LV12210B - The sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy - Google Patents

The sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy Download PDF

Info

Publication number: LV12210B
Authority: LV; Latvia
Prior art keywords: salt; pharmaceutically acceptable; pharmaceutical composition; formula; composition according
Prior art date: 1992-06-05

Application number

LVP-98-237A

Other languages

English (en)

Latvian (lv)

Other versions

LV12210A (lv

Inventor

Raymond Baker

Kendal G. Pitt

Victor G. Matassa

David E. Storey

Carole Olive

Leslie J. Street

Alexander Richard Guiblin

Original Assignee

Merck Sharp & Dohme Ltd

Priority date (The priority date 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 date listed.)

1992-06-05

Filing date

1998-10-26

Publication date

1999-03-20

1992-06-05 Priority claimed from GB929211903A external-priority patent/GB9211903D0/en

1993-04-07 Priority claimed from GB939307306A external-priority patent/GB9307306D0/en

1998-10-26 Application filed by Merck Sharp & Dohme Ltd filed Critical Merck Sharp & Dohme Ltd

1999-01-20 Publication of LV12210A publication Critical patent/LV12210A/xx

1999-03-20 Publication of LV12210B publication Critical patent/LV12210B/en

Links

239000008194 pharmaceutical composition Substances 0.000 title claims description 24
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 title claims description 5
229910021653 sulphate ion Inorganic materials 0.000 title claims description 5
QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 title 1
238000011282 treatment Methods 0.000 claims abstract description 13
ULFRLSNUDGIQQP-UHFFFAOYSA-N rizatriptan Chemical compound C1=C2C(CCN(C)C)=CNC2=CC=C1CN1C=NC=N1 ULFRLSNUDGIQQP-UHFFFAOYSA-N 0.000 claims abstract description 8
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims abstract 2
239000000203 mixture Substances 0.000 claims description 95
150000003839 salts Chemical class 0.000 claims description 65
239000012453 solvate Substances 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 25
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 22
238000000034 method Methods 0.000 claims description 20
239000007864 aqueous solution Substances 0.000 claims description 18
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 16
239000003814 drug Substances 0.000 claims description 13
239000004480 active ingredient Substances 0.000 claims description 11
238000002360 preparation method Methods 0.000 claims description 11
239000003937 drug carrier Substances 0.000 claims description 10
239000007787 solid Substances 0.000 claims description 9
QZAYGJVTTNCVMB-UHFFFAOYSA-N serotonin Chemical compound C1=C(O)C=C2C(CCN)=CNC2=C1 QZAYGJVTTNCVMB-UHFFFAOYSA-N 0.000 claims description 8
239000002552 dosage form Substances 0.000 claims description 6
238000002156 mixing Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 4
239000000872 buffer Substances 0.000 claims description 3
ZFOCEMXPIDAEFX-UHFFFAOYSA-N n,n-dimethyl-2-[5-(1,2,4-triazol-1-ylmethyl)-1h-indol-3-yl]ethanamine;sulfuric acid Chemical compound OS(O)(=O)=O.C1=C2C(CCN(C)C)=CNC2=CC=C1CN1C=NC=N1 ZFOCEMXPIDAEFX-UHFFFAOYSA-N 0.000 claims description 3
239000000018 receptor agonist Substances 0.000 claims description 3
229940044601 receptor agonist Drugs 0.000 claims description 3
239000002904 solvent Substances 0.000 claims description 3
238000002560 therapeutic procedure Methods 0.000 claims description 2
201000010099 disease Diseases 0.000 claims 1
238000011321 prophylaxis Methods 0.000 claims 1
230000001698 pyrogenic effect Effects 0.000 claims 1
150000003467 sulfuric acid derivatives Chemical class 0.000 abstract description 20
208000019695 Migraine disease Diseases 0.000 abstract description 10
206010027599 migraine Diseases 0.000 abstract description 10
239000000556 agonist Substances 0.000 abstract description 8
208000035475 disorder Diseases 0.000 abstract 1
239000000243 solution Substances 0.000 description 53
238000009472 formulation Methods 0.000 description 35
235000011149 sulphuric acid Nutrition 0.000 description 18
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 17
239000001117 sulphuric acid Substances 0.000 description 17
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 16
HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
239000003826 tablet Substances 0.000 description 11
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 10
230000003139 buffering effect Effects 0.000 description 10
229940079593 drug Drugs 0.000 description 9
239000012458 free base Substances 0.000 description 9
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 8
235000019359 magnesium stearate Nutrition 0.000 description 8
229910000030 sodium bicarbonate Inorganic materials 0.000 description 8
