PL424708A1 - Chiral bicyclic imines based on trans-1,2-diaminocyclohexane and method for producing them - Google Patents
Chiral bicyclic imines based on trans-1,2-diaminocyclohexane and method for producing themInfo
- Publication number
- PL424708A1 PL424708A1 PL424708A PL42470818A PL424708A1 PL 424708 A1 PL424708 A1 PL 424708A1 PL 424708 A PL424708 A PL 424708A PL 42470818 A PL42470818 A PL 42470818A PL 424708 A1 PL424708 A1 PL 424708A1
- Authority
- PL
- Poland
- Prior art keywords
- diaminocyclohexane
- trans
- trifluromethyl
- ethylphenyl
- butylphenyl
- Prior art date
Links
- -1 bicyclic imines Chemical class 0.000 title abstract 12
- SSJXIUAHEKJCMH-PHDIDXHHSA-N (1r,2r)-cyclohexane-1,2-diamine Chemical compound N[C@@H]1CCCC[C@H]1N SSJXIUAHEKJCMH-PHDIDXHHSA-N 0.000 title abstract 4
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000003814 drug Substances 0.000 abstract 2
- 125000001624 naphthyl group Chemical group 0.000 abstract 2
- SSJXIUAHEKJCMH-WDSKDSINSA-N (1s,2s)-cyclohexane-1,2-diamine Chemical compound N[C@H]1CCCC[C@@H]1N SSJXIUAHEKJCMH-WDSKDSINSA-N 0.000 abstract 1
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical group C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 abstract 1
- 206010028980 Neoplasm Diseases 0.000 abstract 1
- 230000000844 anti-bacterial effect Effects 0.000 abstract 1
- 230000003178 anti-diabetic effect Effects 0.000 abstract 1
- 230000000840 anti-viral effect Effects 0.000 abstract 1
- 239000003472 antidiabetic agent Substances 0.000 abstract 1
- 238000011914 asymmetric synthesis Methods 0.000 abstract 1
- 201000011510 cancer Diseases 0.000 abstract 1
- 229940079593 drug Drugs 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000002243 precursor Substances 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
Landscapes
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
Zgłoszenie ujawnia Chiralne iminy cykliczne oparte na trans-1,2-diaminocykloheksanie o wzorze ogólnym 1, w którym R oznacza grupy: metylową, izopropylową, triflurometylową, fenylową, 3-etylofenylową, 4-tert-butylofenylową i 1-naftalenową przeznaczone są stosowania w medycynie jako środki zwalczające m.in. komórki rakowe. Związki te są przeznaczone do stosowania w chemii farmaceutycznej oraz w syntezie asymetrycznej jako prekursory leków. Tego typu pochodne oparte na pierścieniu heterocyklicznym, odgrywają ogromną rolę jako związki aktywne biologicznie wykazując m.in. właściwości przeciwbakteryjne, przeciwcukrzycowe, przeciwwirusowe. Przedmiotem zgłoszenia jest również sposób wytwarzania chiralnych imin cyklicznych opartych na trans-1,2-diaminocykloheksanie o wzorze ogólnym 1, w którym R oznacza grupę metylową, izopropylową, triflurometylową, fenylową, 3-etylofenylową, 4-tert-butylofenylową i naftylową charakteryzujący się tym, że (1R, 2R)1,2-diaminocykloheksan lub (1S,2S)-1,2-diaminocykloheksan, poddaje się reakcji z wybranymi ketoestrami o wzorze ogólnym 2, w którym R oznacza grupę metylową, izopropylową, triflurometylową, fenylową, 3-etylofenylową, 4-tert-butylofenylową i naftylową, w temperaturze 293 K, w środowisku rozpuszczalnika organicznego, a pozostałość oczyszcza się.The application discloses Chiral cyclic imines based on trans-1,2-diaminocyclohexane