SU1066997A1 - New heterocyclic triazaspiro-condensed systems - Google Patents
New heterocyclic triazaspiro-condensed systems Download PDFInfo
- Publication number
- SU1066997A1 SU1066997A1 SU823468037A SU3468037A SU1066997A1 SU 1066997 A1 SU1066997 A1 SU 1066997A1 SU 823468037 A SU823468037 A SU 823468037A SU 3468037 A SU3468037 A SU 3468037A SU 1066997 A1 SU1066997 A1 SU 1066997A1
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- triazaspiro
- new heterocyclic
- condensed systems
- methyl
- systems
- Prior art date
Links
- 125000000623 heterocyclic group Chemical group 0.000 title description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 6
- VEYNLAQGTLTBPG-UHFFFAOYSA-N 4-bromo-1-methylpiperidine-4-carbaldehyde Chemical compound CN1CCC(Br)(C=O)CC1 VEYNLAQGTLTBPG-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 2
- -1 N-methyl-4-bromo-formylpiperidine hydrobromide Chemical compound 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 2
- LKIYWJKEOOFVCV-UHFFFAOYSA-N 1-methylpiperidine-4-carbaldehyde Chemical compound CN1CCC(C=O)CC1 LKIYWJKEOOFVCV-UHFFFAOYSA-N 0.000 description 1
- LMVVXOINJRUNNR-UHFFFAOYSA-N 4-bromo-1-methylpiperidine-4-carbaldehyde;hydrobromide Chemical compound Br.CN1CCC(Br)(C=O)CC1 LMVVXOINJRUNNR-UHFFFAOYSA-N 0.000 description 1
- JYZKVJLQFGCECG-UHFFFAOYSA-N 4-hydroxy-1,2,5-trimethylpiperidine-4-carbonitrile Chemical compound CC1CC(O)(C#N)C(C)CN1C JYZKVJLQFGCECG-UHFFFAOYSA-N 0.000 description 1
- ATRRKUHOCOJYRX-UHFFFAOYSA-N Ammonium bicarbonate Chemical compound [NH4+].OC([O-])=O ATRRKUHOCOJYRX-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 1
- 229960000583 acetic acid Drugs 0.000 description 1
- AZDRQVAHHNSJOQ-UHFFFAOYSA-N alumane Chemical compound [AlH3] AZDRQVAHHNSJOQ-UHFFFAOYSA-N 0.000 description 1
- 239000001099 ammonium carbonate Substances 0.000 description 1
- 235000012501 ammonium carbonate Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- QPMLSUSACCOBDK-UHFFFAOYSA-N diazepane Chemical compound C1CCNNCC1 QPMLSUSACCOBDK-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012362 glacial acetic acid Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 230000000506 psychotropic effect Effects 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Hydrogenated Pyridines (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
НОВЫЕ ГЕТЕРОЦИКЛИЧЕСКИЕ ТРИАЗАСПИРО-КОНДЕНСИРОВАННЫЕ СИСТЕМЫ , Общей формулы НИЧсНг)гКН IT in, 2; п 3. |где пNEW HETEROCYCLIC TRIAZASPIRO-CONDENSED SYSTEMS, General Formula NICHSNg) GKN IT in, 2; n 3. | where n
Description
о ;о ;оLtd
ч Изобретение относитс к новым гетероциклическим триазаспиро-конденсированным системам, общей формулы нк-(сн,)й-ж 1 где п 2(а); п 3(6). которые могут найти применение в синтезе биологически активных соед нений. Известно, что пиперазиновый, пиперидиновый и пергидродиазепиновый циклы составл ют структурную о нову многих лекарственных средств и биологически активных соединений Cli. Известны М-замещенные-1-фенил-4 -оксо-1, 3,8-триазаспирО- (4,5 -дека ны, обладающие психотропными свойснгОсно J%- N-СНзСООН The invention relates to novel heterocyclic triazaspiro-condensed systems, of the general formula nk- (cn)-1, where n 2 (a); n 3 (6). which can be used in the synthesis of biologically active compounds. The piperazine, piperidine and perhydrodiazepine cycles are known to constitute the structural basis of many drugs and the biologically active compounds of Cli. Known M-substituted-1-phenyl-4-oxo-1, 3,8-triazaspirO- (4,5-deca that have psychotropic properties, it’s J% - N-CH 2 COOH
г g
HN-(CHz),rN NПример 1. Гидробромид N-метил-4-бром-4-формилпиперидина (III) К 25 мл лед ной уксусной кислоты при охлаждении лед ной водой прибавл ют 7,65 г (0,06 моль) Ы-метил-4-формилпиперидина , затем при перемешива-нии , по мере обесцвечивани , прикапывают 13 г (0,08 моль) брома, поддержива температуру реакционней смеси в пределах 18-20 С. После этого перемешивание продолжают при комнатной температуре еще в течение 1,5 ч. При этом выпадает гидробромид N-мeтил-4-бpoм-фopмилпипepидинa. Осадок разбавл ют 100 мл сухого эфира , отфильтровывают, промывают эфиром и сушат в вакуум-эксикаторе. Выход 16,5 г (96%). Продукт достаточно чист, но при необходимости его можно перекристаллизовать из ацетона ствами С21 и 7,8,10-триметил-1,3,8-триазаспиро- (4,S)-декан-2,4-Дион, получающийс взаимодействием 1,2,5-триметил-4-окси-4-цианопиперидина с карбонатом аммони if 31. Целью изобретени вл етс изыскание новых гетероциклических триазаспиро-конденсированных систем. Цель достигаетс новыми гетероциклическими триазаспиро-конденсированньами системами общей формулы I, которые могут быть получены путем взаимодействи гидробромида N-метил-4-бром-4-формилпиперидина с этилендиамином (дл соединени формулы 1а) или 1,3-диаминопропаном (дл соединени формулы 1б) с последующим восстановлением полученного соединени в среде третичного бутилового спирта при нагревании и повышенном давлении водорода в присутствии Ni-Рене (дл получени соединени формулы 1а) или восстановлением алюмогидридсш лити по следующей схеме: У н.