NO314081B1 - Substituerte isokinolin-derivater og deres anvendelse og fremstilling, samtfarmasöytiske preparater inneholdende forbindelsene - Google Patents
Substituerte isokinolin-derivater og deres anvendelse og fremstilling, samtfarmasöytiske preparater inneholdende forbindelsene Download PDFInfo
- Publication number
- NO314081B1 NO314081B1 NO19994510A NO994510A NO314081B1 NO 314081 B1 NO314081 B1 NO 314081B1 NO 19994510 A NO19994510 A NO 19994510A NO 994510 A NO994510 A NO 994510A NO 314081 B1 NO314081 B1 NO 314081B1
- Authority
- NO
- Norway
- Prior art keywords
- tetrahydroisoquinolin
- methyl
- bromo
- nmr
- iso
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims description 142
- 238000002360 preparation method Methods 0.000 title claims description 35
- 239000000825 pharmaceutical preparation Substances 0.000 title claims description 4
- 125000002183 isoquinolinyl group Chemical class C1(=NC=CC2=CC=CC=C12)* 0.000 title 1
- -1 C-1-C6-alkoxy Chemical group 0.000 claims description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 33
- 238000004519 manufacturing process Methods 0.000 claims description 31
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 23
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 19
- 150000003839 salts Chemical class 0.000 claims description 19
- 238000006243 chemical reaction Methods 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 16
- 208000035475 disorder Diseases 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 14
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- ZPUCINDJVBIVPJ-LJISPDSOSA-N ***e Chemical compound O([C@H]1C[C@@H]2CC[C@@H](N2C)[C@H]1C(=O)OC)C(=O)C1=CC=CC=C1 ZPUCINDJVBIVPJ-LJISPDSOSA-N 0.000 claims description 12
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- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- AHONRCXNXUBHGE-UHFFFAOYSA-N 3,4,5-trimethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound COC1=C(OC)C(OC)=CC(C(=O)NC=2C=C3CN(C)CCC3=CC=2)=C1 AHONRCXNXUBHGE-UHFFFAOYSA-N 0.000 claims description 3
- VOSHURDHUZSVNH-UHFFFAOYSA-N 3-bromo-n-(5-chloro-2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-4-ethoxybenzamide Chemical compound C1=C(Br)C(OCC)=CC=C1C(=O)NC1=CC(Cl)=C(CCN(C)C2)C2=C1 VOSHURDHUZSVNH-UHFFFAOYSA-N 0.000 claims description 3
- PMTOIIMQZMMEPR-UHFFFAOYSA-N 3-chloro-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=CC(Cl)=C1 PMTOIIMQZMMEPR-UHFFFAOYSA-N 0.000 claims description 3
- VLJGTIAWOFBIRR-UHFFFAOYSA-N 5-benzoyl-n-(5-iodo-1,2,3,4-tetrahydroisoquinolin-7-yl)-2-methoxybenzamide Chemical compound C1=C(C(=O)NC=2C=C3CNCCC3=C(I)C=2)C(OC)=CC=C1C(=O)C1=CC=CC=C1 VLJGTIAWOFBIRR-UHFFFAOYSA-N 0.000 claims description 3
- PMRSETIJSQHJTO-UHFFFAOYSA-N 5-benzoyl-n-(7-iodo-2-methyl-3,4-dihydro-1h-isoquinolin-5-yl)-2-methoxybenzamide Chemical compound C1=C(C(=O)NC=2C=3CCN(C)CC=3C=C(I)C=2)C(OC)=CC=C1C(=O)C1=CC=CC=C1 PMRSETIJSQHJTO-UHFFFAOYSA-N 0.000 claims description 3
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
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- KFNMVJFJHCQFAI-UHFFFAOYSA-N 3-cyano-4-ethoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(C#N)C(OCC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 KFNMVJFJHCQFAI-UHFFFAOYSA-N 0.000 claims description 2
- BGJHNIOVHWNFSB-UHFFFAOYSA-N 3-iodo-4-methoxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide Chemical compound C1=C(I)C(OC)=CC=C1C(=O)NC1=CC=C(CCN(C)C2)C2=C1 BGJHNIOVHWNFSB-UHFFFAOYSA-N 0.000 claims description 2
- ALSCJJJLXIVYAR-UHFFFAOYSA-N 4-fluoro-3-methyl-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)benzamide;hydrochloride Chemical compound Cl.C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(F)C(C)=C1 ALSCJJJLXIVYAR-UHFFFAOYSA-N 0.000 claims description 2
