KR940002244A - 카르바페넴 화합물 - Google Patents
카르바페넴 화합물 Download PDFInfo
- Publication number
- KR940002244A KR940002244A KR1019930013541A KR930013541A KR940002244A KR 940002244 A KR940002244 A KR 940002244A KR 1019930013541 A KR1019930013541 A KR 1019930013541A KR 930013541 A KR930013541 A KR 930013541A KR 940002244 A KR940002244 A KR 940002244A
- Authority
- KR
- South Korea
- Prior art keywords
- compound
- formula
- group
- alkyl
- carboxy
- Prior art date
Links
- -1 Carbapenem Compound Chemical class 0.000 title claims 7
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 6
- 239000001257 hydrogen Substances 0.000 claims abstract 6
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 229910052799 carbon Inorganic materials 0.000 claims abstract 4
- 150000002148 esters Chemical class 0.000 claims abstract 4
- 238000001727 in vivo Methods 0.000 claims abstract 4
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims abstract 3
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims abstract 3
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims abstract 3
- 125000004776 1-fluoroethyl group Chemical group [H]C([H])([H])C([H])(F)* 0.000 claims abstract 2
- 125000006163 5-membered heteroaryl group Chemical group 0.000 claims abstract 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000005842 heteroatom Chemical group 0.000 claims abstract 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract 2
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 2
- 239000001301 oxygen Chemical group 0.000 claims abstract 2
- 239000008194 pharmaceutical composition Substances 0.000 claims abstract 2
- 125000000217 alkyl group Chemical group 0.000 claims 8
- 125000006239 protecting group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 4
- 125000003545 alkoxy group Chemical group 0.000 claims 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 4
- 125000001424 substituent group Chemical group 0.000 claims 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 3
- 125000003282 alkyl amino group Chemical group 0.000 claims 2
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000005843 halogen group Chemical group 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- 125000005236 alkanoylamino group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000004104 aryloxy group Chemical group 0.000 claims 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004986 diarylamino group Chemical group 0.000 claims 1
- 239000003937 drug carrier Substances 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 1
- 229910052717 sulfur Inorganic materials 0.000 claims 1
- 239000011593 sulfur Substances 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 239000005864 Sulphur Chemical group 0.000 abstract 1
- 229940041011 carbapenems Drugs 0.000 abstract 1
- 239000003814 drug Substances 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 229940124597 therapeutic agent Drugs 0.000 abstract 1
Classifications
-
- 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
- C07D477/20—Sulfur atoms
-
- 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
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
-
- 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
- C07D413/12—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 linked by a chain containing hetero atoms as chain links
-
- 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
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing three or more hetero rings
-
- 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
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/553—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having one nitrogen atom as the only ring hetero atom
- C07F9/568—Four-membered rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Biochemistry (AREA)
- Oncology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Pharmacology & Pharmacy (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Communicable Diseases (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
본 발명은 카르바페넴에 관한 것으로, 하기 일반식(Ⅰ)의 화합물 또는 이의 약학적으로 허용가능한 염 또는 이의 생체내 가수분해성 에스테르를 제공한다.
상기 식에서 R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고; R2는 수소 또는 C1-4알킬이고; R3는 수소 또는 C1-4알킬이고; A는 하나의 질소원자와 질소, 산소 및 황중에서 선택된 2개 이하의 부가의 헤테로 원자를 함유하는 5-원 헤테로아릴고리이고; 고리내의 탄소원자에 의해 인쇄하는 카르바모일기의 질소에 결합되고; 고리내의 탄소원자상에서 카르복시기로 치환되며, 임의로 할로, 시아노, C1-4알킬, 니트로, 히드록시, 카르복시, C1-4알콕시, 트리플루오로메틸, C1-4알콕시카르보닐, 아미노, C1-4알킬아미노, 디-C1-4알킬아미노, C1-4알킬S(O)n-(이때, n은 O-2임), C1-4알카노일아미노, C1-4알카노일아미노, 카르바모일, C1-4알킬카르바모일 또는 디-C1-4알킬카르바모일에 의해 추가로 치환되며; 어떤 고리에서도 -NH-, H는 C1-4알킬에 의해 임의로 치환된다.
