IL100330A - Salt 3- [2- (dimethylamino) ethyl] - N-methyl-H1-methanesulfonamino sulfate) 2: 1, process for its preparation and a pharmaceutical preparation containing it - Google Patents
Salt 3- [2- (dimethylamino) ethyl] - N-methyl-H1-methanesulfonamino sulfate) 2: 1, process for its preparation and a pharmaceutical preparation containing itInfo
- Publication number
- IL100330A IL100330A IL10033091A IL10033091A IL100330A IL 100330 A IL100330 A IL 100330A IL 10033091 A IL10033091 A IL 10033091A IL 10033091 A IL10033091 A IL 10033091A IL 100330 A IL100330 A IL 100330A
- Authority
- IL
- Israel
- Prior art keywords
- indole
- ethyl
- methyl
- pharmaceutical composition
- salt
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims abstract description 21
- 238000002360 preparation method Methods 0.000 title claims abstract description 10
- GIYWWORAURQCTI-UHFFFAOYSA-N 1-[3-[2-(dimethylamino)ethyl]-1h-indol-5-yl]-n-methylmethanesulfonamide;sulfuric acid Chemical compound OS(O)(=O)=O.CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 GIYWWORAURQCTI-UHFFFAOYSA-N 0.000 title claims abstract description 8
- 238000000034 method Methods 0.000 title claims description 9
- 230000008569 process Effects 0.000 title claims description 7
- 239000012453 solvate Substances 0.000 claims abstract description 22
- 208000019695 Migraine disease Diseases 0.000 claims abstract description 9
- 206010027599 migraine Diseases 0.000 claims abstract description 9
- 238000011282 treatment Methods 0.000 claims abstract description 9
- 208000002193 Pain Diseases 0.000 claims abstract description 5
- 239000000243 solution Substances 0.000 claims description 51
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 25
- 150000003839 salts Chemical class 0.000 claims description 24
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 16
- 239000001117 sulphuric acid Substances 0.000 claims description 16
- 235000011149 sulphuric acid Nutrition 0.000 claims description 16
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 11
- 239000004480 active ingredient Substances 0.000 claims description 10
- KQKPFRSPSRPDEB-UHFFFAOYSA-N sumatriptan Chemical compound CNS(=O)(=O)CC1=CC=C2NC=C(CCN(C)C)C2=C1 KQKPFRSPSRPDEB-UHFFFAOYSA-N 0.000 claims description 10
- 239000003814 drug Substances 0.000 claims description 9
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 6
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 4
- 239000003937 drug carrier Substances 0.000 claims description 3
- 238000002560 therapeutic procedure Methods 0.000 claims description 3
- -1 ide sulphate salt Chemical class 0.000 claims description 2
- 239000002552 dosage form Substances 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 31
- 150000001875 compounds Chemical class 0.000 abstract description 30
- 238000009472 formulation Methods 0.000 abstract description 27
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 36
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 10
- 229960000686 benzalkonium chloride Drugs 0.000 description 5
- CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 5
- 229940067107 phenylethyl alcohol Drugs 0.000 description 5
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 5
- 229940079593 drug Drugs 0.000 description 4
- 150000003890 succinate salts Chemical class 0.000 description 4
- 239000008215 water for injection Substances 0.000 description 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 239000002585 base Substances 0.000 description 3
- 229940081974 saccharin Drugs 0.000 description 3
- 235000019204 saccharin Nutrition 0.000 description 3
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 3
- 238000007789 sealing Methods 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 230000001954 sterilising effect Effects 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 3
