US3920655A - Nitroimidazolyl benzoquinazolines - Google Patents
Nitroimidazolyl benzoquinazolines Download PDFInfo
- Publication number
- US3920655A US3920655A US331114A US33111473A US3920655A US 3920655 A US3920655 A US 3920655A US 331114 A US331114 A US 331114A US 33111473 A US33111473 A US 33111473A US 3920655 A US3920655 A US 3920655A
- Authority
- US
- United States
- Prior art keywords
- carbon atoms
- methyl
- imidazolyl
- phenyl
- alkyl
- 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 - Lifetime
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- -1 Nitroimidazolyl benzoquinazolines Chemical class 0.000 title description 12
- 150000001875 compounds Chemical class 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- ZGQVUIAYWZXNJT-UHFFFAOYSA-N 4-methyl-2-(1-methyl-5-nitroimidazol-2-yl)-5,6-dihydrobenzo[h]quinazoline Chemical compound N=1C(C2=CC=CC=C2CC2)=C2C(C)=NC=1C1=NC=C([N+]([O-])=O)N1C ZGQVUIAYWZXNJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 21
- 239000002253 acid Substances 0.000 abstract description 12
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 11
- 125000000217 alkyl group Chemical group 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 5
- 125000005188 oxoalkyl group Chemical group 0.000 abstract description 4
- 230000002963 trichomonacidal effect Effects 0.000 abstract description 4
- UTMABVXKQIDJCX-UHFFFAOYSA-N 2-(1h-imidazol-2-yl)-4-nitropyrimidine Chemical class [O-][N+](=O)C1=CC=NC(C=2NC=CN=2)=N1 UTMABVXKQIDJCX-UHFFFAOYSA-N 0.000 abstract description 3
- 125000002947 alkylene group Chemical group 0.000 abstract description 3
- 150000002148 esters Chemical class 0.000 abstract description 3
- 125000005113 hydroxyalkoxy group Chemical group 0.000 abstract description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 125000002950 monocyclic group Chemical group 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 10
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 9
- 229940073020 nitrol Drugs 0.000 description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 150000001409 amidines Chemical class 0.000 description 5
- 235000019270 ammonium chloride Nutrition 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
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 235000011054 acetic acid Nutrition 0.000 description 4
- VAOCPAMSLUNLGC-UHFFFAOYSA-N metronidazole Chemical compound CC1=NC=C([N+]([O-])=O)N1CCO VAOCPAMSLUNLGC-UHFFFAOYSA-N 0.000 description 4
- 229960000282 metronidazole Drugs 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- VCRDCCUASWNMQJ-UHFFFAOYSA-N 3-(dimethylamino)-2-(2-hydroxyethoxy)prop-2-enal Chemical compound CN(C)C=C(C=O)OCCO VCRDCCUASWNMQJ-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-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
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- YZEUHQHUFTYLPH-UHFFFAOYSA-N 2-nitroimidazole Chemical compound [O-][N+](=O)C1=NC=CN1 YZEUHQHUFTYLPH-UHFFFAOYSA-N 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 241000224527 Trichomonas vaginalis Species 0.000 description 2
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical compound CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 150000003863 ammonium salts Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 150000007522 mineralic acids Chemical class 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- GQXZMGLLNZTTNN-UHFFFAOYSA-N 2-(5-nitro-1h-imidazol-2-yl)pyrimidine Chemical class N1C([N+](=O)[O-])=CN=C1C1=NC=CC=N1 GQXZMGLLNZTTNN-UHFFFAOYSA-N 0.000 description 1
- QLFJZNGJGFHEQV-UHFFFAOYSA-N 2-[2-(1-methyl-5-nitroimidazol-2-yl)pyrimidin-5-yl]oxyethanol;hydrochloride Chemical compound Cl.CN1C([N+]([O-])=O)=CN=C1C1=NC=C(OCCO)C=N1 QLFJZNGJGFHEQV-UHFFFAOYSA-N 0.000 description 1
- 150000004959 2-nitroimidazoles Chemical class 0.000 description 1
- RQZJIXZNJBCGQC-UHFFFAOYSA-N 3-acetylheptane-2,6-dione Chemical compound CC(=O)CCC(C(C)=O)C(C)=O RQZJIXZNJBCGQC-UHFFFAOYSA-N 0.000 description 1
- QOXOZONBQWIKDA-UHFFFAOYSA-N 3-hydroxypropyl Chemical group [CH2]CCO QOXOZONBQWIKDA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 description 1
- 229930194542 Keto Natural products 0.000 description 1
- WSMYVTOQOOLQHP-UHFFFAOYSA-N Malondialdehyde Chemical compound O=CCC=O WSMYVTOQOOLQHP-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 1
