US2472565A - Pyrimido-2'-cyanine dyes - Google Patents
Pyrimido-2'-cyanine dyes Download PDFInfo
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- US2472565A US2472565A US696028A US69602846A US2472565A US 2472565 A US2472565 A US 2472565A US 696028 A US696028 A US 696028A US 69602846 A US69602846 A US 69602846A US 2472565 A US2472565 A US 2472565A
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- United States
- Prior art keywords
- pyrimido
- dimethyl
- chloride
- toluenesulfonate
- cyanine
- 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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- 239000000975 dye Substances 0.000 title description 9
- 150000001875 compounds Chemical class 0.000 description 13
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- FRWYFWZENXDZMU-UHFFFAOYSA-N 2-iodoquinoline Chemical compound C1=CC=CC2=NC(I)=CC=C21 FRWYFWZENXDZMU-UHFFFAOYSA-N 0.000 description 8
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 5
- 150000003839 salts Chemical group 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 229910021607 Silver chloride Inorganic materials 0.000 description 4
- HKZLPVFGJNLROG-UHFFFAOYSA-M silver monochloride Chemical compound [Cl-].[Ag+] HKZLPVFGJNLROG-UHFFFAOYSA-M 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 3
- -1 silver halide Chemical class 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- QGKMIGUHVLGJBR-UHFFFAOYSA-M (4z)-1-(3-methylbutyl)-4-[[1-(3-methylbutyl)quinolin-1-ium-4-yl]methylidene]quinoline;iodide Chemical class [I-].C12=CC=CC=C2N(CCC(C)C)C=CC1=CC1=CC=[N+](CCC(C)C)C2=CC=CC=C12 QGKMIGUHVLGJBR-UHFFFAOYSA-M 0.000 description 2
- PMYUGMDDIBOXQM-UHFFFAOYSA-M 1-ethylquinolin-1-ium;iodide Chemical compound [I-].C1=CC=C2[N+](CC)=CC=CC2=C1 PMYUGMDDIBOXQM-UHFFFAOYSA-M 0.000 description 2
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 2
- TVNUWBFICZWTRU-UHFFFAOYSA-N 4,6-dimethyl-2-phenylpyrimidine Chemical compound CC1=CC(C)=NC(C=2C=CC=CC=2)=N1 TVNUWBFICZWTRU-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KIWBPDUYBMNFTB-UHFFFAOYSA-N Ethyl hydrogen sulfate Chemical compound CCOS(O)(=O)=O KIWBPDUYBMNFTB-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- SRSXLGNVWSONIS-UHFFFAOYSA-M benzenesulfonate Chemical compound [O-]S(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-M 0.000 description 2
- 229940077388 benzenesulfonate Drugs 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 239000003814 drug Substances 0.000 description 2
- 235000019441 ethanol Nutrition 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229910052709 silver Inorganic materials 0.000 description 2
- 239000004332 silver Substances 0.000 description 2
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- 125000000101 thioether group Chemical group 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- 229940086542 triethylamine Drugs 0.000 description 2
- FYANNKHVPUYSDS-UHFFFAOYSA-N 2-butylsulfanylquinoline Chemical compound C1=CC=CC2=NC(SCCCC)=CC=C21 FYANNKHVPUYSDS-UHFFFAOYSA-N 0.000 description 1
- IIFFFBSAXDNJHX-UHFFFAOYSA-N 2-methyl-n,n-bis(2-methylpropyl)propan-1-amine Chemical compound CC(C)CN(CC(C)C)CC(C)C IIFFFBSAXDNJHX-UHFFFAOYSA-N 0.000 description 1
