CH636615A5 - Pharmaceutically effective, optionally substituted imidazo(1,5-d)-as-triazin-4-(3H)-ones and -thiones - Google Patents
Pharmaceutically effective, optionally substituted imidazo(1,5-d)-as-triazin-4-(3H)-ones and -thiones Download PDFInfo
- Publication number
- CH636615A5 CH636615A5 CH114578A CH114578A CH636615A5 CH 636615 A5 CH636615 A5 CH 636615A5 CH 114578 A CH114578 A CH 114578A CH 114578 A CH114578 A CH 114578A CH 636615 A5 CH636615 A5 CH 636615A5
- Authority
- CH
- Switzerland
- Prior art keywords
- methyl
- phenyl
- carbon atoms
- imidazo
- group
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 claims description 87
- -1 o-propoxyphenyl group Chemical group 0.000 claims description 66
- 238000002360 preparation method Methods 0.000 claims description 65
- 238000000034 method Methods 0.000 claims description 58
- 125000004432 carbon atom Chemical group C* 0.000 claims description 28
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 26
- 239000001257 hydrogen Substances 0.000 claims description 23
- 229910052739 hydrogen Inorganic materials 0.000 claims description 23
- 102000004861 Phosphoric Diester Hydrolases Human genes 0.000 claims description 20
- 108090001050 Phosphoric Diester Hydrolases Proteins 0.000 claims description 20
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 239000002904 solvent Substances 0.000 claims description 17
- 239000000460 chlorine Substances 0.000 claims description 15
- 150000002431 hydrogen Chemical group 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 14
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 14
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
- 238000009835 boiling Methods 0.000 claims description 13
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 11
- 230000008569 process Effects 0.000 claims description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 10
- 239000001301 oxygen Substances 0.000 claims description 10
- 229910052760 oxygen Inorganic materials 0.000 claims description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 8
- 239000007858 starting material Substances 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- ZQEXIXXJFSQPNA-UHFFFAOYSA-N 1h-imidazole-5-carbaldehyde Chemical compound O=CC1=CNC=N1 ZQEXIXXJFSQPNA-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 229910052740 iodine Inorganic materials 0.000 claims description 5
- 230000001225 therapeutic effect Effects 0.000 claims description 5
- 239000012442 inert solvent Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- KGJOHYXBJQXCCC-UHFFFAOYSA-N 8-chloro-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Cl)N=C2C1=CC=CC=C1 KGJOHYXBJQXCCC-UHFFFAOYSA-N 0.000 claims description 3
- 241000124008 Mammalia Species 0.000 claims description 3
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- 239000011630 iodine Substances 0.000 claims description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 claims description 3
- CYQAYERJWZKYML-UHFFFAOYSA-N phosphorus pentasulfide Chemical compound S1P(S2)(=S)SP3(=S)SP1(=S)SP2(=S)S3 CYQAYERJWZKYML-UHFFFAOYSA-N 0.000 claims description 3
- 125000001424 substituent group Chemical class 0.000 claims description 3
- MBPOEUWFBVJHPT-UHFFFAOYSA-N 6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound N12C(=O)NN=CC2=CN=C1C1=CC=CC=C1 MBPOEUWFBVJHPT-UHFFFAOYSA-N 0.000 claims description 2
- MOWCUJJAWXTYQL-UHFFFAOYSA-N 8-iodo-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(I)N=C2C1=CC=CC=C1 MOWCUJJAWXTYQL-UHFFFAOYSA-N 0.000 claims description 2
- OUYFNJMMIHHXCE-UHFFFAOYSA-N 8-methyl-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(C)N=C2C1=CC=CC=C1 OUYFNJMMIHHXCE-UHFFFAOYSA-N 0.000 claims description 2
