US3262930A - Novel 5-nitro-furfurylidene-(2) derivatives and process for producing the same - Google Patents

Novel 5-nitro-furfurylidene-(2) derivatives and process for producing the same Download PDF

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US3262930A
US3262930A US323225A US32322563A US3262930A US 3262930 A US3262930 A US 3262930A US 323225 A US323225 A US 323225A US 32322563 A US32322563 A US 32322563A US 3262930 A US3262930 A US 3262930A
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nitro
dioxide
furfurylidene
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Herlinger Heinz
Mayer Karl-Heinrich
Petersen Siegfried
Bock Marianne
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Bayer AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D307/70—Nitro radicals
    • C07D307/71—Nitro radicals attached in position 5
    • C07D307/72—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2
    • C07D307/74—Nitro radicals attached in position 5 with hydrocarbon radicals, substituted by nitrogen-containing radicals, attached in position 2 by hydrazino or hydrazono or such substituted radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
    • C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the present invention relates, in general, to organic chemistry, and, more particularly, to certain novel 5- nitro-furfurylidene-(l) derivatives and a unique process for producing the same via the reaction of S-nitro-furfurol-(Z) with l-arninotetra-hydro-l,4-thiazine-4,4-dioxide. Additionally, the invention involves the use of the novel compounds of the invention as ant-helmintics of rather specific and unique activity as explained in greater detail hereinafter.
  • the compounds of the invention may be represented by the following structural formula wherein R represents hydrogen, from 1 to 4 lower (C C alkyl radicals, from 1 to 2 aralkyl radicals such as benzyl, or aryl radicals such as phenyl.
  • the indicated reaction of the l-aminotetrahydro-1,4-thiaZine-dioxide with S-ni-tro-furfurol is effected within an organic solvent medium in which both of the starting components are soluble, and in which the desired end-product is insoluble.
  • the compounds of the invention are distinguished by a low order of toxicity and high activity against Trypanosoma cruzi, the causative agent for the Chagas disease as well as other protozoa, e.g., Trypanosoma congolense and Trypanosoma bruceiaus.
  • the Chagas disease the South American form of trypanosomiasis, for example, the semicarbazide of 5-nitro furfurol-(2) has been used hereto-fore.
  • the compounds of the invention were investigated with white mice.
  • the animals were injected with Trypanosoma crwzi, and thereafter treated subcutaneously with the unit dosages indicated in Table I on four successive days, commencing one day after initial injection.
  • blood samples of the treated animals were examined microscopically for Trypanosoma cruzi at intervals of one day, commencing the sixth day after initial injection, and compared with untreated injected control animals of the same species.
  • the animals are treated with an insufficient dosage of the anthelmintics of the invention, the same number of trypanosomes are found in the blood as in that of the control animals designates no effect). If, on the other hand, effective doses of the preparation are administered to the animals, the blood is free of trypanosomes for a few days or even for weeks. With reference to Table I, the ultimate test result is indicated by the designation HE (healing efiect), provided the Trypanosoma cruzi cannot be detected within the peripheral blood of the test animals for four weeks or longer, and a re-infection takes a positive course.
  • HE heating efiect
  • RE recidivation efiect
  • T traces of effect
  • Example I Fifteen (15) grams of l-amino-tetrahydro-l,4-thiazine-4,4-dioxide were treated Within 150 milliliters of acetic acid with 14.1 grams of S-nitro-furfurol-(Z), and the mixture heated for a short time. Orange-red crystals of 1-(5-nitro-furfurylidene-amino)-1,4tetrahydrothiazine- 4,4-dioxide separated out at once which, following filtration via suction and washing with Water, were immediately found to be analytically pure. The melting point, following recrystallization from acetic acid, was found to be 191 C.
  • Example II 1 amino Z-methyI-tetrahydro-1,4-hydroxythiazine-4,4- dioxide, in amount of 15.4 grams, was dissolved in 100 milliliters of alcohol and 5 milliliters of acetic acid, and then added to a solution consisting of 14.1 grams of 5- nitro-furfurol-(2) within 100 milliliters of alcohol.
  • the production of the 1-amino-2-methyl-tetrahydro- 1,4 hydroxythiazine-dioxide used as the starting compound in the foregoing synthesis can be eflfected by (a) reacting Z-mercaptoethanol with propylene oxide in the presence of potassium hydroxide. 2-hydroxyethyl-Z-hydroxypropyl sulphide of boiling point 160 C. at 15 mm. Hg is thus obtained; (b) distillation of 2-hydroxyethyl-2- hydroxypropyl sulphide over p-toluene-sulphonic acid or potassium hydrogen sulphate under normal pressure. 2- methyl-1,4-hydroxythiane is thus obtained (boiling point: -46" C. at 18 mm.
  • Example Ill The 1 amino Z-ethyI-tetrahydro-1,4-thiazine-4,4-dioxide used as the starting compound in the foregoing synthesis may be obtained in a manner analogous to that described above in connection with Example II, (a)-(d), namely:
  • R is a member selected from the group consisting of hydrogen, lower alkyl, benzyl and phenyl.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen- Or Sulfur-Containing Heterocyclic Ring Compounds With Rings Of Six Or More Members (AREA)