또한 본 발명은 본 발명의 화합물의 제조방법, 이의 제조시의 중간체, 이를 치료제로서 사용하는 방법, 및 이를 함유하는 약학적 조성물에 관한 것이다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 일반식(Ⅰ)의 화합물 또는 이의 약학적으로 허용가능한 염 또는 이의 생체내 가수분해성 에스테르:상기 식에서 R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고; R2는 수소 또는 C1-4알킬이고; R3는 수소 또는 C1-4알킬이고; A는 하나의 질소원자와 질소, 산소 및 황중에서 선택된 2개이하의 부가의 헤테로 원자를 함유하는 5-원 헤테로아릴고리이고; 고리내의 탄소원자에 의해 연쇄하는 카르바모일기의 질소에 결합되고; 고리내의 탄소원자상에서 카르복시기로 치환되며, 임의로 할로, 시아노, C1-4알킬, 니트로, 히드록시, 카르복시, C1-4알콕시, 트리플루오로메틸, C1-4알콕시카르보닐, 아미노, C1-4알킬아미노, 디-C1-4알킬아미노, C1-4알킬S(O)n-(이때, n은 O-2임), C1-4알카노일아미노, C1-4알카노일아미노, 카르바모일, C1-4알킬카르바모일 또는 디-C1-4알킬카르바모일에 의해 추가로 치환되며; 어떤 고리에서도 -NH-, H는 C1-4알킬에 의해 임의로 치환된다.
- 제1항에 있어서, R2가 메틸인 화합물.
- 제1항에 있어서, R1이 1-히드록시에틸인 화합물.
- 제1항 또는 제2항에 있어서, 하기 일반식(Ⅳ)로 표시되는 화합물:상기 식에서, A, R3및, A상의 임의의 치환체는 제1항에서 정의한 바와 같다.
- 제4항에 있어서, A상의 임의의 치환체가 할로, 시아노, C1-4알킬, 니트로, 히드록시, 카르복시, C1-4알콕시, 카르바모일, 아미노 및 트리플루오로메틸중에서 선택된 화합물.
- 제1항에 있어서, (1R,5S,6S,8R,2'S,4'S)-2-(2-(5-카르복시티아졸-2-일카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R,5S,6S,8R,2'S,4'S)-2-(2-(5-카르복시-1-H-이미다졸-4-일카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산:(1R,5S,6S,8R,2'S,4'S)-2-(2-(2-카르복시피롤-4-일카르바모일) 피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R,5S,6S,8R,2'S,4'S)-2-(2-(4-카르복시티아졸-2-일카르바모일) 피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; (1R,5S,6S,8R,2'S,4'S)-2-(2-(5-카르복시-1,3,4-티아디아졸-2-일카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산; 및 이들의 약학적으로 허용가능한 염인 화합물.
- 제1항 내지 제6항중 어느 한 항에서 정의한 화합물과 약학적으로 허용가능한 담체를 포함하는 약학적 조성물.
- 하기 일반식(Ⅴ)의 화합물의 보호기를 제거하고, 차후에 필요에 따라, (i) 약학적으로 허용가능한 염을 형성시키거나, (ii) 이를 에스테르화시키므로써 생체내 가수분해성 에스테르를 형성시키는 것을 포함하는, 제1항에서 정의한 화합물을 제조하는 방법.상기 식에서, R2는 제1항에서의 정의된 바와 같고; R10은 R3기(제1항에서 정의한 바와 같음) 또는 아미노 보호기이며; R13은 R1기(제1항에서 정의한 바와 같음), 보호된 히드록시메틸 또는 1-(보호된 히드록시)에틸기이며; R11은 수소 또는 카르복시 보호기이며; R12는 수소 또는 아미노 보호기이며; A는 제1항에서 정의한 바와 같고; R18은 카르복시 또는 보호된 카르복시기이고, 이때 A상의 임의의 치환체는 제1항에서 정의한 바와 같고 임의로 보호되며; 이때 적어도 하나의 보호기가 존재한다.
- (a) 하기 일반식(Ⅵ)의 화합물과 및 (Ⅶ)의 화합물을 반응시키거나; 또는 (b) 하기 일반식(Ⅷ)의 화합물의 고리화시키고; 그후에 필요에 따라, (i) 임의의 보호기를 제거하고; (ii) 약학적으로 허용가능한 염을 형성시키고; (iii) 에스테르화시켜 생체내 가수분해성 에스테르를 형성시키는 것을 포함하는, 제1항에서 정의한 화합물 또는 제8항에서 정의한 일반식(Ⅴ)의 화합물을 제조하는 방법:상기 식에서, A, R2,R10,R11,R12,R13및 R18은 제8항에서 정의된 바와 같고; A상의 임의의 치환체는 제8항에서 정의된 바와 같고; R14,R15및 R16은 각각 C1-6알콕시, 아릴옥시, 디-C1-6알킬아미노 및 디아릴아미노중에서 선택되거나, R14-R16중의 임의의 두개는페닐렌디옥시를 나타내거나, 또는 R14-R16중의 하나는 C1-4알킬, 알릴, 벤질 또는 페닐을 나타내고 나머지 두개는 C1-4알킬, 트리플루오로메틸 또는 페닐중에서 선택되며; 이때, 어떠한 페닐기도 C1-3알킬 또는 C1-3알콕시에 의해 임의로 치환되며; 어떠한 작용기도 임의로 보호된다.
- 제8항에서 정의한 바와 같은 일반식(Ⅴ)의 화합물, 제9항에서 정의한 바와 같은 일반식(Ⅶ) 또는 (Ⅷ)의 화합물, 또는 하기식 일반식(Ⅸ), (ⅩI) 또는 (ⅩⅣ)의 화합물:상기 식에서, A, R2,R10-R13및 R18은 제8항에서 정의한 바와 같고, R17은 보호기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92402103 | 1992-07-21 | ||
| EP92402103.3 | 1992-07-21 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940002244A true KR940002244A (ko) | 1994-02-17 |
| KR100278029B1 KR100278029B1 (ko) | 2001-02-01 |
Family
ID=8211689
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930013541A KR100278029B1 (ko) | 1992-07-21 | 1993-07-19 | 카르바페넴 화합물 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5527793A (ko) |
| JP (1) | JPH06179676A (ko) |
| KR (1) | KR100278029B1 (ko) |
| AT (1) | ATE172462T1 (ko) |
| CA (1) | CA2099817A1 (ko) |
| DE (1) | DE69321671T2 (ko) |
| ES (1) | ES2123031T3 (ko) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB9202298D0 (en) * | 1992-02-04 | 1992-03-18 | Ici Plc | Antibiotic compounds |
| SI1926732T1 (sl) | 2005-09-05 | 2014-02-28 | Ranbaxy Laboratories Limited | Postopek za pripravo karbapenskih spojin |
| CN101613352B (zh) * | 2008-06-25 | 2013-03-27 | 山东轩竹医药科技有限公司 | 含有甲酰胺杂环基巯基吡咯烷的培南衍生物 |
Family Cites Families (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4206219A (en) * | 1978-10-24 | 1980-06-03 | Merck & Co., Inc. | 6- and 1-Substituted-1-carbadethiapen-2-em-3-carboxylic acid |
| US4232036A (en) * | 1978-10-24 | 1980-11-04 | Merck & Co., Inc. | 6-, 1- and 2-Substituted-1-carbadethiapen-2-em-3-carboxylic acids |
| US4218462A (en) * | 1978-10-24 | 1980-08-19 | Merck & Co., Inc. | 6-(1-Hydroxyethyl)-2-(2-aminoethylthio)-1-substituted-1-carbade-thiapen-2-em-3-carboxylic acids |
| US4208422A (en) * | 1978-10-24 | 1980-06-17 | Merck & Co., Inc. | 1-Substituted-pen-2-em-3-carboxylic acids |
| EP0017992A1 (en) * | 1979-04-19 | 1980-10-29 | Merck & Co. Inc. | 2-Substituted-6-substituted-1-carbadethiapen-2-em-3-carboxylic acids, processes for preparing them, antibiotic pharmaceutical compositions containing same and process for preparing intermediates |
| CA1283906C (en) * | 1983-05-09 | 1991-05-07 | Makoto Sunagawa | .beta.-LACTAM COMPOUNDS AND PRODUCTION THEREOF |
| JPS60202886A (ja) * | 1984-03-27 | 1985-10-14 | Sankyo Co Ltd | １―置換カルバペネム―３―カルボン酸誘導体 |
| JPS60233076A (ja) * | 1984-05-03 | 1985-11-19 | Sumitomo Chem Co Ltd | 新規なβ−ラクタム化合物およびその製造法 |
| EP0182213B1 (en) * | 1984-11-08 | 1990-09-26 | Sumitomo Pharmaceuticals Company, Limited | Carbapenem compounds and production thereof |
| ES2051700T3 (es) * | 1986-03-27 | 1994-07-01 | Sumitomo Pharma | Un proceso para la preparacion de un compuesto beta-lactama. |
| US5227376A (en) * | 1990-02-14 | 1993-07-13 | Sumitomo Pharmaceuticals Co., Ltd. | β-lactam compounds and their production |
| AU646012B2 (en) * | 1990-02-23 | 1994-02-03 | Sankyo Company Limited | Carbapenem derivatives having antibiotic activity, their preparation and their use |
| AU644008B2 (en) * | 1990-08-10 | 1993-12-02 | Sumitomo Pharmaceuticals Company, Limited | Beta-lactam compounds, and their production and use |
| GB9107341D0 (en) * | 1991-04-08 | 1991-05-22 | Ici Plc | Antibiotic compounds |
| CA2099811A1 (en) * | 1992-07-21 | 1994-01-22 | Frederic H. Jung | Antibiotic compounds |
| CA2099818A1 (en) * | 1992-07-21 | 1994-01-22 | Frederic H. Jung | Antibiotic compounds |
| AU4912393A (en) * | 1993-06-15 | 1994-12-22 | Dong Kook Pharmaceutical Co., Ltd. | 1-beta-methyl-2-thiolic carbapenem derivatives |
-
1993
- 1993-07-05 CA CA002099817A patent/CA2099817A1/en not_active Abandoned
- 1993-07-07 US US08/086,838 patent/US5527793A/en not_active Expired - Fee Related
- 1993-07-16 ES ES93305609T patent/ES2123031T3/es not_active Expired - Lifetime
- 1993-07-16 DE DE69321671T patent/DE69321671T2/de not_active Expired - Fee Related
- 1993-07-16 AT AT93305609T patent/ATE172462T1/de not_active IP Right Cessation
- 1993-07-19 KR KR1019930013541A patent/KR100278029B1/ko not_active IP Right Cessation
- 1993-07-21 JP JP5180095A patent/JPH06179676A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE69321671D1 (de) | 1998-11-26 |
| DE69321671T2 (de) | 1999-04-01 |
| US5527793A (en) | 1996-06-18 |
| ES2123031T3 (es) | 1999-01-01 |
| KR100278029B1 (ko) | 2001-02-01 |
| JPH06179676A (ja) | 1994-06-28 |
| CA2099817A1 (en) | 1994-01-22 |
| ATE172462T1 (de) | 1998-11-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| KR910021402A (ko) | 항균활성을 갖는 카르바페넴 유도체 및 그의 제법 및 용도 | |
| AU6307290A (en) | Pyrazole derivatives, processes for preparation thereof and pharmaceutical composition comprising the same | |
| KR890011827A (ko) | 화학적 화합물 | |
| RU2003123104A (ru) | Новые гетероциклические соединения, имеющие антибактериальную активность:способ их получения и фармацевтические композиции, содеержащие их | |
| KR940002246A (ko) | 카르바페넴 화합물 | |
| KR930006014A (ko) | 삼환식 복소환식 화합물 | |
| KR940005626A (ko) | 항생 화합물 | |
| KR950017971A (ko) | 신규한 항바이러스성 2, 4-피리미딘디온 유도체 및 그의 제조방법 | |
| KR900003156A (ko) | 진통제 화합물, 그의 제조방법 및 그를 함유하는 약학 조성물 | |
| KR960007593A (ko) | 카르바페넴 화합물 | |
| KR940002244A (ko) | 카르바페넴 화합물 | |
| KR970074773A (ko) | 신규한 항바이러스성 6-아릴옥시 및 6-아릴카르보닐 2, 4-피리미딘디온 유도체 및 그의 제조 방법 | |
| KR940002245A (ko) | 카르바페넴 화합물 | |
| KR900018089A (ko) | (티오) 모르폴리닐 및 피페라지닐 알킬페놀 에테르 유도체 | |
| KR940011450A (ko) | 살진균성 2-알콕시-2-이미다졸린-5-온 유도체 | |
| KR920016456A (ko) | 5-(치환 아미노) -1,2,4-트리아졸로 [1,5-a]피리미딘 유도체 | |
| KR940009189A (ko) | 페넴 화합물 | |
| KR970705539A (ko) | 카르바모일 카르복실산 아미드(carbamoyl carboxylic acid amides) | |
| KR910016755A (ko) | 2-(치환피롤리디닐티오) 카르바페넴 유도체 | |
| KR910006300A (ko) | 신규 화합물 | |
| KR900014322A (ko) | 치환(퀴놀린-2-일-메톡시)페닐-n.n-술포닐우레아, 그의 제조방법 및 약물 용도 | |
| KR940007033A (ko) | 카르바페넴 화합물 | |
| CA1268183A (en) | INTERMEDIATES OF PHOSPHORANE USED IN THE PREPARATION OF ANTIBIOTIC PENEMS | |
| BR9608929A (pt) | Derivados de hidroxilamina anti-isquêmicos e composições farmacêuticas | |
| KR950014111A (ko) | 새로운 카바페넴 유도체 및 그 제조방법 |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E902 | Notification of reason for refusal | ||
| E701 | Decision to grant or registration of patent right | ||
| GRNT | Written decision to grant | ||
| LAPS | Lapse due to unpaid annual fee |