DK167009B1 - Cycloalkanooe1,2-baaindolsulfonamider, isomere og fysiologisk acceptable salte deraf, deres fremstilling og anvendelse samt laegemiddel indeholdende dem - Google Patents
Cycloalkanooe1,2-baaindolsulfonamider, isomere og fysiologisk acceptable salte deraf, deres fremstilling og anvendelse samt laegemiddel indeholdende dem Download PDFInfo
- Publication number
- DK167009B1 DK167009B1 DK087187A DK87187A DK167009B1 DK 167009 B1 DK167009 B1 DK 167009B1 DK 087187 A DK087187 A DK 087187A DK 87187 A DK87187 A DK 87187A DK 167009 B1 DK167009 B1 DK 167009B1
- Authority
- DK
- Denmark
- Prior art keywords
- cycloalkano
- indole
- acid
- sulfonamides
- tetrahydrocarbazole
- Prior art date
Links
- 238000002360 preparation method Methods 0.000 title claims description 17
- 150000003839 salts Chemical class 0.000 title claims description 15
- 229940126601 medicinal product Drugs 0.000 title 1
- -1 dihydroindole sulfonamides Chemical class 0.000 claims description 92
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 claims description 64
- 239000000460 chlorine Substances 0.000 claims description 43
- 238000000034 method Methods 0.000 claims description 37
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 claims description 32
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 claims description 32
- 230000008569 process Effects 0.000 claims description 22
- RYMYQAMZUWJAEO-UHFFFAOYSA-N 1h-indole-2-sulfonamide Chemical class C1=CC=C2NC(S(=O)(=O)N)=CC2=C1 RYMYQAMZUWJAEO-UHFFFAOYSA-N 0.000 claims description 21
- 239000002253 acid Substances 0.000 claims description 17
- 239000012442 inert solvent Substances 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 229940124530 sulfonamide Drugs 0.000 claims description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 9
- 239000003814 drug Substances 0.000 claims description 9
- 239000001257 hydrogen Substances 0.000 claims description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims description 9
- 150000003456 sulfonamides Chemical class 0.000 claims description 9
- LDXDSHIEDAPSSA-UHFFFAOYSA-N ramatroban Chemical compound C1C=2C3=CC=CC=C3N(CCC(=O)O)C=2CCC1NS(=O)(=O)C1=CC=C(F)C=C1 LDXDSHIEDAPSSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003638 chemical reducing agent Substances 0.000 claims description 7
- 229940079593 drug Drugs 0.000 claims description 7
- 125000001153 fluoro group Chemical group F* 0.000 claims description 7
- 150000002475 indoles Chemical class 0.000 claims description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 6
- 229910052801 chlorine Inorganic materials 0.000 claims description 6
- 239000011737 fluorine Substances 0.000 claims description 6
- 229910052731 fluorine Inorganic materials 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 229910052794 bromium Inorganic materials 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 230000001225 therapeutic effect Effects 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- 238000004519 manufacturing process Methods 0.000 claims description 3
- DSNBHJFQCNUKMA-SCKDECHMSA-N thromboxane A2 Chemical compound OC(=O)CCC\C=C/C[C@@H]1[C@@H](/C=C/[C@@H](O)CCCCC)O[C@@H]2O[C@H]1C2 DSNBHJFQCNUKMA-SCKDECHMSA-N 0.000 claims description 3
- 239000005557 antagonist Substances 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- XTFIVUDBNACUBN-UHFFFAOYSA-N 1,3,5-trinitro-1,3,5-triazinane Chemical group [O-][N+](=O)N1CN([N+]([O-])=O)CN([N+]([O-])=O)C1 XTFIVUDBNACUBN-UHFFFAOYSA-N 0.000 claims 1
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- 239000000106 platelet aggregation inhibitor Substances 0.000 claims 1
