DK169675B1 - 4-Imidazolylmethyltetrahydrocarbazoloner, fremgangsmåde til fremstilling deraf samt farmaceutiske præparater indeholdende forbindelserne - Google Patents
4-Imidazolylmethyltetrahydrocarbazoloner, fremgangsmåde til fremstilling deraf samt farmaceutiske præparater indeholdende forbindelserne Download PDFInfo
- Publication number
- DK169675B1 DK169675B1 DK624887A DK624887A DK169675B1 DK 169675 B1 DK169675 B1 DK 169675B1 DK 624887 A DK624887 A DK 624887A DK 624887 A DK624887 A DK 624887A DK 169675 B1 DK169675 B1 DK 169675B1
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- DK
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- Prior art keywords
- methyl
- compound
- formula
- alkyl
- compounds
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- 150000001875 compounds Chemical class 0.000 title claims description 176
- -1 4-Imidazolylmethyl tetrahydrocarbazolones Chemical class 0.000 title claims description 48
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 6
- 238000002360 preparation method Methods 0.000 title claims description 6
- 238000000034 method Methods 0.000 title description 24
- 230000008569 process Effects 0.000 title description 18
- 239000000203 mixture Substances 0.000 claims description 76
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 150000003839 salts Chemical class 0.000 claims description 33
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
- 239000001257 hydrogen Substances 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 16
- 125000006239 protecting group Chemical group 0.000 claims description 16
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
- 125000000304 alkynyl group Chemical group 0.000 claims description 14
- 239000012458 free base Substances 0.000 claims description 13
- 239000012453 solvate Substances 0.000 claims description 13
- ZRIRTEMBXFFOGF-UHFFFAOYSA-N 9-methyl-3-[(5-methyl-1h-imidazol-4-yl)methyl]-2,3-dihydro-1h-carbazol-4-one Chemical group N1C=NC(CC2C(C3=C(N(C4=CC=CC=C43)C)CC2)=O)=C1C ZRIRTEMBXFFOGF-UHFFFAOYSA-N 0.000 claims description 10
- 239000002585 base Substances 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 7
- 239000000546 pharmaceutical excipient Substances 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 5
- 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 4
- 125000004429 atom Chemical group 0.000 claims description 3
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- 230000001590 oxidative effect Effects 0.000 claims description 3
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- FYBPEKLUHPCPQU-UHFFFAOYSA-N 9-methyl-3-[(5-methyl-1h-imidazol-4-yl)methyl]-1,2,3,4-tetrahydrocarbazole Chemical group N1C=NC(CC2CC3=C(N(C4=CC=CC=C43)C)CC2)=C1C FYBPEKLUHPCPQU-UHFFFAOYSA-N 0.000 claims 1
- RQZWYAUHKPTGHP-UHFFFAOYSA-N 9-methyl-3-[(5-methyl-1h-imidazol-4-yl)methyl]-2,3-dihydro-1h-carbazol-4-one;hydrate;hydrochloride Chemical group O.Cl.N1C=NC(CC2C(C3=C(N(C4=CC=CC=C43)C)CC2)=O)=C1C RQZWYAUHKPTGHP-UHFFFAOYSA-N 0.000 claims 1
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- YTJXGDYAEOTOCG-UHFFFAOYSA-N lithium;di(propan-2-yl)azanide;oxolane Chemical compound [Li+].C1CCOC1.CC(C)[N-]C(C)C YTJXGDYAEOTOCG-UHFFFAOYSA-N 0.000 description 1
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- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
