KR840006807A - 페넴 화합물의 제조방법 - Google Patents
페넴 화합물의 제조방법 Download PDFInfo
- Publication number
- KR840006807A KR840006807A KR1019830005593A KR830005593A KR840006807A KR 840006807 A KR840006807 A KR 840006807A KR 1019830005593 A KR1019830005593 A KR 1019830005593A KR 830005593 A KR830005593 A KR 830005593A KR 840006807 A KR840006807 A KR 840006807A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- group
- general formula
- hydrogen
- Prior art date
Links
- -1 penem compound Chemical class 0.000 title claims 8
- 238000004519 manufacturing process Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims 24
- 238000000034 method Methods 0.000 claims 7
- 150000003254 radicals Chemical class 0.000 claims 6
- 229910052739 hydrogen Inorganic materials 0.000 claims 5
- 239000001257 hydrogen Substances 0.000 claims 5
- 125000000217 alkyl group Chemical group 0.000 claims 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 3
- 125000004429 atom Chemical group 0.000 claims 2
- 238000006243 chemical reaction Methods 0.000 claims 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims 2
- 150000003839 salts Chemical class 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 238000007259 addition reaction Methods 0.000 claims 1
- 150000001336 alkenes Chemical class 0.000 claims 1
- 229910052799 carbon Inorganic materials 0.000 claims 1
- 229910052802 copper Inorganic materials 0.000 claims 1
- 239000010949 copper Substances 0.000 claims 1
- 125000004185 ester group Chemical group 0.000 claims 1
- 150000002148 esters Chemical class 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000000623 heterocyclic group Chemical group 0.000 claims 1
- 150000002431 hydrogen Chemical group 0.000 claims 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 1
- 238000003402 intramolecular cyclocondensation reaction Methods 0.000 claims 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 claims 1
- 229910052753 mercury Inorganic materials 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 claims 1
- 239000002184 metal Substances 0.000 claims 1
- 229910052757 nitrogen Inorganic materials 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims 1
- 150000002894 organic compounds Chemical group 0.000 claims 1
- 125000000962 organic group Chemical group 0.000 claims 1
- 125000006239 protecting group Chemical group 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 229910052709 silver Inorganic materials 0.000 claims 1
- 239000004332 silver Substances 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 125000004434 sulfur atom Chemical group 0.000 claims 1
- 150000003573 thiols Chemical class 0.000 claims 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; 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