235000017557 sodium bicarbonate Nutrition 0.000 description 8
239000000546 pharmaceutical excipient Substances 0.000 description 7
-1 pilis Substances 0.000 description 7
229910000029 sodium carbonate Inorganic materials 0.000 description 7
WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 6
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
238000010521 absorption reaction Methods 0.000 description 6
238000001914 filtration Methods 0.000 description 6
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 6
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
239000007921 spray Substances 0.000 description 6
FTLYMKDSHNWQKD-UHFFFAOYSA-N (2,4,5-trichlorophenyl)boronic acid Chemical group OB(O)C1=CC(Cl)=C(Cl)C=C1Cl FTLYMKDSHNWQKD-UHFFFAOYSA-N 0.000 description 5
239000000796 flavoring agent Substances 0.000 description 5
235000019634 flavors Nutrition 0.000 description 5
238000002347 injection Methods 0.000 description 5
239000007924 injection Substances 0.000 description 5
210000000214 mouth Anatomy 0.000 description 5
229940085605 saccharin sodium Drugs 0.000 description 5
239000011780 sodium chloride Substances 0.000 description 5
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 description 5
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
229920002472 Starch Polymers 0.000 description 4
235000011114 ammonium hydroxide Nutrition 0.000 description 4
239000002775 capsule Substances 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
230000000694 effects Effects 0.000 description 4
239000000284 extract Substances 0.000 description 4
239000004615 ingredient Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 4
150000002828 nitro derivatives Chemical class 0.000 description 4
239000000047 product Substances 0.000 description 4
239000008107 starch Substances 0.000 description 4
229940032147 starch Drugs 0.000 description 4
235000019698 starch Nutrition 0.000 description 4
125000001425 triazolyl group Chemical group 0.000 description 4
VOLRSQPSJGXRNJ-UHFFFAOYSA-N 4-nitrobenzyl bromide Chemical compound [O-][N+](=O)C1=CC=C(CBr)C=C1 VOLRSQPSJGXRNJ-UHFFFAOYSA-N 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
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 3
244000246386 Mentha pulegium Species 0.000 description 3
235000016257 Mentha pulegium Nutrition 0.000 description 3
235000004357 Mentha x piperita Nutrition 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
150000001412 amines Chemical class 0.000 description 3
239000000908 ammonium hydroxide Substances 0.000 description 3
229960000686 benzalkonium chloride Drugs 0.000 description 3
CADWTSSKOVRVJC-UHFFFAOYSA-N benzyl(dimethyl)azanium;chloride Chemical compound [Cl-].C[NH+](C)CC1=CC=CC=C1 CADWTSSKOVRVJC-UHFFFAOYSA-N 0.000 description 3
239000007853 buffer solution Substances 0.000 description 3
238000004040 coloring Methods 0.000 description 3
235000001050 hortel pimenta Nutrition 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000003921 oil Substances 0.000 description 3
235000019198 oils Nutrition 0.000 description 3
TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 3
229940067107 phenylethyl alcohol Drugs 0.000 description 3
230000002265 prevention Effects 0.000 description 3
238000010992 reflux Methods 0.000 description 3
229940081974 saccharin Drugs 0.000 description 3
CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 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
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
235000010288 sodium nitrite Nutrition 0.000 description 3
235000010265 sodium sulphite Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
FMCUPJKTGNBGEC-UHFFFAOYSA-N 1,2,4-triazol-4-amine Chemical compound NN1C=NN=C1 FMCUPJKTGNBGEC-UHFFFAOYSA-N 0.000 description 2
OHMHBGPWCHTMQE-UHFFFAOYSA-N 2,2-dichloro-1,1,1-trifluoroethane Chemical compound FC(F)(F)C(Cl)Cl OHMHBGPWCHTMQE-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 2
PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
FBPFZTCFMRRESA-KVTDHHQDSA-N D-Mannitol Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-KVTDHHQDSA-N 0.000 description 2
WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 description 2
SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 2
229930195725 Mannitol Natural products 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
WINXNKPZLFISPD-UHFFFAOYSA-M Saccharin sodium Chemical class [Na+].C1=CC=C2C(=O)[N-]S(=O)(=O)C2=C1 WINXNKPZLFISPD-UHFFFAOYSA-M 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 2
229930006000 Sucrose Natural products 0.000 description 2
239000002253 acid Substances 0.000 description 2
239000000443 aerosol Substances 0.000 description 2
VZTDIZULWFCMLS-UHFFFAOYSA-N ammonium formate Chemical compound [NH4+].[O-]C=O VZTDIZULWFCMLS-UHFFFAOYSA-N 0.000 description 2
