KR920003064B1 - 헤테로시클릭 화합물의 제조방법 - Google Patents
헤테로시클릭 화합물의 제조방법 Download PDFInfo
- Publication number
- KR920003064B1 KR920003064B1 KR1019850000454A KR850000454A KR920003064B1 KR 920003064 B1 KR920003064 B1 KR 920003064B1 KR 1019850000454 A KR1019850000454 A KR 1019850000454A KR 850000454 A KR850000454 A KR 850000454A KR 920003064 B1 KR920003064 B1 KR 920003064B1
- Authority
- KR
- South Korea
- Prior art keywords
- methyl
- compound
- formula
- hydrogen atom
- tetrahydro
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
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- 238000000034 method Methods 0.000 title claims description 39
- 150000002391 heterocyclic compounds Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 165
- 239000000203 mixture Substances 0.000 claims description 56
- 150000003839 salts Chemical class 0.000 claims description 46
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 40
- -1 prop-2-enyl Chemical group 0.000 claims description 35
- 239000002904 solvent Substances 0.000 claims description 31
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 238000002360 preparation method Methods 0.000 claims description 19
- 230000008569 process Effects 0.000 claims description 17
- 239000012458 free base Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- FELGMEQIXOGIFQ-UHFFFAOYSA-N Ondansetron Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 FELGMEQIXOGIFQ-UHFFFAOYSA-N 0.000 claims description 14
- 125000006272 (C3-C7) cycloalkyl group Chemical group 0.000 claims description 12
- MKBLHFILKIKSQM-UHFFFAOYSA-N 9-methyl-3-[(2-methyl-1h-imidazol-3-ium-3-yl)methyl]-2,3-dihydro-1h-carbazol-4-one;chloride Chemical compound Cl.CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C)=C2CC1 MKBLHFILKIKSQM-UHFFFAOYSA-N 0.000 claims description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 5
- 150000004683 dihydrates Chemical class 0.000 claims description 5
- 238000005984 hydrogenation reaction Methods 0.000 claims description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
- 125000006239 protecting group Chemical group 0.000 claims description 4
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- 125000004429 atom Chemical group 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
- 125000006704 (C5-C6) cycloalkyl group Chemical group 0.000 claims description 2
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- LLBZPESJRQGYMB-UHFFFAOYSA-N 4-one Natural products O1C(C(=O)CC)CC(C)C11C2(C)CCC(C3(C)C(C(C)(CO)C(OC4C(C(O)C(O)C(COC5C(C(O)C(O)CO5)OC5C(C(OC6C(C(O)C(O)C(CO)O6)O)C(O)C(CO)O5)OC5C(C(O)C(O)C(C)O5)O)O4)O)CC3)CC3)=C3C2(C)CC1 LLBZPESJRQGYMB-UHFFFAOYSA-N 0.000 claims description 2
- ARFOLUOIUFOCJX-UHFFFAOYSA-N 9-cyclopentyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical compound CC1=NC=CN1CC1C(=O)C(C=2C(=CC=CC=2)N2C3CCCC3)=C2CC1 ARFOLUOIUFOCJX-UHFFFAOYSA-N 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- QCQCHGYLTSGIGX-GHXANHINSA-N 4-[[(3ar,5ar,5br,7ar,9s,11ar,11br,13as)-5a,5b,8,8,11a-pentamethyl-3a-[(5-methylpyridine-3-carbonyl)amino]-2-oxo-1-propan-2-yl-4,5,6,7,7a,9,10,11,11b,12,13,13a-dodecahydro-3h-cyclopenta[a]chrysen-9-yl]oxy]-2,2-dimethyl-4-oxobutanoic acid Chemical compound N([C@@]12CC[C@@]3(C)[C@]4(C)CC[C@H]5C(C)(C)[C@@H](OC(=O)CC(C)(C)C(O)=O)CC[C@]5(C)[C@H]4CC[C@@H]3C1=C(C(C2)=O)C(C)C)C(=O)C1=CN=CC(C)=C1 QCQCHGYLTSGIGX-GHXANHINSA-N 0.000 claims 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 3
- 230000001681 protective effect Effects 0.000 claims 3
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- 235000019441 ethanol Nutrition 0.000 description 38
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 34
- 238000002844 melting Methods 0.000 description 31
- 230000008018 melting Effects 0.000 description 31
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- 239000000725 suspension Substances 0.000 description 24
- 239000003921 oil Substances 0.000 description 20
- 235000019198 oils Nutrition 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 18
- 239000004480 active ingredient Substances 0.000 description 17
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 16
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 15
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 14
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 14
- 238000010992 reflux Methods 0.000 description 14
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- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 11
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 11
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- 238000011282 treatment Methods 0.000 description 9
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 7
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 6
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- 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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- 125000004423 acyloxy group Chemical group 0.000 description 6
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- 238000003756 stirring Methods 0.000 description 6
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 5
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- 150000002576 ketones Chemical class 0.000 description 4
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- UDYFLDICVHJSOY-UHFFFAOYSA-N sulfur trioxide pyridine complex Chemical class O=S(=O)=O.C1=CC=NC=C1 UDYFLDICVHJSOY-UHFFFAOYSA-N 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
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- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- UGNWTBMOAKPKBL-UHFFFAOYSA-N tetrachloro-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(Cl)=C(Cl)C1=O UGNWTBMOAKPKBL-UHFFFAOYSA-N 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
- VAHTXZHIVSIZHA-UHFFFAOYSA-K trichlororhodium trimethylphosphane Chemical compound CP(C)C.CP(C)C.CP(C)C.Cl[Rh](Cl)Cl VAHTXZHIVSIZHA-UHFFFAOYSA-K 0.000 description 1
- JEJAMASKDTUEBZ-UHFFFAOYSA-N tris(1,1,3-tribromo-2,2-dimethylpropyl) phosphate Chemical compound BrCC(C)(C)C(Br)(Br)OP(=O)(OC(Br)(Br)C(C)(C)CBr)OC(Br)(Br)C(C)(C)CBr JEJAMASKDTUEBZ-UHFFFAOYSA-N 0.000 description 1
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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 (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB848401888A GB8401888D0 (en) | 1984-01-25 | 1984-01-25 | Heterocyclic compounds |
| GB84-01888 | 1984-01-25 | ||
| GB8401888 | 1984-01-25 | ||
| GB8425959 | 1984-10-15 | ||
| GB848425959A GB8425959D0 (en) | 1984-10-15 | 1984-10-15 | Heterocyclic compounds |
| GB84-25959 | 1984-10-15 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR850005439A KR850005439A (ko) | 1985-08-26 |
| KR920003064B1 true KR920003064B1 (ko) | 1992-04-13 |
Family
ID=26287221
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019850000454A Expired KR920003064B1 (ko) | 1984-01-25 | 1985-01-25 | 헤테로시클릭 화합물의 제조방법 |
Country Status (29)
Families Citing this family (80)
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| 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 |
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| 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 |
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| 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 |
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| 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 |
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| 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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