IE49578B1 - Novel heterocyclic substituted pyrazinoylguanidines,processes for preparing and a pharmaceutical composition containing the same - Google Patents
Novel heterocyclic substituted pyrazinoylguanidines,processes for preparing and a pharmaceutical composition containing the sameInfo
- Publication number
- IE49578B1 IE49578B1 IE608/80A IE60880A IE49578B1 IE 49578 B1 IE49578 B1 IE 49578B1 IE 608/80 A IE608/80 A IE 608/80A IE 60880 A IE60880 A IE 60880A IE 49578 B1 IE49578 B1 IE 49578B1
- Authority
- IE
- Ireland
- Prior art keywords
- hydrogen
- compound
- diamino
- chloro
- formula
- Prior art date
Links
- 239000008194 pharmaceutical composition Substances 0.000 title claims description 4
- 125000000623 heterocyclic group Chemical group 0.000 title abstract description 3
- 238000000034 method Methods 0.000 title description 13
- -1 heterocyclic pyrazinoylguanidines Chemical class 0.000 claims abstract description 18
- 238000004519 manufacturing process Methods 0.000 claims abstract 3
- 150000001875 compounds Chemical class 0.000 claims description 30
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 17
- 239000001257 hydrogen Substances 0.000 claims description 17
- 229960005206 pyrazinamide Drugs 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000006295 amino methylene group Chemical group [H]N(*)C([H])([H])* 0.000 claims description 9
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- 150000001412 amines Chemical class 0.000 claims description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 7
- 150000003839 salts Chemical class 0.000 claims description 7
- NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 231100000252 nontoxic Toxicity 0.000 claims description 4
- 230000003000 nontoxic effect Effects 0.000 claims description 4
- 125000002373 5 membered heterocyclic group Chemical group 0.000 claims description 3
- 125000004070 6 membered heterocyclic group Chemical group 0.000 claims description 3
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 claims description 3
- ZRALSGWEFCBTJO-UHFFFAOYSA-N anhydrous guanidine Natural products NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 claims description 3
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 claims description 3
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 claims description 3
- 150000002357 guanidines Chemical class 0.000 claims description 3
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 3
- QMEZUZOCLYUADC-UHFFFAOYSA-N hydrate;dihydrochloride Chemical compound O.Cl.Cl QMEZUZOCLYUADC-UHFFFAOYSA-N 0.000 claims description 2
- 125000001475 halogen functional group Chemical group 0.000 claims 3
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- MXVXMUGERGRCGR-UHFFFAOYSA-N 3,5-diamino-6-chloro-n-[[2-(4,5-dihydro-1,3-oxazol-2-yl)hydrazinyl]methylidene]pyrazine-2-carboxamide Chemical compound N1=C(Cl)C(N)=NC(N)=C1C(=O)N=CNNC1=NCCO1 MXVXMUGERGRCGR-UHFFFAOYSA-N 0.000 claims 1
- 101100114416 Neurospora crassa (strain ATCC 24698 / 74-OR23-1A / CBS 708.71 / DSM 1257 / FGSC 987) con-10 gene Proteins 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 239000002934 diuretic Substances 0.000 abstract description 5
- 230000001882 diuretic effect Effects 0.000 abstract description 4
- 239000003795 chemical substances by application Substances 0.000 abstract description 3
- WNBSDCKJFDZMHT-UHFFFAOYSA-N n-(diaminomethylidene)pyrazine-2-carboxamide Chemical class NC(N)=NC(=O)C1=CN=CC=N1 WNBSDCKJFDZMHT-UHFFFAOYSA-N 0.000 abstract description 2
