[go: up one dir, main page]

KR830009107A - 2-페넴 화합물의 제조방법 - Google Patents

2-페넴 화합물의 제조방법 Download PDF

Info

Publication number
KR830009107A
KR830009107A KR1019820000375A KR820000375A KR830009107A KR 830009107 A KR830009107 A KR 830009107A KR 1019820000375 A KR1019820000375 A KR 1019820000375A KR 820000375 A KR820000375 A KR 820000375A KR 830009107 A KR830009107 A KR 830009107A
Authority
KR
South Korea
Prior art keywords
compound
formula
hydrogen
lower alkyl
protecting group
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
KR1019820000375A
Other languages
English (en)
Other versions
KR880001774B1 (ko
Inventor
아폰소 아드리아노
혼 프랭크
Original Assignee
스테이나 칸스타드, 로즈마리 아이젠링
쉐링 코포레이숀
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by 스테이나 칸스타드, 로즈마리 아이젠링, 쉐링 코포레이숀 filed Critical 스테이나 칸스타드, 로즈마리 아이젠링
Publication of KR830009107A publication Critical patent/KR830009107A/ko
Application granted granted Critical
Publication of KR880001774B1 publication Critical patent/KR880001774B1/ko
Expired legal-status Critical Current

Links

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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/02—Preparation
    • C07D477/04—Preparation by forming the ring or condensed ring systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D477/00—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring
    • C07D477/10—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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
    • C07D477/12—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6
    • C07D477/16—Heterocyclic compounds containing 1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. carbapenicillins, thienamycins; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulphur-containing hetero ring with hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 4, and 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 hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached in position 6 with hetero atoms or carbon atoms 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 3
    • C07D477/22—Nitrogen atoms
    • 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
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; 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
    • 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

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Molecular Biology (AREA)
  • Public Health (AREA)
  • Veterinary Medicine (AREA)
  • Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Pharmacology & Pharmacy (AREA)
  • Oncology (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Communicable Diseases (AREA)
  • General Chemical & Material Sciences (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)

Abstract

내용 없음

Description

2-페넴 화합물의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (18)

