SU626702A3 - Method of producing thieno/1,5/benzodiazepine or their salts - Google Patents
Method of producing thieno/1,5/benzodiazepine or their saltsInfo
- Publication number
- SU626702A3 SU626702A3 SU762406250A SU2406250A SU626702A3 SU 626702 A3 SU626702 A3 SU 626702A3 SU 762406250 A SU762406250 A SU 762406250A SU 2406250 A SU2406250 A SU 2406250A SU 626702 A3 SU626702 A3 SU 626702A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- benzodiazepine
- salts
- thieno
- fluoro
- ethyl
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
- C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D333/52—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes
- C07D333/62—Benzo[b]thiophenes; Hydrogenated benzo[b]thiophenes 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 hetero ring
- C07D333/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Biomedical Technology (AREA)
- Neurology (AREA)
- Neurosurgery (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Description
И обрртение отнсхзитс к способу полу чени новых THeHoj l,5j бензоаназепинов, обла/аюшнх венными фармакологЕгческнмн свойствами. С целью расширени арсенала редст воздействн на жнвой организм предлагаетс основанный на известной реаконн N -алкнлнровани ij способ получени тие о 1,5 бензодназешгаов обшей фор1 4улы . т VT.xV ---- где 1 и R - водород нлн галоген; F - группа формулы где R С i - С -алкил, бензил или (CHjj) ОН, гае ц - 2 или 3, кольцо Т - тнофеновое кольао, сконденсированное с диазепиновым дрс н незам ценвое или замешенное одной или дву.м группами, выбранными нз С -С -влкн.ла , С21-С -алкеннла, С.-С/-галогенап«свла , С - -алкааоипа, нитрогруппы, галогена н фенила, или нх солей путем взаимоде ггвн соединени обшей формулы гае F. , R н кольцо Т имеют указанные значени с алквлнруюшкм агентом обшей формулы . гае R имеет указанные Качени , X - еакаионноспособна группа. Целевой продукт выдел ют нзвестнымн приемами в свободн(л состо ннн лн в виде соли. 362 Новые TMeHo l,5J бензодиазепкны могут существовать в трех видах формул в. Радикал Ci-СА алкил - метил, этил, изопропил, Н бутил, втор.бутил, кзобутил и н-Йутил, Раднкал X - .реакционноспособный .атом, такой как хлор, бром йод, или реакнйонноспособна групп фовка, така как тоэил или мезил. t-«. 1,5 бенэодиазепины йвлаютс полезными как в виде свободного основани , так и в форме их солей. Эти соли предпочтительно вл ютс фармацевтически приемлемыми, нетоксичными сол ми подход щих кислот, например неорга нических кислот, таких как сол на , . мистоводородна , азотна , серна шш фосфорна , или органических кислот, таких как органические карбоновые кислотьч, например г лик о лева , малеинова , скск малеинова , фурмарова , блочна , винна лимонна , салицилова , о -ацетоксйбен@ой«на , никотинова или изоникотинова , или органические сульфоновые кислоты, например метансульфонова , этансульфоиовал 2-.оксиэтансульфонова , толуолсульфонова или нафталиН 2 Сульфонова . Помим фар -. мацевтически приемлемых солей получают также соли пикриновой и щавелевой кисло ты, они могут служить- в качестве проме жуточных продуктов при очистке целевых соединений или при получении целевых фар мацевтически приемлемых солей, или вл ютс полезнь ми при идентификации илй оч отке указанных оснований. Пример. 