NO124997B - - Google Patents
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- Publication number
- NO124997B NO124997B NO681425A NO142568A NO124997B NO 124997 B NO124997 B NO 124997B NO 681425 A NO681425 A NO 681425A NO 142568 A NO142568 A NO 142568A NO 124997 B NO124997 B NO 124997B
- Authority
- NO
- Norway
- Prior art keywords
- pyridone
- salts
- amino
- acid
- methyl
- Prior art date
Links
- 150000003839 salts Chemical class 0.000 claims description 16
- 238000000034 method Methods 0.000 claims description 10
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 claims description 5
- 159000000000 sodium salts Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 150000002739 metals Chemical class 0.000 claims 2
- 239000007858 starting material Substances 0.000 claims 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 239000000243 solution Substances 0.000 description 7
- 239000002585 base Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 239000000284 extract Substances 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 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
- 239000005708 Sodium hypochlorite Substances 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 229940072033 potash Drugs 0.000 description 2
- 235000015320 potassium carbonate Nutrition 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 description 2
- SUKJFIGYRHOWBL-UHFFFAOYSA-N sodium hypochlorite Chemical compound [Na+].Cl[O-] SUKJFIGYRHOWBL-UHFFFAOYSA-N 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- JADBQNNRRQRIFM-UHFFFAOYSA-N 1-aminopyridin-2-one Chemical class NN1C=CC=CC1=O JADBQNNRRQRIFM-UHFFFAOYSA-N 0.000 description 1
- WUBBRNOQWQTFEX-UHFFFAOYSA-N 4-aminosalicylic acid Chemical compound NC1=CC=C(C(O)=O)C(O)=C1 WUBBRNOQWQTFEX-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- -1 alkali salts Chemical class 0.000 description 1
- 150000001447 alkali salts Chemical class 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229960004909 aminosalicylic acid Drugs 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 229960004365 benzoic acid Drugs 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000012876 carrier material Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- PSLIMVZEAPALCD-UHFFFAOYSA-N ethanol;ethoxyethane Chemical compound CCO.CCOCC PSLIMVZEAPALCD-UHFFFAOYSA-N 0.000 description 1
- 239000012259 ether extract Substances 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- 239000012433 hydrogen halide Substances 0.000 description 1
- 229910000039 hydrogen halide Inorganic materials 0.000 description 1
- 230000001077 hypotensive effect Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229940098779 methanesulfonic acid Drugs 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 238000009738 saturating Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members 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 ring carbon atoms
- C07D211/40—Oxygen atoms
- C07D211/44—Oxygen atoms attached in position 4
- C07D211/46—Oxygen atoms attached in position 4 having a hydrogen atom as the second substituent in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pyridine Compounds (AREA)
Description
Fremgangsmåte til fremstilling av l-amino-pyridon-(2)-forbindelser.
Gjenstanden for foreliggende oppfinnelse er
;n ny fremgangsmåte til fremstilling av 1-imino-pyridon-(2) med formelen
og dens C-alkyl-derivater samt salter. Som al-kylrest kommer særlig metylresten på tale.
Fremgangsmåten ifølge oppfinnelsen består
i at man omsetter pyridon-(2) eller dets C-alkyl-derivater, eventuelt i form av deres metall-salter, f. eks. alkalisalter, med N-halogenamin,
slik som N-kloramin, og om ønskes, av erholdte
baser fremstiller salter eller omdanner erholdte
salter til frie baser. Således kan man f. eks. om-sette pyridon-(2) eller C-laverealkylpyridon-(2)
med kloramin til de tilsvarende 1-amino-pyridoner-(2).
Reaksjonen utføres fortrinsvis i konsentrert,
vandig oppløsning og i kulden. Alt etter arbeids-måten får man 1-amino-pyridonene i form av
deres baser eller salter. Av basene kan det dannes salter, slik som med hydrogenhalogenidsy-rer, svovelsyre, salpetersyre, fosforsyre, eddik-syre, propionsyre, oksalsyre, eplesyre, sitron-syre, metansulfonsyre, etansulfonsyre, oksye-tansulfonsyre, benzoesyre, salicylsyre, p-amino-salicylsyre eller p-toluolsulfonsyre. Av saltene
fremstiller man på i og for seg kjent måte de
frie baser.
De forbindelser som kan fåes ifølge den nye
fremgangsmåte kan finne flere anvendelser i
teknikken. De er delvis kjent.
l-amino-pyridon-(2) og C-alkyl-l-amino-pyridon-(2) og deres salter er nye og har interes-sante farmakologiske egenskaper. Således viser de en hypotensiv virkning og kan derfor finne terapeutisk anvendelse som blodtrykksenkende middel. Av særlig betydning i denne henseende er l-amino-4-metyl-pyridon-(2) med formelen
og dets salter.
l-amino-pyridon-(2) og dets C-lavere-alkyl-derivater samt deres salter kan anvendes som lege-middel f. eks. i form av farmasøytiske preparater som inneholder disse eller deres salter i blanding med et for ehteral, parenteral eller topikal anvendelse egnet farmasøytisk organiske eller anorganisk, fast eller flytende bæremateriale.