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- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 239000010970 precious metal Substances 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
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- 238000001959 radiotherapy Methods 0.000 description 1
- 229960000620 ranitidine Drugs 0.000 description 1
- VMXUWOKSQNHOCA-LCYFTJDESA-N ranitidine Chemical compound [O-][N+](=O)/C=C(/NC)NCCSCC1=CC=C(CN(C)C)O1 VMXUWOKSQNHOCA-LCYFTJDESA-N 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
- QBERHIJABFXGRZ-UHFFFAOYSA-M rhodium;triphenylphosphane;chloride Chemical compound [Cl-].[Rh].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 QBERHIJABFXGRZ-UHFFFAOYSA-M 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical class OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 1
- 201000000980 schizophrenia Diseases 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
- 238000007086 side reaction Methods 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 1
- 229940080313 sodium starch Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
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- 229960000391 sorbitan trioleate Drugs 0.000 description 1
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- 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
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- 238000007920 subcutaneous administration Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 150000003890 succinate salts Chemical class 0.000 description 1
- 229960004016 sucrose syrup Drugs 0.000 description 1
- JEYKZWRXDALMNG-UHFFFAOYSA-N sufotidine Chemical compound CN1N=C(CS(C)(=O)=O)N=C1NCCCOC1=CC=CC(CN2CCCCC2)=C1 JEYKZWRXDALMNG-UHFFFAOYSA-N 0.000 description 1
- 229950002504 sufotidine Drugs 0.000 description 1
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- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003892 tartrate salts Chemical class 0.000 description 1
- WHRNULOCNSKMGB-UHFFFAOYSA-N tetrahydrofuran thf Chemical compound C1CCOC1.C1CCOC1 WHRNULOCNSKMGB-UHFFFAOYSA-N 0.000 description 1
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- 239000008158 vegetable oil Substances 0.000 description 1
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Classifications
-
- 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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB8628473 | 1986-11-28 | ||
| GB868628473A GB8628473D0 (en) | 1986-11-28 | 1986-11-28 | Chemical compounds |
| GB878726537A GB8726537D0 (en) | 1987-11-12 | 1987-11-12 | Tricyclic ketones |
| GB8726537 | 1987-11-12 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK624887D0 DK624887D0 (da) | 1987-11-27 |
| DK624887A DK624887A (da) | 1988-05-29 |
| DK169675B1 true DK169675B1 (da) | 1995-01-09 |
Family
ID=26291603
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK624887A DK169675B1 (da) | 1986-11-28 | 1987-11-27 | 4-Imidazolylmethyltetrahydrocarbazoloner, fremgangsmåde til fremstilling deraf samt farmaceutiske præparater indeholdende forbindelserne |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4822881A (fr) |
| AT (1) | AT396933B (fr) |
| AU (1) | AU605805B2 (fr) |
| BE (1) | BE1001004A4 (fr) |
| CA (1) | CA1326032C (fr) |
| CH (1) | CH676120A5 (fr) |
| CZ (1) | CZ404591A3 (fr) |
| DE (1) | DE3740352A1 (fr) |
| DK (1) | DK169675B1 (fr) |
| ES (1) | ES2008360A6 (fr) |
