CS230342B1 - Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol- -2-karboxylovej a sposob jeho přípravy - Google Patents
Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol- -2-karboxylovej a sposob jeho přípravy Download PDFInfo
- Publication number
- CS230342B1 CS230342B1 CS88283A CS88283A CS230342B1 CS 230342 B1 CS230342 B1 CS 230342B1 CS 88283 A CS88283 A CS 88283A CS 88283 A CS88283 A CS 88283A CS 230342 B1 CS230342 B1 CS 230342B1
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- carboxylic acid
- indole
- dihydropyrrolo
- furo
- methanol
- Prior art date
Links
- 239000002253 acid Substances 0.000 title claims description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 12
- 238000006243 chemical reaction Methods 0.000 claims description 9
- -1 heterocyclic nitrogen compounds Chemical class 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- HCUARRIEZVDMPT-UHFFFAOYSA-N Indole-2-carboxylic acid Chemical compound C1=CC=C2NC(C(=O)O)=CC2=C1 HCUARRIEZVDMPT-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 8
- 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 claims description 7
- IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 0.000 claims description 7
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 claims description 6
- 239000011541 reaction mixture Substances 0.000 claims description 5
- 239000002904 solvent Substances 0.000 claims description 5
- 230000015572 biosynthetic process Effects 0.000 claims description 4
- 238000009835 boiling Methods 0.000 claims description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000005259 measurement Methods 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 150000003138 primary alcohols Chemical class 0.000 claims description 3
- 150000003333 secondary alcohols Chemical class 0.000 claims description 3
- 230000003595 spectral effect Effects 0.000 claims description 3
- 238000003786 synthesis reaction Methods 0.000 claims description 3
- DZLFRQHFFVRYEE-UHFFFAOYSA-N 1h-indole-2-carbohydrazide Chemical compound C1=CC=C2NC(C(=O)NN)=CC2=C1 DZLFRQHFFVRYEE-UHFFFAOYSA-N 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 150000001540 azides Chemical class 0.000 claims description 2
- 238000000921 elemental analysis Methods 0.000 claims description 2
- ZXWUDCWRJHLBNL-UHFFFAOYSA-N ethyl 4h-furo[3,2-b]indole-2-carboxylate Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)OCC)O2 ZXWUDCWRJHLBNL-UHFFFAOYSA-N 0.000 claims description 2
- 125000004494 ethyl ester group Chemical group 0.000 claims description 2
- 150000004820 halides Chemical class 0.000 claims description 2
- 238000002329 infrared spectrum Methods 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 239000012452 mother liquor Substances 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 229910017464 nitrogen compound Inorganic materials 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 238000001228 spectrum Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 claims description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 claims 2
- 238000005160 1H NMR spectroscopy Methods 0.000 claims 1
- KFHFDJDODKQNHH-UHFFFAOYSA-N N1C(=CC2=C1C=1NC3=CC=CC=C3C=1O2)C(=O)NN Chemical compound N1C(=CC2=C1C=1NC3=CC=CC=C3C=1O2)C(=O)NN KFHFDJDODKQNHH-UHFFFAOYSA-N 0.000 claims 1
- 238000005481 NMR spectroscopy Methods 0.000 claims 1
- 235000021168 barbecue Nutrition 0.000 claims 1
- 239000002178 crystalline material Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 238000002360 preparation method Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- NKGUHSIMKXPTGH-UHFFFAOYSA-N 4h-furo[3,2-b]indole-2-carboxylic acid Chemical compound N1C2=CC=CC=C2C2=C1C=C(C(=O)O)O2 NKGUHSIMKXPTGH-UHFFFAOYSA-N 0.000 description 3
- IOVCWXUNBOPUCH-UHFFFAOYSA-N Nitrous acid Chemical compound ON=O IOVCWXUNBOPUCH-UHFFFAOYSA-N 0.000 description 1
- PPWHTZKZQNXVAE-UHFFFAOYSA-N Tetracaine hydrochloride Chemical compound Cl.CCCCNC1=CC=C(C(=O)OCCN(C)C)C=C1 PPWHTZKZQNXVAE-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000005077 diacylhydrazine group Chemical group 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 239000012429 reaction media Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
POPIS VYNÁLEZU'' V»,1' ‘A K autorskému osvekeniu 230342 (11) (11)
(22) Přihlášené 09 02 83(21) (PV 882-83) (40) Zverejnené 25 11 83 (51) Int. Cl.»C 07 D 491/147 úRad pro vynálezy
A OBJEVY (45) Vydané 15 10 86 (75)
Autor vynálezu KOŘENOVÁ ANNA RNDr, KRUTOŠÍKOVÁ ALŽBĚTA doc. ing. CSc,KOVÁČ JAROSLAV prof. ing. DrSc, BRATISLAVA (54) Hydrazid kyseliny 1,9-dihydropyrolo [2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol--2-karboxylovej a sposob jeho přípravy 1
Hydrazidy karboxylových kyselin možnopřipravit niekolkými sposobmi.
