RU1794079C - Способ получени замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилата в форме цис-энантиомера - Google Patents
Способ получени замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилата в форме цис-энантиомераInfo
- Publication number
- RU1794079C RU1794079C SU864027832A SU4027832A RU1794079C RU 1794079 C RU1794079 C RU 1794079C SU 864027832 A SU864027832 A SU 864027832A SU 4027832 A SU4027832 A SU 4027832A RU 1794079 C RU1794079 C RU 1794079C
- Authority
- RU
- Russia
- Prior art keywords
- carba
- cis
- cephem
- carboxilate
- dethia
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D205/00—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom
- C07D205/02—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D205/06—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D205/08—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams
- C07D205/085—Heterocyclic compounds containing four-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with one oxygen atom directly attached in position 2, e.g. beta-lactams with a nitrogen atom directly attached in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/08—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D263/16—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
- C07D263/18—Oxygen atoms
- C07D263/20—Oxygen atoms attached in position 2
- C07D263/22—Oxygen atoms attached in position 2 with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D463/00—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D463/10—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2
- C07D463/14—Heterocyclic compounds containing 1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbacephalosporins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring with a carbon atom having three bonds to hetero atoms with at the most one bond to halogen, e.g. an ester or nitrile radical, directly attached in position 2 with hetero atoms directly attached in position 7
- C07D463/16—Nitrogen atoms
- C07D463/18—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof
- C07D463/20—Nitrogen atoms further acylated by radicals derived from carboxylic acids or by nitrogen or sulfur analogues thereof with the acylating radicals further substituted by hetero atoms or by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Cephalosporin Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
Ё.
т.пл. 13б-137°С (разл.); а Ь +65,8° (с - 0,6, хлороформ).
Вычислено, %: С 49,40; Н 5,92.
СцН2оМ Юб.
Найдено, %: С 49,47; Н 5,93.
Переэтерификаци .
Бензиловый спирт (20 мл, 193 ммоль) и изопропоксид титана (0,78 мл, 2,62 ммоль) перемешивают в вакууме (1 мм рт.ст.) в течение 45 мин дл удалени изопропанола. Затем колбу накрывают пленкой с отверстием дл ввода аргона и добавл ют диазо- / -кетометиловый эфир (0,963 г, 2,80 ммоль). Раствор выдерживают 52 ч при 36°С, разбавл ют 60 мл диэтилового эфира и обрабатывают 3 мл насыщенного водного раствора сульфата натри . Смесь интенсивно перемешивают в течение ночи и фильтруют через слой цеолита. После отгонки эфира в роторном испарителе бензиловый спирт отгон ют в печи с шариковой трубкой (15 мтор, 50°С). После хроматографировани остатка на 100 г двуокиси кремни получают соответствующий диазо-/ -кетобензиловый. эфир (0,837 г, 72%) в виде твердого белого вещества, т.пл. 152-153°С (разл.), а о + +55,6° (с 0,7, хлороформ).
Вычислено, %: С 57,68; Н 5,81.
C20H24N406.
Найдено, %; С 57,57; Н 5,74. Циклизаци в присутствии соли роди
(II).
Раствор диазо-/ -кетобензилового эфира (0,12 г, 0,29 ммоль) в 6 мл профильтрованного через окись алюмини хлороформа нагревают до кипени с обратным холодильником и обрабатывают димером ацетата роди (II) (1,5 мг, 0,0034 ммоль). После выдержки в течение 20 мин при температуре кипени получают целевой продукт.
-ЯМР-спектр (), 300 МГц), б: 11,3 (с., 1Н, ОН), 7,50-7,30 (м., 5Н, Ar Н), 5.37-5,27 (АВ-структура. 2Н. АгСН2), 5,20- 5,08 (м., 2Н, С7-Н и BOCNH), 3,83-3,72 (м., 1Н, С6-Н1), 2,58-2,45 (м., 2Н, С2-протоны метилена), 2,12-2, 00 (м., 1 Н, один из Ст-про- трнов метилена), 1,74-1,58 (м., 1Н, один из
Ci-протонов метилена), 1,47 (с., 9Н, трет-бу- тил),
П р и м е р 2. п-Нитробензил-7/ -фенок- сиацетиламино-3-окси-1-карба-(1-детиа)-3- -цефем-4-карбоксилат.
Раствор п-нитробензил-2-диазо-З-оксо- 5-(3 /З-феноксиацетиламиноазетидин-2-он4-ил )-лентаноата (20 мг, 0,04 моль), каталитического количества ацетата роди
(II) (около 0,1 мг) в 5 мл хлороформа фильтруют через глинозем. Кип т т с обратным холодильником в течение 30 мин, охлаждают до 0°С и выпаривают в вакууме до получени масла.
н-ЯМР-спектр (90 МГц, , 5: 8,2 (д., J - 8 Гц, 2Н). 7,8 (д., J - 8 Гц, 2Н), 7,5-6,8 (м., 6Н), 5,4 (АВ-квартет, 2Н), 5,4 (м„ 2Н), 4,5 (м„2Н), 3,9 (ддд„ J - 3,4, 9 Гц) и 2,8-1,8 (м., 4Н).
Масс-спектр дл С2зН22№08:468,14168 (М + Н) (вычислено 468,14069).
П р и м е р 3. Трифторметилсульфонило- вый эфир п-нитробензил-7/Ј-феноксиацети- ламино-3-01 си-1-карбат(1-детиа)-3-цефем-4
-карбоксилата (трифлат).
Раствор п-нитробензил-2-диазо-З-оксо5- (3 / -феноксиацетиламиноазетидин-2-он- 4-ил)-пентаноата (478,4 мг, 0,966 ммоль) и ацетата роди (II) (10 мг) в 100 мл хлорофор- ма фильтруют через глинозем, кип т т с об- ратным холодильником в течение 1 ч, охлаждают до 0°С и добавл ют диизопропи- лэтиламин (375 мг, 0,51 мл, 2,90 ммоль) и ангидрид трифторметилсульфокислоты (трифлиновый ангидрид) (272 мг, 0,97 ммоль), перемешивают 30 мин при комнатной температуре, разбавл ют метиленхло- ридом, промывают 0,5 М водным раствором винной кислоты, водой, водным раствором бикарбоната натри и рассолом, сушат над сульфатом натри , выпаривают досуха и очищают остаток, хроматографиру на сили- кагеле и использу в качестве элюента градиент этилацетата и метиленхлорида (0-10%). Выход 258,7мг (45%).
Вычислено, %: С 48,08; Н 3,26; N 7,01.
С24Н2оРз№ОюЗ.
Найдено, %: С 48,07; Н 3,19; N 7,22.
Масс-спектр: 600 (М + Н).