  1. 일반식(II)의 화합물을 3가 유기 포스포러스화합물과 반응시키고 이때 사용된 일반식(II)화합물이 이성체 혼합물인 경우에는 경우에 따라 생성화합물을 입체 이성체로 단리 및 분리시키기전 또는 뒤에 a) 하나이상의 보호그룹의 제거, b) 특정 관능기를 유기산으로 전환, c) 특정관능기를 약제학적으로 허용되는 염으로 전환, 및 d) 특정 관능기를 대사성 에스테를 그룹으로 전환시키는 조작중의 하나이상을 거침을 특징으로 하여 일반식(I)의 화합물 및 그의 약제학적으로 허용되는 염을 제조하는 방법.
    상기 식에서, R1은, 수소, 저급알킬, 아실아미노,(여기서 R4는 수소, 저급알킬, 아릴 또는 헤테로아릴이고, R5는 수소 또는 하이드록시보호그룹이고, R8는 할로겐이다), R9가 저급알킬 수소 또는 -S 보호그룹인 -SR9, 또는그룹을 나타내는데, R10및 R11중 하나는 -N 보호그룹이며 나머지는 수소, 저급알킬, 아릴, 아르알킬 및 아실가운데서 선택되거나 R10및 R11은 각각 수소, 저급알킬, 아르알킬, 아릴 및 아실중에서 선택되는데 단, 하나가 수소인 경우, 나머지는 아실이어야하며; R2는 저급알킬, 아릴, 아르알킬, 아미노알킬, N-보호아미노알킬, 하이드록시알킬, 0-보호하이드록시알킬, 티오알킬, 티오아릴, 티오헤테로아릴, 임의 에스테르화 α-아미노산잔기, 임의 에스테르화 α-(N보호된)아미노산잔기 또는 임의 에스테르화 알킬카복실그룹이며; R3는 니트릴, 테트라졸릴 또는 R6가 수소인 -COOR6, Hal이 할로겐을 나타내며 AIk는 알킬렌 라디칼을 나타내는 라디칼 C(Hal)3-Alk, 저급알킬 아릴, 아릴성그룹, 대사가능한 에스테르그룹 또는 카복시보호그룹이며; X 및 Z는 각각 황, 산소, 라디칼=NR7, (R7이 수소, 아실, 저급알킬, 아릴 또는 N-보호그룹), 또는 n이 1 또는 2인 -(CH2)n-이며, 일반식(II)에서는 R1, R2, R3, X 및 Z가 상기 정의된 바와 같으나 단, R5는 하이드록시 보호그룹이고, R9은 저급알킬 또는 S-보호그룹이며, R7은 수소가 아니고, 치환체 R2중의 카복시 그룹중의 어느것은 에스테르화되어 있으며 R6는 수소가 아니다.
  2. 제1항에 있어서, 3가 유기 포스포러스 화합물이 사이클릭 및/또는 아사이클릭 트리알킬포스파이트, 트리아릴 포스파이트, 혼합알킬아릴 포스파이트 및 혼합 알킬아릴포스포르아미드중에서 선택되고 바람직하게는 트리에틸포스파이트인 방법.
  3. 제2항에 있어서, 일반식(II)화합물 몰당 트리알킬 포스파이트 2몰당량을 사용하고 반응을 20 내지 80℃, 바람직하게는 40 내지 60℃온도에서 시행하는 방법.
  4. 제1항 내지 3항중의 어느하나에 있어서, 다음 일반식(III)의 화합물을 일반식(IV)인 산의 반응성 유도체 바람직하게는 그의 할라이드와 불활성 용매 바람직하게는 할로겐화 탄화수소 용매중 유기염기 바람직하게는 3급아민 존재하에, 산 할라이드를 사용할 경우에는 임의로 할로겐화 수소 경합제를 사용하여 반응시켜 제조된 일반식(II)화합물을 사용하는 방법.
    상기 식중, R1,R2, X, Z 및 R3는 제1항의 일반식(II)에서 정의된 바와 같다.
  5. 제4항에 있어서, 일반식(III)화합물을 일반식(IV)인 산의 반응성 유도체 및 언급된 3급아민 대략 1몰당량(일반식III)의 화합물 몰당), 할로겐화 수소 결합제를 사용할 경우에는 적어도 1몰 당량과 언급된 불활성 용매중에서 혼합함을 특징으로 하는 방법.
  6. 제4항 또는 5항에 있어서, 일반식(IV)의 산할라이드가 알릴옥시 옥살릴클로라이드 또는 바람직하게는 클로로알릴옥시옥살릴클로라이드이며 3급 아민이 디이소프로필에틸아민이고 결합제는 탄산칼슘인 방법.
  7. 제1항 내지 6항중의 어느하나에 있어서, X가 황, -(-CH2-)n- 또는 잔기=NR7(이때 n 및 R7은 1항에서 정의된 바와 같음)인 방법.