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- 239000000243 solution Substances 0.000 description 37
- 125000000143 2-carboxyethyl group Chemical group [H]OC(=O)C([H])([H])C([H])([H])* 0.000 description 34
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 34
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- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 26
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 24
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 22
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 22
- 150000001875 compounds Chemical class 0.000 description 22
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 21
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- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 18
- 239000011541 reaction mixture Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 18
- 235000019441 ethanol Nutrition 0.000 description 17
- 239000002585 base Substances 0.000 description 16
- UFRCIKMHUAOIAT-UHFFFAOYSA-N 2,3,4,9-tetrahydro-1h-carbazol-3-amine Chemical class N1C2=CC=CC=C2C2=C1CCC(N)C2 UFRCIKMHUAOIAT-UHFFFAOYSA-N 0.000 description 15
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 15
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 14
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 14
- 229910052938 sodium sulfate Inorganic materials 0.000 description 14
- 235000011152 sodium sulphate Nutrition 0.000 description 14
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 13
- 229960000583 acetic acid Drugs 0.000 description 13
- 238000001816 cooling Methods 0.000 description 13
- 239000012074 organic phase Substances 0.000 description 13
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 238000010992 reflux Methods 0.000 description 12
- 239000008259 solid foam Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 11
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- 229910052757 nitrogen Inorganic materials 0.000 description 11
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- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 9
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
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- 150000001298 alcohols Chemical class 0.000 description 8
- HKOOXMFOFWEVGF-UHFFFAOYSA-N phenylhydrazine Chemical compound NNC1=CC=CC=C1 HKOOXMFOFWEVGF-UHFFFAOYSA-N 0.000 description 8
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- 150000004031 phenylhydrazines Chemical class 0.000 description 8
- 229910052783 alkali metal Inorganic materials 0.000 description 7
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- 238000002425 crystallisation Methods 0.000 description 7
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- LYGJENNIWJXYER-UHFFFAOYSA-N nitromethane Chemical compound C[N+]([O-])=O LYGJENNIWJXYER-UHFFFAOYSA-N 0.000 description 7
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- 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 6
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- 230000002378 acidificating effect Effects 0.000 description 6
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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
- 239000002244 precipitate Substances 0.000 description 1
- 229940095574 propionic acid Drugs 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- JRBVAOJTPBHRQQ-UHFFFAOYSA-M sodium 3-[3-[(4-fluorophenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoate Chemical compound [Na+].C1C=2C3=CC=CC=C3N(CCC(=O)[O-])C=2CCC1NS(=O)(=O)C1=CC=C(F)C=C1 JRBVAOJTPBHRQQ-UHFFFAOYSA-M 0.000 description 1