10-(4-п-хлорбензил -1-пиперазиш1л)2«-этил-7-фтор-4Н-тие но ,.5J бензодиазепин. Смесь 2-этил 7-фтор-1О( 1-41ипера-. зинил)-4Н тиено|2,3--Ъ1Г1.52бенэоаиазе гаша (1,0 г 0,ООЗ моль), п- лорбензилхлорида (0,38 г, 0,0033 моль) итриати амина (1,0 мл ) в этаноле . (25 мл) кип т т 16 ч с обратным холодильником , выпаривают досуха и цел т между водой и метиленхлори дом. С ганнческве экстракты промывают водой, суша над сульфатом мапш ш шаривавл- в вакууме и получают целевой бензодназв ин в виде твердого вещества, т. пл, 66-168с (СН2;СЕ„гексан). Аналогично получают; 1(5„(4 бензил 1-пиперазинил)-2этил 4Н тиено 2 ,3-Ь1 1 iS бензодиаае ин , т. пл. 79-80 0. В данной реакции бензилбромид выстуает в качестве алкилирующего агента. 10( 4 бензил-1-пиперазинил) .. о L3,.5j бензодиазепин, т.-пл. 19800 0 (этилацетат); 7-фтор-10-.( 4 бензил 1-.пиперазин)4Н тиено|з ,,5J бензодиазепин, . пл. 180 1820С (СНСЕ). 10( 4-.нзил-1.пиперазинил)-4Н-тиео 3,,5 бензодиазепин, т. пл, 21-222, 7-фтор-2«-меткл 1О.( 4 1 1етил-.1-пипеa3HHHn ),3J(l ,5 бензодиаепин , т. пл, 7 фтор 2-этил 1О-( 4 метил-1 ипера иннл)4Н тиено 2 ,,5 бензойиазе-. га, т. пл., . П р и м е р 2. 2-Зтил-7-фтор-1О .4( 2 оксиэтил)-1-пипераз11Нкл1 4Н-тиеHo 2 ,,5 бензодказепин. Смесь 2-этил-7-фтзр-.10( 1-липеразкшш )4Н-.ткено 2.3-Ъ ,5 бензодиазе пина (1,65 г, О,О05 моль) и этиленбромгидрина (1,25 г, О,О1 моль) в 90%-ном этаноле (15О мл) и триэтиламине (2,О2г 0,О2 моль) кип т т 16 ч с обратньпу xoiлодильником в атмосфере азота, выпаривают Jjocyxa, дел т между водой и метиленхлоридом , метиленхлоридный экстракт промывают водой, сушат над сульфатом магни , выпаривают досуха и получают т,пл. 173-175 С целевое соединение, (СН СЕ -гексан). Аналогично получают следукхцие соединени : . , 7-фтор-10- 4 -(2 оксиэтил)-1-пиперазитш 4Н™тйено з , ,5 бензодиазепин , Т.ПЯ. (CHC%), 2«-этил--7-фтор-1О-.4-( 3.оксипропил) 1 Липеразшшп -4Н- .тиено 2,,5 бензодиааепин, т.пл. 145-148 С (С С2 -гексан ), бензодиазепин, т.пл. 172-17;ГС (этилацетат.гексан). 7-.фтор--1О 4- (3 оксипропил)-1 пиперазинил - Н-тиено 3,,б бензодиазепин , д.пл. 138-14ОС (CHCl ); (3-оксипропил)-1-пиперазинил - ™4Н-/гиено L3,,5J бензодиазепин, т.пл. 184°С. Строение полученных соединений подтверждено данными ЯМР- и УФ- спектров .And the attribution of attitudes to the method of obtaining new THeHoj l, 5j benzanoazepines, regional pharmacologists, their diagnostic properties. In order to broaden the arsenal, a reduction in the organism of a stubble organism proposes a method, based on the known N-alkylation reaction ij, of preparing about 1.5 benzene derivatives of the total form1 of oil. t VT.xV ---- where 1 and R is hydrogen nl halogen; F is a group of the formula where R С i is C alkyl, benzyl or (CHjj) OH, hee c is 2 or 3, the T ring is a tinophen colo condensed with diazepine drs n uncensored or mixed with one or two groups selected nz C-C -vlnla, C21-C-alkennla, C.-C / -halogenoplum, C -alkaoipa, nitro, halogen n phenyl, or nx salts by the interaction of the compound of the general formula hei F., R The ring T has the indicated meanings with an alkaline agent of general formula. R has the specified Rolling, X - active group. The target product is isolated by known methods in free form (as a salt. 362 New TMeHo, 5J benzodiazepcans can exist in three types of formulas in. Radical Ci-CA alkyl - methyl, ethyl, isopropyl, H butyl, sec. Butyl , ksobutyl and n-Yutyl, Radnkal X -. reactive. atom, such as chlorine, bromine, iodine, or reactive groups, such as tooyl or mesyl. t- ". 