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/64—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms, e.g. histidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- 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
-
- 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
- C07D205/09—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 sulfur atom directly attached in position 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D499/00—Heterocyclic compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. penicillins, penems; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
- C07D499/88—Compounds with a double bond between positions 2 and 3 and 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Pens And Brushes (AREA)
- Diaphragms For Electromechanical Transducers (AREA)
- Cephalosporin Compounds (AREA)
- Measuring Magnetic Variables (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (6)
- a) 일반식(Ⅱ)의 화합물을 일반식(Ⅲ)의 화합물과 반응시켜 일반식(Ⅳ)의 화합물을 생성시킨후 보호된 카복시그룹 R1을 제거하여 R이 수소인 토오토머 화합물(Va) 및 (Vb)〔화합물(Va)와 그의 토오토모(Vb)는 서로 평영이다〕를 얻고, 경우에 따라서는 이 토오토머 화합물에 공지방법으로 유기라디칼 R을 도입시켜 R이 유기라디칼인 일반식(Ⅰ)의 화합물로 전환시키거나; b) 일반식(Ⅵ)의 화합물을 분자내 폐환반응시켜 토오토머 화합물〔(Va),(Vb)〕을 얻고, 경우에 따라 (a)에서 기술한대로 R이 유기 라디칼인 일반식(Ⅰ)의 화합물로 전환시키거나;〔여기서 R10은 트리플루오로저급알킬이고 R11은 트리플루오로저급알콜과 디하이드록시 저급알킬 중에서 선택한 것이거나; R10은 수소이고 R11은 2-아미노-4-티아졸릴, 5-아미노-2-티아졸릴, 5-니트로-2-티아졸릴, 1-메틸-2-이미다졸릴, 아미노아세틸아미노메틸, N-메틸-카바모일메틸, 디하이드록시저급알킬,및(여기서, R13및 R14는 각각 수소 또는 저급알킬이고, R15및 R16은 각각 수소 또는 저급알킬이거나 R15와 R16이 그들이 부착되어 있는 질소와 함께 환원자수 3내지 6의 헤테로사이클릭 환을 형성한다)중에서 선택한 것이다〕인 일반식(Ⅰ)의 화합물을 제조하기 위해, 상기 (a)공정에서 정의한 일반식〔(Va),(Vb)〕의 토오토머 을화합물 알킬화시키거나; d) R이 공정 (c)에서 정의한 대동인 일반식(Ⅰ)의 화합물을 제조하기 위해, 일반식(VII)의 화합물을 일반식(VIII')의 티올 또는 그들의 반응성 유도체와 반응시키거나 ; e) R이 공정(c)에서 정의한 대로인 일반식(Ⅰ)의 화합물을 제조하기 위해 일반식(Ⅸ)의 화합물을 3가 유기인 화합물과 반응시키고; 상기 공정(a)에서 (e)중, 반응물내 존재하는 관능기는 보호그룹에 의해 보호시킬 수 있고 공정의 적절한 관계에서 제거시킬 수 있으며, 이렇게 얻어진 일반식(Ⅰ)의 화합물을 경우에 따라 보호된 카복실그룹 R2(존재하는 경우)를 탈보호시켜 유리산, 약학적으로 허용된 염 또는 약학적으로 허용된 에스테르로 분리함을 특징으로 하여, 다음 일반식(Ⅰ)의 화합물 및 R이 수소일 때 그들의 토오토머를 제조하는 방법.상기식에서, R은 수소 또는 유리라디칼이고; G는 하이드록시저급알킬, 바람직하게는 1-하이드록시에틸이며; X는 수소, 약학적으로 허용되는 염 형성그룹, 약학적으로 허용되는 에스테르그룹 또는 카복시보호그룹이고; R1과 R2는 같거나 다른 보호된 카복시그룹이며; Met는 친티오성(thiophilic)금속원자이고; Y는 이탈그룹이며; R′는)목적하는 그룹 R과 다른 유기그룹이고; 일반식(Ⅶ′)의 R은 공정(c)에서 정의한 바와 같다.
- 제1(a)항에 있어서, R1이(여기서 R1′는 트리메틸실릴 또는 t-부틸디페닐실릴이고, R2는 R1에서 정의된 그룹으로부터 선택한 것이거나 알릴옥시카보닐이다)임이 특징인 방법.
- 제1(b)항에 있어서, R2가 알릴옥시-카보닐임이 특징인 방법.
- 제1(a)항 또는 제2항에 있어서, Met가 은, 구리 또는 수은 이이 특징인 방법.
- 제1(a), 1(b), 1(c) 및 2항에서 4항까지 중 어드 한 항에 있어서, 일반식 RZ〔여기서 R은 공정1(a) 내지 1(c)에서 정의된 유기라디칼이고 Z는 이탈그룹이다〕의 화합물과 반응시키거나; 공정 1(a)내지 1(c)중의 어느 하나에 있어서 R이 비치환된 또는 치환된 C2∼C6알킬그룹인 일반식(Ⅰ)의 화합물을 제조하기 위해, 1,2-불포화 치환된 또는 비치환된 C2-C6알킬렌을 사용하여 올레핀부가 반응시키거나; 공정 1(a)내지 1(c)중의 어느 하나에 있어서 R이 황원자로부터 2번째 탄소에 하이드록시 그룹을 가지고 임의로 하나 또는 그 이상의 다른 치환체를 가지는 C2-C6알킬그룹인 일반식(Ⅰ)의 화합물을 제조하기 위해, 치환된 또는 비치환된 1,2-에폭시-C2-C6알칸과 반응시킴을 특징으로 하여, 토오토머를 R이 유리라디칼인 일반식(Ⅰ)의 화합물로 변형시키는 방법.
- 제1항에서 5항까지중 어느 한항에 있어서, 입체구조(5R, 6S, 8R) 또는 (5R, 6R, 8S)를 가지는 일반식(Ⅰ)의 화합물을 제조함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (9)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US445,295 | 1982-11-29 | ||
| US445295 | 1982-11-29 | ||
| US06/445,295 US4530793A (en) | 1982-11-29 | 1982-11-29 | Processes for the production of penems |
| US458,511 | 1983-01-17 | ||
| US06/458,511 US4435412A (en) | 1982-11-29 | 1983-01-17 | 5R,6S,8R-2-(1-Methyl-2-imidazolylmethylthio)-6-(1-hydroxyethyl)penem-3-carboxylic acid |
| US06/461,845 US4435413A (en) | 1983-01-28 | 1983-01-28 | (5R-6S,8R)-6-(1-Hydroxyethyl)-2-(2-glycylaminoethylthio)-penem-3-carboxylic acid |
| US461,845 | 1983-01-28 | ||
| US462,723 | 1983-01-31 | ||
| US06/462,723 US4456609A (en) | 1983-01-31 | 1983-01-31 | (5R, 6S, 8R-6-(1-Hydroxyethyl)-2-(2-[methylaminocarbonyl]-ethylthio)-penem-3-carboxylic acid |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR840006807A true KR840006807A (ko) | 1984-12-03 |
| KR880002512B1 KR880002512B1 (ko) | 1988-11-26 |
Family
ID=27503921
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019830005593A KR880002512B1 (ko) | 1982-11-29 | 1983-11-25 | 페넴 화합물 및 이의 제조방법 |
Country Status (14)
| Country | Link |
|---|---|
| EP (2) | EP0345827A1 (ko) |
| JP (1) | JPH0631254B2 (ko) |
| KR (1) | KR880002512B1 (ko) |
| AT (1) | ATE112778T1 (ko) |
| AU (1) | AU575545B2 (ko) |
| DE (1) | DE3382761T2 (ko) |
| DK (1) | DK166152C (ko) |
| FI (1) | FI834305A (ko) |
| GR (1) | GR81289B (ko) |
| HU (1) | HU194889B (ko) |
| IL (1) | IL70327A0 (ko) |
| NO (1) | NO165073C (ko) |
| NZ (1) | NZ206389A (ko) |
| PT (1) | PT77712B (ko) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0091576B1 (en) * | 1982-03-26 | 1987-07-29 | Hoechst Uk Limited | 7-oxo-4-thia-1-azabicyclo(3,2,0)heptane derivatives |
| GB2159519B (en) * | 1982-03-26 | 1986-08-20 | Hoechst Uk Ltd | 7-oxo-4-thia-1-azabicyclo3,2,0heptane derivatives; azetidinones |
| EP0320497A1 (en) * | 1983-01-25 | 1989-06-14 | Merck & Co. Inc. | Substituted 2-thioxopenams, intermediates therefrom and process for preparing substituted 2-thioxopenams and 2-substituted thiopenems |
| DK141784A (da) * | 1983-03-14 | 1984-09-15 | Schering Corp | Penemforbindelser, fremgangsmaader til deres fremstilling samt farmaceutiske praeparater indeholdende disse |
| YU44241B (en) * | 1983-10-14 | 1990-04-30 | Pfizer | Process for making derivatives of 2-azacyclothiopenem |
| US4772597A (en) * | 1983-10-14 | 1988-09-20 | Pfizer Inc. | 2-azacycloalkylthiopenem derivatives |
| US4584133A (en) * | 1983-11-07 | 1986-04-22 | Schering Corporation | Process for the production of penems |
| US4782145A (en) * | 1986-06-02 | 1988-11-01 | Pfizer Inc. | Process for penem derivatives |
| US4767853A (en) * | 1986-07-21 | 1988-08-30 | Schering Corporation | Synthesis of 1-(allyloxycarbonyl)-methyl-3-(hydroxyethyl)-4-beta-naphthoxythiocarbonylthio-2-azetidinones and hydroxy protected analogs thereof |
| PH24872A (en) * | 1986-08-25 | 1990-12-26 | Schering Corp | (5r,6s,8r)-6-(-1-hydroxyethyl)-2-(3r-pyrrolidin-2-one-3-yl)thiopenem-3-carboxylic acid |
| US4992543A (en) * | 1988-10-19 | 1991-02-12 | Pfizer Inc. | Penem derivatives |
| JP2559649B2 (ja) * | 1991-08-30 | 1996-12-04 | 茂 只野 | 薬草入浴剤の製造方法 |
| WO2018071358A1 (en) * | 2016-10-10 | 2018-04-19 | The Johns Hopkins University | Antibacterial agents against d,d- and l,d-transpeptidases |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB207453A (en) * | 1923-03-10 | 1923-11-29 | Thomas Ford | Improvements in automatic stapling, label tacking machines and the like |
| US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
| EP0042026B1 (de) * | 1978-02-02 | 1986-01-08 | Ciba-Geigy Ag | 3,4-Disubstituierte Azetidin-2-onverbindungen und Verfahren zu ihrer Herstellung |
| JPS5625110A (en) * | 1978-12-18 | 1981-03-10 | Bristol Myers Co | Antibacterial |
| IL59081A0 (en) * | 1979-01-10 | 1980-05-30 | Schering Corp | 2-penem compounds and a method for preparing them |
| EP0024832B1 (en) * | 1979-08-10 | 1985-03-13 | Beecham Group Plc | Beta-lactam antibiotics, their preparation, pharmaceutical compositions containing them and their preparation |
| SE8101464L (sv) * | 1980-03-10 | 1981-09-11 | Sankyo Co | 2-penem-3-karboxylsyraderivat, deras framstellning och anvendning |
| JPS56142282A (en) * | 1980-03-10 | 1981-11-06 | Sankyo Co Ltd | Penem-3-carboxylic acid derivative and its preparation |
| JPS572292A (en) * | 1980-06-06 | 1982-01-07 | Sankyo Co Ltd | Production of penem-3-carboxylic derivative |
| EP0046363B1 (en) * | 1980-08-16 | 1984-11-14 | Beecham Group Plc | Process for the preparation of 2-thio penem derivatives and intermediates therefor |
| US4347183A (en) * | 1981-02-02 | 1982-08-31 | Schering Corporation | Process for the synthesis of penems and carbapenems |
| IT1190842B (it) * | 1981-06-30 | 1988-02-24 | Erba Farmitalia | Via di sintesi di derivati otticamente attivi dell'acido 2-penem-3-carbossilico |
| JPS588084A (ja) * | 1981-07-08 | 1983-01-18 | Takeda Chem Ind Ltd | （６ｒ）−置換−（５ｒ）−ペネム−３−カルボン酸誘導体およびその製造法 |
| EP0180252B1 (en) * | 1981-07-15 | 1989-04-26 | Sumitomo Pharmaceuticals Company, Limited | Process of preparing azetidinone compounds |
| JPS5835190A (ja) * | 1981-08-25 | 1983-03-01 | Sankyo Co Ltd | ペネム−３−カルボン酸誘導体 |
| CA1190236A (en) * | 1981-10-23 | 1985-07-09 | Edward J.J. Grabowski | Antibiotic synthesis |
| US4411906A (en) * | 1981-11-25 | 1983-10-25 | Schering Corporation | (5R,6S,8R)-6-(1-Hydroxyethyl)-2-(2-fluoroethylthio)-penem-3-carboxylates |
| EP0087792A1 (en) * | 1982-03-01 | 1983-09-07 | Merck & Co. Inc. | 6-Substituted-2-carbamimidoyl-pen-2-em-3-carboxylic acids, process for preparing them and antibiotic compositions comprising them |
-
1983
- 1983-11-21 DE DE3382761T patent/DE3382761T2/de not_active Expired - Fee Related
- 1983-11-21 EP EP89113483A patent/EP0345827A1/en not_active Withdrawn
- 1983-11-21 EP EP83111615A patent/EP0110280B1/en not_active Expired - Lifetime
- 1983-11-21 AT AT83111615T patent/ATE112778T1/de not_active IP Right Cessation
- 1983-11-24 GR GR73061A patent/GR81289B/el unknown
- 1983-11-24 FI FI834305A patent/FI834305A/fi not_active Application Discontinuation
- 1983-11-24 DK DK538183A patent/DK166152C/da not_active IP Right Cessation
- 1983-11-24 PT PT77712A patent/PT77712B/pt not_active IP Right Cessation
- 1983-11-24 AU AU21676/83A patent/AU575545B2/en not_active Ceased