Oppfinnelsen beskrives nærmere i de føl-gende eksempler. Temperaturen er angitt i Celsius-grader.
Eksempel 1.
I en iskjølt kloraminoppløsning fremstilt ved å tilsette 65 cm<3> av en 1,93-molar nøytral natri-umhypoklorittoppløsning ved 0°C 203 cm<3 >1,84-molar ammoniakk og påfølgende henstand av reaksjonsblandingen i en time i en is-koksalt-kuldeblanding, innføres det av 12 g pyridon-(2) fremstilte natriumsalt av pyridon-(2). Den sterkt alkaliske reaksjohsoppløsning omrøres natten over i en kuldeblanding og ekstraheres i påfølgende 24 timer i en Kutscher-Steudel-apparatur med eter. Ekstrakten .tørket med kaliumkarbonat, gir ved avkjøling til — 10° C krystaller med smeltepunkt 62—63° C. Det således fremstilte l-amino-pyridon-(2) kan om-krystalliseres fra benzol-petroleter. Det dannes fargeløse prismatiske små staver med smeltepunkt 64—66° C.
Den frie base kan omdannes til hydroklorid ved metning av sin eteriske oppløsning med gassformet hydrogenklorid. 1-amino-pyridon-(2)-hydroklorid krystalliserer av eter-etanol eller isopropanol i fargeløse nåler med smeltepunkt 175—177° C.
Eksempel 2.
130 cm3 1,95-molar nøytral natriumhypo-kloritt-oppløsning (0,25 mol) tilsettes ved 0° C 406 cm<3> 1,86-molar ammoniakk (0,75 mol), og reaksjonsblandingen står 1 time i en is-koksalt-kuldeblanding. Denne oppløsning tilsetter man porsjonsvis det av 24 g 4-metyl-pyridon-(2)
(0,25 mol) med 200 cm<3> 50 % natronlut fremstilte natriumsalt. Man rører natten over i en is-koksalt-kuldeblanding og ekstraherer deretter 20 timer i en Kutscher-Steudel-apparatur med eter. Ekstrakten, tørket med natriumsulfat, gir etter inndampning et krystallisat. Det således erholdte l-amino-4-metylpyridon-(2) smelter etter omkrystallisasjon fra benzolpetroleter ved 74—76° C.
Eksempel 3.
Den i eksempel 1 beskrevne iskjølte klor-aminoppløsning tilsettes det av 8,8 g 3-metyl-pyridon-(2) erholdte natriumsalt. Reaksjonsblandingen omrøres i 12 timer i en is-koksalt-kuldeblanding ved en pH-verdi 10. Deretter ekstraheres den 24 timer med eter i en Kutscher-Steudel-appararatur. Eterekstrakten tørkes over pottaske, filtreres og slås sammen med den ekstrakt som fåes ved tre gangers utkokning av pottasken med hver gang 50 cm<3> eter. Ved av-kjøling krystalliserer l-amino-3-metyl-pyridon-(2) med formelen
Det smelter etter omkrystallisasjon fra benzol ved 95—96° C.
På samme måte, idet man går ut fra 5- eller 6-metyl-pyridon-(2), får man l-amino-5-metyl-pyridon-(2) med smeltepunkt 100—101,5° C, eller l-amino-6-metyl-pyridon-(2) med smeltepunkt 70—71,5° C.
Claims (4)
1. Fremgangsmåte til fremstilling av 1-amino-pyridon-(2) med formelen
og dens C-alkyl-derivater og salter av disse,karakterisert ved at man behandler pyridon-(2) eller dens C-alkylderivater med N-halogenamin, og, om ønskes, av erholdte baser fremstiller salter eller omdanner erholdte salter til frie baser.
2. Fremgangsmåte ifølge påstand 1, karakterisert ved at man behandler med en vandig oppløsning av kloramin.
3. Fremgangsmåte ifølge påstandene 1 og 2.karakterisert ved at man som utgangsstoffer anvender pyridon-(2) eller de C-lavere-alkyl-pyridon-(2) eller deres salter med metaller.