  8. 제7항에 있어서, X 및 Z가 모두 S이고, R1이이며, R2가 저급알킬이고 R3가 -COOR6(이때 R6는 아릴 또는 바람직하게는 클로로알릴)인 일반식(I)화합물을 제조하는 방법.
  9. 제1항 내지 7항중의 어느하나에 있어서 X가 (CH2)이고, Z가 S이며 R1이 CH3-CH-OR5이고 R2가 N-보호아미노에틸이며, R2가 -COOR6인 (이때 R5및 R6는 제1항에서 정의된 바와 같음) 일반식(I)의 화합물을 제조하는 방법.
  10. 제1항 내지 8항중의 어느하나에 있어서, R3중의 보호그룹을 제거시키고, R3가 -COOR6일 경우에는 (이때 R6는 알킬, 아릴 또는 알릴릭그룹) R1, R2및 R7중의 보호그룹을 제거시키는 방법.
  11. 제10항에 있어서, 나트륨 또는 칼륨(5R, 6S, 8R)-6-(1-하이드록시에틸)-2-에틸티오-페넴-3-카복실레이트 또는 나트륨 또는 칼륨(5R, 6S, 8R)-6-(1-하이드록시에틸)-2-메틸티오-페넴-3-카복실레이트를 제조하는 방법.
  12. 일반식(V)의 화합물 또는 그의 약제학적으로 허용되는 염.
    상기식에서 R1, R2, R3, X 및 Z는 제1항에서 정의된 바와 같으나, 단, (i) Z 및 X는 동시에 n이 1 또는 2인 -(CH2)n-이 될 수 없으며; (ii) X가 S일때는 Z는 0또는 =NR7이며; (iii) X가 O일때는 Z는 O, S 또는 =NR7이며; (iv) X가 -CH2-이면 Z는 =NR7이나, R7이 H 또는 저급알킬이고 R2가 저급알킬이면 R1은 아실아미노가 될 수 없으며; (v) X가 -(-CH2-)2-이면, Z는 =NR7이어야 한다(상기에서 R7은 제1항에서 정의된 바와 같다).
  13. 제12항에 있어서, X가 =NR7인 화합물 및 그의 약제학적으로 허용되는 염.
  14. 제12항에 있어서, 일반식(VI)의 화합물 및 그의 약제학적으로 허용되는 염.
    상기 식중 G는 저급알콕시 또는 그룹이고 R2, R3및 R7은 제12항에서 정의된 바와 같다.
  15. 제12항에 있어서, 일반식(VII)의 화합물 및 그의 약제학적으로 허용되는 염.
    상기식중, Z, R2및 R3는 제12항에서 정의된 바와 같고 이때 R3는 바람직하게는 -COOR6이며 R6는 제1항에서 정의된 바와 같다.
  16. 제12항 내지 15항중의 어느 하나에 있어서, R1이 하이드록시 보호그룹 또는 N-보호그룹 또는 S-보호그룹을 함유하고 및/또는 R2가 0-보호그룹 또는 N-보호그룹을 함유하며 및/또는 R7이 N-보호그룹이고 R3는 니트릴, 테트라졸릴 또는 -COOR6(이때 R6는 수소 또는 대사성 에스테르 그룹중에서 선택됨)인 화합물 및 그의 약제학적으로 허용되는 염.
  17. 제12항 내지 16항중의 어느 하나에서 정의된 화합물 또는 그의 약제학적으로 허용되는 염을 약제학적으로 허용되는 담체 또는 부형제와 혼합 함유함을 특징으로 하는 약제학적 조성물.
  18. 제12항 내지 16항중의 어느 하나에 있어서, 세균감염증 치료에 사용되는 화합물 또는 약제학으로 허용되는 염.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR8200375A 1981-02-02 1982-01-29 2-페넴 화합물의 제조방법 Expired KR880001774B1 (ko)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US230,774 1981-02-02
US06/230,774 US4347183A (en) 1981-02-02 1981-02-02 Process for the synthesis of penems and carbapenems
US230774 1981-02-02

Publications (2)

Publication Number Publication Date
KR830009107A true KR830009107A (ko) 1983-12-17
KR880001774B1 KR880001774B1 (ko) 1988-09-15

Family

ID=22866531

Family Applications (1)

Application Number Title Priority Date Filing Date
KR8200375A Expired KR880001774B1 (ko) 1981-02-02 1982-01-29 2-페넴 화합물의 제조방법

Country Status (17)

Country Link
US (1) US4347183A (ko)
EP (2) EP0162193A1 (ko)
JP (1) JPS57146777A (ko)
KR (1) KR880001774B1 (ko)
AT (1) ATE21699T1 (ko)
AU (1) AU557691B2 (ko)
DE (1) DE3272792D1 (ko)
DK (1) DK160877C (ko)
FI (1) FI74966C (ko)
HU (1) HU189559B (ko)
IE (1) IE54214B1 (ko)
IL (1) IL64905A (ko)
NO (1) NO159795C (ko)
NZ (1) NZ199599A (ko)
PH (1) PH21195A (ko)
PT (1) PT74356B (ko)
ZA (1) ZA82567B (ko)

Families Citing this family (37)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL8102736A (nl) * 1980-06-06 1982-01-04 Sankyo Co Penem-3-carbonzuurverbindingen en hun bereiding.
GB2083462B (en) * 1980-08-16 1984-05-02 Beecham Group Ltd 2-thiopenem derivatives
EP0069378B1 (en) * 1981-07-08 1987-01-07 Hoechst Uk Limited Antibacterial penem derivatives
ES8305366A1 (es) * 1981-07-08 1983-04-01 Hoechst Uk Ltd "procedimiento para la preparacion de derivados de penem".
US4552873A (en) * 1981-08-19 1985-11-12 Sankyo Company Limited Carbapenem compounds, and compositions containing them
ES523890A0 (es) * 1982-07-08 1985-04-01 Hoechst Uk Ltd Un procedimiento para preparar derivados de penem.
KR900006449B1 (ko) * 1982-08-24 1990-08-31 상꾜 가부시끼가이샤 아제티디논 화합물의 제조방법
US4794109A (en) * 1982-11-16 1988-12-27 Ciba-Geigy Corporation 6-hydroxy-lower alkylpenem compounds, pharmaceutical preparations that contain these compounds, and the use of the latter
DE3366926D1 (en) * 1982-11-16 1986-11-20 Schering Corp Penems, pharmaceutical compositions containing them, process for preparing them
EP0345827A1 (en) * 1982-11-29 1989-12-13 Schering Corporation Process for the production of penem compounds
EP0115308A3 (en) * 1983-01-25 1984-10-10 Merck & Co. Inc. 2-unsaturated alkylthio-pen-2-em-3-carboxylic acids and process for preparing substituted 2-thioxopenams and 2-substituted thiopenems
US4619783A (en) * 1983-06-10 1986-10-28 Pfizer Inc. Process and intermediates for the preparation of penem derivatives
US4725678A (en) * 1983-06-10 1988-02-16 Pfizer Inc. Azetidinone intermediates for the preparation of penem derivatives
US4595539A (en) * 1983-06-10 1986-06-17 Pfizer Inc. Preparation of penem derivatives and azetidinone intermediates
GB8321677D0 (en) * 1983-08-11 1983-09-14 Erba Farmitalia Preparation of penems
US4656165A (en) * 1983-09-02 1987-04-07 Ciba-Geigy Corporation Aminomethyl penem compounds
EP0134301A1 (en) * 1983-09-15 1985-03-20 Merck & Co. Inc. 6-(1'-Hydroxyethyl)-3-substituted amino-1-azabicyclo(3.2.0)-hept-2-en-7-one-2-carboxylic acid
JPS60224672A (ja) * 1984-04-23 1985-11-09 Sumitomo Chem Co Ltd β−ラクタム誘導体の製造法
US4761408A (en) * 1984-11-02 1988-08-02 Ciba-Geigy Corporation Crystalline aminomethyl compound
US4680292A (en) * 1984-12-13 1987-07-14 Merck & Co., Inc. Carbapenems and 1-methylcarbapenems having a 2-heteroaryliumaliphatic substituent
AU577105B2 (en) * 1985-04-02 1988-09-15 T.P.O. :Pharmachim: Acylaminic penicillin derivatives
US4782051A (en) * 1985-06-10 1988-11-01 Merck & Co., Inc. 2-aza-substituted 1-carbadethiapen-2-em-3 carboxylic acids
US4783453A (en) * 1985-06-10 1988-11-08 Merck & Co., Inc. 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids
US5140030A (en) * 1985-06-10 1992-08-18 Merck 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids
EP0208889A1 (en) * 1985-06-10 1987-01-21 Merck & Co. Inc. 2-Aza-substituted 1-carbadethiapen-2-EM-3-carboxylic acids
US4833167A (en) * 1985-06-10 1989-05-23 Merck & Co., Inc. 2-aza-substituted 1-carbadethiapen-2-em-3-carboxylic acids
US5215997A (en) * 1985-09-11 1993-06-01 Ciba-Geigy Corporation Synthesis of beta-lactam compounds
EP0215739B1 (de) * 1985-09-11 1993-09-01 Ciba-Geigy Ag Synthese von Beta-Lactamverbindungen
EP0223397B1 (en) * 1985-10-17 1991-09-04 Pfizer Inc. Process for 2-(1-oxo-3-thiolanyl)-2-penem antibiotics
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
US4876338A (en) * 1986-07-21 1989-10-24 Schering Corporation Synthesis of azetidinones using CuCl
US5075438A (en) * 1986-07-21 1991-12-24 Schering Corporation Synthesis of azetidinones
US5053502A (en) * 1986-07-21 1991-10-01 Schering Corporation Anhydro penicillin derivatives
GB9103034D0 (en) * 1991-02-13 1991-03-27 Fujisawa Pharmaceutical Co Processes for preparing carbapenem derivatives
US9120808B2 (en) 2009-09-15 2015-09-01 Nabriva Therapeutics Ag Substituted clavulanic acid
JP2016069346A (ja) * 2014-09-30 2016-05-09 株式会社日本触媒 チオール化合物
WO2018071358A1 (en) 2016-10-10 2018-04-19 The Johns Hopkins University Antibacterial agents against d,d- and l,d-transpeptidases

