SU554815A3 - Способ получени производных симмтриазоло-(4,3-а)-хинолина или их солей - Google Patents
Способ получени производных симмтриазоло-(4,3-а)-хинолина или их солейInfo
- Publication number
- SU554815A3 SU554815A3 SU1895868A SU1895868A SU554815A3 SU 554815 A3 SU554815 A3 SU 554815A3 SU 1895868 A SU1895868 A SU 1895868A SU 1895868 A SU1895868 A SU 1895868A SU 554815 A3 SU554815 A3 SU 554815A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- quinoline
- triazolo
- salts
- simmtriazolo
- reaction mixture
- Prior art date
Links
- 238000000034 method Methods 0.000 title description 5
- 150000003839 salts Chemical class 0.000 title description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 11
- 239000011541 reaction mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- -1 OKCjrrpyiina Chemical group 0.000 description 6
- 238000010992 reflux Methods 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- 125000001475 halogen functional group Chemical group 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 2
- 125000003282 alkyl amino group Chemical group 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RQKYMHOXEANZSS-UHFFFAOYSA-N 3,4-dihydroquinolin-2-ylhydrazine Chemical compound C1=CC=C2CCC(NN)=NC2=C1 RQKYMHOXEANZSS-UHFFFAOYSA-N 0.000 description 1
- JRXXEXVXTFEBIY-UHFFFAOYSA-N 3-ethoxypropanoic acid Chemical compound CCOCCC(O)=O JRXXEXVXTFEBIY-UHFFFAOYSA-N 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- PIRYKGLQLCKQPG-UHFFFAOYSA-N [1,2,4]triazolo[4,3-a]quinoline Chemical compound C1=CC=C2N3C=NN=C3C=CC2=C1 PIRYKGLQLCKQPG-UHFFFAOYSA-N 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- 239000012445 acidic reagent Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000004849 alkoxymethyl group Chemical group 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- WYACBZDAHNBPPB-UHFFFAOYSA-N diethyl oxalate Chemical compound CCOC(=O)C(=O)OCC WYACBZDAHNBPPB-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000012458 free base Substances 0.000 description 1
- 125000004970 halomethyl group Chemical group 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000004452 microanalysis Methods 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- PXQLVRUNWNTZOS-UHFFFAOYSA-N sulfanyl Chemical class [SH] PXQLVRUNWNTZOS-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms 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
- C07D215/38—Nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US17231771A | 1971-08-16 | 1971-08-16 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU554815A3 true SU554815A3 (ru) | 1977-04-15 |
Family
ID=22627199
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1895868A SU554815A3 (ru) | 1971-08-16 | 1973-03-15 | Способ получени производных симмтриазоло-(4,3-а)-хинолина или их солей |
Country Status (31)
| Country | Link |
|---|---|
| JP (1) | JPS5760321B2 (enExample) |
| KR (1) | KR790000421B1 (enExample) |
| AR (2) | AR195289A1 (enExample) |
| AT (1) | AT324767B (enExample) |
| AU (1) | AU461057B2 (enExample) |
| BE (1) | BE787536A (enExample) |
| BG (3) | BG20354A3 (enExample) |
| CA (1) | CA997766A (enExample) |
| CH (2) | CH564016A5 (enExample) |
| CS (1) | CS190371B2 (enExample) |
| DD (2) | DD107462A5 (enExample) |
| DE (1) | DE2239892A1 (enExample) |
| DK (1) | DK139832B (enExample) |
| EG (1) | EG10668A (enExample) |
| ES (1) | ES405899A1 (enExample) |
| FR (1) | FR2149467B1 (enExample) |
| GB (1) | GB1374369A (enExample) |
| GT (1) | GT197225694A (enExample) |
| HU (1) | HU167272B (enExample) |
| IE (1) | IE36916B1 (enExample) |
