NO782230L - Fremgangsmaate ved fremstilling av n-amidino-3,5-diamino-6-substituert-2-pyrazincarboxamid - Google Patents
Fremgangsmaate ved fremstilling av n-amidino-3,5-diamino-6-substituert-2-pyrazincarboxamidInfo
- Publication number
- NO782230L NO782230L NO782230A NO782230A NO782230L NO 782230 L NO782230 L NO 782230L NO 782230 A NO782230 A NO 782230A NO 782230 A NO782230 A NO 782230A NO 782230 L NO782230 L NO 782230L
- Authority
- NO
- Norway
- Prior art keywords
- diamino
- amidino
- mol
- preparation
- pyrazinecarboxamide
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims description 18
- 238000002360 preparation method Methods 0.000 title claims description 11
- -1 N-AMIDINO-3,5-DIAMINO-6-SUBSTITUTED-2-PYRAZINE CARBOXAMIDE Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 20
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 8
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 5
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 4
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Chemical group 0.000 claims 1
- 229910052740 iodine Inorganic materials 0.000 claims 1
- 239000011630 iodine Substances 0.000 claims 1
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910001868 water Inorganic materials 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 238000000921 elemental analysis Methods 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 239000002934 diuretic Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- XSDQTOBWRPYKKA-UHFFFAOYSA-N amiloride Chemical compound NC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N XSDQTOBWRPYKKA-UHFFFAOYSA-N 0.000 description 5
- LFKABJCYNYIJOL-UHFFFAOYSA-N methyl 3,5-diamino-6-(trifluoromethylsulfanyl)pyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(SC(F)(F)F)=C(N)N=C1N LFKABJCYNYIJOL-UHFFFAOYSA-N 0.000 description 5
- 229960005206 pyrazinamide Drugs 0.000 description 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 4
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- OOQYPDWXJMEILC-UHFFFAOYSA-N methyl 3,5-diamino-6-iodopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(I)=C(N)N=C1N OOQYPDWXJMEILC-UHFFFAOYSA-N 0.000 description 4
- 150000003839 salts Chemical class 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 229940030606 diuretics Drugs 0.000 description 3
- 229960004198 guanidine Drugs 0.000 description 3
- 229960000789 guanidine hydrochloride Drugs 0.000 description 3
- PJJJBBJSCAKJQF-UHFFFAOYSA-N guanidinium chloride Chemical compound [Cl-].NC(N)=[NH2+] PJJJBBJSCAKJQF-UHFFFAOYSA-N 0.000 description 3
- 239000005457 ice water Substances 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 238000001665 trituration Methods 0.000 description 3
- BTLIEENWNROEFS-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)-6-(trifluoromethylsulfanyl)pyrazine-2-carboxamide Chemical compound NC(=N)NC(=O)C1=NC(SC(F)(F)F)=C(N)N=C1N BTLIEENWNROEFS-UHFFFAOYSA-N 0.000 description 2
- PNZSORNWGMHKMO-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)-6-methylsulfanylpyrazine-2-carboxamide;hydrate;hydrochloride Chemical compound O.Cl.CSC1=NC(C(=O)NC(N)=N)=C(N)N=C1N PNZSORNWGMHKMO-UHFFFAOYSA-N 0.000 description 2
- PDVAOHMQCDEZMX-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)-6-phenylsulfanylpyrazine-2-carboxamide Chemical compound N1=C(N)C(C(=O)NC(=N)N)=NC(SC=2C=CC=CC=2)=C1N PDVAOHMQCDEZMX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229960002576 amiloride Drugs 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- DSRGOGFYFTWCRT-UHFFFAOYSA-N methyl 3,5-diamino-6-cyanopyrazine-2-carboxylate Chemical compound COC(=O)C1=NC(C#N)=C(N)N=C1N DSRGOGFYFTWCRT-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- DGGUWHBFABFABP-UHFFFAOYSA-N o-methyl 3,5-diamino-6-methylpyrazine-2-carbothioate Chemical compound COC(=S)C1=NC(C)=C(N)N=C1N DGGUWHBFABFABP-UHFFFAOYSA-N 0.000 description 2
- GBKFTJDKFLXDDF-UHFFFAOYSA-N o-methyl 3,5-diamino-6-phenylpyrazine-2-carbothioate Chemical compound N1=C(N)C(C(=S)OC)=NC(C=2C=CC=CC=2)=C1N GBKFTJDKFLXDDF-UHFFFAOYSA-N 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 239000011591 potassium Substances 0.000 description 2
- 229910052700 potassium Inorganic materials 0.000 description 2
- 238000000746 purification Methods 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- VFWCMGCRMGJXDK-UHFFFAOYSA-N 1-chlorobutane Chemical compound CCCCCl VFWCMGCRMGJXDK-UHFFFAOYSA-N 0.000 description 1