- 229960003708 sumatriptan Drugs 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 206010019233 Headaches Diseases 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- 230000001154 acute effect Effects 0.000 description 2
- 239000012736 aqueous medium Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 230000008570 general process Effects 0.000 description 2
- 231100000869 headache Toxicity 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000014759 maintenance of location Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 2
- 239000000546 pharmaceutical excipient Substances 0.000 description 2
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000003755 preservative agent Substances 0.000 description 2
- 239000008213 purified water Substances 0.000 description 2
- 238000007920 subcutaneous administration Methods 0.000 description 2
- 229910021653 sulphate ion Inorganic materials 0.000 description 2
- NOOLISFMXDJSKH-UTLUCORTSA-N (+)-Neomenthol Chemical compound CC(C)[C@@H]1CC[C@@H](C)C[C@@H]1O NOOLISFMXDJSKH-UTLUCORTSA-N 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical class C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- WEEGYLXZBRQIMU-UHFFFAOYSA-N 1,8-cineole Natural products C1CC2CCC1(C)OC2(C)C WEEGYLXZBRQIMU-UHFFFAOYSA-N 0.000 description 1
- 206010009094 Chronic paroxysmal hemicrania Diseases 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 208000006561 Cluster Headache Diseases 0.000 description 1
- NOOLISFMXDJSKH-UHFFFAOYSA-N DL-menthol Natural products CC(C)C1CCC(C)CC1O NOOLISFMXDJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- WEEGYLXZBRQIMU-WAAGHKOSSA-N Eucalyptol Chemical compound C1C[C@H]2CC[C@]1(C)OC2(C)C WEEGYLXZBRQIMU-WAAGHKOSSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 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
- AFVFQIVMOAPDHO-UHFFFAOYSA-M Methanesulfonate Chemical compound CS([O-])(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- 206010028813 Nausea Diseases 0.000 description 1
- 229920002565 Polyethylene Glycol 400 Polymers 0.000 description 1
- 208000007271 Substance Withdrawal Syndrome Diseases 0.000 description 1
- 206010043269 Tension headache Diseases 0.000 description 1
- 208000008548 Tension-Type Headache Diseases 0.000 description 1
- JKNZUZCGFROMAZ-UHFFFAOYSA-L [Ag+2].[O-]S([O-])(=O)=O Chemical compound [Ag+2].[O-]S([O-])(=O)=O JKNZUZCGFROMAZ-UHFFFAOYSA-L 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000003556 assay Methods 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 239000006172 buffering agent Substances 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229960005233 cineole Drugs 0.000 description 1
- 208000018912 cluster headache syndrome Diseases 0.000 description 1
- 239000006184 cosolvent Substances 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 229940042935 dichlorodifluoromethane Drugs 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000003599 food sweetener Nutrition 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000004677 hydrates Chemical class 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 229940041616 menthol Drugs 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229960001047 methyl salicylate Drugs 0.000 description 1
- 210000003928 nasal cavity Anatomy 0.000 description 1
- 210000002850 nasal mucosa Anatomy 0.000 description 1
- 230000008693 nausea Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000007911 parenteral administration Methods 0.000 description 1
- 208000007777 paroxysmal Hemicrania Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 238000011321 prophylaxis Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 239000003765 sweetening agent Substances 0.000 description 1
- 208000024891 symptom Diseases 0.000 description 1
- 238000011287 therapeutic dose Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
- 208000019553 vascular disease Diseases 0.000 description 1
- 239000005526 vasoconstrictor agent Substances 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
