SU577995A3 - Способ получени производных бензигидрил -п-оксибензил-пиперазина или их солей - Google Patents
Способ получени производных бензигидрил -п-оксибензил-пиперазина или их солейInfo
- Publication number
- SU577995A3 SU577995A3 SU7402082532A SU2082532A SU577995A3 SU 577995 A3 SU577995 A3 SU 577995A3 SU 7402082532 A SU7402082532 A SU 7402082532A SU 2082532 A SU2082532 A SU 2082532A SU 577995 A3 SU577995 A3 SU 577995A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- residue
- general formula
- acid
- acetic
- dissolved
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 5
- 150000003839 salts Chemical class 0.000 title claims 5
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims 8
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 claims 6
- 239000002253 acid Substances 0.000 claims 5
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims 4
- 239000000203 mixture Substances 0.000 claims 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid group Chemical group C(C1=CC=CC=C1)(=O)O WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 3
- 150000001875 compounds Chemical class 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000008346 aqueous phase Substances 0.000 claims 2
- 239000011230 binding agent Substances 0.000 claims 2
- 239000013078 crystal Substances 0.000 claims 2
- 238000010438 heat treatment Methods 0.000 claims 2
- 229910052739 hydrogen Inorganic materials 0.000 claims 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 239000002244 precipitate Substances 0.000 claims 2
- 239000002904 solvent Substances 0.000 claims 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims 1
- BMYNFMYTOJXKLE-UHFFFAOYSA-N 3-azaniumyl-2-hydroxypropanoate Chemical compound NCC(O)C(O)=O BMYNFMYTOJXKLE-UHFFFAOYSA-N 0.000 claims 1
- SEVSMVUOKAMPDO-UHFFFAOYSA-N 4-acetoxy benzaldehyde Chemical compound CC(=O)OC1=CC=C(C=O)C=C1 SEVSMVUOKAMPDO-UHFFFAOYSA-N 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims 1
- 235000011054 acetic acid Nutrition 0.000 claims 1
- 125000000218 acetic acid group Chemical class C(C)(=O)* 0.000 claims 1
- 150000007513 acids Chemical class 0.000 claims 1
- 239000003513 alkali Substances 0.000 claims 1
- 230000029936 alkylation Effects 0.000 claims 1
- 238000005804 alkylation reaction Methods 0.000 claims 1
- 125000004429 atom Chemical group 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 239000003518 caustics Substances 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000003638 chemical reducing agent Substances 0.000 claims 1
- 239000013256 coordination polymer Substances 0.000 claims 1
- 238000000354 decomposition reaction Methods 0.000 claims 1
- 239000003085 diluting agent Substances 0.000 claims 1
- 230000003993 interaction Effects 0.000 claims 1
- 150000007522 mineralic acids Chemical class 0.000 claims 1
- 150000007524 organic acids Chemical class 0.000 claims 1
- 235000005985 organic acids Nutrition 0.000 claims 1
- 229940072033 potash Drugs 0.000 claims 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims 1
- 235000015320 potassium carbonate Nutrition 0.000 claims 1
- 239000000843 powder Substances 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 235000017557 sodium bicarbonate Nutrition 0.000 claims 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 238000003786 synthesis reaction Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/02—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements
- C07D295/027—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring
- C07D295/03—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms containing only hydrogen and carbon atoms in addition to the ring hetero elements containing only one hetero ring with the ring nitrogen atoms directly attached to acyclic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/06—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals
- C07D295/073—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by halogen atoms or nitro radicals with the ring nitrogen atoms and the substituents separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/04—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
- C07D295/08—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms
- C07D295/096—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by singly bound oxygen or sulfur atoms with the ring nitrogen atoms and the oxygen or sulfur atoms separated by carbocyclic rings or by carbon chains interrupted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/16—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms
- C07D295/20—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms acylated on ring nitrogen atoms by radicals derived from carbonic acid, or sulfur or nitrogen analogues thereof
- C07D295/205—Radicals derived from carbonic acid
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Hydrogenated Pyridines (AREA)
- Catalysts (AREA)
Description
(54) СПОСОБ ПОЛУЧЕНИЯ ПРОИЗВОДНЫХ
N-БEнзгидpи ьN- п -ОКСИБЕНЗИЛПИПЕРАЗИНА
Claims (2)
- или их СОЛЕЙ 12 Исходные соединени общей формулы fl можно получить, например, путем взаимодей ВИЯ соединени общей формулы Щ ( JH-IT If rae.i имеет указанные значени , с ,б ензипхп10ридом общей формулы IV где RJ имеет указанные значени . Процесс вааимодействн осушествп ют безводном растворигепё, например в топуопе, бензоле пи диоксане nprf 5012О С в присутствии 1 мопь св зывающего кислоту средства, В качестве св зывйюща- го кислоту средства можно примен ;гь, например , поташ, соду, бикарбонат натри или мольный соединени общей формулы Соедииеии общей формулы I образуют сопи с неорганическими или органическими кислотами в подход щем растворителе. Такими кислотами вл ютс , например, хпористовоаЬродна , фомистоводородна , фосфорна серна , щавелева |, молочна , винна , уксусиа , салицилова , бензойна , лимонна , аскорбинова , адипинова . С избытком кислоты получают дисоли, моносоли, т. е, соли с одним остатком кислоты, получают, подверга соединени общей формулы I рзаимоаействию точно с 1 моль соответствующей кислоты. .Пример. 3,3г N -хлорбензгид-... рил) - N -. ( fl -ацетокснбензил) пиперазииа формулы Сц-.кч 1-гм -V V-O-CO-CH . f полученного обычным путем - восстановитвл ным алкилированием Ы-(П-хлорбензгидрил) липеразина с помощьюп-ацетоксибензальдегида ), раствор ют при слабом нагревании в iS мл этанола, потом прибавл ют 10 мл 2 н раствора едкого натра и смесь нагреваю р течение 8 час до 50 С. Затем смесь охлаждают, концентрируют в вакууме и остаток раствор ют в воде/хлороформе. Водную фазу выдел ют, еще трижды промывают хлороформом,) Ьотом прибавл ют осторсжно 2 н.сол ную кислоту, пока осаждаетс осадок, после чего отсасывают и остаток перекристаппизовывают из топуода. Получают таким образом N (Т1-хпорбенагидрил ) - N- (п-оксибензип)пиперазин в виде бесцветных крисгаппов, с т. пп, 59 С, выход продукта 82%. Дп попучени дигидрохпорида раствор ют продукт в безводном диэтиловом эфире и через раствор пропускают сухой хпористый водород. Днгидрохпорид отсасывают и перекристаппизовывают из безводного этанопа. Получают таким образом М-(п-хпорбенэгидрил )- N-n- оксибензилпиперазин-дигипр хлорид в виде бесцветных кристаллов, т. пл. 23О °С, Найдено,: С 61,8; Н 5,8; N6,1; се 2 2,6. Cz4 гт ъ Вычислвно,%: С 61,8; Н 5,8; N6,0; С1 22,9. (ГТ -хлорбе згидрил) -. - П -оконбензилпиперазин можно обычным образом переводить с помощью серной кислогьГ в сульфат , с т. пл. (с разложением) и с помощью бромистоводородной кислоты - в дигидробромид , т. пл. . П р и м е р 2. 3 rN-бензгидрил - N ( 11 -бензилоксибензил)пиперазина формулы CH-N Ь1- полученного обычным путем - восстановитель ,ным апкигаированием N -банзгидриппиперазина с tl-бензоилоксибензальдегидом, при слабом нагревании раствор ют в 5О мл метанола, потом прибавл ют 10 мл 2 н.раствора едкого капи и смесь нагревают до кипени в течение 6 час с обратным холодильником. Потом смесь охлаждают, концентрируют в вакууме и остаток раствор ют в воде/хлорофор- ме. Водную фазу выдел ют, оп ть трижды промывают хлороформом, потом осторожно :прибавл ют 2 н.сол ную кислоту, пока выдеrii n rt г 1т 1Г1УЧчп О 1л / гчпгтт1Чг1Л гт гм а л етс осадок, затем отсасывают и остаток перекристаллизовывают из диоксана.( Получают таким обраэомМ-бензгидрил-Н - ( fl -оксибензил)пиперазин, выход 79% от теоретического. Формула изобретени 1. Способ получени пpoизвoдныx,N-бeн гидрил -К- h -оксибе зилпиперазииа общей формулы I OH-if ir-eHj-f VOH где R - атом хпора, водорода, или их солей , от пинающий тем, чго N -бензгиарип N -бенаиппн разин обшей формупы } ( где R, имеет указанные значени ; апканоипьный остаток с 1-6 ат ми углерода, бензоипьный остаток, гидропизуют водной щелочью в раст рителе при 2О-10О С с последующим пением целевого продукта в свободном или в виде соли. 2.Сасх;об по п. 1, о г п и ч а ю щ и йс тем, что в качестве расгворигоп испопьауюг эганоп, меганоп. 3, Способ по пп. 1и2, отаича и и с тем, что процесс провод т при 2О-5О °С. Приоритет по признакам: О2.06.72. при R - атом водорода; 12.ОЗ.73 при R -атом хпора. Источники информации, прин тые во внимание при экспертизе: 1.Патенг США ,Nfe 27О9169, кп. 26О268 , 1955.