239000012736 aqueous medium Substances 0.000 description 2
239000007900 aqueous suspension Substances 0.000 description 2
229960001950 benzethonium chloride Drugs 0.000 description 2
UREZNYTWGJKWBI-UHFFFAOYSA-M benzethonium chloride Chemical compound [Cl-].C1=CC(C(C)(C)CC(C)(C)C)=CC=C1OCCOCC[N+](C)(C)CC1=CC=CC=C1 UREZNYTWGJKWBI-UHFFFAOYSA-M 0.000 description 2
WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
239000000686 essence Substances 0.000 description 2
238000011049 filling Methods 0.000 description 2
239000000706 filtrate Substances 0.000 description 2
239000007903 gelatin capsule Substances 0.000 description 2
239000008187 granular material Substances 0.000 description 2
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
150000002500 ions Chemical class 0.000 description 2
239000008101 lactose Substances 0.000 description 2
239000000594 mannitol Substances 0.000 description 2
235000010355 mannitol Nutrition 0.000 description 2
239000000463 material Substances 0.000 description 2
229960001047 methyl salicylate Drugs 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
230000002035 prolonged effect Effects 0.000 description 2
239000000376 reactant Substances 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000007789 sealing Methods 0.000 description 2
230000001954 sterilising effect Effects 0.000 description 2
239000006190 sub-lingual tablet Substances 0.000 description 2
229940098466 sublingual tablet Drugs 0.000 description 2
239000005720 sucrose Substances 0.000 description 2
150000003852 triazoles Chemical class 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
LNAZSHAWQACDHT-XIYTZBAFSA-N (2r,3r,4s,5r,6s)-4,5-dimethoxy-2-(methoxymethyl)-3-[(2s,3r,4s,5r,6r)-3,4,5-trimethoxy-6-(methoxymethyl)oxan-2-yl]oxy-6-[(2r,3r,4s,5r,6r)-4,5,6-trimethoxy-2-(methoxymethyl)oxan-3-yl]oxyoxane Chemical compound CO[C@@H]1[C@@H](OC)[C@H](OC)[C@@H](COC)O[C@H]1O[C@H]1[C@H](OC)[C@@H](OC)[C@H](O[C@H]2[C@@H]([C@@H](OC)[C@H](OC)O[C@@H]2COC)OC)O[C@@H]1COC LNAZSHAWQACDHT-XIYTZBAFSA-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
YFMFNYKEUDLDTL-UHFFFAOYSA-N 1,1,1,2,3,3,3-heptafluoropropane Chemical compound FC(F)(F)C(F)C(F)(F)F YFMFNYKEUDLDTL-UHFFFAOYSA-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
DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical class CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
DDMOUSALMHHKOS-UHFFFAOYSA-N 1,2-dichloro-1,1,2,2-tetrafluoroethane Chemical compound FC(F)(Cl)C(F)(F)Cl DDMOUSALMHHKOS-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
FLEAPQULBLEYNT-UHFFFAOYSA-M 1-[(4-nitrophenyl)methyl]-1,2,4-triazol-4-ium-4-amine;bromide Chemical compound [Br-].C1=[N+](N)C=NN1CC1=CC=C([N+]([O-])=O)C=C1 FLEAPQULBLEYNT-UHFFFAOYSA-M 0.000 description 1
BOUGCJDAQLKBQH-UHFFFAOYSA-N 1-chloro-1,2,2,2-tetrafluoroethane Chemical compound FC(Cl)C(F)(F)F BOUGCJDAQLKBQH-UHFFFAOYSA-N 0.000 description 1
WDZKKBDOGYBYBG-UHFFFAOYSA-N 4,4-dimethoxy-n,n-dimethylbutan-1-amine Chemical compound COC(OC)CCCN(C)C WDZKKBDOGYBYBG-UHFFFAOYSA-N 0.000 description 1
NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
FHVDTGUDJYJELY-UHFFFAOYSA-N 6-{[2-carboxy-4,5-dihydroxy-6-(phosphanyloxy)oxan-3-yl]oxy}-4,5-dihydroxy-3-phosphanyloxane-2-carboxylic acid Chemical compound O1C(C(O)=O)C(P)C(O)C(O)C1OC1C(C(O)=O)OC(OP)C(O)C1O FHVDTGUDJYJELY-UHFFFAOYSA-N 0.000 description 1
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235000010205 Cola acuminata Nutrition 0.000 description 1
244000228088 Cola acuminata Species 0.000 description 1
235000015438 Cola nitida Nutrition 0.000 description 1
229920002261 Corn starch Polymers 0.000 description 1
UDIPTWFVPPPURJ-UHFFFAOYSA-M Cyclamate Chemical class [Na+].[O-]S(=O)(=O)NC1CCCCC1 UDIPTWFVPPPURJ-UHFFFAOYSA-M 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 description 1
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Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
- 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
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P1/00—Drugs for disorders of the alimentary tract or the digestive system
- 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
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- A61P25/00—Drugs for disorders of the nervous system
- A61P25/04—Centrally acting analgesics, e.g. opioids
- A—HUMAN NECESSITIES
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- 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
- A61P43/00—Drugs for specific purposes, not provided for in groups A61P1/00-A61P41/00
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
- A61P9/08—Vasodilators for multiple indications
- 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
- 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

