ES8801247A1 - 3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives - Google Patents
3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivativesInfo
- Publication number
- ES8801247A1 ES8801247A1 ES556101A ES556101A ES8801247A1 ES 8801247 A1 ES8801247 A1 ES 8801247A1 ES 556101 A ES556101 A ES 556101A ES 556101 A ES556101 A ES 556101A ES 8801247 A1 ES8801247 A1 ES 8801247A1
- Authority
- ES
- Spain
- Prior art keywords
- phenyl
- hydrogen
- imidazolylmethyl
- carbazol
- 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
Links
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)
Abstract
Compounds of formula (I). < IMAGE > [wherein R<1> is hydrogen C1-10 alkyl, C3-7 cycloalkyl, C3-6 alkenyl, phenyl or phenyl-C1-3alkyl, and one of the groups represented by R<2>, R<3> and R<4> is hydrogen, C1-6 alkyl, C3-7 cycloalkyl, C2-6 alkenyl or phenyl-C1-3alkyl and each of the other two groups, which may be the same or different, is hydrogen or C1-6alkyl and physiologically acceptable salts and solvates, e.g. hydrates, thereof] are potent selective antagonists at "neuronal" 5-hydroxytryptamine receptors and are useful in the treatment of migraine and psychotic disorders such as schizophrenia.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB848401888A GB8401888D0 (en) | 1984-01-25 | 1984-01-25 | Heterocyclic compounds |
GB848425959A GB8425959D0 (en) | 1984-10-15 | 1984-10-15 | Heterocyclic compounds |
Publications (2)
Publication Number | Publication Date |
---|---|
ES8801247A1 true ES8801247A1 (en) | 1987-12-16 |
ES556101A0 ES556101A0 (en) | 1987-12-16 |
Family
ID=26287221
Family Applications (3)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES539852A Expired ES8609309A1 (en) | 1984-01-25 | 1985-01-25 | 3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives |
ES548430A Expired ES8708224A1 (en) | 1984-01-25 | 1985-10-31 | 3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives |
ES556101A Expired ES8801247A1 (en) | 1984-01-25 | 1986-06-16 | 3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives |
Family Applications Before (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES539852A Expired ES8609309A1 (en) | 1984-01-25 | 1985-01-25 | 3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives |
ES548430A Expired ES8708224A1 (en) | 1984-01-25 | 1985-10-31 | 3-Imidazolylmethyl-1,2,3,9-tetrahydro-4H-carbazol-4-one derivatives |
Country Status (29)
Country | Link |
---|---|
KR (1) | KR920003064B1 (en) |
AT (1) | AT392276B (en) |
AU (1) | AU579132B2 (en) |
BE (1) | BE901576A (en) |
CA (1) | CA1252793A (en) |
CH (1) | CH664152A5 (en) |
CY (1) | CY1479A (en) |
CZ (1) | CZ404391A3 (en) |
DE (2) | DE3502508A1 (en) |
DK (1) | DK169521B1 (en) |
ES (3) | ES8609309A1 (en) |
FI (1) | FI84349C (en) |
FR (1) | FR2561244B1 (en) |
GB (1) | GB2153821B (en) |
GR (1) | GR850219B (en) |
HK (1) | HK33189A (en) |
HU (1) | HU193592B (en) |
IE (1) | IE57809B1 (en) |
IL (1) | IL74165A (en) |
IT (1) | IT1182150B (en) |
LU (2) | LU88268I2 (en) |
NL (2) | NL190373C (en) |
NO (2) | NO164025C (en) |
NZ (1) | NZ210940A (en) |
PH (1) | PH22672A (en) |
PT (1) | PT79890B (en) |
SE (1) | SE460359B (en) |
SG (1) | SG7089G (en) |
SK (1) | SK404391A3 (en) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2043535A1 (en) * | 1992-03-13 | 1993-12-16 | Vita Invest Sa | Procedure for the obtaining of 1,2,3,9-tetrahydro-9-methyl-3- (2-methyl-1H-imidazol-1-il) methyl-4h-carbazol-4-ona. (Machine-translation by Google Translate, not legally binding) |
