US05/958,617 patent/US4189480A/en not_active Expired - Lifetime
- 1978-11-08 NZ NZ188865A patent/NZ188865A/xx unknown
- 1978-11-09 PT PT68769A patent/PT68769A/pt unknown
- 1978-11-09 LU LU80497A patent/LU80497A1/xx unknown
- 1978-11-09 NO NO783770A patent/NO783770L/no unknown
- 1978-11-09 HU HU78RO1000A patent/HU175414B/hu unknown
- 1978-11-09 AR AR274400A patent/AR218943A1/es active
- 1978-11-09 IT IT29635/78A patent/IT1100206B/it active
- 1978-11-09 SE SE7811595A patent/SE7811595L/xx unknown
- 1978-11-09 GB GB7843907A patent/GB2007660B/en not_active Expired
- 1978-11-09 CH CH1153278A patent/CH635590A5/fr not_active IP Right Cessation
- 1978-11-09 DK DK499878A patent/DK499878A/da unknown
- 1978-11-10 AT AT0806378A patent/AT365601B/de not_active IP Right Cessation
- 1978-11-10 FI FI783440A patent/FI63588C/fi not_active IP Right Cessation
- 1978-11-10 ES ES474985A patent/ES474985A1/es not_active Expired
- 1978-11-10 DE DE2848926A patent/DE2848926C3/de not_active Expired
- 1978-11-10 ES ES474986A patent/ES474986A1/es not_active Expired
-
1979
- 1979-08-01 SU SU792790355A patent/SU867312A3/ru active
- 1979-09-20 AR AR278146A patent/AR220228A1/es active
-
1982
- 1982-10-12 YU YU02298/82A patent/YU229882A/xx unknown
Also Published As
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| FI63587C (fi) | Foerfarande foer framstaellning av anti-inflammatoriska halogenerade 4-hydroxi-2-alkyl-3-karbamoyl-2h-tieno-1,2-tiazin-1,1-dioxidderivat | |
| NO122814B (da) | ||
| NO159725B (no) | Analogifremgangsmaate for fremstilling av terapeutisk aktive tieno (3,2-c)pyridinderivater. | |
| IE903453A1 (en) | Derivatives of 2-hydroxythiophene and -furan fused with a¹nitrogen-containing ring, process for preparing these and¹their application in therapy | |
| NO154116B (no) | Fremgangsm¨te og lamellsepareringsapparat for tilf¯rsel og fordeling av en sammensatt v|ske til et lamellseparerings apparat. | |
| US4224445A (en) | Thienothiazine derivatives | |
| FI59253C (fi) | Foerfarande foer framstaellning av terapeutiskt anvaendbara 4-hydroxi-2h-tieno(2,3-e) och (3,4-e)-1,2-tiazin-3-karboxamid-1,1-dioxid-derivat | |
| DK160550B (da) | Tetrahydroisoquinolin-2-ylderivater af carboxylsyrer som thromboxan-a2-antagonister, deres anvendelse i et medicinsk praeparat og farmaceutisk middel indeholdende dem | |
| NO762729L (da) | ||
| IE811112L (en) | Derivatives of 4-hydroxy-3-quinoline carboxylic acid | |
| NO782357L (no) | Fremgangsmaate til fremstilling av bicykliske thia-diaza-forbindelser | |
| DK149230B (da) | Analogifremgangsmaade til fremstilling af 5-benzoyl-6-hydroxy-indan-1-carboxylsyrederivater eller farmaceutisk acceptable salte deraf | |
| NO783770L (no) | Nye derivater av isokinolin. | |
| NO780202L (no) | Fremgangsmaate for fremstilling av nye derivater av isokinolin | |
| IL22791A (en) | Tetrahydro indenopyridine compounds | |
| NO143664B (no) | Analogifremgangsmaate ved fremstilling av terapeutisk aktive dibenzofuranforbindelser | |
| US3086972A (en) | Aza-thiaxanthene derivatives | |
| CS226901B1 (en) | Thiazoloisoquinoline derivatives | |
| DK159110B (da) | 4h-benzo(4,5)cyclohepta(1,2-b)thiophenderivater, fremgangsmaade til fremstilling deraf samt farmaceutiske praeparater indeholdende derivaterne | |
| NO743135L (da) | ||
| NO138210B (no) | Fremgangsmaate for fremstilling av tricykliske forbindelser | |
| NO801360L (no) | Isokinolinderivater. | |
| NO143534B (no) | Analogifremgangsmaate for fremstilling av terapeutisk virksomme derivater av oxatiino(1,4)(2,3-c)pyrrol | |
| KR810001176B1 (ko) | 이소퀴놀린 유도체의 제조방법 | |
| KR810000717B1 (ko) | 이소퀴놀린 유도체의 제조방법 |