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Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Veterinary Medicine (AREA)
Public Health (AREA)
Medicinal Chemistry (AREA)
Animal Behavior & Ethology (AREA)
Life Sciences & Earth Sciences (AREA)
Pharmacology & Pharmacy (AREA)
Bioinformatics & Cheminformatics (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Engineering & Computer Science (AREA)
General Chemical & Material Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Biomedical Technology (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Pain & Pain Management (AREA)
Heart & Thoracic Surgery (AREA)
Cardiology (AREA)
Epidemiology (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicinal Preparation (AREA)
Plural Heterocyclic Compounds (AREA)
Indole Compounds (AREA)

LVP-98-237A 1992-06-05 1998-10-26 The sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy LV12210B (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB929211903A GB9211903D0 (en)	1992-06-05	1992-06-05	Pharmaceutical composition
GB939307306A GB9307306D0 (en)	1993-04-07	1993-04-07	Therapeutic agents

Publications (2)

Publication Number	Publication Date
LV12210A LV12210A (lv)	1999-01-20
LV12210B true LV12210B (en)	1999-03-20

Family

ID=26301005

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
LVP-98-237A LV12210B (en)	1992-06-05	1998-10-26	The sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy

Country Status (27)

Country	Link
US (1)	US5527817A (sk)
EP (1)	EP0573221B1 (sk)
JP (2)	JP2619197B2 (sk)
KR (1)	KR100286411B1 (sk)
CN (1)	CN1043532C (sk)
AT (1)	ATE165602T1 (sk)
AU (2)	AU659311B2 (sk)
BG (1)	BG61976B1 (sk)
CA (1)	CA2097208C (sk)
CZ (1)	CZ282060B6 (sk)
DE (1)	DE69318212T2 (sk)
DK (1)	DK0573221T3 (sk)
ES (1)	ES2116411T3 (sk)
FI (3)	FI106201B (sk)
HK (1)	HK1010050A1 (sk)
HU (1)	HUT71403A (sk)
IL (1)	IL105847A (sk)
LV (1)	LV12210B (sk)
MX (1)	MX9303373A (sk)
NO (1)	NO307420B1 (sk)
NZ (1)	NZ253210A (sk)
RO (1)	RO114326B1 (sk)
RU (1)	RU2130022C1 (sk)
SG (1)	SG50406A1 (sk)
SK (1)	SK279211B6 (sk)
UA (1)	UA27908C2 (sk)
WO (1)	WO1993025547A1 (sk)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE69616335T2 (de) *	1995-07-11	2002-07-11	MERCK & CO., INC.	Ein triazolylmethyl-indol-ethylamin-bisulfat-salz
ZA965837B (en) *	1995-07-11	1997-01-31	Merck & Co Inc	A triazolylmethyl-indole ethylamine bisulfate salt
US6192882B1 (en) *	1997-02-24	2001-02-27	Aradigm Corporation	Formulation and devices for monitoring the efficacy of the delivery of aerosols
US6349719B2 (en)	1997-02-24	2002-02-26	Aradigm Corporation	Formulation and devices for monitoring the efficacy of the delivery of aerosols
CA2348979A1 (en) *	1998-11-02	2000-05-11	Merck & Co., Inc.	Method of treating migraines and pharmaceutical compositions
CN100364991C (zh)	2001-08-15	2008-01-30	法玛西雅厄普约翰美国公司	2,4-二甲基-1h-吡咯-3-甲酰胺衍生物的苹果酸盐的晶体、其制备方法和其组合物
WO2006137083A1 (en) *	2005-06-20	2006-12-28	Natco Pharma Limited	Improved process for the preparation of rizatriptan benzoate
ES2270717B1 (es) *	2005-08-08	2008-03-01	Ragactives, S.L.	Procedimiento para la obtencion de derivados de triptamina.