Families Citing this family (77)
Publication number | Priority date | Publication date | Assignee | Title |
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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 |
DE3680123D1 (en) * | 1985-01-23 | 1991-08-14 | Glaxo Group Ltd | Tetrahydrocarbazolonderivate. |
DE385517T1 (en) * | 1985-03-14 | 1991-07-25 | Beecham Group P.L.C., Brentford, Middlesex, Gb | MEDICINES FOR TREATING EMERGENCY. |
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 |
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 |
US5204356A (en) * | 1985-07-24 | 1993-04-20 | Glaxo Group Limited | Treatment of anxiety |
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 |
NL8701682A (en) * | 1986-07-30 | 1988-02-16 | Sandoz Ag | METHOD FOR THE THERAPEUTIC USE OF SEROTONIN ANTAGONISTS, ACTIVE COMPOUNDS AND PHARMACEUTICAL PREPARATIONS CONTAINING THESE COMPOUNDS |
AT396870B (en) * | 1986-08-07 | 1993-12-27 | Sandoz Ag | Process for the production of a pharmaceutical formulation for the nasal administration of serotonin antagonists |
GB8623819D0 (en) * | 1986-10-03 | 1986-11-05 | Glaxo Group Ltd | Heterocyclic compounds |
EP0279114B2 (en) * | 1986-11-21 | 1995-08-23 | Glaxo Group Limited | Medicaments for the treatment or prevention of the withdrawal syndrome |
GB8627909D0 (en) * | 1986-11-21 | 1986-12-31 | Glaxo Group Ltd | Medicaments |
GR871809B (en) * | 1986-11-28 | 1988-03-07 | Glaxo Group Ltd | Process for the preparation of tricyclic ketones |
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 |
GB8628475D0 (en) * | 1986-11-28 | 1987-01-07 | Glaxo Group Ltd | Medicaments |
US4973594A (en) * | 1986-12-17 | 1990-11-27 | Glaxo Group Limited | Medicaments |
US5200414A (en) * | 1986-12-17 | 1993-04-06 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
IE60991B1 (en) * | 1986-12-17 | 1994-09-07 | Glaxo Group Ltd | Use of ketone derivatives in the treatment of cognitive disorders |
GB8630079D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
US5190954A (en) * | 1986-12-17 | 1993-03-02 | Glaxo Group Limited | Methods for the treatment of cognitive disorders |
GB8630071D0 (en) * | 1986-12-17 | 1987-01-28 | Glaxo Group Ltd | Medicaments |
EP0291172B1 (en) * | 1987-04-14 | 1992-11-19 | Glaxo Group Limited | Ketone derivatives |
DE3874229T2 (en) * | 1987-06-16 | 1993-03-25 | British Tech Group | USE OF DIOXOPIPERIDINE DERIVATIVES FOR PRODUCING A TOPICAL PREPARATION AS AN ANALGETIC. |
DE3822792C2 (en) * | 1987-07-11 | 1997-11-27 | Sandoz Ag | New use of 5HT¶3¶ antagonists |
GB8723157D0 (en) * | 1987-10-02 | 1987-11-04 | Beecham Group Plc | Compounds |
CA1304082C (en) * | 1987-10-22 | 1992-06-23 | Tetsuya Tahara | Benzoxazine compounds and pharmaceutical use thereof |
EP0317088A1 (en) * | 1987-10-22 | 1989-05-24 | Glaxo Group Limited | Ketone derivatives |
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 |
US5116984A (en) * | 1988-04-07 | 1992-05-26 | Glaxo Group Limited | Imidazole derivatives |
DK185489A (en) * | 1988-04-22 | 1989-10-23 | Duphar Int Res | IMIDAZOLYLMETHYL-CYCLOALKANOEBAA INDOLONES, THEIR PREPARATION AND USE |
EP0339959A3 (en) * | 1988-04-27 | 1991-03-20 | Glaxo Group Limited | Lactam derivatives |
GB8812636D0 (en) * | 1988-05-27 | 1988-06-29 | Glaxo Group Ltd | Chemical compounds |