Claims (1)
- Формула изобретени форме цис-энантиомеров, о т л и ч а юСпособ получени замещенных 7-ами-щ и и с тем, что диазоэфир общей форно-3-окси-1-карба- (1-детиа)-3-цефем-4-кар- мулыбоксилата общей формулыОH,Cfflffl R,flONHv „CHjCHie-C-COORjТТRz.. ууЦ1н .где RI и RZ имеют указанные значени , подгде RI - феноксиметил или С1-С4-алкоксиг-вергают циклизации в присутствии соли роруппа , R2 - бензил или п-нитробензил, вдн (II) в качестве катализатора.Т
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/755,982 US4665171A (en) | 1985-07-17 | 1985-07-17 | Process and intermediates for β-lactam antibiotics |
Publications (1)
Publication Number | Publication Date |
---|---|
RU1794079C true RU1794079C (ru) | 1993-02-07 |
Family
ID=25041514
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
SU864027832A RU1794079C (ru) | 1985-07-17 | 1986-07-15 | Способ получени замещенных 7-амино-3-окси-1-карба(1-детиа)-3-цефем-4-карбоксилата в форме цис-энантиомера |
Country Status (22)
Country | Link |
---|---|
US (1) | US4665171A (ru) |
EP (2) | EP0362902B1 (ru) |
JP (2) | JPH0762015B2 (ru) |
KR (1) | KR900005257B1 (ru) |
CN (1) | CN1015178B (ru) |
AR (1) | AR243186A1 (ru) |
AT (2) | ATE63118T1 (ru) |
AU (2) | AU595216B2 (ru) |
CA (1) | CA1310323C (ru) |
DE (2) | DE3650474T2 (ru) |
DK (2) | DK173456B1 (ru) |
ES (2) | ES2000516A6 (ru) |
GR (1) | GR861857B (ru) |
HK (1) | HK1007140A1 (ru) |
HU (2) | HU201931B (ru) |
IE (1) | IE58997B1 (ru) |
IL (1) | IL79420A (ru) |
NZ (1) | NZ216871A (ru) |
PT (1) | PT82989B (ru) |
RU (1) | RU1794079C (ru) |
SU (1) | SU1579460A3 (ru) |
ZA (1) | ZA865274B (ru) |
Families Citing this family (34)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4870169A (en) * | 1985-07-17 | 1989-09-26 | President And Fellows Of Harvard College | Intermediates for beta-lactam antibiotics |
US4673737A (en) * | 1985-08-02 | 1987-06-16 | Harvard University | 7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof |
US4734498A (en) * | 1986-07-10 | 1988-03-29 | Eli Lilly And Company | 3β-succinimidoazetidinones as chiral intermediates |
CA1323370C (en) * | 1986-09-12 | 1993-10-19 | Davis H. Crater | Fluorochemical oxazolidinones |
US4782144A (en) * | 1987-09-14 | 1988-11-01 | Eli Lilly And Company | 1-carba(dethia)-3-hydroxy-3-cephem ester crystalline and crystalline solvate thereof |
US5019571A (en) * | 1988-01-25 | 1991-05-28 | Eli Lilly And Company | 1-carbacephalosporin antibiotics |
US4855418A (en) | 1988-03-23 | 1989-08-08 | Eli Lilly And Company | Process for production of ceophalosporins |
US4820832A (en) * | 1988-03-23 | 1989-04-11 | Eli Lilly And Company | Process for preparing 3-unsubstituted cephalosporins and 1-carba(dethia)cephalosporins |
US4885362A (en) * | 1988-06-06 | 1989-12-05 | Eli Lilly And Company | Azetidinone intermediates for 1-carba(dethia)caphalosporins |
EP0345999A1 (en) * | 1988-06-06 | 1989-12-13 | Eli Lilly And Company | Process for intermediates to 1-carba(1-dethia)-3-cephem-4-carboxylic acids |
EP0345998A1 (en) * | 1988-06-06 | 1989-12-13 | Eli Lilly And Company | Process and intermediates for beta-lactam antibiotics |
CA1334971C (en) * | 1988-06-22 | 1995-03-28 | Eli Lilly And Company | Intermediate for 1-carba(dethia)cephalosporin |
US5453503A (en) * | 1988-10-11 | 1995-09-26 | Eli Lilly And Company | Azetidinone intermediates to carbacephalosporins and process |
KR0169096B1 (ko) * | 1988-10-11 | 1999-01-15 | 리로이 휘테커 | 카바세팔로스포린의 아제티디논 중간체 화합물 및 제조방법 |
US4931557A (en) * | 1988-10-17 | 1990-06-05 | Eli Lilly And Company | Method of resolving cis 3-amino-4-(2-furyl)vinyl)-1-methoxycarbonylmethyl-azetidin-2-one and di-p-toluoyl-tartaric acid salts thereof |
US4931556A (en) * | 1988-10-17 | 1990-06-05 | Eli Lilly And Company | Method of resolving cis 3-amino-4-(2-(2-furyl)eth-1-yl)-methoxycarbonylmethyl-azetidin-2-one and malic acid salts thereof |
JPH02252648A (ja) * | 1989-03-27 | 1990-10-11 | Naomi Iwagou | イオン溶出燒結体 |
US4992545A (en) * | 1989-09-20 | 1991-02-12 | Eli Lilly And Company | Process for preparing 4-substituted azetidinones |
US5106475A (en) * | 1989-09-20 | 1992-04-21 | Eli Lilly And Company | Process for preparing 4-substituted azetidinones |
US5030725A (en) * | 1990-02-06 | 1991-07-09 | Eli Lilly And Company | Method of resolving cis 3-amino-4-[2-(2-furyl)eth-1-yl]-1-methoxycarbonylmethyl-azetidin-2-one using (-)-DAG |
US5051502A (en) * | 1990-06-06 | 1991-09-24 | University Of Notre Dame Du Lac | Rhodium catalyzed cyclization process for bicyclic β-lactams |
DK0479431T3 (da) * | 1990-09-13 | 2000-03-27 | Lilly Co Eli | Mellemprodukter for 1-carbacephalosporiner og fremgangsmåde til fremstilling heraf |
US5089610A (en) * | 1991-04-25 | 1992-02-18 | Eli Lilly And Company | Ring-closure method for 1-carbacephalosporin six-membered ring |
US5521307A (en) * | 1992-02-18 | 1996-05-28 | Eli Lilly And Company | Methods and compounds for the preparation of carbacephems |
JP4212112B2 (ja) | 1996-02-23 | 2009-01-21 | イーライ・リリー・アンド・カンパニー | 非ペプチジルバソプレッシンV1aアンタゴニスト |
AU4224699A (en) | 1999-01-27 | 2000-08-18 | Pharmacia & Upjohn Company | Assays for modulators of elongation factor p activity |
JP4916929B2 (ja) * | 2007-03-23 | 2012-04-18 | ヤマハ発動機株式会社 | 直交型ロボット |
WO2009049238A1 (en) | 2007-10-11 | 2009-04-16 | The Regents Of The University Of California | Compositions and methods of inhibiting n-acylethanolamine-hydrolyzing acid amidase |
CN103269584B (zh) | 2010-07-01 | 2017-05-03 | 阿泽凡药物公司 | 用于治疗创伤后应激障碍的方法 |
WO2014144836A2 (en) | 2013-03-15 | 2014-09-18 | The Regents Of The University Of California | Carbamate derivatives of lactam based n-acylethanolamine acid amidase (naaa) inhibitors |
WO2014144547A2 (en) | 2013-03-15 | 2014-09-18 | The Regents Of The University Of California | Amide derivatives of lactam based n-acylethanolamine acid amidase (naaa) inhibitors |
MX2016012645A (es) | 2014-03-28 | 2017-01-11 | Azevan Pharmaceuticals Inc | Composiciones y metodos para tratar enfermedades neurodegenerativas. |
WO2017221144A1 (en) * | 2016-06-20 | 2017-12-28 | Dr. Reddy's Laboratories Limited | Process for the preparation of elagolix sodium and its polymorph |
CN112500361B (zh) * | 2020-12-27 | 2023-05-12 | 甘肃瀚聚药业有限公司 | 一种(s)-4-苯基-2-恶唑烷酮的制备方法 |
Family Cites Families (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4226866A (en) * | 1972-11-06 | 1980-10-07 | Merck & Co., Inc. | Novel antibiotic analogues of cephalosporins |
US4166816A (en) * | 1975-05-05 | 1979-09-04 | Smithkline Corporation | Methods and intermediates for preparing cis-4-oxoazetidine intermediates |
