KR840008369A - 펜엠화합물의 제조방법 - Google Patents
펜엠화합물의 제조방법 Download PDFInfo
- Publication number
- KR840008369A KR840008369A KR1019840001733A KR840001733A KR840008369A KR 840008369 A KR840008369 A KR 840008369A KR 1019840001733 A KR1019840001733 A KR 1019840001733A KR 840001733 A KR840001733 A KR 840001733A KR 840008369 A KR840008369 A KR 840008369A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- ester
- reacting
- conversion
- Prior art date
Links
- 150000001875 compounds Chemical class 0.000 title claims 8
- 238000000034 method Methods 0.000 title claims 4
- 150000002148 esters Chemical class 0.000 claims 6
- 150000003839 salts Chemical class 0.000 claims 6
- 238000006243 chemical reaction Methods 0.000 claims 4
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 claims 2
- 239000002253 acid Substances 0.000 claims 2
- -1 carbamoyloxyethyl Chemical group 0.000 claims 2
- 125000006239 protecting group Chemical group 0.000 claims 2
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims 1
- 238000010511 deprotection reaction Methods 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims 1
- 238000002955 isolation Methods 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 230000002503 metabolic effect Effects 0.000 claims 1
- 231100000252 nontoxic Toxicity 0.000 claims 1
- 230000003000 nontoxic effect Effects 0.000 claims 1
- 150000002903 organophosphorus compounds Chemical class 0.000 claims 1
- 159000000000 sodium salts Chemical class 0.000 claims 1
- 231100000331 toxic Toxicity 0.000 claims 1
- 230000002588 toxic effect Effects 0.000 claims 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 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
- 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
-
- 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
- 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
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 일반식(1)의 화합물을 트리플루로아세트산 또는 트리클로로아세트산 존재하에 알킬리금속 시아네이트와 바응시키거나, 일반식(II)의 화합물을 구조식(III)의 화합물 또는 그의 반응성 유도체와 반응시키거나, 구조식[IVa, IVb] 화합물을 일반식(V)의 화합물과 반응시키거나, 구조식(VI)의 화합물을 삼가의 유기인 화합물과 반응시키고, 필요하거나 원하면 i) 하나이상의 보호그룹의 탈보호, ii) (5R,6S,8R)입체이성체의 분리, iii) 유리산의 약학적으로 무독한 염 또는 대사가능한 에스테르로의 전환, iv) 염 또는 에스테르의 유리산으로의 전환, v) 에스테르의 에스테르교환 또는 약학적으로 무독한 염으로의 전환, vi) 염의 다른염 또는 에스테르로의 전환공정증 하나이상을 계속해서 수행함을 특징으로하여 신규의 구조식(A)의 5R,6S,8R-6-(1-하이드록시에틸)-2-(2-카바모일옥시에틸티오)펜엠-3-카복실산 및 그의 약학적으로 무독한 염 및 대사가능한 에스테르를 제조하는 방법.상기식에서 Pg는 하이드록시 보호그룹이며, Pr은 카복시보호그룹이고, R은 카바모일옥시에틸 이외의 유기라디칼이며, L은 이탈그룹이고, 일반식(II), 구조식[IVa, IVb] 및 구조식(VI)의 화합물에서 작용성그룹은 필요하거나 원하면 보호시킨다.
- 제1항이 있어, 알칼리금속염을 제조함을 특징으로 하는 방법.
- 제2항에 있어서, 나트륨염을 제조함을 특징으로 하는 방법.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US06/481,551 US4504485A (en) | 1983-04-04 | 1983-04-04 | 5R,6S,8R-6-(1-Hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxylic acid |
US481551 | 1983-04-04 | ||
US481,551 | 1983-04-04 |
Publications (2)
Publication Number | Publication Date |
---|---|
KR840008369A true KR840008369A (ko) | 1984-12-14 |
KR880001989B1 KR880001989B1 (ko) | 1988-10-10 |
Family
ID=23912395
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019840001733A KR880001989B1 (ko) | 1983-04-04 | 1984-04-02 | 펜엠 화합물의 제조방법 |
Country Status (24)
Country | Link |
---|---|
US (1) | US4504485A (ko) |
EP (1) | EP0121502B1 (ko) |
JP (1) | JPS59184185A (ko) |
KR (1) | KR880001989B1 (ko) |
AT (1) | ATE26448T1 (ko) |
AU (1) | AU559521B2 (ko) |
CA (1) | CA1248520A (ko) |
DE (1) | DE3463050D1 (ko) |
DK (1) | DK162286C (ko) |
ES (1) | ES531131A0 (ko) |
FI (1) | FI77867C (ko) |
GB (1) | GB2138420B (ko) |
GR (1) | GR81464B (ko) |
HK (1) | HK59489A (ko) |
HU (1) | HU193430B (ko) |
IE (1) | IE57163B1 (ko) |
IL (1) | IL71413A (ko) |
NO (1) | NO163133C (ko) |
NZ (1) | NZ207704A (ko) |
OA (1) | OA07698A (ko) |
PH (1) | PH20548A (ko) |
PT (1) | PT78347B (ko) |
SG (1) | SG32589G (ko) |
ZA (1) | ZA842434B (ko) |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4634556A (en) * | 1985-05-10 | 1987-01-06 | Schering Corporation | Crystalline sodium (5R, 6S, 8R)-6-(1-hydroxyethyl)-2-(2-carbamoyloxyethylthio)-penem-3-carboxylate and process for making same |
AT392903B (de) * | 1987-10-08 | 1991-07-10 | Hoechst Ag | Pharmazeutische zubereitung enthaltend ein cephalosporin und ein penemantibiotikum |
US4876365A (en) * | 1988-12-05 | 1989-10-24 | Schering Corporation | Intermediate compounds for preparing penems and carbapenems |
KR20010101030A (ko) | 1999-09-17 | 2001-11-14 | 도리이 신이찌로 | 제약학적 항균 조성물 |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4168314A (en) * | 1977-11-17 | 1979-09-18 | Merck & Co., Inc. | 6-(1'-Hydroxyethyl)-2-aminoethylthio-pen-2-em-3-carboxylic acid |
IL59081A0 (en) * | 1979-01-10 | 1980-05-30 | Schering Corp | 2-penem compounds and a method for preparing them |
JPS55153789A (en) * | 1979-04-11 | 1980-11-29 | Sankyo Co Ltd | Penem-3-carboxylic acid derivative and its preparation |
US4482565A (en) * | 1980-02-22 | 1984-11-13 | Farmitalia Carlo Erba S.P.A. | β-Lactam-containing antibacterial agents and β-lactamase inhibitors |
ZA815593B (en) * | 1980-08-16 | 1982-10-27 | Beecham Group Plc | Process for the preparation of 2-thio penem derivatives,certain of these compounds and intermediates therefor |
JPS57176988A (en) * | 1981-04-09 | 1982-10-30 | Sankyo Co Ltd | Penam-3-carboxylic acid derivative and its preparation |
JPS5843978A (ja) * | 1981-09-10 | 1983-03-14 | Sankyo Co Ltd | ペネム−3−カルボン酸誘導体およびその製法 |
-
1983
- 1983-04-04 US US06/481,551 patent/US4504485A/en not_active Expired - Fee Related
-
1984
- 1984-03-30 IL IL71413A patent/IL71413A/xx not_active IP Right Cessation
- 1984-03-30 FI FI841272A patent/FI77867C/fi not_active IP Right Cessation
- 1984-03-30 CA CA000450968A patent/CA1248520A/en not_active Expired
- 1984-03-30 PT PT78347A patent/PT78347B/pt not_active IP Right Cessation
- 1984-03-30 GR GR74271A patent/GR81464B/el unknown
- 1984-03-30 IE IE795/84A patent/IE57163B1/xx unknown
- 1984-03-30 NZ NZ207704A patent/NZ207704A/en unknown
- 1984-03-30 ZA ZA842434A patent/ZA842434B/xx unknown
- 1984-03-30 GB GB08408240A patent/GB2138420B/en not_active Expired
- 1984-03-30 DK DK174584A patent/DK162286C/da active
- 1984-03-30 ES ES531131A patent/ES531131A0/es active Granted
- 1984-04-02 NO NO841292A patent/NO163133C/no unknown
- 1984-04-02 JP JP59065653A patent/JPS59184185A/ja active Granted
- 1984-04-02 KR KR1019840001733A patent/KR880001989B1/ko not_active IP Right Cessation
- 1984-04-02 AU AU26309/84A patent/AU559521B2/en not_active Ceased
- 1984-04-02 PH PH40489A patent/PH20548A/en unknown
- 1984-04-02 OA OA58271A patent/OA07698A/xx unknown
- 1984-04-03 DE DE8484810164T patent/DE3463050D1/de not_active Expired
- 1984-04-03 EP EP84810164A patent/EP0121502B1/en not_active Expired
- 1984-04-03 AT AT84810164T patent/ATE26448T1/de not_active IP Right Cessation
- 1984-04-03 HU HU841329A patent/HU193430B/hu unknown
-
1989
- 1989-05-18 SG SG325/89A patent/SG32589G/en unknown
- 1989-07-27 HK HK594/89A patent/HK59489A/xx unknown
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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: 19930927 Year of fee payment: 6 |
|
LAPS | Lapse due to unpaid annual fee |