- 2.Бюлер К., Пирсон Д. Органически синтезы ,М., Мир, 1й73,ч. 1,с 288.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2226767A DE2226767A1 (de) | 1972-06-02 | 1972-06-02 | N-benzhydryl-n'-p-hydroxybenzylpiperazin und verfahren zu seiner herstellung |
| DE19732312212 DE2312212A1 (de) | 1973-03-12 | 1973-03-12 | N-(p-chlorbenzhydryl)-n'-p-hydroxybenzyl-piperazin und verfahren zu seiner herstellung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU577995A3 true SU577995A3 (ru) | 1977-10-25 |
Family
ID=25763357
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1926943A SU508196A3 (ru) | 1972-06-02 | 1973-05-31 | Способ получени производных -бензгидрил- - -оксибензилпиперазина |
| SU1926942A SU530644A3 (ru) | 1972-06-02 | 1973-05-31 | Способ получени производных бензгидрил- -п-оксибензилпиперазина или их солей |
| SU1926939A SU507238A3 (ru) | 1972-06-02 | 1973-05-31 | Способ получени производных -бензгидрил- -п-оксибензилпиперазина |
| SU7402082532A SU577995A3 (ru) | 1972-06-02 | 1974-12-13 | Способ получени производных бензигидрил -п-оксибензил-пиперазина или их солей |
Family Applications Before (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU1926943A SU508196A3 (ru) | 1972-06-02 | 1973-05-31 | Способ получени производных -бензгидрил- - -оксибензилпиперазина |
| SU1926942A SU530644A3 (ru) | 1972-06-02 | 1973-05-31 | Способ получени производных бензгидрил- -п-оксибензилпиперазина или их солей |
| SU1926939A SU507238A3 (ru) | 1972-06-02 | 1973-05-31 | Способ получени производных -бензгидрил- -п-оксибензилпиперазина |
Country Status (26)
| Country | Link |
|---|---|
| US (1) | US3868377A (ru) |
| JP (1) | JPS4948687A (ru) |
| AR (5) | AR196936A1 (ru) |
| AT (3) | AT331802B (ru) |
| AU (1) | AU470393B2 (ru) |
| BG (3) | BG20371A3 (ru) |
| CA (1) | CA980347A (ru) |
| CH (4) | CH574949A5 (ru) |
| CS (4) | CS182234B2 (ru) |
| DD (1) | DD106644A5 (ru) |
| DK (1) | DK139751C (ru) |
| EG (1) | EG11434A (ru) |
| ES (3) | ES415465A1 (ru) |
| FI (1) | FI55656C (ru) |
| FR (1) | FR2186265B1 (ru) |
| GB (1) | GB1386916A (ru) |
| HU (1) | HU165312B (ru) |
| IE (1) | IE37717B1 (ru) |
| IL (1) | IL42384A (ru) |
| NL (1) | NL7306771A (ru) |
| NO (1) | NO138026C (ru) |
| PH (1) | PH9485A (ru) |
| PL (3) | PL94759B1 (ru) |
| RO (3) | RO62900A (ru) |
| SE (1) | SE396385B (ru) |
| SU (4) | SU508196A3 (ru) |
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS59101475A (ja) * | 1982-12-02 | 1984-06-12 | Nippon Chemiphar Co Ltd | 新規ピペラジン誘導体およびその製造法ならびにこれを含有する脳循環改善剤 |
| HU186656B (en) * | 1982-12-28 | 1985-09-30 | Richter Gedeon Vegyeszet | Process for producing new benzhydryl-piperazine derivatives, acid additionak salts and pharmaceutical compositions containing them |
| GB8320701D0 (en) * | 1983-08-01 | 1983-09-01 | Wellcome Found | Chemotherapeutic agent |
| JPS60222472A (ja) * | 1984-03-30 | 1985-11-07 | Kanebo Ltd | 新規なピペラジン誘導体および該化合物を有効成分とする医薬組成物 |
| ATE107296T1 (de) * | 1988-08-05 | 1994-07-15 | Nippon Chemiphar Co | Optisch aktive piperazin-derivate. |
| FR2661176B1 (fr) * | 1990-04-20 | 1992-06-12 | Adir | Nouveau procede de preparation de la 1-(2,3,4-trimethoxybenzyl) piperazine en amination reductive. |
| PT711289E (pt) * | 1993-07-30 | 2001-02-28 | Delta Pharmaceuticals Inc | Compostos piperazina utilizados em terapia |
| WO1995015958A1 (en) * | 1993-12-08 | 1995-06-15 | Alcon Laboratories, Inc. | Compounds having both potent calcium antagonist and antioxidant activity and use thereof as cytoprotective agents |