Description

United States Patent ice 3 262 930 NOVEL NITRO EURFURYLIDENE (2) DE- RIVATIVES AND PROCESS FOR PRODUC- INC THE SAME Heinz Her-linger, Cologne-Flittard, Karl-Heinrich Mayer and Siegfried Petersen, Leverkusen, and Marianne Bock, Wuppertal-Sonnborn, Germany, assignors to Farbenfabriken Bayer Aktiengesellschaft, Leverkusen,
Germany, a corporation of Germany No Drawing. Filed Nov. 13, 1963, Ser. No. 323,225
Claims priority, application Germany, Nov. 23, 1962,
F 38,378 4 Claims. (Cl. 260-240) The present invention relates, in general, to organic chemistry, and, more particularly, to certain novel 5- nitro-furfurylidene-(l) derivatives and a unique process for producing the same via the reaction of S-nitro-furfurol-(Z) with l-arninotetra-hydro-l,4-thiazine-4,4-dioxide. Additionally, the invention involves the use of the novel compounds of the invention as ant-helmintics of rather specific and unique activity as explained in greater detail hereinafter.
In general, the compounds of the invention may be represented by the following structural formula wherein R represents hydrogen, from 1 to 4 lower (C C alkyl radicals, from 1 to 2 aralkyl radicals such as benzyl, or aryl radicals such as phenyl.
Preferably, the indicated reaction of the l-aminotetrahydro-1,4-thiaZine-dioxide with S-ni-tro-furfurol is effected within an organic solvent medium in which both of the starting components are soluble, and in which the desired end-product is insoluble.
By reference to United States Patent No. 3,001,992 issued to Bellamy et al. on September 26, 1961, there are described certain 5-nitro-furfurylidene (2)-amino compounds carrying heterocyclic substituents, but these compounds exhibit only trace-activity against trypanosomes, or none at all, and are moreover, extremely toxic. Comparative testing of the unique compounds of the invention with respect to both their effectiveness and tox- 3,2629% Patented July 26, 1966 use of the compounds of the invention over known derivatives of somewhat similar chemical structure and similar direction of activity.
Thus, the compounds of the invention are distinguished by a low order of toxicity and high activity against Trypanosoma cruzi, the causative agent for the Chagas disease as well as other protozoa, e.g., Trypanosoma congolense and Trypanosoma bruceiaus. In the former connection, for indications against the Chagas disease (the South American form of trypanosomiasis, for example, the semicarbazide of 5-nitro furfurol-(2) has been used hereto-fore.
In connection with the aforementioned comparative studies, the compounds of the invention were investigated with white mice. The animals were injected with Trypanosoma crwzi, and thereafter treated subcutaneously with the unit dosages indicated in Table I on four successive days, commencing one day after initial injection. For evaluation purposes, blood samples of the treated animals were examined microscopically for Trypanosoma cruzi at intervals of one day, commencing the sixth day after initial injection, and compared with untreated injected control animals of the same species.
As represented by the tabulated results, if the animals are treated with an insufficient dosage of the anthelmintics of the invention, the same number of trypanosomes are found in the blood as in that of the control animals designates no effect). If, on the other hand, effective doses of the preparation are administered to the animals, the blood is free of trypanosomes for a few days or even for weeks. With reference to Table I, the ultimate test result is indicated by the designation HE (healing efiect), provided the Trypanosoma cruzi cannot be detected within the peripheral blood of the test animals for four weeks or longer, and a re-infection takes a positive course. The designation RE (recidivation efiect) indicates a recurrence of trypanosomes in the blood of the treated animals following a temporary negative microscopic examination of more than two days. The designation T (traces of effect) indicates an influence on the infection which could still be detected. The results of the tabulated studies were confirmed on additional strains of Trypanosoma cruzi of various icity readily demonstrates the advance achieved through 4.5 origin.