4. Fremgangsmåte ifølge påstandene 1—3, karakterisert ved at man som utgangsstoff anvender 4-metyl-pyridon-(2) eller dens salter med metaller, fortrinsvis natriumsaltet.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH558967A CH497458A (de) | 1967-04-19 | 1967-04-19 | Verfahren zur Herstellung neuer Phenothiazin-Derivate |
| CH1705667 | 1967-12-05 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO124997B true NO124997B (no) | 1972-07-03 |
Family
ID=25698043
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO681425A NO124997B (no) | 1967-04-19 | 1968-04-16 |
Country Status (17)
| Country | Link |
|---|---|
| US (1) | US3531480A (no) |
| AT (2) | AT292726B (no) |
| AU (2) | AU5480173A (no) |
| BE (1) | BE713802A (no) |
| BG (1) | BG17326A3 (no) |
| CH (1) | CH497458A (no) |
| DE (1) | DE1770218A1 (no) |
| ES (1) | ES352822A1 (no) |
| FR (1) | FR1583822A (no) |
| GB (2) | GB1223314A (no) |
| IE (2) | IE32170B1 (no) |
| IL (2) | IL29842A (no) |
| NL (1) | NL6804983A (no) |
| NO (1) | NO124997B (no) |
| OA (1) | OA03386A (no) |
| RO (1) | RO54395A (no) |
| SE (2) | SE361884B (no) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3857943A (en) * | 1969-03-27 | 1974-12-31 | May & Baker Ltd | New phenothiazine derivatives in the treatment of spasticity of muscles |
| CH511886A (de) * | 1969-07-08 | 1971-08-31 | Sandoz Ag | Verfahren zur Herstellung neuer Furanonderivate |
| US20040259866A1 (en) * | 1998-06-30 | 2004-12-23 | Snutch Terrance P. | Calcium channel blockers comprising two benzhydril moieties |
| US6310059B1 (en) * | 1998-06-30 | 2001-10-30 | Neuromed Technologies, Inc. | Fused ring calcium channel blockers |
| EP2019676A2 (en) * | 2006-05-11 | 2009-02-04 | Neuromed Pharmaceuticals, Ltd. | Method for increasing the bioavailability of benzhydryl piperazine containing compounds |
| MX2013010306A (es) | 2011-03-08 | 2013-12-09 | Zalicus Pharmaceuticals Ltd | Formulaciones de dispersion solida y metodos de uso de las mismas. |
| US8409560B2 (en) | 2011-03-08 | 2013-04-02 | Zalicus Pharmaceuticals Ltd. | Solid dispersion formulations and methods of use thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1212031A (fr) * | 1957-10-21 | 1960-03-21 | Rhone Poulenc Sa | Dérivés de la phénothiazine substitués à l'azote par une chaîne basique comportant un hétérocycle et leur préparation |
-
1967
- 1967-04-19 CH CH558967A patent/CH497458A/de not_active IP Right Cessation
-
1968
- 1968-03-11 GB GB01783/68A patent/GB1223314A/en not_active Expired
- 1968-03-11 GB GB40359/70A patent/GB1223315A/en not_active Expired
- 1968-04-09 NL NL6804983A patent/NL6804983A/xx unknown
- 1968-04-10 SE SE05102/71A patent/SE361884B/xx unknown
- 1968-04-10 SE SE04843/68A patent/SE356520B/xx unknown
- 1968-04-16 NO NO681425A patent/NO124997B/no unknown
- 1968-04-17 IE IE637/71A patent/IE32170B1/xx unknown
- 1968-04-17 IL IL6829842A patent/IL29842A/en unknown
- 1968-04-17 AT AT374668A patent/AT292726B/de not_active IP Right Cessation
- 1968-04-17 DE DE19681770218 patent/DE1770218A1/de active Pending
- 1968-04-17 AT AT1201369A patent/AT293372B/de not_active IP Right Cessation
- 1968-04-17 IL IL6836239A patent/IL36239A/en unknown
- 1968-04-17 ES ES352822A patent/ES352822A1/es not_active Expired
- 1968-04-17 US US721949A patent/US3531480A/en not_active Expired - Lifetime
- 1968-04-17 BE BE713802D patent/BE713802A/xx unknown
- 1968-04-17 BG BG9805A patent/BG17326A3/xx unknown
- 1968-04-17 IE IE444/68A patent/IE32169B1/xx unknown
- 1968-04-18 RO RO196856492A patent/RO54395A/ro unknown
- 1968-04-18 FR FR148511A patent/FR1583822A/fr not_active Expired
- 1968-04-19 OA OA53262A patent/OA03386A/xx unknown
-
1973
- 1973-04-19 AU AU54801/73A patent/AU5480173A/en not_active Expired
- 1973-04-19 AU AU54802/73A patent/AU5480273A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| GB1223315A (en) | 1971-02-24 |
| US3531480A (en) | 1970-09-29 |
| RO54395A (no) | 1973-02-17 |
| OA03386A (fr) | 1970-12-15 |
| BE713802A (no) | 1968-10-17 |
| AT292726B (de) | 1971-09-10 |
| FR1583822A (no) | 1969-12-05 |
| NL6804983A (no) | 1968-10-21 |
| AU5480273A (en) | 1973-07-12 |
| IL29842A0 (en) | 1968-06-20 |
| IL29842A (en) | 1971-05-26 |
| GB1223314A (en) | 1971-02-24 |
| IE32170L (en) | 1968-10-19 |
| DE1770218A1 (de) | 1971-10-14 |
| SE356520B (no) | 1973-05-28 |
| IE32169B1 (en) | 1973-05-02 |
| AT293372B (de) | 1971-10-11 |
| ES352822A1 (es) | 1969-11-16 |
| SE361884B (no) | 1973-11-19 |
| CH497458A (de) | 1970-10-15 |
| AU5480173A (en) | 1973-07-12 |
| IE32169L (en) | 1968-10-19 |
| BG17326A3 (no) | 1973-07-25 |
| IL36239A (en) | 1971-06-23 |
| IE32170B1 (en) | 1973-05-02 |
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