т;(сн,ута,, . .л СНО 2.3 111 с прибавлением сухого эфира, т.пл. 155-156«С. Найдено,%: С 29,40; Н 4,34; N 4,83; Вг- 28,00. С,Нч5 NOBrg Вычислено,%: С 29,29; Н 4,56; N 4,88; Вт- 27,84. ИК-спектр, ), см : 1710 () , 2735 (С-Н альдегид). Пример 2. 9-Метил-А -1,4, 9-триазаспиро-(5,5)-ундекан (IVa). .. : К смеси 14 г углекислого кали , 5 мл воды, 30 мл ацетонитрила, 5,1 г (0,06 моль) 70%-ного раствора этилендис1мина при перемешивании в течение10 мин прикапывают раствор 17,2 г (0,06 моль) гидробромида N-метил-4-бром-4-формилпиперидина (III) в 25 мл ацетонитрила и 15 млHN- (CHz), rN N Example 1. N-methyl-4-bromo-4-formylpiperidine (III) hydrobromide To 25 ml of glacial acetic acid, while cooling with ice water, add 7.65 g (0.06 mol) N -methyl-4-formylpiperidine, then with stirring, as the discoloration, 13 g (0.08 mol) of bromine are added dropwise, maintaining the temperature of the reaction mixture within 18-20 C. After that, the stirring is continued at room temperature for 1 more , 5 h. At the same time N-methyl-4-bromo-formylpiperidine hydrobromide falls out. The precipitate is diluted with 100 ml of dry ether, filtered off, washed with ether and dried in a vacuum desiccator. Yield 16.5 g (96%). The product is sufficiently pure, but if necessary, it can be recrystallized from acetone with C21 and 7,8,10-trimethyl-1,3,8-triazaspiro- (4, S) -decan-2,4-Dione, obtained by the interaction of 1,2 , 5-trimethyl-4-hydroxy-4-cyanopiperidine with ammonium carbonate if 31. The aim of the invention is to find new heterocyclic triazaspiro-condensed systems. The objective is achieved by new heterocyclic triazaspiro condensate systems of general formula I, which can be obtained by reacting N-methyl-4-bromo-4-formylpiperidine hydrobromide with ethylenediamine (for compound of formula 1a) or 1,3-diaminopropane (for compound of formula 1b) with subsequent reduction of the obtained compound in a tertiary butyl alcohol medium under heating and elevated hydrogen pressure in the presence of Ni-Rene (to prepare a compound of formula 1a) or by reduction of the aluminum hydride trace The following scheme: Y Nt; (Sn, Uta ,,.. CHO 2.3 111 with the addition of dry ether, mp. 155-156 "C. Found,%: C 29.40; H 4.34; N 4.83; Br-28.00. C, Hf5 NOBrg Calculated,%: C 29.29; H 4.56; N 4.88; W- 27.84. IR spectrum,), cm: 1710 () , 2735 (C-H aldehyde). Example 2. 9-Methyl-A -1,4, 9-triazaspiro- (5.5) -undecane (IVa). ..: A mixture of 14.2 g (0.06 mol) is added dropwise to a mixture of 14 g of potassium carbonate, 5 ml of water, 30 ml of acetonitrile, 5.1 g (0.06 mol) of a 70% ethylenediamine solution under stirring for 10 min. ) N-methyl-4-bromo-4-formylpiperidine (III) hydrobromide in 25 ml of acetonitrile and 15 ml
Claims (2)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU823468037A SU1066997A1 (en) | 1982-07-09 | 1982-07-09 | New heterocyclic triazaspiro-condensed systems |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| SU823468037A SU1066997A1 (en) | 1982-07-09 | 1982-07-09 | New heterocyclic triazaspiro-condensed systems |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU1066997A1 true SU1066997A1 (en) | 1984-01-15 |
Family
ID=21021637
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU823468037A SU1066997A1 (en) | 1982-07-09 | 1982-07-09 | New heterocyclic triazaspiro-condensed systems |
Country Status (1)
| Country | Link |
|---|---|
| SU (1) | SU1066997A1 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013101A1 (en) * | 1991-12-27 | 1993-07-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridonecarboxylate compound, pharmaceutical use thereof, and spiro compound |
-
1982
- 1982-07-09 SU SU823468037A patent/SU1066997A1/en active
Non-Patent Citations (1)
| Title |
|---|
| 1. Машковский М.Д. Лекарственные средства. М., Медицина, 1978, I, с. 166, 168, III, с. 63. 2.Международна за вка 81/01554, кл. С 07 D 413/06, 413/14, 471/04, опублик. 1981. 3.Вартан н С.А., Тосун н А.О., Мёшак н В.Н. Синтез и превращени 1,2,5-триметил-4-аминопиперидин-4-карбоновойкислоты. Арм.хим.ж. 25, 2, 163 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1993013101A1 (en) * | 1991-12-27 | 1993-07-08 | Yoshitomi Pharmaceutical Industries, Ltd. | Pyridonecarboxylate compound, pharmaceutical use thereof, and spiro compound |
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