TABLE I Activity against Trypanosoma cruzi (mg/kg.) Toxicity 1 (mg/kg.) (subcutaneously) (subcutaneously) 3 Compound (MN-K J-(]H=NR E RE RE RE-T 2 3/3 1/3 0/3 R: NHGO-NH2 N S02 E HE RE RE RE 4) 3/3 0/3 0/3 0/3 -N O 'l T 3/3 2/3 0/3 -N S0 HE RE RE RE 0/3 0/3 0/3 -N S0 HE RE RE RE 5 0/3 0/3 0/3 HE: Healing elicct.
RE: Recidivation effect. '1: Traces of effect.
No effect.
1 With a single treatment.
2 Number of animals destroyed to total number of animals used. 3 Four treatments.
4 Toxic dose; four subcutaneous applications on successive days.
It is believed that the invention may be best understood by reference to the following specific examples illustrating the application of the foregoing principles and procedures in the production of typical compounds of the invention:
Example I Fifteen (15) grams of l-amino-tetrahydro-l,4-thiazine-4,4-dioxide were treated Within 150 milliliters of acetic acid with 14.1 grams of S-nitro-furfurol-(Z), and the mixture heated for a short time. Orange-red crystals of 1-(5-nitro-furfurylidene-amino)-1,4tetrahydrothiazine- 4,4-dioxide separated out at once which, following filtration via suction and washing with Water, were immediately found to be analytically pure. The melting point, following recrystallization from acetic acid, was found to be 191 C.
Analysis.(C H N O S): Molecular weight, 273. Calculated: C, 39.6%; H, 4.03%; N, 15.4%. Found: C, 39.6%; H, 4.25%; N, 15.4%.
Example II 1 amino Z-methyI-tetrahydro-1,4-hydroxythiazine-4,4- dioxide, in amount of 15.4 grams, was dissolved in 100 milliliters of alcohol and 5 milliliters of acetic acid, and then added to a solution consisting of 14.1 grams of 5- nitro-furfurol-(2) within 100 milliliters of alcohol. The
resultant mixture was heated for a brief period of time and then cooled for crystallization. Twenty-eight (28) grams of orange-red crystals of 1-(5-nitrofurfurylideneamino)-tetrahydro-2-methyl-1,4-thiazine-4,4-dioxide separated out of the reaction mixture. The melting point, following recrystallization from dilute acetic acid, was found to be 172 C.
Analysis.(C H N O S): Molecular weight, 287. Calculated: C, 41.8%; H, 4.53%; N, 14.7%. Found: C, 41.92%; H, 4.66%; N, 14.9%.
The production of the 1-amino-2-methyl-tetrahydro- 1,4 hydroxythiazine-dioxide used as the starting compound in the foregoing synthesis can be eflfected by (a) reacting Z-mercaptoethanol with propylene oxide in the presence of potassium hydroxide. 2-hydroxyethyl-Z-hydroxypropyl sulphide of boiling point 160 C. at 15 mm. Hg is thus obtained; (b) distillation of 2-hydroxyethyl-2- hydroxypropyl sulphide over p-toluene-sulphonic acid or potassium hydrogen sulphate under normal pressure. 2- methyl-1,4-hydroxythiane is thus obtained (boiling point: -46" C. at 18 mm. Hg; n =l.4942); (c) oxidation of Z-methyl-l,4hydroxythiane with hydrogen peroxide in acetic acid to form 2-methyl-1,4-tetrahydro-thi0xane-4,4- dioxide (melting point 82 C. following recrystallization from alcohol/ether).
Analysis.-(C H O S): Molecular weight, 150. Calculated: S, 21.3%. Found: S, 21.8%; or (d) reacting 2-methyl-1,4-tetrahydro-thioxane-4,4-dioxide with hydrazine at C. with the use of an excess of hydrazine, leading to 1-amino-2-methyl-1,4-tetrahydro-thiazine-4,4- dioxide (melting point=l15 C.).
Analysis.-(C H N O S): Molecular weight, 164. Calculated: C, 36.6%; H, 7.32%; N, 17.1%. Found: C, 36.4%; H, 7.31%; N, 16.9%.
Example Ill The 1 amino Z-ethyI-tetrahydro-1,4-thiazine-4,4-dioxide used as the starting compound in the foregoing synthesis may be obtained in a manner analogous to that described above in connection with Example II, (a)-(d), namely:
(a) 2 hydroxyethyl 2 hydroxybutyl sulphide (boiling point: 164-165 c. at 18 mm. Hg; n =l.5058);
(b) 2-ethyl-thioxane-(4,l) (boiling point: 55-60 C. at
17 mm. Hg; n =1.4968), and
(c) 2-ethyl-thioxane-(4,1)-dioxide-(4,4) (melting point:
What is claimed is: 1. A compound of the formula:
wherein R is a member selected from the group consisting of hydrogen, lower alkyl, benzyl and phenyl.
2. The chemical compound, 1-(S-nitro-furfurylideneamino)-1,4-tetrahydrothiazine4,4-dioxide.
3. The chemical compound, I-(S-nitro-furfurylideneamino)-tetrahydro-2-methyl-1,4-thiazine-4,4-dioxide.
4. The chemical compound, l-(S-nitro-furfurylideneamino) -tetrahydro-2-ethyl-1,4-thiazine-4,4-dioxide.
References Cited by the Examiner UNITED STATES PATENTS 6/1961 Bellamy et a1. 260-240 WALTER A. MODANCE, Primary Examiner.
I. D. RANDOLPH, Assistant Examiner.