- VIDPFUAQNRZKEX-UHFFFAOYSA-N 4-hydroxy-n-(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)-3-(trifluoromethyl)benzamide Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(O)C(C(F)(F)F)=C1 VIDPFUAQNRZKEX-UHFFFAOYSA-N 0.000 claims description 2
- LRBSCNASLDWCOR-UHFFFAOYSA-N 5-benzoyl-n-(7-iodo-1,2,3,4-tetrahydroisoquinolin-5-yl)-2-methoxybenzamide Chemical compound C1=C(C(=O)NC=2C=3CCNCC=3C=C(I)C=2)C(OC)=CC=C1C(=O)C1=CC=CC=C1 LRBSCNASLDWCOR-UHFFFAOYSA-N 0.000 claims description 2
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- MNRSUGVCPQRZPE-UHFFFAOYSA-N [4-[(2-methyl-3,4-dihydro-1h-isoquinolin-7-yl)carbamoyl]phenyl] acetate Chemical compound C1=C2CN(C)CCC2=CC=C1NC(=O)C1=CC=C(OC(C)=O)C=C1 MNRSUGVCPQRZPE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 2
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- KYXSVGVQGFPNRQ-UHFFFAOYSA-N 2-methyl-1,2,3,4-tetrahydroisoqioniline Natural products C1=CC=C2CN(C)CCC2=C1 KYXSVGVQGFPNRQ-UHFFFAOYSA-N 0.000 claims 1
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- 235000013772 propylene glycol Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical compound CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000003653 radioligand binding assay Methods 0.000 description 1
- 238000011552 rat model Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- AKHNMLFCWUSKQB-UHFFFAOYSA-L sodium thiosulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=S AKHNMLFCWUSKQB-UHFFFAOYSA-L 0.000 description 1
- 235000019345 sodium thiosulphate Nutrition 0.000 description 1
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- 239000004334 sorbic acid Substances 0.000 description 1
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- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000001593 sorbitan monooleate Substances 0.000 description 1
- 235000011069 sorbitan monooleate Nutrition 0.000 description 1
- 229940035049 sorbitan monooleate Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 238000012453 sprague-dawley rat model Methods 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 229940032147 starch Drugs 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000008221 sterile excipient Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000003039 tetrahydroisoquinolinyl group Chemical group C1(NCCC2=CC=CC=C12)* 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- QERYCTSHXKAMIS-UHFFFAOYSA-N thiophene-2-carboxylic acid Chemical class OC(=O)C1=CC=CS1 QERYCTSHXKAMIS-UHFFFAOYSA-N 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 239000003039 volatile agent Substances 0.000 description 1
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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/47—Quinolines; Isoquinolines
- A61K31/472—Non-condensed isoquinolines, e.g. papaverine
- A61K31/4725—Non-condensed isoquinolines, e.g. papaverine containing further heterocyclic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P21/00—Drugs for disorders of the muscular or neuromuscular system
- A61P21/02—Muscle relaxants, e.g. for tetanus or cramps
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/04—Centrally acting analgesics, e.g. opioids
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
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- 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
- A61P25/08—Antiepileptics; Anticonvulsants
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/14—Drugs for disorders of the nervous system for treating abnormal movements, e.g. chorea, dyskinesia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/18—Antipsychotics, i.e. neuroleptics; Drugs for mania or schizophrenia
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- 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
- A61P25/20—Hypnotics; Sedatives
