DE3022302C2 - 3-Amino-5-(4-pyridyl)-1,2,4-triazole und diese enthaltende Arzneimittel - Google Patents
3-Amino-5-(4-pyridyl)-1,2,4-triazole und diese enthaltende ArzneimittelInfo
- Publication number
- DE3022302C2 DE3022302C2 DE3022302A DE3022302A DE3022302C2 DE 3022302 C2 DE3022302 C2 DE 3022302C2 DE 3022302 A DE3022302 A DE 3022302A DE 3022302 A DE3022302 A DE 3022302A DE 3022302 C2 DE3022302 C2 DE 3022302C2
- Authority
- DE
- Germany
- Prior art keywords
- amino
- reaction
- pure
- pyridyl
- mixture
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 239000003814 drug Substances 0.000 title description 4
- PHYOJNNPPUPKEA-UHFFFAOYSA-N 5-pyridin-4-yl-1h-1,2,4-triazol-3-amine Chemical class NC1=NNC(C=2C=CN=CC=2)=N1 PHYOJNNPPUPKEA-UHFFFAOYSA-N 0.000 title description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 114
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 108
- 238000006243 chemical reaction Methods 0.000 description 57
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 50
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- 239000000203 mixture Substances 0.000 description 36
- -1 amino, N-monobenzylamino Chemical group 0.000 description 31
- 239000007787 solid Substances 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 238000005481 NMR spectroscopy Methods 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 25
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
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- 239000011541 reaction mixture Substances 0.000 description 20
- 238000000034 method Methods 0.000 description 18
- 150000001875 compounds Chemical class 0.000 description 17
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 17
- 239000007795 chemical reaction product Substances 0.000 description 16
- 235000011121 sodium hydroxide Nutrition 0.000 description 16
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- 239000012467 final product Substances 0.000 description 14
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- 239000002904 solvent Substances 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 9
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000012299 nitrogen atmosphere Substances 0.000 description 3
- ANRIQLNBZQLTFV-DZUOILHNSA-N pentagastrin Chemical compound C([C@H](NC(=O)[C@H](CC(O)=O)NC(=O)[C@@H](NC(=O)[C@H](CC=1[C]2C=CC=CC2=NC=1)NC(=O)CCNC(=O)OC(C)(C)C)CCSC)C(N)=O)C1=CC=CC=C1 ANRIQLNBZQLTFV-DZUOILHNSA-N 0.000 description 3
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- PEFSXVDJORRUCT-UHFFFAOYSA-N 2-(2,2,2-trifluoroethylamino)pyridine-4-carbohydrazide Chemical compound NNC(=O)C1=CC=NC(NCC(F)(F)F)=C1 PEFSXVDJORRUCT-UHFFFAOYSA-N 0.000 description 2
- GABHVXUZWQTOHL-UHFFFAOYSA-N 2-(ethylamino)pyridine-4-carbohydrazide Chemical compound CCNC1=CC(C(=O)NN)=CC=N1 GABHVXUZWQTOHL-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
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- LJSSPQRYKZTFBZ-UHFFFAOYSA-N 4-(3-amino-1h-1,2,4-triazol-5-yl)-n,n-dimethylpyridin-2-amine Chemical compound C1=NC(N(C)C)=CC(C=2NN=C(N)N=2)=C1 LJSSPQRYKZTFBZ-UHFFFAOYSA-N 0.000 description 2
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- SSBRSHIQIANGKS-UHFFFAOYSA-N [amino(hydroxy)methylidene]azanium;hydrogen sulfate Chemical compound NC(N)=O.OS(O)(=O)=O SSBRSHIQIANGKS-UHFFFAOYSA-N 0.000 description 1
- UDUMWDDMSHXGGQ-UHFFFAOYSA-N [amino(methylsulfanyl)methylidene]-methylazanium;iodide Chemical compound I.CSC(N)=NC UDUMWDDMSHXGGQ-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000000783 alginic acid Substances 0.000 description 1
- 235000010443 alginic acid Nutrition 0.000 description 1
- 229920000615 alginic acid Polymers 0.000 description 1
- 229960001126 alginic acid Drugs 0.000 description 1
