LU87261A1 - Nouveaux derives de la thiouree,leur preparation et leur utilisation comme medicaments - Google Patents
Nouveaux derives de la thiouree,leur preparation et leur utilisation comme medicaments Download PDFInfo
- Publication number
- LU87261A1 LU87261A1 LU87261A LU87261A LU87261A1 LU 87261 A1 LU87261 A1 LU 87261A1 LU 87261 A LU87261 A LU 87261A LU 87261 A LU87261 A LU 87261A LU 87261 A1 LU87261 A1 LU 87261A1
- Authority
- LU
- Luxembourg
- Prior art keywords
- compound
- formula
- hydroxy
- benzyl
- methoxy
- Prior art date
Links
- 239000003814 drug Substances 0.000 title claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 49
- 150000002148 esters Chemical class 0.000 claims description 17
- 150000003839 salts Chemical class 0.000 claims description 17
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 230000000202 analgesic effect Effects 0.000 claims description 7
- 229910052736 halogen Inorganic materials 0.000 claims description 7
- 150000002367 halogens Chemical class 0.000 claims description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
- -1 4-hydroxy-3-methoxy-benzyl Chemical group 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 239000002260 anti-inflammatory agent Substances 0.000 claims description 3
- 229940121363 anti-inflammatory agent Drugs 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 239000008194 pharmaceutical composition Substances 0.000 claims description 3
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 3
- KDXZRBCUTLWBGQ-UHFFFAOYSA-N 1-[2-(4-chlorophenyl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea Chemical compound C1=C(O)C(OC)=CC(C\N=C(/S)NCCC=2C=CC(Cl)=CC=2)=C1 KDXZRBCUTLWBGQ-UHFFFAOYSA-N 0.000 claims description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 230000010933 acylation Effects 0.000 claims description 2
- 238000005917 acylation reaction Methods 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- NGQCHQJXDBGSLB-UHFFFAOYSA-N 1-[(4-hydroxy-3-methoxyphenyl)methyl]-3-[2-(4-phenylmethoxyphenyl)ethyl]thiourea Chemical compound OC1=C(C=C(CNC(=S)NCCC2=CC=C(C=C2)OCC2=CC=CC=C2)C=C1)OC NGQCHQJXDBGSLB-UHFFFAOYSA-N 0.000 claims 1
- XUCOQMNLQOBFPZ-UHFFFAOYSA-N 1-[2-(4-fluorophenyl)ethyl]-3-[(4-hydroxy-3-methoxyphenyl)methyl]thiourea Chemical compound C1=C(O)C(OC)=CC(C\N=C(/S)NCCC=2C=CC(F)=CC=2)=C1 XUCOQMNLQOBFPZ-UHFFFAOYSA-N 0.000 claims 1
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims 1
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims 1
- 101100260565 Dictyostelium discoideum thyA gene Proteins 0.000 claims 1
- 101150068774 thyX gene Proteins 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 241001465754 Metazoa Species 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 208000002193 Pain Diseases 0.000 description 5
- 230000003110 anti-inflammatory effect Effects 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 206010061218 Inflammation Diseases 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000002757 inflammatory effect Effects 0.000 description 3
- 230000004054 inflammatory process Effects 0.000 description 3
- 238000002347 injection Methods 0.000 description 3
- 239000007924 injection Substances 0.000 description 3
- 239000011780 sodium chloride Substances 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 208000001407 Vascular Headaches Diseases 0.000 description 2
- 239000000730 antalgic agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 238000002560 therapeutic procedure Methods 0.000 description 2
- 150000003585 thioureas Chemical class 0.000 description 2
- KLRKBAFQXKDRQU-UHFFFAOYSA-N (4-ethyloxan-4-yl)methanamine Chemical compound CCC1(CN)CCOCC1 KLRKBAFQXKDRQU-UHFFFAOYSA-N 0.000 description 1
- MRJJYUJULSZFDV-UHFFFAOYSA-N 1-chloro-4-(2-isothiocyanatoethyl)benzene Chemical compound ClC1=CC=C(CCN=C=S)C=C1 MRJJYUJULSZFDV-UHFFFAOYSA-N 0.000 description 1