- KJQOUOSLEOQLHV-UHFFFAOYSA-N 2-quinolin-2-ylsulfanyl-1,3-benzothiazole Chemical compound C1=CC=CC2=NC(SC=3SC4=CC=CC=C4N=3)=CC=C21 KJQOUOSLEOQLHV-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 241001465677 Ancylostomatoidea Species 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- COOULFJGBRKEIY-UHFFFAOYSA-M Cl.[Ag]Cl Chemical compound Cl.[Ag]Cl COOULFJGBRKEIY-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-M Thiocyanate anion Chemical compound [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 150000001805 chlorine compounds Chemical group 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VUQUOGPMUUJORT-UHFFFAOYSA-N methyl 4-methylbenzenesulfonate Chemical compound COS(=O)(=O)C1=CC=C(C)C=C1 VUQUOGPMUUJORT-UHFFFAOYSA-N 0.000 description 1
- CZXGXYBOQYQXQD-UHFFFAOYSA-N methyl benzenesulfonate Chemical compound COS(=O)(=O)C1=CC=CC=C1 CZXGXYBOQYQXQD-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 229910001961 silver nitrate Inorganic materials 0.000 description 1
- RHUVFRWZKMEWNS-UHFFFAOYSA-M silver thiocyanate Chemical compound [Ag+].[S-]C#N RHUVFRWZKMEWNS-UHFFFAOYSA-M 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B23/00—Methine or polymethine dyes, e.g. cyanine dyes
- C09B23/02—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups
- C09B23/04—Methine or polymethine dyes, e.g. cyanine dyes the polymethine chain containing an odd number of >CH- or >C[alkyl]- groups one >CH- group, e.g. cyanines, isocyanines, pseudocyanines
Definitions
- This invention relates to new pyrimido-2-cyanine dyes prepared for use as therapeutics.
- the new compounds of this invention can be represented by the following general formula:
- X represents an anion, e. g. chloride, bromide, iodide, p-toluenesulfonate, benzenesulfonate, methylsulfate, ethylsulfate, acetate, propionate, etc.
- These compounds are of particular value in the treatment of worm infestations where the invading organism is of the class Nematoda (round worms).
- the various species of worms affected by these compounds are hookworms, ascarids, filarids and whipworms.
- the compounds wherein X represents chloride, benzenesulfonate, p-toluenesulfonate, methylsulfate, ethylsulfate, acetate or propionate are the more soluble compounds and the most useful thereapeutically.
- a 4,6-dimethyl-2-phenylpyrimidine methyl quaternary salt is condensed with a quinoline ethyl quaternary containing in the a-position an iodine atom or a thioether group.
- the condensations are advantageously effected in the presence of an acid-binding agent (basic condensing agent), e. g. a tertiary amine having an ionization constant greater than at 25 C., such as triethyl-amine, triisopropylamine, triisobutylamine, triethanolamine, N-methylpiperidine, etc., or an alkali metal carbonate, e. g. sodium or potassium carbonate.
- a solvent is advantageously employed as reaction medium, e. g. pyridine, quirroline, ethyl alcohol, isopropyl alcohol, n-propyl alcohol, etc.
- Typical 4,6 dimethyl 2 phenylpyrimidine methyl quaternary salts include the methiodide, the methomethylsulfate, the metho-p-toluenesulfonate, the methobenzenesulfonate, etc. These quaternary salts can be formed by the interaction of 4,6-dimethyl-Z-phenylpyrimidine and an alkyl salt, e. g. methyl iodide, dimethyl sulfate, methyl-p-toluenesulfonate, methyl benzenesulfonate, etc. employing neat if necessary.
