LU85743A1 - Composes heterocycliques - Google Patents
Composes heterocycliques Download PDFInfo
- Publication number
- LU85743A1 LU85743A1 LU85743A LU85743A LU85743A1 LU 85743 A1 LU85743 A1 LU 85743A1 LU 85743 A LU85743 A LU 85743A LU 85743 A LU85743 A LU 85743A LU 85743 A1 LU85743 A1 LU 85743A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- methyl
- compound
- formula
- group
- hydrogen atom
- Prior art date
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- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 125
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 55
- 239000000203 mixture Substances 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 37
- -1 prop-2-enyl Chemical group 0.000 claims description 29
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 21
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 13
- 230000008569 process Effects 0.000 claims description 13
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 12
- 239000012453 solvate Substances 0.000 claims description 12
- 239000012458 free base Substances 0.000 claims description 11
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 6
- 238000005804 alkylation reaction Methods 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
- 239000008194 pharmaceutical composition Substances 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000000174 L-prolyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])[C@@]1([H])C(*)=O 0.000 claims description 3
- 230000029936 alkylation Effects 0.000 claims description 3
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- OMIXENIJKHPBSJ-UHFFFAOYSA-N 9-propan-2-yl-3H-carbazol-4-one Chemical compound CC(C)N1C2=CC=CC=C2C=2C(CC=CC1=2)=O OMIXENIJKHPBSJ-UHFFFAOYSA-N 0.000 claims 1
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims 1
- 108090000623 proteins and genes Proteins 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 109
- 239000000243 solution Substances 0.000 description 64
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 47
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 45
- 239000007787 solid Substances 0.000 description 42
- 235000019441 ethanol Nutrition 0.000 description 38
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 36
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 24
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- 229910021529 ammonia Inorganic materials 0.000 description 16
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
- MOWLUBGHVYJYTK-UHFFFAOYSA-N 3-(2-aminoethyl)indol-3-ol Chemical compound C1=CC=C2C(CCN)(O)C=NC2=C1 MOWLUBGHVYJYTK-UHFFFAOYSA-N 0.000 description 15
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- 238000010992 reflux Methods 0.000 description 14
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- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 7
- 238000004587 chromatography analysis Methods 0.000 description 7
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- 230000001537 neural effect Effects 0.000 description 7
- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 208000019695 Migraine disease Diseases 0.000 description 6
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 125000004423 acyloxy group Chemical group 0.000 description 6
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- 239000012312 sodium hydride Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 5
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- 239000004338 Dichlorodifluoromethane Substances 0.000 description 5
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- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 5
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
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- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 4
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- 125000000008 (C1-C10) alkyl group Chemical group 0.000 description 3