WO2007054979A1 (en) *	2005-11-14	2007-05-18	Matrix Laboratories Ltd	Process for the large scale production of rizatriptan benzoate
CA2688463A1 (en) *	2007-06-04	2008-12-11	Generics [Uk] Limited	Process for the preparation of rizatriptan
CA3010568C (en)	2016-01-27	2023-10-17	Instar Technologies A.S.	Oromucosal nanofiber carriers for therapeutic treatment
WO2024144413A1 (ru) *	2022-12-28	2024-07-04	Общество С Ограниченной Ответственностью "Ферринг Продакшн"	Жидкая фармацевтическая композиция для назального введения, содержащая ризатриптан

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8724912D0 (en) *	1987-10-23	1987-11-25	Wellcome Found	Indole derivatives
GB9026998D0 (en) *	1990-12-12	1991-01-30	Glaxo Group Ltd	Medicaments
CZ283018B6 (cs) *	1991-02-01	1997-12-17	Merck Sharp And Dohme Limited	Deriváty imidazolu, triazolu a tetrazolu a farmaceutické přípravky na jejich bázi

1993
- 1993-05-28 SK SK1479-94A patent/SK279211B6/sk unknown
- 1993-05-28 EP EP93304158A patent/EP0573221B1/en not_active Expired - Lifetime
- 1993-05-28 WO PCT/GB1993/001132 patent/WO1993025547A1/en active IP Right Grant
- 1993-05-28 CA CA002097208A patent/CA2097208C/en not_active Expired - Fee Related
- 1993-05-28 ES ES93304158T patent/ES2116411T3/es not_active Expired - Lifetime
- 1993-05-28 NZ NZ253210A patent/NZ253210A/en unknown
- 1993-05-28 DE DE69318212T patent/DE69318212T2/de not_active Expired - Fee Related
- 1993-05-28 CZ CZ943044A patent/CZ282060B6/cs not_active IP Right Cessation
- 1993-05-28 RO RO94-01910A patent/RO114326B1/ro unknown
- 1993-05-28 JP JP5127463A patent/JP2619197B2/ja not_active Expired - Fee Related
- 1993-05-28 AT AT93304158T patent/ATE165602T1/de not_active IP Right Cessation
- 1993-05-28 KR KR1019940704402A patent/KR100286411B1/ko not_active Expired - Fee Related
- 1993-05-28 HU HU9403478A patent/HUT71403A/hu unknown
- 1993-05-28 RU RU94046380/04A patent/RU2130022C1/ru not_active IP Right Cessation
- 1993-05-28 AU AU39875/93A patent/AU659311B2/en not_active Ceased
- 1993-05-28 DK DK93304158T patent/DK0573221T3/da active
- 1993-05-28 SG SG1996000374A patent/SG50406A1/en unknown
- 1993-05-28 UA UA94129126A patent/UA27908C2/uk unknown
- 1993-05-28 AU AU43372/93A patent/AU4337293A/en not_active Abandoned
- 1993-05-31 IL IL10584793A patent/IL105847A/en not_active IP Right Cessation
- 1993-06-04 MX MX9303373A patent/MX9303373A/es not_active IP Right Cessation
- 1993-06-05 CN CN93108728A patent/CN1043532C/zh not_active Expired - Fee Related
1994
- 1994-10-21 BG BG99132A patent/BG61976B1/bg unknown
- 1994-12-02 NO NO944656A patent/NO307420B1/no not_active IP Right Cessation
- 1994-12-02 FI FI945694A patent/FI106201B/fi active
- 1994-12-07 US US08/350,760 patent/US5527817A/en not_active Expired - Lifetime
1996
- 1996-08-30 JP JP8230809A patent/JP2972150B2/ja not_active Expired - Fee Related
1998
- 1998-09-05 HK HK98110478A patent/HK1010050A1/xx not_active IP Right Cessation
- 1998-10-26 LV LVP-98-237A patent/LV12210B/en unknown
2000
- 2000-08-10 FI FI20001776A patent/FI20001776L/fi unknown
- 2000-08-10 FI FI20001777A patent/FI20001777L/fi unknown