- Typical of the quinoline ethyl quaternary salts which can be employed to prepare these new compounds are: 2-iodoquinoline ethiodide, 2-iodoquinoline etho-p-toluenesulfonate, 2-iodoquino line ethoethylsulfate, Z-phenylmercaptoquinoline ethiodide (Z-phenylthioquinoline ethiodide), 2- (p tolylmercapto quinoline ethiodide, 2 (finaphthylmercapto)quinoline ethiodide, 2-(2,5- dichlorophenylmercapto) quinoline ethiodide, 2- (n-butylmercapto) quinoline ethiodide, 2-(2-benzothiazolylmercapto)quinoline ethiodide, etc. Many of these quinoline ethyl quaternary salts containing a
- Example 1.1'-ethz/l-3,6 dimethyl-2-phenyl- 4- pyrimido-2'-cyanine iodide 21.7 g. (1 mol.) of 4,6-dimethyl-2-phenylpyrimidine methiodide, 27.4 g. (1 mol.) of 2-iodoquinoline ethiodide, cc. of ethyl alcohol and 6.73 g. (2 mol.) of triethylamine were gently refluxed for about 30 minutes. The dye which formed was filtered off, washed on the filter first with water and then with acetone. The washed dye was twice recrystallized from methyl alcohol and obtained as reddish crystals melting "at 247 to 248 C. with decomposition. Iodine, calculated 26.38%; found 26.09%.
- 1-ethyl-3,6-dimethyl-2- phenyli-pyrimido-Z-cyanine iodide can be prepared using an amount of 2-iodoquinoline ethop-toluenesulfonate or 2-iodoquinoline ethoethylsulfate molecularly equivalent to the 2-iodoquinoline ethiodide employed above.
- 4-iodoquinoline ethop-toluenesulfonate or 2-iodoquinoline ethoethylsulfate molecularly equivalent to the 2-iodoquinoline ethiodide employed above.
- Silver chloride was prepared by treating a 15 percent-solution of 340 g. of silver nitrate in distilled-water with concentrated hydrochloric acid (spwg. 1.18) until no furtherprecipitate was formed. The precipitated silver chloride was washed with water by decantation until the liquors were neutral to litmus. The washed silver chloride was filtered off and washed with .methyl alcohol.
- The-so-prepared silver chloride was added to a boi1'ing, stirredsolution of 87.5 g. of 1'-ethyl3-,6- dimethyl-2-phenyl-4-pyrimido-2-cyanine iodide in 4 Lot methyl alcohol. under reflux. The stirring and refluxing were continued for 2 to 4 hours. The solidwas then allowed to settle and then was filtered off 'by suction. The solid on the filter was washed with methyl alcohol. The filtrate and washings were concentrated to a small volume' (300to-400 cc.) on a steamhath.
- the new compound, prepared for use as a therapeutic represented by the following gen- 3.
- the new compound, prepared for use as a therapeutic represented by the following general formula:
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Plural Heterocyclic Compounds (AREA)
- Indole Compounds (AREA)
Description
Patented June 7, 1949 PYRIMIDO-Z -CYANIN E DYES Leslie G. S. Brooker, Rochester, N. Y., and Walter F. Holcomb and Clarence Kenneth Banks, Detroit, Mich., assignors to Eastman Kodak Company, Rochester, N. Y., a corporation of New J ersey No Drawing. Application September 10, 1946, Serial No. 696,028
3 Claims.
This invention relates to new pyrimido-2-cyanine dyes prepared for use as therapeutics.
A large number of dyes of the cyanine class are known. Several of these dyes have found important uses in the field of photography, certain of th dyes acting to extend the spectral sensitivity of photographic silver halide emulsions.
We have now found that certain new compounds of the cyanine type are of particular value in the treatment of particular kinds of worm infestations. It is accordingly an object of our invention to provide new compounds useful as therapeutics. A further object is to provide a process for preparing such new compounds.
The new compounds of this invention can be represented by the following general formula:
wherein X represents an anion, e. g. chloride, bromide, iodide, p-toluenesulfonate, benzenesulfonate, methylsulfate, ethylsulfate, acetate, propionate, etc.
These compounds are of particular value in the treatment of worm infestations where the invading organism is of the class Nematoda (round worms). Among the various species of worms affected by these compounds are hookworms, ascarids, filarids and whipworms. The compounds wherein X represents chloride, benzenesulfonate, p-toluenesulfonate, methylsulfate, ethylsulfate, acetate or propionate are the more soluble compounds and the most useful thereapeutically.
