DE2659528A1 - Organische verbindungen, ihre verwendung und herstellung - Google Patents
Organische verbindungen, ihre verwendung und herstellungInfo
- Publication number
- DE2659528A1 DE2659528A1 DE19762659528 DE2659528A DE2659528A1 DE 2659528 A1 DE2659528 A1 DE 2659528A1 DE 19762659528 DE19762659528 DE 19762659528 DE 2659528 A DE2659528 A DE 2659528A DE 2659528 A1 DE2659528 A1 DE 2659528A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- group
- activity
- lower alkyl
- amidrazones
- 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.)
- Pending
Links
- 230000003569 amebicidal effect Effects 0.000 title abstract description 3
- 230000000694 effects Effects 0.000 title description 2
- 230000002963 trichomonacidal effect Effects 0.000 title description 2
- 230000000844 anti-bacterial effect Effects 0.000 title 1
- 230000002192 coccidiostatic effect Effects 0.000 title 1
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 7
- 239000002253 acid Substances 0.000 claims abstract description 6
- 125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 14
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 239000011593 sulfur Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 5
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 150000002391 heterocyclic compounds Chemical class 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 2
- MTCFGRXMJLQNBG-UHFFFAOYSA-N Serine Natural products OCC(N)C(O)=O MTCFGRXMJLQNBG-UHFFFAOYSA-N 0.000 claims 1
- 125000003607 serino group Chemical class [H]N([H])[C@]([H])(C(=O)[*])C(O[H])([H])[H] 0.000 claims 1
- 239000000203 mixture Substances 0.000 abstract description 2
- DVDDPFRMIWSHHY-UHFFFAOYSA-N n'-amino-1-methyl-5-nitroimidazole-2-carboximidamide Chemical compound CN1C(C(\N)=N\N)=NC=C1[N+]([O-])=O DVDDPFRMIWSHHY-UHFFFAOYSA-N 0.000 abstract description 2
- 238000010992 reflux Methods 0.000 abstract description 2
- GKASDNZWUGIAMG-UHFFFAOYSA-N triethyl orthoformate Chemical compound CCOC(OCC)OCC GKASDNZWUGIAMG-UHFFFAOYSA-N 0.000 abstract description 2
- 150000001411 amidrazones Chemical class 0.000 abstract 1
- 239000003242 anti bacterial agent Substances 0.000 abstract 1
- 230000001165 anti-coccidial effect Effects 0.000 abstract 1
- WBJINCZRORDGAQ-UHFFFAOYSA-N formic acid ethyl ester Natural products CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 abstract 1
- 238000010438 heat treatment Methods 0.000 abstract 1
- -1 Hydroxyethyl group Chemical group 0.000 description 5
- 150000007857 hydrazones Chemical class 0.000 description 4
- 241000224421 Heterolobosea Species 0.000 description 3
- 241001502500 Trichomonadida Species 0.000 description 3
- 210000003001 amoeba Anatomy 0.000 description 3
- 239000002775 capsule Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 230000000973 chemotherapeutic effect Effects 0.000 description 3
- 241000224483 Coccidia Species 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000700159 Rattus Species 0.000 description 2
- 208000005448 Trichomonas Infections Diseases 0.000 description 2
- 206010044620 Trichomoniasis Diseases 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- FJKIXWOMBXYWOQ-UHFFFAOYSA-N ethenoxyethane Chemical group CCOC=C FJKIXWOMBXYWOQ-UHFFFAOYSA-N 0.000 description 2
- 238000001727 in vivo Methods 0.000 description 2
- 244000045947 parasite Species 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- XDHOEHJVXXTEDV-UHFFFAOYSA-N 1-ethoxyprop-1-ene Chemical group CCOC=CC XDHOEHJVXXTEDV-UHFFFAOYSA-N 0.000 description 1
- 208000004881 Amebiasis Diseases 0.000 description 1
- 241000224489 Amoeba Species 0.000 description 1
- 206010001980 Amoebiasis Diseases 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 208000003495 Coccidiosis Diseases 0.000 description 1
- 241000699800 Cricetinae Species 0.000 description 1
- 241000224432 Entamoeba histolytica Species 0.000 description 1
- 206010023076 Isosporiasis Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000699666 Mus <mouse, genus> Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- 241000224527 Trichomonas vaginalis Species 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 229910003460 diamond Inorganic materials 0.000 description 1
- 239000010432 diamond Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000003966 growth inhibitor Substances 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 231100000636 lethal dose Toxicity 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 238000013207 serial dilution Methods 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 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
- C07D233/66—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
- C07D233/91—Nitro radicals
- C07D233/92—Nitro radicals attached in position 4 or 5
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/02—Antiprotozoals, e.g. for leishmaniasis, trichomoniasis, toxoplasmosis
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Tropical Medicine & Parasitology (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH21976 | 1976-01-09 | ||
| CH217476 | 1976-02-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2659528A1 true DE2659528A1 (de) | 1977-07-14 |
Family
ID=25683914
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762659528 Pending DE2659528A1 (de) | 1976-01-09 | 1976-12-30 | Organische verbindungen, ihre verwendung und herstellung |
Country Status (10)
| Country | Link |
|---|---|
| JP (1) | JPS5287161A (cs) |
| AU (1) | AU2116277A (cs) |
| BE (1) | BE850218A (cs) |
| DE (1) | DE2659528A1 (cs) |
| DK (1) | DK477A (cs) |
| FI (1) | FI763742A7 (cs) |
| IL (1) | IL51229A0 (cs) |
| NL (1) | NL7700053A (cs) |
| PT (1) | PT66045B (cs) |
| SE (1) | SE7614715L (cs) |
-
1976
- 1976-12-30 SE SE7614715A patent/SE7614715L/xx unknown
- 1976-12-30 DE DE19762659528 patent/DE2659528A1/de active Pending
- 1976-12-30 FI FI763742A patent/FI763742A7/fi not_active Application Discontinuation
-
1977
- 1977-01-03 DK DK477A patent/DK477A/da unknown
- 1977-01-05 NL NL7700053A patent/NL7700053A/xx unknown
- 1977-01-07 BE BE173947A patent/BE850218A/xx unknown
- 1977-01-07 AU AU21162/77A patent/AU2116277A/en not_active Expired
- 1977-01-07 IL IL51229A patent/IL51229A0/xx unknown
- 1977-01-07 PT PT66045A patent/PT66045B/pt unknown
- 1977-01-08 JP JP111977A patent/JPS5287161A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| FI763742A7 (cs) | 1977-07-10 |
| IL51229A0 (en) | 1977-03-31 |
| PT66045A (fr) | 1977-02-01 |
| PT66045B (fr) | 1978-08-03 |
| AU2116277A (en) | 1978-07-13 |
| SE7614715L (sv) | 1977-07-10 |
| JPS5287161A (en) | 1977-07-20 |
| DK477A (da) | 1977-07-10 |
| BE850218A (fr) | 1977-07-07 |
| NL7700053A (nl) | 1977-07-12 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OHJ | Non-payment of the annual fee |