DE2036935C3 - Diisonicotinsäurehydrazid-methansulfonat des d(+)2^>-(Äthylendiimino)-di-lbutanols, Verfahren zur Herstellung desselben und diese Verbindung enthaltende Arzneimittel - Google Patents
Diisonicotinsäurehydrazid-methansulfonat des d(+)2^>-(Äthylendiimino)-di-lbutanols, Verfahren zur Herstellung desselben und diese Verbindung enthaltende ArzneimittelInfo
- Publication number
- DE2036935C3 DE2036935C3 DE2036935A DE2036935A DE2036935C3 DE 2036935 C3 DE2036935 C3 DE 2036935C3 DE 2036935 A DE2036935 A DE 2036935A DE 2036935 A DE2036935 A DE 2036935A DE 2036935 C3 DE2036935 C3 DE 2036935C3
- Authority
- DE
- Germany
- Prior art keywords
- methanesulfonate
- compound
- ethylenediimino
- isoniazid
- diisonicotinic
- 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
Links
- 150000001875 compounds Chemical class 0.000 title claims description 29
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 title claims description 9
- 239000002253 acid Substances 0.000 title claims description 6
- -1 ethylenediimino Chemical group 0.000 title claims description 4
- 238000000034 method Methods 0.000 title claims description 4
- 238000002360 preparation method Methods 0.000 title claims description 4
- 239000003814 drug Substances 0.000 title description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N 1-butanol Substances CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 2
- 239000003513 alkali Substances 0.000 claims description 2
- TWBYWOBDOCUKOW-UHFFFAOYSA-N isonicotinic acid Chemical compound OC(=O)C1=CC=NC=C1 TWBYWOBDOCUKOW-UHFFFAOYSA-N 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 1
- AEUTYOVWOVBAKS-UWVGGRQHSA-N ethambutol Chemical compound CC[C@@H](CO)NCCN[C@@H](CC)CO AEUTYOVWOVBAKS-UWVGGRQHSA-N 0.000 description 27
- GQZQCROBCYNTMU-UHFFFAOYSA-N methaniazide Chemical compound OS(=O)(=O)CNNC(=O)C1=CC=NC=C1 GQZQCROBCYNTMU-UHFFFAOYSA-N 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
- 238000012360 testing method Methods 0.000 description 13
- 241001465754 Metazoa Species 0.000 description 12
- QRXWMOHMRWLFEY-UHFFFAOYSA-N isoniazide Chemical compound NNC(=O)C1=CC=NC=C1 QRXWMOHMRWLFEY-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- 229960000285 ethambutol Drugs 0.000 description 11
- 229960003350 isoniazid Drugs 0.000 description 10
- 241000700198 Cavia Species 0.000 description 9
- 239000002609 medium Substances 0.000 description 8
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 208000015181 infectious disease Diseases 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000002401 inhibitory effect Effects 0.000 description 5
- 239000003208 petroleum Substances 0.000 description 5
- 201000008827 tuberculosis Diseases 0.000 description 5
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 238000002425 crystallisation Methods 0.000 description 4
- 230000008025 crystallization Effects 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- 238000011835 investigation Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 235000015097 nutrients Nutrition 0.000 description 4
- 230000001717 pathogenic effect Effects 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 4
- 230000001580 bacterial effect Effects 0.000 description 3
- 230000003385 bacteriostatic effect Effects 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- AEUTYOVWOVBAKS-UHFFFAOYSA-N 2-[2-(1-hydroxybutan-2-ylamino)ethylamino]-1-butanol Chemical class CCC(CO)NCCNC(CC)CO AEUTYOVWOVBAKS-UHFFFAOYSA-N 0.000 description 2
- 102000009027 Albumins Human genes 0.000 description 2