To prepare the compounds formulated above, a 4,6-dimethyl-2-phenylpyrimidine methyl quaternary salt is condensed with a quinoline ethyl quaternary containing in the a-position an iodine atom or a thioether group. The condensations are advantageously effected in the presence of an acid-binding agent (basic condensing agent), e. g. a tertiary amine having an ionization constant greater than at 25 C., such as triethyl-amine, triisopropylamine, triisobutylamine, triethanolamine, N-methylpiperidine, etc., or an alkali metal carbonate, e. g. sodium or potassium carbonate. A solvent is advantageously employed as reaction medium, e. g. pyridine, quirroline, ethyl alcohol, isopropyl alcohol, n-propyl alcohol, etc.
Typical 4,6 dimethyl 2 phenylpyrimidine methyl quaternary salts include the methiodide, the methomethylsulfate, the metho-p-toluenesulfonate, the methobenzenesulfonate, etc. These quaternary salts can be formed by the interaction of 4,6-dimethyl-Z-phenylpyrimidine and an alkyl salt, e. g. methyl iodide, dimethyl sulfate, methyl-p-toluenesulfonate, methyl benzenesulfonate, etc. employing neat if necessary.
Typical of the quinoline ethyl quaternary salts which can be employed to prepare these new compounds are: 2-iodoquinoline ethiodide, 2-iodoquinoline etho-p-toluenesulfonate, 2-iodoquino line ethoethylsulfate, Z-phenylmercaptoquinoline ethiodide (Z-phenylthioquinoline ethiodide), 2- (p tolylmercapto quinoline ethiodide, 2 (finaphthylmercapto)quinoline ethiodide, 2-(2,5- dichlorophenylmercapto) quinoline ethiodide, 2- (n-butylmercapto) quinoline ethiodide, 2-(2-benzothiazolylmercapto)quinoline ethiodide, etc. Many of these quinoline ethyl quaternary salts containing a, thioether group are described in United States Patent 2,117,936, dated May 17, 1938.
It is advantageous to prepare the iodide form of the new compounds and employ this to prepare more soluble forms, such as the chloride, the
acetate, etc.
Example 1.1'-ethz/l-3,6 dimethyl-2-phenyl- 4- pyrimido-2'-cyanine iodide 21.7 g. (1 mol.) of 4,6-dimethyl-2-phenylpyrimidine methiodide, 27.4 g. (1 mol.) of 2-iodoquinoline ethiodide, cc. of ethyl alcohol and 6.73 g. (2 mol.) of triethylamine were gently refluxed for about 30 minutes. The dye which formed was filtered off, washed on the filter first with water and then with acetone. The washed dye was twice recrystallized from methyl alcohol and obtained as reddish crystals melting "at 247 to 248 C. with decomposition. Iodine, calculated 26.38%; found 26.09%.
In a similar manner 1-ethyl-3,6-dimethyl-2- phenyli-pyrimido-Z-cyanine iodide can be prepared using an amount of 2-iodoquinoline ethop-toluenesulfonate or 2-iodoquinoline ethoethylsulfate molecularly equivalent to the 2-iodoquinoline ethiodide employed above. Using 4,6-
3 dimethyl-Z-phenylpyrimidine metho-p-toluenesulfonate and 2-iodoquinoline etho-p-toluenesulfonate, the same dye ion is obtained. Using 4,6 dimethyl-2-phenylpyrimidine metho-ptluenesulfonate and 2 -.methylmercaptoquinoline etho-p-toluenesulfonate, 1' ethyl-3,6-d'imethyl- 2 phenyl-4-pyrimido-2-cyanine-p-toluenesulfonate is obtained.