- C07D209/14—Radicals substituted by nitrogen atoms, not forming part of a nitro radical
- C07D209/16—Tryptamines
-
- 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
- A61P25/00—Drugs for disorders of the nervous system
- A61P25/06—Antimigraine agents
-
- 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]
- A61P29/02—Non-central analgesic, antipyretic or antiinflammatory agents, e.g. antirheumatic agents; Non-steroidal antiinflammatory drugs [NSAID] without antiinflammatory effect
Landscapes
- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Pain & Pain Management (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurosurgery (AREA)
- Neurology (AREA)
- Rheumatology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Indole Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB909026998A GB9026998D0 (en) | 1990-12-12 | 1990-12-12 | Medicaments |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL100330A0 IL100330A0 (en) | 1992-09-06 |
| IL100330A true IL100330A (en) | 1996-06-18 |
Family
ID=10686904
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL10033091A IL100330A (en) | 1990-12-12 | 1991-12-11 | Salt 3- [2- (dimethylamino) ethyl] - N-methyl-H1-methanesulfonamino sulfate) 2: 1, process for its preparation and a pharmaceutical preparation containing it |
Country Status (36)
| Country | Link |
|---|---|
| US (2) | US5554639A (cs) |
| EP (1) | EP0490689B1 (cs) |
| JP (1) | JP2994037B2 (cs) |
| KR (1) | KR100211479B1 (cs) |
| CN (2) | CN1030890C (cs) |
| AP (1) | AP230A (cs) |
| AT (1) | ATE119881T1 (cs) |
| AU (1) | AU650706B2 (cs) |
| BE (1) | BE1005085A3 (cs) |
| CA (1) | CA2098302C (cs) |
| CH (1) | CH684192A5 (cs) |
| CY (1) | CY2005A (cs) |
| CZ (1) | CZ281931B6 (cs) |
| DE (1) | DE69108200T2 (cs) |
| DK (1) | DK0490689T3 (cs) |
| EG (1) | EG20219A (cs) |
| ES (1) | ES2069836T3 (cs) |
| FR (1) | FR2670487B1 (cs) |
| GB (2) | GB9026998D0 (cs) |
| GR (1) | GR3015430T3 (cs) |
| HK (1) | HK82697A (cs) |
| HU (1) | HU211937A9 (cs) |
| IE (1) | IE62894B1 (cs) |
| IL (1) | IL100330A (cs) |
| IS (1) | IS1706B (cs) |
| IT (1) | IT1252868B (cs) |
| MX (1) | MX9102501A (cs) |
| MY (1) | MY109265A (cs) |
| NL (1) | NL9102071A (cs) |
| NZ (1) | NZ240942A (cs) |
| PT (1) | PT99757B (cs) |
| RU (1) | RU2108328C1 (cs) |
| TW (2) | TW300886B (cs) |
| WO (1) | WO1992010477A1 (cs) |
| YU (1) | YU48926B (cs) |
| ZA (1) | ZA919750B (cs) |
Families Citing this family (63)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2619197B2 (ja) * | 1992-06-05 | 1997-06-11 | メルク シャープ エンド ドーム リミテッド | 置換トリアゾールの硫酸塩、その医薬組成物及び治療に於けるその使用 |
| FR2749846B1 (fr) * | 1996-06-17 | 1998-09-11 | Pf Medicament | Sel de methanesulfonate d'une arylpiperazine derivee de tryptamine et ses solvates pour usage pharmaceutique |
| US8022095B2 (en) * | 1996-08-16 | 2011-09-20 | Pozen, Inc. | Methods of treating headaches using 5-HT agonists in combination with long-acting NSAIDs |
| US6106837A (en) * | 1997-05-15 | 2000-08-22 | Hirsch; Alan R. | Method of treating headaches, and article of manufacture therefor |
| US6066092A (en) * | 1997-11-06 | 2000-05-23 | Cady; Roger K. | Preemptive prophylaxis of migraine device and method |
| US7189753B1 (en) | 1997-11-06 | 2007-03-13 | Cady Roger K | Preemptive prophylaxis of migraine |
| US6426084B1 (en) | 2000-06-19 | 2002-07-30 | Neal R. Cutler | Treatment of sexual dysfunction in certain patient groups |
| US6132757A (en) * | 1998-05-01 | 2000-10-17 | Neal R. Cutler | Treatment of sexual dysfunction in certain patient groups |
| US6187790B1 (en) | 1999-03-04 | 2001-02-13 | Neal R. Cutler | Use of cilostazol for treatment of sexual dysfunction |
| GB9926250D0 (en) * | 1999-11-06 | 2000-01-12 | Knoll Ag | Chemical process |
| US6610271B2 (en) * | 2000-05-10 | 2003-08-26 | University Of Kentucky Research Foundation | System and method for intranasal administration of lorazepam |
| US20040115133A1 (en) * | 2000-05-10 | 2004-06-17 | Wermeling Daniel P. | Intranasal opioid compositions |