US5173493A (en) * | 1988-09-27 | 1992-12-22 | Fujisawa Pharmaceutical Company, Ltd. | Pyridoindole derivatives and processes for preparation thereof |
US5290785A (en) * | 1988-09-27 | 1994-03-01 | Fujisawa Pharmaceutical Co., Ltd. | Therapeutic agent for ischemic diseases |
AU627221B2 (en) * | 1988-09-27 | 1992-08-20 | Fujisawa Pharmaceutical Co., Ltd. | Pyridoindole derivatives and processes for preparation thereof |
FR2639944B1 (en) * | 1988-12-06 | 1991-01-18 | Adir | NEW INDOLE DERIVATIVES, THEIR PREPARATION PROCESS AND THE PHARMACEUTICAL COMPOSITIONS CONTAINING THEM |
EP0377238A1 (en) * | 1988-12-22 | 1990-07-11 | Duphar International Research B.V | New annelated indolo (3,2-c)-lactams |
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 |
CA2012092A1 (en) * | 1989-03-13 | 1990-09-13 | Tadao Okegawa | 5-ht3 receptor antagonist |
ATE97803T1 (en) * | 1989-04-21 | 1993-12-15 | Sandoz Ag | THERAPEUTIC USE OF 5-HT3 RECEPTOR ANTAGONISTS. |
GB8914804D0 (en) * | 1989-06-28 | 1989-08-16 | Glaxo Group Ltd | Process |
US5276050A (en) * | 1989-08-01 | 1994-01-04 | Glaxo Group Limited | Medicaments |
GB8917557D0 (en) * | 1989-08-01 | 1989-09-13 | Glaxo Group Ltd | Medicaments |
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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 |
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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 |
AU683447B2 (en) * | 1993-03-08 | 1997-11-13 | Fujisawa Pharmaceutical Co., Ltd. | Medicament for treating or preventing cerebrovascular diseases |
GB9310756D0 (en) * | 1993-05-25 | 1993-07-14 | Glaxo Lab Sa | Compositions |
GB2325409B (en) * | 1994-06-28 | 1999-02-10 | Kenneth Francis Prendergast | Pharmaceutical use of ondansetron/cyclodextrin complexes |
GB9423588D0 (en) * | 1994-11-22 | 1995-01-11 | Glaxo Wellcome Inc | Compositions |
US6365743B1 (en) | 1995-10-13 | 2002-04-02 | Duphar International Research B.V. | Process for the preparation of enantiomerically pure imidazolyl compounds |
AU702594B2 (en) * | 1995-10-13 | 1999-02-25 | 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 |
WO2000051582A2 (en) | 1999-03-01 | 2000-09-08 | Sepracor Inc. | Methods for treating apnea and apnea disorders using optically pure r(+)ondansetron |
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 |
PT1499623E (en) | 2002-04-29 | 2007-08-10 | Teva Gyogyszergyar Zartkoeruee | De |
FI6164U1 (en) * | 2003-01-09 | 2004-03-15 | Synthon Bv | Ondansetronformer |
GB2398071B (en) * | 2003-01-24 | 2006-06-07 | Synthon Bv | Process for making ondansetron and intermediate thereof |
ES2238001B1 (en) * | 2004-01-21 | 2006-11-01 | Vita Cientifica, S.L. | NEW POLYMORPHIC FORMS OF ONDANSETRON, PROCEDURES FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING THEM AND THEIR USE AS ANANTIMETICS. |
US7288660B2 (en) | 2004-05-07 | 2007-10-30 | Taro Pharmaceutical Industries Limited | 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 |
ES2432618T3 (en) | 2009-05-20 | 2013-12-04 | Inserm (Institut National De La Santé Et De La Recherche Medicale) | Serotonin 5-HT3 receptor antagonists for use in the treatment or prevention of a pathology of the inner ear with vestibular deficit |
SI2432467T1 (en) | 2009-05-20 | 2018-06-29 | Inserm (Institut National De La Sante Et De La Recherche Medicale) | Serotonin 5-ht3 receptor antagonists for use in the treatment of lesional vestibular disorders |