Also Published As

Publication number	Publication date
SK279211B6 (sk)	1998-08-05
DE69318212T2 (de)	1998-11-19
BG61976B1 (bg)	1998-11-30
NZ253210A (en)	1995-09-26
FI945694A0 (fi)	1994-12-02
ES2116411T3 (es)	1998-07-16
BG99132A (bg)	1995-07-28
AU659311B2 (en)	1995-05-11
FI106201B (fi)	2000-12-15
JPH09176155A (ja)	1997-07-08
CA2097208A1 (en)	1993-12-06
NO944656D0 (no)	1994-12-02
UA27908C2 (uk)	2000-10-16
HK1010050A1 (en)	1999-06-11
NO307420B1 (no)	2000-04-03
JP2619197B2 (ja)	1997-06-11
CN1089263A (zh)	1994-07-13
LV12210A (lv)	1999-01-20
FI20001776L (fi)	2000-08-10
SK147994A3 (en)	1995-07-11
RU2130022C1 (ru)	1999-05-10
AU3987593A (en)	1993-12-09
ATE165602T1 (de)	1998-05-15
IL105847A0 (en)	1993-09-22
EP0573221B1 (en)	1998-04-29
JPH0641121A (ja)	1994-02-15
RO114326B1 (ro)	1999-03-30
SG50406A1 (en)	1998-07-20
HU9403478D0 (en)	1995-02-28
RU94046380A (ru)	1996-12-10
EP0573221A1 (en)	1993-12-08
CA2097208C (en)	2005-02-08
HUT71403A (en)	1995-11-28
IL105847A (en)	1998-09-24
US5527817A (en)	1996-06-18
CN1043532C (zh)	1999-06-02
JP2972150B2 (ja)	1999-11-08
FI20001777L (fi)	2000-08-10
MX9303373A (es)	1995-01-31
AU4337293A (en)	1994-01-04
CZ282060B6 (cs)	1997-05-14
KR950701922A (ko)	1995-05-17
NO944656L (no)	1994-12-02
DK0573221T3 (da)	1998-10-07
DE69318212D1 (de)	1998-06-04
FI945694L (fi)	1994-12-02
WO1993025547A1 (en)	1993-12-23
KR100286411B1 (ko)	2001-04-16
CZ304494A3 (en)	1995-09-13

Publication	Publication Date	Title
EP0490689B1 (en)	1995-03-15	3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulphonamide sulphate (2:1)
JPH0291068A (ja)	1990-03-30	化合物
US5527817A (en)	1996-06-18	Sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy
US5834502A (en)	1998-11-10	Triazolylmethyl-indole ethylamine bisulfate salt
CA2225416C (en)	2009-02-24	A triazolylmethyl-indole ethylamine bisulfate salt
HRP940225A2 (en)	1997-08-31	The sulphate salt of a substituted triazole, pharmaceutical compositions thereof, and their use in therapy