- GKBLFYRYGLVWNL-UHFFFAOYSA-N 8-methyl-6-propyl-3h-imidazo[1,5-d][1,2,4]triazine-4-thione Chemical compound C1=NNC(=S)N2C(CCC)=NC(C)=C21 GKBLFYRYGLVWNL-UHFFFAOYSA-N 0.000 claims description 2
- 239000003937 drug carrier Substances 0.000 claims description 2
- 238000006798 ring closing metathesis reaction Methods 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 3
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims 2
- 229910052736 halogen Inorganic materials 0.000 claims 2
- 150000002367 halogens Chemical class 0.000 claims 2
- 125000001624 naphthyl group Chemical group 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- CCUKYVFHEMANRO-UHFFFAOYSA-N 6-cyclohexyl-8-methyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(C)N=C2C1CCCCC1 CCUKYVFHEMANRO-UHFFFAOYSA-N 0.000 claims 1
- GPQDFZOLGWYHJU-UHFFFAOYSA-N 8-bromo-6-phenyl-3h-imidazo[1,5-d][1,2,4]triazin-4-one Chemical compound C1=NNC(=O)N2C1=C(Br)N=C2C1=CC=CC=C1 GPQDFZOLGWYHJU-UHFFFAOYSA-N 0.000 claims 1
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical class [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims 1
- VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 claims 1
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- 238000002844 melting Methods 0.000 description 25
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- PJCOTVYIUUFDEI-UHFFFAOYSA-N methyl N-[(5-methyl-2-phenyl-1H-imidazol-4-yl)methylideneamino]carbamodithioate Chemical compound N1C(C)=C(C=NNC(=S)SC)N=C1C1=CC=CC=C1 PJCOTVYIUUFDEI-UHFFFAOYSA-N 0.000 description 1
- DXZGYFBHHFRAGR-UHFFFAOYSA-N methyl N-[(5-methyl-2-propyl-1H-imidazol-4-yl)methylideneamino]carbamodithioate Chemical compound CCCC1=NC(C=NNC(=S)SC)=C(C)N1 DXZGYFBHHFRAGR-UHFFFAOYSA-N 0.000 description 1
- MBXNQZHITVCSLJ-UHFFFAOYSA-N methyl fluorosulfonate Chemical compound COS(F)(=O)=O MBXNQZHITVCSLJ-UHFFFAOYSA-N 0.000 description 1
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 description 1
- GYNNXHKOJHMOHS-UHFFFAOYSA-N methyl-cycloheptane Natural products CC1CCCCCC1 GYNNXHKOJHMOHS-UHFFFAOYSA-N 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 210000003205 muscle Anatomy 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 210000003739 neck Anatomy 0.000 description 1
- 108010028584 nucleotidase Proteins 0.000 description 1
- 239000002773 nucleotide Substances 0.000 description 1
- 125000003729 nucleotide group Chemical group 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- SUSQOBVLVYHIEX-UHFFFAOYSA-N phenylacetonitrile Chemical compound N#CCC1=CC=CC=C1 SUSQOBVLVYHIEX-UHFFFAOYSA-N 0.000 description 1
- 229940075930 picrate Drugs 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-M picrate anion Chemical compound [O-]C1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-M 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- JAMNHZBIQDNHMM-UHFFFAOYSA-N pivalonitrile Chemical compound CC(C)(C)C#N JAMNHZBIQDNHMM-UHFFFAOYSA-N 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000011736 potassium bicarbonate Substances 0.000 description 1
- 229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
- 235000015497 potassium bicarbonate Nutrition 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229920001592 potato starch Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002335 preservative effect Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 230000002285 radioactive effect Effects 0.000 description 1
- 239000001044 red dye Substances 0.000 description 1
- 238000007670 refining Methods 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- XWGJFPHUCFXLBL-UHFFFAOYSA-M rongalite Chemical compound [Na+].OCS([O-])=O XWGJFPHUCFXLBL-UHFFFAOYSA-M 0.000 description 1