- OBTZDIRUQWFRFZ-UHFFFAOYSA-N 2-(5-methylfuran-2-yl)-n-(4-methylphenyl)quinoline-4-carboxamide Chemical compound O1C(C)=CC=C1C1=CC(C(=O)NC=2C=CC(C)=CC=2)=C(C=CC=C2)C2=N1 OBTZDIRUQWFRFZ-UHFFFAOYSA-N 0.000 description 1
- LESDXSAOLROCQI-UHFFFAOYSA-N 3,5-diamino-6-cyano-n-(diaminomethylidene)pyrazine-2-carboxamide Chemical compound NC(=N)NC(=O)C1=NC(C#N)=C(N)N=C1N LESDXSAOLROCQI-UHFFFAOYSA-N 0.000 description 1
- FQLNUEDBHFYKHG-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)-6-(trifluoromethylsulfanyl)pyrazine-2-carboxamide;hydrate Chemical compound O.NC(=N)NC(=O)C1=NC(SC(F)(F)F)=C(N)N=C1N FQLNUEDBHFYKHG-UHFFFAOYSA-N 0.000 description 1
- FKXYVYMLZGVJIM-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)-6-iodopyrazine-2-carboxamide Chemical compound NC(N)=NC(=O)C1=NC(I)=C(N)N=C1N FKXYVYMLZGVJIM-UHFFFAOYSA-N 0.000 description 1
- OISRMKAPQONEBW-UHFFFAOYSA-N 3,5-diamino-n-(diaminomethylidene)-6-iodopyrazine-2-carboxamide;hydrochloride Chemical compound Cl.NC(=N)NC(=O)C1=NC(I)=C(N)N=C1N OISRMKAPQONEBW-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 102100025027 E3 ubiquitin-protein ligase TRIM69 Human genes 0.000 description 1
- 101000830203 Homo sapiens E3 ubiquitin-protein ligase TRIM69 Proteins 0.000 description 1
- 206010020772 Hypertension Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 208000010428 Muscle Weakness Diseases 0.000 description 1
- 206010028372 Muscular weakness Diseases 0.000 description 1
- 206010030113 Oedema Diseases 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- RTEXIPZMMDUXMR-UHFFFAOYSA-N benzene;ethyl acetate Chemical compound CCOC(C)=O.C1=CC=CC=C1 RTEXIPZMMDUXMR-UHFFFAOYSA-N 0.000 description 1
- MDHYEMXUFSJLGV-UHFFFAOYSA-N beta-phenethyl acetate Natural products CC(=O)OCCC1=CC=CC=C1 MDHYEMXUFSJLGV-UHFFFAOYSA-N 0.000 description 1
- QHACEJBZGFEEJE-UHFFFAOYSA-L bis(trifluoromethylsulfanyl)mercury Chemical compound [Hg+2].FC(F)(F)[S-].FC(F)(F)[S-] QHACEJBZGFEEJE-UHFFFAOYSA-L 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- BCCLDZVXWYCMMP-UHFFFAOYSA-M copper(1+);trifluoromethanethiolate Chemical compound [Cu+].FC(F)(F)[S-] BCCLDZVXWYCMMP-UHFFFAOYSA-M 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 230000001882 diuretic effect Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WISBTQFQQVVPFL-UHFFFAOYSA-N n-bromo-n-methylmethanamine Chemical compound CN(C)Br WISBTQFQQVVPFL-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 150000003109 potassium Chemical class 0.000 description 1
- 229910001414 potassium ion Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical class OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 description 1
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical compound NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D241/00—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings
- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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
- C07D241/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D241/26—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with nitrogen atoms directly attached to ring carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/02—Acyclic compounds
-
- 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
- A61P7/10—Antioedematous agents; Diuretics
Landscapes
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Diabetes (AREA)
- Pharmacology & Pharmacy (AREA)
- Hematology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Cephalosporin Compounds (AREA)
- Liquid Crystal Substances (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/811,011 US4196292A (en) | 1977-06-29 | 1977-06-29 | 6-Substituted amiloride derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO782230L true NO782230L (no) | 1979-01-02 |
Family
ID=25205286
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO782230A NO782230L (no) | 1977-06-29 | 1978-06-28 | Fremgangsmaate ved fremstilling av n-amidino-3,5-diamino-6-substituert-2-pyrazincarboxamid |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4196292A (de) |
| EP (1) | EP0000200B1 (de) |
| JP (1) | JPS5412389A (de) |
| AT (1) | AT362795B (de) |
| DE (1) | DE2861684D1 (de) |
| DK (1) | DK290278A (de) |
| ES (1) | ES471244A1 (de) |