- 241001502500 Trichomonadida Species 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical class [H]C([H])([H])C(*)=O 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000004423 acyloxy group Chemical group 0.000 description 1
- 229940040526 anhydrous sodium acetate Drugs 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 229940088710 antibiotic agent Drugs 0.000 description 1
- 239000004599 antimicrobial Substances 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000002512 chemotherapy Methods 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000008298 dragée Substances 0.000 description 1
- 150000002081 enamines Chemical class 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000004957 nitroimidazoles Chemical class 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000006187 pill Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 238000000746 purification Methods 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
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- the compounds of this invention are nitroimidazolyl pyrimidines of the general Formula I N N II II 0211 I I and physiologically acceptable salts thereof, wherein X is alkyl of 1-4 carbon atoms, R and R which can be alike or different, are a hydrogen atom, alkyl of one to four carbon atoms, phenyl, trifluoromethyl or a thienyl group, and R is a hydrogen atom, alkyl of 1-4 carbon atoms, hydroxyalkoxy of 2-4 carbon atoms, which can be esterified by alkanoic acid of l-4 carbon atoms, i.e., alkanoyloxyalkoxy, oxoalkyl, i.e., keto substituted alkyl, containing a total of 3-6 carbon atoms, or when R;
- R is phenyl, an alkylene having l-2 carbon atoms in the chain joined to the 2-position of the phenyl ring.
- alkyl of 1-4 carbon atoms are methyl, ethyl, n-propyl, isobutyl, etc., preferably methyl.
- hydroxyalkoxy and esters thereof of an alkanoic acid are hydroxyethyl, 2-hydroxypropyl, 3- hydroxypropyl, acetoxyethyl, propionyloxyethyl and 3-acetoxypropy1.
- oxoalkyl examples include acetylmethyl, acetylethyl and propionylmethyl.
- physiologically acceptable acids which can be employed to form the acid addition of salts of this invention are inorganic acids, e.g., hydrochloric acid, sulfuric acid, etc., and organic mono-, diand tricarboxylic acids, e.g., acetic acid, propionic acid, lactic acid, citric acid, benzoic acid, succinic acid, heptagluconic acid, etc.
- inorganic acids e.g., hydrochloric acid, sulfuric acid, etc.
- organic mono-, diand tricarboxylic acids e.g., acetic acid, propionic acid, lactic acid, citric acid, benzoic acid, succinic acid, heptagluconic acid, etc.
- the exact nature of the acid is not critical, so long as it forms a physiologically acceptable acid addition salt.
- novel compounds of this invention can be produced in a conventional manner, for example, by reacting an amidine of the general Formula II N NH 1 l -c 11 OZN N wherein X has the values given above, or a salt thereof, preferably the hydrochloride.
- R R and R have the values given above, or a reactive functional derivative thereof, and subsequently saponifying any acyloxy groups present in' the condensation product to hydroxy groups, or esterifying free hydroxy groups, and optionally converting the compounds into the salts thereof with inorganic or organic acids.
- Suitable derivatives of the dicarbonyl compound are reactive derivatives such as, for example, the acetal or, if R and R both are H, an enamine.
- reaction of the amidine (II) and/or the salt thereof, the latter optionally mixed with ammonium chloride, with the B-dicarbonyl compounds or the derivatives thereof can be effected in the absence or in the presence of a solvent, e.g., acetic acid, acetic anhydride, dimethylformamide, alcohol, to which can be Minimum inhibitory Concentration Against Trichomonas Vaginalis Compound g/ml.)
- a solvent e.g., acetic acid, acetic anhydride, dimethylformamide, alcohol
- Thenovel compounds can be administered topically or systemically in the pharmaceutically customary forms of application, such as pills, dragees, capsules,
- PREPARATION 9.9 g. (50 millimoles) of the ethyl ester of S-nitro-lmethyl-2-imidazolyl-iminocarboxylic acid and 2.7 g. (50 millimoles) of pulverized ammonium chloride are boiled for 72 hours in methanol. After evaporation of the solvent, the residue is digested in the hot state with 100 ml. of ethyl acetate; yield: 6.1 g. (47% of theory) of an equimolar mixture of 5-nitro-l-methyl-2-imidazolylcarboxamidinium chloride and ammonium chloride; m.p. 225-227 C.