- 108010088751 Albumins Proteins 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- 238000010521 absorption reaction Methods 0.000 description 2
- 230000037396 body weight Effects 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 229940098779 methanesulfonic acid Drugs 0.000 description 2
- 229950007577 methaniazide Drugs 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000011780 sodium chloride Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 208000024891 symptom Diseases 0.000 description 2
- 230000001225 therapeutic effect Effects 0.000 description 2
- AUAHHJJRFHRVPV-UHFFFAOYSA-N 1-hydroxybutan-2-yl-[2-(1-hydroxybutan-2-ylazaniumyl)ethyl]azanium;dichloride Chemical compound Cl.Cl.CCC(CO)NCCNC(CC)CO AUAHHJJRFHRVPV-UHFFFAOYSA-N 0.000 description 1
- WSLPUXWJTSNFGB-UHFFFAOYSA-N 4-[2-(4-hydroxybutylamino)ethylamino]butan-1-ol Chemical compound OCCCCNCCNCCCCO WSLPUXWJTSNFGB-UHFFFAOYSA-N 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 241000700199 Cavia porcellus Species 0.000 description 1
- 238000011887 Necropsy Methods 0.000 description 1
- 206010044756 Tuberculous infections Diseases 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000007059 acute toxicity Effects 0.000 description 1
- 231100000403 acute toxicity Toxicity 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZMXDDKWLCZADIW-UHFFFAOYSA-N dimethylformamide Substances CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
- 201000010099 disease Diseases 0.000 description 1
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- AUAHHJJRFHRVPV-BZDVOYDHSA-N ethambutol dihydrochloride Chemical compound [Cl-].[Cl-].CC[C@@H](CO)[NH2+]CC[NH2+][C@@H](CC)CO AUAHHJJRFHRVPV-BZDVOYDHSA-N 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- MGJURKDLIJVDEO-UHFFFAOYSA-N formaldehyde;hydrate Chemical class O.O=C MGJURKDLIJVDEO-UHFFFAOYSA-N 0.000 description 1
- 210000004013 groin Anatomy 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 238000007912 intraperitoneal administration Methods 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 210000004072 lung Anatomy 0.000 description 1
- FDZZZRQASAIRJF-UHFFFAOYSA-M malachite green Chemical compound [Cl-].C1=CC(N(C)C)=CC=C1C(C=1C=CC=CC=1)=C1C=CC(=[N+](C)C)C=C1 FDZZZRQASAIRJF-UHFFFAOYSA-M 0.000 description 1
- 229940107698 malachite green Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- RZRNNGMKQASFBS-UHFFFAOYSA-N methanesulfonic acid;pyridine-4-carbohydrazide Chemical compound CS(O)(=O)=O.NNC(=O)C1=CC=NC=C1 RZRNNGMKQASFBS-UHFFFAOYSA-N 0.000 description 1
- 230000002969 morbid Effects 0.000 description 1
- 210000005036 nerve Anatomy 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000002085 persistent effect Effects 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001373 regressive effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 231100000161 signs of toxicity Toxicity 0.000 description 1
- 210000000952 spleen Anatomy 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000008174 sterile solution Substances 0.000 description 1
- 239000007929 subcutaneous injection Substances 0.000 description 1
- 238000010254 subcutaneous injection Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 230000004083 survival effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 230000001549 tubercolostatic effect Effects 0.000 description 1
- 238000000108 ultra-filtration Methods 0.000 description 1
- 238000002211 ultraviolet spectrum Methods 0.000 description 1
- 238000002255 vaccination Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/86—Hydrazides; Thio or imino analogues thereof