| FI (1) | FI781966A (de) |
| HU (1) | HU178302B (de) |
| IT (1) | IT1105454B (de) |
| NO (1) | NO782230L (de) |
| PL (1) | PL119097B1 (de) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4362724A (en) * | 1980-05-19 | 1982-12-07 | Merck & Co., Inc. | Method of treating edema and hypertension and pharmaceutical composition therefor in which the active ingredient comprises a novel substituted pyrazinyl-1,2,4-oxadiazole and a kaliuretic diuretic |
| US4594349A (en) * | 1982-01-04 | 1986-06-10 | Beyer Jr Karl H | Hyperuretic agents |
| US4952582A (en) * | 1982-01-04 | 1990-08-28 | Beyer Jr Karl H | Pyrazinoylguanidine and derivatives thereof having few polar substituents and being useful as hyperuretic agents |
| WO1990009792A1 (en) * | 1989-03-03 | 1990-09-07 | The General Hospital Corporation | Topical application of amiloride or analogues thereof for treatment of inflammation |
| US6858615B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenyl guanidine sodium channel blockers |
| US6858614B2 (en) | 2002-02-19 | 2005-02-22 | Parion Sciences, Inc. | Phenolic guanidine sodium channel blockers |
| US6903105B2 (en) * | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
| US7745442B2 (en) | 2003-08-20 | 2010-06-29 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens |
| US20090253714A1 (en) * | 2003-08-20 | 2009-10-08 | Johnson Michael R | Methods of reducing risk of infection from pathogens |
| US20070021439A1 (en) * | 2005-07-25 | 2007-01-25 | Parion Sciences, Inc. | Methods of reducing risk of infection from pathogens with soluble amide and ester pyrazinoylguanidine sodium channel blockers |
| AR086745A1 (es) | 2011-06-27 | 2014-01-22 | Parion Sciences Inc | 3,5-diamino-6-cloro-n-(n-(4-(4-(2-(hexil(2,3,4,5,6-pentahidroxihexil)amino)etoxi)fenil)butil)carbamimidoil)pirazina-2-carboxamida |
| AU2013363215B2 (en) | 2012-12-17 | 2018-03-01 | Parion Sciences, Inc. | 3,5-diamino-6-chloro-N-(N-(4-phenylbutyl)carbamimidoyl) pyrazine-2- carboxamide compounds |
| EP3150585A1 (de) | 2012-12-17 | 2017-04-05 | Parion Sciences, Inc. | Chloro-pyrazin-carboxamid-derivate mit blockierungsaktivität des epithelialen natriumkanals |
| US9102633B2 (en) | 2013-12-13 | 2015-08-11 | Parion Sciences, Inc. | Arylalkyl- and aryloxyalkyl-substituted epithelial sodium channel blocking compounds |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB286896A (en) * | 1927-03-29 | 1928-03-15 | Arthur William Howarth | Improvements in smokers' pipes |
| US3305552A (en) * | 1965-11-22 | 1967-02-21 | Merck & Co Inc | 3-aminopyrazinoic acids and process for their preparation |
| US3507865A (en) * | 1967-04-27 | 1970-04-21 | Merck & Co Inc | 3-hydroxy- and 3-mercaptopyrazinamidoguanidines the corresponding ethers and thioethers and processes for their preparation |
| US3573306A (en) * | 1969-03-05 | 1971-03-30 | Merck & Co Inc | Process for preparation of n-substituted 3,5-diamino-6-halopyrazinamides |
-
1977
- 1977-06-29 US US05/811,011 patent/US4196292A/en not_active Expired - Lifetime
-
1978
- 1978-06-20 FI FI781966A patent/FI781966A/fi not_active Application Discontinuation
- 1978-06-22 HU HU78ME2174A patent/HU178302B/hu unknown
- 1978-06-22 IT IT49984/78A patent/IT1105454B/it active
- 1978-06-27 PL PL1978207947A patent/PL119097B1/pl unknown
- 1978-06-28 DE DE7878100264T patent/DE2861684D1/de not_active Expired
- 1978-06-28 AT AT0469078A patent/AT362795B/de not_active IP Right Cessation
- 1978-06-28 DK DK290278A patent/DK290278A/da unknown
- 1978-06-28 NO NO782230A patent/NO782230L/no unknown
- 1978-06-28 ES ES471244A patent/ES471244A1/es not_active Expired
- 1978-06-28 EP EP78100264A patent/EP0000200B1/de not_active Expired
- 1978-06-29 JP JP7924078A patent/JPS5412389A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AT362795B (de) | 1981-06-10 |
| PL119097B1 (en) | 1981-11-30 |
| DK290278A (da) | 1978-12-30 |
| DE2861684D1 (en) | 1982-04-29 |
| ES471244A1 (es) | 1979-10-01 |
| FI781966A (fi) | 1978-12-30 |
| IT7849984A0 (it) | 1978-06-22 |
| IT1105454B (it) | 1985-11-04 |
| PL207947A1 (pl) | 1979-10-22 |
| EP0000200B1 (de) | 1982-03-24 |
| EP0000200A1 (de) | 1979-01-10 |
| HU178302B (en) | 1982-04-28 |
| ATA469078A (de) | 1980-11-15 |
| US4196292A (en) | 1980-04-01 |
| JPS5412389A (en) | 1979-01-30 |
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