- 229960000581 salicylamide Drugs 0.000 description 1
- 238000003345 scintillation counting Methods 0.000 description 1
- 150000003333 secondary alcohols Chemical class 0.000 description 1
- 239000004208 shellac Substances 0.000 description 1
- ZLGIYFNHBLSMPS-ATJNOEHPSA-N shellac Chemical compound OCCCCCC(O)C(O)CCCCCCCC(O)=O.C1C23[C@H](C(O)=O)CCC2[C@](C)(CO)[C@@H]1C(C(O)=O)=C[C@@H]3O ZLGIYFNHBLSMPS-ATJNOEHPSA-N 0.000 description 1
- 229940113147 shellac Drugs 0.000 description 1
- 235000013874 shellac Nutrition 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 239000003998 snake venom Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- BEOOHQFXGBMRKU-UHFFFAOYSA-N sodium cyanoborohydride Chemical compound [Na+].[B-]C#N BEOOHQFXGBMRKU-UHFFFAOYSA-N 0.000 description 1
- HRZFUMHJMZEROT-UHFFFAOYSA-L sodium disulfite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])(=O)=O HRZFUMHJMZEROT-UHFFFAOYSA-L 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 229940001584 sodium metabisulfite Drugs 0.000 description 1
- 235000010262 sodium metabisulphite Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 238000000527 sonication Methods 0.000 description 1
- 238000011699 spontaneously hypertensive rat Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 239000011550 stock solution Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- RTKIYNMVFMVABJ-UHFFFAOYSA-L thimerosal Chemical compound [Na+].CC[Hg]SC1=CC=CC=C1C([O-])=O RTKIYNMVFMVABJ-UHFFFAOYSA-L 0.000 description 1
- 229940033663 thimerosal Drugs 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000012773 waffles Nutrition 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
Classifications
-
- 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
- C07D233/64—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 substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- 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
- A61P9/12—Antihypertensives
-
- 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
- C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D233/28—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D233/30—Oxygen or sulfur atoms
- C07D233/40—Two or more oxygen 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
- C07D233/66—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 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
- C07D233/68—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Life Sciences & Earth Sciences (AREA)
- Cardiology (AREA)
- Heart & Thoracic Surgery (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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US76531777A | 1977-02-03 | 1977-02-03 | |
| US76531877A | 1977-02-03 | 1977-02-03 | |
| US84317377A | 1977-10-18 | 1977-10-18 | |
| US05/843,174 US4107307A (en) | 1977-02-03 | 1977-10-18 | Imidazo [1,5-d]-as-triazine-4(3H)-ones and thiones |
| US05/848,836 US4124766A (en) | 1977-02-03 | 1977-11-07 | Substituted 3-(4-imidazolylmethylene)carbazic and thiocarbazic acid esters |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH636615A5 true CH636615A5 (en) | 1983-06-15 |
Family
ID=27542181
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH114578A CH636615A5 (en) | 1977-02-03 | 1978-02-02 | Pharmaceutically effective, optionally substituted imidazo(1,5-d)-as-triazin-4-(3H)-ones and -thiones |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS596316B2 (da) |
| AR (1) | AR224613A1 (da) |
| BE (1) | BE863567A (da) |
| CA (1) | CA1097638A (da) |
| CH (1) | CH636615A5 (da) |
| DE (1) | DE2804435A1 (da) |
| DK (1) | DK48778A (da) |