- EXAMPLE 1 4,6-Dimethyl-2-( 5 -nitrol -methyl-2-imidazolyl pyrimidine 0.52 g. (2 millimoles) of an equimolar mixture of 5- nitro-l -methyl-2-imidazolyl-carboxamidinium chloride and ammonium chloride, 0.21 g. (2.1 millilmoles) of acetylacetone, and 0.33 g. of anhydrous sodium acetate are boiled in 4 ml. of acetic acid for 2 hours. Thereafter, the reaction mixture is concentrated to dryness, the residue is triturated with water, and recrystallized from isopropanol. Yield: 0.32 g. (69% of theory), m.p. l48l 50 C.
- EXAMPLE 3 5-( 2-Acetoxyethoxy)-2-( 5-nitrol -methyl-2- imidazolyl )-pyrimidine
- the compound is obtained analogously to Example 1 with 3-dimethylamino-2(2-hydroxyethoxy)-acrolein; in this process, acetic anhydride can also be employed in place of acetic acid.
- acetic anhydride can also be employed in place of acetic acid.
- the residue is mixed with water, the product is extracted with ethyl acetate, and the residue of the ethyl acetate extract is triturated with methanol; m.p. l48l50 C.
- EXAMPLE 5 5-( 2-Hydroxyethoxy)-2-( S-nitrol -methyl-2- imidazolyl)-pyrimidine Hydrochloride 0.78 g. (5 millimoles) of 3-dimethylamino-2-(2- hydroxyethoxy)-acrolein and 1.3 g. (5 millimoles) of an equimolar mixture of S-nitro-l-methyl-2-imidazolylcarboxamidinium chloride and ammonium chloride are added to 5 ml. of 1N sodium methylate solution in methanol. After refluxing for 20 hours, the methanol is distilled off, the residue is maintained at C. for 30 minutes, and mixed with water.
- the product is extracted with ethyl acetate, the ethyl acetate is concentrated, and the residue is digested with isopropanol.
- the thus-obtained free base is converted, with methanolic hydrochloric acid, into the hydrochloride, m.p. l58l60 C.
- the same product is obtained by heating equimolar amounts of S-nitro-l-methyl-Z-imidazolyl-carboxamidine and 3-dimethylamino-2-(2-hydroxyethoxy)- acrolein in dimethylformamide or without solvent and converting the mixture thus obtained optionally after removing the solvent by evaporation into the hydrochloride.
- EXAMPLE 6 5-( 2-Acetoxyethoxy )-2-( S-nitrol -methyl-2- imidazolyl )-pyrimidine 0.29 g. (l millimole) of 5-(2-hydroxyethoxy)-2-(5- nitro-l -methyl-2-imidazolyl)-pyrimidine hydrochloride means of preparative layer chromatography; m.p. 1 C. (from ethyl acetate).
- EXAMPLE 8 4,6-Dimethyl-5-( Z-acetylethyl )-2-( 5-nitrol -methyl-2- imidazolyl )-pyrimidine
- the compound is obtained analogously to Example 7 with 3-acetyl-2,6-heptanedione; m.p. 142 C. (from ethyl acetate).
- EXAMPLE 10 4-Trifluoromethyl-2-( S-nitro- 1 -methyl-2-imidazolyl 6-(2-thienyl)-pyrimidine The compound is obtained in accordance with Example 7 with l-thenoyl-3,3,3-trifluoroacetone. Purification is effected by recrystallization from ethyl acetate; m.p. 188 C.
- EXAMPLE 11 4-Methyl-6-phenyl-2-(S-nitro-1-methyl-2'imidazolyl)- pyrimidine The compound is obtained in analogy to Example 7 with Z-acetylacetophenone. The product is purified by recrystallization from ethyl acetate; m.p. C.