- OUKRVBIEMBFEOL-UHFFFAOYSA-M sodium 3-[3-[(4-methylphenyl)sulfonylamino]-1,2,3,4-tetrahydrocarbazol-9-yl]propanoate Chemical compound [Na+].C1=CC(C)=CC=C1S(=O)(=O)NC1CC(C=2C(=CC=CC=2)N2CCC([O-])=O)=C2CC1 OUKRVBIEMBFEOL-UHFFFAOYSA-M 0.000 description 1
- 239000001488 sodium phosphate Substances 0.000 description 1
- 229910000162 sodium phosphate Inorganic materials 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 125000006296 sulfonyl amino group Chemical group [H]N(*)S(*)(=O)=O 0.000 description 1
- 229940032330 sulfuric acid Drugs 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 238000009901 transfer hydrogenation reaction Methods 0.000 description 1
- DBGVGMSCBYYSLD-UHFFFAOYSA-N tributylstannane Chemical compound CCCC[SnH](CCCC)CCCC DBGVGMSCBYYSLD-UHFFFAOYSA-N 0.000 description 1
- AKQNYQDSIDKVJZ-UHFFFAOYSA-N triphenylsilane Chemical compound C1=CC=CC=C1[SiH](C=1C=CC=CC=1)C1=CC=CC=C1 AKQNYQDSIDKVJZ-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- 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
- C07D209/02—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom condensed with one carbocyclic ring
- C07D209/04—Indoles; Hydrogenated indoles
- C07D209/10—Indoles; Hydrogenated indoles with substituted hydrocarbon radicals attached to carbon atoms of the hetero ring
- C07D209/12—Radicals substituted by oxygen 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
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P7/00—Drugs for disorders of the blood or the extracellular fluid
- A61P7/02—Antithrombotic agents; Anticoagulants; Platelet aggregation inhibitors
-
- 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
- C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
-
- 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
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/10—Spiro-condensed systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Pulmonology (AREA)
- Hematology (AREA)
- Diabetes (AREA)
- Immunology (AREA)
- Indole Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3605566 | 1986-02-21 | ||
| DE3605566 | 1986-02-21 | ||
| DE3631824 | 1986-09-19 | ||
| DE19863631824 DE3631824A1 (de) | 1986-02-21 | 1986-09-19 | Cycloalkano(1.2-b)indol-sulfonamide |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DK87187D0 DK87187D0 (da) | 1987-02-20 |
| DK87187A DK87187A (da) | 1987-08-22 |
| DK167009B1 true DK167009B1 (da) | 1993-08-16 |
Family
ID=25841196
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DK087187A DK167009B1 (da) | 1986-02-21 | 1987-02-20 | Cycloalkanooe1,2-baaindolsulfonamider, isomere og fysiologisk acceptable salte deraf, deres fremstilling og anvendelse samt laegemiddel indeholdende dem |
Country Status (19)
| Country | Link |
|---|---|
| US (3) | US4827032A (cs) |
| EP (1) | EP0242518B1 (cs) |
| JP (1) | JPH075552B2 (cs) |
| KR (2) | KR940007302B1 (cs) |
| AU (1) | AU595855B2 (cs) |
| CA (1) | CA1309414C (cs) |
| CS (1) | CS275837B6 (cs) |
| DE (2) | DE3631824A1 (cs) |
| DK (1) | DK167009B1 (cs) |
| ES (1) | ES2028801T3 (cs) |
| FI (1) | FI86544C (cs) |
| GR (1) | GR3001763T3 (cs) |
| HU (1) | HU198686B (cs) |
| IE (1) | IE59470B1 (cs) |
| IL (1) | IL81611A (cs) |
| NO (1) | NO171633C (cs) |
| NZ (1) | NZ219319A (cs) |
| PH (1) | PH24491A (cs) |
| PT (1) | PT84316B (cs) |
Families Citing this family (36)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3826371A1 (de) * | 1988-08-03 | 1990-02-08 | Bayer Ag | Tetrahydro-1-benz-(c,d)-indolpropionsaeure-sulfonamide |
| DE3829455A1 (de) * | 1988-08-31 | 1990-03-15 | Boehringer Mannheim Gmbh | Sulfonamidoalkyl-cyclohexan-verbindungen, verfahren zu ihrer herstellung sowie arzneimittel |
| US5070099A (en) * | 1988-10-31 | 1991-12-03 | E. R. Squibb & Sons, Inc. | Arylthioalkylphenyl carboxylic acids, derivatives thereof, compositions containing same method of use |
| US4959383A (en) * | 1988-10-31 | 1990-09-25 | E. R. Squibb & Sons, Inc. | Phenylsulfone alkenoic acids, derivatives thereof, compositions containing same and method of use |
| US5006542A (en) * | 1988-10-31 | 1991-04-09 | E. R. Squibb & Sons, Inc. | Arylthioalkylphenyl carboxylic acids, derivatives thereof, compositions containing same and method of use |
| GB8924392D0 (en) * | 1989-10-30 | 1989-12-20 | Bayer Ag | Substituted cycloalkano/b/dihydroindole-and-indolesulphonamides |
| GB9008108D0 (en) * | 1990-04-10 | 1990-06-06 | Bayer Ag | Cycloalkano(b)dihydroindoles and-indolesulphonamides substituted by heterocycles |
| DE4027278A1 (de) * | 1990-08-29 | 1992-03-05 | Bayer Ag | Heterocyclisch substituierte indolsulfonamide |
| US5827871A (en) * | 1991-06-26 | 1998-10-27 | Smithkline Beecham Plc | Medicaments 1,2,3,4-tetrahydrocarbazoles and 5-HT1 agonist use thereof |
| DE4131346A1 (de) * | 1991-09-20 | 1993-03-25 | Bayer Ag | Indolsulfonamid substituierte dihydropyridine, verfahren zu ihrer herstellung und ihre verwendung in arzneimitteln |
| EP0603432B1 (en) * | 1992-12-18 | 1998-10-21 | Smithkline Beecham Plc | Tetrahydrocarbazole derivatives for the manufacture of a medicament for the treatment of a disease where a 5-HT1-like agonist is indicated |
| DE19507751A1 (de) * | 1995-03-06 | 1996-09-12 | Bayer Ag | Verfahren zur Herstellung von substituierten 1,2,3,4-Tetrahydrocarbazolen |
| US5708187A (en) * | 1996-06-27 | 1998-01-13 | Eli Lilly And Company | 6-substituted-1,2,3,4-tetrahydro-9H-carbazoles and 7-substituted-10H-cyclohepta 7,6-B!indoles: New 5-HT1F agonists |
| DE19757983A1 (de) * | 1997-12-24 | 1999-07-01 | Bayer Yakuhin Ltd | Thermodynamisch stabile Form von (r)-3[[(4-Fluorophenyl)sulfonyl]amino]-1,2,3,4-tetrahydro-9H-carbazol-0-propansäure (Ramatroban) |
| ES2443022T3 (es) * | 2005-08-12 | 2014-02-17 | Merck Frosst Canada Inc. | Derivados de indol como antagonistas del receptor CRTH2 |
| US7662831B2 (en) * | 2006-07-27 | 2010-02-16 | Wyeth Llc | Tetracyclic indoles as potassium channel modulators |
| US7601856B2 (en) * | 2006-07-27 | 2009-10-13 | Wyeth | Benzofurans as potassium ion channel modulators |
| SI2051962T1 (sl) | 2006-08-07 | 2012-02-29 | Actelion Pharmaceuticals Ltd | Derivati (3-amino-1,2,3,4-tetrahidro-9h-karbazol-9-il)-ocetne kisline |
| GB0624090D0 (en) * | 2006-12-01 | 2007-01-10 | Selamine Ltd | Ramipril amine salts |
| GB0624087D0 (en) * | 2006-12-01 | 2007-01-10 | Selamine Ltd | Ramipril combination salt |
| GB0624084D0 (en) * | 2006-12-01 | 2007-01-10 | Selamine Ltd | Ramipril amino acid salts |
| ATE543501T1 (de) * | 2006-12-20 | 2012-02-15 | Cardoz Ab | Kombination von pemirolast und ramatroban zur verwendung bei der behandlung von entzündlichen erkrankungen |
| CA2675520A1 (en) * | 2007-01-16 | 2008-07-24 | Cardoz Ab | New combination for use in the treatment of inflammatory disorders |
| WO2009007674A2 (en) * | 2007-07-11 | 2009-01-15 | Cardoz Ab | Combination for use in the treatment of atherosclerosis comprising a mast cell inhibitor and ramatroban or seratrodast |
| US8501959B2 (en) * | 2008-06-24 | 2013-08-06 | Panmira Pharmaceuticals, Llc | Cycloalkane[B]indole antagonists of prostaglandin D2 receptors |
| ES2378755T3 (es) | 2008-07-15 | 2012-04-17 | F. Hoffmann-La Roche Ag | �?cidos aminotetrahidroindazoloacéticos |
| RU2011124149A (ru) | 2008-11-17 | 2012-12-27 | Ф.Хоффманн-Ля Рош Аг | Нафтилуксусные кислоты |
| EP2346819B1 (en) | 2008-11-17 | 2013-04-10 | F. Hoffmann-La Roche AG | Naphthylacetic acids |
| WO2010055006A1 (en) | 2008-11-17 | 2010-05-20 | F. Hoffmann-La Roche Ag | Naphthylacetic acids used as crth2 antagonists or partial agonists |
| MA34094B1 (fr) | 2010-03-22 | 2013-03-05 | Actelion Pharmaceuticals Ltd | Dérivés de 3-(hétéroarylamino)-1,2,3,4-tétrahydro-9h-carbazole et leur utilisation comme modulateurs du récepteur de la prostaglandine d2 |
| CN103459389B (zh) | 2011-04-14 | 2016-03-30 | 埃科特莱茵药品有限公司 | 7-(杂芳基-氨基)-6,7,8,9-四氢吡啶并[1,2-a]吲哚乙酸衍生物和其作为前列腺素D2受体调节剂的用途 |
| US8470884B2 (en) | 2011-11-09 | 2013-06-25 | Hoffmann-La Roche Inc. | Alkenyl naphthylacetic acids |
| TWI649321B (zh) | 2014-03-17 | 2019-02-01 | 瑞士商愛杜西亞製藥有限公司 | 氮雜吲哚乙酸衍生物及彼等作為前列腺素ｄ２受體調節劑之用途 |
| AU2015233046A1 (en) | 2014-03-18 | 2016-11-03 | Idorsia Pharmaceuticals Ltd | Azaindole acetic acid derivatives and their use as prostaglandin D2 receptor modulators |
| JP6770522B2 (ja) | 2015-02-13 | 2020-10-14 | アンスティチュ ナショナル ドゥ ラ サンテ エ ドゥ ラ ルシェルシュ メディカル | 全身性エリテマトーデスを予防し、及び／又は、治療するためのｐｔｇｄｒ−１及び／又はｐｔｇｄｒ−２アンタゴニスト |
| WO2017046125A1 (en) | 2015-09-15 | 2017-03-23 | Actelion Pharmaceuticals Ltd | Crystalline forms |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1415322A (fr) * | 1963-12-09 | 1965-10-22 | Eastman Kodak Co | Nouveaux composés de 3-sulfamidocyclobutanone et de 3-sulfamidocyclobutanol |
| US3642816A (en) * | 1967-08-10 | 1972-02-15 | Sterling Drug Inc | 3-acetamido-1 2 3 4-tetrahydrocarbazole |
| JPS4713658Y1 (cs) * | 1969-12-18 | 1972-05-18 | ||
| CH586678A5 (cs) * | 1970-05-25 | 1977-04-15 | Hoffmann La Roche | |
| DE2226702A1 (de) * | 1972-05-25 | 1973-12-13 | Schering Ag | Neue mittel zur behandlung des diabetes mellitus |
| JPS5186117A (en) * | 1975-01-27 | 1976-07-28 | Tanabe Seiyaku Co | Johoseibiryushiseizainoseiho |
| US4235901A (en) * | 1978-05-08 | 1980-11-25 | American Home Products Corporation | 1-Hydroxyalkanamine pyrano(3,4-b)indole compositions and use thereof |
-
1986
- 1986-09-19 DE DE19863631824 patent/DE3631824A1/de not_active Withdrawn
-
1987
- 1987-02-04 NO NO870437A patent/NO171633C/no unknown
- 1987-02-11 EP EP87101901A patent/EP0242518B1/de not_active Expired - Lifetime
- 1987-02-11 ES ES198787101901T patent/ES2028801T3/es not_active Expired - Lifetime
- 1987-02-11 DE DE8787101901T patent/DE3769191D1/de not_active Expired - Lifetime
- 1987-02-13 AU AU68808/87A patent/AU595855B2/en not_active Expired
- 1987-02-18 IL IL81611A patent/IL81611A/xx not_active IP Right Cessation
- 1987-02-18 NZ NZ219319A patent/NZ219319A/en unknown
- 1987-02-19 PT PT84316A patent/PT84316B/pt not_active IP Right Cessation
- 1987-02-19 CA CA000530077A patent/CA1309414C/en not_active Expired - Lifetime
- 1987-02-19 HU HU87650A patent/HU198686B/hu unknown
- 1987-02-19 FI FI870693A patent/FI86544C/fi not_active IP Right Cessation
- 1987-02-19 PH PH34883A patent/PH24491A/en unknown
- 1987-02-19 CS CS871093A patent/CS275837B6/cs unknown
- 1987-02-20 KR KR1019870001410A patent/KR940007302B1/ko not_active Expired - Lifetime
- 1987-02-20 DK DK087187A patent/DK167009B1/da not_active IP Right Cessation
- 1987-02-20 IE IE43987A patent/IE59470B1/en not_active IP Right Cessation
- 1987-07-31 KR KR87008383A patent/KR960001914B1/ko not_active Expired - Fee Related
-
1988
- 1988-06-29 US US07/212,840 patent/US4827032A/en not_active Expired - Lifetime
-
1989
- 1989-02-08 US US07/308,152 patent/US4904797A/en not_active Expired - Lifetime
- 1989-11-28 US US07/442,043 patent/US4965258A/en not_active Expired - Lifetime
-
1991
- 1991-04-11 GR GR91400361T patent/GR3001763T3/el unknown
-
1992
- 1992-02-27 JP JP4076232A patent/JPH075552B2/ja not_active Expired - Lifetime
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| B1 | Patent granted (law 1993) | ||
| PUP | Patent expired |