Example 2. 1'-ethyl-3,6-dimethyle2=phenylpyrimido-2-cyanine chloride Silver chloride was prepared by treating a 15 percent-solution of 340 g. of silver nitrate in distilled-water with concentrated hydrochloric acid (spwg. 1.18) until no furtherprecipitate was formed. The precipitated silver chloride was washed with water by decantation until the liquors were neutral to litmus. The washed silver chloride was filtered off and washed with .methyl alcohol.
:The-so-prepared silver chloride was added to a boi1'ing, stirredsolution of 87.5 g. of 1'-ethyl3-,6- dimethyl-2-phenyl-4-pyrimido-2-cyanine iodide in 4 Lot methyl alcohol. under reflux. The stirring and refluxing were continued for 2 to 4 hours. The solidwas then allowed to settle and then was filtered off 'by suction. The solid on the filter was washed with methyl alcohol. The filtrate and washings were concentrated to a small volume' (300to-400 cc.) on a steamhath. .The small volume was then cooled and poured into a large beaker and then diethyl ether was added until precipitation of 1'-ethyl-3,6-dimethyl-2-phenyl- 4+pyrimido-2'-cyaninechloride ceased (1200 to 1500 cc. of ether). The mixture was then chilled and-filtered by suction. The dye-chloride was dried in a steam cabinet. The dye-chloride was thus obtained reddish-orange plates melting at 247 to 248 C. with decomposition. Chloride. calculated 9.10%; found 9.08%.
Using silver. acetate instead'of silver chloride, 1' ethyl-3,6-dimethyl-2-phenyl-4-pyrimido-2'- cyanine acetate can be prepared. With silver thiocyanate, 1 thyl-3,6-dimethyl-2-phenyl-4- pyrimidmT-cyan'ine thiocyanate can be prepared. iThe dye-chloride can also be'prepared "by the following general formula:
wherein X represents an anion.
2. The new compound, prepared for use as a therapeutic, represented by the following gen- 3. The new compound, prepared for use as a therapeutic, represented by the following general formula:
on. H H t 5 6 Cz s l 1 LESLIE G. S. BROOKER. WALTER F. HOLCOMB. CLARENCE KENNETH BANKS.
REFERENCES CITED "Thefollowing references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,310,640 Kendall Feb. 9, 1943 FOREIGN PATENTS Number Country Date 425,609 Great Britain Sept. 13, 1933
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US696028A US2472565A (en) | 1946-09-10 | 1946-09-10 | Pyrimido-2'-cyanine dyes |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US696028A US2472565A (en) | 1946-09-10 | 1946-09-10 | Pyrimido-2'-cyanine dyes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2472565A true US2472565A (en) | 1949-06-07 |
Family
ID=24795407
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US696028A Expired - Lifetime US2472565A (en) | 1946-09-10 | 1946-09-10 | Pyrimido-2'-cyanine dyes |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2472565A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2845418A (en) * | 1954-12-02 | 1958-07-29 | Ilford Ltd | Cyanine dyestuffs |
| US3000738A (en) * | 1955-02-07 | 1961-09-19 | Agfa Ag | Optically sensitized photographic silver halide emulsion |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB425609A (en) * | 1933-09-12 | 1935-03-12 | John David Kendall | Improvements in or relating to the production and use of dyes having a methine or polymethine linkage |
| US2310640A (en) * | 1933-05-18 | 1943-02-09 | Ilford Ltd | Production of compounds of the cyanine type |
-
1946
- 1946-09-10 US US696028A patent/US2472565A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2310640A (en) * | 1933-05-18 | 1943-02-09 | Ilford Ltd | Production of compounds of the cyanine type |
| GB425609A (en) * | 1933-09-12 | 1935-03-12 | John David Kendall | Improvements in or relating to the production and use of dyes having a methine or polymethine linkage |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2845418A (en) * | 1954-12-02 | 1958-07-29 | Ilford Ltd | Cyanine dyestuffs |
| US3000738A (en) * | 1955-02-07 | 1961-09-19 | Agfa Ag | Optically sensitized photographic silver halide emulsion |
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