- DEHXIHUIYSXZNH-UHFFFAOYSA-N 1-chloro-4-(isothiocyanatomethyl)benzene Chemical compound ClC1=CC=C(CN=C=S)C=C1 DEHXIHUIYSXZNH-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 208000000094 Chronic Pain Diseases 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010019233 Headaches Diseases 0.000 description 1
- 208000004454 Hyperalgesia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 208000019695 Migraine disease Diseases 0.000 description 1
- 229920005439 Perspex® Polymers 0.000 description 1
- 201000004681 Psoriasis Diseases 0.000 description 1
- 208000003782 Raynaud disease Diseases 0.000 description 1
- 208000012322 Raynaud phenomenon Diseases 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 1
- 206010043269 Tension headache Diseases 0.000 description 1
- 208000008548 Tension-Type Headache Diseases 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 206010003246 arthritis Diseases 0.000 description 1
- 238000013475 authorization Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 208000035475 disorder Diseases 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 239000000284 extract Substances 0.000 description 1
- 208000030533 eye disease Diseases 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 231100000869 headache Toxicity 0.000 description 1
- 239000003701 inert diluent Substances 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 230000004968 inflammatory condition Effects 0.000 description 1
- 208000027866 inflammatory disease Diseases 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 206010027599 migraine Diseases 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- 208000004296 neuralgia Diseases 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 230000004962 physiological condition Effects 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000011477 surgical intervention Methods 0.000 description 1
- 239000012730 sustained-release form Substances 0.000 description 1
- 208000011580 syndromic disease Diseases 0.000 description 1
- 230000002792 vascular Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/04—Derivatives of thiourea
- C07C335/06—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms
- C07C335/10—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton
- C07C335/12—Derivatives of thiourea having nitrogen atoms of thiourea groups bound to acyclic carbon atoms of an unsaturated carbon skeleton the carbon skeleton containing six-membered aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P29/00—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID]
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Pain & Pain Management (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Rheumatology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB878715357A GB8715357D0 (en) | 1987-06-30 | 1987-06-30 | Organic compounds |
| GB8715357 | 1987-06-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| LU87261A1 true LU87261A1 (fr) | 1989-03-08 |
Family
ID=10619833
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| LU87261A LU87261A1 (fr) | 1987-06-30 | 1988-06-28 | Nouveaux derives de la thiouree,leur preparation et leur utilisation comme medicaments |
Country Status (16)
| Country | Link |
|---|---|
| JP (1) | JPS6426551A (es) |
| KR (1) | KR890000417A (es) |
| AU (1) | AU1846488A (es) |
| DE (1) | DE3821317A1 (es) |
| DK (1) | DK356588A (es) |
| ES (1) | ES2010284A6 (es) |
| FI (1) | FI883097A7 (es) |
| FR (1) | FR2617477A1 (es) |
| GB (2) | GB8715357D0 (es) |
| IL (1) | IL86890A0 (es) |
| IT (1) | IT1219676B (es) |
| LU (1) | LU87261A1 (es) |
| NL (1) | NL8801659A (es) |
| PT (1) | PT87854B (es) |
| SE (1) | SE8802412L (es) |
| ZA (1) | ZA884693B (es) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5099030A (en) * | 1987-03-09 | 1992-03-24 | The Procter & Gamble Company | Novel compounds, pharmaceutical compositions, and methods for treating inflammation and pain |
| US5045565A (en) * | 1987-03-09 | 1991-09-03 | The Procter & Gamble Company | Novel compounds, pharmaceutical compositions, and methods for treating inflammation and pain |
| US5461075A (en) * | 1988-06-17 | 1995-10-24 | The Procter & Gamble Company | Use of vanilloids for the prevention of lesions due to herpes simplex infections |
| GR880100400A (el) * | 1988-06-21 | 1990-05-11 | Sandoz Ag | Μεθοδος παρασκευης παραγωγων θειουριας |
| HU206082B (en) * | 1988-12-23 | 1992-08-28 | Sandoz Ag | Process for producing capsaicin derivatives and pharmaceutical compositions comprising such compounds |
| US5403868A (en) * | 1988-12-23 | 1995-04-04 | Sandoz Ltd. | Capsaicin derivatives |
| HU210683B (en) * | 1990-06-18 | 1995-06-28 | Sandoz Ag | Process for producing n-benzyl-n1-(phenyl-alkyl)-thiourea derivatives and pharmaceutical compositions containing the same |
| TW476996B (en) | 2000-02-28 | 2002-02-21 | Mitsubishi Material Silicon | Semiconductor manufacturing method and semiconductor manufacturing apparatus |
| US6545182B2 (en) * | 2000-04-13 | 2003-04-08 | Allergan Sales, Inc. | Methods and compositions for modulating alpha adrenergic receptor activity |
| US6313172B1 (en) * | 2000-04-13 | 2001-11-06 | Allergan Sales, Inc. | Methods and compositions for modulating alpha adrenergic receptor activity |
| EP1303483B1 (en) * | 2000-08-21 | 2008-04-23 | Pacific Corporation | Novel thiourea derivatives and the pharmaceutical compositions containing the same |
| ES2266227T3 (es) | 2000-08-21 | 2007-03-01 | Pacific Corporation | Nuevos compuestos de (tio)urea y composiciones farmaceuticas que los contienen. |
| ITMI20041231A1 (it) * | 2004-06-18 | 2004-09-18 | Pharmeste Srl | Antagonisti del recettore dei vanilloidi trpv1 |
| EP1939173A1 (en) * | 2006-12-21 | 2008-07-02 | Pharmeste S.r.l. | O-substituted-dibenzyl urea- or thiourea- derivatives as trpv1 receptor antagonists |
-
1987
- 1987-06-30 GB GB878715357A patent/GB8715357D0/en active Pending
-
1988
- 1988-06-24 DE DE3821317A patent/DE3821317A1/de not_active Withdrawn
- 1988-06-27 FR FR8808719A patent/FR2617477A1/fr not_active Withdrawn
- 1988-06-27 GB GB08815258A patent/GB2206347A/en not_active Withdrawn
- 1988-06-28 AU AU18464/88A patent/AU1846488A/en not_active Abandoned
- 1988-06-28 IT IT48132/88A patent/IT1219676B/it active
- 1988-06-28 DK DK356588A patent/DK356588A/da not_active Application Discontinuation
- 1988-06-28 LU LU87261A patent/LU87261A1/fr unknown
- 1988-06-28 FI FI883097A patent/FI883097A7/fi not_active Application Discontinuation
- 1988-06-28 SE SE8802412A patent/SE8802412L/ not_active Application Discontinuation
- 1988-06-28 IL IL86890A patent/IL86890A0/xx unknown
- 1988-06-28 PT PT87854A patent/PT87854B/pt not_active IP Right Cessation
- 1988-06-29 KR KR1019880007885A patent/KR890000417A/ko not_active Withdrawn
- 1988-06-29 JP JP63162367A patent/JPS6426551A/ja active Pending
- 1988-06-30 NL NL8801659A patent/NL8801659A/nl not_active Application Discontinuation
- 1988-06-30 ES ES8802065A patent/ES2010284A6/es not_active Expired
- 1988-06-30 ZA ZA884693A patent/ZA884693B/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT8848132A0 (it) | 1988-06-28 |
| PT87854A (pt) | 1988-07-01 |
| GB8815258D0 (en) | 1988-08-03 |
| FI883097A0 (fi) | 1988-06-28 |
| KR890000417A (ko) | 1989-03-14 |
| DE3821317A1 (de) | 1989-01-12 |
| NL8801659A (nl) | 1989-01-16 |
| SE8802412D0 (sv) | 1988-06-28 |
| GB8715357D0 (en) | 1987-08-05 |
| SE8802412L (sv) | 1988-12-31 |
| FR2617477A1 (fr) | 1989-01-06 |
| IL86890A0 (en) | 1988-11-30 |
| ES2010284A6 (es) | 1989-11-01 |
| ZA884693B (en) | 1990-03-28 |
| FI883097A7 (fi) | 1988-12-31 |
| AU1846488A (en) | 1989-01-05 |
| PT87854B (pt) | 1992-10-30 |
| DK356588A (da) | 1988-12-31 |
| IT1219676B (it) | 1990-05-24 |
| DK356588D0 (da) | 1988-06-28 |
| GB2206347A (en) | 1989-01-05 |
| JPS6426551A (en) | 1989-01-27 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| BE1000071A4 (fr) | Derives d'indole, procede pour leur preparation et compositions pharmaceutiques les contenant. | |
| LU87261A1 (fr) | Nouveaux derives de la thiouree,leur preparation et leur utilisation comme medicaments | |
| CH642618A5 (fr) | Phenethanolamines et compositions pharmaceutiques en contenant. | |
| CA1265794A (fr) | 4h-triazolo [4,3-a] [1,4] benzodiazepines, leur procede de preparation, leur application comme medicaments et les compositions les renfermant | |
| EP0003199A2 (fr) | Nouveaux dérivés du tétrahydro pyridinyl indole et leurs sels, le procédé de préparation, l'application à titre de médicaments de ces nouveaux produits et les compositions pharmaceutiques les renfermant | |
| CH628344A5 (fr) | Procede de preparation de nouveaux derives du piperidyl-indole et de leurs sels. | |
| EP0012639A2 (fr) | Nouveaux dérivés de l'acide 3-quinoléine carboxylique, leur procédé de préparation, leur application comme médicament et les compositions pharmaceutiques les renfermant | |
| EP0022118A1 (fr) | Nouveaux dérivés de sulfonyl-aniline, leur procédé de préparation et leur application en thérapeutique | |
| CH649994A5 (fr) | Derives du 4h-1,2,4-triazole, procedes de preparation et compositions les renfermant. | |
| EP0024960B1 (fr) | Nouvelles phénoxyamines hétérocycliques substituées, procédé pour leur préparation et leur application comme anesthésiques locaux | |
| EP1753725B1 (fr) | Derives de tetrahydroisoquinolilsulfonamides, leur preparation et leur utilisation en therapeutique | |
| LU81565A1 (fr) | Nouvelles imidazoquinoxalines et leurs sels,leur procede de preparation,leur application a titre de medicaments et les compositions pharmaceutiques les renfermant | |
| EP1776340A1 (fr) | Derives de n-(1 h-indolyl)-i h-ind0le-2-carb0xamides, leur preparation et leur application en therapeutique | |
| CA2030401C (fr) | Inhibition du syndrome d'abstinence | |
| FR2467840A1 (fr) | Acides benzoyl-3 nitro-2 phenylacetiques et sels metalliques, amides et esters correspondants utiles notamment comme medicaments anti-inflammatoires compositions therapeutiques et formes pharmaceutiques les contenant et procedes et intermediaires pour leur preparation | |
| EP0022705B1 (fr) | Nouveaux dérivés du tétrahydropyridinyl-indole et leurs sels, leur préparation, leur application comme médicaments et les compositions les renfermant | |
| LU87129A1 (fr) | Nouvel acide piperazinecarboxylique,sa preparation et son utilisation comme medicament | |
| MC2105A1 (fr) | Derives de tetrahydronaphtalene | |
| EP0275221B1 (fr) | Nouveaux dérivés du N-(1H-indol 4-yl) benzamide ainsi que leurs sels, leur application à titre de médicaments et les compositions les renfermant | |
| FR2617478A1 (fr) | Nouveaux derives d'aryl-heteroaryl cetones, leur procede de preparation ainsi que leur application a titre de medicament | |
| EP0275762A1 (fr) | Dérivés de l'indole carboxamide ainsi que leurs sels, procédé et intermédiaires de préparation, application à titre de médicaments de ces dérivés et compositions les renfermant | |
| LU81832A1 (fr) | Nouveaux derives d'acyl-1h-1,2,4-triazoles et leur procede de preparation | |
| CA1064489A (fr) | Procede d'obtention de nouveaux benzene sulfonamides | |
| FR2458550A1 (fr) | Nouveaux derives du tetrahydropyridinyl-indole, leurs sels, procede de preparation, application a titre de medicaments et compositions les renfermant | |
| CH648295A5 (fr) | Acides 2-amino-3-(alkylthiobenzyl)-phenylacetiques et leurs derives. |