| FR (1) | FR2384772A1 (da) |
| GB (1) | GB1597671A (da) |
| GR (1) | GR73810B (da) |
| IE (1) | IE46511B1 (da) |
| IL (1) | IL53783A (da) |
| NL (1) | NL7801230A (da) |
| SE (1) | SE7801270L (da) |
| YU (1) | YU22078A (da) |
Families Citing this family (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3212749A1 (de) * | 1982-04-06 | 1983-10-13 | Basf Ag, 6700 Ludwigshafen | Neue 5-substituierte 4-methylimidazole und verfahren zu ihrer herstellung |
| DE3302413A1 (de) * | 1983-01-21 | 1984-07-26 | Schering AG, 1000 Berlin und 4709 Bergkamen | Triazinone, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit selektiver herbizider wirkung |
| JPS6337712A (ja) * | 1986-08-01 | 1988-02-18 | Hitachi Ltd | 電界効果トランジスタの保護回路 |
| JPH02185069A (ja) * | 1988-12-02 | 1990-07-19 | Motorola Inc | 高エネルギー阻止能力及び温度補償された阻止電圧を具備する半導体デバイス |
| RU2103262C1 (ru) * | 1992-07-16 | 1998-01-27 | Лонца АГ Гампель/Валлис | Способ получения 2-замещенных 5-хлоримидазол-4-карбальдегидов |
| US5484939A (en) * | 1993-03-12 | 1996-01-16 | Lonza Ltd. | 2-substituted 5-chlorimidazoles |
| US5442075A (en) * | 1993-03-12 | 1995-08-15 | Lonza Ltd. | Process for the production of 2-substituted 5-chlorimidazole-4-carbaldehydes |
| ATE157655T1 (de) * | 1993-03-12 | 1997-09-15 | Lonza Ag | Verfahren zur herstellung von gegebenfalls 2- substituierten 5-chlorimidazolen |
| CA2135541C (en) * | 1993-11-15 | 2006-01-10 | Gareth Griffiths | Process for the preparation of 2-substituted 5-chloroimidazole-4-carbaldehydes |
| CA2175420C (en) * | 1995-05-17 | 2007-04-10 | Gareth Griffiths | Process for the preparation of optionally 2-substituted 5-chloroimidazole-4-carbaldehydes |
| JP4103149B2 (ja) | 1996-01-05 | 2008-06-18 | ロンザ リミテッド | ２−置換５−クロロイミダゾール−４−カルブアルデヒドの製造方法 |
| FR2842809A1 (fr) * | 2002-07-26 | 2004-01-30 | Greenpharma Sas | NOUVELLES PYRAZOLO[1,5-a]-1,3,5-TRIAZINES SUBSTITUEES ET LEURS ANALOGUES, COMPOSITIONS PHARMACEUTIQUES LES CONTENANT, UTILISATION A TITRE DE MEDICAMENT ET PROCEDES POUR LEUR PREPARATION |
-
1978
- 1978-01-11 IL IL53783A patent/IL53783A/xx unknown
- 1978-01-13 GR GR55160A patent/GR73810B/el unknown
- 1978-01-16 GB GB1728/78A patent/GB1597671A/en not_active Expired
- 1978-01-23 AR AR270809A patent/AR224613A1/es active
- 1978-01-31 IE IE208/78A patent/IE46511B1/en unknown
- 1978-01-31 YU YU00220/78A patent/YU22078A/xx unknown
- 1978-02-02 DE DE19782804435 patent/DE2804435A1/de not_active Withdrawn
- 1978-02-02 NL NL7801230A patent/NL7801230A/xx not_active Application Discontinuation
- 1978-02-02 BE BE184833A patent/BE863567A/xx not_active IP Right Cessation
- 1978-02-02 CH CH114578A patent/CH636615A5/de not_active IP Right Cessation
- 1978-02-02 DK DK48778A patent/DK48778A/da not_active Application Discontinuation
- 1978-02-02 CA CA296,027A patent/CA1097638A/en not_active Expired
- 1978-02-02 SE SE7801270A patent/SE7801270L/xx unknown
- 1978-02-03 FR FR7803141A patent/FR2384772A1/fr not_active Withdrawn
- 1978-02-03 JP JP53010649A patent/JPS596316B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| FR2384772A1 (fr) | 1978-10-20 |
| DK48778A (da) | 1978-08-04 |
| YU22078A (en) | 1983-12-31 |
| IL53783A (en) | 1982-08-31 |
| CA1097638A (en) | 1981-03-17 |
| GR73810B (da) | 1984-04-17 |
| JPS5398994A (en) | 1978-08-29 |
| IE46511B1 (en) | 1983-07-13 |
| DE2804435A1 (de) | 1978-08-17 |
| BE863567A (fr) | 1978-08-02 |
| SE7801270L (sv) | 1978-09-29 |
| IE780208L (en) | 1978-08-03 |
| NL7801230A (nl) | 1978-08-07 |
| IL53783A0 (en) | 1978-04-30 |
| JPS596316B2 (ja) | 1984-02-10 |
| AR224613A1 (es) | 1981-12-30 |
| GB1597671A (en) | 1981-09-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |