KR940007033A - 카르바페넴 화합물 - Google Patents
카르바페넴 화합물 Download PDFInfo
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- KR940007033A KR940007033A KR1019930019555A KR930019555A KR940007033A KR 940007033 A KR940007033 A KR 940007033A KR 1019930019555 A KR1019930019555 A KR 1019930019555A KR 930019555 A KR930019555 A KR 930019555A KR 940007033 A KR940007033 A KR 940007033A
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- hydroxyethyl
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- ylthio
- carboxylic acid
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- -1 Carbapenem Compound Chemical class 0.000 title claims 11
- 150000001875 compounds Chemical class 0.000 claims abstract 18
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract 9
- 239000001257 hydrogen Substances 0.000 claims abstract 9
- 125000004066 1-hydroxyethyl group Chemical group [H]OC([H])([*])C([H])([H])[H] 0.000 claims abstract 5
- 150000002148 esters Chemical class 0.000 claims abstract 5
- 229910052760 oxygen Inorganic materials 0.000 claims abstract 5
- 150000003839 salts Chemical class 0.000 claims abstract 5
- 238000001727 in vivo Methods 0.000 claims abstract 4
- 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
- 125000006239 protecting group Chemical group 0.000 claims 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims 5
- 125000005115 alkyl carbamoyl group Chemical group 0.000 claims 4
- 125000000217 alkyl group Chemical group 0.000 claims 4
- 125000003302 alkenyloxy group Chemical group 0.000 claims 2
- 125000003545 alkoxy group Chemical group 0.000 claims 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 2
- 125000004093 cyano group Chemical group *C#N 0.000 claims 2
- 125000001475 halogen functional group Chemical group 0.000 claims 2
- 150000002431 hydrogen Chemical class 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims 1
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003118 aryl 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
- 230000032050 esterification Effects 0.000 claims 1
- 238000005886 esterification reaction Methods 0.000 claims 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 claims 1
- 125000000524 functional group Chemical group 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000008194 pharmaceutical composition Substances 0.000 claims 1
- 235000013311 vegetables Nutrition 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000001424 substituent group Chemical group 0.000 abstract 1
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- 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
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- 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
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- 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
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- 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
- C07D207/04—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 no double bonds between ring members or between ring members and non-ring members
- C07D207/10—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 no 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
- C07D207/16—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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- 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
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- 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
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- C07D—HETEROCYCLIC COMPOUNDS
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- C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
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- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
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Abstract
본 발명은 하기 일반식(Ⅰ)의 화합물 또는 그것이 약학적 허용염 또는 그것의 생체내 가수분해성 에스테르를 제공한다.
상기 식중, A는 하기 식(lA) 또는 (lB)의 기이고,
R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고, R2는 수소 또는 C1-C4알킬이고, R3와 R4는 동일하거나 상이하며, 수소, 할로, 시아노, C1-2알킬, 니트로, 히드로시, 카르복시, C1-2알콕시, C1-2알콕시카르보닐, 카르바모일, C1-2알킬카르바모일, 디-C1-2알킬카바모일, 트리플루오로메틸 및 C3-4알케닐옥시중에서 선택되며, X는 O,S(O)x(x는 0,1 또는 2임), -CONR5-또는 -NR5(R5는 수소 또는 C1-6알칸디일)가 임의로 삽입된 C1-6알킨디일이거나, O,S(O)x -NR5(x 및 R5는 전술한 바와 같음)가 임의로 삽입된 C1-3알켄디일이고, 단, 다음의 i) 및 ii를 조건으로 한다.
