DE2611733A1 - Substituierte 5,6-dialkoxyindazol- 3-carbonsaeurehydrazide, solche enthaltende arzneimittel und verfahren zur herstellung derselben - Google Patents
Substituierte 5,6-dialkoxyindazol- 3-carbonsaeurehydrazide, solche enthaltende arzneimittel und verfahren zur herstellung derselbenInfo
- Publication number
- DE2611733A1 DE2611733A1 DE19762611733 DE2611733A DE2611733A1 DE 2611733 A1 DE2611733 A1 DE 2611733A1 DE 19762611733 DE19762611733 DE 19762611733 DE 2611733 A DE2611733 A DE 2611733A DE 2611733 A1 DE2611733 A1 DE 2611733A1
- Authority
- DE
- Germany
- Prior art keywords
- carboxylic acid
- dialkoxyindazole
- carbon atoms
- general formula
- acid hydrazide
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 6
- 239000003814 drug Substances 0.000 title claims description 5
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 title description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 23
- 125000004432 carbon atom Chemical group C* 0.000 claims description 11
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 239000004480 active ingredient Substances 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 5
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 4
- 239000011707 mineral Substances 0.000 claims description 4
- 229910052717 sulfur Chemical group 0.000 claims description 4
- 239000011593 sulfur Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
- 239000007864 aqueous solution Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 239000000645 desinfectant Substances 0.000 claims description 2
- 229940079593 drug Drugs 0.000 claims description 2
- 238000001640 fractional crystallisation Methods 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 230000002401 inhibitory effect Effects 0.000 description 7
- -1 5,6-diethoxyindazole-3- -carboxylic Chemical compound 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 241000191967 Staphylococcus aureus Species 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 241000191940 Staphylococcus Species 0.000 description 4
- 210000002615 epidermis Anatomy 0.000 description 4
- 244000005700 microbiome Species 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 241000588724 Escherichia coli Species 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000001580 bacterial effect Effects 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- WIIZWVCIJKGZOK-RKDXNWHRSA-N chloramphenicol Chemical compound ClC(Cl)C(=O)N[C@H](CO)[C@H](O)C1=CC=C([N+]([O-])=O)C=C1 WIIZWVCIJKGZOK-RKDXNWHRSA-N 0.000 description 2
- 229960005091 chloramphenicol Drugs 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 239000000825 pharmaceutical preparation Substances 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- NWZSZGALRFJKBT-KNIFDHDWSA-N (2s)-2,6-diaminohexanoic acid;(2s)-2-hydroxybutanedioic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O.NCCCC[C@H](N)C(O)=O NWZSZGALRFJKBT-KNIFDHDWSA-N 0.000 description 1
- GKLSVNJLMNZUJO-UHFFFAOYSA-N 1-ethyl-5,6-dimethoxyindazole-3-carboxamide Chemical compound COC1=C(OC)C=C2N(CC)N=C(C(N)=O)C2=C1 GKLSVNJLMNZUJO-UHFFFAOYSA-N 0.000 description 1
- JOUPSJAGJHYWLM-UHFFFAOYSA-N 1h-indazole-3-carbohydrazide Chemical class C1=CC=C2C(C(=O)NN)=NNC2=C1 JOUPSJAGJHYWLM-UHFFFAOYSA-N 0.000 description 1
- BHXVYTQDWMQVBI-UHFFFAOYSA-N 1h-indazole-3-carboxylic acid Chemical compound C1=CC=C2C(C(=O)O)=NNC2=C1 BHXVYTQDWMQVBI-UHFFFAOYSA-N 0.000 description 1
- STUCOFMCGRLQJY-UHFFFAOYSA-N 5,6-dimethoxy-1h-indazole-3-carbohydrazide Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(=O)NN)=NN2 STUCOFMCGRLQJY-UHFFFAOYSA-N 0.000 description 1
- CGODQEMLWTXHAT-UHFFFAOYSA-N 5,6-dimethoxy-1h-indazole-3-carboxamide Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(N)=O)=NN2 CGODQEMLWTXHAT-UHFFFAOYSA-N 0.000 description 1