1,5 beneodiazepines are useful both as a free base and and in the form of their salts. These salts are preferably pharmaceutically acceptable, non-toxic salts. and suitable acids, for example, inorganic acids, such as hydrochloric, hydrosulfuric, nitric, sulfuric phosphoric, or organic acids, such as organic carboxylic acids, for example, oleukene, maleic, maleskin, furmarova, block, wine citric, salicylic, o-acetoxyben @ oi “on, nicotinic or isonicotinic, or organic sulfonic acids, for example methanesulfonic, ethanesulfonic 2-.-oxyethanesulfonic, toluenesulfonic or naphtaliN 2 sulfonic. Mark headlights -. salts of acceptable salts also receive salts of picric and oxalic acids, they can serve as intermediates in the purification of the target compounds or in the preparation of the target pharmaceutically acceptable salts, or they are useful in identifying these reasons. Example. 10- (4-p-chlorobenzyl -1-piperazisl) 2 "-ethyl-7-fluoro-4H-tie but .5J benzodiazepine. A mixture of 2-ethyl 7-fluoro-1O (1-41ipera-. Zinyl) -4H thieno | 2,3 - 1Г1.52beneoaiase gash (1.0 g 0, OOZ mol), p-lorbenzyl chloride (0.38 g, 0.0033 mol) itriate amine (1.0 ml) in ethanol. (25 ml) are refluxed for 16 hours, evaporated to dryness and intact between water and methylene chloride. From Hannescawe extracts are washed with water, dried over sulphate mumsh sharivavl- in vacuum and get the target benzodnane yn in the form of a solid, so pl. 66-168s (CH2; CE „hexane). Similarly receive; 1 (5 „(4 benzyl 1-piperazinyl) -2ethyl 4H thieno 2, 3-Ü1 1 iS benzodiaein, t. Pl. 79-80 0. In this reaction, benzyl bromide acts as an alkylating agent. 10 (4 benzyl-1 piperazinyl) .. about L3, .5j benzodiazepine, mp - 19800 0 (ethyl acetate); 7-fluoro-10 -. (4 benzyl 1-piperazine) 4H thieno | s ,, 5J benzodiazepine, pl. 180 1820С (СНСЕ). 10 (4-.snyl-1.piperazinyl) -4H-thieo 3,, 5 benzodiazepine, m.p., 21-222, 7-fluoro-2 "-metcl 1O. (4 1 1ethyl- .1-pipea3HHHn), 3J (l, 5 benzodiaepine, mp, 7 fluoro 2-ethyl 1O- (4 methyl-1 iper innl) 4H thieno 2, 5 benzoiaza ga, mp, pl. R u mme r 2. 2-Ztil-7-fluoro-1O .4 (2 hydroxyethyl) -1-piperaz11Nkl1 4N-tieHo 2 ,, 5 ba nzodkazepin. A mixture of 2-ethyl-7-ftzr-.10 (1-liperazshsh) 4H-.tkeno 2.3-b, 5 benzodiazine pina (1.65 g, O, O05 mol) and ethylene bromohydrin (1.25 g, O, O1 mol) in 90% ethanol (15 O ml) and triethylamine (2, O2 0, O2 mol) are boiled for 16 h with reverse nitrogen in a nitrogen atmosphere, evaporated with Jjocyxa, divided between water and methylene chloride, the methylene chloride extract is washed with water , dried over magnesium sulfate, evaporated to dryness and get t, pl. 173-175 C target compound, (CH CE-hexane). Similarly, the following compounds are prepared:. , 7-fluoro-10-4- (2 hydroxyethyl) -1-piperazitsh 4H ™ tyeno z, 5 benzodiazepine, T.PYA. (CHC%), 2 "-ethyl - 7-fluoro-1O-.4- (3.oxypropyl) 1 Liperase-4H-type 2, 5 benzodiaepine, 145-148 C (C 2 -hexane), benzodiazepine, so pl. 172-17; HS (ethyl acetate-hexane). 7-fluorine - 1O 4- (3 hydroxypropyl) -1 piperazinyl - H-thieno 3, b. Benzodiazepine, d. 138-14 ° C (CHCl); (3-hydroxypropyl) -1-piperazinyl - ™ 4H- / hyeno L3,, 5J benzodiazepine, m.p. 184 ° C. The structure of the compounds obtained was confirmed by NMR and UV spectra.