i) 상기 삽입기(O,S(O)x, -NR5, -CONR5-)는 고리 A에 직접적으로 연결될 수 있으나, -COOH기 또는 x의 임의의 C=C결합에는 직접 연결될 수 없으며, ii)상기 삽입기가 -SO-또는 -SO2-일때, COOH기에 대해 β위치가 아니거나 x에 내재된 C=C결합이 있는 경우 §위치가 아니어야 한다.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 하기 일반식(Ⅰ)의 화합물 또는 그것의 약학적 허용염 또는 그것의 생채내 가수분해성 에스테르.상기 식중, A는 하기 식(lA) 또는 (lB)의 기이고,R1은 1-히드록시에틸, 1-플루오로에틸 또는 히드록시메틸이고, R2는 수소 또는 C1-4알킬이고, R3와 R4는 동일하거나 상이하며, 수소, 할로, 시아노, C1-2알킬, 니트로, 히드록시, 카르복시, C1-2알콕시카르보닐, 카르바모일, C1-4알킬카르바모일, 디-C1-2알킬카바모일, 트리플루오로메틸 및 C3-4알케닐옥시중에서 선택되며, X는 O,S(O)x(x는 0,1 또는 2임), -CONR5-또는 -NR5(R5는 수소 또는 C1-6알칸디일)가 임의로 삽입된 C1-6알칸디일이거나, O,S(O)x 또는 (x 및 R5는 전술한 바와 같음)가 임의로 삽입된 C2-6알켄디일이고,i) 상기 삽입기(O,S(O)x, -NR5, -CONR5-)는 고리 A에 직접적으로 연결될 수 있으나, -COOH기 또는 x의 임의의 C=C결합에는 직접 연결될 수 없으며, ii)상기 삽입기가 -SO-또는 -SO2-일때, COOH기에 대해 β위치가 아니거나 x에 내재된 C=C결합이 있는 경우위치가 아니여야 한다.
- 제1항에 있어서, R1이 1-히드록시에틸인 화합물.
- 제1항 또는 제2항에 있어서, 하기식(Ⅳ)인 화합물.상기식중, A 및 X는 제1항에서 정의된 바와 같다.
- 제3항에 있어서, X는 메틸렌, 에틸렌, 옥시메틸렌, 비닐렌, 메톡옥시메틸렌 및 티오메틸인 화합물.
- 제1항 내지 제4항중 어느 한 항에 있어서, R3와 R4(A내의)가 각각 수소, 할로, 시아노, C1-4알킬, 니트로, 히드록시, 카르복시, C1-4알콕시, 카르바모일, 알킬카르바모일, 디-C1-4알킬카르바모일, 트리플루오로메틸 및 C3-4알케닐옥시중에서 선택되는 화합물.
- 제1항에 있어서, [1R,5S,6S,8R,2'S,4'S]-2-(2-(3-E-2-카르복시-1-에테닐)페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-E-2-카르복시-1-에테닐)-6-히드록시-페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시에틸페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시네메톡시페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시메틸)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시메틸페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시메틸아미노카르보닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시메틸아미노카르보닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2'S,4'S)-2-(2-(3-카르복시메틸티오페닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, (1R,5S,6S,8R,2`S,4`S)-2-(2-(3-카르복시메틸카르바모일-5-티에닐카르바모일)피롤리딘-4-일티오)-6-(1-히드록시에틸)-1-메틸카르바페넴-3-카르복실산, 및 그것의 약학적 허용염 및 생체내 가수분해성 에스테르인 화합물.
- 제1항 내지 제6항중 어느 한 항의 화합물과 약학적 허용 담체를 포함하는 약학적 조성물.
- 하기 일반식(Ⅴ)의 화합물을 탈보호시키는 단계 및 이어서 필요한 경우에는, (i) 약학적 허용염을 형성하는 단계, (ii) 에스테르화시킴으로써 생체내 가수분해성 에스테르를 형성시키는 단계를 포함하는, 제1항의 화합물을 제조하는 방법.상기 식중, A,X 및 R2내지 R4는 제1항에서 정의된 바와 같고(R3와 R4는 적당하게 임의로 보호됨), R6및 R7은 수소 또는 카르복사 보호기이고, R8는 수소 또는 아미노 보호기이고, R9는 수소 또는 아미노 보호기이고, R10은 R1기, 보호된 히드록시메틸 또는 보호된 1-히드록시에틸이고, 하나 이상의 보호기가 존재한다.
- (a) 하기 일반식(Ⅵ)의 화합물과 하기 일반식(Ⅶ)의 화합물을 반응시키거나, 또는 (b)하기 일반식(Ⅷ)화합물을 고리화한후, 이어서 필요한 경우, (i)임의의 보호기를 제거하고, (ii)약학적 허용염을 형성시키고, (iii)에스테르화시켜 생체내 가수분해성 에스테르를 형성시키는 단계를 포함하는, 제1항의 화합물 또는 제8항에서 규정된 식(Ⅴ)의 화합물을 제조하는 방법.상기식중, A, X 및 R2내지 R11은 제8항에 정의된 바와 같고, L은 이탈기이고, R10내지 R13은 각각 C1-6알킬아미노 및 디아릴아미노중에서 선택되거나, R11내지 R13중 임의의 두개는 o-페닐렌디옥시를 나타내거나 또는 R11내지 R13중 하나는 C1-4알킬, 아릴, 벤질 또는 페닐을 나타내며, 임의의 페닐기는 C1-3알킬 또는 C1-3알콕시로 임의 치환되며 임의로 작용기는 임의로 보호된다.