| FI (1) | FI92062C (fr) |
| FR (1) | FR2611366B1 (fr) |
| GB (1) | GB2202530B (fr) |
| GR (1) | GR871809B (fr) |
| HK (1) | HK51591A (fr) |
| IE (1) | IE61510B1 (fr) |
| IL (1) | IL84635A (fr) |
| IT (1) | IT1211936B (fr) |
| NL (1) | NL8702851A (fr) |
| NO (1) | NO172581C (fr) |
| NZ (1) | NZ222725A (fr) |
| PH (1) | PH30436A (fr) |
| SE (1) | SE467255B (fr) |
| SG (1) | SG46591G (fr) |
Families Citing this family (32)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB8518742D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
| US5202343A (en) * | 1986-11-28 | 1993-04-13 | Glaxo Group Limited | Tricyclic ketones useful as HT3 -receptor antagonists |
| GB8812002D0 (en) * | 1988-05-20 | 1988-06-22 | Glaxo Group Ltd | Chemical compounds |
| DE3822792C2 (de) * | 1987-07-11 | 1997-11-27 | Sandoz Ag | Neue Verwendung von 5HT¶3¶-Antagonisten |
| US5360800A (en) * | 1987-09-03 | 1994-11-01 | Glaxo Group Limited | Tetrahydro-1H-pyrido[4,3-b]indol-1-one derivatives |
| GB8720693D0 (en) * | 1987-09-03 | 1987-10-07 | Glaxo Group Ltd | Chemical compounds |
| JPH01258673A (ja) * | 1987-10-22 | 1989-10-16 | Glaxo Group Ltd | ケトン誘導体 |
| US5116984A (en) * | 1988-04-07 | 1992-05-26 | 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 |
| EP0350129A1 (fr) * | 1988-07-07 | 1990-01-10 | Duphar International Research B.V | Indole cétones annelées avec un substituant imidazolylalkyle |
| EP0353983B1 (fr) * | 1988-08-02 | 1996-05-29 | Glaxo Group Limited | Dérivés lactamiques |
| HU207078B (en) * | 1988-08-02 | 1993-03-01 | Glaxo Group Ltd | Process for producing lactam derivatives and pharmaceutical compositions comprising such compounds |
| JPH02167280A (ja) * | 1988-08-15 | 1990-06-27 | Glaxo Group Ltd | ラクタム誘導体 |
| GB8820650D0 (en) * | 1988-09-01 | 1988-10-05 | Glaxo Group Ltd | Medicaments |
| GB8820653D0 (en) * | 1988-09-01 | 1988-10-05 | Glaxo Group Ltd | Medicaments |
| GB8820651D0 (en) * | 1988-09-01 | 1988-10-05 | Glaxo Group Ltd | Medicaments |
| JPH02180885A (ja) * | 1988-09-01 | 1990-07-13 | Glaxo Group Ltd | ラクタム誘導体 |
| AU627221B2 (en) * | 1988-09-27 | 1992-08-20 | Fujisawa Pharmaceutical Co., Ltd. | Pyridoindole derivatives and processes for preparation thereof |
| GB8823980D0 (en) * | 1988-10-13 | 1988-11-23 | Glaxo Group Ltd | Chemical compounds |
| US5223625A (en) * | 1988-12-22 | 1993-06-29 | Duphar International Research B.V. | Annelated indolo [3,2,-C]lactams |
| GB8904551D0 (en) * | 1989-02-28 | 1989-04-12 | Glaxo Group Ltd | Chemical compounds |
| GB8904552D0 (en) | 1989-02-28 | 1989-04-12 | Glaxo Group Ltd | Chemical process |
| HU204049B (en) * | 1989-02-28 | 1991-11-28 | Glaxo Group Ltd | Process for producing lactam derivatives and pharmaceutical compositions comprising same |
| DK0422154T3 (da) | 1989-04-21 | 1994-03-07 | Sandoz Ag | Terapeutisk anvendelse af 5-HT3-receptorantagonister |
| GB8928208D0 (en) * | 1989-12-13 | 1990-02-14 | Glaxo Group Ltd | Medicaments |
| HU211081B (en) * | 1990-12-18 | 1995-10-30 | Sandoz Ag | Process for producing indole derivatives as serotonin antagonists and pharmaceutical compositions containing the same |
| KR100368895B1 (ko) * | 2000-03-30 | 2003-01-24 | 하나제약 주식회사 | 1,2,3,9-테트라하이드로-9-메틸-3-[(2-메틸-1ｈ-이미다졸-1-일)메틸]-4ｈ-카바졸-4-온의 제조방법 |
| US6770655B2 (en) | 2002-01-18 | 2004-08-03 | Aryx Therapeutics | 5-HT3 receptor antagonists and methods of use |