Claims (1)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB51240/74A GB1533235A (en) | 1974-11-26 | 1974-11-26 | Benzodiazepine derivatives |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU626702A3 true SU626702A3 (en) | 1978-09-30 |
Family
ID=10459213
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742191705A SU629879A3 (en) | 1974-11-26 | 1974-11-25 | Method of obtaining thieno(1,5)-benzodiazepines or salts thereof |
| SU762406250A SU626702A3 (en) | 1974-11-26 | 1976-10-07 | Method of producing thieno/1,5/benzodiazepine or their salts |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU742191705A SU629879A3 (en) | 1974-11-26 | 1974-11-25 | Method of obtaining thieno(1,5)-benzodiazepines or salts thereof |
Country Status (30)
| Country | Link |
|---|---|
| JP (1) | JPS6044314B2 (en) |
| AR (1) | AR221203A1 (en) |
| AT (1) | AT351547B (en) |
| AU (1) | AU506340B2 (en) |
| BE (1) | BE835932A (en) |
| BG (1) | BG29573A3 (en) |
| CA (1) | CA1075687A (en) |
| CH (2) | CH613455A5 (en) |
| CS (1) | CS236753B2 (en) |
| DD (1) | DD123343A5 (en) |
| DE (1) | DE2552403C2 (en) |
| DK (1) | DK146887C (en) |
| ES (1) | ES443011A1 (en) |
| FR (1) | FR2292479A1 (en) |
| GB (1) | GB1533235A (en) |
| HK (1) | HK58681A (en) |
| HU (1) | HU172493B (en) |
| IE (1) | IE42564B1 (en) |
| IL (1) | IL48502A (en) |
| KE (1) | KE3163A (en) |
| MY (1) | MY8200149A (en) |
| NL (1) | NL186088C (en) |
| NZ (1) | NZ179335A (en) |
| PH (2) | PH11669A (en) |
| PL (1) | PL100135B1 (en) |
| RO (1) | RO69912A (en) |
| SE (2) | SE421209B (en) |
| SU (2) | SU629879A3 (en) |
| YU (1) | YU298375A (en) |
| ZA (1) | ZA757344B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2125574C1 (en) * | 1992-05-29 | 1999-01-27 | Лилли Индастриз Лимитед | Thienobenzodiazepines or pharmaceutically acceptable salts thereof, process for preparing thereof, and pharmaceutical composition |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IL62792A (en) * | 1980-05-07 | 1985-02-28 | Byk Gulden Lomberg Chem Fab | Acylated dihydrothienodiazepinone compounds,process for their preparation,and medicaments containing them |
| GB8819059D0 (en) * | 1988-08-11 | 1988-09-14 | Lilly Industries Ltd | Benzodiazepine compounds & their use as pharmaceuticals |
| GB9009229D0 (en) | 1990-04-25 | 1990-06-20 | Lilly Industries Ltd | Pharmaceutical compounds |
| US6043358A (en) | 1995-11-01 | 2000-03-28 | Merck & Co., Inc. | Hexahydro-5-imino-1,4-heteroazepine derivatives as inhibitors of nitric oxide synthases |
| JP3188715B2 (en) * | 1995-11-01 | 2001-07-16 | メルク エンド カンパニー インコーポレーテッド | Hexahydro-5-imino-1,4-heteroazepine derivatives as inhibitors of nitric oxide synthase |
| HUP0003718A3 (en) * | 1997-09-02 | 2002-11-28 | Welfide Corp | Fused thiophene derivatives, use thereof and pharmaceutical compositions containing them |
| RU2185383C1 (en) * | 2001-05-22 | 2002-07-20 | Институт молекулярной генетики РАН | 2-methyl-4-(4-methyl-1-piperazinyl)-10h-thieno-[2,3-b][1,5]benzodiazepine high-labeled with tritium |
| PL199016B1 (en) * | 2002-06-20 | 2008-08-29 | Adamed Sp Z Oo | Method of manufacture of alanzapine, new derivative of n-demethyl olanzapine and method of manufacture of new derivative of n-demethyl olanzapine |
| SI21270A (en) | 2002-07-15 | 2004-02-29 | Krka, Tovarna Zdravil, D.D., Novo Mesto | Crystal forms of olanzapine and procedures for their preparation |
