NO177748B - Fremgangsmåte for å redusere en karbonylinneholdende acridin - Google Patents
Fremgangsmåte for å redusere en karbonylinneholdende acridin Download PDFInfo
- Publication number
- NO177748B NO177748B NO911255A NO911255A NO177748B NO 177748 B NO177748 B NO 177748B NO 911255 A NO911255 A NO 911255A NO 911255 A NO911255 A NO 911255A NO 177748 B NO177748 B NO 177748B
- Authority
- NO
- Norway
- Prior art keywords
- lower alkyl
- solvent
- formula
- alkali metal
- platinum
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims abstract 11
- DZBUGLKDJFMEHC-UHFFFAOYSA-N acridine Chemical compound C1=CC=CC2=CC3=CC=CC=C3N=C21 DZBUGLKDJFMEHC-UHFFFAOYSA-N 0.000 title claims abstract 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 title claims abstract 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 7
- 239000001257 hydrogen Substances 0.000 claims abstract 7
- 150000002431 hydrogen Chemical group 0.000 claims abstract 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract 2
- 229910052736 halogen Inorganic materials 0.000 claims abstract 2
- 150000002367 halogens Chemical class 0.000 claims abstract 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims 9
- 125000000217 alkyl group Chemical group 0.000 claims 7
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical group [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 6
- 239000002904 solvent Substances 0.000 claims 5
- 229910052783 alkali metal Inorganic materials 0.000 claims 4
- 150000001340 alkali metals Chemical class 0.000 claims 4
- 239000002585 base Substances 0.000 claims 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical group [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims 3
- 239000003054 catalyst Substances 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 2
- 235000010290 biphenyl Nutrition 0.000 claims 2
- 239000004305 biphenyl Substances 0.000 claims 2
- 125000006267 biphenyl group Chemical group 0.000 claims 2
- 229910000510 noble metal Inorganic materials 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims 2
- 229910052697 platinum Inorganic materials 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 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 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 150000001251 acridines Chemical class 0.000 claims 1
- 150000004703 alkoxides Chemical class 0.000 claims 1
- 125000003282 alkyl amino group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 claims 1
- PQVSTLUFSYVLTO-UHFFFAOYSA-N ethyl n-ethoxycarbonylcarbamate Chemical compound CCOC(=O)NC(=O)OCC PQVSTLUFSYVLTO-UHFFFAOYSA-N 0.000 claims 1
- 150000004677 hydrates Chemical class 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- GLXDVVHUTZTUQK-UHFFFAOYSA-M lithium hydroxide monohydrate Substances [Li+].O.[OH-] GLXDVVHUTZTUQK-UHFFFAOYSA-M 0.000 claims 1
- 229940040692 lithium hydroxide monohydrate Drugs 0.000 claims 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 claims 1
- 150000003057 platinum Chemical class 0.000 claims 1
- 229910003446 platinum oxide Inorganic materials 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 125000001544 thienyl group Chemical group 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
- C07D219/04—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems 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 carbon atoms of the ring system
- C07D219/08—Nitrogen atoms
- C07D219/10—Nitrogen atoms attached in position 9
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Chemically Coating (AREA)
- Encapsulation Of And Coatings For Semiconductor Or Solid State Devices (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Cephalosporin Compounds (AREA)
- Manufacturing Of Electric Cables (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Chemical Treatment Of Metals (AREA)
- Saccharide Compounds (AREA)
- Pyridine Compounds (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Catalysts (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Carbon And Carbon Compounds (AREA)
- Mechanical Treatment Of Semiconductor (AREA)
- Electrical Discharge Machining, Electrochemical Machining, And Combined Machining (AREA)
- Electroplating Methods And Accessories (AREA)
- Manufacturing Of Printed Wiring (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Claims (9)
1.
Fremgangsmåte for redusering av et karbonylinneholdende acridinderivat med formel I til en forbindelse med formel:
der n er 1, 2 eller 3 og X er hydrogen, halogen eller trifluormetyl; R^ er hydrogen, laverealkyl, dilaverealkyl-aminolaverealkyl, fenyllaverealkyl, difenyllaverealkyl, thienyllaverealkyl, oksygen-brobundet fenyllaverealkyl, oksygen-brobundet difenyllaverealkyl, karakterisert ved at den omfatter reaksjon av nevnte karbonylinneholdende acridin med en edelmetallkatalysator under hydrogentrykk i nærvær av en alkalimetallbase i et passende oppløsningsmiddel fortrinnsvis et laverealkanol-oppløsningsmiddel som har 2 til 8 karbonatomer valgt fra gruppen etanol, 1-propanol, 2-propanol og 1-butanol, og ved en forhøyet temperatur fortrinnsvis 40-100°C.