Syntéza hydrazidov reakciou karboxylo-vých kyselin s hydrazínom je najmenej vhod-ná metoda, lebo vyžaduje eliminovat z re-akčného prostredia vodu. Nevýhoda přípra-vy hydrazidov z chloridov a anhydridov ky-selin spočívá v tom, že bez ohl'adu na mo-lárny poměr oboch reakčných komponentovproduktom bývajú diacylhydrazíny. Za naj-výhodnejšiu metodu sa pokládá přípravahydrazidov využitím esterov karboxylovýchkyselin ako východiskových látok. Z prepa-ratívneho hladiska bola táto reakcia pre-skúmaná už Curtiom a spolupracovníkmi[Chem. Ber. 35, 3229(1902)]. Prebytkom hyd-razínu možno potlačit vznik N,N-diacylhyd-razínu, ktorý vzniká ako vedlajší produktreakcie.
Stúdiom literatury sa ukázalo, že hydrazidkyseliny l,9-dihydropyrolo[2‘,3‘:4,5]furo-[3,2-b]indol-2-karboxylovej nebol doterazpřipravený.
Predmetom vynálezu je hydrazid kyseliny1,9-dihydropyrolo [ 2‘,3‘:4,5 ] furo'[ 3,2-b ] indol--2-karboxylovej vzorca I
(I ) a sposob jeho přípravy.
Podstata sposobu přípravy hydrazidu ky-seliny l,9-dihydropyrolo[2‘,3‘:4,5]furo-[ 3,2-b]indol-2-karboxylovej spočívá v tom,že sa na etylester kyseliny 1,9-dihydropyro-lo [ 2‘,3‘: 4,5 ]furtí[ 3,2-b ] indol-2-karboxylovej(Čsl. aut. osvědč. 193 130) vzorca II
230342 (íl)
Claims (2)
1. Hydrazid kyseliny 1,9-dihydropyrolo-[ 2‘ ,3 ‘: 4,5 j fůro [ 3,2-b ] indol-2-karboxylove jvzorca I vynalezu lo[ 2‘,3‘: 4,5 j fůro [ 3,2-b j indol-2-karboxylovejvzorca II
(I )
2. Spůsob přípravy hydrazidu kyseliny 1,9--dihydropyrolo [ 2 ‘, 3‘: 4,5 ] fůro [ 3,2-b ] indol-2--karboxylovej podlá bodu 1, vyznačený tým,že sa na etylester kyseliny 1,9-dihydropyro- působí hydrazínhydrátom v metanole, etanole alebo vyšších primárných alebo sekundárnych alkoholoch pri teplote varu rozpúšfadla.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88283A CS230342B1 (cs) | 1983-02-09 | 1983-02-09 | Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol- -2-karboxylovej a sposob jeho přípravy |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS88283A CS230342B1 (cs) | 1983-02-09 | 1983-02-09 | Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol- -2-karboxylovej a sposob jeho přípravy |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS230342B1 true CS230342B1 (cs) | 1984-08-13 |
Family
ID=5341828
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS88283A CS230342B1 (cs) | 1983-02-09 | 1983-02-09 | Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol- -2-karboxylovej a sposob jeho přípravy |
Country Status (1)
| Country | Link |
|---|---|
| CS (1) | CS230342B1 (cs) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407854A (zh) * | 2018-08-17 | 2019-11-05 | 北京加科思图新药研发有限公司 | 新的四环化合物 |