- IWUGDDTXRWFNJY-UHFFFAOYSA-N 5,6-dimethoxy-1h-indazole-3-carboxylic acid Chemical compound C1=C(OC)C(OC)=CC2=C1C(C(O)=O)=NN2 IWUGDDTXRWFNJY-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 101100356682 Caenorhabditis elegans rho-1 gene Proteins 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- 241000699670 Mus sp. Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- QOERYXGIRHBDNW-UHFFFAOYSA-N acetic acid;5-nitrothiophene-2-carbaldehyde Chemical compound CC(O)=O.CC(O)=O.[O-][N+](=O)C1=CC=C(C=O)S1 QOERYXGIRHBDNW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004448 alkyl carbonyl group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 230000000845 anti-microbial effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000003763 carbonization Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000004292 cyclic ethers Chemical class 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CNUDBTRUORMMPA-UHFFFAOYSA-N formylthiophene Chemical compound O=CC1=CC=CS1 CNUDBTRUORMMPA-UHFFFAOYSA-N 0.000 description 1
- 150000003278 haem Chemical class 0.000 description 1
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- 238000006396 nitration reaction Methods 0.000 description 1
- IAIWVQXQOWNYOU-FPYGCLRLSA-N nitrofural Chemical compound NC(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 IAIWVQXQOWNYOU-FPYGCLRLSA-N 0.000 description 1
- NXFQHRVNIOXGAQ-YCRREMRBSA-N nitrofurantoin Chemical compound O1C([N+](=O)[O-])=CC=C1\C=N\N1C(=O)NC(=O)C1 NXFQHRVNIOXGAQ-YCRREMRBSA-N 0.000 description 1
- 229960000564 nitrofurantoin Drugs 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 230000000144 pharmacologic effect Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000013558 reference substance Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 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
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HU75EE00002316A HU171739B (hu) | 1975-03-19 | 1975-03-19 | Sposob poluchenija zamehhennykh gidrazidov indazol-karbonovoj kisloty |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2611733A1 true DE2611733A1 (de) | 1976-10-07 |
Family
ID=10995604
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762611733 Withdrawn DE2611733A1 (de) | 1975-03-19 | 1976-03-19 | Substituierte 5,6-dialkoxyindazol- 3-carbonsaeurehydrazide, solche enthaltende arzneimittel und verfahren zur herstellung derselben |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS51115471A (enExample) |
| AT (1) | AT349009B (enExample) |
| CH (1) | CH619225A5 (enExample) |
| CS (1) | CS188133B2 (enExample) |
| DE (1) | DE2611733A1 (enExample) |
| DK (1) | DK138688B (enExample) |
| GB (1) | GB1538558A (enExample) |
| HU (1) | HU171739B (enExample) |
| NL (1) | NL7602893A (enExample) |
| SE (1) | SE420922B (enExample) |
| YU (1) | YU68176A (enExample) |
-
1975
- 1975-03-19 HU HU75EE00002316A patent/HU171739B/hu unknown
-
1976
- 1976-03-16 CH CH324976A patent/CH619225A5/de not_active IP Right Cessation
- 1976-03-16 DK DK113776AA patent/DK138688B/da unknown
- 1976-03-16 YU YU00681/76A patent/YU68176A/xx unknown
- 1976-03-17 CS CS761737A patent/CS188133B2/cs unknown
- 1976-03-17 AT AT198676A patent/AT349009B/de not_active IP Right Cessation
- 1976-03-17 SE SE7603362A patent/SE420922B/xx unknown
- 1976-03-19 NL NL7602893A patent/NL7602893A/xx not_active Application Discontinuation
- 1976-03-19 GB GB11287/76A patent/GB1538558A/en not_active Expired
- 1976-03-19 JP JP51029375A patent/JPS51115471A/ja active Pending
- 1976-03-19 DE DE19762611733 patent/DE2611733A1/de not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| DK113776A (enExample) | 1976-09-20 |
| CS188133B2 (en) | 1979-02-28 |
| SE420922B (sv) | 1981-11-09 |
| YU68176A (en) | 1983-01-21 |
| HU171739B (hu) | 1978-03-28 |
| GB1538558A (en) | 1979-01-24 |
| DK138688C (enExample) | 1979-03-26 |
| SE7603362L (sv) | 1976-09-20 |
| ATA198676A (de) | 1978-08-15 |
| DK138688B (da) | 1978-10-16 |
| AT349009B (de) | 1979-03-12 |
| JPS51115471A (en) | 1976-10-12 |
| NL7602893A (nl) | 1976-09-21 |
| CH619225A5 (en) | 1980-09-15 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8141 | Disposal/no request for examination |