- X is methyl.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/568,117 US3966732A (en) | 1972-02-19 | 1975-04-14 | Nitroimidazolyl pyrimidines |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19722208518 DE2208518A1 (de) | 1972-02-19 | 1972-02-19 | Nitroimidazole |
| DE19722255079 DE2255079A1 (de) | 1972-11-07 | 1972-11-07 | Nitroimidazolylpyrimidine |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US05/568,117 Division US3966732A (en) | 1972-02-19 | 1975-04-14 | Nitroimidazolyl pyrimidines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3920655A true US3920655A (en) | 1975-11-18 |
Family
ID=25762760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US331114A Expired - Lifetime US3920655A (en) | 1972-02-19 | 1973-02-09 | Nitroimidazolyl benzoquinazolines |
Country Status (11)
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055642A (en) * | 1975-05-12 | 1977-10-25 | Sandoz Ltd. | Imidazolyl-2-quinazoline derivatives |
| US4256887A (en) * | 1978-04-06 | 1981-03-17 | Merck & Co., Inc. | 1,2,4-Triazoles and a method for their preparation |
| US4323570A (en) * | 1978-11-15 | 1982-04-06 | Beiersdorf Aktiengesellschaft | Substituted aminopyrimidines |
| US4434167A (en) | 1979-11-07 | 1984-02-28 | Beiersdorf Aktiengesellschaft | Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia |
| US4769378A (en) * | 1986-03-31 | 1988-09-06 | Eli Lilly And Company | Indenopyrimidine aromatase inhibitors |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1920635C3 (de) * | 1969-04-19 | 1979-06-28 | Schering Ag, 1000 Berlin Und 4619 Bergkamen | 2-(l-MethyI-5-nitro-2-imidazolyl)benzimidazole |
| IT1043840B (it) * | 1971-05-08 | 1980-02-29 | Poli Ind Chimica Spa | Pirimidine 2 5 disostituite e processo per la loro preparazione |
-
0
- BE BE795636D patent/BE795636A/xx unknown
-
1972
- 1972-12-27 DD DD167919A patent/DD105226A5/xx unknown
-
1973
- 1973-02-09 US US331114A patent/US3920655A/en not_active Expired - Lifetime
- 1973-02-16 FR FR7305530A patent/FR2183670B1/fr not_active Expired
- 1973-02-16 AT AT141973A patent/AT328455B/de not_active IP Right Cessation
- 1973-02-16 CH CH227973A patent/CH577995A5/xx not_active IP Right Cessation
- 1973-02-19 CA CA164,004A patent/CA974242A/en not_active Expired
- 1973-02-19 GB GB794173A patent/GB1425261A/en not_active Expired
- 1973-02-19 AU AU52334/73A patent/AU5233473A/en not_active Expired
- 1973-02-19 NL NL7302292A patent/NL7302292A/xx not_active Application Discontinuation
- 1973-02-19 JP JP48020097A patent/JPS4886881A/ja active Pending
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4055642A (en) * | 1975-05-12 | 1977-10-25 | Sandoz Ltd. | Imidazolyl-2-quinazoline derivatives |
| US4256887A (en) * | 1978-04-06 | 1981-03-17 | Merck & Co., Inc. | 1,2,4-Triazoles and a method for their preparation |
| US4323570A (en) * | 1978-11-15 | 1982-04-06 | Beiersdorf Aktiengesellschaft | Substituted aminopyrimidines |
| US4434167A (en) | 1979-11-07 | 1984-02-28 | Beiersdorf Aktiengesellschaft | Pyrimidyl thioureas useful for the treatment of hypertension and hyperlipidemia |
| US4769378A (en) * | 1986-03-31 | 1988-09-06 | Eli Lilly And Company | Indenopyrimidine aromatase inhibitors |
Also Published As
| Publication number | Publication date |
|---|---|
| JPS4886881A (enrdf_load_stackoverflow) | 1973-11-15 |
| BE795636A (fr) | 1973-08-20 |
| AU5233473A (en) | 1974-08-22 |
| DD105226A5 (enrdf_load_stackoverflow) | 1974-04-12 |
| GB1425261A (en) | 1976-02-18 |
| FR2183670A1 (enrdf_load_stackoverflow) | 1973-12-21 |
| ATA141973A (de) | 1975-06-15 |
| CA974242A (en) | 1975-09-09 |
| NL7302292A (enrdf_load_stackoverflow) | 1973-08-21 |
| CH577995A5 (enrdf_load_stackoverflow) | 1976-07-30 |
| AT328455B (de) | 1976-03-25 |
| FR2183670B1 (enrdf_load_stackoverflow) | 1975-10-31 |
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