- 150000004781 alginic acids Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical class NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 230000001458 anti-acid effect Effects 0.000 description 1
- 230000003712 anti-aging effect Effects 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000003637 basic solution Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002026 chloroform extract Substances 0.000 description 1
- 239000012230 colorless oil Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- ZZTURJAZCMUWEP-UHFFFAOYSA-N diaminomethylideneazanium;hydrogen sulfate Chemical compound NC(N)=N.OS(O)(=O)=O ZZTURJAZCMUWEP-UHFFFAOYSA-N 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 238000004455 differential thermal analysis Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 238000001647 drug administration Methods 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-M ethanesulfonate Chemical compound CCS([O-])(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-M 0.000 description 1
- UTUNZTDXEIGXKD-UHFFFAOYSA-N ethoxyethane;sulfuric acid Chemical compound CCOCC.OS(O)(=O)=O UTUNZTDXEIGXKD-UHFFFAOYSA-N 0.000 description 1
- LIWAQLJGPBVORC-UHFFFAOYSA-N ethylmethylamine Chemical compound CCNC LIWAQLJGPBVORC-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 230000004927 fusion Effects 0.000 description 1
- 230000027119 gastric acid secretion Effects 0.000 description 1
- 201000005917 gastric ulcer Diseases 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000001990 intravenous administration Methods 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 229940126601 medicinal product Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000008177 pharmaceutical agent Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000006798 ring closing metathesis reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 210000003462 vein Anatomy 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/79—Acids; Esters
-
- 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
- A61P1/04—Drugs for disorders of the alimentary tract or the digestive system for ulcers, gastritis or reflux esophagitis, e.g. antacids, inhibitors of acid secretion, mucosal protectants
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Pharmacology & Pharmacy (AREA)
- Bioinformatics & Cheminformatics (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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/049,737 US4276297A (en) | 1979-06-18 | 1979-06-18 | Pyridylaminotriazole therapeutic agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE3022302A1 DE3022302A1 (de) | 1981-01-08 |
| DE3022302C2 true DE3022302C2 (de) | 1984-03-01 |
Family
ID=21961428
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE3022302A Expired DE3022302C2 (de) | 1979-06-18 | 1980-06-13 | 3-Amino-5-(4-pyridyl)-1,2,4-triazole und diese enthaltende Arzneimittel |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4276297A (enExample) |
| JP (1) | JPS565477A (enExample) |
| KR (2) | KR840002173B1 (enExample) |
| AR (2) | AR225766A1 (enExample) |
| AT (2) | AT375655B (enExample) |
| BE (1) | BE883859A (enExample) |
| CA (1) | CA1140133A (enExample) |
| CH (1) | CH644375A5 (enExample) |
| DE (1) | DE3022302C2 (enExample) |
| DK (1) | DK258180A (enExample) |
| ES (2) | ES492522A0 (enExample) |
| FI (1) | FI69842C (enExample) |
| FR (1) | FR2459241A1 (enExample) |
| GB (1) | GB2053910B (enExample) |
| GR (1) | GR68731B (enExample) |
| IE (1) | IE49913B1 (enExample) |
| IL (1) | IL60332A (enExample) |
| IT (1) | IT1140993B (enExample) |
| LU (1) | LU82527A1 (enExample) |
| NL (1) | NL182641C (enExample) |
| PH (1) | PH16875A (enExample) |
| PT (1) | PT71399A (enExample) |
| SE (1) | SE441745B (enExample) |
| YU (2) | YU41717B (enExample) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AR230994A1 (es) * | 1981-08-31 | 1984-08-31 | Pfizer | Procedimiento para preparar compuesto de 3'-substituido-5'-(2-amino-4-piridil)-1',2',4'-triazol |