Family Cites Families (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NL178005C (nl) 1972-11-06 1986-01-02 Merck & Co Inc Werkwijze voor het bereiden van een farmaceutisch preparaat met antibacteriele werking, alsmede werkwijze ter bereiding van een cefalosporine-antibioticum.
US4293599A (en) * 1974-10-29 1981-10-06 Nippon Paint Co., Ltd. Method of forming decorative relief pattern and pattern-forming device therefor
US4172899A (en) * 1975-12-09 1979-10-30 Microlife Technics, Inc. Preparation of creamed cottage cheese with a Streptococcus diacetilactis mutant
GB1591438A (en) 1976-09-09 1981-06-24 Glaxo Lab Ltd Clavem derivatives
US4234596A (en) * 1976-11-19 1980-11-18 Merck & Co., Inc. 3-(2-Aminoethylthio)-6-(1-hydroxyethyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid
US4172895A (en) * 1977-12-28 1979-10-30 Merck & Co., Inc. 6-(1'-Hydroxyethyl)-2-aminoethylthio-oxapen-2-em-3-carboxylic acid
EP0003960B1 (de) 1978-02-02 1983-06-29 Ciba-Geigy Ag 6-Substituierte Thia-Azaverbindungen, ihre Herstellung und diese enthaltende pharmazeutische Präparate
EP0004132A1 (en) * 1978-03-04 1979-09-19 Beecham Group Plc Esters of beta-lactam antibiotics, a process for their preparation pharmaceutical compositions containing them and the compounds for use as antibacterial agents
US4203902A (en) * 1978-04-21 1980-05-20 Merck & Co., Inc. Process for preparing 6- and 2-substituted-1-carbadethiapen-2-em-3-carboxylic acids
US4217453A (en) * 1978-07-24 1980-08-12 Merck & Co., Inc. 6-Amido-3-substituted-amino-1-azabicyclo[3.2.0]hept-2-en-7-one-2-carboxylic acid
JPS5559193A (en) * 1978-09-20 1980-05-02 Glaxo Group Ltd Bblactam compound
US4206219A (en) * 1978-10-24 1980-06-03 Merck & Co., Inc. 6- and 1-Substituted-1-carbadethiapen-2-em-3-carboxylic acid
IL59081A0 (en) * 1979-01-10 1980-05-30 Schering Corp 2-penem compounds and a method for preparing them
US4314942A (en) * 1979-01-10 1982-02-09 Schering Corporation Deprotection of allylic esters, carbonates and carbamates catalyzed by palladium compounds
NO155548C (no) * 1979-02-10 1987-04-15 Kyowa Hakko Kogyo Kk Fremgangsmaate til fremstilling av optisk aktive cefalosporin-analoger.
GB2042508B (en) * 1979-02-14 1983-02-23 Beecham Group Ltd 3-alkoxy-penem derivatives
GB2045235A (en) 1979-03-26 1980-10-29 Hoechst Uk Ltd Cyclisation of sulphides
GB2046746B (en) 1979-03-26 1983-05-18 Hoechst Uk Ltd Production of polycyclic beta -lactams by the cyclisation of sulphides
GB2045236A (en) 1979-03-26 1980-10-29 Hoechst Uk Ltd Oxapenem derivatives
US4269771A (en) * 1979-04-06 1981-05-26 Farmitalia Carlo Erba Total synthesis of 7-oxo-4-thia-1-azabicyclo-[3,2,0]-heptane-2-carboxyl derivatives useful as β-lactamase inhibitors and antibacterial agents
EP0025602B1 (en) * 1979-09-13 1984-12-19 Kyowa Hakko Kogyo Co., Ltd Acylated cephalosporin analogs, process for their preparation and pharmaceutical compositions comprising them
DE3069524D1 (en) 1979-12-20 1984-11-29 Hoechst Uk Ltd Penem derivatives
EP0035188B1 (en) * 1980-02-28 1985-04-17 Schering Corporation 2-penem compounds, pharmaceutical compositions containing them and methods for their preparation
JPS579784A (en) * 1980-06-23 1982-01-19 Sankyo Co Ltd Production of penem-3-carboxylic derivative

Also Published As

Publication number Publication date
DK160877B (da) 1991-04-29
IE54214B1 (en) 1989-07-19
NO820264L (no) 1982-08-03
FI74966C (fi) 1988-04-11
FI820281L (fi) 1982-08-03
EP0058317B1 (en) 1986-08-27
IL64905A0 (en) 1982-04-30
PT74356A (en) 1982-02-01
IL64905A (en) 1986-04-29
EP0162193A1 (en) 1985-11-27
ZA82567B (en) 1983-01-26
DK38982A (da) 1982-08-03
ATE21699T1 (de) 1986-09-15
HU189559B (en) 1986-07-28
PH21195A (en) 1987-08-19
IE820211L (en) 1982-08-02
NZ199599A (en) 1985-11-08
US4347183A (en) 1982-08-31
NO159795C (no) 1989-02-08
EP0058317A1 (en) 1982-08-25
NO159795B (no) 1988-10-31
DE3272792D1 (en) 1986-10-02
JPS57146777A (en) 1982-09-10
KR880001774B1 (ko) 1988-09-15
PT74356B (en) 1984-05-30
AU7991782A (en) 1982-08-12
FI74966B (fi) 1987-12-31
AU557691B2 (en) 1987-01-08
DK160877C (da) 1991-10-14

Similar Documents

Publication Publication Date Title
KR830009107A (ko) 2-페넴 화합물의 제조방법
ATE12492T1 (de) Aryloxypropanolamine, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel.
US5030732A (en) Aminoethylphosphinic acid derivatives
KR920000731A (ko) 신규 이미다졸 유도체, 그의 제조 방법, 그로부터 얻어진 신규 중간체, 의약으로서의 용도 및 그를 함유하는 제약 조성물
ATE14579T1 (de) Pharmazeutische heterocyclische verbindungen, verfahren zu ihrer herstellung und sie enthaltende zusammensetzungen.
ATE46696T1 (de) 1- und 1,1-disubstituierte, 6-substituierte, 2carbamimidoyl-1-carbadethiapen-2-em-3carbons|uren, verfahren zur herstellung und diese enthaltende antibiotische zusammensetzung.
ES8200645A1 (es) Un procedimiento para la preparacion de un muramildipeptido.
ES8306160A1 (es) "procedimiento para preparar un nuevo compuesto de cefem".
KR910018363A (ko) 3,5-이치환된 2-이소옥사졸린 및 이소옥사졸, 이의 제조방법 이를 함유하는 약제 및 이의 용도
KR930703336A (ko) 신규한 메틸렌비스포스폰산 유도체
KR850004472A (ko) 4h-3,i-벤즈옥사진-4-온 유도체의 제조방법
ES8201576A1 (es) Procedimiento para la obtencion de compuestos de acido di- glicidil-isocianurico n-sustituidos
ATE144516T1 (de) Verfahren zur herstellung von cephalosporinzwischenverbindungen
FR2806726B1 (fr) Procede de preparation de la (2s,3r,4s)-4-hydroxyisoleucine et de ses analogues
ES8303353A1 (es) Un procedimiento para la preparacion de nuevos derivados de caprilolactama.
JPS5283396A (en) Novel compound physiologically acceptable salts thereof process for preparing same and medical composition containing same
ES467090A1 (es) Procedimiento de preparacion de nuevas oximas derivadas del acido 3-tiadiazolil-tiometil-7-amino-tiazolil-acetamido-ce- falosporanico
ATE212637T1 (de) Anitbiotisch wirksame cephalosporine und verfahren zu ihrer herstellung
NZ219758A (en) Heterocyclic ester derivatives of 1,4 dihydropyridin-3,5-dicarboxylic acids intermediates and pharmaceutical compositions
DK173182A (da) Fremgangsmaade til fremstilling af 4"-deoxy-4"-methylen-oleandomycin-forbindelser eller syreadditionssalte deraf
US4545942A (en) Amino-acid derivatives, their preparation and their use as pharmaceuticals
ES481602A1 (es) Un procedimiento para la preparacion de derivados de la hi- dantoina.
ATE29251T1 (de) Aminopyridincarbonsaeure-derivate, verfahren zu ihrer herstellung und diese enthaltende pharmazeutische zusammensetzungen.
ES8307254A1 (es) Un procedimiento para la preparacion de un enantiomero de beta-lactama.
IL66633A0 (en) 1-aryloxy-3-alkylamino-propan-2-ols,their preparation and pharmaceutical compositions containing them

Legal Events

Date Code Title Description
PA0109 Patent application

St.27 status event code: A-0-1-A10-A12-nap-PA0109

R17-X000 Change to representative recorded

St.27 status event code: A-3-3-R10-R17-oth-X000

PG1501 Laying open of application

St.27 status event code: A-1-1-Q10-Q12-nap-PG1501

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PA0201 Request for examination

St.27 status event code: A-1-2-D10-D11-exm-PA0201

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PE0902 Notice of grounds for rejection

St.27 status event code: A-1-2-D10-D21-exm-PE0902

P11-X000 Amendment of application requested

St.27 status event code: A-2-2-P10-P11-nap-X000

P13-X000 Application amended

St.27 status event code: A-2-2-P10-P13-nap-X000

PG1605 Publication of application before grant of patent

St.27 status event code: A-2-2-Q10-Q13-nap-PG1605

PE0701 Decision of registration

St.27 status event code: A-1-2-D10-D22-exm-PE0701

PR0701 Registration of establishment

St.27 status event code: A-2-4-F10-F11-exm-PR0701

PR1002 Payment of registration fee

St.27 status event code: A-2-2-U10-U11-oth-PR1002

Fee payment year number: 1

PC1903 Unpaid annual fee

St.27 status event code: A-4-4-U10-U13-oth-PC1903

Not in force date: 19910914

Payment event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

PC1903 Unpaid annual fee

St.27 status event code: N-4-6-H10-H13-oth-PC1903

Ip right cessation event data comment text: Termination Category : DEFAULT_OF_REGISTRATION_FEE

Not in force date: 19910914

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000

R18-X000 Changes to party contact information recorded

St.27 status event code: A-5-5-R10-R18-oth-X000