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| ES369952A ES369952A1 (es) | 1969-07-28 | 1969-07-28 | Procedimiento de fabricacion de un nuevo derivado dihidra- cinico de accion antituberculosa. |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2036935A1 DE2036935A1 (de) | 1971-02-18 |
| DE2036935B2 DE2036935B2 (de) | 1978-02-09 |
| DE2036935C3 true DE2036935C3 (de) | 1978-10-12 |
Family
ID=8453522
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2036935A Expired DE2036935C3 (de) | 1969-07-28 | 1970-07-24 | Diisonicotinsäurehydrazid-methansulfonat des d(+)2^>-(Äthylendiimino)-di-lbutanols, Verfahren zur Herstellung desselben und diese Verbindung enthaltende Arzneimittel |
Country Status (8)
| Country | Link |
|---|---|
| US (1) | US3718655A (enExample) |
| BE (1) | BE753862A (enExample) |
| CH (1) | CH517743A (enExample) |
| DE (1) | DE2036935C3 (enExample) |
| ES (1) | ES369952A1 (enExample) |
| FR (1) | FR2059568B1 (enExample) |
| GB (1) | GB1294299A (enExample) |
| ZA (1) | ZA705224B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH563356A5 (enExample) * | 1972-05-17 | 1975-06-30 | Esteve Dr Lab Del Sa | |
| KR820002345B1 (ko) * | 1981-07-07 | 1982-12-23 | 한국과학기술원 | 에탐부톨술폰산 유도체의 제조방법 |
| US7456222B2 (en) | 2002-05-17 | 2008-11-25 | Sequella, Inc. | Anti tubercular drug: compositions and methods |
| US7652039B2 (en) | 2002-05-17 | 2010-01-26 | Sequella, Inc. | Methods of use and compositions for the diagnosis and treatment of infectious disease |
| US20040033986A1 (en) * | 2002-05-17 | 2004-02-19 | Protopopova Marina Nikolaevna | Anti tubercular drug: compositions and methods |
| EP1670314A4 (en) * | 2003-09-05 | 2009-02-25 | Sequella Inc | METHODS AND COMPOSITIONS INCLUDE DIAMINE AS A NEW THERAPEUTIC FOR TUBERCULOSIS |
| US20090281054A1 (en) * | 2008-05-06 | 2009-11-12 | Venkata Reddy | Compositions and methods comprising capuramycin analogues |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2759944A (en) * | 1952-04-21 | 1956-08-21 | Erba Carlo Spa | Derivatives of carboxylic acid hydrazides and method of making them |
| US2923714A (en) * | 1958-02-13 | 1960-02-02 | Hoffmann La Roche | 1-picolinoyl-2-benzyl hydrazine and salts |
| DE1122064B (de) * | 1960-01-09 | 1962-01-18 | Basf Ag | Verfahren zur Einfuehrung von alyphatischen Kohlenwasserstoffresten in organische Verbindungen, die Hydroxylgruppen, tertiaere Aminogruppen, aromatische gebundene Sulfhydrylgruppen und bzw. oder aromatisch gebundene primaere oder sekundaere Aminogruppen enthalten |
-
1969
- 1969-07-28 ES ES369952A patent/ES369952A1/es not_active Expired
-
1970
- 1970-07-23 GB GB35706/70A patent/GB1294299A/en not_active Expired
- 1970-07-24 BE BE753862D patent/BE753862A/xx not_active IP Right Cessation
- 1970-07-24 DE DE2036935A patent/DE2036935C3/de not_active Expired
- 1970-07-28 ZA ZA705224*A patent/ZA705224B/xx unknown
- 1970-07-28 US US00059010A patent/US3718655A/en not_active Expired - Lifetime
- 1970-07-28 FR FR7027824A patent/FR2059568B1/fr not_active Expired
- 1970-07-28 CH CH1140270A patent/CH517743A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| ES369952A1 (es) | 1971-07-16 |
| BE753862A (fr) | 1970-12-31 |
| ZA705224B (en) | 1971-04-28 |
| FR2059568B1 (enExample) | 1974-08-30 |
| FR2059568A1 (enExample) | 1971-06-04 |
| US3718655A (en) | 1973-02-27 |
| DE2036935A1 (de) | 1971-02-18 |
| CH517743A (fr) | 1972-01-15 |
| DE2036935B2 (de) | 1978-02-09 |
| GB1294299A (en) | 1972-10-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) |