CN115611864A (en) * | 2022-11-01 | 2023-01-17 | 常州兰陵制药有限公司 | Ondansetron compound and preparation method and application thereof |
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US3740404A (en) * | 1969-05-09 | 1973-06-19 | American Cyanamid Co | Piperidinomethylenedihydrocarbazolones |
US3634420A (en) * | 1969-05-09 | 1972-01-11 | American Cyanamid Co | 3(morpholinomethyl)-2 3-dihydro-carbazol-4(1h)-ones |
DE3680123D1 (en) * | 1985-01-23 | 1991-08-14 | Glaxo Group Ltd | Tetrahydrocarbazolonderivate. |
-
1985
- 1985-01-25 NZ NZ210940A patent/NZ210940A/en unknown
- 1985-01-25 PT PT79890A patent/PT79890B/en unknown
- 1985-01-25 FI FI850323A patent/FI84349C/en not_active IP Right Cessation
- 1985-01-25 IE IE187/85A patent/IE57809B1/en not_active IP Right Cessation
- 1985-01-25 ES ES539852A patent/ES8609309A1/en not_active Expired
- 1985-01-25 DE DE19853502508 patent/DE3502508A1/en active Granted
- 1985-01-25 GB GB08501889A patent/GB2153821B/en not_active Expired
- 1985-01-25 LU LU88268C patent/LU88268I2/xx unknown
- 1985-01-25 HU HU85296A patent/HU193592B/en unknown
- 1985-01-25 SE SE8500368A patent/SE460359B/en not_active IP Right Cessation
- 1985-01-25 IL IL74165A patent/IL74165A/en not_active IP Right Cessation
- 1985-01-25 NL NLAANVRAGE8500202,A patent/NL190373C/en not_active IP Right Cessation
- 1985-01-25 PH PH31770A patent/PH22672A/en unknown
- 1985-01-25 GR GR850219A patent/GR850219B/el active IP Right Revival
- 1985-01-25 LU LU85743A patent/LU85743A1/en active Protection Beyond IP Right Term
- 1985-01-25 BE BE0/214394A patent/BE901576A/en not_active IP Right Cessation
- 1985-01-25 AT AT204/85A patent/AT392276B/en not_active IP Right Cessation
- 1985-01-25 DE DE1993175046 patent/DE19375046I2/en active Active
- 1985-01-25 DK DK035785A patent/DK169521B1/en not_active IP Right Cessation
- 1985-01-25 CA CA000472888A patent/CA1252793A/en not_active Expired
- 1985-01-25 AU AU38097/85A patent/AU579132B2/en not_active Expired
- 1985-01-25 FR FR8501056A patent/FR2561244B1/en not_active Expired
- 1985-01-25 KR KR1019850000454A patent/KR920003064B1/en not_active IP Right Cessation
- 1985-01-25 NO NO850300A patent/NO164025C/en not_active IP Right Cessation
- 1985-01-25 IT IT47600/85A patent/IT1182150B/en active Protection Beyond IP Right Term
- 1985-01-25 CH CH346/85A patent/CH664152A5/en not_active IP Right Cessation
- 1985-10-31 ES ES548430A patent/ES8708224A1/en not_active Expired
-
1986
- 1986-06-16 ES ES556101A patent/ES8801247A1/en not_active Expired
-
1989
- 1989-02-09 SG SG70/89A patent/SG7089G/en unknown
- 1989-04-20 HK HK331/89A patent/HK33189A/en not_active IP Right Cessation
- 1989-07-21 CY CY1479A patent/CY1479A/en unknown
-
1991
- 1991-12-23 CZ CS914043A patent/CZ404391A3/en unknown
- 1991-12-23 SK SK4043-91A patent/SK404391A3/en unknown
-
1994
- 1994-05-31 NL NL940009C patent/NL940009I2/en unknown
- 1994-11-09 NO NO1994022C patent/NO1994022I1/en unknown
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
ES2043535A1 (en) * | 1992-03-13 | 1993-12-16 | Vita Invest Sa | Procedure for the obtaining of 1,2,3,9-tetrahydro-9-methyl-3- (2-methyl-1H-imidazol-1-il) methyl-4h-carbazol-4-ona. (Machine-translation by Google Translate, not legally binding) |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
FD1A | Patent lapsed |
Effective date: 20071029 |