of general formula 1, wherein R is methyl, isopropyl, trifluromethyl, phenyl, 3-ethylphenyl, 4-tert-butylphenyl and 1-naphthalene groups are intended for use in medicine as a means of combating, among others cancer cells. These compounds are intended for use in pharmaceutical chemistry and in asymmetric synthesis as drug precursors. Derivatives of this type based on the heterocyclic ring play a huge role as biologically active compounds showing, among others antibacterial, antidiabetic and antiviral properties. The subject of the application is also a process for the preparation of chiral cyclic imines based on trans-1,2-diaminocyclohexane of general formula 1, wherein R is methyl, isopropyl, trifluromethyl, phenyl, 3-ethylphenyl, 4-tert-butylphenyl and naphthyl group characterized by this that (1R, 2R) 1,2-diaminocyclohexane or (1S, 2S) -1,2-diaminocyclohexane is reacted with selected ketoesters of general formula 2 in which R is methyl, isopropyl, trifluromethyl, phenyl, 3 -ethylphenyl, 4-tert-butylphenyl and naphthyl, at 293 K, in an organic solvent medium, and the residue is purified.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424708A PL231881B1 (en) | 2018-02-28 | 2018-02-28 | Chiral bicyclic imines based on trans-1,2-diaminocyclohexane and method for producing them |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PL424708A PL231881B1 (en) | 2018-02-28 | 2018-02-28 | Chiral bicyclic imines based on trans-1,2-diaminocyclohexane and method for producing them |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| PL424708A1 true PL424708A1 (en) | 2018-07-30 |
| PL231881B1 PL231881B1 (en) | 2019-04-30 |
Family
ID=62954734
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PL424708A PL231881B1 (en) | 2018-02-28 | 2018-02-28 | Chiral bicyclic imines based on trans-1,2-diaminocyclohexane and method for producing them |
Country Status (1)
| Country | Link |
|---|---|
| PL (1) | PL231881B1 (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL427827A1 (en) * | 2018-11-21 | 2019-05-20 | Politechnika Wroclawska | Bicyclic imines and enamines and method for producing them |
| PL427399A1 (en) * | 2018-10-15 | 2019-06-03 | Politechnika Wroclawska | Chirally substituted bicyclic imines based on trans 1,2-diaminocyclohexane and method for producing them |
| PL427400A1 (en) * | 2018-10-15 | 2019-07-29 | Politechnika Wrocławska | Method for obtaining bicyclic imines of (4aR,8aR)-4a,5,6,7,8,8a-hexahydroquinoxaline-2(1H)-one and 6,8-dimethylquinoxaline-2(1H)-one |
-
2018
- 2018-02-28 PL PL424708A patent/PL231881B1/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| PL427399A1 (en) * | 2018-10-15 | 2019-06-03 | Politechnika Wroclawska | Chirally substituted bicyclic imines based on trans 1,2-diaminocyclohexane and method for producing them |
| PL427400A1 (en) * | 2018-10-15 | 2019-07-29 | Politechnika Wrocławska | Method for obtaining bicyclic imines of (4aR,8aR)-4a,5,6,7,8,8a-hexahydroquinoxaline-2(1H)-one and 6,8-dimethylquinoxaline-2(1H)-one |
| PL427827A1 (en) * | 2018-11-21 | 2019-05-20 | Politechnika Wroclawska | Bicyclic imines and enamines and method for producing them |
| PL233209B1 (en) * | 2018-11-21 | 2019-09-30 | Politechnika Wroclawska | Bicyclic imines and enamines and method for producing them |