- 제8항의 방법으로 제조된 식(Ⅴ)의 화합물, 제9항의 방법으로 제조된 식(Ⅶ) 또는 식(Ⅷ)의 화합물 또는 하기 식(Ⅸ),(ⅩⅡ) 또는 (ⅩⅣ)의 화합물.상기 식중, A,X 및 R2-R4, R6-R10은 제9항에서 정의된 바와 같으며, R14는 보호기이다.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP92402648.7 | 1992-09-28 | ||
| EP92402648 | 1992-09-28 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| KR940007033A true KR940007033A (ko) | 1994-04-26 |
| KR100293118B1 KR100293118B1 (ko) | 2001-09-17 |
Family
ID=8211714
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019930019555A KR100293118B1 (ko) | 1992-09-28 | 1993-09-24 | 카르바페넴화합물 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US5527791A (ko) |
| JP (1) | JPH06211860A (ko) |
| KR (1) | KR100293118B1 (ko) |
| AT (1) | ATE190615T1 (ko) |
| CA (1) | CA2106141A1 (ko) |
| DE (1) | DE69328061T2 (ko) |
| ES (1) | ES2144446T3 (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 |
| US7932381B2 (en) * | 2005-02-15 | 2011-04-26 | Shionogi & Co., Ltd. | Process for producing carbapenem derivative and intermediate crystal therefor |
| US7989554B2 (en) * | 2006-01-10 | 2011-08-02 | Enzon Pharmaceuticals, Inc. | Reacting polyalkylene oxide with base, tertiary alkyl haloacetate, then acid to prepare polyalkylene oxide carboxylic acid |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4232036A (en) * | 1978-10-24 | 1980-11-04 | Merck & Co., Inc. | 6-, 1- and 2-Substituted-1-carbadethiapen-2-em-3-carboxylic acids |
| US4208422A (en) * | 1978-10-24 | 1980-06-17 | Merck & Co., Inc. | 1-Substituted-pen-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 |
| US4206219A (en) * | 1978-10-24 | 1980-06-03 | Merck & Co., Inc. | 6- and 1-Substituted-1-carbadethiapen-2-em-3-carboxylic acid |
| 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 |
| DE3579888D1 (de) * | 1984-11-08 | 1990-10-31 | Sumitomo Pharma | Carbapenemverbindungen und deren herstellung. |
| ES2051700T3 (es) * | 1986-03-27 | 1994-07-01 | Sumitomo Pharma | Un proceso para la preparacion de un compuesto beta-lactama. |
| IE910606A1 (en) * | 1990-02-23 | 1991-08-28 | Sankyo Co | Carbapenem derivatives having antibiotic activity, their¹preparation 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 |
-
1993
- 1993-09-14 CA CA002106141A patent/CA2106141A1/en not_active Abandoned
- 1993-09-21 US US08/123,998 patent/US5527791A/en not_active Expired - Fee Related
- 1993-09-23 DE DE69328061T patent/DE69328061T2/de not_active Expired - Fee Related
- 1993-09-23 AT AT93307551T patent/ATE190615T1/de not_active IP Right Cessation
- 1993-09-23 ES ES93307551T patent/ES2144446T3/es not_active Expired - Lifetime
- 1993-09-24 KR KR1019930019555A patent/KR100293118B1/ko not_active IP Right Cessation
- 1993-09-28 JP JP5241519A patent/JPH06211860A/ja active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| DE69328061T2 (de) | 2000-09-28 |
| DE69328061D1 (de) | 2000-04-20 |
| KR100293118B1 (ko) | 2001-09-17 |
| JPH06211860A (ja) | 1994-08-02 |
| ATE190615T1 (de) | 2000-04-15 |
| ES2144446T3 (es) | 2000-06-16 |
| CA2106141A1 (en) | 1994-03-29 |
| US5527791A (en) | 1996-06-18 |
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