| IL (1) | IL40060A (enExample) |
| IT (1) | IT962096B (enExample) |
| MY (1) | MY7800200A (enExample) |
| NL (1) | NL177173C (enExample) |
| PH (1) | PH10204A (enExample) |
| PL (1) | PL94442B1 (enExample) |
| RO (2) | RO79165A (enExample) |
| SE (2) | SE405313B (enExample) |
| SU (1) | SU554815A3 (enExample) |
| YU (1) | YU36937B (enExample) |
| ZA (1) | ZA725365B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR7801924A (pt) * | 1977-03-29 | 1978-10-24 | Capsugel Ag | Capsula de seguranca carregada com material viscoso e processo para sua producao |
| JPS61186648U (enExample) * | 1984-12-29 | 1986-11-20 | ||
| AT393764B (de) * | 1986-09-02 | 1991-12-10 | System Elektrotechnik Gotthold | Starthilfekabel |
| JPS63166228U (enExample) * | 1987-04-21 | 1988-10-28 | ||
| CA2540021A1 (en) | 2003-09-26 | 2005-04-07 | Rigel Pharmaceuticals, Inc. | Hcv inhibitors and methods of using them |
| US7569580B2 (en) | 2004-06-03 | 2009-08-04 | Rigel Pharmaceuticals, Inc. | Heterotricyclic compounds for use as HCV inhibitors |
| CA2636043A1 (en) * | 2006-01-23 | 2007-08-02 | Amira Pharmaceuticals, Inc. | Tricyclic inhibitors of 5-lipoxygenase |
-
0
- BE BE787536D patent/BE787536A/xx not_active IP Right Cessation
-
1971
- 1971-08-16 ES ES405899A patent/ES405899A1/es not_active Expired
-
1972
- 1972-08-04 ZA ZA725365A patent/ZA725365B/xx unknown
- 1972-08-07 IL IL40060A patent/IL40060A/en unknown
- 1972-08-09 YU YU2043/72A patent/YU36937B/xx unknown
- 1972-08-09 AU AU45397/72A patent/AU461057B2/en not_active Expired
- 1972-08-10 CA CA149,119A patent/CA997766A/en not_active Expired
- 1972-08-10 NL NLAANVRAGE7210957,A patent/NL177173C/xx not_active IP Right Cessation
- 1972-08-12 IT IT52168/72A patent/IT962096B/it active
- 1972-08-14 KR KR7201228A patent/KR790000421B1/ko not_active Expired
- 1972-08-14 PL PL1972157263A patent/PL94442B1/pl unknown
- 1972-08-14 DE DE2239892A patent/DE2239892A1/de not_active Withdrawn
- 1972-08-14 GT GT197225694A patent/GT197225694A/es unknown
- 1972-08-14 IE IE1125/72A patent/IE36916B1/xx unknown
- 1972-08-15 HU HU72EI427A patent/HU167272B/hu unknown
- 1972-08-15 CH CH411774A patent/CH564016A5/xx not_active IP Right Cessation
- 1972-08-15 CH CH1209772A patent/CH552942A/fr not_active IP Right Cessation
- 1972-08-15 GB GB3798972A patent/GB1374369A/en not_active Expired
- 1972-08-15 EG EG335/72A patent/EG10668A/xx active
- 1972-08-15 SE SE7210551A patent/SE405313B/xx unknown
- 1972-08-15 DK DK402572AA patent/DK139832B/da not_active IP Right Cessation
- 1972-08-15 CS CS725667A patent/CS190371B2/cs unknown
- 1972-08-16 RO RO7282499A patent/RO79165A/ro unknown
- 1972-08-16 BG BG024103A patent/BG20354A3/xx unknown
- 1972-08-16 DD DD173662*A patent/DD107462A5/xx unknown
- 1972-08-16 DD DD165089A patent/DD104176A5/xx unknown
- 1972-08-16 FR FR7229270A patent/FR2149467B1/fr not_active Expired
- 1972-08-16 PH PH13806A patent/PH10204A/en unknown
- 1972-08-16 JP JP47082060A patent/JPS5760321B2/ja not_active Expired
- 1972-08-16 AR AR243610A patent/AR195289A1/es active
- 1972-08-16 BG BG024104D patent/BG24409A3/xx unknown
- 1972-08-16 BG BG21209A patent/BG19623A1/xx unknown
- 1972-08-16 AT AT704672A patent/AT324767B/de not_active IP Right Cessation
- 1972-08-16 RO RO197271972A patent/RO63409A/ro unknown
-
1973
- 1973-03-15 SU SU1895868A patent/SU554815A3/ru active
- 1973-05-04 AR AR247862A patent/AR215825A1/es active
-
1975
- 1975-06-27 SE SE7507384A patent/SE422059B/xx not_active IP Right Cessation
-
1978
- 1978-12-30 MY MY200/78A patent/MY7800200A/xx unknown
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