Also Published As
| Publication number | Publication date |
|---|---|
| PL231881B1 (en) | 2019-04-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| IL278297B2 (en) | Transmutable heterocyclic PTPN11 inhibitors | |
| MA42232B1 (en) | New amino acid derivatives, process for their preparation and pharmaceutical compositions containing them | |
| PE20040164A1 (en) | MIMETICS OF GLUCOCORTICOIDS, PROCEDURES FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS | |
| FR3037957B1 (en) | NOVEL HYDROXYESTER DERIVATIVES, PROCESS FOR PREPARING THEM AND PHARMACEUTICAL COMPOSITIONS CONTAINING SAME | |
| AR067896A1 (en) | PROCEDURE FOR SYNTHESIZING USEFUL COMPOUNDS TO TREAT HEPATITIS C | |
| CY1114702T1 (en) | NEW INTERIOR CLEAN BETA AGONISTS, METHOD OF PRODUCTION AND USE OF THEM AS MEDICINES | |
| MA45223B1 (en) | New piperidinyl derivatives substituted by (hetero) aryl, their preparation process and pharmaceutical compositions containing them | |
| NO20061406L (en) | Organic compounds | |
| AR093047A1 (en) | NITROGEN HETEROCICLICAL COMPOUNDS | |
| AR045999A1 (en) | ETER COMPOSITE OF PIPERIDINE, ITS USE FOR THE MANUFACTURE OF A MEDICINAL PRODUCT, PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND PROCEDURE TO PREPARE IT | |
| RU2019120181A (en) | Antimicrobial peptides | |
| PH12021550788A1 (en) | New amino-pyrimidonyl-piperidinyl derivatives, a process for their preparation and pharmaceutical compositions containing them | |
| RU2396264C2 (en) | Chromane derivatives and use thereof as 5-ht receptor ligands | |
| AR054508A1 (en) | BENCILPIPERAZINE COMPOSITE, ITS USE TO PREPARE A MEDICINAL PRODUCT, PROCEDURES FOR THE PREPARATION OF SUCH COMPOUND AND INTERMEDIATE COMPOUNDS, SUCH INTERMEDIARY COMPOUNDS, PHARMACEUTICAL COMPOSITION THAT INCLUDES IT AND PROCEDURE TO PREPARE IT | |
| EA200701856A1 (en) | TETRAHYDROPYRIDAZAZEPIN-8-ONE AND RELATED COMPOUNDS FOR THE TREATMENT OF SCHIZOPHRENIA | |
| UY29894A1 (en) | ACID DERIVATIVES (2 - ((2S) -2-HYDROXIPROPIL) OXI) PHENYL) ACETIC AND ACID (2 - ((2S) -2-HYDROXIPROPIL) OXI) PHENYL) PROPANOIC SUBSTITUTED, PHARMACEUTICAL COMPOSITIONS OF PREPARATION AND PROCEDURE APPLICATIONS | |
| CN105017036B (en) | There is the 2-(virtue aminoethylamino of bactericidal activity) benzyl alcohol compounds and application thereof | |
| PY2265622A (en) | PREPARATION OF THIAZOLYL-PIPERIDINYL COMPOUNDS CONTAINING PHENYLSULFILLIMINES OR SULFOXIMINES AND INTERMEDIATES THEREOF | |
| AR041026A1 (en) | DERIVATIVES OF ARIL- AND HETEROARILMORFOLINA, ITS USE IN THE PREPARATION OF A PHARMACEUTICAL MEDICINAL AND COMPOSITION | |
| EA201891691A1 (en) | ASYMMETRIC BENZOLSULPHONYLMOLECHENIA AND THEIR APPLICATION IN MEDICINE | |
| DK3194360T3 (en) | 4-OXO-N- (4-HYDROXYPHENYL) RETINAMIDE DERIVATIVES AS THERAPEUTIC AGENTS FOR TREATMENT OF CANCER | |
| TH106486A (en) | New types of 9-substrate-5-carboxy-oxadiazino-quinolone derivatives, their preparations and their use as antibacterial drugs. | |
| NZ801119A (en) | Certain chemical entities, compositions, and methods | |
| TH83933A (en) | 2-methyl-4-phenyl-5-oxo-1,4,5,6,7,8-hexahydroquinoline derivatives. | |
| TH1901006321A (en) | Substituted indoline derivatives inhibit dengue virus self-replication. |