- 230000001452 natriuretic effect Effects 0.000 abstract description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229910001868 water Inorganic materials 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000000921 elemental analysis Methods 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000013256 coordination polymer Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- URLKBWYHVLBVBO-UHFFFAOYSA-N Para-Xylene Chemical group CC1=CC=C(C)C=C1 URLKBWYHVLBVBO-UHFFFAOYSA-N 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 238000010992 reflux Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
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- DRSHXJFUUPIBHX-UHFFFAOYSA-N COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 Chemical compound COc1ccc(cc1)N1N=CC2C=NC(Nc3cc(OC)c(OC)c(OCCCN4CCN(C)CC4)c3)=NC12 DRSHXJFUUPIBHX-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- DEYNCJGOBKTQET-UHFFFAOYSA-N (3,5-diamino-6-chloropyrazin-2-yl)-imidazol-1-ylmethanone Chemical compound N1=C(Cl)C(N)=NC(N)=C1C(=O)N1C=NC=C1 DEYNCJGOBKTQET-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 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 3
- 238000011065 in-situ storage Methods 0.000 description 3
- FPJBJFLCMMEBPC-UHFFFAOYSA-N methyl n'-(3,5-diamino-6-chloropyrazine-2-carbonyl)carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC(=O)C1=NC(Cl)=C(N)N=C1N FPJBJFLCMMEBPC-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000376 reactant Substances 0.000 description 3
- 230000000894 saliuretic effect Effects 0.000 description 3
- 239000003826 tablet Substances 0.000 description 3
- KRGXPZGGGIOSTF-UHFFFAOYSA-N 2-amino-6-chloro-n-cyano-5-(propan-2-ylamino)-1h-pyrazine-2-carboxamide Chemical compound CC(C)NC1=C(Cl)NC(N)(C(=O)NC#N)C=N1 KRGXPZGGGIOSTF-UHFFFAOYSA-N 0.000 description 2
- HTOBKSLMCGDULE-UHFFFAOYSA-N 3,5-diamino-6-chloro-n-[(2-pyridin-3-ylhydrazinyl)methylidene]pyrazine-2-carboxamide Chemical compound N1=C(Cl)C(N)=NC(N)=C1C(=O)N=CNNC1=CC=CN=C1 HTOBKSLMCGDULE-UHFFFAOYSA-N 0.000 description 2
- CSXDJDPMACBTKT-UHFFFAOYSA-N 3,5-diamino-6-chloro-n-[[2-(1h-imidazol-2-yl)hydrazinyl]methylidene]pyrazine-2-carboxamide Chemical compound N1=C(Cl)C(N)=NC(N)=C1C(=O)N=CNNC1=NC=CN1 CSXDJDPMACBTKT-UHFFFAOYSA-N 0.000 description 2
- OCSQJDAUOOHJEI-UHFFFAOYSA-N 3,5-diamino-6-chloropyrazine-2-carboxylic acid Chemical compound NC1=NC(N)=C(C(O)=O)N=C1Cl OCSQJDAUOOHJEI-UHFFFAOYSA-N 0.000 description 2
- XWINUZHQCMPRBW-UHFFFAOYSA-N 3-amino-n-carbamothioyl-6-chloro-5-(propan-2-ylamino)pyrazine-2-carboxamide Chemical compound CC(C)NC1=NC(N)=C(C(=O)NC(N)=S)N=C1Cl XWINUZHQCMPRBW-UHFFFAOYSA-N 0.000 description 2
- CUYKNJBYIJFRCU-UHFFFAOYSA-N 3-aminopyridine Chemical compound NC1=CC=CN=C1 CUYKNJBYIJFRCU-UHFFFAOYSA-N 0.000 description 2
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- 241001465754 Metazoa Species 0.000 description 2
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- 235000011114 ammonium hydroxide Nutrition 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 230000029142 excretion Effects 0.000 description 2
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- 125000005843 halogen group Chemical group 0.000 description 2
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- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- NFLMXXUXQOFMRZ-UHFFFAOYSA-N methyl n'-[3-amino-6-chloro-5-(dimethylamino)pyrazine-2-carbonyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC(=O)C1=NC(Cl)=C(N(C)C)N=C1N NFLMXXUXQOFMRZ-UHFFFAOYSA-N 0.000 description 2