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- 239000004533 oil dispersion Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- HBEQXAKJSGXAIQ-UHFFFAOYSA-N oxopalladium Chemical compound [Pd]=O HBEQXAKJSGXAIQ-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- 229940124641 pain reliever Drugs 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229910003445 palladium oxide Inorganic materials 0.000 description 1
- 229960005489 paracetamol Drugs 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 210000000578 peripheral nerve Anatomy 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- CUQOHAYJWVTKDE-UHFFFAOYSA-N potassium;butan-1-olate Chemical compound [K+].CCCC[O-] CUQOHAYJWVTKDE-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 235000010232 propyl p-hydroxybenzoate Nutrition 0.000 description 1
- QELSKZZBTMNZEB-UHFFFAOYSA-N propylparaben Chemical class CCCOC(=O)C1=CC=C(O)C=C1 QELSKZZBTMNZEB-UHFFFAOYSA-N 0.000 description 1
- 230000037047 psychomotor activity Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- SONJTKJMTWTJCT-UHFFFAOYSA-K rhodium(iii) chloride Chemical compound [Cl-].[Cl-].[Cl-].[Rh+3] SONJTKJMTWTJCT-UHFFFAOYSA-K 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- OTNVGWMVOULBFZ-UHFFFAOYSA-N sodium;hydrochloride Chemical compound [Na].Cl OTNVGWMVOULBFZ-UHFFFAOYSA-N 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 235000010356 sorbitol Nutrition 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 229960004016 sucrose syrup Drugs 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 150000003461 sulfonyl halides Chemical class 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000002511 suppository base Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229960001367 tartaric acid Drugs 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 230000009466 transformation Effects 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 210000001186 vagus nerve Anatomy 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 230000025033 vasoconstriction Effects 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
- C07D209/88—Carbazoles; Hydrogenated carbazoles 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 ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848401888A GB8401888D0 (en) | 1984-01-25 | 1984-01-25 | Heterocyclic compounds |
| GB8401888 | 1984-01-25 | ||
| GB8425959 | 1984-10-15 | ||
| GB848425959A GB8425959D0 (en) | 1984-10-15 | 1984-10-15 | Heterocyclic compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU85743A1 true LU85743A1 (fr) | 1986-08-04 |
Family
ID=26287221
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU85743A LU85743A1 (fr) | 1984-01-25 | 1985-01-25 | Composes heterocycliques |
| LU88268C LU88268I2 (enrdf_load_html_response) | 1984-01-25 | 1985-01-25 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU88268C LU88268I2 (enrdf_load_html_response) | 1984-01-25 | 1985-01-25 |
Country Status (29)
Families Citing this family (80)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4695578A (en) * | 1984-01-25 | 1987-09-22 | Glaxo Group Limited | 1,2,3,9-tetrahydro-3-imidazol-1-ylmethyl-4H-carbazol-4-ones, composition containing them, and method of using them to treat neuronal 5HT function disturbances |
| EP0191562B1 (en) * | 1985-01-23 | 1991-07-10 | Glaxo Group Limited | Tetrahydrocarbazolone derivatives |
| DE3688296T2 (de) * | 1985-03-14 | 1993-11-04 | Beecham Group Plc | Arzneimittel zur behandlung von erbrechen. |
| US5578628A (en) * | 1985-06-25 | 1996-11-26 | Glaxo Group Limited | Medicaments for the treatment of nausea and vomiting |
| GB8516083D0 (en) * | 1985-06-25 | 1985-07-31 | Glaxo Group Ltd | Heterocyclic compounds |
| US5204356A (en) * | 1985-07-24 | 1993-04-20 | Glaxo Group Limited | Treatment of anxiety |