2.
Fremgangsmåte ifølge krav 1, karakterisert ved at edelmetallkatalysatoren er platina, platinaoksid eller et platinasalt.
3.
Fremgangsmåte ifølge krav 1, karakterisert ved at alkalimetallbasen blir valgt fra 1itiumhydroksid og dens hydrater, natriumhydroksid og lavere alkoksider._av natrium eller litium.
4.
Fremgangsmåte ifølge krav 3, karakterisert ved at alkalimetallbasen er natriumhydroksid eller litiumhydroksidmonohydrat.
5.
Fremgangsmåte ifølge krav 1, karakterisert ved at oppløsningsmidlet er 1-butanol.
6.
Fremgangsmåte ifølge krav 1, karakterisert ved at 2 til 1056 v/v vann blir tilsatt oppløsningsmidlet.
7.
Fremgangsmåte ifølge krav 1, karakterisert ved at temperaturen er 60-80"C.
8.
Fremgangsmåte ifølge krav 1, karakterisert ved at katalysatoren er platina, alkalimetallbasen er litiumhydroksid og oppløsningsmidlet er 1-butanol.
9.
Fremgangsmåte ifølge krav 1, karakterisert ved at forbindelsen med formel Ia
der R1=H, X=Hogn=2,
eller et farmasøytisk aksepterbart syreaddisjonssalt derav reduseres til en forbindelse med formel Ila
eller et farmasøytisk aksepterbart syreaddisjonssalt derav.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/500,967 US5053513A (en) | 1990-03-29 | 1990-03-29 | Method of reducing a carbonyl containing acridine |
Publications (4)
| Publication Number | Publication Date |
|---|---|
| NO911255D0 NO911255D0 (no) | 1991-03-27 |
| NO911255L NO911255L (no) | 1991-09-30 |
| NO177748B true NO177748B (no) | 1995-08-07 |
| NO177748C NO177748C (no) | 1995-11-15 |
Family
ID=23991612
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO911255A NO177748C (no) | 1990-03-29 | 1991-03-27 | Fremgangsmåte for å redusere en karbonylinneholdende acridin |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US5053513A (no) |
| EP (1) | EP0449172B1 (no) |
| JP (1) | JPH07113017B2 (no) |
| KR (1) | KR0178275B1 (no) |
| CN (1) | CN1032649C (no) |
| AT (1) | ATE138913T1 (no) |
| AU (1) | AU640759B2 (no) |
| BR (1) | BR9101252A (no) |
| CA (1) | CA2039318A1 (no) |
| CS (1) | CS83591A2 (no) |
| DE (1) | DE69119961T2 (no) |
| DK (1) | DK0449172T3 (no) |
| ES (1) | ES2099717T3 (no) |
| FI (1) | FI98366C (no) |
| GR (1) | GR3020518T3 (no) |
| HU (1) | HUT57732A (no) |
| IE (1) | IE76463B1 (no) |
| IL (1) | IL97697A (no) |
| NO (1) | NO177748C (no) |
| NZ (1) | NZ237603A (no) |
| PL (1) | PL165759B1 (no) |
| PT (1) | PT97196B (no) |
| RU (1) | RU2069659C1 (no) |
| ZA (1) | ZA912365B (no) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5210087A (en) * | 1991-02-13 | 1993-05-11 | Hoechst-Roussel Pharmaceuticals Inc. | 9-aminotetrahydroacridines and related compounds |
| RU2024509C1 (ru) * | 1991-05-07 | 1994-12-15 | Всероссийский научный центр по безопасности биологически активных веществ | Производные 9-аминоакридина или их соли с органическими или неорганическими кислотами, проявляющие психотропную, антиамнестическую и липидрегулирующую активность |
| US5247091A (en) * | 1992-07-30 | 1993-09-21 | Hoechst Celanese Corporation | Preparation of enamines in aqueous media |
| ES2059263B1 (es) * | 1992-10-27 | 1995-10-01 | Vita Invest Sa | Procedimiento para la obtencion del (+)-9-amino-1,2,3,4-tetrahidroacridin-1-ol. |
| GB201312228D0 (en) | 2013-07-08 | 2013-08-21 | Ludlow Michael | A lip skin and a method and apparatus for forming a lip skin |