- HKABNDNBYBSGFY-UHFFFAOYSA-N methyl n'-[3-amino-6-chloro-5-(propan-2-ylamino)pyrazine-2-carbonyl]carbamimidothioate;hydroiodide Chemical compound I.CSC(=N)NC(=O)C1=NC(Cl)=C(NC(C)C)N=C1N HKABNDNBYBSGFY-UHFFFAOYSA-N 0.000 description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- IPEHBUMCGVEMRF-UHFFFAOYSA-N pyrazinecarboxamide Chemical class NC(=O)C1=CN=CC=N1 IPEHBUMCGVEMRF-UHFFFAOYSA-N 0.000 description 2
- 238000001226 reprecipitation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- NDNUYJUBUCCJGR-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)guanidine;dihydrochloride Chemical compound Cl.Cl.NC(=N)NC1=NC=CN1 NDNUYJUBUCCJGR-UHFFFAOYSA-N 0.000 description 1
- XRSZZKUZQREUHY-UHFFFAOYSA-N 2-(4,5-dihydro-1,3-oxazol-2-yl)guanidine;sulfuric acid Chemical compound OS(O)(=O)=O.NC(N)=NC1=NCCO1 XRSZZKUZQREUHY-UHFFFAOYSA-N 0.000 description 1
- FJISUHIGEMWUHA-UHFFFAOYSA-N 2-(4,5-dihydro-1h-imidazol-2-yl)guanidine Chemical compound NC(=N)NC1=NCCN1 FJISUHIGEMWUHA-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
- JIVPVXMEBJLZRO-CQSZACIVSA-N 2-chloro-5-[(1r)-1-hydroxy-3-oxo-2h-isoindol-1-yl]benzenesulfonamide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC([C@@]2(O)C3=CC=CC=C3C(=O)N2)=C1 JIVPVXMEBJLZRO-CQSZACIVSA-N 0.000 description 1
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- ZULAWPWZPUHKNH-UHFFFAOYSA-N 3,5-diamino-6-chloro-n-[[2-(1,1-dioxothiolan-3-yl)hydrazinyl]methylidene]pyrazine-2-carboxamide;hydrate Chemical compound O.N1=C(Cl)C(N)=NC(N)=C1C(=O)N=CNNC1CS(=O)(=O)CC1 ZULAWPWZPUHKNH-UHFFFAOYSA-N 0.000 description 1
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- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910001415 sodium ion Inorganic materials 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000005550 wet granulation 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
- 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)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Diabetes (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Hematology (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Glass Compositions (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/024,293 US4246406A (en) | 1979-03-27 | 1979-03-27 | Heterocyclic substituted pyrazinoylguanidines |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE800608L IE800608L (en) | 1980-09-27 |
| IE49578B1 true IE49578B1 (en) | 1985-10-30 |
Family
ID=21819847
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE608/80A IE49578B1 (en) | 1979-03-27 | 1980-03-25 | Novel heterocyclic substituted pyrazinoylguanidines,processes for preparing and a pharmaceutical composition containing the same |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4246406A (enExample) |
| EP (1) | EP0017152B1 (enExample) |
| JP (2) | JPS55130965A (enExample) |
| AT (1) | ATE2323T1 (enExample) |
| AU (1) | AU533298B2 (enExample) |
| DE (1) | DE3061733D1 (enExample) |
| DK (1) | DK129180A (enExample) |
| IE (1) | IE49578B1 (enExample) |
| NO (1) | NO152560C (enExample) |
| ZA (1) | ZA801770B (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4594349A (en) * | 1982-01-04 | 1986-06-10 | Beyer Jr Karl H | Hyperuretic agents |
| US4496573A (en) * | 1982-08-24 | 1985-01-29 | William H. Rorer, Inc. | 1-Pyridylmethyl-3-acyl guanidines |
| US4512991A (en) * | 1982-12-27 | 1985-04-23 | Merck & Co., Inc. | 3-Acyl-2-amino-5-halo-6-(substituted)pyrazine antimicrobial compounds |
| 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 |
| US7109224B2 (en) * | 2002-11-06 | 2006-09-19 | Bristol-Myers Squibb Co. | Acyl guanidine compounds and use thereof |
| US6903105B2 (en) * | 2003-02-19 | 2005-06-07 | Parion Sciences, Inc. | Sodium channel blockers |
| AU2004266704B2 (en) * | 2003-08-18 | 2012-02-23 | Parion Sciences, Inc. | Capped pyrazinoylguanidine 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 |
| US7399766B2 (en) * | 2004-08-18 | 2008-07-15 | Parion Sciences, Inc. | Soluble amide & ester pyrazinoylguanidine sodium channel blockers |
| 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 |
| GB0526244D0 (en) | 2005-12-22 | 2006-02-01 | Novartis Ag | Organic compounds |
| US8318935B2 (en) | 2007-05-07 | 2012-11-27 | Novartis Ag | Organic compounds 75074 |
| EP2231280B1 (en) | 2007-12-10 | 2016-08-10 | Novartis AG | Amiloride-like Pyrazine-carboxamides as ENaC blockers |
| EP2813227A1 (en) | 2009-10-22 | 2014-12-17 | Vertex Pharmaceuticals Incorporated | Compositions for treatment of cystic fibrosis and other chronic diseases |
| 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 |
| CN108658876A (zh) | 2012-12-17 | 2018-10-16 | 帕里昂科学公司 | 3,5-二氨基-6-氯-n-(n-(4-苯基丁基)甲脒基)吡嗪-2-甲酰胺化合物 |
| CN105073717B (zh) | 2012-12-17 | 2018-05-22 | 帕里昂科学公司 | 可用于治疗由黏膜水化不足造成的疾病的氯-吡嗪甲酰胺衍生物 |
| US9102633B2 (en) | 2013-12-13 | 2015-08-11 | Parion Sciences, Inc. | Arylalkyl- and aryloxyalkyl-substituted epithelial sodium channel blocking compounds |
| WO2025133218A1 (en) * | 2023-12-21 | 2025-06-26 | Phamri Norden Ab | Pyrazine derivatives for the treatment of skin disorders |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL299931A (enExample) * | 1962-10-30 | |||
| NL6409714A (enExample) * | 1962-10-30 | 1965-10-01 | ||
| US3328404A (en) * | 1966-08-25 | 1967-06-27 | Merck & Co Inc | Derivatives of pyrazine |
| US3432502A (en) * | 1966-08-25 | 1969-03-11 | Merck & Co Inc | Preparation of pyrazinoylguanidine and pyrazinamidoguanidine products |
| NL6707564A (enExample) * | 1966-08-25 | 1968-02-26 | ||
| US4087526A (en) * | 1976-07-23 | 1978-05-02 | Merck & Co., Inc. | (3-Amino-5-substituted-6-fluoropyrazinoyl or pyrazamido)-guanidines and their derivatives bearing substituents on the guanidino nitrogens |
-
1979
- 1979-03-27 US US06/024,293 patent/US4246406A/en not_active Expired - Lifetime
-
1980
- 1980-03-18 AU AU56536/80A patent/AU533298B2/en not_active Ceased
- 1980-03-25 ZA ZA00801770A patent/ZA801770B/xx unknown
- 1980-03-25 IE IE608/80A patent/IE49578B1/en unknown
- 1980-03-26 AT AT80101589T patent/ATE2323T1/de not_active IP Right Cessation
- 1980-03-26 EP EP80101589A patent/EP0017152B1/en not_active Expired
- 1980-03-26 DE DE8080101589T patent/DE3061733D1/de not_active Expired
- 1980-03-26 NO NO800878A patent/NO152560C/no unknown
- 1980-03-26 DK DK129180A patent/DK129180A/da not_active IP Right Cessation
- 1980-03-27 JP JP8038319A patent/JPS55130965A/ja active Pending
-
1981
- 1981-03-18 JP JP3804081A patent/JPS56158771A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE3061733D1 (en) | 1983-03-03 |
| ZA801770B (en) | 1981-11-25 |
| NO152560B (no) | 1985-07-08 |
| IE800608L (en) | 1980-09-27 |
| JPS56158771A (en) | 1981-12-07 |
| NO152560C (no) | 1985-10-16 |
| EP0017152A1 (en) | 1980-10-15 |
| NO800878L (no) | 1980-09-29 |
| AU5653680A (en) | 1980-10-02 |
| AU533298B2 (en) | 1983-11-17 |
| ATE2323T1 (de) | 1983-02-15 |
| JPS55130965A (enExample) | 1980-10-11 |
| DK129180A (da) | 1980-09-28 |
| EP0017152B1 (en) | 1983-01-26 |
| US4246406A (en) | 1981-01-20 |
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