Claims (1)

1. A COMPOUND OF THE FORMULA:
US323225A 1962-11-23 1963-11-13 Novel 5-nitro-furfurylidene-(2) derivatives and process for producing the same Expired - Lifetime US3262930A (en)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3488348A (en) * 1966-01-05 1970-01-06 Bayer Ag 5-nitro-furfurylidene-(2)-imino derivatives and their preparation
US3755308A (en) * 1970-04-25 1973-08-28 Bayer Ag Nitrofurfurylideneamino derivative of octahydrobenzthiazine-1,-dioxide and process for its preparation
WO2010000398A1 (en) * 2008-07-02 2010-01-07 Bayer Animal Health Gmbh Nifurtimox for treating diseases caused by trichomonadida
WO2010000399A1 (en) * 2008-07-02 2010-01-07 Bayer Animal Health Gmbh Use of nifurtimox for treating giardiasis
EP3750527A1 (en) 2019-06-13 2020-12-16 Bayer AG Stable tablet formulation of nifurtimox and process for producing the same

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1670840A1 (en) * 1967-03-31 1971-03-11 Bayer Ag Process for the preparation of tetra-hydro-1,4-thiazine-1,1-dioxides
US8406309B2 (en) 2005-10-21 2013-03-26 Qualcomm Incorporated Video rate adaptation to reverse link conditions

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001992A (en) * 1961-09-26 S-niteo-z-fubftjewdene

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3001992A (en) * 1961-09-26 S-niteo-z-fubftjewdene

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3488348A (en) * 1966-01-05 1970-01-06 Bayer Ag 5-nitro-furfurylidene-(2)-imino derivatives and their preparation
US3755308A (en) * 1970-04-25 1973-08-28 Bayer Ag Nitrofurfurylideneamino derivative of octahydrobenzthiazine-1,-dioxide and process for its preparation
WO2010000398A1 (en) * 2008-07-02 2010-01-07 Bayer Animal Health Gmbh Nifurtimox for treating diseases caused by trichomonadida
WO2010000399A1 (en) * 2008-07-02 2010-01-07 Bayer Animal Health Gmbh Use of nifurtimox for treating giardiasis
US20110105388A1 (en) * 2008-07-02 2011-05-05 Bayer Animal Health Gmbh Novel possibility of controlling giardiosis
US20110118176A1 (en) * 2008-07-02 2011-05-19 Bayer Animal Health Gmbh Novel possibility of controlling diseases caused by trichomonadida
JP2011526264A (en) * 2008-07-02 2011-10-06 バイエル・アニマル・ヘルス・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング Nifurtimox for the treatment of diseases caused by Trichomonas eyes
CN102083440B (en) * 2008-07-02 2013-03-27 拜耳知识产权有限责任公司 Nifurtimox for treating diseases caused by trichomonadida
US8440612B2 (en) 2008-07-02 2013-05-14 Bayer Intellectual Property Gmbh Controlling giardiosis
US8440613B2 (en) 2008-07-02 2013-05-14 Bayer Intellectual Property Gmbh Controlling diseases caused by trichomonadida
CN102083441B (en) * 2008-07-02 2013-07-24 拜耳知识产权有限责任公司 Use of nifurtimox for treating giardiasis
AU2009266125B2 (en) * 2008-07-02 2015-06-04 Bayer Intellectual Property Gmbh Use of nifurtimox for treating giardiasis
EP3750527A1 (en) 2019-06-13 2020-12-16 Bayer AG Stable tablet formulation of nifurtimox and process for producing the same
WO2020249500A1 (en) 2019-06-13 2020-12-17 Bayer Aktiengesellschaft Stable tablet formulation of nifurtimox and process for producing the same

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