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- 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
- A61P25/22—Anxiolytics
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/28—Drugs for disorders of the nervous system for treating neurodegenerative disorders of the central nervous system, e.g. nootropic agents, cognition enhancers, drugs for treating Alzheimer's disease or other forms of dementia
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- A—HUMAN NECESSITIES
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- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61P25/30—Drugs for disorders of the nervous system for treating abuse or dependence
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/08—Drugs for disorders of the metabolism for glucose homeostasis
- A61P3/10—Drugs for disorders of the metabolism for glucose homeostasis for hyperglycaemia, e.g. antidiabetics
-
- 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
- C07D217/04—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
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom 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 ring carbon atoms
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/02—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 two hetero rings
- C07D417/12—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 two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Engineering & Computer Science (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Neurology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Neurosurgery (AREA)
- Biomedical Technology (AREA)
- Pain & Pain Management (AREA)
- Psychiatry (AREA)
- Diabetes (AREA)
- Orthopedic Medicine & Surgery (AREA)
- Physical Education & Sports Medicine (AREA)
- Epidemiology (AREA)
- Emergency Medicine (AREA)
- Psychology (AREA)
- Obesity (AREA)
- Endocrinology (AREA)
- Hospice & Palliative Care (AREA)
- Anesthesiology (AREA)
- Addiction (AREA)
- Hematology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GBGB9705619.6A GB9705619D0 (en) | 1997-03-18 | 1997-03-18 | Novel compounds |
GBGB9726695.1A GB9726695D0 (en) | 1997-12-17 | 1997-12-17 | Novel compounds |
PCT/GB1998/000782 WO1998041508A1 (en) | 1997-03-18 | 1998-03-16 | Substituted isoquinoline derivatives and their use as anticonvulsants |
Publications (3)
Publication Number | Publication Date |
---|---|
NO994510D0 NO994510D0 (no) | 1999-09-17 |
NO994510L NO994510L (no) | 1999-09-17 |
NO314081B1 true NO314081B1 (no) | 2003-01-27 |
Family
ID=26311215
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO19994510A NO314081B1 (no) | 1997-03-18 | 1999-09-17 | Substituerte isokinolin-derivater og deres anvendelse og fremstilling, samtfarmasöytiske preparater inneholdende forbindelsene |
Country Status (16)
Country | Link |
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EP (1) | EP0968190A1 (ko) |
JP (1) | JP3690423B2 (ko) |
KR (1) | KR100568654B1 (ko) |
CN (1) | CN1183116C (ko) |
AR (1) | AR012092A1 (ko) |
AU (1) | AU737955B2 (ko) |
BR (1) | BR9809047A (ko) |
CA (1) | CA2284218A1 (ko) |
CO (1) | CO4950553A1 (ko) |
IL (1) | IL131756A0 (ko) |
NO (1) | NO314081B1 (ko) |
NZ (1) | NZ337424A (ko) |
PL (1) | PL192116B1 (ko) |
TR (1) | TR199902283T2 (ko) |
TW (1) | TW555694B (ko) |
WO (1) | WO1998041508A1 (ko) |
Families Citing this family (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB9726695D0 (en) | 1997-12-17 | 1998-02-18 | Smithkline Beecham Plc | Novel compounds |
WO1999021836A1 (en) * | 1997-10-24 | 1999-05-06 | Smithkline Beecham Plc | Substituted isoquinoline derivatives and their use as anticonvulsants |
GB9817424D0 (en) | 1998-08-11 | 1998-10-07 | Smithkline Beecham Plc | Novel compounds |
US20020006908A1 (en) * | 1998-12-03 | 2002-01-17 | Daniel P. Van Kammen | Anticonvulsant derivatives useful in treating schizophrenia |