| JP2518515Y2 (ja) * | 1993-09-22 | 1996-11-27 | 茂郎 槇島 | 水虫用医療包帯 |
| PL415073A1 (pl) * | 2014-12-19 | 2016-06-20 | Oncoarendi Therapeutics Spółka Z Ograniczoną Odpowiedzialnością | Podstawione aminotriazole przydatne jako inhibitory kwaśnej chitynazy ssaków |
| WO2022034121A1 (en) | 2020-08-11 | 2022-02-17 | Université De Strasbourg | H2 blockers targeting liver macrophages for the prevention and treatment of liver disease and cancer |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1925654U (de) | 1965-07-23 | 1965-10-21 | Alfons Mann | Zusatzeinrichtung fuer vergaser an benzinmotoren zur steigerung der motorenleistung. |
| CH521419A (de) * | 1968-03-01 | 1972-04-15 | Ciba Geigy Ag | Verfahren zur Herstellung neuer Azofarbstoffe |
| GB1264798A (enExample) | 1968-07-10 | 1972-02-23 | ||
| US3647814A (en) * | 1969-07-03 | 1972-03-07 | Rohm & Haas | Method for preparing 4-substituted-1 2 4-triazoles |
| NL7112373A (enExample) * | 1970-09-25 | 1972-03-28 | ||
| NL7112372A (enExample) * | 1970-09-25 | 1972-03-28 | ||
| GB1403866A (en) * | 1971-12-06 | 1975-08-28 | Wyeth John & Brother Ltd | Derivatives of 3-amino-1,2,4-triazoles |
| US3879404A (en) * | 1972-07-07 | 1975-04-22 | John J Baldwin | Certain 5-(pyridyl)-3(phenyl)-1,2,4-triazoles |
| US3873563A (en) * | 1972-09-29 | 1975-03-25 | Sakai Chemical Industry Co | Method for manufacturing 4-amino-1,2,4-triazoles |
| US3928361A (en) * | 1973-05-21 | 1975-12-23 | Merck & Co Inc | 1-(Sulfamoylphenylalkyl)-3,5-dipyridyl-1,2,4 triazoles |
| US3984558A (en) * | 1973-05-21 | 1976-10-05 | Merck & Co., Inc. | 1,3,5-Trisubstituted-1,2,4-triazole compounds used as bronchodilators |
-
1979
- 1979-06-18 US US06/049,737 patent/US4276297A/en not_active Expired - Lifetime
-
1980
- 1980-06-06 CH CH440280A patent/CH644375A5/fr not_active IP Right Cessation
- 1980-06-06 AR AR281310A patent/AR225766A1/es active
- 1980-06-12 GR GR62187A patent/GR68731B/el unknown
- 1980-06-13 DE DE3022302A patent/DE3022302C2/de not_active Expired
- 1980-06-16 JP JP8126680A patent/JPS565477A/ja active Granted
- 1980-06-16 CA CA000354112A patent/CA1140133A/en not_active Expired
- 1980-06-16 PT PT71399A patent/PT71399A/pt unknown
- 1980-06-16 LU LU82527A patent/LU82527A1/fr unknown
- 1980-06-16 FI FI801929A patent/FI69842C/fi not_active IP Right Cessation
- 1980-06-16 PH PH24137A patent/PH16875A/en unknown
- 1980-06-16 YU YU1587/80A patent/YU41717B/xx unknown
- 1980-06-17 DK DK258180A patent/DK258180A/da not_active Application Discontinuation
- 1980-06-17 BE BE0/201060A patent/BE883859A/fr not_active IP Right Cessation
- 1980-06-17 FR FR8013401A patent/FR2459241A1/fr active Granted
- 1980-06-17 SE SE8004498A patent/SE441745B/sv not_active IP Right Cessation
- 1980-06-17 AT AT0319280A patent/AT375655B/de not_active IP Right Cessation
- 1980-06-17 KR KR1019800002385A patent/KR840002173B1/ko not_active Expired
- 1980-06-17 GB GB8019674A patent/GB2053910B/en not_active Expired
- 1980-06-17 IL IL60332A patent/IL60332A/xx unknown
- 1980-06-17 IE IE1250/80A patent/IE49913B1/en unknown
- 1980-06-17 NL NLAANVRAGE8003496,A patent/NL182641C/xx not_active IP Right Cessation
- 1980-06-17 ES ES492522A patent/ES492522A0/es active Granted
- 1980-06-17 IT IT22825/80A patent/IT1140993B/it active
-
1981
- 1981-01-26 ES ES498821A patent/ES8201155A1/es not_active Expired
- 1981-08-04 AR AR286650A patent/AR227436A1/es active
-
1982
- 1982-11-24 YU YU2633/82A patent/YU41536B/xx unknown
-
1983
- 1983-08-29 AT AT0307583A patent/AT375656B/de not_active IP Right Cessation
-
1984
- 1984-04-30 KR KR1019840002324A patent/KR840002172B1/ko not_active Expired
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| OAP | Request for examination filed | ||
| OD | Request for examination | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |