KR830001941A - β-락타마제-억제제로서의 6-B-치환 페닐실란산의 제조방법 - Google Patents
β-락타마제-억제제로서의 6-B-치환 페닐실란산의 제조방법 Download PDFInfo
- Publication number
- KR830001941A KR830001941A KR1019800000921A KR800000921A KR830001941A KR 830001941 A KR830001941 A KR 830001941A KR 1019800000921 A KR1019800000921 A KR 1019800000921A KR 800000921 A KR800000921 A KR 800000921A KR 830001941 A KR830001941 A KR 830001941A
- Authority
- KR
- South Korea
- Prior art keywords
- carboxy protecting
- integer
- chlorine
- carbon atoms
- group
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 2
- 239000002253 acid Substances 0.000 title 1
- 239000003781 beta lactamase inhibitor Substances 0.000 title 1
- 229940126813 beta-lactamase inhibitor Drugs 0.000 title 1
- PARWUHTVGZSQPD-UHFFFAOYSA-N phenylsilane Chemical class [SiH3]C1=CC=CC=C1 PARWUHTVGZSQPD-UHFFFAOYSA-N 0.000 title 1
- 229940126085 β‑Lactamase Inhibitor Drugs 0.000 title 1
- 229930182555 Penicillin Natural products 0.000 claims 5
- 229940049954 penicillin Drugs 0.000 claims 5
- 150000001875 compounds Chemical class 0.000 claims 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims 3
- 229910052801 chlorine Inorganic materials 0.000 claims 3
- 239000000460 chlorine Chemical group 0.000 claims 3
- 229910052740 iodine Chemical group 0.000 claims 3
- 125000004414 alkyl thio group Chemical group 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 229910052731 fluorine Inorganic materials 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 238000001727 in vivo Methods 0.000 claims 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical group ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 1
- SYKNUAWMBRIEKB-UHFFFAOYSA-N [Cl].[Br] Chemical compound [Cl].[Br] SYKNUAWMBRIEKB-UHFFFAOYSA-N 0.000 claims 1
- 125000003545 alkoxy group Chemical group 0.000 claims 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 1
- 229910052794 bromium Inorganic materials 0.000 claims 1
- 125000005997 bromomethyl group Chemical group 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 229910052739 hydrogen Inorganic materials 0.000 claims 1
- 239000001257 hydrogen Substances 0.000 claims 1
- 239000011630 iodine Chemical group 0.000 claims 1
- 229910000096 monohydride Inorganic materials 0.000 claims 1
- -1 salt compounds Chemical class 0.000 claims 1
Classifications
-
- 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
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
-
- 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
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—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
-
- 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
-
- 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)
- Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Medicinal Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Abstract
내용 없음
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (3)
- 다음 구조식(Ⅴ) 또는 약리학적으로 허용되는 이들의 염기성으로 구성되는 군의 화합물.상기 구조식에서R는 불소, 염소 및 요드원자, 플루오로메틸, 클로로메틸, 브로모메틸, 1개 내지 4개 탄소원자의 알콕시 또는 1개 내지 4개 탄소원자의 알킬티오이고,n은 0 내지 2의 정수이며,R1은 페니실린 카르복시 보호기들이다.단 R이 알킬티오, 염소, 또는 요드원자인 경우 n은 0 내지 1의 정수이다.
- 6-α-브로모에피머를 거의 함유하지 않는 구조식(Ⅵ)화합물군 또는 약리학적으로 허용되는 이들의 염기염 화합물.상기 구조식에서 R14는 페니실린 카르복시 보호기들이다.
- 다음 구조식(Ⅰ)의 화합물을 유기주석 1수소화물(Organotin monohydride)과 약 0 내지 110℃에서 반응시키고 R19가 기존의 페니실린 카르복시 보호기인 경우는 이어서 R19를 제거하여 다음 구조식(Ⅱ)군의 화합물을 제조하는 방법.상기 구조식에서R15는 불소, 염소 브롬, 및 요드원자, 1개 내지 4개 탄소원자 알콕시 및 1개 내지 4개 탄소원자 알킬티오이고,n은 0 내지 2의 정수이며,R13은 수소 또는 생체내에서 쉽게 가수분해되는 에스테르 형성 잔유기이고,X는 염소, 브롬 또는 요드원자이며또는 R19는 생체내에서 쉽게 가분해 되는 에스테르 형성 잔유기 또는 기존의 페니실린 카르복시 보호기이다. 단 R19가 기존의 페니실린 카르복시 보호기인 경우n은 0내지 1의 정수이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US1780979A | 1979-03-05 | 1979-03-05 | |
US17809 | 1979-03-05 | ||
US017809 | 1979-03-05 | ||
US96832 | 1979-11-23 | ||
US06/096,832 US4397783A (en) | 1979-03-05 | 1979-11-23 | Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners |
Publications (2)
Publication Number | Publication Date |
---|---|
KR830001941A true KR830001941A (ko) | 1983-05-19 |
KR840000589B1 KR840000589B1 (ko) | 1984-04-24 |
Family
ID=26690341
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019800000921A KR840000589B1 (ko) | 1979-03-05 | 1980-03-04 | 6-β-치환된 페니실란산의 제조방법 |
Country Status (29)
Country | Link |
---|---|
US (1) | US4397783A (ko) |
KR (1) | KR840000589B1 (ko) |
AR (1) | AR225758A1 (ko) |
AT (1) | AT369744B (ko) |
AU (1) | AU518472B2 (ko) |
CA (1) | CA1154011A (ko) |
CH (1) | CH648850A5 (ko) |
DD (1) | DD149366A5 (ko) |
DE (1) | DE3008316C2 (ko) |
DK (1) | DK157136C (ko) |
ES (1) | ES489186A0 (ko) |
FI (1) | FI71739C (ko) |
FR (1) | FR2450837A1 (ko) |
GB (1) | GB2047684B (ko) |
GR (1) | GR67697B (ko) |
HK (1) | HK66687A (ko) |
IE (1) | IE51931B1 (ko) |
IL (1) | IL59514A (ko) |
IT (1) | IT1130301B (ko) |
KE (1) | KE3456A (ko) |
LU (1) | LU82219A1 (ko) |
MY (1) | MY8500320A (ko) |
NL (1) | NL8001286A (ko) |
NO (1) | NO800617L (ko) |
OA (1) | OA06496A (ko) |
PH (2) | PH18550A (ko) |
PT (1) | PT70898A (ko) |
SE (1) | SE451329B (ko) |
SG (1) | SG56484G (ko) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4518530A (en) * | 1979-03-05 | 1985-05-21 | Pfizer Inc. | 6-β-Substituted penicillanic acids as β-lactamase inhibitors |
IE49770B1 (en) * | 1979-05-21 | 1985-12-11 | Leo Pharm Prod Ltd | 6beta-halopenicillanic acid derivatives |
US4511512A (en) * | 1980-05-01 | 1985-04-16 | Leo Pharmaceutical Products Ltd. A/S (Lovens Kemiske Produktionsaktiensel skab) | Substantially pure dicyclohexyl ammonium 6-β-bromo-penicillanate |
IE51846B1 (en) * | 1980-11-17 | 1987-04-15 | Leo Pharm Prod Ltd | Pharmaceutical preparation for veterinary use and an appliance containing it |
EP0139047A1 (en) * | 1983-10-18 | 1985-05-02 | Gist-Brocades N.V. | Process for the preparation of 6,6-dibromopenicillanic acid 1,1-dioxide |
GB8522156D0 (en) * | 1985-09-06 | 1985-10-09 | Leo Pharm Prod Ltd | Producing chemical compounds |
WO1987006230A1 (en) * | 1986-04-10 | 1987-10-22 | Leo Pharmaceutical Products Ltd. A/S | Method for preparing penicillanic acid derivatives |
PA8579701A1 (es) * | 2002-08-23 | 2005-05-24 | Pfizer Prod Inc | Profarmaco inhibidor de beta-lactamasa |
EP1636240A1 (en) * | 2003-06-05 | 2006-03-22 | Pfizer Products Inc. | Beta-lactamase inhibitor prodrug |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5749555B2 (ko) * | 1973-04-04 | 1982-10-22 | ||
US4093625A (en) * | 1976-08-09 | 1978-06-06 | Massachusetts Institute Of Technology | 6-Sulfur analogs of penicillins and cephalosporins |
US4180506A (en) * | 1978-01-18 | 1979-12-25 | Rex Pratt | 6β-Bromo penicillanic acid |
US4203992A (en) * | 1978-12-11 | 1980-05-20 | E. R. Squibb & Sons, Inc. | β-Bromopenicillanic acid sulfone |
CA1158639A (en) * | 1978-12-11 | 1983-12-13 | Eric M. Gordon | 6-bromopenicillanic acid sulfone |
IL59081A0 (en) * | 1979-01-10 | 1980-05-30 | Schering Corp | 2-penem compounds and a method for preparing them |
DE3068390D1 (en) * | 1979-01-10 | 1984-08-09 | Beecham Group Plc | Penicillin derivatives, process for their preparation and pharmaceutical compositions containing certain of these compounds |
-
1979
- 1979-11-23 US US06/096,832 patent/US4397783A/en not_active Expired - Lifetime
-
1980
- 1980-03-03 PH PH23716A patent/PH18550A/en unknown
- 1980-03-03 GB GB8007142A patent/GB2047684B/en not_active Expired
- 1980-03-03 IL IL59514A patent/IL59514A/xx not_active IP Right Cessation
- 1980-03-03 LU LU82219A patent/LU82219A1/fr unknown
- 1980-03-03 GR GR61335A patent/GR67697B/el unknown
- 1980-03-04 IE IE428/80A patent/IE51931B1/en not_active IP Right Cessation
- 1980-03-04 DK DK092880A patent/DK157136C/da not_active IP Right Cessation
- 1980-03-04 CA CA000346906A patent/CA1154011A/en not_active Expired
- 1980-03-04 AT AT0118980A patent/AT369744B/de not_active IP Right Cessation
- 1980-03-04 PT PT70898A patent/PT70898A/pt unknown
- 1980-03-04 DE DE3008316A patent/DE3008316C2/de not_active Expired
- 1980-03-04 SE SE8001689A patent/SE451329B/sv not_active IP Right Cessation
- 1980-03-04 DD DD80219434A patent/DD149366A5/de unknown
- 1980-03-04 AR AR225758A patent/AR225758A1/es active
- 1980-03-04 NO NO800617A patent/NO800617L/no unknown
- 1980-03-04 AU AU56105/80A patent/AU518472B2/en not_active Ceased
- 1980-03-04 KR KR1019800000921A patent/KR840000589B1/ko active
- 1980-03-04 FI FI800662A patent/FI71739C/fi not_active IP Right Cessation
- 1980-03-04 NL NL8001286A patent/NL8001286A/nl not_active Application Discontinuation
- 1980-03-04 FR FR8004765A patent/FR2450837A1/fr active Granted
- 1980-03-04 ES ES489186A patent/ES489186A0/es active Granted
- 1980-03-04 CH CH1715/80A patent/CH648850A5/de not_active IP Right Cessation
- 1980-03-05 IT IT20368/80A patent/IT1130301B/it active
- 1980-03-27 OA OA57065A patent/OA06496A/xx unknown
- 1980-09-12 PH PH24569A patent/PH17879A/en unknown
-
1984
- 1984-08-13 SG SG564/84A patent/SG56484G/en unknown
- 1984-09-24 KE KE3456A patent/KE3456A/xx unknown
-
1985
- 1985-12-30 MY MY320/85A patent/MY8500320A/xx unknown
-
1987
- 1987-09-17 HK HK666/87A patent/HK66687A/xx unknown
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