ATE306481T1 (de) * | 1999-05-12 | 2005-10-15 | Ortho Mcneil Pharm Inc | Pyrazolecarboxamide zur behandlung von fettleibigkeit und anderen erkrankungen |
FR2795724B1 (fr) * | 1999-07-02 | 2002-12-13 | Sanofi Synthelabo | Nouveaux derives du benzene, un procede pour leur preparation et les compositions pharmaceutiques les contenant |
GB9915589D0 (en) * | 1999-07-02 | 1999-09-01 | Smithkline Beecham Plc | Novel compounds |
ES2316777T3 (es) | 2002-02-15 | 2009-04-16 | Glaxo Group Limited | Moduladores de receptores vainilloides. |
GB0210762D0 (en) * | 2002-05-10 | 2002-06-19 | Glaxo Group Ltd | Compounds |
WO2004014388A1 (en) * | 2002-08-13 | 2004-02-19 | Warner-Lambert Company Llc | 6,6-fused heteroaryl derivatives as matrix metalloproteinase inhibitors |
GB0226724D0 (en) | 2002-11-15 | 2002-12-24 | Merck Sharp & Dohme | Therapeutic agents |
MXPA05013434A (es) | 2003-06-12 | 2006-03-17 | Astellas Pharma Inc | Derivados de benzamida o sal del mismo. |
BRPI0415167A (pt) * | 2003-10-07 | 2006-11-28 | Renovis Inc | composto de amina como ligandos de canal de ìon e usos dos mesmos |
GB2413129A (en) * | 2003-10-07 | 2005-10-19 | Renovis Inc | Aromatic amide compounds as ion channel ligands and uses thereof |
CA2553968A1 (en) * | 2004-01-23 | 2005-08-11 | Amgen Inc. | Vanilloid receptor ligands and their use in treatments of inflammatory and neuropathic pain |
JP2008513426A (ja) * | 2004-09-20 | 2008-05-01 | バイオリポックス エービー | 炎症の治療に有用なピラゾール化合物 |
SE0403117D0 (sv) * | 2004-12-21 | 2004-12-21 | Astrazeneca Ab | New compounds 1 |
CA2659539A1 (en) | 2006-08-01 | 2008-02-07 | Glaxo Group Limited | Pyrazolo[3,4-b]pyridine compounds, and their use as pde4 inhibitors |
CN106608901B (zh) * | 2015-10-22 | 2020-10-16 | 彭莉 | 二羟基二甲基四氢异喹啉-3-甲酰-Lys(Lys-Ala),其合成,活性及应用 |
CN111138359A (zh) * | 2020-01-19 | 2020-05-12 | 浙江农林大学暨阳学院 | 制备3-羰基-4-叠氮基-n-苯磺酰基-1,2,3,4-四氢异喹啉类化合物的方法 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
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US4022900A (en) * | 1970-09-09 | 1977-05-10 | Marion Laboratories, Inc. | Compositions containing 1,2,3,4-tetrahydroisoquinolines used as hypotensive agents |
CZ416498A3 (cs) * | 1996-06-17 | 1999-06-16 | Smithkline Beecham Plc | Substituovaný benzamidový derivát a jeho použití jako antikonvulsantu |
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1998
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- 1998-03-16 CN CNB988048809A patent/CN1183116C/zh not_active Expired - Fee Related
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- 1998-03-16 TR TR1999/02283T patent/TR199902283T2/xx unknown
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- 1998-03-16 WO PCT/GB1998/000782 patent/WO1998041508A1/en not_active Application Discontinuation
- 1998-03-16 CA CA002284218A patent/CA2284218A1/en not_active Abandoned
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1999
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Also Published As
Publication number | Publication date |
---|---|
NO994510D0 (no) | 1999-09-17 |
JP2001515504A (ja) | 2001-09-18 |
CA2284218A1 (en) | 1998-09-24 |
TR199902283T2 (xx) | 1999-12-21 |
WO1998041508A1 (en) | 1998-09-24 |
IL131756A0 (en) | 2001-03-19 |
NO994510L (no) | 1999-09-17 |
PL192116B1 (pl) | 2006-08-31 |
CO4950553A1 (es) | 2000-09-01 |
AU737955B2 (en) | 2001-09-06 |
KR100568654B1 (ko) | 2006-04-07 |
EP0968190A1 (en) | 2000-01-05 |
CN1255124A (zh) | 2000-05-31 |
JP3690423B2 (ja) | 2005-08-31 |
TW555694B (en) | 2003-10-01 |
PL335676A1 (en) | 2000-05-08 |
AU6412898A (en) | 1998-10-12 |
NZ337424A (en) | 2001-08-31 |
KR20000076342A (ko) | 2000-12-26 |
BR9809047A (pt) | 2000-08-01 |
AR012092A1 (es) | 2000-09-27 |
CN1183116C (zh) | 2005-01-05 |
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