| GB8518741D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| GB8518743D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8518658D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Medicaments |
| GB8518742D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| GB8518745D0 (en) | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8617994D0 (en) * | 1986-07-23 | 1986-08-28 | Glaxo Group Ltd | Heterocyclic compounds |
| HU202108B (en) * | 1986-07-30 | 1991-02-28 | Sandoz Ag | Process for producing pharmaceutical compositions containing serotonine antqgonistic derivatives of indol-carboxylic acid or imidazolyl-methyl-carbazol |
| AT396870B (de) * | 1986-08-07 | 1993-12-27 | Sandoz Ag | Verfahren zur herstellung einer galenischen formulierung zur nasalen verabreichung von serotoninantagonisten |
| GB8623819D0 (en) * | 1986-10-03 | 1986-11-05 | Glaxo Group Ltd | Heterocyclic compounds |
| JP2765845B2 (ja) * | 1986-11-21 | 1998-06-18 | グラクソ、グループ、リミテッド | 中止症候群の予防の治療薬 |
| GB8627909D0 (en) * | 1986-11-21 | 1986-12-31 | Glaxo Group Ltd | Medicaments |
| US5202343A (en) * | 1986-11-28 | 1993-04-13 | Glaxo Group Limited | Tricyclic ketones useful as HT3 -receptor antagonists |
| GR871809B (en) * | 1986-11-28 | 1988-03-07 | Glaxo Group Ltd | Process for the preparation of tricyclic ketones |
| GB8628475D0 (en) * | 1986-11-28 | 1987-01-07 | Glaxo Group Ltd | Medicaments |
| GB8812002D0 (en) * | 1988-05-20 | 1988-06-22 | Glaxo Group Ltd | Chemical compounds |
| GB8630071D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
| JPS63277622A (ja) * | 1986-12-17 | 1988-11-15 | グラクソ、グループ、リミテッド | 医薬 |
| US5200414A (en) * | 1986-12-17 | 1993-04-06 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
| NZ222950A (en) * | 1986-12-17 | 1997-06-24 | Glaxo Group Ltd | Use of 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1h-imidazol-1-yl)methyl] -4h- carbazol-4-one for the manufacture of medicaments |
| US5190954A (en) * | 1986-12-17 | 1993-03-02 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
| GB8630079D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
| DE3876006T2 (de) * | 1987-04-14 | 1993-03-25 | Glaxo Group Ltd | Keton-derivate. |
| DE3874229T2 (de) * | 1987-06-16 | 1993-03-25 | British Tech Group | Verwendung von dioxopiperidin-derivaten zur herstellung eines topischen praeparates als analgetika. |
| DE3822792C2 (de) * | 1987-07-11 | 1997-11-27 | Sandoz Ag | Neue Verwendung von 5HT¶3¶-Antagonisten |
| GB8723157D0 (en) * | 1987-10-02 | 1987-11-04 | Beecham Group Plc | Compounds |
| EP0317088A1 (en) * | 1987-10-22 | 1989-05-24 | Glaxo Group Limited | Ketone derivatives |
| CA1304082C (en) * | 1987-10-22 | 1992-06-23 | Tetsuya Tahara | Benzoxazine compounds and pharmaceutical use thereof |
| US5225431A (en) * | 1987-10-23 | 1993-07-06 | Burroughs Wellcome Co. | Therapeutic substituted indole compounds and compositions thereof |
| GB8805269D0 (en) * | 1988-03-04 | 1988-04-07 | Glaxo Group Ltd | Medicaments |
| EP0336759A1 (en) * | 1988-04-07 | 1989-10-11 | Glaxo Group Limited | Imidazole derivatives |
| DK185489A (da) * | 1988-04-22 | 1989-10-23 | Duphar Int Res | Imidazolylmethyl-cycloalkanoebaaindoloner, deres fremstilling og anvendelse |
| US4985422A (en) * | 1988-04-27 | 1991-01-15 | Glaxo Group Limited | Lactam derivatives |
| GB8812636D0 (en) * | 1988-05-27 | 1988-06-29 | Glaxo Group Ltd | Chemical compounds |
| US5290785A (en) * | 1988-09-27 | 1994-03-01 | Fujisawa Pharmaceutical Co., Ltd. | Therapeutic agent for ischemic diseases |
| US5173493A (en) * | 1988-09-27 | 1992-12-22 | Fujisawa Pharmaceutical Company, Ltd. | Pyridoindole derivatives and processes for preparation thereof |
| AU627221B2 (en) * | 1988-09-27 | 1992-08-20 | Fujisawa Pharmaceutical Co., Ltd. | Pyridoindole derivatives and processes for preparation thereof |
| FR2639944B1 (fr) * | 1988-12-06 | 1991-01-18 | Adir | Nouveaux derives de l'indole, leur procede de preparation et les compositions pharmaceutiques qui les contiennent |