| US6451813B1 (en) | 2001-01-26 | 2002-09-17 | R. T. Alamo Ventures I, Llc | Treatment of gastroparesis in certain patient groups |
| US6562838B2 (en) * | 2001-01-26 | 2003-05-13 | R. T. Alamo Ventures I, L.L.C. | Treatment of cardiovascular disease with quinolinone enantiomers |
| US6458804B1 (en) | 2001-01-26 | 2002-10-01 | R.T. Alamo Venturesi, Llc | Methods for the treatment of central nervous system disorders in certain patient groups |
| US20040176359A1 (en) * | 2001-02-20 | 2004-09-09 | University Of Kentucky Research Foundation | Intranasal Benzodiazepine compositions |
| US20030096748A1 (en) * | 2001-06-04 | 2003-05-22 | The Regents Of The University Of Michigan | Methods and compositions for the treatment of diseases associated with signal transduction aberrations |
| ES2312585T3 (es) * | 2001-06-05 | 2009-03-01 | Ronald Aung-Din | Terapia contra la migraña por via topica. |
| US8329734B2 (en) | 2009-07-27 | 2012-12-11 | Afgin Pharma Llc | Topical therapy for migraine |
| US7041677B2 (en) * | 2002-03-01 | 2006-05-09 | R.T. Alamo Ventures I, Llc | Use of monochloroflosequinan in the treatment of sexual dysfunction |
| US7208628B2 (en) * | 2002-05-13 | 2007-04-24 | Kansas State University Research Foundation | Compositions and methods for the treatment of hepatitis C virus infection |
| US7074893B2 (en) * | 2002-06-03 | 2006-07-11 | Regents Of The University Of Michigan | Methods and compositions for the treatment of diseases associated with signal transduction aberrations |
| US20040068000A1 (en) * | 2002-10-02 | 2004-04-08 | Mintong Guo | Compression coated tablets |
| DK1575566T3 (da) * | 2002-12-26 | 2012-03-26 | Pozen Inc | Flerlagsdoseringsformer indeholdende naproxen og triptaner |
| US20080213363A1 (en) * | 2003-01-23 | 2008-09-04 | Singh Nikhilesh N | Methods and compositions for delivering 5-HT3 antagonists across the oral mucosa |
| WO2004076403A1 (en) * | 2003-02-24 | 2004-09-10 | Transform Pharmaceuticals, Inc. | Sumatriptan crystalline forms, pharmaceutical compositions and methods |
| EP1644004A4 (en) | 2003-06-20 | 2010-10-06 | Ronald Aung-Din | LOCAL THERAPY FOR THE TREATMENT OF MIGRAINS, MUSCLE CLARIFICATIONS, MUSCLE SPASMS, SPASTICITY AND RELATED CONDITIONS |
| US20050089558A1 (en) * | 2003-10-28 | 2005-04-28 | Alamo Pharmaceuticals, Llc | Compositions and methods for the co-formulation and administration of tramadol and propoxyphene |
| US20050269402A1 (en) * | 2004-06-03 | 2005-12-08 | Tyfone, Inc. | System and method for securing financial transactions |
| CA2569964A1 (en) * | 2004-06-10 | 2005-12-29 | Duramed Pharmaceuticals, Inc. | Formulations of sumatriptan for absorption across biological membranes, and methods of making and using the same |
| MY147767A (en) | 2004-06-16 | 2013-01-31 | Janssen Pharmaceutica Nv | Novel sulfamate and sulfamide derivatives useful for the treatment of epilepsy and related disorders |
| WO2006127184A1 (en) | 2005-05-20 | 2006-11-30 | Janssen Pharmaceutica N.V. | Process for preparation of sulfamide derivatives |
| US20070166336A1 (en) * | 2005-12-13 | 2007-07-19 | David Delmarre | Stable and palatable oral liquid sumatriptan compositions |
| US8691867B2 (en) | 2005-12-19 | 2014-04-08 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocycle sulfamide derivatives for the treatment of substance abuse and addiction |
| US8937096B2 (en) | 2005-12-19 | 2015-01-20 | Janssen Pharmaceutica Nv | Use of benzo-fused heterocyle sulfamide derivatives for the treatment of mania and bipolar disorder |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2162522B (en) * | 1984-08-01 | 1988-02-24 | Glaxo Group Ltd | An indole derivative |
| GB8615599D0 (en) * | 1986-06-26 | 1986-07-30 | Glaxo Group Ltd | Chemical compounds |
| GB8928208D0 (en) * | 1989-12-13 | 1990-02-14 | Glaxo Group Ltd | Medicaments |
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1990
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