- 1983-11-24 NZ NZ206389A patent/NZ206389A/en unknown
- 1983-11-25 IL IL70327A patent/IL70327A0/xx unknown
- 1983-11-25 NO NO834331A patent/NO165073C/no unknown
- 1983-11-25 JP JP58221927A patent/JPH0631254B2/ja not_active Expired - Lifetime
- 1983-11-25 KR KR1019830005593A patent/KR880002512B1/ko not_active IP Right Cessation
- 1983-11-28 HU HU834073A patent/HU194889B/hu not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP0110280A1 (en) | 1984-06-13 |
| DE3382761D1 (de) | 1994-11-17 |
| EP0110280B1 (en) | 1994-10-12 |
| FI834305A (fi) | 1984-05-30 |
| DK538183D0 (da) | 1983-11-24 |
| DK166152B (da) | 1993-03-15 |
| DK166152C (da) | 1993-08-09 |
| KR880002512B1 (ko) | 1988-11-26 |
| NZ206389A (en) | 1986-10-08 |
| PT77712B (en) | 1986-05-12 |
| GR81289B (ko) | 1984-12-11 |
| AU575545B2 (en) | 1988-08-04 |
| FI834305A0 (fi) | 1983-11-24 |
| ATE112778T1 (de) | 1994-10-15 |
| JPS59108789A (ja) | 1984-06-23 |
| IL70327A0 (en) | 1984-02-29 |
| JPH0631254B2 (ja) | 1994-04-27 |
| NO834331L (no) | 1984-05-30 |
| DE3382761T2 (de) | 1995-03-09 |
| NO165073C (no) | 1990-12-19 |
| AU2167683A (en) | 1984-06-07 |
| EP0345827A1 (en) | 1989-12-13 |
| DK538183A (da) | 1984-05-30 |
| PT77712A (en) | 1983-12-01 |
| NO165073B (no) | 1990-09-10 |
| HU194889B (en) | 1988-03-28 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR840006807A (ko) | 페넴 화합물의 제조방법 | |
| IE40014L (en) | Heterocyclic-alkylamino-heterocyclic compounds | |
| KR870008889A (ko) | 베타-락탐화합물, 및 그의 제조 방법 | |
| KR850001757A (ko) | 페넴화합물의 제조방법 | |
| EP0234484A1 (en) | Novel azetidinone derivatives | |
| AU596606B2 (en) | Azetidin-2-one derivatives and process for production thereof | |
| HU193959B (en) | Process for producing anhydropenicillin derivatives | |
| EP0000645B1 (en) | Isopenicillins, processes for their preparation, and compositions containing them | |
| KR860008185A (ko) | 페넴 화합물의 제조방법 | |
| KR850008173A (ko) | 세팔로 스포린 및 그의 제조 중간체의 제조방법 | |
| IE59871B1 (en) | Process for penem derivatives | |
| CA2190408A1 (en) | Process for preparing acetoxyazetidinone derivative and intermediate thereof | |
| KR870003110A (ko) | 카바펜엠 항생제 | |
| AU666559B2 (en) | 4-acylthio azetidinones | |
| EP0230248A1 (en) | Beta-lactam compound and process for preparing the same | |
| KR960010640A (ko) | 2-(2-치환된 피롤리딘-4-일)티오-카바페넴 유도체의 신규 제조방법 | |
| GB2220203A (en) | Process for penems; 6-bromopenems | |
| AU2639999A (en) | Intermediate compounds in the synthesis of the a ring moiety of 2-substituted vitamin d derivatives | |
| JPH05286975A (ja) | １−アザビシクロ［３．３．０オクタン誘導体の製法 | |
| KR940014401A (ko) | 신규 트리아졸로 피리미딘 티온 화합물 및 이의 제조방법 | |
| ES8302687A1 (es) | "procedimiento para la preparacion de derivados de 2-oxa-biciclo (3.3.0) octano". | |
| KR930017901A (ko) | 카바세펨의 제조를 위한 신규한 방법 및 화합물 | |
| KR930016382A (ko) | 벤조페논 유도체의 제조방법 | |
| KR940014405A (ko) | 페넴 화합물(sun-5555)의 제조방법 | |
| JPH0267269A (ja) | ピラゾリジン誘導体およびピラゾリジノン誘導体 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| G160 | Decision to publish patent application | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| FPAY | Annual fee payment |
Payment date: 19941026 Year of fee payment: 7 |
|
| LAPS | Lapse due to unpaid annual fee |