| DE10301923B3 (en) * | 2003-01-17 | 2004-09-16 | Krka Tovarna Zdravil, D.D. | Process and intermediates for the production of olanzapine |
| AR047461A1 (en) * | 2004-01-27 | 2006-01-18 | Synthon Bv | TRAINING, PURIFICATION AND USE OF N-FORMILOLANZAPINE |
| AR048272A1 (en) | 2004-03-18 | 2006-04-12 | Lek Pharmaceuticals | SYNTHESIS OF 2 METHYL - 4- (4- METHYL -1- PIPERAZINIL) - 10 H- TIENO (2,3-B) (1,5) BENZODIAZEPIN AND ITS SALTS, METHODS FOR THEIR PREPARATION, PHARMACEUTICAL COMPOSITIONS CONTAINING IT AND ITS USE IN THE MANUFACTURE OF MEDICINES FOR THE TREATMENT OF MENTAL DISEASES. |
| EP1778243B1 (en) * | 2004-06-30 | 2012-10-31 | Athersys, Inc. | Substituted azepine derivatives as serotonin receptor modulators |
| EP2292624A1 (en) | 2009-07-20 | 2011-03-09 | LEK Pharmaceuticals d.d. | Process for the purification of olanzapine |
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1974
- 1974-11-25 SU SU742191705A patent/SU629879A3/en active
- 1974-11-26 GB GB51240/74A patent/GB1533235A/en not_active Expired
-
1975
- 1975-11-20 CA CA240,082A patent/CA1075687A/en not_active Expired
- 1975-11-20 IL IL48502A patent/IL48502A/en unknown
- 1975-11-20 DK DK524175A patent/DK146887C/en active
- 1975-11-21 PH PH17788A patent/PH11669A/en unknown
- 1975-11-21 AU AU86858/75A patent/AU506340B2/en not_active Expired
- 1975-11-22 DE DE2552403A patent/DE2552403C2/en not_active Expired
- 1975-11-24 SE SE7513185A patent/SE421209B/en not_active IP Right Cessation
- 1975-11-24 CH CH604478A patent/CH613455A5/en not_active IP Right Cessation
- 1975-11-24 CH CH1517275A patent/CH613454A5/en not_active IP Right Cessation
- 1975-11-24 ZA ZA757344A patent/ZA757344B/en unknown
- 1975-11-24 NZ NZ179335A patent/NZ179335A/en unknown
- 1975-11-25 FR FR7535900A patent/FR2292479A1/en active Granted
- 1975-11-25 IE IE2565/75A patent/IE42564B1/en unknown
- 1975-11-25 AR AR261340A patent/AR221203A1/en active
- 1975-11-25 RO RO7584018A patent/RO69912A/en unknown
- 1975-11-25 DD DD189666A patent/DD123343A5/xx unknown
- 1975-11-25 JP JP50141080A patent/JPS6044314B2/en not_active Expired
- 1975-11-25 YU YU02983/75A patent/YU298375A/en unknown
- 1975-11-25 BE BE6045266A patent/BE835932A/en not_active IP Right Cessation
- 1975-11-26 NL NLAANVRAGE7513833,A patent/NL186088C/en not_active IP Right Cessation
- 1975-11-26 AT AT898275A patent/AT351547B/en not_active IP Right Cessation
- 1975-11-26 PL PL1975184991A patent/PL100135B1/en unknown
- 1975-11-26 CS CS757991A patent/CS236753B2/en unknown
- 1975-11-26 ES ES443011A patent/ES443011A1/en not_active Expired
- 1975-11-26 BG BG031601A patent/BG29573A3/en unknown
- 1975-11-26 HU HU75LI00000284A patent/HU172493B/en unknown
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1976
- 1976-10-07 SU SU762406250A patent/SU626702A3/en active
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1977
- 1977-02-22 PH PH19480A patent/PH24534A/en unknown
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1978
- 1978-11-27 SE SE7812194A patent/SE429045B/en not_active IP Right Cessation
-
1981
- 1981-09-24 KE KE3163A patent/KE3163A/en unknown
- 1981-11-26 HK HK586/81A patent/HK58681A/en unknown
-
1982
- 1982-12-30 MY MY149/82A patent/MY8200149A/en unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2125574C1 (en) * | 1992-05-29 | 1999-01-27 | Лилли Индастриз Лимитед | Thienobenzodiazepines or pharmaceutically acceptable salts thereof, process for preparing thereof, and pharmaceutical composition |
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