| US5223625A (en) * | 1988-12-22 | 1993-06-29 | Duphar International Research B.V. | Annelated indolo [3,2,-C]lactams |
| CA2004911A1 (en) * | 1988-12-22 | 1990-06-22 | Mitsuaki Ohta | 4,5,6,7-tetrahydrobenzimidazole derivatives |
| EP0377238A1 (en) * | 1988-12-22 | 1990-07-11 | Duphar International Research B.V | New annelated indolo (3,2-c)-lactams |
| EP0392663A1 (en) * | 1989-03-13 | 1990-10-17 | Ono Pharmaceutical Co., Ltd. | Carboline derivative as a 5-HT3 receptor antagonist |
| ATE97803T1 (de) * | 1989-04-21 | 1993-12-15 | Sandoz Ag | Therapeutische verwendung von 5-ht3-rezeptorantagonisten. |
| GB8914804D0 (en) * | 1989-06-28 | 1989-08-16 | Glaxo Group Ltd | Process |
| GB8917557D0 (en) * | 1989-08-01 | 1989-09-13 | Glaxo Group Ltd | Medicaments |
| US5276050A (en) * | 1989-08-01 | 1994-01-04 | Glaxo Group Limited | Medicaments |
| US5126343A (en) * | 1989-09-11 | 1992-06-30 | G. D. Searle & Co. | N-azabicyclo [3.3.0]octane amides of aromatic acids |
| GB2236751B (en) | 1989-10-14 | 1993-04-28 | Wyeth John & Brother Ltd | Heterocyclic compounds |
| GB8928837D0 (en) * | 1989-12-21 | 1990-02-28 | Beecham Group Plc | Pharmaceuticals |
| US5187166A (en) * | 1990-07-31 | 1993-02-16 | Nisshin Flour Milling Co., Ltd. | Azabicyclo derivatives and their use as antiemetics |
| JPH06508836A (ja) * | 1991-06-26 | 1994-10-06 | セプラコア，インコーポレーテッド | 光学的に純粋なｒ（＋）オンダンセトロンを使用する嘔吐、吐き気および他の障害の治療のための方法および組成物 |
| JPH05310732A (ja) * | 1992-03-12 | 1993-11-22 | Mitsubishi Kasei Corp | シンノリン−３−カルボン酸誘導体 |
| ES2043535B1 (es) * | 1992-03-13 | 1994-08-01 | Vita Invest Sa | Procedimiento para la obtencion de la 1,2,3,9-tetrahidro-9-metil-3-(2-metil-1h-imidazol-1-il)metil*-4h-carbazol-4-ona. |
| CA2106642C (en) * | 1992-10-14 | 2005-08-16 | Peter Bod | Carbazolone derivatives and process for preparing the same |
| HU212934B (en) | 1992-10-14 | 1996-12-30 | Richter Gedeon Vegyeszet | Process for producing novel alkoxalylated carbazolone derivatives |
| CN1118990A (zh) * | 1993-03-08 | 1996-03-20 | 藤泽药品工业株式会社 | 治疗或预防脑血管疾病药物 |
| GB9310756D0 (en) * | 1993-05-25 | 1993-07-14 | Glaxo Lab Sa | Compositions |
| GB2325408B (en) * | 1994-06-28 | 1999-01-27 | Kenneth Francis Prendergast | Chewing gum formulation comprising ondansetron |
| GB9423588D0 (en) * | 1994-11-22 | 1995-01-11 | Glaxo Wellcome Inc | Compositions |
| AU702594B2 (en) * | 1995-10-13 | 1999-02-25 | Duphar International Research B.V. | Process for the preparation of enantiomerically pure imidazolyl compounds |
| US6365743B1 (en) | 1995-10-13 | 2002-04-02 | Duphar International Research B.V. | Process for the preparation of enantiomerically pure imidazolyl compounds |
| US5969137A (en) * | 1996-09-19 | 1999-10-19 | Virginia Commonwealth University | Benzylamidine derivatives with serotonin receptor binding activity |
| JP2002538102A (ja) | 1999-03-01 | 2002-11-12 | セプラコア インコーポレーテッド | 光学的に純粋なｒ（＋）オンダンセトロンを使用する無呼吸および無呼吸障害の治療方法 |
| EP1207160A1 (en) * | 2000-11-20 | 2002-05-22 | Hanmi Pharm. Co., Ltd. | Process for the preparation of 1,2,3,9-tetrahydro-9-methyl-3-((2-methyl-1H-imidazol-1-yl)-methyl)-4H-carbazol-4-one |
| RU2207340C2 (ru) * | 2001-08-10 | 2003-06-27 | Ципла Лтд. | Способ получения 1,2,3,9-тетрагидро-9-метил-3-[(2-метил-1н-имидазол-1-ил)метил]-4н-карбазол -4-она или его фармацевтически приемлемых солей |
| US7098345B2 (en) | 2002-04-29 | 2006-08-29 | TEVA Gyógyszergyár Zárkörüen Müködö Részvénytársaság | Process for preparing 1,2,3,9-tetrahydro-9-methyl-3-[(2-methyl-1H-imidazol-1-YL)methyl]-4H-carbazol-4-one |
| FI6164U1 (fi) * | 2003-01-09 | 2004-03-15 | Synthon Bv | Ondansetronmuotoja |
| GB2398071B (en) * | 2003-01-24 | 2006-06-07 | Synthon Bv | Process for making ondansetron and intermediate thereof |
| ES2238001B1 (es) * | 2004-01-21 | 2006-11-01 | Vita Cientifica, S.L. | Nuevas formas polimorficas de ondansetron, procedimientos para su preparacion, composiciones farmaceuticas que los contienen y su uso como aantiemeticos. |