| RU2567388C1 (ru) * | 2014-12-10 | 2015-11-10 | Открытое акционерное общество "Нижегородский химико-фармацевтический завод" | Способ получения 9-бутиламино-3,3-диметил-3,4-дигидроакридин-1(2н)-она гидрохлорида |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4835275A (en) * | 1984-10-25 | 1989-05-30 | Hoechst-Roussel Pharmaceuticals, Inc. | Method of preparing 9-amino-1,2,3,4,-tetrahydroacridin-1-ones and related compounds |
| US4695573A (en) * | 1984-10-25 | 1987-09-22 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| US4631286A (en) * | 1984-10-25 | 1986-12-23 | Hoechst-Roussel Pharmaceuticals Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| DE3582995D1 (de) * | 1984-10-25 | 1991-07-04 | Hoechst Roussel Pharma | 9-amino-1,2,3,4-tetrahydroacridin-1-ol und verwandte verbindungen, verfahren zu ihrer herstellung und verwendung als arzneimittel. |
| US4754050A (en) * | 1984-10-25 | 1988-06-28 | Hoechst-Roussel Pharmaceuticals, Inc. | 9-amino-1,2,3,4-tetrahydroacridin-1-ol and related compounds |
| US4851536A (en) * | 1987-05-07 | 1989-07-25 | American Home Products Corporation | Cyclohexylquinolines as inhibitors of interleukin 1 |
| US4868177A (en) * | 1988-11-09 | 1989-09-19 | Hoechst-Roussel Pharmaceuticals, Inc. | 1,2,3,4-tetrahydro-1,9-acridinediamines, pharmaceutical compositions and use |
| GB8827704D0 (en) * | 1988-11-28 | 1988-12-29 | Fujisawa Pharmaceutical Co | New acridine derivatives & processes for their production |
| US5155226A (en) * | 1991-02-19 | 1992-10-13 | Hoechst-Roussel Pharmaceuticals Incorporated | Method for the preparation of 9-amino-1,2,3,4-tetrahydroacridine |
-
1990
- 1990-03-29 US US07/500,967 patent/US5053513A/en not_active Expired - Fee Related
-
1991
- 1991-03-25 AT AT91104661T patent/ATE138913T1/de not_active IP Right Cessation
- 1991-03-25 DE DE69119961T patent/DE69119961T2/de not_active Expired - Fee Related
- 1991-03-25 DK DK91104661.3T patent/DK0449172T3/da active
- 1991-03-25 EP EP91104661A patent/EP0449172B1/en not_active Expired - Lifetime
- 1991-03-25 ES ES91104661T patent/ES2099717T3/es not_active Expired - Lifetime
- 1991-03-27 CS CS91835A patent/CS83591A2/cs unknown
- 1991-03-27 NZ NZ237603A patent/NZ237603A/en unknown
- 1991-03-27 KR KR1019910004757A patent/KR0178275B1/ko not_active IP Right Cessation
- 1991-03-27 FI FI911513A patent/FI98366C/fi active
- 1991-03-27 IL IL9769791A patent/IL97697A/en not_active IP Right Cessation
- 1991-03-27 NO NO911255A patent/NO177748C/no unknown
- 1991-03-28 JP JP3087252A patent/JPH07113017B2/ja not_active Expired - Lifetime
- 1991-03-28 IE IE107091A patent/IE76463B1/en not_active IP Right Cessation
- 1991-03-28 CA CA002039318A patent/CA2039318A1/en not_active Abandoned
- 1991-03-28 BR BR919101252A patent/BR9101252A/pt unknown
- 1991-03-28 ZA ZA912365A patent/ZA912365B/xx unknown
- 1991-03-28 CN CN91101914A patent/CN1032649C/zh not_active Expired - Fee Related
- 1991-03-28 RU SU914895044A patent/RU2069659C1/ru active
- 1991-03-28 PL PL91289656A patent/PL165759B1/pl unknown
- 1991-03-28 PT PT97196A patent/PT97196B/pt not_active IP Right Cessation
- 1991-03-28 AU AU73870/91A patent/AU640759B2/en not_active Ceased
- 1991-03-29 HU HU911055A patent/HUT57732A/hu unknown
-
1996
- 1996-07-11 GR GR960401878T patent/GR3020518T3/el unknown
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