| WO2009147389A2 (en) * | 2008-06-02 | 2009-12-10 | Cipla Limited | Processes for the synthesis of levocetirizine and intermediates for use therein |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2709169A (en) * | 1955-05-24 | X c chs | ||
| US3051710A (en) * | 1959-12-21 | 1962-08-28 | Lakeside Lab Inc | Glycolic acid amide derivatives of piperazine and use thereof |
-
1973
- 1973-05-15 NL NL7306771A patent/NL7306771A/xx not_active Application Discontinuation
- 1973-05-28 IE IE855/73A patent/IE37717B1/xx unknown
- 1973-05-29 BG BG026973A patent/BG20371A3/xx unknown
- 1973-05-29 CS CS7300003883A patent/CS182234B2/cs unknown
- 1973-05-29 IL IL42384A patent/IL42384A/en unknown
- 1973-05-29 RO RO7374944A patent/RO62900A/ro unknown
- 1973-05-29 RO RO7382540A patent/RO68379A/ro unknown
- 1973-05-29 CS CS7600004284A patent/CS182248B2/cs unknown
- 1973-05-29 CS CS3877A patent/CS178429B2/cs unknown
- 1973-05-29 US US364764A patent/US3868377A/en not_active Expired - Lifetime
- 1973-05-29 BG BG026972A patent/BG20596A3/xx unknown
- 1973-05-29 BG BG023741A patent/BG20595A3/xx unknown
- 1973-05-29 CS CS3878A patent/CS178430B2/cs unknown
- 1973-05-29 RO RO7382539A patent/RO68378A/ro unknown
- 1973-05-30 SE SE7307692A patent/SE396385B/xx unknown
- 1973-05-30 GB GB2571073A patent/GB1386916A/en not_active Expired
- 1973-05-31 PL PL1973186639A patent/PL94759B1/pl unknown
- 1973-05-31 JP JP48060375A patent/JPS4948687A/ja active Pending
- 1973-05-31 SU SU1926943A patent/SU508196A3/ru active
- 1973-05-31 EG EG206/73A patent/EG11434A/xx active
- 1973-05-31 PL PL1973186638A patent/PL97129B1/pl unknown
- 1973-05-31 AU AU56343/73A patent/AU470393B2/en not_active Expired
- 1973-05-31 AR AR248325A patent/AR196936A1/es active
- 1973-05-31 SU SU1926942A patent/SU530644A3/ru active
- 1973-05-31 PH PH14678*UA patent/PH9485A/en unknown
- 1973-05-31 SU SU1926939A patent/SU507238A3/ru active
- 1973-05-31 PL PL1973162986A patent/PL91050B1/pl unknown
- 1973-05-31 DD DD171224A patent/DD106644A5/xx unknown
- 1973-05-31 AR AR248327A patent/AR201001A1/es active
- 1973-05-31 HU HUCA347A patent/HU165312B/hu unknown
- 1973-05-31 AR AR248326A patent/AR194688A1/es active
- 1973-05-31 CA CA172,824A patent/CA980347A/en not_active Expired
- 1973-06-01 ES ES73415465A patent/ES415465A1/es not_active Expired
- 1973-06-01 ES ES415464A patent/ES415464A1/es not_active Expired
- 1973-06-01 AT AT483173A patent/AT331802B/de not_active IP Right Cessation
- 1973-06-01 FR FR7319998A patent/FR2186265B1/fr not_active Expired
- 1973-06-01 AT AT483273A patent/AT331252B/de not_active IP Right Cessation
- 1973-06-01 AT AT483073A patent/AT331801B/de not_active IP Right Cessation
- 1973-06-01 DK DK304673A patent/DK139751C/da active
- 1973-06-01 ES ES415466A patent/ES415466A1/es not_active Expired
- 1973-06-01 FI FI1797/73A patent/FI55656C/fi active
- 1973-06-01 NO NO2303/73A patent/NO138026C/no unknown
- 1973-06-04 CH CH802873A patent/CH574949A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH1193576A patent/CH594651A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH802973A patent/CH579064A5/xx not_active IP Right Cessation
- 1973-06-04 CH CH803073A patent/CH593959A5/xx not_active IP Right Cessation
-
1974
- 1974-01-01 AR AR252417A patent/AR204987A1/es active
- 1974-02-18 AR AR252416A patent/AR200764A1/es active
- 1974-12-13 SU SU7402082532A patent/SU577995A3/ru active
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