| EP2253316B1 (fr) | 2009-05-20 | 2013-08-14 | INSERM (Institut National de la Santé et de la Recherche Médicale) | Antagonistes du récepteur 5-HT3 de la sérotonine pour une utilisation dans le traitement ou la prévention d'une pathologie de l'oreille interne avec déficits vestibulaires |
| JP5955767B2 (ja) | 2009-05-20 | 2016-07-20 | インセルム（インスティチュート ナショナル デ ラ サンテ エ デ ラ リシェルシェ メディカル） | 損傷性前庭障害の処置における使用のためのセロトニン５−ｈｔ３受容体拮抗薬 |
Family Cites Families (12)
| 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 |
| GB1365296A (en) * | 1970-10-30 | 1974-08-29 | Unilever Ltd | Dentifrice compositions |
| US4176230A (en) * | 1977-08-04 | 1979-11-27 | Hoffmann-La Roche Inc. | 5-(6-Alkylindol-3-ylmethylene)-1,3-dimethyl-2-(methylimino)-4-imidazolidinones |
| CA1141384A (fr) * | 1978-11-01 | 1983-02-15 | Morton Harfenist | Composes pharmaceutiques heterocycliques, leur preparation et leur utilisation; les intermediaires pour ces composes et leurs preparations |
| DK151884C (da) * | 1979-03-07 | 1988-06-13 | Pfizer | Analogifremgangsmaade til fremstilling af 3-(1-imidazolylalkyl)indolderivater eller farmaceutisk acceptable syreadditionssalte deraf |
| 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 |
| DE3502508A1 (de) * | 1984-01-25 | 1985-08-14 | Glaxo Group Ltd., London | Heterocyclische verbindungen |
| AU583343B2 (en) * | 1985-01-23 | 1989-04-27 | Glaxo Group Limited | Heterocyclic compounds |
| GB8518743D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8518745D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Heterocyclic compounds |
| GB8518741D0 (en) * | 1985-07-24 | 1985-08-29 | Glaxo Group Ltd | Process |
-
1987
- 1987-11-26 GR GR871809A patent/GR871809B/el unknown
- 1987-11-27 ES ES8703405A patent/ES2008360A6/es not_active Expired
- 1987-11-27 US US07/126,202 patent/US4822881A/en not_active Expired - Fee Related
- 1987-11-27 IE IE323287A patent/IE61510B1/en not_active IP Right Cessation
- 1987-11-27 IT IT8748642A patent/IT1211936B/it active
- 1987-11-27 GB GB8727835A patent/GB2202530B/en not_active Expired - Fee Related
- 1987-11-27 AU AU81845/87A patent/AU605805B2/en not_active Ceased
- 1987-11-27 NL NL8702851A patent/NL8702851A/nl not_active Application Discontinuation
- 1987-11-27 FI FI875235A patent/FI92062C/fi not_active IP Right Cessation
- 1987-11-27 CH CH4614/87A patent/CH676120A5/fr not_active IP Right Cessation
- 1987-11-27 FR FR878716488A patent/FR2611366B1/fr not_active Expired - Fee Related
- 1987-11-27 AT AT0312487A patent/AT396933B/de not_active IP Right Cessation
- 1987-11-27 IL IL84635A patent/IL84635A/xx not_active IP Right Cessation
- 1987-11-27 BE BE8701353A patent/BE1001004A4/fr not_active IP Right Cessation
- 1987-11-27 NO NO874959A patent/NO172581C/no unknown
- 1987-11-27 NZ NZ222725A patent/NZ222725A/xx unknown
- 1987-11-27 SE SE8704746A patent/SE467255B/sv not_active IP Right Cessation
- 1987-11-27 PH PH36132A patent/PH30436A/en unknown
- 1987-11-27 DK DK624887A patent/DK169675B1/da active
- 1987-11-27 CA CA000552963A patent/CA1326032C/fr not_active Expired - Fee Related
- 1987-11-27 DE DE19873740352 patent/DE3740352A1/de not_active Ceased
-
1991
- 1991-06-18 SG SG46591A patent/SG46591G/en unknown
- 1991-07-04 HK HK515/91A patent/HK51591A/xx not_active IP Right Cessation
- 1991-12-23 CZ CS914045A patent/CZ404591A3/cs unknown
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