-
1983
- 1983-02-09 CS CS88283A patent/CS230342B1/cs unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110407854A (zh) * | 2018-08-17 | 2019-11-05 | 北京加科思图新药研发有限公司 | 新的四环化合物 |
| CN110407854B (zh) * | 2018-08-17 | 2020-09-15 | 北京加科思新药研发有限公司 | 新的四环化合物 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Blicke et al. | Reactions of 1, 3-Dimethyl-5, 6-diaminouracil | |
| AU2017284702B2 (en) | Pyrrolopyrimidine crystal for preparing JAK inhibitor | |
| US3047462A (en) | Quinazolone anti-inflammatory composition | |
| CH398626A (de) | Verfahren zur Herstellung neuer Pyrazolopyrimidine | |
| SU978730A3 (ru) | Способ получени этилового эфира 9-фенилгидразоно-6-метил-4-оксо-6,7,8,9-тетрагидро-4н-пиридо/1,2-а/-пиримидин-3-карбоновой кислоты | |
| JPS61178983A (ja) | スピロ−第４級アンモニウムハロゲン化物類およびその製法 | |
| EP0264081B1 (de) | Oxadiazolylalkylpurin-Derivate, ihre Herstellung und ihre Verwendung in pharmazeutischen Mitteln | |
| DE69226157T2 (de) | Antiallergische, entzündungshemmende und anti-PAF Pyridazinverbindungen | |
| US4960773A (en) | Xanthine derivatives | |
| CH396926A (de) | Verfahren zur Herstellung neuer Pyrazolopyrimidine | |
| KR20040007683A (ko) | 잘레플론의 제조 방법 | |
| AU611235B2 (en) | Process for preparing bis(3,5-dioxpiperazinyl) alkanes or alkenes | |
| CS204005B2 (en) | Process for preparing 2-brom-6-fluor-n-2-imidazolidinylidenbenzamine and additive salts with acids thereof | |
| CS230342B1 (cs) | Hydrazid kyseliny 1,9-dihydropyrolo[2‘,3‘: 4,5 ] fůro[ 3,2-b Jindol- -2-karboxylovej a sposob jeho přípravy | |
| Wiley et al. | Hydrogen cyanide chemistry. 6. Cyanogen condensation with cyanide, C7N7 | |
| SE437030B (sv) | 3-substituerade tetrahydro-pyrrolo/1,2-a/pyrimidiner, forfarande for framstellning derav och farmaceutiska preparat innehallande dessa foreningar | |
| DE69027300T2 (de) | 1,2-dihydro-2-oxoquinoxalinderivate, deren herstellung und verwendung in der therapie | |
| JPS6322562A (ja) | 強心性、ホスホジエステラ−ゼ画分１１１抑制性及び／又は腎血管拡張性を持った４−窒素置換イソキノリノ−ル化合物 | |
| CS226929B1 (en) | Hydrazides of furo (3,2-b)pyrol-5-carboxylic acids and method of preparing same | |
| Hajpál et al. | Synthesis of as‐triazino [5, 6‐b] quinoline, a new heterocyclic ring system | |
| RU2777444C1 (ru) | 1-(Фенил(фенилимино)метил) пирролидин-2,5-дион и способ его получения | |
| CA1051901A (en) | Derivatives of furo(2,3-d) pyrazolo(3,4-b) pyridines | |
| SU417424A1 (cs) | ||
| JPS60222484A (ja) | １，４−オキサチイノ〔２，３−ｃ〕ピロ−ル誘導体の製造法 | |
| US3654276A (en) | Process for manufacturing imidazoles |