| CA2565854A1 (en) | 2004-05-07 | 2005-11-17 | Taro Pharmaceutical Industries Ltd. | Process for preparing ondansetron hydrochloride dihydrate having a defined particle size |
| US20090170872A1 (en) * | 2005-07-05 | 2009-07-02 | Orchid Research Laboratories Limited | Compounds and Their Pharmaceutical Use |
| EP2253316B1 (en) | 2009-05-20 | 2013-08-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Serotonin 5-HT3 receptor antagonists for use in the treatment or prevention of an inner ear pathology with vestibular deficits |
| PL2432467T3 (pl) | 2009-05-20 | 2018-07-31 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Zastosowanie antagonistów receptora 5-ht3 serotoniny w leczeniu zaburzeń przedsionkowych ze zmianami chorobowymi |
| CN115611864A (zh) * | 2022-11-01 | 2023-01-17 | 常州兰陵制药有限公司 | 一种昂丹司琼类化合物及其制备方法与应用 |
| GB202301322D0 (en) | 2023-01-30 | 2023-03-15 | Therakind Ltd | Antiemetic pharmaceutical compositions for nasal delivery |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3634420A (en) * | 1969-05-09 | 1972-01-11 | American Cyanamid Co | 3(morpholinomethyl)-2 3-dihydro-carbazol-4(1h)-ones |
| US3740404A (en) * | 1969-05-09 | 1973-06-19 | American Cyanamid Co | Piperidinomethylenedihydrocarbazolones |
| EP0191562B1 (en) * | 1985-01-23 | 1991-07-10 | Glaxo Group Limited | Tetrahydrocarbazolone derivatives |
-
1985
- 1985-01-25 GR GR850219A patent/GR850219B/el active IP Right Revival
- 1985-01-25 IE IE187/85A patent/IE57809B1/en not_active IP Right Cessation
- 1985-01-25 NO NO850300A patent/NO164025C/no not_active IP Right Cessation
- 1985-01-25 SE SE8500368A patent/SE460359B/sv not_active IP Right Cessation
- 1985-01-25 CA CA000472888A patent/CA1252793A/en not_active Expired
- 1985-01-25 CH CH346/85A patent/CH664152A5/fr not_active IP Right Cessation
- 1985-01-25 IL IL74165A patent/IL74165A/xx not_active IP Right Cessation
- 1985-01-25 LU LU85743A patent/LU85743A1/fr active Protection Beyond IP Right Term
- 1985-01-25 DE DE19853502508 patent/DE3502508A1/de active Granted
- 1985-01-25 DK DK035785A patent/DK169521B1/da not_active IP Right Cessation
- 1985-01-25 AU AU38097/85A patent/AU579132B2/en not_active Expired
- 1985-01-25 PT PT79890A patent/PT79890B/pt unknown
- 1985-01-25 FI FI850323A patent/FI84349C/fi not_active IP Right Cessation
- 1985-01-25 ES ES539852A patent/ES8609309A1/es not_active Expired
- 1985-01-25 IT IT47600/85A patent/IT1182150B/it active Protection Beyond IP Right Term
- 1985-01-25 NZ NZ210940A patent/NZ210940A/xx unknown
- 1985-01-25 LU LU88268C patent/LU88268I2/xx unknown
- 1985-01-25 BE BE0/214394A patent/BE901576A/fr not_active IP Right Cessation
- 1985-01-25 PH PH31770A patent/PH22672A/en unknown
- 1985-01-25 GB GB08501889A patent/GB2153821B/en not_active Expired
- 1985-01-25 AT AT204/85A patent/AT392276B/de not_active IP Right Cessation
- 1985-01-25 DE DE1993175046 patent/DE19375046I2/de active Active
- 1985-01-25 HU HU85296A patent/HU193592B/hu unknown
- 1985-01-25 FR FR8501056A patent/FR2561244B1/fr not_active Expired
- 1985-01-25 KR KR1019850000454A patent/KR920003064B1/ko not_active Expired
- 1985-01-25 NL NLAANVRAGE8500202,A patent/NL190373C/xx not_active IP Right Cessation
- 1985-10-31 ES ES548430A patent/ES8708224A1/es not_active Expired
-
1986
- 1986-06-16 ES ES556101A patent/ES8801247A1/es not_active Expired
-
1989
- 1989-02-09 SG SG70/89A patent/SG7089G/en unknown
- 1989-04-20 HK HK331/89A patent/HK33189A/xx not_active IP Right Cessation
- 1989-07-21 CY CY1479A patent/CY1479A/en unknown
-
1991
- 1991-12-23 CZ CS914043A patent/CZ404391A3/cs unknown
- 1991-12-23 SK SK4043-91A patent/SK277923B6/sk unknown
-
1994
- 1994-05-31 NL NL940009C patent/NL940009I2/nl unknown
- 1994-11-09 NO NO1994022C patent/NO1994022I1/no unknown
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