US4200572A (en) * | 1975-09-03 | 1980-04-29 | Smithkline Corporation | Substituted azetidinones |
ZA766941B (en) * | 1975-11-21 | 1978-06-28 | Merck & Co Inc | 3-(substituted thio)cephalosporins,derivatives and nuclear analogues thereof |
US4174316A (en) * | 1978-08-14 | 1979-11-13 | Merck & Co., Inc. | 4-Iodomethylazetidin-2-one |
US4472576A (en) * | 1982-12-03 | 1984-09-18 | Merck & Co., Inc. | Processes for the production of antibiotic 1-oxadethiacephalosporins |
US4502994A (en) | 1982-12-09 | 1985-03-05 | Hoffmann-La Roche Inc. | Enantiomeric synthesis of 3-amino-4-carbamoyloxymethyl-2-azetidonone-1-sulfate |
US4751299A (en) * | 1983-11-18 | 1988-06-14 | Takeda Chemical Industries, Ltd. | Optically active β-lactams and method of their production |
US4673737A (en) | 1985-08-02 | 1987-06-16 | Harvard University | 7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof |
-
1985
- 1985-07-17 US US06/755,982 patent/US4665171A/en not_active Expired - Fee Related
-
1986
- 1986-07-15 AU AU60166/86A patent/AU595216B2/en not_active Expired
- 1986-07-15 HU HU862911A patent/HU201931B/hu not_active IP Right Cessation
- 1986-07-15 EP EP89120951A patent/EP0362902B1/en not_active Expired - Lifetime
- 1986-07-15 AT AT86305424T patent/ATE63118T1/de not_active IP Right Cessation
- 1986-07-15 ZA ZA865274A patent/ZA865274B/xx unknown
- 1986-07-15 IL IL79420A patent/IL79420A/xx not_active IP Right Cessation
- 1986-07-15 PT PT82989A patent/PT82989B/pt not_active IP Right Cessation
- 1986-07-15 DE DE3650474T patent/DE3650474T2/de not_active Expired - Fee Related
- 1986-07-15 HU HU906465A patent/HU906465D0/hu unknown
- 1986-07-15 AT AT89120951T patent/ATE133172T1/de not_active IP Right Cessation
- 1986-07-15 RU SU864027832A patent/RU1794079C/ru active
- 1986-07-15 DK DK198603356A patent/DK173456B1/da not_active IP Right Cessation
- 1986-07-15 EP EP86305424A patent/EP0209352B1/en not_active Expired - Lifetime
- 1986-07-15 DE DE8686305424T patent/DE3679002D1/de not_active Expired - Lifetime
- 1986-07-16 CA CA000513971A patent/CA1310323C/en not_active Expired - Lifetime
- 1986-07-16 ES ES8600341A patent/ES2000516A6/es not_active Expired
- 1986-07-16 GR GR861857A patent/GR861857B/el unknown
- 1986-07-16 JP JP61168982A patent/JPH0762015B2/ja not_active Expired - Lifetime
- 1986-07-16 KR KR1019860005753A patent/KR900005257B1/ko not_active IP Right Cessation
- 1986-07-16 NZ NZ216871A patent/NZ216871A/xx unknown
- 1986-07-16 CN CN86104783A patent/CN1015178B/zh not_active Expired
- 1986-07-16 IE IE190086A patent/IE58997B1/en not_active IP Right Cessation
- 1986-07-17 AR AR86304531A patent/AR243186A1/es active
-
1987
- 1987-06-05 SU SU874202676A patent/SU1579460A3/ru active
- 1987-12-31 ES ES8703788A patent/ES2005752A6/es not_active Expired
-
1990
- 1990-01-12 AU AU47934/90A patent/AU619938B2/en not_active Ceased
-
1994
- 1994-12-21 JP JP6318486A patent/JP2634775B2/ja not_active Expired - Lifetime
-
1996
- 1996-02-15 DK DK016096A patent/DK16096A/da not_active Application Discontinuation
-
1998
- 1998-06-22 HK HK98105920A patent/HK1007140A1/xx not_active IP Right Cessation
Non-Patent Citations (1)
Title |
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Европейский патент № 0014476, кл. С 07 D 471/04, 1930. * |
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